# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name R.Guilard 'Fanny Chaux' 'Franck Denat' 'Enrique Espinosa' _publ_contact_author_name 'Roger Guilard' _publ_contact_author_address ; Laboratoire d'Ingenierie Universite de Bourgogne LIMSAG UMR 5633 Faculte des Sciences Mirande 9 avenue Alain Savary, BP 47870 DIJON cedex 21078 FRANCE ; _publ_contact_author_email ROGER.GUILARD@U-BOURGOGNE.FR _publ_requested_journal 'Chemical Communications' _publ_section_title ; An easy route towards regioselectively difunctionalized cyclens and new cryptands ; data_fac614 _database_code_depnum_ccdc_archive 'CCDC 619209' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H40 Fe2 N4' _chemical_formula_sum 'C30 H40 Fe2 N4' _chemical_formula_weight 568.36 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.8821(4) _cell_length_b 12.4231(3) _cell_length_c 10.8980(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.4660(10) _cell_angle_gamma 90.00 _cell_volume 2628.32(11) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3133 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.131 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5717 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.56 _reflns_number_total 3025 _reflns_number_gt 2278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0386P)^2^+0.0846P] 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 3025 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 Fe1 Fe -0.155672(13) 0.35810(2) -0.30236(2) 0.01767(10) Uani 1 1 d . . . N1 N -0.06487(7) 0.21355(12) 0.07571(13) 0.0178(4) Uani 1 1 d . . . N2 N 0.08743(8) 0.20700(13) 0.16558(14) 0.0200(4) Uani 1 1 d . . . HN2 H 0.0583(9) 0.2463(17) 0.1958(17) 0.0231(12) Uiso 1 1 d . . . C1 C -0.02237(9) 0.12772(15) 0.03972(18) 0.0199(4) Uani 1 1 d . . . H1A H -0.0430 0.1036 -0.0446 0.0231(12) Uiso 1 1 calc R . . H1B H -0.0215 0.0671 0.0962 0.0231(12) Uiso 1 1 calc R . . C2 C 0.05127(10) 0.16464(16) 0.04386(17) 0.0210(4) Uani 1 1 d . . . H2A H 0.0773 0.1043 0.0218 0.0231(12) Uiso 1 1 calc R . . H2B H 0.0503 0.2200 -0.0193 0.0231(12) Uiso 1 1 calc R . . C3 C 0.11235(10) 0.12324(15) 0.25889(17) 0.0217(4) Uani 1 1 d . . . H3A H 0.1540 0.0912 0.2424 0.0231(12) Uiso 1 1 calc R . . H3B H 0.0779 0.0671 0.2531 0.0231(12) Uiso 1 1 calc R . . C4 C 0.12714(9) 0.17189(17) 0.39005(17) 0.0210(4) Uani 1 1 d . . . H4A H 0.1476 0.1175 0.4504 0.0231(12) Uiso 1 1 calc R . . H4B H 0.1602 0.2299 0.3940 0.0231(12) Uiso 1 1 calc R . . C11 C -0.08100(9) 0.29952(15) -0.01960(16) 0.0189(4) Uani 1 1 d . . . H11A H -0.0382 0.3241 -0.0391 0.0231(12) Uiso 1 1 calc R . . H11B H -0.1008 0.3597 0.0170 0.0231(12) Uiso 1 1 calc R . . C12 C -0.12973(9) 0.26881(15) -0.14102(16) 0.0180(4) Uani 1 1 d . . . C13 C -0.11426(10) 0.21163(15) -0.24549(17) 0.0213(4) Uani 1 1 d . . . H13 H -0.0710 0.1869 -0.2521 0.0231(12) Uiso 1 1 calc R . . C14 C -0.17632(10) 0.19917(16) -0.33732(18) 0.0248(5) Uani 1 1 d . . . H14 H -0.1806 0.1650 -0.4146 0.0231(12) Uiso 1 1 calc R . . C15 C -0.23051(10) 0.24742(17) -0.29155(18) 0.0249(5) Uani 1 1 d . . . H15 H -0.2766 0.2505 -0.3330 0.0231(12) Uiso 1 1 calc R . . C16 C -0.20169(9) 0.29031(16) -0.17061(17) 0.0220(4) Uani 1 1 d . . . H16 H -0.2260 0.3265 -0.1192 0.0231(12) Uiso 1 1 calc R . . C17 C -0.10503(10) 0.50259(15) -0.27128(18) 0.0213(4) Uani 1 1 d . . . H17 H -0.0779 0.5263 -0.1957 0.0231(12) Uiso 1 1 calc R . . C18 C -0.08196(10) 0.44236(15) -0.36553(17) 0.0222(4) Uani 1 1 d . . . H18 H -0.0370 0.4198 -0.3621 0.0231(12) Uiso 1 1 calc R . . C19 C -0.13933(10) 0.42280(17) -0.46544(18) 0.0261(5) Uani 1 1 d . . . H19 H -0.1388 0.3851 -0.5389 0.0231(12) Uiso 1 1 calc R . . C20 C -0.19765(11) 0.47120(16) -0.43304(19) 0.0283(5) Uani 1 1 d . . . H20 H -0.2422 0.4709 -0.4821 0.0231(12) Uiso 1 1 calc R . . C21 C -0.17686(10) 0.51999(16) -0.31348(19) 0.0259(5) Uani 1 1 d . . . H21 H -0.2052 0.5569 -0.2703 0.0231(12) 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 Fe1 0.01869(16) 0.01827(17) 0.01600(15) 0.00104(12) 0.00364(11) -0.00038(12) N1 0.0172(8) 0.0181(9) 0.0181(8) 0.0022(7) 0.0040(6) 0.0016(7) N2 0.0200(9) 0.0221(10) 0.0184(8) -0.0020(7) 0.0053(7) 0.0022(7) C1 0.0222(10) 0.0184(11) 0.0184(9) -0.0005(8) 0.0029(8) 0.0013(8) C2 0.0224(10) 0.0221(11) 0.0194(10) -0.0021(8) 0.0062(8) 0.0022(8) C3 0.0181(10) 0.0257(12) 0.0213(10) -0.0020(8) 0.0041(8) 0.0020(8) C4 0.0179(10) 0.0262(11) 0.0190(10) -0.0013(8) 0.0040(8) 0.0006(8) C11 0.0208(10) 0.0182(11) 0.0178(9) 0.0006(8) 0.0045(8) 