# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dapbip _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N2 O2 S, 0.5 (C10 H8 N2)' _chemical_formula_sum 'C17 H16 N3 O2 S' _chemical_formula_weight 326.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 21/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 5.8451(3) _cell_length_b 7.7034(4) _cell_length_c 34.6478(16) _cell_angle_alpha 90.00 _cell_angle_beta 91.116(2) _cell_angle_gamma 90.00 _cell_volume 1559.80(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 30.290 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details 'SADABS (Bruker,2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18138 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 30.29 _reflns_number_total 4662 _reflns_number_gt 3593 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER SMART (Bruker, 2005)' _computing_cell_refinement 'BRUKER SMART (Bruker, 2005)' _computing_data_reduction 'BRUKER SAINT (Bruker, 2005)' _computing_structure_solution 'SIR 97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP 3.2 (Farrugia, 1997) and Mercury 3.0' _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^ > 2\s(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^)+(0.0618P)^2^+0.4139P] 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_extinction_coef ? _refine_ls_number_reflns 4662 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 C1 C -0.0381(3) -0.3656(2) 0.13606(4) 0.0212(3) Uani 1 1 d . . . C2 C -0.1815(3) -0.2213(2) 0.13489(4) 0.0228(3) Uani 1 1 d . . . H2 H -0.3222 -0.2245 0.1469 0.027 Uiso 1 1 calc R . . C3 C -0.1137(3) -0.0735(2) 0.11576(5) 0.0241(3) Uani 1 1 d . . . H3 H -0.2100 0.0226 0.1149 0.029 Uiso 1 1 calc R . . C4 C 0.0984(3) -0.0662(2) 0.09757(5) 0.0248(3) Uani 1 1 d . . . C5 C 0.2400(3) -0.2127(2) 0.09929(5) 0.0271(3) Uani 1 1 d . . . H5 H 0.3811 -0.2102 0.0873 0.032 Uiso 1 1 calc R . . C6 C 0.1735(3) -0.3601(2) 0.11840(5) 0.0261(3) Uani 1 1 d . . . H6 H 0.2699 -0.4562 0.1195 0.031 Uiso 1 1 calc R . . C7 C -0.0600(3) -0.5198(2) 0.20929(4) 0.0218(3) Uani 1 1 d . . . C8 C -0.2220(3) -0.4422(2) 0.23277(5) 0.0247(3) Uani 1 1 d . . . H8 H -0.3626 -0.4074 0.2224 0.030 Uiso 1 1 calc R . . C9 C -0.1728(3) -0.4174(2) 0.27144(5) 0.0253(3) Uani 1 1 d . . . H9 H -0.2818 -0.3670 0.2871 0.030 Uiso 1 1 calc R . . C10 C 0.0389(3) -0.4670(2) 0.28741(5) 0.0232(3) Uani 1 1 d . . . C11 C 0.1984(3) -0.5485(2) 0.26371(5) 0.0253(3) Uani 1 1 d . . . H11 H 0.3375 -0.5860 0.2742 0.030 Uiso 1 1 calc R . . C12 C 0.1502(3) -0.5733(2) 0.22495(5) 0.0246(3) Uani 1 1 d . . . H12 H 0.2577 -0.6256 0.2093 0.029 Uiso 1 1 calc R . . C13 C 0.6228(4) 0.3682(3) 0.05296(7) 0.0597(7) Uani 1 1 d . . . H13 H 0.5314 0.4037 0.0732 0.072 Uiso 1 1 calc R . . C14 C 0.7769(4) 0.4866(3) 0.03859(7) 0.0579(7) Uani 1 1 d . . . H14 H 0.7871 0.5975 0.0491 0.069 Uiso 1 1 calc R . . C15 C 0.9160(3) 0.4390(2) 0.00845(5) 0.0282(4) Uani 1 1 d . . . C16 C 0.8941(3) 0.2696(3) -0.00424(5) 0.0353(4) Uani 1 1 d . . . H16 H 0.9873 0.2288 -0.0237 0.042 Uiso 1 1 