# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email patel@iitg.ernet.in _publ_contact_author_name 'Bhisma Patel' loop_ _publ_author_name 'Bhisma Patel' 'Saroj Rout' 'Srimant Guin' 'Jayashree Nath' data_10q _database_code_depnum_ccdc_archive 'CCDC 829313' #TrackingRef '- BT final cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N2 S' _chemical_formula_weight 253.34 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M ' I 41' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x+1/2, z+1/4' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-y+1/2, x+1, z+3/4' '-x+1, -y+1, z+1' 'y+1, -x+1/2, z+5/4' _cell_length_a 14.9330(16) _cell_length_b 14.9330(16) _cell_length_c 12.2771(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2737.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2645 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 21.01 _exptl_crystal_description Rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064.0 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.914 _exptl_absorpt_correction_T_max 0.946 _exptl_absorpt_process_details multi-sca _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 11792 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 26.15 _reflns_number_total 2726 _reflns_number_gt 2243 _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^)+(0.0950P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.96(10) _refine_ls_number_reflns 2655 _refine_ls_number_parameters 165 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.61732(4) 0.22042(4) 0.24809(6) 0.0739(2) Uani 1 1 d . . . N1 N 0.49195(16) 0.12105(13) 0.33385(19) 0.0695(5) Uani 1 1 d . . . N2 N 0.61471(17) 0.03931(15) 0.27237(19) 0.0770(6) Uani 1 1 d . . . C5 C 0.3854(2) 0.23729(19) 0.3915(2) 0.0747(7) Uani 1 1 d . . . H5 H 0.3451 0.1959 0.4197 0.090 Uiso 1 1 calc R . . C4 C 0.3674(2) 0.3303(2) 0.3964(3) 0.0815(8) Uani 1 1 d . . . H4 H 0.3148 0.3500 0.4292 0.098 Uiso 1 1 calc R . . C3 C 0.4255(2) 0.39147(19) 0.3541(3) 0.0853(9) Uani 1 1 d . . . H3 H 0.4123 0.4522 0.3591 0.102 Uiso 1 1 calc R . . C2 C 0.5031(2) 0.36458(19) 0.3045(3) 0.0813(8) Uani 1 1 d . . . H2 H 0.5417 0.4063 0.2735 0.098 Uiso 1 1 calc R . . C1 C 0.52298(19) 0.27376(17) 0.3013(2) 0.0654(6) Uani 1 1 d . . . C6 C 0.46464(17) 0.20977(15) 0.3435(2) 0.0634(6) Uani 1 1 d . . . C7 C 0.57004(18) 0.11727(16) 0.2879(2) 0.0649(6) Uani 1 1 d . . . C8 C 0.70109(18) 0.0330(2) 0.2180(3) 0.0765(7) Uani 1 1 d . . . H8 H 0.7384 0.0829 0.2431 0.092 Uiso 1 1 calc R . . C9 C 0.7457(3) -0.0532(3) 0.2525(4) 0.1178(14) Uani 1 1 d . . . H9A H 0.7507 -0.0547 0.3304 0.177 Uiso 1 1 calc R . . H9B H 0.8044 -0.0566 0.2207 0.177 Uiso 1 1 calc R . . H9C H 0.7105 -0.1031 0.2282 0.177 Uiso 1 1 calc R . . C10 C 0.69415(16) 0.03858(16) 0.0957(2) 0.0662(6) Uani 1 1 d . . . C11 C 0.7566(3) 0.0860(3) 0.0372(4) 0.1159(13) Uani 1 1 d . . . H11 H 0.8005 0.1193 0.0725 0.139 Uiso 1 1 calc R . . C12 