#==============================================================================
data_global
#==============================================================================

_publ_contact_author               'Darren J Dixon'
_publ_contact_author_email          darren.dixon@chem.ox.ac.uk

loop_
_publ_author_name
_publ_author_address
 'Jakubec, Pavol '
;    
Chemistry Research Laboratory,
University of Oxford,
Mansfield Road, 
Oxford OX1 3TA, UK.
;
'Cockfield, Dane M.'
;     
School of Chemistry, 
The University of Manchester,
Manchester 
M13 9PL, UK.
;
'Helliwell, Madeleine'
;     
School of Chemistry, 
The University of Manchester,
Manchester 
M13 9PL, UK.
;
'Raftery, James'
;    
School of Chemistry, 
The University of Manchester,
Manchester 
M13 9PL, UK.
;
'Dixon, Darren J.'
;    
Chemistry Research Laboratory,
University of Oxford,
Mansfield Road, 
Oxford OX1 3TA. UK.
;
_journal_name_full                 
 'Beilstein Journal of Organic Chemistry'
_journal_volume                    '?'
_journal_page_first                '?'
_journal_page_last                 '?'
_journal_year                      '2011'
_ccdc_journal_depnumber            '?'

_publ_section_title
;
Stereoselective, nitro-Mannich/lactamization cascades for the direct 
synthesis of heavily decorated 5-nitro piperidin-2-ones and related 
heterocycles.
;

_publ_section_abstract
;  
A versatile nitro-Mannich / lactamization cascade for the direct 
stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and 
related heterocycles has been developed. A highly enantioenriched substituted 
5-nitropiperidin-2-one was synthesized in four component one-pot reaction 
combining an enantioselective Michael addition with the diastereoselective
nitro-Mannich / lactamization cascade. Protodenitration and chemoselective
reductive manipulation of the heterocycles can be used to install contiguous
and fully substituted stereocentres in the synthesis of substituted piperidines. 
;

  
#==============================================================================
data_1g     #s2730abs 
#==============================================================================
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_publ_section_exptl_refinement 
; 
The structure was solved by the direct methods. 
All non-H atoms were refined anisotropically. 
H atoms were included in calculated positions. 
;
  
_publ_section_references 
; 
Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison,
Wisconsin, USA.

M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, 
 G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori 
 and R. Spagna 
 SIR2004: an improved tool for crystal structure determination 
 and refinement 
 J. Appl. Cryst. (2005). 38, 381-388 

Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97.
University of Göttingen, Germany.

Sheldrick, G, M. (2005). CELL_NOW. University
of Göttingen, Germany.

Sheldrick, G, M. (2007). TWINABS. University
of Göttingen, Germany.

Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13. 

; 
  
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety         'C19 H21 N3 O6' 
_chemical_formula_sum 
 'C19 H21 N3 O6' 
_chemical_formula_weight          387.39 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    Pna2(1) 
_symmetry_space_group_name_Hall P2c-2n 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, z+1/2' 
 'x+1/2, -y+1/2, z' 
 '-x+1/2, y+1/2, z+1/2' 
  
_cell_length_a                    11.405(2) 
_cell_length_b                    14.943(3) 
_cell_length_c                    10.8676(18) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1852.2(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     4725 
_cell_measurement_theta_min       2.25 
_cell_measurement_theta_max       26.09 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.55 
_exptl_crystal_size_mid           0.50 
_exptl_crystal_size_min           0.50 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.389 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              816 
_exptl_absorpt_coefficient_mu     0.105 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9446 
_exptl_absorpt_correction_T_max   0.9495 
_exptl_absorpt_process_details    'SADABS'
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10299 
_diffrn_reflns_av_R_equivalents   0.0250 
_diffrn_reflns_av_sigmaI/netI     0.0192 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        18 
_diffrn_reflns_limit_l_min        -8 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          2.25 
_diffrn_reflns_theta_max          26.37 
_reflns_number_total              1996 
_reflns_number_gt                 1946 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0369P)²+0.3675P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          1996 
_refine_ls_number_parameters      255 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0280 
_refine_ls_R_factor_gt            0.0271 
_refine_ls_wR_factor_ref          0.0672 
_refine_ls_wR_factor_gt           0.0667 
_refine_ls_goodness_of_fit_ref    1.091 
_refine_ls_restrained_S_all       1.091 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.43762(11) 0.01633(8) 0.71553(14) 0.0197(3) Uani 1 1 d . . . 
O2 O 0.16616(11) -0.03207(8) 0.56022(13) 0.0177(3) Uani 1 1 d . . . 
O3 O -0.07541(11) 0.18666(10) 0.68926(15) 0.0254(3) Uani 1 1 d . . . 
O4 O 0.05373(13) 0.28493(9) 0.74531(14) 0.0254(3) Uani 1 1 d . . . 
O5 O 0.10145(13) -0.00952(9) 0.92357(17) 0.0297(4) Uani 1 1 d . . . 
O6 O 0.00425(11) 0.11973(8) 0.94774(14) 0.0206(3) Uani 1 1 d . . . 
H6 H -0.0471 0.0872 0.9804 0.031 Uiso 1 1 calc R . . 
N1 N 0.28930(13) 0.08263(10) 0.81892(16) 0.0161(3) Uani 1 1 d . . . 
N2 N 0.28719(13) 0.01691(10) 0.40548(16) 0.0179(3) Uani 1 1 d . . . 
N3 N 0.02498(13) 0.20987(10) 0.71369(16) 0.0176(3) Uani 1 1 d . . . 
C1 C 0.34703(15) 0.06020(11) 0.71396(18) 0.0144(4) Uani 1 1 d . . . 
C2 C 0.30022(15) 0.09521(12) 0.59074(18) 0.0138(4) Uani 1 1 d . . . 
C3 C 0.21289(15) 0.17389(11) 0.61139(18) 0.0134(3) Uani 1 1 d . . . 
H3A H 0.2570 0.2223 0.6549 0.016 Uiso 1 1 calc R . . 
C4 C 0.11986(15) 0.14009(11) 0.69992(18) 0.0136(3) Uani 1 1 d . . . 
H4 H 0.0855 0.0829 0.6687 0.016 Uiso 1 1 calc R . . 
C5 C 0.17479(15) 0.12541(11) 0.82734(18) 0.0146(4) Uani 1 1 d . . . 
H5 H 0.1849 0.1850 0.8677 0.018 Uiso 1 1 calc R . . 
C6 C 0.34982(18) 0.07271(13) 0.93881(19) 0.0219(4) Uani 1 1 d . . . 
H6A H 0.4222 0.0370 0.9280 0.026 Uiso 1 1 calc R . . 
H6B H 0.2983 0.0408 0.9975 0.026 Uiso 1 1 calc R . . 
C7 C 0.37999(18) 0.16317(14) 0.9889(2) 0.0245(4) Uani 1 1 d . . . 
H7 H 0.4457 0.1934 0.9551 0.029 Uiso 1 1 calc R . . 
C8 C 0.3207(2) 0.20320(17) 1.0771(2) 0.0342(5) Uani 1 1 d . . . 
H8A H 0.2546 0.1746 1.1127 0.041 Uiso 1 1 calc R . . 
H8B H 0.3442 0.2607 1.1051 0.041 Uiso 1 1 calc R . . 
C9 C 0.24319(15) 0.01854(11) 0.51775(18) 0.0149(4) Uani 1 1 d . . . 
C10 C 0.40253(16) 0.12318(12) 0.50606(18) 0.0161(4) Uani 1 1 d . . . 
H10A H 0.4128 0.1890 0.5067 0.019 Uiso 1 1 calc R . . 
H10B H 0.4767 0.0948 0.5328 0.019 Uiso 1 1 calc R . . 
C11 C 0.36741(17) 0.09054(12) 0.37820(19) 0.0176(4) Uani 1 1 d . . . 