calc R . . C17 C 0.7346(3) 0.1608(3) 0.01183(6) 0.0397(5) Uani 1 1 d . . . H17 H 0.7234 0.0480 0.0024 0.048 Uiso 1 1 calc R . . N1 N 0.1612(3) 0.0798(2) 0.07819(5) 0.0344(4) Uani 1 1 d . . . N2 N 0.0857(3) -0.4390(2) 0.32617(4) 0.0303(3) Uani 1 1 d . . . N3 N 0.5960(3) 0.2073(2) 0.03996(5) 0.0396(4) Uani 1 1 d . . . O1 O -0.3688(2) -0.56917(15) 0.15594(3) 0.0292(3) Uani 1 1 d . . . O2 O 0.0169(2) -0.69448(15) 0.14702(3) 0.0310(3) Uani 1 1 d . . . S1 S -0.12283(7) -0.55280(5) 0.160305(11) 0.02293(11) Uani 1 1 d . . . H1N1 H 0.091(4) 0.172(3) 0.0840(6) 0.045(6) Uiso 1 1 d . . . H1N2 H 0.005(4) -0.353(3) 0.3348(6) 0.041(6) Uiso 1 1 d . . . H2N1 H 0.295(4) 0.085(3) 0.0711(7) 0.043(6) Uiso 1 1 d . . . H2N2 H 0.231(4) -0.442(3) 0.3331(7) 0.045(7) 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 C1 0.0202(7) 0.0221(7) 0.0211(7) -0.0023(6) -0.0017(5) 0.0012(6) C2 0.0195(7) 0.0230(7) 0.0260(8) -0.0027(6) 0.0037(6) 0.0017(6) C3 0.0227(8) 0.0209(7) 0.0289(8) -0.0017(6) 0.0033(6) 0.0028(6) C4 0.0266(8) 0.0269(8) 0.0210(7) -0.0040(6) 0.0020(6) -0.0030(6) C5 0.0198(8) 0.0358(9) 0.0258(8) -0.0043(7) 0.0036(6) 0.0011(6) C6 0.0210(8) 0.0292(8) 0.0280(8) -0.0039(6) -0.0005(6) 0.0076(6) C7 0.0222(8) 0.0177(7) 0.0254(7) -0.0011(6) -0.0022(6) 0.0004(5) C8 0.0192(8) 0.0227(7) 0.0320(8) -0.0013(6) -0.0026(6) 0.0036(6) C9 0.0235(8) 0.0230(7) 0.0295(8) -0.0028(6) 0.0037(6) 0.0010(6) C10 0.0247(8) 0.0195(7) 0.0253(7) 0.0029(6) -0.0005(6) -0.0073(6) C11 0.0190(7) 0.0273(8) 0.0295(8) 0.0024(6) -0.0042(6) 0.0002(6) C12 0.0213(8) 0.0234(7) 0.0290(8) -0.0012(6) -0.0006(6) 0.0037(6) C13 0.0663(16) 0.0529(14) 0.0617(15) -0.0129(12) 0.0434(13) -0.0179(12) C14 0.0702(16) 0.0411(11) 0.0640(15) -0.0195(11) 0.0443(13) -0.0189(11) C15 0.0285(9) 0.0342(9) 0.0222(8) -0.0026(7) 0.0046(6) -0.0058(7) C16 0.0363(10) 0.0384(10) 0.0314(9) -0.0068(8) 0.0105(8) -0.0055(8) C17 0.0417(11) 0.0365(10) 0.0412(11) -0.0057(8) 0.0076(8) -0.0110(8) N1 0.0332(9) 0.0312(8) 0.0395(9) 0.0026(7) 0.0141(7) -0.0021(7) N2 0.0301(8) 0.0352(8) 0.0257(7) 0.0019(6) -0.0007(6) -0.0069(7) N3 0.0361(9) 0.0440(9) 0.0389(9) 0.0011(7) 0.0088(7) -0.0103(7) O1 0.0247(6) 0.0285(6) 0.0342(6) 0.0022(5) -0.0080(5) -0.0043(5) O2 0.0400(7) 0.0209(6) 0.0318(6) -0.0064(5) -0.0042(5) 0.0075(5) S1 0.0239(2) 0.01885(18) 0.0259(2) -0.00247(14) -0.00371(14) 0.00187(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C6 1.391(2) . ? C1 C2 1.392(2) . ? C1 S1 1.7455(16) . ? C2 C3 1.380(2) . ? C3 C4 1.403(2) . ? C4 N1 1.363(2) . ? C4 C5 1.400(2) . ? C5 C6 1.375(2) . ? C7 C8 1.395(2) . ? C7 C12 1.395(2) . ? C7 S1 1.7483(16) . ? C8 C9 1.378(2) . ? C9 C10 1.399(2) . ? C10 N2 1.382(2) . ? C10 C11 1.403(2) . ? C11 C12 1.380(2) . ? C13 N3 1.327(3) . ? C13 C14 1.381(3) . ? C14 C15 1.386(2) . ? C15 C16 1.382(2) . ? C15 C15 1.487(3) 3_765 ? C16 C17 1.379(3) . ? C17 N3 1.329(2) . ? O1 S1 1.4479(12) . ? O2 S1 1.4441(12) . ? 