# Electronic Supplementary Material (ESI) for RSC Advances # 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_on-di #TrackingRef 'on-di.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Cl0 O2 S' _chemical_formula_weight 206.25 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P21/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 9.1727(12) _cell_length_b 12.4922(14) _cell_length_c 15.7956(17) _cell_angle_alpha 90.00 _cell_angle_beta 104.861(12) _cell_angle_gamma 90.00 _cell_volume 1749.4(4) _cell_formula_units_Z 7 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 8585 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 29.11 _reflns_number_total 4016 _reflns_number_gt 2556 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0913P)^2^+0.6929P] 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 4016 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1034 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1954 _refine_ls_wR_factor_gt 0.1618 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 S001 S 0.37467(10) 0.45669(7) 0.30633(6) 0.0445(3) Uani 1 1 d . . . Cl Cl 0.70763(13) 0.24526(9) 0.25118(7) 0.0656(3) Uani 1 1 d . . . S002 S 0.22727(12) 0.24683(8) 0.23872(7) 0.0544(3) Uani 1 1 d . . . O004 O 0.5579(3) 0.6456(2) 0.39716(18) 0.0658(8) Uani 1 1 d . . . O005 O 0.7739(3) 0.2580(2) 0.51625(18) 0.0609(8) Uani 1 1 d . . . C006 C 0.8022(4) 0.4459(3) 0.5289(2) 0.0421(8) Uani 1 1 d . . . C007 C 0.6088(4) 0.5586(3) 0.4258(2) 0.0424(8) Uani 1 1 d . . . C008 C 0.5900(4) 0.3588(3) 0.4164(2) 0.0389(7) Uani 1 1 d . . . C009 C 0.3709(4) 0.3191(3) 0.3083(2) 0.0408(8) Uani 1 1 d . . . C010 C 0.6571(4) 0.1050(3) 0.3736(2) 0.0472(8) Uani 1 1 d . . . C011 C 0.8210(4) 0.6384(3) 0.5374(2) 0.0514(9) Uani 1 1 d . . . H011 H 0.7835 0.7056 0.5177 0.062 Uiso 1 1 calc R . . C012 C 0.9327(4) 0.4384(3) 0.5980(2) 0.0516(9) Uani 1 1 d . . . H012 H 0.9706 0.3716 0.6184 0.062 Uiso 1 1 calc R . . C013 C 0.7479(4) 0.5474(3) 0.4984(2) 0.0408(8) Uani 1 1 d . . . C014 C 0.7272(4) 0.3463(3) 0.4896(2) 0.0430(8) Uani 1 1 d . . . C015 C 0.9494(4) 0.6299(3) 0.6053(3) 0.0573(10) Uani 1 1 d . . . H015 H 0.9988 0.6914 0.6308 0.069 Uiso 1 1 calc R . . C016 C 0.8778(5) 0.0791(4) 0.3191(3) 0.0671(12) Uani 1 1 d . . . H016 H 0.9380 0.1011 0.2831 0.081 Uiso 1 1 calc R . . C017 C 0.5384(4) 0.4594(3) 0.3889(2) 0.0400(7) Uani 1 1 d . . . C018 C 0.7488(4) 0.1364(3) 0.3211(2) 0.0497(9) Uani 1 1 d . . . C019 C 0.4942(4) 0.2767(3) 0.3696(2) 0.0434(8) Uani 1 1 d . . . C020 C 0.6995(5) 0.0133(3) 0.4246(3) 0.0645(11) Uani 1 1 d . . . H020 H 0.6409 -0.0095 0.4613 0.077 Uiso 1 1 calc R . . O O 0.4108(4) 0.1062(3) 0.3925(3) 0.0997(13) Uani 1 1 d . . . C022 C 0.5141(4) 0.1597(3) 0.3798(3) 0.0524(9) Uani 1 1 d . . . C023 C 1.0053(4) 0.5304(4) 0.6359(3) 0.0585(10) Uani 1 1 d . . . H023 H 1.0918 0.5253 0.6819 0.070 Uiso 1 1 calc R . . C024 C 0.9153(6) -0.0096(4) 0.3703(4) 0.0810(14) Uani 1 1 d . . . H024 H 1.0027 -0.0472 0.3702 0.097 Uiso 1 1 calc R . . C025 C 0.8257(6) -0.0434(4) 0.4216(3) 0.0797(14) Uani 1 1 d . . . H025 H 0.8504 -0.1054 0.4548 0.096 Uiso 1 1 calc R . . C026 C 0.1317(5) 0.3498(3) 0.1665(3) 0.0693(12) Uani 1 1 d . . . H02A H 0.0479 0.3193 0.1240 0.104 Uiso 1 1 calc R . . H02B H 0.2002 0.3819 0.1371 0.104 Uiso 1 1 calc R . . H02C H 0.0956 0.4034 0.1997 0.104 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 S001 