# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_date 'Tue Nov 13 19:08:35 2001' _audit_creation_method 'by teXsan' _audit_update_record ? _journal_coden_Cambridge 207 loop_ _publ_author_name 'Sashida, Haruki' 'Akiba, Kin-ya' 'Minoura, Mao' 'Ohyanagi, Kazuo' #------------------------------------------------------------------------------ # SUBMISSION DETAILS _publ_contact_author_name 'Prof Haruki Sashida' _publ_contact_author_address ; Faculty of Pharmaceutical Sciences Hokuriku University Kanagawa-machi, Kanazawa 920-1181, Japan. ; _publ_contact_author_email 'h-sashida@hokuriku-u.ac.jp' _publ_contact_author_fax '+81-76-229-2781' _publ_contact_author_phone '+81-76-229-6165' _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 1' #------------------------------------------------------------------------------ # TITLE AND AUTHOR LIST _publ_section_title ; Studies on tellurium-containing heterocycles. Part 18. Preparation and structure of 2-benzotelluropyrylium salts and 2-benzoselenopyrylium salts ; _publ_author_name ; Haruki Sashida, Kazuo Ohyanagi, Mao Minoura and Kin-ya Akiba ; _publ_author_address ; Faculty of Pharmaceutical Sciences, Hokuriku University Kanagawa-machi, Kanazawa 920-1181, Japan. Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Sagamihara, Kanagawa 228-8555, Japan. Advanced Research Center for Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan. ; #------------------------------------------------------------------------------ # TEXT _publ_section_abstract ; Preparation and structure of 2-benzotelluropyrylium salts and 2-benzoselenopyrylium salts are reported. ; _publ_section_comment ; The first structural characterization of 2-benzotelluropyrylium tetrafluoroborate and its selenium analogues are reported. ; _publ_section_references ; Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; #------------------------------------------------------------------------------ data_MMDIP149Te993Sashi190 _database_code_CSD 175478 #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C13 H15 B F4 Te ' _chemical_formula_moiety 'C13 H15 B F4 Te ' _chemical_formula_weight 385.67 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pnma' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,1/2-z -x,1/2+y,-z 1/2-x,-y,1/2+z -x,-y,-z 1/2-x,1/2+y,1/2+z x,1/2-y,z 1/2+x,y,1/2-z _cell_length_a 14.2630(5) _cell_length_b 6.7450(2) _cell_length_c 14.3100(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1376.68(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 190.0 #------------------------------------------------------------------------------ _exptl_crystal_description 'prisms' _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.861 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 2.189 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K¥a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'MAC Science DIP2030 Imaging Plate' _diffrn_measurement_method ¥w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 1904 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 27.25 _diffrn_measured_fraction_theta_max 0.9911 _diffrn_reflns_theta_full 27.25 _diffrn_measured_fraction_theta_full 0.9911 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 0 