Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'L. Brammer' 'Harry Adams' 'Stephen L. Purver' 'Fiorenzo Zordan' _publ_contact_author_name 'Dr Lee Brammer' _publ_contact_author_address ; Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF UNITED KINGDOM ; _publ_contact_author_email LEE.BRAMMER@SHEFFIELD.AC.UK _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Halometallate and halide ions: nucleophiles in competition for hydrogen bond and halogen bond formation in salts of the type (HpyX-n)p[MXq]X {HpyX-n = n-halopyridinium (n = 3, 4); p = 2, 3; q = 4, 6; X = halogen} ; data_ilb263t _database_code_depnum_ccdc_archive 'CCDC 266454' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C5 H5 N I), Au Br3.35 Cl0.65, 2(Cl0.35 Br0.15)' _chemical_formula_sum 'C10 H10 Au Br4 Cl I2 N2' _chemical_formula_weight 948.64 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 Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pcca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 16.113(3) _cell_length_b 4.2049(9) _cell_length_c 28.340(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1920.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2533 _cell_measurement_theta_min 2.520 _cell_measurement_theta_max 26.765 _exptl_crystal_description sheet _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 18.660 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1130 _exptl_absorpt_correction_T_max 0.6985 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 1000 CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14815 _diffrn_reflns_av_R_equivalents 0.1003 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 27.88 _reflns_number_total 2277 _reflns_number_gt 1480 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+2.5152P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2277 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1343 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Au1 Au 0.2500 -0.5000 0.23798(2) 0.0222(2) Uani 1 2 d S . . Br1 Br 0.2500 -0.5000 0.15300(7) 0.0374(5) Uani 1 2 d S A . Br2 Br 0.10749(8) -0.6742(4) 0.23892(5) 0.0450(4) Uani 1 1 d . A . Br3 Br 0.2500 -0.5000 0.32146(10) 0.0285(10) Uani 0.352(12) 2 d SP A 1 Cl1 Cl 0.2500 -0.5000 0.32146(10) 0.0285(10) Uani 0.648(12) 2 d SP A 2 N1 N -0.1005(7) -0.857(3) 0.1033(4) 0.036(3) Uani 1 1 d . . . H1 H -0.1515 -0.7934 0.0974 0.044 Uiso 1 1 calc R . . C2 C -0.0410(7) -0.787(3) 0.0723(5) 0.028(3) Uani 1 1 d . . . H2 H -0.0543 -0.6768 0.0440 0.033 Uiso 1 1 calc R . . C3 C 0.0398(7) -0.874(3) 0.0814(4) 0.026(3) Uani 1 1 d . . . I1 I 0.13184(4) -0.75202(18) 0.03271(3) 0.0265(2) Uani 1 1 d . . . C4 C 0.0571(7) -1.039(3) 0.1223(5) 0.030(3) Uani 1 1 d . . . H4 H 0.1124 -1.1024 0.1291 0.035 Uiso 1 1 calc R . . C5 C -0.0064(8) -1.111(3) 0.1531(5) 0.033(3) Uani 1 1 d . . . H5 H 0.0053 -1.2246 0.1814 0.039 Uiso 1 1 calc R . . C6 C -0.0860(8) -1.021(3) 0.1433(5) 0.033(3) Uani 1 1 d . . . H6 H -0.1302 -1.0735 0.1641 0.040 Uiso 1 1 calc R . . Br Br -0.2500 -0.5000 0.05618(11) 0.0373(12) Uani 0.302(14) 2 d SP B 1 Cl Cl -0.2500 -0.5000 0.05618(11) 0.0373(12) Uani 0.698(14) 2 d SP B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.0177(3) 0.0225(3) 0.0265(4) 0.000 0.000 0.0031(2) Br1 0.0347(9) 0.0448(11) 0.0328(10) 0.000 0.000 0.0111(8) Br2 0.0275(7) 0.0624(10) 0.0452(9) 0.0047(7) -0.0043(6) -0.0092(6) Br3 0.0242(14) 0.0359(17) 0.0255(17) 0.000 0.000 0.0004(12) Cl1 0.0242(14) 0.0359(17) 0.0255(17) 0.000 0.000 0.0004(12) N1 0.025(5) 0.047(7) 0.037(7) -0.004(6) 0.001(5) 0.000(5) C2 0.021(6) 0.034(7) 0.028(7) -0.009(6) 0.000(5) 0.002(5) C3 0.027(6) 0.028(6) 0.025(7) -0.003(5) 0.005(5) 0.007(5) I1 0.0208(4) 0.0286(4) 0.0302(4) -0.0021(3) 0.0027(3) 0.0032(3) C4 0.025(6) 0.030(7) 0.033(7) -0.007(6) -0.010(6) 0.013(5) C5 0.040(7) 0.027(6) 0.031(8) 0.001(6) -0.001(6) -0.003(6) C6 0.029(6) 0.036(7) 0.035(7) -0.006(6) 0.006(6) -0.011(6) Br 0.0207(16) 0.060(2) 0.032(2) 0.000 0.000 0.0060(14) Cl 0.0207(16) 0.060(2) 0.032(2) 0.000 0.000 0.0060(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 Cl1 2.366(3) . ? Au1 Br3 2.366(3) . ? Au1 Br1 2.408(2) . ? Au1 Br2 2.4105(14) . ? Au1 Br2 2.4105(14) 2_545 ? N1 C2 1.333(15) . ? N1 C6 1.347(16) . ? N1 H1 0.8800 . ? C2 C3 1.377(16) . ? C2 H2 0.9500 . ? C3 C4 1.378(17) . ? C3 I1 2.090(12) . ? C4 C5 1.381(17) . ? C4 H4 0.9500 . ? C5 C6 1.366(17) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Au1 Br3 0.0 . . ? Cl1 Au1 Br1 180.0 . . ? Br3 Au1 Br1 180.0 . . ? Cl1 Au1 Br2 89.37(4) . . ? Br3 Au1 Br2 89.37(4) . . ? Br1 Au1 Br2 90.63(4) . . ? Cl1 Au1 Br2 89.37(4) . 