0.0479(5) 0.0383(5) 0.0457(5) -0.0011(4) 0.0090(4) -0.0006(4) Cl 0.0699(7) 0.0713(8) 0.0571(6) 0.0044(5) 0.0188(5) -0.0044(5) S002 0.0553(6) 0.0418(6) 0.0610(6) -0.0061(4) 0.0059(4) -0.0043(4) O004 0.0787(19) 0.0386(15) 0.0674(18) 0.0026(13) -0.0042(14) 0.0018(14) O005 0.0763(19) 0.0424(16) 0.0562(17) 0.0030(12) 0.0030(13) 0.0081(13) C006 0.0432(18) 0.047(2) 0.0388(17) -0.0031(15) 0.0162(14) 0.0016(16) C007 0.0510(19) 0.0350(19) 0.0427(18) 0.0003(14) 0.0148(15) 0.0003(16) C008 0.0448(18) 0.0340(18) 0.0413(18) -0.0008(13) 0.0175(14) -0.0005(15) C009 0.0430(18) 0.0367(19) 0.0453(19) -0.0029(14) 0.0164(14) -0.0041(15) C010 0.050(2) 0.0377(19) 0.050(2) -0.0073(15) 0.0060(16) -0.0037(16) C011 0.052(2) 0.046(2) 0.058(2) -0.0039(17) 0.0181(17) -0.0044(17) C012 0.048(2) 0.055(2) 0.052(2) 0.0034(17) 0.0127(16) 0.0076(18) C013 0.0399(17) 0.042(2) 0.0439(18) -0.0033(14) 0.0178(14) -0.0022(15) C014 0.052(2) 0.040(2) 0.0410(18) 0.0013(14) 0.0186(15) 0.0004(16) C015 0.051(2) 0.058(3) 0.064(2) -0.0150(19) 0.0172(18) -0.0111(19) C016 0.061(3) 0.073(3) 0.071(3) -0.021(2) 0.025(2) 0.005(2) C017 0.0442(18) 0.0393(19) 0.0393(17) -0.0017(14) 0.0157(14) -0.0014(15) C018 0.053(2) 0.048(2) 0.045(2) -0.0131(16) 0.0069(16) -0.0037(17) C019 0.0495(19) 0.0375(19) 0.048(2) 0.0017(14) 0.0215(15) -0.0032(16) C020 0.070(3) 0.047(2) 0.072(3) -0.002(2) 0.009(2) 0.003(2) O 0.066(2) 0.057(2) 0.187(4) 0.031(2) 0.052(2) -0.0025(17) C022 0.051(2) 0.043(2) 0.064(2) 0.0040(17) 0.0159(17) -0.0016(18) C023 0.047(2) 0.071(3) 0.054(2) -0.0091(19) 0.0072(16) -0.002(2) C024 0.071(3) 0.070(3) 0.097(4) -0.013(3) 0.012(3) 0.017(3) C025 0.088(4) 0.050(3) 0.088(3) 0.000(2) -0.001(3) 0.017(3) C026 0.075(3) 0.051(2) 0.067(3) -0.008(2) -0.010(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S001 C017 1.719(3) . ? S001 C009 1.720(4) . ? Cl C018 1.731(4) . ? S002 C009 1.736(3) . ? S002 C026 1.792(4) . ? O004 C007 1.223(4) . ? O005 C014 1.219(4) . ? C006 C013 1.401(5) . ? C006 C012 1.401(5) . ? C006 C014 1.479(5) . ? C007 C017 1.448(5) . ? C007 C013 1.487(5) . ? C008 C017 1.374(5) . ? C008 C019 1.427(5) . ? C008 C014 1.483(5) . ? C009 C019 1.392(5) . ? C010 C018 1.381(5) . ? C010 C020 1.398(5) . ? C010 C022 1.504(5) . ? C011 C015 1.380(5) . ? C011 C013 1.382(5) . ? C011 H011 0.9300 . ? C012 C023 1.385(5) . ? C012 H012 0.9300 . ? C015 C023 1.383(6) . ? C015 H015 0.9300 . ? C016 C024 1.363(7) . ? C016 C018 1.390(5) . ? C016 H016 0.9300 . ? C019 C022 1.476(5) . ? C020 C025 1.369(6) . ? C020 H020 0.9300 . ? O C022 1.217(5) . ? C023 H023 0.9300 . ? C024 C025 1.361(7) . ? C024 H024 0.9300 . ? C025 H025 0.9300 . ? C026 H02A 0.9600 . ? C026 H02B 0.9600 . ? C026 H02C 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 C017 S001 C009 91.37(16) . . ? C009 S002 C026 101.40(18) . . ? C013 C006 C012 119.1(3) . . ? C013 C006 C014 122.0(3) . . ? C012 C006 C014 118.9(3) . . ? O004 C007 C017 121.6(3) . . ? O004 C007 C013 122.6(3) . . ? C017 C007 C013 115.8(3) . . ? C017 C008 C019 112.2(3) . . ? C017 C008 C014 119.8(3) . . ? C019 C008 C014 127.9(3) . . ? C019 C009 S001 112.1(3) . . ? C019 C009 S002 126.3(3) . . ? S001 C009 S002 121.6(2) . . ? C018 C010 C020 117.2(4) . . ? C018 C010 C022 125.9(3) . . ? C020 C010 C022 116.9(3) . . ? C015 C011 C013 120.2(4) . . ? C015 C011 H011 119.9 . . ? C013 C011 H011 119.9 . . ? C023 C012 C006 120.1(4) . . ? C023 C012 H012 119.9 . . ? C006 