# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_compound1 _database_code_CSD 167340 _audit_creation_method SHELXL _publ_contact_author_name 'Antonio Luque' _publ_contact_author_address ; Antonio Luque Departamento de Quimica Inorganica Facultad de Ciencias Universidad del Pais Vasco Apdo. 644 E-48080 Bilbao Spain ; _publ_contact_author_email 'qipluara@lg.ehu.es' _publ_contact_author_fax '+34-944 648 500' _publ_contact_author_phone '+34-946 012 701' _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemisty, Paper Ref.:B104085P' _publ_section_title ; Crystal packing and physical properties of pyridinium tetrabromocuprate(II) complexes assembled via hydrogen bonds and aromatic stacking interactions ; loop_ _publ_author_name _publ_author_address 'Antonio Luque' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Jon Sertucha' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Oscar Castillo' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Pascual Roman' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; _chemical_name_systematic ; bis(pyridinium) tetrabromocuprate(II) ; _chemical_name_common ? _chemical_formula_moiety '2(C5H6N), (CuBr4)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10H12Br4Cu1N2' _chemical_formula_weight 543.37 _chemical_melting_point ? _chemical_compound_source 'ethanolic synthesis' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.291 2.468 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.162(1) _cell_length_b 14.249(1) _cell_length_c 13.862(1) _cell_angle_alpha 90.00 _cell_angle_beta 94.77(2) _cell_angle_gamma 90.00 _cell_volume 1606.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.6 _cell_measurement_theta_max 13.3 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'dark-violet' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 2.24(1) _exptl_crystal_density_diffrn 2.247 _exptl_crystal_density_method flotation _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 11.289 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_process_details 'DIFABS (Walker and Stuart, 1989)' _exptl_absorpt_correction_T_min 0.125 _exptl_absorpt_correction_T_max 0.184 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius CAD4 diffractometer' _diffrn_measurement_method '\w/2\q mode' _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 1 _diffrn_reflns_number 2517 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 29.96 _reflns_number_total 2342 _reflns_number_gt 1023 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 programs' _computing_cell_refinement 'local programs' _computing_data_reduction 'XRAY-76 (Stewart, 1976)' _computing_structure_solution 'DIRDIF-92 (Beurskens, 1992)' _computing_structure_refinement 'XRAY-76 (Stewart, 1976)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement on F. Weighted R-factors wR and all goodnesses of fit S, conventional R-factors R are based on F. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'PESOS (Martinez-Ripoll, 1975)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1023 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.071 _refine_ls_R_factor_gt 0.043 _refine_ls_wR_factor_all 0.097 _refine_ls_wR_factor_ref 0.050 _refine_ls_goodness_of_fit_all 1.43 _refine_ls_goodness_of_fit_ref 1.19 _refine_ls_shift/su_max 0.08 _refine_ls_shift/su_mean 0.01 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.50000 0.02996(9) 0.25000 0.0436(4) Uani 1 