Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Elizabeth Papish' _publ_contact_author_email EP322@DREXEL.EDU _publ_section_title ; How Are Tris(triazolyl)borate Ligands Electronically Different From Tris(pyrazolyl)borate Ligands? A Study of (TtztBu,Me)CuCO [TtztBu,Me = tris(3-t-butyl-5-methyl-1,2,4-triazolyl)borate] ; loop_ _publ_author_name 'Elizabeth Papish' 'Trisha M. Donahue' 'Kirsten R. Wells' 'Glenn P A Yap' # Attachment 'lizp016x.cif' data_lizp016x _database_code_depnum_ccdc_archive 'CCDC 672237' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H37 B Cu N9 O, H2 O' _chemical_formula_sum 'C22 H39 B Cu N9 O2' _chemical_formula_weight 535.97 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' B B 0.0013 0.0007 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.664(3) _cell_length_b 9.933(3) _cell_length_c 16.753(7) _cell_angle_alpha 76.31(3) _cell_angle_beta 83.934(18) _cell_angle_gamma 64.89(2) _cell_volume 1414.8(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 991 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.86 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.807 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8463 _exptl_absorpt_correction_T_max 0.9144 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. ; _diffrn_ambient_temperature 120(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 AXS APEX diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 1 _diffrn_reflns_number 14018 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0299 _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 -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7009 _reflns_number_gt 6444 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material 'SHELXTL (Sheldrick, 2001)' _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^)+(0.0499P)^2^+0.8042P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7009 _refine_ls_number_parameters 339 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.011 _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 0.35720(2) 0.011290(19) 0.295830(11) 0.02347(7) Uani 1 1 d . . . B1 B 0.23769(18) 0.20233(18) 0.12632(10) 0.0197(3) Uani 1 1 d . . . H1 H 0.195(2) 0.270(2) 0.0669(11) 0.024 Uiso 1 1 d . . . N1 N 0.47955(14) 0.10765(14) 0.21039(8) 0.0229(2) Uani 1 1 d . . . N2 N 0.40006(14) 0.18780(14) 0.13776(7) 0.0211(2) Uani 1 1 d . . . N3 N 0.61996(15) 0.20789(15) 0.12281(8) 0.0260(3) Uani 1 1 d . . . N4 N 0.29360(14) -0.06798(13) 0.20744(8) 0.0221(2) Uani 1 1 d . . . N5 N 0.24459(14) 0.04065(13) 