data_152c1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 N O4' _chemical_formula_weight 301.33 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2401(1) _cell_length_b 35.6299(4) _cell_length_c 9.4474(1) _cell_angle_alpha 90.00 _cell_angle_beta 100.319(1) _cell_angle_gamma 90.00 _cell_volume 3060.00(6) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description lathes _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.093 _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 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13504 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_k_max 46 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6926 _reflns_number_gt 5353 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0425P)^2^+1.3140P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0108(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6926 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.003 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 N1 N 0.25128(14) 0.20615(3) 0.44418(14) 0.0306(3) Uani 1 1 d . . . C2 C 0.33566(16) 0.19093(4) 0.56480(16) 0.0300(3) Uani 1 1 d . . . C3 C 0.32743(15) 0.14816(4) 0.54954(14) 0.0240(3) Uani 1 1 d . . . H3 H 0.4250 0.1382 0.5558 0.029 Uiso 1 1 d R . . C4 C 0.25273(15) 0.12945(4) 0.66778(15) 0.0269(3) Uani 1 1 d . . . C5 C 0.17656(17) 0.09279(4) 0.60738(17) 0.0319(3) Uani 1 1 d . . . H5A H 0.0856 0.0992 0.5460 0.038 Uiso 1 1 d R . . H5B H 0.1530 0.0786 0.6866 0.038 Uiso 1 1 d R . . C6 C 0.26371(17) 0.06802(4) 0.52570(18) 0.0350(4) Uani 1 1 d . . . C7 C 0.27579(16) 0.07492(4) 0.38570(17) 0.0326(3) Uani 1 1 d . . . C8 C 0.21820(15) 0.11079(4) 0.31815(16) 0.0284(3) Uani 1 1 d . . . C9 C 0.13959(17) 0.11476(5) 0.17649(17) 0.0372(4) Uani 1 1 d . . . H9 H 0.1171 0.0929 0.1173 0.045 Uiso 1 1 d R . . C10 C 0.09479(17) 0.14968(6) 0.12288(16) 0.0415(4) Uani 1 1 d . . . H10 H 0.0424 0.1515 0.0257 0.050 Uiso 1 1 d R . . C11 C 0.12413(17) 0.18243(5) 0.20328(17) 0.0362(4) Uani 1 1 d . . . H11 H 0.0937 0.2067 0.1646 0.043 Uiso 1 1 d R . . C12 C 0.19990(15) 0.17833(4) 0.34242(15) 0.0272(3) Uani 1 1 d . . . C13 C 0.24406(14) 0.14329(4) 0.39893(15) 0.0239(3) Uani 1 1 d . . . C14 C 0.2323(2) 0.24626(4) 0.4188(2) 0.0467(4) Uani 1 1 d . . . H14A H 0.2776 0.2596 0.5036 0.070 Uiso 1 1 d R . . H14B H 0.2779 0.2535 0.3393 0.070 Uiso 1 1 d R . . H14C H 0.1294 0.2522 0.3974 0.070 Uiso 1 1 d R . . O15 O 0.40190(13) 0.20885(3) 0.66631(13) 0.0425(3) Uani 1 1 d . . . C16 C 0.13335(17) 0.15488(5) 0.70865(17) 0.0355(4) Uani 1 1 d . . . H16A H 0.0892 0.1425 0.7806 0.053 Uiso 1 1 d R . . H16B H 0.1770 0.1780 0.7466 0.053 Uiso 1 1 d R . . H16C H 0.0594 0.1600 0.6257 0.053 Uiso 1 1 d R . . C17 C 0.36934(18) 0.12139(6) 0.80040(17) 0.0439(4) Uani 1 1 d . . . H17A H 0.3243 0.1098 0.8734 0.066 Uiso 1 1 d R . . H17B H 0.4423 0.1048 0.7746 0.066 Uiso 1 1 d R . . H17C H 0.4151 0.1445 0.8364 0.066 Uiso 1 1 d R . . O18 O 0.32313(15) 0.03834(3) 0.60153(16) 0.0506(3) Uani 1 1 d . . . C19 C 0.35098(18) 0.04716(5) 0.3115(2) 0.0397(4) Uani 1 1 d . . . O20 O 0.40548(14) 0.01807(3) 0.36655(16) 0.0530(4) Uani 1 1 d . . . O21 O 0.35455(14) 0.05597(3) 0.17400(14) 0.0473(3) Uani 1 1 d . . . C22 C 0.4187(2) 0.02810(6) 0.0923(3) 0.0617(6) Uani 1 1 d . . . H22A H 0.4165 0.0366 -0.0045 0.093 Uiso 1 1 d R . . H22B H 0.5188 0.0239 0.1382 0.093 Uiso 1 1 d R . . H22C H 0.3644 0.0051 0.0909 0.093 Uiso 1 1 d R . . N1' N 0.78539(13) 0.18225(3) 0.58830(12) 0.0265(3) Uani 1 1 d . . . C2' C 0.81778(15) 0.19522(4) 0.45996(15) 0.0266(3) Uani 1 1 d . . . C3' C 0.78918(15) 0.16306(4) 0.35071(14) 0.0224(3) Uani 1 1 d . . . H3' H 0.8771 0.1583 0.3127 0.027 