d . . Br1 Br 0.27843(8) 0.13663(7) 0.21739(7) 0.0549(4) Uani 1 d . . Br2 Br 0.37261(9) -0.07579(7) 0.35178(8) 0.0644(4) Uani 1 d . . N11 N 0.1609(9) 0.1121(7) 0.4464(6) 0.062(3) Uani 1 d . . C12 C 0.0725(9) 0.1912(8) 0.4368(8) 0.062(4) Uani 1 d . . C13 C 0.0007(9) 0.2249(9) 0.5139(9) 0.063(4) Uani 1 d . . C14 C 0.0225(9) 0.1792(8) 0.5997(7) 0.064(3) Uani 1 d . . C15 C 0.1194(9) 0.0997(8) 0.6076(8) 0.067(3) Uani 1 d . . C16 C 0.1874(9) 0.0681(9) 0.5293(8) 0.068(4) Uani 1 d . . H11 H 0.228(7) 0.085(6) 0.399(5) 0.04(2) Uiso 1 d . . H12 H 0.055(8) 0.212(7) 0.383(6) 0.03(1) Uiso 1 d . . H13 H -0.041(8) 0.274(7) 0.514(7) 0.04(2) Uiso 1 d . . H14 H -0.042(7) 0.200(7) 0.654(7) 0.05(2) Uiso 1 d . . H15 H 0.135(7) 0.055(7) 0.673(7) 0.07(3) Uiso 1 d . . H16 H 0.267(7) 0.041(8) 0.532(8) 0.07(3) Uiso 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0411(7) 0.0460(7) 0.0441(7) 0 0.0036(6) 0 Br1 0.0484(5) 0.0598(5) 0.0564(5) 0.0095(4) 0.0009(4) 0.0137(4) Br2 0.0703(6) 0.0588(6) 0.0662(6) 0.0017(5) 0.0166(5) 0.0183(5) N11 0.056(5) 0.082(6) 0.048(4) 0.001(4) 0.006(4) -0.013(4) C12 0.061(6) 0.079(7) 0.043(5) -0.018(6) -0.010(4) 0.015(5) C13 0.064(6) 0.058(6) 0.067(7) -0.004(5) 0.000(5) 0.005(5) C14 0.074(6) 0.069(6) 0.050(5) 0.004(6) 0.013(5) -0.001(5) C15 0.082(7) 0.060(5) 0.057(5) 0.008(5) -0.008(5) 0.010(5) C16 0.066(6) 0.075(7) 0.061(6) 0.016(6) -0.001(5) 0.003(5) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 Br1 2.377(1) . yes Cu1 Br2 2.364(1) . yes N11 C12 1.34(1) . no N11 C16 1.31(1) . no C12 C13 1.35(2) . no C13 C14 1.35(2) . no C14 C15 1.38(1) . no C15 C16 1.34(2) . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Cu1 Br1 100.49(6) . 2_655 yes Br1 Cu1 Br2 98.96(4) . . yes Br1 Cu1 Br2 131.28(3) . 2_655 yes Br2 Cu1 Br1 131.28(4) . 2_655 yes Br2 Cu1 Br2 100.78(6) . 2_655 yes Br1 Cu1 Br2 98.96(4) 2_655 2_655 yes C12 N11 C16 123(1) . . no N11 C12 C13 119(1) . . no C12 C13 C14 119(1) . . no C13 C14 C15 120(1) . . no C14 C15 C16 119(1) . . no N11 C16 C15 120(1) . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N11 H11 Br1 0.97(7) 2.69(7) 3.41(1) 132(6) . yes N11 H11 Br2 0.97(7) 2.68(8) 3.50(1) 142(6) . yes _refine_diff_density_max 0.64 _refine_diff_density_min -0.87 #===END # CIF-file generated for (2-mepyH)2[CuBr4] data_compound2 _database_code_CSD 167341 _audit_creation_method SHELXL _publ_contact_author_name 'Antonio Luque' _publ_contact_author_address ; Antonio Luque Departamento de Quimica Inorganica Facultad de Ciencias Universidad del Pais Vasco Apdo. 644 E-48080 Bilbao Spain ; _publ_contact_author_email 'qipluara@lg.ehu.es' _publ_contact_author_fax '+34-944 648 500' _publ_contact_author_phone '+34-946 012 701' _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemisty' _publ_section_title ; Crystal packing and physical properties of pyridinium tetrabromocuprate(II) complexes assembled via hydrogen bonds and aromatic stacking interactions ; loop_ _publ_author_name _publ_author_address 'Antonio Luque' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Jon Sertucha' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Oscar Castillo' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Pascual Roman' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; _chemical_name_systematic ; bis(2-methylpyridinium) tetrabromocuprate(II) ; _chemical_name_common ? _chemical_formula_moiety '2(C6H8N), (CuBr4)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12H16Br4Cu1N2' _chemical_formula_weight 