# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Mark Turnbull' _publ_contact_author_email MTURNBULL@CLARKU.EDU _publ_section_title ; Transition metal complexes of 2-amino-3,5-dihalopyridines: Syntheses, structures and magnetic properties of (3,5-diCAPH)2CuX4 and (3,5-diBAPH)2CuX4. ; loop_ _publ_author_name 'Mark Turnbull' 'Bruce Foxman' 'Christopher Landee' 'Grant W. Tremelling' 'Roger Willett' # Attachment '1.CIF' data_gwt2 _database_code_depnum_ccdc_archive 'CCDC 727538' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-amino-3,5-dichloropyridinium) tetrachlorocuprate ; _chemical_name_common 'bis(2-amino-3,5-dichloropyridinium) tetrachlorocuprate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl8 Cu N4' _chemical_formula_weight 533.36 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2075(15) _cell_length_b 9.2718(16) _cell_length_c 13.0297(18) _cell_angle_alpha 94.383(12) _cell_angle_beta 96.358(13) _cell_angle_gamma 106.088(18) _cell_volume 940.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 5.04 _cell_measurement_theta_max 12.46 _exptl_crystal_description platelet _exptl_crystal_colour green _exptl_crystal_size_max .5 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 526 _exptl_absorpt_coefficient_mu 2.297 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6177 _exptl_absorpt_correction_T_max 0.7005 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2782 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 21.95 _reflns_number_total 2225 _reflns_number_gt 1842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0675P)^2^+1.0268P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0015(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2225 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Cu Cu 0.32191(7) 0.46866(7) 0.27331(4) 0.0368(3) Uani 1 1 d . . . Cl1 Cl 0.28799(17) 0.59250(19) 0.13497(11) 0.0597(5) Uani 1 1 d . . . Cl2 Cl 0.05858(17) 0.47009(17) 0.31219(11) 0.0520(4) Uani 1 1 d . . . Cl3 Cl 0.32238(17) 0.27794(17) 0.36880(11) 0.0576(5) Uani 1 1 d . . . Cl4 Cl 0.60752(16) 0.52354(19) 0.26600(11) 0.0597(5) Uani 1 1 d . . . N11 N -0.0187(6) 0.2512(5) 0.4926(3) 0.0421(12) Uani 1 1 d . . . H11 H 0.022(8) 0.298(7) 0.454(5) 0.051 Uiso 1 1 d . . . N12 N -0.2694(7) 0.2988(7) 0.4295(4) 0.0607(16) Uani 1 1 d . . . H12B H -0.361(9) 0.301(8) 0.433(6) 0.073 Uiso 1 1 d . . . H12A H -0.224(9) 0.348(8) 0.392(6) 0.073 Uiso 1 1 d . . . C12 C -0.1827(7) 0.2426(6) 0.4986(4) 0.0405(13) Uani 1 1 d . . . C13 C -0.2553(6) 0.1658(6) 0.5811(4) 0.0405(12) Uani 1 1 d . . . C14 C -0.1605(6) 0.1065(6) 0.6474(4) 0.0407(12) Uani 1 1 d . . . H14 H -0.2092 0.0565 0.7007 0.049 Uiso 1 1 calc R . . C15 C 0.0091(6) 0.1195(6) 0.6369(4) 0.0406(13) Uani 1 1 d . . . C16 C 0.0803(6) 0.1949(6) 0.5592(4) 0.0437(13) Uani 1 1 d . . . H16 H 0.1947 0.2074 0.5521 0.052 Uiso 1 1 calc R . . Cl13 Cl -0.46144(18) 0.1595(2) 0.59669(12) 0.0625(5) Uani 1 1 d . . . Cl15 Cl 0.13168(18) 0.04063(18) 0.71921(11) 0.0561(4) Uani 1 1 d . . . N21 N -0.3363(6) 0.7027(5) 0.0585(3) 0.0443(12) Uani 1 1 d . . . H21A H -0.367(8) 0.658(7) 0.101(5) 0.053 Uiso 1 1 d . . . N22 N -0.0892(8) 0.6407(7) 0.1151(4) 0.0575(15) Uani 1 1 d . . . H22A H 0.020(8) 0.630(7) 0.111(5) 0.069 Uiso 1 1 d . . . H22B H -0.136(10) 0.604(9) 0.142(6) 0.069 Uiso 1 1 d . . . C22 C -0.1745(7) 0.7047(6) 0.0494(4) 0.0382(12) Uani 1 1 d . . . C23 C -0.1022(6) 0.7815(6) -0.0325(4) 0.0392(12) Uani 1 1 d . . . C24 C -0.1948(6) 0.8480(6) -0.0959(4) 0.0412(13) Uani 1 1 d . . . H24A H -0.1464 0.8981 -0.1492 0.049 Uiso 1 1 calc R . . C25 C -0.3613(6) 0.8418(6) -0.0815(4) 0.0430(13) Uani 1 1 d . . . C26 C -0.4303(7) 0.7679(6) -0.0037(4) 0.0448(13) Uani 1 1 d . . . H26A H -0.5421 0.7623 0.0067 0.054 Uiso 1 1 calc R . . Cl23 Cl 0.10335(17) 0.78688(19) -0.04990(11) 0.0593(5) Uani 1 1 d . . . Cl25 Cl -0.4793(2) 0.9295(2) -0.15961(12) 0.0672(5) 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 Cu 0.0352(4) 0.0476(4) 0.0334(4) 0.0208(3) 0.0085(3) 0.0153(3) Cl1 0.0461(8) 0.0922(12) 0.0559(9) 0.0521(8) 0.0167(7) 0.0293(8) Cl2 0.0432(7) 0.0723(10) 0.0562(8) 0.0387(7) 0.0205(6) 0.0286(7) Cl3 0.0504(8) 0.0767(11) 0.0639(9) 0.0496(8) 0.0223(7) 0.0316(7) Cl4 0.0368(7) 0.0873(11) 0.0671(9) 0.0502(8) 0.0149(7) 0.0234(7) N11 0.041(3) 0.057(3) 