# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Brammer, L.' _publ_contact_author_email lee.brammer@sheffield.ac.uk _publ_section_title ; Synthesis and polymorphism of (4-ClpyH)2[CuCl4]: solid-gas and solid-solid reactions ; loop_ _publ_author_name Brammer, L. data_compound1_150K _database_code_depnum_ccdc_archive 'CCDC 793198' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Cl4 Cu N2' _chemical_formula_weight 361.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.787(3) _cell_length_b 7.549(5) _cell_length_c 11.992(8) _cell_angle_alpha 74.198(8) _cell_angle_beta 88.428(7) _cell_angle_gamma 85.816(7) _cell_volume 329.0(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1612 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 26.46 _exptl_crystal_description blue _exptl_crystal_colour needle _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.825 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 179 _exptl_absorpt_coefficient_mu 2.447 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9527 _exptl_absorpt_correction_T_max 0.9976 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6998 _diffrn_radiation_type ? _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'Rigaku SATURN CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4675 _diffrn_reflns_av_R_equivalents 0.0961 _diffrn_reflns_av_sigmaI/netI 0.1102 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _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 1.76 _diffrn_reflns_theta_max 27.58 _reflns_number_total 1462 _reflns_number_gt 967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku Crystal Clear' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0308P)^2^+10.7314P] 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 1462 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1625 _refine_ls_R_factor_gt 0.1111 _refine_ls_wR_factor_ref 0.2743 _refine_ls_wR_factor_gt 0.2526 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.168 _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 0.0000 0.0281(7) Uani 1 2 d S . . Cl1 Cl 0.0920(8) 0.2327(4) -0.0915(3) 0.0285(8) Uani 1 1 d . . . N1 N 0.469(3) 0.0986(15) 0.1422(10) 0.027(2) Uani 1 1 d . . . C2 C 0.532(4) 0.2756(19) 0.1336(13) 0.032(3) Uani 1 1 d . . . H2 H 0.6187 0.3491 0.0622 0.039 Uiso 1 1 calc R . . C6 C 0.358(4) -0.0064(19) 0.2450(12) 0.034(3) Uani 1 1 d . . . H6 H 0.3292 -0.1332 0.2528 0.040 Uiso 1 1 calc R . . C3 C 0.475(4) 0.3536(19) 0.2246(12) 0.032(3) Uani 1 1 d . . . H3 H 0.5236 0.4782 0.2165 0.038 Uiso 1 1 calc R . . C5 C 0.284(4) 0.0624(19) 0.3409(12) 0.030(3) Uani 1 1 d . . . H5 H 0.1954 -0.0136 0.4113 0.036 Uiso 1 1 calc R . . C4 C 0.343(4) 0.2446(19) 0.3296(12) 0.032(3) Uani 1 1 d . . . Cl2 Cl 0.2496(11) 0.3395(6) 0.4447(3) 0.0437(10) 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 0.0253(15) 0.0296(14) 0.0297(13) -0.0103(11) 0.0021(10) 0.0041(10) Cl1 0.0198(18) 0.0230(16) 0.0414(19) -0.0069(14) 0.0037(14) -0.0017(13) N1 0.023(6) 0.027(6) 0.033(6) -0.012(5) -0.007(5) 0.004(5) C2 0.022(7) 0.033(7) 0.038(8) -0.003(6) 0.004(6) 0.000(6) C6 0.041(9) 0.023(7) 