0.13519(7) 0.0205(2) Uani 1 1 d . . . N6 N 0.24081(16) -0.16830(15) 0.11374(9) 0.0270(3) Uani 1 1 d . . . N7 N 0.16624(14) 0.21403(14) 0.27640(7) 0.0215(2) Uani 1 1 d . . . N8 N 0.13300(13) 0.27784(13) 0.19399(7) 0.0197(2) Uani 1 1 d . . . N9 N -0.04121(15) 0.43657(14) 0.26319(8) 0.0233(2) Uani 1 1 d . . . O1 O 0.4728(2) -0.1818(2) 0.45759(10) 0.0580(4) Uani 1 1 d . . . C1 C 0.4290(2) -0.1074(2) 0.39518(11) 0.0354(4) Uani 1 1 d . . . C2 C 0.61029(17) 0.12325(16) 0.19838(10) 0.0239(3) Uani 1 1 d . . . C3 C 0.48778(17) 0.24508(17) 0.08704(9) 0.0239(3) Uani 1 1 d . . . C4 C 0.73649(18) 0.05008(18) 0.26163(11) 0.0287(3) Uani 1 1 d . . . C5 C 0.7941(2) -0.1245(2) 0.27620(14) 0.0430(4) Uani 1 1 d . . . H5A H 0.7088 -0.1533 0.2947 0.065 Uiso 1 1 calc R . . H5B H 0.8737 -0.1733 0.3183 0.065 Uiso 1 1 calc R . . H5C H 0.8363 -0.1577 0.2249 0.065 Uiso 1 1 calc R . . C6 C 0.6749(2) 0.1019(2) 0.34268(11) 0.0357(4) Uani 1 1 d . . . H6A H 0.6403 0.2125 0.3335 0.054 Uiso 1 1 calc R . . H6B H 0.7562 0.0516 0.3838 0.054 Uiso 1 1 calc R . . H6C H 0.5890 0.0747 0.3623 0.054 Uiso 1 1 calc R . . C7 C 0.8691(2) 0.0952(2) 0.23045(13) 0.0411(4) Uani 1 1 d . . . H7A H 0.8323 0.2061 0.2203 0.062 Uiso 1 1 calc R . . H7B H 0.9098 0.0607 0.1793 0.062 Uiso 1 1 calc R . . H7C H 0.9499 0.0476 0.2719 0.062 Uiso 1 1 calc R . . C8 C 0.44258(19) 0.3352(2) 0.00153(10) 0.0316(3) Uani 1 1 d . . . H8A H 0.4231 0.2740 -0.0303 0.047 Uiso 1 1 calc R . . H8B H 0.5253 0.3628 -0.0245 0.047 Uiso 1 1 calc R . . H8C H 0.3497 0.4279 0.0034 0.047 Uiso 1 1 calc R . . C9 C 0.05804(17) 0.31436(16) 0.31484(9) 0.0223(3) Uani 1 1 d . . . C10 C 0.00903(16) 0.41030(16) 0.18856(9) 0.0211(3) Uani 1 1 d . . . C11 C 0.04744(19) 0.29381(18) 0.40780(9) 0.0256(3) Uani 1 1 d . . . C12 C 0.0186(2) 0.1509(2) 0.44535(11) 0.0360(4) Uani 1 1 d . . . H12A H -0.0767 0.1619 0.4236 0.054 Uiso 1 1 calc R . . H12B H 0.0105 0.1383 0.5052 0.054 Uiso 1 1 calc R . . H12C H 0.1036 0.0614 0.4312 0.054 Uiso 1 1 calc R . . C13 C 0.1964(2) 0.2769(2) 0.44169(10) 0.0317(3) Uani 1 1 d . . . H13A H 0.1885 0.2642 0.5016 0.048 Uiso 1 1 calc R . . H13B H 0.2145 0.3681 0.4178 0.048 Uiso 1 1 calc R . . H13C H 0.2815 0.1875 0.4274 0.048 Uiso 1 1 calc R . . C14 C -0.0867(2) 0.4326(2) 0.43047(11) 0.0375(4) Uani 1 1 d . . . H14A H -0.1822 0.4402 0.4108 0.056 Uiso 1 1 calc R . . H14B H -0.0717 0.5250 0.4048 0.056 Uiso 1 1 calc R . . H14C H -0.0918 0.4214 0.4903 0.056 Uiso 1 1 calc R . . C15 C -0.06188(18) 0.51483(17) 0.10967(9) 0.0265(3) Uani 1 1 d . . . H15A H -0.1522 