# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 # CCDC Number: 440/237 data_2a _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4S)-4-Benzyl-3-(4,5-dimethyl-3-pyrazolyl)-1,3-oxazolidin-2-one ; _chemical_formula_sum 'C15 H17 N3 O2' _chemical_formula_weight 271.32 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.486(4) _cell_length_b 12.445(1) _cell_length_c 18.327(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1479.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.45 _cell_measurement_theta_max 13.71 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega/2theta scan' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1297 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 24.95 _reflns_number_total 1297 _reflns_number_gt 1119 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 (Enraf-Nonius)' _computing_cell_refinement 'CAD4 (Enraf-Nonius)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0907P)^2^+0.0000P] 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 0.035(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 5(2) _refine_ls_number_reflns 1297 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.0405(4) -0.1132(2) -0.15802(14) 0.0545(7) Uani 1 d . . . H1 H 0.005(6) -0.045(3) -0.1568(18) 0.065 Uiso 1 d . . . N2 N -0.1717(4) -0.13909(18) -0.21225(14) 0.0517(6) Uani 1 d . . . C3 C -0.1932(4) -0.2441(2) -0.20494(16) 0.0450(6) Uani 1 d . . . C4 C -0.0776(5) -0.2870(2) -0.14767(17) 0.0542(7) Uani 1 d . . . C5 C 0.0227(5) -0.1984(3) -0.11897(18) 0.0569(7) Uani 1 d . . . C6 C 0.1744(7) -0.1876(4) -0.0584(2) 0.0871(12) Uani 1 d . . . H6A H 0.2118 -0.1135 -0.0528 0.131 Uiso 1 calc R . . H6B H 0.2952 -0.2291 -0.0695 0.131 Uiso 1 calc R . . H6C H 0.1139 -0.2134 -0.0139 0.131 Uiso 1 calc R . . N7 N -0.3232(3) -0.30159(17) -0.25369(15) 0.0484(6) Uani 1 d . . . C8 C -0.2493(5) -0.3744(2) -0.29986(16) 0.0485(6) Uani 1 d . . . O9 O -0.4038(3) -0.42790(18) -0.33275(13) 0.0636(6) Uani 1 d . . . C10 C -0.5965(5) -0.3929(2) -0.3029(2) 0.0640(9) Uani 1 d . . . H10A H -0.6614 -0.4509 -0.2760 0.077 Uiso 1 calc R . . H10B H -0.6888 -0.3704 -0.3417 0.077 Uiso 1 calc R . . C11 C -0.5496(4) -0.2984(2) -0.2520(2) 0.0531(7) Uani 1 d . . . H11 H -0.5977 -0.3156 -0.2027 0.064 Uiso 1 calc R . . O12 O -0.0697(3) -0.39423(16) -0.31357(12) 0.0596(6) Uani 1 d . . . C13 C -0.6393(3) -0.19136(15) -0.27554(11) 0.0564(8) Uani 1 d . . . H13A H -0.7869 -0.1932 -0.2673 0.068 Uiso 1 calc R . . H13B H -0.5826 -0.1357 -0.2444 0.068 Uiso 1 calc R . . C14 C -0.6014(3) -0.15977(15) -0.35412(11) 0.0558(8) Uani 1 d R . . C15 C -0.7562(3) -0.17558(15) -0.40547(11) 0.0729(10) Uani 1 d R . . H15 H -0.8824 -0.2046 -0.3916 0.087 Uiso 1 calc R . . C16 C -0.7200(9) -0.1475(3) -0.4778(2) 0.0890(13) Uani 1 d . . . H16 H -0.8236 -0.1574 -0.5122 0.107 Uiso 1 calc R . . C17 C -0.5351(9) -0.1055(3) -0.4992(2) 0.0911(14) Uani 1 d . . . H17 H -0.5126 -0.0878 -0.5478 0.109 Uiso 1 calc R . . C18 C -0.3819(7) -0.0895(3) -0.4480(2) 0.0830(11) Uani 1 d . . . H18 H -0.2553 -0.0611 -0.4621 0.100 Uiso 1 calc R . . C19 C -0.4175(6) -0.1160(3) -0.3758(2) 0.0670(9) Uani 1 d . . . H19 H -0.3148 -0.1038 -0.3414 0.080 Uiso 1 calc R . . C20 C -0.0632(8) -0.4020(3) -0.1246(2) 0.0827(11) Uani 1 d . . . H20A H -0.1516 -0.4450 -0.1548 0.124 Uiso 1 calc R . . H20B H -0.1053 -0.4085 -0.0746 0.124 Uiso 1 calc R . . H20C H 0.0766 -0.4263 -0.1296 0.124 Uiso 1 calc R . . 