C 0.7527(4) 0.0831(4) -0.0788(6) 0.151(2) Uani 1 1 d . . . H12 H 0.7944 0.1150 -0.1196 0.181 Uiso 1 1 calc R . . C15 C 0.6305(4) -0.0076(3) 0.0390(3) 0.1174(15) Uani 1 1 d . . . H15 H 0.5871 -0.0396 0.0769 0.141 Uiso 1 1 calc R . . C14 C 0.6293(5) -0.0078(3) -0.0732(4) 0.151(2) Uani 1 1 d . . . H14 H 0.5847 -0.0389 -0.1102 0.182 Uiso 1 1 calc R . . C13 C 0.6911(5) 0.0360(3) -0.1284(4) 0.149(2) Uani 1 1 d . . . H13 H 0.6909 0.0334 -0.2040 0.178 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 S1 0.0794(4) 0.0731(4) 0.0692(4) -0.0010(3) 0.0036(3) -0.0067(3) N1 0.0842(13) 0.0617(11) 0.0627(12) 0.0097(10) 0.0144(11) 0.0104(9) N2 0.0881(14) 0.0758(12) 0.0672(15) 0.0032(11) 0.0176(12) 0.0185(10) C5 0.0930(18) 0.0685(14) 0.0627(15) 0.0074(12) 0.0069(13) 0.0174(13) C4 0.097(2) 0.0755(17) 0.0716(17) -0.0020(14) -0.0057(15) 0.0285(15) C3 0.115(2) 0.0617(14) 0.0789(19) 0.0056(14) -0.0091(17) 0.0178(15) C2 0.111(2) 0.0625(14) 0.0704(17) 0.0027(12) -0.0131(16) -0.0050(14) C1 0.0835(16) 0.0643(13) 0.0485(11) 0.0023(11) -0.0079(11) -0.0002(11) C6 0.0837(15) 0.0597(12) 0.0470(11) 0.0084(11) -0.0014(11) 0.0094(10) C7 0.0840(15) 0.0615(12) 0.0493(11) 0.0017(10) 0.0034(11) 0.0088(11) C8 0.0661(14) 0.0889(17) 0.0746(17) -0.0150(14) -0.0038(12) 0.0076(12) C9 0.112(2) 0.150(3) 0.092(2) -0.001(3) -0.007(2) 0.064(2) C10 0.0654(13) 0.0638(13) 0.0696(15) -0.0088(12) 0.0142(12) -0.0017(10) C11 0.0798(19) 0.141(3) 0.127(3) 0.024(3) 0.029(2) -0.015(2) C12 0.151(5) 0.146(5) 0.156(6) 0.049(4) 0.094(4) 0.022(4) C15 0.172(4) 0.106(2) 0.0744(19) -0.0003(18) -0.010(2) -0.061(3) C14 0.267(7) 0.107(3) 0.080(3) -0.008(2) -0.025(4) -0.044(4) C13 0.264(8) 0.097(3) 0.084(3) 0.005(2) 0.046(4) 0.063(4) _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 C1 1.745(3) . ? S1 C7 1.764(3) . ? N1 C7 1.296(3) . ? N1 C6 1.391(3) . ? N2 C7 1.355(3) . ? N2 C8 1.455(4) . ? C5 C6 1.385(4) . ? C5 C4 1.415(4) . ? C5 H5 0.9300 . ? C4 C3 1.363(5) . ? C4 H4 0.9300 . ? C3 C2 1.370(5) . ? C3 H3 0.9300 . ? C2 C1 1.389(4) . ? C2 H2 0.9300 . ? C1 C6 1.393(4) . ? C8 C10 1.508(4) . ? C8 C9 1.510(5) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.365(5) . ? C10 C11 1.374(5) . ? C11 C12 1.426(9) . ? C11 H11 0.9300 . ? C12 C13 1.309(9) . ? C12 H12 0.9300 . ? C15 C14 1.378(7) . ? C15 H15 0.9300 . ? C14 C13 1.318(8) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? 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 C1 S1 C7 88.38(12) . . ? C7 N1 C6 110.0(2) . . ? C7 N2 C8 123.8(2) . . ? C6 C5 C4 118.1(3) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C3 C4 C5 121.4(3) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C2 C1 118.7(3) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C1 C6 121.7(3) . . ? C2 C1 S1 129.0(2) . . ? C6 C1 S1 109.33(18) . . ? C5 C6 N1 124.7(2) . . ? C5 C6 C1 119.3(2) . . ? N1 C6 C1 116.0(2) . . ? N1 C7 N2 122.8(2) . . ? N1 C7 S1 116.27(18) . . ? N2 C7 S1 