Uiso 1 1 d R . . C4' C 0.65881(15) 0.17168(4) 0.22312(15) 0.0258(3) Uani 1 1 d . . . C5' C 0.57760(16) 0.13462(4) 0.17542(15) 0.0291(3) Uani 1 1 d . . . H5'A H 0.5086 0.1392 0.0884 0.035 Uiso 1 1 d R . . H5'B H 0.5226 0.1273 0.2481 0.035 Uiso 1 1 d R . . C6' C 0.67409(16) 0.10245(4) 0.15037(15) 0.0289(3) Uani 1 1 d . . . C7' C 0.75014(15) 0.08129(4) 0.25947(15) 0.0259(3) Uani 1 1 d . . . C8' C 0.74631(14) 0.09282(4) 0.40961(14) 0.0232(3) Uani 1 1 d . . . C9' C 0.72260(16) 0.06808(4) 0.51937(15) 0.0279(3) Uani 1 1 d . . . H9' H 0.7108 0.0417 0.4990 0.034 Uiso 1 1 d R . . C10' C 0.71637(16) 0.08153(4) 0.65576(15) 0.0306(3) Uani 1 1 d . . . H10' H 0.6996 0.0642 0.7289 0.037 Uiso 1 1 d R . . C11' C 0.73413(16) 0.11947(4) 0.69082(15) 0.0285(3) Uani 1 1 d . . . H11' H 0.7304 0.1286 0.7858 0.034 Uiso 1 1 d R . . C12' C 0.75703(14) 0.14348(4) 0.58181(14) 0.0233(3) Uani 1 1 d . . . C13' C 0.76119(14) 0.13055(4) 0.44342(14) 0.0217(3) Uani 1 1 d . . . C14' C 0.79688(19) 0.20472(4) 0.71825(17) 0.0364(4) Uani 1 1 d . . . H14D H 0.8161 0.2304 0.6964 0.055 Uiso 1 1 d R . . H14E H 0.7066 0.2033 0.7550 0.055 Uiso 1 1 d R . . H14F H 0.8762 0.1953 0.7892 0.055 Uiso 1 1 d R . . O15' O 0.86038(13) 0.22679(3) 0.44011(12) 0.0362(3) Uani 1 1 d . . . C16' C 0.54663(16) 0.19825(5) 0.27100(17) 0.0347(4) Uani 1 1 d . . . H16D H 0.4689 0.2029 0.1909 0.052 Uiso 1 1 d R . . H16E H 0.5067 0.1868 0.3476 0.052 Uiso 1 1 d R . . H16F H 0.5933 0.2215 0.3038 0.052 Uiso 1 1 d R . . C17' C 0.71837(18) 0.18902(5) 0.09691(16) 0.0345(4) Uani 1 1 d . . . H17D H 0.6384 0.1943 0.0195 0.052 Uiso 1 1 d R . . H17E H 0.7695 0.2119 0.1274 0.052 Uiso 1 1 d R . . H17F H 0.7850 0.1717 0.0646 0.052 Uiso 1 1 d R . . O18' O 0.67670(14) 0.09568(3) 0.01108(11) 0.0397(3) Uani 1 1 d . . . C19' C 0.83769(16) 0.05018(4) 0.22183(16) 0.0300(3) Uani 1 1 d . . . O20' O 0.84151(14) 0.04073(3) 0.09697(12) 0.0420(3) Uani 1 1 d . . . O21' O 0.91603(12) 0.03210(3) 0.33354(12) 0.0354(3) Uani 1 1 d . . . C22' C 1.0013(2) 0.00054(5) 0.2972(2) 0.0462(4) Uani 1 1 d . . . H22D H 1.0530 -0.0108 0.3839 0.069 Uiso 1 1 d R . . H22E H 0.9369 -0.0176 0.2436 0.069 Uiso 1 1 d R . . H22F H 1.0707 0.0092 0.2401 0.069 Uiso 1 1 d R . . H18' H 0.742(2) 0.0745(7) 0.012(2) 0.070(7) Uiso 1 1 d . . . H18 H 0.376(3) 0.0248(8) 0.541(3) 0.107(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0343(7) 0.0221(6) 0.0384(7) 0.0002(5) 0.0149(6) 0.0006(5) C2 0.0296(8) 0.0286(8) 0.0347(8) -0.0061(6) 0.0137(6) -0.0051(6) C3 0.0203(6) 0.0261(7) 0.0254(7) -0.0021(6) 0.0039(5) -0.0008(5) C4 0.0243(7) 0.0317(8) 0.0243(7) 0.0026(6) 0.0038(5) 0.0002(6) C5 0.0310(8) 0.0304(8) 0.0360(8) 0.0042(6) 0.0103(6) -0.0025(6) C6 0.0337(8) 0.0226(7) 0.0492(10) 0.0012(7) 0.0087(7) -0.0028(6) C7 0.0287(8) 0.0254(8) 0.0446(9) -0.0088(7) 0.0089(7) -0.0026(6) C8 0.0234(7) 0.0325(8) 0.0306(8) -0.0071(6) 0.0085(6) -0.0022(6) C9 0.0288(8) 0.0534(10) 0.0299(8) -0.0142(7) 0.0068(6) -0.0018(7) C10 0.0307(8) 0.0723(13) 0.0217(8) -0.0002(8) 0.0051(6) 0.0074(8) C11 0.0313(8) 0.0483(10) 0.0318(8) 0.0122(7) 0.0129(7) 0.0097(7) C12 0.0244(7) 0.0307(8) 0.0290(7) 0.0026(6) 0.0116(6) 0.0026(6) C13 0.0206(6) 0.0273(7) 0.0248(7) -0.0005(6) 0.0069(5) 0.0000(5) C14 0.0586(11) 0.0235(8) 0.0646(12) 0.0061(8) 0.0285(9) 0.0042(8) O15 0.0445(7) 0.0400(7) 0.0446(7) -0.0185(5) 0.0119(5) -0.0135(5) C16 0.0334(8) 0.0396(9) 0.0361(8) -0.0040(7) 0.0131(7) -0.0020(7) C17 0.0347(9) 0.0649(12) 0.0298(8) 0.0114(8) -0.0003(7) -0.0022(8) O18 0.0586(8) 0.0272(6) 0.0691(9) 0.0119(6) 0.0201(7) 0.0071(6) C19 0.0328(8) 0.0276(8) 0.0608(12) -0.0149(8) 0.0142(8) -0.0076(7) O20 0.0498(7) 0.0263(6) 0.0850(10) -0.0116(6) 0.0178(7) 