# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_maj _database_code_depnum_ccdc_archive 'CCDC 915122' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis-(2-amino-5-iodopyridinium) diaquatrichlorocuprate chloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 Cl4 Cu I2 N4 O2' _chemical_formula_weight 683.41 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 4.06780(10) _cell_length_b 16.2705(6) _cell_length_c 14.8387(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.127(2) _cell_angle_gamma 90.00 _cell_volume 976.49(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9992 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 33.54 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 646 _exptl_absorpt_coefficient_mu 4.838 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1876 _exptl_absorpt_correction_T_max 0.4763 _exptl_absorpt_process_details SADABS _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26671 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2954 _reflns_number_gt 2680 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. The structure is disordered so as to give the illusion of a ladder structure, aligned parallel to the a-axis, whereas, in fact, each Cu site is discrete. The crystallographically unique Cu site is only half occupied by Cu. Because of space group symmetry, there are two complete crystallographically related apparent ladders in each unit cell. Within each apparent ladder, the Cu sites are alternately occupied, but the occupancy of these apparent ladders is uncorrelated -- consistent with the absence of any evidence for a unit cell doubling. The disorder then means that the hydrogens on the crystallographically unique water molecule are disodered. The tables of bond distances and angles have been edited to remove non- sensical entries arising from the disorder. ; _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^)+(0.0125P)^2^+0.7308P] 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 0.00146(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2954 _refine_ls_number_parameters 128 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0189 _refine_ls_wR_factor_ref 0.0435 _refine_ls_wR_factor_gt 0.0423 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.005 _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 Cu1 Cu 0.03426(10) 0.99202(3) 0.60423(3) 0.01195(9) Uani 0.50 1 d P . . Cl1 Cl 0.07616(10) 0.90657(3) 0.72705(3) 0.01856(9) Uani 1 1 d . . . Cl2 Cl 0.00416(11) 1.11598(3) 0.53398(4) 0.02264(10) Uani 1 1 d . . . O1 O 0.5365(3) 0.99626(10) 0.60985(10) 0.0224(3) Uani 1 1 d D . . H1A H 0.427(9) 0.965(2) 0.641(3) 0.027 Uiso 0.50 1 d PD A 1 H1B H 0.389(8) 1.029(2) 0.587(3) 0.027 Uiso 0.50 1 d PD B 1 H1C H 0.673(8) 0.963(2) 0.636(3) 0.027 Uiso 0.50 1 d PD C 2 H1D H 0.635(9) 1.020(3) 0.571(2) 0.027 Uiso 0.50 1 d PD D 2 N11 N 0.5751(4) 0.24890(10) 0.84799(11) 0.0182(3) Uani 1 1 d U . . H11 H 0.6350 0.2986 0.8386 0.022 Uiso 1 1 calc R . . C12 C 0.6144(4) 0.19214(12) 0.78357(13) 0.0182(4) Uani 1 1 d U . . N12 N 0.7522(5) 0.21507(13) 0.70988(13) 0.0259(4) Uani 1 1 d U . . H12A H 0.802(6) 0.2599(18) 0.7046(19) 0.031 Uiso 1 1 d . . . H12B H 0.787(7) 0.1819(18) 0.6702(19) 0.031 Uiso 1 1 d . . . C13 C 0.5091(5) 0.11137(12) 0.79889(14) 0.0216(4) Uani 1 1 d U . . H13 H 0.5295 0.0708 0.7557 0.026 Uiso 1 1 calc R . . C14 C 0.3771(5) 0.09268(12) 0.87716(14) 0.0190(4) Uani 1 1 d U . . H14 H 0.3076 0.0393 0.8871 0.023 Uiso 1 1 calc R . . C15 C 0.3454(4) 0.15401(12) 0.94340(12) 0.0159(3) Uani 1 1 d U . . I1 I 0.18078(3) 0.124192(8) 1.067902(8) 0.01793(5) Uani 1 1 d . . . C16 C 0.4457(4) 0.23185(12) 0.92703(13) 0.0177(4) Uani 1 1 d U . . H16 H 0.4262 0.2732 0.9694 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 Cu1 0.01066(17) 0.0128(2) 0.0126(2) 0.00155(15) 0.00231(14) 0.00030(14) Cl1 0.01840(19) 0.0203(2) 0.0176(2) 0.00570(17) 0.00485(15) 0.00313(15) Cl2 0.0185(2) 0.0171(2) 0.0334(3) 0.00857(19) 0.00820(18) 0.00191(15) O1 0.0194(6) 0.0253(8) 0.0231(8) 0.0087(6) 0.0043(5) 0.0030(5) N11 0.0210(7) 0.0136(7) 0.0205(8) -0.0001(6) 0.0046(6) -0.0005(6) C12 0.0190(8) 0.0187(9) 0.0166(9) -0.0003(7) 0.0008(6) 0.0020(7) N12 0.0379(10) 0.0208(9) 0.0203(9) 0.0002(7) 0.0098(7) -0.0008(7) C13 0.0285(9) 0.0166(9) 0.0198(10) -0.0065(7) 0.0033(7) -0.0013(7) C14 0.0219(8) 0.0130(9) 