C012 H012 119.9 . . ? C011 C013 C006 120.1(3) . . ? C011 C013 C007 119.2(3) . . ? C006 C013 C007 120.6(3) . . ? O005 C014 C006 122.1(3) . . ? O005 C014 C008 121.1(3) . . ? C006 C014 C008 116.7(3) . . ? C011 C015 C023 120.5(4) . . ? C011 C015 H015 119.8 . . ? C023 C015 H015 119.8 . . ? C024 C016 C018 119.5(4) . . ? C024 C016 H016 120.3 . . ? C018 C016 H016 120.3 . . ? C008 C017 C007 125.0(3) . . ? C008 C017 S001 112.6(3) . . ? C007 C017 S001 122.3(3) . . ? C010 C018 C016 121.4(4) . . ? C010 C018 Cl 122.6(3) . . ? C016 C018 Cl 116.0(3) . . ? C009 C019 C008 111.7(3) . . ? C009 C019 C022 120.6(3) . . ? C008 C019 C022 127.8(3) . . ? C025 C020 C010 121.1(4) . . ? C025 C020 H020 119.4 . . ? C010 C020 H020 119.4 . . ? O C022 C019 118.8(3) . . ? O C022 C010 119.4(4) . . ? C019 C022 C010 121.8(3) . . ? C015 C023 C012 120.0(4) . . ? C015 C023 H023 120.0 . . ? C012 C023 H023 120.0 . . ? C025 C024 C016 120.4(4) . . ? C025 C024 H024 119.8 . . ? C016 C024 H024 119.8 . . ? C024 C025 C020 120.4(5) . . ? C024 C025 H025 119.8 . . ? C020 C025 H025 119.8 . . ? S002 C026 H02A 109.5 . . ? S002 C026 H02B 109.5 . . ? H02A C026 H02B 109.5 . . ? S002 C026 H02C 109.5 . . ? H02A C026 H02C 109.5 . . ? H02B C026 H02C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.855 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.045 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 881391' ####################################################################### # # 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_thiophene-1 #TrackingRef 'thiophene-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common naphtho[b]thiophene _chemical_melting_point 215 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H10 O3 S3' _chemical_formula_weight 370.46 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' _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 8.245(5) _cell_length_b 8.504(5) _cell_length_c 12.515(5) _cell_angle_alpha 97.900(5) _cell_angle_beta 92.639(5) _cell_angle_gamma 113.007(5) _cell_volume 795.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.480 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 5744 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 28.95 _reflns_number_total 3594 _reflns_number_gt 2775 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0664P)^2^+0.2506P] 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 3594 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 S001 S -0.05748(8) -0.37363(8) 0.88350(5) 0.04367(18) Uani 1 1 d . . . S2 S -0.10671(9) -0.50221(8) 0.64019(5) 0.04710(19) Uani 1 1 d . . . S3 S 0.31590(10) 0.06792(10) 0.49878(6) 0.0568(2) Uani 1 1 d . . . O2 O 0.4597(3) 0.1350(3) 0.82897(15) 0.0645(6) Uani 1 1 d . . . C005 C 0.1360(4) -0.1061(3) 1.05357(19) 0.0447(6) Uani 1 1 d . . . O1 O 0.2616(3) -0.2461(2) 0.59304(15) 0.0568(5) Uani 1 1 d . . . C007 C 0.3900(3) 0.1515(3) 1.00946(19) 0.0444(6) Uani 1 1 d . . . O3 O 0.0429(3) -0.1856(3) 1.11818(15) 0.0651(6) Uani 1 1 d . . . C009 C 0.1536(4) 0.1354(4) 0.6608(2) 0.0445(6) Uani 1 1 d . . . H009 H 0.0943 0.1282 0.7225 0.081(13) Uani 1 1 calc R . . C010 C 0.1999(3) -0.0920(3) 0.85937(17) 0.0373(5) Uani 1 1 d . . . C011 C 0.0012(3) -0.3475(3) 0.75464(18) 0.0372(5) Uani 1 1 d . . . C012 C 0.2850(4) 0.0658(3) 1.08655(19) 0.0449(6) Uani 1 1 d . . . C013 C 0.2146(3) -0.1447(3) 0.64886(17) 0.0388(5) Uani 1 1 d . . . C014 C 0.5287(4) 0.3114(4) 1.0426(2) 0.0560(7) Uani 1 1 d . . . H014 H 0.5972 0.3691 0.9918 0.067 Uiso 1 1 calc R . . C015 C 0.2199(3) 0.0127(3) 0.61386(17) 0.0372(5) Uani 1 1 d . . . C016 C 0.1048(3) -0.1748(3) 0.93771(18) 0.0394(5) Uani 1 1 d . . . C017 C 0.3260(4) 0.1419(4) 1.1957(2) 0.0580(7) Uani 1 1 d . . . H017 H 0.2591 0.0853 1.2474 0.070 Uiso 1 1 calc R . . C018 C 0.3570(3) 0.0715(3) 0.89263(19) 0.0421(5) Uani 1 1 d . . . C019 C -0.2782(5) -0.6621(4) 0.6957(3) 0.0636(9) Uani 1 1 d . . . H01A H -0.3467 -0.7568 0.6390 0.16(2) Uani 1 1 calc R . . H01B H -0.3537 -0.6118 0.7284 0.116(17) Uani 1 1 calc R . . H01C H -0.2265 -0.7038 0.7497 0.114(17) Uani 1 1 calc R . . C020 C 0.5657(5) 0.3859(5) 1.1518(3) 0.0689(9) Uani 1 1 d . . . H020 H 0.6585 0.4938 1.1739 0.082(11) Uani 1 1 calc R . . C021 C 0.1408(3) -0.1903(3) 0.75306(17) 0.0366(5) Uani 1 1 d . . . C022 C 0.1927(5) 0.2696(5) 0.5981(3) 0.0652(9) Uani 1 1 d . . . H022 H 0.1626 0.3639 0.6155 0.080(11) Uani 1 1 calc R . . C023 C 0.4653(5) 0.3005(5) 1.2272(3) 0.0682(9) Uani 1 1 d . . . H023 H 0.4919 0.3504 1.3002 0.094(12) Uani 1 1 calc R . . C024 C 0.2776(5) 0.2489(5) 0.5107(3) 0.0653(8) Uani 1 1 d . . . H024 H 0.3112 0.3268 0.4624 0.116(15) Uani 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 S001 0.0515(4) 0.0426(3) 0.0382(3) 0.0164(2) 0.0179(3) 0.0157(3) S2 0.0547(4) 0.0410(3) 0.0392(3) 0.0066(2) 0.0091(3) 0.0120(3) S3 0.0675(5) 0.0692(5) 0.0426(4) 0.0247(3) 0.0216(3) 0.0302(4) O2 0.0562(11) 0.0717(13) 0.0411(10) 0.0123(9) 0.0127(9) -0.0020(10) C005 0.0610(15) 0.0514(14) 0.0336(12) 0.0145(10) 0.0157(11) 0.0319(12) O1 0.0793(13) 0.0510(11) 0.0451(10) 0.0103(8) 0.0311(10) 0.0281(10) C007 0.0513(14) 0.0476(14) 0.0376(12) 0.0069(10) 0.0021(11) 0.0236(11) O3 0.0911(15) 0.0707(13) 0.0373(9) 0.0200(9) 0.0301(10) 0.0305(11) C009 0.0462(14) 0.0525(15) 0.0369(12) 0.0120(11) 0.0114(10) 0.0197(12) H009 0.039(19) 0.022(16) 0.17(4) -0.03(2) -0.04(2) 0.016(15) C010 0.0434(12) 0.0418(12) 0.0303(10) 0.0100(9) 0.0116(9) 0.0186(10) C011 0.0427(12) 0.0389(11) 0.0335(11) 0.0101(9) 0.0126(9) 0.0179(10) C012 0.0592(15) 0.0539(14) 0.0316(11) 0.0075(10) 0.0050(10) 0.0332(12) C013 0.0396(12) 0.0430(12) 0.0296(10) 0.0078(9) 0.0110(9) 0.0107(10) C014 0.0586(16) 0.0539(16) 0.0506(15) 0.0030(12) 0.0003(13) 0.0198(13) C015 0.0345(11) 0.0465(12) 0.0270(10) 0.0078(9) 0.0074(9) 0.0113(9) C016 0.0495(13) 0.0426(12) 0.0320(11) 0.0122(9) 0.0142(10) 0.0217(10) C017 0.078(2) 0.0701(19) 0.0358(13) 0.0046(12) 0.0059(13) 0.0412(17) C018 0.0472(13) 0.0455(13) 0.0343(11) 0.0115(10) 0.0090(10) 0.0173(11) C019 0.062(2) 0.0462(17) 0.066(2) 0.0112(15) 0.0141(17) 0.0027(14) H01A 0.29(7) 0.02(2) 0.09(3) -0.01(2) 0.06(4) 0.00(3) H01B 0.09(3) 0.14(4) 0.07(3) 0.04(3) 0.04(2) -0.01(3) H01C 0.07(3) 0.03(2) 0.20(5) -0.01(3) -0.02(3) -0.018(18) C020 0.074(2) 0.064(2) 0.0586(19) -0.0130(16) -0.0137(17) 0.0261(17) H020 0.10(3) 0.07(3) 0.06(2) -0.015(19) -0.01(2) 0.02(2) C021 0.0407(12) 0.0399(11) 0.0307(10) 0.0087(9) 0.0105(9) 0.0159(9) C022 0.073(2) 0.067(2) 0.071(2) 0.0170(17) 0.0079(16) 0.0430(18) H022 0.08(3) 0.08(3) 0.07(2) 0.05(2) 0.025(19) 0.00(2) C023 0.086(2) 0.078(2) 0.0411(16) -0.0100(15) -0.0090(16) 0.042(2) H023 0.08(3) 0.05(2) 0.11(3) 0.00(2) -0.02(2) -0.016(19) C024 0.080(2) 0.072(2) 0.0588(18) 0.0357(16) 0.0165(16) 0.0360(18) H024 0.16(4) 0.10(3) 0.10(3) 0.02(3) 0.03(3) 0.07(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. 