571.44 _chemical_melting_point 388 _chemical_compound_source 'ethanolic synthesis' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.291 2.468 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.789(3) _cell_length_b 8.744(2) _cell_length_c 15.518(3) _cell_angle_alpha 90.0 _cell_angle_beta 135.15(3) _cell_angle_gamma 90.0 _cell_volume 1798(1) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 13.5 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'dark-violet' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 2.12(1) _exptl_crystal_density_diffrn 2.111 _exptl_crystal_density_method flotation _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 10.093 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_process_details 'DIFABS (Walker and Stuart, 1989)' _exptl_absorpt_correction_T_min 0.176 _exptl_absorpt_correction_T_max 0.298 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius CAD4 diffractometer' _diffrn_measurement_method '\w/2\q mode' _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 2841 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 29.87 _reflns_number_total 2591 _reflns_number_gt 1066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 programs' _computing_cell_refinement 'local programs' _computing_data_reduction 'XRAY-76 (Stewart, 1976)' _computing_structure_solution 'DIRDIF-92 (Beurskens, 1992)' _computing_structure_refinement 'XRAY-76 (Stewart, 1976)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement on F. Weighted R-factors wR and all goodnesses of fit S, conventional R-factors R are based on F. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'PESOS (Martinez-Ripoll, 1975)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1066 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.071 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_all 0.101 _refine_ls_wR_factor_ref 0.045 _refine_ls_goodness_of_fit_all 1.48 _refine_ls_goodness_of_fit_ref 1.11 _refine_ls_shift/su_max 0.08 _refine_ls_shift/su_mean 0.01 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.50000 0.52473(14) 0.75000 0.0348(4) Uani 1 d . . Br1 Br 0.61215(7) 0.64781(9) 0.74784(9) 0.0439(3) Uani 1 d . . Br2 Br 0.38072(7) 0.4210(9) 0.54905(8) 0.0486(3) Uani 1 d . . N11 N 0.3883(7) 0.7670(9) 0.4540(8) 0.050(3) Uani 1 d . . C12 C 0.3773(6) 0.9159(9) 0.4630(7) 0.038(3) Uani 1 d . . C13 C 0.3587(7) 1.0151(9) 0.3790(9) 0.050(3) Uani 1 d . . C14 C 0.3496(8) 0.9589(10) 0.2888(9) 0.053(3) Uani 1 d . . C15 C 0.3612(9) 0.8052(12) 0.2839(9) 0.058(4) Uani 1 d . . C16 C 0.3791(9) 0.7103(11) 0.3676(11) 0.062(4) Uani 1 d . . C17 C 0.3837(9) 0.9633(12) 0.5604(11) 0.061(4) Uani 1 d . . H11 H 0.401(5) 0.701(7) 0.512(7) 0.03(1) Uiso 1 d . . H13 H 0.352 1.099 0.374 0.05 Uiso 1 d . . H14 H 0.366 1.025 0.265 0.05 Uiso 1 d . . H15 H 0.381 0.745 0.244 0.05 Uiso 1 d . . H16 H 0.390 0.589 0.384 0.05 Uiso 1 d . . H171 H 0.453 0.933 0.643 0.05 Uiso 1 d . . H172 H 0.331 0.910 0.550 0.05 Uiso 1 d . . H173 H 0.378 1.077 0.570 0.05 Uiso 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0350(7) 0.0364(8) 0.0335(7) 0 0.0245(6) 0 Br1 0.0410(5) 0.0442(5) 0.0543(5) -0.0023(4) 0.0365(4) 0.0009(4) Br2 0.0522(5) 0.0456(5) 0.0380(4) -0.0093(4) 0.0285(4) -0.0092(4) N11 0.061(5) 0.040(4) 0.057(5) 0.014(4) 0.045(4) 0.013(4) C12 0.036(4) 0.039(5) 0.043(4) 0.000(4) 0.029(4) -0.003(4) C13 0.043(5) 0.039(5) 0.060(6) -0.002(4) 0.034(5) 0.005(5) C14 0.065(6) 0.053(6) 0.049(5) -0.002(5) 0.043(5) 0.008(4) C15 0.070(7) 0.067(7) 0.046(5) -0.005(5) 0.044(5) -0.005(5) C16 0.072(7) 0.040(5) 0.067(7) 0.000(5) 0.047(6) -0.012(5) C17 0.070(6) 0.067(7) 0.063(6) 0.002(6) 0.053(6) 0.001(5) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 Br1 2.387(1) . yes Cu1 Br2 2.379(3) . yes N11 C12 1.34(1) . no N11 C16 1.32(2) . no C12 C13 1.39(2) . no C12 C17 1.49(2) . no C13 C14 1.38(2) . no C14 C15 1.37(1) . no C15 C16 1.37(2) . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Cu1 Br1 126.41(6) . 2_656 yes Br1 Cu1 Br2 100.03(9) . . yes Br1 Cu1 Br2 99.76(4) . 2_656 yes Br2 Cu1 Br1 99.76(4) . 2_656 yes Br2 Cu1 Br2 135.19(6) . 2_656 yes Br1 Cu1 Br2 100.03(9) 2_656 2_656 yes C12 N11 C16 124(1) . . no N11 C12 C13 118(1) . . no N11 C12 C17 118(1) . . no C13 C12 C17 124(1) . . no C12 C13 C14 120(1) . . no C13 C14 C15 120(1) . . no C14 C15 C16 119(1) . . no N11 C16 C15 120(1) . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N11 H11 Br2 0.95(8) 2.60(7) 3.41(1) 144(6) . yes _refine_diff_density_max 0.73 _refine_diff_density_min -1.07 #===END # CIF-file generated for (3-mepyH)2[CuBr4] data_compound3 _database_code_CSD 167342 _audit_creation_method SHELXL _publ_contact_author_name 'Antonio Luque' _publ_contact_author_address ; Antonio Luque Departamento de Quimica Inorganica Facultad de Ciencias Universidad del Pais Vasco Apdo. 644 E-48080 Bilbao Spain ; _publ_contact_author_email 'qipluara@lg.ehu.es' _publ_contact_author_fax '+34-944 648 500' _publ_contact_author_phone '+34-946 012 701' _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemisty' _publ_section_title ; Crystal packing and physical properties of pyridinium tetrabromocuprate(II) complexes assembled via hydrogen bonds and aromatic stacking interactions ; loop_ _publ_author_name _publ_author_address 'Antonio Luque' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Jon Sertucha' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Oscar Castillo' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Pascual Roman' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; _chemical_name_systematic ; bis(3-methylpyridinium) tetrabromocuprate(II) ; _chemical_name_common ? _chemical_formula_moiety '2(C6H8N), (CuBr4)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12H16Br4Cu1N2' _chemical_formula_weight 571.44 _chemical_melting_point 408 _chemical_compound_source 'ethanolic synthesis' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.291 2.468 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 0.0000 '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 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 9.165(1) _cell_length_b 13.592(2) _cell_length_c 14.404(3) _cell_angle_alpha 90.0 _cell_angle_beta 102.41(2) _cell_angle_gamma 90.0 _cell_volume 1752.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.1 _cell_measurement_theta_max 13.8 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'dark-violet' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 2.16(1) _exptl_crystal_density_diffrn 2.166 _exptl_crystal_density_method flotation _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 10.355 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_process_details 'DIFABS (Walker and Stuart, 1989)' _exptl_absorpt_correction_T_min 0.072 _exptl_absorpt_correction_T_max 0.075 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius CAD4 diffractometer' _diffrn_measurement_method '\w/2\q mode' _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 1 _diffrn_reflns_number 5474 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.0 _diffrn_reflns_theta_max 30.0 _reflns_number_total 5097 _reflns_number_gt 1594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 programs' _computing_cell_refinement 'local programs' _computing_data_reduction 'XRAY-76 (Stewart, 1976)' _computing_structure_solution 'DIRDIF-92 (Beurskens, 1992)' _computing_structure_refinement 'XRAY-76 (Stewart, 1976)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement on F. Weighted R-factors wR and all goodnesses of fit S, conventional R-factors R are based on F. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'PESOS (Martinez-Ripoll, 1975)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1594 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.081 _refine_ls_R_factor_gt 0.040 _refine_ls_wR_factor_all 0.077 _refine_ls_wR_factor_ref 0.040 _refine_ls_goodness_of_fit_all 1.43 _refine_ls_goodness_of_fit_ref 1.16 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_shift/su_max 0.06 _refine_ls_shift/su_mean 0.02 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.55309(9) 0.45741(7) 0.20240(8) 0.0380(3) Uani 1 d . . Br1 Br 0.46000(9) 0.58074(7) 0.29165(8) 0.0544(4) Uani 1 d . . Br2 Br 0.34900(8) 0.34544(7) 0.17878(6) 0.0461(4) Uani 1 d . . Br3 Br 0.75638(7) 0.34359(9) 0.23206(6) 0.0515(5) Uani 1 d . . Br4 Br 0.65628(9) 0.56533(7) 0.10287(8) 0.0534(4) Uani 1 d . . N11 N 0.4407(8) 0.7586(6) 0.0876(5) 0.041(3) Uani 1 d . . C12 C 0.4585(9) 0.7842(7) 0.0035(7) 0.046(4) Uani 1 d . . C13 C 0.3922(9) 0.8691(7) -0.0402(6) 0.046(4) Uani 1 d . . C14 C 0.3091(9) 0.9236(8) 0.0089(8) 0.055(4) Uani 1 d . . C15 C 0.2927(9) 0.8948(9) 0.0973(7) 0.055(4) Uani 1 d . . C16 C 0.3599(10) 0.8111(10) 0.1366(7) 0.055(4) Uani 1 d . . C17 C 0.4166(12) 0.8979(9) -0.1375(7) 0.071(5) Uani 1 d . . N21 N 0.8641(8) 0.3799(6) 0.0258(5) 0.047(3) Uani 1 d . . C22 C 0.9493(9) 0.3005(8) 0.0353(6) 0.042(4) Uani 1 d . . C23 C 1.0174(9) 0.2714(7) -0.0361(5) 0.037(3) Uani 1 d . . C24 C 0.9933(10) 0.3249(8) -0.1186(7) 0.052(4) Uani 1 d . . C25 C 0.9055(11) 0.4075(9) -0.1253(6) 0.058(4) Uani 1 d . . C26 C 0.8405(9) 0.4349(8) -0.0549(8) 0.055(4) Uani 1 d . . C27 C 1.1118(11) 0.1803(8) -0.0236(8) 0.060(4) Uani 1 d . . H11 H 0.498(7) 0.697(6) 0.122(6) 0.04(1) Uiso 1 d . . H12 H 0.529 0.748 -0.006 0.05 Uiso 1 d . . H14 H 0.264 0.974 -0.018 0.05 Uiso 1 d . . H15 H 0.224 0.925 0.128 0.05 Uiso 1 d . . H16 H 0.346 0.783 0.204 0.05 Uiso 1 d . . H171 H 0.527 0.905 -0.134 0.05 Uiso 1 d . . H172 H 0.380 0.842 -0.183 0.05 Uiso 1 d . . H173 H 0.369 0.959 -0.170 0.05 Uiso 1 d . . H21 H 0.821(7) 0.398(6) 0.076(5) 0.04(1) Uiso 1 d . . H22 H 0.961 0.274 0.105 0.05 Uiso 1 d . . H24 H 1.043 0.303 -0.167 0.05 Uiso 1 d . . H25 H 0.886 0.448 -0.187 0.05 Uiso 1 d . . H26 H 0.755 0.484 -0.060 0.05 Uiso 1 d . . H271 H 1.056 0.123 -0.010 0.05 Uiso 1 d . . H272 H 1.200 0.191 0.037 0.05 Uiso 1 d . . H273 H 1.169 0.161 -0.074 0.05 Uiso 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0356(6) 0.0401(6) 0.0375(6) 0.0005(7) 0.0062(5) 0.0003(7) Br1 0.0550(7) 0.0539(7) 0.0557(7) -0.0004(7) 0.0149(5) -0.0170(7) Br2 0.0444(6) 0.0476(7) 0.0467(7) -0.0073(5) 0.0107(5) -0.0024(5) Br3 0.0474(7) 0.0567(8) 0.0492(8) 0.0167(6) 0.0079(6) 0.0141(6) Br4 0.0577(6) 