0.6027 0.1214 0.040 Uiso 1 1 calc R . . H15B H -0.0922 0.4606 0.0780 0.040 Uiso 1 1 calc R . . H15C H 0.0122 0.5498 0.0778 0.040 Uiso 1 1 calc R . . C16 C 0.28876(16) -0.19134(16) 0.19111(9) 0.0232(3) Uani 1 1 d . . . C17 C 0.21621(17) -0.02320(17) 0.08073(9) 0.0244(3) Uani 1 1 d . . . C18 C 0.34123(18) -0.34420(17) 0.25159(10) 0.0275(3) Uani 1 1 d . . . C19 C 0.2561(2) -0.3265(2) 0.33390(11) 0.0360(4) Uani 1 1 d . . . H19A H 0.2699 -0.2487 0.3547 0.054 Uiso 1 1 calc R . . H19B H 0.2972 -0.4238 0.3737 0.054 Uiso 1 1 calc R . . H19C H 0.1470 -0.2958 0.3259 0.054 Uiso 1 1 calc R . . C20 C 0.3087(2) -0.4572(2) 0.21648(12) 0.0393(4) Uani 1 1 d . . . H20A H 0.3445 -0.5561 0.2551 0.059 Uiso 1 1 calc R . . H20B H 0.3624 -0.4689 0.1639 0.059 Uiso 1 1 calc R . . H20C H 0.1986 -0.4189 0.2081 0.059 Uiso 1 1 calc R . . C21 C 0.5143(2) -0.4042(2) 0.26440(13) 0.0405(4) Uani 1 1 d . . . H21A H 0.5357 -0.3297 0.2842 0.061 Uiso 1 1 calc R . . H21B H 0.5680 -0.4206 0.2122 0.061 Uiso 1 1 calc R . . H21C H 0.5494 -0.5007 0.3050 0.061 Uiso 1 1 calc R . . C22 C 0.1683(2) 0.05608(19) -0.00616(10) 0.0319(3) Uani 1 1 d . . . H22A H 0.1475 -0.0108 -0.0331 0.048 Uiso 1 1 calc R . . H22B H 0.2503 0.0809 -0.0357 0.048 Uiso 1 1 calc R . . H22C H 0.0757 0.1499 -0.0065 0.048 Uiso 1 1 calc R . . O2 O 0.81912(16) 0.31310(16) 0.00504(9) 0.0379(3) Uani 1 1 d D . . H2 H 0.765(3) 0.286(3) 0.0471(13) 0.060(8) Uiso 1 1 d D . . H3 H 0.808(4) 0.274(4) -0.0358(16) 0.079(10) Uiso 1 1 d 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 0.02586(10) 0.02128(10) 0.02524(11) -0.00114(7) -0.00451(7) -0.01259(8) B1 0.0191(7) 0.0201(7) 0.0238(7) -0.0051(5) -0.0008(5) -0.0113(6) N1 0.0208(6) 0.0224(6) 0.0282(6) -0.0042(5) -0.0045(5) -0.0111(5) N2 0.0207(5) 0.0210(5) 0.0245(6) -0.0045(4) -0.0020(4) -0.0112(5) N3 0.0229(6) 0.0274(6) 0.0319(7) -0.0076(5) -0.0003(5) -0.0137(5) N4 0.0226(6) 0.0181(5) 0.0268(6) -0.0025(4) -0.0020(5) -0.0104(5) N5 0.0218(5) 0.0198(5) 0.0233(6) -0.0046(4) -0.0016(4) -0.0114(4) N6 0.0302(7) 0.0227(6) 0.0339(7) -0.0084(5) 0.0003(5) -0.0152(5) N7 0.0260(6) 0.0220(5) 0.0207(5) -0.0029(4) -0.0021(4) -0.0144(5) N8 0.0208(5) 0.0194(5) 0.0222(5) -0.0034(4) -0.0022(4) -0.0116(4) N9 0.0250(6) 0.0214(6) 0.0258(6) -0.0056(5) -0.0002(5) -0.0115(5) O1 0.0671(11) 0.0584(10) 0.0423(8) 0.0122(7) -0.0211(7) -0.0273(8) C1 0.0397(9) 0.0346(8) 0.0342(8) -0.0016(7) -0.0092(7) -0.0186(7) C2 0.0232(7) 0.0206(6) 0.0318(7) -0.0079(5) -0.0001(5) -0.0114(5) C3 0.0216(6) 0.0241(7) 0.0300(7) -0.0085(5) 0.0028(5) -0.0126(5) C4 