# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_2-(4-methoxybenzyl)-5-methylbenzo[d]thiazole _database_code_depnum_ccdc_archive 'CCDC 858803' #TrackingRef 'platon.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 N2 O S' _chemical_formula_weight 270.35 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 'P2(1)/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 12.7576(3) _cell_length_b 5.59810(10) _cell_length_c 21.6854(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.7180(10) _cell_angle_gamma 90.00 _cell_volume 1371.01(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9965 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 29.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9040 _exptl_absorpt_correction_T_max 0.9450 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20722 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 29.47 _reflns_number_total 3786 _reflns_number_gt 3046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0813P)^2^+0.2614P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_number_reflns 3786 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.004 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 S1 S 0.56975(4) 0.91382(8) 0.88568(2) 0.05371(15) Uani 1 1 d . . . O1 O 1.00248(11) 1.3221(3) 1.13781(7) 0.0711(4) Uani 1 1 d . . . N1 N 0.62884(13) 0.6832(3) 1.00708(7) 0.0609(4) Uani 1 1 d . . . H1N H 0.6062 0.6187 1.0305 0.073 Uiso 1 1 d R . . N2 N 0.46809(12) 0.5385(2) 0.90591(7) 0.0478(3) Uani 1 1 d . . . C1 C 0.39289(14) 0.8768(3) 0.74589(8) 0.0516(3) Uani 1 1 d . . . H1 H 0.4217 1.0110 0.7334 0.062 Uiso 1 1 calc R . . C2 C 0.44711(13) 0.7951(3) 0.81437(8) 0.0448(3) Uani 1 1 d . . . C3 C 0.40637(13) 0.5945(2) 0.83539(8) 0.0434(3) Uani 1 1 d . . . C4 C 0.30952(15) 0.4697(3) 0.78492(9) 0.0523(3) Uani 1 1 d . . . H4 H 0.2814 0.3337 0.7970 0.063 Uiso 1 1 calc R . . C5 C 0.25590(15) 0.5509(3) 0.71677(9) 0.0551(4) Uani 1 1 d . . . H5 H 0.1916 0.4668 0.6834 0.066 Uiso 1 1 calc R . . C6 C 0.23198(18) 0.8451(4) 0.62258(10) 0.0696(5) Uani 1 1 d . . . H6A H 0.1807 0.9749 0.6198 0.104 Uiso 1 1 calc R . . H6B H 0.1859 0.7184 0.5923 0.104 Uiso 1 1 calc R . . H6C H 0.2891 0.8998 0.6087 0.104 Uiso 1 1 calc R . . C7 C 0.81431(15) 1.1662(3) 1.12365(10) 0.0580(4) Uani 1 1 d . . . H7 H 0.8130 1.2709 1.1566 0.070 Uiso 1 1 calc R . . C8 C 0.90789(13) 1.1693(3) 1.10806(8) 0.0519(4) Uani 1 1 d . . . C9 C 0.90982(15) 1.0114(4) 1.06000(9) 0.0642(5) Uani 1 1 d . . . H9 H 0.9725 1.0148 1.0493 0.077 Uiso 1 1 calc R . . C10 C 0.81957(16) 0.8481(4) 1.02748(9) 0.0641(5) Uani 1 1 d . . . H10 H 0.8232 0.7374 0.9965 0.077 Uiso 1 1 calc R . . C11 C 0.72307(13) 0.8489(3) 1.04100(8) 0.0500(3) Uani 1 1 d . . . C12 C 0.72220(14) 1.0049(3) 1.08955(9) 0.0561(4) Uani 1 1 d . . . H12 H 0.6591 1.0027 1.0998 0.067 Uiso 1 1 calc R . . C13 C 1.0050(2) 1.4863(4) 1.18792(11) 0.0798(6) Uani 1 1 d . . . H13A H 0.9375 1.5901 1.1668 0.120 Uiso 1 1 calc R . . H13B H 1.0762 1.5796 1.2052 0.120 Uiso 1 1 calc R . . H13C H 1.0029 1.4010 1.2257 0.120 Uiso 1 1 calc R . . C14 C 0.55477(13) 