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1665 _reflns_number_gt 1572 _reflns_threshold_expression F^2^>3.0¥s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1006 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1572 _refine_ls_number_parameters 109 _refine_ls_goodness_of_fit_ref 1.356 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[¥s^2^(Fo) + 0.00540|Fo|^2^]' _refine_ls_shift/su_max 0.0020 _refine_diff_density_max 1.47 _refine_diff_density_min -2.38 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'B' 'B' 0.001 0.001 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'F' 'F' 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'Te' 'Te' -0.531 1.675 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Te1 Te 1.12024(3) 0.2500 0.72389(3) 0.0311(2) Uani 1.00 d S . . F1 F 0.7234(3) 0.5900(7) 0.5911(4) 0.141(2) Uani 1.00 d . . . F2 F 0.6012(4) 0.7500 0.6567(4) 0.061(1) Uani 1.00 d S . . F3 F 0.7424(5) 0.7500 0.7203(3) 0.136(4) Uani 1.00 d S . . C1 C 1.1134(4) 0.2500 0.5841(5) 0.031(1) Uani 1.00 d S . . C2 C 0.9786(3) 0.2500 0.7443(5) 0.027(1) Uani 1.00 d S . . C3 C 0.9184(3) 0.2500 0.6693(4) 0.028(1) Uani 1.00 d S . . C4 C 0.8599(4) 0.2500 0.5104(5) 0.032(1) Uani 1.00 d S . . C5 C 0.8718(4) 0.2500 0.4163(6) 0.035(2) Uani 1.00 d S . . C6 C 0.9635(5) 0.2500 0.3751(4) 0.036(1) Uani 1.00 d S . . C7 C 1.0396(4) 0.2500 0.4320(4) 0.036(1) Uani 1.00 d S . . C8 C 0.9382(4) 0.2500 0.5715(3) 0.028(1) Uani 1.00 d S . . C9 C 1.0310(4) 0.2500 0.5319(3) 0.026(1) Uani 1.00 d S . . C10 C 0.9420(5) 0.2500 0.8452(4) 0.032(1) Uani 1.00 d S . . C11 C 0.8815(3) 0.0637(8) 0.8604(4) 0.041(1) Uani 1.00 d . . . C12 C 1.0214(5) 0.2500 0.9174(4) 0.042(2) Uani 1.00 d S . . B1 B 0.6993(5) 0.7500 0.6400(4) 0.032(1) Uani 1.00 d S . . H1 H 1.1713 0.2500 0.5507 0.0354 Uiso 1.00 calc S . . H2 H 0.8542 0.2500 0.6854 0.0293 Uiso 1.00 calc S . . H3 H 0.7977 0.2500 0.5354 0.0370 Uiso 1.00 calc S . . H4 H 0.8182 0.2500 0.3758 0.0402 Uiso 1.00 calc S . . H5 H 0.9701 0.2500 0.3085 0.0428 Uiso 1.00 calc S . . H6 H 1.1014 0.2500 0.4042 0.0379 Uiso 1.00 calc S . . H7 H 0.9184 -0.0529 0.8504 0.0474 Uiso 1.00 calc . . . H8 H 0.8575 0.0617 0.9222 0.0474 Uiso 1.00 calc . . . H9 H 0.8302 0.0618 0.8172 0.0474 Uiso 1.00 calc . . . H10 H 1.0605 0.3638 0.9088 0.0450 Uiso 0.50 calc P . . H11 H 1.0592 0.1339 0.9102 0.0450 Uiso 0.50 calc P . . H12 H 0.9964 0.2500 0.9788 0.0450 Uiso 1.00 calc S . . 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 Te1 0.0245(4) 0.0398(4) 0.0291(4) 0.0000 -0.00273(9) 0.0000 F1 0.063(3) 0.145(4) 0.215(6) -0.008(2) 0.016(3) -0.123(4) F2 0.037(2) 0.090(4) 0.056(3) 0.0000 0.009(2) 0.0000 F3 0.071(5) 0.29(1) 0.049(3) 0.0000 -0.025(2) 0.0000 C1 0.029(3) 0.037(3) 0.027(3) 0.0000 0.001(2) 0.0000 C2 0.024(3) 0.026(2) 0.031(2) 0.0000 0.006(3) 0.0000 C3 0.016(3) 0.038(2) 0.029(3) 0.0000 0.003(2) 0.0000 C4 0.036(3) 0.027(2) 0.033(3) 0.0000 -0.004(2) 0.0000 C5 0.040(4) 0.033(3) 0.033(4) 0.0000 -0.011(2) 0.0000 C6 0.050(4) 0.026(2) 0.031(3) 0.0000 0.000(2) 0.0000 C7 0.047(3) 0.028(2) 0.033(2) 0.0000 0.004(2) 0.0000 C8 0.033(3) 0.021(2) 0.029(2) 0.0000 -0.001(2) 0.0000 C9 0.033(3) 0.024(2) 0.020(2) 0.0000 -0.004(2) 0.0000 C10 0.036(3) 0.029(2) 0.029(3) 0.0000 0.007(2) 0.0000 C11 0.051(3) 0.037(2) 0.036(2) -0.007(1) 