 
data_ta0507h 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ?
_chemical_absolute_configuration syn 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C24 H31 N O4' 
_chemical_formula_weight          397.50 
 
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' 
 'O'  'O'   0.0106   0.0060 
 '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' 
 
_symmetry_cell_setting            'monoclinic' 
_symmetry_space_group_name_H-M    'P2(1)' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    6.6454(3) 
_cell_length_b                    17.9624(9) 
_cell_length_c                    9.3062(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  98.981(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      1097.24(9) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'colorless' 
_exptl_crystal_size_max           0.24 
_exptl_crystal_size_mid           0.19 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.203 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              428 
_exptl_absorpt_coefficient_mu     0.081 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.9808 
_exptl_absorpt_correction_T_max   0.9903 
_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   'Bruker CCD area detector'  
_diffrn_measurement_method        'omega scan'  
_diffrn_detector_area_resol_mean  3 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             11570 
_diffrn_reflns_av_R_equivalents   0.0397 
_diffrn_reflns_av_sigmaI/netI     0.0646 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -22 
_diffrn_reflns_limit_k_max        22 
_diffrn_reflns_limit_l_min        -11 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          2.49 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              4209 
_reflns_number_gt                 2685 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker Apex II (Bruker, 2006)'   
_computing_cell_refinement        
'Bruker Apex II and SAINT (Bruker, 2006)'  
_computing_data_reduction         SAINT 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     
'Mercury 2.3 (Macrae et al., 2008)' 
_computing_publication_material   'Bruker Apex II'   
 
_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)+(0.0586P)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_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    2.3(13) 
_refine_ls_number_reflns          4209 
_refine_ls_number_parameters      266 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0845 
_refine_ls_R_factor_gt            0.0462 
_refine_ls_wR_factor_ref          0.1153 
_refine_ls_wR_factor_gt           0.1039 
_refine_ls_goodness_of_fit_ref    0.923 
_refine_ls_restrained_S_all       0.922 
_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 
N15 N 0.5270(3) 0.42912(12) 0.4009(2) 0.0364(5) Uani 1 1 d . . . 
H15A H 0.3962 0.4253 0.3584 0.044 Uiso 1 1 calc R . . 
H15B H 0.6043 0.4309 0.3297 0.044 Uiso 1 1 calc R . . 
C3 C -0.0122(3) 0.44040(15) 1.2224(2) 0.0341(6) Uani 1 1 d . . . 
O1 O 0.1099(2) 0.41868(12) 1.33328(16) 0.0468(5) Uani 1 1 d . . . 
C12 C 0.1079(3) 0.40733(14) 0.9784(2) 0.0365(6) Uani 1 1 d . . . 
C16 C 0.5533(4) 0.50080(16) 0.4849(3) 0.0453(7) Uani 1 1 d . . . 
H16A H 0.4713 0.4990 0.5625 0.054 Uiso 1 1 calc R . . 
H16B H 0.6947 0.5057 0.5294 0.054 Uiso 1 1 calc R . . 
C23 C 0.5826(4) 0.36111(16) 0.4905(3) 0.0474(7) Uani 1 1 d . . . 
H23A H 0.7271 0.3620 0.5285 0.057 Uiso 1 1 calc R . . 
H23B H 0.5083 0.3605 0.5723 0.057 Uiso 1 1 calc R . . 
C24 C 0.5334(4) 0.29280(15) 0.4011(3) 0.0453(7) Uani 1 1 d . . . 
C17 C 0.4936(4) 0.56772(16) 0.3928(3) 0.0471(8) Uani 1 1 d . . . 
C18 C 0.3095(5) 0.60201(19) 0.3920(4) 0.0665(9) Uani 1 1 d . . . 
H18 H 0.2183 0.5833 0.4492 0.080 Uiso 1 1 calc R . . 
C4 C 0.0802(3) 0.46706(15) 1.0915(3) 0.0348(6) Uani 1 1 d . . . 
H4 H 0.2160 0.4866 1.1290 0.042 Uiso 1 1 calc R . . 
C29 C 0.3513(5) 0.25648(18) 0.4041(4) 0.0577(8) Uani 1 1 d . . . 