0.6886(3) 0.93769(8) 0.0468(3) Uani 1 1 d . . . C15 C 0.29506(14) 0.7546(3) 0.69643(8) 0.0526(4) Uani 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 S1 0.0525(2) 0.0580(3) 0.0502(2) 0.00286(16) 0.02352(18) -0.01491(16) O1 0.0530(7) 0.0832(9) 0.0715(8) -0.0142(7) 0.0241(6) -0.0198(6) N1 0.0595(8) 0.0743(9) 0.0436(7) 0.0037(6) 0.0194(6) -0.0212(7) N2 0.0530(7) 0.0460(6) 0.0454(6) -0.0003(5) 0.0236(5) -0.0073(5) C1 0.0559(8) 0.0529(8) 0.0515(8) 0.0068(6) 0.0297(7) 0.0024(6) C2 0.0454(7) 0.0465(7) 0.0469(7) -0.0003(6) 0.0251(6) -0.0012(5) C3 0.0470(7) 0.0426(7) 0.0450(7) -0.0024(5) 0.0250(6) -0.0007(5) C4 0.0579(8) 0.0470(7) 0.0523(8) -0.0060(6) 0.0260(7) -0.0082(6) C5 0.0524(8) 0.0589(9) 0.0492(8) -0.0098(7) 0.0195(7) -0.0019(7) C6 0.0660(11) 0.0861(13) 0.0505(9) 0.0093(9) 0.0219(8) 0.0155(9) C7 0.0543(8) 0.0589(9) 0.0646(10) -0.0096(8) 0.0310(8) -0.0020(7) C8 0.0402(7) 0.0605(9) 0.0482(8) 0.0026(7) 0.0148(6) -0.0036(6) C9 0.0456(8) 0.0979(13) 0.0538(9) -0.0112(9) 0.0271(7) -0.0101(8) C10 0.0566(9) 0.0876(12) 0.0505(9) -0.0182(8) 0.0270(7) -0.0107(9) C11 0.0462(7) 0.0591(8) 0.0404(7) 0.0045(6) 0.0166(6) -0.0060(6) C12 0.0480(8) 0.0634(9) 0.0628(10) -0.0006(8) 0.0308(7) -0.0006(7) C13 0.0872(14) 0.0761(13) 0.0681(12) -0.0133(10) 0.0293(11) -0.0293(11) C14 0.0472(7) 0.0502(8) 0.0460(7) 0.0015(6) 0.0241(6) -0.0042(6) C15 0.0523(8) 0.0602(9) 0.0474(8) 0.0015(7) 0.0249(7) 0.0100(7) _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 S1 C2 1.7408(15) . ? S1 C14 1.7604(15) . ? O1 C8 1.371(2) . ? O1 C13 1.412(3) . ? N1 C14 1.355(2) . ? N1 C11 1.423(2) . ? N1 H1N 0.7797 . ? N2 C14 1.3018(19) . ? N2 C3 1.3917(19) . ? C1 C15 1.390(2) . ? C1 C2 1.392(2) . ? C1 H1 0.9300 . ? C2 C3 1.400(2) . ? C3 C4 1.398(2) . ? C4 C5 1.385(2) . ? C4 H4 0.9300 . ? C5 C15 1.396(3) . ? C5 H5 0.9300 . ? C6 C15 1.507(2) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.384(2) . ? C7 C12 1.391(2) . ? C7 H7 0.9300 . ? C8 C9 1.376(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 C11 1.392(2) . ? C10 H10 0.9300 . ? C11 C12 1.372(2) . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C14 88.57(7) . . ? C8 O1 C13 117.89(15) . . ? C14 N1 C11 123.00(14) . . ? C14 N1 H1N 117.1 . . ? C11 N1 H1N 116.4 . . ? C14 N2 C3 110.10(12) . . ? C15 C1 C2 118.94(15) . . ? C15 C1 H1 120.5 . . ? C2 C1 H1 120.5 . . ? C1 C2 C3 122.38(14) . . ? C1 C2 S1 128.13(12) . . ? C3 C2 S1 109.49(11) . . ? N2 C3 C4 126.17(13) . . ? N2 C3 C2 115.61(13) . . ? C4 C3 C2 118.21(14) . . ? C5 C4 C3 119.32(15) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C15 122.23(15) . . ? C4 C5 H5 118.9 . . ? C15 C5 H5 118.9 . . ? C15 C6 H6A 109.5 . . ? C15 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C15 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 119.33(16) . . ? C8 C7 H7 120.3 . . ? C12 C7 H7 120.3 . . ? O1 C8 C9 115.81(14) . . ? O1 C8 C7 124.30(16) . . ? C9 C8 C7 119.89(15) . . ? C8 C9 C10 120.55(15) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 119.98(17) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 119.18(15) . . ? C12 C11 N1 