0.009(2) 0.005(2) C12 0.048(4) 0.054(3) 0.023(2) 0.0000 0.006(3) 0.0000 B1 0.031(3) 0.042(3) 0.022(2) 0.0000 0.004(2) 0.0000 #------------------------------------------------------------------------------ _computing_data_collection 'DENZO' _computing_cell_refinement 'DENZO' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag TE1 C1 2.003(7) . . yes TE1 C2 2.042(5) . . yes F1 B1 1.330(5) . . yes F2 B1 1.421(7) . . yes F3 B1 1.304(7) . . yes C1 C9 1.392(7) . . yes C1 H1 0.955 . . no C2 C3 1.374(8) . . yes C2 C10 1.536(9) . . yes C2 H2 1.963 . . no C3 C8 1.429(7) . . yes C3 H2 0.944 . . no C4 C5 1.36(1) . . yes C4 C8 1.418(8) . . yes C4 H3 0.957 . . no C4 H4 2.015 . . no C5 C6 1.434(9) . . yes C5 H3 2.005 . . no C5 H4 0.959 . . no C5 H5 2.085 . . no C6 C7 1.357(8) . . yes C6 H4 2.072 . . no C6 H5 0.957 . . no C6 H6 2.012 . . no C7 C9 1.436(7) . . yes C7 H5 2.026 . . no C7 H6 0.968 . . no C8 C9 1.439(8) . . yes C8 H2 2.024 . . no C8 H3 2.070 . . no C9 H1 2.020 . . no C9 H6 2.086 . . no C10 C11 1.539(6) . . yes C10 C11 1.539(6) . 7_555 yes C10 C12 1.533(9) . . yes C10 H7 2.072 . . no C10 H7 2.072 . 7_555 no C10 H8 2.069 . . no C10 H8 2.069 . 7_555 no C10 H9 2.078 . . no C10 H9 2.078 . 7_555 no C10 H10 2.067 . . no C10 H10 2.067 . 7_555 no C10 H11 2.067 . . no C10 H11 2.067 . 7_555 no C10 H12 2.064 . . no C11 H7 0.957 . . no C11 H8 0.948 . . no C11 H9 0.959 . . no C12 H10 0.957 . . no C12 H10 0.957 . 7_555 no C12 H11 0.956 . . no C12 H11 0.956 . 7_555 no C12 H12 0.948 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 TE1 C2 95.4(3) . . . yes TE1 C1 C9 125.2(4) . . . yes TE1 C1 H1 117.2 . . . no C9 C1 H1 117.5 . . . no TE1 C2 C3 120.5(5) . . . yes TE1 C2 C10 118.1(5) . . . yes TE1 C2 H2 146.4 . . . no C3 C2 C10 121.5(5) . . . yes C3 C2 H2 25.9 . . . no C10 C2 H2 95.5 . . . no C2 C3 C8 129.9(5) . . . yes C2 C3 H2 114.5 . . . no C8 C3 H2 115.6 . . . no C5 C4 C8 120.9(6) . . . yes C5 C4 H3 119.1 . . . no C5 C4 H4 24.3 . . . no C8 C4 H3 120.0 . . . no C8 C4 H4 145.2 . . . no H3 C4 H4 94.8 . . . no C4 C5 C6 121.4(5) . . . yes C4 C5 H3 24.6 . . . no C4 C5 H4 120.0 . . . no C4 C5 H5 144.9 . . . no C6 C5 H3 146.1 . . . no C6 C5 H4 118.6 . . . no C6 C5 H5 23.4 . . . no H3 C5 H4 95.3 . . . no H3 C5 H5 169.5 . . . no H4 C5 H5 95.1 . . . no C5 C6 C7 118.8(5) . . . yes C5 C6 H4 24.0 . . . no C5 C6 H5 120.0 . . . no C5 C6 H6 143.8 . . . no C7 C6 H4 142.8 . . . no C7 C6 H5 121.2 . . . no C7 C6 H6 24.9 . . . no H4 C6 H5 96.0 . . . no H4 C6 H6 167.7 . . . no H5 C6 H6 96.3 . . . no C6 C7 C9 122.0(5) . . . yes C6 C7 H5 23.8 . . . no C6 C7 H6 118.9 . . . no C9 C7 H5 145.8 . . . no C9 C7 H6 119.2 . . . no H5 C7 H6 95.0 . . . no C3 C8 C4 116.6(5) . . . yes C3 C8 C9 124.6(5) . . . yes C3 C8 H2 24.9 . . . no C3 C8 H3 93.0 . . . no C4 C8 C9 118.8(5) . . . yes C4 C8 H2 91.7 . . . no C4 C8 H3 23.6 . . . no C9 C8 H2 149.5 . . . no C9 C8 H3 142.4 . . . no H2 C8 H3 68.1 . . . no C1 C9 C7 117.5(5) . . . yes C1 C9 C8 124.4(5) . . . yes C1 C9 H1 24.8 . . . no C1 C9 H6 93.6 . . . no C7 C9 C8 118.1(5) . . . yes C7 C9 H1 92.7 . . . no C7 C9 H6 23.9 . . . no C8 C9 H1 149.2 . . . no C8 C9 H6 142.0 . . . no H1 C9 H6 68.8 . . . no C2 C10 C11 108.9(3) . . . yes C2 C10 C11 108.9(3) . . 7_555 yes C2 C10 C12 112.5(5) . . . yes C2 C10 H7 95.1 . . . no C2 C10 H7 95.1 . . 