# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Dr. Guoping Yong Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, ; _publ_contact_author_email gpyong@ustc.edu.cn #TrackingRef '- Compd1-2.CIF' _publ_contact_author_name 'Dr. Guoping Yong' _publ_author_name 'Guoping Yong' data_1 _database_code_depnum_ccdc_archive 'CCDC 900322' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H8 N4 O2' _chemical_formula_weight 288.26 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 3.78300(10) _cell_length_b 13.7734(3) _cell_length_c 11.4497(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.218(3) _cell_angle_gamma 90.00 _cell_volume 593.07(3) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1619 _cell_measurement_theta_min 3.2060 _cell_measurement_theta_max 69.2813 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 0.781 _exptl_absorpt_correction_T_min 0.772 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1921 _diffrn_reflns_av_R_equivalents 0.0128 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 6.43 _diffrn_reflns_theta_max 66.54 _reflns_number_total 1043 _reflns_number_gt 986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0549P)^2^+0.2250P] 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 1043 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 C6 C 0.3986(4) 0.09431(11) 0.97384(13) 0.0356(4) Uani 1 1 d . . . O1 O 0.9158(3) -0.04206(8) 1.20567(10) 0.0475(4) Uani 1 1 d . . . N2 N 0.3358(3) 0.19341(9) 0.97453(11) 0.0353(3) Uani 1 1 d . . . N1 N 0.6631(4) 0.15575(9) 1.14650(12) 0.0393(4) Uani 1 1 d . . . C8 C 0.7255(4) -0.02411(11) 1.11475(13) 0.0359(4) Uani 1 1 d . . . C2 C 0.4709(4) 0.32694(12) 1.10685(15) 0.0416(4) Uani 1 1 d . . . H2A H 0.5743 0.3519 1.1779 0.050 Uiso 1 1 calc R . . C5 C 0.1625(4) 0.25400(12) 0.89204(14) 0.0409(4) Uani 1 1 d . . . H5A H 0.0620 0.2297 0.8202 0.049 Uiso 1 1 calc R . . C1 C 0.4986(4) 0.22761(11) 1.08148(13) 0.0365(4) Uani 1 1 d . . . C7 C 0.5993(4) 0.07552(11) 1.08037(13) 0.0354(4) Uani 1 1 d . . . C3 C 0.2902(4) 0.38601(12) 1.02576(16) 0.0459(4) Uani 1 1 d . . . H3A H 0.2655 0.4516 1.0426 0.055 Uiso 1 1 calc R . . C4 C 0.1402(5) 0.34933(12) 0.91680(16) 0.0455(4) Uani 1 1 d . . . H4A H 0.0248 0.3912 0.8614 0.055 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 C6 0.0367(7) 0.0326(8) 0.0370(8) 0.0014(6) 0.0024(6) 0.0012(6) O1 0.0588(7) 0.0424(7) 0.0376(6) 0.0027(5) -0.0116(5) 0.0002(5) N2 0.0365(7) 0.0329(7) 0.0364(7) -0.0001(5) 0.0031(5) 0.0000(5) N1 0.0428(7) 0.0366(7) 0.0372(7) -0.0026(5) -0.0009(6) -0.0011(5) C8 0.0356(7) 0.0395(8) 0.0319(7) 0.0029(6) 0.0006(6) -0.0007(6) C2 0.0426(8) 0.0399(9) 0.0421(9) -0.0056(7) 0.0031(7) -0.0017(7) C5 0.0412(8) 0.0434(9) 0.0372(8) 0.0047(7) 0.0004(7) 0.0030(7) C1 0.0356(8) 0.0375(8) 0.0360(8) 