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 0.0515(15) 0.0426(13) 0.0693(16) -0.0048(11) -0.0034(12) -0.0028(11) N2 0.0431(12) 0.0437(12) 0.0683(14) -0.0042(11) -0.0058(11) 0.0028(10) C3 0.0361(13) 0.0386(13) 0.0603(15) -0.0063(12) 0.0046(12) 0.0036(11) C4 0.0559(16) 0.0473(15) 0.0595(16) 0.0013(13) 0.0013(14) 0.0041(14) C5 0.0548(17) 0.0562(18) 0.0596(17) -0.0031(14) 0.0004(13) 0.0017(14) C6 0.102(3) 0.083(3) 0.077(2) -0.004(2) -0.028(2) 0.004(2) N7 0.0305(11) 0.0438(11) 0.0710(14) -0.0083(13) 0.0033(10) 0.0027(9) C8 0.0394(13) 0.0420(13) 0.0642(15) -0.0012(13) 0.0004(12) -0.0019(11) O9 0.0447(11) 0.0571(12) 0.0891(15) -0.0175(11) -0.0036(11) -0.0070(10) C10 0.0392(14) 0.0458(16) 0.107(3) 0.0013(16) -0.0009(16) -0.0069(12) C11 0.0271(13) 0.0563(15) 0.0759(17) 0.0034(16) 0.0084(13) -0.0033(11) O12 0.0372(11) 0.0588(13) 0.0828(14) -0.0148(10) 0.0075(10) 0.0044(9) C13 0.0340(14) 0.0540(15) 0.081(2) -0.0071(14) 0.0066(13) 0.0076(12) C14 0.0495(16) 0.0412(14) 0.077(2) -0.0052(13) -0.0043(14) 0.0090(12) C15 0.0634(19) 0.0596(19) 0.096(3) -0.0091(19) -0.019(2) 0.0052(16) C16 0.114(4) 0.065(2) 0.088(3) -0.005(2) -0.034(3) 0.003(2) C17 0.145(4) 0.063(2) 0.065(2) 0.0041(17) -0.007(3) 0.003(3) C18 0.093(3) 0.082(2) 0.074(2) 0.006(2) 0.000(2) -0.014(2) C19 0.0639(19) 0.0610(18) 0.076(2) 0.0010(16) -0.0068(18) -0.0105(17) C20 0.107(3) 0.056(2) 0.085(2) 0.0162(17) -0.010(2) 0.001(2) _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 C5 1.343(4) . ? N1 N2 1.348(4) . ? N2 C3 1.321(3) . ? C3 C4 1.396(4) . ? C3 N7 1.422(3) . ? C4 C5 1.384(4) . ? C4 C20 1.495(4) . ? C5 C6 1.489(5) . ? N7 C8 1.329(4) . ? N7 C11 1.469(3) . ? C8 O12 1.217(4) . ? C8 O9 1.346(4) . ? O9 C10 1.432(4) . ? C10 C11 1.532(5) . ? C11 C13 1.516(3) . ? C13 C14 1.5128 . ? C14 C19 1.371(4) . ? C14 C15 1.3900 . ? C15 C16 1.391(5) . ? C16 C17 1.365(7) . ? C17 C18 1.381(7) . ? C18 C19 1.383(6) . ? 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 C5 N1 N2 113.4(2) . . ? C3 N2 N1 103.2(2) . . ? N2 C3 C4 113.5(3) . . ? N2 C3 N7 119.8(3) . . ? C4 C3 N7 126.7(3) . . ? C5 C4 C3 103.5(3) . . ? C5 C4 C20 128.8(3) . . ? C3 C4 C20 127.8(3) . . ? N1 C5 C4 106.4(3) . . ? N1 C5 C6 121.9(3) . . ? C4 C5 C6 131.7(3) . . ? C8 N7 C3 122.0(2) . . ? C8 N7 C11 113.1(2) . . ? C3 N7 C11 124.5(2) . . ? O12 C8 N7 128.0(3) . . ? O12 C8 O9 121.3(3) . . ? N7 C8 O9 110.7(2) . . ? C8 O9 C10 109.2(2) . . ? O9 C10 C11 107.0(2) . . ? N7 C11 C13 113.6(2) . . ? N7 C11 C10 99.5(2) . . ? C13 C11 C10 115.2(3) . . ? C14 C13 C11 115.91(15) . . ? C19 C14 C15 119.24(18) . . ? C19 C14 C13 121.38(18) . . ? C15 C14 C13 119.4 . . ? C14 C15 C16 119.2(2) . . ? C17 C16 C15 121.2(4) . . ? C16 C17 C18 119.5(4) . . ? C17 C18 C19 119.7(4) . . ? C14 C19 C18 121.2(4) . . ? _diffrn_measured_fraction_theta_max 0.851 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.851 _refine_diff_density_max 0.134 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.033 data_3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4S)-4-Benzyl-3-(4-benzyl-5-methyl-3-pyrazolyl)-1,3-oxazolidin-2-one ; _chemical_formula_sum 'C21 H21 N3 O2' _chemical_formula_weight 347.41 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.601(9) _cell_length_b 14.743(4) _cell_length_c 