# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jie-Peng Zhang' _publ_contact_author_email zhangjp7@mail.sysu.edu.cn loop_ _publ_author_name 'Da Chen' 'Yi-Jiang Liu' 'Yan-Yong Lin' 'Jie-Peng Zhang' ; Xiao-Ming Chen ; data_1a _database_code_depnum_ccdc_archive 'CCDC 809084' #TrackingRef '1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H3 Cu N4' _chemical_formula_weight 146.62 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' 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 3.6325(6) _cell_length_b 10.2841(17) _cell_length_c 10.4812(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.379(3) _cell_angle_gamma 90.00 _cell_volume 388.30(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 5.442 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7725 _exptl_absorpt_correction_T_max 0.8989 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method '/w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1419 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 25.93 _reflns_number_total 733 _reflns_number_gt 567 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0372P)^2^+8.0442P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 733 _refine_ls_number_parameters 76 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.1399(4) 0.38592(10) 0.39304(10) 0.0273(4) Uani 1 1 d . . . N1 N 0.164(2) 0.3525(7) 0.5781(7) 0.0261(19) Uani 1 1 d . . . N2 N 0.028(2) 0.4387(7) 0.6632(6) 0.0237(18) Uani 1 1 d . . . N3 N 0.181(2) 0.2544(7) 0.7694(6) 0.0220(17) Uani 1 1 d . . . N4 N 0.392(3) 0.1343(8) 0.5949(8) 0.033(2) Uani 1 1 d . . . H4A H 0.55(3) 0.152(10) 0.540(10) 0.04(3) Uiso 1 1 d . . . H4B H 0.54(3) 0.099(11) 0.660(11) 0.04(3) Uiso 1 1 d . . . C1 C 0.257(3) 0.2467(8) 0.6456(7) 0.0209(19) Uani 1 1 d . . . C2 C 0.048(3) 0.3756(9) 0.7738(8) 0.025(2) Uani 1 1 d . . . H2 H -0.09(2) 0.411(7) 0.840(7) 0.01(2) Uiso 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 0.0517(8) 0.0162(6) 0.0153(6) -0.0014(5) 0.0099(5) 0.0014(6) N1 0.049(5) 0.016(4) 0.014(3) 0.000(3) 0.007(3) 0.011(4) N2 0.047(5) 0.013(4) 0.012(3) -0.003(3) 0.007(3) 0.003(4) N3 0.036(5) 0.016(4) 0.013(3) 0.001(3) 0.001(3) -0.002(3) N4 0.059(6) 0.021(4) 0.022(4) 0.000(4) 0.018(4) 0.007(5) C1 0.036(5) 0.019(4) 0.008(4) 0.000(3) 0.002(3) 0.001(4) C2 0.040(6) 0.018(4) 0.020(4) -0.002(4) 0.012(4) 0.003(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 N3 1.958(7) 4_565 ? Cu1 N1 1.961(7) . ? Cu1 N2 1.969(7) 3_566 ? N1 C1 1.319(11) . ? N1 N2 1.392(10) . ? N2 C2 1.322(11) . ? N2 Cu1 1.969(7) 3_566 ? N3 C2 1.339(11) . ? N3 C1 1.363(10) . ? N3 Cu1 1.958(7) 4_566 ? N4 C1 1.388(11) . ? N4 H4A 0.88(11) . ? N4 H4B 0.89(11) . ? C2 H2 0.99(8) . ? 