0.035(2) 0.026(2) 0.011(2) 0.018(2) N12 0.046(3) 0.091(4) 0.057(3) 0.050(3) 0.014(3) 0.027(3) C12 0.040(3) 0.052(3) 0.033(3) 0.016(3) 0.002(2) 0.018(3) C13 0.036(3) 0.054(3) 0.035(3) 0.019(3) 0.009(2) 0.013(2) C14 0.041(3) 0.050(3) 0.037(3) 0.017(2) 0.015(2) 0.016(2) C15 0.042(3) 0.054(3) 0.030(3) 0.019(2) 0.000(2) 0.017(3) C16 0.037(3) 0.057(3) 0.038(3) 0.014(3) 0.006(2) 0.013(3) Cl13 0.0433(8) 0.1009(13) 0.0593(9) 0.0373(9) 0.0195(7) 0.0348(8) Cl15 0.0525(8) 0.0763(10) 0.0501(8) 0.0310(7) 0.0032(6) 0.0311(8) N21 0.043(3) 0.061(3) 0.035(2) 0.028(2) 0.013(2) 0.016(2) N22 0.056(4) 0.082(4) 0.048(3) 0.035(3) 0.016(3) 0.032(3) C22 0.044(3) 0.046(3) 0.029(3) 0.011(2) 0.007(2) 0.017(2) C23 0.041(3) 0.046(3) 0.036(3) 0.015(2) 0.007(2) 0.017(2) C24 0.044(3) 0.050(3) 0.033(3) 0.020(2) 0.014(2) 0.012(3) C25 0.043(3) 0.057(3) 0.039(3) 0.027(3) 0.010(2) 0.022(3) C26 0.045(3) 0.057(4) 0.044(3) 0.021(3) 0.014(3) 0.027(3) Cl23 0.0422(8) 0.0866(11) 0.0616(9) 0.0344(8) 0.0167(7) 0.0282(7) Cl25 0.0642(10) 0.0969(13) 0.0646(10) 0.0465(9) 0.0177(8) 0.0496(9) _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 Cu Cl3 2.2392(14) . ? Cu Cl1 2.2421(14) . ? Cu Cl4 2.2713(15) . ? Cu Cl2 2.2771(15) . ? N11 C12 1.337(7) . ? N11 C16 1.354(7) . ? N11 H11 0.74(6) . ? N12 C12 1.313(7) . ? N12 H12B 0.76(7) . ? N12 H12A 0.75(7) . ? C12 C13 1.428(7) . ? C13 C14 1.348(7) . ? C13 Cl13 1.712(5) . ? C14 C15 1.386(7) . ? C14 H14 0.9300 . ? C15 C16 1.367(7) . ? C15 Cl15 1.728(5) . ? C16 H16 0.9300 . ? N21 C22 1.341(7) . ? N21 C26 1.347(7) . ? N21 H21A 0.74(6) . ? N22 C22 1.323(7) . ? N22 H22A 0.93(7) . ? N22 H22B 0.60(7) . ? C22 C23 1.422(7) . ? C23 C24 1.356(7) . ? C23 Cl23 1.714(5) . ? C24 C25 1.386(7) . ? C24 H24A 0.9300 . ? C25 C26 1.355(7) . ? C25 Cl25 1.726(5) . ? C26 H26A 0.9300 . ? 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 Cu Cl1 160.26(7) . . ? Cl3 Cu Cl4 92.76(5) . . ? Cl1 Cu Cl4 90.67(5) . . ? Cl3 Cu Cl2 91.07(5) . . ? Cl1 Cu Cl2 90.74(5) . . ? Cl4 Cu Cl2 164.57(7) . . ? C12 N11 C16 124.6(5) . . ? C12 N11 H11 116(5) . . ? C16 N11 H11 118(5) . . ? C12 N12 H12B 123(6) . . ? C12 N12 H12A 120(5) . . ? H12B N12 H12A 115(8) . . ? N12 C12 N11 120.3(5) . . ? N12 C12 C13 123.5(5) . . ? N11 C12 C13 116.1(4) . . ? C14 C13 C12 120.5(5) . . ? C14 C13 Cl13 121.3(4) . . ? C12 C13 Cl13 118.2(4) . . ? C13 C14 C15 120.5(5) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 119.3(4) . . ? C16 C15 Cl15 119.3(4) . . ? C14 C15 Cl15 121.3(4) . . ? N11 C16 C15 118.9(5) . . ? N11 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C22 N21 C26 124.4(5) . . ? C22 N21 H21A 111(5) . . ? C26 N21 H21A 125(5) . . ? C22 N22 H22A 126(4) . . ? C22 N22 H22B 111(8) . . ? H22A N22 H22B 121(9) . . ? N22 C22 N21 120.8(5) . . ? N22 C22 C23 123.2(5) . . ? N21 C22 C23 116.0(4) . . ? C24 C23 C22 120.4(5) . . ? C24 C23 Cl23 120.9(4) . . ? C22 C23 Cl23 118.7(4) . . ? C23 C24 C25 120.3(4) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? C26 C25 C24 119.1(5) . . ? C26 C25 Cl25 120.0(4) . . ? C24 C25 Cl25 120.9(4) . . ? N21 C26 C25 119.7(5) . . ? N21 C26 H26A 120.1 . . ? C25 C26 H26A 120.1 . . ? 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 N12 -179.1(6) . . . . ? C16 N11 C12 C13 -1.0(8) . . . . ? N12 C12 C13 C14 177.9(6) . . . . ? N11 C12 C13 C14 -0.1(8) . . . . ? N12 C12 C13 Cl13 -5.3(8) . . . . ? N11 C12 C13 Cl13 176.8(4) . . . . ? C12 C13 C14 C15 0.2(8) . . . . ? Cl13 C13 C14 C15 -176.6(4) . . . . ? C13 C14 C15 C16 0.8(8) . . . . ? C13 C14 C15 Cl15 -178.5(4) . . . . ? C12 N11 C16 C15 2.1(8) . . . . ? C14 C15 C16 N11 -1.9(8) . . . . ? Cl15 C15 C16 N11 177.4(4) . . . . ? C26 N21 C22 N22 178.5(6) . . . . ? C26 N21 C22 C23 -0.2(8) . . . . ? N22 C22 C23 C24 -178.4(5) . . . . ? N21 C22 C23 C24 0.3(8) . . . . ? N22 C22 C23 Cl23 2.1(8) . . . . ? N21 C22 C23 Cl23 -179.2(4) . . . . ? C22 C23 C24 C25 0.0(8) . . . . ? Cl23 C23 C24 C25 179.5(4) . . . . ? C23 C24 C25 C26 -0.3(8) . . . . ? C23 C24 C25 Cl25 178.5(4) . . . . ? C22 N21 C26 C25 -0.1(9) . . . . ? C24 C25 C26 N21 0.3(9) . . . . ? Cl25 C25 C26 N21 -178.5(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 Cl2 0.74(6) 2.52(6) 3.223(4) 160(6) . N11 H11 Cl3 0.74(6) 2.86(6) 3.343(5) 126(6) . N12 H12B Cl3 0.76(7) 2.59(7) 3.304(6) 158(7) 1_455 N12 H12A Cl2 0.75(7) 