7_555 no C2 C10 H8 134.3 . . . no C2 C10 H8 134.3 . . 7_555 no C2 C10 H9 94.6 . . . no C2 C10 H9 94.6 . . 7_555 no C2 C10 H10 97.8 . . . no C2 C10 H10 97.8 . . 7_555 no C2 C10 H11 98.6 . . . no C2 C10 H11 98.6 . . 7_555 no C2 C10 H12 138.1 . . . no C11 C10 C11 109.4(5) . . 7_555 yes C11 C10 C12 108.6(3) . . . yes C11 C10 H7 25.7 . . . no C11 C10 H7 135.1 . . 7_555 no C11 C10 H8 25.5 . . . no C11 C10 H8 95.7 . . 7_555 no C11 C10 H9 25.6 . . . no C11 C10 H9 95.5 . . 7_555 no C11 C10 H10 134.3 . . . no C11 C10 H10 95.3 . . 7_555 no C11 C10 H11 94.6 . . . no C11 C10 H11 134.3 . . 7_555 no C11 C10 H12 94.5 . . . no C11 C10 C12 108.6(3) 7_555 . . yes C11 C10 H7 135.1 7_555 . . no C11 C10 H7 25.7 7_555 . 7_555 no C11 C10 H8 95.7 7_555 . . no C11 C10 H8 25.5 7_555 . 7_555 no C11 C10 H9 95.5 7_555 . . no C11 C10 H9 25.6 7_555 . 7_555 no C11 C10 H10 95.3 7_555 . . no C11 C10 H10 134.3 7_555 . 7_555 no C11 C10 H11 134.3 7_555 . . no C11 C10 H11 94.6 7_555 . 7_555 no C11 C10 H12 94.5 7_555 . . no C12 C10 H7 95.5 . . . no C12 C10 H7 95.5 . . 7_555 no C12 C10 H8 94.1 . . . no C12 C10 H8 94.1 . . 7_555 no C12 C10 H9 134.2 . . . no C12 C10 H9 134.2 . . 7_555 no C12 C10 H10 25.8 . . . no C12 C10 H10 25.8 . . 7_555 no C12 C10 H11 25.8 . . . no C12 C10 H11 25.8 . . 7_555 no C12 C10 H12 25.5 . . . no H7 C10 H7 160.8 . . 7_555 no H7 C10 H8 44.0 . . . no H7 C10 H8 119.4 . . 7_555 no H7 C10 H9 43.9 . . . no H7 C10 H9 119.0 . . 7_555 no H7 C10 H10 118.9 . . . no H7 C10 H10 75.6 . . 7_555 no H7 C10 H11 75.0 . . . no H7 C10 H11 119.3 . . 7_555 no H7 C10 H12 91.6 . . . no H7 C10 H8 119.4 7_555 . . no H7 C10 H8 44.0 7_555 . 7_555 no H7 C10 H9 119.0 7_555 . . no H7 C10 H9 43.9 7_555 . 7_555 no H7 C10 H10 75.6 7_555 . . no H7 C10 H10 118.9 7_555 . 7_555 no H7 C10 H11 119.3 7_555 . . no H7 C10 H11 75.0 7_555 . 7_555 no H7 C10 H12 91.6 7_555 . . no H8 C10 H8 75.8 . . 7_555 no H8 C10 H9 43.9 . . . no H8 C10 H9 91.7 . . 7_555 no H8 C10 H10 118.0 . . . no H8 C10 H10 90.8 . . 7_555 no H8 C10 H11 89.9 . . . no H8 C10 H11 117.7 . . 7_555 no H8 C10 H12 74.1 . . . no H8 C10 H9 91.7 7_555 . . no H8 C10 H9 43.9 7_555 . 7_555 no H8 C10 H10 90.8 7_555 . . no H8 C10 H10 118.0 7_555 . 7_555 no H8 C10 H11 117.7 7_555 . . no H8 C10 H11 89.9 7_555 . 7_555 no H8 C10 H12 74.1 7_555 . . no H9 C10 H9 75.3 . . 7_555 no H9 C10 H10 160.0 . . . no H9 C10 H10 119.0 . . 7_555 no H9 C10 H11 118.4 . . . no H9 C10 H11 159.9 . . 7_555 no H9 C10 H12 117.8 . . . no H9 C10 H10 119.0 7_555 . . no H9 C10 H10 160.0 7_555 . 7_555 no H9 C10 H11 159.9 7_555 . . no H9 C10 H11 118.4 7_555 . 7_555 no H9 C10 H12 117.8 7_555 . . no H10 C10 H10 43.6 . . 7_555 no H10 C10 H11 44.1 . . . no H10 C10 H11 0.9 . . 7_555 no H10 C10 H12 44.3 . . . no H10 C10 H11 0.9 7_555 . . no H10 C10 H11 44.1 7_555 . 7_555 no H10 C10 H12 44.3 7_555 . . no H11 C10 H11 44.5 . . 7_555 no H11 C10 H12 43.9 . . . no H11 C10 H12 43.9 7_555 . . no C10 C11 H7 110.0 . . . no C10 C11 H8 110.3 . . . no C10 C11 H9 110.4 . . . no H7 C11 H8 109.1 . . . no H7 C11 H9 108.2 . . . no H8 C11 H9 108.9 . . . no C10 C12 H10 110.0 . . . no C10 C12 H10 110.0 . . 7_555 no C10 C12 H11 110.0 . . . no C10 C12 H11 110.0 . . 7_555 no C10 C12 H12 110.3 . . . no H10 C12 H10 106.8 . . 