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. ; 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 S001 C016 1.715(3) . ? S001 C011 1.723(2) . ? S2 C011 1.739(2) . ? S2 C019 1.783(3) . ? S3 C024 1.677(3) . ? S3 C015 1.709(2) . ? O2 C018 1.211(3) . ? C005 O3 1.226(3) . ? C005 C016 1.458(3) . ? C005 C012 1.483(4) . ? O1 C013 1.226(3) . ? C007 C014 1.384(4) . ? C007 C012 1.410(4) . ? C007 C018 1.490(3) . ? C009 C022 1.416(4) . ? C009 C015 1.428(4) . ? C009 H009 0.9300 . ? C010 C016 1.379(3) . ? C010 C021 1.422(3) . ? C010 C018 1.472(3) . ? C011 C021 1.385(3) . ? C012 C017 1.394(4) . ? C013 C015 1.450(3) . ? C013 C021 1.500(3) . ? C014 C020 1.391(4) . ? C014 H014 0.9300 . ? C017 C023 1.377(5) . ? C017 H017 0.9300 . ? C019 H01A 0.9600 . ? C019 H01B 0.9600 . ? C019 H01C 0.9600 . ? C020 C023 1.376(5) . ? C020 H020 0.9300 . ? C022 C024 1.353(5) . ? C022 H022 0.9300 . ? C023 H023 0.9300 . ? C024 H024 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 C016 S001 C011 91.34(11) . . ? C011 S2 C019 102.00(15) . . ? C024 S3 C015 92.17(14) . . ? O3 C005 C016 121.5(3) . . ? O3 C005 C012 123.0(2) . . ? C016 C005 C012 115.5(2) . . ? C014 C007 C012 119.7(2) . . ? C014 C007 C018 119.0(2) . . ? C012 C007 C018 121.2(2) . . ? C022 C009 C015 109.0(2) . . ? C022 C009 H009 125.5 . . ? C015 C009 H009 125.5 . . ? C016 C010 C021 113.0(2) . . ? C016 C010 C018 119.3(2) . . ? C021 C010 C018 127.3(2) . . ? C021 C011 S001 112.56(17) . . ? C021 C011 S2 124.46(17) . . ? S001 C011 S2 122.98(13) . . ? C017 C012 C007 119.3(3) . . ? C017 C012 C005 119.7(3) . . ? C007 C012 C005 121.0(2) . . ? O1 C013 C015 121.7(2) . . ? O1 C013 C021 118.7(2) . . ? C015 C013 C021 119.50(19) . . ? C007 C014 C020 120.0(3) . . ? C007 C014 H014 120.0 . . ? C020 C014 H014 120.0 . . ? C009 C015 C013 129.8(2) . . ? C009 C015 S3 111.62(18) . . ? C013 C015 S3 118.55(16) . . ? C010 C016 C005 125.3(2) . . ? C010 C016 S001 112.01(17) . . ? C005 C016 S001 122.73(18) . . ? C023 C017 C012 120.1(3) . . ? C023 C017 H017 119.9 . . ? C012 C017 H017 119.9 . . ? O2 C018 C010 121.6(2) . . ? O2 C018 C007 121.0(2) . . ? C010 C018 C007 117.2(2) . . ? S2 C019 H01A 109.5 . . ? S2 C019 H01B 109.5 . . ? H01A C019 H01B 109.5 . . ? S2 C019 H01C 109.5 . . ? H01A C019 H01C 109.5 . . ? H01B C019 H01C 109.5 . . ? C023 C020 C014 120.2(3) . . ? C023 C020 H020 119.9 . . ? C014 C020 H020 119.9 . . ? C011 C021 C010 111.10(19) . . ? C011 C021 C013 120.8(2) . . ? C010 C021 C013 128.1(2) . . ? C024 C022 C009 114.2(3) . . ? C024 C022 H022 122.9 . . ? C009 C022 H022 122.9 . . ? C020 C023 C017 120.7(3) . . ? C020 C023 H023 119.7 . . ? C017 C023 H023 119.7 . . ? C022 C024 S3 112.9(2) . . ? C022 C024 H024 123.5 . . ? S3 C024 H024 123.5 . . ? 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 C016 S001 C011 C021 -0.27(18) . . . . ? C016 S001 C011 S2 -179.58(16) . . . . ? C019 S2 C011 C021 -176.2(2) . . . . ? C019 S2 C011 S001 3.0(2) . . . . ? C014 C007 C012 C017 -1.8(4) . . . . ? C018 C007 C012 C017 177.0(2) . . . . ? C014 C007 C012 C005 -179.7(2) . . . . ? C018 C007 C012 C005 -1.0(4) . . . . ? O3 C005 C012 C017 1.3(4) . . . . ? C016 C005 C012 C017 -179.6(2) . . . . ? O3 C005 C012 C007 179.2(2) . . . . ? C016 C005 C012 C007 -1.7(3) . . . . ? C012 C007 C014 C020 0.9(4) . . . . ? C018 C007 C014 C020 -177.9(3) . . . . ? C022 C009 C015 C013 