Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Masahito Ochiai' 'Kazunori Miyamoto' 'Motoo Shiro' 'Takashi Suefuji' _publ_contact_author_name 'Prof Masahito Ochiai' _publ_contact_author_address ; Faculty of Pharmaceutical Sciences University of Tpokushima Shomachi 1-78 Tokushima 770-8505 JAPAN ; _publ_contact_author_email MOCHIAI@PH2.TOKUSHIMA-U.AC.JP _publ_requested_journal 'Chemical Communications' _publ_section_title ; Solid State Structures of Pentacoordinated l3-Iodanes with Trigonal Bipyramidal Geometry: Synthesis of Diphenyl- and Alkynyl(phenyl)-l3-iodane Complexes with 1,10-Phenanthroline ; #------------------------------------------------------------------------------ # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ # TEXT _publ_section_references ; ENTER OTHER REFERENCES Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999). SIR97. A New Tool for Crystal Structure Determination and Refinement. J. App. Cryst., 32, 115-119. Higashi, T. (1995). ABSCOR. Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan. Johnson, C. K. (1976). ORTEP-II. A FORTRAN Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory. Tennessee, USA. MSC & Rigaku. (1999). teXsan. Single Crystal Structure Analysis Software. Version 1.10. Molecular Structure Corporation, Texsas, USA and Rigaku Corporation, Tokyo, Japan. Rigaku (1998). PROCESS-AUTO. Automatic Data Acquisition and Processing Package for Imaging Plate Diffractometer. Rigaku Corporation, Tokyo, Japan ; #------------------------------------------------------------------------------ data_RGK801raplt_Tokushima_Univ _database_code_CSD 198725 _audit_creation_date 'Tue Aug 6 11:12:41 2002' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C24.50 H19 B Cl F4 I N2 ' _chemical_formula_moiety 'C24 H18 I N2 1+, B F4 1-, 0.5(C H2 Cl2)' _chemical_formula_weight 590.59 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,1/2-z -x,-y,-z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 13.230(4) _cell_length_b 10.440(3) _cell_length_c 34.25(1) _cell_angle_alpha 90 _cell_angle_beta 97.60(3) _cell_angle_gamma 90 _cell_volume 4688(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 23260 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 30.1 _cell_measurement_temperature 93.2 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.030 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.673 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 1.528 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_absorpt_correction_T_min 0.753 _exptl_absorpt_correction_T_max 0.955 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K?a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method ?w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 27719 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_theta_max 30.03 _diffrn_measured_fraction_theta_max 0.9974 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.9974 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 48 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -3.