# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Mark Turnbull' _publ_contact_author_email MTURNBULL@CLARKU.EDU _publ_section_title ; Synthesis, Structure, and Magnetic Properties of bis(monosubstituted-pyrazine)dihalocopper (II) [where substituent = Cl, CN, OCH3, OCH2CH3 and halogen = Cl or Br] ; loop_ _publ_author_name 'Mark Turnbull' 'Susan N. Herringer' 'Geoffrey Jameson' 'Christopher Landee' 'Alyssa J. Longendyke' ; S.Telfer ; 'Jan Wikaira' # Attachment 'AJCPUB.CIF' data_ajcc _database_code_depnum_ccdc_archive 'CCDC 752901' #TrackingRef 'AJCPUB.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(methoxypyrazine)dichlorocopper(II) ; _chemical_name_common Bis(methoxypyrazine)dichlorocopper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 Cl2 Cu N4 O2' _chemical_formula_weight 354.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 3.7836(4) _cell_length_b 7.4197(9) _cell_length_c 11.5656(19) _cell_angle_alpha 89.802(11) _cell_angle_beta 88.856(9) _cell_angle_gamma 83.324(9) _cell_volume 322.42(7) _cell_formula_units_Z 1 _cell_measurement_temperature 123 _cell_measurement_reflns_used 758 _cell_measurement_theta_min 7.6 _cell_measurement_theta_max 70.2 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 2 _exptl_crystal_size_mid 0.012 _exptl_crystal_size_min 0.012 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.827 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 179 _exptl_absorpt_coefficient_mu 6.252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.14 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rigaku MM007 rotating anode' _diffrn_radiation_monochromator 'Rigaku VariMax-HF Confocal Optical System' _diffrn_measurement_device_type 'Rigaku Spider' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3981 _diffrn_reflns_av_R_equivalents 0.1541 _diffrn_reflns_av_sigmaI/netI 0.0983 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 6.00 _diffrn_reflns_theta_max 70.05 _reflns_number_total 1100 _reflns_number_gt 1031 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_data_reduction 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; This data set had to be processed in five independent batches, which meant that merging of batches was sub-optimal. The Rint value is thus somewhat higher than otherwise expected and this is apparent in the large number of bad equivalents (some of which are also possibly due to the prescence ofsmall attached crystallites. Nonetheless, this structure refined will with exceptionally good esds on the bond lengths. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1644P)^2^+0.1375P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1100 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.2252 _refine_ls_wR_factor_gt 0.2204 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 0.5000 1.0000 0.0000 0.0324(5) Uani 1 2 d S . . Cl1 Cl 0.0785(2) 1.19921(11) 0.09065(6) 0.0307(5) Uani 1 1 d . . . O1 O 0.7845(8) 0.8648(4) 0.4338(2) 0.0356(7) Uani 1 1 d . . . N1 N 0.5974(8) 0.6176(4) 0.3390(3) 0.0321(8) Uani 1 1 d . . . N4 N 0.5277(8) 0.8383(4) 0.1425(3) 0.0316(8) Uani 1 1 d . . . C6 C 0.4921(10) 0.5590(5) 0.2378(3) 0.0345(9) Uani 1 1 d . . . H6 H 0.4400 0.4398 0.2335 0.041 Uiso 1 1 calc R . . C3 C 0.6328(10) 0.9027(5) 0.2410(3) 0.0326(9) Uani 1 1 d . . . H3 H 0.6827 1.0222 0.2454 0.039 Uiso 1 1 calc R . . C2 C 0.6691(9) 0.7892(5) 0.3400(3) 0.0304(8) Uani 1 1 d . . . C5 C 0.4551(10) 0.6645(5) 0.1385(3) 0.0350(9) Uani 1 1 d . . . H5 H 0.3814 0.6162 0.0702 0.042 Uiso 1 1 calc R . . C7 C 0.8178(11) 0.7545(5) 0.5377(3) 0.0360(9) Uani 1 1 d . . . H7A H 0.5974 0.7061 0.5537 0.054 Uiso 1 1 calc R . . H7B H 0.8735 0.8277 0.6016 0.054 Uiso 1 1 calc R . . H7C H 1.0046 0.6566 0.5264 0.054 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 0.0381(8) 0.0389(7) 0.0183(7) 0.0036(4) 0.0041(4) 0.0019(5) Cl1 0.0318(7) 0.0376(7) 0.0222(7) 0.0009(5) 0.0031(5) -0.0032(5) O1 0.0462(15) 