0.0216(10) -0.0002(7) -0.0006(7) -0.0013(7) C15 0.0136(7) 0.0177(9) 0.0165(9) 0.0003(7) 0.0018(6) 0.0015(6) I1 0.01425(6) 0.02094(7) 0.01900(7) 0.00198(5) 0.00360(4) 0.00016(4) C16 0.0173(8) 0.0167(9) 0.0195(9) -0.0034(7) 0.0039(6) 0.0007(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 Cu1 O1 2.0365(14) 1_455 ? Cu1 O1 2.0370(14) . ? Cu1 Cl2 2.2676(6) . ? Cu1 Cl1 2.2842(6) . ? Cu1 Cl2 2.6926(7) 3_576 ? O1 H1A 0.846(10) . ? O1 H1B 0.845(10) . ? O1 H1C 0.840(10) . ? O1 H1D 0.835(10) . ? N11 C12 1.351(2) . ? N11 C16 1.364(2) . ? N11 H11 0.8600 . ? C12 N12 1.334(3) . ? C12 C13 1.408(3) . ? N12 H12A 0.76(3) . ? N12 H12B 0.82(3) . ? C13 C14 1.365(3) . ? C13 H13 0.9300 . ? C14 C15 1.416(3) . ? C14 H14 0.9300 . ? C15 C16 1.360(3) . ? C15 I1 2.0882(18) . ? C16 H16 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 O1 Cu1 O1 173.93(10) 1_455 . ? O1 Cu1 Cl2 89.06(5) 1_455 . ? O1 Cu1 Cl2 89.62(5) . . ? O1 Cu1 Cl1 88.73(5) 1_455 . ? O1 Cu1 Cl1 89.93(5) . . ? Cl2 Cu1 Cl1 154.68(3) . . ? O1 Cu1 Cl2 94.36(5) 1_455 3_576 ? O1 Cu1 Cl2 91.70(5) . 3_576 ? Cl2 Cu1 Cl2 103.56(2) . 3_576 ? Cl1 Cu1 Cl2 101.76(2) . 3_576 ? Cu1 O1 H1A 126(3) 1_655 . ? Cu1 O1 H1B 132(3) 1_655 . ? H1A O1 H1B 102(2) . . ? Cu1 O1 H1C 128(3) . . ? Cu1 O1 H1D 123(3) . . ? H1C O1 H1D 106(2) . . ? C12 N11 C16 123.71(17) . . ? C12 N11 H11 118.1 . . ? C16 N11 H11 118.1 . . ? N12 C12 N11 118.73(19) . . ? N12 C12 C13 123.70(19) . . ? N11 C12 C13 117.56(17) . . ? C12 N12 H12A 119(2) . . ? C12 N12 H12B 121.4(19) . . ? H12A N12 H12B 119(3) . . ? C14 C13 C12 119.96(18) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.46(18) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 118.73(17) . . ? C16 C15 I1 120.32(14) . . ? C14 C15 I1 120.79(14) . . ? C15 C16 N11 119.57(17) . . ? C15 C16 H16 120.2 . . ? N11 C16 H16 120.2 . . ? 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 -178.16(18) . . . . ? C16 N11 C12 C13 1.2(3) . . . . ? N12 C12 C13 C14 178.5(2) . . . . ? N11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 C16 0.7(3) . . . . ? C13 C14 C15 I1 -174.86(15) . . . . ? C14 C15 C16 N11 -0.3(3) . . . . ? I1 C15 C16 N11 175.23(13) . . . . ? C12 N11 C16 C15 -0.7(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 O1 H1A Cl1 0.846(10) 2.227(14) 3.0588(14) 168(4) . O1 H1B Cl2 0.845(10) 2.194(10) 3.0382(15) 177(5) . O1 H1C Cl1 0.840(10) 2.208(16) 3.0263(15) 165(5) 1_655 O1 H1D Cl2 0.835(10) 2.27(3) 3.0229(15) 150(5) 1_655 N11 H11 Cl1 0.76(3) 2.47(3) 3.1912(17) 160(2) 2_646 N12 H12A Cl1 0.76(3) 2.62(3) 3.306(2) 151(3) 2_646 N12 H12B Cl2 0.82(3) 2.53(3) 3.322(2) 162(2) 1_645 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.568 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.095 data_uj3 _database_code_depnum_ccdc_archive 'CCDC 915123' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(3-iodopyridinium) diaquatrichlorocuprate chloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 Cl4 Cu1 I2 N2 O2' _chemical_formula_weight 653.36 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 4.1214(5) _cell_length_b 16.791(2) _cell_length_c 13.5186(13) _cell_angle_alpha 90.00 _cell_angle_beta 92.598(10) _cell_angle_gamma 90.00 _cell_volume 934.56(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 766 _cell_measurement_theta_min 3.0107 _cell_measurement_theta_max 29.0104 _exptl_crystal_description needle _exptl_crystal_colour 'light blue' _exptl_crystal_size_max 0.4214 _exptl_crystal_size_mid 0.0263 _exptl_crystal_size_min 0.0131 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 614 _exptl_absorpt_coefficient_mu 5.046 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.151 _exptl_absorpt_correction_T_max 0.623 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0534 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'No decay was observed' _diffrn_reflns_number 3944 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1909 _reflns_number_gt 1413 _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. The structure is disordered so as to give the illusion of a ladder structure, aligned parallel to the a-axis, whereas, in fact, each Cu site is discrete. The crystallographically unique Cu site is only half occupied by Cu. Because of space group symmetry, there are two complete crystallographically related apparent ladders in each unit cell. Within each