# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Robin Hicks' 'Michael J. Ferguson' 'Joe B. Gilroy' 'Bryan D. Koivisto' 'Robert McDonald' _publ_contact_author_name 'Robin Hicks' _publ_contact_author_address ; Chemistry Department University of Victoria PO Box 3065 Victoria BC V8W 3V6 CANADA ; _publ_contact_author_email RHICKS@UVIC.CA _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; Magnetostructural studies of copper (II) - verdazyl radical complexes ; data_vic0542 _database_code_depnum_ccdc_archive 'CCDC 601280' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 Cl2 Cu N5 O' _chemical_formula_sum 'C13 H18 Cl2 Cu N5 O' _chemical_formula_weight 394.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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 17.2769(13) _cell_length_b 10.7994(8) _cell_length_c 17.8486(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3330.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6520 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 26.32 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.37 _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 1.640 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4826 _exptl_absorpt_correction_T_max 0.5821 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24421 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0119 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3417 _reflns_number_gt 3155 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _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^)+(0.0089P)^2^+10.7806P] 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 3417 _refine_ls_number_parameters 226 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.373 _refine_ls_restrained_S_all 1.372 _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 Cu Cu 0.06101(3) 0.35454(4) -0.00049(3) 0.03115(15) Uani 1 1 d . . . Cl1 Cl 0.01282(12) 0.21601(14) -0.07909(8) 0.0780(5) Uani 1 1 d . . . Cl2 Cl 0.06115(6) 0.51183(10) -0.08004(6) 0.0377(2) Uani 1 1 d . . . O O 0.2541(3) 0.6989(4) 0.0977(3) 0.0829(15) Uani 1 1 d . . . N1 N 0.1928(2) 0.5258(3) 0.0542(2) 0.0403(9) Uani 1 1 d . . . N2 N 0.14553(18) 0.4282(3) 0.06746(19) 0.0289(7) Uani 1 1 d . A . N3 N 0.1761(3) 0.5934(4) 0.1785(2) 0.0633(14) Uani 1 1 d D . . N4 N 0.1367(3) 0.4895(3) 0.1958(2) 0.0475(10) Uani 1 1 d . A . N10 N 0.05020(17) 0.2476(3) 0.09104(19) 0.0283(7) Uani 1 1 d . . . C1 C 0.1215(2) 0.4159(4) 0.1391(2) 0.0309(9) Uani 1 1 d . . . C2 C 0.2097(3) 0.6135(4) 0.1098(4) 0.0577(15) Uani 1 1 d . A . C3 C 0.2423(3) 0.5140(5) -0.0132(3) 0.0490(12) Uani 1 1 d . . . H3 H 0.2178 0.4499 -0.0460 0.059 Uiso 1 1 calc R . . C4 C 0.2471(4) 0.6325(5) -0.0589(4) 0.0694(17) Uani 1 1 d . . . H4A H 0.1948 0.6600 -0.0720 0.083 Uiso 1 1 calc R . . H4B H 0.2766 0.6169 -0.1049 0.083 Uiso 1 1 calc R . . H4C H 0.2730 0.6968 -0.0295 0.083 Uiso 1 1 calc R . . C5 C 0.3215(3) 0.4643(6) 0.0092(4) 0.075(2) Uani 1 1 d . . . H5A H 0.3151 0.3879 0.0382 0.090 Uiso 1 1 calc R . . H5B H 0.3485 0.5262 0.0398 0.090 Uiso 1 1 calc R . . H5C H 0.3519 0.4470 -0.0359 0.090 Uiso 1 1 calc R . . C6A C 0.1776(6) 0.6720(8) 0.2466(4) 0.044(2) Uani 0.55 1 d PD A 1 H6A H 0.1391 0.6351 0.2820 0.052 Uiso 0.55 1 calc PR A 1 C7A C 0.1500(16) 0.8032(14) 0.2311(17) 0.055(5) Uani 0.55 1 d PD A 1 H7AA H 0.1506 0.8511 0.2777 0.066 Uiso 0.55 1 calc PR A 1 H7AB H 0.0972 0.8007 0.2111 0.066 Uiso 0.55 1 calc PR A 1 H7AC H 0.1844 0.8423 0.1944 0.066 Uiso 0.55 1 calc PR A 1 C8A C 0.2564(5) 0.6542(13) 0.2828(7) 0.058(3) Uani 0.55 1 d PD A 1 H8AA H 0.2595 0.7039 0.3286 0.070 Uiso 0.55 1 calc PR A 1 H8AB H 0.2969 0.6805 0.2479 0.070 Uiso 0.55 1 calc PR A 1 H8AC H 0.2636 0.5666 0.2952 0.070 Uiso 0.55 1 calc PR A 1 C6B C 0.2149(6) 0.6826(8) 0.2291(5) 0.038(3) Uani 0.45 1 d PD A 2 H6B H 0.2650 0.7142 0.2087 0.046 Uiso 0.45 1 calc PR A 2 C7B C 0.1556(17) 0.784(2) 0.242(2) 0.068(7) Uani 0.45 1 d PD A 2 H7BA H 0.1469 0.8294 0.1949 0.082 Uiso 0.45 1 calc PR A 2 H7BB H 0.1748 0.8419 0.2801 0.082 Uiso 0.45 1 calc PR A 2 H7BC H 0.1068 0.7477 0.2588 0.082 Uiso 0.45 1 calc PR A 2 C8B C 0.2242(9) 0.6137(11) 0.3028(6) 0.054(4) Uani 0.45 1 d PD A 2 H8BA H 0.2639 0.5495 0.2973 0.065 Uiso 0.45 1 calc PR A 2 H8BB H 0.1749 0.5751 0.3166 0.065 Uiso 0.45 1 calc PR A 2 H8BC H 0.2399 0.6720 0.3421 0.065 Uiso 0.45 1 calc PR A 2 C11 C 0.0779(2) 0.3009(4) 0.1529(2) 0.0304(8) Uani 1 1 d . A . C12 C 0.0696(3) 0.2497(4) 0.2238(2) 0.0412(10) Uani 1 1 d . . . H12 H 0.0879 0.2915 0.2671 0.049 Uiso 1 1 calc R A . C13 C 0.0337(3) 0.1355(5) 0.2290(3) 0.0510(13) Uani 1 1 d . A . H13 H 0.0271 0.0971 0.2765 0.061 Uiso 1 1 calc R . . C14 C 0.0078(3) 0.0784(4) 0.1654(3) 0.0478(12) Uani 1 1 d . . . H14 H -0.0152 -0.0014 0.1681 0.057 Uiso 1 1 calc R A . C15 C 0.0154(2) 0.1375(4) 0.0969(3) 0.0369(10) Uani 1 1 d . A . H15 H -0.0046 0.0989 0.0532 0.044 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 Cu 0.0355(3) 0.0286(3) 0.0293(3) 0.0007(2) -0.0083(2) -0.0038(2) Cl1 0.1359(15) 0.0612(9) 0.0369(7) -0.0042(6) -0.0205(8) -0.0460(9) Cl2 