18.895(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1839(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.80 _cell_measurement_theta_max 12.43 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 1.08 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega/2theta scan' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1613 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0871 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 24.95 _reflns_number_total 1613 _reflns_number_gt 1036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 (Enraf-Nonius)' _computing_cell_refinement 'CAD4 (Enraf-Nonius)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+0.0000P] 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 none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3(3) _refine_ls_number_reflns 1613 _refine_ls_number_parameters 238 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.891 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.0208(6) -1.0389(3) -0.7018(2) 0.0675(11) Uani 1 d . . . H1 H -0.011(7) -1.097(3) -0.700(2) 0.081 Uiso 1 d . . . N2 N 0.1178(6) -0.9988(2) -0.7442(2) 0.0628(9) Uani 1 d . . . C3 C 0.0930(5) -0.9120(3) -0.72924(19) 0.0458(10) Uani 1 d . . . C4 C -0.0535(6) -0.8948(3) -0.6776(2) 0.0477(10) Uani 1 d . . . C5 C -0.1271(6) -0.9801(3) -0.6618(2) 0.0557(11) Uani 1 d . . . C6 C -0.2913(7) -1.0095(3) -0.6121(3) 0.0778(14) Uani 1 d . . . H6A H -0.3045 -1.0743 -0.6137 0.117 Uiso 1 calc R . . H6B H -0.4171 -0.9820 -0.6259 0.117 Uiso 1 calc R . . H6C H -0.2576 -0.9910 -0.5648 0.117 Uiso 1 calc R . . N7 N 0.2166(4) -0.8469(2) -0.76295(16) 0.0450(8) Uani 1 d . . . C8 C 0.1451(6) -0.7712(3) -0.7929(2) 0.0513(10) Uani 1 d . . . O9 O 0.2981(4) -0.71396(18) -0.80938(15) 0.0569(7) Uani 1 d . . . C10 C 0.4811(5) -0.7478(3) -0.7770(2) 0.0590(11) Uani 1 d . . . H10A H 0.5100 -0.7155 -0.7335 0.071 Uiso 1 calc R . . H10B H 0.5955 -0.7411 -0.8088 0.071 Uiso 1 calc R . . C11 C 0.4399(5) -0.8472(2) -0.7622(2) 0.0490(9) Uani 1 d . . . H11 H 0.4875 -0.8622 -0.7145 0.059 Uiso 1 calc R . . O12 O -0.0307(4) -0.75020(19) -0.80511(16) 0.0644(8) Uani 1 d . . . C13 C 0.5309(6) -0.9141(3) -0.8152(2) 0.0541(11) Uani 1 d . . . H13A H 0.6773 -0.9093 -0.8133 0.065 Uiso 1 calc R . . H13B H 0.4947 -0.9752 -0.8009 0.065 Uiso 1 calc R . . C14 C 0.4638(6) -0.8999(3) -0.8896(2) 0.0532(10) Uani 1 d D . . C15 C 0.2809(7) -0.9372(3) -0.9138(2) 0.0698(13) Uani 1 d D . . H15 H 0.2013 -0.9717 -0.8834 0.084 Uiso 1 calc R . . C16 C 0.2193(9) -0.9228(4) -0.9823(3) 0.0899(17) Uani 1 d D . . H16 H 0.0992 -0.9489 -0.9980 0.108 Uiso 1 calc R . . C17 C 0.3304(11) -0.8708(4) -1.0280(3) 0.104(2) Uani 1 d D . . H17 H 0.2862 -0.8606 -1.0741 0.124 Uiso 1 calc R . . C18 C 0.5082(11) -0.8342(4) -1.0043(3) 0.0997(19) Uani 1 d D . . H18 H 0.5857 -0.7990 -1.0348 0.120 Uiso 1 calc R . . C19 C 0.5745(8) -0.8484(3) -0.9366(3) 0.0767(13) Uani 1 d D . . H19 H 0.6964 -0.8228 -0.9221 0.092 Uiso 1 calc R . . C20 C -0.1101(6) -0.8066(3) -0.6450(2) 0.0526(10) Uani 1 d . . . H20A H -0.2006 -0.8180 -0.6055 0.063 Uiso 1 calc R . . H20B H -0.1836 -0.7708 -0.6795 0.063 Uiso 1 calc R . . C21 C 0.0687(5) -0.7520(2) -0.61877(19) 0.0448(9) Uani 1 d D . . C22 C 0.2308(5) -0.7945(3) -0.5850(2) 0.0547(10) Uani 1 d D . . H22 H 0.2334 -0.8573 -0.5805 0.066 Uiso 1 calc R . . C23 C 0.3878(6) -0.7426(4) -0.5582(2) 0.0705(13) Uani 1 d D . . H23 H 0.4955 -0.7710 -0.5355 0.085 Uiso 1 calc R . . C24 C 0.3870(8) -0.6503(4) -0.5645(3) 0.0913(18) Uani 1 d D . . H24 H 0.4938 -0.6161 -0.5466 0.110 Uiso 1 calc R . . C25 C 0.2253(10) -0.6083(3) -0.5977(3) 0.0895(17) Uani 1 d D . . H25 H 0.2222 -0.5454 -0.6016 0.107 Uiso 1 calc R . . C26 C 0.0689(7) -0.6596(3) -0.6248(2) 0.0656(11) Uani 1 d D . . H26 H -0.0382 -0.6309 -0.6477 0.079 Uiso 1 calc R . . 