H11A H 0.3277 0.1384 0.3309 0.021 Uiso 1 1 calc R . . 
H11B H 0.4365 0.0694 0.3313 0.021 Uiso 1 1 calc R . . 
C12 C 0.2477(2) -0.04347(14) 0.3085(2) 0.0273(5) Uani 1 1 d . . . 
H12A H 0.2196 -0.0994 0.3453 0.041 Uiso 1 1 calc R . . 
H12B H 0.3131 -0.0564 0.2528 0.041 Uiso 1 1 calc R . . 
H12C H 0.1839 -0.0152 0.2623 0.041 Uiso 1 1 calc R . . 
C13 C 0.16682(15) 0.21371(12) 0.49280(18) 0.0147(4) Uani 1 1 d . . . 
C14 C 0.08034(16) 0.17149(12) 0.42340(19) 0.0172(4) Uani 1 1 d . . . 
H14 H 0.0457 0.1177 0.4525 0.021 Uiso 1 1 calc R . . 
C15 C 0.04448(17) 0.20778(13) 0.31181(19) 0.0206(4) Uani 1 1 d . . . 
H15 H -0.0147 0.1787 0.2650 0.025 Uiso 1 1 calc R . . 
C16 C 0.09468(18) 0.28626(14) 0.2685(2) 0.0225(4) Uani 1 1 d . . . 
H16 H 0.0708 0.3104 0.1916 0.027 Uiso 1 1 calc R . . 
C17 C 0.17983(17) 0.32926(13) 0.3377(2) 0.0208(4) Uani 1 1 d . . . 
H17 H 0.2140 0.3832 0.3085 0.025 Uiso 1 1 calc R . . 
C18 C 0.21520(16) 0.29360(12) 0.44973(19) 0.0175(4) Uani 1 1 d . . . 
H18 H 0.2727 0.3238 0.4974 0.021 Uiso 1 1 calc R . . 
C19 C 0.09075(16) 0.06911(12) 0.90602(18) 0.0168(4) Uani 1 1 d . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C1 1.224(2) . ? 
O2 C9 1.248(2) . ? 
O3 N3 1.225(2) . ? 
O4 N3 1.218(2) . ? 
O5 C19 1.197(2) . ? 
O6 C19 1.323(2) . ? 
O6 H6 0.8400 . ? 
N1 C1 1.359(3) . ? 
N1 C5 1.457(2) . ? 
N1 C6 1.482(3) . ? 
N2 C9 1.319(3) . ? 
N2 C12 1.459(3) . ? 
N2 C11 1.461(2) . ? 
N3 C4 1.510(2) . ? 
C1 C2 1.534(3) . ? 
C2 C9 1.538(2) . ? 
C2 C10 1.544(3) . ? 
C2 C3 1.557(2) . ? 
C3 C13 1.514(3) . ? 
C3 C4 1.519(3) . ? 
C3 H3A 1.0000 . ? 
C4 C5 1.536(3) . ? 
C4 H4 1.0000 . ? 
C5 C19 1.535(2) . ? 
C5 H5 1.0000 . ? 
C6 C7 1.497(3) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 C8 1.317(3) . ? 
C7 H7 0.9500 . ? 
C8 H8A 0.9500 . ? 
C8 H8B 0.9500 . ? 
C10 C11 1.526(3) . ? 
C10 H10A 0.9900 . ? 
C10 H10B 0.9900 . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 H12A 0.9800 . ? 
C12 H12B 0.9800 . ? 
C12 H12C 0.9800 . ? 
C13 C14 1.393(3) . ? 
C13 C18 1.396(3) . ? 
C14 C15 1.390(3) . ? 
C14 H14 0.9500 . ? 
C15 C16 1.388(3) . ? 
C15 H15 0.9500 . ? 
C16 C17 1.387(3) . ? 
C16 H16 0.9500 . ? 
C17 C18 1.389(3) . ? 
C17 H17 0.9500 . ? 
C18 H18 0.9500 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C19 O6 H6 109.5 . . ? 
C1 N1 C5 126.53(16) . . ? 
C1 N1 C6 119.18(14) . . ? 
C5 N1 C6 113.97(15) . . ? 
C9 N2 C12 124.21(17) . . ? 
C9 N2 C11 114.31(16) . . ? 
C12 N2 C11 120.83(17) . . ? 
O4 N3 O3 124.99(16) . . ? 
O4 N3 C4 118.08(15) . . ? 
O3 N3 C4 116.91(15) . . ? 
O1 C1 N1 121.97(18) . . ? 
O1 C1 C2 119.26(17) . . ? 
N1 C1 C2 118.69(15) . . ? 
C1 C2 C9 110.09(15) . . ? 
C1 C2 C10 110.47(15) . . ? 
C9 C2 C10 102.35(15) . . ? 
C1 C2 C3 110.75(15) . . ? 
C9 C2 C3 111.49(14) . . ? 
C10 C2 C3 111.41(14) . . ? 
C13 C3 C4 115.32(14) . . ? 
C13 C3 C2 113.34(15) . . ? 
C4 C3 C2 106.68(13) . . ? 
C13 C3 H3A 107.0 . . ? 
C4 C3 H3A 107.0 . . ? 
C2 C3 H3A 107.0 . . ? 
N3 C4 C3 109.50(14) . . ? 
N3 C4 C5 107.56(14) . . ? 
C3 C4 C5 109.50(14) . . ? 
N3 C4 H4 110.1 . . ? 
C3 C4 H4 110.1 . . ? 
C5 C4 H4 110.1 . . ? 
N1 C5 C19 110.74(14) . . ? 
N1 C5 C4 111.82(15) . . ? 
C19 C5 C4 109.01(14) . . ? 
N1 C5 H5 108.4 . . ? 
C19 C5 H5 108.4 . . ? 
C4 C5 H5 108.4 . . ? 
N1 C6 C7 109.66(16) . . ? 
N1 C6 H6A 109.7 . . ? 
C7 C6 H6A 109.7 . . ? 
N1 C6 H6B 109.7 . . ? 
C7 C6 H6B 109.7 . . ? 
H6A C6 H6B 108.2 . . ? 
C8 C7 C6 123.9(2) . . ? 
C8 C7 H7 118.1 . . ? 
C6 C7 H7 118.1 . . ? 
C7 C8 H8A 120.0 . . ? 
C7 C8 H8B 120.0 . . ? 
H8A C8 H8B 120.0 . . ? 
O2 C9 N2 126.77(18) . . ? 
O2 C9 C2 123.96(18) . . ? 
N2 C9 C2 109.26(16) . . ? 
C11 C10 C2 104.94(14) . . ? 
C11 C10 H10A 110.8 . . ? 
C2 C10 H10A 110.8 . . ? 
C11 C10 H10B 110.8 . . ? 
C2 C10 H10B 110.8 . . ? 
H10A C10 H10B 108.8 . . ? 
N2 C11 C10 102.73(15) . . ? 
N2 C11 H11A 111.2 . . ? 
C10 C11 H11A 111.2 . . ? 
N2 C11 H11B 111.2 . . ? 
C10 C11 H11B 111.2 . . ? 
H11A C11 H11B 109.1 . . ? 
N2 C12 H12A 109.5 . . ? 
N2 C12 H12B 109.5 . . ? 
H12A C12 H12B 109.5 . . ? 
N2 C12 H12C 109.5 . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
C14 C13 C18 119.06(18) . . ? 
C14 C13 C3 121.93(16) . . ? 
C18 C13 C3 118.98(16) . . ? 
C15 C14 C13 120.28(17) . . ? 
C15 C14 H14 119.9 . . ? 
C13 C14 H14 119.9 . . ? 
C16 C15 C14 120.30(18) . . ? 
C16 C15 H15 119.8 . . ? 
C14 C15 H15 119.8 . . ? 
C15 C16 C17 119.77(19) . . ? 
C15 C16 H16 120.1 . . ? 
C17 C16 H16 120.1 . . ? 
C18 C17 C16 120.09(18) . . ? 
C18 C17 H17 120.0 . . ? 
C16 C17 H17 120.0 . . ? 
C17 C18 C13 120.48(18) . . ? 
C17 C18 H18 119.8 . . ? 
C13 C18 H18 119.8 . . ? 
O5 C19 O6 125.64(18) . . ? 
O5 C19 C5 124.27(17) . . ? 
O6 C19 C5 110.06(14) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C5 N1 C1 O1 -172.50(16) . . . . ? 
C6 N1 C1 O1 14.4(2) . . . . ? 
C5 N1 C1 C2 10.7(2) . . . . ? 
C6 N1 C1 C2 -162.37(16) . . . . ? 
O1 C1 C2 C9 75.7(2) . . . . ? 
N1 C1 C2 C9 -107.43(18) . . . . ? 
O1 C1 C2 C10 -36.6(2) . . . . ? 
N1 C1 C2 C10 140.25(16) . . . . ? 
O1 C1 C2 C3 -160.57(15) . . . . ? 
N1 C1 C2 C3 16.3(2) . . . . ? 
C1 C2 C3 C13 177.91(15) . . . . ? 
C9 C2 C3 C13 -59.14(19) . . . . ? 
C10 C2 C3 C13 54.52(19) . . . . ? 
C1 C2 C3 C4 -54.10(18) . . . . ? 
C9 C2 C3 C4 68.85(19) . . . . ? 
C10 C2 C3 C4 -177.49(15) . . . . ? 
O4 N3 C4 C3 -55.4(2) . . . . ? 
O3 N3 C4 C3 123.06(18) . . . . ? 
O4 N3 C4 C5 63.5(2) . . . . ? 
O3 N3 C4 C5 -118.03(17) . . . . ? 
C13 C3 C4 N3 -47.2(2) . . . . ? 
C2 C3 C4 N3 -174.06(14) . . . . ? 
C13 C3 C4 C5 -164.93(14) . . . . ? 
C2 C3 C4 C5 68.24(17) . . . . ? 
C1 N1 C5 C19 124.34(18) . . . . ? 
C6 N1 C5 C19 -62.28(19) . . . . ? 
C1 N1 C5 C4 2.5(2) . . . . ? 
C6 N1 C5 C4 175.93(15) . . . . ? 
N3 C4 C5 N1 -161.50(13) . . . . ? 
C3 C4 C5 N1 -42.60(18) . . . . ? 
N3 C4 C5 C19 75.72(17) . . . . ? 
C3 C4 C5 C19 -165.38(14) . . . . ? 
C1 N1 C6 C7 107.88(19) . . . . ? 
C5 N1 C6 C7 -66.0(2) . . . . ? 
N1 C6 C7 C8 102.4(2) . . . . ? 
C12 N2 C9 O2 3.1(3) . . . . ? 
C11 N2 C9 O2 173.83(17) . . . . ? 
C12 N2 C9 C2 -175.83(17) . . . . ? 
C11 N2 C9 C2 -5.1(2) . . . . ? 
C1 C2 C9 O2 52.3(2) . . . . ? 
C10 C2 C9 O2 169.76(16) . . . . ? 
C3 C2 C9 O2 -71.0(2) . . . . ? 
C1 C2 C9 N2 -128.79(16) . . . . ? 
C10 C2 C9 N2 -11.32(18) . . . . ? 
C3 C2 C9 N2 107.88(17) . . . . ? 
C1 C2 C10 C11 139.39(15) . . . . ? 
C9 C2 C10 C11 22.19(17) . . . . ? 
C3 C2 C10 C11 -97.06(17) . . . . ? 
C9 N2 C11 C10 19.4(2) . . . . ? 
C12 N2 C11 C10 -169.53(16) . . . . ? 
C2 C10 C11 N2 -24.91(18) . . . . ? 
C4 C3 C13 C14 -46.5(2) . . . . ? 
C2 C3 C13 C14 76.9(2) . . . . ? 
C4 C3 C13 C18 135.69(17) . . . . ? 
C2 C3 C13 C18 -100.95(18) . . . . ? 
C18 C13 C14 C15 1.1(3) . . . . ? 
C3 C13 C14 C15 -176.70(16) . . . . ? 
C13 C14 C15 C16 0.1(3) . . . . ? 
C14 C15 C16 C17 -0.9(3) . . . . ? 
C15 C16 C17 C18 0.4(3) . . . . ? 
C16 C17 C18 C13 0.9(3) . . . . ? 
C14 C13 C18 C17 -1.7(3) . . . . ? 
C3 C13 C18 C17 176.24(16) . . . . ? 
N1 C5 C19 O5 -22.9(3) . . . . ? 
C4 C5 C19 O5 100.5(2) . . . . ? 
N1 C5 C19 O6 158.83(15) . . . . ? 
C4 C5 C19 O6 -77.74(18) . . . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O6 H6 O2  0.84 1.81 2.6434(18) 171.6 2 
  
