# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Israel Agranat' 'Shmuel Cohen' 'Amalia Levy' _publ_contact_author_name 'Prof Israel Agranat' _publ_contact_author_address ; Department of Organic Chemistry The Hebrew University of Jerusalem Philadelphia Building 201/205 Department of Organic Chemistry The Hebrew University of Jerusalem Jerusalem 91904 ISRAEL ; _publ_contact_author_email ISRIA@VMS.HUJI.AC.IL _publ_section_title ; Overcrowded 1,8-Diazafluorenylidene-Chalcoxanthenes. Introducing Nitrogens at the Fjord Regions of Bistricyclic Aromatic Enes ; #------------------------------------------------------------------------------ data_Compound_14 _database_code_CSD 207024 #------------------------------------------------------------------------------ _audit_creation_date 'Sun Feb 9 16:42:32 2003' _audit_creation_method 'from TEXRAY.INF file' #------------------------------------------------------------------------------ _computing_data_collection 'Philips PW1100 Diffractometer Control' _computing_cell_refinement 'Philips PW1100 Diffractometer Control' _computing_data_reduction teXsan _computing_structure_solution SHELXS86 _computing_structure_refinement teXsan _computing_publication_material teXsan #------------------------------------------------------------------------------ _cell_length_a 12.579(2) _cell_length_b 11.920(2) _cell_length_c 12.202(2) _cell_angle_alpha 90 _cell_angle_beta 92.68(1) _cell_angle_gamma 90 _cell_volume 1827.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293.2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 13.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' 1/2-x,1/2+y,1/2-z ' -x, -y, -z' 1/2+x,1/2-y,1/2+z #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.420 _exptl_crystal_size_mid 0.380 _exptl_crystal_size_min 0.250 _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_meas 0.000 _chemical_formula_weight 457.99 _chemical_formula_moiety 'C24 H14 N2 Te' _exptl_crystal_F_000 896.00 _exptl_absorpt_coefficient_mu 1.638 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details Walker&Stuart_DIFABS _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.44 #------------------------------------------------------------------------------ _diffrn_special_details none _diffrn_ambient_temperature 293.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector scintillation _diffrn_measurement_device 'Philips PW1100' _diffrn_measurement_method 'omega/2-theta scans' _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 6 2 1 _diffrn_reflns_number 5782 _reflns_number_total 5782 _reflns_number_observed 3444 _reflns_observed_criterion 3.00 _diffrn_reflns_av_R_equivalents 1.95 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_reduction_process ? _diffrn_orient_matrix_UB_11 0.01269 _diffrn_orient_matrix_UB_12 -0.05809 _diffrn_orient_matrix_UB_13 -0.00030 _diffrn_orient_matrix_UB_21 -0.03645 _diffrn_orient_matrix_UB_22 -0.00818 _diffrn_orient_matrix_UB_23 -0.04558 _diffrn_orient_matrix_UB_31 0.04134 _diffrn_orient_matrix_UB_32 0.01066 _diffrn_orient_matrix_UB_33 -0.03637 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 