2_545 ? Br3 Au1 Br2 89.37(4) . 2_545 ? Br1 Au1 Br2 90.63(4) . 2_545 ? Br2 Au1 Br2 178.73(8) . 2_545 ? C2 N1 C6 122.9(11) . . ? C2 N1 H1 118.6 . . ? C6 N1 H1 118.6 . . ? N1 C2 C3 119.9(12) . . ? N1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 118.9(11) . . ? C2 C3 I1 118.8(9) . . ? C4 C3 I1 122.3(9) . . ? C3 C4 C5 119.6(11) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.3(13) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? N1 C6 C5 118.5(12) . . ? N1 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.769 _refine_diff_density_min -2.020 _refine_diff_density_rms 0.319 data_ilb32m _database_code_depnum_ccdc_archive 'CCDC 266455' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C5 H5 Cl N), 2(Cl4 Fe), Cl' _chemical_formula_sum 'C15 H15 Cl12 Fe2 N3' _chemical_formula_weight 774.40 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 Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.5518(11) _cell_length_b 13.7363(10) _cell_length_c 14.6547(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.3890(10) _cell_angle_gamma 90.00 _cell_volume 2926.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14339 _cell_measurement_theta_min 2.5025 _cell_measurement_theta_max 28.277 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 2.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4727 _exptl_absorpt_correction_T_max 0.5532 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 1000 CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30498 _diffrn_reflns_av_R_equivalents 0.0885 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.33 _reflns_number_total 7143 _reflns_number_gt 5759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SHELTXL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELTXL' _computing_publication_material 'Bruker SHELTXL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7143 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Fe1 Fe 0.669100(19) -0.28469(2) 0.315047(19) 0.02850(8) Uani 1 1 d . . . Cl1 Cl 0.67513(4) -0.29605(4) 0.46436(4) 0.04016(13) Uani 1 1 d . . . Cl2 Cl 0.65255(4) -0.43262(4) 0.26065(4) 0.04469(14) Uani 1 1 d . . . Cl3 Cl 0.79341(4) -0.21469(5) 0.26739(4) 0.05138(17) Uani 1 1 d . . . Cl4 Cl 0.55291(4) -0.19127(4) 0.27327(4) 0.04165(14) Uani 1 1 d . . . Fe2 Fe 0.828677(19) 0.21276(2) -0.372496(19) 0.02760(8) Uani 1 1 d . . . Cl5 Cl 0.71605(4) 0.13114(4) -0.31461(4) 0.04097(14) Uani 1 1 d . . . Cl6 Cl 0.82950(4) 0.36088(4) -0.31609(3) 0.03670(13) Uani 1 1 d . . . Cl7 Cl 0.96068(4) 0.14289(4) -0.33575(4) 0.03906(13) Uani 1 1 d . . . Cl8 Cl 0.80944(4) 0.22660(4) -0.52147(3) 0.03674(13) Uani 1 1 d . . . Cl9 Cl 0.53703(3) 0.06678(4) 0.38078(3) 0.03179(12) Uani 1 1 d . . . N11 N 0.59281(11) 0.03147(13) 0.17949(11) 0.0305(4) Uani 1 1 d . . . H11 H 0.5866 0.0154 0.2370 0.037 Uiso 1 1 calc R . . C12 C 0.55858(14) 0.11614(16) 0.14965(14) 0.0342(5) Uani 1 1 d . . . H12 H 0.5291 0.1585 0.1905 0.041 Uiso 1 1 calc R . . C13 C 0.56593(15) 0.14226(16) 0.05976(15) 0.0366(5) Uani 1 1 d . . . H13 H 0.5410 0.2020 0.0375 0.044 Uiso 1 1 calc R . . C14 C 0.61040(13) 0.07972(15) 0.00235(13) 0.0295(4) Uani 1 1 d . . . Cl14 Cl 0.62143(4) 0.11015(4) -0.10984(3) 0.04240(14) Uani 1 1 d . . . C15 C 0.64599(14) -0.00760(15) 0.03473(14) 0.0323(4) Uani 1 1 d . . . H15 H 0.6763 -0.0509 -0.0046 0.039 Uiso 1 1 calc R . . C16 C 0.63638(15) -0.03009(16) 0.12494(14) 0.0356(5) Uani 1 1 d . . . H16 H 0.6606 -0.0895 0.1489 0.043 Uiso 1 1 calc R . . N21 N 0.68639(11) -0.03959(13) 0.50295(12) 0.0344(4) Uani 1 1 d . . . H21 H 0.6306 -0.0213 0.4850 0.041 