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              26.37 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.211 
_refine_diff_density_min   -0.155 
_refine_diff_density_rms    0.036 


#==============================================================================
data_2a     #s2668abs
#============================================================================== 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_publ_section_exptl_refinement
;
The structure was solved by direct methods.
All non-H atoms were refined anisotropically. 
H atoms were included in calculated positions. 
;

_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety         'C23 H23 N3 O4' 
_chemical_formula_sum 
 'C23 H23 N3 O4' 
_chemical_formula_weight          405.44 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    Pn 
_symmetry_space_group_name_Hall P-2yac 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 'x+1/2, -y, z+1/2' 
  
_cell_length_a                    6.4732(5) 
_cell_length_b                    10.4674(7) 
_cell_length_c                    14.5108(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  95.0500(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      979.40(12) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     5832 
_cell_measurement_theta_min       2.40 
_cell_measurement_theta_max       26.35 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.60 
_exptl_crystal_size_mid           0.30 
_exptl_crystal_size_min           0.30 
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn     1.375 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              428 
_exptl_absorpt_coefficient_mu     0.095 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9449 
_exptl_absorpt_correction_T_max   0.9719 
_exptl_absorpt_process_details    'SADABS'
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             7591 
_diffrn_reflns_av_R_equivalents   0.0141 
_diffrn_reflns_av_sigmaI/netI     0.0130 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          1.95 
_diffrn_reflns_theta_max          26.39 
_reflns_number_total              2000 
_reflns_number_gt                 1977 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0424P)²+0.2331P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2000 
_refine_ls_number_parameters      272 
_refine_ls_number_restraints      2 
_refine_ls_R_factor_all           0.0276 
_refine_ls_R_factor_gt            0.0273 
_refine_ls_wR_factor_ref          0.0715 
_refine_ls_wR_factor_gt           0.0713 
_refine_ls_goodness_of_fit_ref    1.088 
_refine_ls_restrained_S_all       1.087 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.7408(2) 0.38010(14) 1.04171(10) 0.0210(3) Uani 1 1 d . . . 
O2 O 0.3475(2) 0.16668(14) 1.00985(10) 0.0203(3) Uani 1 1 d . . . 
O3 O 0.0333(2) 0.28544(14) 0.71367(10) 0.0216(3) Uani 1 1 d . . . 
O4 O 0.3220(2) 0.33759(14) 0.65892(9) 0.0213(3) Uani 1 1 d . . . 
N1 N 0.4872(2) 0.45568(15) 0.93887(11) 0.0167(3) Uani 1 1 d . . . 
N2 N 0.6346(3) 0.04195(16) 0.99788(12) 0.0188(3) Uani 1 1 d . . . 
N3 N 0.2174(2) 0.31359(14) 0.72295(11) 0.0152(3) Uani 1 1 d . . . 
C1 C 0.6297(3) 0.36661(18) 0.96986(13) 0.0156(4) Uani 1 1 d . . . 
C2 C 0.6316(3) 0.23761(18) 0.91982(13) 0.0148(4) Uani 1 1 d . . . 
C3 C 0.5216(3) 0.23899(18) 0.82045(13) 0.0138(3) Uani 1 1 d . . . 
H3 H 0.6159 0.2837 0.7799 0.017 Uiso 1 1 calc R . . 
C4 C 0.3241(3) 0.31823(18) 0.81987(12) 0.0138(4) Uani 1 1 d . . . 
H4 H 0.2312 0.2815 0.8646 0.017 Uiso 1 1 calc R . . 
C5 C 0.3767(3) 0.45794(17) 0.84566(13) 0.0149(4) Uani 1 1 d . . . 
H5 H 0.4723 0.4923 0.8011 0.018 Uiso 1 1 calc R . . 
C6 C 0.1833(3) 0.54145(17) 0.84146(13) 0.0162(4) Uani 1 1 d . . . 
C7 C 0.0925(3) 0.57972(18) 0.75488(14) 0.0192(4) Uani 1 1 d . . . 
H7 H 0.1575 0.5585 0.7007 0.023 Uiso 1 1 calc R . . 
C8 C -0.0915(3) 0.64836(19) 0.74714(15) 0.0228(4) Uani 1 1 d . . . 
H8 H -0.1536 0.6726 0.6880 0.027 Uiso 1 1 calc R . . 
C9 C -0.1847(3) 0.6816(2) 0.82674(16) 0.0238(4) Uani 1 1 d . . . 
H9 H -0.3128 0.7265 0.8220 0.029 Uiso 1 1 calc R . . 
C10 C -0.0896(3) 0.6490(2) 0.91289(15) 0.0221(4) Uani 1 1 d . . . 
H10 H -0.1511 0.6746 0.9670 0.027 Uiso 1 1 calc R . . 
C11 C 0.0942(3) 0.57940(19) 0.92151(14) 0.0187(4) Uani 1 1 d . . . 
C12 C 0.2105(3) 0.5553(2) 1.01425(14) 0.0238(4) Uani 1 1 d . . . 
H12A H 0.1724 0.4708 1.0383 0.029 Uiso 1 1 calc R . . 
H12B H 0.1754 0.6216 1.0590 0.029 Uiso 1 1 calc R . . 
C13 C 0.4401(3) 0.5593(2) 1.00179(15) 0.0219(4) Uani 1 1 d . . . 
H13A H 0.4770 0.6427 0.9756 0.026 Uiso 1 1 calc R . . 
H13B H 0.5215 0.5483 1.0623 0.026 Uiso 1 1 calc R . . 
C14 C 0.5182(3) 0.14627(18) 0.98222(13) 0.0156(4) Uani 1 1 d . . . 
C15 C 0.8237(3) 0.03939(19) 0.95074(14) 0.0203(4) Uani 1 1 d . . . 
H15A H 0.8087 -0.0174 0.8960 0.024 Uiso 1 1 calc R . . 
H15B H 0.9433 0.0105 0.9928 0.024 Uiso 1 1 calc R . . 
C16 C 0.8492(3) 0.17927(19) 0.92210(13) 0.0180(4) Uani 1 1 d . . . 
H16A H 0.9464 0.2245 0.9675 0.022 Uiso 1 1 calc R . . 
H16B H 0.9028 0.1846 0.8604 0.022 Uiso 1 1 calc R . . 
C17 C 0.5661(4) -0.0683(2) 1.04710(17) 0.0281(5) Uani 1 1 d . . . 
H17A H 0.4515 -0.0436 1.0832 0.042 Uiso 1 1 calc R . . 
H17B H 0.6814 -0.1010 1.0888 0.042 Uiso 1 1 calc R . . 
H17C H 0.5190 -0.1349 1.0026 0.042 Uiso 1 1 calc R . . 
C18 C 0.4809(3) 0.10555(18) 0.78025(13) 0.0158(4) Uani 1 1 d . . . 
C19 C 0.3182(3) 0.02969(19) 0.80597(14) 0.0184(4) Uani 1 1 d . . . 
H19 H 0.2313 0.0602 0.8506 0.022 Uiso 1 1 calc R . . 
C20 C 0.2826(3) -0.0902(2) 0.76670(15) 0.0228(4) Uani 1 1 d . . . 
H20 H 0.1717 -0.1412 0.7848 0.027 Uiso 1 1 calc R . . 
C21 C 0.4077(3) -0.13612(19) 0.70139(14) 0.0228(4) Uani 1 1 d . . . 
H21 H 0.3817 -0.2176 0.6740 0.027 Uiso 1 1 calc R . . 
C22 C 0.5714(3) -0.0619(2) 0.67629(14) 0.0225(4) Uani 1 1 d . . . 
H22 H 0.6597 -0.0936 0.6326 0.027 Uiso 1 1 calc R . . 
C23 C 0.6066(3) 0.0589(2) 0.71490(13) 0.0183(4) Uani 1 1 d . . . 
H23 H 0.7172 0.1098 0.6965 0.022 Uiso 1 1 calc R . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C1 1.221(2) . ? 
O2 C14 1.227(2) . ? 
O3 N3 1.224(2) . ? 
O4 N3 1.223(2) . ? 
N1 C1 1.360(3) . ? 
N1 C13 1.467(2) . ? 
N1 C5 1.474(2) . ? 
N2 C14 1.335(3) . ? 
N2 C17 1.447(3) . ? 
N2 C15 1.454(3) . ? 
N3 C4 1.512(2) . ? 
C1 C2 1.534(3) . ? 
C2 C16 1.533(3) . ? 
C2 C14 1.546(3) . ? 
C2 C3 1.551(2) . ? 
C3 C4 1.524(3) . ? 
C3 C18 1.528(3) . ? 
C3 H3 1.0000 . ? 
C4 C5 1.540(2) . ? 
C4 H4 1.0000 . ? 
C5 C6 1.524(3) . ? 
C5 H5 1.0000 . ? 
C6 C7 1.398(3) . ? 
C6 C11 1.399(3) . ? 
C7 C8 1.387(3) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.394(3) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.387(3) . ? 
C9 H9 0.9500 . ? 
C10 C11 1.391(3) . ? 
C10 H10 0.9500 . ? 
C11 C12 1.504(3) . ? 
C12 C13 1.514(3) . ? 
C12 H12A 0.9900 . ? 
C12 H12B 0.9900 . ? 
C13 H13A 0.9900 . ? 
C13 H13B 0.9900 . ? 
C15 C16 1.535(3) . ? 
C15 H15A 0.9900 . ? 
C15 H15B 0.9900 . ? 
C16 H16A 0.9900 . ? 
C16 H16B 0.9900 . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C17 H17C 0.9800 . ? 
C18 C23 1.391(3) . ? 
C18 C19 1.396(3) . ? 
C19 C20 1.389(3) . ? 
C19 H19 0.9500 . ? 
C20 C21 1.385(3) . ? 
C20 H20 0.9500 . ? 
C21 C22 1.388(3) . ? 
C21 H21 0.9500 . ? 
C22 C23 1.394(3) . ? 
C22 H22 0.9500 . ? 
C23 H23 0.9500 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C1 N1 C13 118.23(15) . . ? 
C1 N1 C5 125.10(15) . . ? 
C13 N1 C5 116.67(15) . . ? 
C14 N2 C17 122.93(18) . . ? 
C14 N2 C15 114.90(16) . . ? 
C17 N2 C15 121.64(17) . . ? 
O4 N3 O3 124.39(16) . . ? 
O4 N3 C4 117.51(14) . . ? 
O3 N3 C4 118.10(15) . . ? 
O1 C1 N1 122.29(17) . . ? 
O1 C1 C2 118.51(17) . . ? 
N1 C1 C2 118.71(16) . . ? 
C16 C2 C1 112.71(15) . . ? 
C16 C2 C14 102.94(15) . . ? 
C1 C2 C14 104.08(15) . . ? 
C16 C2 C3 111.67(15) . . ? 
C1 C2 C3 114.20(15) . . ? 
C14 C2 C3 110.34(15) . . ? 
C4 C3 C18 112.27(15) . . ? 
C4 C3 C2 109.05(14) . . ? 
C18 C3 C2 113.34(15) . . ? 
C4 C3 H3 107.3 . . ? 
C18 C3 H3 107.3 . . ? 
C2 C3 H3 107.3 . . ? 
N3 C4 C3 107.58(14) . . ? 
N3 C4 C5 109.24(14) . . ? 
C3 C4 C5 110.38(14) . . ? 
N3 C4 H4 109.9 . . ? 
C3 C4 H4 109.9 . . ? 
C5 C4 H4 109.9 . . ? 
N1 C5 C6 112.13(15) . . ? 
N1 C5 C4 106.67(14) . . ? 
C6 C5 C4 111.83(15) . . ? 
N1 C5 H5 108.7 . . ? 
C6 C5 H5 108.7 . . ? 
C4 C5 H5 108.7 . . ? 
C7 C6 C11 119.54(18) . . ? 
C7 C6 C5 118.65(17) . . ? 
C11 C6 C5 121.81(17) . . ? 
C8 C7 C6 120.76(19) . . ? 
C8 C7 H7 119.6 . . ? 
C6 C7 H7 119.6 . . ? 
C7 C8 C9 119.59(19) . . ? 
C7 C8 H8 120.2 . . ? 
C9 C8 H8 120.2 . . ? 
C10 C9 C8 119.70(19) . . ? 
C10 C9 H9 120.1 . . ? 
C8 C9 H9 120.1 . . ? 
C9 C10 C11 121.21(19) . . ? 
C9 C10 H10 119.4 . . ? 
C11 C10 H10 119.4 . . ? 
C10 C11 C6 119.07(18) . . ? 
C10 C11 C12 121.66(18) . . ? 
C6 C11 C12 118.98(18) . . ? 
C11 C12 C13 107.95(17) . . ? 
C11 C12 H12A 110.1 . . ? 
C13 C12 H12A 110.1 . . ? 
C11 C12 H12B 110.1 . . ? 
C13 C12 H12B 110.1 . . ? 
H12A C12 H12B 108.4 . . ? 
N1 C13 C12 108.31(17) . . ? 
N1 C13 H13A 110.0 . . ? 
C12 C13 H13A 110.0 . . ? 
N1 C13 H13B 110.0 . . ? 
C12 C13 H13B 110.0 . . ? 
H13A C13 H13B 108.4 . . ? 
O2 C14 N2 126.72(18) . . ? 
O2 C14 C2 124.86(17) . . ? 
N2 C14 C2 108.39(16) . . ? 
N2 C15 C16 103.00(15) . . ? 
N2 C15 H15A 111.2 . . ? 
C16 C15 H15A 111.2 . . ? 
N2 C15 H15B 111.2 . . ? 
C16 C15 H15B 111.2 . . ? 
H15A C15 H15B 109.1 . . ? 
C2 C16 C15 105.38(16) . . ? 
C2 C16 H16A 110.7 . . ? 
C15 C16 H16A 110.7 . . ? 
C2 C16 H16B 110.7 . . ? 
C15 C16 H16B 110.7 . . ? 
H16A C16 H16B 108.8 . . ? 
N2 C17 H17A 109.5 . . ? 
N2 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
N2 C17 H17C 109.5 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
C23 C18 C19 118.87(18) . . ? 
C23 C18 C3 119.31(17) . . ? 
C19 C18 C3 121.82(17) . . ? 
C20 C19 C18 120.40(18) . . ? 
C20 C19 H19 119.8 . . ? 
C18 C19 H19 119.8 . . ? 
C21 C20 C19 120.53(19) . . ? 
C21 C20 H20 119.7 . . ? 
C19 C20 H20 119.7 . . ? 
C20 C21 C22 119.41(19) . . ? 
C20 C21 H21 120.3 . . ? 
C22 C21 H21 120.3 . . ? 
C21 C22 C23 120.25(19) . . ? 
C21 C22 H22 119.9 . . ? 
C23 C22 H22 119.9 . . ? 
C18 C23 C22 120.52(19) . . ? 
C18 C23 H23 119.7 . . ? 
C22 C23 H23 119.7 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C13 N1 C1 O1 -11.2(3) . . . . ? 
C5 N1 C1 O1 167.87(17) . . . . ? 
C13 N1 C1 C2 160.66(17) . . . . ? 
C5 N1 C1 C2 -20.2(3) . . . . ? 
O1 C1 C2 C16 -39.3(2) . . . . ? 
N1 C1 C2 C16 148.52(17) . . . . ? 
O1 C1 C2 C14 71.5(2) . . . . ? 
N1 C1 C2 C14 -100.67(18) . . . . ? 
O1 C1 C2 C3 -168.11(16) . . . . ? 
N1 C1 C2 C3 19.7(2) . . . . ? 
C16 C2 C3 C4 -170.20(15) . . . . ? 
C1 C2 C3 C4 -40.9(2) . . . . ? 
C14 C2 C3 C4 75.95(19) . . . . ? 
C16 C2 C3 C18 63.9(2) . . . . ? 
C1 C2 C3 C18 -166.71(16) . . . . ? 
C14 C2 C3 C18 -49.9(2) . . . . ? 
O4 N3 C4 C3 -49.9(2) . . . . ? 
O3 N3 C4 C3 129.61(16) . . . . ? 
O4 N3 C4 C5 69.9(2) . . . . ? 
O3 N3 C4 C5 -110.55(17) . . . . ? 
C18 C3 C4 N3 -51.56(19) . . . . ? 
C2 C3 C4 N3 -178.03(14) . . . . ? 
C18 C3 C4 C5 -170.67(15) . . . . ? 
C2 C3 C4 C5 62.86(18) . . . . ? 
C1 N1 C5 C6 162.03(17) . . . . ? 
C13 N1 C5 C6 -18.9(2) . . . . ? 
C1 N1 C5 C4 39.3(2) . . . . ? 
C13 N1 C5 C4 -141.60(16) . . . . ? 
N3 C4 C5 N1 -177.79(14) . . . . ? 
C3 C4 C5 N1 -59.69(18) . . . . ? 
N3 C4 C5 C6 59.27(18) . . . . ? 
C3 C4 C5 C6 177.38(15) . . . . ? 
N1 C5 C6 C7 163.79(16) . . . . ? 
C4 C5 C6 C7 -76.4(2) . . . . ? 
N1 C5 C6 C11 -16.8(2) . . . . ? 
C4 C5 C6 C11 102.95(19) . . . . ? 
C11 C6 C7 C8 -3.8(3) . . . . ? 
C5 C6 C7 C8 175.57(17) . . . . ? 
C6 C7 C8 C9 1.2(3) . . . . ? 
C7 C8 C9 C10 1.8(3) . . . . ? 
C8 C9 C10 C11 -2.3(3) . . . . ? 
C9 C10 C11 C6 -0.3(3) . . . . ? 
C9 C10 C11 C12 173.4(2) . . . . ? 
C7 C6 C11 C10 3.4(3) . . . . ? 
C5 C6 C11 C10 -176.04(17) . . . . ? 
C7 C6 C11 C12 -170.57(19) . . . . ? 
C5 C6 C11 C12 10.0(3) . . . . ? 
C10 C11 C12 C13 -143.89(19) . . . . ? 
C6 C11 C12 C13 29.9(3) . . . . ? 
C1 N1 C13 C12 -121.56(19) . . . . ? 
C5 N1 C13 C12 59.3(2) . . . . ? 
C11 C12 C13 N1 -62.7(2) . . . . ? 
C17 N2 C14 O2 3.8(3) . . . . ? 
C15 N2 C14 O2 175.57(18) . . . . ? 
C17 N2 C14 C2 -174.36(18) . . . . ? 
C15 N2 C14 C2 -2.6(2) . . . . ? 
C16 C2 C14 O2 169.59(18) . . . . ? 
C1 C2 C14 O2 51.8(2) . . . . ? 
C3 C2 C14 O2 -71.1(2) . . . . ? 
C16 C2 C14 N2 -12.2(2) . . . . ? 
C1 C2 C14 N2 -129.93(16) . . . . ? 
C3 C2 C14 N2 107.14(17) . . . . ? 
C14 N2 C15 C16 16.2(2) . . . . ? 
C17 N2 C15 C16 -171.92(18) . . . . ? 
C1 C2 C16 C15 132.75(16) . . . . ? 
C14 C2 C16 C15 21.23(19) . . . . ? 
C3 C2 C16 C15 -97.13(18) . . . . ? 
N2 C15 C16 C2 -22.67(19) . . . . ? 
C4 C3 C18 C23 132.27(18) . . . . ? 
C2 C3 C18 C23 -103.62(19) . . . . ? 
C4 C3 C18 C19 -46.5(2) . . . . ? 
C2 C3 C18 C19 77.6(2) . . . . ? 
C23 C18 C19 C20 -0.1(3) . . . . ? 
C3 C18 C19 C20 178.68(18) . . . . ? 
C18 C19 C20 C21 -0.1(3) . . . . ? 
C19 C20 C21 C22 0.9(3) . . . . ? 
C20 C21 C22 C23 -1.5(3) . . . . ? 
C19 C18 C23 C22 -0.4(3) . . . . ? 
C3 C18 C23 C22 -179.25(18) . . . . ? 
C21 C22 C23 C18 1.2(3) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.995 
_diffrn_reflns_theta_full              26.39 
_diffrn_measured_fraction_theta_full   0.995 
_refine_diff_density_max    0.235 
_refine_diff_density_min   -0.167 
_refine_diff_density_rms    0.035 