0.0038(5) O21 0.0491(7) 0.0366(7) 0.0623(8) -0.0222(6) 0.0260(6) -0.0028(5) C22 0.0612(13) 0.0473(11) 0.0855(15) -0.0387(11) 0.0373(11) -0.0065(9) N1' 0.0325(6) 0.0231(6) 0.0244(6) -0.0007(5) 0.0062(5) 0.0023(5) C2' 0.0271(7) 0.0235(7) 0.0289(7) 0.0032(6) 0.0045(6) 0.0021(6) C3' 0.0235(7) 0.0225(7) 0.0218(7) 0.0027(5) 0.0055(5) 0.0011(5) C4' 0.0255(7) 0.0276(7) 0.0241(7) 0.0072(6) 0.0040(5) 0.0033(6) C5' 0.0267(7) 0.0341(8) 0.0243(7) 0.0049(6) -0.0014(6) 0.0011(6) C6' 0.0328(8) 0.0306(8) 0.0221(7) -0.0009(6) 0.0013(6) -0.0053(6) C7' 0.0277(7) 0.0245(7) 0.0242(7) -0.0007(6) 0.0012(5) -0.0029(6) C8' 0.0213(6) 0.0248(7) 0.0223(7) 0.0017(5) 0.0006(5) -0.0005(5) C9' 0.0306(7) 0.0228(7) 0.0294(7) 0.0046(6) 0.0025(6) -0.0021(6) C10' 0.0345(8) 0.0319(8) 0.0257(7) 0.0104(6) 0.0058(6) -0.0018(6) C11' 0.0298(7) 0.0334(8) 0.0227(7) 0.0038(6) 0.0058(6) 0.0012(6) C12' 0.0224(7) 0.0243(7) 0.0231(7) 0.0010(5) 0.0035(5) 0.0013(5) C13' 0.0189(6) 0.0248(7) 0.0211(6) 0.0045(5) 0.0026(5) 0.0007(5) C14' 0.0491(10) 0.0293(8) 0.0306(8) -0.0063(6) 0.0070(7) 0.0039(7) O15' 0.0471(7) 0.0231(5) 0.0387(6) 0.0025(5) 0.0084(5) -0.0044(5) C16' 0.0283(8) 0.0370(9) 0.0388(9) 0.0053(7) 0.0062(7) 0.0076(6) C17' 0.0375(8) 0.0383(9) 0.0279(8) 0.0117(7) 0.0061(6) 0.0025(7) O18' 0.0544(7) 0.0428(7) 0.0200(5) -0.0017(5) 0.0015(5) 0.0034(6) C19' 0.0330(8) 0.0245(7) 0.0316(8) -0.0020(6) 0.0036(6) -0.0036(6) O20' 0.0561(7) 0.0370(6) 0.0332(6) -0.0095(5) 0.0084(5) 0.0032(5) O21' 0.0376(6) 0.0283(6) 0.0389(6) -0.0002(5) 0.0033(5) 0.0076(5) C22' 0.0453(10) 0.0320(9) 0.0614(12) -0.0033(8) 0.0096(9) 0.0116(8) _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 N1 C2 1.372(2) . ? N1 C12 1.4033(19) . ? N1 C14 1.454(2) . ? C2 O15 1.2215(18) . ? C2 C3 1.531(2) . ? C3 C13 1.5018(19) . ? C3 C4 1.5636(19) . ? C3 H3 0.9601 . ? C4 C17 1.526(2) . ? C4 C16 1.529(2) . ? C4 C5 1.544(2) . ? C5 C6 1.498(2) . ? C5 H5A 0.9599 . ? C5 H5B 0.9602 . ? C6 O18 1.3389(19) . ? C6 C7 1.369(2) . ? C7 C19 1.458(2) . ? C7 C8 1.484(2) . ? C8 C13 1.384(2) . ? C8 C9 1.411(2) . ? C9 C10 1.379(3) . ? C9 H9 0.9601 . ? C10 C11 1.392(3) . ? C10 H10 0.9600 . ? C11 C12 1.382(2) . ? C11 H11 0.9602 . ? C12 C13 1.390(2) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9601 . ? C16 H16A 0.9600 . ? C16 H16B 0.9599 . ? C16 H16C 0.9601 . ? C17 H17A 0.9600 . ? C17 H17B 0.9598 . ? C17 H17C 0.9599 . ? O18 H18 0.94(3) . ? C19 O20 1.227(2) . ? C19 O21 1.343(2) . ? O21 C22 1.4483(19) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9601 . ? N1' C2' 1.3796(18) . ? N1' C12' 1.4052(18) . ? N1' C14' 1.4537(18) . ? C2' O15' 1.2173(17) . ? C2' C3' 1.5330(19) . ? C3' C13' 1.5023(18) . ? C3' C4' 1.5742(18) . ? C3' H3' 0.9600 . ? C4' C16' 1.531(2) . ? C4' C17' 1.530(2) . ? C4' C5' 1.546(2) . ? C5' C6' 1.497(2) . ? C5' H5'A 0.9600 . ? C5' H5'B 0.9600 . ? C6' O18' 1.3423(18) . ? C6' C7' 1.366(2) . ? C7' C19' 1.454(2) . ? C7' C8' 1.4832(19) . ? C8' C13' 1.3830(19) . ? C8' C9' 1.4076(19) . ? C9' C10' 1.386(2) . ? C9' H9' 0.9603 . ? C10' C11' 1.395(2) . ? C10' H10' 0.9601 . ? C11' C12' 1.3839(19) . ? C11' H11' 0.9601 . ? C12' C13' 1.3932(19) . ? C14' H14D 0.9599 . ? C14' H14E 0.9600 . ? C14' H14F 0.9601 . ? C16' H16D 0.9600 . ? C16' H16E 0.9599 . ? C16' H16F 0.9600 . ? C17' H17D 0.9600 . ? C17' H17E 0.9602 . ? C17' H17F 0.9599 . ? O18' H18' 0.97(2) . ? C19' O20' 1.2333(18) . ? C19' O21' 1.3338(18) . ? O21' C22' 1.4489(19) . ? C22' H22D 0.9602 . ? C22' H22E 0.9600 . ? C22' H22F 0.9599 . ? 