0.034(7) -0.005(6) -0.004(6) 0.001(6) C3 0.030(8) 0.026(7) 0.040(8) -0.008(6) -0.003(6) -0.008(6) C5 0.027(8) 0.035(7) 0.028(7) -0.007(6) 0.006(6) -0.005(6) C4 0.029(8) 0.034(8) 0.036(8) -0.016(6) -0.007(6) -0.001(6) Cl2 0.045(2) 0.047(2) 0.047(2) -0.0256(18) 0.0033(18) -0.0051(18) _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 N1 2.035(11) 2_655 ? Cu1 N1 2.035(11) . ? Cu1 Cl1 2.307(3) 2_655 ? Cu1 Cl1 2.307(3) . ? N1 C6 1.346(17) . ? N1 C2 1.350(17) . ? C2 C3 1.38(2) . ? C2 H2 0.9500 . ? C6 C5 1.400(19) . ? C6 H6 0.9500 . ? C3 C4 1.40(2) . ? C3 H3 0.9500 . ? C5 C4 1.379(19) . ? C5 H5 0.9500 . ? C4 Cl2 1.738(14) . ? 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 179.999(1) 2_655 . ? N1 Cu1 Cl1 89.4(3) 2_655 2_655 ? N1 Cu1 Cl1 90.6(3) . 2_655 ? N1 Cu1 Cl1 90.6(3) 2_655 . ? N1 Cu1 Cl1 89.4(3) . . ? Cl1 Cu1 Cl1 180.0 2_655 . ? C6 N1 C2 118.3(12) . . ? C6 N1 Cu1 120.8(9) . . ? C2 N1 Cu1 120.7(9) . . ? N1 C2 C3 122.5(13) . . ? N1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? N1 C6 C5 123.1(12) . . ? N1 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? C2 C3 C4 118.5(12) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C4 C5 C6 117.6(13) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? C5 C4 C3 120.0(13) . . ? C5 C4 Cl2 119.9(11) . . ? C3 C4 Cl2 120.1(11) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.493 _refine_diff_density_min -1.016 _refine_diff_density_rms 0.225 #===END # compound 2 (phase I) (100 K) data_compound2_phaseI_100K _database_code_depnum_ccdc_archive 'CCDC 793199' #TrackingRef '- Brammer_solid-gas_solid-solid_rxn_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl6 Cu N2' _chemical_formula_weight 434.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5585(4) _cell_length_b 27.3760(13) _cell_length_c 8.7184(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.492(2) _cell_angle_gamma 90.00 _cell_volume 1628.39(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9510 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 27.60 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 2.311 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5344 _exptl_absorpt_correction_T_max 0.7851 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 34269 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.63 _reflns_number_total 3783 _reflns_number_gt 3574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0158P)^2^+0.9430P] 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 3783 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0191 _refine_ls_R_factor_gt 0.0176 _refine_ls_wR_factor_ref 0.0420 _refine_ls_wR_factor_gt 0.0415 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.002 _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 0.96104(2) 0.120991(6) 0.55703(2) 0.01398(5) Uani 1 1 d . . . Cl2 Cl 0.65270(5) 0.101980(13) 0.38349(4) 0.02071(8) Uani 1 1 d . . . Cl3 Cl 1.04354(5) 0.159753(12) 0.36537(4) 0.01838(7) Uani 1 1 d . . . Cl4 Cl 1.24144(5) 0.077007(12) 0.67439(4) 0.01786(7) Uani 1 1 d . . . Cl5 Cl 0.93413(5) 0.146823(12) 0.78997(4) 0.01841(7) Uani 1 1 d . . . Cl1 Cl 0.26327(5) 