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 0.089(3) 0.0427(18) 0.070(2) -0.0036(19) 0.016(2) -0.017(2) N2 0.074(2) 0.0462(17) 0.068(2) -0.0047(19) 0.015(2) -0.0066(19) C3 0.045(2) 0.047(2) 0.046(2) 0.0009(18) -0.0037(18) -0.0072(18) C4 0.040(2) 0.049(2) 0.054(2) -0.003(2) -0.005(2) -0.0049(19) C5 0.053(2) 0.057(3) 0.057(3) 0.000(2) 0.004(2) -0.009(2) C6 0.073(3) 0.079(3) 0.081(3) 0.003(3) 0.023(3) -0.016(3) N7 0.0326(16) 0.0449(16) 0.058(2) 0.0013(17) 0.0007(15) -0.0007(14) C8 0.049(2) 0.050(3) 0.055(3) -0.0019(19) 0.0012(19) 0.003(2) O9 0.0400(14) 0.0503(15) 0.080(2) 0.0138(15) 0.0041(14) -0.0025(13) C10 0.0322(18) 0.059(2) 0.086(3) -0.003(2) -0.003(2) -0.008(2) C11 0.0328(18) 0.055(2) 0.059(3) 0.000(2) -0.0067(18) 0.0033(19) O12 0.0308(13) 0.0743(18) 0.088(2) 0.0119(17) -0.0034(14) 0.0092(14) C13 0.042(2) 0.051(3) 0.069(3) -0.002(2) -0.002(2) 0.0062(19) C14 0.045(2) 0.051(2) 0.064(3) -0.003(2) 0.005(2) 0.011(2) C15 0.063(3) 0.078(3) 0.068(3) -0.011(2) 0.000(3) -0.002(2) C16 0.084(4) 0.112(5) 0.074(4) -0.017(3) -0.018(3) 0.014(3) C17 0.136(6) 0.115(6) 0.060(4) 0.000(4) -0.012(4) 0.037(5) C18 0.129(5) 0.092(4) 0.077(4) 0.015(3) 0.030(4) 0.010(4) C19 0.080(3) 0.075(3) 0.075(4) 0.002(3) 0.016(3) 0.001(3) C20 0.037(2) 0.060(2) 0.061(2) -0.004(2) 0.0005(18) -0.0004(19) C21 0.0403(18) 0.050(2) 0.044(2) -0.0055(19) 0.0049(18) -0.0024(19) C22 0.047(2) 0.064(3) 0.053(2) -0.008(2) 0.001(2) 0.004(2) C23 0.052(2) 0.101(4) 0.059(3) -0.016(3) -0.005(2) -0.001(3) C24 0.073(4) 0.115(5) 0.086(4) -0.022(4) 0.001(3) -0.037(4) C25 0.117(5) 0.065(3) 0.087(4) -0.002(3) 0.008(4) -0.036(3) C26 0.076(3) 0.054(3) 0.066(3) 0.003(2) 0.001(3) -0.004(3) _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 C5 1.348(5) . ? N1 N2 1.352(5) . ? N2 C3 1.321(4) . ? C3 C4 1.397(5) . ? C3 N7 1.412(5) . ? C4 C5 1.381(5) . ? C4 C20 1.486(5) . ? C5 C6 1.498(6) . ? N7 C8 1.337(5) . ? N7 C11 1.474(5) . ? C8 O12 1.223(5) . ? C8 O9 1.353(5) . ? O9 C10 1.443(4) . ? C10 C11 1.516(5) . ? C11 C13 1.528(6) . ? C13 C14 1.488(6) . ? C14 C19 1.379(6) . ? C14 C15 1.404(5) . ? C15 C16 1.373(6) . ? C16 C17 1.368(7) . ? C17 C18 1.367(7) . ? C18 C19 1.367(6) . ? C20 C21 1.512(5) . ? C21 C26 1.367(5) . ? C21 C22 1.395(5) . ? C22 C23 1.384(5) . ? C23 C24 1.366(6) . ? C24 C25 1.384(7) . ? C25 C26 1.379(6) . ? 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 C5 N1 N2 113.8(3) . . ? C3 N2 N1 102.3(3) . . ? N2 C3 C4 114.3(3) . . ? N2 C3 N7 119.4(3) . . ? C4 C3 N7 126.3(3) . . ? C5 C4 C3 103.2(3) . . ? C5 C4 C20 128.2(4) . . ? C3 C4 C20 128.5(3) . . ? N1 C5 C4 106.4(4) . . ? N1 C5 C6 122.8(4) . . ? C4 C5 C6 130.8(4) . . ? C8 N7 C3 123.7(3) . . ? C8 N7 C11 111.1(3) . . ? C3 N7 C11 124.8(3) . . ? O12 C8 N7 128.8(4) . . ? O12 C8 O9 120.4(4) . . ? N7 C8 O9 110.8(3) . . ? C8 O9 C10 108.1(3) . . ? O9 C10 C11 105.2(3) . . ? N7 C11 C10 100.0(3) . . ? N7 C11 C13 112.9(3) . . ? C10 C11 C13 115.6(4) . . ? C14 C13 