0.0006(8) C12 0.0196(10) 0.0174(11) 0.0174(9) 0.0045(8) 0.0051(8) -0.0004(8) C13 0.0261(11) 0.0180(11) 0.0199(10) 0.0032(8) 0.0052(8) 0.0029(8) C14 0.0347(12) 0.0176(11) 0.0211(10) -0.0023(8) 0.0039(9) -0.0041(9) C15 0.0217(10) 0.0268(12) 0.0249(10) 0.0041(9) 0.0023(8) -0.0064(9) C16 0.0206(10) 0.0258(12) 0.0209(10) 0.0025(9) 0.0075(8) -0.0013(8) C17 0.0264(11) 0.0175(11) 0.0195(10) -0.0004(8) 0.0036(8) -0.0039(8) C18 0.0229(10) 0.0210(11) 0.0242(10) 0.0030(9) 0.0080(8) -0.0043(9) C19 0.0400(13) 0.0223(12) 0.0159(10) 0.0011(8) 0.0060(9) -0.0068(10) C20 0.0287(11) 0.0219(12) 0.0285(11) 0.0074(9) -0.0067(9) -0.0015(9) C21 0.0281(11) 0.0195(11) 0.0305(11) 0.0015(9) 0.0070(9) 0.0034(9) _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 Fe1 C14 2.036(2) . ? Fe1 C13 2.0378(19) . ? Fe1 C18 2.0379(18) . ? Fe1 C19 2.0396(19) . ? Fe1 C16 2.0433(18) . ? Fe1 C20 2.0459(19) . ? Fe1 C15 2.048(2) . ? Fe1 C12 2.0485(17) . ? Fe1 C17 2.0502(19) . ? Fe1 C21 2.053(2) . ? N1 C4 1.463(2) 2 ? N1 C1 1.466(2) . ? N1 C11 1.476(2) . ? N2 C2 1.463(2) . ? N2 C3 1.465(2) . ? N2 HN2 0.87(2) . ? C1 C2 1.526(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.521(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N1 1.463(2) 2 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C11 C12 1.511(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C16 1.422(3) . ? C12 C13 1.431(2) . ? C13 C14 1.419(3) . ? C13 H13 0.9300 . ? C14 C15 1.415(3) . ? C14 H14 0.9300 . ? C15 C16 1.423(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C21 1.419(3) . ? C17 C18 1.424(3) . ? C17 H17 0.9300 . ? C18 C19 1.418(3) . ? C18 H18 0.9300 . ? C19 C20 1.417(3) . ? C19 H19 0.9300 . ? C20 C21 1.415(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 Fe1 C13 40.79(8) . . ? C14 Fe1 C18 124.45(8) . . ? C13 Fe1 C18 106.77(8) . . ? C14 Fe1 C19 106.42(8) . . ? C13 Fe1 C19 119.14(8) . . ? C18 Fe1 C19 40.69(7) . . ? C14 Fe1 C16 68.22(8) . . ? C13 Fe1 C16 68.35(7) . . ? C18 Fe1 C16 155.90(8) . . ? C19 Fe1 C16 162.65(8) . . ? C14 Fe1 C20 120.02(8) . . ? C13 Fe1 C20 154.45(8) . . ? C18 Fe1 C20 68.11(8) . . ? C19 Fe1 C20 40.58(8) . . ? C16 Fe1 C20 126.51(8) . . ? C14 Fe1 C15 40.53(8) . . ? C13 Fe1 C15 68.52(8) . . ? C18 Fe1 C15 161.57(8) . . ? C19 Fe1 C15 124.69(8) . . ? C16 Fe1 C15 40.69(7) . . ? C20 Fe1 C15 107.99(8) . . ? C14 Fe1 C12 68.82(8) . . ? C13 Fe1 C12 40.99(7) . . ? C18 Fe1 C12 120.13(8) . . ? C19 Fe1 C12 154.61(8) . . ? C16 Fe1 C12 40.68(7) . . ? C20 Fe1 C12 163.46(8) . . ? C15 Fe1 C12 68.81(7) . . ? C14 Fe1 C17 162.19(8) . . ? C13 Fe1 C17 125.44(8) . . ? C18 Fe1 C17 40.78(7) . . ? C19 Fe1 C17 68.53(8) . . ? C16 Fe1 C17 121.55(8) . . ? C20 Fe1 C17 68.02(8) . . ? C15 Fe1 C17 156.25(8) . . ? C12 Fe1 C17 107.98(8) . . ? C14 Fe1 C21 155.30(9) . . ? C13 Fe1 C21 163.13(8) . . ? C18 Fe1 C21 68.30(8) . . ? C19 Fe1 C21 68.39(8) . . ? C16 Fe1 C21 109.14(8) . . ? C20 Fe1 C21 40.40(8) . . ? C15 Fe1 C21 121.25(8) . . ? C12 Fe1 C21 126.27(8) . . ? C17 Fe1 C21 40.47(8) . . ? C4 N1 C1 112.31(15) 2 . ? C4 N1 C11 111.61(14) 2 . ? C1 N1 C11 112.85(14) . . ? C2 N2 C3 113.59(15) . . ? C2 N2 HN2 107.8(12) . . ? C3 N2 HN2 106.7(13) . . ? N1 C1 C2 112.24(15) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? N2 C2 C1 114.54(15) . . ? N2 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? N2 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? N2 C3 C4 109.75(16) . . ? N2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? N2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? N1 C4 C3 112.20(15) 2 . ? N1 C4 H4A 109.2 2 . ? C3 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 2 . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N1 C11 C12 115.76(15) . . ? N1 C11 H11A 108.3 . . ? C12 C11 H11A 108.3 . . ? N1 C11 H11B 108.3 . . ? C12 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? C16 C12 C13 106.94(16) . . ? C16 C12 C11 125.09(16) . . ? C13 C12 C11 127.96(16) . . ? C16 C12 Fe1 69.46(10) . . ? C13 C12 Fe1 69.10(10) . . ? C11 C12 Fe1 127.60(13) . . ? C14 C13 C12 108.16(17) . . ? C14 C13 Fe1 69.53(11) . . ? C12 C13 Fe1 69.91(10) . . ? C14 C13 H13 125.9 . . ? C12 C13 H13 125.9 . . ? Fe1 C13 H13 126.2 . . ? C15 C14 C13 108.51(17) . . ? C15 C14 Fe1 70.20(12) . . ? C13 C14 Fe1 69.68(11) . . ? C15 C14 H14 125.7 . . ? C13 C14 H14 125.7 . . ? Fe1 C14 H14 126.0 . . ? C14 C15 C16 107.48(17) . . ? C14 C15 Fe1 69.27(11) . . ? C16 C15 Fe1 69.48(11) . . ? C14 C15 H15 126.3 . . ? C16 C15 H15 126.3 . . ? Fe1 C15 H15 126.6 . . ? C12 C16 C15 