0.0391(5) 0.0393(5) 0.0346(5) 0.0083(4) -0.0035(4) 0.0088(4) O 0.091(3) 0.044(2) 0.114(4) 0.007(2) -0.042(3) -0.034(2) N1 0.041(2) 0.0301(18) 0.050(2) 0.0095(17) -0.0135(18) -0.0102(16) N2 0.0277(16) 0.0239(16) 0.0353(18) 0.0027(14) -0.0098(14) -0.0029(13) N3 0.106(4) 0.029(2) 0.055(3) -0.003(2) -0.040(3) -0.008(2) N4 0.069(3) 0.032(2) 0.041(2) -0.0068(17) -0.020(2) 0.0065(19) N10 0.0246(15) 0.0251(15) 0.0353(18) -0.0014(14) -0.0035(14) 0.0029(13) C1 0.036(2) 0.0285(19) 0.028(2) -0.0004(16) -0.0105(17) 0.0064(17) C2 0.067(3) 0.029(2) 0.077(4) 0.002(2) -0.040(3) -0.010(2) C3 0.039(2) 0.044(3) 0.064(3) 0.015(2) -0.006(2) -0.011(2) C4 0.069(4) 0.058(3) 0.081(4) 0.034(3) -0.003(3) -0.016(3) C5 0.035(3) 0.068(4) 0.123(6) 0.027(4) -0.005(3) -0.006(3) C6A 0.053(6) 0.040(5) 0.038(5) -0.011(4) -0.002(5) -0.010(5) C7A 0.069(11) 0.043(8) 0.054(10) -0.003(6) 0.004(10) 0.009(7) C8A 0.045(6) 0.078(9) 0.051(7) -0.020(6) -0.009(5) -0.005(6) C6B 0.028(5) 0.040(6) 0.047(7) -0.008(5) -0.001(5) -0.018(5) C7B 0.075(14) 0.059(12) 0.071(16) -0.021(12) -0.044(11) 0.009(11) C8B 0.071(10) 0.046(7) 0.045(8) -0.022(6) -0.030(7) -0.001(7) C11 0.0286(19) 0.0296(19) 0.033(2) -0.0028(17) -0.0030(16) 0.0090(16) C12 0.050(3) 0.043(2) 0.031(2) 0.0010(19) 0.003(2) 0.009(2) C13 0.062(3) 0.053(3) 0.038(3) 0.015(2) 0.012(2) 0.005(3) C14 0.051(3) 0.035(2) 0.057(3) 0.006(2) 0.016(2) -0.005(2) C15 0.033(2) 0.031(2) 0.047(3) -0.0015(19) 0.0035(19) -0.0024(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N10 2.009(3) . ? Cu N2 2.058(3) . ? Cu Cl1 2.2136(13) . ? Cu Cl2 2.2140(11) . ? O C2 1.219(6) . ? N1 N2 1.355(5) . ? N1 C2 1.402(6) . ? N1 C3 1.482(6) . ? N2 C1 1.351(5) . ? N3 N4 1.348(6) . ? N3 C2 1.375(8) . ? N3 C6B 1.481(2) . ? N3 C6A 1.483(2) . ? N4 C1 1.313(5) . ? N10 C11 1.334(5) . ? N10 C15 1.337(5) . ? C1 C11 1.473(6) . ? C3 C4 1.520(7) . ? C3 C5 1.523(7) . ? C6A C8A 1.519(2) . ? C6A C7A 1.520(2) . ? C6B C8B 1.520(2) . ? C6B C7B 1.520(2) . ? C11 C12 1.388(6) . ? C12 C13 1.383(7) . ? C13 C14 1.368(7) . ? C14 C15 1.385(6) . ? 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 N10 Cu N2 78.98(13) . . ? N10 Cu Cl1 95.27(10) . . ? N2 Cu Cl1 154.36(11) . . ? N10 Cu Cl2 164.26(10) . . ? N2 Cu Cl2 94.63(9) . . ? Cl1 Cu Cl2 96.46(5) . . ? N2 N1 C2 121.9(4) . . ? N2 N1 C3 115.0(4) . . ? C2 N1 C3 120.8(4) . . ? C1 N2 N1 115.2(3) . . ? C1 N2 Cu 107.6(3) . . ? N1 N2 Cu 128.8(3) . . ? N4 N3 C2 123.2(4) . . ? N4 N3 C6B 129.1(5) . . ? C2 N3 C6B 104.5(6) . . ? N4 N3 C6A 107.3(6) . . ? C2 N3 C6A 129.4(6) . . ? C1 N4 N3 115.4(4) . . ? C11 N10 C15 118.7(4) . . ? C11 N10 Cu 113.0(3) . . ? C15 N10 Cu 128.1(3) . . ? N4 C1 N2 127.5(4) . . ? N4 C1 C11 119.0(4) . . ? N2 C1 C11 113.4(3) . . ? O C2 N3 122.8(5) . . ? O C2 N1 121.2(6) . . ? N3 C2 N1 115.9(4) . . ? N1 C3 C4 113.3(5) . . ? N1 C3 C5 109.6(4) . . ? C4 C3 C5 112.9(4) . . ? N3 C6A C8A 106.9(7) . . ? N3 C6A C7A 112.2(13) . . ? C8A C6A C7A 118.5(16) . . ? N3 C6B C8B 104.9(7) . . ? N3 C6B C7B 104.9(16) . . ? C8B C6B C7B 107.3(16) . . ? N10 C11 C12 123.0(4) . . ? N10 C11 C1 114.2(3) . . ? C12 C11 C1 122.8(4) . . ? C13 C12 C11 117.6(4) . . ? C14 C13 C12 119.5(4) . . ? C13 C14 C15 119.6(4) . . ? N10 C15 C14 121.5(4) . . ? 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 C2 N1 N2 C1 -5.5(6) . . . . ? C3 N1 N2 C1 157.5(4) . . . . ? C2 N1 N2 Cu 138.3(4) . . . . ? C3 N1 N2 Cu -58.7(5) . . . . ? N10 Cu N2 C1 -31.6(3) . . . . ? Cl1 Cu N2 C1 -110.7(3) . . . . ? Cl2 Cu N2 C1 133.8(2) . . . . ? N10 Cu N2 N1 -177.5(4) . . . . ? Cl1 Cu N2 N1 103.4(4) . . . . ? Cl2 Cu N2 N1 -12.1(3) . . . . ? C2 N3 N4 C1 -10.5(7) . . . . ? C6B N3 N4 C1 -167.2(7) . . . . ? C6A N3 N4 C1 171.9(5) . . . . ? N2 Cu N10 C11 22.5(3) . . . . ? Cl1 Cu N10 C11 177.3(3) . . . . ? Cl2 Cu N10 C11 -44.7(5) . . . . ? N2 Cu N10 C15 -162.0(3) . . . . ? Cl1 Cu N10 C15 -7.3(3) . . . . ? Cl2 Cu N10 C15 130.8(4) . . . . ? N3 N4 C1 N2 5.2(7) . . . . ? N3 N4 C1 C11 -179.3(4) . . . . ? N1 N2 C1 N4 2.5(6) . . . . ? Cu N2 C1 N4 -148.6(4) . . . . ? N1 N2 C1 C11 -173.2(3) . . . . ? Cu N2 C1 C11 35.7(4) . . . . ? N4 N3 C2 O -169.4(5) . . . . ? C6B N3 C2 O -7.9(8) . . . . ? C6A N3 C2 O 7.6(10) . . . . ? N4 N3 C2 N1 7.7(8) . . . . ? C6B N3 C2 N1 169.2(6) . . . . ? C6A N3 C2 N1 -175.3(6) . . . . ? N2 N1 C2 O 177.9(4) . . . . ? C3 N1 C2 O 15.9(7) . . . . ? N2 N1 C2 N3 0.7(7) . . . . ? C3 N1 C2 N3 -161.3(4) . . . . ? N2 N1 C3 C4 137.5(4) . . . . ? C2 N1 C3 C4 -59.3(6) . . . . ? N2 N1 C3 C5 -95.4(5) . . . . ? C2 N1 C3 C5 67.7(6) . . . . ? N4 N3 C6A C8A 100.2(9) . . . . ? C2 N3 C6A C8A -77.1(10) . . . . ? N4 N3 C6A C7A -128.2(13) . . . . ? C2 N3 C6A C7A 54.4(15) . . . . ? N4 N3 C6B C8B 17.8(13) . . . . ? C2 N3 C6B C8B -142.3(9) . . . . ? N4 N3 C6B C7B -95.1(16) . . . . ? C2 N3 C6B C7B 104.9(15) . . . . ? C15 N10 C11 C12 -2.6(6) . . . . ? Cu N10 C11 C12 173.3(3) . . . . ? C15 N10 C11 C1 174.5(3) . . . . ? Cu N10 C11 C1 -9.6(4) . . . . ? N4 C1 C11 N10 165.4(4) . . . . ? N2 C1 C11 N10 -18.6(5) . . . . ? N4 C1 C11 C12 -17.5(6) . . . . ? N2 C1 C11 C12 