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 C6 C1 C2 120.20(15) . . ? C6 C1 S1 119.97(12) . . ? C2 C1 S1 119.83(12) . . ? C3 C2 C1 119.65(14) . . ? C2 C3 C4 120.90(15) . . ? N1 C4 C5 121.38(16) . . ? N1 C4 C3 120.21(16) . . ? C5 C4 C3 118.40(15) . . ? C6 C5 C4 120.92(15) . . ? C5 C6 C1 119.93(15) . . ? C8 C7 C12 120.17(15) . . ? C8 C7 S1 119.74(12) . . ? C12 C7 S1 120.08(12) . . ? C9 C8 C7 119.67(15) . . ? C8 C9 C10 120.86(15) . . ? N2 C10 C9 119.90(16) . . ? N2 C10 C11 121.16(15) . . ? C9 C10 C11 118.92(15) . . ? C12 C11 C10 120.43(15) . . ? C11 C12 C7 119.91(15) . . ? N3 C13 C14 124.6(2) . . ? C13 C14 C15 119.5(2) . . ? C16 C15 C14 115.95(16) . . ? C16 C15 C15 121.94(19) . 3_765 ? C14 C15 C15 122.1(2) . 3_765 ? C17 C16 C15 120.29(17) . . ? N3 C17 C16 124.01(19) . . ? C13 N3 C17 115.53(17) . . ? O2 S1 O1 117.87(7) . . ? O2 S1 C1 107.67(7) . . ? O1 S1 C1 108.18(7) . . ? O2 S1 C7 108.06(7) . . ? O1 S1 C7 107.67(7) . . ? C1 S1 C7 106.90(7) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.29 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.428 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 948443' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dapcapro _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N2 O2 S, C6 H11 N O' _chemical_formula_sum 'C18 H23 N3 O3 S' _chemical_formula_weight 361.45 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 21/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 8.2700(6) _cell_length_b 37.058(3) _cell_length_c 5.9595(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.089(4) _cell_angle_gamma 90.00 _cell_volume 1803.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 28.160 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.986 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'SADABS (Bruker,2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16909 _diffrn_reflns_av_R_equivalents 0.0982 _diffrn_reflns_av_sigmaI/netI 0.1239 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 49 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 28.16 _reflns_number_total 4375 _reflns_number_gt 2360 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER SMART (Bruker, 2005)' _computing_cell_refinement 'BRUKER SMART (Bruker, 2005)' _computing_data_reduction 'BRUKER SAINT (Bruker, 2005)' _computing_structure_solution 'SIR 97 (Altomare et al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP 3.2 (Farrugia, 1997) and Mercury 3.0' _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^ > 2\s(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^)+(0.0409P)^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 0.0072(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4375 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1363 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _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 C1 C 0.2355(2) 0.13889(7) 0.5052(4) 0.0201(6) Uani 1 1 d . . . C2 C 0.1994(3) 0.11236(8) 0.6534(4) 0.0243(6) Uani 1 1 d . . . H2 H 0.1636 0.1189 0.7880 0.029 Uiso 1 1 calc R . . C3 C 0.2160(3) 0.07654(8) 0.6040(4) 0.0266(6) Uani 1 1 d . . . H3 H 0.1902 0.0590 0.7044 0.032 Uiso 1 1 calc R . . C4 