# Electronic Supplementary Material (ESI) for Green Chemistry # 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_ox-am _database_code_depnum_ccdc_archive 'CCDC 889622' #TrackingRef 'ox-am.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'C10 H8 N2 O S2' _chemical_melting_point 379 _chemical_formula_moiety 'C10 H8 N2 O S2' _chemical_formula_sum 'C10 H8 N2 O S2' _chemical_formula_weight 236.32 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4617(15) _cell_length_b 7.5189(18) _cell_length_c 9.840(2) _cell_angle_alpha 109.76(2) _cell_angle_beta 90.103(17) _cell_angle_gamma 90.706(18) _cell_volume 519.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 598 _cell_measurement_theta_min 2.9680 _cell_measurement_theta_max 28.9250 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.483 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_T_max 0.865 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0938 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2760 _diffrn_reflns_av_R_equivalents 0.0109 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 28.99 _reflns_number_total 2760 _reflns_number_gt 1397 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0556P)^2^+0.0449P] 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 2760 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 N1 N -0.1543(3) 0.6368(3) 0.8602(2) 0.0496(6) Uani 1 1 d . . . N21 N -0.1349(4) 0.5945(4) 0.7229(3) 0.0611(7) Uani 1 1 d . . . C9 C 0.1348(4) 0.7472(3) 0.8594(3) 0.0355(6) Uani 1 1 d . . . C10 C 0.4518(4) 0.8227(4) 0.7541(3) 0.0523(8) Uani 1 1 d . . . H10A H 0.5713 0.8737 0.7743 0.078 Uiso 1 1 calc R . . H10C H 0.3867 0.8909 0.7038 0.078 Uiso 1 1 calc R . . H10B H 0.4567 0.6917 0.6953 0.078 Uiso 1 1 calc R . . S1 S 0.34084(10) 0.84453(10) 0.92052(7) 0.0443(2) Uani 1 1 d . . . S2 S 0.07162(11) 0.66021(10) 0.68419(7) 0.0508(3) Uani 1 1 d . . . O1 O 0.1341(3) 0.8669(3) 1.1583(2) 0.0548(5) Uani 1 1 d . . . C8 C -0.0100(4) 0.7219(3) 0.9412(3) 0.0360(6) Uani 1 1 d . . . C5 C -0.1287(4) 0.8297(4) 1.3404(3) 0.0495(7) Uani 1 1 d . . . H5 H -0.0174 0.8805 1.3771 0.059 Uiso 1 1 calc R . . C6 C -0.1569(4) 0.7641(3) 1.1918(3) 0.0347(6) Uani 1 1 d . . . C7 C -0.0037(4) 0.7875(3) 1.1010(3) 0.0377(6) Uani 1 1 d . . . C1 C -0.3236(4) 0.6885(4) 1.1403(3) 0.0431(7) Uani 1 1 d . . . H1 H -0.3455 0.6432 1.0413 0.052 Uiso 1 1 calc R . . C3 C -0.4277(4) 0.7462(4) 1.3807(3) 0.0535(8) Uani 1 1 d . . . H3 H -0.5188 0.7410 1.4436 0.064 Uiso 1 1 calc R . . C4 C -0.2623(5) 0.8209(4) 1.4342(3) 0.0569(8) Uani 1 1 d . . . H4 H -0.2410 0.8652 1.5332 0.068 Uiso 1 1 calc R . . C2 C -0.4579(4) 0.6795(4) 1.2342(3) 0.0496(7) Uani 1 1 d . . . H2 H -0.5693 0.6280 1.1981 0.059 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 N1 0.0389(14) 0.0675(14) 0.0373(13) 0.0111(11) -0.0020(11) -0.0062(12) N21 0.0475(16) 0.0889(18) 0.0366(14) 0.0081(13) -0.0024(12) -0.0105(15) C9 0.0403(15) 0.0336(12) 0.0329(13) 0.0115(10) 0.0029(11) 0.0070(12) C10 0.0461(18) 0.0623(17) 0.0482(17) 0.0183(14) 0.0135(14) 0.0028(15) S1 0.0374(4) 0.0564(4) 0.0394(4) 0.0168(3) 