Uiso 1 1 calc R . . C22 C 0.75563(15) -0.02133(17) 0.44872(15) 0.0382(5) Uani 1 1 d . . . H22 H 0.7441 0.0107 0.3919 0.046 Uiso 1 1 calc R . . C23 C 0.84319(14) -0.04860(16) 0.47472(15) 0.0369(5) Uani 1 1 d . . . H23 H 0.8931 -0.0359 0.4367 0.044 Uiso 1 1 calc R . . C24 C 0.85714(13) -0.09498(15) 0.55763(14) 0.0303(4) Uani 1 1 d . . . Cl24 Cl 0.96619(4) -0.12893(4) 0.59385(4) 0.04449(15) Uani 1 1 d . . . C25 C 0.78442(14) -0.11373(17) 0.61251(14) 0.0363(5) Uani 1 1 d . . . H25 H 0.7940 -0.1463 0.6693 0.044 Uiso 1 1 calc R . . C26 C 0.69807(14) -0.08445(17) 0.58337(15) 0.0374(5) Uani 1 1 d . . . H26 H 0.6469 -0.0960 0.6201 0.045 Uiso 1 1 calc R . . N31 N 0.56921(11) 0.27677(14) 0.44866(12) 0.0341(4) Uani 1 1 d . . . H31 H 0.5584 0.2285 0.4102 0.041 Uiso 1 1 calc R . . C32 C 0.56898(14) 0.25866(17) 0.53834(15) 0.0354(5) Uani 1 1 d . . . H32 H 0.5567 0.1947 0.5594 0.042 Uiso 1 1 calc R . . C33 C 0.58643(14) 0.33195(16) 0.59988(15) 0.0356(5) Uani 1 1 d . . . H33 H 0.5863 0.3197 0.6637 0.043 Uiso 1 1 calc R . . C34 C 0.60416(13) 0.42405(16) 0.56726(14) 0.0323(4) Uani 1 1 d . . . Cl34 Cl 0.62642(4) 0.51652(4) 0.64307(4) 0.04497(14) Uani 1 1 d . . . C35 C 0.60330(15) 0.44154(17) 0.47367(15) 0.0368(5) Uani 1 1 d . . . H35 H 0.6150 0.5048 0.4507 0.044 Uiso 1 1 calc R . . C36 C 0.58512(15) 0.36516(17) 0.41541(15) 0.0382(5) Uani 1 1 d . . . H36 H 0.5839 0.3753 0.3512 0.046 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.02927(15) 0.03059(16) 0.02543(15) 0.00262(12) -0.00146(11) 0.00017(12) Cl1 0.0535(3) 0.0410(3) 0.0255(2) -0.0007(2) -0.0044(2) 0.0002(2) Cl2 0.0668(4) 0.0355(3) 0.0315(3) -0.0039(2) -0.0019(3) 0.0022(3) Cl3 0.0337(3) 0.0699(4) 0.0506(3) 0.0169(3) 0.0016(3) -0.0097(3) Cl4 0.0353(3) 0.0426(3) 0.0472(3) 0.0182(3) 0.0033(2) 0.0063(2) Fe2 0.02901(15) 0.03102(16) 0.02289(14) 0.00178(12) 0.00236(11) 0.00007(12) Cl5 0.0374(3) 0.0471(3) 0.0387(3) 0.0102(2) 0.0056(2) -0.0070(2) Cl6 0.0435(3) 0.0360(3) 0.0309(2) -0.0056(2) 0.0050(2) 0.0005(2) Cl7 0.0332(3) 0.0406(3) 0.0434(3) 0.0084(2) 0.0006(2) 0.0045(2) Cl8 0.0452(3) 0.0422(3) 0.0229(2) -0.0005(2) 0.0018(2) 0.0018(2) Cl9 0.0322(2) 0.0390(3) 0.0240(2) -0.0009(2) -0.00080(18) 0.0047(2) N11 0.0306(8) 0.0388(10) 0.0222(8) 0.0027(7) 0.0024(7) -0.0018(8) C12 0.0320(10) 0.0412(12) 0.0295(10) -0.0054(10) 0.0015(8) 0.0030(9) C13 0.0411(12) 0.0374(12) 0.0314(10) 0.0037(10) 0.0019(9) 0.0095(10) C14 0.0302(9) 0.0356(11) 0.0224(9) 0.0012(8) -0.0023(8) -0.0023(9) Cl14 0.0582(3) 0.0467(3) 0.0223(2) 0.0056(2) 0.0016(2) 0.0080(3) C15 0.0364(10) 0.0314(10) 0.0292(10) -0.0006(9) 0.0041(9) 0.0029(9) C16 0.0412(11) 0.0334(11) 0.0325(11) 0.0059(9) 0.0035(9) 0.0030(9) N21 0.0284(8) 0.0360(10) 0.0382(10) -0.0071(8) -0.0053(7) 0.0053(7) C22 0.0430(12) 0.0394(12) 0.0318(10) 0.0049(10) -0.0029(9) -0.0004(10) C23 0.0331(10) 0.0403(12) 0.0378(11) 0.0052(10) 0.0064(9) -0.0018(9) C24 0.0253(9) 0.0323(10) 0.0329(10) -0.0041(9) -0.0031(8) 0.0013(8) Cl24 0.0281(2) 0.0454(3) 0.0591(4) 0.0000(3) -0.0084(2) 0.0047(2) C25 0.0349(11) 0.0465(13) 0.0271(10) 0.0006(10) -0.0020(8) 0.0007(10) C26 0.0298(10) 0.0496(14) 0.0331(11) -0.0019(10) 0.0038(9) 0.0005(10) N31 0.0303(9) 0.0396(10) 0.0324(9) -0.0085(8) -0.0008(7) 0.0040(8) C32 0.0329(10) 0.0376(11) 0.0357(11) 0.0025(10) 0.0005(9) -0.0028(9) C33 0.0327(10) 0.0452(13) 0.0287(10) 0.0012(10) 0.0003(8) -0.0023(10) C34 0.0253(9) 0.0403(12) 0.0312(10) -0.0053(9) 0.0000(8) 0.0028(9) Cl34 0.0525(3) 0.0414(3) 0.0405(3) -0.0107(3) -0.0050(3) 0.0008(3) C35 0.0424(12) 0.0353(11) 0.0332(11) 0.0027(10) 0.0067(9) 0.0056(10) C36 0.0403(11) 0.0466(13) 0.0280(10) 0.0001(10) 0.0064(9) 0.0091(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 Cl3 2.1885(6) . ? Fe1 Cl4 2.1895(6) . ? Fe1 Cl1 2.1917(6) . ? Fe1 Cl2 2.1924(6) . ? Fe2 Cl5 2.1860(6) . ? Fe2 Cl7 2.1942(6) . ? Fe2 Cl6 2.1960(6) . ? Fe2 Cl8 2.1977(6) . ? N11 C12 1.332(3) . ? N11 C16 1.341(3) . ? C12 C13 1.374(3) . ? C13 C14 1.382(3) . ? C14 C15 1.383(3) . ? C14 Cl14 1.710(2) . ? C15 C16 1.370(3) . ? N21 C22 1.333(3) . ? N21 C26 1.334(3) . ? C22 C23 1.367(3) . ? C23 