C 0.2716(3) 0.06610(8) 0.4028(4) 0.0252(6) Uani 1 1 d . . . C5 C 0.3087(3) 0.09310(8) 0.2566(4) 0.0283(6) Uani 1 1 d . . . H5 H 0.3467 0.0867 0.1232 0.034 Uiso 1 1 calc R . . C6 C 0.2902(3) 0.12897(7) 0.3051(4) 0.0251(6) Uani 1 1 d . . . H6 H 0.3143 0.1466 0.2043 0.030 Uiso 1 1 calc R . . C7 C 0.0099(3) 0.19517(6) 0.4309(4) 0.0186(5) Uani 1 1 d . . . C8 C -0.1256(3) 0.18670(7) 0.5336(4) 0.0211(6) Uani 1 1 d . . . H8 H -0.1108 0.1757 0.6756 0.025 Uiso 1 1 calc R . . C9 C -0.2803(3) 0.19452(7) 0.4262(4) 0.0261(6) Uani 1 1 d . . . H9 H -0.3698 0.1891 0.4971 0.031 Uiso 1 1 calc R . . C10 C -0.3055(3) 0.21055(7) 0.2116(4) 0.0249(6) Uani 1 1 d . . . C11 C -0.1684(3) 0.21826(7) 0.1077(4) 0.0253(6) Uani 1 1 d . . . H11 H -0.1830 0.2286 -0.0362 0.030 Uiso 1 1 calc R . . C12 C -0.0125(3) 0.21061(7) 0.2167(4) 0.0235(6) Uani 1 1 d . . . H12 H 0.0775 0.2158 0.1464 0.028 Uiso 1 1 calc R . . C13 C 0.6972(3) 0.03426(7) 1.1084(4) 0.0245(6) Uani 1 1 d . . . C14 C 0.8496(3) 0.05562(7) 1.1965(4) 0.0302(7) Uani 1 1 d . . . H14A H 0.9284 0.0524 1.0937 0.036 Uiso 1 1 calc R . . H14B H 0.8976 0.0460 1.3433 0.036 Uiso 1 1 calc R . . C15 C 0.8193(3) 0.09569(7) 1.2215(4) 0.0317(7) Uani 1 1 d . . . H15A H 0.9070 0.1055 1.3318 0.038 Uiso 1 1 calc R . . H15B H 0.7180 0.0988 1.2820 0.038 Uiso 1 1 calc R . . C16 C 0.8084(3) 0.11745(7) 1.0037(4) 0.0314(7) Uani 1 1 d . . . H16A H 0.7979 0.1428 1.0402 0.038 Uiso 1 1 calc R . . H16B H 0.9102 0.1146 0.9441 0.038 Uiso 1 1 calc R . . C17 C 0.6678(3) 0.10733(8) 0.8186(4) 0.0312(7) Uani 1 1 d . . . H17A H 0.5653 0.1122 0.8725 0.037 Uiso 1 1 calc R . . H17B H 0.6720 0.1226 0.6872 0.037 Uiso 1 1 calc R . . C18 C 0.6694(3) 0.06829(8) 0.7455(4) 0.0309(7) Uani 1 1 d . . . H18A H 0.5991 0.0658 0.5999 0.037 Uiso 1 1 calc R . . H18B H 0.7798 0.0620 0.7239 0.037 Uiso 1 1 calc R . . N1 N 0.2830(3) 0.03018(7) 0.3496(5) 0.0359(6) Uani 1 1 d . . . N2 N -0.4591(3) 0.21972(8) 0.1088(6) 0.0497(8) Uani 1 1 d . . . N3 N 0.6158(3) 0.04266(6) 0.9049(3) 0.0253(5) Uani 1 1 d . . . O1 O 0.20749(19) 0.18661(5) 0.8108(3) 0.0338(5) Uani 1 1 d . . . O2 O 0.32211(18) 0.20540(5) 0.4670(3) 0.0346(5) Uani 1 1 d . . . O3 O 0.6464(2) 0.01038(5) 1.2262(3) 0.0364(5) Uani 1 1 d . . . S1 S 0.20640(7) 0.184385(19) 0.56912(11) 0.02496(19) Uani 1 1 d . . . H1N1 H 0.286(3) 0.0123(8) 0.472(5) 0.047(9) Uiso 1 1 d . . . H1N2 H -0.547(4) 0.2128(8) 0.168(5) 0.058(10) Uiso 1 1 d . . . H1N3 H 0.532(3) 0.0281(8) 0.866(4) 0.044(9) Uiso 1 1 d . . . H2N1 H 0.339(3) 0.0263(8) 0.255(5) 0.051(11) Uiso 1 1 d . . . H2N2 H -0.473(3) 0.2286(8) -0.019(5) 0.040(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 C1 0.0141(11) 0.0214(16) 0.0236(13) 0.0012(12) -0.0001(9) 0.0032(10) C2 0.0190(12) 0.0300(18) 0.0237(13) -0.0007(13) 0.0025(10) 0.0040(11) C3 0.0244(12) 0.0283(17) 0.0263(14) 0.0102(13) 0.0015(11) 0.0010(12) C4 0.0228(12) 0.0254(17) 0.0260(14) 0.0016(14) 0.0000(10) 0.0064(11) C5 0.0315(13) 0.0292(19) 0.0253(14) 0.0024(14) 0.0076(11) 0.0092(12) C6 0.0226(12) 0.0275(18) 0.0259(14) 0.0064(13) 0.0060(10) 