# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Krystian, Pluta' 'Malgorzata, Nowak' 'Kinga, Suwinska' _publ_contact_author_name 'Dr Krystian Pluta' _publ_contact_author_address ; Department of Organic Chemistry Silesian School of Medicine Jagiellonska 4 Sosnowiec 41-200 POLAND ; _publ_contact_author_email 'PLUTA@SLAM.KATOWICE.PL' _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Synthesis of novel heteropentacenes containing nitrogen, sulfur and oxygen or selenium ; _ccdc_temp_data_collection 293 _ccdc_ls_R_squared 0.1068 _ccdc_disorder no _ccdc_comments ; ? ; data_kp05 _database_code_CSD 190255 _audit_creation_date 2002-02-13T08:02:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 5,7-Diaza-6-selena-13-thiapentacene also: diquino[3,2-b;2',3'-e][1,4]thiaselenin also: 1,4-thiaselenino[3,2-b;5,6-b']diquinoline ; _chemical_formula_moiety 'C18 H10 N2 S Se' _chemical_formula_sum 'C18 H10 N2 S Se' _chemical_formula_weight 365.30 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'Pnma' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 14.3960(1) _cell_length_b 16.1410(4) _cell_length_c 6.1360(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1425.8(1) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1817 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'needle' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.776 _exptl_absorpt_correction_type 'none' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method ; ; 85 frames via \f rotation and 15 frames via \o rotation (rotation angle 2\%) and 2*400 s per frame ; _diffrn_detector_area_resol_mean ; 1242 (horizontal) x 1152 (vertical) pixels, CCD pixel size is 22.5 x 22.5 \mm which gives at the input a pixel of 110 x 110 \mm (with 2 x 2 binning) ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3139 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1673 _reflns_number_gt 1379 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect data collection software (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0441P)^2^+1.2962P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0027(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1673 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 Se1 Se 0.87411(4) 0.7500 0.08218(7) 0.0526(2) Uani 1 2 d S . . S1 S 0.74897(7) 0.7500 0.55569(17) 0.0374(3) Uani 1 2 d S . . N1 N 0.90108(17) 0.59025(15) 0.2000(4) 0.0374(6) Uani 1 1 d . . . C2 C 0.86341(18) 0.65810(18) 0.2756(4) 0.0324(6) Uani 1 1 d . . . C3 C 0.81691(18) 0.66380(17) 0.4802(4) 0.0318(6) Uani 1 1 d . . . C4 C 0.81502(19) 0.59501(18) 0.6093(5) 0.0348(6) Uani 1 1 d . . . H4 H 0.7884 0.5976 0.7472 0.042 Uiso 1 1 calc R . . C5 C 0.85355(19) 0.51998(19) 0.5333(5) 0.0358(6) Uani 1 1 d . . . C6 C 0.8513(2) 0.4455(2) 0.6541(6) 0.0469(8) Uani 1 1 d . . . H6 H 0.8248 0.4450 0.7924 0.056 Uiso 1 1 calc R . . C7 C 0.8873(2) 0.3745(2) 0.5706(6) 0.0549(10) Uani 1 1 d . . . H7 H 0.8850 0.3258 0.6513 0.066 Uiso 1 1 calc R . . C8 C 0.9277(2) 0.3745(2) 0.3630(7) 0.0533(9) Uani 1 1 d . . . H8 H 0.9520 0.3255 0.3073 0.064 Uiso 1 1 calc R . . C9 C 0.9322(2) 0.44497(19) 0.2411(6) 0.0454(7) Uani 1 1 d . . . H9 H 0.9600 0.4439 0.1043 0.055 Uiso 1 1 calc R . . C10 C 0.89446(19) 0.51969(18) 0.3229(5) 0.0352(6) 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 Se1 0.0919(5) 0.0351(3) 0.0307(3) 0.000 0.0065(2) 0.000 S1 0.0371(6) 0.0331(6) 0.0420(6) 0.000 0.0067(4) 0.000 N1 0.0430(14) 0.0316(13) 0.0376(13) -0.0014(10) 0.0027(10) -0.0019(11) C2 0.0364(15) 0.0291(14) 0.0318(14) 