2.64(7) 3.320(6) 150(7) . N12 H12A Cl4 0.75(7) 2.90(7) 3.357(5) 122(6) 1_455 N21 H21A Cl4 0.74(6) 2.57(7) 3.289(5) 165(6) 1_455 N21 H21A Cl1 0.74(6) 2.82(6) 3.261(5) 121(6) 1_455 N22 H22A Cl1 0.93(7) 2.31(7) 3.234(6) 169(6) . N22 H22B Cl4 0.60(7) 2.77(8) 3.340(5) 159(10) 1_455 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 21.95 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.791 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.102 # Attachment '2.CIF' data_mmt143 _database_code_depnum_ccdc_archive 'CCDC 727539' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Br4 Cl4 Cu N4' _chemical_formula_weight 711.20 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' Cu Cu 0.3201 1.2651 '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 11.5372(5) _cell_length_b 11.3089(5) _cell_length_c 15.9944(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.196(2) _cell_angle_gamma 90.00 _cell_volume 1993.55(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9886 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 30.00 _exptl_crystal_description irregular _exptl_crystal_colour black _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1340 _exptl_absorpt_coefficient_mu 9.649 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.0668 _exptl_absorpt_correction_T_max 0.1450 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49601 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5814 _reflns_number_gt 5257 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0147P)^2^+1.5355P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00150(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5814 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0179 _refine_ls_wR_factor_ref 0.0392 _refine_ls_wR_factor_gt 0.0383 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.003 _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 Cu Cu 0.440989(18) 1.026816(18) 0.204821(13) 0.01501(5) Uani 1 1 d . . . Br1 Br 0.339814(14) 1.175700(15) 0.101033(11) 0.01675(4) Uani 1 1 d . . . Br2 Br 0.433484(15) 0.823379(15) 0.234315(12) 0.01935(4) Uani 1 1 d . . . Br3 Br 0.359743(15) 1.090616(16) 0.318334(11) 0.01823(4) Uani 1 1 d . . . Br4 Br 0.623164(15) 1.021256(17) 0.162085(13) 0.02195(5) Uani 1 1 d . . . N21 N 0.40723(13) 1.55881(13) 0.33847(10) 0.0168(3) Uani 1 1 d . . . H21 H 0.339(2) 1.5830(19) 0.3086(14) 0.020 Uiso 1 1 d . . . C22 C 0.44476(15) 1.45555(15) 0.31355(11) 0.0152(3) Uani 1 1 d . . . N22 N 0.37081(14) 1.39376(15) 0.24919(11) 0.0205(3) Uani 1 1 d . . . H22B H 0.296(2) 1.409(2) 0.2284(14) 0.025 Uiso 1 1 d . . . H22A H 0.389(2) 1.323(2) 0.2425(15) 0.025 Uiso 1 1 d . . . C23 C 0.56522(15) 1.42047(15) 0.35869(11) 0.0167(3) Uani 1 1 d . . . Cl23 Cl 0.61940(4) 1.29294(4) 0.32560(3) 0.02628(10) Uani 1 1 d . . . C24 C 0.63516(15) 1.48619(16) 0.42605(11) 0.0184(3) Uani 1 1 d . . . H24 H 0.7155 1.4620 0.4562 0.022 Uiso 1 1 calc R . . C25 C 0.58704(16) 1.59029(16) 0.45051(11) 0.0187(3) Uani 1 1 d . . . Cl25 Cl 0.67171(4) 1.66962(5) 0.53969(3) 0.02793(10) Uani 1 1 d . . . C26 C 0.47431(16) 1.62654(16) 0.40575(12) 0.0186(3) Uani 1 1 d . . . H26 H 0.4424 1.6981 0.4209 0.022 Uiso 1 1 calc R . . N11 N 0.91738(13) 0.76596(14) 0.46328(10) 0.0189(3) Uani 1 1 d . . . H11 H 0.928(2) 0.708(2) 0.4396(15) 0.023 Uiso 1 1 d . . . C12 C 0.81205(15) 0.82440(16) 0.42950(11) 0.0173(3) Uani 1 1 d . . . N12 N 0.73522(15) 0.78756(16) 0.35525(11) 0.0212(3) Uani 1 1 d . . . H12B H 0.750(2) 0.730(2) 0.3345(15) 0.025 Uiso 1 1 d . . . H12A H 0.673(2) 0.821(2) 0.3366(15) 0.025 Uiso 1 1 d . . . C13 C 0.79220(15) 0.92390(15) 0.47729(11) 0.0175(3) Uani 1 1 d . . . Cl13 Cl 0.65682(4) 0.99737(4) 0.43781(3) 0.02781(10) Uani 1 1 d . . . C14 C 0.87716(16) 0.95869(16) 0.55235(12) 0.0193(3) Uani 1 1 d . . . H14 H 0.8634 1.0259 0.5837 0.023 Uiso 1 1 calc R . . C15 C 0.98542(15) 0.89360(16) 0.58268(11) 0.0180(3) Uani 1 1 d . . . Cl15 Cl 1.09742(4) 0.93780(4) 0.67514(3) 0.02281(9) Uani 1 1 d . . . C16 C 1.00365(15) 0.79703(17) 0.53835(12) 0.0199(3) Uani 1 1 d . . . H16 H 1.0757 0.7516 0.5593 0.024 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 Cu 0.01484(9) 0.01391(10) 0.01681(10) 0.00086(8) 0.00548(7) 0.00075(7) Br1 0.01603(8) 0.01699(8) 0.01645(8) 0.00167(6) 0.00359(6) 0.00091(6) Br2 0.02074(8) 0.01367(8) 