96 0.003 0.002 'International Tables' H 0 56 0.000 0.000 'International Tables' N 0 8 0.006 0.003 'International Tables' Te 0 4 -0.531 1.675 'International Tables' #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type Te(10) 0.22705(3) 0.61179(3) 0.43896(3) 0.048 Uani N(1') -0.0260(4) 0.3548(4) 0.2313(4) 0.046 Uani N(8') 0.3018(4) 0.4370(5) 0.0423(4) 0.052 Uani C(1) 0.1207(4) 0.2668(5) 0.3980(5) 0.044 Uani C(2) 0.0701(5) 0.2440(6) 0.4943(6) 0.054 Uani C(2') -0.1244(5) 0.3271(6) 0.1916(6) 0.055 Uani C(3) 0.0610(5) 0.3262(6) 0.5726(5) 0.053 Uani C(3') -0.1518(6) 0.3124(6) 0.0817(7) 0.064 Uani C(4) 0.1035(5) 0.4306(6) 0.5576(5) 0.047 Uani C(4') -0.0775(6) 0.3293(6) 0.0054(6) 0.057 Uani C(4a) 0.1556(4) 0.4549(4) 0.4630(4) 0.036 Uani C(4a') 0.0249(5) 0.3581(4) 0.0425(4) 0.042 Uani C(4b') 0.1205(5) 0.3828(4) -0.0123(4) 0.044 Uani C(5) 0.4571(4) 0.5627(5) 0.3813(5) 0.045 Uani C(5') 0.1432(7) 0.3849(6) -0.1211(5) 0.061 Uani C(6) 0.5374(5) 0.5017(6) 0.3389(5) 0.053 Uani C(6') 0.2448(8) 0.4131(7) -0.1476(6) 0.072 Uani C(7) 0.5154(5) 0.4087(6) 0.2748(5) 0.050 Uani C(7') 0.3196(7) 0.4386(7) -0.0649(6) 0.065 Uani C(8a) 0.3275(4) 0.4376(4) 0.2952(4) 0.035 Uani C(8a') 0.2037(5) 0.4084(4) 0.0664(4) 0.041 Uani C(8) 0.4116(4) 0.3755(5) 0.2539(5) 0.043 Uani C(9a) 0.1616(4) 0.3746(4) 0.3812(4) 0.034 Uani C(9a') 0.0470(5) 0.3663(4) 0.1557(4) 0.041 Uani C(9) 0.2144(4) 0.4010(4) 0.2770(4) 0.032 Uani C(9') 0.1619(4) 0.3941(4) 0.1780(4) 0.036 Uani C(10a) 0.3517(4) 0.5294(4) 0.3617(4) 0.036 Uani H(1) 0.127(6) 0.210(6) 0.344(6) 0.05(2) Uiso H(2) 0.042(5) 0.171(6) 0.506(5) 0.06(2) Uiso H(2') -0.178(4) 0.317(4) 0.243(4) 0.07(1) Uiso H(3) 0.025(5) 0.310(6) 0.638(6) 0.06(2) Uiso H(3') -0.222(5) 0.291(5) 0.059(5) 0.08(2) Uiso H(4) 0.097(4) 0.487(5) 0.612(5) 0.06(1) Uiso H(4') -0.095(5) 0.321(5) -0.071(5) 0.07(2) Uiso H(5) 0.473(4) 0.628(4) 0.424(5) 0.05(1) Uiso H(5') 0.090(7) 0.367(6) -0.177(7) 0.07(2) Uiso H(6) 0.609(5) 0.524(5) 0.354(5) 0.06(2) Uiso H(6') 0.263(6) 0.415(6) -0.222(6) 0.09(2) Uiso H(7) 0.572(5) 0.367(5) 0.245(5) 0.06(2) Uiso H(7') 0.389(6) 0.459(6) -0.086(6) 0.08(2) Uiso H(8) 0.397(3) 0.310(4) 0.211(4) 0.052(10) Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Te(10) 0.0473(2) 0.0464(2) 0.0512(3) 0.0021(2) 0.0032(2) -0.0084(2) N(1') 0.037(2) 0.062(3) 0.038(3) -0.003(2) -0.009(2) 0.003(2) N(8') 0.053(3) 0.076(3) 0.026(3) 0.007(3) 0.002(2) 0.007(2) C(1) 0.038(3) 0.050(3) 0.041(3) -0.005(2) -0.017(2) 0.008(3) C(2) 0.039(3) 0.073(4) 0.048(4) -0.018(3) -0.012(3) 0.026(3) C(2') 0.037(3) 0.073(4) 0.055(4) -0.008(3) -0.013(3) 0.007(3) C(3) 0.035(3) 0.087(5) 0.037(3) -0.003(3) -0.001(3) 0.021(3) C(3') 0.040(3) 0.072(4) 0.076(5) -0.010(3) -0.026(4) 0.000(4) C(4) 0.037(3) 0.078(4) 0.026(3) 0.009(3) -0.002(2) 0.007(3) C(4') 0.067(4) 0.061(4) 0.039(4) 0.004(3) -0.035(3) -0.005(3) C(4a) 0.031(2) 0.052(3) 0.025(3) 0.005(2) -0.004(2) 0.000(2) C(4a') 0.051(3) 0.042(3) 0.031(3) 0.007(2) -0.017(2) -0.002(2) C(4b') 0.058(3) 0.049(3) 0.024(3) 0.012(3) -0.012(2) -0.002(2) C(5) 0.043(3) 0.054(3) 0.038(3) -0.012(3) 0.000(3) -0.004(3) C(5') 0.087(5) 0.065(4) 0.028(3) 