0.216495(13) 0.11927(4) 0.02184(8) Uani 1 1 d . . . N1 N 0.68794(17) 0.30381(5) 0.54665(15) 0.0205(2) Uani 1 1 d . . . H1A H 0.7722 0.3212 0.6315 0.025 Uiso 1 1 calc R . . C2 C 0.5546(2) 0.32711(5) 0.41111(18) 0.0211(3) Uani 1 1 d . . . H2A H 0.5525 0.3618 0.4079 0.025 Uiso 1 1 calc R . . C3 C 0.4205(2) 0.30088(5) 0.27640(18) 0.0187(3) Uani 1 1 d . . . H3A H 0.3260 0.3170 0.1791 0.022 Uiso 1 1 calc R . . C4 C 0.42741(19) 0.25024(5) 0.28679(17) 0.0168(3) Uani 1 1 d . . . C5 C 0.5665(2) 0.22662(5) 0.42898(18) 0.0211(3) Uani 1 1 d . . . H5A H 0.5705 0.1920 0.4366 0.025 Uiso 1 1 calc R . . C6 C 0.6978(2) 0.25488(6) 0.55793(18) 0.0218(3) Uani 1 1 d . . . H6A H 0.7960 0.2398 0.6555 0.026 Uiso 1 1 calc R . . Cl11 Cl 0.70960(5) 1.043977(12) 1.06269(4) 0.01822(7) Uani 1 1 d . . . N11 N 0.77979(16) 0.94898(4) 0.68182(14) 0.0159(2) Uani 1 1 d . . . H11A H 0.7938 0.9300 0.6064 0.019 Uiso 1 1 calc R . . C12 C 0.79875(18) 0.92924(5) 0.82871(17) 0.0162(3) Uani 1 1 d . . . H12A H 0.8269 0.8954 0.8499 0.019 Uiso 1 1 calc R . . C13 C 0.77727(18) 0.95819(5) 0.94901(17) 0.0157(3) Uani 1 1 d . . . H13A H 0.7909 0.9449 1.0541 0.019 Uiso 1 1 calc R . . C14 C 0.73523(18) 1.00730(5) 0.91241(16) 0.0145(3) Uani 1 1 d . . . C15 C 0.71652(19) 1.02726(5) 0.75951(17) 0.0171(3) Uani 1 1 d . . . H15A H 0.6883 1.0609 0.7351 0.021 Uiso 1 1 calc R . . C16 C 0.74034(19) 0.99651(5) 0.64453(17) 0.0175(3) Uani 1 1 d . . . H16A H 0.7289 1.0089 0.5389 0.021 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01235(8) 0.01745(9) 0.01095(8) 0.00012(6) 0.00391(6) 0.00110(6) Cl2 0.01437(14) 0.02087(17) 0.02151(17) -0.00519(13) 0.00263(12) -0.00166(12) Cl3 0.01912(15) 0.02163(17) 0.01320(15) 0.00476(12) 0.00582(12) 0.00160(12) Cl4 0.01853(15) 0.02286(17) 0.01211(15) 0.00402(12) 0.00653(12) 0.00726(12) Cl5 0.02136(15) 0.01967(16) 0.01512(15) -0.00228(12) 0.00873(12) 0.00136(12) Cl1 0.02465(16) 0.02241(17) 0.01805(16) -0.00500(13) 0.00881(13) -0.00831(13) N1 0.0176(5) 0.0247(6) 0.0161(6) -0.0023(5) 0.0043(5) -0.0041(5) C2 0.0237(7) 0.0178(7) 0.0199(7) 0.0010(6) 0.0076(6) -0.0024(6) C3 0.0187(6) 0.0197(7) 0.0156(7) 0.0027(5) 0.0053(5) 0.0003(5) C4 0.0169(6) 0.0199(7) 0.0148(6) -0.0030(5) 0.0081(5) -0.0025(5) C5 0.0264(7) 0.0174(7) 0.0214(7) 0.0015(6) 0.0122(6) 0.0037(6) C6 0.0204(7) 0.0259(8) 0.0178(7) 0.0041(6) 0.0068(6) 0.0063(6) Cl11 0.01931(15) 0.01942(16) 0.01602(15) -0.00344(12) 0.00768(12) 0.00015(12) N11 0.0139(5) 0.0201(6) 0.0139(5) -0.0024(4) 0.0062(4) -0.0007(4) C12 0.0143(6) 0.0164(6) 0.0177(7) 0.0013(5) 0.0068(5) -0.0001(5) C13 0.0135(6) 0.0197(7) 0.0131(6) 0.0020(5) 0.0051(5) -0.0004(5) C14 0.0104(5) 0.0187(7) 0.0138(6) -0.0034(5) 0.0046(5) -0.0024(5) C15 0.0149(6) 0.0172(7) 0.0176(7) 0.0016(5) 0.0055(5) -0.0005(5) C16 0.0147(6) 0.0235(7) 0.0135(6) 0.0029(5) 0.0053(5) -0.0004(5) _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 Cl2 2.2264(4) . ? Cu1 Cl5 2.2408(4) . ? Cu1 Cl4 2.2632(4) . ? Cu1 Cl3 2.2812(4) . ? Cl1 C4 1.7223(14) . ? N1 C2 1.3393(18) . ? N1 C6 1.343(2) . ? N1 H1A 0.8800 . ? C2 C3 1.378(2) . ? C2 H2A 0.9500 . ? C3 C4 1.389(2) . ? C3 H3A 0.9500 . ? C4 C5 