158.6(4) . . . . ? N10 C11 C12 C13 2.8(6) . . . . ? C1 C11 C12 C13 -174.1(4) . . . . ? C11 C12 C13 C14 -0.3(7) . . . . ? C12 C13 C14 C15 -2.3(8) . . . . ? C11 N10 C15 C14 -0.1(6) . . . . ? Cu N10 C15 C14 -175.4(3) . . . . ? C13 C14 C15 N10 2.6(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.589 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.083 # Attachment 'vic0529.cif' data_vic0529 _database_code_depnum_ccdc_archive 'CCDC 601281' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H10 Cl2 Cu N5 O' _chemical_formula_sum 'C9 H10 Cl2 Cu N5 O' _chemical_formula_weight 338.66 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' O O 0.0106 0.0060 '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 Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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 14.9568(12) _cell_length_b 9.9809(8) _cell_length_c 17.3231(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2586.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 5454 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 26.29 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 2.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4522 _exptl_absorpt_correction_T_max 0.5446 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17717 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2639 _reflns_number_gt 2386 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _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^)+(0.0350P)^2^+1.5117P] 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 2639 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0269 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0626 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 Cu Cu 0.051123(14) 0.21308(2) 0.545350(12) 0.02492(9) Uani 1 1 d . . . Cl1 Cl -0.07296(3) 0.23723(6) 0.61464(3) 0.03747(13) Uani 1 1 d . . . Cl2 Cl 0.15520(3) 0.21830(5) 0.63475(3) 0.03324(12) Uani 1 1 d . . . O O 0.30667(9) -0.09654(16) 0.44326(8) 0.0407(3) Uani 1 1 d . . . N1 N 0.17854(10) 0.00611(15) 0.48226(8) 0.0267(3) Uani 1 1 d . . . N2 N 0.11025(9) 0.09140(15) 0.46921(8) 0.0233(3) Uani 1 1 d . . . N3 N 0.23105(10) 0.03384(17) 0.35711(9) 0.0306(3) Uani 1 1 d . . . N4 N 0.16200(10) 0.11419(16) 0.33972(8) 0.0288(3) Uani 1 1 d . . . N10 N 0.00236(10) 0.29267(14) 0.44866(8) 0.0239(3) Uani 1 1 d . . . C1 C 0.10796(11) 0.14266(18) 0.39662(9) 0.0236(3) Uani 1 1 d . . . C2 C 0.24430(12) -0.02363(19) 0.42862(11) 0.0299(4) Uani 1 1 d . . . C3 C 0.17475(14) -0.0750(2) 0.55256(11) 0.0343(4) Uani 1 1 d . . . H3A H 0.2199 -0.0431 0.5892 0.041 Uiso 1 1 calc R . . H3B H 0.1866 -0.1690 0.5397 0.041 Uiso 1 1 calc R . . H3C H 0.1152 -0.0672 0.5758 0.041 Uiso 1 1 calc R . . C4 C 0.29198(14) 0.0002(3) 0.29393(12) 0.0458(5) Uani 1 1 d . . . H4A H 0.2740 0.0486 0.2472 0.055 Uiso 1 1 calc R . . H4B H 0.2897 -0.0964 0.2842 0.055 Uiso 1 1 calc R . . H4C H 0.3531 0.0259 0.3081 0.055 Uiso 1 1 calc R . . C11 C 0.03724(11) 0.24218(19) 0.38343(10) 0.0244(3) Uani 1 1 d . . . C12 C 0.01030(13) 0.2835(2) 0.31062(11) 0.0322(4) Uani 1 1 d . . . H12 H 0.0352 0.2448 0.2653 0.039 Uiso 1 1 calc R . . C13 C -0.05379(13) 0.3826(2) 0.30613(12) 0.0394(5) Uani 1 1 d . . . H13 H -0.0737 0.4137 0.2572 0.047 Uiso 1 1 calc R . . C14 C -0.08894(14) 0.4364(2) 0.37299(12) 0.0377(5) Uani 1 1 d . . . H14 H -0.1325 0.5056 0.3706 0.045 Uiso 1 1 calc R . . C15 C -0.05999(12) 0.38850(19) 0.44336(11) 0.0300(4) Uani 1 1 d . . . H15 H -0.0850 0.4245 0.4893 0.036 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 Cu 0.02743(13) 0.02984(14) 0.01748(13) -0.00184(8) 0.00050(8) 0.00208(8) Cl1 0.0343(2) 0.0528(3) 0.0253(2) -0.0060(2) 0.00716(19) 0.0001(2) Cl2 0.0376(3) 0.0395(3) 0.0226(2) 0.00290(17) -0.00599(18) -0.00046(18) O 0.0331(8) 0.0467(8) 0.0424(8) -0.0057(7) -0.0049(6) 0.0152(7) N1 0.0287(7) 0.0259(7) 0.0254(7) -0.0010(6) -0.0035(6) 0.0040(6) N2 0.0248(7) 0.0246(7) 0.0207(7) -0.0019(6) -0.0023(6) 0.0017(6) N3 0.0257(8) 0.0395(9) 0.0264(8) -0.0078(7) 0.0007(6) 0.0059(7) N4 0.0277(8) 0.0361(8) 0.0225(7) -0.0052(6) -0.0007(6) 0.0034(6) N10 0.0233(7) 0.0257(7) 0.0226(7) -0.0013(6) 0.0003(5) 0.0005(6) C1 0.0243(8) 0.0265(9) 0.0200(8) -0.0033(7) -0.0018(6) -0.0007(7) C2 0.0269(9) 0.0309(10) 0.0318(10) -0.0081(8) -0.0029(7) 0.0019(8) C3 0.0375(10) 0.0309(10) 0.0345(10) 0.0075(8) -0.0038(8) 0.0020(8) C4 0.0390(11) 0.0658(15) 0.0326(11) -0.0136(10) 0.0071(9) 0.0138(10) C11 0.0244(8) 0.0274(8) 0.0213(8) -0.0009(7) 0.0002(7) -0.0015(7) C12 0.0341(10) 0.0414(11) 0.0212(8) 0.0009(7) -0.0021(8) 0.0047(8) C13 0.0420(11) 0.0468(12) 0.0293(10) 0.0078(9) -0.0075(8) 0.0076(9) C14 0.0342(10) 0.0355(10) 0.0432(11) 0.0034(9) -0.0050(9) 0.0106(8) C15 0.0277(9) 0.0291(9) 0.0332(10) -0.0036(8) 0.0005(7) 0.0036(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 Cu N10 1.9921(15) . ? Cu N2 1.9992(14) . ? Cu Cl2 2.1965(5) . ? Cu Cl1 2.2234(5) . ? O C2 1.210(2) . ? N1 N2 1.349(2) . ? N1 C2 1.385(2) . ? N1 C3 1.463(2) . ? N2 C1 1.358(2) . ? N3 N4 1.342(2) . ? N3 C2 1.379(3) . ? N3 C4 1.463(2) . ? N4 C1 1.306(2) . ? N10 C15 1.339(2) . ? N10 C11 1.343(2) . ? C1 C11 1.469(2) . ? C11 C12 1.387(3) . ? C12 C13 1.380(3) . ? C13 C14 1.381(3) . ? C14 C15 1.379(3) . ? 