108.90(17) . . ? C12 C16 Fe1 69.85(10) . . ? C15 C16 Fe1 69.83(11) . . ? C12 C16 H16 125.5 . . ? C15 C16 H16 125.5 . . ? Fe1 C16 H16 126.4 . . ? C21 C17 C18 107.73(17) . . ? C21 C17 Fe1 69.87(11) . . ? C18 C17 Fe1 69.15(11) . . ? C21 C17 H17 126.1 . . ? C18 C17 H17 126.1 . . ? Fe1 C17 H17 126.4 . . ? C19 C18 C17 108.24(18) . . ? C19 C18 Fe1 69.72(11) . . ? C17 C18 Fe1 70.07(11) . . ? C19 C18 H18 125.9 . . ? C17 C18 H18 125.9 . . ? Fe1 C18 H18 125.9 . . ? C20 C19 C18 107.57(18) . . ? C20 C19 Fe1 69.95(11) . . ? C18 C19 Fe1 69.59(11) . . ? C20 C19 H19 126.2 . . ? C18 C19 H19 126.2 . . ? Fe1 C19 H19 125.8 . . ? C21 C20 C19 108.61(17) . . ? C21 C20 Fe1 70.07(11) . . ? C19 C20 Fe1 69.47(11) . . ? C21 C20 H20 125.7 . . ? C19 C20 H20 125.7 . . ? Fe1 C20 H20 126.3 . . ? C20 C21 C17 107.85(18) . . ? C20 C21 Fe1 69.53(11) . . ? C17 C21 Fe1 69.66(11) . . ? C20 C21 H21 126.1 . . ? C17 C21 H21 126.1 . . ? Fe1 C21 H21 126.3 . . ? 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 C4 N1 C1 C2 -162.11(15) 2 . . . ? C11 N1 C1 C2 70.67(19) . . . . ? C3 N2 C2 C1 77.5(2) . . . . ? N1 C1 C2 N2 56.7(2) . . . . ? C2 N2 C3 C4 -161.30(15) . . . . ? N2 C3 C4 N1 64.1(2) . . . 2 ? C4 N1 C11 C12 -58.0(2) 2 . . . ? C1 N1 C11 C12 69.62(19) . . . . ? N1 C11 C12 C16 97.9(2) . . . . ? N1 C11 C12 C13 -80.4(2) . . . . ? N1 C11 C12 Fe1 -172.15(12) . . . . ? C14 Fe1 C12 C16 -80.81(12) . . . . ? C13 Fe1 C12 C16 -118.43(16) . . . . ? C18 Fe1 C12 C16 160.73(11) . . . . ? C19 Fe1 C12 C16 -164.55(17) . . . . ? C20 Fe1 C12 C16 44.6(3) . . . . ? C15 Fe1 C12 C16 -37.20(11) . . . . ? C17 Fe1 C12 C16 117.80(12) . . . . ? C21 Fe1 C12 C16 76.73(14) . . . . ? C14 Fe1 C12 C13 37.62(11) . . . . ? C18 Fe1 C12 C13 -80.84(13) . . . . ? C19 Fe1 C12 C13 -46.1(2) . . . . ? C16 Fe1 C12 C13 118.43(16) . . . . ? C20 Fe1 C12 C13 163.1(2) . . . . ? C15 Fe1 C12 C13 81.23(12) . . . . ? C17 Fe1 C12 C13 -123.77(11) . . . . ? C21 Fe1 C12 C13 -164.84(11) . . . . ? C14 Fe1 C12 C11 160.09(18) . . . . ? C13 Fe1 C12 C11 122.5(2) . . . . ? C18 Fe1 C12 C11 41.64(19) . . . . ? C19 Fe1 C12 C11 76.4(3) . . . . ? C16 Fe1 C12 C11 -119.1(2) . . . . ? C20 Fe1 C12 C11 -74.5(3) . . . . ? C15 Fe1 C12 C11 -156.29(18) . . . . ? C17 Fe1 C12 C11 -1.30(18) . . . . ? C21 Fe1 C12 C11 -42.37(19) . . . . ? C16 C12 C13 C14 0.2(2) . . . . ? C11 C12 C13 C14 178.74(17) . . . . ? Fe1 C12 C13 C14 -59.22(13) . . . . ? C16 C12 C13 Fe1 59.41(13) . . . . ? C11 C12 C13 Fe1 -122.04(19) . . . . ? C18 Fe1 C13 C14 -123.71(12) . . . . ? C19 Fe1 C13 C14 -81.33(13) . . . . ? C16 Fe1 C13 C14 81.31(12) . . . . ? C20 Fe1 C13 C14 -49.5(2) . . . . ? C15 Fe1 C13 C14 37.41(11) . . . . ? C12 Fe1 C13 C14 119.39(16) . . . . ? C17 Fe1 C13 C14 -164.58(11) . . . . ? C21 Fe1 C13 C14 166.0(2) . . . . ? C14 Fe1 C13 C12 -119.39(16) . . . . ? C18 Fe1 C13 C12 116.90(11) . . . . ? C19 Fe1 C13 C12 159.28(11) . . . . ? C16 Fe1 C13 C12 -38.08(11) . . . . ? C20 Fe1 C13 C12 -168.92(16) . . . . ? C15 Fe1 C13 C12 -81.98(11) . . . . ? C17 Fe1 C13 C12 76.03(13) . . . . ? C21 Fe1 C13 C12 46.6(3) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? Fe1 C13 C14 C15 -59.67(14) . . . . ? C12 C13 C14 Fe1 59.45(13) . . . . ? C13 Fe1 C14 C15 119.55(16) . . . . ? C18 Fe1 C14 C15 -165.48(11) . . . . ? C19 Fe1 C14 C15 -124.62(12) . . . . ? C16 Fe1 C14 C15 37.89(11) . . . . ? C20 Fe1 C14 C15 -82.71(13) . . . . ? C12 Fe1 C14 C15 81.76(11) . . . . ? C17 Fe1 C14 C15 164.6(2) . . . . ? C21 Fe1 C14 C15 -50.8(2) . . . . ? C18 Fe1 C14 C13 74.97(13) . . . . ? C19 Fe1 C14 C13 115.82(12) . . . . ? C16 Fe1 C14 C13 -81.66(12) . . . . ? C20 Fe1 C14 C13 157.74(12) . . . . ? C15 Fe1 C14 C13 -119.55(16) . . . . ? C12 Fe1 C14 C13 -37.80(11) . . . . ? C17 Fe1 C14 C13 45.1(3) . . . . ? C21 Fe1 C14 C13 -170.31(16) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? Fe1 C14 C15 C16 -59.19(14) . . . . ? C13 C14 C15 Fe1 59.35(13) . . . . ? C13 Fe1 C15 C14 -37.64(11) . . . . ? C18 Fe1 C15 C14 40.8(3) . . . . ? C19 Fe1 C15 C14 73.72(14) . . . . ? C16 Fe1 C15 C14 -118.98(16) . . . . ? C20 Fe1 C15 C14 115.44(12) . . . . ? C12 Fe1 C15 C14 -81.79(12) . . . . ? C17 Fe1 C15 C14 -168.40(17) . . . . ? C21 Fe1 C15 C14 157.76(12) . . . . ? C14 Fe1 C15 C16 118.98(16) . . . . ? C13 Fe1 C15 C16 81.35(12) . . . . ? C18 Fe1 C15 C16 159.8(2) . . . . ? C19 Fe1 C15 C16 -167.30(12) . . . . ? C20 Fe1 C15 C16 -125.57(12) . . . . ? C12 Fe1 C15 C16 37.19(11) . . . . ? C17 Fe1 C15 C16 -49.4(2) . . . . ? C21 Fe1 C15 C16 -83.26(13) . . . . ? C13 C12 C16 C15 -0.1(2) . . . . ? C11 