C11 114.2(3) . . ? C19 C14 C15 117.4(4) . . ? C19 C14 C13 122.0(4) . . ? C15 C14 C13 120.6(4) . . ? C16 C15 C14 120.1(5) . . ? C17 C16 C15 121.5(5) . . ? C18 C17 C16 118.3(5) . . ? C17 C18 C19 121.4(6) . . ? C18 C19 C14 121.2(5) . . ? C4 C20 C21 113.9(3) . . ? C26 C21 C22 119.0(4) . . ? C26 C21 C20 120.3(4) . . ? C22 C21 C20 120.6(3) . . ? C23 C22 C21 119.6(4) . . ? C24 C23 C22 121.0(5) . . ? C23 C24 C25 119.2(5) . . ? C26 C25 C24 120.0(5) . . ? C21 C26 C25 121.1(5) . . ? _diffrn_measured_fraction_theta_max 0.857 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.857 _refine_diff_density_max 0.110 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.031 data_4a _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2R)-N-(5-methyl-3-pyrazolyl)bornane-10,2-sultam ; _chemical_formula_sum 'C14 H21 N3 O2 S' _chemical_formula_weight 295.40 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.309(2) _cell_length_b 12.306(4) _cell_length_c 13.322(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.80(2) _cell_angle_gamma 90.00 _cell_volume 1475.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.40 _cell_measurement_theta_max 13.88 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega/2theta scan' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2726 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2726 _reflns_number_gt 2519 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 (Enraf-Nonius)' _computing_cell_refinement 'CAD4 (Enraf-Nonius)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.1109P] 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 none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(7) _refine_ls_number_reflns 2726 _refine_ls_number_parameters 369 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.048 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N101 N -0.0305(3) -0.2674(2) -0.44921(19) 0.0466(5) Uani 1 d . . . H101 H 0.042(5) -0.308(4) -0.463(3) 0.093(14) Uiso 1 d . . . N102 N -0.1374(2) -0.2264(2) -0.52906(17) 0.0446(5) Uani 1 d . . . C103 C -0.2096(3) -0.1591(2) -0.48270(19) 0.0384(5) Uani 1 d . . . C104 C -0.1535(4) -0.1602(3) -0.3757(2) 0.0641(9) Uani 1 d . . . H104 H -0.1880 -0.1212 -0.3268 0.077 Uiso 1 calc R . . C105 C -0.0371(4) -0.2307(3) -0.3578(2) 0.0575(8) Uani 1 d . . . C106 C 0.0700(6) -0.2697(4) -0.2603(3) 0.1012(18) Uani 1 d . . . H10A H 0.1380 -0.3206 -0.2777 0.152 Uiso 1 calc R . . H10B H 0.0162 -0.3045 -0.2166 0.152 Uiso 1 calc R . . H10C H 0.1243 -0.2090 -0.2242 0.152 Uiso 1 calc R . . N107 N -0.3336(2) -0.10206(18) -0.54292(15) 0.0365(5) Uani 1 d . . . S108 S -0.29873(7) 0.00086(6) -0.61365(5) 0.04357(18) Uani 1 d . . . C109 C -0.4862(3) 0.0462(2) -0.6543(2) 0.0454(6) Uani 1 d . . . H10D H -0.4913 0.1245 -0.6480 0.054 Uiso 1 calc R . . H10E H -0.5298 0.0261 -0.7260 0.054 Uiso 1 calc R . . C110 C -0.5678(3) -0.0096(2) -0.5828(2) 0.0380(5) Uani 1 d . . . C111 C -0.4533(3) -0.0679(2) -0.49518(19) 0.0366(6) Uani 1 d . . . H111 H -0.4148 -0.0186 -0.4367 0.044 Uiso 1 calc R . . C112 C -0.5426(3) -0.1607(2) -0.4633(2) 0.0457(6) Uani 1 d . . . H11A H -0.5102 -0.2309 -0.4823 0.055 Uiso 1 calc R . . H11B H -0.5345 -0.1596 -0.3892 0.055 Uiso 1 calc R . . C113 C -0.7014(3) -0.1347(3) -0.5260(2) 0.0502(7) Uani 1 d . . . H113 H -0.7715 -0.1947 -0.5291 0.060 Uiso 1 calc R . . C114 C -0.7497(4) -0.0288(3) -0.4846(3) 