C24 1.379(3) . ? C24 C25 1.380(3) . ? C24 Cl24 1.7168(19) . ? C25 C26 1.371(3) . ? N31 C36 1.332(3) . ? N31 C32 1.338(3) . ? C32 C33 1.368(3) . ? C33 C34 1.381(3) . ? C34 C35 1.392(3) . ? C34 Cl34 1.709(2) . ? C35 C36 1.371(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl3 Fe1 Cl4 106.99(3) . . ? Cl3 Fe1 Cl1 110.53(3) . . ? Cl4 Fe1 Cl1 108.61(2) . . ? Cl3 Fe1 Cl2 111.77(3) . . ? Cl4 Fe1 Cl2 111.70(3) . . ? Cl1 Fe1 Cl2 107.23(2) . . ? Cl5 Fe2 Cl7 110.08(2) . . ? Cl5 Fe2 Cl6 108.76(2) . . ? Cl7 Fe2 Cl6 108.78(2) . . ? Cl5 Fe2 Cl8 111.30(2) . . ? Cl7 Fe2 Cl8 110.83(2) . . ? Cl6 Fe2 Cl8 106.99(2) . . ? C12 N11 C16 122.32(18) . . ? N11 C12 C13 120.0(2) . . ? C12 C13 C14 118.6(2) . . ? C13 C14 C15 120.57(19) . . ? C13 C14 Cl14 119.89(16) . . ? C15 C14 Cl14 119.55(16) . . ? C16 C15 C14 118.35(19) . . ? N11 C16 C15 120.2(2) . . ? C22 N21 C26 122.81(18) . . ? N21 C22 C23 120.1(2) . . ? C22 C23 C24 118.3(2) . . ? C23 C24 C25 120.75(19) . . ? C23 C24 Cl24 119.87(16) . . ? C25 C24 Cl24 119.38(16) . . ? C26 C25 C24 118.6(2) . . ? N21 C26 C25 119.5(2) . . ? C36 N31 C32 122.4(2) . . ? N31 C32 C33 120.2(2) . . ? C32 C33 C34 118.6(2) . . ? C33 C34 C35 120.3(2) . . ? C33 C34 Cl34 119.28(17) . . ? C35 C34 Cl34 120.38(18) . . ? C36 C35 C34 118.4(2) . . ? N31 C36 C35 120.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 1.1(3) . . . . ? N11 C12 C13 C14 -0.9(3) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C12 C13 C14 Cl14 -179.63(17) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? Cl14 C14 C15 C16 179.86(17) . . . . ? C12 N11 C16 C15 -0.9(3) . . . . ? C14 C15 C16 N11 0.5(3) . . . . ? C26 N21 C22 C23 -0.2(3) . . . . ? N21 C22 C23 C24 0.1(3) . . . . ? C22 C23 C24 C25 0.3(3) . . . . ? C22 C23 C24 Cl24 -179.04(17) . . . . ? C23 C24 C25 C26 -0.6(3) . . . . ? Cl24 C24 C25 C26 178.75(17) . . . . ? C22 N21 C26 C25 -0.1(3) . . . . ? C24 C25 C26 N21 0.5(3) . . . . ? C36 N31 C32 C33 -0.7(3) . . . . ? N31 C32 C33 C34 -0.1(3) . . . . ? C32 C33 C34 C35 0.6(3) . . . . ? C32 C33 C34 Cl34 -179.83(16) . . . . ? C33 C34 C35 C36 -0.4(3) . . . . ? Cl34 C34 C35 C36 -179.99(16) . . . . ? C32 N31 C36 C35 0.9(3) . . . . ? C34 C35 C36 N31 -0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.977 # 99.9% completeness to theta 26.37 degrees _refine_diff_density_max 0.585 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.078 data_ilb18m _database_code_depnum_ccdc_archive 'CCDC 266456' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(c5 h5 br n), 2(cl4 Fe), Cl' _chemical_formula_sum 'C15 H15 Br3 Cl9 Fe2 N3' _chemical_formula_weight 907.78 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 Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.583(11) _cell_length_b 13.960(10) _cell_length_c 14.695(11) _cell_angle_alpha 90.00 _cell_angle_beta 91.716(14) _cell_angle_gamma 90.00 _cell_volume 2990(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3908 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 26.29 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.016 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 5.795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1757 _exptl_absorpt_correction_T_max 0.2585 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 1000 CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18984 _diffrn_reflns_av_R_equivalents 0.1409 _diffrn_reflns_av_sigmaI/netI 0.1412 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.64 _reflns_number_total 7323 _reflns_number_gt 3550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1001P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7323 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1413 _refine_ls_R_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.2075 _refine_ls_wR_factor_gt 0.1691 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Fe1 Fe 0.82125(8) 0.28154(9) 0.67461(8) 0.0376(3) Uani 1 1 d . . . Fe2 Fe 0.88270(8) 0.21401(9) 0.17264(8) 0.0356(3) Uani 1 1 d . . . Cl1 Cl 0.77666(18) 0.2132(2) 0.79908(16) 0.0646(8) Uani 1 1 d . . . Cl2 Cl 0.78292(16) 0.18656(18) 0.56182(14) 