H29 H 0.2638 0.2733 0.4660 0.069 Uiso 1 1 calc R . . 
C7 C 0.1419(3) 0.45637(15) 0.8471(2) 0.0382(6) Uani 1 1 d . . . 
C22 C 0.6254(6) 0.59828(19) 0.3073(4) 0.0736(10) Uani 1 1 d . . . 
H22 H 0.7521 0.5763 0.3068 0.088 Uiso 1 1 calc R . . 
C25 C 0.6637(5) 0.26636(18) 0.3102(4) 0.0628(9) Uani 1 1 d . . . 
H25 H 0.7883 0.2896 0.3083 0.075 Uiso 1 1 calc R . . 
C26 C 0.6078(7) 0.2048(2) 0.2215(4) 0.0800(11) Uani 1 1 d . . . 
H26 H 0.6947 0.1869 0.1603 0.096 Uiso 1 1 calc R . . 
C14 C -0.0854(5) 0.36019(19) 0.9398(4) 0.0716(10) Uani 1 1 d . . . 
H14A H -0.0665 0.3250 0.8654 0.107 Uiso 1 1 calc R . . 
H14B H -0.1986 0.3920 0.9050 0.107 Uiso 1 1 calc R . . 
H14C H -0.1122 0.3340 1.0247 0.107 Uiso 1 1 calc R . . 
C19 C 0.2576(6) 0.6648(2) 0.3061(6) 0.0898(13) Uani 1 1 d . . . 
H19 H 0.1320 0.6878 0.3052 0.108 Uiso 1 1 calc R . . 
C21 C 0.5742(8) 0.6593(2) 0.2245(5) 0.1049(16) Uani 1 1 d . . . 
H21 H 0.6658 0.6784 0.1681 0.126 Uiso 1 1 calc R . . 
C5 C -0.0391(5) 0.53029(17) 1.0066(3) 0.0572(8) Uani 1 1 d . . . 
H5A H -0.1813 0.5287 1.0190 0.069 Uiso 1 1 calc R . . 
H5B H 0.0170 0.5782 1.0398 0.069 Uiso 1 1 calc R . . 
C28 C 0.2969(6) 0.1950(2) 0.3156(4) 0.0753(10) Uani 1 1 d . . . 
H28 H 0.1741 0.1707 0.3187 0.090 Uiso 1 1 calc R . . 
C6 C -0.0178(5) 0.51776(18) 0.8473(3) 0.0625(9) Uani 1 1 d . . . 
H6A H 0.0264 0.5631 0.8050 0.075 Uiso 1 1 calc R . . 
H6B H -0.1469 0.5024 0.7918 0.075 Uiso 1 1 calc R . . 
C27 C 0.4227(7) 0.1707(2) 0.2252(4) 0.0807(12) Uani 1 1 d . . . 
H27 H 0.3841 0.1304 0.1644 0.097 Uiso 1 1 calc R . . 
C20 C 0.3939(10) 0.6924(3) 0.2226(5) 0.1029(15) Uani 1 1 d . . . 
H20 H 0.3606 0.7342 0.1648 0.124 Uiso 1 1 calc R . . 
C13 C 0.2872(5) 0.35616(19) 1.0340(3) 0.0784(11) Uani 1 1 d . . . 
H13A H 0.2563 0.3279 1.1154 0.118 Uiso 1 1 calc R . . 
H13B H 0.4070 0.3856 1.0637 0.118 Uiso 1 1 calc R . . 
H13C H 0.3108 0.3228 0.9577 0.118 Uiso 1 1 calc R . . 
O2 O -0.1997(2) 0.44071(12) 1.21409(18) 0.0530(5) Uani 1 1 d . . . 
O9 O 0.0571(3) 0.45801(13) 0.59029(19) 0.0577(6) Uani 1 1 d . . . 
H9 H 0.0702 0.4361 0.5150 0.087 Uiso 1 1 calc R . . 
O10 O 0.1686(5) 0.35225(15) 0.6862(2) 0.1022(10) Uani 1 1 d . . . 
C8 C 0.1229(4) 0.41558(18) 0.7021(3) 0.0432(7) Uani 1 1 d . . . 