0.0219(7) 0.0288(7) 0.0383(8) -0.0057(6) -0.0065(6) -0.0127(6) C5 0.0333(9) 0.0294(8) 0.0617(12) -0.0049(8) -0.0162(8) -0.0075(7) C6 0.0369(9) 0.0414(9) 0.0352(8) -0.0058(7) -0.0101(7) -0.0212(8) C7 0.0280(8) 0.0533(11) 0.0478(10) -0.0042(9) -0.0085(7) -0.0238(8) C8 0.0273(7) 0.0402(9) 0.0304(8) -0.0009(6) 0.0004(6) -0.0206(7) C9 0.0266(7) 0.0225(6) 0.0245(7) -0.0053(5) 0.0000(5) -0.0164(6) C10 0.0207(6) 0.0201(6) 0.0266(7) -0.0051(5) -0.0008(5) -0.0121(5) C11 0.0331(8) 0.0274(7) 0.0225(6) -0.0057(5) 0.0010(6) -0.0185(6) C12 0.0523(11) 0.0399(9) 0.0284(8) -0.0043(7) 0.0032(7) -0.0333(8) C13 0.0408(9) 0.0366(8) 0.0265(7) -0.0081(6) -0.0010(6) -0.0233(7) C14 0.0410(9) 0.0406(9) 0.0293(8) -0.0136(7) 0.0040(7) -0.0130(8) C15 0.0267(7) 0.0233(7) 0.0260(7) -0.0027(5) -0.0029(6) -0.0077(6) C16 0.0201(6) 0.0215(6) 0.0320(7) -0.0064(5) 0.0017(5) -0.0124(5) C17 0.0246(7) 0.0236(7) 0.0294(7) -0.0082(6) 0.0004(5) -0.0128(6) C18 0.0270(7) 0.0193(6) 0.0372(8) -0.0029(6) -0.0001(6) -0.0121(6) C19 0.0425(9) 0.0312(8) 0.0371(9) -0.0012(7) 0.0021(7) -0.0216(7) C20 0.0554(11) 0.0243(8) 0.0454(10) -0.0051(7) -0.0012(8) -0.0242(8) C21 0.0318(9) 0.0259(8) 0.0577(12) 0.0008(8) -0.0039(8) -0.0103(7) C22 0.0444(9) 0.0269(7) 0.0309(8) -0.0070(6) -0.0068(7) -0.0188(7) O2 0.0391(7) 0.0387(7) 0.0472(8) -0.0151(6) 0.0067(6) -0.0254(6) _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 C1 1.8064(19) . ? Cu1 N7 2.0565(15) . ? Cu1 N1 2.0778(14) . ? Cu1 N4 2.0846(14) . ? B1 N2 1.5421(19) . ? B1 N8 1.545(2) . ? B1 N5 1.5503(19) . ? N1 C2 1.3261(19) . ? N1 N2 1.3873(18) . ? N2 C3 1.3389(19) . ? N3 C3 1.336(2) . ? N3 C2 1.362(2) . ? N4 C16 1.3373(18) . ? N4 N5 1.3867(18) . ? N5 C17 1.3358(19) . ? N6 C17 1.341(2) . ? N6 C16 1.358(2) . ? N7 C9 1.333(2) . ? N7 N8 1.3847(17) . ? N8 C10 1.3428(19) . ? N9 C10 1.336(2) . ? N9 C9 1.354(2) . ? O1 C1 1.132(2) . ? C2 C4 1.515(2) . ? C3 C8 1.496(2) . ? C4 C7 1.533(2) . ? C4 C6 1.537(3) . ? C4 C5 1.545(2) . ? C9 C11 1.520(2) . ? C10 C15 1.494(2) . ? C11 C13 1.531(2) . ? C11 C14 1.534(2) . ? C11 C12 1.538(2) . ? C16 C18 1.522(2) . ? C17 C22 1.498(2) . ? C18 C20 1.535(2) . ? C18 C19 1.536(2) . ? C18 C21 1.539(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 C1 Cu1 N7 125.27(8) . . ? C1 Cu1 N1 124.41(7) . . ? N7 Cu1 N1 90.60(6) . . ? C1 Cu1 N4 122.09(7) . . ? N7 Cu1 N4 92.85(5) . . ? N1 Cu1 N4 92.20(5) . . ? N2 B1 N8 108.45(11) . . ? N2 B1 N5 108.55(11) . . ? N8 B1 N5 109.64(11) . . ? C2 N1 N2 104.30(12) . . ? C2 N1 Cu1 143.22(11) . . ? N2 N1 Cu1 