#==============================================================================
data_2a-doubleprime     #s2685
#==============================================================================
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_publ_section_exptl_refinement
;
The structure was solved by direct methods.
All non-H atoms were refined anisotropically. 
H atoms were included in calculated positions. 
;

_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C23 H23 N3 O4'
_chemical_formula_sum 
 'C23 H23 N3 O4' 
_chemical_formula_weight          405.44 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    Pbca 
_symmetry_space_group_name_Hall -P2ac2ab 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, y, -z-1/2' 
 'x, -y-1/2, z-1/2' 
 '-x-1/2, y-1/2, z' 
  
_cell_length_a                    15.0761(19) 
_cell_length_b                    10.7200(13) 
_cell_length_c                    23.726(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3834.5(8) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     4679 
_cell_measurement_theta_min       2.18 
_cell_measurement_theta_max       26.24 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.45 
_exptl_crystal_size_mid           0.40 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.405 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1712 
_exptl_absorpt_coefficient_mu     0.098 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             28298 
_diffrn_reflns_av_R_equivalents   0.0832 
_diffrn_reflns_av_sigmaI/netI     0.0593 
_diffrn_reflns_limit_h_min        -18 
_diffrn_reflns_limit_h_max        18 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -29 
_diffrn_reflns_limit_l_max        29 
_diffrn_reflns_theta_min          1.72 
_diffrn_reflns_theta_max          26.46 
_reflns_number_total              3950 
_reflns_number_gt                 2577 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0580P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3950 
_refine_ls_number_parameters      272 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0718 
_refine_ls_R_factor_gt            0.0416 
_refine_ls_wR_factor_ref          0.1026 
_refine_ls_wR_factor_gt           0.0930 
_refine_ls_goodness_of_fit_ref    0.891 
_refine_ls_restrained_S_all       0.891 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.21478(8) -0.03039(11) 0.20910(5) 0.0251(3) Uani 1 1 d . . . 
O2 O 0.37365(8) -0.07005(11) 0.11191(5) 0.0243(3) Uani 1 1 d . . . 
O3 O 0.51762(10) 0.37563(12) 0.25640(6) 0.0404(4) Uani 1 1 d . . . 
O4 O 0.56966(9) 0.18748(14) 0.25005(6) 0.0368(4) Uani 1 1 d . . . 
N1 N 0.31377(9) 0.05062(14) 0.27054(6) 0.0231(4) Uani 1 1 d . . . 
N2 N 0.25520(10) 0.04778(13) 0.08394(6) 0.0221(3) Uani 1 1 d . . . 
N3 N 0.50867(11) 0.26295(15) 0.24958(6) 0.0274(4) Uani 1 1 d . . . 
C1 C 0.28022(11) 0.03513(16) 0.21838(8) 0.0216(4) Uani 1 1 d . . . 
C2 C 0.32141(11) 0.10659(16) 0.16913(7) 0.0197(4) Uani 1 1 d . . . 
C3 C 0.41751(11) 0.14827(16) 0.18214(7) 0.0198(4) Uani 1 1 d . . . 
H3 H 0.4537 0.0708 0.1869 0.024 Uiso 1 1 calc R . . 
C4 C 0.41593(11) 0.21462(16) 0.23935(7) 0.0203(4) Uani 1 1 d . . . 
H4 H 0.3725 0.2851 0.2388 0.024 Uiso 1 1 calc R . . 
C5 C 0.39311(11) 0.12243(16) 0.28684(7) 0.0206(4) Uani 1 1 d . . . 
H5 H 0.4436 0.0625 0.2905 0.025 Uiso 1 1 calc R . . 
C6 C 0.37989(11) 0.18528(16) 0.34417(7) 0.0203(4) Uani 1 1 d . . . 
C7 C 0.44961(12) 0.25237(17) 0.36822(7) 0.0227(4) Uani 1 1 d . . . 
H7 H 0.5042 0.2590 0.3484 0.027 Uiso 1 1 calc R . . 
C8 C 0.44107(13) 0.30932(17) 0.42010(8) 0.0259(4) Uani 1 1 d . . . 
H8 H 0.4895 0.3545 0.4356 0.031 Uiso 1 1 calc R . . 
C9 C 0.36238(12) 0.30068(17) 0.44940(8) 0.0280(4) Uani 1 1 d . . . 
H9 H 0.3558 0.3408 0.4849 0.034 Uiso 1 1 calc R . . 
C10 C 0.29317(12) 0.23295(18) 0.42657(8) 0.0279(4) Uani 1 1 d . . . 
H10 H 0.2388 0.2274 0.4467 0.033 Uiso 1 1 calc R . . 
C11 C 0.30116(12) 0.17255(17) 0.37482(8) 0.0238(4) Uani 1 1 d . . . 
C12 C 0.22943(12) 0.0851(2) 0.35508(8) 0.0308(5) Uani 1 1 d . . . 
H12A H 0.1838 0.1321 0.3339 0.037 Uiso 1 1 calc R . . 
H12B H 0.2005 0.0452 0.3879 0.037 Uiso 1 1 calc R . . 
C13 C 0.27031(13) -0.01341(18) 0.31759(8) 0.0309(5) Uani 1 1 d . . . 
H13A H 0.3142 -0.0630 0.3391 0.037 Uiso 1 1 calc R . . 
H13B H 0.2239 -0.0705 0.3033 0.037 Uiso 1 1 calc R . . 
C14 C 0.32154(11) 0.01653(16) 0.11890(8) 0.0206(4) Uani 1 1 d . . . 
C15 C 0.19826(12) 0.14656(16) 0.10589(8) 0.0252(4) Uani 1 1 d . . . 
H15A H 0.1434 0.1116 0.1225 0.030 Uiso 1 1 calc R . . 
H15B H 0.1820 0.2064 0.0758 0.030 Uiso 1 1 calc R . . 
C16 C 0.25517(12) 0.20886(16) 0.15077(8) 0.0226(4) Uani 1 1 d . . . 
H16A H 0.2184 0.2365 0.1830 0.027 Uiso 1 1 calc R . . 
H16B H 0.2868 0.2820 0.1351 0.027 Uiso 1 1 calc R . . 
C17 C 0.23161(12) -0.02718(17) 0.03563(8) 0.0265(4) Uani 1 1 d . . . 
H17A H 0.2800 -0.0852 0.0271 0.040 Uiso 1 1 calc R . . 
H17B H 0.2213 0.0272 0.0031 0.040 Uiso 1 1 calc R . . 
H17C H 0.1775 -0.0744 0.0439 0.040 Uiso 1 1 calc R . . 
C18 C 0.45975(11) 0.22334(16) 0.13502(7) 0.0207(4) Uani 1 1 d . . . 
C19 C 0.45422(11) 0.35293(17) 0.13133(7) 0.0222(4) Uani 1 1 d . . . 
H19 H 0.4218 0.3982 0.1589 0.027 Uiso 1 1 calc R . . 
C20 C 0.49584(11) 0.41623(18) 0.08759(8) 0.0256(4) Uani 1 1 d . . . 
H20 H 0.4928 0.5047 0.0859 0.031 Uiso 1 1 calc R . . 
C21 C 0.54168(12) 0.35095(19) 0.04648(8) 0.0295(5) Uani 1 1 d . . . 
H21 H 0.5690 0.3942 0.0162 0.035 Uiso 1 1 calc R . . 
C22 C 0.54742(12) 0.22214(18) 0.04981(8) 0.0277(4) Uani 1 1 d . . . 
H22 H 0.5785 0.1768 0.0216 0.033 Uiso 1 1 calc R . . 
C23 C 0.50805(11) 0.15969(17) 0.09408(7) 0.0237(4) Uani 1 1 d . . . 
H23 H 0.5140 0.0717 0.0967 0.028 Uiso 1 1 calc R . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C1 1.2310(19) . ? 
O2 C14 1.227(2) . ? 
O3 N3 1.2262(19) . ? 
O4 N3 1.225(2) . ? 
N1 C1 1.347(2) . ? 
N1 C13 1.465(2) . ? 
N1 C5 1.474(2) . ? 
N2 C14 1.342(2) . ? 
N2 C17 1.444(2) . ? 
N2 C15 1.459(2) . ? 
N3 C4 1.511(2) . ? 
C1 C2 1.529(2) . ? 
C2 C14 1.534(2) . ? 
C2 C16 1.546(2) . ? 
C2 C3 1.547(2) . ? 
C3 C18 1.518(2) . ? 
C3 C4 1.533(2) . ? 
C3 H3 1.0000 . ? 
C4 C5 1.538(2) . ? 
C4 H4 1.0000 . ? 
C5 C6 1.531(2) . ? 
C5 H5 1.0000 . ? 
C6 C7 1.396(2) . ? 
C6 C11 1.399(2) . ? 
C7 C8 1.380(3) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.378(3) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.382(3) . ? 
C9 H9 0.9500 . ? 
C10 C11 1.393(3) . ? 
C10 H10 0.9500 . ? 
C11 C12 1.506(3) . ? 
C12 C13 1.512(3) . ? 
C12 H12A 0.9900 . ? 
C12 H12B 0.9900 . ? 
C13 H13A 0.9900 . ? 
C13 H13B 0.9900 . ? 
C15 C16 1.522(2) . ? 
C15 H15A 0.9900 . ? 
C15 H15B 0.9900 . ? 
C16 H16A 0.9900 . ? 
C16 H16B 0.9900 . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C17 H17C 0.9800 . ? 
C18 C19 1.394(3) . ? 