120.35(15) . . ? C10 C11 N1 120.42(16) . . ? C11 C12 C7 120.99(15) . . ? C11 C12 H12 119.5 . . ? C7 C12 H12 119.5 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 N1 123.74(14) . . ? N2 C14 S1 116.20(11) . . ? N1 C14 S1 120.02(11) . . ? C1 C15 C5 118.89(15) . . ? C1 C15 C6 119.92(17) . . ? C5 C15 C6 121.18(16) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.789 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.043 data_nk-2-82-u _database_code_depnum_ccdc_archive 'CCDC 878730' #TrackingRef 'Chek Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 I N2 S' _chemical_formula_sum 'C15 H13 I N2 S' _chemical_formula_weight 380.24 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' I I -0.4742 1.8119 '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 10.3691(3) _cell_length_b 17.6590(5) _cell_length_c 8.2111(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.2050(10) _cell_angle_gamma 90.00 _cell_volume 1491.65(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 2.274 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.400 _exptl_absorpt_correction_T_max 0.529 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17440 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.62 _reflns_number_total 3452 _reflns_number_gt 2792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0470P)^2^+0.5064P] 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 3270 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 I1 I 0.15364(2) 0.065999(10) 0.35755(3) 0.05588(10) Uani 1 1 d . . . C7 C 0.3269(2) 0.29164(13) 0.4162(3) 0.0341(5) Uani 1 1 d . . . C6 C 0.5170(2) 0.37499(14) 0.4584(3) 0.0368(5) Uani 1 1 d . . . C3 C 0.6088(3) 0.44074(16) 0.7520(4) 0.0490(7) Uani 1 1 d . . . H3 H 0.6404 0.4627 0.8520 0.059 Uiso 1 1 calc R . . C13 C 0.0454(3) 0.29622(15) 0.4680(3) 0.0425(6) Uani 1 1 d . . . H13 H 0.0800 0.3446 0.4614 0.051 Uiso 1 1 calc R . . C9 C 0.0584(2) 0.16291(14) 0.4302(3) 0.0377(5) Uani 1 1 d . . . C10 C -0.0615(3) 0.15395(16) 0.4877(3) 0.0459(6) Uani 1 1 d . . . H10 H -0.0970 0.1058 0.4932 0.055 Uiso 1 1 calc R . . C5 C 0.4513(2) 0.36294(13) 0.5945(3) 0.0352(5) Uani 1 1 d . . . C12 C -0.0725(3) 0.28693(16) 0.5279(3) 0.0454(6) Uani 1 1 d . . . H12 H -0.1149 0.3292 0.5628 0.055 Uiso 1 1 calc R . . C11 C -0.1288(2) 0.21646(17) 0.5371(3) 0.0456(6) Uani 1 1 d . . . C4 C 0.4991(3) 0.39577(16) 0.7435(3) 0.0455(6) Uani 1 1 d . . . H4 H 0.4579 0.3876 0.8363 0.055 Uiso 1 1 calc R . . C8 C 0.1132(2) 0.23393(14) 0.4174(3) 0.0350(5) Uani 1 1 d . . . C1 C 0.6274(3) 0.42055(15) 0.4678(4) 0.0432(6) Uani 1 1 d . . . H1 H 0.6694 0.4283 0.3756 0.052 Uiso 1 1 calc R . . C2 C 0.6739(3) 0.45436(15) 0.6163(4) 0.0437(6) Uani 1 1 d . . . N2 N 0.2310(2) 0.24456(12) 0.3497(3) 0.0404(5) Uani 1 1 d . . . H2N H 0.2423 0.2200 0.2622 0.049 Uiso 1 1 calc R . . S1 S 0.44107(7) 0.32469(4) 0.29027(8) 0.04459(17) Uani 1 1 d . . . N1 N 0.34211(19) 0.31590(11) 0.5662(2) 0.0351(4) Uani 1 1 d . . . C15 C -0.2599(3) 0.2066(2) 0.5992(4) 0.0635(9) Uani 1 1 d . . . H15A H -0.2702 0.2447 0.6800 0.095 Uiso 1 1 calc R . . H15B H -0.2642 