0.0009(6) 0.0023(6) 0.0002(6) C7 0.0366(7) 0.0351(8) 0.0342(8) -0.0017(6) 0.0020(6) -0.0024(6) C3 0.0462(9) 0.0337(8) 0.0580(11) -0.0009(7) 0.0071(8) 0.0034(7) C4 0.0468(9) 0.0403(9) 0.0489(10) 0.0063(7) 0.0030(7) 0.0072(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C6 N2 1.386(2) . ? C6 C7 1.389(2) . ? C6 C8 1.442(2) 3_657 ? O1 C8 1.2251(19) . ? N2 C5 1.3728(19) . ? N2 C1 1.3917(19) . ? N1 C7 1.3465(19) . ? N1 C1 1.349(2) . ? C8 C6 1.442(2) 3_657 ? C8 C7 1.492(2) . ? C2 C3 1.362(2) . ? C2 C1 1.405(2) . ? C2 H2A 0.9300 . ? C5 C4 1.348(2) . ? C5 H5A 0.9300 . ? C3 C4 1.407(3) . ? C3 H3A 0.9300 . ? C4 H4A 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 N2 C6 C7 104.84(13) . . ? N2 C6 C8 128.42(13) . 3_657 ? C7 C6 C8 126.70(14) . 3_657 ? C5 N2 C6 131.63(13) . . ? C5 N2 C1 122.17(14) . . ? C6 N2 C1 106.19(12) . . ? C7 N1 C1 104.35(13) . . ? O1 C8 C6 125.36(15) . 3_657 ? O1 C8 C7 123.48(15) . . ? C6 C8 C7 111.14(13) 3_657 . ? C3 C2 C1 118.96(15) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C4 C5 N2 118.92(15) . . ? C4 C5 H5A 120.5 . . ? N2 C5 H5A 120.5 . . ? N1 C1 N2 111.76(13) . . ? N1 C1 C2 129.83(15) . . ? N2 C1 C2 118.41(14) . . ? N1 C7 C6 112.86(14) . . ? N1 C7 C8 125.02(14) . . ? C6 C7 C8 122.12(14) . . ? C2 C3 C4 120.96(16) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 120.52(16) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C6 N2 C5 177.78(15) . . . . ? C8 C6 N2 C5 -4.4(3) 3_657 . . . ? C7 C6 N2 C1 -0.65(15) . . . . ? C8 C6 N2 C1 177.20(15) 3_657 . . . ? C6 N2 C5 C4 179.82(16) . . . . ? C1 N2 C5 C4 -2.0(2) . . . . ? C7 N1 C1 N2 -0.74(17) . . . . ? C7 N1 C1 C2 178.95(16) . . . . ? C5 N2 C1 N1 -177.72(13) . . . . ? C6 N2 C1 N1 0.89(17) . . . . ? C5 N2 C1 C2 2.6(2) . . . . ? C6 N2 C1 C2 -178.84(14) . . . . ? C3 C2 C1 N1 179.60(16) . . . . ? C3 C2 C1 N2 -0.7(2) . . . . ? C1 N1 C7 C6 0.31(17) . . . . ? C1 N1 C7 C8 -179.61(14) . . . . ? N2 C6 C7 N1 0.23(17) . . . . ? C8 C6 C7 N1 -177.67(14) 3_657 . . . ? N2 C6 C7 C8 -179.86(13) . . . . ? C8 C6 C7 C8 2.2(3) 3_657 . . . ? O1 C8 C7 N1 -3.5(2) . . . . ? C6 C8 C7 N1 177.97(14) 3_657 . . . ? O1 C8 C7 C6 176.64(14) . . . . ? C6 C8 C7 C6 -1.9(2) 3_657 . . . ? C1 C2 C3 C4 -1.6(2) . . . . ? N2 C5 C4 C3 -0.4(2) . . . . ? C2 C3 C4 C5 2.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 66.54 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.203 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.036 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 900323' #TrackingRef '- Compd1-2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H4 Cl Cu N2 O' _chemical_formula_weight 243.12 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 3.8062(4) _cell_length_b 9.0241(9) _cell_length_c 11.0195(7) _cell_angle_alpha 76.628(8) _cell_angle_beta 89.855(7) _cell_angle_gamma 85.583(8) _cell_volume 367.09(6) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1918 _cell_measurement_theta_min 4.1207 _cell_measurement_theta_max 69.5316 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 7.