0.006(4) -0.007(3) -0.004(3) C(6) 0.035(3) 0.080(4) 0.044(4) -0.012(3) -0.003(3) 0.006(3) C(6') 0.110(7) 0.087(5) 0.020(3) 0.018(5) 0.005(4) 0.008(3) C(7) 0.035(3) 0.074(4) 0.041(3) 0.002(3) 0.009(2) 0.000(3) C(7') 0.070(5) 0.085(5) 0.041(4) 0.018(4) 0.016(4) 0.020(4) C(8a) 0.039(3) 0.045(3) 0.019(2) 0.001(2) -0.001(2) 0.002(2) C(8a') 0.047(3) 0.049(3) 0.025(3) 0.005(2) -0.004(2) 0.002(2) C(8) 0.038(3) 0.057(3) 0.034(3) 0.000(2) 0.000(2) -0.009(3) C(9a) 0.028(2) 0.051(3) 0.023(2) -0.003(2) -0.005(2) 0.002(2) C(9a') 0.046(3) 0.048(3) 0.029(3) 0.004(2) -0.010(2) -0.001(2) C(9) 0.032(2) 0.043(2) 0.021(2) 0.002(2) -0.004(2) 0.001(2) C(9') 0.041(3) 0.046(2) 0.021(2) 0.005(2) -0.006(2) 0.004(2) C(10a) 0.034(2) 0.045(2) 0.030(3) -0.004(2) -0.001(2) 0.005(2) #------------------------------------------------------------------------------ _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_extinction_coef 16.47666 _refine_ls_number_reflns 3444 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.047 _refine_ls_wR_factor_obs 0.065 _refine_ls_goodness_of_fit_obs 2.080 _refine_ls_shift/esd_max 0.0010 _refine_diff_density_max 0.68 _refine_diff_density_min -0.90 #------------------------------------------------------------------------------ _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Te(10) C(4a) 2.102(5) Te(10) C(10a) 2.110(5) N(1') C(2') 1.348(7) N(1') C(9a') 1.339(7) N(8') C(7') 1.337(8) N(8') C(8a') 1.327(8) C(1) C(2) 1.389(9) C(1) C(9a) 1.403(7) C(2) C(3) 1.38(1) C(2') C(3') 1.380(10) C(3) C(4) 1.370(10) C(3') C(4') 1.37(1) C(4) C(4a) 1.383(8) C(4') C(4a') 1.388(8) C(4a) C(9a) 1.388(7) C(4a') C(4b') 1.434(9) C(4a') C(9a') 1.400(7) C(4b') C(5') 1.371(9) C(4b') C(8a') 1.420(8) C(5) C(6) 1.365(9) C(5) C(10a) 1.393(7) C(5') C(6') 1.37(1) C(6) C(7) 1.377(9) C(6') C(7') 1.38(1) C(7) C(8) 1.377(8) C(8a) C(8) 1.404(8) C(8a) C(9) 1.494(7) C(8a) C(10a) 1.388(7) C(8a') C(9') 1.493(7) C(9a) C(9) 1.495(7) C(9a') C(9') 1.495(8) C(9) C(9') 1.352(7) #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C(4a) Te(10) C(10a) 88.8(2) C(2') N(1') C(9a') 115.1(5) C(7') N(8') C(8a') 114.8(6) C(2) C(1) C(9a) 119.3(6) C(1) C(2) C(3) 120.3(6) N(1') C(2') C(3') 124.3(7) C(2) C(3) C(4) 120.5(6) C(2') C(3') C(4') 119.7(6) C(3) C(4) C(4a) 120.3(6) C(3') C(4') C(4a') 118.0(6) Te(10) C(4a) C(4) 121.7(4) Te(10) C(4a) C(9a) 118.4(4) C(4) C(4a) C(9a) 120.0(5) C(4') C(4a') C(4b') 133.2(6) C(4') C(4a') C(9a') 118.5(6) C(4b') C(4a') C(9a') 108.3(5) C(4a') C(4b') C(5') 132.2(6) C(4a') C(4b') C(8a') 109.6(5) C(5') C(4b') C(8a') 118.1(6) C(6) C(5) C(10a) 119.8(6) C(4b') C(5') C(6') 118.0(7) C(5) C(6) C(7) 120.8(6) C(5') C(6') C(7') 119.4(7) C(6) C(7) C(8) 120.0(6) N(8') C(7') C(6') 124.9(8) C(8) C(8a) C(9) 121.4(5) C(8) C(8a) C(10a) 118.5(5) C(9) C(8a) C(10a) 119.9(5) N(8') C(8a') C(4b') 124.7(5) N(8') C(8a') C(9') 127.1(5) C(4b') C(8a') C(9') 108.2(5) C(7) C(8) C(8a) 120.4(5) C(1) C(9a) C(4a) 119.6(5) C(1) C(9a) C(9) 119.8(5) C(4a) C(9a) C(9) 120.5(4) N(1') C(9a') C(4a') 124.2(5) N(1') C(9a') C(9') 125.8(5) C(4a') C(9a') C(9') 109.9(5) C(8a) C(9) C(9a) 113.1(4) C(8a) C(9) C(9') 124.9(5) C(9a) C(9) C(9') 