1.3924(19) . ? C5 C6 1.374(2) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? Cl11 C14 1.7264(13) . ? N11 C12 1.3396(18) . ? N11 C16 1.3434(18) . ? N11 H11A 0.8800 . ? C12 C13 1.3788(19) . ? C12 H12A 0.9500 . ? C13 C14 1.3868(19) . ? C13 H13A 0.9500 . ? C14 C15 1.3903(19) . ? C15 C16 1.379(2) . ? C15 H15A 0.9500 . ? C16 H16A 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 Cl2 Cu1 Cl5 102.292(14) . . ? Cl2 Cu1 Cl4 133.282(15) . . ? Cl5 Cu1 Cl4 101.000(13) . . ? Cl2 Cu1 Cl3 98.462(14) . . ? Cl5 Cu1 Cl3 132.618(15) . . ? Cl4 Cu1 Cl3 94.624(13) . . ? C2 N1 C6 122.46(13) . . ? C2 N1 H1A 118.8 . . ? C6 N1 H1A 118.8 . . ? N1 C2 C3 120.13(13) . . ? N1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C2 C3 C4 118.14(13) . . ? C2 C3 H3A 120.9 . . ? C4 C3 H3A 120.9 . . ? C3 C4 C5 120.97(13) . . ? C3 C4 Cl1 119.15(11) . . ? C5 C4 Cl1 119.88(11) . . ? C6 C5 C4 118.01(13) . . ? C6 C5 H5A 121.0 . . ? C4 C5 H5A 121.0 . . ? N1 C6 C5 120.28(13) . . ? N1 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C12 N11 C16 122.91(12) . . ? C12 N11 H11A 118.5 . . ? C16 N11 H11A 118.5 . . ? N11 C12 C13 119.75(13) . . ? N11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C12 C13 C14 118.20(12) . . ? C12 C13 H13A 120.9 . . ? C14 C13 H13A 120.9 . . ? C13 C14 C15 121.34(13) . . ? C13 C14 Cl11 118.60(10) . . ? C15 C14 Cl11 120.05(11) . . ? C16 C15 C14 117.78(13) . . ? C16 C15 H15A 121.1 . . ? C14 C15 H15A 121.1 . . ? N11 C16 C15 120.01(13) . . ? N11 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.324 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.050 #===END # compound 2 (phase I) (150 K) data_compound2_phaseI_150K _database_code_depnum_ccdc_archive 'CCDC 793200' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C5 H5 Cl N), Cl4 Cu ' _chemical_formula_sum 'C10 H10 Cl6 Cu N2' _chemical_formula_weight 434.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5780(15) _cell_length_b 27.411(6) _cell_length_c 8.7224(17) _cell_angle_alpha 90.00 _cell_angle_beta 115.57(3) _cell_angle_gamma 90.00 _cell_volume 1634.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 936 _cell_measurement_theta_min 3.331 _cell_measurement_theta_max 28.150 _exptl_crystal_description 'flat prism' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 2.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4749 _exptl_absorpt_correction_T_max 0.7696 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14426 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 28.35 _reflns_number_total 3932 _reflns_number_gt 3325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0361P)^2^+0.2939P] 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 3932 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0695 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.04014(3) 0.121003(9) 0.44409(3) 0.02233(8) Uani 1 1 d . . . Cl2 Cl 0.34805(7) 0.102472(19) 0.61751(7) 0.03196(13) Uani 1 1 d . . . Cl3 Cl -0.04223(7) 0.159364(18) 0.63591(6) 0.02823(12) Uani 1 1 d . . . Cl4 Cl -0.23836(7) 0.076808(18) 0.32667(6) 0.02755(12) Uani 1 1 d . . . Cl5 Cl 0.06588(7) 0.146876(18) 0.21120(7) 