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 6837 _reflns_number_gt 4707 _reflns_threshold_expression F^2^>2.0?s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.1959 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 6837 _refine_ls_number_parameters 288 _refine_ls_goodness_of_fit_ref 1.372 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[?s^2^(Fo^2^) + (0.08400(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0013 _refine_diff_density_max 1.75 _refine_diff_density_min -1.83 _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) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 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) ; I I -0.474 1.812 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Cl Cl 0.148 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # 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 I1 I 0.85072(2) -0.17758(4) 0.63200(1) 0.0391(1) Uani 1.00 d . . . Cl1 Cl 0.9518(3) 0.0351(4) 0.7431(1) 0.078(1) Uiso 0.50 d P C A Cl2 Cl 1.1078(4) 0.1701(4) 0.7964(1) 0.081(1) Uiso 0.50 d P C A F1 F 0.4723(3) -0.0888(4) 0.6201(1) 0.0571(10) Uiso 1.00 d . . . F2 F 0.5602(3) -0.0851(4) 0.6814(1) 0.065(1) Uiso 1.00 d . . . F3 F 0.6383(6) -0.0715(7) 0.6298(2) 0.053(2) Uiso 0.50 d P T B F3' F 0.6250(7) -0.2116(8) 0.6332(3) 0.062(2) Uiso 0.50 d P T C F4 F 0.5663(6) -0.2613(7) 0.6418(2) 0.050(2) Uiso 0.50 d P T B F4' F 0.4808(8) -0.2537(10) 0.6570(3) 0.078(3) Uiso 0.50 d P T C N1 N 0.8851(3) -0.2613(4) 0.5460(1) 0.034(1) Uani 1.00 d . . . N2 N 0.8744(3) -0.0076(4) 0.5659(1) 0.033(1) Uani 1.00 d . . . C1 C 0.8460(4) -0.2556(5) 0.6889(2) 0.035(1) Uani 1.00 d . . . C2 C 0.8055(8) -0.1811(6) 0.7161(2) 0.073(3) Uani 1.00 d . . . C3 C 0.8014(9) -0.2340(9) 0.7531(2) 0.089(3) Uani 1.00 d . . . C4 C 0.8380(6) -0.3543(7) 0.7620(2) 0.058(2) Uani 1.00 d . . . C5 C 0.8761(5) -0.4270(6) 0.7344(2) 0.050(2) Uani 1.00 d . . . C6 C 0.8799(5) -0.3790(6) 0.6969(2) 0.044(2) Uani 1.00 d . . . C7 C 1.0101(4) -0.1698(5) 0.6356(2) 0.036(1) Uani 1.00 d . . . C8 C 1.0580(5) -0.0566(6) 0.6471(2) 0.046(2) Uani 1.00 d . . . C9 C 1.1628(5) -0.0512(7) 0.6494(2) 0.053(2) Uani 1.00 d . . . C10 C 1.2181(5) -0.1592(7) 0.6417(2) 0.049(2) Uani 1.00 d . . . C11 C 1.1684(4) -0.2725(7) 0.6304(2) 0.043(2) Uani 1.00 d . . . C12 C 1.0628(4) -0.2807(6) 0.6272(2) 0.039(1) Uani 1.00 d . . . C13 C 0.8858(4) -0.3842(5) 0.5361(2) 0.038(1) Uani 1.00 d . . . C14 C 0.8831(4) -0.4266(5) 0.4973(2) 0.036(1) Uani 1.00 d . . . C15 C 0.8773(4) -0.3378(5) 0.4673(2) 0.035(1) Uani 1.00 d . . . C16 C 0.8747(4) -0.2058(5) 0.4767(2) 0.032(1) Uani 1.00 d . . . C17 C 0.8709(4) -0.1084(5) 0.4468(1) 0.033(1) Uani 1.00 d . . . C18 C 0.8700(4) 0.0175(5) 0.4572(2) 0.036(1) Uani 1.00 d . . . C19 C 0.8714(4) 0.0549(5) 0.4973(1) 0.031(1) Uani 1.00 d . . . C20 C 0.8704(4) 0.1857(5) 0.5086(2) 0.036(1) Uani 1.00 d . . . C21 C 0.8729(4) 0.2154(5) 0.5476(2) 0.040(1) Uani 1.00 d . . . C22 C 0.8729(4) 0.1161(5) 0.5754(2) 0.038(1) Uani 1.00 d . . . C23 C 0.8743(3) -0.0386(5) 0.5272(1) 0.028(1) Uani 1.00 d . . . C24 C 0.8773(3) -0.1728(5) 0.5166(2) 0.029(1) Uani 1.00 d . . . C25 C 1.014(1) 0.187(1) 0.7640(4) 0.053(3) Uiso 0.50 d P C A B1 B 0.557(1) -0.128(2) 0.6420(4) 0.035(3) Uiso 0.50 d P T B B1' B 0.541(1) -0.155(2) 0.6485(4) 0.035(3) Uiso 0.50 d P T C H2 H 0.7816 -0.0971 0.7098 0.0864 Uiso 1.00 calc . . . H3 H 0.7721 -0.1862 0.7724 0.1071 Uiso 1.00 calc . . . H4 H 0.8378 -0.3870 0.7879 0.0709 Uiso 1.00 calc . . . H5 H 0.9005 -0.5112 0.7408 0.0605 Uiso 1.00 calc . . . H6 H 0.9047 -0.4295 0.6772 0.0527 Uiso 1.00 calc . . . H8 H 1.0202 0.0161 0.6535 0.0552 Uiso 1.00 calc . . . H9 H 1.1978 0.0267 0.6561 0.0638 Uiso 1.00 calc . . . H10 H 1.2903 -0.1553 0.6441 0.0589 Uiso 1.00 calc . . . H11 H 1.2070 -0.3454 0.6247 0.0521 Uiso 1.00 calc . . . H12 H 1.0277 -0.3584 0.6199 0.0472 Uiso 1.00 calc . . . H13 H 0.8886 -0.4466 0.5565 0.0457 Uiso 1.00 calc . . . H14 H 0.8851 -0.5155 0.4916 0.0431 Uiso 1.00 calc . . . H15 H 0.8755 -0.3651 0.4408 0.0421 Uiso 1.00 calc . . . H17 H 0.8694 -0.1317 0.4199 0.0395 Uiso 1.00 calc . . . H18 H 0.8686 0.0813 0.4374 0.0429 Uiso 1.00 calc . . . H20 H 0.8682 0.2517 0.4894 0.0434 Uiso 1.00 calc . . . H21 H 0.8744 0.3025 0.5560 0.0476 Uiso 1.00 calc . . . H22 H 0.8721 0.1381 0.6023 0.0452 Uiso 1.00 calc . . . H25a H 1.0331 0.2373 0.7422 0.0622 Uiso 0.50 calc P C A H25b H 0.9614 0.2379 0.7746 0.0622 Uiso 0.50 calc P C A 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 I1 0.0257(2) 0.0543(3) 0.0372(2) 0.0046(2) 0.0043(1) 0.0081(2) N1 0.029(2) 0.032(2) 0.040(2) 0.002(2) 0.001(2) 0.006(2) N2 0.026(2) 0.032(2) 0.042(2) -0.001(2) 0.005(2) -0.001(2) C1 0.028(3) 0.041(3) 0.035(3) 0.003(2) -0.001(2) 0.001(2) C2 0.135(8) 0.042(4) 0.047(4) 0.025(4) 0.037(4) 0.007(3) C3 0.16(1) 0.069(5) 0.047(4) 0.023(6) 0.040(5) -0.006(4) C4 0.075(5) 0.054(4) 0.041(3) -0.003(4) -0.003(3) 0.011(3) C5 0.048(4) 0.041(3) 0.060(4) 0.005(3) 0.001(3) 0.016(3) C6 0.037(3) 0.040(3) 0.056(3) 0.008(3) 0.009(3) 0.003(3) C7 0.024(2) 0.044(3) 0.039(3) 0.004(2) 0.005(2) 0.007(2) C8 0.041(3) 0.044(3) 0.053(3) 0.001(3) 0.004(3) 0.003(3) C9 0.046(4) 0.054(4) 0.057(4) -0.017(3) -0.003(3) 0.011(3) C10 0.028(3) 0.069(4) 0.051(3) -0.004(3) 0.003(2) 0.014(3) C11 0.031(3) 0.054(3) 0.046(3) 0.012(3) 0.008(2) 0.006(3) C12 0.030(3) 0.047(3) 0.041(3) 0.002(2) 0.004(2) 0.004(2) C13 0.030(3) 0.030(3) 0.053(3) 0.000(2) 0.000(2) 0.009(2) C14 0.026(2) 0.028(3) 0.054(3) -0.001(2) 0.003(2) 0.001(2) C15 0.025(2) 0.032(3) 0.047(3) -0.001(2) 0.001(2) 0.001(2) C16 0.023(2) 0.032(3) 0.041(3) -0.001(2) 0.004(2) 0.001(2) C17 0.033(3) 0.030(3) 0.034(2) -0.005(2) -0.002(2) 0.005(2) C18 0.032(3) 0.033(3) 0.041(3) -0.001(2) -0.003(2) 0.005(2) C19 0.020(2) 0.033(3) 0.040(3) -0.003(2) 0.004(2) 0.007(2) C20 0.022(2) 0.029(2) 0.057(3) -0.002(2) 0.002(2) 0.010(2) C21 0.022(2) 0.028(2) 0.068(4) 0.002(2) -0.002(2) -0.006(2) C22 0.032(3) 0.035(3) 0.046(3) 0.004(2) 0.005(2) -0.003(2) C23 0.015(2) 0.030(2) 0.040(2) 0.001(2) 0.004(2) 0.002(2) C24 0.019(2) 0.027(2) 0.041(3) 0.007(2) 0.005(2) 0.005(2) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'teXsan (MSC & Rigaku, 1999)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'teXsan (MSC & Rigaku, 1999)' _computing_publication_material 'teXsan (MSC & Rigaku, 1999)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' #------------------------------------------------------------------------------ _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 I1 C1 2.120(5) . . yes I1 C7 2.098(5) . . yes CL1 C25 1.89(1) . . yes CL2 C25 1.57(1) . . yes F1 B1 1.33(2) . . yes F2 B1 1.42(1) . . yes F3 B1 1.34(2) . . yes F4 B1 1.40(2) . . yes F1 B1' 1.42(2) . . yes F2 B1' 1.33(1) . . yes F3' B1' 1.42(2) . . yes F4' B1' 1.36(2) . . yes N1 C13 1.327(7) . . yes N1 C24 1.360(7) . . yes N2 C22 1.332(7) . . yes N2 C23 1.365(7) . . yes C1 C2 1.376(9) . . yes C1 C6 1.379(8) . . yes C2 C3 1.39(1) . . yes C2 H2 0.946 . . no C3 C4 1.37(1) . . yes C3 H3 0.950 . . no C4 C5 1.36(1) . . yes C4 H4 0.951 . . no C5 C6 1.385(9) . . yes C5 H5 0.952 . . no C6 H6 0.949 . . no C7 C8 1.373(8) . . yes C7 C12 1.401(8) . . yes C8 C9 1.379(9) . . yes C8 H8 0.950 . . no C9 C10 1.388(10) . . yes C9 H9 0.949 . . no C10 C11 1.383(9) . . yes C10 H10 0.949 . . no C11 C12 1.390(8) . . yes C11 H11 0.951 . . no C12 H12 0.951 . . no C13 C14 1.395(8) . . yes C13 H13 0.952 . . no C14 C15 1.381(8) . . yes C14 H14 0.949 . . no C15 C16 1.417(7) . . yes C15 H15 0.949 . . no C16 C17 1.438(7) . . yes C16 C24 1.405(8) . . yes C17 C18 1.362(8) . . yes C17 H17 0.951 . . no C18 C19 1.425(7) . . yes C18 H18 0.949 . . no C19 C20 1.420(7) . . yes C19 C23 1.411(7) . . yes C20 C21 1.368(9) . . yes C20 H20 0.950 . . no C21 C22 1.407(9) . . yes C21 H21 0.952 . . no C22 H22 0.952 . . no C23 C24 1.449(7) . . yes C25 H25a 0.972 . . no C25 H25b 0.976 . . 