0.0395(14) 0.0214(12) 0.0026(11) 0.0009(11) -0.0072(12) N1 0.0320(16) 0.0390(17) 0.0253(14) 0.0029(12) 0.0021(11) -0.0048(13) N4 0.0307(16) 0.0420(17) 0.0209(13) 0.0010(12) 0.0050(10) -0.0002(12) C6 0.0342(19) 0.0369(18) 0.0321(18) 0.0019(14) 0.0026(15) -0.0035(15) C3 0.037(2) 0.0387(19) 0.0213(16) 0.0031(14) 0.0045(14) -0.0037(15) C2 0.0310(17) 0.039(2) 0.0202(16) 0.0016(13) 0.0020(13) -0.0030(15) C5 0.0361(18) 0.042(2) 0.0256(17) 0.0000(14) 0.0035(14) -0.0013(16) C7 0.044(2) 0.044(2) 0.0207(17) 0.0059(14) -0.0048(14) -0.0091(17) _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 N4 2.032(3) 2_675 ? Cu1 N4 2.032(3) . ? Cu1 Cl1 2.2854(8) . ? Cu1 Cl1 2.2854(8) 2_675 ? Cu1 Cl1 2.9883(9) 1_655 ? Cl1 Cu1 2.9883(9) 1_455 ? O1 C2 1.327(4) . ? O1 C7 1.451(4) . ? N1 C2 1.333(5) . ? N1 C6 1.334(5) . ? N4 C3 1.323(5) . ? N4 C5 1.350(5) . ? C6 C5 1.388(5) . ? C3 C2 1.418(5) . ? C3 H3 0.9300 . ? C5 H5 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? 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 N4 Cu1 N4 180.00(17) 2_675 . ? N4 Cu1 Cl1 89.77(8) 2_675 . ? N4 Cu1 Cl1 90.23(8) . . ? N4 Cu1 Cl1 90.23(8) 2_675 2_675 ? N4 Cu1 Cl1 89.77(8) . 2_675 ? Cl1 Cu1 Cl1 180.0 . 2_675 ? N4 Cu1 Cl1 89.76(10) 2_675 1_655 ? N4 Cu1 Cl1 90.24(10) . 1_655 ? Cl1 Cu1 Cl1 90.68(3) . 1_655 ? Cl1 Cu1 Cl1 89.32(3) 2_675 1_655 ? Cu1 Cl1 Cu1 90.68(3) . 1_455 ? C2 O1 C7 117.1(3) . . ? C2 N1 C6 115.3(3) . . ? C3 N4 C5 118.9(3) . . ? C3 N4 Cu1 119.2(3) . . ? C5 N4 Cu1 121.9(2) . . ? N1 C6 C5 124.2(4) . . ? N1 C6 H6 117.9 . . ? C5 C6 H6 117.9 . . ? N4 C3 C2 120.0(3) . . ? N4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? O1 C2 N1 122.0(3) . . ? O1 C2 C3 115.4(3) . . ? N1 C2 C3 122.5(3) . . ? N4 C5 C6 119.1(3) . . ? N4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 70.05 _diffrn_measured_fraction_theta_full 0.896 _refine_diff_density_max 1.041 _refine_diff_density_min -0.913 _refine_diff_density_rms 0.199 # Attachment 'AJLAPUB.CIF' data_ajla _database_code_depnum_ccdc_archive 'CCDC 752902' #TrackingRef 'AJLAPUB.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(methoxypyrazine)dibromocopper(II) ; _chemical_name_common Bis(methoxypyrazine)dibromocopper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 Br2 Cu N4 O2' _chemical_formula_weight 443.60 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.9265(3) _cell_length_b 7.4714(6) _cell_length_c 11.5678(9) _cell_angle_alpha 88.598(4) _cell_angle_beta 88.971(4) _cell_angle_gamma 82.340(4) _cell_volume 336.19(5) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6120 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour green _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 215 _exptl_absorpt_coefficient_mu 7.569 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1189 _exptl_absorpt_correction_T_max 0.4898 _exptl_absorpt_process_details 'via SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7325 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1529 _reflns_number_gt 1413 _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.4197P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1529 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0250 _refine_ls_R_factor_gt 0.0213 _refine_ls_wR_factor_ref 0.0601 _refine_ls_wR_factor_gt 0.0567 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.5000 0.0000 0.0000 0.01991(12) Uani 1 2 d S . . Br1 Br 0.07540(6) 0.21471(3) 0.09428(2) 0.01724(9) Uani 1 1 d . . . N1 N 0.3963(6) 0.3752(3) -0.34457(18) 0.0196(4) Uani 1 1 d . . . C2 C 0.3267(6) 0.2072(3) -0.3415(2) 0.0178(5) Uani 1 1 d . . . C3 C 0.3646(6) 0.0959(3) -0.2425(2) 0.0196(5) Uani 1 1 d . . . H3 H 0.3177 -0.0254 -0.2454 0.024 Uiso 1 1 calc R . . N4 N 0.4656(5) 0.1588(3) -0.14431(18) 0.0184(4) Uani 1 1 d . . . C5 C 0.5343(6) 0.3309(3) -0.1445(2) 0.0202(5) Uani 1 1 d . . . H5 H 0.6046 0.3805 -0.0754 0.024 Uiso 1 1 calc R . . C6 C 0.5032(7) 0.4347(3) -0.2443(2) 0.0202(5) Uani 