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 N10 Cu N2 81.34(6) . . ? N10 Cu Cl2 147.44(5) . . ? N2 Cu Cl2 99.56(4) . . ? N10 Cu Cl1 96.03(5) . . ? N2 Cu Cl1 142.31(5) . . ? Cl2 Cu Cl1 102.02(2) . . ? N2 N1 C2 124.09(15) . . ? N2 N1 C3 117.34(15) . . ? C2 N1 C3 117.85(15) . . ? N1 N2 C1 114.34(14) . . ? N1 N2 Cu 127.43(11) . . ? C1 N2 Cu 111.77(11) . . ? N4 N3 C2 124.11(15) . . ? N4 N3 C4 116.64(16) . . ? C2 N3 C4 119.14(16) . . ? C1 N4 N3 115.90(15) . . ? C15 N10 C11 118.75(16) . . ? C15 N10 Cu 126.69(13) . . ? C11 N10 Cu 114.56(12) . . ? N4 C1 N2 126.96(16) . . ? N4 C1 C11 118.38(16) . . ? N2 C1 C11 114.64(15) . . ? O C2 N3 123.30(18) . . ? O C2 N1 122.39(18) . . ? N3 C2 N1 114.28(16) . . ? N10 C11 C12 122.75(17) . . ? N10 C11 C1 113.74(15) . . ? C12 C11 C1 123.49(16) . . ? C13 C12 C11 117.79(18) . . ? C12 C13 C14 119.75(19) . . ? C15 C14 C13 119.14(18) . . ? N10 C15 C14 121.80(18) . . ? 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 C2 N1 N2 C1 3.0(2) . . . . ? C3 N1 N2 C1 -167.04(15) . . . . ? C2 N1 N2 Cu -146.14(14) . . . . ? C3 N1 N2 Cu 43.8(2) . . . . ? N10 Cu N2 N1 165.91(15) . . . . ? Cl2 Cu N2 N1 18.88(14) . . . . ? Cl1 Cu N2 N1 -105.42(14) . . . . ? N10 Cu N2 C1 16.08(12) . . . . ? Cl2 Cu N2 C1 -130.95(11) . . . . ? Cl1 Cu N2 C1 104.75(12) . . . . ? C2 N3 N4 C1 3.5(3) . . . . ? C4 N3 N4 C1 179.63(18) . . . . ? N2 Cu N10 C15 172.93(16) . . . . ? Cl2 Cu N10 C15 -92.84(17) . . . . ? Cl1 Cu N10 C15 30.86(16) . . . . ? N2 Cu N10 C11 -6.97(12) . . . . ? Cl2 Cu N10 C11 87.26(14) . . . . ? Cl1 Cu N10 C11 -149.04(12) . . . . ? N3 N4 C1 N2 -5.7(3) . . . . ? N3 N4 C1 C11 173.08(15) . . . . ? N1 N2 C1 N4 2.6(3) . . . . ? Cu N2 C1 N4 156.58(15) . . . . ? N1 N2 C1 C11 -176.26(14) . . . . ? Cu N2 C1 C11 -22.23(18) . . . . ? N4 N3 C2 O 179.55(18) . . . . ? C4 N3 C2 O 3.5(3) . . . . ? N4 N3 C2 N1 1.3(3) . . . . ? C4 N3 C2 N1 -174.76(17) . . . . ? N2 N1 C2 O 176.97(17) . . . . ? C3 N1 C2 O -13.0(3) . . . . ? N2 N1 C2 N3 -4.7(2) . . . . ? C3 N1 C2 N3 165.32(16) . . . . ? C15 N10 C11 C12 -1.1(3) . . . . ? Cu N10 C11 C12 178.77(15) . . . . ? C15 N10 C11 C1 177.17(16) . . . . ? Cu N10 C11 C1 -2.92(19) . . . . ? N4 C1 C11 N10 -161.99(16) . . . . ? N2 C1 C11 N10 16.9(2) . . . . ? N4 C1 C11 C12 16.3(3) . . . . ? N2 C1 C11 C12 -164.77(17) . . . . ? N10 C11 C12 C13 1.3(3) . . . . ? C1 C11 C12 C13 -176.82(18) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C11 N10 C15 C14 -0.1(3) . . . . ? Cu N10 C15 C14 180.00(15) . . . . ? C13 C14 C15 N10 1.1(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.364 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.059 # Attachment 'vic0549.cif' data_vic0549 _database_code_depnum_ccdc_archive 'CCDC 601282' _audit_creation_method SHELXL-97 _chemical_name_systematic 1,5-diisopropyl-3-(2-pyridyl)-6-oxoverdazyl _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 N5 O' _chemical_formula_sum 'C13 H18 N5 O' _chemical_formula_weight 260.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.1997(13) _cell_length_b 26.482(7) _cell_length_c 10.429(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.785(4) _cell_angle_gamma 90.00 _cell_volume 1394.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2098 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 25.85 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9454 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10570 _diffrn_reflns_av_R_equivalents 0.0706 _diffrn_reflns_av_sigmaI/netI 0.0618 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 26.41 _reflns_number_total 2853 _reflns_number_gt 1647 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _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^)+(0.0479P)^2^+0.1626P] 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 2853 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1148 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 O O -0.3554(3) 0.45900(6) 0.17708(14) 0.0538(5) Uani 1 1 d . . . N1 N -0.0227(3) 0.40630(6) 0.27629(15) 0.0327(4) Uani 1 1 d . . . N2 N 0.1567(3) 0.36916(6) 0.27118(15) 0.0331(4) Uani 1 1 d . . . N3 N -0.1819(3) 0.40491(7) 0.05002(16) 0.0410(5) Uani 1 1 d . . . N4 N -0.0074(3) 0.36769(6) 0.03813(16) 0.0383(5) Uani 1 1 d . . . N10 N 0.5556(3) 0.30782(6) 0.23374(16) 0.0409(5) Uani 1 1 d . . . C1 C 0.1496(4) 0.35251(7) 0.15066(18) 0.0300(5) Uani 1 1 d . . . C2 C -0.1994(4) 0.42573(8) 0.1683(2) 0.0375(5) Uani 1 1 d . . . C3 C -0.0233(4) 0.42371(7) 0.41018(19) 0.0347(5) Uani 1 1 d . . . H3 H -0.1685 0.4491 0.4028 0.042 Uiso 1 1 calc R . . C4 C -0.0806(5) 0.37996(8) 0.4929(2) 0.0444(6) Uani 1 1 d . . . H4A H -0.2518 0.3649 0.4503 0.053 Uiso 1 1 calc R . . H4B H -0.0860 0.3922 0.5809 0.053 Uiso 1 1 calc R . . H4C H 0.0590 0.3545 0.5009 0.053 Uiso 1 1 calc R . . C5 C 0.2360(5) 0.44947(8) 0.4717(2) 0.0492(6) Uani 1 1 d . . . H5A H 0.2632 