C12 C16 C15 -178.70(17) . . . . ? Fe1 C12 C16 C15 59.08(14) . . . . ? C13 C12 C16 Fe1 -59.19(12) . . . . ? C11 C12 C16 Fe1 122.22(18) . . . . ? C14 C15 C16 C12 0.0(2) . . . . ? Fe1 C15 C16 C12 -59.09(13) . . . . ? C14 C15 C16 Fe1 59.07(14) . . . . ? C14 Fe1 C16 C12 82.41(12) . . . . ? C13 Fe1 C16 C12 38.36(11) . . . . ? C18 Fe1 C16 C12 -44.4(2) . . . . ? C19 Fe1 C16 C12 157.5(3) . . . . ? C20 Fe1 C16 C12 -165.59(11) . . . . ? C15 Fe1 C16 C12 120.16(17) . . . . ? C17 Fe1 C16 C12 -80.87(13) . . . . ? C21 Fe1 C16 C12 -123.83(12) . . . . ? C14 Fe1 C16 C15 -37.74(12) . . . . ? C13 Fe1 C16 C15 -81.80(13) . . . . ? C18 Fe1 C16 C15 -164.51(18) . . . . ? C19 Fe1 C16 C15 37.3(3) . . . . ? C20 Fe1 C16 C15 74.25(15) . . . . ? C12 Fe1 C16 C15 -120.16(17) . . . . ? C17 Fe1 C16 C15 158.97(12) . . . . ? C21 Fe1 C16 C15 116.01(12) . . . . ? C14 Fe1 C17 C21 158.1(2) . . . . ? C13 Fe1 C17 C21 -167.30(11) . . . . ? C18 Fe1 C17 C21 119.12(17) . . . . ? C19 Fe1 C17 C21 81.45(12) . . . . ? C16 Fe1 C17 C21 -82.72(13) . . . . ? C20 Fe1 C17 C21 37.61(12) . . . . ? C15 Fe1 C17 C21 -47.2(2) . . . . ? C12 Fe1 C17 C21 -125.30(12) . . . . ? C14 Fe1 C17 C18 39.0(3) . . . . ? C13 Fe1 C17 C18 73.58(14) . . . . ? C19 Fe1 C17 C18 -37.67(12) . . . . ? C16 Fe1 C17 C18 158.16(11) . . . . ? C20 Fe1 C17 C18 -81.51(13) . . . . ? C15 Fe1 C17 C18 -166.32(17) . . . . ? C12 Fe1 C17 C18 115.58(12) . . . . ? C21 Fe1 C17 C18 -119.12(17) . . . . ? C21 C17 C18 C19 0.0(2) . . . . ? Fe1 C17 C18 C19 59.49(13) . . . . ? C21 C17 C18 Fe1 -59.45(13) . . . . ? C14 Fe1 C18 C19 74.23(14) . . . . ? C13 Fe1 C18 C19 115.45(12) . . . . ? C16 Fe1 C18 C19 -170.21(18) . . . . ? C20 Fe1 C18 C19 -37.99(12) . . . . ? C15 Fe1 C18 C19 43.2(3) . . . . ? C12 Fe1 C18 C19 158.00(12) . . . . ? C17 Fe1 C18 C19 -119.26(17) . . . . ? C21 Fe1 C18 C19 -81.66(13) . . . . ? C14 Fe1 C18 C17 -166.51(11) . . . . ? C13 Fe1 C18 C17 -125.29(12) . . . . ? C19 Fe1 C18 C17 119.26(17) . . . . ? C16 Fe1 C18 C17 -50.9(2) . . . . ? C20 Fe1 C18 C17 81.27(12) . . . . ? C15 Fe1 C18 C17 162.5(2) . . . . ? C12 Fe1 C18 C17 -82.73(13) . . . . ? C21 Fe1 C18 C17 37.61(11) . . . . ? C17 C18 C19 C20 0.2(2) . . . . ? Fe1 C18 C19 C20 59.90(13) . . . . ? C17 C18 C19 Fe1 -59.72(13) . . . . ? C14 Fe1 C19 C20 117.23(12) . . . . ? C13 Fe1 C19 C20 159.55(11) . . . . ? C18 Fe1 C19 C20 -118.60(17) . . . . ? C16 Fe1 C19 C20 47.9(3) . . . . ? C15 Fe1 C19 C20 76.67(15) . . . . ? C12 Fe1 C19 C20 -167.68(16) . . . . ? C17 Fe1 C19 C20 -80.84(12) . . . . ? C21 Fe1 C19 C20 -37.19(11) . . . . ? C14 Fe1 C19 C18 -124.17(12) . . . . ? C13 Fe1 C19 C18 -81.85(13) . . . . ? C16 Fe1 C19 C18 166.5(2) . . . . ? C20 Fe1 C19 C18 118.60(17) . . . . ? C15 Fe1 C19 C18 -164.73(12) . . . . ? C12 Fe1 C19 C18 -49.1(2) . . . . ? C17 Fe1 C19 C18 37.76(12) . . . . ? C21 Fe1 C19 C18 81.41(13) . . . . ? C18 C19 C20 C21 -0.3(2) . . . . ? Fe1 C19 C20 C21 59.33(14) . . . . ? C18 C19 C20 Fe1 -59.67(13) . . . . ? C14 Fe1 C20 C21 160.05(12) . . . . ? C13 Fe1 C20 C21 -164.93(16) . . . . ? C18 Fe1 C20 C21 -81.80(13) . . . . ? C19 Fe1 C20 C21 -119.89(17) . . . . ? C16 Fe1 C20 C21 76.10(14) . . . . ? C15 Fe1 C20 C21 117.38(12) . . . . ? C12 Fe1 C20 C21 41.4(3) . . . . ? C17 Fe1 C20 C21 -37.67(12) . . . . ? C14 Fe1 C20 C19 -80.06(14) . . . . ? C13 Fe1 C20 C19 -45.0(2) . . . . ? C18 Fe1 C20 C19 38.09(12) . . . . ? C16 Fe1 C20 C19 -164.01(11) . . . . ? C15 Fe1 C20 C19 -122.73(12) . . . . ? C12 Fe1 C20 C19 161.2(2) . . . . ? C17 Fe1 C20 C19 82.21(12) . . . . ? C21 Fe1 C20 C19 119.89(17) . . . . ? C19 C20 C21 C17 0.4(2) . . . . ? Fe1 C20 C21 C17 59.33(13) . . . . ? C19 C20 C21 Fe1 -58.95(14) . . . . ? C18 C17 C21 C20 -0.3(2) . . . . ? Fe1 C17 C21 C20 -59.25(14) . . . . ? C18 C17 C21 Fe1 58.99(13) . . . . ? C14 Fe1 C21 C20 -45.0(2) . . . . ? C13 Fe1 C21 C20 157.3(2) . . . . ? C18 Fe1 C21 C20 81.28(13) . . . . ? C19 Fe1 C21 C20 37.35(12) . . . . ? C16 Fe1 C21 C20 -124.32(12) . . . . ? C15 Fe1 C21 C20 -81.05(14) . . . . ? C12 Fe1 C21 C20 -166.51(11) . . . . ? C17 Fe1 C21 C20 119.17(17) . . . . ? C14 Fe1 C21 C17 -164.16(16) . . . . ? C13 Fe1 C21 C17 38.1(3) . . . . ? C18 Fe1 C21 C17 -37.89(11) . . . . ? C19 Fe1 C21 C17 -81.82(12) . . . . ? C16 Fe1 C21 C17 116.51(12) . . . . ? C20 Fe1 C21 C17 -119.17(17) . . . . ? C15 Fe1 C21 C17 159.78(11) . . . . ? C12 Fe1 C21 C17 74.32(14) . . . . ? 