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 I1 C7 96.4(2) . . . yes C13 N1 C24 118.1(5) . . . yes C22 N2 C23 117.9(5) . . . yes I1 C1 C2 117.8(4) . . . yes I1 C1 C6 119.5(4) . . . yes C2 C1 C6 122.6(5) . . . yes C1 C2 C3 117.3(7) . . . yes C1 C2 H2 121.2 . . . no C3 C2 H2 121.5 . . . no C2 C3 C4 120.9(7) . . . yes C2 C3 H3 119.5 . . . no C4 C3 H3 119.6 . . . no C3 C4 C5 120.8(6) . . . yes C3 C4 H4 119.6 . . . no C5 C4 H4 119.7 . . . no C4 C5 C6 120.3(6) . . . yes C4 C5 H5 119.9 . . . no C6 C5 H5 119.8 . . . no C1 C6 C5 118.1(6) . . . yes C1 C6 H6 120.8 . . . no C5 C6 H6 121.1 . . . no I1 C7 C8 118.2(4) . . . yes I1 C7 C12 118.6(4) . . . yes C8 C7 C12 123.2(5) . . . yes C7 C8 C9 118.3(6) . . . yes C7 C8 H8 121.0 . . . no C9 C8 H8 120.7 . . . no C8 C9 C10 120.4(6) . . . yes C8 C9 H9 120.2 . . . no C10 C9 H9 119.4 . . . no C9 C10 C11 120.4(6) . . . yes C9 C10 H10 119.9 . . . no C11 C10 H10 119.8 . . . no C10 C11 C12 120.7(6) . . . yes C10 C11 H11 119.7 . . . no C12 C11 H11 119.6 . . . no C7 C12 C11 117.1(6) . . . yes C7 C12 H12 121.3 . . . no C11 C12 H12 121.6 . . . no N1 C13 C14 123.3(5) . . . yes N1 C13 H13 118.4 . . . no C14 C13 H13 118.3 . . . no C13 C14 C15 119.2(5) . . . yes C13 C14 H14 120.6 . . . no C15 C14 H14 120.1 . . . no C14 C15 C16 119.0(5) . . . yes C14 C15 H15 120.3 . . . no C16 C15 H15 120.8 . . . no C15 C16 C17 121.7(5) . . . yes C15 C16 C24 117.5(5) . . . yes C17 C16 C24 120.8(5) . . . yes C16 C17 C18 119.8(5) . . . yes C16 C17 H17 120.1 . . . no C18 C17 H17 120.1 . . . no C17 C18 C19 121.1(5) . . . yes C17 C18 H18 119.4 . . . no C19 C18 H18 119.5 . . . no C18 C19 C20 121.7(5) . . . yes C18 C19 C23 120.3(5) . . . yes C20 C19 C23 118.0(5) . . . yes C19 C20 C21 118.9(5) . . . yes C19 C20 H20 120.6 . . . no C21 C20 H20 120.5 . . . no C20 C21 C22 119.4(5) . . . yes C20 C21 H21 120.5 . . . no C22 C21 H21 120.1 . . . no N2 C22 C21 123.3(5) . . . yes N2 C22 H22 118.1 . . . no C21 C22 H22 118.6 . . . no N2 C23 C19 122.5(5) . . . yes N2 C23 C24 118.5(4) . . . yes C19 C23 C24 119.0(5) . . . yes N1 C24 C16 122.9(5) . . . yes N1 C24 C23 118.2(5) . . . yes C16 C24 C23 118.9(4) . . . yes CL1 C25 CL2 115.9(8) . . . yes CL1 C25 H25a 107.8 . . . no CL1 C25 H25b 107.6 . . . no CL2 C25 H25a 109.8 . . . no CL2 C25 H25b 109.6 . . . no H25a C25 H25b 105.6 . . . no F1 B1 F2 110(1) . . . yes F1 B1 F3 109(1) . . . yes F1 B1 F4 111(1) . . . yes F2 B1 F3 103(1) . . . yes F2 B1 F4 109(1) . . . yes F3 B1 F4 111(1) . . . yes F1 B1' F2 110(1) . . . yes F1 B1' F3' 114(1) . . . yes F1 B1' F4' 99(1) . . . yes F2 B1' F3' 118(1) . . . yes F2 B1' F4' 106(1) . . . yes F3' B1' F4' 105(1) . . . 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 I1 N2 2.925(4) . . ? I1 F3 3.012(8) . . ? I1 F3' 3.013(10) . . ? I1 N1 3.164(4) . . ? CL1 C2 3.04(1) . . ? CL1 C3 3.49(1) . . ? CL2 C3 3.28(1) . 5_555 ? CL2 F4 3.404(9) . 6_656 ? CL2 C4 3.42(1) . 5_555 ? CL2 C10 3.419(8) . 6_756 ? CL2 B1' 3.43(2) . 6_656 ? CL2 F2 3.536(7) . 6_656 ? F1 C21 3.348(7) . 5_445 ? F1 C12 3.430(7) . 5_455 ? F2 C25 3.25(1) . 