Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Xiao-Ming Chen' _publ_contact_author_address # Name and address of author for correspondence ; Chen, Xiao-Ming School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou, 510275 P. R. China ; _publ_contact_author_phone 86-20-84113986 _publ_contact_author_fax '86 20 84112245' _publ_contact_author_email cescxm@zsu.edu.cn _publ_requested_coeditor_name ? _publ_section_title ; Supramolecular isomerism within three-dimensional 3-connnected nets: Exceptional synthesis and characterization of trimorphic copper(I) 3,5-dimethyl-1,2,4-triazolate ; loop_ _publ_author_name _publ_author_address 'Jie-Peng Zhang' ; School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou 510275 P. R. China ; 'Yan-Yong Lin' ; School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou 510275 P. R. China ; 'Xiao-Chun Huang' ; School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou 510275 P. R. China ; 'Xiao-Ming Chen' ; School of Chemistry and Chemical Engineering Sun Yat-Sen University Guangzhou 510275 P. R. China ; #=================================END data_2 _database_code_depnum_ccdc_archive 'CCDC 267903' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H6 Cu N3' _chemical_formula_weight 159.66 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 tetragonal _symmetry_space_group_name_H-M I-42d loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y, -z+3/4' 'x+1/2, -y, -z+3/4' '-y+1/2, -x, z+3/4' 'y+1/2, x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' '-x+1, y+1/2, -z+5/4' 'x+1, -y+1/2, -z+5/4' '-y+1, -x+1/2, z+5/4' 'y+1, x+1/2, z+5/4' _cell_length_a 14.0247(5) _cell_length_b 14.0247(5) _cell_length_c 5.2884(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1040.19(9) _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 needle-like _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.039 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 4.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4968 _exptl_absorpt_correction_T_max 0.6865 _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_reflns_number 4503 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.00 _reflns_number_total 629 _reflns_number_gt 622 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINT _computing_data_reduction SAINT _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^)+(0.0396P)^2^+1.0392P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(3) _refine_ls_number_reflns 629 _refine_ls_number_parameters 39 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0201 _refine_ls_R_factor_gt 0.0197 _refine_ls_wR_factor_ref 0.0572 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 C1 C 0.45676(15) 0.79771(14) 0.2801(5) 0.0203(4) Uani 1 1 d . . . C2 C 0.48668(18) 0.86177(16) 0.4904(5) 0.0277(5) Uani 1 1 d . . . H2A H 0.4313 0.8836 0.5801 0.042 Uiso 1 1 calc R . . H2B H 0.5204 0.9155 0.4225 0.042 Uiso 1 1 calc R . . H2C H 0.5276 0.8275 0.6041 0.042 Uiso 1 1 calc R . . N1 N 0.36599(13) 0.78093(13) 0.2273(4) 0.0211(4) Uani 1 1 d . . . N2 N 0.51715(16) 0.7500 0.1250 0.0202(5) Uani 1 2 d S . . Cu1 Cu 0.2500 0.83515(3) 0.3750 0.02464(14) Uani 1 2 d S . . 