# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_General _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef 'ns208py345I.cif' _audit_creation_date 2011-08-05 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Toyonobu Usuki' _publ_contact_author_email t-usuki@sophia.ac.jp _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_footnote _publ_author_address ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku (2010). CrystalStructure. Version 4.0. Rigaku Corporation, Tokyo, Japan. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. SIR92 Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122. Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; loop_ _publ_author_name 'Toyonobu Usuki' H.Yamada T.Hayashi H.Yanuma Y.Koseki N.Suzuki Y.Masuyama 'Yong Lin' #============================================================================== data_Py345I _database_code_depnum_ccdc_archive 'CCDC 853163' #TrackingRef 'ns208py345I.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C5 H2 I3 N' _chemical_formula_moiety 'C5 H2 I3 N' _chemical_formula_weight 456.79 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 18.560(6) _cell_length_b 9.955(3) _cell_length_c 11.987(4) _cell_angle_alpha 90.0000 _cell_angle_beta 129.4130(8) _cell_angle_gamma 90.0000 _cell_volume 1711.1(9) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2534 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 29.13 _cell_measurement_temperature 299 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 3.546 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584.00 _exptl_absorpt_coefficient_mu 10.883 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.339 _exptl_absorpt_correction_T_max 0.580 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 299 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.314 _diffrn_reflns_number 6176 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measured_fraction_theta_full 0.972 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. 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 1913 _reflns_number_gt 1568 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0937 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 1913 _refine_ls_number_parameters 82 _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0268P)^2^+12.1220P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.750 _refine_diff_density_min -1.050 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; I I -0.4742 1.8119 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.38262(4) 0.54507(6) 0.76842(6) 0.04140(19) Uani 1.0 8 d . . . I2 I 0.37859(5) 0.21416(6) 0.88979(6) 0.0434(2) Uani 1.0 8 d . . . I3 I 0.36353(5) -0.06897(6) 0.68308(7) 0.0480(2) Uani 1.0 8 d . . . N1 N 0.3739(5) 0.2756(8) 0.4802(8) 0.0373(17) Uani 1.0 8 d . . . C1 C 0.3777(6) 0.3805(9) 0.5535(9) 0.0346(19) Uani 1.0 8 d . . . C2 C 0.3772(6) 0.3695(8) 0.6682(9) 0.0281(17) Uani 1.0 8 d . . . C3 C 0.3751(5) 0.2399(8) 0.7138(8) 0.0263(16) Uani 1.0 8 d . . . C4 C 0.3721(6) 0.1319(8) 0.6383(9) 0.0306(18) Uani 1.0 8 d . . . C5 C 0.3696(6) 0.1520(9) 0.5221(9) 0.0341(19) Uani 1.0 8 d . . . H1 H 0.3808 0.4661 0.5257 0.0416 Uiso 1.0 8 calc R . . H5 H 0.3647 0.0777 0.4706 0.0410 Uiso 1.0 8 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I1 0.0623(4) 0.0284(3) 0.0389(4) 0.0026(3) 0.0347(4) -0.0015(3) I2 0.0628(4) 0.0415(4) 0.0379(4) -0.0048(3) 0.0376(4) 0.0019(3) I3 0.0713(5) 0.0273(3) 0.0498(4) -0.0015(3) 0.0405(4) 0.0047(3) N1 0.052(5) 0.036(4) 0.039(4) 0.004(4) 0.036(4) 0.002(4) C1 0.043(5) 0.036(5) 0.025(5) 0.004(4) 0.021(4) 0.004(4) C2 0.029(4) 0.033(5) 0.026(4) -0.003(4) 0.020(4) -0.007(4) C3 0.026(4) 0.033(5) 0.020(4) 0.002(4) 0.015(4) 