179.2(3) . . . . ? C022 C009 C015 S3 -1.6(3) . . . . ? O1 C013 C015 C009 172.3(3) . . . . ? C021 C013 C015 C009 -4.4(4) . . . . ? O1 C013 C015 S3 -6.9(3) . . . . ? C021 C013 C015 S3 176.41(16) . . . . ? C024 S3 C015 C009 1.3(2) . . . . ? C024 S3 C015 C013 -179.3(2) . . . . ? C021 C010 C016 C005 179.6(2) . . . . ? C018 C010 C016 C005 6.2(4) . . . . ? C021 C010 C016 S001 0.1(3) . . . . ? C018 C010 C016 S001 -173.27(17) . . . . ? O3 C005 C016 C010 178.1(2) . . . . ? C012 C005 C016 C010 -1.0(3) . . . . ? O3 C005 C016 S001 -2.5(4) . . . . ? C012 C005 C016 S001 178.39(17) . . . . ? C011 S001 C016 C010 0.08(18) . . . . ? C011 S001 C016 C005 -179.4(2) . . . . ? C007 C012 C017 C023 1.3(4) . . . . ? C005 C012 C017 C023 179.3(3) . . . . ? C016 C010 C018 O2 168.6(2) . . . . ? C021 C010 C018 O2 -3.8(4) . . . . ? C016 C010 C018 C007 -8.4(3) . . . . ? C021 C010 C018 C007 179.3(2) . . . . ? C014 C007 C018 O2 7.7(4) . . . . ? C012 C007 C018 O2 -171.0(2) . . . . ? C014 C007 C018 C010 -175.3(2) . . . . ? C012 C007 C018 C010 5.9(3) . . . . ? C007 C014 C020 C023 0.4(5) . . . . ? S001 C011 C021 C010 0.4(3) . . . . ? S2 C011 C021 C010 179.68(17) . . . . ? S001 C011 C021 C013 178.50(17) . . . . ? S2 C011 C021 C013 -2.2(3) . . . . ? C016 C010 C021 C011 -0.3(3) . . . . ? C018 C010 C021 C011 172.4(2) . . . . ? C016 C010 C021 C013 -178.3(2) . . . . ? C018 C010 C021 C013 -5.5(4) . . . . ? O1 C013 C021 C011 -53.5(3) . . . . ? C015 C013 C021 C011 123.3(2) . . . . ? O1 C013 C021 C010 124.3(3) . . . . ? C015 C013 C021 C010 -59.0(3) . . . . ? C015 C009 C022 C024 1.1(4) . . . . ? C014 C020 C023 C017 -0.9(5) . . . . ? C012 C017 C023 C020 0.0(5) . . . . ? C009 C022 C024 S3 -0.1(4) . . . . ? C015 S3 C024 C022 -0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.853 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.370 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 881392' ####################################################################### # # 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_gr-505 #TrackingRef 'gr-505.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O3 S' _chemical_formula_weight 327.39 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 ? _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1217(14) _cell_length_b 11.429(3) _cell_length_c 11.589(3) _cell_angle_alpha 85.145(19) _cell_angle_beta 83.541(19) _cell_angle_gamma 80.709(19) _cell_volume 793.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 6181 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 29.40 _reflns_number_total 3668 _reflns_number_gt 2170 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1313P)^2^+1.0416P] 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 3668 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1626 _refine_ls_R_factor_gt 0.1058 _refine_ls_wR_factor_ref 0.3071 _refine_ls_wR_factor_gt 0.2586 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 S001 S 0.2378(2) 0.07101(12) 0.58697(11) 0.0461(4) Uani 1 1 d . . . O2AA O 0.0613(7) 0.1781(4) 0.3566(3) 0.0613(11) Uani 1 1 d . . . O0AA O -0.4745(6) 0.2874(4) 0.7442(3) 0.0622(11) Uani 1 1 d . . . C9BA C -0.0018(8) 0.1625(4) 0.5593(4) 0.0410(11) Uani 1 1 d . . . O O -0.2042(7) 0.0851(4) 0.9454(3) 0.0624(11) Uani 1 1 d . . . C0AA C -0.2815(9) 0.2806(4) 0.4391(4) 0.0421(11) Uani 1 1 d . . . C1AA C -0.1316(8) 0.1929(4) 0.6609(4) 0.0373(10) Uani 1 1 