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 C1 0.0199(9) 0.0152(9) 0.0256(10) -0.0021(9) 0.0013(8) -0.0002(7) C2 0.0281(12) 0.0255(11) 0.0296(11) -0.0081(10) 0.0004(10) -0.0041(9) N1 0.0162(8) 0.0161(7) 0.0312(10) -0.0033(7) 0.0028(8) 0.0007(6) N2 0.0123(10) 0.0207(10) 0.0275(11) -0.0028(13) 0.000 0.000 Cu1 0.01649(19) 0.0251(2) 0.0324(2) 0.000 0.00461(17) 0.000 _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 C1 N1 1.324(3) . ? C1 N2 1.356(3) . ? C1 C2 1.490(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? N1 N1 1.387(4) 14_464 ? N1 Cu1 1.9582(18) . ? N2 C1 1.356(3) 14_464 ? N2 Cu1 2.071(2) 12_655 ? Cu1 N1 1.9582(18) 5 ? Cu1 N2 2.071(2) 11_465 ? 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 C1 N2 112.65(19) . . ? N1 C1 C2 122.4(2) . . ? N2 C1 C2 125.0(2) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 N1 N1 106.01(13) . 14_464 ? C1 N1 Cu1 130.19(17) . . ? N1 N1 Cu1 123.65(6) 14_464 . ? C1 N2 C1 102.7(2) 14_464 . ? C1 N2 Cu1 128.66(12) 14_464 12_655 ? C1 N2 Cu1 128.66(12) . 12_655 ? N1 Cu1 N1 134.29(11) 5 . ? N1 Cu1 N2 112.85(6) 5 11_465 ? N1 Cu1 N2 112.85(6) . 11_465 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.462 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.063 #===============================END data_3 _database_code_depnum_ccdc_archive 'CCDC 267904' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H6 Cu N3' _chemical_formula_weight 159.66 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 Iba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 8.0423(7) _cell_length_b 11.5310(10) _cell_length_c 17.3505(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1609.0(2) _cell_formula_units_Z 12 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate-like _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.977 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 3.944 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4388 _exptl_absorpt_correction_T_max 0.6938 _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_reflns_number 3910 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.99 _reflns_number_total 1778 _reflns_number_gt 1657 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINT _computing_data_reduction SAINT _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^)+(0.0353P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.047(19) _refine_ls_number_reflns 1778 _refine_ls_number_parameters 113 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0653 _refine_ls_wR_factor_gt 0.0643 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.81814(5) 0.58397(3) 0.29292(2) 0.01688(12) Uani 1 1 d . . . N1 N 0.9289(4) 0.5349(3) 0.19132(17) 0.0158(7) Uani 1 1 d . . . N2 N 1.0000 0.5000 0.0685(3) 0.0205(10) Uani 1 2 d S . . N3 N 0.7851(4) 0.4253(2) 0.33204(19) 0.0142(6) Uani 1 1 d . . . N4 N 0.8710(3) 0.3803(3) 0.39367(19) 0.0136(6) Uani 1 1 d . . . N5 N 0.7533(4) 0.2341(2) 0.32957(18) 0.0142(7) Uani 1 1 d . . . C1 C 0.8904(4) 0.5506(3) 0.1178(2) 0.0156(8) Uani 1 1 d . . . C2 C 0.7389(5) 0.6133(4) 0.0921(3) 0.0302(11) Uani 1 1 d . . . H2A H 0.6986 0.6613 0.1332 0.045 Uiso 1 1 calc R . . H2B H 0.6548 0.5582 0.0779 0.045 Uiso 1 1 calc R . . H2C H 0.7655 0.6608 0.0484 0.045 Uiso 1 1 calc R . . C3 C 0.7169(3) 0.3360(3) 0.2953(3) 0.0142(6) Uani 1 1 d . . . C4 C 0.8491(4) 0.2657(3) 0.3911(2) 0.0137(7) Uani 1 1 d . . . C5 C 0.6118(5) 0.3476(4) 0.2258(2) 0.0290(10) Uani 1 1 d . . . H5A H 0.5291 0.4062 0.2344 0.044 Uiso 1 1 calc R . . H5B H 0.5582 0.2749 0.2153 0.044 Uiso 1 1 calc R . . H5C H 0.6798 0.3691 0.1827 0.044 Uiso 1 1 calc R . . C6 C 0.9212(5) 0.1826(3) 0.4469(3) 0.0266(9) Uani 1 1 d . . . H6A H 0.9801 0.2243 0.4862 0.040 Uiso 1 1 calc R . . H6B H 0.9966 0.1316 0.4206 0.040 Uiso 1 1 calc R . . H6C H 0.8337 0.1379 0.4700 0.040 Uiso 1 1 calc R . . Cu2 Cu 1.0000 0.5000 0.45514(4) 0.01708(15) Uani 1 2 d S . . 