0.02222(9) 0.00196(6) 0.00417(6) -0.00011(6) Br3 0.01895(8) 0.01989(9) 0.01641(8) -0.00227(6) 0.00609(6) 0.00008(6) Br4 0.01662(8) 0.02223(9) 0.02956(10) 0.00654(7) 0.01078(7) 0.00396(6) N21 0.0148(6) 0.0159(7) 0.0188(7) 0.0010(6) 0.0036(5) 0.0002(5) C22 0.0158(7) 0.0146(8) 0.0165(8) 0.0026(6) 0.0067(6) -0.0014(6) N22 0.0169(7) 0.0183(8) 0.0250(8) -0.0035(6) 0.0040(6) 0.0003(6) C23 0.0162(7) 0.0144(8) 0.0211(8) 0.0033(6) 0.0083(6) 0.0014(6) Cl23 0.0204(2) 0.0178(2) 0.0417(3) -0.00165(19) 0.01091(18) 0.00307(16) C24 0.0150(7) 0.0214(9) 0.0187(8) 0.0069(7) 0.0050(6) -0.0017(6) C25 0.0223(8) 0.0201(9) 0.0145(8) 0.0007(7) 0.0068(6) -0.0079(7) Cl25 0.0346(2) 0.0328(3) 0.0157(2) -0.00389(18) 0.00637(17) -0.0165(2) C26 0.0230(8) 0.0152(8) 0.0204(8) -0.0008(7) 0.0106(7) -0.0031(6) N11 0.0190(7) 0.0184(8) 0.0191(7) -0.0046(6) 0.0055(6) 0.0022(6) C12 0.0162(7) 0.0190(8) 0.0177(8) 0.0017(7) 0.0063(6) -0.0018(6) N12 0.0212(7) 0.0217(8) 0.0186(8) -0.0030(6) 0.0026(6) 0.0020(6) C13 0.0186(8) 0.0164(8) 0.0182(8) 0.0036(7) 0.0065(6) 0.0027(6) Cl13 0.0260(2) 0.0293(2) 0.0259(2) 0.00051(19) 0.00419(17) 0.01163(18) C14 0.0254(9) 0.0161(8) 0.0186(8) 0.0001(7) 0.0099(7) -0.0001(7) C15 0.0182(8) 0.0211(9) 0.0149(8) 0.0006(7) 0.0051(6) -0.0038(6) Cl15 0.0236(2) 0.0263(2) 0.0168(2) -0.00274(17) 0.00325(15) -0.00487(17) C16 0.0171(8) 0.0234(9) 0.0180(8) 0.0000(7) 0.0034(6) 0.0005(7) _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 Cu Br2 2.3552(3) . ? Cu Br3 2.3879(3) . ? Cu Br4 2.3954(3) . ? Cu Br1 2.4099(3) . ? N21 C22 1.346(2) . ? N21 C26 1.361(2) . ? C22 N22 1.325(2) . ? C22 C23 1.420(2) . ? C23 C24 1.360(2) . ? C23 Cl23 1.7166(18) . ? C24 C25 1.406(3) . ? C25 C26 1.350(2) . ? C25 Cl25 1.7233(18) . ? N11 C12 1.348(2) . ? N11 C16 1.360(2) . ? C12 N12 1.322(2) . ? C12 C13 1.416(2) . ? C13 C14 1.364(2) . ? C13 Cl13 1.7162(17) . ? C14 C15 1.407(2) . ? C15 C16 1.352(3) . ? C15 Cl15 1.7252(17) . ? 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 Br2 Cu Br3 95.562(10) . . ? Br2 Cu Br4 96.825(9) . . ? Br3 Cu Br4 143.099(11) . . ? Br2 Cu Br1 141.394(11) . . ? Br3 Cu Br1 95.369(10) . . ? Br4 Cu Br1 96.255(10) . . ? C22 N21 C26 124.41(15) . . ? N22 C22 N21 119.86(16) . . ? N22 C22 C23 123.78(16) . . ? N21 C22 C23 116.35(15) . . ? C24 C23 C22 120.81(16) . . ? C24 C23 Cl23 121.23(13) . . ? C22 C23 Cl23 117.95(13) . . ? C23 C24 C25 119.18(15) . . ? C26 C25 C24 120.31(16) . . ? C26 C25 Cl25 120.16(15) . . ? C24 C25 Cl25 119.51(13) . . ? C25 C26 N21 118.82(16) . . ? C12 N11 C16 124.40(16) . . ? N12 C12 N11 119.42(17) . . ? N12 C12 C13 124.24(17) . . ? N11 C12 C13 116.33(16) . . ? C14 C13 C12 121.01(16) . . ? C14 C13 Cl13 121.54(14) . . ? C12 C13 Cl13 117.44(13) . . ? C13 C14 C15 119.09(17) . . ? C16 C15 C14 120.12(16) . . ? C16 C15 Cl15 119.36(14) . . ? C14 C15 Cl15 120.50(14) . . ? C15 C16 N11 119.01(16) . . ? 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 C26 N21 C22 N22 177.45(16) . . . . ? C26 N21 C22 C23 -3.5(2) . . . . ? N22 C22 C23 C24 -177.94(17) . . . . ? N21 C22 C23 C24 3.0(2) . . . . ? N22 C22 C23 Cl23 2.1(2) . . . . ? N21 C22 C23 Cl23 -176.96(12) . . . . ? C22 C23 C24 C25 -0.3(2) . . . . ? Cl23 C23 C24 C25 179.69(13) . . . . ? C23 C24 C25 C26 -2.2(3) . . . . ? C23 C24 C25 Cl25 176.31(13) . . . . ? C24 C25 C26 N21 1.9(3) . . . . ? Cl25 C25 C26 N21 -176.61(13) . . . . ? C22 N21 C26 C25 1.1(3) . . . . ? C16 N11 C12 N12 178.97(17) . . . . ? C16 N11 C12 C13 -0.5(3) . . . . ? N12 C12 C13 C14 -178.22(18) . . . . ? N11 C12 C13 C14 1.2(3) . . . . ? N12 C12 C13 Cl13 2.6(2) . . . . ? N11 C12 C13 Cl13 -177.97(13) . . . . ? C12 C13 C14 C15 -0.6(3) . . . . ? Cl13 C13 C14 C15 178.62(13) . . . . ? C13 C14 C15 C16 -0.9(3) . . . . ? C13 C14 C15 Cl15 177.65(14) . . . . ? C14 C15 C16 N11 1.6(3) . . . . ? Cl15 C15 C16 N11 -176.96(13) . . . . ? C12 N11 C16 C15 -0.