0.0028(3) -0.0064(4) S2 0.0492(5) 0.0661(5) 0.0322(4) 0.0104(3) 0.0015(3) -0.0014(4) O1 0.0408(12) 0.0800(13) 0.0404(11) 0.0168(10) -0.0046(9) -0.0171(11) C8 0.0340(15) 0.0403(13) 0.0315(13) 0.0092(10) 0.0007(11) 0.0007(12) C5 0.0471(18) 0.0634(17) 0.0371(15) 0.0161(13) -0.0016(14) -0.0080(15) C6 0.0362(14) 0.0341(12) 0.0350(13) 0.0134(10) 0.0018(11) 0.0033(12) C7 0.0383(15) 0.0394(13) 0.0355(14) 0.0129(11) 0.0001(12) 0.0014(13) C1 0.0415(17) 0.0494(15) 0.0363(14) 0.0120(12) 0.0004(13) -0.0033(14) C3 0.053(2) 0.0616(18) 0.0481(18) 0.0214(14) 0.0148(16) 0.0008(17) C4 0.061(2) 0.076(2) 0.0341(15) 0.0188(14) 0.0050(15) -0.0047(18) C2 0.0401(17) 0.0552(16) 0.0500(17) 0.0136(13) 0.0028(14) -0.0082(15) _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 N1 N21 1.288(3) . ? N1 C8 1.356(3) . ? N21 S2 1.695(3) . ? C9 C8 1.397(4) . ? C9 S2 1.688(3) . ? C9 S1 1.712(3) . ? C10 S1 1.794(3) . ? C10 H10A 0.9600 . ? C10 H10C 0.9600 . ? C10 H10B 0.9600 . ? O1 C7 1.220(3) . ? C8 C7 1.481(3) . ? C5 C4 1.375(4) . ? C5 C6 1.391(3) . ? C5 H5 0.9300 . ? C6 C1 1.383(4) . ? C6 C7 1.497(4) . ? C1 C2 1.381(4) . ? C1 H1 0.9300 . ? C3 C2 1.374(4) . ? C3 C4 1.377(4) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C2 H2 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 N21 N1 C8 115.1(2) . . ? N1 N21 S2 110.8(2) . . ? C8 C9 S2 107.2(2) . . ? C8 C9 S1 127.7(2) . . ? S2 C9 S1 125.02(15) . . ? S1 C10 H10A 109.5 . . ? S1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? S1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? C9 S1 C10 101.37(14) . . ? C9 S2 N21 93.39(13) . . ? N1 C8 C9 113.5(2) . . ? N1 C8 C7 124.4(2) . . ? C9 C8 C7 122.0(2) . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 118.1(2) . . ? C1 C6 C7 125.4(2) . . ? C5 C6 C7 116.5(2) . . ? O1 C7 C8 116.6(2) . . ? O1 C7 C6 120.0(2) . . ? C8 C7 C6 123.4(2) . . ? C2 C1 C6 120.7(3) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? _diffrn_measured_fraction_theta_max 0.684 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full ? _refine_diff_density_max 0.227 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.056 data_ms-21-a _database_code_depnum_ccdc_archive 'CCDC 914821' #TrackingRef 'ms-21-a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common C11H10N2O2S2 _chemical_melting_point ? _chemical_formula_moiety C11H10N2O2S2 _chemical_formula_sum 'C11 H10 N2 O2 S2' _chemical_formula_weight 266.35 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' S S 0.1246 0.1234 '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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0015(6) _cell_length_b 8.1903(6) _cell_length_c 9.1812(6) _cell_angle_alpha 85.565(5) _cell_angle_beta 75.327(6) _cell_angle_gamma 86.509(6) _cell_volume 579.79(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1143 _cell_measurement_theta_min 3.2770 _cell_measurement_theta_max 28.8420 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.449 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97138 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4121 