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.115 _exptl_absorpt_correction_T_max 0.136 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2596 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 69.66 _reflns_number_total 1347 _reflns_number_gt 1264 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0436P)^2^+0.3990P] 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 1347 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.32334(13) 0.94081(6) 0.63419(5) 0.0476(2) Uani 1 1 d . . . N1 N 0.2776(6) 1.2552(2) 0.85846(19) 0.0256(5) Uani 1 1 d . . . O1 O 0.0761(6) 0.7519(2) 0.8958(2) 0.0423(5) Uani 1 1 d . . . C2 C 0.6034(7) 1.4420(3) 0.6685(3) 0.0339(6) Uani 1 1 d . . . H2 H 0.7148 1.5075 0.6049 0.041 Uiso 1 1 calc R . . C6 C 0.1284(7) 1.1360(3) 0.9396(2) 0.0259(5) Uani 1 1 d . . . C3 C 0.5573(7) 1.2965(3) 0.6580(3) 0.0312(6) Uani 1 1 d . . . H3 H 0.6364 1.2621 0.5887 0.037 Uiso 1 1 calc R . . C5 C 0.3242(7) 1.4014(3) 0.8680(3) 0.0314(6) Uani 1 1 d . . . H5 H 0.2469 1.4355 0.9377 0.038 Uiso 1 1 calc R . . C1 C 0.4850(8) 1.4949(3) 0.7739(3) 0.0357(6) Uani 1 1 d . . . H1 H 0.5179 1.5944 0.7787 0.043 Uiso 1 1 calc R . . N2 N 0.3078(6) 1.0538(3) 0.7685(2) 0.0271(5) Uani 1 1 d . . . C7 C 0.1533(6) 1.0160(3) 0.8817(2) 0.0251(5) Uani 1 1 d . . . C4 C 0.3870(7) 1.2009(3) 0.7552(2) 0.0254(5) Uani 1 1 d . . . C8 C 0.0329(7) 0.8625(3) 0.9404(2) 0.0276(5) Uani 1 1 d . . . Cl1 Cl -0.15940(17) 0.82579(8) 0.57761(6) 0.0347(2) 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 0.0572(3) 0.0495(3) 0.0461(3) -0.0291(2) 0.0100(2) -0.0114(2) N1 0.0288(11) 0.0257(10) 0.0228(10) -0.0070(8) -0.0003(8) -0.0002(8) O1 0.0660(14) 0.0301(10) 0.0351(11) -0.0157(9) 0.0127(10) -0.0063(9) C2 0.0374(15) 0.0333(14) 0.0303(14) -0.0047(11) 0.0018(11) -0.0065(11) C6 0.0289(12) 0.0254(12) 0.0234(12) -0.0061(10) 0.0003(10) 0.0000(9) C3 0.0315(13) 0.0376(14) 0.0253(13) -0.0081(11) 0.0020(10) -0.0052(11) C5 0.0372(14) 0.0277(13) 0.0324(14) -0.0131(11) 0.0018(11) -0.0031(11) C1 0.0401(15) 0.0280(13) 0.0399(15) -0.0084(12) 0.0003(12) -0.0068(11) N2 0.0300(11) 0.0283(11) 0.0250(10) -0.0106(9) 0.0012(8) -0.0022(8) C7 0.0266(12) 0.0265(12) 0.0231(12) -0.0079(10) 0.0003(9) -0.0006(9) C4 0.0264(12) 0.0281(12) 0.0235(12) -0.0105(10) -0.0007(9) 0.0003(10) C8 0.0316(13) 0.0275(13) 0.0249(13) -0.0093(10) -0.0004(10) 0.0003(10) Cl1 0.0331(4) 0.0369(4) 0.0382(4) -0.0153(3) 0.0074(3) -0.0090(3) _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 N2 1.980(2) . ? Cu1 Cl1 2.3067(9) 1_655 ? Cu1 Cl1 2.3326(8) . ? N1 C5 1.373(3) . ? N1 C6 1.387(3) . ? N1 C4 1.389(3) . ? O1 C8 1.212(3) . ? C2 C3 1.369(4) . ? C2 C1 1.415(4) . ? C2 H2 0.9300 . ? C6 C7 1.375(4) . ? C6 C8 1.459(4) 2_577 ? C3 C4 1.403(4) . ? C3 H3 0.9300 . ? C5 C1 1.354(4) . ? C5 H5 0.9300 . ? C1 H1 0.9300 . ? N2 C4 1.359(3) . ? N2 C7 1.360(3) . ? C7 C8 1.493(4) . ? C8 C6 1.459(4) 2_577 ? Cl1 Cu1 2.3067(9) 1_455 ? 