# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H7 N4 O7 Zn2, O' _chemical_formula_sum 'C15 H7 N4 O8 Zn2' _chemical_formula_weight 502.03 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' Zn Zn 0.2839 1.4301 '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 8.4724(15) _cell_length_b 9.3461(17) _cell_length_c 11.4906(19) _cell_angle_alpha 82.012(2) _cell_angle_beta 76.920(2) _cell_angle_gamma 69.835(2) _cell_volume 830.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour ORANGE _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.009 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 2.948 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4717 _exptl_absorpt_correction_T_max 0.6190 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4182 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2878 _reflns_number_gt 2687 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+1.1599P] 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 2878 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 O8 O 0.423(5) 0.113(6) 0.120(4) 0.98(7) Uani 1 1 d . . . C1 C 0.4522(5) -0.2410(4) 0.3520(3) 0.0263(8) Uani 1 1 d . . . C2 C 0.3776(4) -0.1530(4) 0.4612(3) 0.0218(7) Uani 1 1 d . . . C3 C 0.3662(4) -0.2251(4) 0.5747(3) 0.0223(7) Uani 1 1 d . . . H1 H 0.4002 -0.3312 0.5850 0.027 Uiso 1 1 calc R . . C4 C 0.3033(4) -0.1368(4) 0.6733(3) 0.0220(7) Uani 1 1 d . . . C5 C 0.2467(5) 0.0209(4) 0.6576(3) 0.0238(7) Uani 1 1 d . . . H2 H 0.2014 0.0796 0.7237 0.029 Uiso 1 1 calc R . . C6 C 0.2576(4) 0.0907(4) 0.5442(3) 0.0217(7) Uani 1 1 d . . . C7 C 0.3233(4) 0.0051(4) 0.4453(3) 0.0230(7) Uani 1 1 d . . . H3 H 0.3311 0.0529 0.3687 0.028 Uiso 1 1 calc R . . C8 C 0.2963(4) -0.2085(4) 0.7972(3) 0.0228(7) Uani 1 1 d . . . C9 C 0.1559(4) 0.3304(4) 0.4361(3) 0.0226(7) Uani 1 1 d . . . C10 C 0.0444(5) 0.2952(4) 0.3820(4) 0.0298(8) Uani 1 1 d . . . H4 H 0.0104 0.2100 0.4099 0.036 Uiso 1 1 calc R . . C11 C -0.0145(5) 0.3868(4) 0.2875(4) 0.0293(8) Uani 1 1 d . . . H5 H -0.0866 0.3618 0.2496 0.035 Uiso 1 1 calc R . . C12 C 0.0307(4) 0.5168(4) 0.2466(3) 0.0229(7) Uani 1 1 d . . . C13 C 0.1405(5) 0.5516(4) 0.3037(3) 0.0260(7) Uani 1 1 d . . . H6 H 0.1717 0.6386 0.2781 0.031 Uiso 1 1 calc R . . C14 C 0.2025(5) 0.4579(4) 0.3974(3) 0.0262(8) Uani 1 1 d . . . H7 H 0.2765 0.4810 0.4348 0.031 Uiso 1 1 calc R . . C15 C -0.0390(4) 0.6142(4) 0.1473(3) 0.0217(7) Uani 1 1 d . . . N1 N -0.1865(4) 0.6227(3) 0.1171(3) 