6_646 ? F2 C4 3.270(8) . 6_656 ? F2 C6 3.307(7) . 5_455 ? F2 C5 3.334(8) . 6_656 ? F2 C2 3.45(1) . . ? F3 C11 3.15(1) . 5_455 ? F3 C12 3.19(1) . 5_455 ? F3 C15 3.435(9) . 7_646 ? F3' C1 3.30(1) . . ? F3' C17 3.33(1) . 7_646 ? F3' C2 3.47(1) . . ? F3' C15 3.48(1) . 7_646 ? F4 C8 3.091(10) . 5_445 ? F4 C9 3.28(1) . 5_445 ? F4 C22 3.438(10) . 5_445 ? F4 C17 3.525(9) . 7_646 ? F4 C25 3.56(2) . 6_646 ? F4' C25 2.77(2) . 6_646 ? F4' C22 3.26(1) . 5_445 ? F4' C8 3.35(1) . 5_445 ? F4' C10 3.59(1) . 1_455 ? N1 C12 3.404(7) . . ? N1 C7 3.427(7) . . ? N1 C16 3.439(7) . 7_646 ? N1 C15 3.593(7) . 7_646 ? N2 C7 3.265(7) . . ? N2 C8 3.480(8) . . ? N2 C18 3.576(7) . 3_756 ? C5 C5 3.31(1) . 2_756 ? C6 C9 3.590(9) . 5_445 ? C13 C17 3.522(8) . 7_646 ? C13 C16 3.544(8) . 7_646 ? C14 C23 3.417(7) . 7_646 ? C14 C14 3.44(1) . 3_746 ? C14 C24 3.568(7) . 7_646 ? C15 C24 3.486(7) . 7_646 ? C15 C23 3.599(7) . 7_646 ? C16 C20 3.349(7) . 3_756 ? C16 C21 3.547(8) . 3_756 ? C17 C21 3.551(8) . 3_756 ? C17 C22 3.571(8) . 3_756 ? C18 C23 3.361(7) . 3_756 ? C19 C19 3.571(10) . 3_756 ? C19 C23 3.577(7) . 3_756 ? C20 C20 3.44(1) . 7_656 ? C20 C24 3.559(7) . 3_756 ? C25 B1' 3.58(2) . 6_656 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_General1 _database_code_CSD 198779 _audit_creation_date 'Tue Sep 17 16:28:59 2002' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C24 H22 B F4 I N2' _chemical_formula_moiety 'C12 H14 I 1+, B F4 1-, C12 H8 N2' _chemical_formula_weight 552.16 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 7.183(2) _cell_length_b 17.257(5) _cell_length_c 18.711(5) _cell_angle_alpha 90 _cell_angle_beta 102.80(3) _cell_angle_gamma 90 _cell_volume 2261(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 19352 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.1 _cell_measurement_temperature 93.2 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096.00 _exptl_absorpt_coefficient_mu 1.463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_absorpt_correction_T_min 0.599 _exptl_absorpt_correction_T_max 0.864 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K?a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method ?w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 25941 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_theta_max 30.03 _diffrn_measured_fraction_theta_max 0.9747 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.9747 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -3.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 6445 _reflns_number_gt 4364 _reflns_threshold_expression F^2^>2.0?s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0489 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 6445 _refine_ls_number_parameters 289 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[?s^2^(Fo^2^) + (0.00200(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0009 _refine_diff_density_max 0.95 _refine_diff_density_min -1.48 _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) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 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) ; I I -0.474 1.812 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # 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 I1 I 0.56963(2) 0.235942(9) 0.44244(1) 0.01696(3) Uani 1.00 d . . . F1 F 0.4047(2) 0.20777(9) 0.56707(9) 0.0346(5) Uani 1.00 d . . . F2 F 0.0841(2) 0.18921(10) 0.54952(9) 0.0399(5) Uani 1.00 d . . . F3 F 0.2901(3) 0.11477(9) 0.63156(10) 