d . . . C2AA C -0.0610(8) 0.2039(4) 0.4448(4) 0.0378(11) Uani 1 1 d . . . C3AA C -0.1322(7) 0.1642(4) 0.8855(4) 0.0397(11) Uani 1 1 d . . . C4AA C -0.3537(8) 0.2657(4) 0.6563(4) 0.0410(11) Uani 1 1 d . . . C5AA C -0.0386(8) 0.1441(4) 0.7620(4) 0.0395(11) Uani 1 1 d . . . C6AA C -0.4245(8) 0.3074(4) 0.5392(4) 0.0380(11) Uani 1 1 d . . . C8AA C 0.1634(8) 0.0721(4) 0.7369(4) 0.0400(11) Uani 1 1 d . . . C9AA C -0.1104(8) 0.2795(5) 0.9391(4) 0.0453(12) Uani 1 1 d . . . C0BA C -0.6313(9) 0.3743(5) 0.5287(5) 0.0477(12) Uani 1 1 d . . . H0BA H -0.7273 0.3926 0.5950 0.057 Uiso 1 1 calc R . . C1BA C -0.3498(10) 0.3234(5) 0.3308(5) 0.0557(14) Uani 1 1 d . . . H1BA H -0.2551 0.3068 0.2637 0.067 Uiso 1 1 calc R . . C2BA C 0.5140(8) -0.0553(5) 0.7712(5) 0.0527(14) Uani 1 1 d . . . H2B1 H 0.5835 -0.0941 0.8374 0.079 Uiso 1 1 calc R . . H2B2 H 0.6055 -0.0008 0.7312 0.079 Uiso 1 1 calc R . . H2B3 H 0.4960 -0.1136 0.7195 0.079 Uiso 1 1 calc R . . C3BA C -0.5547(11) 0.3897(6) 0.3222(5) 0.0640(17) Uani 1 1 d . . . H3BA H -0.5980 0.4184 0.2494 0.077 Uiso 1 1 calc R . . C4BA C -0.0336(11) 0.3746(5) 0.8495(5) 0.0625(16) Uani 1 1 d . . . H4B1 H -0.1436 0.3982 0.7958 0.094 Uiso 1 1 calc R . . H4B2 H 0.1050 0.3428 0.8079 0.094 Uiso 1 1 calc R . . H4B3 H -0.0139 0.4423 0.8887 0.094 Uiso 1 1 calc R . . C5BA C -0.3315(10) 0.3285(6) 1.0045(5) 0.0638(16) Uani 1 1 d . . . H5B1 H -0.4410 0.3514 0.9504 0.096 Uiso 1 1 calc R . . H5B2 H -0.3140 0.3965 1.0439 0.096 Uiso 1 1 calc R . . H5B3 H -0.3788 0.2684 1.0604 0.096 Uiso 1 1 calc R . . C6BA C -0.6961(10) 0.4141(5) 0.4197(5) 0.0563(15) Uani 1 1 d . . . H6BA H -0.8366 0.4577 0.4130 0.068 Uiso 1 1 calc R . . C7BA C 0.0664(11) 0.2436(6) 1.0237(5) 0.0680(17) Uani 1 1 d . . . H7B1 H 0.0198 0.1844 1.0808 0.102 Uiso 1 1 calc R . . H7B2 H 0.0861 0.3120 1.0619 0.102 Uiso 1 1 calc R . . H7B3 H 0.2046 0.2119 0.9818 0.102 Uiso 1 1 calc R . . N12 N 0.2976(7) 0.0094(4) 0.8099(4) 0.0537(12) Uani 1 1 d . . . H12 H 0.2545 0.0071 0.8832 0.064 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 S001 0.0518(8) 0.0523(8) 0.0326(7) -0.0011(5) 0.0024(5) -0.0087(6) O2AA 0.070(3) 0.077(3) 0.033(2) -0.0065(18) 0.0045(18) -0.004(2) O0AA 0.050(2) 0.098(3) 0.032(2) 0.0032(19) 0.0024(16) -0.001(2) C9BA 0.048(3) 0.045(3) 0.030(2) -0.0015(19) 0.006(2) -0.016(2) O 0.087(3) 0.070(3) 0.033(2) 0.0085(17) 0.0043(19) -0.033(2) C0AA 0.057(3) 0.042(3) 0.030(2) 0.0039(19) -0.007(2) -0.018(2) C1AA 0.039(2) 0.046(3) 0.029(2) 0.0000(19) 0.0006(19) -0.018(2) C2AA 0.040(2) 0.047(3) 0.028(2) -0.0030(19) 0.0044(19) -0.017(2) C3AA 0.038(2) 0.053(3) 0.028(2) 0.003(2) -0.0042(19) -0.007(2) C4AA 0.046(3) 0.050(3) 0.028(2) 0.002(2) -0.001(2) -0.016(2) C5AA 0.046(3) 0.047(3) 0.027(2) -0.0007(19) -0.0011(19) -0.013(2) C6AA 0.043(3) 0.041(3) 0.033(2) -0.0011(19) -0.003(2) -0.018(2) C8AA 0.039(2) 0.045(3) 0.036(3) -0.004(2) 0.003(2) -0.014(2) C9AA 0.050(3) 0.052(3) 0.033(3) 0.001(2) -0.002(2) -0.004(2) C0BA 0.052(3) 0.054(3) 0.039(3) 0.003(2) -0.006(2) -0.016(2) C1BA 0.074(4) 0.062(3) 0.031(3) 0.003(2) -0.010(3) -0.009(3) C2BA 0.043(3) 0.056(3) 0.059(4) 0.005(3) -0.014(3) -0.005(2) C3BA 0.088(5) 0.070(4) 0.034(3) 0.004(3) -0.021(3) -0.006(3) C4BA 0.079(4) 0.052(3) 0.056(4) 0.001(3) -0.002(3) -0.015(3) C5BA 0.064(4) 0.074(4) 0.051(4) -0.013(3) -0.001(3) -0.002(3) C6BA 0.056(3) 0.064(4) 0.052(4) 0.004(3) -0.021(3) -0.009(3) C7BA 0.079(4) 