0.0054(12) C7 0.0167(11) 0.0153(15) 0.0241(13) -0.0013(11) 0.0036(9) 0.0023(10) C8 0.0221(11) 0.0159(15) 0.0258(13) 0.0011(12) 0.0058(10) 0.0025(11) C9 0.0188(12) 0.0203(16) 0.0406(15) 0.0023(13) 0.0087(11) -0.0008(11) C10 0.0186(12) 0.0183(15) 0.0353(15) 0.0031(13) -0.0031(10) -0.0002(11) C11 0.0317(13) 0.0202(16) 0.0233(13) 0.0018(12) 0.0023(11) 0.0031(12) C12 0.0255(12) 0.0193(16) 0.0280(14) -0.0057(12) 0.0110(11) 0.0002(11) C13 0.0235(12) 0.0201(16) 0.0294(14) -0.0010(13) 0.0028(11) 0.0006(11) C14 0.0263(13) 0.0292(18) 0.0319(15) 0.0039(13) -0.0055(11) -0.0050(12) C15 0.0318(14) 0.0294(19) 0.0312(15) -0.0043(14) -0.0033(11) -0.0091(12) C16 0.0347(14) 0.0243(17) 0.0354(15) -0.0025(14) 0.0058(12) -0.0059(12) C17 0.0342(14) 0.0264(18) 0.0336(16) 0.0093(14) 0.0067(12) -0.0011(12) C18 0.0331(14) 0.0342(19) 0.0247(14) 0.0006(14) 0.0027(11) -0.0078(13) N1 0.0477(15) 0.0254(17) 0.0356(15) 0.0000(14) 0.0095(12) 0.0087(12) N2 0.0239(13) 0.060(2) 0.061(2) 0.0270(17) -0.0052(13) 0.0013(13) N3 0.0250(11) 0.0209(14) 0.0288(12) 0.0023(11) 0.0008(9) -0.0070(10) O1 0.0294(9) 0.0425(13) 0.0267(10) -0.0122(9) -0.0038(7) 0.0065(9) O2 0.0172(9) 0.0302(12) 0.0570(13) -0.0020(10) 0.0078(8) -0.0072(8) O3 0.0402(11) 0.0278(12) 0.0380(11) 0.0089(10) -0.0034(9) -0.0124(9) S1 0.0160(3) 0.0267(4) 0.0312(4) -0.0043(3) 0.0006(2) 0.0003(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C2 1.385(3) . ? C1 C6 1.390(3) . ? C1 S1 1.754(3) . ? C2 C3 1.371(4) . ? C3 C4 1.405(3) . ? C4 N1 1.375(3) . ? C4 C5 1.392(3) . ? C5 C6 1.374(3) . ? C7 C12 1.384(3) . ? C7 C8 1.395(3) . ? C7 S1 1.748(2) . ? C8 C9 1.368(3) . ? C9 C10 1.396(3) . ? C10 N2 1.364(3) . ? C10 C11 1.404(3) . ? C11 C12 1.378(3) . ? C13 O3 1.243(3) . ? C13 N3 1.328(3) . ? C13 C14 1.510(3) . ? C14 C15 1.517(4) . ? C15 C16 1.519(3) . ? C16 C17 1.518(3) . ? C17 C18 1.511(4) . ? C18 N3 1.460(3) . ? O1 S1 1.4412(16) . ? O2 S1 1.4412(17) . ? 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 C1 C6 119.4(2) . . ? C2 C1 S1 119.55(19) . . ? C6 C1 S1 121.00(19) . . ? C3 C2 C1 120.7(2) . . ? C2 C3 C4 120.5(2) . . ? N1 C4 C5 121.4(2) . . ? N1 C4 C3 120.5(2) . . ? C5 C4 C3 118.1(3) . . ? C6 C5 C4 121.4(2) . . ? C5 C6 C1 119.9(2) . . ? C12 C7 C8 119.8(2) . . ? C12 C7 S1 120.56(17) . . ? C8 C7 S1 119.57(18) . . ? C9 C8 C7 120.3(2) . . ? C8 C9 C10 120.8(2) . . ? N2 C10 C9 120.7(2) . . ? N2 C10 C11 120.7(2) . . ? C9 C10 C11 118.5(2) . . ? C12 C11 C10 120.7(2) . . ? C11 C12 C7 119.9(2) . . ? O3 C13 N3 121.0(2) . . ? O3 C13 C14 121.0(2) . . ? N3 C13 C14 118.0(2) . . ? C13 C14 C15 113.9(2) . . ? C14 C15 C16 115.1(2) . . ? C17 C16 C15 115.2(2) . . ? C18 C17 C16 113.9(2) . . ? N3 C18 C17 114.7(2) . . ? C13 N3 C18 125.8(2) . . ? O1 S1 O2 119.43(11) . . ? O1 S1 C7 108.45(10) . . ? O2 S1 C7 107.89(11) . . ? O1 S1 C1 107.02(11) . . ? O2 S1 C1 107.75(11) . . ? C7 S1 C1 105.47(11) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.16 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.279 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 948444'