1 1 d . . . H6 H 0.5597 0.5544 -0.2425 0.024 Uiso 1 1 calc R . . O1 O 0.2125(5) 0.1326(3) -0.43512(15) 0.0237(4) Uani 1 1 d . . . C7 C 0.1812(8) 0.2419(4) -0.5394(2) 0.0261(6) Uani 1 1 d . . . H7A H 0.0041 0.3458 -0.5282 0.031 Uiso 1 1 calc R . . H7B H 0.1165 0.1699 -0.6031 0.031 Uiso 1 1 calc R . . H7C H 0.4016 0.2847 -0.5579 0.031 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 0.0245(2) 0.0196(2) 0.0132(2) 0.00404(16) 0.00300(16) 0.00507(17) Br1 0.01549(14) 0.01780(14) 0.01818(14) -0.00072(9) 0.00105(9) -0.00137(9) N1 0.0233(11) 0.0184(10) 0.0171(10) 0.0037(8) -0.0021(8) -0.0037(8) C2 0.0173(11) 0.0191(12) 0.0172(12) -0.0003(9) -0.0003(9) -0.0034(9) C3 0.0214(12) 0.0184(12) 0.0189(12) 0.0011(9) 0.0012(9) -0.0025(9) N4 0.0180(10) 0.0186(10) 0.0170(10) 0.0022(8) 0.0014(8) 0.0023(8) C5 0.0214(12) 0.0205(12) 0.0181(12) -0.0012(9) -0.0018(9) -0.0008(9) C6 0.0230(12) 0.0165(12) 0.0215(12) 0.0008(9) -0.0016(9) -0.0040(9) O1 0.0355(10) 0.0233(9) 0.0139(9) 0.0011(7) -0.0055(7) -0.0098(8) C7 0.0345(15) 0.0282(14) 0.0168(12) 0.0038(10) -0.0068(10) -0.0085(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 Cu1 N4 2.020(2) . ? Cu1 N4 2.020(2) 2_655 ? Cu1 Br1 2.4186(3) . ? Cu1 Br1 2.4186(3) 2_655 ? Cu1 Br1 3.1635(3) 2 ? Br1 Cu1 3.1635(3) 1_455 ? N1 C2 1.319(3) . ? N1 C6 1.346(3) . ? C2 O1 1.340(3) . ? C2 C3 1.398(4) . ? C3 N4 1.326(3) . ? C3 H3 0.9500 . ? N4 C5 1.349(3) . ? C5 C6 1.373(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O1 C7 1.438(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? 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 N4 Cu1 N4 180.00(12) . 2_655 ? N4 Cu1 Br1 89.67(6) . . ? N4 Cu1 Br1 90.33(6) 2_655 . ? N4 Cu1 Br1 90.33(6) . 2_655 ? N4 Cu1 Br1 89.67(6) 2_655 2_655 ? Br1 Cu1 Br1 180.0 . 2_655 ? N4 Cu1 Br1 90.01(6) . 2 ? N4 Cu1 Br1 89.99(6) 2_655 2 ? Br1 Cu1 Br1 91.648(9) . 2 ? Br1 Cu1 Br1 88.352(9) 2_655 2 ? Cu1 Br1 Cu1 88.352(9) . 1_455 ? C2 N1 C6 115.3(2) . . ? N1 C2 O1 121.2(2) . . ? N1 C2 C3 123.1(2) . . ? O1 C2 C3 115.7(2) . . ? N4 C3 C2 120.3(2) . . ? N4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 N4 C5 117.8(2) . . ? C3 N4 Cu1 119.98(17) . . ? C5 N4 Cu1 122.20(17) . . ? N4 C5 C6 120.2(2) . . ? N4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? N1 C6 C5 123.2(2) . . ? N1 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? C2 O1 C7 116.9(2) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 N4 Cu1 Br1 Cu1 90.00(6) . . . 1_455 ? N4 Cu1 Br1 Cu1 -90.00(6) 2_655 . . 1_455 ? Br1 Cu1 Br1 Cu1 -144(100) 2_655 . . 1_455 ? Br1 Cu1 Br1 Cu1 0.0 2 . . 1_455 ? C6 N1 C2 O1 178.9(2) . . . . ? C6 N1 C2 C3 -0.9(4) . . . . ? N1 C2 C3 N4 1.9(4) . . . . ? O1 C2 C3 N4 -177.9(2) . . . . ? C2 C3 N4 C5 -1.0(4) . . . . ? C2 C3 N4 Cu1 177.40(18) . . . . ? N4 Cu1 N4 C3 145(100) 2_655 . . . ? Br1 Cu1 N4 C3 -119.09(18) . . . . ? Br1 Cu1 N4 C3 60.91(18) 2_655 . . . ? Br1 Cu1 N4 C3 -27.44(18) 2 . . . ? N4 Cu1 N4 C5 -37(100) 2_655 . . . ? Br1 Cu1 N4 C5 59.23(19) . . . . ? Br1 Cu1 N4 C5 -120.77(19) 2_655 . . . ? Br1 Cu1 N4 C5 150.88(19) 2 . . . ? C3 N4 C5 C6 -0.8(4) . . . . ? Cu1 N4 C5 C6 -179.12(18) . . . . ? C2 N1 C6 C5 -0.9(4) . . . . ? N4 C5 C6 N1 1.8(4) . . . . ? N1 C2 O1 C7 2.1(4) . . . . ? C3 C2 O1 C7 -178.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.881 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.104 # Attachment 'AJLBPUB.CIF' data_ajlb _database_code_depnum_ccdc_archive 'CCDC 752903' #TrackingRef 'AJLBPUB.