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 N2 HN2 N1 0.87(2) 2.548(18) 2.976(2) 111.0(15) . N2 HN2 N1 0.87(2) 2.498(18) 2.950(2) 112.9(15) 2 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.336 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.064 #======================================================================== #===END data_fac671 _database_code_depnum_ccdc_archive 'CCDC 619210' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 Cu N4 O, 2(Cl O4)' _chemical_formula_sum 'C22 H30 Cl2 Cu N4 O9' _chemical_formula_weight 628.94 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.1266(2) _cell_length_b 13.4493(3) _cell_length_c 15.1931(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.260(1) _cell_angle_gamma 90.00 _cell_volume 2471.06(8) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 5831 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description Prism _exptl_crystal_colour Dark-red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1300 _exptl_absorpt_coefficient_mu 1.162 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10890 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.55 _reflns_number_total 5676 _reflns_number_gt 4025 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0474P)^2^+2.6136P] 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 5676 _refine_ls_number_parameters 380 _refine_ls_number_restraints 65 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.26809(3) 0.22507(3) 0.47660(2) 0.01722(12) Uani 1 1 d . . . N1 N 0.4279(2) 0.21326(18) 0.50536(16) 0.0159(5) Uani 1 1 d . . . N2 N 0.2987(2) 0.22180(12) 0.34890(15) 0.0192(6) Uani 1 1 d D . . HN2 H 0.2924 0.2867 0.3156 0.021 Uiso 1 1 d D . . N3 N 0.1117(2) 0.20310(18) 0.44112(16) 0.0146(5) Uani 1 1 d . . . N4 N 0.2427(2) 0.16291(15) 0.59302(12) 0.0173(6) Uani 1 1 d D . . HN4 H 0.2446 0.2137 0.6420 0.021 Uiso 1 1 d D . . O1 O 0.25427(17) 0.38100(16) 0.50944(14) 0.0201(5) Uani 1 1 d . . . C1 C 0.4632(3) 0.1489(3) 0.4323(2) 0.0222(7) Uani 1 1 d . . . H1A H 0.4375 0.0800 0.4409 0.0211(17) Uiso 1 1 calc R . . H1B H 0.5449 0.1480 0.4335 0.0211(17) Uiso 1 1 calc R . . C2 C 0.4150(3) 0.1880(3) 0.3426(2) 0.0240(8) Uani 1 1 d . . . H2A H 0.4605 0.2442 0.3237 0.0211(17) Uiso 1 1 calc R . . H2B H 0.4170 0.1347 0.2978 0.0211(17) Uiso 1 1 calc R . . C3 C 0.2113(3) 0.1516(2) 0.3139(2) 0.0197(7) Uani 1 1 d . . . H3A H 0.2265 0.0839 0.3373 0.0211(17) Uiso 1 1 calc R . . H3B H 0.2090 0.1490 0.2487 0.0211(17) Uiso 1 1 calc R . . C4 C 0.1017(3) 0.1895(2) 0.3433(2) 0.0192(7) Uani 1 1 d . . . H4A H 0.0825 0.2536 0.3140 0.0211(17) Uiso 1 1 calc R . . H4B H 0.0422 0.1411 0.3266 0.0211(17) Uiso 1 1 calc R . . C5 C 0.0870(3) 0.1095(2) 0.4886(2) 0.0178(7) Uani 1 1 d . . . H5A H 0.1209 0.0525 0.4594 0.0211(17) Uiso 1 1 calc R . . H5B H 0.0060 0.0989 0.4854 0.0211(17) Uiso 1 1 calc R . . C6 C 0.1317(2) 0.1142(2) 0.5853(2) 0.0198(7) Uani 1 1 d . . . H6A H 0.0799 0.1522 0.6198 0.0211(17) Uiso 1 1 calc R . . H6B H 0.1378 0.0460 0.6098 0.0211(17) Uiso 1 1 calc R . . C7 C 0.3413(2) 0.0977(2) 0.6065(2) 0.0191(7) Uani 1 1 d . . . H7A H 0.3363 0.0421 0.5636 0.0211(17) Uiso 1 1 calc R . . H7B H 0.3463 0.0695 0.6669 0.0211(17) Uiso 1 1 calc R . . C8 C 0.4426(3) 0.1613(2) 0.5929(2) 0.0188(7) Uani 1 1 d . . . H8A H 0.4528 0.2111 0.6408 0.0211(17) Uiso 1 1 calc R . . H8B H 0.5094 0.1188 0.5948 0.0211(17) Uiso 1 1 calc R . . C11 C 0.4825(3) 0.3124(2) 0.5036(2) 0.0185(7) Uani 1 1 d . . . H11A H 0.4701 0.3400 0.4432 0.0211(17) Uiso 1 1 calc R . . H11B H 0.5632 0.3029 0.5157 0.0211(17) Uiso 1 1 calc R . . C12 C 0.4440(2) 0.3878(2) 0.5679(2) 0.0167(7) Uani 1 1 d . . . C13 C 0.5217(3) 0.4294(2) 0.6300(2) 0.0215(7) Uani 1 1 d . . . H13 H 0.5953 0.4049 0.6335 0.0211(17) Uiso 1 1 calc R . . C14 C 0.4952(3) 0.5050(3) 0.6867(2) 0.0251(8) Uani 1 1 d . . . H14 H 0.5502 0.5324 0.7274 0.0211(17) Uiso 1 1 calc R . . C15 C 0.3880(3) 0.5403(2) 0.6834(2) 0.0253(8) Uani 1 1 d . . . H15 H 0.3692 0.5923 0.7218 0.0211(17) Uiso 1 1 calc R . . C16 C 0.3079(3) 0.4999(2) 0.6244(2) 0.0231(7) Uani 1 1 d . . . H16 H 0.2338 0.5232 0.6230 0.0211(17) Uiso 1 1 calc R . . C17 C 0.3360(2) 0.4257(2) 0.5677(2) 0.0173(7) Uani 1 1 d . . . C31 C 0.0433(2) 0.2872(2) 0.4712(2) 0.0167(7) Uani 1 1 d . . . H31A H 0.0506 0.2895 0.5365 0.0211(17) Uiso 1 1 calc R . . H31B H -0.0353 0.2738 0.4527 0.0211(17) Uiso 1 1 calc R . . C32 C 0.0737(2) 0.3879(2) 0.4362(2) 0.0153(6) Uani 1 1 d . . . C33 C -0.0028(3) 0.4385(2) 0.3809(2) 0.0189(7) Uani 1 1 d . . . H33 H -0.0689 0.4053 0.3601 0.0211(17) Uiso 1 1 calc R . . C34 C 0.0135(3) 0.5355(2) 0.3549(2) 0.0218(7) Uani 1 1 d . . . H34 H -0.0411 0.5686 