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 N3 Cu1 N1 121.9(3) 4_565 . ? N3 Cu1 N2 121.6(3) 4_565 3_566 ? N1 Cu1 N2 115.4(3) . 3_566 ? C1 N1 N2 105.7(6) . . ? C1 N1 Cu1 130.6(6) . . ? N2 N1 Cu1 123.2(5) . . ? C2 N2 N1 105.3(7) . . ? C2 N2 Cu1 133.9(6) . 3_566 ? N1 N2 Cu1 120.8(5) . 3_566 ? C2 N3 C1 101.9(7) . . ? C2 N3 Cu1 127.2(6) . 4_566 ? C1 N3 Cu1 129.0(6) . 4_566 ? C1 N4 H4A 112(7) . . ? C1 N4 H4B 105(7) . . ? H4A N4 H4B 102(10) . . ? N1 C1 N3 113.1(7) . . ? N1 C1 N4 124.1(7) . . ? N3 C1 N4 122.6(8) . . ? N2 C2 N3 114.0(8) . . ? N2 C2 H2 117(5) . . ? N3 C2 H2 126(5) . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.93 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.891 _refine_diff_density_min -0.928 _refine_diff_density_rms 0.215 # Attachment '1b.cif' data_1b _database_code_depnum_ccdc_archive 'CCDC 809085' #TrackingRef '1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H3 Cu N4' _chemical_formula_weight 146.62 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.3115(9) _cell_length_b 10.4977(10) _cell_length_c 14.7439(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1596.0(3) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 5.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4172 _exptl_absorpt_correction_T_max 0.4663 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method '/w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6472 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1560 _reflns_number_gt 1327 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0626P)^2^+3.4956P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1560 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.38493(6) 0.36740(6) 0.84947(4) 0.0234(2) Uani 1 1 d . . . Cu2 Cu 0.61412(6) 0.59701(6) 0.91845(4) 0.0234(2) Uani 1 1 d . . . N1 N 0.3523(4) 0.5511(4) 0.8404(3) 0.0226(9) Uani 1 1 d . . . N2 N 0.4399(4) 0.6437(4) 0.8711(3) 0.0213(9) Uani 1 1 d . . . N3 N 0.2541(4) 0.7416(4) 0.8361(3) 0.0216(9) Uani 1 1 d . . . N4 N 0.1332(4) 0.5585(5) 0.7936(3) 0.0269(10) Uani 1 1 d . . . H4A H 0.146(5) 0.488(6) 0.770(3) 0.018(14) Uiso 1 1 d . . . H4B H 0.090(5) 0.600(5) 0.768(4) 0.017(15) Uiso 1 1 d . . . N5 N 0.6498(4) 0.4141(4) 0.9180(3) 0.0216(9) Uani 1 1 d . . . N6 N 0.5644(4) 0.3224(4) 0.8831(3) 0.0227(9) Uani 1 1 d . . . N7 N 0.7490(4) 0.2249(4) 0.9218(3) 0.0222(9) Uani 1 1 d . . . N8 N 0.8664(4) 0.4072(5) 0.9738(3) 0.0258(10) Uani 1 1 d . . . H8A H 0.852(5) 0.476(6) 0.997(4) 0.019(14) Uiso 1 1 d . . . H8B H 0.912(7) 0.360(7) 1.007(5) 0.05(2) Uiso 1 1 d . . . C1 C 0.2458(5) 0.6156(4) 0.8198(3) 0.0189(10) Uani 1 1 d . . . C2 C 0.3783(5) 0.7529(5) 0.8669(4) 0.0236(11) Uani 1 1 d . . . H2 H 0.420(5) 0.832(6) 0.884(4) 