0.4777 0.4157 0.059 Uiso 1 1 calc R . . H5B H 0.3814 0.4252 0.4797 0.059 Uiso 1 1 calc R . . H5C H 0.2315 0.4621 0.5594 0.059 Uiso 1 1 calc R . . C6 C -0.3463(4) 0.42392(9) -0.0765(2) 0.0479(6) Uani 1 1 d . . . H6 H -0.4796 0.4480 -0.0563 0.058 Uiso 1 1 calc R . . C7 C -0.1768(6) 0.45213(10) -0.1500(2) 0.0676(8) Uani 1 1 d . . . H7A H -0.0855 0.4797 -0.0948 0.081 Uiso 1 1 calc R . . H7B H -0.2883 0.4660 -0.2316 0.081 Uiso 1 1 calc R . . H7C H -0.0459 0.4291 -0.1717 0.081 Uiso 1 1 calc R . . C8 C -0.4923(5) 0.38129(11) -0.1563(2) 0.0699(8) Uani 1 1 d . . . H8A H -0.6018 0.3640 -0.1053 0.084 Uiso 1 1 calc R . . H8B H -0.3650 0.3574 -0.1778 0.084 Uiso 1 1 calc R . . H8C H -0.6058 0.3946 -0.2382 0.084 Uiso 1 1 calc R . . C11 C 0.3346(4) 0.31086(7) 0.13898(18) 0.0302(5) Uani 1 1 d . . . C12 C 0.2751(4) 0.27726(8) 0.0354(2) 0.0432(6) Uani 1 1 d . . . H12 H 0.1157 0.2808 -0.0311 0.052 Uiso 1 1 calc R . . C13 C 0.4481(5) 0.23856(8) 0.0288(2) 0.0494(6) Uani 1 1 d . . . H13 H 0.4098 0.2148 -0.0414 0.059 Uiso 1 1 calc R . . C14 C 0.6756(5) 0.23515(8) 0.1255(2) 0.0480(6) Uani 1 1 d . . . H14 H 0.7995 0.2089 0.1243 0.058 Uiso 1 1 calc R . . C15 C 0.7220(5) 0.27035(8) 0.2245(2) 0.0483(6) Uani 1 1 d . . . H15 H 0.8826 0.2680 0.2906 0.058 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 O 0.0623(11) 0.0548(10) 0.0441(10) 0.0057(8) 0.0121(8) 0.0302(9) N1 0.0394(10) 0.0299(9) 0.0281(9) 0.0000(8) 0.0066(8) 0.0081(8) N2 0.0375(10) 0.0324(9) 0.0284(9) -0.0029(8) 0.0060(8) 0.0066(8) N3 0.0460(11) 0.0484(11) 0.0265(9) 0.0046(8) 0.0046(8) 0.0171(9) N4 0.0417(11) 0.0412(10) 0.0303(10) 0.0004(8) 0.0051(8) 0.0106(9) N10 0.0435(11) 0.0362(10) 0.0392(10) -0.0013(8) 0.0026(9) 0.0086(9) C1 0.0335(12) 0.0285(10) 0.0266(11) 0.0000(9) 0.0044(9) 0.0012(9) C2 0.0405(13) 0.0376(12) 0.0342(12) 0.0061(10) 0.0086(11) 0.0071(11) C3 0.0427(13) 0.0317(11) 0.0291(11) -0.0055(9) 0.0075(10) 0.0064(10) C4 0.0561(14) 0.0462(13) 0.0329(12) -0.0023(10) 0.0143(11) -0.0023(12) C5 0.0599(16) 0.0424(13) 0.0441(14) -0.0089(11) 0.0099(12) -0.0096(12) C6 0.0500(15) 0.0613(15) 0.0292(12) 0.0093(11) 0.0029(11) 0.0233(12) C7 0.079(2) 0.0662(18) 0.0498(16) 0.0234(14) -0.0004(14) -0.0041(15) C8 0.0584(16) 0.095(2) 0.0451(15) 0.0185(15) -0.0095(13) -0.0153(16) C11 0.0348(12) 0.0293(11) 0.0276(11) 0.0001(9) 0.0095(10) 0.0007(9) C12 0.0420(13) 0.0489(14) 0.0379(13) -0.0105(11) 0.0082(11) 0.0046(11) C13 0.0586(16) 0.0433(13) 0.0509(14) -0.0161(12) 0.0219(13) -0.0023(12) C14 0.0548(15) 0.0331(12) 0.0612(16) -0.0012(12) 0.0240(14) 0.0099(11) C15 0.0446(14) 0.0461(14) 0.0515(14) 0.0037(12) 0.0061(12) 0.0143(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 O C2 1.216(2) . ? N1 N2 1.365(2) . ? N1 C2 1.373(2) . ? N1 C3 1.471(2) . ? N2 C1 1.324(2) . ? N3 N4 1.365(2) . ? N3 C2 1.374(3) . ? N3 C6 1.479(2) . ? N4 C1 1.322(2) . ? N10 C11 1.328(2) . ? N10 C15 1.335(3) . ? C1 C11 1.488(3) . ? C3 C5 1.511(3) . ? C3 C4 1.516(3) . ? C6 C7 1.498(3) . ? C6 C8 1.498(3) . ? C11 C12 1.377(3) . ? C12 C13 1.376(3) . ? C13 C14 1.363(3) . ? C14 C15 1.368(3) . ? 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 N1 C2 124.62(16) . . ? N2 N1 C3 114.77(15) . . ? C2 N1 C3 120.57(16) . . ? C1 N2 N1 114.33(15) . . ? N4 N3 C2 123.99(16) . . ? N4 N3 C6 114.84(16) . . ? C2 N3 C6 121.09(17) . . ? C1 N4 N3 114.95(16) . . ? C11 N10 C15 116.89(18) . . ? N4 C1 N2 127.81(18) . . ? N4 C1 C11 115.29(17) . . ? N2 C1 C11 116.88(17) . . ? O C2 N1 122.57(19) . . ? O C2 N3 123.13(19) . . ? N1 C2 N3 114.30(18) . . ? N1 C3 C5 109.92(17) . . ? N1 C3 C4 110.22(16) . . ? C5 C3 C4 112.34(17) . . ? N3 C6 C7 109.93(18) . . ? N3 C6 C8 110.37(19) . . ? C7 C6 C8 111.9(2) . . ? N10 C11 C12 122.52(18) . . ? N10 C11 C1 116.49(17) . . ? C12 C11 C1 120.99(18) . . ? C13 C12 C11 119.6(2) . . ? C14 C13 C12 118.3(2) . . ? C13 C14 C15 118.6(2) . . ? N10 C15 C14 124.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 N2 C1 0.2(3) . . . . ? C3 N1 N2 C1 177.77(17) . . . . ? C2 N3 N4 C1 -0.3(3) . . . . ? C6 N3 N4 C1 176.56(18) . . . . ? N3 N4 C1 N2 -0.2(3) . . . . ? N3 N4 C1 C11 178.18(16) . . . . ? N1 N2 C1 N4 0.3(3) . . . . ? N1 N2 C1 C11 -178.11(15) . . . . ? N2 N1 C2 O -179.68(19) . . . . ? C3 N1 C2 O 2.8(3) . . . . ? N2 N1 C2 N3 -0.6(3) . . . . ? C3 N1 C2 N3 -178.05(18) . . . . ? N4 N3 C2 O 179.72(19) . . . . ? C6 N3 C2 O 3.1(3) . . . . ? N4 N3 C2 N1 0.6(3) . . . . ? C6 N3 C2 N1 -176.01(18) . . . . ? N2 N1 C3 C5 65.8(2) . . . . ? C2 N1 C3 C5 -116.5(2) . . . . ? N2 N1 C3 C4 -58.6(2) . . . . ? C2 N1 C3 C4 119.2(2) . . . . ? N4 N3 C6 C7 -68.4(2) . . . . ? C2 N3 C6 C7 108.6(2) . . . . ? N4 N3 C6 C8 55.6(2) . . . . ? C2 N3 C6 C8 -127.5(2) . . . . ? C15 N10 C11 C12 0.3(3) . . . . ? C15 N10 C11 C1 179.58(18) . . . . ? N4 C1 C11 N10 154.47(18) . . . . ? N2 C1 C11 N10 -26.9(3) . . . . ? N4 C1 C11 C12 -26.2(3) . . . . ? N2 C1 C11 C12 152.38(19) . . . . ? N10 C11 C12 C13 0.5(3) . . . . ? C1 C11 C12 C13 -178.75(18) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C11 N10 C15 C14 -1.1(3) . . . . ? C13 C14 C15 N10 1.