C18 C23 1.392(2) . ? 
C19 C20 1.390(2) . ? 
C19 H19 0.9500 . ? 
C20 C21 1.385(3) . ? 
C20 H20 0.9500 . ? 
C21 C22 1.386(3) . ? 
C21 H21 0.9500 . ? 
C22 C23 1.380(3) . ? 
C22 H22 0.9500 . ? 
C23 H23 0.9500 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C1 N1 C13 118.32(15) . . ? 
C1 N1 C5 127.58(15) . . ? 
C13 N1 C5 114.06(14) . . ? 
C14 N2 C17 122.36(15) . . ? 
C14 N2 C15 113.51(14) . . ? 
C17 N2 C15 122.83(14) . . ? 
O3 N3 O4 124.53(17) . . ? 
O3 N3 C4 117.44(16) . . ? 
O4 N3 C4 118.02(15) . . ? 
O1 C1 N1 122.37(16) . . ? 
O1 C1 C2 118.35(16) . . ? 
N1 C1 C2 119.19(15) . . ? 
C1 C2 C14 106.19(14) . . ? 
C1 C2 C16 107.96(14) . . ? 
C14 C2 C16 103.20(14) . . ? 
C1 C2 C3 111.88(14) . . ? 
C14 C2 C3 109.61(14) . . ? 
C16 C2 C3 117.16(14) . . ? 
C18 C3 C4 114.38(14) . . ? 
C18 C3 C2 113.53(14) . . ? 
C4 C3 C2 107.22(14) . . ? 
C18 C3 H3 107.1 . . ? 
C4 C3 H3 107.1 . . ? 
C2 C3 H3 107.1 . . ? 
N3 C4 C3 106.68(13) . . ? 
N3 C4 C5 108.05(14) . . ? 
C3 C4 C5 110.74(14) . . ? 
N3 C4 H4 110.4 . . ? 
C3 C4 H4 110.4 . . ? 
C5 C4 H4 110.4 . . ? 
N1 C5 C6 110.92(14) . . ? 
N1 C5 C4 108.97(14) . . ? 
C6 C5 C4 113.41(14) . . ? 
N1 C5 H5 107.8 . . ? 
C6 C5 H5 107.8 . . ? 
C4 C5 H5 107.8 . . ? 
C7 C6 C11 118.48(16) . . ? 
C7 C6 C5 119.47(15) . . ? 
C11 C6 C5 121.97(16) . . ? 
C8 C7 C6 121.50(17) . . ? 
C8 C7 H7 119.3 . . ? 
C6 C7 H7 119.3 . . ? 
C9 C8 C7 120.03(18) . . ? 
C9 C8 H8 120.0 . . ? 
C7 C8 H8 120.0 . . ? 
C10 C9 C8 119.19(18) . . ? 
C10 C9 H9 120.4 . . ? 
C8 C9 H9 120.4 . . ? 
C9 C10 C11 121.62(17) . . ? 
C9 C10 H10 119.2 . . ? 
C11 C10 H10 119.2 . . ? 
C10 C11 C6 119.10(17) . . ? 
C10 C11 C12 120.08(16) . . ? 
C6 C11 C12 120.56(16) . . ? 
C11 C12 C13 108.97(15) . . ? 
C11 C12 H12A 109.9 . . ? 
C13 C12 H12A 109.9 . . ? 
C11 C12 H12B 109.9 . . ? 
C13 C12 H12B 109.9 . . ? 
H12A C12 H12B 108.3 . . ? 
N1 C13 C12 107.66(15) . . ? 
N1 C13 H13A 110.2 . . ? 
C12 C13 H13A 110.2 . . ? 
N1 C13 H13B 110.2 . . ? 
C12 C13 H13B 110.2 . . ? 
H13A C13 H13B 108.5 . . ? 
O2 C14 N2 125.61(16) . . ? 
O2 C14 C2 125.59(16) . . ? 
N2 C14 C2 108.80(14) . . ? 
N2 C15 C16 103.68(14) . . ? 
N2 C15 H15A 111.0 . . ? 
C16 C15 H15A 111.0 . . ? 
N2 C15 H15B 111.0 . . ? 
C16 C15 H15B 111.0 . . ? 
H15A C15 H15B 109.0 . . ? 
C15 C16 C2 104.49(14) . . ? 
C15 C16 H16A 110.9 . . ? 
C2 C16 H16A 110.9 . . ? 
C15 C16 H16B 110.9 . . ? 
C2 C16 H16B 110.9 . . ? 
H16A C16 H16B 108.9 . . ? 
N2 C17 H17A 109.5 . . ? 
N2 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
N2 C17 H17C 109.5 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
C19 C18 C23 118.40(16) . . ? 
C19 C18 C3 123.33(16) . . ? 
C23 C18 C3 118.26(16) . . ? 
C20 C19 C18 120.42(17) . . ? 
C20 C19 H19 119.8 . . ? 
C18 C19 H19 119.8 . . ? 
C21 C20 C19 120.29(18) . . ? 
C21 C20 H20 119.9 . . ? 
C19 C20 H20 119.9 . . ? 
C22 C21 C20 119.63(18) . . ? 
C22 C21 H21 120.2 . . ? 
C20 C21 H21 120.2 . . ? 
C23 C22 C21 120.00(18) . . ? 
C23 C22 H22 120.0 . . ? 
C21 C22 H22 120.0 . . ? 
C22 C23 C18 121.21(17) . . ? 
C22 C23 H23 119.4 . . ? 
C18 C23 H23 119.4 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C13 N1 C1 O1 0.1(3) . . . . ? 
C5 N1 C1 O1 177.63(16) . . . . ? 
C13 N1 C1 C2 176.72(15) . . . . ? 
C5 N1 C1 C2 -5.7(3) . . . . ? 
O1 C1 C2 C14 -41.9(2) . . . . ? 
N1 C1 C2 C14 141.37(16) . . . . ? 
O1 C1 C2 C16 68.26(19) . . . . ? 
N1 C1 C2 C16 -108.51(17) . . . . ? 
O1 C1 C2 C3 -161.40(15) . . . . ? 
N1 C1 C2 C3 21.8(2) . . . . ? 
C1 C2 C3 C18 -178.07(14) . . . . ? 
C14 C2 C3 C18 64.41(19) . . . . ? 
C16 C2 C3 C18 -52.7(2) . . . . ? 
C1 C2 C3 C4 -50.74(18) . . . . ? 
C14 C2 C3 C4 -168.26(14) . . . . ? 
C16 C2 C3 C4 74.67(18) . . . . ? 
O3 N3 C4 C3 121.18(16) . . . . ? 
O4 N3 C4 C3 -58.26(19) . . . . ? 
O3 N3 C4 C5 -119.71(16) . . . . ? 
O4 N3 C4 C5 60.85(19) . . . . ? 
C18 C3 C4 N3 -49.17(19) . . . . ? 
C2 C3 C4 N3 -175.99(14) . . . . ? 
C18 C3 C4 C5 -166.51(14) . . . . ? 
C2 C3 C4 C5 66.66(17) . . . . ? 
C1 N1 C5 C6 144.65(17) . . . . ? 
C13 N1 C5 C6 -37.7(2) . . . . ? 
C1 N1 C5 C4 19.1(2) . . . . ? 
C13 N1 C5 C4 -163.25(15) . . . . ? 
N3 C4 C5 N1 -165.77(13) . . . . ? 
C3 C4 C5 N1 -49.26(18) . . . . ? 
N3 C4 C5 C6 70.16(18) . . . . ? 
C3 C4 C5 C6 -173.34(14) . . . . ? 
N1 C5 C6 C7 176.67(15) . . . . ? 
C4 C5 C6 C7 -60.3(2) . . . . ? 
N1 C5 C6 C11 -0.1(2) . . . . ? 
C4 C5 C6 C11 122.92(18) . . . . ? 
C11 C6 C7 C8 -2.4(3) . . . . ? 
C5 C6 C7 C8 -179.23(16) . . . . ? 
C6 C7 C8 C9 0.0(3) . . . . ? 
C7 C8 C9 C10 1.0(3) . . . . ? 
C8 C9 C10 C11 0.4(3) . . . . ? 
C9 C10 C11 C6 -2.8(3) . . . . ? 
C9 C10 C11 C12 171.39(17) . . . . ? 
C7 C6 C11 C10 3.7(3) . . . . ? 
C5 C6 C11 C10 -179.54(16) . . . . ? 
C7 C6 C11 C12 -170.46(17) . . . . ? 
C5 C6 C11 C12 6.3(3) . . . . ? 
C10 C11 C12 C13 -150.94(17) . . . . ? 
C6 C11 C12 C13 23.1(2) . . . . ? 
C1 N1 C13 C12 -113.14(18) . . . . ? 
C5 N1 C13 C12 68.99(19) . . . . ? 
C11 C12 C13 N1 -58.24(19) . . . . ? 
C17 N2 C14 O2 6.6(3) . . . . ? 
C15 N2 C14 O2 173.93(16) . . . . ? 
C17 N2 C14 C2 -173.24(15) . . . . ? 
C15 N2 C14 C2 -5.93(19) . . . . ? 
C1 C2 C14 O2 -76.8(2) . . . . ? 
C16 C2 C14 O2 169.72(16) . . . . ? 
C3 C2 C14 O2 44.2(2) . . . . ? 
C1 C2 C14 N2 103.03(16) . . . . ? 
C16 C2 C14 N2 -10.42(18) . . . . ? 
C3 C2 C14 N2 -135.95(15) . . . . ? 
C14 N2 C15 C16 19.94(19) . . . . ? 
C17 N2 C15 C16 -172.81(16) . . . . ? 
N2 C15 C16 C2 -24.89(18) . . . . ? 
C1 C2 C16 C15 -90.53(17) . . . . ? 
C14 C2 C16 C15 21.62(17) . . . . ? 
C3 C2 C16 C15 142.12(15) . . . . ? 
C4 C3 C18 C19 -33.5(2) . . . . ? 
C2 C3 C18 C19 90.0(2) . . . . ? 
C4 C3 C18 C23 145.08(16) . . . . ? 
C2 C3 C18 C23 -91.42(19) . . . . ? 
C23 C18 C19 C20 0.2(3) . . . . ? 
C3 C18 C19 C20 178.82(16) . . . . ? 
C18 C19 C20 C21 1.4(3) . . . . ? 
C19 C20 C21 C22 -1.3(3) . . . . ? 
C20 C21 C22 C23 -0.4(3) . . . . ? 
C21 C22 C23 C18 2.1(3) . . . . ? 
C19 C18 C23 C22 -2.0(3) . . . . ? 
C3 C18 C23 C22 179.37(16) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              26.46 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.217 
_refine_diff_density_min   -0.277 
_refine_diff_density_rms    0.046 


#==============================================================================
data_6e 
#==============================================================================
_audit_creation_date        09-06-09
_audit_creation_method CRYSTALS_ver_12.86

_oxford_structure_analysis_title  '6110'
_chemical_name_systematic         .
_chemical_melting_point           'not measured'

_cell_length_a                    6.65270(10)
_cell_length_b                    14.3997(2)
_cell_length_c                    14.2861(2)
_cell_angle_alpha                 90
_cell_angle_beta                  91.7612(6)
_cell_angle_gamma                 90
_cell_volume                      1367.92(3)
 