0.02831(12) Uani 1 1 d . . . N1 N 0.3132(3) 0.19615(6) -0.0455(2) 0.0308(4) Uani 1 1 d . . . H1 H 0.2312 0.1791 -0.1284 0.037 Uiso 1 1 calc R . . C2 C 0.3020(3) 0.24476(8) -0.0570(3) 0.0329(5) Uani 1 1 d . . . H2 H 0.2054 0.2595 -0.1522 0.039 Uiso 1 1 calc R . . C3 C 0.4330(3) 0.27279(8) 0.0718(3) 0.0307(5) Uani 1 1 d . . . H3 H 0.4283 0.3067 0.0646 0.037 Uiso 1 1 calc R . . C4 C 0.5730(3) 0.24944(7) 0.2135(3) 0.0250(4) Uani 1 1 d . . . Cl1 Cl 0.73712(8) 0.28320(2) 0.38053(7) 0.03372(13) Uani 1 1 d . . . C5 C 0.5801(3) 0.19913(7) 0.2235(3) 0.0287(4) Uani 1 1 d . . . H5 H 0.6729 0.1834 0.3186 0.034 Uiso 1 1 calc R . . C6 C 0.4464(3) 0.17302(8) 0.0893(3) 0.0318(5) Uani 1 1 d . . . H6 H 0.4487 0.1391 0.0923 0.038 Uiso 1 1 calc R . . N11 N 0.7797(2) 0.05062(6) 0.6818(2) 0.0237(4) Uani 1 1 d . . . H11 H 0.7938 0.0692 0.6084 0.028 Uiso 1 1 calc R . . C12 C 0.7979(3) 0.07031(7) 0.8283(3) 0.0251(4) Uani 1 1 d . . . H12 H 0.8246 0.1034 0.8488 0.030 Uiso 1 1 calc R . . C13 C 0.7771(3) 0.04144(7) 0.9483(3) 0.0234(4) Uani 1 1 d . . . H13 H 0.7909 0.0545 1.0514 0.028 Uiso 1 1 calc R . . C14 C 0.7352(3) -0.00732(7) 0.9122(3) 0.0226(4) Uani 1 1 d . . . Cl11 Cl 0.70964(7) -0.043946(18) 1.06212(7) 0.02842(12) Uani 1 1 d . . . C15 C 0.7169(3) -0.02719(7) 0.7598(3) 0.0258(4) Uani 1 1 d . . . H15 H 0.6895 -0.0601 0.7361 0.031 Uiso 1 1 calc R . . C16 C 0.7406(3) 0.00335(8) 0.6446(3) 0.0260(4) Uani 1 1 d . . . H16 H 0.7295 -0.0089 0.5413 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 0.02003(13) 0.02596(14) 0.01914(14) -0.00006(10) 0.00672(10) -0.00157(9) Cl2 0.0225(3) 0.0308(3) 0.0345(3) 0.0081(2) 0.0046(2) 0.00262(19) Cl3 0.0293(3) 0.0320(3) 0.0214(3) -0.0069(2) 0.0090(2) -0.0023(2) Cl4 0.0286(3) 0.0335(3) 0.0201(2) -0.0058(2) 0.0101(2) -0.0103(2) Cl5 0.0333(3) 0.0283(3) 0.0247(3) 0.0037(2) 0.0137(2) -0.0015(2) N1 0.0270(9) 0.0342(10) 0.0255(10) -0.0043(8) 0.0059(8) -0.0058(7) C2 0.0292(12) 0.0394(12) 0.0271(11) 0.0062(10) 0.0093(10) 0.0085(9) C3 0.0379(12) 0.0244(10) 0.0314(12) 0.0018(9) 0.0163(10) 0.0040(9) C4 0.0262(10) 0.0267(10) 0.0242(11) -0.0043(8) 0.0128(9) -0.0038(8) Cl1 0.0373(3) 0.0335(3) 0.0291(3) -0.0073(2) 0.0132(2) -0.0121(2) C5 0.0276(11) 0.0284(11) 0.0247(11) 0.0038(9) 0.0061(9) 0.0011(8) C6 0.0356(12) 0.0248(11) 0.0308(12) 0.0002(9) 0.0104(10) -0.0035(9) N11 0.0205(8) 0.0286(9) 0.0221(9) 0.0044(7) 0.0093(7) 0.0022(6) C12 0.0225(10) 0.0248(10) 0.0279(11) -0.0009(8) 0.0109(9) 0.0005(8) C13 0.0209(10) 0.0272(10) 0.0208(10) -0.0008(8) 0.0077(8) 0.0017(7) C14 0.0164(9) 0.0274(10) 0.0228(10) 0.0037(8) 0.0075(8) 0.0032(7) Cl11 0.0300(3) 0.0287(3) 0.0263(3) 0.0052(2) 0.0120(2) -0.00001(19) C15 0.0233(10) 0.0244(10) 0.0268(11) -0.0025(8) 0.0080(9) 0.0004(8) C16 0.0219(10) 0.0329(11) 0.0209(10) -0.0032(8) 0.0071(9) 0.0012(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 Cl2 2.2233(10) . ? Cu1 Cl5 2.2382(7) . ? Cu1 Cl4 2.2594(8) . ? Cu1 Cl3 2.2796(6) . ? N1 C6 1.334(3) . ? N1 C2 1.336(3) . ? N1 H1 0.8600 . ? C2 C3 1.369(3) . ? C2 H2 0.9300 . ? C3 C4 1.389(3) . ? C3 H3 0.9300 . ? C4 C5 1.381(3) . ? C4 Cl1 1.721(2) . ? C5 C6 