0.003(4) C4 0.033(4) 0.026(4) 0.029(5) -0.001(4) 0.018(4) 0.004(4) C5 0.039(5) 0.037(5) 0.033(5) 0.001(4) 0.026(4) -0.003(4) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 I1 C2 2.087(10) yes . . I2 C3 2.085(11) yes . . I3 C4 2.103(9) yes . . N1 C1 1.337(14) yes . . N1 C5 1.350(13) yes . . C1 C2 1.385(17) yes . . C2 C3 1.411(13) yes . . C3 C4 1.383(14) yes . . C4 C5 1.378(17) yes . . C1 H1 0.930 no . . C5 H5 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 N1 C5 117.3(11) yes . . . N1 C1 C2 124.0(9) yes . . . I1 C2 C1 118.5(7) yes . . . I1 C2 C3 123.1(8) yes . . . C1 C2 C3 118.4(9) yes . . . I2 C3 C2 120.9(7) yes . . . I2 C3 C4 122.0(7) yes . . . C2 C3 C4 117.2(10) yes . . . I3 C4 C3 123.4(9) yes . . . I3 C4 C5 115.9(7) yes . . . C3 C4 C5 120.7(9) yes . . . N1 C5 C4 122.4(9) yes . . . N1 C1 H1 118.015 no . . . C2 C1 H1 118.019 no . . . N1 C5 H5 118.824 no . . . C4 C5 H5 118.808 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 -2.2(12) no . . . . C5 N1 C1 C2 -0.2(12) no . . . . N1 C1 C2 I1 -179.6(7) no . . . . N1 C1 C2 C3 1.7(12) no . . . . I1 C2 C3 I2 -0.7(9) no . . . . I1 C2 C3 C4 -179.6(4) no . . . . C1 C2 C3 I2 178.0(6) no . . . . C1 C2 C3 C4 -1.0(10) no . . . . I2 C3 C4 I3 3.4(9) no . . . . I2 C3 C4 C5 179.8(5) no . . . . C2 C3 C4 I3 -177.7(6) no . . . . C2 C3 C4 C5 -1.2(11) no . . . . I3 C4 C5 N1 179.6(5) no . . . . C3 C4 C5 N1 2.9(12) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 N1 C3 2.808(16) no . . C1 C4 2.702(13) no . . C2 C5 2.731(14) no . . I1 N1 3.191(10) no . 4_565 I1 C1 3.554(12) no . 4_565 N1 I1 3.191(10) no . 4_564 C1 I1 3.554(12) no . 4_564 C1 C2 3.545(10) no . 2_656 C2 C1 3.545(10) no . 2_656 I1 H1 2.9938 no . . I3 H5 2.9479 no . . C1 H5 3.1347 no . . C3 H1 3.2361 no . . C3 H5 3.2288 no . . C5 H1 3.1322 no . . I1 H1 3.4967 no . 2_656 I1 H1 3.1070 no . 4_565 I2 H1 3.5638 no . 4_565 I2 H5 3.1250 no . 4_555 I3 H5 3.4340 no . 4_555 H1 I1 3.4967 no . 2_656 H1 I1 3.1070 no . 4_564 H1 I2 3.5638 no . 4_564 H5 I2 3.1250 no . 4_554 H5 I3 3.4340 no . 4_554 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== #============================================================================== data_Py345IBI _database_code_depnum_ccdc_archive 'CCDC 853164' #TrackingRef 'ns210py345IBI.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C5 H2 Br I2 N' _chemical_formula_moiety 'C5 H2 Br I2 N' _chemical_formula_weight 409.79 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 7.065(6) _cell_length_b 12.192(11) _cell_length_c 9.672(8) _cell_angle_alpha 90.0000 _cell_angle_beta 89.993(5) _cell_angle_gamma 90.0000 _cell_volume 833.1(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2204 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 299 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 3.267 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720.00 _exptl_absorpt_coefficient_mu 12.279 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'NUMABS (Rigaku, 1999)' _exptl_absorpt_correction_T_min 0.304 _exptl_absorpt_correction_T_max 0.541 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 299 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.314 _diffrn_reflns_number 5431 _diffrn_reflns_av_R_equivalents 0.0850 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.898 _diffrn_measured_fraction_theta_full 0.898 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. 