apparent ladder, the Cu sites are alternately occupied, but the occupancy of these apparent ladders is uncorrelated -- consistent with the absence of any evidence for a unit cell doubling. The disorder then means that the hydrogens on the crystallographically unique water molecule are disodered. The tables of bond distances and angles have been edited to remove non- sensical entries arising from the disorder. ; _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^)+(0.0124P)^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 1909 _refine_ls_number_parameters 115 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.0636 _refine_ls_wR_factor_gt 0.0579 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.016 _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 Cu1 Cu 0.5084(3) 0.44796(9) 0.09849(10) 0.0275(4) Uani 0.50 1 d PD . . Cl1 Cl 0.5277(3) 0.45806(9) 0.26348(10) 0.0358(4) Uani 1 1 d . . . Cl2 Cl 0.4797(4) 0.39059(11) -0.05236(11) 0.0454(4) Uani 1 1 d . . . O1 O 1.0073(9) 0.4424(3) 0.0997(3) 0.0450(12) Uani 1 1 d D . . H1A H 1.127(8) 0.478(4) 0.127(7) 0.054 Uiso 0.50 1 d PD A 1 H1B H 1.109(9) 0.433(6) 0.048(3) 0.054 Uiso 0.50 1 d PD B 1 H1D H 0.902(9) 0.469(5) 0.140(5) 0.054 Uiso 0.50 1 d PD C 2 H1C H 0.890(8) 0.445(7) 0.048(2) 0.054 Uiso 0.50 1 d PD D 2 N11 N -0.1332(13) 0.3623(3) 0.7533(4) 0.0378(15) Uani 1 1 d . . . H11 H -0.236(13) 0.394(3) 0.786(4) 0.045 Uiso 1 1 d . . . C12 C -0.1031(15) 0.2864(4) 0.7794(5) 0.0451(18) Uani 1 1 d . . . H12 H -0.1772 0.2697 0.8400 0.054 Uiso 1 1 calc R . . C13 C 0.0339(17) 0.2331(4) 0.7192(5) 0.0524(19) Uani 1 1 d . . . H13 H 0.0543 0.1799 0.7375 0.063 Uiso 1 1 calc R . . C14 C 0.1432(15) 0.2594(4) 0.6296(5) 0.0444(18) Uani 1 1 d . . . H14 H 0.2381 0.2237 0.5870 0.053 Uiso 1 1 calc R . . C15 C 0.1124(13) 0.3376(4) 0.6035(4) 0.0286(14) Uani 1 1 d . . . C16 C -0.0332(13) 0.3888(4) 0.6665(4) 0.0338(15) Uani 1 1 d . . . H16 H -0.0626 0.4419 0.6491 0.041 Uiso 1 1 calc R . . I1 I 0.27539(9) 0.38188(3) 0.46985(3) 0.03851(14) 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 Cu1 0.0250(8) 0.0375(9) 0.0206(7) -0.0011(7) 0.0065(6) 0.0021(7) Cl1 0.0332(9) 0.0497(10) 0.0250(8) -0.0002(8) 0.0071(7) -0.0005(8) Cl2 0.0406(9) 0.0645(12) 0.0317(8) -0.0150(9) 0.0088(7) 0.0009(9) O1 0.039(3) 0.069(4) 0.027(3) -0.005(3) 0.006(2) 0.004(2) N11 0.045(4) 0.041(4) 0.028(3) -0.009(3) 0.009(3) 0.005(3) C12 0.059(5) 0.046(4) 0.030(4) 0.005(4) 0.003(3) -0.003(4) C13 0.080(5) 0.040(4) 0.038(4) 0.003(4) 0.011(4) 0.015(4) C14 0.065(5) 0.038(4) 0.031(4) -0.010(4) 0.010(3) 0.007(4) C15 0.036(4) 0.030(4) 0.020(3) -0.003(3) 0.004(3) 0.002(3) C16 0.034(3) 0.037(4) 0.031(3) 0.004(3) 0.000(3) -0.005(3) I1 0.0358(2) 0.0502(3) 0.0300(2) 0.0029(2) 0.00588(18) -0.0011(2) _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 Cu1 O1 2.058(4) . ? Cu1 O1 2.068(4) 1_455 ? Cu1 Cl1 2.2347(19) . ? Cu1 Cl2 2.254(2) . ? Cu1 Cl2 2.783(2) 3_665 ? O1 Cu1 2.068(4) 1_655 ? O1 H1A 0.84(2) . ? O1 H1B 0.84(2) . ? O1 H1D 0.839(19) . ? O1 H1C 0.84(2) . ? N11 C12 1.326(7) . ? N11 C16 1.336(7) . ? N11 H11 0.82(5) . ? C12 C13 1.352(8) . ? C12 H12 0.9300 . ? C13 C14 1.384(8) . ? C13 H13 0.9300 . ? C14 C15 1.364(8) . ? C14 H14 0.9300 . ? C15 C16 1.368(8) . ? C15 I1 2.093(6) . ? C16 H16 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 O1 Cu1 O1 174.7(3) . 1_455 ? O1 Cu1 Cl1 90.28(13) . . ? O1 Cu1 Cl1 89.18(13) 1_455 . ? O1 Cu1 Cl2 89.96(13) . . ? Cl1 Cu1 Cl2 159.01(10) . . ? O1 Cu1 Cl2 91.06(16) . 3_665 ? O1 Cu1 Cl2 94.24(16) 1_455 3_665 ? Cl1 Cu1 Cl2 98.60(7) . 3_665 ? Cl2 Cu1 Cl2 102.38(7) . 3_665 ? Cu1 O1 H1A 122(3) . . ? Cu1 O1 H1B 122(3) . . ? H1A O1 H1B 101(3) . . ? Cu1 O1 H1D 122(3) 1_655 . ? Cu1 O1 H1C 122(3) 1_655 . ? H1D O1 H1C 103(3) . . ? C12 N11 C16 121.6(6) . . ? C12 N11 H11 121(4) . . ? C16 N11 H11 117(4) . . ? N11 C12 C13 120.8(6) . . ? N11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C14 118.5(6) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C15 C14 C13 120.2(6) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 118.8(6) . . ? C14 C15 I1 122.3(5) . . ? C16 C15 I1 118.8(4) . . ? N11 C16 C15 120.0(6) . . ? N11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? 