0.0529(6) Uani 1 1 d . . . Cl3 Cl 0.76226(15) 0.42479(18) 0.65700(17) 0.0535(6) Uani 1 1 d . . . Cl4 Cl 0.96995(14) 0.29815(18) 0.67773(16) 0.0529(6) Uani 1 1 d . . . Cl5 Cl 0.82825(15) 0.13075(18) 0.28423(15) 0.0494(6) Uani 1 1 d . . . Cl6 Cl 0.84656(16) 0.14638(18) 0.04220(15) 0.0494(6) Uani 1 1 d . . . Cl7 Cl 0.82134(15) 0.35657(17) 0.17348(15) 0.0473(6) Uani 1 1 d . . . Cl8 Cl 1.03106(14) 0.23146(17) 0.18987(15) 0.0470(6) Uani 1 1 d . . . Cl9 Cl 0.38192(13) 0.57331(16) 0.04083(13) 0.0402(5) Uani 1 1 d . . . N31 N 0.1797(5) 0.5361(5) 0.0918(4) 0.0406(17) Uani 1 1 d . . . H31 H 0.2383 0.5226 0.0862 0.049 Uiso 1 1 calc R . . C32 C 0.1274(6) 0.4741(6) 0.1366(6) 0.040(2) Uani 1 1 d . . . H32 H 0.1530 0.4171 0.1619 0.048 Uiso 1 1 calc R . . C33 C 0.0378(5) 0.4943(6) 0.1449(5) 0.0385(19) Uani 1 1 d . . . H33 H -0.0007 0.4509 0.1758 0.046 Uiso 1 1 calc R . . C34 C 0.0019(5) 0.5768(6) 0.1093(5) 0.0326(18) Uani 1 1 d . . . Br34 Br -0.12177(6) 0.60697(7) 0.12263(6) 0.0480(3) Uani 1 1 d . . . C35 C 0.0568(6) 0.6397(7) 0.0633(6) 0.047(2) Uani 1 1 d . . . H35 H 0.0327 0.6972 0.0378 0.056 Uiso 1 1 calc R . . C36 C 0.1479(6) 0.6160(7) 0.0558(5) 0.042(2) Uani 1 1 d . . . H36 H 0.1878 0.6575 0.0244 0.050 Uiso 1 1 calc R . . N11 N 0.4466(5) 0.7806(6) 0.0740(4) 0.0426(18) Uani 1 1 d . . . H11 H 0.4065 0.7341 0.0653 0.051 Uiso 1 1 calc R . . C12 C 0.4170(6) 0.8684(7) 0.0923(6) 0.050(2) Uani 1 1 d . . . H12 H 0.3530 0.8802 0.0957 0.060 Uiso 1 1 calc R . . C13 C 0.4778(6) 0.9417(8) 0.1061(6) 0.050(2) Uani 1 1 d . . . H13 H 0.4571 1.0048 0.1184 0.059 Uiso 1 1 calc R . . C14 C 0.5698(5) 0.9216(6) 0.1018(5) 0.0354(18) Uani 1 1 d . . . Br14 Br 0.65704(6) 1.01802(8) 0.11914(7) 0.0538(3) Uani 1 1 d . . . C15 C 0.5989(6) 0.8320(7) 0.0814(6) 0.048(2) Uani 1 1 d . . . H15 H 0.6624 0.8185 0.0760 0.058 Uiso 1 1 calc R . . C16 C 0.5344(7) 0.7619(7) 0.0687(6) 0.049(2) Uani 1 1 d . . . H16 H 0.5536 0.6984 0.0558 0.058 Uiso 1 1 calc R . . N21 N 0.5015(5) 0.4611(5) 0.1840(4) 0.0438(18) Uani 1 1 d . . . H21 H 0.4816 0.4784 0.1293 0.053 Uiso 1 1 calc R . . C22 C 0.5807(6) 0.4150(7) 0.1923(6) 0.048(2) Uani 1 1 d . . . H22 H 0.6161 0.4025 0.1404 0.057 Uiso 1 1 calc R . . C23 C 0.6110(6) 0.3857(6) 0.2771(6) 0.044(2) Uani 1 1 d . . . H23 H 0.6661 0.3499 0.2842 0.053 Uiso 1 1 calc R . . C24 C 0.5612(5) 0.4083(6) 0.3511(5) 0.0319(18) Uani 1 1 d . . . Br24 Br 0.60462(7) 0.37148(7) 0.46750(6) 0.0488(3) Uani 1 1 d . . . C26 C 0.4504(7) 0.4823(7) 0.2556(6) 0.050(2) Uani 1 1 d . . . H26 H 0.3939 0.5153 0.2468 0.060 Uiso 1 1 calc R . . C25 C 0.4795(6) 0.4565(6) 0.3408(5) 0.040(2) Uani 1 1 d . . . H25 H 0.4441 0.4714 0.3921 0.049 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0300(6) 0.0454(8) 0.0369(6) 0.0003(5) -0.0065(5) -0.0038(6) Fe2 0.0259(6) 0.0420(7) 0.0386(6) 0.0006(5) -0.0008(5) -0.0026(5) Cl1 0.0576(15) 0.093(2) 0.0428(12) 0.0149(13) -0.0032(10) -0.0170(15) Cl2 0.0551(14) 0.0602(15) 0.0431(12) -0.0059(11) -0.0029(10) -0.0238(13) Cl3 0.0357(12) 0.0552(15) 0.0690(15) -0.0017(12) -0.0097(10) 0.0049(11) Cl4 0.0296(11) 0.0607(16) 0.0677(15) -0.0026(12) -0.0133(10) -0.0011(11) Cl5 0.0385(12) 0.0628(15) 0.0470(12) 0.0104(11) 0.0028(9) -0.0082(11) Cl6 0.0480(13) 0.0558(15) 0.0441(12) -0.0045(10) -0.0038(9) -0.0122(12) Cl7 0.0342(12) 0.0533(14) 0.0546(13) -0.0009(11) 0.0017(9) 0.0070(11) Cl8 0.0273(11) 0.0612(15) 0.0521(12) -0.0017(11) -0.0041(8) -0.0035(10) Cl9 0.0274(10) 0.0533(14) 0.0393(10) 0.0034(10) -0.0047(8) -0.0018(10) N31 0.028(4) 0.057(5) 0.036(4) -0.006(3) -0.002(3) 0.006(4) C32 0.036(5) 0.032(5) 0.050(5) 0.002(4) -0.005(4) -0.001(4) C33 0.029(4) 0.043(5) 0.043(4) 0.002(4) 0.001(3) -0.002(4) C34 0.022(4) 0.046(5) 0.030(4) -0.003(4) -0.007(3) -0.002(4) Br34 0.0251(4) 0.0568(6) 0.0615(6) 0.0066(5) -0.0057(4) 0.0031(4) C35 0.030(5) 0.049(6) 0.061(6) 0.008(5) -0.005(4) 0.004(4) C36 0.035(5) 0.056(6) 0.035(4) 0.009(4) -0.002(3) 0.001(4) N11 0.037(4) 0.049(5) 0.041(4) 0.008(3) -0.006(3) -0.008(4) C12 0.033(5) 0.053(6) 0.064(6) 0.016(5) -0.005(4) 0.003(5) C13 0.048(6) 0.055(6) 0.045(5) 0.004(5) 0.002(4) 