121.9(4) C(8a') C(9') C(9a') 103.8(4) C(8a') C(9') C(9) 129.0(5) C(9a') C(9') C(9) 127.2(5) Te(10) C(10a) C(5) 120.7(4) Te(10) C(10a) C(8a) 118.7(4) C(5) C(10a) C(8a) 120.4(5) #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data__Compound_13 _database_code_CSD 207025 #------------------------------------------------------------------------------ _audit_creation_date 'Sun Feb 9 16:19:19 2003' _audit_creation_method 'from TEXRAY.INF file' #------------------------------------------------------------------------------ _computing_data_collection 'Philips PW1100 Diffractometer Control' _computing_cell_refinement 'Philips PW1100 Diffractometer Control' _computing_data_reduction teXsan _computing_structure_solution SHELXS86 _computing_structure_refinement teXsan _computing_publication_material teXsan #------------------------------------------------------------------------------ _cell_length_a 18.713(3) _cell_length_b 9.553(2) _cell_length_c 4.831(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 863.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293.2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 14.0 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P m n 21 ' _symmetry_Int_Tables_number 31 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x, -y,1/2+z' #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_meas 0.000 _chemical_formula_weight 409.35 _chemical_formula_moiety 'C24 H14 N2 Se' _exptl_crystal_F_000 412.00 _exptl_absorpt_coefficient_mu 2.185 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details Walker&Stuart_DIFABS _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.79 #------------------------------------------------------------------------------ _diffrn_special_details none _diffrn_ambient_temperature 293.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector scintillation _diffrn_measurement_device 'Philips PW1100' _diffrn_measurement_method 'omega/2-theta scans' _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 5 5 1 _diffrn_reflns_number 2021 _reflns_number_total 2021 _reflns_number_observed 1004 _reflns_observed_criterion 2.00 _diffrn_reflns_av_R_equivalents 2.64 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2 _diffrn_reflns_theta_max 27.48 _diffrn_orient_matrix_UB_11 0.00193 _diffrn_orient_matrix_UB_12 0.07428 _diffrn_orient_matrix_UB_13 0.00275 _diffrn_orient_matrix_UB_21 -0.03778 _diffrn_orient_matrix_UB_22 0.00397 _diffrn_orient_matrix_UB_23 -0.01322 _diffrn_orient_matrix_UB_31 -0.00339 _diffrn_orient_matrix_UB_32 -0.00095 _diffrn_orient_matrix_UB_33 0.14650 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 48 0.003 0.002 'International Tables' H 0 28 0.000 0.000 'International Tables' N 0 4 0.006 0.003 'International Tables' Se 0 2 -0.093 2.226 'International Tables' #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type Se(10) 1.000 0.01310(6) 0.740 0.040 Uani N(1') 0.8683(2) 0.4843(4) 0.627(1) 0.040 Uani C(1) 0.8833(2) 0.2651(5) 0.202(1) 0.035 Uani C(2) 0.8252(2) 0.1824(6) 0.134(1) 0.044 Uani C(2') 0.8217(2) 0.5661(5) 0.765(2) 0.046 Uani C(3) 0.8165(2) 0.0539(5) 