C11 C 0.3538(5) 0.4926(2) 0.8671(4) 0.0794(12) Uani 1 1 d . . . 
H11A H 0.4562 0.4545 0.8735 0.119 Uiso 1 1 calc R . . 
H11B H 0.3734 0.5216 0.9548 0.119 Uiso 1 1 calc R . . 
H11C H 0.3642 0.5243 0.7855 0.119 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 
N15 C23 1.493(3) . ? 
N15 C16 1.502(3) . ? 
N15 H15A 0.9000 . ? 
N15 H15B 0.9000 . ? 
C3 O2 1.237(2) . ? 
C3 O1 1.270(3) . ? 
C3 C4 1.524(3) . ? 
C12 C13 1.530(4) . ? 
C12 C14 1.533(4) . ? 
C12 C4 1.534(3) . ? 
C12 C7 1.551(3) . ? 
C16 C17 1.494(4) . ? 
C16 H16A 0.9700 . ? 
C16 H16B 0.9700 . ? 
C23 C24 1.490(4) . ? 
C23 H23A 0.9700 . ? 
C23 H23B 0.9700 . ? 
C24 C29 1.379(4) . ? 
C24 C25 1.385(4) . ? 
C17 C18 1.369(4) . ? 
C17 C22 1.385(4) . ? 
C18 C19 1.394(5) . ? 
C18 H18 0.9300 . ? 
C4 C5 1.532(4) . ? 
C4 H4 0.9800 . ? 
C29 C28 1.392(5) . ? 
C29 H29 0.9300 . ? 
C7 C8 1.523(4) . ? 
C7 C6 1.531(4) . ? 
C7 C11 1.536(4) . ? 
C22 C21 1.352(5) . ? 
C22 H22 0.9300 . ? 
C25 C26 1.395(5) . ? 
C25 H25 0.9300 . ? 
C26 C27 1.379(5) . ? 
C26 H26 0.9300 . ? 
C14 H14A 0.9600 . ? 
C14 H14B 0.9600 . ? 
C14 H14C 0.9600 . ? 
C19 C20 1.374(6) . ? 
C19 H19 0.9300 . ? 
C21 C20 1.335(6) . ? 
C21 H21 0.9300 . ? 
C5 C6 1.527(4) . ? 
C5 H5A 0.9700 . ? 
C5 H5B 0.9700 . ? 
C28 C27 1.347(5) . ? 
C28 H28 0.9300 . ? 
C6 H6A 0.9700 . ? 
C6 H6B 0.9700 . ? 
C27 H27 0.9300 . ? 
C20 H20 0.9300 . ? 
C13 H13A 0.9600 . ? 
C13 H13B 0.9600 . ? 
C13 H13C 0.9600 . ? 
O9 C8 1.309(3) . ? 
O9 H9 0.8200 . ? 
O10 C8 1.193(3) . ? 
C11 H11A 0.9600 . ? 
C11 H11B 0.9600 . ? 
C11 H11C 0.9600 . ? 
 
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 
C23 N15 C16 114.33(17) . . ? 
C23 N15 H15A 108.7 . . ? 
C16 N15 H15A 108.7 . . ? 
C23 N15 H15B 108.7 . . ? 
C16 N15 H15B 108.7 . . ? 
H15A N15 H15B 107.6 . . ? 
O2 C3 O1 124.2(2) . . ? 
O2 C3 C4 118.4(2) . . ? 
O1 C3 C4 117.38(19) . . ? 
C13 C12 C14 109.1(3) . . ? 
C13 C12 C4 111.0(2) . . ? 
C14 C12 C4 111.2(2) . . ? 
C13 C12 C7 114.0(2) . . ? 
C14 C12 C7 110.4(2) . . ? 
C4 C12 C7 101.02(18) . . ? 
C17 C16 N15 113.1(2) . . ? 
C17 C16 H16A 109.0 . . ? 
N15 C16 H16A 109.0 . . ? 
C17 C16 H16B 109.0 . . ? 
N15 C16 H16B 109.0 . . ? 
H16A C16 H16B 107.8 . . ? 