7_555 no H10 C12 H11 108.4 . . . no H10 C12 H11 1.9 . . 7_555 no H10 C12 H12 109.8 . . . no H10 C12 H11 1.9 7_555 . . no H10 C12 H11 108.4 7_555 . 7_555 no H10 C12 H12 109.8 7_555 . . no H11 C12 H11 110.0 . . 7_555 no H11 C12 H12 108.2 . . . no H11 C12 H12 108.2 7_555 . . no F1 B1 F1 108.4(6) . . 7_565 yes F1 B1 F2 110.0(4) . . . yes F1 B1 F3 110.0(4) . . . yes F1 B1 F2 110.0(4) 7_565 . . yes F1 B1 F3 110.0(4) 7_565 . . yes F2 B1 F3 108.4(6) . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F1 C4 3.223(6) . . ? F2 C6 3.258(8) . 4_665 ? F3 C5 3.243(9) . 4_665 ? F3 C11 3.526(7) . 1_565 ? F3 C11 3.526(7) . 7_555 ? C1 C5 3.3791(5) . 3_756 ? C1 C5 3.3791(5) . 3_746 ? C7 C8 3.3877(8) . 3_756 ? C7 C8 3.3877(8) . 3_746 ? #------------------------------------------------------------------------------ #---END #------------------------------------------------------------------------------ data_MMDIP151SePy992190 _database_code_CSD 175479 _audit_creation_date 'Tue Nov 13 19:06:10 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C13 H15 B F4 Se ' _chemical_formula_moiety 'C13 H15 B F4 Se ' _chemical_formula_weight 337.03 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pnma' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,1/2-z -x,1/2+y,-z 1/2-x,-y,1/2+z -x,-y,-z 1/2-x,1/2+y,1/2+z x,1/2-y,z 1/2+x,y,1/2-z _cell_length_a 13.8420(4) _cell_length_b 6.7860(1) _cell_length_c 14.2960(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1342.85(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 273.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 2.824 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K¥a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'MAC Science DIP2030 Imaging Plate' _diffrn_measurement_method ¥w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 1875 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 27.25 _diffrn_measured_fraction_theta_max 0.9963 _diffrn_reflns_theta_full 27.25 _diffrn_measured_fraction_theta_full 0.9963 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 0 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1625 _reflns_number_gt 1528 _reflns_threshold_expression F^2^>3.0¥s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1083 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1528 _refine_ls_number_parameters 109 _refine_ls_goodness_of_fit_ref 1.475 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[¥s^2^(Fo) + 0.00533|Fo|^2^]' _refine_ls_shift/su_max 0.0012 _refine_diff_density_max 1.32 _refine_diff_density_min -1.44 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'Se' 'Se' -0.093 2.226 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'F' 'F' 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'B' 'B' 0.001 0.001 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.89384(3) 0.2500 0.78721(3) 0.0315(2) Uani 1.00 d S . . F1 F 0.9008(2) 0.7500 0.6499(4) 0.062(1) Uani 1.00 d S . . F2 F 0.7656(3) 0.9048(8) 0.6853(4) 0.172(3) Uani 1.00 d . . . F3 F 0.7743(4) 0.7500 0.5575(3) 0.164(3) Uani 1.00 d S . . C C 1.1149(3) 0.4362(7) 0.6391(3) 0.043(1) Uani 1.00 d . . . C1 C 0.8956(3) 0.2500 0.9135(4) 0.032(1) Uani 1.00 d S . . C2 C 1.0249(3) 0.2500 0.7609(3) 0.0267(9) Uani 1.00 d S . . C3 C 1.0909(3) 0.2500 0.8317(3) 