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(ethoxypyrazine)dibromocopper(II) ; _chemical_name_common Bis(ethoxypyrazine)dibromocopper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Br Cu0.50 N2 O' _chemical_formula_weight 235.82 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.9268(2) _cell_length_b 8.0343(5) _cell_length_c 12.3763(7) _cell_angle_alpha 87.676(4) _cell_angle_beta 85.607(4) _cell_angle_gamma 85.486(4) _cell_volume 387.87(4) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3748 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 31.18 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.019 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 231 _exptl_absorpt_coefficient_mu 6.567 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3750 _exptl_absorpt_correction_T_max 0.6744 _exptl_absorpt_process_details 'via SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 8199 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1768 _reflns_number_gt 1506 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0706P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1768 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 0.0000 0.5000 0.0000 0.0177(2) Uani 1 2 d S . . Br1 Br 0.42979(9) 0.31550(5) -0.09613(3) 0.01613(16) Uani 1 1 d . . . N1 N -0.0622(9) 0.8928(5) -0.3032(3) 0.0192(7) Uani 1 1 d . . . C2 C -0.1175(10) 0.7344(5) -0.3100(3) 0.0162(8) Uani 1 1 d . . . C3 C -0.0828(11) 0.6172(5) -0.2230(3) 0.0170(8) Uani 1 1 d . . . H3 H -0.1197 0.5034 -0.2324 0.020 Uiso 1 1 calc R . . N4 N 0.0006(9) 0.6651(5) -0.1288(3) 0.0166(7) Uani 1 1 d . . . C5 C 0.0594(11) 0.8280(6) -0.1196(3) 0.0190(9) Uani 1 1 d . . . H5 H 0.1220 0.8655 -0.0526 0.023 Uiso 1 1 calc R . . C6 C 0.0296(11) 0.9376(6) -0.2053(3) 0.0210(9) Uani 1 1 d . . . H6 H 0.0749 1.0505 -0.1966 0.025 Uiso 1 1 calc R . . C7 C -0.3014(11) 0.7983(5) -0.4864(3) 0.0183(9) Uani 1 1 d . . . H7A H -0.1023 0.8627 -0.5100 0.022 Uiso 1 1 calc R . . H7B H -0.4925 0.8770 -0.4593 0.022 Uiso 1 1 calc R . . C8 C -0.4058(12) 0.7036(6) -0.5790(3) 0.0236(10) Uani 1 1 d . . . H8A H -0.2124 0.6284 -0.6062 0.028 Uiso 1 1 calc R . . H8B H -0.4745 0.7824 -0.6373 0.028 Uiso 1 1 calc R . . H8C H -0.5987 0.6381 -0.5540 0.028 Uiso 1 1 calc R . . O1 O -0.2121(8) 0.6749(4) -0.4024(2) 0.0194(6) 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 0.0239(4) 0.0191(4) 0.0085(4) 0.0032(3) -0.0007(3) 0.0049(3) Br1 0.0168(2) 0.0184(3) 0.0133(2) -0.00117(15) -0.00225(15) -0.00032(16) N1 0.0260(18) 0.0182(19) 0.0137(17) 0.0025(14) -0.0028(14) -0.0045(15) C2 0.0197(19) 0.018(2) 0.0116(19) -0.0006(15) -0.0031(15) -0.0015(16) C3 0.023(2) 0.0134(19) 0.0141(19) -0.0009(15) -0.0015(16) -0.0007(16) N4 0.0202(16) 0.0190(18) 0.0100(16) 0.0025(13) -0.0023(13) 0.0024(14) C5 0.021(2) 0.023(2) 0.0138(19) -0.0055(16) -0.0039(16) -0.0017(17) C6 0.028(2) 0.017(2) 0.019(2) -0.0011(16) -0.0011(17) -0.0067(18) C7 0.024(2) 0.020(2) 0.011(2) 0.0069(16) -0.0048(16) -0.0008(17) C8 0.031(2) 0.027(2) 0.013(2) 0.0010(17) -0.0095(17) -0.002(2) O1 0.0339(16) 0.0166(15) 0.0092(14) 0.0022(11) -0.0107(12) -0.0036(13) _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 N4 2.032(3) . ? Cu1 N4 2.032(3) 2_565 ? Cu1 Br1 2.4296(4) . ? Cu1 Br1 2.4296(4) 2_565 ? Cu1 Br1 3.1145(4) 1_455 ? Br1 Cu1 3.1145(4) 1_655 ? N1 C2 1.315(6) . ? N1 C6 1.360(5) . ? C2 O1 1.347(5) . ? C2 C3 1.409(6) . ? C3 N4 1.315(5) . ? C3 H3 0.9500 . ? N4 C5 1.357(6) . ? C5 C6 1.357(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.451(5) . ? C7 C8 1.500(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 N4 Cu1 N4 180.0(2) . 2_565 ? N4 Cu1 Br1 90.74(10) . . ? N4 Cu1 Br1 89.26(10) 2_565 . ? N4 Cu1 Br1 89.26(10) . 2_565 ? N4 Cu1 Br1 90.74(10) 2_565 2_565 ? Br1 Cu1 Br1 180.000(15) . 2_565 ? N4 Cu1 Br1 90.04(10) . 1_455 ? N4 Cu1 Br1 89.96(10) 2_565 1_455 ? Br1 Cu1 Br1 89.306(12) . 1_455 ? Br1 Cu1 Br1 90.694(12) 2_565 1_455 ? Cu1 Br1 Cu1 89.306(12) . 1_655 ? C2 N1 C6 115.4(4) . . ? N1 C2 O1 121.1(4) . . ? N1 C2 C3 123.0(4) . . ? O1 C2 C3 115.9(4) . . ? N4 C3 C2 120.1(4) . . ? N4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 N4 C5 118.1(3) . . ? C3 N4 Cu1 119.5(3) . . ? C5 N4 Cu1 122.3(3) . . ? C6 C5 N4 120.6(4) . . ? C6 C5 H5 119.7 . . ? N4 C5 H5 119.7 . . ? C5 C6 N1 122.8(4) . . ? C5 C6 H6 118.6 . . ? N1 C6 H6 118.6 . . ? O1 C7 C8 106.5(4) . . ? O1 C7 H7A 110.4 . . ? C8 C7 H7A 110.4 . . ? O1 C7 H7B 110.4 . . ? C8 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 O1 C7 116.3(3) . . ? 