1.373(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N11 C16 1.338(3) . ? N11 C12 1.338(3) . ? N11 H11 0.8600 . ? C12 C13 1.375(3) . ? C12 H12 0.9300 . ? C13 C14 1.379(3) . ? C13 H13 0.9300 . ? C14 C15 1.387(3) . ? C14 Cl11 1.724(2) . ? C15 C16 1.378(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Cu1 Cl5 102.29(3) . . ? Cl2 Cu1 Cl4 133.36(3) . . ? Cl5 Cu1 Cl4 100.88(3) . . ? Cl2 Cu1 Cl3 98.37(3) . . ? Cl5 Cu1 Cl3 132.75(2) . . ? Cl4 Cu1 Cl3 94.70(3) . . ? C6 N1 C2 122.66(19) . . ? C6 N1 H1 118.7 . . ? C2 N1 H1 118.7 . . ? N1 C2 C3 119.9(2) . . ? N1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 118.4(2) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 120.69(19) . . ? C5 C4 Cl1 119.25(17) . . ? C3 C4 Cl1 120.05(16) . . ? C6 C5 C4 118.1(2) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? N1 C6 C5 120.2(2) . . ? N1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C16 N11 C12 122.91(17) . . ? C16 N11 H11 118.5 . . ? C12 N11 H11 118.5 . . ? N11 C12 C13 119.78(19) . . ? N11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 118.33(19) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C13 C14 C15 121.18(18) . . ? C13 C14 Cl11 118.77(16) . . ? C15 C14 Cl11 120.04(16) . . ? C16 C15 C14 118.02(19) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? N11 C16 C15 119.76(19) . . ? N11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 1.2(3) . . . . ? N1 C2 C3 C4 -1.1(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C2 C3 C4 Cl1 -178.52(16) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? Cl1 C4 C5 C6 179.39(16) . . . . ? C2 N1 C6 C5 -0.3(3) . . . . ? C4 C5 C6 N1 -0.6(3) . . . . ? C16 N11 C12 C13 0.3(3) . . . . ? N11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 0.9(3) . . . . ? C12 C13 C14 Cl11 179.74(14) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? Cl11 C14 C15 C16 -179.29(14) . . . . ? C12 N11 C16 C15 0.2(3) . . . . ? C14 C15 C16 N11 -0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.963 # 100% completeness to theta 26.372 degrees _refine_diff_density_max 0.490 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.075 #===END # compound 2 (phase II) (150 K) data_compound2_phaseII_150K _database_code_depnum_ccdc_archive 'CCDC 793201' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl6 Cu N2' _chemical_formula_weight 434.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 16.263(3) _cell_length_b 7.3876(15) _cell_length_c 13.645(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.33(3) _cell_angle_gamma 90.00 _cell_volume 1617.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2187 _cell_measurement_theta_min 2.538 _cell_measurement_theta_max 23.294 _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 2.326 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3247 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 23.29 _reflns_number_total 1165 _reflns_number_gt 1055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0420P)^2^+0.5495P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1165 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0654 _refine_ls_wR_factor_gt 