0.0431(5) Uani 1.00 d . . . F4 F 0.2519(2) 0.2421(1) 0.65568(8) 0.0322(5) Uani 1.00 d . . . N1 N 0.7456(3) 0.3614(1) 0.5075(1) 0.0172(5) Uani 1.00 d . . . N2 N 0.5401(3) 0.4094(1) 0.3715(1) 0.0208(6) Uani 1.00 d . . . C1 C 0.7233(3) 0.2489(1) 0.3591(1) 0.0152(6) Uani 1.00 d . . . C2 C 0.9191(3) 0.2561(1) 0.3799(1) 0.0214(6) Uani 1.00 d . . . C3 C 1.0172(3) 0.2694(2) 0.3248(1) 0.0245(7) Uani 1.00 d . . . C4 C 0.9210(4) 0.2742(2) 0.2523(1) 0.0243(7) Uani 1.00 d . . . C5 C 0.7251(3) 0.2653(2) 0.2335(1) 0.0233(6) Uani 1.00 d . . . C6 C 0.6222(3) 0.2524(1) 0.2873(1) 0.0210(7) Uani 1.00 d . . . C7 C 0.4373(4) 0.1361(1) 0.4018(1) 0.0227(7) Uani 1.00 d . . . C8 C 0.3281(4) 0.0833(1) 0.3934(1) 0.0191(7) Uani 1.00 d . . . C9 C 0.1917(4) 0.0183(1) 0.3843(1) 0.0204(7) Uani 1.00 d . . . C10 C 0.2688(6) -0.0443(2) 0.4394(3) 0.078(1) Uani 1.00 d . . . C11 C 0.0032(5) 0.0481(2) 0.3979(3) 0.071(1) Uani 1.00 d . . . C12 C 0.1587(7) -0.0129(2) 0.3077(2) 0.083(2) Uani 1.00 d . . . C13 C 0.8437(4) 0.3400(1) 0.5734(1) 0.0202(7) Uani 1.00 d . . . C14 C 0.9317(4) 0.3916(2) 0.6278(1) 0.0242(7) Uani 1.00 d . . . C15 C 0.9157(4) 0.4694(2) 0.6128(1) 0.0245(7) Uani 1.00 d . . . C16 C 0.8153(3) 0.4947(1) 0.5441(1) 0.0201(7) Uani 1.00 d . . . C17 C 0.7994(4) 0.5753(1) 0.5254(2) 0.0238(7) Uani 1.00 d . . . C18 C 0.7067(4) 0.5991(1) 0.4587(2) 0.0254(8) Uani 1.00 d . . . C19 C 0.6186(4) 0.5442(1) 0.4037(2) 0.0211(7) Uani 1.00 d . . . C20 C 0.5235(4) 0.5669(2) 0.3329(2) 0.0283(8) Uani 1.00 d . . . C21 C 0.4402(4) 0.5118(2) 0.2837(2) 0.0312(8) Uani 1.00 d . . . C22 C 0.4502(4) 0.4340(2) 0.3059(2) 0.0268(8) Uani 1.00 d . . . C23 C 0.6260(3) 0.4642(1) 0.4202(1) 0.0188(7) Uani 1.00 d . . . C24 C 0.7304(3) 0.4387(1) 0.4920(1) 0.0166(6) Uani 1.00 d . . . B1 B 0.2562(4) 0.1878(2) 0.6013(2) 0.0223(8) Uani 1.00 d . . . H1 H 0.9850 0.2525 0.4298 0.0272 Uiso 1.00 calc . . . H2 H 1.1527 0.2749 0.3372 0.0310 Uiso 1.00 calc . . . H3 H 0.9903 0.2841 0.2153 0.0294 Uiso 1.00 calc . . . H4 H 0.6596 0.2672 0.1833 0.0299 Uiso 1.00 calc . . . H5 H 0.4865 0.2462 0.2749 0.0239 Uiso 1.00 calc . . . H6 H 0.3631 -0.0731 0.4235 0.0881 Uiso 1.00 calc . . . H7 H 0.1663 -0.0776 0.4446 0.0881 Uiso 1.00 calc . . . H8 H 0.3213 -0.0209 0.4856 0.0881 Uiso 1.00 calc . . . H9 H -0.0827 0.0063 0.3977 0.0834 Uiso 1.00 calc . . . H10 H 0.0233 0.0747 0.4431 0.0834 Uiso 1.00 calc . . . H11 H -0.0531 0.0835 0.3592 0.0834 Uiso 1.00 calc . . . H12 H 0.1679 0.0276 0.2745 0.0957 Uiso 1.00 calc . . . H13 H 0.0369 -0.0364 0.2947 0.0957 Uiso 1.00 calc . . . H14 H 0.2544 -0.0512 0.3053 0.0957 Uiso 1.00 calc . . . H15 H 0.8555 0.2859 0.5840 0.0251 Uiso 1.00 calc . . . H16 H 1.0004 0.3736 0.6743 0.0308 Uiso 1.00 calc . . . H17 H 0.9726 0.5062 0.6492 0.0296 Uiso 1.00 calc . . . H18 H 0.8555 0.6126 0.5612 0.0315 Uiso 1.00 calc . . . H19 H 0.6989 0.6528 0.4476 0.0317 Uiso 1.00 calc . . . H20 H 0.5163 0.6203 0.3196 0.0363 Uiso 1.00 calc . . . H21 H 0.3770 0.5259 0.2350 0.0373 Uiso 1.00 calc . . . H22 H 0.3882 0.3961 0.2714 0.0326 Uiso 1.00 calc . . . 