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 N4 Cu1 Br1 Cu1 89.97(10) . . . 1_655 ? N4 Cu1 Br1 Cu1 -90.03(10) 2_565 . . 1_655 ? Br1 Cu1 Br1 Cu1 -76(100) 2_565 . . 1_655 ? Br1 Cu1 Br1 Cu1 180.0 1_455 . . 1_655 ? C6 N1 C2 O1 179.5(4) . . . . ? C6 N1 C2 C3 -0.4(6) . . . . ? N1 C2 C3 N4 1.6(7) . . . . ? O1 C2 C3 N4 -178.3(4) . . . . ? C2 C3 N4 C5 -1.6(6) . . . . ? C2 C3 N4 Cu1 173.5(3) . . . . ? N4 Cu1 N4 C3 27(100) 2_565 . . . ? Br1 Cu1 N4 C3 60.3(3) . . . . ? Br1 Cu1 N4 C3 -119.7(3) 2_565 . . . ? Br1 Cu1 N4 C3 -29.0(3) 1_455 . . . ? N4 Cu1 N4 C5 -158(100) 2_565 . . . ? Br1 Cu1 N4 C5 -124.8(3) . . . . ? Br1 Cu1 N4 C5 55.2(3) 2_565 . . . ? Br1 Cu1 N4 C5 145.9(3) 1_455 . . . ? C3 N4 C5 C6 0.5(6) . . . . ? Cu1 N4 C5 C6 -174.5(3) . . . . ? N4 C5 C6 N1 0.7(7) . . . . ? C2 N1 C6 C5 -0.7(7) . . . . ? N1 C2 O1 C7 -9.5(6) . . . . ? C3 C2 O1 C7 170.5(4) . . . . ? C8 C7 O1 C2 -178.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.144 _refine_diff_density_min -1.030 _refine_diff_density_rms 0.269 # Attachment 'AJLDPUB.CIF' data_ajld_a _database_code_depnum_ccdc_archive 'CCDC 752904' #TrackingRef 'AJLDPUB.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(ethoxypyrazine)dichlorocopper(II) ; _chemical_name_common Bis(ethoxypyrazine)dichlorocopper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Cl2 Cu N4 O2' _chemical_formula_weight 382.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 '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 3.8018(4) _cell_length_b 8.0135(6) _cell_length_c 12.2611(9) _cell_angle_alpha 89.610(4) _cell_angle_beta 86.245(5) _cell_angle_gamma 86.619(5) _cell_volume 372.09(6) _cell_formula_units_Z 1 _cell_measurement_temperature 123 _cell_measurement_reflns_used 1194 _cell_measurement_theta_min 6.60 _cell_measurement_theta_max 71.3 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 1.5 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 195 _exptl_absorpt_coefficient_mu 5.466 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.542 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rigaku MM007 rotating anode' _diffrn_radiation_monochromator 'Rigaku VariMax-HF Confocal Optical System' _diffrn_measurement_device_type 'Rigaku Spider' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3292 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 6.60 _diffrn_reflns_theta_max 70.06 _reflns_number_total 1084 _reflns_number_gt 951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_data_reduction 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; An unlucky crystal orientation means that although I/sig(I) is excellent out to the limit of 0.81 A resolution, the completeness of the data is less satisfactory. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0722P)^2^+0.4847P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1084 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 0.5000 0.0000 1.0000 0.0237(3) Uani 1 2 d S . . Cl1 Cl 0.0818(3) 0.17015(10) 1.09414(6) 0.0220(3) Uani 1 1 d . . . O1 O 0.2839(9) 0.1767(3) 0.59793(19) 0.0246(8) Uani 1 1 d . . . N1 N 0.4440(10) 0.3963(4) 0.7037(2) 0.0227(9) Uani 1 1 d . . . N4 N 0.5028(10) 0.1660(4) 0.8749(2) 0.0217(9) Uani 1 1 d . . . C3 C 0.4136(13) 0.1191(5) 0.7781(3) 0.0220(10) Uani 1 1 d . . . H3 H 0.3697 0.0079 0.7663 0.026 Uiso 1 1 calc R . . C2 C 0.3841(12) 0.2359(5) 0.6924(3) 0.0213(10) Uani 1 1 d . . . C6 C 0.5450(13) 0.4401(5) 0.8032(3) 0.0243(10) Uani 1 1 d . . . H6 H 0.5978 0.5503 0.8141 0.029 Uiso 1 1 calc R . . C7 C 0.1915(13) 0.2999(5) 0.5149(3) 0.0234(10) Uani 1 1 d . . . H7A H 0.3932 0.3643 0.4936 0.028 Uiso 1 1 calc R . . H7B H -0.0002 0.3761 0.5431 0.028 Uiso 1 1 calc R . . C8 C 0.0805(13) 0.2060(5) 0.4183(3) 0.0275(11) Uani 1 1 d . . . H8A H 0.2763 0.1359 0.3884 0.041 Uiso 1 1 calc R . . H8B H 0.0051 0.2841 0.3635 0.041 Uiso 1 1 