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.157 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.037 # Attachment 'vic0550.cif' data_vic0550 _database_code_depnum_ccdc_archive 'CCDC 601283' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 Cu F12 N6 O5' _chemical_formula_sum 'C18 H13 Cu F12 N6 O5' _chemical_formula_weight 684.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8110(9) _cell_length_b 10.9073(10) _cell_length_c 12.5202(12) _cell_angle_alpha 78.5653(14) _cell_angle_beta 83.4835(14) _cell_angle_gamma 73.6999(14) _cell_volume 1258.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4227 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.74 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.808 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.000 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.6561 _exptl_absorpt_correction_T_max 0.9333 _exptl_absorpt_process_details 'Bruker SHELXTL (Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10006 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.43 _reflns_number_total 5142 _reflns_number_gt 4003 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _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^)+(0.0653P)^2^+0.6849P] 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 5142 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.25987(4) 0.26558(4) 0.21931(3) 0.02989(14) Uani 1 1 d . . . F21 F 0.7511(3) 0.3806(3) 0.2048(2) 0.0776(9) Uani 1 1 d . . . F22 F 0.6416(4) 0.3349(4) 0.3552(2) 0.0999(12) Uani 1 1 d . . . F23 F 0.5657(3) 0.5112(3) 0.2564(4) 0.1076(13) Uani 1 1 d . . . F24 F 0.5108(3) 0.1418(4) -0.1115(3) 0.1027(13) Uani 1 1 d . . . F25 F 0.6864(3) 0.0622(3) -0.0171(2) 0.0924(10) Uani 1 1 d . . . F26 F 0.6619(4) 0.2452(3) -0.1110(3) 0.1112(13) Uani 1 1 d . . . F31 F -0.0517(3) 0.0976(2) 0.0881(2) 0.0738(8) Uani 1 1 d . . . F32 F 0.0142(3) -0.0920(2) 0.1805(2) 0.0767(9) Uani 1 1 d . . . F33 F -0.1221(3) 0.0615(3) 0.2551(3) 0.0905(10) Uani 1 1 d . . . F34 F 0.4172(3) -0.2310(2) 0.3810(3) 0.0910(11) Uani 1 1 d . . . F35 F 0.4302(4) -0.1006(3) 0.4820(2) 0.0953(11) Uani 1 1 d . . . F36 F 0.5695(3) -0.1222(3) 0.3422(3) 0.0986(11) Uani 1 1 d . . . O1 O -0.1131(3) 0.3074(3) 0.62335(19) 0.0474(6) Uani 1 1 d . . . O21 O 0.4097(2) 0.3390(2) 0.25138(18) 0.0347(5) Uani 1 1 d . . . O22 O 0.3814(2) 0.2274(3) 0.0620(2) 0.0436(6) Uani 1 1 d . . . O31 O 0.1142(2) 0.1855(2) 0.18697(18) 0.0333(5) Uani 1 1 d . . . O32 O 0.3641(2) 0.1004(2) 0.3003(2) 0.0387(6) Uani 1 1 d . . . N1 N 0.0397(3) 0.2975(3) 0.4726(2) 0.0345(6) Uani 1 1 d . . . N2 N 0.0754(3) 0.3454(3) 0.3675(2) 0.0326(6) Uani 1 1 d . . . N3 N -0.1666(3) 0.4641(3) 0.4731(2) 0.0336(6) Uani 1 1 d . . . N4 N -0.1368(3) 0.5181(3) 0.3687(2) 0.0320(6) Uani 1 1 d . . . N11 N 0.1439(3) 0.4385(2) 0.1592(2) 0.0306(6) Uani 1 1 d . . . N12 N -0.0370(3) 0.6138(3) 0.1444(2) 0.0335(6) Uani 1 1 d . . . C1 C -0.0161(3) 0.4533(3) 0.3232(2) 0.0275(6) Uani 1 1 d . . . C2 C -0.0829(4) 0.3529(3) 0.5307(3) 0.0341(7) Uani 1 1 d . . . C3 C 0.1372(4) 0.1790(4) 0.5232(3) 0.0556(11) Uani 1 1 d . . . H3A H 0.1372 0.1793 0.6014 0.067 Uiso 1 1 calc R . . H3B H 0.2333 0.1737 0.4894 0.067 Uiso 1 1 calc R . . H3C H 0.1068 0.1040 0.5130 0.067 Uiso 1 1 calc R . . C4 C -0.3036(4) 0.5279(4) 0.5236(3) 0.0465(9) Uani 1 1 d . . . H4A H -0.2914 0.5326 0.5992 0.056 Uiso 1 1 calc R . . H4B H -0.3723 0.4781 0.5228 0.056 Uiso 1 1 calc R . . H4C H -0.3386 0.6158 0.4826 0.056 Uiso 1 1 calc R . . C11 C 0.0265(3) 0.5027(3) 0.2101(2) 0.0283(6) Uani 1 1 d . . . C12 C 0.1557(4) 0.5137(3) 0.0586(3) 0.0400(8) Uani 1 1 d . . . H12 H 0.2303 0.4935 0.0043 0.048 Uiso 1 1 calc R . . C13 C 0.0454(4) 0.6203(3) 0.0490(3) 0.0422(8) Uani 1 1 d . . . H13 H 0.0279 0.6878 -0.0128 0.051 Uiso 1 1 calc R . . C14 C -0.1697(4) 0.7113(3) 0.1659(3) 0.0446(9) Uani 1 1 d . . . H14A H -0.1934 0.7758 0.0995 0.053 Uiso 1 1 calc R . . H14B H -0.1575 0.7543 0.2245 0.053 Uiso 1 1 calc R . . H14C H -0.2467 0.6688 0.1880 0.053 Uiso 1 1 calc R . . C21 C 0.6242(4) 0.3882(4) 0.2542(3) 0.0438(9) Uani 1 1 d . . . C22 C 0.5294(3) 0.3304(3) 0.2004(3) 0.0332(7) Uani 1 1 d . . . C23 C 0.5843(4) 0.2799(4) 0.1077(3) 0.0417(8) Uani 1 1 d . . . H23 H 0.6798 0.2788 0.0832 0.050 Uiso 1 1 calc R . . C24 C 0.5069(4) 0.2298(3) 0.0472(3) 0.0371(8) Uani 1 1 d . . . C25 C 0.5905(4) 0.1706(4) -0.0503(3) 0.0505(10) Uani 1 1 d . . . C31 C -0.0112(4) 0.0330(4) 0.1837(3) 0.0489(10) Uani 1 1 d . . . C32 C 0.1163(3) 0.0679(3) 0.2179(3) 0.0309(7) Uani 1 1 d . . . C33 C 0.2142(3) -0.0291(3) 0.2799(3) 0.0342(7) Uani 1 1 d . . . H33 H 0.2004 -0.1137 0.2989 0.041 Uiso 1 1 calc R . . C34 C 0.3311(3) -0.0052(3) 0.3146(3) 0.0348(7) Uani 1 1 d . . . C35 C 0.4364(5) -0.1165(4) 0.3812(4) 0.0536(11) 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 Cu 0.0251(2) 0.0310(2) 0.0346(2) -0.00428(16) -0.00236(15) -0.00997(15) F21 0.0497(14) 0.141(3) 0.0720(17) -0.0513(17) 0.0145(12) -0.0586(16) F22 0.123(3) 0.169(3) 0.0454(15) -0.0025(17) -0.0222(16) -0.104(3) F23 0.075(2) 