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 O1 H1A Cl2 0.84(2) 2.95(7) 3.588(5) 134(8) 3_765 O1 H1A Cl1 0.84(2) 2.44(8) 3.023(4) 127(9) 1_655 O1 H1B Cl2 0.84(2) 2.21(3) 3.023(4) 163(7) 1_655 O1 H1C Cl2 0.84(2) 2.31(5) 3.051(4) 149(9) . O1 H1D Cl1 0.839(19) 2.33(6) 3.045(4) 143(9) . N11 H11 Cl2 0.82(5) 2.53(6) 3.171(5) 137(5) 1_456 N11 H11 Cl1 0.82(5) 2.83(6) 3.429(6) 132(5) 3_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.595 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.134 data_cgsw _database_code_depnum_ccdc_archive 'CCDC 915124' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(5-amino-2-iodopyridinium) diaquotrichlorocuprate chloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 Cl4 Cu I2 N4 O2' _chemical_formula_weight 683.41 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 8.1232(3) _cell_length_b 8.9577(4) _cell_length_c 13.9151(7) _cell_angle_alpha 79.998(2) _cell_angle_beta 78.4190(10) _cell_angle_gamma 85.351(2) _cell_volume 975.73(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9845 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 638 _exptl_absorpt_coefficient_mu 4.841 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1656 _exptl_absorpt_correction_T_max 0.5718 _exptl_absorpt_process_details 'via SADABS' _exptl_special_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.0889 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.6154. The \l/2 correction factor is 0.0015. ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36983 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 33.14 _reflns_number_total 7427 _reflns_number_gt 6356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'SAINT v7.53A (Bruker, 2008)' _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst.(2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst.(2008). A64, 112-122 ; _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. The structure is disordered so as to give the illusion of a ladder structure, whereas, in fact, each Cu site is discrete. The Cu1 site is occupied at 0.8151(10) and the Cu2 site at 1-0.8151. The two 2-amino-5-iodo-pyridine groups are both protonated at the pyridine nitrogen atom. The four chloro groups and two water molecules are present in full occupancy, and the copper ions are distributed, unequally, into the two holes created. This leads to disorder of the hydrogen atoms attached to the water molecules, being projected away from Cu1 when the oxygen atom is coordinated to Cu1 or away from Cu2 when the oxygen atom is coordinated to Cu2. With the exception of the oxygen-attached hydrogen atoms in the low occupancy configuation (when Cu2 is coordinated to the water), all other hydrogen atoms were clearly observed. Initially, the two Cu sites were constrained to have identical atomic displacement parameters, but substantial residual electron density at the Cu2 site (+/- 2 e^-^ %\A^-3^), coupled with the very high resolution data, permitted simultaneous refinement of occupancy and atomic displacement parameters. R1(observed) and wR2(all data) decreased substantially. The tables of bond distances and angles have been edited to remove non- sensical entries arising from the disorder. ; _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^)+(0.0059P)^2^+2.0700P] 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 0.00039(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7427 _refine_ls_number_parameters 245 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0511 _refine_ls_wR_factor_gt 0.0488 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.087 _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 Cu1 Cu 0.78699(3) 0.59083(3) 0.87900(2) 0.00795(7) Uani 0.8151(10) 1 d PD . . Cu2 Cu 0.2863(2) 0.5910(2) 0.87943(17) 0.0334(5) Uani 0.1849(10) 1 d P . . Cl4 Cl 0.35020(6) 0.56728(6) 0.71261(4) 0.01635(9) Uani 1 1 d . . . Cl1 Cl 0.84851(6) 0.56590(6) 0.71349(4) 0.01572(9) Uani 1 1 d . . . Cl3 Cl 0.73210(7) 0.70695(7) 1.01555(4) 0.01983(10) Uani 1 1 d . . . Cl2 Cl 0.77277(6) 0.31567(6) 0.97276(4) 0.01716(9) Uani 1 1 d . . . I2 I 0.427816(16) 0.281869(16) 0.494061(10) 0.01582(4) Uani 1 1 d . . . I1 I 0.077372(17) 0.718497(16) 0.499465(10) 0.01695(4) Uani 1 1 d . . . C13 C 0.2611(3) 0.9779(2) 0.35385(16) 0.0180(4) Uani 1 1 d . . . H13 H 0.2128 1.0386 0.4010 0.022 Uiso 1 1 calc R . . C23 C 0.2417(3) 0.0254(3) 0.64291(17) 0.0184(4) Uani 1 1 d . . . H23 H 0.2866 -0.0365 0.5960 0.022 Uiso 1 1 calc R . . N25 N -0.0397(3) 0.0061(2) 0.88685(16) 0.0258(4) Uani 1 1 d D . . H25A H -0.092(4) 0.068(3) 0.920(2) 0.031 Uiso 1 1 d D . . H25B H -0.070(4) -0.080(3) 0.899(2) 0.031 Uiso 1 1 d D . . N15 N 0.5508(3) 1.0058(2) 0.11201(16) 0.0238(4) Uani 1 1 d D . . H15A H 0.587(4) 0.950(3) 0.071(2) 0.029 Uiso 1 1 d D . . H15B H 0.564(4) 1.098(3) 0.094(2) 0.029 Uiso 1 1 d D . . O2 O 1.0297(2) 0.6178(2) 0.87114(12) 0.0195(3) Uani 1 1 d D . . H2A H 1.107(3) 0.595(4) 0.830(2) 0.023 Uiso 0.8151(10) 1 d PD . . H2B H 1.074(3) 0.621(4) 0.919(2) 0.023 Uiso 0.8151(10) 1 d PD . . O1 O 0.5436(2) 0.6134(2) 0.87279(12) 0.0194(3) Uani 1 1 d D . . H1A H 0.499(3) 0.591(4) 0.831(2) 0.023 Uiso 0.8151(10) 1 d PD . . H1B H 0.468(3) 0.614(4) 0.9215(19) 0.023 Uiso 0.8151(10) 1 d PD . . N21 N 0.2164(2) 0.2618(2) 0.69632(13) 0.0152(3) Uani 1 1 d . . . H21 H 0.2429 0.3551 0.6864 0.018 Uiso 1 1 calc R . . C15 C 0.4433(3) 0.9498(2) 0.19582(16) 0.0161(4) Uani 1 1 d . . . C25 C 0.0658(3) 0.0587(2) 0.80146(16) 0.0162(4) Uani 1 1 d . . . C12 C 0.2246(3) 0.8258(2) 0.36939(15) 0.0149(4) Uani 1 1 d . . . C16 C 0.4005(3) 0.7977(2) 0.21392(16) 0.0167(4) Uani 1 1 d . . . H16 H 0.4448 0.7346 0.1676 0.020 Uiso 1 1 calc R . . C22 C 0.2818(3) 0.1772(2) 0.62563(15) 0.0147(3) Uani 1 1 d . . . C14 C 0.3692(3) 1.0397(2) 0.26856(17) 0.0189(4) Uani 1 1 d . . . H14 H 0.3933 1.1415 0.2591 0.023 Uiso 1 1 calc R . . C24 C 0.1356(3) -0.0335(2) 0.72949(17) 0.0189(4) Uani 1 1 d . . . H24 H 0.1099 -0.1351 0.7404 0.023 Uiso 1 1 calc R . . C26 C 0.1124(3) 0.2098(2) 0.78144(16) 0.0163(4) Uani 1 1 d . . . H26 H 0.0710 0.2743 0.8273 0.020 Uiso 1 1 calc R . . N11 N 0.2954(2) 0.7427(2) 0.29831(14) 0.0162(3) Uani 1 1 d . . . H11 H 0.2720 0.6487 0.3075 0.019 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 Cu1 0.00765(12) 0.01025(13) 0.00554(12) -0.00166(9) 0.00038(8) -0.00119(9) Cu2 0.0260(9) 0.0235(9) 0.0543(13) -0.0128(8) -0.0106(8) 0.0000(7) Cl4 0.0159(2) 0.0196(2) 0.0139(2) -0.00462(17) -0.00065(16) -0.00459(17) Cl1 0.0174(2) 0.0182(2) 0.01170(19) -0.00404(16) -0.00032(16) -0.00462(17) Cl3 0.0172(2) 0.0257(3) 0.0187(2) -0.0126(2) -0.00107(17) 0.00013(18) Cl2 0.0159(2) 0.0191(2) 0.0171(2) -0.00654(18) -0.00163(16) -0.00036(17) I2 0.01329(6) 0.01845(7) 0.01516(6) -0.00261(5) -0.00107(4) -0.00182(4) I1 0.01363(6) 0.01952(7) 0.01700(7) -0.00237(5) -0.00116(4) -0.00239(4) C13 0.0208(9) 0.0160(9) 0.0173(9) -0.0060(7) -0.0016(7) 0.0013(7) C23 0.0206(9) 0.0160(9) 0.0183(9) -0.0067(8) -0.0002(8) 0.0006(7) N25 0.0326(11) 0.0168(9) 0.0223(10) -0.0019(8) 0.0067(8) -0.0006(8) N15 0.0309(10) 0.0176(9) 0.0181(9) -0.0007(7) 0.0047(8) 0.0003(8) O2 0.0131(6) 0.0310(9) 0.0153(7) -0.0083(6) -0.0006(5) -0.0021(6) O1 0.0137(7) 0.0300(9) 0.0150(7) -0.0062(6) -0.0015(5) -0.0016(6) N21 0.0175(8) 0.0131(8) 0.0153(8) -0.0038(6) -0.0022(6) -0.0016(6) C15 0.0178(9) 0.0150(9) 0.0154(9) -0.0021(7) -0.0043(7) 0.0018(7) C25 0.0179(9) 0.0155(9) 0.0144(9) -0.0021(7) -0.0018(7) 0.0009(7) C12 0.0137(8) 0.0168(9) 0.0145(9) -0.0030(7) -0.0030(7) -0.0013(7) C16 0.0197(9) 0.0156(9) 0.0150(9) -0.0049(7) -0.0023(7) 0.0006(7) C22 0.0147(8) 0.0165(9) 0.0133(8) -0.0033(7) -0.0025(7) -0.0005(7) C14 0.0230(10) 0.0129(9) 0.0197(10) -0.0025(7) -0.0026(8) 0.0013(7) C24 0.0235(10) 0.0131(9) 0.0187(10) -0.0024(7) -0.0005(8) -0.0009(7) C26 0.0195(9) 0.0151(9) 0.0141(9) -0.0040(7) -0.0021(7) 0.0004(7) N11 0.0193(8) 0.0126(8) 0.0174(8) -0.0039(6) -0.0035(6) -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 Cu1 O2 1.9844(16) . ? Cu1 O1 1.9886(16) . ? Cu1 Cl3 2.2721(6) . ? Cu1 Cl1 2.3027(6) . ? Cu1 Cl2 2.5806(6) . ? Cu2 O1 2.098(2) . ? Cu2 O2 2.103(2) 1_455 ? Cu2 Cl2 2.301(2) 2_667 ? Cu2 Cl4 2.318(2) . ? Cl2 Cu2 2.301(2) 2_667 ? I2 C22 2.086(2) . ? I1 C12 2.084(2) . ? C13 C14 1.385(3) . ? C13 C12 1.389(3) . ? C13 H13 0.9300 . ? C23 C24 1.382(3) . ? C23 C22 1.393(3) . ? C23 H23 0.9300 . ? N25 C25 1.353(3) . ? N25 H25A 0.82(2) . ? N25 H25B 0.81(2) . ? N15 C15 1.354(3) . ? N15 H15A 0.82(2) . ? N15 H15B 0.83(2) . ? O2 Cu2 2.103(2) 1_655 ? O2 H2A 0.81(2) . ? O2 H2B 0.82(2) . ? O1 H1A 0.80(2) . ? O1 H1B 0.82(2) . ? N21 C26 1.344(3) . ? N21 C22 1.345(3) . ? N21 H21 0.8600 . ? C15 C16 1.401(3) . ? C15 C14 1.413(3) . ? C25 C26 1.401(3) . ? C25 C24 1.411(3) . ? C12 N11 1.350(3) . ? C16 N11 1.347(3) . ? C16 H16 0.9300 . ? C14 H14 0.9300 . ? C24 H24 0.9300 . ? C26 H26 0.9300 . ? N11 H11 0.8600 . ? 