112.48(9) . . ? C3 N2 N1 107.96(12) . . ? C3 N2 B1 130.59(13) . . ? N1 N2 B1 121.44(11) . . ? C3 N3 C2 104.12(13) . . ? C16 N4 N5 103.83(12) . . ? C16 N4 Cu1 143.44(11) . . ? N5 N4 Cu1 112.60(9) . . ? C17 N5 N4 108.29(12) . . ? C17 N5 B1 130.58(13) . . ? N4 N5 B1 121.06(11) . . ? C17 N6 C16 103.92(13) . . ? C9 N7 N8 103.69(12) . . ? C9 N7 Cu1 143.11(10) . . ? N8 N7 Cu1 113.19(9) . . ? C10 N8 N7 108.08(12) . . ? C10 N8 B1 130.68(12) . . ? N7 N8 B1 121.10(12) . . ? C10 N9 C9 103.83(13) . . ? O1 C1 Cu1 179.41(19) . . ? N1 C2 N3 112.89(14) . . ? N1 C2 C4 123.01(14) . . ? N3 C2 C4 124.08(14) . . ? N3 C3 N2 110.73(14) . . ? N3 C3 C8 125.57(14) . . ? N2 C3 C8 123.69(14) . . ? C2 C4 C7 110.11(14) . . ? C2 C4 C6 109.91(14) . . ? C7 C4 C6 109.25(14) . . ? C2 C4 C5 108.58(14) . . ? C7 C4 C5 109.38(15) . . ? C6 C4 C5 109.59(16) . . ? N7 C9 N9 113.59(13) . . ? N7 C9 C11 123.23(14) . . ? N9 C9 C11 123.18(14) . . ? N9 C10 N8 110.81(13) . . ? N9 C10 C15 124.68(13) . . ? N8 C10 C15 124.51(13) . . ? C9 C11 C13 109.97(13) . . ? C9 C11 C14 109.22(14) . . ? C13 C11 C14 109.84(14) . . ? C9 C11 C12 109.44(13) . . ? C13 C11 C12 109.59(14) . . ? C14 C11 C12 108.77(14) . . ? N4 C16 N6 113.12(13) . . ? N4 C16 C18 123.07(14) . . ? N6 C16 C18 123.70(13) . . ? N5 C17 N6 110.83(14) . . ? N5 C17 C22 124.18(13) . . ? N6 C17 C22 124.97(14) . . ? C16 C18 C20 109.69(14) . . ? C16 C18 C19 110.37(13) . . ? C20 C18 C19 108.98(14) . . ? C16 C18 C21 108.30(13) . . ? C20 C18 C21 109.40(15) . . ? C19 C18 C21 110.09(15) . . ? 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 C1 Cu1 N1 C2 -3.4(2) . . . . ? N7 Cu1 N1 C2 131.63(17) . . . . ? N4 Cu1 N1 C2 -135.50(17) . . . . ? C1 Cu1 N1 N2 177.20(10) . . . . ? N7 Cu1 N1 N2 -47.79(10) . . . . ? N4 Cu1 N1 N2 45.08(10) . . . . ? C2 N1 N2 C3 0.38(15) . . . . ? Cu1 N1 N2 C3 -179.98(9) . . . . ? C2 N1 N2 B1 -178.43(12) . . . . ? Cu1 N1 N2 B1 1.21(15) . . . . ? N8 B1 N2 C3 -120.15(16) . . . . ? N5 B1 N2 C3 120.80(16) . . . . ? N8 B1 N2 N1 58.37(16) . . . . ? N5 B1 N2 N1 -60.68(16) . . . . ? C1 Cu1 N4 C16 -4.0(2) . . . . ? N7 Cu1 N4 C16 -139.49(17) . . . . ? N1 Cu1 N4 C16 129.80(17) . . . . ? C1 Cu1 N4 N5 -178.82(10) . . . . ? N7 Cu1 N4 N5 45.65(10) . . . . ? N1 Cu1 N4 N5 -45.06(10) . . . . ? C16 N4 N5 C17 -0.92(15) . . . . ? Cu1 N4 N5 C17 175.93(9) . . . . ? C16 N4 N5 B1 -178.05(12) . . . . ? Cu1 N4 N5 B1 -1.20(15) . . . . ? N2 B1 N5 C17 -115.88(16) . . . . ? N8 B1 N5 C17 125.82(15) . . . . ? N2 B1 N5 N4 60.54(16) . . . . ? N8 B1 N5 N4 -57.77(16) . . . . ? C1 Cu1 N7 