0.071(2) 0.203(4) -0.065(2) -0.028(2) -0.0259(16) F24 0.0470(15) 0.196(4) 0.086(2) -0.100(2) -0.0002(14) -0.0142(19) F25 0.079(2) 0.100(2) 0.080(2) -0.0464(18) -0.0081(16) 0.0262(18) F26 0.152(3) 0.119(3) 0.082(2) -0.054(2) 0.071(2) -0.072(3) F31 0.0904(19) 0.0650(16) 0.0769(18) 0.0282(13) -0.0570(15) -0.0460(14) F32 0.0848(18) 0.0432(14) 0.115(2) 0.0145(13) -0.0573(17) -0.0365(13) F33 0.0394(14) 0.129(3) 0.107(2) -0.009(2) 0.0025(15) -0.0396(16) F34 0.103(2) 0.0335(13) 0.136(3) 0.0015(14) -0.078(2) -0.0012(13) F35 0.145(3) 0.0689(19) 0.0634(18) 0.0008(14) -0.0594(19) -0.0025(18) F36 0.0461(16) 0.088(2) 0.142(3) 0.003(2) -0.0359(17) 0.0096(15) O1 0.0542(16) 0.0505(15) 0.0342(14) 0.0000(11) 0.0092(11) -0.0181(13) O21 0.0281(12) 0.0440(13) 0.0376(12) -0.0135(10) 0.0034(10) -0.0164(10) O22 0.0310(13) 0.0623(17) 0.0449(14) -0.0244(12) 0.0018(11) -0.0152(11) O31 0.0281(11) 0.0297(12) 0.0413(13) 0.0011(9) -0.0089(10) -0.0087(9) O32 0.0317(12) 0.0357(13) 0.0494(15) -0.0064(11) -0.0139(10) -0.0063(10) N1 0.0370(15) 0.0334(15) 0.0288(14) -0.0009(11) -0.0003(11) -0.0061(12) N2 0.0306(14) 0.0356(15) 0.0278(14) -0.0005(11) -0.0013(11) -0.0067(12) N3 0.0299(14) 0.0364(15) 0.0353(15) -0.0081(12) 0.0027(11) -0.0105(12) N4 0.0293(14) 0.0318(14) 0.0345(15) -0.0048(11) -0.0018(11) -0.0082(11) N11 0.0299(14) 0.0310(14) 0.0310(14) -0.0003(11) -0.0009(11) -0.0124(11) N12 0.0376(15) 0.0276(14) 0.0352(15) 0.0028(11) -0.0085(12) -0.0117(12) C1 0.0267(15) 0.0285(16) 0.0300(16) -0.0028(12) -0.0053(12) -0.0119(12) C2 0.0377(18) 0.0332(17) 0.0347(18) -0.0072(14) -0.0005(14) -0.0147(14) C3 0.059(3) 0.053(2) 0.036(2) 0.0088(17) -0.0037(18) 0.004(2) C4 0.0343(19) 0.054(2) 0.049(2) -0.0166(18) 0.0075(16) -0.0079(17) C11 0.0288(16) 0.0267(15) 0.0308(16) 0.0006(12) -0.0068(13) -0.0114(13) C12 0.049(2) 0.0401(19) 0.0319(18) 0.0033(14) 0.0039(15) -0.0234(17) C13 0.054(2) 0.0371(19) 0.0370(19) 0.0078(15) -0.0085(16) -0.0226(17) C14 0.042(2) 0.0285(18) 0.057(2) 0.0045(16) -0.0116(17) -0.0044(15) C21 0.0367(19) 0.056(2) 0.047(2) -0.0164(18) 0.0034(16) -0.0234(17) C22 0.0301(17) 0.0377(18) 0.0351(17) -0.0054(14) -0.0029(13) -0.0147(14) C23 0.0289(17) 0.061(2) 0.0395(19) -0.0161(17) 0.0033(14) -0.0169(16) C24 0.0319(18) 0.045(2) 0.0332(18) -0.0106(15) -0.0005(14) -0.0062(15) C25 0.0337(19) 0.074(3) 0.047(2) -0.029(2) 0.0028(17) -0.0102(19) C31 0.047(2) 0.046(2) 0.056(2) 0.0108(18) -0.0201(19) -0.0230(18) C32 0.0315(16) 0.0316(17) 0.0299(16) -0.0041(13) -0.0026(13) -0.0095(13) C33 0.0401(18) 0.0267(16) 0.0357(18) -0.0023(13) -0.0057(14) -0.0097(14) C34 0.0348(17) 0.0329(18) 0.0348(17) -0.0069(14) -0.0067(14) -0.0035(14) C35 0.056(3) 0.038(2) 0.066(3) -0.0055(19) -0.030(2) -0.0032(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 Cu O32 1.948(2) . ? Cu N11 1.961(3) . ? Cu O21 1.971(2) . ? Cu O31 1.985(2) . ? Cu O22 2.234(2) . ? Cu N2 2.544(3) . ? F21 C21 1.314(4) . ? F22 C21 1.291(5) . ? F23 C21 1.308(5) . ? F24 C25 1.291(4) . ? F25 C25 1.314(5) . ? F26 C25 1.299(5) . ? F31 C31 1.305(4) . ? F32 C31 1.324(5) . ? F33 C31 1.334(5) . ? F34 C35 1.316(5) . ? F35 C35 1.299(5) . ? F36 C35 1.329(5) . ? O1 C2 1.207(4) . ? O21 C22 1.260(4) . ? O22 C24 1.231(4) . ? O31 C32 1.260(4) . ? O32 C34 1.256(4) . ? N1 N2 1.361(4) . ? N1 C2 1.381(4) . ? N1 C3 1.451(4) . ? N2 C1 1.327(4) . ? N3 N4 1.359(4) . ? N3 C2 1.376(4) . ? N3 C4 1.465(4) . ? N4 C1 1.328(4) . ? N11 C11 1.334(4) . ? N11 C12 1.372(4) . ? N12 C11 1.353(4) . ? N12 C13 1.366(4) . ? N12 C14 1.468(4) . ? C1 C11 1.470(4) . ? C12 C13 1.344(5) . ? C21 C22 1.535(5) . ? C22 C23 1.373(5) . ? C23 C24 1.406(5) . ? C24 C25 1.539(5) . ? C31 C32 1.531(5) . ? C32 C33 1.384(4) . ? C33 C34 1.378(5) . ? C34 C35 1.526(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 O32 Cu N11 171.44(10) . . ? O32 Cu O21 87.20(10) . . ? N11 Cu O21 91.31(10) . . ? O32 Cu O31 91.04(9) . . ? N11 Cu O31 90.59(10) . . ? O21 Cu O31 177.93(9) . . ? O32 Cu O22 92.91(10) . . ? N11 Cu O22 95.48(10) . . ? O21 Cu O22 88.65(9) . . ? O31 Cu O22 90.37(9) . . ? O32 Cu N2 99.92(9) . . ? N11 Cu N2 71.92(10) . . ? O21 Cu N2 97.73(9) . . ? O31 Cu N2 83.63(9) . . ? O22 Cu N2 165.90(9) . . ? C22 O21 Cu 126.0(2) . . ? C24 O22 Cu 120.4(2) . . ? C32 O31 Cu 124.5(2) . . ? C34 O32 Cu 126.2(2) . . ? N2 N1 C2 124.1(3) . . ? N2 N1 C3 116.3(3) . . ? C2 N1 C3 119.6(3) . . ? C1 N2 N1 115.0(3) . . ? C1 N2 Cu 108.37(19) . . ? N1 N2 Cu 136.0(2) . . ? N4 N3 C2 125.3(3) . . ? N4 N3 C4 115.6(3) . . ? C2 N3 C4 119.0(3) . . ? C1 N4 N3 114.0(3) . . ? C11 N11 C12 105.9(3) . . ? C11 N11 Cu 124.1(2) . . ? C12 N11 Cu 129.8(2) . . ? C11 N12 C13 106.9(3) . . ? C11 N12 C14 128.8(3) . . ? C13 N12 C14 124.3(3) . . ? N2 C1 N4 127.8(3) . . ? N2 C1 C11 113.4(3) . . ? N4 C1 C11 118.7(3) . . ? O1 C2 N3 123.4(3) . . ? O1 C2 N1 122.8(3) . . ? N3 C2 N1 113.8(3) . . ? N11 C11 N12 110.4(3) . . ? N11 C11 C1 121.1(3) . . ? N12 C11 C1 128.5(3) . . ? C13 C12 N11 109.4(3) . . ? C12 C13 N12 107.3(3) . . ? F22 C21 F23 104.9(4) . . ? F22 C21 F21 107.5(3) . . ? F23 C21 F21 106.3(3) . . ? F22 