0.261(2) 0.044 Uani C(3') 0.8401(3) 0.6690(5) 0.949(1) 0.048 Uani C(4) 0.8663(3) 0.0054(4) 0.445(1) 0.041 Uani C(4') 0.9118(3) 0.6961(5) 1.001(1) 0.048 Uani C(4a) 0.9263(2) 0.0860(4) 0.508(1) 0.030 Uani C(4a') 0.9611(2) 0.6150(4) 0.861(1) 0.036 Uani C(9) 1.000 0.3014(6) 0.460(1) 0.029 Uani C(9') 1.000 0.4305(6) 0.571(1) 0.030 Uani C(9a) 0.9337(2) 0.2189(4) 0.396(1) 0.030 Uani C(9a') 0.9373(2) 0.5090(4) 0.6802(9) 0.032 Uani H(1) 0.889 0.354 0.117 0.042 Uiso H(2) 0.791 0.214 0.001 0.053 Uiso H(2') 0.772 0.551 0.732 0.055 Uiso H(3) 0.776 -0.001 0.220 0.053 Uiso H(3') 0.804 0.722 1.040 0.058 Uiso H(4) 0.860 -0.083 0.530 0.049 Uiso H(4') 0.926 0.767 1.127 0.057 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Se(10) 0.0377(3) 0.0418(4) 0.0411(4) 0.000 0.000 0.0138(5) N(1') 0.036(2) 0.036(2) 0.049(2) 0.005(2) -0.001(2) 0.005(2) C(1) 0.038(2) 0.041(2) 0.025(3) 0.004(2) 0.000(2) 0.004(2) C(2) 0.032(2) 0.061(3) 0.040(3) 0.006(2) -0.011(2) -0.008(3) C(2') 0.041(2) 0.044(2) 0.051(3) 0.008(2) 0.011(4) 0.006(4) C(3) 0.035(2) 0.053(2) 0.045(3) -0.009(2) -0.002(4) -0.008(4) C(3') 0.052(3) 0.040(3) 0.052(3) 0.013(2) 0.010(3) -0.001(3) C(4) 0.037(2) 0.038(2) 0.047(3) -0.009(2) 0.005(2) -0.004(2) C(4') 0.055(3) 0.031(2) 0.057(4) 0.005(2) 0.006(3) -0.006(3) C(4a) 0.032(2) 0.032(2) 0.027(2) 0.000(2) 0.004(2) 0.002(2) C(4a') 0.044(2) 0.025(2) 0.039(3) 0.003(2) 0.004(2) 0.004(2) C(9) 0.032(3) 0.028(3) 0.026(3) 0.000 0.000 0.002(3) C(9') 0.035(3) 0.023(3) 0.032(4) 0.000 0.000 0.009(3) C(9a) 0.024(2) 0.034(2) 0.030(3) 0.004(2) -0.001(2) -0.002(2) C(9a') 0.036(2) 0.026(2) 0.034(4) 0.002(2) 0.001(2) 0.005(2) #------------------------------------------------------------------------------ _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_extinction_coef 16.93120 _refine_ls_number_reflns 1004 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.036 _refine_ls_wR_factor_obs 0.042 _refine_ls_goodness_of_fit_obs 1.400 _refine_ls_shift/esd_max 0.0010 _refine_diff_density_max 0.33 _refine_diff_density_min -0.57 #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Se(10) C(4a) 1.910(4) Se(10) C(4a) 1.910(4) N(1') C(2') 1.346(7) N(1') C(9a') 1.337(6) C(1) C(2) 1.383(6) C(1) C(9a) 1.399(6) C(2) C(3) 1.382(8) C(2') C(3') 1.368(8) C(3) C(4) 1.367(9) C(3') C(4') 1.388(7) C(4) C(4a) 1.395(6) C(4') C(4a') 1.383(6) C(4a) C(9a) 1.387(6) C(4a') C(4a') 1.457(8) C(4a') C(9a') 1.408(6) C(9) C(9') 1.344(8) C(9) C(9a) 1.503(5) C(9) C(9a) 1.503(5) C(9') C(9a') 1.489(6) C(9') C(9a') 1.489(6) #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C(4a) Se(10) C(4a) 92.5(3) C(2') N(1') C(9a') 115.3(4) C(2) C(1) C(9a) 120.5(4) C(1) C(2) C(3) 119.6(5) N(1') C(2') C(3') 125.1(5) C(2) C(3) C(4) 120.6(4) C(2') C(3') C(4') 119.6(5) C(3) C(4) C(4a) 120.1(4) C(3') C(4') C(4a') 116.8(5) Se(10) C(4a) C(4) 120.5(3) Se(10) C(4a) C(9a) 119.4(3) C(4) C(4a) C(9a) 120.1(4) C(4') C(4a') C(4a') 131.9(3) C(4') C(4a') C(9a') 119.7(4) C(4a') C(4a') C(9a') 108.4(3) C(9') C(9) C(9a) 124.3(2) C(9') C(9) C(9a) 124.3(2) C(9a) C(9) C(9a) 111.3(5) C(9) C(9') C(9a') 127.1(3) C(9) C(9') C(9a') 127.1(3) C(9a') C(9') C(9a') 