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 C2 N1 C12 111.21(12) . . ? C2 N1 C14 124.00(14) . . ? C12 N1 C14 124.43(14) . . ? O15 C2 N1 125.14(15) . . ? O15 C2 C3 127.14(15) . . ? N1 C2 C3 107.70(12) . . ? C13 C3 C2 102.28(11) . . ? C13 C3 C4 114.23(11) . . ? C2 C3 C4 112.20(11) . . ? C13 C3 H3 109.4 . . ? C2 C3 H3 109.3 . . ? C4 C3 H3 109.2 . . ? C17 C4 C16 109.83(13) . . ? C17 C4 C5 110.62(13) . . ? C16 C4 C5 107.02(12) . . ? C17 C4 C3 109.25(12) . . ? C16 C4 C3 111.01(12) . . ? C5 C4 C3 109.09(11) . . ? C6 C5 C4 115.92(12) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.2 . . ? C6 C5 H5B 108.0 . . ? C4 C5 H5B 108.0 . . ? H5A C5 H5B 107.5 . . ? O18 C6 C7 124.20(15) . . ? O18 C6 C5 113.35(14) . . ? C7 C6 C5 122.41(14) . . ? C6 C7 C19 118.07(15) . . ? C6 C7 C8 119.01(13) . . ? C19 C7 C8 122.86(15) . . ? C13 C8 C9 116.61(14) . . ? C13 C8 C7 118.05(13) . . ? C9 C8 C7 125.34(14) . . ? C10 C9 C8 120.58(15) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 122.66(14) . . ? C9 C10 H10 118.6 . . ? C11 C10 H10 118.7 . . ? C12 C11 C10 116.50(15) . . ? C12 C11 H11 121.4 . . ? C10 C11 H11 122.1 . . ? C11 C12 C13 121.62(14) . . ? C11 C12 N1 128.93(14) . . ? C13 C12 N1 109.36(12) . . ? C8 C13 C12 122.00(13) . . ? C8 C13 C3 128.88(13) . . ? C12 C13 C3 109.00(12) . . ? N1 C14 H14A 109.1 . . ? N1 C14 H14B 109.6 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.7 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C4 C16 H16A 108.9 . . ? C4 C16 H16B 109.3 . . ? H16A C16 H16B 109.5 . . ? C4 C16 H16C 110.2 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C4 C17 H17A 109.7 . . ? C4 C17 H17B 109.4 . . ? H17A C17 H17B 109.5 . . ? C4 C17 H17C 109.3 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C6 O18 H18 106.6(18) . . ? O20 C19 O21 121.89(15) . . ? O20 C19 C7 124.36(17) . . ? O21 C19 C7 113.75(15) . . ? C19 O21 C22 116.02(16) . . ? O21 C22 H22A 110.6 . . ? O21 C22 H22B 108.5 . . ? H22A C22 H22B 109.5 . . ? O21 C22 H22C 109.3 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2' N1' C12' 111.05(11) . . ? C2' N1' C14' 124.27(12) . . ? C12' N1' C14' 124.28(12) . . ? O15' C2' N1' 124.89(13) . . ? O15' C2' C3' 127.48(13) . . ? N1' C2' C3' 107.63(11) . . ? C13' C3' C2' 102.17(11) . . ? C13' C3' C4' 114.13(11) . . ? C2' C3' C4' 112.69(11) . . ? C13' C3' H3' 109.1 . . ? C2' C3' H3' 109.2 . . ? C4' C3' H3' 109.3 . . ? C16' C4' C17' 109.75(12) . . ? C16' C4' C5' 107.18(12) . . ? C17' C4' C5' 109.96(12) . . ? C16' C4' C3' 111.11(12) . . ? C17' C4' C3' 110.04(11) . . ? C5' C4' C3' 108.75(11) . . ? C6' C5' C4' 115.38(12) . . ? C6' C5' H5'A 108.6 . . ? C4' C5' H5'A 108.5 . . ? C6' C5' H5'B 108.2 . . ? C4' C5' H5'B 108.3 . . ? H5'A C5' H5'B 107.6 . . ? O18' C6' C7' 122.93(14) . . ? O18' C6' C5' 114.10(12) . . ? C7' C6' C5' 122.95(13) . . ? C6' C7' C19' 118.04(13) . . ? C6' C7' C8' 118.15(13) . . ? C19' C7' C8' 123.70(12) . . ? C13' C8' C9' 117.44(13) . . ? C13' C8' C7' 118.14(12) . . ? C9' C8' C7' 124.38(13) . . ? C10' C9' C8' 120.42(14) . . ? C10' C9' H9' 120.1 . . ? C8' C9' H9' 119.4 . . ? C9' C10' C11' 122.23(13) . . ? C9' C10' H10' 119.0 . . ? C11' C10' H10' 118.7 . . ? C12' C11' C10' 116.72(13) . . ? C12' C11' H11' 121.5 . . ? C10' C11' H11' 121.7 . . ? C11' C12' C13' 121.84(13) . . ? C11' C12' N1' 128.85(13) . . ? C13' C12' N1' 109.25(12) . . ? C8' C13' C12' 121.32(12) . . ? C8' C13' C3' 129.45(12) . . ? C12' C13' C3' 109.19(12) . . ? N1' C14' H14D 109.3 . . ? N1' C14' H14E 109.9 . . ? H14D C14' H14E 109.5 . . ? N1' C14' H14F 109.2 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? C4' C16' H16D 109.0 . . ? C4' C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? C4' C16' H16F 109.9 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? C4' C17' H17D 109.7 . . ? C4' C17' H17E 109.6 . . ? H17D C17' H17E 109.5 . . ? C4' C17' H17F 109.1 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? C6' O18' H18' 104.5(13) . . ? O20' C19' O21' 121.37(14) . . ? O20' C19' C7' 123.69(14) . . ? O21' C19' C7' 114.94(13) . . ? C19' O21' C22' 115.35(13) . . ? O21' C22' H22D 109.5 . . ? O21' C22' H22E 109.7 . . ? H22D C22' H22E 109.4 . . ? O21' C22' H22F 109.3 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 109.5 . . ? 