0.077(4) 0.053(4) -0.006(3) -0.030(3) -0.008(3) N12 0.055(3) 0.068(3) 0.036(2) 0.003(2) -0.005(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S001 C9BA 1.703(5) . ? S001 C8AA 1.747(5) . ? O2AA C2AA 1.225(5) . ? O0AA C4AA 1.208(6) . ? C9BA C1AA 1.381(6) . ? C9BA C2AA 1.437(7) . ? O C3AA 1.203(6) . ? C0AA C1BA 1.392(7) . ? C0AA C6AA 1.397(6) . ? C0AA C2AA 1.491(7) . ? C1AA C5AA 1.394(6) . ? C1AA C4AA 1.479(7) . ? C3AA C5AA 1.503(6) . ? C3AA C9AA 1.535(7) . ? C4AA C6AA 1.487(6) . ? C5AA C8AA 1.386(7) . ? C6AA C0BA 1.382(7) . ? C8AA N12 1.329(6) . ? C9AA C5BA 1.521(7) . ? C9AA C7BA 1.526(7) . ? C9AA C4BA 1.531(8) . ? C0BA C6BA 1.384(7) . ? C0BA H0BA 0.9300 . ? C1BA C3BA 1.366(8) . ? C1BA H1BA 0.9300 . ? C2BA N12 1.452(7) . ? C2BA H2B1 0.9600 . ? C2BA H2B2 0.9600 . ? C2BA H2B3 0.9600 . ? C3BA C6BA 1.364(8) . ? C3BA H3BA 0.9300 . ? C4BA H4B1 0.9600 . ? C4BA H4B2 0.9600 . ? C4BA H4B3 0.9600 . ? C5BA H5B1 0.9600 . ? C5BA H5B2 0.9600 . ? C5BA H5B3 0.9600 . ? C6BA H6BA 0.9300 . ? C7BA H7B1 0.9600 . ? C7BA H7B2 0.9600 . ? C7BA H7B3 0.9600 . ? N12 H12 0.8600 . ? 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 C9BA S001 C8AA 91.4(2) . . ? C1AA C9BA C2AA 124.1(5) . . ? C1AA C9BA S001 111.6(4) . . ? C2AA C9BA S001 124.3(4) . . ? C1BA C0AA C6AA 119.1(5) . . ? C1BA C0AA C2AA 119.1(5) . . ? C6AA C0AA C2AA 121.8(4) . . ? C9BA C1AA C5AA 114.1(4) . . ? C9BA C1AA C4AA 120.3(4) . . ? C5AA C1AA C4AA 125.6(4) . . ? O2AA C2AA C9BA 122.4(5) . . ? O2AA C2AA C0AA 121.6(4) . . ? C9BA C2AA C0AA 116.0(4) . . ? O C3AA C5AA 119.7(4) . . ? O C3AA C9AA 119.9(4) . . ? C5AA C3AA C9AA 119.9(4) . . ? O0AA C4AA C1AA 121.1(4) . . ? O0AA C4AA C6AA 121.6(5) . . ? C1AA C4AA C6AA 117.3(4) . . ? C8AA C5AA C1AA 111.6(4) . . ? C8AA C5AA C3AA 121.2(4) . . ? C1AA C5AA C3AA 127.2(4) . . ? C0BA C6AA C0AA 119.4(5) . . ? C0BA C6AA C4AA 120.2(4) . . ? C0AA C6AA C4AA 120.4(4) . . ? N12 C8AA C5AA 128.9(4) . . ? N12 C8AA S001 119.8(4) . . ? C5AA C8AA S001 111.3(4) . . ? C5BA C9AA C7BA 110.2(5) . . ? C5BA C9AA C4BA 109.9(5) . . ? C7BA C9AA C4BA 108.6(5) . . ? C5BA C9AA C3AA 109.6(4) . . ? C7BA C9AA C3AA 105.2(4) . . ? C4BA C9AA C3AA 113.4(4) . . ? C6BA C0BA C6AA 120.2(5) . . ? C6BA C0BA H0BA 119.9 . . ? C6AA C0BA H0BA 119.9 . . ? C3BA C1BA C0AA 120.6(5) . . ? C3BA C1BA H1BA 119.7 . . ? C0AA C1BA H1BA 119.7 . . ? N12 C2BA H2B1 109.5 . . ? N12 C2BA H2B2 109.5 . . ? H2B1 C2BA H2B2 109.5 . . ? N12 C2BA H2B3 109.5 . . ? H2B1 C2BA H2B3 109.5 . . ? H2B2 C2BA H2B3 109.5 . . ? C6BA C3BA C1BA 120.4(5) . . ? C6BA C3BA H3BA 119.8 . . ? C1BA C3BA H3BA 119.8 . . ? C9AA C4BA H4B1 109.5 . . ? C9AA C4BA H4B2 109.5 . . ? H4B1 C4BA H4B2 109.5 . . ? C9AA C4BA H4B3 109.5 . . ? H4B1 C4BA H4B3 109.5 . . ? H4B2 C4BA H4B3 109.5 . . ? C9AA C5BA H5B1 109.5 . . ? C9AA C5BA H5B2 109.5 . . ? H5B1 C5BA H5B2 109.5 . . ? C9AA C5BA H5B3 109.5 . . ? H5B1 C5BA H5B3 109.5 . . ? H5B2 C5BA H5B3 109.5 . . ? C3BA C6BA C0BA 120.3(5) . . ? C3BA C6BA H6BA 119.8 . . ? C0BA C6BA H6BA 119.8 . . ? C9AA C7BA H7B1 109.5 . . ? C9AA C7BA H7B2 109.5 . . ? H7B1 C7BA H7B2 109.5 . . ? C9AA C7BA H7B3 109.5 . . ? H7B1 C7BA H7B3 109.5 . . ? H7B2 C7BA H7B3 109.5 . . ? C8AA N12 C2BA 122.9(4) . . ? C8AA N12 H12 118.6 . . ? C2BA N12 H12 118.6 . . ? _diffrn_measured_fraction_theta_max 0.836 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.751 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 915292'