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N21 H21 Br3 0.84(2) 2.58(2) 3.3674(15) 158.3(19) 2 N21 H21 Br1 0.84(2) 3.03(2) 3.5267(15) 119.8(17) 2 N22 H22B Br3 0.84(2) 2.69(2) 3.3910(17) 142.1(19) 2 N22 H22B Br2 0.84(2) 3.04(2) 3.6845(16) 134.6(19) 2 N22 H22A Br1 0.84(2) 2.73(2) 3.3650(17) 134(2) . N22 H22A Br3 0.84(2) 2.96(2) 3.6160(17) 137.1(19) . N11 H11 Br4 0.79(2) 2.62(2) 3.3679(16) 159(2) 2_645 N11 H11 Br1 0.79(2) 2.96(2) 3.4134(15) 119.6(19) 2_645 N12 H12B Br4 0.77(2) 2.77(3) 3.4762(18) 153(2) 2_645 N12 H12A Cl13 0.79(2) 2.61(2) 2.9830(19) 111.0(19) . N12 H12A Br2 0.79(2) 2.76(2) 3.4702(16) 150(2) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.600 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.076 # Attachment '3.CIF' data_mmt133 _database_code_depnum_ccdc_archive 'CCDC 727540' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Br4 Cl4 Cu N4' _chemical_formula_weight 711.20 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' Cu Cu 0.3201 1.2651 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.3124(10) _cell_length_b 7.9776(5) _cell_length_c 14.6739(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.001(3) _cell_angle_gamma 90.00 _cell_volume 1904.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9502 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 29.97 _exptl_crystal_description square _exptl_crystal_colour yellow _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1340 _exptl_absorpt_coefficient_mu 10.098 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.0778 _exptl_absorpt_correction_T_max 0.2499 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45303 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 29.98 _reflns_number_total 5541 _reflns_number_gt 4929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0104P)^2^+2.7715P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5541 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_ref 0.0431 _refine_ls_wR_factor_gt 0.0398 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 Cu Cu 0.797061(15) 0.06040(3) 0.821861(16) 0.01381(5) Uani 1 1 d . . . Cl1 Cl 0.67112(3) -0.04443(7) 0.83734(3) 0.01773(10) Uani 1 1 d . . . Cl2 Cl 0.82338(3) 0.13500(7) 0.96954(3) 0.02007(10) Uani 1 1 d . . . Cl3 Cl 0.76938(3) 0.19847(7) 0.68701(3) 0.01783(10) Uani 1 1 d . . . Cl4 Cl 0.92521(3) -0.01415(7) 0.79920(3) 0.01837(10) Uani 1 1 d . . . N11 N 0.58559(11) 0.1392(2) 0.62681(12) 0.0155(3) Uani 1 1 d . . . H11 H 0.6316(16) 0.135(3) 0.6482(17) 0.019 Uiso 1 1 d . . . C12 C 0.57288(12) 0.2237(3) 0.54694(14) 0.0148(4) Uani 1 1 d . . . N12 N 0.63630(12) 0.2892(3) 0.50831(14) 0.0200(4) Uani 1 1 d . . . H12A H 0.6834(18) 0.283(3) 0.5324(18) 0.024 Uiso 1 1 d . . . H12B H 0.6306(17) 0.343(3) 0.4602(19) 0.024 Uiso 1 1 d . . . C13 C 0.49003(12) 0.2334(3) 0.51036(13) 0.0137(4) Uani 1 1 d . . . Br13 Br 0.467257(13) 0.34927(3) 0.400023(14) 0.01725(5) Uani 1 1 d . . . C14 C 0.42786(12) 0.1631(3) 0.55463(13) 0.0142(4) Uani 1 1 d . . . H14 H 0.3726 0.1729 0.5301 0.017 Uiso 1 1 calc R . . C15 C 0.44596(12) 0.0757(3) 0.63708(13) 0.0145(4) Uani 1 1 d . . . Br15 Br 0.361747(13) -0.02875(3) 0.697942(14) 0.01821(5) Uani 1 1 d . . . C16 C 0.52510(13) 0.0660(3) 0.67195(14) 0.0154(4) Uani 1 1 d . . . H16 H 0.5381 0.0082 0.7277 0.018 Uiso 1 1 calc R . . N21 N 0.98450(11) -0.2368(2) 1.02642(12) 0.0157(3) Uani 1 1 d . . . H21 H 1.0309(16) -0.197(3) 1.0434(17) 0.019 Uiso 1 1 d . . . C22 C 0.97731(12) -0.3222(3) 0.94628(13) 0.0142(4) Uani 1 1 d . . . N22 N 1.04298(11) -0.3434(2) 0.89893(13) 0.0175(4) Uani 1 1 d . . . H22A H 1.0889(17) -0.303(3) 0.9177(18) 0.021 Uiso 1 1 d . . . H22B H 1.0401(16) -0.395(3) 0.8480(18) 0.021 Uiso 1 1 d . . . C23 C 0.89874(13) -0.3881(3) 0.92045(13) 0.0153(4) Uani 1 1 d . . . Br23 Br 0.883636(13) -0.51396(3) 0.812799(14) 0.01825(5) Uani 1 1 d . . . C24 C 0.83445(13) -0.3649(3) 0.97376(14) 0.0168(4) Uani 1 1 d . . . H24 H 0.7819 -0.4100 0.9557 0.020 Uiso 1 1 calc R . . C25 C 0.84634(13) -0.2739(3) 1.05547(14) 0.0169(4) Uani 1 1 d . . . Br25 Br 0.757349(13) -0.23573(3) 1.127546(15) 0.02366(5) Uani 1 1 d . . . C26 C 0.92164(13) -0.2116(3) 1.08124(14) 0.0175(4) Uani 1 1 d . . . H26 H 0.9305 -0.1512 1.1368 0.021 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 Cu 0.01002(11) 0.01886(13) 0.01256(11) 0.00136(9) 0.00084(9) -0.00060(9) Cl1 0.0124(2) 0.0225(2) 0.0184(2) -0.00051(18) 0.00220(18) -0.00415(19) Cl2 0.0141(2) 0.0319(3) 0.0143(2) -0.00299(19) 0.00126(18) -0.0038(2) Cl3 0.0126(2) 0.0259(3) 0.0147(2) 0.00483(18) -0.00099(17) -0.0018(2) Cl4 0.0121(2) 0.0241(3) 0.0191(2) 0.00376(19) 0.00245(18) 0.00259(19) N11 0.0089(8) 0.0208(9) 0.0163(8) -0.0013(7) -0.0020(6) 0.0006(7) C12 0.0132(9) 0.0156(10) 