C24 C23 N15 110.4(2) . . ? 
C24 C23 H23A 109.6 . . ? 
N15 C23 H23A 109.6 . . ? 
C24 C23 H23B 109.6 . . ? 
N15 C23 H23B 109.6 . . ? 
H23A C23 H23B 108.1 . . ? 
C29 C24 C25 119.0(3) . . ? 
C29 C24 C23 119.7(3) . . ? 
C25 C24 C23 121.3(3) . . ? 
C18 C17 C22 117.6(3) . . ? 
C18 C17 C16 121.5(3) . . ? 
C22 C17 C16 120.9(3) . . ? 
C17 C18 C19 120.5(4) . . ? 
C17 C18 H18 119.7 . . ? 
C19 C18 H18 119.7 . . ? 
C3 C4 C5 113.9(2) . . ? 
C3 C4 C12 115.8(2) . . ? 
C5 C4 C12 105.78(19) . . ? 
C3 C4 H4 107.0 . . ? 
C5 C4 H4 107.0 . . ? 
C12 C4 H4 107.0 . . ? 
C24 C29 C28 120.7(3) . . ? 
C24 C29 H29 119.6 . . ? 
C28 C29 H29 119.6 . . ? 
C8 C7 C6 112.7(2) . . ? 
C8 C7 C11 105.00(19) . . ? 
C6 C7 C11 108.5(3) . . ? 
C8 C7 C12 115.0(2) . . ? 
C6 C7 C12 102.81(18) . . ? 
C11 C7 C12 112.9(2) . . ? 
C21 C22 C17 121.5(4) . . ? 
C21 C22 H22 119.2 . . ? 
C17 C22 H22 119.2 . . ? 
C24 C25 C26 119.9(3) . . ? 
C24 C25 H25 120.0 . . ? 
C26 C25 H25 120.0 . . ? 
C27 C26 C25 119.5(3) . . ? 
C27 C26 H26 120.2 . . ? 
C25 C26 H26 120.2 . . ? 
C12 C14 H14A 109.5 . . ? 
C12 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C12 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C20 C19 C18 119.3(4) . . ? 
C20 C19 H19 120.3 . . ? 
C18 C19 H19 120.3 . . ? 
C20 C21 C22 121.0(4) . . ? 
C20 C21 H21 119.5 . . ? 
C22 C21 H21 119.5 . . ? 
C6 C5 C4 105.8(2) . . ? 
C6 C5 H5A 110.6 . . ? 
C4 C5 H5A 110.6 . . ? 
C6 C5 H5B 110.6 . . ? 
C4 C5 H5B 110.6 . . ? 
H5A C5 H5B 108.7 . . ? 
C27 C28 C29 119.8(4) . . ? 
C27 C28 H28 120.1 . . ? 
C29 C28 H28 120.1 . . ? 
C5 C6 C7 106.1(2) . . ? 
C5 C6 H6A 110.5 . . ? 
C7 C6 H6A 110.5 . . ? 
C5 C6 H6B 110.5 . . ? 
C7 C6 H6B 110.5 . . ? 
H6A C6 H6B 108.7 . . ? 
C28 C27 C26 121.0(4) . . ? 
C28 C27 H27 119.5 . . ? 
C26 C27 H27 119.5 . . ? 
C21 C20 C19 120.1(4) . . ? 
C21 C20 H20 120.0 . . ? 
C19 C20 H20 120.0 . . ? 
C12 C13 H13A 109.5 . . ? 
C12 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C12 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C8 O9 H9 109.5 . . ? 
O10 C8 O9 121.1(3) . . ? 
O10 C8 C7 125.6(3) . . ? 
O9 C8 C7 113.3(2) . . ? 
C7 C11 H11A 109.5 . . ? 
C7 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C7 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
 
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 
N15 H15A O1  0.90 1.88 2.752(2) 161.3 1_554 
N15 H15B O2  0.90 1.82 2.711(2) 168.6 1_654 
O9 H9 O1  0.82 1.78 2.570(2) 161.4 1_554 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.156 
_refine_diff_density_min   -0.149 
_refine_diff_density_rms    0.033 