0.025(14) Uiso 1 1 d . . . C3 C 0.7565(4) 0.3504(4) 0.9399(3) 0.0191(10) Uani 1 1 d . . . C4 C 0.6285(5) 0.2131(5) 0.8868(4) 0.0251(11) Uani 1 1 d . . . H4 H 0.593(5) 0.133(5) 0.871(3) 0.011(12) Uiso 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 0.0117(3) 0.0159(4) 0.0427(4) 0.0001(2) -0.0009(2) -0.0018(2) Cu2 0.0128(4) 0.0164(4) 0.0410(4) -0.0013(2) -0.0013(2) -0.0015(2) N1 0.0115(19) 0.013(2) 0.043(2) 0.0001(17) -0.0063(17) -0.0007(16) N2 0.009(2) 0.014(2) 0.041(2) -0.0009(16) 0.0003(17) -0.0028(16) N3 0.012(2) 0.018(2) 0.035(2) -0.0021(17) 0.0025(16) 0.0037(17) N4 0.019(2) 0.018(2) 0.044(3) -0.002(2) -0.0111(19) 0.004(2) N5 0.012(2) 0.010(2) 0.042(2) -0.0020(16) -0.0040(17) 0.0004(15) N6 0.010(2) 0.019(2) 0.039(2) -0.0006(17) -0.0024(17) -0.0039(17) N7 0.010(2) 0.018(2) 0.038(2) 0.0003(17) -0.0007(16) 0.0038(16) N8 0.012(2) 0.026(3) 0.039(3) -0.002(2) -0.0075(18) -0.0006(18) C1 0.013(2) 0.019(2) 0.025(2) 0.0008(18) 0.0052(18) -0.0009(18) C2 0.013(2) 0.019(3) 0.038(3) 0.000(2) -0.001(2) 0.000(2) C3 0.012(2) 0.018(2) 0.028(2) 0.0006(18) 0.0016(18) -0.0013(19) C4 0.017(3) 0.020(3) 0.039(3) -0.005(2) 0.001(2) -0.001(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 N3 1.959(4) 8_655 ? Cu1 N1 1.962(4) . ? Cu1 N6 1.974(4) . ? Cu2 N7 1.948(4) 8_765 ? Cu2 N5 1.955(4) . ? Cu2 N2 1.988(4) . ? N1 C1 1.325(6) . ? N1 N2 1.402(6) . ? N2 C2 1.312(7) . ? N3 C1 1.348(6) . ? N3 C2 1.363(6) . ? N3 Cu1 1.959(4) 8_665 ? N4 C1 1.363(6) . ? N4 H4A 0.83(6) . ? N4 H4B 0.73(5) . ? N5 C3 1.327(6) . ? N5 N6 1.403(6) . ? N6 C4 1.325(7) . ? N7 C3 1.347(6) . ? N7 C4 1.352(6) . ? N7 Cu2 1.948(4) 8_755 ? N8 C3 1.374(6) . ? N8 H8A 0.81(6) . ? N8 H8B 0.84(7) . ? C2 H2 0.96(6) . ? C4 H4 0.95(5) . ? 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 N3 Cu1 N1 122.02(17) 8_655 . ? N3 Cu1 N6 123.37(17) 8_655 . ? N1 Cu1 N6 114.42(17) . . ? N7 Cu2 N5 122.69(17) 8_765 . ? N7 Cu2 N2 119.58(17) 8_765 . ? N5 Cu2 N2 114.26(17) . . ? C1 N1 N2 104.7(4) . . ? C1 N1 Cu1 131.3(3) . . ? N2 N1 Cu1 123.3(3) . . ? C2 N2 N1 106.1(4) . . ? C2 N2 Cu2 132.0(3) . . ? N1 N2 Cu2 121.7(3) . . ? C1 N3 C2 101.8(4) . . ? C1 N3 Cu1 129.3(3) . 8_665 ? C2 N3 Cu1 126.5(3) . 8_665 ? C1 N4 H4A 112(3) . . ? C1 N4 H4B 114(4) . . ? H4A N4 H4B 114(6) . . ? C3 N5 N6 105.3(4) . . ? C3 N5 Cu2 130.5(3) . . ? N6 N5 Cu2 123.8(3) . . ? C4 N6 N5 105.5(4) . . ? C4 N6 Cu1 133.3(4) . . ? N5 N6 Cu1 121.1(3) . . ? C3 N7 C4 102.6(4) . . ? C3 N7 Cu2 129.6(3) . 8_755 ? C4 N7 Cu2 126.4(4) . 