C9 4.86(19) . . . . ? N1 Cu1 N7 C9 -129.54(16) . . . . ? N4 Cu1 N7 C9 138.23(16) . . . . ? C1 Cu1 N7 N8 -177.06(10) . . . . ? N1 Cu1 N7 N8 48.54(9) . . . . ? N4 Cu1 N7 N8 -43.69(9) . . . . ? C9 N7 N8 C10 0.07(14) . . . . ? Cu1 N7 N8 C10 -178.75(9) . . . . ? C9 N7 N8 B1 176.21(11) . . . . ? Cu1 N7 N8 B1 -2.60(14) . . . . ? N2 B1 N8 C10 117.47(15) . . . . ? N5 B1 N8 C10 -124.16(15) . . . . ? N2 B1 N8 N7 -57.70(15) . . . . ? N5 B1 N8 N7 60.67(16) . . . . ? N2 N1 C2 N3 -0.10(16) . . . . ? Cu1 N1 C2 N3 -179.55(12) . . . . ? N2 N1 C2 C4 -178.39(13) . . . . ? Cu1 N1 C2 C4 2.2(3) . . . . ? C3 N3 C2 N1 -0.22(17) . . . . ? C3 N3 C2 C4 178.06(14) . . . . ? C2 N3 C3 N2 0.47(16) . . . . ? C2 N3 C3 C8 -178.26(15) . . . . ? N1 N2 C3 N3 -0.55(16) . . . . ? B1 N2 C3 N3 178.12(13) . . . . ? N1 N2 C3 C8 178.21(14) . . . . ? B1 N2 C3 C8 -3.1(2) . . . . ? N1 C2 C4 C7 -177.74(15) . . . . ? N3 C2 C4 C7 4.2(2) . . . . ? N1 C2 C4 C6 -57.34(19) . . . . ? N3 C2 C4 C6 124.55(16) . . . . ? N1 C2 C4 C5 62.5(2) . . . . ? N3 C2 C4 C5 -115.58(17) . . . . ? N8 N7 C9 N9 0.10(15) . . . . ? Cu1 N7 C9 N9 178.28(12) . . . . ? N8 N7 C9 C11 -179.69(12) . . . . ? Cu1 N7 C9 C11 -1.5(2) . . . . ? C10 N9 C9 N7 -0.22(16) . . . . ? C10 N9 C9 C11 179.57(13) . . . . ? C9 N9 C10 N8 0.25(15) . . . . ? C9 N9 C10 C15 -179.10(13) . . . . ? N7 N8 C10 N9 -0.21(15) . . . . ? B1 N8 C10 N9 -175.86(13) . . . . ? N7 N8 C10 C15 179.15(13) . . . . ? B1 N8 C10 C15 3.5(2) . . . . ? N7 C9 C11 C13 57.51(18) . . . . ? N9 C9 C11 C13 -122.26(15) . . . . ? N7 C9 C11 C14 178.11(14) . . . . ? N9 C9 C11 C14 -1.7(2) . . . . ? N7 C9 C11 C12 -62.92(19) . . . . ? N9 C9 C11 C12 117.31(16) . . . . ? N5 N4 C16 N6 0.23(16) . . . . ? Cu1 N4 C16 N6 -174.89(12) . . . . ? N5 N4 C16 C18 176.67(13) . . . . ? Cu1 N4 C16 C18 1.6(3) . . . . ? C17 N6 C16 N4 0.54(17) . . . . ? C17 N6 C16 C18 -175.88(13) . . . . ? N4 N5 C17 N6 1.32(17) . . . . ? B1 N5 C17 N6 178.09(13) . . . . ? N4 N5 C17 C22 -176.87(14) . . . . ? B1 N5 C17 C22 -0.1(2) . . . . ? C16 N6 C17 N5 -1.13(17) . . . . ? C16 N6 C17 C22 177.05(15) . . . . ? N4 C16 C18 C20 175.58(14) . . . . ? N6 C16 C18 C20 -8.4(2) . . . . ? N4 C16 C18 C19 55.49(19) . . . . ? N6 C16 C18 C19 -128.44(16) . . . . ? N4 C16 C18 C21 -65.08(19) . . . . ? N6 C16 C18 C21 110.99(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 N3 0.891(17) 2.063(18) 2.936(2) 166(3) . O2 H3 N6 0.897(18) 2.06(4) 2.944(2) 170(3) 2_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.675 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.081