0.0454(7) 0.0621(7) 0.0066(6) 0.0243(5) 0.0115(6) N11 0.034(4) 0.045(5) 0.038(5) -0.003(4) -0.005(4) -0.007(4) C12 0.040(6) 0.052(7) 0.042(7) 0.011(5) 0.003(5) 0.003(5) C13 0.041(6) 0.051(7) 0.040(6) -0.000(5) -0.005(5) -0.006(5) C14 0.046(6) 0.056(7) 0.057(7) 0.007(5) -0.000(6) -0.005(6) C15 0.044(6) 0.066(8) 0.055(8) -0.000(6) 0.008(5) -0.017(7) C16 0.045(7) 0.071(9) 0.049(7) 0.007(6) 0.011(6) 0.001(7) C17 0.092(9) 0.060(8) 0.054(8) -0.019(7) -0.000(7) 0.018(6) N21 0.044(5) 0.051(5) 0.046(6) -0.002(5) 0.007(4) -0.004(4) C22 0.040(5) 0.061(8) 0.026(6) 0.001(6) 0.007(5) 0.001(5) C23 0.030(5) 0.055(7) 0.024(5) -0.005(5) -0.000(4) -0.009(5) C24 0.043(6) 0.067(8) 0.045(7) -0.002(6) 0.008(5) -0.012(6) C25 0.064(7) 0.072(9) 0.037(6) -0.007(7) 0.007(6) 0.001(6) C26 0.041(6) 0.053(7) 0.065(8) 0.004(5) 0.000(6) 0.003(7) C27 0.061(7) 0.061(8) 0.059(8) 0.008(6) 0.018(6) -0.007(6) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 Br1 2.380(2) . yes Cu1 Br2 2.379(1) . yes Cu1 Br3 2.389(1) . yes Cu1 Br4 2.384(2) . yes N11 C12 1.30(1) . no N11 C16 1.33(1) . no C12 C13 1.39(1) . no C13 C14 1.36(1) . no C13 C17 1.52(1) . no C14 C15 1.37(2) . no C15 C16 1.36(2) . no N21 C22 1.32(1) . no N21 C26 1.36(1) . no C22 C23 1.37(1) . no C23 C24 1.37(1) . no C23 C27 1.50(1) . no C24 C25 1.37(2) . no C25 C26 1.34(2) . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Cu1 Br2 99.54(5) . . yes Br1 Cu1 Br3 135.74(6) . . yes Br1 Cu1 Br4 97.24(5) . . yes Br2 Cu1 Br3 99.81(6) . . yes Br2 Cu1 Br4 135.16(6) . . yes Br3 Cu1 Br4 96.38(5) . . yes C12 N11 C16 123(1) . . no N11 C12 C13 121(1) . . no C12 C13 C14 117(1) . . no C12 C13 C17 120(1) . . no C14 C13 C17 123(1) . . no C13 C14 C15 121(1) . . no C14 C15 C16 120(1) . . no N11 C16 C15 119(1) . . no C22 N21 C26 121(1) . . no N21 C22 C23 121(1) . . no C22 C23 C24 119(1) . . no C22 C23 C27 120(1) . . no C24 C23 C27 122(1) . . no C23 C24 C25 119(1) . . no C24 C25 C26 122(1) . . no N21 C26 C25 119(1) . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N11 H11 Br4 1.05(8) 2.36(8) 3.27(1) 144(6) . yes N21 H21 Br3 0.93(7) 2.55(7) 3.36(1) 146(7) . yes _refine_diff_density_max 0.83 _refine_diff_density_min -0.57 #===END # CIF-file generated for (4-mepyH)2[CuBr4] data_compound4 _database_code_CSD 167343 _audit_creation_method SHELXL _publ_contact_author_name 'Antonio Luque' _publ_contact_author_address ; Antonio Luque Departamento de Quimica Inorganica Facultad de Ciencias Universidad del Pais Vasco Apdo. 644 E-48080 Bilbao Spain ; _publ_contact_author_email 'qipluara@lg.ehu.es' _publ_contact_author_fax '+34-944 648 500' _publ_contact_author_phone '+34-946 012 701' _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemisty' _publ_section_title ; Crystal packing and physical properties of pyridinium tetrabromocuprate(II) complexes assembled via hydrogen bonds and aromatic stacking interactions ; loop_ _publ_author_name _publ_author_address 'Antonio Luque' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Jon Sertucha' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Oscar Castillo' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; 'Pascual Roman' ; Departamento de Quimica Inorganica, Facultad de Ciencias, Universidad del Pais Vasco, Apdo. 644, E-48080 Bilbao, Spain ; _chemical_name_systematic ; bis(4-methylpyridinium) tetrabromocuprate(II) ; _chemical_name_common ? _chemical_formula_moiety '2(C6H8N), (CuBr4)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12H16Br4Cu1N2' _chemical_formula_weight 571.44 _chemical_melting_point 383 _chemical_compound_source 'ethanolic synthesis' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.291 2.468 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 0.0000 '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 8.483(2) _cell_length_b 9.399(2) _cell_length_c 13.227(2) _cell_angle_alpha 96.29(3) _cell_angle_beta 91.29(3) _cell_angle_gamma 116.41(2) _cell_volume 935.