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 N2 Cu1 Cl1 122.18(7) . 1_655 ? N2 Cu1 Cl1 123.08(7) . . ? Cl1 Cu1 Cl1 110.25(3) 1_655 . ? C5 N1 C6 131.1(2) . . ? C5 N1 C4 122.2(2) . . ? C6 N1 C4 106.8(2) . . ? C3 C2 C1 121.4(3) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C7 C6 N1 105.7(2) . . ? C7 C6 C8 126.6(2) . 2_577 ? N1 C6 C8 127.7(2) . 2_577 ? C2 C3 C4 117.9(3) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C1 C5 N1 118.6(3) . . ? C1 C5 H5 120.7 . . ? N1 C5 H5 120.7 . . ? C5 C1 C2 120.4(3) . . ? C5 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C4 N2 C7 105.2(2) . . ? C4 N2 Cu1 125.38(18) . . ? C7 N2 Cu1 128.18(18) . . ? N2 C7 C6 111.9(2) . . ? N2 C7 C8 125.2(2) . . ? C6 C7 C8 122.9(2) . . ? N2 C4 N1 110.5(2) . . ? N2 C4 C3 130.0(2) . . ? N1 C4 C3 119.6(2) . . ? O1 C8 C6 125.4(3) . 2_577 ? O1 C8 C7 124.2(2) . . ? C6 C8 C7 110.4(2) 2_577 . ? Cu1 Cl1 Cu1 110.25(3) 1_455 . ? 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 C5 N1 C6 C7 -179.9(3) . . . . ? C4 N1 C6 C7 -0.2(3) . . . . ? C5 N1 C6 C8 1.9(4) . . . 2_577 ? C4 N1 C6 C8 -178.3(2) . . . 2_577 ? C1 C2 C3 C4 0.3(4) . . . . ? C6 N1 C5 C1 179.1(3) . . . . ? C4 N1 C5 C1 -0.6(4) . . . . ? N1 C5 C1 C2 -0.3(4) . . . . ? C3 C2 C1 C5 0.4(4) . . . . ? Cl1 Cu1 N2 C4 82.2(2) 1_655 . . . ? Cl1 Cu1 N2 C4 -123.86(19) . . . . ? Cl1 Cu1 N2 C7 -112.5(2) 1_655 . . . ? Cl1 Cu1 N2 C7 41.4(2) . . . . ? C4 N2 C7 C6 0.8(3) . . . . ? Cu1 N2 C7 C6 -166.80(18) . . . . ? C4 N2 C7 C8 -177.3(2) . . . . ? Cu1 N2 C7 C8 15.0(4) . . . . ? N1 C6 C7 N2 -0.4(3) . . . . ? C8 C6 C7 N2 177.8(2) 2_577 . . . ? N1 C6 C7 C8 177.8(2) . . . . ? C8 C6 C7 C8 -4.0(5) 2_577 . . . ? C7 N2 C4 N1 -0.9(3) . . . . ? Cu1 N2 C4 N1 167.13(16) . . . . ? C7 N2 C4 C3 178.1(3) . . . . ? Cu1 N2 C4 C3 -13.8(4) . . . . ? C5 N1 C4 N2 -179.5(2) . . . . ? C6 N1 C4 N2 0.7(3) . . . . ? C5 N1 C4 C3 1.3(4) . . . . ? C6 N1 C4 C3 -178.4(2) . . . . ? C2 C3 C4 N2 179.9(3) . . . . ? C2 C3 C4 N1 -1.1(4) . . . . ? N2 C7 C8 O1 3.8(4) . . . . ? C6 C7 C8 O1 -174.1(3) . . . . ? N2 C7 C8 C6 -178.6(2) . . . 2_577 ? C6 C7 C8 C6 3.4(4) . . . 2_577 ? N2 Cu1 Cl1 Cu1 23.39(10) . . . 1_455 ? Cl1 Cu1 Cl1 Cu1 180.0 1_655 . . 1_455 ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 69.66 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.399 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.073 #===END