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 I1 0.01889(7) 0.01479(6) 0.01882(8) -0.00364(9) 0.00768(5) -0.00056(9) F1 0.044(1) 0.0315(8) 0.037(1) -0.0021(8) 0.0277(8) 0.0002(8) F2 0.037(1) 0.044(1) 0.032(1) 0.0034(8) -0.0071(8) -0.0061(8) F3 0.051(1) 0.0288(9) 0.044(1) -0.0090(8) 0.0001(9) 0.0180(8) F4 0.0282(8) 0.045(1) 0.0263(9) -0.0031(8) 0.0116(7) -0.0103(8) N1 0.019(1) 0.016(1) 0.020(1) -0.0020(9) 0.0111(9) 0.0001(9) N2 0.023(1) 0.020(1) 0.022(1) 0.0016(9) 0.0092(10) 0.0002(9) C1 0.020(1) 0.010(1) 0.018(1) -0.0005(9) 0.0102(9) -0.0013(9) C2 0.021(1) 0.021(1) 0.022(1) 0.000(1) 0.0039(10) -0.001(1) C3 0.019(1) 0.025(1) 0.032(1) -0.001(1) 0.010(1) -0.003(1) C4 0.028(1) 0.021(2) 0.029(2) -0.003(1) 0.017(1) -0.002(1) C5 0.028(1) 0.024(1) 0.019(1) 0.001(1) 0.009(1) -0.004(1) C6 0.021(1) 0.021(2) 0.022(1) -0.001(1) 0.0066(10) -0.004(1) C7 0.025(1) 0.021(1) 0.022(1) -0.001(1) 0.006(1) 0.000(1) C8 0.024(1) 0.017(1) 0.017(1) 0.001(1) 0.007(1) 0.001(1) C9 0.024(1) 0.017(1) 0.020(1) -0.006(1) 0.003(1) -0.001(1) C10 0.052(2) 0.045(2) 0.112(4) -0.034(2) -0.032(2) 0.049(2) C11 0.034(2) 0.036(2) 0.150(4) -0.019(2) 0.033(2) -0.031(2) C12 0.138(4) 0.075(3) 0.046(2) -0.083(3) 0.041(3) -0.032(2) C13 0.020(1) 0.020(1) 0.023(1) -0.001(1) 0.011(1) 0.002(1) C14 0.023(1) 0.030(1) 0.021(1) -0.004(1) 0.009(1) 0.000(1) C15 0.025(1) 0.027(1) 0.025(2) -0.006(1) 0.013(1) -0.008(1) C16 0.018(1) 0.019(1) 0.028(2) -0.004(1) 0.014(1) -0.004(1) C17 0.023(1) 0.015(1) 0.038(2) -0.007(1) 0.017(1) -0.007(1) C18 0.021(1) 0.011(1) 0.050(2) -0.001(1) 0.022(1) 0.000(1) C19 0.018(1) 0.016(1) 0.033(2) 0.003(1) 0.016(1) 0.005(1) C20 0.026(1) 0.021(1) 0.042(2) 0.008(1) 0.018(1) 0.011(1) C21 0.029(2) 0.037(2) 0.030(2) 0.010(1) 0.010(1) 0.013(1) C22 0.026(1) 0.028(2) 0.028(2) 0.007(1) 0.009(1) 0.003(1) C23 0.017(1) 0.019(1) 0.024(1) 0.002(1) 0.013(1) 0.000(1) C24 0.016(1) 0.016(1) 0.021(1) 0.0005(10) 0.011(1) -0.001(1) B1 0.025(2) 0.023(2) 0.019(2) -0.001(1) 0.005(1) 0.002(1) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'teXsan (MSC & Rigaku, 1999)' _computing_structure_solution 'PATTY (Beurskens, 1994)' _computing_structure_refinement 'teXsan (MSC & Rigaku, 1999)' _computing_publication_material 'teXsan (MSC & Rigaku, 1999)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' #------------------------------------------------------------------------------ _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 I1 C1 2.112(2) . . yes I1 C7 2.032(3) . . yes F1 B1 1.403(3) . . yes F2 B1 1.391(3) . . yes F3 B1 1.381(3) . . yes F4 B1 1.389(3) . . yes N1 C13 1.331(3) . . yes N1 C24 1.365(3) . . yes N2 C22 1.323(3) . . yes N2 C23 1.362(3) . . yes C1 C2 1.379(3) . . yes C1 C6 1.380(3) . . yes C2 C3 1.390(3) . . yes C2 H1 0.951 . . no C3 C4 1.382(4) . . yes C3 H2 0.954 . . no C4 C5 1.381(4) . . yes C4 H3 0.953 . . no C5 C6 1.392(3) . . yes C5 H4 0.954 . . no C6 H5 0.957 . . no C7 C8 1.189(3) . . yes C8 C9 1.475(3) . . yes C9 C10 1.511(4) . . yes C9 C11 1.521(4) . . yes C9 C12 1.500(4) . . yes C10 H6 0.939 . . no C10 H7 0.956 . . no C10 H8 0.954 . . no C11 H9 0.949 . . no C11 H10 0.946 . . no C11 H11 0.964 . . no C12 H12 0.948 . . no C12 H13 0.946 . . no C12 H14 0.961 . . no C13 C14 1.395(4) . . yes C13 H15 0.954 . . no C14 C15 1.372(4) . . yes C14 H16 0.951 . . no C15 C16 1.396(4) . . yes C15 H17 0.955 . . no C16 C17 1.432(3) . . yes C16 C24 1.413(3) . . yes C17 C18 1.342(4) . . yes C17 H18 0.953 . . no C18 C19 1.438(4) . . yes C18 H19 0.949 . . no C19 C20 1.405(4) . . yes C19 C23 1.413(3) . . yes C20 C21 1.367(4) . . yes C20 H20 0.955 . . no C21 C22 1.402(4) . . yes C21 H21 0.956 . . no C22 H22 0.957 . . no C23 C24 1.454(4) . . yes #------------------------------------------------------------------------------ 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 I1 C7 95.23(9) . . . yes C13 N1 C24 118.0(2) . . . yes C22 N2 C23 117.0(2) . . . yes I1 C1 C2 118.0(2) . . . yes