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 C12 N1 C2 O15 175.10(14) . . . . ? C14 N1 C2 O15 1.8(2) . . . . ? C12 N1 C2 C3 -6.36(15) . . . . ? C14 N1 C2 C3 -179.68(13) . . . . ? O15 C2 C3 C13 -174.83(14) . . . . ? N1 C2 C3 C13 6.67(14) . . . . ? O15 C2 C3 C4 62.32(19) . . . . ? N1 C2 C3 C4 -116.18(12) . . . . ? C13 C3 C4 C17 156.17(13) . . . . ? C2 C3 C4 C17 -88.01(15) . . . . ? C13 C3 C4 C16 -82.56(15) . . . . ? C2 C3 C4 C16 33.26(16) . . . . ? C13 C3 C4 C5 35.14(16) . . . . ? C2 C3 C4 C5 150.95(12) . . . . ? C17 C4 C5 C6 -75.73(17) . . . . ? C16 C4 C5 C6 164.65(13) . . . . ? C3 C4 C5 C6 44.47(17) . . . . ? C4 C5 C6 O18 102.69(16) . . . . ? C4 C5 C6 C7 -79.38(19) . . . . ? O18 C6 C7 C19 3.6(2) . . . . ? C5 C6 C7 C19 -174.09(14) . . . . ? O18 C6 C7 C8 -173.75(14) . . . . ? C5 C6 C7 C8 8.5(2) . . . . ? C6 C7 C8 C13 41.9(2) . . . . ? C19 C7 C8 C13 -135.35(15) . . . . ? C6 C7 C8 C9 -138.77(16) . . . . ? C19 C7 C8 C9 44.0(2) . . . . ? C13 C8 C9 C10 1.3(2) . . . . ? C7 C8 C9 C10 -178.03(14) . . . . ? C8 C9 C10 C11 0.2(2) . . . . ? C9 C10 C11 C12 -0.8(2) . . . . ? C10 C11 C12 C13 -0.1(2) . . . . ? C10 C11 C12 N1 176.06(14) . . . . ? C2 N1 C12 C11 -173.29(14) . . . . ? C14 N1 C12 C11 0.0(2) . . . . ? C2 N1 C12 C13 3.27(16) . . . . ? C14 N1 C12 C13 176.57(13) . . . . ? C9 C8 C13 C12 -2.3(2) . . . . ? C7 C8 C13 C12 177.12(13) . . . . ? C9 C8 C13 C3 -177.99(13) . . . . ? C7 C8 C13 C3 1.4(2) . . . . ? C11 C12 C13 C8 1.7(2) . . . . ? N1 C12 C13 C8 -175.11(12) . . . . ? C11 C12 C13 C3 178.21(13) . . . . ? N1 C12 C13 C3 1.35(15) . . . . ? C2 C3 C13 C8 171.34(14) . . . . ? C4 C3 C13 C8 -67.19(18) . . . . ? C2 C3 C13 C12 -4.80(14) . . . . ? C4 C3 C13 C12 116.66(13) . . . . ? C6 C7 C19 O20 -0.6(2) . . . . ? C8 C7 C19 O20 176.61(15) . . . . ? C6 C7 C19 O21 178.63(14) . . . . ? C8 C7 C19 O21 -4.1(2) . . . . ? O20 C19 O21 C22 3.5(2) . . . . ? C7 C19 O21 C22 -175.77(14) . . . . ? C12' N1' C2' O15' -172.57(14) . . . . ? C14' N1' C2' O15' 0.4(2) . . . . ? C12' N1' C2' C3' 7.84(15) . . . . ? C14' N1' C2' C3' -179.19(13) . . . . ? O15' C2' C3' C13' 172.02(14) . . . . ? N1' C2' C3' C13' -8.40(14) . . . . ? O15' C2' C3' C4' -65.06(19) . . . . ? N1' C2' C3' C4' 114.51(12) . . . . ? C13' C3' C4' C16' 87.37(15) . . . . ? C2' C3' C4' C16' -28.58(16) . . . . ? C13' C3' C4' C17' -150.87(12) . . . . ? C2' C3' C4' C17' 93.18(14) . . . . ? C13' C3' C4' C5' -30.37(15) . . . . ? C2' C3' C4' C5' -146.32(12) . . . . ? C16' C4' C5' C6' -169.15(12) . . . . ? C17' C4' C5' C6' 71.61(15) . . . . ? C3' C4' C5' C6' -48.95(16) . . . . ? C4' C5' C6' O18' -101.98(14) . . . . ? C4' C5' C6' C7' 79.45(18) . . . . ? O18' C6' C7' C19' 0.1(2) . . . . ? C5' C6' C7' C19' 178.58(13) . . . . ? O18' C6' C7' C8' 176.31(13) . . . . ? C5' C6' C7' C8' -5.2(2) . . . . ? C6' C7' C8' C13' -43.03(18) . . . . ? C19' C7' C8' C13' 132.92(14) . . . . ? C6' C7' C8' C9' 134.30(15) . . . . ? C19' C7' C8' C9' -49.8(2) . . . . ? C13' C8' C9' C10' -0.7(2) . . . . ? C7' C8' C9' C10' -178.04(13) . . . . ? C8' C9' C10' C11' -0.5(2) . . . . ? C9' C10' C11' C12' 0.6(2) . . . . ? C10' C11' C12' C13' 0.4(2) . . . . ? C10' C11' C12' N1' -176.48(14) . . . . ? C2' N1' C12' C11' 173.39(14) . . . . ? C14' N1' C12' C11' 