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 O2 Cu1 O1 166.93(8) . . ? O2 Cu1 Cl3 88.18(5) . . ? O1 Cu1 Cl3 89.27(5) . . ? O2 Cu1 Cl1 88.21(5) . . ? O1 Cu1 Cl1 89.53(5) . . ? Cl3 Cu1 Cl1 158.69(2) . . ? O2 Cu1 Cl2 98.32(6) . . ? O1 Cu1 Cl2 94.71(5) . . ? Cl3 Cu1 Cl2 96.78(2) . . ? Cl1 Cu1 Cl2 104.52(2) . . ? O1 Cu2 O2 167.64(13) . 1_455 ? O1 Cu2 Cl2 89.56(9) . 2_667 ? O2 Cu2 Cl2 89.61(9) 1_455 2_667 ? O1 Cu2 Cl4 88.02(9) . . ? O2 Cu2 Cl4 89.43(9) 1_455 . ? Cl2 Cu2 Cl4 164.22(10) 2_667 . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C24 C23 C22 120.3(2) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 N25 H25A 118(2) . . ? C25 N25 H25B 122(2) . . ? H25A N25 H25B 118(3) . . ? C15 N15 H15A 119(2) . . ? C15 N15 H15B 123(2) . . ? H15A N15 H15B 117(3) . . ? Cu1 O2 H2A 127.5(17) . . ? Cu1 O2 H2B 125.2(17) . . ? H2A O2 H2B 103(2) . . ? Cu1 O1 H1A 127.8(18) . . ? Cu1 O1 H1B 124.1(17) . . ? H1A O1 H1B 104(2) . . ? C26 N21 C22 124.04(18) . . ? C26 N21 H21 118.0 . . ? C22 N21 H21 118.0 . . ? N15 C15 C16 120.7(2) . . ? N15 C15 C14 122.4(2) . . ? C16 C15 C14 116.9(2) . . ? N25 C25 C26 120.4(2) . . ? N25 C25 C24 122.8(2) . . ? C26 C25 C24 116.80(19) . . ? N11 C12 C13 117.82(19) . . ? N11 C12 I1 118.86(15) . . ? C13 C12 I1 123.24(15) . . ? N11 C16 C15 120.13(19) . . ? N11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N21 C22 C23 117.81(19) . . ? N21 C22 I2 118.51(15) . . ? C23 C22 I2 123.62(15) . . ? C13 C14 C15 120.8(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C23 C24 C25 120.7(2) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? N21 C26 C25 120.31(19) . . ? N21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C16 N11 C12 124.09(19) . . ? C16 N11 H11 118.0 . . ? C12 N11 H11 118.0 . . ? 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 O2 H2A Cl4 0.81(2) 2.32(2) 3.1145(16) 170(3) 1_655 O2 H2B Cl2 0.82(2) 2.30(2) 3.1071(17) 166(3) 2_767 O1 H1A Cl4 0.80(2) 2.28(2) 3.0720(17) 171(3) . O1 H1B Cl2 0.82(2) 2.31(2) 3.1016(16) 162(3) 2_667 N25 H25A Cl2 0.82(2) 2.55(2) 3.343(2) 162(3) 1_455 N15 H15A Cl3 0.82(2) 2.56(2) 3.310(2) 153(3) 1_554 N21 H21 Cl4 0.88(3) 2.24(3) 3.0842(19) 160(3) . N11 H11 Cl1 0.82(3) 2.33(3) 3.1300(19) 166(3) 2_666 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.429 _refine_diff_density_min -1.221 _refine_diff_density_rms 0.117 data_jg128 _database_code_depnum_ccdc_archive 'CCDC 915125' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2-amino-5-bromopyridinium) diaquatrichlorocuprate chloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 Br2 Cl4 Cu N4 O2' _chemical_formula_weight 589.43 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' O O 0.0106 0.0060 '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 7.948(2) _cell_length_b 16.162(5) _cell_length_c 14.896(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.180(4) _cell_angle_gamma 90.00 _cell_volume 1905.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.054 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 5.911 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8911 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(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 23481 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3840 _reflns_number_gt 2952 _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. The structure is disordered so as to give the illusion of a ladder structure, whereas, in fact, each Cu site is discrete. The Cu1 site is occupied at 0.9592(6) and the Cu2 site at 1-0.9592(6). The two 2-amino-5-bromo pyridine groups are both protonated at the pyridine nitrogen atom. The four chloro groups and two water molecules are present in full occupancy, and the copper ions are distributed, unequally, into the two holes created. This leads to disorder of the hydrogen atoms attached to the water molecules, being projected away from Cu1 when the oxygen atom is coordinated to Cu1 or away from Cu2 when the oxygen atom is coordinated to Cu2. With the exception of the oxygen-attached hydrogen atoms in the low occupancy configuation (when Cu2 is coordinated to the water), all other hydrogen atoms were clearly observed. The two Cu sites were constrained to have identical atomic displacement parameters. The tables of bond distances and angles have