calc R . . H8C H -0.1109 0.1381 0.4411 0.041 Uiso 1 1 calc R . . C5 C 0.5726(13) 0.3292(5) 0.8882(3) 0.0249(10) Uani 1 1 d . . . H5 H 0.6393 0.3656 0.9553 0.030 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 0.0343(8) 0.0229(5) 0.0131(4) 0.0042(3) 0.0002(3) 0.0026(4) Cl1 0.0258(9) 0.0227(5) 0.0174(5) 0.0015(3) 0.0000(4) -0.0013(5) O1 0.038(2) 0.0194(13) 0.0168(12) 0.0040(9) -0.0069(12) -0.0013(13) N1 0.025(3) 0.0252(17) 0.0185(15) 0.0032(12) -0.0020(13) -0.0038(16) N4 0.027(3) 0.0228(15) 0.0150(14) 0.0015(11) -0.0011(13) 0.0040(15) C3 0.029(3) 0.0192(17) 0.0176(17) 0.0031(13) -0.0016(16) -0.0003(18) C2 0.026(3) 0.0242(19) 0.0145(17) 0.0012(13) -0.0043(15) -0.0004(18) C6 0.028(3) 0.0239(19) 0.0211(18) 0.0000(14) -0.0006(16) -0.0060(19) C7 0.031(3) 0.0222(18) 0.0174(17) 0.0077(13) -0.0047(16) -0.0043(19) C8 0.033(4) 0.031(2) 0.0186(18) 0.0032(15) -0.0071(17) -0.002(2) C5 0.027(3) 0.028(2) 0.0193(18) -0.0010(14) 0.0001(16) -0.0009(19) _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 N4 2.023(3) 2_657 ? Cu1 N4 2.023(3) . ? Cu1 Cl1 2.2901(10) 2_657 ? Cu1 Cl1 2.2901(10) . ? Cu1 Cl1 2.9656(10) 1_655 ? Cl1 Cu1 2.9656(10) 1_455 ? O1 C2 1.340(4) . ? O1 C7 1.458(4) . ? N1 C2 1.329(5) . ? N1 C6 1.357(5) . ? N4 C3 1.319(5) . ? N4 C5 1.363(5) . ? C3 C2 1.408(5) . ? C3 H3 0.9300 . ? C6 C5 1.371(5) . ? C6 H6 0.9300 . ? C7 C8 1.504(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C5 H5 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 N4 Cu1 N4 180.000(1) 2_657 . ? N4 Cu1 Cl1 89.27(10) 2_657 2_657 ? N4 Cu1 Cl1 90.73(10) . 2_657 ? N4 Cu1 Cl1 90.73(10) 2_657 . ? N4 Cu1 Cl1 89.27(10) . . ? Cl1 Cu1 Cl1 180.000(1) 2_657 . ? N4 Cu1 Cl1 90.14(10) 2_657 1_655 ? N4 Cu1 Cl1 89.86(10) . 1_655 ? Cl1 Cu1 Cl1 88.25(3) 2_657 1_655 ? Cl1 Cu1 Cl1 91.75(3) . 1_655 ? Cu1 Cl1 Cu1 91.75(3) . 1_455 ? C2 O1 C7 116.8(3) . . ? C2 N1 C6 115.4(3) . . ? C3 N4 C5 117.9(3) . . ? C3 N4 Cu1 119.6(2) . . ? C5 N4 Cu1 122.3(2) . . ? N4 C3 C2 120.6(3) . . ? N4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? N1 C2 O1 121.2(3) . . ? N1 C2 C3 122.7(3) . . ? O1 C2 C3 116.1(3) . . ? N1 C6 C5 123.0(3) . . ? N1 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? O1 C7 C8 107.4(3) . . ? O1 C7 H7A 110.2 . . ? C8 C7 H7A 110.2 . . ? O1 C7 H7B 110.2 . . ? C8 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C5 C6 120.3(3) . . ? N4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? _diffrn_measured_fraction_theta_max 0.765 _diffrn_reflns_theta_full 70.06 _diffrn_measured_fraction_theta_full 0.765 _refine_diff_density_max 1.192 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.106 # Attachment 'SNHFPUB.CIF' data_snhf _database_code_depnum_ccdc_archive 'CCDC 752905' #TrackingRef 'SNHFPUB.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(chloropyrazine)dibromocopper (II) ; _chemical_name_common 'bis(chloropyrazine)dibromocopper (ii)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H6 Br2 Cl2 Cu N4' _chemical_formula_weight 452.43 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' 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 3.8740(2) _cell_length_b 10.0112(5) _cell_length_c 16.1150(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.495(3) _cell_angle_gamma 90.00 _cell_volume 620.98(5) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 9426 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 33.46 _exptl_crystal_description needle _exptl_crystal_colour gold _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 430 _exptl_absorpt_coefficient_mu 8.603 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0823 _exptl_absorpt_correction_T_max 0.6263 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16527 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 34.49 _reflns_number_total 2349 _reflns_number_gt 2075 _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+1.4306P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2349 