0.3175 0.0211(17) Uiso 1 1 calc R . . C35 C 0.1105(3) 0.5842(2) 0.3840(2) 0.0211(7) Uani 1 1 d . . . H35 H 0.1218 0.6514 0.3677 0.0211(17) Uiso 1 1 calc R . . C36 C 0.1907(3) 0.5344(2) 0.4367(2) 0.0201(7) Uani 1 1 d . . . H36 H 0.2578 0.5669 0.4558 0.0211(17) Uiso 1 1 calc R . . C37 C 0.1724(2) 0.4372(2) 0.4613(2) 0.0168(7) Uani 1 1 d . . . Cl1 Cl 0.25954(6) 0.36470(6) 1.13631(5) 0.02017(18) Uani 1 1 d . . . O11 O 0.2098(2) 0.26887(16) 1.12149(17) 0.0302(6) Uani 1 1 d . . . O12 O 0.37531(19) 0.3601(2) 1.12399(19) 0.0410(7) Uani 1 1 d . . . O13 O 0.2452(2) 0.39567(18) 1.22579(16) 0.0358(6) Uani 1 1 d . . . O14 O 0.20695(19) 0.43630(17) 1.07652(15) 0.0285(6) Uani 1 1 d . . . Cl2 Cl 0.25514(7) 0.29510(6) 0.81533(6) 0.0260(2) Uani 1 1 d D . . O21A O 0.2146(7) 0.2517(6) 0.8938(5) 0.043(3) Uani 0.50 1 d PDU A 1 O22A O 0.3292(5) 0.2249(4) 0.7792(4) 0.0247(15) Uani 0.50 1 d PDU A 1 O23A O 0.1640(6) 0.3158(6) 0.7540(5) 0.058(3) Uani 0.50 1 d PDU A 1 O24A O 0.3174(5) 0.3839(4) 0.8418(4) 0.0377(15) Uani 0.50 1 d PDU A 1 O21B O 0.2666(6) 0.3974(4) 0.8322(5) 0.056(2) Uani 0.50 1 d PDU A 2 O22B O 0.3470(5) 0.2584(5) 0.7697(5) 0.036(2) Uani 0.50 1 d PDU A 2 O23B O 0.2412(7) 0.2377(6) 0.8926(4) 0.036(2) Uani 0.50 1 d PDU A 2 O24B O 0.1595(5) 0.2839(5) 0.7511(4) 0.0315(17) Uani 0.50 1 d PDU A 2 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 0.0158(2) 0.0186(2) 0.0169(2) 0.00028(16) -0.00097(15) 0.00034(16) N1 0.0137(13) 0.0180(14) 0.0158(13) -0.0007(11) 0.0008(10) 0.0003(11) N2 0.0176(13) 0.0222(14) 0.0179(14) -0.0009(12) 0.0017(11) 0.0015(11) N3 0.0166(13) 0.0133(13) 0.0135(13) 0.0000(10) -0.0019(10) 0.0001(10) N4 0.0160(13) 0.0175(14) 0.0186(14) 0.0019(11) 0.0021(11) 0.0002(11) O1 0.0143(11) 0.0145(11) 0.0299(13) -0.0046(10) -0.0089(9) 0.0010(9) C1 0.0184(17) 0.0242(18) 0.0242(18) -0.0042(14) 0.0035(14) 0.0052(14) C2 0.0207(17) 0.033(2) 0.0185(17) -0.0063(15) 0.0037(14) 0.0025(15) C3 0.0214(17) 0.0202(17) 0.0170(16) -0.0021(13) -0.0015(13) -0.0018(13) C4 0.0203(17) 0.0190(16) 0.0177(16) -0.0036(13) -0.0032(13) 0.0003(13) C5 0.0172(16) 0.0127(15) 0.0238(17) 0.0024(13) 0.0027(13) 0.0001(12) C6 0.0181(16) 0.0211(17) 0.0202(17) 0.0052(13) 0.0002(13) -0.0021(13) C7 0.0181(16) 0.0179(16) 0.0209(17) 0.0013(14) -0.0016(13) 0.0014(13) C8 0.0173(16) 0.0201(17) 0.0185(16) 0.0016(13) -0.0020(13) 0.0025(13) C11 0.0143(15) 0.0202(17) 0.0206(17) 0.0025(14) -0.0005(13) -0.0004(13) C12 0.0158(15) 0.0157(16) 0.0181(16) 0.0039(13) -0.0016(12) -0.0012(12) C13 0.0173(16) 0.0227(18) 0.0234(17) 0.0049(15) -0.0061(13) -0.0030(14) C14 0.032(2) 0.0223(18) 0.0195(17) 0.0033(14) -0.0091(15) -0.0067(15) C15 0.036(2) 0.0190(17) 0.0209(18) -0.0022(14) -0.0005(15) -0.0011(15) C16 0.0218(18) 0.0195(17) 0.0281(19) -0.0011(15) 0.0022(14) 0.0010(14) C17 0.0184(16) 0.0135(15) 0.0191(16) 0.0030(13) -0.0050(13) -0.0036(13) C31 0.0117(15) 0.0181(16) 0.0199(16) -0.0012(13) -0.0012(12) 0.0022(12) C32 0.0148(15) 0.0137(15) 0.0175(16) -0.0002(13) 0.0016(12) -0.0001(12) C33 0.0186(16) 0.0156(16) 0.0218(17) -0.0025(13) -0.0022(13) 0.0011(13) C34 0.0222(18) 0.0259(18) 0.0170(17) 0.0013(14) -0.0004(13) 0.0074(14) C35 0.0270(18) 0.0165(17) 0.0206(17) 0.0018(14) 0.0069(14) -0.0007(14) C36 0.0181(17) 0.0195(17) 0.0230(18) -0.0016(14) 0.0037(14) -0.0035(13) C37 0.0139(15) 0.0178(16) 0.0184(16) -0.0008(13) 0.0003(12) 0.0053(12) Cl1 0.0174(4) 0.0176(4) 0.0251(4) 0.0024(3) -0.0016(3) -0.0015(3) O11 0.0297(14) 0.0147(12) 0.0449(16) 0.0022(11) -0.0065(12) -0.0064(10) O12 0.0142(13) 0.0464(17) 0.0627(19) -0.0004(14) 0.0045(12) -0.0007(12) O13 0.0555(17) 0.0259(14) 0.0264(14) 0.0005(11) 0.0053(12) 0.0052(13) O14 0.0323(14) 0.0198(12) 0.0315(14) 0.0096(11) -0.0101(11) -0.0017(10) Cl2 0.0262(4) 0.0194(4) 0.0328(5) -0.0014(3) 0.0060(4) 0.0007(3) O21A 0.044(4) 0.044(3) 0.041(3) 0.002(2) 0.013(2) 0.000(2) O22A 0.025(2) 0.024(3) 0.026(2) -0.005(2) 0.0039(19) 0.004(2) O23A 0.049(3) 0.052(4) 0.072(4) 0.020(3) -0.009(2) 0.011(3) O24A 0.039(3) 0.026(2) 0.049(3) -0.008(2) 0.010(2) -0.008(2) O21B 0.064(3) 0.042(3) 0.062(3) -0.007(2) 0.005(3) -0.002(2) O22B 0.029(3) 0.042(3) 0.039(3) -0.006(2) 0.008(2) -0.001(2) O23B 0.037(3) 0.036(3) 0.035(3) 0.008(2) 0.010(2) -0.001(2) O24B 0.024(2) 0.027(3) 0.043(3) 0.010(2) -0.005(2) 0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.955(2) . ? Cu1 N1 1.962(2) . ? Cu1 N4 2.001(2) . ? Cu1 N2 2.003(2) . ? Cu1 O1 2.165(2) . ? N1 C11 1.490(4) . ? N1 C1 1.494(4) . ? N1 C8 1.501(4) . ? N2 C3 1.488(4) . ? N2 C2 1.492(4) . ? N2 