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 28.91 _reflns_number_total 2614 _reflns_number_gt 1888 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0614P)^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_extinction_coef ? _refine_ls_number_reflns 2614 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.08448(8) 0.10810(8) 0.10644(6) 0.0464(2) Uani 1 1 d . . . S2 S -0.01344(8) 0.34476(8) 0.35311(6) 0.0508(2) Uani 1 1 d . . . O2 O 0.2775(2) 0.3117(2) -0.12310(18) 0.0597(5) Uani 1 1 d . . . C5 C 0.3667(3) 0.5820(3) -0.1382(2) 0.0380(5) Uani 1 1 d . . . O1 O 0.6527(2) 0.9581(2) -0.39447(18) 0.0535(5) Uani 1 1 d . . . N1 N 0.1444(3) 0.5673(3) 0.1869(2) 0.0513(5) Uani 1 1 d . . . C8 C 0.2721(3) 0.4383(3) -0.0589(2) 0.0404(5) Uani 1 1 d . . . C2 C 0.5551(3) 0.8406(3) -0.3054(2) 0.0414(5) Uani 1 1 d . . . C10 C 0.0854(3) 0.2974(3) 0.1753(2) 0.0390(5) Uani 1 1 d . . . C6 C 0.3540(3) 0.7371(3) -0.0836(2) 0.0448(6) Uani 1 1 d . . . H008 H 0.2813 0.7551 0.0108 0.054 Uiso 1 1 calc R . . C9 C 0.1666(3) 0.4358(3) 0.0998(2) 0.0388(5) Uani 1 1 d . . . C3 C 0.5697(3) 0.6869(3) -0.3625(3) 0.0477(6) Uani 1 1 d . . . H010 H 0.6428 0.6695 -0.4568 0.057 Uiso 1 1 calc R . . C4 C 0.4773(3) 0.5617(3) -0.2810(2) 0.0455(6) Uani 1 1 d . . . H011 H 0.4880 0.4598 -0.3214 0.055 Uiso 1 1 calc R . . C7 C 0.4461(3) 0.8650(3) -0.1655(3) 0.0475(6) Uani 1 1 d . . . H012 H 0.4348 0.9677 -0.1265 0.057 Uiso 1 1 calc R . . N2 N 0.0526(3) 0.5400(3) 0.3228(2) 0.0601(6) Uani 1 1 d . . . C1 C 0.6236(4) 1.1199(3) -0.3468(3) 0.0638(8) Uani 1 1 d . . . H01A H 0.6993 1.1917 -0.4177 0.096 Uiso 1 1 calc R . . H01B H 0.6462 1.1225 -0.2492 0.096 Uiso 1 1 calc R . . H01C H 0.5056 1.1552 -0.3411 0.096 Uiso 1 1 calc R . . C11 C -0.0460(3) -0.0034(3) 0.2684(3) 0.0559(7) Uani 1 1 d . . . H01D H -0.0563 -0.1135 0.2438 0.084 Uiso 1 1 calc R . . H01E H -0.1588 0.0496 0.2966 0.084 Uiso 1 1 calc R . . H01F H 0.0077 -0.0055 0.3509 0.084 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 0.0580(4) 0.0376(4) 0.0421(3) -0.0122(3) -0.0045(3) -0.0137(3) S2 0.0634(4) 0.0448(4) 0.0385(3) -0.0128(3) 0.0036(3) -0.0144(3) O2 0.0793(13) 0.0460(11) 0.0479(10) -0.0194(8) 0.0035(8) -0.0189(9) C5 0.0444(13) 0.0357(13) 0.0347(11) -0.0054(9) -0.0099(9) -0.0033(10) O1 0.0609(11) 0.0411(10) 0.0489(10) 0.0011(8) 0.0040(8) -0.0068(8) N1 0.0734(14) 0.0366(12) 0.0393(11) -0.0108(9) -0.0018(10) -0.0093(10) C8 0.0463(13) 0.0380(13) 0.0379(12) -0.0088(10) -0.0090(10) -0.0070(10) C2 0.0420(13) 0.0380(14) 0.0421(12) 0.0015(10) -0.0078(10) -0.0011(10) C10 0.0435(12) 0.0381(13) 0.0361(11) -0.0109(10) -0.0080(9) -0.0050(10) C6 0.0538(15) 0.0386(14) 0.0364(12) -0.0044(10) -0.0005(10) -0.0021(11) C9 0.0444(13) 0.0341(13) 0.0379(12) -0.0083(9) -0.0076(10) -0.0062(10) C3 0.0561(15) 0.0473(15) 0.0356(12) -0.0080(11) -0.0026(10) -0.0028(12) C4 0.0561(15) 0.0407(14) 0.0379(12) -0.0108(10) -0.0057(10) -0.0041(11) C7 0.0554(15) 0.0346(13) 0.0472(13) -0.0064(11) -0.0015(11) -0.0033(11) N2 0.0874(17) 0.0387(13) 0.0442(12) -0.0140(10) 0.0082(11) -0.0161(11) C1 0.0748(19) 0.0393(16) 0.0658(17) 