0.0260(6) Uani 1 1 d . . . N2 N -0.2041(4) 0.7226(4) 0.0209(3) 0.0316(7) Uani 1 1 d . . . N3 N -0.0751(4) 0.7725(4) -0.0069(3) 0.0307(7) Uani 1 1 d . . . N4 N 0.0322(4) 0.7059(3) 0.0705(3) 0.0252(6) Uani 1 1 d . . . O1 O 0.4515(4) -0.3749(3) 0.0709(3) 0.0487(9) Uani 1 1 d . . . O2 O 0.4551(4) -0.1713(4) 0.2516(2) 0.0440(7) Uani 1 1 d . . . O3 O 0.5123(4) -0.3849(3) 0.3625(2) 0.0311(6) Uani 1 1 d . . . O4 O 0.3379(4) -0.3500(3) 0.8160(2) 0.0322(6) Uani 1 1 d . . . O5 O 0.2455(4) -0.1217(3) 0.8813(2) 0.0343(6) Uani 1 1 d . . . O6 O 0.2125(3) 0.2479(3) 0.5361(2) 0.0276(6) Uani 1 1 d . . . O7 O 0.1761(4) 0.9404(3) 0.1464(3) 0.0356(6) Uani 1 1 d . . . Zn1 Zn 0.59285(5) -0.42281(4) 0.18914(3) 0.02180(15) Uani 1 1 d . . . Zn2 Zn 0.24389(5) 0.76910(5) 0.03901(4) 0.02532(16) 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 O8 0.89(8) 1.34(12) 1.05(10) 0.91(10) -0.83(9) -0.76(8) C1 0.0254(18) 0.034(2) 0.0231(19) -0.0030(15) -0.0086(14) -0.0111(15) C2 0.0216(17) 0.0276(18) 0.0183(17) -0.0002(13) -0.0092(13) -0.0079(14) C3 0.0252(17) 0.0211(17) 0.0217(18) 0.0006(13) -0.0069(14) -0.0081(14) C4 0.0236(17) 0.0247(17) 0.0192(17) 0.0033(13) -0.0059(13) -0.0103(14) C5 0.0282(18) 0.0244(18) 0.0195(17) -0.0009(14) -0.0075(14) -0.0075(14) C6 0.0226(17) 0.0187(16) 0.0234(18) 0.0040(13) -0.0098(13) -0.0047(13) C7 0.0258(17) 0.0270(18) 0.0174(17) 0.0049(13) -0.0112(13) -0.0081(14) C8 0.0254(17) 0.0236(18) 0.0211(18) 0.0037(14) -0.0084(14) -0.0096(14) C9 0.0244(17) 0.0213(17) 0.0180(17) 0.0032(13) -0.0072(14) -0.0021(13) C10 0.032(2) 0.0269(19) 0.036(2) 0.0100(16) -0.0141(16) -0.0169(16) C11 0.032(2) 0.0268(19) 0.034(2) 0.0062(16) -0.0171(16) -0.0123(16) C12 0.0231(17) 0.0224(17) 0.0225(18) 0.0034(13) -0.0075(14) -0.0062(13) C13 0.0319(19) 0.0261(18) 0.0237(18) 0.0059(14) -0.0088(14) -0.0146(15) C14 0.0288(18) 0.0284(18) 0.0244(18) 0.0027(14) -0.0107(15) -0.0113(15) C15 0.0230(17) 0.0237(17) 0.0186(17) 0.0016(13) -0.0060(13) -0.0078(14) N1 0.0281(16) 0.0285(16) 0.0230(15) 0.0088(12) -0.0119(12) -0.0107(13) N2 0.0331(17) 0.0390(18) 0.0261(17) 0.0135(13) -0.0157(13) -0.0156(15) N3 0.0349(17) 0.0328(17) 0.0263(16) 0.0127(13) -0.0140(13) -0.0139(14) N4 0.0268(16) 0.0289(16) 0.0222(16) 0.0084(12) -0.0112(12) -0.0117(13) O1 0.0476(18) 0.0444(17) 0.0494(19) -0.0244(15) -0.0359(15) 0.0159(14) O2 0.063(2) 0.0427(17) 0.0196(14) -0.0028(12) -0.0099(13) -0.0079(15) O3 0.0416(15) 0.0269(14) 0.0240(13) -0.0057(11) -0.0036(11) -0.0104(12) O4 