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 0.02477(19) 0.00420(19) 0.0217(2) -0.0025(2) -0.0009(2) 0.00323(16) N1 0.0210(13) 0.0157(17) 0.0108(18) 0.0014(12) 0.0023(12) 0.0081(12) N2 0.023(2) 0.031(3) 0.008(2) 0.000 0.000 0.015(2) N3 0.0275(15) 0.0062(15) 0.0090(16) 0.0024(12) -0.0043(13) -0.0035(13) N4 0.0193(12) 0.0087(14) 0.0126(15) 0.0017(12) -0.0047(13) -0.0041(11) N5 0.0210(15) 0.0048(15) 0.0170(16) 0.0022(13) -0.0041(13) -0.0035(12) C1 0.0173(17) 0.0193(19) 0.0102(19) 0.0036(15) 0.0017(15) 0.0114(15) C2 0.025(2) 0.047(3) 0.018(2) 0.006(2) -0.0014(18) 0.022(2) C3 0.0208(14) 0.0061(14) 0.0155(17) -0.0010(17) -0.004(2) -0.0040(12) C4 0.0168(14) 0.0113(18) 0.0130(18) 0.0019(15) -0.0010(14) -0.0028(13) C5 0.046(2) 0.019(2) 0.022(3) 0.0028(17) -0.0185(19) -0.0019(18) C6 0.0313(19) 0.021(2) 0.027(2) 0.0106(19) -0.0078(19) 0.0007(16) Cu2 0.0216(3) 0.0213(3) 0.0083(3) 0.000 0.000 -0.0060(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 N5 1.932(3) 4_655 ? Cu1 N3 1.969(3) . ? Cu1 N1 2.055(3) . ? N1 C1 1.325(5) . ? N1 N1 1.398(5) 2_765 ? N2 C1 1.360(5) . ? N2 C1 1.360(5) 2_765 ? N2 Cu2 1.967(4) 7_454 ? N3 C3 1.330(4) . ? N3 N4 1.375(4) . ? N4 C4 1.334(4) . ? N4 Cu2 2.029(3) . ? N5 C3 1.349(4) . ? N5 C4 1.367(4) . ? N5 Cu1 1.932(3) 4_645 ? C1 C2 1.485(5) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C5 1.478(6) . ? C4 C6 1.480(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? Cu2 N2 1.967(4) 7_455 ? Cu2 N4 2.029(3) 2_765 ? 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 N5 Cu1 N3 132.76(13) 4_655 . ? N5 Cu1 N1 131.17(12) 4_655 . ? N3 Cu1 N1 95.64(13) . . ? C1 N1 N1 105.68(19) . 2_765 ? C1 N1 Cu1 133.4(2) . . ? N1 N1 Cu1 120.87(8) 2_765 . ? C1 N2 C1 102.0(4) . 2_765 ? C1 N2 Cu2 129.0(2) . 7_454 ? C1 N2 Cu2 129.0(2) 2_765 7_454 ? C3 N3 N4 106.7(3) . . ? C3 N3 Cu1 127.6(3) . . ? N4 N3 Cu1 123.4(2) . . ? C4 N4 N3 106.4(3) . . ? C4 N4 Cu2 139.3(3) . . ? N3 N4 Cu2 114.1(2) . . ? C3 N5 C4 103.6(3) . . ? C3 N5 Cu1 124.8(2) . 4_645 ? C4 N5 Cu1 131.6(2) . 4_645 ? N1 C1 N2 113.3(3) . . ? N1 C1 C2 123.3(3) . . ? N2 C1 C2 123.4(4) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N3 C3 N5 112.0(3) . . ? N3 C3 C5 123.8(3) . . ? N5 C3 C5 124.2(3) . . ? N4 C4 N5 111.4(3) . . ? N4 C4 C6 124.6(3) . . ? N5 C4 C6 124.0(3) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 Cu2 N4 121.71(9) 7_455 . ? N2 Cu2 N4 121.71(9) 7_455 2_765 ? N4 Cu2 N4 116.58(18) . 2_765 ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.962 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.096 #End of Crystallographic Information File #====================================== data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 279779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H6 Cu N3' _chemical_formula_weight 159.66 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 tetragonal _symmetry_space_group_name_H-M P4(2)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 13.470(2) _cell_length_b 13.470(2) _cell_length_c 6.142(2) _cell_angle_alpha 90.00(2) _cell_angle_beta 