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.7 _cell_measurement_theta_max 13.3 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'dark-violet' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 2.04(1) _exptl_crystal_density_diffrn 2.028 _exptl_crystal_density_method flotation _exptl_crystal_F_000 542 _exptl_absorpt_coefficient_mu 9.696 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_process_details 'DIFABS (Walker and Stuart, 1989)' _exptl_absorpt_correction_T_min 0.260 _exptl_absorpt_correction_T_max 0.379 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius CAD4 diffractometer' _diffrn_measurement_method '\w/2\q mode' _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 1 _diffrn_reflns_number 5659 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.0 _diffrn_reflns_theta_max 30.0 _reflns_number_total 5438 _reflns_number_gt 1121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 programs' _computing_cell_refinement 'local programs' _computing_data_reduction 'XRAY-76 (Stewart, 1976)' _computing_structure_solution 'DIRDIF-92 (Beurskens, 1992)' _computing_structure_refinement 'XRAY-76 (Stewart, 1976)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material ? _refine_special_details ; Refinement on F. Weighted R-factors wR and all goodnesses of fit S, conventional R-factors R are based on F. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'PESOS (Martinez-Ripoll, 1975)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens calc _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1121 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.087 _refine_ls_R_factor_gt 0.045 _refine_ls_wR_factor_all 0.101 _refine_ls_wR_factor_ref 0.045 _refine_ls_goodness_of_fit_all 1.54 _refine_ls_goodness_of_fit_ref 1.20 _refine_ls_shift/su_max 0.06 _refine_ls_shift/su_mean 0.02 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.1114(2) 0.0153(2) 0.2345(2) 0.052(1) Uani 1 d . . Br1 Br 0.1211(2) -0.2084(2) 0.3042(2) 0.064(1) Uani 1 d . . Br2 Br 0.4068(2) 0.1824(1) 0.2104(2) 0.067(1) Uani 1 d . . Br3 Br 0.0251(2) 0.2024(2) 0.3286(2) 0.060(1) Uani 1 d . . Br4 Br -0.1568(2) -0.1299(1) 0.1269(2) 0.063(1) Uani 1 d . . N11 N 0.8244(14) 0.2182(15) 0.1046(8) 0.056(8) Uani 1 d . . C12 C 0.7337(29) 0.1449(22) 0.0137(17) 0.084(14) Uani 1 d . . C13 C 0.6853(17) 0.2255(15) -0.0493(8) 0.052(9) Uani 1 d . . C14 C 0.7245(17) 0.3850(18) -0.0208(10) 0.059(10) Uani 1 d . . C15 C 0.8099(18) 0.4588(16) 0.0788(9) 0.053(9) Uani 1 d . . C16 C 0.8615(18) 0.3691(19) 0.1363(8) 0.054(10) Uani 1 d . . C17 C 0.6751(25) 0.4774(22) -0.0908(12) 0.084(13) Uani 1 d . . N21 N 0.2696(28) 0.2058(36) 0.6198(13) 0.172(18) Uani 1 d . . C22 C 0.3015(39) 0.1178(28) 0.5424(23) 0.131(19) Uani 1 d . . C23 C 0.4534(25) 0.1750(27) 0.4857(9) 0.077(13) Uani 1 d . . C24 C 0.5770(16) 0.3271(19) 0.5231(11) 0.049(10) Uani 1 d . . C25 C 0.5561(17) 0.4125(23) 0.6019(14) 0.069(11) Uani 1 d . . C26 C 0.3948(42) 0.3446(33) 0.6494(11) 0.113(19) Uani 1 d . . C27 C 0.7506(33) 0.3919(30) 0.4718(14) 0.115(17) Uani 1 d . . H11 H 0.868 0.160 0.151 0.05 Uiso 1 c . . H12 H 0.700 0.025 -0.011 0.05 Uiso 1 c . . H13 H 0.620 0.175 -0.121 0.05 Uiso 1 c . . H15 H 0.829 0.573 0.102 0.05 Uiso 1 c . . H16 H 0.928 0.426 0.207 0.05 Uiso 1 c . . H171 H 0.543 0.423 -0.105 0.05 Uiso 1 c . . H172 H 0.732 0.479 -0.155 0.05 Uiso 1 c . . H173 H 0.703 0.596 -0.069 0.05 Uiso 1 c . . H21 H 0.171 0.176 0.665 0.05 Uiso 1 c . . H22 H 0.201 0.003 0.530 0.05 Uiso 1 c . . H23 H 0.469 0.105 0.424 0.05 Uiso 1 c . . H25 H 0.653 0.526 0.631 0.05 Uiso 1 c . . H26 H 0.399 0.424 0.714 0.05 Uiso 1 c . . H271 H 0.722 0.386 0.394 0.05 Uiso 1 c . . H272 H 0.807 0.317 0.477 0.05 Uiso 1 c . . H273 H 0.840 0.502 0.495 0.05 Uiso 1 c . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.046(1) 0.051(1) 0.057(2) 0.021(1) 0.008(1) 0.009(1) Br1 0.076(1) 0.064(1) 0.060(2) 0.037(1) 0.003(1) 0.016(1) Br2 0.060(1) 0.059(1) 0.060(1) 0.029(1) 0.007(1) -0.002(1) Br3 0.052(1) 0.073(1) 0.067(2) 0.017(1) 0.017(1) 0.012(1) Br4 0.066(1) 0.049(1) 0.071(2) 0.025(1) -0.017(1) 0.000(1) N11 0.049(9) 0.061(13) 0.055(13) 0.022(8) 0.012(9) 0.010(10) C12 0.112(19) 0.072(15) 0.098(22) 0.065(15) 0.015(17) 0.024(16) C13 0.064(13) 0.048(12) 0.054(12) 0.035(10) 0.012(10) -0.002(10) C14 0.039(10) 0.078(15) 0.073(17) 0.032(11) 0.023(11) 0.032(13) C15 0.054(11) 0.055(12) 0.050(14) 0.024(10) 0.008(10) 0.004(11) C16 0.052(12) 0.057(14) 0.046(12) 0.021(10) 0.005(10) 0.001(11) C17 0.105(17) 0.092(16) 0.087(18) 0.068(14) 0.001(14) 0.039(14) N21 0.137(22) 0.178(27) 0.042(15) -0.058(21) 0.007(14) -0.047(18) C22 0.148(30) 0.080(20) 0.099(26) -0.003(20) -0.085(24) 0.009(20) C23 0.058(13) 0.114(21) 0.053(15) 0.032(15) 0.030(13) 0.020(14) C24 0.025(11) 0.064(14) 0.059(15) 0.022(11) 0.010(10) 0.013(11) C25 0.026(11) 0.094(16) 0.074(16) 0.011(11) 0.007(11) 0.028(15) C26 0.167(32) 0.124(23) 0.027(14) 0.053(24) -0.008(17) -0.014(15) C27 0.119(23) 0.124(23) 0.075(19) 0.041(19) -0.021(16) -0.029(17) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 Br1 2.419(3) . yes Cu1 Br2 2.344(2) . yes Cu1 Br3 2.426(3) . yes Cu1 Br4 2.394(2) . yes N11 C12 1.35(2) . no N11 C16 1.32(2) . no C12 C13 1.35(3) . no C13 C14 1.39(2) . no C14 C15 1.43(2) . no C14 C17 1.50(2) . no C15 C16 1.39(2) . no N21 C22 1.35(4) . no N21 C26 1.27(3) . no C22 C23 1.42(4) . no C23 C24 1.37(2) . no C24 C25 1.31(3) . no C24 C27 1.53(3) . no C25 C26 1.42(3) . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Cu1 Br2 104.2(1) . . yes Br1 Cu1 Br3 123.5(1) . . yes Br1 Cu1 Br4 98.4(1) . . yes Br2 Cu1 Br3 101.6(1) . . yes Br2 Cu1 Br4 135.8(1) . . yes Br3 Cu1 Br4 96.6(1) . . yes C12 N11 C16 121(1) . . no N11 C12 C13 121(2) . . no C12 C13 C14 121(1) . . no C13 C14 C15 118(1) . . no C13 C14 C17 121(1) . . no C15 C14 C17 121(1) . . no C14 C15 C16 117(1) . . no N11 C16 C15 123(1) . . no C22 N21 C26 116(2) . . no N21 C22 C23 125(2) . . no C22 C23 C24 113(2) . . no C23 C24 C25 123(2) . . no C23 C24 C27 116(2) . . no C25 C24 C27 120(2) . . no C24 C25 C26 118(2) . . no N21 C26 C25 124(2) . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N11 H11 Br3 1.03 2.57 3.44(1) 141 1_655 yes N11 H11 Br4 1.03 2.62 3.39(1) 131 1_655 yes N21 H21 Br1 1.00 2.66 3.50(3) 142 2_556 yes N21 H21 Br4 1.00 2.83 3.57(2) 131 2_556 yes _refine_diff_density_max 0.76 _refine_diff_density_min -0.80 #===END