data_global
_audit_creation_method            SHELXL-2014
_audit_creation_date                               2016-09-29

data_I
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety         'C15 H15 N O5' 
_chemical_formula_sum            'C15 H15 N O5' 
_chemical_formula_weight          289.28

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.29127(13)
_cell_length_b                    8.31167(15)
_cell_length_c                    11.5175(2)
_cell_angle_alpha                 82.3378(11)
_cell_angle_beta                  80.5820(10)
_cell_angle_gamma                 84.9113(10)
_cell_volume                      680.84(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     193(2)
_cell_measurement_reflns_used                      11412
_cell_measurement_theta_min                        3.92
_cell_measurement_theta_max                        68.17
 
_exptl_crystal_description                         block
_exptl_crystal_colour                              colorless
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.411          
_exptl_crystal_F_000              304
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.600
_exptl_crystal_size_mid           0.500
_exptl_crystal_size_min           0.300
_exptl_absorpt_coefficient_mu     0.896
_shelx_estimated_absorpt_T_min    0.615
_shelx_estimated_absorpt_T_max    0.775
_exptl_absorpt_correction_type                     numerical
_exptl_absorpt_process_details                    'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min                    0.616
_exptl_absorpt_correction_T_max                    0.764
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       193(2)
_diffrn_radiation_wavelength      1.54187
_diffrn_radiation_type            CuK\a
_diffrn_source                    'rotating anode'                     
_diffrn_measurement_device_type                   'Rigaku R-AXIS RAPID'
_diffrn_measurement_method                         ω
_diffrn_detector_area_resol_mean                   10.000
_diffrn_reflns_number             12382
_diffrn_reflns_av_unetI/netI      0.0193
_diffrn_reflns_av_R_equivalents   0.0356
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.919
_diffrn_reflns_theta_max          68.168
_diffrn_reflns_theta_full         67.687
_diffrn_measured_fraction_theta_max   0.987
_diffrn_measured_fraction_theta_full  0.987
_diffrn_reflns_Laue_measured_fraction_max    0.987
_diffrn_reflns_Laue_measured_fraction_full   0.987
_diffrn_reflns_point_group_measured_fraction_max   0.987
_diffrn_reflns_point_group_measured_fraction_full  0.987
_reflns_number_total              2454
_reflns_number_gt                 2189
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection                        'RAPID AUTO (Rigaku, 2004)'
_computing_cell_refinement                        'RAPID AUTO'
_computing_data_reduction                         'RAPID AUTO'
_computing_structure_solution
                                             'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement   'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0695P)²+0.2618P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.024(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2454
_refine_ls_number_parameters      193
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0448
_refine_ls_R_factor_gt            0.0404
_refine_ls_wR_factor_ref          0.1196
_refine_ls_wR_factor_gt           0.1094
_refine_ls_goodness_of_fit_ref    1.071
_refine_ls_restrained_S_all       1.071
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.18964(15) 0.18665(13) 0.79058(10) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.55001(17) 0.38419(15) 0.84079(12) 0.0396(3) Uani 1 1 d . . . . .
O3 O 0.37438(14) 0.64343(12) 0.70605(9) 0.0267(3) Uani 1 1 d . . . . .
O4 O 0.14685(15) 0.54077(13) 0.85909(9) 0.0295(3) Uani 1 1 d . . . . .
O5 O -0.12480(17) 0.32361(14) 0.59756(11) 0.0379(3) Uani 1 1 d . . . . .
N1 N 0.06548(17) 0.30636(15) 0.73568(11) 0.0250(3) Uani 1 1 d . . . . .
C1 C 0.1648(2) 0.44676(18) 0.67153(13) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.0763 0.5343 0.6400 0.029 Uiso 1 1 calc R U . . .
C2 C 0.2744(2) 0.50914(18) 0.75901(13) 0.0240(3) Uani 1 1 d . . . . .
C3 C 0.4229(2) 0.37067(19) 0.78923(13) 0.0259(4) Uani 1 1 d . . . . .
C4 C 0.3846(2) 0.21629(19) 0.74177(14) 0.0269(4) Uani 1 1 d . . . . .
H4 H 0.4711 0.1224 0.7665 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4133(2) 0.2585(2) 0.61009(14) 0.0302(4) Uani 1 1 d . . . . .
H5 H 0.5020 0.2009 0.5580 0.036 Uiso 1 1 calc R U . . .
C6 C 0.3033(2) 0.38395(19) 0.57271(14) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.3110 0.4295 0.4920 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2605(2) 0.78671(19) 0.67383(16) 0.0336(4) Uani 1 1 d . . . . .
H7A H 0.2023 0.7711 0.6056 0.040 Uiso 1 1 calc R U . . .
H7B H 0.3379 0.8800 0.6530 0.040 Uiso 1 1 calc R U . . .
H7C H 0.1635 0.8071 0.7409 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2213(3) 0.6049(2) 0.95036(15) 0.0378(4) Uani 1 1 d . . . . .
H8A H 0.1217 0.6204 1.0170 0.045 Uiso 1 1 calc R U . . .
H8B H 0.2728 0.7096 0.9186 0.045 Uiso 1 1 calc R U . . .
H8C H 0.3199 0.5284 0.9776 0.045 Uiso 1 1 calc R U . . .
C9 C -0.0612(2) 0.24285(18) 0.67982(13) 0.0256(4) Uani 1 1 d . . . . .
C10 C -0.1272(2) 0.07976(18) 0.73082(14) 0.0248(3) Uani 1 1 d . . . . .
C11 C -0.1489(2) 0.0256(2) 0.85134(14) 0.0316(4) Uani 1 1 d . . . . .
H11 H -0.1136 0.0904 0.9049 0.038 Uiso 1 1 calc R U . . .
C12 C -0.2223(3) -0.1231(2) 0.89329(17) 0.0412(4) Uani 1 1 d . . . . .
H12 H -0.2376 -0.1598 0.9758 0.049 Uiso 1 1 calc R U . . .
C13 C -0.2732(3) -0.2186(2) 0.81568(18) 0.0425(5) Uani 1 1 d . . . . .
H13 H -0.3233 -0.3205 0.8449 0.051 Uiso 1 1 calc R U . . .
C14 C -0.2510(2) -0.1655(2) 0.69588(17) 0.0363(4) Uani 1 1 d . . . . .
H14 H -0.2851 -0.2313 0.6425 0.044 Uiso 1 1 calc R U . . .
C15 C -0.1793(2) -0.0166(2) 0.65313(14) 0.0286(4) Uani 1 1 d . . . . .
H15 H -0.1655 0.0200 0.5706 0.034 Uiso 1 1 calc R U . . .
 