104.0(5) C(1) C(9a) C(4a) 118.8(4) C(1) C(9a) C(9) 122.0(4) C(4a) C(9a) C(9) 118.8(4) N(1') C(9a') C(4a') 123.4(4) N(1') C(9a') C(9') 127.2(4) C(4a') C(9a') C(9') 109.4(4) data_Compound_12 _database_code_CSD 207026 #------------------------------------------------------------------------------ _audit_creation_date 'Sun Feb 9 12:43:08 2003' _audit_creation_method 'from TEXRAY.INF file' #------------------------------------------------------------------------------ _computing_data_collection 'CAD4 Diffractometer Control' _computing_cell_refinement 'CAD4 Diffractometer Control' _computing_data_reduction teXsan _computing_structure_solution SHELXS86 _computing_structure_refinement teXsan _computing_publication_material teXsan #------------------------------------------------------------------------------ _cell_length_a 18.811(4) _cell_length_b 9.702(3) _cell_length_c 4.639(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 846.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293.2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 22.0 _cell_measurement_theta_max 30.0 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P m n 21 ' _symmetry_Int_Tables_number 31 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x, -y,1/2+z' #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_meas 0.000 _chemical_formula_weight 362.45 _chemical_formula_moiety 'C24 H14 N2 S' _exptl_crystal_F_000 376.00 _exptl_absorpt_coefficient_mu 1.767 #------------------------------------------------------------------------------ _diffrn_special_details none _diffrn_ambient_temperature 293.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector scintillation _diffrn_measurement_device CAD4 _diffrn_measurement_method 'omega/2-theta scans' _diffrn_standards_number 1 _diffrn_standards_interval_count 200 _diffrn_standards_decay_% -0.28 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 9 1 1 _diffrn_reflns_number 1701 _reflns_number_total 1701 _reflns_number_observed 880 _reflns_observed_criterion 2.00 _diffrn_reflns_av_R_equivalents 4.55 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2 _diffrn_reflns_theta_max 69.89 _diffrn_orient_matrix_UB_11 -0.00866 _diffrn_orient_matrix_UB_12 -0.09114 _diffrn_orient_matrix_UB_13 -0.09425 _diffrn_orient_matrix_UB_21 0.00809 _diffrn_orient_matrix_UB_22 -0.04747 _diffrn_orient_matrix_UB_23 0.18856 _diffrn_orient_matrix_UB_31 -0.05182 _diffrn_orient_matrix_UB_32 0.00785 _diffrn_orient_matrix_UB_33 0.04513 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 48 0.018 0.009 'International Tables' H 0 28 0.000 0.000 'International Tables' N 0 4 0.031 0.018 'International Tables' S 0 2 0.333 0.557 'International Tables' #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type S(10) 1.000 0.52066(9) 0.329(4) 0.046 Uani N(1') 0.8690(1) 0.9862(2) 0.229(4) 0.048 Uani C(1) 0.8821(1) 0.7655(3) -0.190(4) 0.044 Uani C(2) 0.8244(2) 0.6821(3) -0.251(4) 0.052 Uani C(2') 0.8234(2) 1.0689(3) 0.363(4) 0.054 Uani C(3) 0.8187(2) 0.5539(3) -0.123(4) 0.051 Uani C(3') 0.8415(2) 1.1762(3) 0.545(4) 0.059 Uani C(4a) 0.9300(1) 0.5880(3) 0.114(4) 0.037 Uani C(4a') 