HN2 1.0089 . ? N3 C5 1.492(4) . ? N3 C4 1.493(4) . ? N3 C31 1.494(4) . ? N4 C7 1.485(4) . ? N4 C6 1.493(4) . ? N4 HN4 1.0088 . ? O1 C37 1.408(3) . ? O1 C17 1.414(3) . ? C1 C2 1.536(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.522(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.529(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.524(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C11 C12 1.506(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.399(4) . ? C12 C17 1.406(4) . ? C13 C14 1.386(5) . ? C13 H13 0.9500 . ? C14 C15 1.381(5) . ? C14 H14 0.9500 . ? C15 C16 1.383(5) . ? C15 H15 0.9500 . ? C16 C17 1.377(4) . ? C16 H16 0.9500 . ? C31 C32 1.510(4) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.384(4) . ? C32 C37 1.396(4) . ? C33 C34 1.382(4) . ? C33 H33 0.9500 . ? C34 C35 1.390(4) . ? C34 H34 0.9500 . ? C35 C36 1.385(4) . ? C35 H35 0.9500 . ? C36 C37 1.383(4) . ? C36 H36 0.9500 . ? Cl1 O12 1.431(2) . ? Cl1 O11 1.434(2) . ? Cl1 O14 1.440(2) . ? Cl1 O13 1.445(2) . ? Cl2 O21B 1.405(6) . ? Cl2 O23A 1.419(4) . ? Cl2 O23B 1.425(4) . ? Cl2 O22A 1.440(5) . ? Cl2 O22B 1.442(6) . ? Cl2 O21A 1.446(6) . ? Cl2 O24A 1.453(5) . ? Cl2 O24B 1.467(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N1 166.27(10) . . ? N3 Cu1 N4 88.33(10) . . ? N1 Cu1 N4 89.07(10) . . ? N3 Cu1 N2 88.58(10) . . ? N1 Cu1 N2 87.88(10) . . ? N4 Cu1 N2 154.03(6) . . ? N3 Cu1 O1 96.88(9) . . ? N1 Cu1 O1 96.85(9) . . ? N4 Cu1 O1 100.45(7) . . ? N2 Cu1 O1 105.52(8) . . ? C11 N1 C1 110.7(2) . . ? C11 N1 C8 114.1(2) . . ? C1 N1 C8 111.5(2) . . ? C11 N1 Cu1 110.88(18) . . ? C1 N1 Cu1 102.35(18) . . ? C8 N1 Cu1 106.58(18) . . ? C3 N2 C2 115.8(2) . . ? C3 N2 Cu1 100.48(16) . . ? C2 N2 Cu1 108.24(17) . . ? C3 N2 HN2 110.1 . . ? C2 N2 HN2 105.5 . . ? Cu1 N2 HN2 117.0 . . ? C5 N3 C4 111.9(2) . . ? C5 N3 C31 110.8(2) . . ? C4 N3 C31 113.0(2) . . ? C5 N3 Cu1 102.67(18) . . ? C4 N3 Cu1 107.38(18) . . ? C31 N3 Cu1 110.51(18) . . ? C7 N4 C6 117.6(2) . . ? C7 N4 Cu1 101.14(17) . . ? C6 N4 Cu1 108.10(16) . . ? C7 N4 HN4 108.9 . . ? C6 N4 HN4 109.1 . . ? Cu1 N4 HN4 111.8 . . ? C37 O1 C17 122.1(2) . . ? C37 O1 Cu1 117.63(17) . . ? C17 O1 Cu1 119.59(17) . . ? N1 C1 C2 110.5(3) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? N2 C2 C1 110.3(2) . . ? N2 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? N2 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N2 C3 C4 107.3(2) . . ? N2 C3 H3A 110.3 . . ? C4 C3 H3A 110.3 . . ? N2 C3 H3B 110.3 . . ? C4 C3 H3B 110.3 . . ? H3A C3 H3B 108.5 . . ? N3 C4 C3 109.0(2) . . ? N3 C4 H4A 109.9 . . ? C3 C4 H4A 109.9 . . ? N3 C4 H4B 109.9 . . ? C3 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N3 C5 C6 111.2(2) . . ? N3 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N3 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N4 C6 C5 110.3(2) . . ? N4 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N4 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N4 C7 C8 107.4(2) . . ? N4 C7 H7A 110.2 . . ? C8 C7 H7A 110.2 . . ? N4 C7 H7B 110.2 . . ? C8 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? N1 C8 C7 109.7(2) . . ? N1 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N1 C11 C12 115.5(3) . . ? N1 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? N1 C11 H11B 108.4 . . ? C12 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C17 115.9(3) . . ? C13 C12 C11 118.8(3) . . ? C17 C12 C11 125.2(3) . . ? C14 C13 C12 122.5(3) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C15 C14 C13 119.4(3) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 119.7(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C12 122.4(3) . . ? C16 C17 O1 120.3(3) . . ? C12 C17 O1 117.2(3) . . ? N3 C31 C32 114.6(2) . . ? N3 C31 H31A 108.6 . . ? C32 C31 H31A 108.6 . . ? N3 C31 H31B 108.6 . . ? C32 C31 H31B 108.6 . . ? H31A C31 H31B 107.6 . . ? C33 C32 C37 117.1(3) . . ? C33 C32 C31 118.9(3) . . ? C37 C32 C31 123.8(3) . . ? C34 C33 C32 122.3(3) . . ? C34 C33 H33 118.9 . . ? C32 C33 H33 118.9 . . ? C33 C34 C35 119.3(3) . . ? C33 C34 H34 120.4 . . ? C35 C34 H34 120.4 . . ? C36 C35 C34 119.9(3) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C37 C36 C35 119.5(3) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C36 C37 C32 121.8(3) . . ? C36 C37 O1 121.8(3) . . ? C32 C37 O1 116.4(3) . . ? O12 Cl1 O11 110.27(16) . . ? O12 Cl1 O14 109.81(16) . . ? O11 Cl1 O14 109.91(14) . . ? O12 Cl1 O13 108.85(17) . . ? O11 Cl1 O13 109.17(16) . . ? O14 Cl1 O13 