8_755 ? C3 N8 H8A 112(4) . . ? C3 N8 H8B 115(5) . . ? H8A N8 H8B 113(6) . . ? N1 C1 N3 114.1(4) . . ? N1 C1 N4 123.1(4) . . ? N3 C1 N4 122.4(4) . . ? N2 C2 N3 113.3(5) . . ? N2 C2 H2 121(3) . . ? N3 C2 H2 125(3) . . ? N5 C3 N7 113.4(4) . . ? N5 C3 N8 123.6(4) . . ? N7 C3 N8 122.9(4) . . ? N6 C4 N7 113.3(5) . . ? N6 C4 H4 124(3) . . ? N7 C4 H4 122(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.986 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.163 # Attachment '1g.cif' data_1g _database_code_depnum_ccdc_archive 'CCDC 809086' #TrackingRef '1g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H3 Cu N4' _chemical_formula_weight 146.62 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' 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 8.4608(7) _cell_length_b 10.3198(9) _cell_length_c 10.5728(9) _cell_angle_alpha 90.00 _cell_angle_beta 118.944(8) _cell_angle_gamma 90.00 _cell_volume 807.84(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 5.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4209 _exptl_absorpt_correction_T_max 0.5075 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method '/w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4719 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1532 _reflns_number_gt 1251 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0620P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1532 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0903 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.30203(6) 0.61691(4) -0.01241(4) 0.02573(18) Uani 1 1 d . . . Cu2 Cu 0.16193(6) 0.38474(4) 0.16136(4) 0.02503(18) Uani 1 1 d . . . N1 N 0.3202(4) 0.6471(3) 0.1791(3) 0.0231(6) Uani 1 1 d . . . N2 N 0.2581(4) 0.5579(3) 0.2462(3) 0.0255(6) Uani 1 1 d . . . N3 N 0.3331(4) 0.7416(2) 0.3754(3) 0.0229(6) Uani 1 1 d . . . N4 N 0.4169(5) 0.8669(3) 0.2253(4) 0.0294(7) Uani 1 1 d . . . N5 N 0.1604(4) 0.3519(3) -0.0223(3) 0.0233(6) Uani 1 1 d . . . N6 N 0.2323(4) 0.4368(3) -0.0853(3) 0.0239(6) Uani 1 1 d . . . N7 N 0.1560(4) 0.2527(2) -0.2125(3) 0.0222(6) Uani 1 1 d . . . N8 N 0.0490(5) 0.1347(3) -0.0730(4) 0.0301(7) Uani 1 1 d . . . C1 C 0.3621(4) 0.7532(3) 0.2613(3) 0.0211(7) Uani 1 1 d . . . C2 C 0.2686(5) 0.6182(3) 0.3602(4) 0.0250(8) Uani 1 1 d . . . C3 C 0.1171(4) 0.2452(3) -0.1028(3) 0.0203(7) Uani 1 1 d . . . C4 C 0.2259(5) 0.3741(3) -0.1965(4) 0.0241(8) Uani 1 1 d . . . H4 H 0.265(4) 0.413(3) -0.265(4) 0.023(9) Uiso 1 1 d . . . H4A H 0.469(5) 0.850(4) 0.176(4) 0.032(12) Uiso 1 1 d . . . H4B H 0.475(6) 0.908(4) 0.290(5) 0.032(13) Uiso 1 1 d . . . H2 H 0.228(4) 0.577(3) 0.430(4) 0.025(9) Uiso 1 1 d . . . H8B H -0.023(6) 0.096(4) -0.159(5) 0.050(14) Uiso 1 1 d . . . H8A H -0.012(5) 0.151(4) -0.034(4) 0.017(10) Uiso 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 0.0451(3) 0.0142(3) 0.0243(3) 0.00133(15) 0.0219(2) -0.00054(16) Cu2 0.0427(3) 0.0145(3) 