_symmetry_cell_setting            'Monoclinic' 
_symmetry_space_group_name_H-M    'P 1 21/n 1 ' 
_symmetry_space_group_name_Hall   '-P 2yn ' 
loop_
 _symmetry_equiv_pos_as_xyz
 'x,y,z'
 '-x,-y,-z'
 '-x+1/2,y+1/2,-z+1/2'
 'x+1/2,-y+1/2,z+1/2'

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source  
 C       0.0033   0.0016   2.3100  20.8439   1.0200  10.2075   1.5886   0.5687
   0.8650  51.6512   0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 H       0.0000   0.0000   0.4930  10.5109   0.3229  26.1257   0.1402   3.1424
   0.0408  57.7998   0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 N       0.0061   0.0033  12.2126   0.0057   3.1322   9.8933   2.0125  28.9975
   1.1663   0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 O       0.0106   0.0060   3.0485  13.2771   2.2868   5.7011   1.5463   0.3239
   0.8670  32.9089   0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 
 
_cell_formula_units_Z                    4

# Given Formula = C13 H16 N2 O6 
# Dc =      1.44 Fooo =    624.00 Mu =      1.15 M =    296.28
# Found Formula = C13 H16 N2 O6 
# Dc =      1.44 FOOO =    624.00 Mu =      1.15 M =    296.28

_chemical_formula_sum             'C13 H16 N2 O6'
_chemical_formula_moiety          'C13 H16 N2 O6'
_chemical_compound_source                .
_chemical_formula_weight            296.28
 
 
_cell_measurement_reflns_used         3228
_cell_measurement_theta_min              5
_cell_measurement_theta_max             27
_cell_measurement_temperature          150
 
_exptl_crystal_description        'plate' 
_exptl_crystal_colour             'clear_pale_colourless' 
_exptl_crystal_size_min           0.10 
_exptl_crystal_size_mid           0.16 
_exptl_crystal_size_max           0.48 
 
_exptl_crystal_density_diffrn     1.439 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_method     'not measured' 
# Non-dispersive F(000): 
_exptl_crystal_F_000              624 
_exptl_absorpt_coefficient_mu     0.115 
 
# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_process_details    'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_exptl_absorpt_correction_T_min   0.83 
_exptl_absorpt_correction_T_max   0.99 
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device        'Nonius KappaCCD' 
_diffrn_measurement_device_type   'Area' 
_diffrn_radiation_monochromator   'graphite' 
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength           0.71073
_diffrn_measurement_method        ω 
 
# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection        'COLLECT (Nonius, 1997-2001).' 
_computing_cell_refinement        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_computing_data_reduction         'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_computing_structure_solution     'SIR92 (Altomare et al., 1994)' 
_computing_structure_refinement   'CRYSTALS (Betteridge et al., 2003)' 
_computing_publication_material   'CRYSTALS (Betteridge et al., 2003)' 
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)' 
 
_diffrn_standards_interval_time   . 
_diffrn_standards_interval_count  . 
_diffrn_standards_number          0 
_diffrn_standards_decay_%         . 
 
_diffrn_ambient_temperature        150
_diffrn_reflns_number             21820 
_reflns_number_total              3120 
_diffrn_reflns_av_R_equivalents   0.038 
# Number of reflections with Friedels Law is 3120 
# Number of reflections without Friedels Law is 6130 
# Theoretical number of reflections is about 3130 
 
 
_diffrn_reflns_theta_min          5.110 
_diffrn_reflns_theta_max          27.459 
_diffrn_measured_fraction_theta_max 0.993 
 
_diffrn_reflns_theta_full         26.910 
_diffrn_measured_fraction_theta_full 0.993 
 
 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        18 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_reflns_limit_h_min               -8 
_reflns_limit_h_max               8 
_reflns_limit_k_min               0 
_reflns_limit_k_max               18 
_reflns_limit_l_min               0 
_reflns_limit_l_max               18 
 
_oxford_diffrn_Wilson_B_factor    2.02 
_oxford_diffrn_Wilson_scale       2.15 
 
_atom_sites_solution_primary      direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens    geom
 
_refine_diff_density_min          -0.31 
_refine_diff_density_max          0.35 
 
 
# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 
 
 
# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref     I>-3.0\s(I)
_refine_ls_number_reflns          3120 
_refine_ls_number_restraints      0 
_refine_ls_number_parameters      190 
_oxford_refine_ls_R_factor_ref    0.0502 
_refine_ls_wR_factor_ref          0.0865 
_refine_ls_goodness_of_fit_ref    0.9401 
_refine_ls_shift/su_max           0.000499 
 
 
# The values computed from all data 
_oxford_reflns_number_all         3120 
_refine_ls_R_factor_all           0.0502 
_refine_ls_wR_factor_all          0.0865 
 
# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression      I>2.0σ(I)
_reflns_number_gt                 2479 
_refine_ls_R_factor_gt            0.0356 
_refine_ls_wR_factor_gt           0.0814 
 
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration  '.' 
 
 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full
_refine_ls_hydrogen_treatment     constr         # none, undef, noref, refall,
                                                 # refxyz, refU, constr or mixed
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.63P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
# Insert your own references if required - in alphabetical order 
_publ_section_references 
; 
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., 
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. 
 
Betteridge, P.W., Carruthers, J.R., Cooper, R.I., 
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 
 
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. 
 
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, 
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. 
New York: Academic Press. 
 
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical 
Crystallography Laboratory, Oxford, UK. 
; 

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.70440(14) 0.07194(6) 0.42170(6) 0.0254 1.0000 Uani . . . . . . . 
C2 C 0.66876(17) 0.15017(8) 0.44624(8) 0.0183 1.0000 Uani . . . . . . . 
O3 O 0.64739(13) 0.22185(6) 0.38749(6) 0.0240 1.0000 Uani . . . . . . . 
C4 C 0.6658(2) 0.20112(10) 0.28878(8) 0.0270 1.0000 Uani . . . . . . . 
C5 C 0.63510(17) 0.18147(8) 0.54698(8) 0.0173 1.0000 Uani . . . . . . . 
C6 C 0.66543(17) 0.09745(8) 0.61408(8) 0.0178 1.0000 Uani . . . . . . . 
C7 C 0.59216(17) 0.11422(8) 0.71135(8) 0.0188 1.0000 Uani . . . . . . . 
C8 C 0.44305(19) 0.06684(9) 0.75203(8) 0.0229 1.0000 Uani . . . . . . . 
O9 O 0.41743(14) 0.09682(7) 0.84189(6) 0.0276 1.0000 Uani . . . . . . . 
C10 C 0.55601(19) 0.16556(10) 0.85704(9) 0.0277 1.0000 Uani . . . . . . . 
C11 C 0.66559(19) 0.17904(10) 0.78068(9) 0.0259 1.0000 Uani . . . . . . . 
C12 C 0.88541(18) 0.06446(8) 0.61955(9) 0.0217 1.0000 Uani . . . . . . . 
N13 N 0.89163(16) -0.02847(8) 0.66666(8) 0.0280 1.0000 Uani . . . . . . . 
O14 O 0.98057(15) -0.03478(8) 0.74243(7) 0.0383 1.0000 Uani . . . . . . . 
O15 O 0.80651(19) -0.09311(7) 0.62725(10) 0.0549 1.0000 Uani . . . . . . . 
C16 C 0.77673(18) 0.26411(8) 0.56745(8) 0.0187 1.0000 Uani . . . . . . . 
O17 O 0.96046(13) 0.25772(6) 0.57985(6) 0.0247 1.0000 Uani . . . . . . . 
N18 N 0.67005(16) 0.34262(7) 0.56600(7) 0.0233 1.0000 Uani . . . . . . . 
C19 C 0.45800(19) 0.33063(9) 0.54081(9) 0.0267 1.0000 Uani . . . . . . . 
C20 C 0.42354(18) 0.22598(9) 0.55188(9) 0.0219 1.0000 Uani . . . . . . . 
C21 C 0.7634(2) 0.43376(9) 0.56709(10) 0.0323 1.0000 Uani . . . . . . . 
H43 H 0.6535 0.2608 0.2570 0.0389 1.0000 Uiso R . . . . . . 
H41 H 0.7968 0.1728 0.2785 0.0395 1.0000 Uiso R . . . . . . 
H42 H 0.5547 0.1602 0.2682 0.0398 1.0000 Uiso R . . . . . . 
H61 H 0.5880 0.0456 0.5860 0.0211 1.0000 Uiso R . . . . . . 
H81 H 0.3593 0.0175 0.7252 0.0268 1.0000 Uiso R . . . . . . 
H101 H 0.5620 0.1968 0.9167 0.0329 1.0000 Uiso R . . . . . . 
H111 H 0.7718 0.2241 0.7741 0.0307 1.0000 Uiso R . . . . . . 
H121 H 0.9693 0.1055 0.6575 0.0253 1.0000 Uiso R . . . . . . 
H122 H 0.9376 0.0565 0.5563 0.0255 1.0000 Uiso R . . . . . . 
H191 H 0.3719 0.3671 0.5825 0.0315 1.0000 Uiso R . . . . . . 
H192 H 0.4331 0.3504 0.4753 0.0310 1.0000 Uiso R . . . . . . 
H201 H 0.3687 0.2130 0.6135 0.0251 1.0000 Uiso R . . . . . . 
H202 H 0.3338 0.2017 0.5024 0.0252 1.0000 Uiso R . . . . . . 
H212 H 0.6914 0.4744 0.6076 0.0480 1.0000 Uiso R . . . . . . 
H213 H 0.9025 0.4267 0.5897 0.0495 1.0000 Uiso R . . . . . . 
H211 H 0.7617 0.4596 0.5039 0.0482 1.0000 Uiso R . . . . . . 