0.4(2) . . . . ? C2' N1' C12' C13' -3.84(16) . . . . ? C14' N1' C12' C13' -176.81(13) . . . . ? C9' C8' C13' C12' 1.76(19) . . . . ? C7' C8' C13' C12' 179.28(12) . . . . ? C9' C8' C13' C3' 179.01(13) . . . . ? C7' C8' C13' C3' -3.5(2) . . . . ? C11' C12' C13' C8' -1.7(2) . . . . ? N1' C12' C13' C8' 175.77(12) . . . . ? C11' C12' C13' C3' -179.44(12) . . . . ? N1' C12' C13' C3' -1.98(15) . . . . ? C2' C3' C13' C8' -171.27(13) . . . . ? C4' C3' C13' C8' 66.79(18) . . . . ? C2' C3' C13' C12' 6.23(14) . . . . ? C4' C3' C13' C12' -115.70(13) . . . . ? C6' C7' C19' O20' -3.6(2) . . . . ? C8' C7' C19' O20' -179.57(14) . . . . ? C6' C7' C19' O21' 176.15(13) . . . . ? C8' C7' C19' O21' 0.2(2) . . . . ? O20' C19' O21' C22' -1.5(2) . . . . ? C7' C19' O21' C22' 178.75(13) . . . . ? 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 O18 H18 O20 0.94(3) 1.74(3) 2.576(2) 146(3) . O18' H18' O20' 0.97(2) 1.63(2) 2.5235(17) 151(2) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.254 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.038 ###=END data_rwh59c-17 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 N O3' _chemical_formula_weight 285.33 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5637(2) _cell_length_b 15.9280(3) _cell_length_c 10.1072(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.491(1) _cell_angle_gamma 90.00 _cell_volume 1460.15(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.089 _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 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6210 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3334 _reflns_number_gt 2783 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0396P)^2^+0.9243P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refal _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3334 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.062 _refine_ls_shift/su_mean 0.007 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 N1 N 0.66576(16) 0.67463(9) 0.46002(16) 0.0227(3) Uani 1 1 d . . . C2 C 0.58301(19) 0.67264(11) 0.54899(19) 0.0224(4) Uani 1 1 d . . . C3 C 0.44556(18) 0.64186(10) 0.48296(18) 0.0195(4) Uani 1 1 d . . . C4 C 0.32414(19) 0.62502(11) 0.54536(18) 0.0231(4) Uani 1 1 d . . . C5 C 0.2450(2) 0.54293(12) 0.4792(2) 0.0260(4) Uani 1 1 d . . . C6 C 0.13999(19) 0.55366(11) 0.3351(2) 0.0241(4) Uani 1 1 d . . . C7 C 0.17619(19) 0.57607(10) 0.21927(19) 0.0211(4) Uani 1 1 d . . . C8 C 0.33146(18) 0.59025(10) 0.22251(17) 0.0187(4) Uani 1 1 d . . . C9 C 0.3756(2) 0.57380(11) 0.10603(19) 0.0231(4) Uani 1 1 d . . . C10 C 0.5175(2) 0.59299(12) 0.10232(19) 0.0260(4) Uani 1 1 d . . . C11 C 0.6222(2) 0.62833(11) 0.21430(19) 0.0242(4) Uani 1 1 d . . . C12 C 0.58263(18) 0.64252(10) 0.33376(18) 0.0203(4) Uani 1 1 d . . . C13 C 0.44100(18) 0.62254(10) 0.34213(17) 0.0181(4) Uani 1 1 d . . . C14 C 0.8175(2) 0.70200(15) 0.4940(3) 0.0340(5) Uani 1 1 d . . . C15 C 0.3897(3) 0.61105(16) 0.7034(2) 0.0363(5) Uani 1 1 d . . . C16 C 0.2158(2) 0.69898(13) 0.5181(2) 0.0325(5) Uani 1 1 d . . . O17 O 0.00003(15) 0.54028(9) 0.33157(16) 0.0347(4) Uani 1 1 d . . . C18 C 0.0530(2) 0.59233(11) 0.0918(2) 0.0263(4) Uani 1 1 d . . . O19 O -0.07726(15) 0.57632(10) 0.07844(15) 0.0378(4) Uani 1 1 d . . . O20 O 0.08927(14) 0.62859(8) -0.01127(14) 0.0309(3) Uani 1 1 d . . . C21 C -0.0296(3) 0.64605(15) -0.1384(2) 0.0372(5) Uani 1 1 d . . . H2 H 0.628(2) 0.6913(13) 0.646(2) 0.028(5) Uiso 1 1 d . . . H5A H 0.321(2) 0.5023(13) 0.479(2) 0.026(5) Uiso 1 1 d . . . H5B H 0.190(2) 0.5225(13) 0.538(2) 0.034(6) Uiso 1 1 d . . . H9 H 0.307(2) 0.5494(12) 0.025(2) 0.024(5) Uiso 1 1 d . . . H10 H 0.537(2) 0.5810(13) 0.017(2) 0.028(5) Uiso 1 