90.00(2) _cell_angle_gamma 90.00(2) _cell_volume 1114.6(5) _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-like _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.903 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 3.796 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3955 _exptl_absorpt_correction_T_max 0.5173 _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_reflns_number 7811 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 30.00 _reflns_number_total 1593 _reflns_number_gt 1431 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINT _computing_data_reduction SAINT _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^)+(0.0307P)^2^+0.7062P] 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 1593 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0260 _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0624 _refine_ls_wR_factor_gt 0.0614 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.600572(14) 0.474453(15) 0.17130(3) 0.02499(9) Uani 1 1 d . . . N1 N 0.51324(10) 0.23502(10) -0.2023(2) 0.0248(3) Uani 1 1 d . . . N2 N 0.53451(9) 0.36938(9) 0.0039(2) 0.0243(3) Uani 1 1 d . . . N3 N 0.47161(10) 0.39442(10) -0.1671(2) 0.0256(3) Uani 1 1 d . . . C1 C 0.55623(11) 0.27410(11) -0.0232(3) 0.0247(3) Uani 1 1 d . . . C2 C 0.46082(11) 0.31240(12) -0.2854(3) 0.0255(3) Uani 1 1 d . . . C3 C 0.61665(17) 0.21573(14) 0.1323(4) 0.0413(5) Uani 1 1 d . . . H3A H 0.6475 0.2598 0.2349 0.062 Uiso 1 1 calc R . . H3D H 0.6669 0.1798 0.0543 0.062 Uiso 1 1 calc R . . H3B H 0.5747 0.1697 0.2084 0.062 Uiso 1 1 calc R . . C4 C 0.39877(15) 0.30616(15) -0.4860(3) 0.0405(5) Uani 1 1 d . . . H4D H 0.3498 0.3579 -0.4839 0.061 Uiso 1 1 calc R . . H4A H 0.3663 0.2428 -0.4913 0.061 Uiso 1 1 calc R . . H4B H 0.4403 0.3138 -0.6120 0.061 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 0.02087(11) 0.02242(12) 0.03167(14) -0.00312(8) -0.00641(7) -0.00010(6) N1 0.0226(6) 0.0191(6) 0.0327(7) -0.0050(5) 0.0007(5) 0.0004(5) N2 0.0213(6) 0.0199(6) 0.0315(7) -0.0035(5) -0.0053(5) 0.0014(5) N3 0.0220(6) 0.0209(6) 0.0339(8) -0.0046(5) -0.0077(5) 0.0026(5) C1 0.0229(7) 0.0190(7) 0.0322(8) -0.0012(6) 0.0003(6) -0.0002(5) C2 0.0210(7) 0.0228(7) 0.0328(9) -0.0064(6) -0.0013(6) -0.0002(6) C3 0.0514(12) 0.0288(9) 0.0436(11) 0.0006(8) -0.0117(9) 0.0104(8) C4 0.0394(10) 0.0402(10) 0.0419(10) -0.0151(9) -0.0139(8) 0.0074(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 N2 1.9628(13) . ? Cu1 N1 1.9774(14) 4_565 ? Cu1 N3 2.0163(14) 5_665 ? N1 C1 1.350(2) . ? N1 C2 1.359(2) . ? N1 Cu1 1.9774(14) 3_644 ? N2 C1 1.3269(19) . ? N2 N3 1.3911(19) . ? N3 C2 1.330(2) . ? N3 Cu1 2.0163(14) 5_665 ? C1 C3 1.481(2) . ? C2 C4 1.492(2) . ? 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 N1 132.95(5) . 4_565 ? N2 Cu1 N3 113.98(5) . 5_665 ? N1 Cu1 N3 111.91(6) 4_565 5_665 ? C1 N1 C2 103.29(13) . . ? C1 N1 Cu1 129.87(11) . 3_644 ? C2 N1 Cu1 126.78(11) . 3_644 ? C1 N2 N3 105.93(13) . . ? C1 N2 Cu1 131.54(11) . . ? N3 N2 Cu1 119.80(10) . . ? C2 N3 N2 106.11(13) . . ? C2 N3 Cu1 131.92(11) . 5_665 ? N2 N3 Cu1 121.04(10) . 5_665 ? N2 C1 N1 112.61(14) . . ? N2 C1 C3 123.65(16) . . ? N1 C1 C3 123.66(15) . . ? N3 C2 N1 112.05(14) . . ? N3 C2 C4 124.00(15) . . ? N1 C2 C4 123.96(15) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.327 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.062