120.9(2) . . ? N2 C8 C10 113.1(2) . . ? N2 C8 C9 108.5(3) . . ? C10 C8 C9 110.9(3) . . ? N2 C8 H8 108.1 . . ? C10 C8 H8 108.1 . . ? C9 C8 H8 108.1 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 117.8(4) . . ? C15 C10 C8 121.8(3) . . ? C11 C10 C8 120.2(3) . . ? C10 C11 C12 118.6(5) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 120.6(5) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C10 C15 C14 121.3(4) . . ? C10 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C13 C14 C15 120.2(5) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C12 C13 C14 121.4(5) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? 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 C6 C5 C4 C3 0.8(4) . . . . ? C5 C4 C3 C2 0.6(5) . . . . ? C4 C3 C2 C1 -2.1(5) . . . . ? C3 C2 C1 C6 2.4(4) . . . . ? C3 C2 C1 S1 -177.8(2) . . . . ? C7 S1 C1 C2 179.9(3) . . . . ? C7 S1 C1 C6 -0.2(2) . . . . ? C4 C5 C6 N1 179.2(3) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C7 N1 C6 C5 -178.3(3) . . . . ? C7 N1 C6 C1 1.5(3) . . . . ? C2 C1 C6 C5 -1.0(4) . . . . ? S1 C1 C6 C5 179.2(2) . . . . ? C2 C1 C6 N1 179.2(3) . . . . ? S1 C1 C6 N1 -0.7(3) . . . . ? C6 N1 C7 N2 177.1(3) . . . . ? C6 N1 C7 S1 -1.7(3) . . . . ? C8 N2 C7 N1 178.0(3) . . . . ? C8 N2 C7 S1 -3.2(4) . . . . ? C1 S1 C7 N1 1.2(2) . . . . ? C1 S1 C7 N2 -177.7(2) . . . . ? C7 N2 C8 C10 -78.0(3) . . . . ? C7 N2 C8 C9 158.5(3) . . . . ? N2 C8 C10 C15 -44.5(4) . . . . ? C9 C8 C10 C15 77.7(4) . . . . ? N2 C8 C10 C11 140.2(3) . . . . ? C9 C8 C10 C11 -97.6(4) . . . . ? C15 C10 C11 C12 -1.2(6) . . . . ? C8 C10 C11 C12 174.3(4) . . . . ? C10 C11 C12 C13 -0.2(8) . . . . ? C11 C10 C15 C14 0.8(7) . . . . ? C8 C10 C15 C14 -174.7(5) . . . . ? C10 C15 C14 C13 1.1(10) . . . . ? C11 C12 C13 C14 2.1(9) . . . . ? C15 C14 C13 C12 -2.5(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.15 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.353 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.117 data_1b _database_code_depnum_ccdc_archive 'CCDC 876212' #TrackingRef '- BT final cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 N2 S2' _chemical_formula_weight 236.37 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' 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 10.130(2) _cell_length_b 8.1511(15) _cell_length_c 13.600(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.902(10) _cell_angle_gamma 90.00 _cell_volume 1120.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5697 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 27.96 _exptl_crystal_description Rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.442 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_T_max 0.884 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 13975 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.33 _reflns_number_total 2761 _reflns_number_gt 2255 _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^)+(0.0548P)^2^+0.2070P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2761 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 S1 S 0.56995(4) 0.03297(5) 0.18236(3) 0.04791(14) Uani 1 1 d . . . S2 S 0.08450(6) 0.19330(7) 0.30711(4) 0.06779(18) Uani 1 1 d . . . N1 N 0.44061(13) 0.22827(17) 0.05780(9) 0.0479(3) Uani 1 1 d . . . N2 N 0.30691(15) 0.0997(2) 0.16887(11) 0.0641(4) Uani 1 1 d . . . C2 C 0.79276(17) 0.1229(2) 0.07961(12) 0.0529(4) Uani 1 1 d . . . H2 H 0.8491 0.0586 0.1204 0.064 Uiso 1 1 calc R . . C3 C 0.84079(18) 0.2119(2) 0.00268(13) 0.0566(4) Uani 1 1 d . . . H3 H 0.9301 0.2064 -0.0090 0.068 Uiso 1 1 calc R . . C4 C 0.75609(19) 0.3089(2) -0.05688(12) 0.0555(4) Uani 1 1 d . . . H4 H 0.7898 0.3678 -0.1081 0.067 Uiso 1 1 calc R . . C5 C 0.62292(18) 0.3202(2) -0.04188(12) 0.0523(4) Uani 1 1 d . . . H5 H 0.5677 0.3866 -0.0822 0.063 Uiso 1 1 calc R . . C1 C 0.65895(15) 0.13228(19) 0.09418(10) 0.0414(3) Uani 1 1 d . . . C6 C 0.57211(15) 0.23053(19) 0.03456(10) 0.0412(3) Uani 1 1 d . . . C7 C 0.42445(16) 0.1307(2) 0.13165(11) 0.0439(3) Uani 1 1 d . . . C11 C 0.29133(19) -0.0011(2) 0.25540(13) 0.0577(4) Uani 1 1 d . . . H11A H 0.3757 -0.0508 0.2762 0.069 Uiso 1 1 calc R . . H11B H 0.2289 -0.0886 0.2386 0.069 Uiso 1 1 calc R . . C10 C 0.2427(2) 0.0976(3) 0.33918(13) 0.0612(5) Uani 1 1 d . . . H10A H 0.3073 0.1818 0.3579 0.073 Uiso 1 1 calc R . . H10B H 0.2347 0.0263 0.3956 0.073 Uiso 1 1 calc R . . C8 C 0.18689(18) 0.1758(3) 0.12487(13) 0.0598(5) Uani 1 1 d . . . H8A H 0.1227 0.0912 0.1061 0.072 Uiso 1 1 calc R . . H8B H 0.2073 0.2344 0.0657 0.072 Uiso 1 1 calc R . . C9 C 0.12781(18) 0.2937(2) 0.19579(14) 0.0555(4) Uani 1 1 d . . . H9A H 0.0493 0.3437 0.1638 0.067 Uiso 1 1 calc R . . H9B H 0.1910 0.3804 0.2125 0.067 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 S1 0.0453(2) 0.0554(3) 0.0432(2) 0.01283(17) 0.00454(16) 0.01169(17) S2 0.0685(3) 0.0690(3) 0.0689(3) -0.0053(2) 0.0264(2) 0.0029(2) N1 0.0470(8) 0.0554(8) 0.0416(6) 0.0098(6) 0.0040(5) 0.0109(6) N2 0.0473(8) 0.0921(12) 0.0545(8) 0.0288(8) 0.0157(6) 0.0226(8) C2 0.0461(9) 0.0618(10) 0.0511(9) 0.0062(8) 0.0041(7) 0.0075(8) C3 0.0478(10) 0.0682(12) 0.0547(9) 0.0000(8) 0.0108(7) -0.0017(8) C4 0.0619(11) 0.0608(11) 0.0451(8) 0.0043(8) 0.0128(8) -0.0078(8) C5 0.0584(10) 0.0555(10) 0.0430(8) 0.0093(7) 0.0034(7) 0.0043(8) C1 0.0444(8) 0.0440(8) 0.0358(7) 0.0001(6) 0.0031(6) 0.0041(6) C6 0.0448(8) 0.0438(8) 0.0350(7) -0.0005(6) 0.0032(6) 0.0044(6) C7 0.0446(8) 0.0491(9) 0.0384(7) 0.0034(6) 0.0045(6) 0.0110(7) C11 0.0552(10) 0.0612(11) 0.0581(10) 0.0166(8) 0.0141(8) 0.0076(8) C10 0.0699(12) 0.0639(12) 0.0501(9) 0.0084(8) 0.0063(8) -0.0104(9) C8 0.0423(9) 0.0858(14) 0.0517(9) 0.0112(9) 0.0053(7) 0.0152(9) C9 0.0467(9) 0.0506(10) 0.0687(11) 0.0023(8) 0.0005(8) -0.0017(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 C1 1.7475(16) . ? S1 C7 1.7734(15) . ? S2 C9 