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0727 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _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 0.5000 0.5000 0.0000 0.01551(10) Uani 1 2 d S . . Br1 Br 0.15571(6) 0.36902(2) 0.085739(15) 0.01525(7) Uani 1 1 d . . . N1 N 0.6004(7) 0.8520(2) 0.20618(15) 0.0209(4) Uani 1 1 d . . . C2 C 0.4591(7) 0.8701(2) 0.12874(17) 0.0160(4) Uani 1 1 d . . . C3 C 0.4304(7) 0.7708(2) 0.06804(15) 0.0156(4) Uani 1 1 d . . . H3 H 0.3344 0.7909 0.0126 0.019 Uiso 1 1 calc R . . N4 N 0.5391(6) 0.6467(2) 0.08828(13) 0.0151(4) Uani 1 1 d . . . C5 C 0.6755(7) 0.6240(2) 0.16754(17) 0.0187(5) Uani 1 1 d . . . H5 H 0.7498 0.5366 0.1841 0.022 Uiso 1 1 calc R . . C6 C 0.7084(8) 0.7273(3) 0.22529(17) 0.0219(5) Uani 1 1 d . . . H6 H 0.8113 0.7090 0.2804 0.026 Uiso 1 1 calc R . . Cl1 Cl 0.30254(19) 1.02806(6) 0.10266(5) 0.02333(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 0.0248(2) 0.00741(17) 0.0152(2) -0.00264(14) 0.00654(16) -0.00314(14) Br1 0.01813(12) 0.01087(11) 0.01713(12) 0.00097(8) 0.00366(8) -0.00045(8) N1 0.0294(12) 0.0129(9) 0.0195(11) -0.0033(8) -0.0010(9) 0.0020(8) C2 0.0187(10) 0.0088(9) 0.0203(11) -0.0013(8) 0.0008(8) 0.0007(8) C3 0.0215(11) 0.0104(9) 0.0148(10) 0.0001(8) 0.0014(8) -0.0011(8) N4 0.0218(10) 0.0089(8) 0.0151(9) -0.0010(7) 0.0037(7) -0.0010(7) C5 0.0257(12) 0.0116(10) 0.0189(12) 0.0005(8) 0.0025(9) 0.0025(9) C6 0.0314(13) 0.0156(11) 0.0172(11) -0.0006(9) -0.0032(10) 0.0031(10) Cl1 0.0310(3) 0.0096(2) 0.0285(3) -0.0013(2) -0.0006(3) 0.0046(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 N4 2.039(2) . ? Cu1 N4 2.039(2) 3_665 ? Cu1 Br1 2.4134(2) 3_665 ? Cu1 Br1 2.4134(2) . ? Cu1 Br1 3.0475(3) 1_655 ? Br1 Cu1 3.0475(3) 1_455 ? N1 C2 1.317(3) . ? N1 C6 1.341(3) . ? C2 C3 1.390(3) . ? C2 Cl1 1.729(2) . ? C3 N4 1.340(3) . ? N4 C5 1.345(3) . ? C5 C6 1.387(4) . ? 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 N4 Cu1 N4 180.00(12) . 3_665 ? N4 Cu1 Br1 90.33(6) . 3_665 ? N4 Cu1 Br1 89.67(6) 3_665 3_665 ? N4 Cu1 Br1 89.67(6) . . ? N4 Cu1 Br1 90.33(6) 3_665 . ? Br1 Cu1 Br1 180.0 3_665 . ? N4 Cu1 Br1 90.08(6) . 1_655 ? N4 Cu1 Br1 89.92(6) 3_665 1_655 ? Br1 Cu1 Br1 90.405(8) 3_665 1_655 ? Br1 Cu1 Br1 89.595(8) . 1_655 ? Cu1 Br1 Cu1 89.595(8) . 1_455 ? C2 N1 C6 115.5(2) . . ? N1 C2 C3 124.1(2) . . ? N1 C2 Cl1 116.92(19) . . ? C3 C2 Cl1 119.0(2) . . ? N4 C3 C2 119.6(2) . . ? C3 N4 C5 117.8(2) . . ? C3 N4 Cu1 120.11(17) . . ? C5 N4 Cu1 122.06(17) . . ? N4 C5 C6 120.5(2) . . ? N1 C6 C5 122.5(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 N4 Cu1 Br1 Cu1 89.92(6) . . . 1_455 ? N4 Cu1 Br1 Cu1 -90.08(6) 3_665 . . 1_455 ? Br1 Cu1 Br1 Cu1 158(100) 3_665 . . 1_455 ? Br1 Cu1 Br1 Cu1 180.0 1_655 . . 1_455 ? C6 N1 C2 C3 -2.4(4) . . . . ? C6 N1 C2 Cl1 177.8(2) . . . . ? N1 C2 C3 N4 2.6(4) . . . . ? Cl1 C2 C3 N4 -177.5(2) . . . . ? C2 C3 N4 C5 -0.5(4) . . . . ? C2 C3 N4 Cu1 -179.88(19) . . . . ? N4 Cu1 N4 C3 100(100) 3_665 . . . ? Br1 Cu1 N4 C3 57.31(19) 3_665 . . . ? Br1 Cu1 N4 C3 -122.69(19) . . . . ? Br1 Cu1 N4 C3 147.72(19) 1_655 . . . ? N4 Cu1 N4 C5 -80(100) 3_665 . . . ? Br1 Cu1 N4 C5 -122.0(2) 3_665 . . . ? Br1 Cu1 N4 C5 58.0(2) . . . . ? Br1 Cu1 N4 C5 -31.6(2) 1_655 . . . ? C3 N4 C5 C6 -1.5(4) . . . . ? Cu1 N4 C5 C6 177.9(2) . . . . ? C2 N1 C6 C5 0.3(4) . . . . ? N4 C5 C6 N1 1.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 34.49 _diffrn_measured_fraction_theta_full 0.896 _refine_diff_density_max 1.102 _refine_diff_density_min -0.978 _refine_diff_density_rms 0.167 # Attachment 'snhepub.cif' data_snhenm _database_code_depnum_ccdc_archive 'CCDC 752906' #TrackingRef 'snhepub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(chloropyrazine)dichlorocopper(II) ; _chemical_name_common bis(chloropyrazine)dichlorocopper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H6 Cl4 Cu1 N4' _chemical_formula_weight 363.