1 d . . . H11 H 0.718(2) 0.6421(13) 0.211(2) 0.028(5) Uiso 1 1 d . . . H14A H 0.884(3) 0.6542(17) 0.506(3) 0.050(7) Uiso 1 1 d . . . H14B H 0.845(3) 0.7326(16) 0.581(3) 0.047(7) Uiso 1 1 d . . . H14C H 0.829(3) 0.7396(18) 0.420(3) 0.058(8) Uiso 1 1 d . . . H15A H 0.458(3) 0.5611(16) 0.719(2) 0.046(7) Uiso 1 1 d . . . H15B H 0.443(3) 0.6647(16) 0.749(2) 0.045(6) Uiso 1 1 d . . . H15C H 0.309(3) 0.6002(16) 0.746(3) 0.052(7) Uiso 1 1 d . . . H16A H 0.136(3) 0.6879(15) 0.558(2) 0.043(6) Uiso 1 1 d . . . H16B H 0.274(2) 0.7505(16) 0.561(2) 0.042(6) Uiso 1 1 d . . . H16C H 0.167(3) 0.7097(15) 0.415(3) 0.043(6) Uiso 1 1 d . . . H17 H -0.055(3) 0.5510(18) 0.235(3) 0.064(8) Uiso 1 1 d . . . H21A H -0.092(3) 0.6908(17) -0.122(3) 0.051(7) Uiso 1 1 d . . . H21B H -0.087(3) 0.5941(18) -0.170(3) 0.054(7) Uiso 1 1 d . . . H21C H 0.019(3) 0.663(2) -0.206(3) 0.080(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0182(7) 0.0233(8) 0.0254(8) 0.0007(6) 0.0052(6) -0.0015(6) C2 0.0230(9) 0.0220(9) 0.0204(9) 0.0001(7) 0.0043(7) 0.0017(7) C3 0.0222(8) 0.0172(8) 0.0193(8) 0.0017(7) 0.0068(7) 0.0028(7) C4 0.0244(9) 0.0271(9) 0.0203(9) -0.0007(7) 0.0107(7) 0.0008(7) C5 0.0275(9) 0.0258(10) 0.0295(10) 0.0037(8) 0.0160(8) -0.0015(8) C6 0.0208(9) 0.0209(9) 0.0331(10) -0.0050(8) 0.0122(8) -0.0030(7) C7 0.0209(9) 0.0172(8) 0.0246(9) -0.0030(7) 0.0064(7) -0.0007(7) C8 0.0207(8) 0.0155(8) 0.0203(9) 0.0022(7) 0.0070(7) 0.0020(6) C9 0.0264(9) 0.0231(9) 0.0196(9) -0.0006(7) 0.0070(8) 0.0032(7) C10 0.0319(10) 0.0287(10) 0.0216(9) 0.0032(8) 0.0145(8) 0.0054(8) C11 0.0229(9) 0.0246(9) 0.0294(10) 0.0064(8) 0.0144(8) 0.0026(7) C12 0.0201(8) 0.0173(8) 0.0234(9) 0.0037(7) 0.0066(7) 0.0017(7) C13 0.0200(8) 0.0143(8) 0.0207(9) 0.0024(6) 0.0074(7) 0.0015(7) C14 0.0207(10) 0.0400(12) 0.0397(13) -0.0023(10) 0.0071(9) -0.0071(9) C15 0.0410(12) 0.0483(14) 0.0228(10) 0.0015(9) 0.0148(9) -0.0015(11) C16 0.0284(10) 0.0326(11) 0.0399(13) -0.0077(9) 0.0157(10) 0.0035(9) O17 0.0241(7) 0.0445(9) 0.0387(9) -0.0035(7) 0.0146(6) -0.0075(6) C18 0.0258(10) 0.0210(9) 0.0308(10) -0.0047(8) 0.0072(8) 0.0004(7) O19 0.0221(7) 0.0481(9) 0.0383(9) -0.0051(7) 0.0028(6) -0.0026(6) O20 0.0306(7) 0.0280(7) 0.0280(7) 0.0039(6) 0.0005(6) 0.0006(6) C21 0.0400(12) 0.0305(11) 0.0292(11) -0.0008(9) -0.0060(9) 0.0029(10) _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 N1 C2 1.374(2) . ? N1 C12 1.371(2) . ? N1 C14 1.449(2) . ? C2 C3 1.363(2) . ? C2 H2 0.98(2) . ? C3 C13 1.443(2) . ? C3 C4 1.511(2) . ? C4 C16 1.535(3) . ? C4 C15 1.536(3) . ? C4 C5 1.552(3) . ? C5 C6 1.494(3) . ? C5 H5A 0.98(2) . ? C5 H5B 0.97(2) . ? C6 O17 1.345(2) . ? C6 C7 1.369(3) . ? C7 C18 1.467(3) . ? C7 C8 1.492(2) . ? C8 C9 1.396(2) . ? C8 C13 1.421(2) . ? C9 C10 1.403(3) . ? C9 H9 0.95(2) . ? C10 C11 1.372(3) . ? C10 H10 0.96(2) . ? C11 C12 1.394(2) . ? C11 H11 0.96(2) . ? C12 C13 1.420(2) . ? C14 H14A 0.97(3) . ? C14 H14B 0.96(3) . ? C14 H14C 0.99(3) . ? C15 H15A 1.01(3) . ? C15 H15B 1.03(3) . ? C15 H15C 1.01(3) . ? C16 H16A 0.99(2) . ? C16 H16B 1.01(2) . ? C16 H16C 1.01(2) . ? O17 H17 0.97(3) . ? C18 O19 1.237(2) . ? C18 O20 1.330(2) . ? O20 C21 1.447(2) . ? C21 H21A 0.98(3) . ? C21 H21B 0.99(3) . ? C21 H21C 0.98(3) . ? 