108.80(15) . . ? O21B Cl2 O23B 113.3(4) . . ? O23A Cl2 O22A 110.9(4) . . ? O21B Cl2 O22B 110.7(4) . . ? O23B Cl2 O22B 110.7(4) . . ? O23A Cl2 O21A 109.0(5) . . ? O22A Cl2 O21A 108.0(4) . . ? O23A Cl2 O24A 112.5(4) . . ? O22A Cl2 O24A 108.5(3) . . ? O21A Cl2 O24A 107.8(4) . . ? O21B Cl2 O24B 106.5(4) . . ? O23B Cl2 O24B 110.9(4) . . ? O22B Cl2 O24B 104.2(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 N3 Cu1 N1 C11 159.0(4) . . . . ? N4 Cu1 N1 C11 -121.91(19) . . . . ? N2 Cu1 N1 C11 83.88(19) . . . . ? O1 Cu1 N1 C11 -21.5(2) . . . . ? N3 Cu1 N1 C1 41.0(5) . . . . ? N4 Cu1 N1 C1 120.06(18) . . . . ? N2 Cu1 N1 C1 -34.15(18) . . . . ? O1 Cu1 N1 C1 -139.53(18) . . . . ? N3 Cu1 N1 C8 -76.2(5) . . . . ? N4 Cu1 N1 C8 2.87(18) . . . . ? N2 Cu1 N1 C8 -151.34(19) . . . . ? O1 Cu1 N1 C8 103.28(19) . . . . ? N3 Cu1 N2 C3 -31.25(17) . . . . ? N1 Cu1 N2 C3 135.49(17) . . . . ? N4 Cu1 N2 C3 52.0(3) . . . . ? O1 Cu1 N2 C3 -127.99(15) . . . . ? N3 Cu1 N2 C2 -153.07(19) . . . . ? N1 Cu1 N2 C2 13.66(19) . . . . ? N4 Cu1 N2 C2 -69.8(3) . . . . ? O1 Cu1 N2 C2 110.18(18) . . . . ? N1 Cu1 N3 C5 46.7(5) . . . . ? N4 Cu1 N3 C5 -32.43(17) . . . . ? N2 Cu1 N3 C5 121.78(17) . . . . ? O1 Cu1 N3 C5 -132.76(18) . . . . ? N1 Cu1 N3 C4 -71.4(5) . . . . ? N4 Cu1 N3 C4 -150.55(18) . . . . ? N2 Cu1 N3 C4 3.67(18) . . . . ? O1 Cu1 N3 C4 109.13(19) . . . . ? N1 Cu1 N3 C31 164.9(4) . . . . ? N4 Cu1 N3 C31 85.76(19) . . . . ? N2 Cu1 N3 C31 -120.02(19) . . . . ? O1 Cu1 N3 C31 -14.6(2) . . . . ? N3 Cu1 N4 C7 136.30(16) . . . . ? N1 Cu1 N4 C7 -30.22(16) . . . . ? N2 Cu1 N4 C7 53.0(3) . . . . ? O1 Cu1 N4 C7 -127.01(15) . . . . ? N3 Cu1 N4 C6 12.18(18) . . . . ? N1 Cu1 N4 C6 -154.34(18) . . . . ? N2 Cu1 N4 C6 -71.1(3) . . . . ? O1 Cu1 N4 C6 108.87(17) . . . . ? N3 Cu1 O1 C37 -31.5(2) . . . . ? N1 Cu1 O1 C37 148.6(2) . . . . ? N4 Cu1 O1 C37 -121.1(2) . . . . ? N2 Cu1 O1 C37 58.9(2) . . . . ? N3 Cu1 O1 C17 157.7(2) . . . . ? N1 Cu1 O1 C17 -22.2(2) . . . . ? N4 Cu1 O1 C17 68.1(2) . . . . ? N2 Cu1 O1 C17 -111.9(2) . . . . ? C11 N1 C1 C2 -69.6(3) . . . . ? C8 N1 C1 C2 162.2(3) . . . . ? Cu1 N1 C1 C2 48.6(3) . . . . ? C3 N2 C2 C1 -101.1(3) . . . . ? Cu1 N2 C2 C1 10.7(3) . . . . ? N1 C1 C2 N2 -40.4(4) . . . . ? C2 N2 C3 C4 168.6(2) . . . . ? Cu1 N2 C3 C4 52.3(2) . . . . ? C5 N3 C4 C3 -86.7(3) . . . . ? C31 N3 C4 C3 147.4(2) . . . . ? Cu1 N3 C4 C3 25.3(3) . . . . ? N2 C3 C4 N3 -53.8(3) . . . . ? C4 N3 C5 C6 162.1(2) . . . . ? C31 N3 C5 C6 -70.8(3) . . . . ? Cu1 N3 C5 C6 47.2(3) . . . . ? C7 N4 C6 C5 -102.0(3) . . . . ? Cu1 N4 C6 C5 11.6(3) . . . . ? N3 C5 C6 N4 -40.1(3) . . . . ? C6 N4 C7 C8 168.3(2) . . . . ? Cu1 N4 C7 C8 50.9(2) . . . . ? C11 N1 C8 C7 148.3(3) . . . . ? C1 N1 C8 C7 -85.4(3) . . . . ? Cu1 N1 C8 C7 25.6(3) . . . . ? N4 C7 C8 N1 -53.1(3) . . . . ? C1 N1 C11 C12 173.6(2) . . . . ? C8 N1 C11 C12 -59.7(3) . . . . ? Cu1 N1 C11 C12 60.7(3) . . . . ? N1 C11 C12 C13 121.7(3) . . . . ? N1 C11 C12 C17 -62.6(4) . . . . ? C17 C12 C13 C14 -1.5(5) . . . . ? C11 C12 C13 C14 174.5(3) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? C14 C15 C16 C17 -1.3(5) . . . . ? C15 C16 C17 C12 0.8(5) . . . . ? C15 C16 C17 O1 177.5(3) . . . . ? C13 C12 C17 C16 0.6(5) . . . . ? C11 C12 C17 C16 -175.2(3) . . . . ? C13 C12 C17 O1 -176.2(3) . . . . ? C11 C12 C17 O1 8.0(4) . . . . ? C37 O1 C17 C16 43.5(4) . . . . ? Cu1 O1 C17 C16 -146.1(2) . . . . ? C37 O1 C17 C12 -139.6(3) . . . . ? Cu1 O1 C17 C12 30.8(3) . . . . ? C5 N3 C31 C32 171.9(2) . . . . ? C4 N3 C31 C32 -61.6(3) . . . . ? Cu1 N3 C31 C32 58.8(3) . . . . ? N3 C31 C32 C33 115.9(3) . . . . ? N3 C31 C32 C37 -68.9(4) . . . . ? C37 C32 C33 C34 -3.5(5) . . . . ? C31 C32 C33 C34 172.0(3) . . . . ? C32 C33 C34 C35 0.9(5) . . . . ? C33 C34 C35 C36 1.6(5) . . . . ? C34 C35 C36 C37 -1.3(5) . . . . ? C35 C36 C37 C32 -1.6(5) . . . . ? C35 C36 C37 O1 175.3(3) . . . . ? C33 C32 C37 C36 3.9(5) . . . . ? C31 C32 C37 C36 -171.4(3) . . . . ? C33 C32 C37 O1 -173.2(3) . . . . ? C31 C32 C37 O1 11.5(4) . . . . ? C17 O1 C37 C36 28.7(4) . . . . ? Cu1 O1 C37 C36 -141.9(3) . . . . ? C17 O1 C37 C32 -154.3(3) . . . . ? Cu1 O1 C37 C32 35.1(3) . . . . ? 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 N2 HN2 O13 1.01 2.05 3.034(3) 163.2 1_554 N4 HN4 O24B 1.01 2.23 3.129(8) 148.1 . N4 HN4 O22A 1.01 2.26 3.058(7) 135.2 . N4 HN4 O22B 1.01 2.30 3.154(7) 141.2 . N4 HN4 O23A 1.01 2.45 3.387(10) 154.7 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.599 _refine_diff_density_min -0.724 _refine_diff_density_rms 0.092