_refine_ls_extinction_method 
    'None'
_oxford_refine_ls_scale 0.6863(16) 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_site_symmetry_1
 _geom_bond_atom_site_label_2
 _geom_bond_site_symmetry_2
 _geom_bond_distance
 _geom_bond_publ_flag
O1 . C2 . 1.2055(15)    yes
C2 . O3 . 1.3351(14)    yes
C2 . C5 . 1.5312(16)    yes
O3 . C4 . 1.4504(14)    yes
C4 . H43 . 0.975    no
C4 . H41 . 0.977    no
C4 . H42 . 0.984    no
C5 . C6 . 1.5529(16)    yes
C5 . C16 . 1.5402(16)    yes
C5 . C20 . 1.5500(16)    yes
C6 . C7 . 1.5062(16)    yes
C6 . C12 . 1.5383(16)    yes
C6 . H61 . 0.985    no
C7 . C8 . 1.3501(17)    yes
C7 . C11 . 1.4357(17)    yes
C8 . O9 . 1.3700(14)    yes
C8 . H81 . 0.974    no
O9 . C10 . 1.3654(16)    yes
C10 . C11 . 1.3445(19)    yes
C10 . H101 . 0.964    no
C11 . H111 . 0.966    no
C12 . N13 . 1.4979(16)    yes
C12 . H121 . 0.968    no
C12 . H122 . 0.985    no
N13 . O14 . 1.2210(15)    yes
N13 . O15 . 1.2183(16)    yes
C16 . O17 . 1.2331(15)    yes
C16 . N18 . 1.3347(15)    yes
N18 . C19 . 1.4553(16)    yes
N18 . C21 . 1.4520(16)    yes
C19 . C20 . 1.5332(18)    yes
C19 . H191 . 0.990    no
C19 . H192 . 0.987    no
C20 . H201 . 0.981    no
C20 . H202 . 0.975    no
C21 . H212 . 0.961    no
C21 . H213 . 0.976    no
C21 . H211 . 0.976    no
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_site_symmetry_1
 _geom_angle_atom_site_label_2
 _geom_angle_site_symmetry_2
 _geom_angle_atom_site_label_3
 _geom_angle_site_symmetry_3
 _geom_angle
 _geom_angle_publ_flag
O1 . C2 . O3 . 123.90(11)    yes
O1 . C2 . C5 . 125.74(11)    yes
O3 . C2 . C5 . 110.33(10)    yes
C2 . O3 . C4 . 116.20(10)    yes
O3 . C4 . H43 . 105.3    no
O3 . C4 . H41 . 109.5    no
H43 . C4 . H41 . 111.1    no
O3 . C4 . H42 . 109.2    no
H43 . C4 . H42 . 109.7    no
H41 . C4 . H42 . 111.7    no
C2 . C5 . C6 . 109.32(9)    yes
C2 . C5 . C16 . 107.43(9)    yes
C6 . C5 . C16 . 114.69(9)    yes
C2 . C5 . C20 . 108.86(9)    yes
C6 . C5 . C20 . 113.28(9)    yes
C16 . C5 . C20 . 102.89(9)    yes
C5 . C6 . C7 . 113.89(9)    yes
C5 . C6 . C12 . 112.17(9)    yes
C7 . C6 . C12 . 109.70(10)    yes
C5 . C6 . H61 . 106.4    no
C7 . C6 . H61 . 108.5    no
C12 . C6 . H61 . 105.8    no
C6 . C7 . C8 . 125.38(11)    yes
C6 . C7 . C11 . 128.90(11)    yes
C8 . C7 . C11 . 105.69(11)    yes
C7 . C8 . O9 . 111.00(11)    yes
C7 . C8 . H81 . 128.2    no
O9 . C8 . H81 . 120.8    no
C8 . O9 . C10 . 105.90(10)    yes
O9 . C10 . C11 . 110.88(11)    yes
O9 . C10 . H101 . 119.2    no
C11 . C10 . H101 . 129.9    no
C7 . C11 . C10 . 106.52(11)    yes
C7 . C11 . H111 . 127.1    no
C10 . C11 . H111 . 126.3    no
C6 . C12 . N13 . 108.17(10)    yes
C6 . C12 . H121 . 111.8    no
N13 . C12 . H121 . 106.7    no
C6 . C12 . H122 . 110.5    no
N13 . C12 . H122 . 107.6    no
H121 . C12 . H122 . 111.8    no
C12 . N13 . O14 . 118.08(11)    yes
C12 . N13 . O15 . 117.97(11)    yes
O14 . N13 . O15 . 123.96(12)    yes
C5 . C16 . O17 . 124.58(11)    yes
C5 . C16 . N18 . 109.24(10)    yes
O17 . C16 . N18 . 126.14(11)    yes
C16 . N18 . C19 . 114.48(10)    yes
C16 . N18 . C21 . 122.58(11)    yes
C19 . N18 . C21 . 121.40(11)    yes
N18 . C19 . C20 . 103.77(10)    yes
N18 . C19 . H191 . 111.3    no
C20 . C19 . H191 . 111.6    no
N18 . C19 . H192 . 109.5    no
C20 . C19 . H192 . 111.1    no
H191 . C19 . H192 . 109.5    no
C19 . C20 . C5 . 105.24(10)    yes
C19 . C20 . H201 . 109.9    no
C5 . C20 . H201 . 109.0    no
C19 . C20 . H202 . 111.5    no
C5 . C20 . H202 . 110.9    no
H201 . C20 . H202 . 110.2    no
N18 . C21 . H212 . 109.6    no
N18 . C21 . H213 . 108.1    no
H212 . C21 . H213 . 110.4    no
N18 . C21 . H211 . 110.0    no
H212 . C21 . H211 . 109.5    no
H213 . C21 . H211 . 109.2    no
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_site_symmetry_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_site_symmetry_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_site_symmetry_A
 _geom_hbond_angle_DHA
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_publ_flag
C4 . H41 . O14 2_756 152 0.98 2.50 3.3963(18)    yes
C6 . H61 . O1 2_656 154 0.98 2.58 3.4909(18)    yes
C8 . H81 . O1 2_656 142 0.97 2.49 3.3115(18)    yes
C10 . H101 . O17 4_455 158 0.96 2.53 3.4470(18)    yes
C20 . H202 . O15 2_656 160 0.98 2.58 3.5087(18)    yes
C21 . H212 . O14 3_656 138 0.96 2.46 3.2429(18)    yes


#==============================================================================
data_11c 
#==============================================================================
_audit_creation_date        09-05-06
_audit_creation_method CRYSTALS_ver_12.87

_oxford_structure_analysis_title  '6105'
_chemical_name_systematic         .
_chemical_melting_point           'not measured'

_cell_length_a                    20.7471(6)
_cell_length_b                    7.3739(2)
_cell_length_c                    12.0188(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90.9587(14)
_cell_angle_gamma                 90
_cell_volume                      1838.46(9)
 
_symmetry_cell_setting            'monoclinic' 
_symmetry_space_group_name_H-M    'P 1 21/c 1 ' 
_symmetry_space_group_name_Hall   '-P 2ybc' 
loop_
 _symmetry_equiv_pos_as_xyz
 'x,y,z'
 '-x,-y,-z'
 '-x,y+1/2,-z+1/2'
 'x,-y+1/2,z+1/2'

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source  
 C       0.0033   0.0016   2.3100  20.8439   1.0200  10.2075   1.5886   0.5687
   0.8650  51.6512   0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 H       0.0000   0.0000   0.4930  10.5109   0.3229  26.1257   0.1402   3.1424
   0.0408  57.7998   0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 N       0.0061   0.0033  12.2126   0.0057   3.1322   9.8933   2.0125  28.9975
   1.1663   0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 O       0.0106   0.0060   3.0485  13.2771   2.2868   5.7011   1.5463   0.3239
   0.8670  32.9089   0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 
 
_cell_formula_units_Z                    4

# Given Formula = C23 H25 N2 O1 
# Dc =      1.25 Fooo =    744.00 Mu =      0.77 M =    345.46
# Found Formula = C23 H26 N2 O1 
# Dc =      1.25 FOOO =    744.00 Mu =      0.77 M =    346.47

_chemical_formula_sum             'C23 H26 N2 O1'
_chemical_formula_moiety          'C23 H26 N2 O1'
_chemical_compound_source                .
_chemical_formula_weight            346.47
 
 
_cell_measurement_reflns_used         4193
_cell_measurement_theta_min              5
_cell_measurement_theta_max             27
_cell_measurement_temperature          150
 
_exptl_crystal_description        'plate' 
_exptl_crystal_colour             'clear_pale_colourless' 
_exptl_crystal_size_min           0.060 
_exptl_crystal_size_mid           0.180 
_exptl_crystal_size_max           0.180 
 
_exptl_crystal_density_diffrn     1.252 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_method     'not measured' 
# Non-dispersive F(000): 
_exptl_crystal_F_000              744 
_exptl_absorpt_coefficient_mu     0.077 
 
# Sheldrick geometric approximatio 0.99 1.00 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_process_details    'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_exptl_absorpt_correction_T_min   0.94 
_exptl_absorpt_correction_T_max   1.00 
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device        'Nonius KappaCCD' 
_diffrn_measurement_device_type   'Area' 
_diffrn_radiation_monochromator   'graphite' 
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength           0.71073
_diffrn_measurement_method        ω 
 
# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection        'COLLECT (Nonius, 1997-2001).' 
_computing_cell_refinement        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_computing_data_reduction         'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_computing_structure_solution     'SIR92 (Altomare et al., 1994)' 
_computing_structure_refinement   'CRYSTALS (Betteridge et al., 2003)' 
_computing_publication_material   'CRYSTALS (Betteridge et al., 2003)' 
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)' 
 
_diffrn_standards_interval_time   . 
_diffrn_standards_interval_count  . 
_diffrn_standards_number          0 
_diffrn_standards_decay_%         . 
 
_diffrn_ambient_temperature        150
_diffrn_reflns_number             17146 
_reflns_number_total              4194 
_diffrn_reflns_av_R_equivalents   0.058 
# Number of reflections with Friedels Law is 4194 
# Number of reflections without Friedels Law is 6254 
# Theoretical number of reflections is about 4240 
 
 
_diffrn_reflns_theta_min          5.119 
_diffrn_reflns_theta_max          27.540 
_diffrn_measured_fraction_theta_max 0.987 
 
_diffrn_reflns_theta_full         25.887 
_diffrn_measured_fraction_theta_full 0.990 
 
 
_diffrn_reflns_limit_h_min        -26 
_diffrn_reflns_limit_h_max        26 
_diffrn_reflns_limit_k_min        -7 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_reflns_limit_h_min               0 
_reflns_limit_h_max               26 
_reflns_limit_k_min               -9 
_reflns_limit_k_max               0 
_reflns_limit_l_min               -15 
_reflns_limit_l_max               15 
 
_oxford_diffrn_Wilson_B_factor    0.00 
_oxford_diffrn_Wilson_scale       0.00 
 
_atom_sites_solution_primary      direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens    geom
 
_refine_diff_density_min          -0.39 
_refine_diff_density_max          0.44 
 
 
# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 
 
 
# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref     I>-3.0\s(I)
_refine_ls_number_reflns          4194 
_refine_ls_number_restraints      0 
_refine_ls_number_parameters      235 
_oxford_refine_ls_R_factor_ref    0.0891 
_refine_ls_wR_factor_ref          0.1558 
_refine_ls_goodness_of_fit_ref    0.9724 
_refine_ls_shift/su_max           0.000194 
 
 
# The values computed from all data 
_oxford_reflns_number_all         4194 
_refine_ls_R_factor_all           0.0891 
_refine_ls_wR_factor_all          0.1558 
 
# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression      I>2.0σ(I)
_reflns_number_gt                 2739 
_refine_ls_R_factor_gt            0.0501 
_refine_ls_wR_factor_gt           0.1161 
 
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration  '.' 
 
 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full
_refine_ls_hydrogen_treatment     none           # none, undef, noref, refall,
                                                 # refxyz, refU, constr or mixed
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 14.6 21.9 10.9 2.98 
;
# Insert your own references if required - in alphabetical order 
_publ_section_references 
; 
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., 
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. 
 
Betteridge, P.W., Carruthers, J.R., Cooper, R.I., 
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 
 
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. 
 
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, 
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. 
New York: Academic Press. 
 
Prince, E. 
Mathematical Techniques in Crystallography 
and Materials Science 
Springer-Verlag, New York, 1982. 
 
Watkin D.J. (1994). 
Acta Cryst, A50, 411-437. 
 
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical 
Crystallography Laboratory, Oxford, UK. 
; 