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 C2 N1 C12 108.44(14) . . ? C2 N1 C14 126.40(16) . . ? C12 N1 C14 125.09(16) . . ? C3 C2 N1 110.74(16) . . ? C3 C2 H2 130.2(12) . . ? N1 C2 H2 119.0(12) . . ? C2 C3 C13 106.40(15) . . ? C2 C3 C4 127.53(16) . . ? C13 C3 C4 125.94(15) . . ? C3 C4 C16 110.68(15) . . ? C3 C4 C15 110.22(15) . . ? C16 C4 C15 109.13(16) . . ? C3 C4 C5 107.70(14) . . ? C16 C4 C5 111.09(16) . . ? C15 C4 C5 107.97(16) . . ? C6 C5 C4 114.14(15) . . ? C6 C5 H5A 110.1(12) . . ? C4 C5 H5A 107.3(12) . . ? C6 C5 H5B 108.0(13) . . ? C4 C5 H5B 107.7(13) . . ? H5A C5 H5B 109.5(17) . . ? O17 C6 C7 122.56(17) . . ? O17 C6 C5 111.32(16) . . ? C7 C6 C5 126.11(16) . . ? C6 C7 C18 116.52(16) . . ? C6 C7 C8 122.71(16) . . ? C18 C7 C8 120.60(16) . . ? C9 C8 C13 116.55(15) . . ? C9 C8 C7 121.21(16) . . ? C13 C8 C7 122.23(15) . . ? C8 C9 C10 122.37(17) . . ? C8 C9 H9 119.4(12) . . ? C10 C9 H9 118.3(12) . . ? C11 C10 C9 121.79(17) . . ? C11 C10 H10 121.5(12) . . ? C9 C10 H10 116.7(12) . . ? C10 C11 C12 116.95(16) . . ? C10 C11 H11 121.8(12) . . ? C12 C11 H11 121.2(12) . . ? N1 C12 C11 129.08(16) . . ? N1 C12 C13 108.11(14) . . ? C11 C12 C13 122.80(16) . . ? C12 C13 C8 119.35(15) . . ? C12 C13 C3 106.26(15) . . ? C8 C13 C3 134.39(15) . . ? N1 C14 H14A 111.0(15) . . ? N1 C14 H14B 109.1(14) . . ? H14A C14 H14B 108(2) . . ? N1 C14 H14C 110.3(15) . . ? H14A C14 H14C 110(2) . . ? H14B C14 H14C 108(2) . . ? C4 C15 H15A 108.0(14) . . ? C4 C15 H15B 109.2(13) . . ? H15A C15 H15B 112.6(19) . . ? C4 C15 H15C 110.5(14) . . ? H15A C15 H15C 110(2) . . ? H15B C15 H15C 106.6(19) . . ? C4 C16 H16A 110.7(14) . . ? C4 C16 H16B 107.1(13) . . ? H16A C16 H16B 111.6(18) . . ? C4 C16 H16C 112.4(13) . . ? H16A C16 H16C 106.6(19) . . ? H16B C16 H16C 108.4(19) . . ? C6 O17 H17 102.6(17) . . ? O19 C18 O20 120.52(17) . . ? O19 C18 C7 124.09(18) . . ? O20 C18 C7 115.37(16) . . ? C18 O20 C21 116.90(17) . . ? O20 C21 H21A 109.8(15) . . ? O20 C21 H21B 108.8(15) . . ? H21A C21 H21B 111(2) . . ? O20 C21 H21C 105.1(18) . . ? H21A C21 H21C 112(2) . . ? H21B C21 H21C 110(2) . . ? 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 C12 N1 C2 C3 -1.6(2) . . . . ? C14 N1 C2 C3 -178.83(18) . . . . ? N1 C2 C3 C13 0.3(2) . . . . ? N1 C2 C3 C4 176.35(16) . . . . ? C2 C3 C4 C16 96.8(2) . . . . ? C13 C3 C4 C16 -87.8(2) . . . . ? C2 C3 C4 C15 -24.0(3) . . . . ? C13 C3 C4 C15 151.33(18) . . . . ? C2 C3 C4 C5 -141.55(18) . . . . ? C13 C3 C4 C5 33.8(2) . . . . ? C3 C4 C5 C6 -77.81(18) . . . . ? C16 C4 C5 C6 43.6(2) . . . . ? C15 C4 C5 C6 163.18(16) . . . . ? C4 C5 C6 O17 -113.69(17) . . . . ? C4 C5 C6 C7 64.9(2) . . . . ? O17 C6 C7 C18 5.3(3) . . . . ? C5 C6 C7 C18 -173.12(17) . . . . ? O17 C6 C7 C8 -179.46(15) . . . . ? C5 C6 C7 C8 2.1(3) . . . . ? C6 C7 C8 C9 149.23(17) . . . . ? C18 C7 C8 C9 -35.7(2) . . . . ? C6 C7 C8 C13 -32.1(3) . . . . ? C18 C7 C8 C13 143.01(17) . . . . ? C13 C8 C9 C10 -4.1(3) . . . . ? C7 C8 C9 C10 174.64(16) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C9 C10 C11 C12 1.6(3) . . . . ? C2 N1 C12 C11 -176.60(17) . . . . ? C14 N1 C12 C11 0.7(3) . . . . ? C2 N1 C12 C13 2.18(19) . . . . ? C14 N1 C12 C13 179.49(17) . . . . ? C10 C11 C12 N1 178.20(17) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? N1 C12 C13 C8 178.13(14) . . . . ? C11 C12 C13 C8 -3.0(2) . . . . ? N1 C12 C13 C3 -1.97(18) . . . . ? C11 C12 C13 C3 176.90(16) . . . . ? C9 C8 C13 C12 5.1(2) . . . . ? C7 C8 C13 C12 -173.67(15) . . . . ? C9 C8 C13 C3 -174.78(18) . . . . ? C7 C8 C13 C3 6.5(3) . . . . ? C2 C3 C13 C12 1.02(18) . . . . ? C4 C3 C13 C12 -175.11(16) . . . . ? C2 C3 C13 C8 -179.10(18) . . . . ? C4 C3 C13 C8 4.8(3) . . . . ? C6 C7 C18 O19 -10.1(3) . . . . ? C8 C7 C18 O19 174.55(17) . . . . ? C6 C7 C18 O20 168.14(16) . . . . ? C8 C7 C18 O20 -7.2(2) . . . . ? O19 C18 O20 C21 -1.3(3) . . . . ? C7 C18 O20 C21 -179.63(16) . . . . ? 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 O17 H17 O19 0.97(3) 1.58(3) 2.494(2) 156(3) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.324 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.042