 
_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 N1 1.4384(16) . ?
O1 C4 1.4701(18) . ?
O2 C3 1.2001(19) . ?
O3 C2 1.4024(17) . ?
O3 C7 1.4327(19) . ?
O4 C2 1.3961(18) . ?
O4 C8 1.4390(19) . ?
O5 C9 1.2175(19) . ?
N1 C9 1.3845(19) . ?
N1 C1 1.4754(18) . ?
C1 C6 1.509(2) . ?
C1 C2 1.5490(19) . ?
C1 H1 1.0000 . ?
C2 C3 1.554(2) . ?
C3 C4 1.524(2) . ?
C4 C5 1.495(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.327(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.492(2) . ?
C10 C11 1.389(2) . ?
C10 C15 1.394(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 H15 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
N1 O1 C4 110.48(10) . . ?
C2 O3 C7 114.45(11) . . ?
C2 O4 C8 115.88(12) . . ?
C9 N1 O1 114.58(11) . . ?
C9 N1 C1 117.75(12) . . ?
O1 N1 C1 111.60(11) . . ?
N1 C1 C6 107.02(12) . . ?
N1 C1 C2 107.40(12) . . ?
C6 C1 C2 108.25(12) . . ?
N1 C1 H1 111.3 . . ?
C6 C1 H1 111.3 . . ?
C2 C1 H1 111.3 . . ?
O4 C2 O3 113.55(11) . . ?
O4 C2 C1 107.29(12) . . ?
O3 C2 C1 111.82(12) . . ?
O4 C2 C3 111.69(12) . . ?
O3 C2 C3 105.87(11) . . ?
C1 C2 C3 106.45(11) . . ?
O2 C3 C4 125.24(14) . . ?
O2 C3 C2 124.99(14) . . ?
C4 C3 C2 109.76(12) . . ?
O1 C4 C5 112.39(12) . . ?
O1 C4 C3 105.45(12) . . ?
C5 C4 C3 104.55(13) . . ?
O1 C4 H4 111.4 . . ?
C5 C4 H4 111.4 . . ?
C3 C4 H4 111.4 . . ?
C6 C5 C4 113.75(14) . . ?
C6 C5 H5 123.1 . . ?
C4 C5 H5 123.1 . . ?
C5 C6 C1 113.05(14) . . ?
C5 C6 H6 123.5 . . ?
C1 C6 H6 123.5 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 C9 N1 120.34(14) . . ?
O5 C9 C10 121.99(13) . . ?
N1 C9 C10 117.47(13) . . ?
C11 C10 C15 119.49(14) . . ?
C11 C10 C9 123.03(14) . . ?
C15 C10 C9 117.36(14) . . ?
C12 C11 C10 119.87(15) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.40(17) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.87(16) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.21(15) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.16(15) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
 