0.0620(9) Uani 1 d . . . H11C H -0.7246 -0.0287 -0.4094 0.074 Uiso 1 calc R . . H11D H -0.8559 -0.0175 -0.5108 0.074 Uiso 1 calc R . . C115 C -0.6610(4) 0.0590(3) -0.5263(3) 0.0560(8) Uani 1 d . . . H11E H -0.7266 0.1082 -0.5737 0.067 Uiso 1 calc R . . H11F H -0.5982 0.1006 -0.4700 0.067 Uiso 1 calc R . . C116 C -0.6783(3) -0.1024(2) -0.6324(2) 0.0459(6) Uani 1 d . . . C117 C -0.8179(4) -0.0576(4) -0.7099(3) 0.0736(10) Uani 1 d . . . H11G H -0.8602 -0.0006 -0.6774 0.110 Uiso 1 calc R . . H11H H -0.8892 -0.1149 -0.7306 0.110 Uiso 1 calc R . . H11I H -0.7911 -0.0293 -0.7698 0.110 Uiso 1 calc R . . C118 C -0.6147(4) -0.1914(3) -0.6881(2) 0.0572(8) Uani 1 d . . . H11J H -0.6039 -0.1642 -0.7533 0.086 Uiso 1 calc R . . H11K H -0.6808 -0.2526 -0.7002 0.086 Uiso 1 calc R . . H11L H -0.5194 -0.2134 -0.6459 0.086 Uiso 1 calc R . . O119 O -0.2414(3) -0.0386(3) -0.69553(17) 0.0732(8) Uani 1 d . . . O120 O -0.2128(3) 0.0832(2) -0.54830(19) 0.0722(7) Uani 1 d . . . N201 N -0.7590(3) 0.1526(2) -1.2630(2) 0.0546(7) Uani 1 d . . . H201 H -0.744(4) 0.199(3) -1.303(3) 0.068(12) Uiso 1 d . . . N202 N -0.6264(3) 0.1098(2) -1.2092(2) 0.0555(6) Uani 1 d . . . C203 C -0.6655(3) 0.0283(2) -1.15893(18) 0.0406(6) Uani 1 d . . . C204 C -0.8201(3) 0.0186(3) -1.1787(2) 0.0542(8) Uani 1 d . . . H204 H -0.8734 -0.0326 -1.1516 0.065 Uiso 1 calc R . . C205 C -0.8755(3) 0.1009(3) -1.2466(2) 0.0507(7) Uani 1 d . . . C206 C -1.0299(4) 0.1358(4) -1.2962(3) 0.0793(12) Uani 1 d . . . H20A H -1.0280 0.1979 -1.3394 0.119 Uiso 1 calc R . . H20B H -1.0792 0.1544 -1.2435 0.119 Uiso 1 calc R . . H20C H -1.0824 0.0775 -1.3378 0.119 Uiso 1 calc R . . N207 N -0.5576(2) -0.0384(2) -1.09510(17) 0.0423(5) Uani 1 d . . . S208 S -0.59874(8) -0.09079(7) -0.99011(5) 0.0502(2) Uani 1 d . . . C209 C -0.4184(3) -0.1423(3) -0.9345(2) 0.0550(8) Uani 1 d . . . H20D H -0.3883 -0.1263 -0.8608 0.066 Uiso 1 calc R . . H20E H -0.4164 -0.2204 -0.9437 0.066 Uiso 1 calc R . . C210 C -0.3153(3) -0.0868(2) -0.99020(19) 0.0418(6) Uani 1 d . . . C211 C -0.4027(3) 0.0007(2) -1.0646(2) 0.0423(6) Uani 1 d . . . H211 H -0.3976 0.0704 -1.0284 0.051 Uiso 1 calc R . . C212 C -0.3214(3) 0.0087(3) -1.1509(2) 0.0524(7) Uani 1 d . . . H21A H -0.2954 0.0832 -1.1620 0.063 Uiso 1 calc R . . H21B H -0.3805 -0.0212 -1.2156 0.063 Uiso 1 calc R . . C213 C -0.1817(3) -0.0609(3) -1.1059(2) 0.0525(8) Uani 1 d . . . H213 H -0.1250 -0.0797 -1.1561 0.063 Uiso 1 calc R . . C214 C -0.0906(3) -0.0042(4) -1.0078(3) 0.0710(10) Uani 1 d . . . H21C H -0.0840 0.0733 -1.0191 0.085 Uiso 1 calc R . . H21D H 0.0090 -0.0341 -0.9863 0.085 Uiso 1 calc R . . C215 C -0.1785(3) -0.0276(3) -0.9258(2) 0.0611(9) Uani 1 d . . . H21E H -0.1220 -0.0732 -0.8702 0.073 Uiso 1 calc R . . H21F H -0.2056 0.0391 -0.8965 0.073 Uiso 1 calc R . . C216 C -0.2476(3) -0.1582(3) -1.0624(2) 0.0521(7) Uani 1 d . . . C217 C -0.1296(5) -0.2389(4) -1.0023(3) 0.0852(13) Uani 1 d . . . H21G H -0.1780 -0.2977 -0.9766 0.128 Uiso 1 calc R . . H21H H -0.0640 -0.2022 -0.9450 0.128 Uiso 1 calc R . . H21I H -0.0736 -0.2670 -1.0478 0.128 Uiso 1 calc R . . C218 C -0.3595(5) -0.2249(3) -1.1426(3) 0.0720(10) Uani 1 d . . . H21J H -0.3951 -0.2841 -1.1086 0.108 Uiso 1 calc R . . H21K H -0.3122 -0.2532 -1.1933 0.108 Uiso 1 calc R . . H21L H -0.4415 -0.1796 -1.1764 0.108 Uiso 1 calc R . . O219 O -0.6308(3) -0.0072(3) -0.92466(18) 0.0829(8) Uani 1 d . . . O220 O -0.7080(3) -0.1725(3) -1.0212(2) 0.0829(9) Uani 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 N101 0.0365(11) 0.0455(13) 0.0578(14) -0.0003(12) 0.0122(10) 0.0080(10) N102 0.0374(12) 0.0497(13) 0.0469(12) -0.0027(11) 0.0108(10) 0.0075(10) C103 0.0363(12) 0.0386(13) 0.0392(12) -0.0027(11) 0.0076(10) 0.0010(11) C104 0.075(2) 0.067(2) 0.0415(15) -0.0129(15) -0.0011(14) 0.0292(18) C105 0.0564(17) 0.0546(18) 0.0509(16) -0.0085(15) -0.0055(13) 0.0151(15) C106 0.116(4) 0.097(3) 0.064(2) -0.016(2) -0.026(2) 0.056(3) N107 0.0311(10) 0.0412(12) 0.0374(10) 0.0015(10) 0.0090(8) 0.0021(9) S108 0.0380(3) 0.0541(4) 0.0388(3) 0.0059(3) 0.0102(2) -0.0068(3) C109 0.0468(15) 0.0387(14) 0.0477(14) 0.0082(12) 0.0067(12) 0.0007(12) C110 0.0357(12) 0.0309(13) 0.0467(13) 0.0020(11) 0.0092(10) 0.0029(11) C111 0.0371(12) 0.0375(14) 0.0355(12) -0.0018(10) 0.0098(10) 0.0013(11) C112 0.0484(15) 0.0418(15) 0.0516(15) 0.0077(13) 0.0213(12) 0.0023(12) C113 0.0406(14) 0.0466(16) 0.0679(18) 0.0029(14) 0.0224(14) -0.0047(12) C114 0.0519(17) 0.062(2) 0.082(2) 0.0008(17) 0.0345(17) 0.0084(15) C115 0.0538(17) 0.0423(16) 0.075(2) -0.0038(15) 0.0219(16) 0.0090(14) C116 0.0344(12) 0.0458(15) 0.0539(15) 0.0011(13) 0.0046(11) -0.0036(12) C117 0.0421(15) 0.085(3) 0.082(2) 0.007(2) -0.0048(16) -0.0031(18) C118 0.0597(18) 0.0517(17) 0.0589(17) -0.0147(15) 0.0128(14) -0.0159(15) O119 0.0664(13) 0.112(2) 0.0487(11) 0.0166(14) 0.0291(11) 0.0187(15) O120 0.0623(14) 0.0730(16) 0.0715(14) 0.0090(13) -0.0009(11) -0.0359(13) N201 0.0512(14) 0.0558(15) 0.0537(15) 0.0191(14) 0.0075(12) 0.0073(12) N202 0.0439(12) 0.0585(16) 0.0611(14) 0.0215(13) 0.0078(11) 0.0044(12) C203 0.0392(13) 0.0471(16) 0.0344(12) 0.0040(11) 0.0070(10) 0.0056(11) C204 0.0403(14) 0.066(2) 0.0561(16) 0.0197(16) 0.0119(12) 0.0068(15) C205 0.0471(15) 0.0606(18) 0.0426(15) 0.0051(14) 0.0082(12) 0.0133(15) C206 0.0500(18) 0.104(3) 0.078(2) 0.030(2) 0.0055(17) 0.020(2) N207 0.0368(11) 0.0477(13) 0.0411(11) 0.0114(10) 0.0076(9) 0.0023(10) S208 0.0402(3) 0.0670(5) 0.0439(3) 0.0163(3) 0.0115(3) 0.0019(3) C209 0.0441(14) 0.071(2) 0.0472(15) 0.0211(15) 0.0073(12) 0.0025(15) C210 0.0362(12) 0.0512(15) 0.0352(12) 0.0028(13) 0.0040(10) 0.0015(12) C211 0.0394(12) 0.0427(14) 0.0438(13) 0.0008(13) 0.0091(10) -0.0034(12) C212 0.0448(14) 0.0600(18) 0.0538(15) 0.0144(16) 0.0153(12) 0.0010(15) C213 0.0395(14) 0.075(2) 0.0443(14) 0.0031(15) 0.0128(12) 0.0049(15) C214 0.0471(16) 0.101(3) 0.0619(18) -0.001(2) 0.0078(14) -0.019(2) C215 0.0432(14) 0.090(3) 0.0457(15) -0.0084(17) 0.0029(12) -0.0082(16) C216 0.0524(16) 0.0564(18) 0.0457(14) 0.0036(14) 0.0093(13) 0.0099(15) C217 0.083(3) 0.088(3) 0.087(3) 0.023(2) 0.024(2) 0.041(2) C218 0.090(3) 0.057(2) 0.068(2) -0.0151(18) 0.0180(19) -0.0002(19) O219 0.0954(18) 0.106(2) 0.0551(13) 0.0106(15) 0.0339(13) 0.0364(18) O220 0.0570(13) 0.099(2) 0.0848(17) 0.0369(16) 0.0025(12) -0.0302(14) _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 N101 C105 1.315(4) . ? N101 N102 1.355(3) . ? N102 C103 1.315(3) . ? C103 C104 1.387(4) . ? C103 N107 1.413(3) . ? C104 C105 1.360(4) . ? C105 C106 1.500(4) . ? N107 C111 1.478(3) . ? N107 S108 1.659(2) . ? S108 O119 1.417(2) . ? S108 O120 1.438(2) . ? S108 C109 1.780(3) . ? C109 C110 1.524(4) . ? C110 C115 1.539(4) . ? C110 C111 