0.0013(11) -0.0014(11) -0.0050(12) C3 0.0328(14) 0.0288(14) 0.0337(14) -0.0002(11) -0.0015(11) -0.0036(12) C4 0.0342(15) 0.0356(16) 0.0345(15) 0.0031(12) 0.0022(11) -0.0057(13) C5 0.0307(14) 0.0319(15) 0.0448(16) 0.0029(13) -0.0014(12) -0.0062(12) C6 0.0437(18) 0.0402(18) 0.057(2) 0.0141(15) 0.0025(14) -0.0044(15) C7 0.050(2) 0.0309(18) 0.083(3) 0.0176(17) -0.0008(17) -0.0044(15) C8 0.0453(19) 0.0297(17) 0.085(2) -0.0032(16) 0.0020(18) -0.0013(15) C9 0.0426(17) 0.0345(17) 0.0592(19) -0.0040(14) 0.0026(15) -0.0038(14) C10 0.0337(15) 0.0298(15) 0.0422(16) -0.0015(13) -0.0027(11) -0.0037(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Se1 C2 1.906(3) 8_575 ? Se1 C2 1.906(3) . ? S1 C3 1.763(3) 8_575 ? S1 C3 1.763(3) . ? N1 C2 1.307(4) . ? N1 C10 1.369(4) . ? C2 C3 1.426(4) . ? C3 C4 1.364(4) . ? C4 C5 1.411(4) . ? C5 C6 1.413(4) . ? C5 C10 1.419(4) . ? C6 C7 1.358(5) . ? C7 C8 1.400(5) . ? C8 C9 1.363(5) . ? C9 C10 1.414(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 C2 Se1 C2 102.20(17) 8_575 . ? C3 S1 C3 104.25(18) 8_575 . ? C2 N1 C10 118.2(2) . . ? N1 C2 C3 124.2(3) . . ? N1 C2 Se1 113.4(2) . . ? C3 C2 Se1 122.4(2) . . ? C4 C3 C2 117.9(3) . . ? C4 C3 S1 118.6(2) . . ? C2 C3 S1 122.9(2) . . ? C3 C4 C5 119.9(3) . . ? C4 C5 C6 123.2(3) . . ? C4 C5 C10 117.8(3) . . ? C6 C5 C10 119.0(3) . . ? C7 C6 C5 120.7(3) . . ? C6 C7 C8 120.1(3) . . ? C9 C8 C7 121.3(3) . . ? C8 C9 C10 119.9(3) . . ? N1 C10 C9 119.2(3) . . ? N1 C10 C5 121.8(3) . . ? C9 C10 C5 119.0(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 C10 N1 C2 C3 1.0(4) . . . . ? C10 N1 C2 Se1 -177.76(19) . . . . ? C2 Se1 C2 N1 -156.51(15) 8_575 . . . ? C2 Se1 C2 C3 24.7(3) 8_575 . . . ? N1 C2 C3 C4 2.9(4) . . . . ? Se1 C2 C3 C4 -178.4(2) . . . . ? N1 C2 C3 S1 -168.1(2) . . . . ? Se1 C2 C3 S1 10.6(3) . . . . ? C3 S1 C3 C4 143.98(17) 8_575 . . . ? C3 S1 C3 C2 -45.1(3) 8_575 . . . ? C2 C3 C4 C5 -3.7(4) . . . . ? S1 C3 C4 C5 167.7(2) . . . . ? C3 C4 C5 C6 -177.7(3) . . . . ? C3 C4 C5 C10 0.8(4) . . . . ? C4 C5 C6 C7 178.2(3) . . . . ? C10 C5 C6 C7 -0.3(5) . . . . ? C5 C6 C7 C8 0.4(5) . . . . ? C6 C7 C8 C9 0.2(5) . . . . ? C7 C8 C9 C10 -0.8(5) . . . . ? C2 N1 C10 C9 178.0(3) . . . . ? C2 N1 C10 C5 -4.1(4) . . . . ? C8 C9 C10 N1 178.8(3) . . . . ? C8 C9 C10 C5 0.9(4) . . . . ? C4 C5 C10 N1 3.2(4) . . . . ? C6 C5 C10 N1 -178.2(3) . . . . ? C4 C5 C10 C9 -178.9(3) . . . . ? C6 C5 C10 C9 -0.3(4) . . . . ? data_kp06 _database_code_CSD 190256 _audit_creation_date 2002-02-13T08:02:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 14-cyjano-14-phenyl-5,7-diaza-13-thiapentacene also: 14-cyjano-14-phenyldiquino[3,2-b;2',3'-e]thiopyran; also: 14-cyjano-14-phenylthiopyrano[3,2-b;5,6- b']diquinoline ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H15 N3 S' _chemical_formula_weight 401.47 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'Pnma' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 9.8440(3) _cell_length_b 15.5250(3) _cell_length_c 13.2510(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2025.1(1) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2466 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'block' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method ; ; 66 frames via \f rotation and 24 frames via \o rotation (rotation angle 2\%) and 2*20 s per frame ; _diffrn_detector_area_resol_mean ; 1242 (horizontal) x 1152 (vertical) pixels, CCD pixel size is 22.5 x 22.5 \mm which gives at the input a pixel of 110 x 110 \mm (with 2 x 2 binning) ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4485 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2397 _reflns_number_gt 1776 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect data collection software (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0547P)^2^+0.3047P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.005(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2397 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0.07078(6) 0.7500 0.69141(4) 0.0509(2) Uani 1 2 d S . . N1 N 0.30544(11) 0.60638(8) 0.87296(8) 0.0407(3) Uani 1 1 d . . . C2 C 0.23190(13) 0.66902(9) 0.83448(10) 0.0370(3) Uani 1 1 d . . . C3 C 0.16789(13) 0.66414(10) 0.73841(11) 0.0413(4) Uani 1 1 d . . . C4 C 0.18227(15) 0.59061(11) 0.68362(11) 0.0492(4) Uani 1 1 d . . . H4 H 0.1413 0.5861 0.6206 0.059 Uiso 1 1 calc R . . C5 C 0.25872(15) 0.52143(10) 0.72182(12) 0.0488(4) Uani 1 1 d . . . C6 C 0.2790(2) 0.44366(12) 0.66923(15) 0.0672(5) Uani 1 1 d . . . H6 H 0.2390 0.4358 0.6063 0.081 Uiso 1 1 calc R . . C7 C 0.3564(2) 0.38006(13) 0.70972(16) 0.0746(6) Uani 1 1 d . . . H7 H 0.3700 0.3293 0.6739 0.090 Uiso 1 1 calc R . . C8 C 0.41630(18) 0.39018(12) 0.80513(14) 0.0629(5) Uani 1 1 d . . . H8 H 0.4687 0.3460 0.8323 0.076 Uiso 1 1 calc R . . C9 C 0.39790(16) 0.46430(11) 0.85794(13) 0.0518(4) Uani 1 1 d . . . H9 H 0.4375 0.4703 0.9213 0.062 Uiso 1 1 calc R . . C10 C 0.31978(14) 0.53218(10) 0.81803(11) 0.0427(4) Uani 1 1 d . . . C21 C 0.21069(19) 0.7500 0.89834(15) 0.0379(5) Uani 1 2 d S . . C23 C 0.0650(2) 0.7500 0.94418(15) 0.0460(5) Uani 1 2 d S . . N2 N 0.3747(2) 0.7500 1.05348(14) 0.0554(5) Uani 1 2 d S . . C22 C 0.3064(2) 0.7500 0.98422(15) 0.0395(5) Uani 1 2 d S . . C24 C 0.00205(18) 0.67370(14) 0.96831(14) 0.0716(6) Uani 1 1 d . . . H24 H 0.0438 0.6216 0.9527 0.086 Uiso 1 1 calc R . . C25 C -0.1235(2) 0.67411(17) 1.01580(17) 0.0929(8) Uani 1 1 d . . . H25 H -0.1661 0.6223 1.0312 0.111 Uiso 1 1 calc R . . C26 C -0.1846(3) 0.7500 1.0400(2) 0.0935(11) Uani 1 2 d S . . H26 H -0.2680 0.7500 1.0730 0.112 Uiso 1 2 calc SR . . 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 0.0455(3) 0.0461(4) 0.0613(4) 0.000 -0.0212(3) 0.000 N1 0.0402(6) 0.0365(7) 0.0454(7) 0.0031(6) -0.0028(5) -0.0035(5) C2 0.0334(6) 0.0366(8) 0.0411(8) 0.0007(6) -0.0014(6) -0.0054(6) C3 0.0363(7) 0.0409(9) 0.0469(8) 0.0003(7) -0.0068(6) -0.0046(7) C4 0.0515(9) 0.0460(10) 0.0499(9) -0.0055(7) -0.0131(7) -0.0051(8) C5 0.0493(8) 0.0402(9) 0.0570(10) -0.0055(7) -0.0060(7) -0.0046(7) C6 0.0850(13) 0.0475(11) 0.0692(12) -0.0161(9) -0.0169(10) 0.0023(10) C7 0.0920(14) 0.0420(11) 0.0898(14) -0.0168(10) -0.0106(12) 0.0101(10) C8 0.0635(11) 0.0384(10) 0.0869(13) 0.0028(9) -0.0061(9) 0.0059(8) C9 0.0513(9) 0.0408(9) 0.0634(10) 0.0054(8) -0.0077(8) -0.0029(8) C10 0.0383(7) 0.0362(8) 0.0536(9) -0.0006(7) -0.0014(6) -0.0054(6) C21 0.0353(10) 0.0394(12) 0.0390(10) 0.000 -0.0028(8) 0.000 C23 0.0359(10) 0.0609(15) 0.0412(11) 0.000 0.0012(9) 0.000 N2 0.0625(12) 0.0532(13) 0.0505(11) 0.000 -0.0124(10) 0.000 C22 0.0398(10) 0.0379(12) 0.0409(11) 0.000 0.0017(9) 0.000 C24 0.0551(10) 0.0759(14) 0.0838(13) 0.0022(11) 0.0183(9) -0.0102(10) C25 0.0643(12) 0.115(2) 0.0996(16) 0.0037(15) 0.0286(12) -0.0266(14) C26 0.0498(16) 0.139(3) 0.091(2) 0.000 0.0244(16) 0.000 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C3 1.7546(15) 8_575 ? S1 C3 1.7546(15) . ? N1 C2 1.3153(17) . ? N1 C10 1.3699(19) . ? C2 C3 1.4225(19) . ? C2 C21 1.5297(18) . ? C3 C4 1.360(2) . ? C4 C5 1.406(2) . ? C5 C6 1.408(2) . ? C5 C10 1.419(2) . ?