0.002(5) C14 0.035(5) 0.037(5) 0.034(4) 0.000(4) -0.003(3) 0.001(4) Br14 0.0405(5) 0.0576(7) 0.0627(6) -0.0019(5) -0.0106(4) -0.0085(5) C15 0.031(5) 0.065(7) 0.049(5) -0.011(5) -0.005(4) -0.010(5) C16 0.050(6) 0.049(6) 0.046(5) -0.005(4) -0.007(4) 0.004(5) N21 0.048(5) 0.056(5) 0.026(3) 0.008(3) -0.012(3) -0.008(4) C22 0.036(5) 0.071(7) 0.036(4) 0.002(5) -0.001(4) -0.012(5) C23 0.036(5) 0.054(6) 0.042(5) -0.002(4) -0.002(4) 0.002(4) C24 0.030(4) 0.039(5) 0.026(4) -0.004(3) -0.006(3) -0.004(4) Br24 0.0547(6) 0.0573(6) 0.0338(4) 0.0034(4) -0.0096(4) 0.0019(5) C26 0.049(6) 0.052(6) 0.047(5) 0.003(4) -0.011(4) 0.008(5) C25 0.040(5) 0.045(5) 0.037(4) -0.002(4) 0.007(4) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 Cl1 2.180(3) . ? Fe1 Cl4 2.180(3) . ? Fe1 Cl2 2.182(3) . ? Fe1 Cl3 2.189(3) . ? Fe2 Cl5 2.179(3) . ? Fe2 Cl7 2.182(3) . ? Fe2 Cl8 2.184(3) . ? Fe2 Cl6 2.187(3) . ? N31 C36 1.314(11) . ? N31 C32 1.340(11) . ? C32 C33 1.346(11) . ? C33 C34 1.363(12) . ? C34 C35 1.379(12) . ? C34 Br34 1.868(8) . ? C35 C36 1.376(12) . ? N11 C16 1.311(11) . ? N11 C12 1.330(12) . ? C12 C13 1.366(13) . ? C13 C14 1.374(12) . ? C14 C15 1.357(12) . ? C14 Br14 1.864(8) . ? C15 C16 1.367(12) . ? N21 C22 1.325(11) . ? N21 C26 1.341(11) . ? C22 C23 1.372(11) . ? C23 C24 1.363(11) . ? C24 C25 1.372(11) . ? C24 Br24 1.878(7) . ? C26 C25 1.359(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Fe1 Cl4 110.52(10) . . ? Cl1 Fe1 Cl2 107.18(12) . . ? Cl4 Fe1 Cl2 108.22(11) . . ? Cl1 Fe1 Cl3 111.90(12) . . ? Cl4 Fe1 Cl3 107.00(11) . . ? Cl2 Fe1 Cl3 111.99(11) . . ? Cl5 Fe2 Cl7 108.87(11) . . ? Cl5 Fe2 Cl8 110.74(10) . . ? Cl7 Fe2 Cl8 107.61(11) . . ? Cl5 Fe2 Cl6 110.22(11) . . ? Cl7 Fe2 Cl6 108.10(10) . . ? Cl8 Fe2 Cl6 111.20(10) . . ? C36 N31 C32 123.1(8) . . ? N31 C32 C33 118.6(8) . . ? C32 C33 C34 120.3(8) . . ? C33 C34 C35 120.3(7) . . ? C33 C34 Br34 120.7(6) . . ? C35 C34 Br34 119.0(6) . . ? C36 C35 C34 117.6(8) . . ? N31 C36 C35 120.1(9) . . ? C16 N11 C12 121.3(8) . . ? N11 C12 C13 120.5(9) . . ? C12 C13 C14 118.1(9) . . ? C15 C14 C13 120.7(8) . . ? C15 C14 Br14 118.6(6) . . ? C13 C14 Br14 120.6(7) . . ? C14 C15 C16 118.1(9) . . ? N11 C16 C15 121.2(9) . . ? C22 N21 C26 122.6(7) . . ? N21 C22 C23 119.0(8) . . ? C24 C23 C22 119.4(8) . . ? C23 C24 C25 120.5(7) . . ? C23 C24 Br24 119.3(6) . . ? C25 C24 Br24 120.2(6) . . ? N21 C26 C25 119.9(9) . . ? C26 C25 C24 118.6(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C36 N31 C32 C33 0.3(12) . . . . ? N31 C32 C33 C34 -0.8(12) . . . . ? C32 C33 C34 C35 0.9(12) . . . . ? C32 C33 C34 Br34 -178.6(6) . . . . ? C33 C34 C35 C36 -0.4(13) . . . . ? Br34 C34 C35 C36 179.1(6) . . . . ? C32 N31 C36 C35 0.2(12) . . . . ? C34 C35 C36 N31 -0.1(13) . . . . ? C16 N11 C12 C13 -0.1(13) . . . . ? N11 C12 C13 C14 -0.9(13) . . . . ? C12 C13 C14 C15 2.1(12) . . . . ? C12 C13 C14 Br14 179.6(6) . . . . ? C13 C14 C15 C16 -2.5(13) . . . . ? Br14 C14 C15 C16 -180.0(6) . . . . ? C12 N11 C16 C15 -0.3(13) . . . . ? C14 C15 C16 N11 1.5(13) . . . . ? C26 N21 C22 C23 1.6(13) . . . . ? N21 C22 C23 C24 -3.0(13) . . . . ? C22 C23 C24 C25 2.7(13) . . . . ? C22 C23 C24 Br24 -178.1(7) . . . . ? C22 N21 C26 C25 0.1(14) . . . . ? N21 C26 C25 C24 -0.4(14) . . . . ? C23 C24 C25 C26 -1.1(13) . . . . ? Br24 C24 C25 C26 179.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 28.64 _diffrn_measured_fraction_theta_full 0.952 # 99.5% completeness to theta 26.37 degrees _refine_diff_density_max 1.817 _refine_diff_density_min -1.678 _refine_diff_density_rms 0.193 data_ilb388m _database_code_depnum_ccdc_archive 'CCDC 266457' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C5 H5 Cl N), Cl6 Pt, Cl' _chemical_formula_sum 'C15 H15 Cl10 N3 Pt' _chemical_formula_weight 786.91 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 Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.894(2) _cell_length_b 21.852(4) _cell_length_c 11.640(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.807(3) _cell_angle_gamma 90.00 _cell_volume 2486.