0.0156(9) -0.0029(7) 0.0020(7) -0.0002(8) N12 0.0111(8) 0.0293(11) 0.0196(9) 0.0034(8) 0.0007(7) -0.0023(8) C13 0.0127(9) 0.0154(10) 0.0127(9) -0.0002(7) -0.0012(7) 0.0017(8) Br13 0.01614(10) 0.01980(10) 0.01577(9) 0.00376(7) 0.00076(7) -0.00006(8) C14 0.0110(9) 0.0161(10) 0.0151(9) -0.0024(7) -0.0008(7) 0.0002(8) C15 0.0130(9) 0.0167(10) 0.0140(9) -0.0018(7) 0.0019(7) -0.0014(8) Br15 0.01535(10) 0.02299(11) 0.01658(9) 0.00202(8) 0.00315(7) -0.00332(8) C16 0.0150(10) 0.0175(10) 0.0137(9) -0.0007(7) 0.0009(7) 0.0010(8) N21 0.0107(8) 0.0196(9) 0.0164(8) -0.0005(7) -0.0016(7) -0.0018(7) C22 0.0131(9) 0.0148(9) 0.0143(9) 0.0036(7) -0.0014(7) 0.0008(8) N22 0.0118(8) 0.0237(10) 0.0169(9) -0.0017(7) 0.0006(7) -0.0011(7) C23 0.0162(10) 0.0163(10) 0.0132(9) 0.0013(7) -0.0004(7) -0.0006(8) Br23 0.01752(10) 0.02230(11) 0.01480(9) -0.00153(8) 0.00025(7) -0.00380(8) C24 0.0114(9) 0.0205(10) 0.0180(10) 0.0017(8) -0.0018(8) -0.0012(8) C25 0.0114(9) 0.0219(11) 0.0172(9) 0.0008(8) 0.0008(8) 0.0012(8) Br25 0.01404(10) 0.03356(13) 0.02399(11) -0.00562(9) 0.00565(8) -0.00046(9) C26 0.0148(10) 0.0209(10) 0.0166(9) -0.0018(8) 0.0004(8) 0.0013(8) _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 Cu Cl4 2.2206(6) . ? Cu Cl1 2.2443(6) . ? Cu Cl2 2.2594(6) . ? Cu Cl3 2.2821(5) . ? N11 C12 1.355(3) . ? N11 C16 1.358(3) . ? C12 N12 1.321(3) . ? C12 C13 1.421(3) . ? C13 C14 1.363(3) . ? C13 Br13 1.879(2) . ? C14 C15 1.410(3) . ? C15 C16 1.357(3) . ? C15 Br15 1.884(2) . ? N21 C22 1.357(3) . ? N21 C26 1.362(3) . ? C22 N22 1.328(3) . ? C22 C23 1.412(3) . ? C23 C24 1.364(3) . ? C23 Br23 1.873(2) . ? C24 C25 1.403(3) . ? C25 C26 1.354(3) . ? C25 Br25 1.880(2) . ? 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 Cl4 Cu Cl1 142.50(2) . . ? Cl4 Cu Cl2 95.53(2) . . ? Cl1 Cu Cl2 96.61(2) . . ? Cl4 Cu Cl3 97.51(2) . . ? Cl1 Cu Cl3 98.08(2) . . ? Cl2 Cu Cl3 135.84(2) . . ? C12 N11 C16 124.27(18) . . ? N12 C12 N11 119.37(19) . . ? N12 C12 C13 124.7(2) . . ? N11 C12 C13 115.96(18) . . ? C14 C13 C12 121.15(18) . . ? C14 C13 Br13 120.29(15) . . ? C12 C13 Br13 118.55(15) . . ? C13 C14 C15 119.64(19) . . ? C16 C15 C14 119.25(18) . . ? C16 C15 Br15 120.11(15) . . ? C14 C15 Br15 120.64(15) . . ? C15 C16 N11 119.72(19) . . ? C22 N21 C26 124.26(19) . . ? N22 C22 N21 119.57(19) . . ? N22 C22 C23 124.2(2) . . ? N21 C22 C23 116.19(18) . . ? C24 C23 C22 121.00(19) . . ? C24 C23 Br23 119.69(16) . . ? C22 C23 Br23 119.30(15) . . ? C23 C24 C25 119.6(2) . . ? C26 C25 C24 119.79(19) . . ? C26 C25 Br25 120.30(16) . . ? C24 C25 Br25 119.90(15) . . ? C25 C26 N21 119.1(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 N12 -179.5(2) . . . . ? C16 N11 C12 C13 0.0(3) . . . . ? N12 C12 C13 C14 -179.7(2) . . . . ? N11 C12 C13 C14 0.8(3) . . . . ? N12 C12 C13 Br13 -0.8(3) . . . . ? N11 C12 C13 Br13 179.74(14) . . . . ? C12 C13 C14 C15 -1.5(3) . . . . ? Br13 C13 C14 C15 179.63(15) . . . . ? C13 C14 C15 C16 1.3(3) . . . . ? C13 C14 C15 Br15 -178.04(15) . . . . ? C14 C15 C16 N11 -0.4(3) . . . . ? Br15 C15 C16 N11 178.87(15) . . . . ? C12 N11 C16 C15 -0.2(3) . . . . ? C26 N21 C22 N22 -178.3(2) . . . . ? C26 N21 C22 C23 -0.3(3) . . . . ? N22 C22 C23 C24 178.3(2) . . . . ? N21 C22 C23 C24 0.4(3) . . . . ? N22 C22 C23 Br23 -0.1(3) . . . . ? N21 C22 C23 Br23 -178.00(15) . . . . ? C22 C23 C24 C25 0.1(3) . . . . ? Br23 C23 C24 C25 178.50(16) . . . . ? C23 C24 C25 C26 -0.7(3) . . . . ? C23 C24 C25 Br25 178.15(16) . . . . ? C24 C25 C26 N21 0.8(3) . . . . ? Br25 C25 C26 N21 -178.05(16) . . . . ? C22 N21 C26 C25 -0.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 Cl3 0.79(3) 2.33(3) 3.1020(19) 163(3) . N12 H12A Cl2 0.82(3) 2.61(3) 3.201(2) 130(2) 4_565 N12 H12A Cl3 0.82(3) 2.67(3) 3.364(2) 143(2) . N12 H12B Cl1 0.83(3) 2.54(3) 3.311(2) 157(2) 4_565 N21 H21 Cl2 0.84(3) 2.45(3) 3.2340(19) 156(2) 3_757 N21 H21 Cl4 0.84(3) 2.91(3) 3.4928(19) 128(2) 3_757 N22 H22A Cl2 0.85(3) 2.50(3) 3.264(2) 151(2) 3_757 N22 H22A Cl3 0.85(3) 2.86(3) 3.4073(19) 124(2) 2_746 N22 H22B Cl4 0.85(3) 2.46(3) 3.284(2) 163(2) 2_746 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.98 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.759 _refine_diff_density_min -0.674 _refine_diff_density_rms 0.123 # Attachment '4.CIF' data_bt253 _database_code_depnum_ccdc_archive 'CCDC 727541' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-amino-3,5-dibromopyridinium) tetrabromocuprate ; _chemical_name_common 'bis(2-amino-3,5-dibromopyridinium) tetrabromocuprate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Br8 Cu N4' _chemical_formula_weight 889.04 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' Cu Cu 0.3201 1.2651 '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 11.5870(11) _cell_length_b 11.5942(11) _cell_length_c 16.5555(15) _cell_angle_alpha 90.00 _cell_angle_beta 107.096(2) _cell_angle_gamma 90.00 _cell_volume 2125.