1.801(2) . ? S2 C10 1.809(2) . ? N1 C7 1.2999(19) . ? N1 C6 1.390(2) . ? N2 C7 1.349(2) . ? N2 C11 1.453(2) . ? N2 C8 1.457(2) . ? C2 C1 1.385(2) . ? C2 C3 1.388(2) . ? C2 H2 0.9300 . ? C3 C4 1.387(3) . ? C3 H3 0.9300 . ? C4 C5 1.381(3) . ? C4 H4 0.9300 . ? C5 C6 1.397(2) . ? C5 H5 0.9300 . ? C1 C6 1.406(2) . ? C11 C10 1.504(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C8 C9 1.514(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? 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 C1 S1 C7 88.79(7) . . ? C9 S2 C10 97.82(9) . . ? C7 N1 C6 110.91(12) . . ? C7 N2 C11 123.88(14) . . ? C7 N2 C8 119.95(14) . . ? C11 N2 C8 116.10(15) . . ? C1 C2 C3 118.40(16) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C2 C3 C4 120.23(17) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 121.56(16) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 119.22(15) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C2 C1 C6 121.93(15) . . ? C2 C1 S1 128.92(12) . . ? C6 C1 S1 109.15(11) . . ? N1 C6 C5 125.69(14) . . ? N1 C6 C1 115.66(13) . . ? C5 C6 C1 118.65(15) . . ? N1 C7 N2 124.43(14) . . ? N1 C7 S1 115.48(12) . . ? N2 C7 S1 120.08(12) . . ? N2 C11 C10 111.74(15) . . ? N2 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? N2 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C11 C10 S2 112.21(13) . . ? C11 C10 H10A 109.2 . . ? S2 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? S2 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N2 C8 C9 111.32(15) . . ? N2 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? N2 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C8 C9 S2 112.13(13) . . ? C8 C9 H9A 109.2 . . ? S2 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? S2 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? 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 C1 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C3 C2 C1 C6 -1.0(3) . . . . ? C3 C2 C1 S1 178.80(13) . . . . ? C7 S1 C1 C2 -179.62(17) . . . . ? C7 S1 C1 C6 0.19(11) . . . . ? C7 N1 C6 C5 178.86(15) . . . . ? C7 N1 C6 C1 -0.8(2) . . . . ? C4 C5 C6 N1 -179.31(16) . . . . ? C4 C5 C6 C1 0.4(2) . . . . ? C2 C1 C6 N1 -179.87(15) . . . . ? S1 C1 C6 N1 0.31(17) . . . . ? C2 C1 C6 C5 0.4(2) . . . . ? S1 C1 C6 C5 -179.41(12) . . . . ? C6 N1 C7 N2 -177.94(16) . . . . ? C6 N1 C7 S1 0.98(18) . . . . ? C11 N2 C7 N1 -175.82(17) . . . . ? C8 N2 C7 N1 1.0(3) . . . . ? C11 N2 C7 S1 5.3(3) . . . . ? C8 N2 C7 S1 -177.86(15) . . . . ? C1 S1 C7 N1 -0.70(13) . . . . ? C1 S1 C7 N2 178.27(15) . . . . ? C7 N2 C11 C10 114.5(2) . . . . ? C8 N2 C11 C10 -62.4(2) . . . . ? N2 C11 C10 S2 59.54(19) . . . . ? C9 S2 C10 C11 -52.68(15) . . . . ? C7 N2 C8 C9 -114.60(19) . . . . ? C11 N2 C8 C9 62.5(2) . . . . ? N2 C8 C9 S2 -60.00(19) . . . . ? C10 S2 C9 C8 52.89(15) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.309 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.052