0.029(1) Uani 1.00 d S . . C4 C 1.1534(3) 0.2500 0.9911(3) 0.034(1) Uani 1.00 d S . . C5 C 1.1395(5) 0.2500 1.0868(4) 0.040(1) Uani 1.00 d S . . C6 C 1.0467(4) 0.2500 1.1244(3) 0.037(1) Uani 1.00 d S . . C7 C 0.9663(4) 0.2500 1.0680(3) 0.033(1) Uani 1.00 d S . . C8 C 1.0734(4) 0.2500 0.9299(3) 0.028(1) Uani 1.00 d S . . C9 C 0.9790(3) 0.2500 0.9682(3) 0.0277(9) Uani 1.00 d S . . C10 C 1.0550(4) 0.2500 0.6571(3) 0.030(1) Uani 1.00 d S . . C11 C 0.9677(4) 0.2500 0.5926(4) 0.041(1) Uani 1.00 d S . . B1 B 0.8015(4) 0.7500 0.6428(3) 0.036(1) Uani 1.00 d S . . H1 H 0.8353 0.2500 0.9441 0.0369 Uiso 1.00 calc S . . H2 H 1.1579 0.2500 0.8144 0.0332 Uiso 1.00 calc S . . H3 H 1.2183 0.2500 0.9665 0.0383 Uiso 1.00 calc S . . H4 H 1.1948 0.2500 1.1264 0.0447 Uiso 1.00 calc S . . H5 H 1.0383 0.2500 1.1921 0.0431 Uiso 1.00 calc S . . H6 H 0.9024 0.2500 1.0937 0.0403 Uiso 1.00 calc S . . H7 H 1.0768 0.5512 0.6524 0.0510 Uiso 1.00 calc . . . H8 H 1.1345 0.4410 0.5754 0.0510 Uiso 1.00 calc . . . H9 H 1.1704 0.4378 0.6783 0.0510 Uiso 1.00 calc . . . H10 H 0.9296 0.1346 0.6014 0.0472 Uiso 0.50 calc P . . H11 H 0.9887 0.2500 0.5281 0.0472 Uiso 1.00 calc S . . H12 H 0.9284 0.3631 0.6029 0.0472 Uiso 0.50 calc P . . 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 Se1 0.0247(5) 0.0401(5) 0.0297(5) 0.0000 -0.0025(1) 0.0000 F1 0.034(2) 0.080(3) 0.072(3) 0.0000 -0.012(2) 0.0000 F2 0.084(3) 0.147(5) 0.284(7) 0.021(3) 0.005(4) -0.139(5) F3 0.046(2) 0.40(1) 0.041(2) 0.0000 -0.011(2) 0.0000 C 0.051(2) 0.041(2) 0.036(2) -0.010(1) 0.006(1) 0.005(1) C1 0.028(3) 0.035(2) 0.031(2) 0.0000 0.005(1) 0.0000 C2 0.026(2) 0.031(2) 0.023(2) 0.0000 -0.002(2) 0.0000 C3 0.025(2) 0.033(2) 0.030(2) 0.0000 -0.002(2) 0.0000 C4 0.030(2) 0.039(2) 0.032(2) 0.0000 -0.005(2) 0.0000 C5 0.048(3) 0.036(2) 0.036(3) 0.0000 -0.009(2) 0.0000 C6 0.055(3) 0.034(2) 0.023(2) 0.0000 -0.002(2) 0.0000 C7 0.046(3) 0.027(2) 0.026(2) 0.0000 0.003(2) 0.0000 C8 0.031(2) 0.027(2) 0.027(2) 0.0000 -0.001(2) 0.0000 C9 0.033(2) 0.025(2) 0.025(2) 0.0000 0.003(2) 0.0000 C10 0.037(2) 0.030(2) 0.024(2) 0.0000 0.002(2) 0.0000 C11 0.046(3) 0.049(3) 0.030(2) 0.0000 -0.005(2) 0.0000 B1 0.030(3) 0.047(3) 0.031(2) 0.0000 -0.001(2) 0.0000 #------------------------------------------------------------------------------ _computing_data_collection 'DENZO' _computing_cell_refinement 'DENZO' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag SE1 C1 1.806(5) . . yes SE1 C2 1.853(4) . . yes F1 B1 1.379(7) . . yes F2 F2 2.10(1) . 7_565 yes F2 F3 2.111(6) . . yes F2 B1 1.312(5) . . yes F3 B1 1.276(7) . . yes C C10 1.533(5) . . yes C H7 0.961 . . no C H8 0.951 . . no C H9 0.950 . . no C1 C9 1.394(7) . . yes C1 H1 0.941 . . no C2 C3 1.363(6) . . yes C2 C10 1.541(6) . . yes C2 H2 1.993 . . no C3 C8 1.425(6) . . yes C3 H2 0.960 . . no C4 C5 1.382(7) . . yes C4 C8 1.411(7) . . yes C4 H3 0.964 . . no C4 H4 2.018 . . no C5 C6 1.393(9) . . yes C5 H3 2.036 . . no C5 H4 0.952 . . no C5 H5 2.056 . . no C6 C7 1.375(7) . . yes C6 H4 2.050 . . no C6 H5 0.974 . . no C6 H6 2.044 . . no C7 C9 1.438(5) . . yes C7 H5 2.035 . . no C7 H6 0.958 . . no C8 C9 1.418(7) . . yes C8 H2 2.023 . . no C8 H3 2.072 . . no C9 H1 2.018 . . no C9 H6 2.085 . . no C10 C11 1.520(8) . . yes C10 H7 2.067 . . no C10 H7 2.067 . 