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.27215(6) 0.5407(2) 0.44560(11) 0.0319 1.0000 Uani . . . . . . . 
C2 C 0.28332(9) 0.5130(3) 0.54490(16) 0.0273 1.0000 Uani . . . . . . . 
N3 N 0.32683(8) 0.3903(2) 0.58294(14) 0.0339 1.0000 Uani . . . . . . . 
C4 C 0.37218(12) 0.3021(3) 0.5102(2) 0.0443 1.0000 Uani . . . . . . . 
C5 C 0.33803(12) 0.3969(3) 0.70227(18) 0.0413 1.0000 Uani . . . . . . . 
C6 C 0.27861(12) 0.4959(3) 0.74402(18) 0.0404 1.0000 Uani . . . . . . . 
C7 C 0.25365(9) 0.6095(3) 0.64436(16) 0.0295 1.0000 Uani . . . . . . . 
C8 C 0.17961(10) 0.6093(3) 0.64069(18) 0.0350 1.0000 Uani . . . . . . . 
N9 N 0.15245(8) 0.7202(2) 0.55080(15) 0.0323 1.0000 Uani . . . . . . . 
C10 C 0.17031(9) 0.9101(3) 0.56475(18) 0.0320 1.0000 Uani . . . . . . . 
C11 C 0.24397(9) 0.9245(3) 0.56203(17) 0.0305 1.0000 Uani . . . . . . . 
C12 C 0.27682(9) 0.8088(3) 0.65194(16) 0.0290 1.0000 Uani . . . . . . . 
C13 C 0.34980(9) 0.8298(3) 0.65198(16) 0.0270 1.0000 Uani . . . . . . . 
C14 C 0.38568(10) 0.8006(3) 0.55571(16) 0.0303 1.0000 Uani . . . . . . . 
C15 C 0.45243(10) 0.8193(3) 0.55744(18) 0.0344 1.0000 Uani . . . . . . . 
C16 C 0.48419(10) 0.8702(3) 0.65481(19) 0.0394 1.0000 Uani . . . . . . . 
C17 C 0.44920(11) 0.9026(3) 0.74958(19) 0.0399 1.0000 Uani . . . . . . . 
C18 C 0.38239(10) 0.8828(3) 0.74832(17) 0.0329 1.0000 Uani . . . . . . . 
C19 C 0.13821(9) 1.0270(3) 0.47558(17) 0.0325 1.0000 Uani . . . . . . . 
C20 C 0.16135(10) 1.2010(3) 0.45491(19) 0.0382 1.0000 Uani . . . . . . . 
C21 C 0.13493(11) 1.3099(3) 0.3722(2) 0.0418 1.0000 Uani . . . . . . . 
C22 C 0.08424(11) 1.2435(3) 0.3078(2) 0.0438 1.0000 Uani . . . . . . . 
C23 C 0.05962(10) 1.0734(3) 0.3292(2) 0.0415 1.0000 Uani . . . . . . . 
C24 C 0.08549(9) 0.9641(3) 0.41335(19) 0.0363 1.0000 Uani . . . . . . . 
C25 C 0.05718(10) 0.7800(3) 0.4358(2) 0.0433 1.0000 Uani . . . . . . . 
C26 C 0.08208(10) 0.7008(3) 0.5446(2) 0.0412 1.0000 Uani . . . . . . . 
H41 H 0.3844 0.1817 0.5418 0.0661 1.0000 Uiso R . . . . . . 
H43 H 0.3511 0.2853 0.4357 0.0659 1.0000 Uiso R . . . . . . 
H42 H 0.4113 0.3765 0.5023 0.0661 1.0000 Uiso R . . . . . . 
H51 H 0.3414 0.2718 0.7319 0.0490 1.0000 Uiso R . . . . . . 
H52 H 0.3779 0.4689 0.7202 0.0493 1.0000 Uiso R . . . . . . 
H61 H 0.2457 0.4073 0.7652 0.0484 1.0000 Uiso R . . . . . . 
H62 H 0.2899 0.5748 0.8069 0.0484 1.0000 Uiso R . . . . . . 
H82 H 0.1645 0.6538 0.7146 0.0414 1.0000 Uiso R . . . . . . 
H81 H 0.1649 0.4829 0.6299 0.0404 1.0000 Uiso R . . . . . . 
H101 H 0.1562 0.9544 0.6398 0.0381 1.0000 Uiso R . . . . . . 
H112 H 0.2573 1.0526 0.5734 0.0366 1.0000 Uiso R . . . . . . 
H111 H 0.2580 0.8840 0.4883 0.0358 1.0000 Uiso R . . . . . . 
H121 H 0.2619 0.8528 0.7244 0.0351 1.0000 Uiso R . . . . . . 
H141 H 0.3633 0.7651 0.4886 0.0366 1.0000 Uiso R . . . . . . 
H151 H 0.4763 0.7990 0.4894 0.0415 1.0000 Uiso R . . . . . . 
H161 H 0.5303 0.8830 0.6560 0.0471 1.0000 Uiso R . . . . . . 
H171 H 0.4702 0.9410 0.8170 0.0477 1.0000 Uiso R . . . . . . 
H181 H 0.3580 0.9073 0.8153 0.0394 1.0000 Uiso R . . . . . . 
H201 H 0.1972 1.2462 0.4984 0.0463 1.0000 Uiso R . . . . . . 
H211 H 0.1517 1.4287 0.3601 0.0500 1.0000 Uiso R . . . . . . 
H221 H 0.0661 1.3150 0.2487 0.0532 1.0000 Uiso R . . . . . . 
H231 H 0.0246 1.0284 0.2841 0.0499 1.0000 Uiso R . . . . . . 
H251 H 0.0095 0.7894 0.4377 0.0527 1.0000 Uiso R . . . . . . 
H252 H 0.0695 0.6953 0.3746 0.0516 1.0000 Uiso R . . . . . . 
H261 H 0.0619 0.7659 0.6095 0.0485 1.0000 Uiso R . . . . . . 
H262 H 0.0711 0.5699 0.5485 0.0479 1.0000 Uiso R . . . . . . 

_refine_ls_extinction_method 
    'None'
_oxford_refine_ls_scale 0.4332(9) 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_site_symmetry_1
 _geom_bond_atom_site_label_2
 _geom_bond_site_symmetry_2
 _geom_bond_distance
 _geom_bond_publ_flag
O1 . C2 . 1.229(2)    yes
C2 . N3 . 1.352(3)    yes
C2 . C7 . 1.529(3)    yes
N3 . C4 . 1.449(3)    yes
N3 . C5 . 1.450(3)    yes
C4 . H41 . 0.996    no
C4 . H43 . 0.998    no
C4 . H42 . 0.986    no
C5 . C6 . 1.525(3)    yes
C5 . H51 . 0.991    no
C5 . H52 . 1.003    no
C6 . C7 . 1.544(3)    yes
C6 . H61 . 0.982    no
C6 . H62 . 0.979    no
C7 . C8 . 1.536(3)    yes
C7 . C12 . 1.549(3)    yes
C8 . N9 . 1.460(3)    yes
C8 . H82 . 1.002    no
C8 . H81 . 0.988    no
N9 . C10 . 1.458(3)    yes
N9 . C26 . 1.468(2)    yes
C10 . C11 . 1.533(3)    yes
C10 . C19 . 1.520(3)    yes
C10 . H101 . 1.008    no
C11 . C12 . 1.528(3)    yes
C11 . H112 . 0.994    no
C11 . H111 . 0.984    no
C12 . C13 . 1.522(3)    yes
C12 . H121 . 0.984    no
C13 . C14 . 1.403(3)    yes
C13 . C18 . 1.387(3)    yes
C14 . C15 . 1.392(3)    yes
C14 . H141 . 0.960    no
C15 . C16 . 1.385(3)    yes
C15 . H151 . 0.975    no
C16 . C17 . 1.382(3)    yes
C16 . H161 . 0.961    no
C17 . C18 . 1.394(3)    yes
C17 . H171 . 0.956    no
C18 . H181 . 0.974    no
C19 . C20 . 1.394(3)    yes
C19 . C24 . 1.394(3)    yes
C20 . C21 . 1.384(3)    yes
C20 . H201 . 0.962    no
C21 . C22 . 1.385(3)    yes
C21 . H211 . 0.954    no
C22 . C23 . 1.380(4)    yes
C22 . H221 . 0.956    no
C23 . C24 . 1.394(3)    yes
C23 . H231 . 0.959    no
C24 . C25 . 1.505(3)    yes
C25 . C26 . 1.516(4)    yes
C25 . H251 . 0.992    no
C25 . H252 . 1.001    no
C26 . H261 . 1.012    no
C26 . H262 . 0.992    no
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_site_symmetry_1
 _geom_angle_atom_site_label_2
 _geom_angle_site_symmetry_2
 _geom_angle_atom_site_label_3
 _geom_angle_site_symmetry_3
 _geom_angle
 _geom_angle_publ_flag
O1 . C2 . N3 . 123.61(18)    yes
O1 . C2 . C7 . 127.58(18)    yes
N3 . C2 . C7 . 108.79(16)    yes
C2 . N3 . C4 . 122.20(18)    yes
C2 . N3 . C5 . 114.02(18)    yes
C4 . N3 . C5 . 121.12(18)    yes
N3 . C4 . H41 . 109.4    no
N3 . C4 . H43 . 108.6    no
H41 . C4 . H43 . 109.7    no
N3 . C4 . H42 . 110.6    no
H41 . C4 . H42 . 109.1    no
H43 . C4 . H42 . 109.4    no
N3 . C5 . C6 . 102.97(17)    yes
N3 . C5 . H51 . 109.4    no
C6 . C5 . H51 . 112.3    no
N3 . C5 . H52 . 110.4    no
C6 . C5 . H52 . 110.1    no
H51 . C5 . H52 . 111.3    no
C5 . C6 . C7 . 105.47(16)    yes
C5 . C6 . H61 . 109.7    no
C7 . C6 . H61 . 109.6    no
C5 . C6 . H62 . 110.8    no
C7 . C6 . H62 . 110.4    no
H61 . C6 . H62 . 110.7    no
C6 . C7 . C2 . 102.71(17)    yes
C6 . C7 . C8 . 110.13(17)    yes
C2 . C7 . C8 . 113.13(17)    yes
C6 . C7 . C12 . 111.69(17)    yes
C2 . C7 . C12 . 111.02(15)    yes
C8 . C7 . C12 . 108.16(17)    yes
C7 . C8 . N9 . 113.21(16)    yes
C7 . C8 . H82 . 107.5    no
N9 . C8 . H82 . 110.5    no
C7 . C8 . H81 . 108.1    no
N9 . C8 . H81 . 108.5    no
H82 . C8 . H81 . 109.0    no
C8 . N9 . C10 . 111.01(17)    yes
C8 . N9 . C26 . 110.72(17)    yes
C10 . N9 . C26 . 110.51(17)    yes
N9 . C10 . C11 . 108.40(16)    yes
N9 . C10 . C19 . 110.87(17)    yes
C11 . C10 . C19 . 111.77(17)    yes
N9 . C10 . H101 . 109.7    no
C11 . C10 . H101 . 107.5    no
C19 . C10 . H101 . 108.5    no
C10 . C11 . C12 . 112.30(17)    yes
C10 . C11 . H112 . 109.8    no
C12 . C11 . H112 . 108.2    no
C10 . C11 . H111 . 107.9    no
C12 . C11 . H111 . 109.4    no
H112 . C11 . H111 . 109.1    no
C7 . C12 . C11 . 110.73(16)    yes
C7 . C12 . C13 . 113.86(16)    yes
C11 . C12 . C13 . 112.04(16)    yes
C7 . C12 . H121 . 105.3    no
C11 . C12 . H121 . 107.4    no
C13 . C12 . H121 . 107.0    no
C12 . C13 . C14 . 121.72(17)    yes
C12 . C13 . C18 . 119.99(17)    yes
C14 . C13 . C18 . 118.28(18)    yes
C13 . C14 . C15 . 120.94(18)    yes
C13 . C14 . H141 . 118.6    no
C15 . C14 . H141 . 120.4    no
C14 . C15 . C16 . 119.91(19)    yes
C14 . C15 . H151 . 119.5    no
C16 . C15 . H151 . 120.6    no
C15 . C16 . C17 . 119.6(2)    yes
C15 . C16 . H161 . 119.9    no
C17 . C16 . H161 . 120.5    no
C16 . C17 . C18 . 120.6(2)    yes
C16 . C17 . H171 . 120.7    no
C18 . C17 . H171 . 118.6    no
C17 . C18 . C13 . 120.6(2)    yes
C17 . C18 . H181 . 120.1    no
C13 . C18 . H181 . 119.3    no
C10 . C19 . C20 . 119.97(18)    yes
C10 . C19 . C24 . 121.3(2)    yes
C20 . C19 . C24 . 118.7(2)    yes
C19 . C20 . C21 . 121.9(2)    yes
C19 . C20 . H201 . 119.2    no
C21 . C20 . H201 . 118.9    no
C20 . C21 . C22 . 118.9(2)    yes
C20 . C21 . H211 . 120.1    no
C22 . C21 . H211 . 121.0    no
C21 . C22 . C23 . 119.8(2)    yes
C21 . C22 . H221 . 120.3    no
C23 . C22 . H221 . 119.8    no
C22 . C23 . C24 . 121.4(2)    yes
C22 . C23 . H231 . 119.3    no
C24 . C23 . H231 . 119.3    no
C19 . C24 . C23 . 119.1(2)    yes
C19 . C24 . C25 . 120.6(2)    yes
C23 . C24 . C25 . 120.34(19)    yes
C24 . C25 . C26 . 111.95(19)    yes
C24 . C25 . H251 . 109.5    no
C26 . C25 . H251 . 109.4    no
C24 . C25 . H252 . 109.0    no
C26 . C25 . H252 . 107.8    no
H251 . C25 . H252 . 109.1    no
C25 . C26 . N9 . 109.29(18)    yes
C25 . C26 . H261 . 110.1    no
N9 . C26 . H261 . 109.8    no
C25 . C26 . H262 . 109.9    no
N9 . C26 . H262 . 108.8    no
H261 . C26 . H262 . 109.1    no
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_site_symmetry_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_site_symmetry_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_site_symmetry_A
 _geom_hbond_angle_DHA
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_publ_flag
C14 . H141 . O1 . 134 0.96 2.56 3.297(3)    yes
C18 . H181 . O1 4_565 164 0.97 2.42 3.369(3)    yes