C21 C22 112.2(3) . . ? F23 C21 C22 111.0(3) . . ? F21 C21 C22 114.3(3) . . ? O21 C22 C23 130.7(3) . . ? O21 C22 C21 111.8(3) . . ? C23 C22 C21 117.6(3) . . ? C22 C23 C24 123.6(3) . . ? O22 C24 C23 128.5(3) . . ? O22 C24 C25 116.0(3) . . ? C23 C24 C25 115.5(3) . . ? F24 C25 F26 108.5(4) . . ? F24 C25 F25 106.2(4) . . ? F26 C25 F25 104.9(4) . . ? F24 C25 C24 113.1(3) . . ? F26 C25 C24 112.6(3) . . ? F25 C25 C24 111.1(3) . . ? F31 C31 F32 107.6(3) . . ? F31 C31 F33 107.1(3) . . ? F32 C31 F33 106.6(3) . . ? F31 C31 C32 112.2(3) . . ? F32 C31 C32 112.9(3) . . ? F33 C31 C32 110.1(3) . . ? O31 C32 C33 128.7(3) . . ? O31 C32 C31 113.4(3) . . ? C33 C32 C31 117.8(3) . . ? C34 C33 C32 121.3(3) . . ? O32 C34 C33 128.2(3) . . ? O32 C34 C35 112.9(3) . . ? C33 C34 C35 118.9(3) . . ? F35 C35 F34 108.3(4) . . ? F35 C35 F36 106.3(4) . . ? F34 C35 F36 106.3(4) . . ? F35 C35 C34 111.2(3) . . ? F34 C35 C34 113.4(3) . . ? F36 C35 C34 111.1(4) . . ? 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 O32 Cu O21 C22 81.2(3) . . . . ? N11 Cu O21 C22 -107.2(3) . . . . ? O31 Cu O21 C22 50(3) . . . . ? O22 Cu O21 C22 -11.7(3) . . . . ? N2 Cu O21 C22 -179.1(3) . . . . ? O32 Cu O22 C24 -71.3(3) . . . . ? N11 Cu O22 C24 107.0(3) . . . . ? O21 Cu O22 C24 15.8(3) . . . . ? O31 Cu O22 C24 -162.4(3) . . . . ? N2 Cu O22 C24 133.1(4) . . . . ? O32 Cu O31 C32 -0.3(3) . . . . ? N11 Cu O31 C32 -171.9(2) . . . . ? O21 Cu O31 C32 31(3) . . . . ? O22 Cu O31 C32 92.7(3) . . . . ? N2 Cu O31 C32 -100.1(2) . . . . ? N11 Cu O32 C34 101.6(7) . . . . ? O21 Cu O32 C34 -178.3(3) . . . . ? O31 Cu O32 C34 0.6(3) . . . . ? O22 Cu O32 C34 -89.8(3) . . . . ? N2 Cu O32 C34 84.4(3) . . . . ? C2 N1 N2 C1 1.1(4) . . . . ? C3 N1 N2 C1 179.6(3) . . . . ? C2 N1 N2 Cu -168.4(2) . . . . ? C3 N1 N2 Cu 10.1(5) . . . . ? O32 Cu N2 C1 -173.7(2) . . . . ? N11 Cu N2 C1 8.9(2) . . . . ? O21 Cu N2 C1 97.8(2) . . . . ? O31 Cu N2 C1 -83.8(2) . . . . ? O22 Cu N2 C1 -18.5(5) . . . . ? O32 Cu N2 N1 -3.7(3) . . . . ? N11 Cu N2 N1 179.0(3) . . . . ? O21 Cu N2 N1 -92.2(3) . . . . ? O31 Cu N2 N1 86.3(3) . . . . ? O22 Cu N2 N1 151.5(3) . . . . ? C2 N3 N4 C1 0.3(4) . . . . ? C4 N3 N4 C1 -176.1(3) . . . . ? O32 Cu N11 C11 -26.2(8) . . . . ? O21 Cu N11 C11 -106.1(2) . . . . ? O31 Cu N11 C11 74.7(3) . . . . ? O22 Cu N11 C11 165.1(2) . . . . ? N2 Cu N11 C11 -8.4(2) . . . . ? O32 Cu N11 C12 159.1(6) . . . . ? O21 Cu N11 C12 79.3(3) . . . . ? O31 Cu N11 C12 -99.9(3) . . . . ? O22 Cu N11 C12 -9.5(3) . . . . ? N2 Cu N11 C12 177.0(3) . . . . ? N1 N2 C1 N4 -0.5(5) . . . . ? Cu N2 C1 N4 171.9(3) . . . . ? N1 N2 C1 C11 179.6(3) . . . . ? Cu N2 C1 C11 -8.0(3) . . . . ? N3 N4 C1 N2 -0.2(5) . . . . ? N3 N4 C1 C11 179.7(3) . . . . ? N4 N3 C2 O1 -179.6(3) . . . . ? C4 N3 C2 O1 -3.4(5) . . . . ? N4 N3 C2 N1 0.3(5) . . . . ? C4 N3 C2 N1 176.5(3) . . . . ? N2 N1 C2 O1 178.9(3) . . . . ? C3 N1 C2 O1 0.4(5) . . . . ? N2 N1 C2 N3 -1.0(4) . . . . ? C3 N1 C2 N3 -179.5(3) . . . . ? C12 N11 C11 N12 1.2(4) . . . . ? Cu N11 C11 N12 -174.5(2) . . . . ? C12 N11 C11 C1 -176.9(3) . . . . ? Cu N11 C11 C1 7.3(4) . . . . ? C13 N12 C11 N11 -0.9(4) . . . . ? C14 N12 C11 N11 178.2(3) . . . . ? C13 N12 C11 C1 177.0(3) . . . . ? C14 N12 C11 C1 -3.9(5) . . . . ? N2 C1 C11 N11 2.6(4) . . . . ? N4 C1 C11 N11 -177.4(3) . . . . ? N2 C1 C11 N12 -175.2(3) . . . . ? N4 C1 C11 N12 4.8(5) . . . . ? C11 N11 C12 C13 -1.0(4) . . . . ? Cu N11 C12 C13 174.4(2) . . . . ? N11 C12 C13 N12 0.5(4) . . . . ? C11 N12 C13 C12 0.3(4) . . . . ? C14 N12 C13 C12 -178.9(3) . . . . ? Cu O21 C22 C23 5.7(5) . . . . ? Cu O21 C22 C21 -174.8(2) . . . . ? F22 C21 C22 O21 56.6(4) . . . . ? F23 C21 C22 O21 -60.4(4) . . . . ? F21 C21 C22 O21 179.4(3) . . . . ? F22 C21 C22 C23 -123.8(4) . . . . ? F23 C21 C22 C23 119.2(4) . . . . ? F21 C21 C22 C23 -1.0(5) . . . . ? O21 C22 C23 C24 2.8(6) . . . . ? C21 C22 C23 C24 -176.8(3) . . . . ? Cu O22 C24 C23 -14.4(5) . . . . ? Cu O22 C24 C25 165.6(3) . . . . ? C22 C23 C24 O22 3.5(6) . . . . ? C22 C23 C24 C25 -176.6(4) . . . . ? O22 C24 C25 F24 8.6(6) . . . . ? C23 C24 C25 F24 -171.3(4) . . . . ? O22 C24 C25 F26 132.0(4) . . . . ? C23 C24 C25 F26 -47.9(5) . . . . ? O22 C24 C25 F25 -110.6(4) . . . . ? C23 C24 C25 F25 69.4(5) . . . . ? Cu O31 C32 C33 0.9(5) . . . . ? Cu O31 C32 C31 178.6(2) . . . . ? F31 C31 C32 O31 35.5(5) . . . . ? F32 C31 C32 O31 157.3(3) . . . . ? F33 C31 C32 O31 -83.7(4) . . . . ? F31 C31 C32 C33 -146.6(3) . . . . ? F32 C31 C32 C33 -24.7(5) . . . . ? F33 C31 C32 C33 94.3(4) . . . . ? O31 C32 C33 C34 -1.9(6) . . . . ? C31 C32 C33 C34 -179.5(3) . . . . ? Cu O32 C34 C33 -1.8(5) . . . . ? Cu O32 C34 C35 179.5(2) . . . . ? C32 C33 C34 O32 2.3(6) . . . . ? C32 C33 C34 C35 -179.0(3) . . . . ? O32 C34 C35 F35 68.7(5) . . . . ? C33 C34 C35 F35 -110.1(4) . . . . ? O32 C34 C35 F34 -169.0(4) . . . . ? C33 C34 C35 F34 12.2(5) . . . . ? O32 C34 C35 F36 -49.4(4) . . . . ? C33 C34 C35 F36 131.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.676 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.076