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 '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 3.7176(2) _cell_length_b 9.8367(15) _cell_length_c 16.0242(17) _cell_angle_alpha 90.00 _cell_angle_beta 94.381(6) _cell_angle_gamma 90.00 _cell_volume 584.28(11) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1217 _cell_measurement_theta_min 6.74 _cell_measurement_theta_max 72.82 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.002 _exptl_crystal_size_min 0.002 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.066 _exptl_crystal_F_000 358 _exptl_absorpt_coefficient_mu 10.901 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.38 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rigaku MM007 rotating anode' _diffrn_radiation_monochromator 'Rigaku VariMax-HF Confocal Optical System' _diffrn_measurement_device_type 'Rigaku Spider' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6420 _diffrn_reflns_av_R_equivalents 0.3841 _diffrn_reflns_av_sigmaI/netI 0.3631 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 7.14 _diffrn_reflns_theta_max 58.82 _reflns_number_total 805 _reflns_number_gt 240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_data_reduction 'FSProcess in Process-Auto (Rigaku, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 805 _refine_ls_number_parameters 79 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.2832 _refine_ls_R_factor_gt 0.1109 _refine_ls_wR_factor_ref 0.3055 _refine_ls_wR_factor_gt 0.2118 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.888 _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 Cl1 Cl 1.2191(13) 0.5377(5) 0.3969(3) 0.087(2) Uani 1 1 d . . . Cu1 Cu 1.0000 0.0000 0.5000 0.091(2) Uani 1 2 d S . . Cl2 Cl 0.6412(13) 0.1262(5) 0.5792(3) 0.085(2) Uani 1 1 d . . . N1 N 0.974(4) 0.1502(18) 0.4095(12) 0.084(5) Uani 1 1 d U . . N2 N 0.925(5) 0.3569(17) 0.2920(13) 0.088(5) Uani 1 1 d U . . C1 C 1.058(5) 0.380(2) 0.3671(17) 0.073(6) Uani 1 1 d U . . C3 C 0.844(5) 0.128(2) 0.3311(16) 0.076(6) Uani 1 1 d U . . H3 H 0.7709 0.0391 0.3145 0.091 Uiso 1 1 calc R . . C2 C 1.090(5) 0.278(2) 0.4306(14) 0.081(6) Uani 1 1 d U . . H2 H 1.1890 0.2985 0.4856 0.098 Uiso 1 1 calc R . . C4 C 0.815(5) 0.231(2) 0.2747(14) 0.090(7) Uani 1 1 d U . . H4 H 0.7105 0.2113 0.2200 0.108 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 Cl1 0.094(4) 0.070(3) 0.098(5) -0.003(3) 0.010(3) -0.003(3) Cu1 0.094(3) 0.085(3) 0.095(4) 0.000(3) 0.019(3) 0.005(2) Cl2 0.090(4) 0.075(4) 0.093(4) 0.001(3) 0.018(3) -0.004(2) N1 0.097(11) 0.078(11) 0.077(12) -0.008(10) -0.002(10) 0.006(9) N2 0.100(11) 0.069(10) 0.098(13) 0.014(10) 0.021(10) -0.011(9) C1 0.066(11) 0.077(13) 0.076(14) 0.004(12) 0.011(11) 0.025(9) C3 0.085(12) 0.064(12) 0.077(14) -0.012(11) -0.006(11) 0.015(9) C2 0.084(12) 0.099(14) 0.065(13) -0.022(12) 0.029(10) -0.002(11) C4 0.090(13) 0.078(13) 0.102(15) 0.011(13) 0.004(11) 0.017(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 Cl1 C1 1.72(2) . ? Cu1 N1 2.067(17) 3_756 ? Cu1 N1 2.067(17) . ? Cu1 Cl2 2.278(5) . ? Cu1 Cl2 2.278(5) 3_756 ? N1 C3 1.33(2) . ? N1 C2 1.36(2) . ? N2 C1 1.29(2) . ? N2 C4 1.33(2) . ? C1 C2 1.42(2) . ? C3 C4 1.35(2) . ? C3 H3 0.9500 . ? C2 H2 0.9500 . ? C4 H4 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 N1 Cu1 N1 180.000(4) 3_756 . ? N1 Cu1 Cl2 89.8(5) 3_756 . ? N1 Cu1 Cl2 90.2(5) . . ? N1 Cu1 Cl2 90.2(5) 3_756 3_756 ? N1 Cu1 Cl2 89.8(5) . 3_756 ? Cl2 Cu1 Cl2 180.0(2) . 3_756 ? C3 N1 C2 118(2) . . ? C3 N1 Cu1 122.7(16) . . ? C2 N1 Cu1 119.3(15) . . ? C1 N2 C4 117(2) . . ? N2 C1 C2 124(2) . . ? N2 C1 Cl1 121(2) . . ? C2 C1 Cl1 115.3(18) . . ? N1 C3 C4 121(2) . . ? N1 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? N1 C2 C1 117.5(19) . . ? N1 C2 H2 121.2 . . ? C1 C2 H2 121.2 . . ? N2 C4 C3 123(2) . . ? N2 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 58.82 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.510 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.149