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
C4 O1 N1 C9 121.96(13) . . . . ?
C4 O1 N1 C1 -15.08(15) . . . . ?
C9 N1 C1 C6 -72.02(16) . . . . ?
O1 N1 C1 C6 63.54(14) . . . . ?
C9 N1 C1 C2 171.94(12) . . . . ?
O1 N1 C1 C2 -52.51(15) . . . . ?
C8 O4 C2 O3 -54.20(18) . . . . ?
C8 O4 C2 C1 -178.28(13) . . . . ?
C8 O4 C2 C3 65.43(16) . . . . ?
C7 O3 C2 O4 -55.70(16) . . . . ?
C7 O3 C2 C1 65.88(16) . . . . ?
C7 O3 C2 C3 -178.60(12) . . . . ?
N1 C1 C2 O4 -54.93(15) . . . . ?
C6 C1 C2 O4 -170.16(12) . . . . ?
N1 C1 C2 O3 179.94(11) . . . . ?
C6 C1 C2 O3 64.71(15) . . . . ?
N1 C1 C2 C3 64.77(14) . . . . ?
C6 C1 C2 C3 -50.46(15) . . . . ?
O4 C2 C3 O2 -74.43(19) . . . . ?
O3 C2 C3 O2 49.63(19) . . . . ?
C1 C2 C3 O2 168.77(15) . . . . ?
O4 C2 C3 C4 106.48(14) . . . . ?
O3 C2 C3 C4 -129.45(12) . . . . ?
C1 C2 C3 C4 -10.32(16) . . . . ?
N1 O1 C4 C5 -42.75(16) . . . . ?
N1 O1 C4 C3 70.57(14) . . . . ?
O2 C3 C4 O1 127.12(16) . . . . ?
C2 C3 C4 O1 -53.79(15) . . . . ?
O2 C3 C4 C5 -114.19(17) . . . . ?
C2 C3 C4 C5 64.89(15) . . . . ?
O1 C4 C5 C6 55.08(17) . . . . ?
C3 C4 C5 C6 -58.79(16) . . . . ?
C4 C5 C6 C1 -4.31(19) . . . . ?
N1 C1 C6 C5 -52.91(16) . . . . ?
C2 C1 C6 C5 62.57(16) . . . . ?
O1 N1 C9 O5 -153.50(14) . . . . ?
C1 N1 C9 O5 -19.2(2) . . . . ?
O1 N1 C9 C10 31.59(18) . . . . ?
C1 N1 C9 C10 165.87(12) . . . . ?
O5 C9 C10 C11 -141.90(17) . . . . ?
N1 C9 C10 C11 32.9(2) . . . . ?
O5 C9 C10 C15 34.1(2) . . . . ?
N1 C9 C10 C15 -151.03(14) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?
C9 C10 C11 C12 175.86(15) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
C9 C10 C15 C14 -176.58(14) . . . . ?
 
_refine_diff_density_max    0.282
_refine_diff_density_min   -0.318
_refine_diff_density_rms    0.056

_shelxl_version_number 2014-3