0.1573 0.6477 0.095 Uiso 1 1 calc R . . H15C H -0.3280 0.2115 0.5092 0.095 Uiso 1 1 calc R . . C14 C 0.7918(3) 0.50450(18) 0.6293(4) 0.0591(8) Uani 1 1 d . . . H14A H 0.7962 0.5292 0.5260 0.089 Uiso 1 1 calc R . . H14B H 0.8685 0.4744 0.6572 0.089 Uiso 1 1 calc R . . H14C H 0.7861 0.5419 0.7130 0.089 Uiso 1 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 I1 0.05850(16) 0.03873(13) 0.07321(18) 0.00314(8) 0.01924(11) 0.00288(7) C7 0.0328(12) 0.0349(12) 0.0362(12) 0.0031(9) 0.0103(9) -0.0010(9) C6 0.0345(12) 0.0361(12) 0.0408(14) 0.0008(9) 0.0084(10) -0.0011(9) C3 0.0460(16) 0.0542(17) 0.0453(16) -0.0036(11) -0.0001(12) -0.0081(12) C13 0.0393(13) 0.0406(13) 0.0482(15) -0.0063(11) 0.0080(11) -0.0074(10) C9 0.0373(12) 0.0385(12) 0.0376(13) 0.0014(10) 0.0064(10) -0.0022(10) C10 0.0444(14) 0.0465(15) 0.0479(15) 0.0047(11) 0.0104(12) -0.0104(11) C5 0.0319(11) 0.0360(12) 0.0382(13) 0.0030(9) 0.0058(9) -0.0009(9) C12 0.0368(13) 0.0521(16) 0.0478(16) -0.0072(11) 0.0069(11) 0.0037(11) C11 0.0340(13) 0.0646(17) 0.0389(14) -0.0007(11) 0.0079(10) -0.0045(12) C4 0.0436(14) 0.0557(16) 0.0373(14) 0.0013(11) 0.0057(11) -0.0076(12) C8 0.0355(12) 0.0390(12) 0.0314(12) -0.0015(9) 0.0078(9) -0.0069(10) C1 0.0384(14) 0.0440(14) 0.0488(15) 0.0044(11) 0.0118(11) -0.0067(11) C2 0.0347(13) 0.0370(13) 0.0587(17) 0.0044(11) 0.0025(11) -0.0036(10) N2 0.0407(11) 0.0447(12) 0.0386(12) -0.0106(9) 0.0157(9) -0.0113(9) S1 0.0442(4) 0.0544(4) 0.0384(3) -0.0060(3) 0.0178(3) -0.0149(3) N1 0.0342(10) 0.0389(11) 0.0331(11) 0.0009(8) 0.0074(8) -0.0061(8) C15 0.0400(16) 0.089(2) 0.066(2) -0.0018(17) 0.0213(14) -0.0088(15) C14 0.0442(16) 0.0566(18) 0.075(2) 0.0026(15) 0.0015(14) -0.0149(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 I1 C9 2.099(2) . ? C7 N1 1.294(3) . ? C7 N2 1.357(3) . ? C7 S1 1.766(2) . ? C6 C1 1.393(3) . ? C6 C5 1.396(3) . ? C6 S1 1.744(3) . ? C3 C4 1.382(4) . ? C3 C2 1.394(4) . ? C13 C12 1.383(4) . ? C13 C8 1.397(4) . ? C9 C8 1.386(3) . ? C9 C10 1.394(3) . ? C10 C11 1.393(4) . ? C5 C4 1.388(4) . ? C5 N1 1.400(3) . ? C12 C11 1.381(4) . ? C11 C15 1.521(4) . ? C8 N2 1.417(3) . ? C1 C2 1.389(4) . ? C2 C14 1.502(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C7 N2 125.6(2) . . ? N1 C7 S1 115.90(18) . . ? N2 C7 S1 118.53(18) . . ? C1 C6 C5 121.5(2) . . ? C1 C6 S1 128.6(2) . . ? C5 C6 S1 109.81(17) . . ? C4 C3 C2 122.5(3) . . ? C12 C13 C8 120.8(2) . . ? C8 C9 C10 121.3(2) . . ? C8 C9 I1 120.29(18) . . ? C10 C9 I1 118.37(18) . . ? C11 C10 C9 120.6(2) . . ? C4 C5 C6 119.1(2) . . ? C4 C5 N1 125.9(2) . . ? C6 C5 N1 115.0(2) . . ? C11 C12 C13 121.7(3) . . ? C12 C11 C10 117.9(2) . . ? C12 C11 C15 121.6(3) . . ? C10 C11 C15 120.5(3) . . ? C3 C4 C5 119.0(3) . . ? C9 C8 C13 117.6(2) . . ? C9 C8 N2 122.1(2) . . ? C13 C8 N2 120.2(2) . . ? C2 C1 C6 119.3(3) . . ? C1 C2 C3 118.5(2) . . ? C1 C2 C14 120.4(3) . . ? C3 C2 C14 121.1(3) . . ? C7 N2 C8 123.2(2) . . ? C6 S1 C7 88.52(11) . . ? C7 N1 C5 110.75(19) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.582 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.081