7_555 no C10 H8 2.063 . . no C10 H8 2.063 . 7_555 no C10 H9 2.066 . . no C10 H9 2.066 . 7_555 no C10 H10 2.064 . . no C10 H10 2.064 . 7_555 no C10 H11 2.060 . . no C10 H12 2.065 . . no C10 H12 2.065 . 7_555 no C11 H10 0.953 . . no C11 H10 0.953 . 7_555 no C11 H11 0.967 . . no C11 H12 0.952 . . no C11 H12 0.952 . 7_555 no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 SE1 C2 101.0(2) . . . yes F2 F2 F3 60.1(2) 7_565 . . yes F2 F2 B1 36.8(3) 7_565 . . yes F3 F2 B1 34.8(3) . . . yes F2 F3 F2 59.7(4) . . 7_565 yes F2 F3 B1 35.9(2) . . . yes F2 F3 B1 35.9(2) 7_565 . . yes C10 C H7 109.8 . . . no C10 C H8 110.1 . . . no C10 C H9 110.4 . . . no H7 C H8 108.5 . . . no H7 C H9 108.6 . . . no H8 C H9 109.5 . . . no SE1 C1 C9 124.8(3) . . . yes SE1 C1 H1 116.9 . . . no C9 C1 H1 118.3 . . . no SE1 C2 C3 120.3(3) . . . yes SE1 C2 C10 117.4(3) . . . yes SE1 C2 H2 145.7 . . . no C3 C2 C10 122.3(4) . . . yes C3 C2 H2 25.4 . . . no C10 C2 H2 96.9 . . . no C2 C3 C8 128.2(4) . . . yes C2 C3 H2 117.1 . . . no C8 C3 H2 114.7 . . . no C5 C4 C8 120.3(5) . . . yes C5 C4 H3 119.3 . . . no C5 C4 H4 24.5 . . . no C8 C4 H3 120.4 . . . no C8 C4 H4 144.8 . . . no H3 C4 H4 94.9 . . . no C4 C5 C6 120.7(5) . . . yes C4 C5 H3 24.4 . . . no C4 C5 H4 118.5 . . . no C4 C5 H5 145.1 . . . no C6 C5 H3 145.1 . . . no C6 C5 H4 120.7 . . . no C6 C5 H5 24.3 . . . no H3 C5 H4 94.2 . . . no H3 C5 H5 169.4 . . . no H4 C5 H5 96.4 . . . no C5 C6 C7 121.3(4) . . . yes C5 C6 H4 23.5 . . . no C5 C6 H5 119.5 . . . no C5 C6 H6 144.9 . . . no C7 C6 H4 144.8 . . . no C7 C6 H5 119.1 . . . no C7 C6 H6 23.6 . . . no H4 C6 H5 96.0 . . . no H4 C6 H6 168.4 . . . no H5 C6 H6 95.6 . . . no C6 C7 C9 119.0(5) . . . yes C6 C7 H5 24.7 . . . no C6 C7 H6 121.4 . . . no C9 C7 H5 143.7 . . . no C9 C7 H6 119.6 . . . no H5 C7 H6 96.7 . . . no C3 C8 C4 118.5(4) . . . yes C3 C8 C9 122.4(4) . . . yes C3 C8 H2 25.6 . . . no C3 C8 H3 94.9 . . . no C4 C8 C9 119.0(4) . . . yes C4 C8 H2 93.0 . . . no C4 C8 H3 23.7 . . . no C9 C8 H2 148.0 . . . no C9 C8 H3 142.7 . . . no H2 C8 H3 69.3 . . . no C1 C9 C7 117.1(4) . . . yes C1 C9 C8 123.2(4) . . . yes C1 C9 H1 24.2 . . . no C1 C9 H6 93.5 . . . no C7 C9 C8 119.7(4) . . . yes C7 C9 H1 92.8 . . . no C7 C9 H6 23.5 . . . no C8 C9 H1 147.5 . . . no C8 C9 H6 143.2 . . . no H1 C9 H6 69.3 . . . no C C10 C 111.0(4) . . 7_555 yes C C10 C2 107.9(2) . . . yes C C10 C11 109.2(3) . . . yes C C10 H7 25.9 . . . no C C10 H7 136.9 . . 7_555 no C C10 H8 25.6 . . . no C C10 H8 97.7 . . 7_555 no C C10 H9 25.5 . . . no C C10 H9 96.6 . . 7_555 no C C10 H10 134.7 . . . no C C10 H10 94.5 . . 7_555 no C C10 H11 95.2 . . . no C C10 H12 95.2 . . . no C C10 H12 134.7 . . 7_555 no C C10 C2 107.9(2) 7_555 . . yes C C10 C11 109.2(3) 7_555 . . yes C C10 H7 136.9 7_555 . . no C C10 H7 25.9 7_555 . 7_555 no C C10 H8 97.7 7_555 . . no C C10 H8 25.6 7_555 . 7_555 no C C10 H9 96.6 7_555 . . no C C10 H9 25.5 7_555 . 7_555 no C C10 H10 94.5 7_555 . . no C C10 H10 134.7 7_555 . 7_555 no C C10 H11 95.2 7_555 . . no C C10 H12 134.7 7_555 . . no C C10 H12 95.2 7_555 . 7_555 no C2 C10 C11 111.7(4) . . . yes C2 C10 H7 94.1 . . . no C2 C10 H7 94.1 . . 7_555 no C2 C10 H8 133.5 . . . no C2 C10 H8 133.5 . . 7_555 no C2 C10 H9 93.9 . . . no C2 C10 H9 93.9 . . 