been edited to remove non- sensical entries arising from the disorder. ; _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^)+(0.0280P)^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 3840 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0521 _refine_ls_wR_factor_gt 0.0492 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _refine_ls_shift/su_max 0.010 _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 Cu2 Cu -0.2349(9) 0.5114(4) 0.1076(5) 0.01707(8) Uani 0.0408(6) 1 d P . . Cu1 Cu 0.26518(4) 0.509084(18) 0.10727(2) 0.01707(8) Uani 0.9592(6) 1 d P . . Cl3 Cl 0.25365(8) 0.38122(4) 0.04245(4) 0.02561(15) Uani 1 1 d . . . Cl1 Cl 0.28321(8) 0.59579(4) 0.23012(4) 0.02579(15) Uani 1 1 d . . . Cl2 Cl 0.25053(7) 0.61398(4) -0.02530(4) 0.02249(14) Uani 1 1 d . . . Cl4 Cl -0.21690(8) 0.59938(4) 0.22944(4) 0.02591(15) Uani 1 1 d . . . O1 O 0.0231(2) 0.50350(13) 0.11385(13) 0.0276(5) Uani 1 1 d . . . H1A H -0.048(4) 0.4780(18) 0.089(2) 0.033 Uiso 0.9592(6) 1 d P . . H1B H -0.052(4) 0.5333(18) 0.140(2) 0.033 Uiso 0.9592(6) 1 d P . . O2 O 0.5101(2) 0.50499(13) 0.11313(13) 0.0275(5) Uani 1 1 d . . . H2A H 0.582(4) 0.5321(18) 0.140(2) 0.033 Uiso 0.9592(6) 1 d P . . H2B H 0.574(4) 0.4758(18) 0.0794(19) 0.033 Uiso 0.9592(6) 1 d P . . N11 N 0.5418(3) 0.25474(14) 0.34986(15) 0.0233(5) Uani 1 1 d . . . H11 H 0.575(3) 0.2097(17) 0.3371(18) 0.028 Uiso 1 1 d . . . C12 C 0.5551(3) 0.31190(17) 0.28533(18) 0.0264(6) Uani 1 1 d . . . N12 N 0.6199(3) 0.28967(16) 0.20948(17) 0.0360(6) Uani 1 1 d . . . H12A H 0.643(4) 0.2412(19) 0.203(2) 0.043 Uiso 1 1 d . . . H12B H 0.623(4) 0.3233(19) 0.167(2) 0.043 Uiso 1 1 d . . . C13 C 0.5016(4) 0.39356(17) 0.30351(19) 0.0332(7) Uani 1 1 d . . . H13 H 0.5091 0.4360 0.2599 0.040 Uiso 1 1 d R . . C14 C 0.4386(3) 0.41124(16) 0.38405(19) 0.0298(6) Uani 1 1 d . . . H14 H 0.4024 0.4658 0.3962 0.036 Uiso 1 1 d R . . C15 C 0.4280(3) 0.34839(16) 0.44921(17) 0.0245(6) Uani 1 1 d . . . Br1 Br 0.35043(3) 0.372732(17) 0.562826(18) 0.02949(8) Uani 1 1 d . . . C16 C 0.4809(3) 0.27072(15) 0.43086(17) 0.0234(6) Uani 1 1 d . . . H16 H 0.4746 0.2280 0.4742 0.028 Uiso 1 1 d R . . N21 N -0.0334(3) 0.74654(14) 0.64488(15) 0.0242(5) Uani 1 1 d . . . H21 H -0.059(3) 0.7925(17) 0.6534(19) 0.029 Uiso 1 1 d . . . C22 C -0.0462(3) 0.69054(16) 0.71115(17) 0.0252(6) Uani 1 1 d . . . N22 N -0.1071(4) 0.71443(16) 0.78713(18) 0.0402(7) Uani 1 1 d . . . H22A H -0.130(4) 0.761(2) 0.797(2) 0.048 Uiso 1 1 d . . . H22B H -0.111(4) 0.681(2) 0.828(2) 0.048 Uiso 1 1 d . . . C23 C 0.0060(4) 0.60829(16) 0.69469(19) 0.0328(7) Uani 1 1 d . . . H23 H -0.0027 0.5667 0.7391 0.039 Uiso 1 1 d R . . C24 C 0.0673(3) 0.58877(16) 0.61473(18) 0.0293(6) Uani 1 1 d . . . H24 H 0.1041 0.5339 0.6045 0.035 Uiso 1 1 d R . . C25 C 0.0766(3) 0.64981(16) 0.54742(17) 0.0230(6) Uani 1 1 d . . . Br2 Br 0.15032(3) 0.623168(17) 0.433967(18) 0.02988(8) Uani 1 1 d . . . C26 C 0.0254(3) 0.72822(16) 0.56408(17) 0.0244(6) Uani 1 1 d . . . H26 H 0.0310 0.7700 0.5196 0.029 Uiso 1 1 d 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 Cu2 0.01513(15) 0.01954(16) 0.01687(15) -0.00179(13) 0.00319(11) -0.00052(13) Cu1 0.01513(15) 0.01954(16) 0.01687(15) -0.00179(13) 0.00319(11) -0.00052(13) Cl3 0.0260(3) 0.0207(3) 0.0312(4) -0.0061(3) 0.0085(3) -0.0022(3) Cl1 0.0267(3) 0.0293(4) 0.0221(3) -0.0086(3) 0.0067(3) -0.0039(3) Cl2 0.0226(3) 0.0205(3) 0.0250(3) 0.0000(3) 0.0058(2) -0.0003(2) Cl4 0.0221(3) 0.0306(4) 0.0256(3) -0.0067(3) 0.0058(3) -0.0033(3) O1 0.0156(10) 0.0344(12) 0.0332(11) -0.0130(9) 0.0035(8) -0.0021(8) O2 0.0168(10) 0.0355(12) 0.0304(11) -0.0123(9) 0.0035(8) -0.0010(8) N11 0.0247(13) 0.0180(11) 0.0275(13) 0.0023(10) 0.0039(9) 0.0010(10) C12 0.0241(15) 0.0307(16) 0.0239(15) 0.0051(12) -0.0012(11) -0.0028(12) N12 0.0523(17) 0.0293(14) 0.0275(14) 0.0063(12) 0.0106(12) 0.0017(13) C13 0.0430(18) 0.0249(15) 0.0312(16) 0.0113(12) 0.0004(13) 0.0006(13) C14 0.0328(16) 0.0207(15) 0.0351(17) 0.0016(12) -0.0020(12) 0.0036(12) C15 0.0209(14) 0.0297(15) 0.0223(14) -0.0006(12) -0.0007(11) -0.0015(11) Br1 0.02653(15) 0.03226(16) 0.03023(16) -0.00407(12) 0.00554(11) -0.00005(12) C16 0.0224(14) 0.0230(14) 0.0250(15) 0.0065(11) 0.0033(11) -0.0002(11) N21 0.0286(13) 0.0166(11) 0.0280(13) 0.0030(10) 0.0053(9) 0.0014(10) C22 0.0293(15) 0.0248(15) 0.0216(14) 0.0011(11) 