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6808 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 29.68 _exptl_crystal_description 'irregular block' _exptl_crystal_colour orange _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.778 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1628 _exptl_absorpt_coefficient_mu 16.065 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2487 _exptl_absorpt_correction_T_max 0.7394 _exptl_absorpt_process_details 'via SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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/Siemens SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <0.01 _diffrn_reflns_number 12243 _diffrn_reflns_av_R_equivalents 0.0735 _diffrn_reflns_av_sigmaI/netI 0.0771 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3746 _reflns_number_gt 2217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v. 5.626' _computing_cell_refinement 'Bruker SAINT+ v. 6.36a' _computing_data_reduction 'Bruker SAINT+ v. 6.36a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'XCIF, Bruker SHELXTL v. 6.12' _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^)+(0.0235P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3746 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0703 _refine_ls_wR_factor_gt 0.0585 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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 Cu Cu 0.56253(8) 0.02913(8) 0.29618(6) 0.0408(3) Uani 1 1 d . . . Br1 Br 0.66297(7) 0.17432(7) 0.39659(5) 0.0449(2) Uani 1 1 d . . . Br2 Br 0.64397(7) 0.09201(7) 0.18587(5) 0.0475(2) Uani 1 1 d . . . Br3 Br 0.37885(7) 0.02763(8) 0.33596(6) 0.0562(3) Uani 1 1 d . . . Br4 Br 0.56689(8) -0.16965(7) 0.26639(5) 0.0538(2) Uani 1 1 d . . . N11 N 0.4169(6) 0.2678(6) 0.4595(4) 0.0462(18) Uani 1 1 d . . . H11 H 0.438(6) 0.200(6) 0.433(4) 0.055 Uiso 1 1 d . . . N12 N 0.2350(6) 0.2894(6) 0.3591(5) 0.051(2) Uani 1 1 d . . . H12A H 0.259(7) 0.219(6) 0.331(4) 0.062 Uiso 1 1 d . . . H12B H 0.177(7) 0.329(7) 0.339(5) 0.062 Uiso 1 1 d . . . C12 C 0.3116(7) 0.3238(7) 0.4309(5) 0.041(2) Uani 1 1 d . . . C13 C 0.2920(7) 0.4180(7) 0.4802(5) 0.044(2) Uani 1 1 d . . . C14 C 0.3788(7) 0.4473(6) 0.5518(5) 0.039(2) Uani 1 1 d . . . H14 H 0.3662 0.5096 0.5835 0.047 Uiso 1 1 calc R . . C15 C 0.4857(7) 0.3862(7) 0.5786(5) 0.040(2) Uani 1 1 d . . . C16 C 0.5040(7) 0.2952(7) 0.5322(5) 0.048(2) Uani 1 1 d . . . H16 H 0.5748 0.2523 0.5498 0.058 Uiso 1 1 calc R . . Br13 Br 0.14351(8) 0.49453(8) 0.44250(6) 0.0614(3) Uani 1 1 d . . . Br15 Br 0.61013(7) 0.42928(7) 0.67542(5) 0.0513(2) Uani 1 1 d . . . N21 N 0.5886(6) 0.5568(6) 0.1673(4) 0.0403(17) Uani 1 1 d . . . H21 H 0.657(6) 0.583(6) 0.192(4) 0.048 Uiso 1 1 d . . . N22 N 0.6233(6) 0.3990(6) 0.2539(5) 0.049(2) Uani 1 1 d . . . H22B H 0.692(7) 0.408(7) 0.275(5) 0.059 Uiso 1 1 d . . . H22A H 0.595(7) 0.329(6) 0.259(5) 0.059 Uiso 1 1 d . . . C22 C 0.5502(7) 0.4561(6) 0.1908(5) 0.0333(18) Uani 1 1 d . . . C23 C 0.4339(6) 0.4210(6) 0.1434(5) 0.0381(19) Uani 1 1 d . . . C24 C 0.3671(7) 0.4838(7) 0.0759(5) 0.042(2) Uani 1 1 d . . . H24 H 0.2903 0.4594 0.0452 0.051 Uiso 1 1 calc R . . C25 C 0.4149(7) 0.5841(7) 0.0536(5) 0.041(2) Uani 1 1 d . . . C26 C 0.5254(7) 0.6219(7) 0.1003(5) 0.045(2) Uani 1 1 d . . . H26 H 0.5572 0.6905 0.0869 0.054 Uiso 1 1 calc R . . Br23 Br 0.37130(8) 0.28513(7) 0.17682(6) 0.0624(3) Uani 1 1 d . . . Br25 Br 0.32877(9) 0.66538(9) -0.04341(5) 0.0682(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 Cu 0.0400(6) 0.0388(6) 0.0442(6) -0.0010(5) 0.0135(5) -0.0011(5) Br1 0.0432(5) 0.0449(5) 0.0449(5) -0.0050(4) 0.0105(4) -0.0024(4) Br2 0.0458(5) 0.0542(5) 0.0425(5) 0.0074(4) 0.0130(4) 