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11669 _cell_measurement_theta_min 2.685 _cell_measurement_theta_max 27.813 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.102 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 6.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2221 _exptl_absorpt_correction_T_max 0.6884 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 1000 CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28134 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.91 _reflns_number_total 5783 _reflns_number_gt 4875 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+18.9668P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5783 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Pt1 Pt 0.23725(3) 0.240488(12) 0.46530(2) 0.01975(11) Uani 1 1 d . . . Cl1 Cl 0.09945(16) 0.16290(8) 0.36432(14) 0.0214(3) Uani 1 1 d . . . Cl2 Cl 0.40033(15) 0.22755(7) 0.33855(13) 0.0169(3) Uani 1 1 d . . . Cl3 Cl 0.37447(16) 0.31549(8) 0.57092(14) 0.0220(3) Uani 1 1 d . . . Cl4 Cl 0.07280(16) 0.25327(7) 0.59262(13) 0.0167(3) Uani 1 1 d . . . Cl5 Cl 0.34734(15) 0.16126(7) 0.58626(13) 0.0191(3) Uani 1 1 d . . . Cl6 Cl 0.12666(16) 0.31761(7) 0.34256(13) 0.0203(3) Uani 1 1 d . . . N1 N 0.2295(5) 0.3113(3) 0.9636(5) 0.0230(13) Uani 1 1 d . . . H1 H 0.2235 0.3515 0.9663 0.028 Uiso 1 1 calc R . . C2 C 0.1955(7) 0.2795(4) 1.0520(6) 0.0246(15) Uani 1 1 d . . . H2 H 0.1649 0.3001 1.1153 0.030 Uiso 1 1 calc R . . C3 C 0.2048(6) 0.2164(3) 1.0517(6) 0.0197(13) Uani 1 1 d . . . H3 H 0.1819 0.1926 1.1141 0.024 Uiso 1 1 calc R . . C4 C 0.2488(6) 0.1897(3) 0.9568(5) 0.0160(12) Uani 1 1 d . . . Cl01 Cl 0.2641(2) 0.11074(8) 0.95329(17) 0.0305(4) Uani 1 1 d . . . C5 C 0.2832(6) 0.2234(3) 0.8655(5) 0.0186(13) Uani 1 1 d . . . H5 H 0.3135 0.2040 0.8010 0.022 Uiso 1 1 calc R . . C6 C 0.2721(7) 0.2864(3) 0.8712(6) 0.0200(13) Uani 1 1 d . . . H6 H 0.2945 0.3114 0.8101 0.024 Uiso 1 1 calc R . . N11 N -0.0375(6) -0.1147(3) 0.3400(6) 0.0270(13) Uani 1 1 d . . . H11 H -0.0632 -0.1450 0.3815 0.032 Uiso 1 1 calc R . . C12 C -0.0798(8) -0.0583(4) 0.3593(7) 0.0303(16) Uani 1 1 d . . . H12 H -0.1373 -0.0516 0.4164 0.036 Uiso 1 1 calc R . . C13 C -0.0408(7) -0.0099(3) 0.2971(6) 0.0248(14) Uani 1 1 d . . . H13 H -0.0682 0.0307 0.3118 0.030 Uiso 1 1 calc R . . C14 C 0.0393(7) -0.0218(3) 0.2128(6) 0.0225(14) Uani 1 1 d . . . Cl11 Cl 0.0893(2) 0.03768(10) 0.13172(17) 0.0408(5) Uani 1 1 d . . . C15 C 0.0823(7) -0.0808(4) 0.1929(7) 0.0268(15) Uani 1 1 d . . . H15 H 0.1374 -0.0889 0.1346 0.032 Uiso 1 1 calc R . . C16 C 0.0426(8) -0.1272(3) 0.2601(7) 0.0299(16) Uani 1 1 d . . . H16 H 0.0719 -0.1680 0.2500 0.036 Uiso 1 1 calc R . . N21 N 0.3952(6) 0.0154(3) 0.3464(5) 0.0214(12) Uani 1 1 d . . . H21 H 0.3455 0.0080 0.4014 0.026 Uiso 1 1 calc R . . C22 C 0.4526(8) -0.0319(3) 0.2994(6) 0.0263(15) Uani 1 1 d . . . H22 H 0.4391 -0.0723 0.3255 0.032 Uiso 1 1 calc R . . C23 C 0.5301(8) -0.0223(3) 0.2145(7) 0.0299(16) Uani 1 1 d . . . H23 H 0.5703 -0.0557 0.1798 0.036 Uiso 1 1 calc R . . C24 C 0.5494(7) 0.0373(3) 0.1796(6) 0.0235(14) Uani 1 1 d . . . Cl21 Cl 0.6496(3) 0.05163(11) 0.0754(2) 0.0462(5) Uani 1 1 d . . . C25 C 0.4874(7) 0.0850(3) 0.2280(6) 0.0249(14) Uani 1 1 d . . . H25 H 0.4983 0.1258 0.2025 0.030 Uiso 1 1 calc R . . C26 C 0.4097(7) 0.0734(3) 0.3136(7) 0.0265(15) Uani 1 1 d . . . H26 H 0.3672 0.1058 0.3489 0.032 Uiso 1 1 calc R . . Cl Cl 0.24470(17) 0.45017(8) 0.97783(14) 0.0235(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pt1 0.01900(15) 0.02065(17) 0.01970(15) 0.00028(9) 0.00328(10) 0.00120(9) Cl1 0.0169(7) 0.0205(8) 0.0258(8) -0.0074(6) 0.0005(6) -0.0030(6) Cl2 0.0174(7) 0.0169(7) 0.0178(7) 0.0012(5) 0.0071(5) 0.0014(5) Cl3 0.0157(7) 0.0221(8) 0.0278(8) -0.0088(6) 0.0021(6) -0.0016(6) Cl4 0.0156(7) 0.0190(7) 0.0159(7) 0.0021(5) 0.0041(5) 0.0040(5) Cl5 0.0189(7) 0.0220(8) 0.0169(7) 0.0045(6) 0.0042(6) 0.0074(6) Cl6 0.0191(7) 0.0219(8) 0.0203(7) 0.0060(6) 0.0044(6) 0.0050(6) N1 0.019(3) 0.017(3) 0.032(3) -0.008(2) -0.001(2) -0.002(2) C2 0.016(3) 0.033(4) 0.024(3) -0.013(3) 0.001(3) 0.001(3) C3 0.013(3) 0.029(4) 