0.0643 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.04428(5) 0.7500 0.02364(17) Uani 1 2 d S . . Cl1 Cl -0.08043(4) -0.16548(8) 0.65770(5) 0.0266(2) Uani 1 1 d . . . Cl2 Cl 0.09427(4) 0.22862(9) 0.70346(5) 0.0325(2) Uani 1 1 d . . . N1 N 0.40658(13) -0.1833(3) 0.38785(16) 0.0271(5) Uani 1 1 d . . . H1 H 0.4411 -0.2272 0.3504 0.032 Uiso 1 1 calc R . . C2 C 0.43135(16) -0.1769(4) 0.4865(2) 0.0282(6) Uani 1 1 d . . . H2 H 0.4848 -0.2211 0.5148 0.034 Uiso 1 1 calc R . . C3 C 0.37930(16) -0.1064(3) 0.5464(2) 0.0266(6) Uani 1 1 d . . . H3 H 0.3959 -0.1002 0.6164 0.032 Uiso 1 1 calc R . . C4 C 0.30161(16) -0.0444(3) 0.5019(2) 0.0219(6) Uani 1 1 d . . . Cl4 Cl 0.23373(4) 0.04372(8) 0.57477(5) 0.0274(2) Uani 1 1 d . . . C5 C 0.27692(16) -0.0542(3) 0.40068(19) 0.0242(6) Uani 1 1 d . . . H5 H 0.2234 -0.0127 0.3707 0.029 Uiso 1 1 calc R . . C6 C 0.33160(16) -0.1256(3) 0.3442(2) 0.0269(6) Uani 1 1 d . . . H6 H 0.3162 -0.1340 0.2742 0.032 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 0.0186(3) 0.0214(3) 0.0314(3) 0.000 0.00549(19) 0.000 Cl1 0.0169(3) 0.0307(4) 0.0312(4) -0.0044(3) 0.0001(3) 0.0002(3) Cl2 0.0328(4) 0.0325(4) 0.0347(4) -0.0004(3) 0.0133(3) -0.0091(3) N1 0.0266(13) 0.0259(12) 0.0316(14) -0.0007(10) 0.0133(10) 0.0032(10) C2 0.0188(14) 0.0278(15) 0.0370(18) 0.0022(12) 0.0017(12) -0.0018(11) C3 0.0254(15) 0.0273(14) 0.0259(15) -0.0015(12) 0.0005(12) -0.0007(12) C4 0.0205(14) 0.0184(13) 0.0284(15) 0.0003(11) 0.0082(11) -0.0020(10) Cl4 0.0251(4) 0.0290(4) 0.0300(4) -0.0035(3) 0.0102(3) 0.0007(3) C5 0.0211(14) 0.0241(15) 0.0271(16) 0.0036(11) 0.0030(12) 0.0011(11) C6 0.0314(16) 0.0256(15) 0.0238(15) 0.0025(11) 0.0047(12) 0.0008(12) _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 Cl2 2.2190(8) . ? Cu1 Cl2 2.2190(8) 2_556 ? Cu1 Cl1 2.2725(8) . ? Cu1 Cl1 2.2725(8) 2_556 ? N1 C6 1.337(3) . ? N1 C2 1.342(3) . ? N1 H1 0.8800 . ? C2 C3 1.372(4) . ? C2 H2 0.9500 . ? C3 C4 1.388(4) . ? C3 H3 0.9500 . ? C4 C5 1.377(4) . ? C4 Cl4 1.728(3) . ? C5 C6 1.373(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Cu1 Cl2 104.28(4) . 2_556 ? Cl2 Cu1 Cl1 128.48(3) . . ? Cl2 Cu1 Cl1 102.40(3) 2_556 . ? Cl2 Cu1 Cl1 102.40(3) . 2_556 ? Cl2 Cu1 Cl1 128.48(3) 2_556 2_556 ? Cl1 Cu1 Cl1 94.02(4) . 2_556 ? C6 N1 C2 122.6(2) . . ? C6 N1 H1 118.7 . . ? C2 N1 H1 118.7 . . ? N1 C2 C3 119.8(2) . . ? N1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 118.0(2) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 121.3(2) . . ? C5 C4 Cl4 119.2(2) . . ? C3 C4 Cl4 119.6(2) . . ? C6 C5 C4 118.2(2) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? N1 C6 C5 120.0(2) . . ? N1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? 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 C6 N1 C2 C3 -1.0(4) . . . . ? N1 C2 C3 C4 0.4(4) . . . . ? C2 C3 C4 C5 0.5(4) . . . . ? C2 C3 C4 Cl4 179.5(2) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? Cl4 C4 C5 C6 -179.66(19) . . . . ? C2 N1 C6 C5 0.8(4) . . . . ? C4 C5 C6 N1 0.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.346 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.066 #===END