0.0247(3) 0.00060(15) 0.0217(2) -0.00137(17) N1 0.0364(15) 0.0130(13) 0.0257(14) -0.0026(11) 0.0197(13) -0.0024(11) N2 0.0437(16) 0.0131(13) 0.0241(13) -0.0004(11) 0.0199(13) -0.0026(12) N3 0.0359(15) 0.0156(14) 0.0217(13) -0.0039(11) 0.0175(13) -0.0033(12) N4 0.0422(19) 0.0198(16) 0.0308(18) -0.0037(13) 0.0213(17) -0.0079(14) N5 0.0394(16) 0.0142(14) 0.0241(13) -0.0011(11) 0.0216(13) -0.0027(12) N6 0.0403(16) 0.0127(13) 0.0234(13) -0.0010(11) 0.0192(13) -0.0032(12) N7 0.0349(15) 0.0142(14) 0.0230(14) -0.0025(10) 0.0183(13) -0.0011(11) N8 0.0424(19) 0.0222(16) 0.0343(17) -0.0063(13) 0.0254(17) -0.0095(14) C1 0.0277(16) 0.0154(16) 0.0240(15) -0.0010(12) 0.0154(14) 0.0003(13) C2 0.039(2) 0.0157(17) 0.0250(17) -0.0016(13) 0.0197(16) -0.0009(14) C3 0.0294(16) 0.0131(16) 0.0182(15) 0.0015(12) 0.0113(14) 0.0018(13) C4 0.0374(19) 0.0154(17) 0.0236(16) 0.0008(13) 0.0181(16) 0.0007(14) _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 N3 1.978(3) 4_575 ? Cu1 N1 1.980(3) . ? Cu1 N6 1.989(3) . ? Cu2 N7 1.964(3) 4_566 ? Cu2 N5 1.965(3) . ? Cu2 N2 1.988(3) . ? N1 C1 1.335(4) . ? N1 N2 1.410(4) . ? N2 C2 1.321(4) . ? N3 C1 1.347(4) . ? N3 C2 1.363(4) . ? N3 Cu1 1.978(3) 4_576 ? N4 C1 1.382(4) . ? N4 H4A 0.84(4) . ? N4 H4B 0.75(4) . ? N5 C3 1.330(4) . ? N5 N6 1.404(4) . ? N6 C4 1.320(4) . ? N7 C3 1.353(4) . ? N7 C4 1.361(4) . ? N7 Cu2 1.964(3) 4_565 ? N8 C3 1.381(4) . ? N8 H8B 0.91(4) . ? N8 H8A 0.82(4) . ? C2 H2 1.04(4) . ? C4 H4 1.01(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 N3 Cu1 N1 122.04(11) 4_575 . ? N3 Cu1 N6 123.93(11) 4_575 . ? N1 Cu1 N6 113.88(11) . . ? N7 Cu2 N5 123.81(11) 4_566 . ? N7 Cu2 N2 118.81(11) 4_566 . ? N5 Cu2 N2 113.98(11) . . ? C1 N1 N2 104.7(3) . . ? C1 N1 Cu1 131.3(2) . . ? N2 N1 Cu1 123.3(2) . . ? C2 N2 N1 105.9(3) . . ? C2 N2 Cu2 131.9(2) . . ? N1 N2 Cu2 122.0(2) . . ? C1 N3 C2 102.3(3) . . ? C1 N3 Cu1 127.3(2) . 4_576 ? C2 N3 Cu1 126.7(2) . 4_576 ? C1 N4 H4A 109(3) . . ? C1 N4 H4B 113(3) . . ? H4A N4 H4B 112(4) . . ? C3 N5 N6 105.2(3) . . ? C3 N5 Cu2 130.0(2) . . ? N6 N5 Cu2 124.3(2) . . ? C4 N6 N5 106.1(3) . . ? C4 N6 Cu1 132.8(2) . . ? N5 N6 Cu1 120.9(2) . . ? C3 N7 C4 102.6(3) . . ? C3 N7 Cu2 129.6(2) . 4_565 ? C4 N7 Cu2 126.7(2) . 4_565 ? C3 N8 H8B 107(3) . . ? C3 N8 H8A 113(3) . . ? H8B N8 H8A 108(4) . . ? N1 C1 N3 113.8(3) . . ? N1 C1 N4 122.4(3) . . ? N3 C1 N4 123.6(3) . . ? N2 C2 N3 113.2(3) . . ? N2 C2 H2 124(2) . . ? N3 C2 H2 123(2) . . ? N5 C3 N7 113.2(3) . . ? N5 C3 N8 123.7(3) . . ? N7 C3 N8 123.0(3) . . ? N6 C4 N7 112.9(3) . . ? N6 C4 H4 124(2) . . ? N7 C4 H4 123(2) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.915 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.122