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 1716 _reflns_number_gt 1066 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1020 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 1716 _refine_ls_number_parameters 82 _refine_ls_goodness_of_fit_ref 0.888 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0315P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 1.690 _refine_diff_density_min -1.050 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Br Br -0.2901 2.4595 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; I I -0.4742 1.8119 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.25003(11) 0.15416(5) 0.71493(6) 0.0426(3) Uani 1.0 4 d . . . I2 I 0.24987(13) 0.05077(6) 1.33714(7) 0.0546(3) Uani 1.0 4 d . . . Br1 Br 0.2496(2) 0.23740(8) 1.05793(10) 0.0485(4) Uani 1.0 4 d . . . N1 N 0.2507(14) -0.1391(6) 0.9640(8) 0.035(2) Uani 1.0 4 d . . . C1 C 0.2501(16) -0.0648(7) 0.8611(10) 0.038(3) Uani 1.0 4 d . . . C2 C 0.2487(16) 0.0470(7) 0.8851(10) 0.033(3) Uani 1.0 4 d . . . C3 C 0.2498(16) 0.0856(7) 1.0217(10) 0.031(3) Uani 1.0 4 d . . . C4 C 0.2500(17) 0.0086(8) 1.1246(10) 0.036(3) Uani 1.0 4 d . . . C5 C 0.2504(16) -0.1024(8) 1.0933(10) 0.037(3) Uani 1.0 4 d . . . H1 H 0.2506 -0.0897 0.7702 0.0457 Uiso 1.0 4 calc R . . H5 H 0.2506 -0.1529 1.1653 0.0444 Uiso 1.0 4 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I1 0.0685(6) 0.0293(4) 0.0300(4) 0.0001(4) -0.0036(4) 0.0040(3) I2 0.0851(8) 0.0524(5) 0.0262(4) 0.0003(5) -0.0040(4) -0.0054(3) Br1 0.0775(10) 0.0288(6) 0.0392(6) -0.0006(6) -0.0037(6) -0.0096(4) N1 0.048(6) 0.029(4) 0.029(5) 0.002(4) -0.002(4) -0.006(4) C1 0.051(8) 0.025(5) 0.038(6) -0.001(5) 0.001(6) 0.004(4) C2 0.039(7) 0.025(5) 0.033(6) -0.004(5) -0.003(5) -0.001(4) C3 0.031(7) 0.029(5) 0.034(6) -0.000(5) -0.003(5) -0.015(4) C4 0.043(8) 0.039(6) 0.025(6) 0.001(5) 0.001(5) -0.002(4) C5 0.038(7) 0.041(6) 0.032(6) -0.000(5) -0.005(5) 0.007(5) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 I1 C2 2.101(9) yes . . I2 C4 2.119(10) yes . . Br1 C3 1.884(8) yes . . N1 C1 1.346(12) yes . . N1 C5 1.328(12) yes . . C1 C2 1.383(12) yes . . C2 C3 1.402(13) yes . . C3 C4 1.369(13) yes . . C4 C5 1.386(14) yes . . C1 H1 0.930 no . . C5 H5 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 N1 C5 118.0(8) yes . . . N1 C1 C2 122.6(9) yes . . . I1 C2 C1 118.8(7) yes . . . I1 C2 C3 122.0(6) yes . . . C1 C2 C3 119.3(8) yes . . . Br1 C3 C2 120.3(7) yes . . . Br1 C3 C4 122.6(7) yes . . . C2 C3 C4 117.1(8) yes . . . I2 C4 C3 122.6(7) yes . . . I2 C4 C5 116.7(7) yes . . . C3 C4 C5 120.6(9) yes . . . N1 C5 C4 122.4(9) yes . . . N1 C1 H1 118.683 no . . . C2 C1 H1 118.681 no . . . N1 C5 H5 118.802 no . . . C4 C5 H5 118.810 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 -0.1(16) no . . . . C5 N1 C1 C2 -0.2(16) no . . . . N1 C1 C2 I1 179.5(9) no . . . . N1 C1 C2 C3 0.7(17) no . . . . I1 C2 C3 Br1 0.7(13) no . . . . I1 C2 C3 C4 -179.6(6) no . . . . C1 C2 C3 Br1 179.6(9) no . . . . C1 C2 C3 C4 -0.7(15) no . . . . Br1 C3 C4 I2 0.1(14) no . . . . Br1 C3 C4 C5 -179.9(7) no . . . . C2 C3 C4 I2 -179.6(8) no . . . . C2 C3 C4 C5 0.4(16) no . . . . I2 C4 C5 N1 -180.0(7) no . . . . C3 C4 C5 N1 0.0(18) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 I1 Br1 3.469(3) no . . I2 Br1 3.531(3) no . . N1 C3 2.796(11) no . . C1 C4 2.702(14) no . . C2 C5 2.715(13) no . . I1 N1 3.057(8) no . 2_556 I1 C1 3.504(9) no . 2_556 N1 I1 3.057(8) no . 2_546 N1 C3 3.598(15) no . 3_557 N1 C3 3.592(15) no . 3_657 C1 I1 3.504(9) no . 2_546 C2 C4 3.589(17) no . 3_557 C2 C5 3.596(16) no . 3_557 C3 N1 3.598(15) no . 3_557 C3 N1 3.592(15) no . 3_657 C4 C2 3.589(17) no . 3_557 C5 C2 3.596(16) no . 3_557 I1 H1 3.0203 no . . I2 H5 2.9877 no . . C1 H5 3.1323 no . . C3 H1 3.2375 no . . C3 H5 3.2221 no . . C5 H1 3.1287 no . . I1 H1 3.1267 no . 2_556 Br1 H5 2.9926 no . 2_557 H1 I1 3.1267 no . 2_546 H5 Br1 2.9926 no . 2_547 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================