0.0034(11) -0.0053(11) N22 0.0638(19) 0.0290(15) 0.0296(15) 0.0049(12) 0.0147(13) 0.0000(14) C23 0.0448(18) 0.0228(15) 0.0309(16) 0.0090(12) 0.0049(13) -0.0012(13) C24 0.0354(17) 0.0194(14) 0.0326(16) -0.0003(12) 0.0007(12) 0.0019(12) C25 0.0207(14) 0.0248(14) 0.0232(14) -0.0010(11) 0.0011(10) -0.0016(11) Br2 0.02750(16) 0.03419(17) 0.02861(15) -0.00506(12) 0.00613(11) -0.00008(12) C26 0.0219(14) 0.0265(15) 0.0256(15) 0.0061(12) 0.0055(11) -0.0013(11) _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 Cu2 O2 2.039(7) 1_455 ? Cu2 Cl4 2.299(7) . ? Cu2 Cl2 2.366(7) 3_565 ? Cu1 O1 1.9376(18) . ? Cu1 O2 1.9417(18) . ? Cu1 Cl3 2.2793(8) . ? Cu1 Cl1 2.2991(8) . ? Cu1 Cl2 2.5973(9) . ? Cl2 Cu2 2.366(7) 3_565 ? O1 H1A 0.77(3) . ? O1 H1B 0.88(3) . ? O2 Cu2 2.039(7) 1_655 ? O2 H2A 0.80(3) . ? O2 H2B 0.88(3) . ? N11 C12 1.344(3) . ? N11 C16 1.365(3) . ? N11 H11 0.80(3) . ? C12 N12 1.333(4) . ? C12 C13 1.420(4) . ? N12 H12A 0.81(3) . ? N12 H12B 0.83(3) . ? C13 C14 1.371(4) . ? C13 H13 0.9500 . ? C14 C15 1.413(4) . ? C14 H14 0.9501 . ? C15 C16 1.359(4) . ? C15 Br1 1.894(3) . ? C16 H16 0.9501 . ? N21 C22 1.350(3) . ? N21 C26 1.363(3) . ? N21 H21 0.78(3) . ? C22 N22 1.328(3) . ? C22 C23 1.420(4) . ? N22 H22A 0.79(3) . ? N22 H22B 0.82(3) . ? C23 C24 1.364(4) . ? C23 H23 0.9501 . ? C24 C25 1.413(4) . ? C24 H24 0.9499 . ? C25 C26 1.360(3) . ? C25 Br2 1.888(3) . ? 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 O2 Cu2 Cl4 89.5(3) 1_455 . ? O2 Cu2 Cl2 88.4(3) 1_455 3_565 ? Cl4 Cu2 Cl2 159.2(3) . 3_565 ? O1 Cu1 O2 172.85(9) . . ? O1 Cu1 Cl3 88.69(6) . . ? O2 Cu1 Cl3 89.43(6) . . ? O1 Cu1 Cl1 88.79(6) . . ? O2 Cu1 Cl1 89.70(6) . . ? Cl3 Cu1 Cl1 152.50(3) . . ? O1 Cu1 Cl2 95.29(6) . . ? O2 Cu1 Cl2 91.85(6) . . ? Cl3 Cu1 Cl2 105.80(3) . . ? Cl1 Cu1 Cl2 101.69(3) . . ? Cu1 O1 H1A 134(2) . . ? Cu1 O1 H1B 134.9(19) . . ? H1A O1 H1B 91(3) . . ? Cu1 O2 H2A 132(2) . . ? Cu1 O2 H2B 128.1(18) . . ? H2A O2 H2B 99(3) . . ? C12 N11 C16 124.0(2) . . ? C12 N11 H11 114(2) . . ? C16 N11 H11 122(2) . . ? N12 C12 N11 118.8(3) . . ? N12 C12 C13 123.9(3) . . ? N11 C12 C13 117.3(3) . . ? C12 N12 H12A 118(2) . . ? C12 N12 H12B 120(2) . . ? H12A N12 H12B 121(3) . . ? C14 C13 C12 120.0(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 119.2(2) . . ? C16 C15 Br1 120.2(2) . . ? C14 C15 Br1 120.6(2) . . ? C15 C16 N11 119.6(2) . . ? C15 C16 H16 120.0 . . ? N11 C16 H16 120.5 . . ? C22 N21 C26 123.7(2) . . ? C22 N21 H21 119(2) . . ? C26 N21 H21 118(2) . . ? N22 C22 N21 119.1(2) . . ? N22 C22 C23 123.6(2) . . ? N21 C22 C23 117.3(2) . . ? C22 N22 H22A 122(3) . . ? C22 N22 H22B 119(2) . . ? H22A N22 H22B 118(3) . . ? C24 C23 C22 120.0(2) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.3(2) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 120.0 . . ? C26 C25 C24 119.0(2) . . ? C26 C25 Br2 119.86(19) . . ? C24 C25 Br2 121.1(2) . . ? C25 C26 N21 119.7(2) . . ? C25 C26 H26 120.1 . . ? N21 C26 H26 120.2 . . ? 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 178.6(2) . . . . ? C16 N11 C12 C13 -0.1(4) . . . . ? N12 C12 C13 C14 -179.0(3) . . . . ? N11 C12 C13 C14 -0.4(4) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C13 C14 C15 C16 0.0(4) . . . . ? C13 C14 C15 Br1 177.3(2) . . . . ? C14 C15 C16 N11 -0.5(4) . . . . ? Br1 C15 C16 N11 -177.79(18) . . . . ? C12 N11 C16 C15 0.5(4) . . . . ? C26 N21 C22 N22 -179.2(3) . . . . ? C26 N21 C22 C23 0.4(4) . . . . ? N22 C22 C23 C24 -180.0(3) . . . . ? N21 C22 C23 C24 0.4(4) . . . . ? C22 C23 C24 C25 -1.0(4) . . . . ? C23 C24 C25 C26 0.7(4) . . . . ? C23 C24 C25 Br2 -176.8(2) . . . . ? C24 C25 C26 N21 0.1(4) . . . . ? Br2 C25 C26 N21 177.68(19) . . . . ? C22 N21 C26 C25 -0.7(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 N22 H22A Cl1 0.79(3) 2.59(3) 3.279(3) 147(3) 4_576 N22 H22B Cl3 0.82(3) 2.53(3) 3.275(3) 152(3) 3_566 N21 H21 Cl1 0.78(3) 2.53(3) 3.250(2) 154(3) 4_576 N12 H12B Cl2 0.83(3) 2.62(3) 3.395(3) 154(3) 3_665 N12 H12A Cl4 0.81(3) 2.55(3) 3.279(3) 149(3) 2_545 N11 H11 Cl4 0.80(3) 2.37(3) 3.152(2) 163(3) 2_545 O2 H2B Cl2 0.88(3) 2.22(3) 3.079(2) 166(3) 3_665 O2 H2A Cl4 0.80(3) 2.27(3) 3.059(2) 173(3) 1_655 O1 H1B Cl4 0.88(3) 2.22(3) 3.098(2) 170(3) . O1 H1A Cl2 0.77(3) 2.33(3) 3.091(2) 172(3) 3_565 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.469 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.073