0.9615(2) 1.1195(2) 0.455(4) 0.045 Uani C(4) 0.8703(2) 0.5070(2) 0.061(4) 0.045 Uani C(4') 0.9130(2) 1.2028(3) 0.592(4) 0.053 Uani C(9a) 0.9346(1) 0.7205(2) -0.001(4) 0.035 Uani C(9a') 0.9378(2) 1.0111(2) 0.277(4) 0.040 Uani C(9) 1.000 0.8024(3) 0.061(4) 0.035 Uani C(9') 1.000 0.9318(4) 0.170(4) 0.039 Uani H(1) 0.885 0.860 -0.257 0.070 Uiso H(2) 0.792 0.713 -0.415 0.070 Uiso H(2') 0.775 1.045 0.321 0.070 Uiso H(3) 0.776 0.494 -0.179 0.070 Uiso H(3') 0.802 1.225 0.673 0.070 Uiso H(4) 0.865 0.409 0.119 0.070 Uiso H(4') 0.928 1.273 0.734 0.070 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(10) 0.0470(6) 0.0435(5) 0.0488(6) 0.000 0.000 0.0135(5) N(1') 0.044(1) 0.042(1) 0.058(2) 0.0063(9) 0.003(2) 0.005(1) C(1) 0.043(2) 0.048(1) 0.043(1) 0.002(1) 0.000(2) 0.003(1) C(2) 0.042(2) 0.069(2) 0.045(2) 0.001(1) -0.009(1) -0.004(2) C(2') 0.049(2) 0.050(1) 0.061(2) 0.012(1) 0.007(2) 0.011(2) C(3) 0.040(2) 0.058(2) 0.054(2) -0.009(1) 0.000(2) -0.012(2) C(3') 0.061(2) 0.050(1) 0.066(2) 0.016(1) 0.012(2) 0.001(2) C(4a) 0.037(1) 0.039(1) 0.036(1) 0.0012(9) 0.001(1) -0.002(1) C(4a') 0.055(2) 0.034(1) 0.045(1) 0.000(1) -0.001(1) 0.006(1) C(4) 0.040(2) 0.044(1) 0.051(2) -0.007(1) 0.008(2) -0.004(1) C(4') 0.067(2) 0.038(1) 0.055(2) 0.007(1) 0.004(2) -0.002(1) C(9a) 0.031(1) 0.036(1) 0.037(1) 0.0026(9) 0.002(1) -0.002(1) C(9a') 0.047(2) 0.031(1) 0.043(2) 0.005(1) 0.002(2) 0.0080(10) C(9) 0.034(2) 0.034(1) 0.038(2) 0.000 0.000 0.004(2) C(9') 0.040(2) 0.033(2) 0.046(2) 0.000 0.000 0.009(2) #------------------------------------------------------------------------------ _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_extinction_coef 29.40995 _refine_ls_number_reflns 880 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.038 _refine_ls_wR_factor_obs 0.050 _refine_ls_goodness_of_fit_obs 2.700 _refine_ls_shift/esd_max 0.0000 _refine_diff_density_max 0.22 _refine_diff_density_min -0.28 #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S(10) C(4a) 1.775(3) S(10) C(4a) 1.775(3) N(1') C(2') 1.328(4) N(1') C(9a') 1.334(4) C(1) C(2) 1.384(4) C(1) C(9a) 1.390(4) C(2) C(3) 1.383(4) C(2') C(3') 1.385(5) C(3) C(4) 1.371(5) C(3') C(4') 1.387(4) C(4a) C(4) 1.393(4) C(4a) C(9a) 1.396(4) C(4a') C(4a') 1.450(6) C(4a') C(4') 1.376(4) C(4a') C(9a') 1.410(4) C(9a) C(9) 1.492(3) C(9a') C(9') 1.486(4) C(9) C(9') 1.354(5) #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C(4a) S(10) C(4a) 95.8(2) C(2') N(1') C(9a') 116.0(3) C(2) C(1) C(9a) 120.2(3) C(1) C(2) C(3) 119.9(3) N(1') C(2') C(3') 125.6(3) C(2) C(3) C(4) 120.8(2) C(2') C(3') C(4') 118.3(3) S(10) C(4a) C(4) 119.4(2) S(10) C(4a) C(9a) 120.5(2) C(4) C(4a) C(9a) 120.1(2) C(4a') C(4a') C(4') 131.5(2) C(4a') C(4a') C(9a') 108.4(2) C(4') C(4a') C(9a') 120.0(3) C(3) C(4) C(4a) 119.6(3) C(3') C(4') C(4a') 117.4(3) C(1) C(9a) C(4a) 119.2(2) C(1) C(9a) C(9) 122.6(2) C(4a) C(9a) C(9) 117.9(2) N(1') C(9a') C(4a') 122.7(3) N(1') C(9a') C(9') 127.9(3) C(4a') C(9a') C(9') 109.4(3) C(9a) C(9) C(9a) 111.0(3) C(9a) C(9) C(9') 124.5(1) C(9a) C(9) C(9') 124.5(1) C(9a') C(9') C(9a') 104.0(3) C(9a') C(9') C(9) 127.2(1) C(9a') C(9') C(9) 127.2(1)