1.542(3) . ? C110 C116 1.566(4) . ? C111 C112 1.535(4) . ? C112 C113 1.534(4) . ? C113 C114 1.526(4) . ? C113 C116 1.539(4) . ? C114 C115 1.547(5) . ? C116 C118 1.525(4) . ? C116 C117 1.540(4) . ? N201 C205 1.322(4) . ? N201 N202 1.365(3) . ? N202 C203 1.307(4) . ? C203 C204 1.400(4) . ? C203 N207 1.404(3) . ? C204 C205 1.368(4) . ? C205 C206 1.484(4) . ? N207 C211 1.475(3) . ? N207 S208 1.671(2) . ? S208 O220 1.415(3) . ? S208 O219 1.428(3) . ? S208 C209 1.770(3) . ? C209 C210 1.518(4) . ? C210 C215 1.526(4) . ? C210 C211 1.547(4) . ? C210 C216 1.550(4) . ? C211 C212 1.533(4) . ? C212 C213 1.544(4) . ? C213 C216 1.526(5) . ? C213 C214 1.533(5) . ? C214 C215 1.550(4) . ? C216 C218 1.527(5) . ? C216 C217 1.545(5) . ? 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 C105 N101 N102 113.6(2) . . ? C103 N102 N101 103.1(2) . . ? N102 C103 C104 111.9(2) . . ? N102 C103 N107 119.2(2) . . ? C104 C103 N107 128.8(2) . . ? C105 C104 C103 105.1(3) . . ? N101 C105 C104 106.2(3) . . ? N101 C105 C106 120.9(3) . . ? C104 C105 C106 132.8(3) . . ? C103 N107 C111 119.57(19) . . ? C103 N107 S108 116.85(16) . . ? C111 N107 S108 107.79(16) . . ? O119 S108 O120 116.52(16) . . ? O119 S108 N107 110.02(15) . . ? O120 S108 N107 110.68(13) . . ? O119 S108 C109 113.97(14) . . ? O120 S108 C109 108.31(15) . . ? N107 S108 C109 95.34(12) . . ? C110 C109 S108 105.96(18) . . ? C109 C110 C115 119.4(2) . . ? C109 C110 C111 108.92(19) . . ? C115 C110 C111 104.6(2) . . ? C109 C110 C116 116.3(2) . . ? C115 C110 C116 102.4(2) . . ? C111 C110 C116 103.5(2) . . ? N107 C111 C112 115.4(2) . . ? N107 C111 C110 104.94(19) . . ? C112 C111 C110 103.71(19) . . ? C113 C112 C111 102.0(2) . . ? C114 C113 C112 108.3(3) . . ? C114 C113 C116 103.6(3) . . ? C112 C113 C116 102.3(2) . . ? C113 C114 C115 103.5(2) . . ? C110 C115 C114 102.2(2) . . ? C118 C116 C113 115.2(3) . . ? C118 C116 C117 107.3(3) . . ? C113 C116 C117 114.6(2) . . ? C118 C116 C110 115.7(2) . . ? C113 C116 C110 91.8(2) . . ? C117 C116 C110 111.9(3) . . ? C205 N201 N202 113.4(3) . . ? C203 N202 N201 103.4(2) . . ? N202 C203 C204 112.1(2) . . ? N202 C203 N207 120.6(2) . . ? C204 C203 N207 127.3(3) . . ? C205 C204 C203 104.9(3) . . ? N201 C205 C204 106.2(3) . . ? N201 C205 C206 122.0(3) . . ? C204 C205 C206 131.8(3) . . ? C203 N207 C211 118.3(2) . . ? C203 N207 S208 116.83(17) . . ? C211 N207 S208 108.19(16) . . ? O220 S208 O219 116.35(19) . . ? O220 S208 N207 109.30(14) . . ? O219 S208 N207 111.20(15) . . ? O220 S208 C209 113.70(18) . . ? O219 S208 C209 109.01(16) . . ? N207 S208 C209 95.33(12) . . ? C210 C209 S208 106.5(2) . . ? C209 C210 C215 118.7(2) . . ? C209 C210 C211 109.4(2) . . ? C215 C210 C211 104.8(2) . . ? C209 C210 C216 117.2(3) . . ? C215 C210 C216 101.9(2) . . ? C211 C210 C216 103.2(2) . . ? N207 C211 C212 116.7(2) . . ? N207 C211 C210 105.5(2) . . ? C212 C211 C210 104.2(2) . . ? C211 C212 C213 101.7(2) . . ? C216 C213 C214 102.8(3) . . ? C216 C213 C212 101.6(2) . . ? C214 C213 C212 107.9(3) . . ? C213 C214 C215 103.8(3) . . ? C210 C215 C214 102.0(2) . . ? C213 C216 C218 115.2(3) . . ? C213 C216 C217 113.6(3) . . ? C218 C216 C217 106.5(3) . . ? C213 C216 C210 93.3(2) . . ? C218 C216 C210 115.3(3) . . ? C217 C216 C210 113.0(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.152 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.036