I1 C1 C6 118.4(2) . . . yes C2 C1 C6 123.6(2) . . . yes C1 C2 C3 117.3(2) . . . yes C1 C2 H1 121.7 . . . no C3 C2 H1 121.0 . . . no C2 C3 C4 120.8(2) . . . yes C2 C3 H2 119.6 . . . no C4 C3 H2 119.6 . . . no C3 C4 C5 120.2(2) . . . yes C3 C4 H3 119.7 . . . no C5 C4 H3 120.1 . . . no C4 C5 C6 120.5(2) . . . yes C4 C5 H4 120.0 . . . no C6 C5 H4 119.5 . . . no C1 C6 C5 117.5(2) . . . yes C1 C6 H5 121.3 . . . no C5 C6 H5 121.2 . . . no I1 C7 C8 159.8(2) . . . yes C7 C8 C9 178.9(3) . . . yes C8 C9 C10 109.4(2) . . . yes C8 C9 C11 108.5(2) . . . yes C8 C9 C12 110.1(2) . . . yes C10 C9 C11 109.5(3) . . . yes C10 C9 C12 110.5(3) . . . yes C11 C9 C12 108.8(3) . . . yes C9 C10 H6 110.1 . . . no C9 C10 H7 109.0 . . . no C9 C10 H8 109.1 . . . no H6 C10 H7 109.9 . . . no H6 C10 H8 110.0 . . . no H7 C10 H8 108.6 . . . no C9 C11 H9 110.2 . . . no C9 C11 H10 110.4 . . . no C9 C11 H11 109.3 . . . no H9 C11 H10 109.9 . . . no H9 C11 H11 108.4 . . . no H10 C11 H11 108.6 . . . no C9 C12 H12 110.0 . . . no C9 C12 H13 110.0 . . . no C9 C12 H14 109.2 . . . no H12 C12 H13 110.0 . . . no H12 C12 H14 108.7 . . . no H13 C12 H14 108.8 . . . no N1 C13 C14 124.1(2) . . . yes N1 C13 H15 118.0 . . . no C14 C13 H15 117.9 . . . no C13 C14 C15 118.1(2) . . . yes C13 C14 H16 121.3 . . . no C15 C14 H16 120.6 . . . no C14 C15 C16 119.8(2) . . . yes C14 C15 H17 120.1 . . . no C16 C15 H17 120.1 . . . no C15 C16 C17 121.7(2) . . . yes C15 C16 C24 118.5(2) . . . yes C17 C16 C24 119.7(2) . . . yes C16 C17 C18 121.4(2) . . . yes C16 C17 H18 119.0 . . . no C18 C17 H18 119.6 . . . no C17 C18 C19 120.8(2) . . . yes C17 C18 H19 119.7 . . . no C19 C18 H19 119.5 . . . no C18 C19 C20 122.4(2) . . . yes C18 C19 C23 119.9(2) . . . yes C20 C19 C23 117.7(2) . . . yes C19 C20 C21 119.4(2) . . . yes C19 C20 H20 120.2 . . . no C21 C20 H20 120.4 . . . no C20 C21 C22 118.7(3) . . . yes C20 C21 H21 120.6 . . . no C22 C21 H21 120.7 . . . no N2 C22 C21 124.4(3) . . . yes N2 C22 H22 117.7 . . . no C21 C22 H22 117.9 . . . no N2 C23 C19 122.9(2) . . . yes N2 C23 C24 118.3(2) . . . yes C19 C23 C24 118.9(2) . . . yes N1 C24 C16 121.4(2) . . . yes N1 C24 C23 119.5(2) . . . yes C16 C24 C23 119.1(2) . . . yes F1 B1 F2 109.0(2) . . . yes F1 B1 F3 109.2(2) . . . yes F1 B1 F4 108.1(2) . . . yes F2 B1 F3 110.5(2) . . . yes F2 B1 F4 109.7(2) . . . yes F3 B1 F4 110.2(2) . . . 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 I1 N1 2.661(2) . . ? I1 F1 2.882(1) . . ? I1 N2 3.263(2) . . ? I1 C13 3.311(3) . . ? F1 C7 3.386(3) . . ? F1 C18 3.437(3) . 3_666 ? F1 C5 3.470(3) . 4_555 ? F2 C13 3.208(3) . 1_455 ? F2 C2 3.339(3) . 1_455 ? F2 C10 3.599(4) . 3_556 ? F3 C22 3.318(3) . 4_555 ? F3 C11 3.482(4) . 3_556 ? F3 C21 3.560(4) . 4_555 ? F4 C6 3.201(3) . 4_555 ? F4 C4 3.302(3) . 4_455 ? F4 C5 3.391(3) . 4_555 ? F4 C14 3.418(3) . 1_455 ? F4 C13 3.438(3) . 1_455 ? F4 C18 3.530(3) . 3_666 ? N1 C1 3.362(3) . . ? N1 C2 3.445(3) . . ? N1 C18 3.513(3) . 3_666 ? N2 C1 3.098(3) . . ? N2 C6 3.253(3) . . ? N2 C17 3.439(3) . 3_666 ? C6 C22 3.415(4) . . ? C13 C18 3.572(4) . 3_766 ? C14 C18 3.355(4) . 3_766 ? C14 C20 3.579(4) . 3_666 ? C14 C19 3.586(4) . 3_766 ? C15 C19 3.435(4) . 3_766 ? C15 C18 3.486(4) . 3_766 ? C15 C21 3.548(4) . 3_666 ? C15 C20 3.577(4) . 3_666 ? C16 C16 3.426(5) . 3_766 ? C16 C23 3.455(3) . 3_666 ? C16 C17 3.522(3) . 3_766 ? C16 C19 3.531(3) . 3_666 ? C17 C24 3.473(4) . 3_766 ? C17 C23 3.496(3) . 3_666 ? C18 C24 3.525(3) . 3_666 ? C19 C24 3.514(3) . 3_666 ?