0.017(3) -0.001(3) 0.003(2) 0.001(3) C4 0.009(3) 0.022(3) 0.016(3) -0.002(2) -0.001(2) 0.001(2) Cl01 0.0345(9) 0.0191(9) 0.0383(10) 0.0018(7) 0.0073(8) 0.0031(7) C5 0.014(3) 0.028(4) 0.014(3) -0.003(3) 0.003(2) 0.001(3) C6 0.019(3) 0.020(3) 0.019(3) 0.001(3) -0.001(2) -0.004(3) N11 0.026(3) 0.020(3) 0.037(3) 0.003(3) 0.010(3) -0.005(2) C12 0.031(4) 0.027(4) 0.037(4) -0.001(3) 0.018(3) -0.003(3) C13 0.030(4) 0.016(3) 0.029(4) -0.002(3) 0.005(3) 0.004(3) C14 0.023(3) 0.018(3) 0.026(3) -0.002(3) 0.002(3) -0.005(3) Cl11 0.0569(13) 0.0340(11) 0.0317(10) 0.0061(8) 0.0066(9) -0.0187(9) C15 0.021(3) 0.030(4) 0.031(4) -0.007(3) 0.009(3) 0.000(3) C16 0.030(4) 0.017(4) 0.042(4) -0.008(3) 0.000(3) 0.004(3) N21 0.020(3) 0.021(3) 0.025(3) 0.002(2) 0.008(2) 0.000(2) C22 0.031(4) 0.019(3) 0.031(4) 0.003(3) 0.012(3) -0.003(3) C23 0.038(4) 0.016(3) 0.041(4) -0.005(3) 0.020(3) 0.003(3) C24 0.028(4) 0.021(3) 0.023(3) 0.003(3) 0.008(3) -0.004(3) Cl21 0.0576(13) 0.0433(12) 0.0455(12) 0.0031(10) 0.0326(11) -0.0099(10) C25 0.032(4) 0.018(3) 0.023(3) 0.005(3) 0.000(3) -0.001(3) C26 0.027(4) 0.022(4) 0.031(4) -0.001(3) 0.008(3) 0.003(3) Cl 0.0281(8) 0.0168(8) 0.0276(8) -0.0010(6) 0.0103(7) -0.0016(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pt1 Cl3 2.3515(16) . ? Pt1 Cl2 2.3641(15) . ? Pt1 Cl6 2.3663(16) . ? Pt1 Cl1 2.3715(16) . ? Pt1 Cl4 2.3790(15) . ? Pt1 Cl5 2.3867(15) . ? N1 C2 1.327(10) . ? N1 C6 1.330(9) . ? N1 H1 0.8800 . ? C2 C3 1.382(11) . ? C2 H2 0.9500 . ? C3 C4 1.377(9) . ? C3 H3 0.9500 . ? C4 C5 1.377(9) . ? C4 Cl01 1.734(7) . ? C5 C6 1.384(10) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? N11 C12 1.333(10) . ? N11 C16 1.339(10) . ? N11 H11 0.8800 . ? C12 C13 1.369(10) . ? C12 H12 0.9500 . ? C13 C14 1.377(10) . ? C13 H13 0.9500 . ? C14 C15 1.389(10) . ? C14 Cl11 1.723(7) . ? C15 C16 1.374(11) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N21 C22 1.335(9) . ? N21 C26 1.338(9) . ? N21 H21 0.8800 . ? C22 C23 1.357(10) . ? C22 H22 0.9500 . ? C23 C24 1.387(10) . ? C23 H23 0.9500 . ? C24 C25 1.374(10) . ? C24 Cl21 1.708(7) . ? C25 C26 1.372(10) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl3 Pt1 Cl2 90.86(6) . . ? Cl3 Pt1 Cl6 89.76(6) . . ? Cl2 Pt1 Cl6 90.29(5) . . ? Cl3 Pt1 Cl1 178.15(6) . . ? Cl2 Pt1 Cl1 90.04(6) . . ? Cl6 Pt1 Cl1 91.85(6) . . ? Cl3 Pt1 Cl4 89.29(6) . . ? Cl2 Pt1 Cl4 179.85(6) . . ? Cl6 Pt1 Cl4 89.73(5) . . ? Cl1 Pt1 Cl4 89.81(6) . . ? Cl3 Pt1 Cl5 91.28(6) . . ? Cl2 Pt1 Cl5 89.31(5) . . ? Cl6 Pt1 Cl5 178.89(6) . . ? Cl1 Pt1 Cl5 87.11(6) . . ? Cl4 Pt1 Cl5 90.66(5) . . ? C2 N1 C6 124.2(7) . . ? C2 N1 H1 117.9 . . ? C6 N1 H1 117.9 . . ? N1 C2 C3 119.7(6) . . ? N1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 117.1(6) . . ? C4 C3 H3 121.5 . . ? C2 C3 H3 121.5 . . ? C5 C4 C3 122.6(7) . . ? C5 C4 Cl01 118.7(5) . . ? C3 C4 Cl01 118.7(5) . . ? C4 C5 C6 117.6(6) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? N1 C6 C5 118.9(6) . . ? N1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C12 N11 C16 122.6(7) . . ? C12 N11 H11 118.7 . . ? C16 N11 H11 118.7 . . ? N11 C12 C13 120.3(7) . . ? N11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 118.1(7) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? C13 C14 C15 121.2(7) . . ? C13 C14 Cl11 119.5(6) . . ? C15 C14 Cl11 119.2(6) . . ? C16 C15 C14 117.9(7) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? N11 C16 C15 119.8(7) . . ? N11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C22 N21 C26 123.0(6) . . ? C22 N21 H21 118.5 . . ? C26 N21 H21 118.5 . . ? N21 C22 C23 120.2(7) . . ? N21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C24 118.4(7) . . ? C22 C23 H23 120.8 . . ? C24 C23 H23 120.8 . . ? C25 C24 C23 120.2(6) . . ? C25 C24 Cl21 119.7(5) . . ? C23 C24 Cl21 120.0(6) . . ? C26 C25 C24 119.4(7) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? N21 C26 C25 118.7(7) . . ? N21 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.973 # 99.4% completeness to theta 26.37 degrees _refine_diff_density_max 1.733 _refine_diff_density_min -0.952 _refine_diff_density_rms 0.234