7_555 no C2 C10 H10 98.3 . . . no C2 C10 H10 98.3 . . 7_555 no C2 C10 H11 137.9 . . . no C2 C10 H12 97.6 . . . no C2 C10 H12 97.6 . . 7_555 no C11 C10 H7 95.5 . . . no C11 C10 H7 95.5 . . 7_555 no C11 C10 H8 94.7 . . . no C11 C10 H8 94.7 . . 7_555 no C11 C10 H9 134.7 . . . no C11 C10 H9 134.7 . . 7_555 no C11 C10 H10 25.5 . . . no C11 C10 H10 25.5 . . 7_555 no C11 C10 H11 26.2 . . . no C11 C10 H12 25.5 . . . no C11 C10 H12 25.5 . . 7_555 no H7 C10 H7 162.8 . . 7_555 no H7 C10 H8 44.1 . . . no H7 C10 H8 121.7 . . 7_555 no H7 C10 H9 44.1 . . . no H7 C10 H9 120.1 . . 7_555 no H7 C10 H10 119.1 . . . no H7 C10 H10 74.6 . . 7_555 no H7 C10 H11 92.1 . . . no H7 C10 H12 75.2 . . . no H7 C10 H12 118.7 . . 7_555 no H7 C10 H8 121.7 7_555 . . no H7 C10 H8 44.1 7_555 . 7_555 no H7 C10 H9 120.1 7_555 . . no H7 C10 H9 44.1 7_555 . 7_555 no H7 C10 H10 74.6 7_555 . . no H7 C10 H10 119.1 7_555 . 7_555 no H7 C10 H11 92.1 7_555 . . no H7 C10 H12 118.7 7_555 . . no H7 C10 H12 75.2 7_555 . 7_555 no H8 C10 H8 77.9 . . 7_555 no H8 C10 H9 44.1 . . . no H8 C10 H9 93.3 . . 7_555 no H8 C10 H10 118.0 . . . no H8 C10 H10 89.6 . . 7_555 no H8 C10 H11 74.4 . . . no H8 C10 H12 90.4 . . . no H8 C10 H12 118.3 . . 7_555 no H8 C10 H9 93.3 7_555 . . no H8 C10 H9 44.1 7_555 . 7_555 no H8 C10 H10 89.6 7_555 . . no H8 C10 H10 118.0 7_555 . 7_555 no H8 C10 H11 74.4 7_555 . . no H8 C10 H12 118.3 7_555 . . no H8 C10 H12 90.4 7_555 . 7_555 no H9 C10 H9 76.2 . . 7_555 no H9 C10 H10 160.2 . . . no H9 C10 H10 118.2 . . 7_555 no H9 C10 H11 118.4 . . . no H9 C10 H12 118.8 . . . no H9 C10 H12 160.2 . . 7_555 no H9 C10 H10 118.2 7_555 . . no H9 C10 H10 160.2 7_555 . 7_555 no H9 C10 H11 118.4 7_555 . . no H9 C10 H12 160.2 7_555 . . no H9 C10 H12 118.8 7_555 . 7_555 no H10 C10 H10 44.6 . . 7_555 no H10 C10 H11 44.0 . . . no H10 C10 H12 44.1 . . . no H10 C10 H12 0.9 . . 7_555 no H10 C10 H11 44.0 7_555 . . no H10 C10 H12 0.9 7_555 . . no H10 C10 H12 44.1 7_555 . 7_555 no H11 C10 H12 44.4 . . . no H11 C10 H12 44.4 . . 7_555 no H12 C10 H12 43.7 . . 7_555 no C10 C11 H10 111.1 . . . no C10 C11 H10 111.1 . . 7_555 no C10 C11 H11 109.8 . . . no C10 C11 H12 111.1 . . . no C10 C11 H12 111.1 . . 7_555 no H10 C11 H10 110.6 . . 7_555 no H10 C11 H11 107.0 . . . no H10 C11 H12 109.0 . . . no H10 C11 H12 1.9 . . 7_555 no H10 C11 H11 107.0 7_555 . . no H10 C11 H12 1.9 7_555 . . no H10 C11 H12 109.0 7_555 . 7_555 no H11 C11 H12 108.6 . . . no H11 C11 H12 108.6 . . 7_555 no H12 C11 H12 107.4 . . 7_555 no F1 B1 F2 110.1(4) . . . yes F1 B1 F2 110.1(4) . . 7_565 yes F1 B1 F3 111.4(5) . . . yes F2 B1 F2 106.5(7) . . 7_565 yes F2 B1 F3 109.3(4) . . . yes F2 B1 F3 109.3(4) 7_565 . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag SE1 F2 3.281(5) . 1_545 ? SE1 F2 3.281(5) . 7_565 ? F1 C6 3.307(7) . 3_757 ? F2 C3 3.375(6) . 2_466 ? F2 C 3.437(6) . 2_466 ? F3 C1 3.125(6) . 4_664 ? F3 C7 3.333(7) . 4_664 ? F3 C 3.442(6) . 3_756 ? F3 C 3.442(6) . 5_766 ? C1 C5 3.428(1) . 3_757 ? C1 C5 3.428(1) . 3_747 ? C1 C6 3.528(2) . 3_757 ? C1 C6 3.528(2) . 3_747 ? C7 C8 3.437(1) . 3_757 ? C7 C8 3.437(1) . 3_747 ? C7 C9 3.515(2) . 3_757 ? C7 C9 3.515(2) . 3_747 ? C9 C9 3.561(3) . 3_757 ? C9 C9 3.561(3) . 3_747 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------