0.0055(13) 0.0017(14) -0.0066(14) C11 0.0720(18) 0.0455(16) 0.0486(14) -0.0037(12) -0.0081(12) -0.0174(13) _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 S1 C10 1.720(2) . ? S1 C11 1.804(3) . ? S2 C10 1.687(2) . ? S2 N2 1.695(2) . ? O2 C8 1.226(3) . ? C5 C6 1.390(3) . ? C5 C4 1.400(3) . ? C5 C8 1.478(3) . ? O1 C2 1.360(3) . ? O1 C1 1.415(3) . ? N1 N2 1.288(3) . ? N1 C9 1.367(3) . ? C8 C9 1.487(3) . ? C2 C7 1.379(3) . ? C2 C3 1.388(3) . ? C10 C9 1.388(3) . ? C6 C7 1.377(3) . ? C6 H008 0.9300 . ? C3 C4 1.360(3) . ? C3 H010 0.9300 . ? C4 H011 0.9300 . ? C7 H012 0.9300 . ? C1 H01A 0.9600 . ? C1 H01B 0.9600 . ? C1 H01C 0.9600 . ? C11 H01D 0.9600 . ? C11 H01E 0.9600 . ? C11 H01F 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 C10 S1 C11 101.40(11) . . ? C10 S2 N2 93.01(10) . . ? C6 C5 C4 116.8(2) . . ? C6 C5 C8 125.49(19) . . ? C4 C5 C8 117.7(2) . . ? C2 O1 C1 116.80(18) . . ? N2 N1 C9 114.4(2) . . ? O2 C8 C5 120.5(2) . . ? O2 C8 C9 115.9(2) . . ? C5 C8 C9 123.64(19) . . ? O1 C2 C7 124.5(2) . . ? O1 C2 C3 116.15(19) . . ? C7 C2 C3 119.3(2) . . ? C9 C10 S2 107.79(16) . . ? C9 C10 S1 127.72(17) . . ? S2 C10 S1 124.49(15) . . ? C7 C6 C5 121.8(2) . . ? C7 C6 H008 119.1 . . ? C5 C6 H008 119.1 . . ? N1 C9 C10 113.49(19) . . ? N1 C9 C8 123.5(2) . . ? C10 C9 C8 123.0(2) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H010 119.9 . . ? C2 C3 H010 119.9 . . ? C3 C4 C5 121.9(2) . . ? C3 C4 H011 119.1 . . ? C5 C4 H011 119.1 . . ? C2 C7 C6 120.0(2) . . ? C2 C7 H012 120.0 . . ? C6 C7 H012 120.0 . . ? N1 N2 S2 111.32(15) . . ? O1 C1 H01A 109.5 . . ? O1 C1 H01B 109.5 . . ? H01A C1 H01B 109.5 . . ? O1 C1 H01C 109.5 . . ? H01A C1 H01C 109.5 . . ? H01B C1 H01C 109.5 . . ? S1 C11 H01D 109.5 . . ? S1 C11 H01E 109.5 . . ? H01D C11 H01E 109.5 . . ? S1 C11 H01F 109.5 . . ? H01D C11 H01F 109.5 . . ? H01E C11 H01F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C5 C8 O2 172.0(2) . . . . ? C4 C5 C8 O2 -7.3(3) . . . . ? C6 C5 C8 C9 -8.1(4) . . . . ? C4 C5 C8 C9 172.6(2) . . . . ? C1 O1 C2 C7 -7.8(3) . . . . ? C1 O1 C2 C3 172.4(2) . . . . ? N2 S2 C10 C9 0.30(18) . . . . ? N2 S2 C10 S1 179.34(15) . . . . ? C11 S1 C10 C9 -179.9(2) . . . . ? C11 S1 C10 S2 1.22(18) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C8 C5 C6 C7 -179.5(2) . . . . ? N2 N1 C9 C10 -0.1(3) . . . . ? N2 N1 C9 C8 -178.1(2) . . . . ? S2 C10 C9 N1 -0.2(3) . . . . ? S1 C10 C9 N1 -179.19(16) . . . . ? S2 C10 C9 C8 177.90(17) . . . . ? S1 C10 C9 C8 -1.1(3) . . . . ? O2 C8 C9 N1 -178.9(2) . . . . ? C5 C8 C9 N1 1.2(4) . . . . ? O2 C8 C9 C10 3.2(3) . . . . ? C5 C8 C9 C10 -176.7(2) . . . . ? O1 C2 C3 C4 179.8(2) . . . . ? C7 C2 C3 C4 -0.1(4) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C6 C5 C4 C3 0.6(3) . . . . ? C8 C5 C4 C3 180.0(2) . . . . ? O1 C2 C7 C6 -179.4(2) . . . . ? C3 C2 C7 C6 0.4(4) . . . . ? C5 C6 C7 C2 -0.3(4) . . . . ? C9 N1 N2 S2 0.3(3) . . . . ? C10 S2 N2 N1 -0.35(19) . . . . ? _diffrn_measured_fraction_theta_max 0.856 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.363 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.055