0.0022(4) Br3 0.0438(5) 0.0582(6) 0.0727(6) -0.0115(5) 0.0266(5) -0.0088(5) Br4 0.0591(6) 0.0382(5) 0.0590(6) -0.0057(5) 0.0093(5) 0.0010(4) N11 0.042(4) 0.049(5) 0.048(5) -0.009(4) 0.014(4) 0.006(4) N12 0.053(5) 0.052(5) 0.047(5) 0.002(4) 0.013(4) 0.009(4) C12 0.030(5) 0.060(6) 0.031(5) 0.002(5) 0.004(4) -0.010(4) C13 0.044(5) 0.047(5) 0.041(5) 0.006(4) 0.014(4) 0.007(4) C14 0.056(5) 0.030(5) 0.035(5) -0.002(4) 0.019(4) 0.000(4) C15 0.047(5) 0.037(5) 0.038(5) 0.002(4) 0.017(4) 0.003(4) C16 0.044(5) 0.058(6) 0.042(5) -0.003(5) 0.010(4) 0.002(5) Br13 0.0551(6) 0.0660(6) 0.0608(6) 0.0056(5) 0.0136(5) 0.0202(5) Br15 0.0506(5) 0.0576(6) 0.0431(5) -0.0028(4) 0.0095(4) -0.0042(4) N21 0.034(4) 0.039(4) 0.046(5) -0.002(4) 0.009(4) -0.008(3) N22 0.043(5) 0.038(4) 0.063(5) 0.007(4) 0.012(4) 0.002(4) C22 0.036(5) 0.023(4) 0.043(5) 0.006(4) 0.017(4) 0.008(4) C23 0.028(4) 0.040(5) 0.052(5) -0.009(4) 0.020(4) -0.004(4) C24 0.031(4) 0.052(5) 0.039(5) -0.006(4) 0.003(4) 0.007(4) C25 0.054(6) 0.038(5) 0.031(5) -0.002(4) 0.013(4) 0.011(4) C26 0.059(6) 0.034(5) 0.045(5) 0.000(4) 0.020(5) 0.002(4) Br23 0.0507(6) 0.0417(5) 0.0989(8) 0.0027(5) 0.0282(5) -0.0069(4) Br25 0.0875(7) 0.0752(7) 0.0416(5) 0.0087(5) 0.0185(5) 0.0397(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 Cu Br4 2.3606(12) . ? Cu Br2 2.4022(12) . ? Cu Br3 2.4058(12) . ? Cu Br1 2.4112(12) . ? N11 C12 1.340(9) . ? N11 C16 1.361(9) . ? N12 C12 1.319(9) . ? C12 C13 1.422(10) . ? C13 C14 1.353(9) . ? C13 Br13 1.872(7) . ? C14 C15 1.382(10) . ? C15 C16 1.359(10) . ? C15 Br15 1.881(8) . ? N21 C22 1.347(8) . ? N21 C26 1.363(9) . ? N22 C22 1.315(9) . ? C22 C23 1.406(9) . ? C23 C24 1.368(9) . ? C23 Br23 1.884(7) . ? C24 C25 1.384(10) . ? C25 C26 1.359(10) . ? C25 Br25 1.877(7) . ? 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 Br4 Cu Br2 95.75(4) . . ? Br4 Cu Br3 97.19(5) . . ? Br2 Cu Br3 141.92(5) . . ? Br4 Cu Br1 142.19(5) . . ? Br2 Cu Br1 95.42(4) . . ? Br3 Cu Br1 95.91(4) . . ? C12 N11 C16 124.1(7) . . ? N12 C12 N11 118.3(8) . . ? N12 C12 C13 124.8(8) . . ? N11 C12 C13 116.9(7) . . ? C14 C13 C12 119.5(7) . . ? C14 C13 Br13 123.1(6) . . ? C12 C13 Br13 117.3(6) . . ? C13 C14 C15 121.2(7) . . ? C16 C15 C14 119.4(7) . . ? C16 C15 Br15 118.7(6) . . ? C14 C15 Br15 121.9(6) . . ? C15 C16 N11 118.9(8) . . ? C22 N21 C26 124.8(7) . . ? N22 C22 N21 118.4(7) . . ? N22 C22 C23 125.9(7) . . ? N21 C22 C23 115.7(7) . . ? C24 C23 C22 121.4(7) . . ? C24 C23 Br23 120.8(6) . . ? C22 C23 Br23 117.8(6) . . ? C23 C24 C25 119.4(7) . . ? C26 C25 C24 120.2(7) . . ? C26 C25 Br25 120.0(6) . . ? C24 C25 Br25 119.7(6) . . ? C25 C26 N21 118.4(7) . . ? 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 N12 179.4(7) . . . . ? C16 N11 C12 C13 0.5(11) . . . . ? N12 C12 C13 C14 -178.2(8) . . . . ? N11 C12 C13 C14 0.6(11) . . . . ? N12 C12 C13 Br13 2.8(10) . . . . ? N11 C12 C13 Br13 -178.4(5) . . . . ? C12 C13 C14 C15 -0.9(11) . . . . ? Br13 C13 C14 C15 178.1(5) . . . . ? C13 C14 C15 C16 0.0(11) . . . . ? C13 C14 C15 Br15 177.4(6) . . . . ? C14 C15 C16 N11 1.1(11) . . . . ? Br15 C15 C16 N11 -176.3(6) . . . . ? C12 N11 C16 C15 -1.4(12) . . . . ? C26 N21 C22 N22 176.3(7) . . . . ? C26 N21 C22 C23 -2.9(10) . . . . ? N22 C22 C23 C24 -176.6(8) . . . . ? N21 C22 C23 C24 2.5(10) . . . . ? N22 C22 C23 Br23 4.3(10) . . . . ? N21 C22 C23 Br23 -176.6(5) . . . . ? C22 C23 C24 C25 0.0(11) . . . . ? Br23 C23 C24 C25 179.1(5) . . . . ? C23 C24 C25 C26 -2.4(11) . . . . ? C23 C24 C25 Br25 175.7(5) . . . . ? C24 C25 C26 N21 2.1(11) . . . . ? Br25 C25 C26 N21 -176.0(5) . . . . ? C22 N21 C26 C25 0.7(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 Br3 0.96(7) 2.53(7) 3.406(7) 151(6) . N11 H11 Br1 0.96(7) 2.86(7) 3.483(7) 123(5) . N12 H12A Br3 1.02(7) 2.60(7) 3.536(7) 152(6) . N12 H12B Br13 0.80(7) 2.67(8) 3.091(8) 114(7) . N12 H12B Br4 0.80(7) 2.85(8) 3.536(7) 145(7) 2 N21 H21 Br2 0.83(7) 2.59(7) 3.353(6) 154(7) 2_655 N21 H21 Br1 0.83(7) 3.07(7) 3.612(6) 125(6) 2_655 N22 H22B Br2 0.77(7) 2.81(8) 3.419(7) 138(8) 2_655 N22 H22A Br23 0.89(7) 2.60(7) 3.116(7) 118(6) . N22 H22A Br1 0.89(7) 2.82(7) 3.455(7) 129(6) . N22 H22A Br2 0.89(7) 3.12(7) 3.762(7) 131(6) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.656 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.133