0.0508(17) 0.0192(13) 0.0290(14) 0.0067(10) -0.0189(12) -0.0106(12) O5 0.0577(18) 0.0269(13) 0.0156(12) 0.0034(10) -0.0058(12) -0.0128(12) O6 0.0434(15) 0.0199(12) 0.0197(13) 0.0041(10) -0.0144(11) -0.0075(11) O7 0.0460(17) 0.0330(15) 0.0278(14) -0.0003(11) -0.0131(12) -0.0098(13) Zn1 0.0248(2) 0.0238(2) 0.0178(2) 0.00111(16) -0.00822(16) -0.00765(18) Zn2 0.0266(3) 0.0286(3) 0.0200(2) 0.00531(17) -0.00908(17) -0.00777(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 C1 O2 1.244(5) . ? C1 O3 1.262(5) . ? C1 C2 1.490(5) . ? C2 C3 1.381(5) . ? C2 C7 1.386(5) . ? C3 C4 1.391(5) . ? C3 H1 0.9300 . ? C4 C5 1.383(5) . ? C4 C8 1.484(5) . ? C5 C6 1.372(5) . ? C5 H2 0.9300 . ? C6 C7 1.378(5) . ? C6 O6 1.380(4) . ? C7 H3 0.9300 . ? C8 O4 1.246(4) . ? C8 O5 1.252(4) . ? C9 C14 1.368(5) . ? C9 O6 1.376(4) . ? C9 C10 1.388(5) . ? C10 C11 1.361(5) . ? C10 H4 0.9300 . ? C11 C12 1.387(5) . ? C11 H5 0.9300 . ? C12 C13 1.394(5) . ? C12 C15 1.459(5) . ? C13 C14 1.371(5) . ? C13 H6 0.9300 . ? C14 H7 0.9300 . ? C15 N4 1.335(4) . ? C15 N1 1.345(5) . ? N1 N2 1.345(4) . ? N1 Zn1 2.027(3) 1_465 ? N2 N3 1.290(5) . ? N3 N4 1.352(4) . ? N4 Zn2 2.018(3) . ? O1 Zn2 1.887(3) 1_545 ? O1 Zn1 1.918(3) . ? O2 Zn1 2.366(3) . ? O3 Zn1 1.993(3) . ? O4 Zn1 2.004(2) 2_646 ? O5 Zn2 1.952(3) 1_546 ? O7 Zn2 2.003(3) . ? Zn1 O4 2.004(2) 2_646 ? Zn1 N1 2.027(3) 1_645 ? Zn2 O1 1.887(3) 1_565 ? Zn2 O5 1.952(3) 1_564 ? 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 O2 C1 O3 120.9(3) . . ? O2 C1 C2 119.4(3) . . ? O3 C1 C2 119.8(3) . . ? C3 C2 C7 120.7(3) . . ? C3 C2 C1 121.6(3) . . ? C7 C2 C1 117.6(3) . . ? C2 C3 C4 119.0(3) . . ? C2 C3 H1 120.5 . . ? C4 C3 H1 120.5 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 C8 118.5(3) . . ? C3 C4 C8 121.2(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H2 120.1 . . ? C4 C5 H2 120.1 . . ? C5 C6 C7 120.6(3) . . ? C5 C6 O6 116.4(3) . . ? C7 C6 O6 122.8(3) . . ? C6 C7 C2 119.4(3) . . ? C6 C7 H3 120.3 . . ? C2 C7 H3 120.3 . . ? O4 C8 O5 121.6(3) . . ? O4 C8 C4 120.8(3) . . ? O5 C8 C4 117.5(3) . . ? C14 C9 O6 117.1(3) . . ? C14 C9 C10 120.6(3) . . ? O6 C9 C10 122.1(3) . . ? C11 C10 C9 119.1(3) . . ? C11 C10 H4 120.4 . . ? C9 C10 H4 120.4 . . ? C10 C11 C12 121.4(3) . . ? C10 C11 H5 119.3 . . ? C12 C11 H5 119.3 . . ? C11 C12 C13 118.5(3) . . ? C11 C12 C15 119.6(3) . . ? C13 C12 C15 121.8(3) . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H6 119.9 . . ? C12 C13 H6 119.9 . . ? C9 C14 C13 120.1(3) . . ? C9 C14 H7 119.9 . . ? C13 C14 H7 119.9 . . ? N4 C15 N1 108.9(3) . . ? N4 C15 C12 126.6(3) . . ? N1 C15 C12 124.5(3) . . ? N2 N1 C15 106.2(3) . . ? N2 N1 Zn1 111.6(2) . 1_465 ? C15 N1 Zn1 140.1(2) . 1_465 ? N3 N2 N1 109.5(3) . . ? N2 N3 N4 109.0(3) . . ? C15 N4 N3 106.4(3) . . ? C15 N4 Zn2 139.1(2) . . ? N3 N4 Zn2 114.5(2) . . ? Zn2 O1 Zn1 139.25(16) 1_545 . ? C1 O2 Zn1 81.6(2) . . ? C1 O3 Zn1 98.2(2) . . ? C8 O4 Zn1 168.5(3) . 2_646 ? C8 O5 Zn2 113.2(2) . 1_546 ? C9 O6 C6 119.8(3) . . ? O1 Zn1 O3 126.15(13) . . ? O1 Zn1 O4 95.57(12) . 2_646 ? O3 Zn1 O4 104.72(11) . 2_646 ? O1 Zn1 N1 109.42(14) . 1_645 ? O3 Zn1 N1 113.29(12) . 1_645 ? O4 Zn1 N1 103.30(12) 2_646 1_645 ? O1 Zn1 O2 88.87(11) . . ? O3 Zn1 O2 59.25(10) . . ? O4 Zn1 O2 161.91(11) 2_646 . ? N1 Zn1 O2 91.65(12) 1_645 . ? O1 Zn2 O5 118.02(14) 1_565 1_564 ? O1 Zn2 O7 108.23(12) 1_565 . ? O5 Zn2 O7 101.69(11) 1_564 . ? O1 Zn2 N4 119.15(14) 1_565 . ? O5 Zn2 N4 104.41(12) 1_564 . ? O7 Zn2 N4 103.02(13) . . ? 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 O2 C1 C2 C3 177.8(3) . . . . ? O3 C1 C2 C3 -2.5(5) . . . . ? O2 C1 C2 C7 -3.8(5) . . . . ? O3 C1 C2 C7 176.0(3) . . . . ? C7 C2 C3 C4 -1.6(5) . . . . ? C1 C2 C3 C4 176.8(3) . . . . ? C2 C3 C4 C5 2.5(5) . . . . ? C2 C3 C4 C8 -177.0(3) . . . . ? C3 C4 C5 C6 -2.0(5) . . . . ? C8 C4 C5 C6 177.5(3) . . . . ? C4 C5 C6 C7 0.5(5) . . . . ? C4 C5 C6 O6 -174.6(3) . . . . ? C5 C6 C7 C2 0.4(5) . . . . ? O6 C6 C7 C2 175.2(3) . . . . ? C3 C2 C7 C6 0.1(5) . . . . ? C1 C2 C7 C6 -178.3(3) . . . . ? C5 C4 C8 O4 176.5(3) . . . . ? C3 C4 C8 O4 -4.0(5) . . . . ? C5 C4 C8 O5 -2.8(5) . . . . ? C3 C4 C8 O5 176.7(3) . . . . ? C14 C9 C10 C11 1.8(6) . . . . ? O6 C9 C10 C11 176.2(3) . . . . ? C9 C10 C11 C12 -1.9(6) . . . . ? C10 C11 C12 C13 0.7(6) . . . . ? C10 C11 C12 C15 -178.3(4) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C15 C12 C13 C14 179.5(3) . . . . ? O6 C9 C14 C13 -175.3(3) . . . . ? C10 C9 C14 C13 -0.6(6) . . . . ? C12 C13 C14 C9 -0.6(6) . . . . ? C11 C12 C15 N4 -154.0(4) . . . . ? C13 C12 C15 N4 27.0(6) . . . . ? C11 C12 C15 N1 24.5(5) . . . . ? C13 C12 C15 N1 -154.5(4) . . . . ? N4 C15 N1 N2 -0.5(4) . . . . ? C12 C15 N1 N2 -179.2(3) . . . . ? N4 C15 N1 Zn1 -160.9(3) . . . 1_465 ? C12 C15 N1 Zn1 20.4(6) . . . 1_465 ? C15 N1 N2 N3 0.2(4) . . . . ? Zn1 N1 N2 N3 166.8(3) 1_465 . . . ? N1 N2 N3 N4 0.2(4) . . . . ? N1 C15 N4 N3 0.6(4) . . . . ? C12 C15 N4 N3 179.3(3) . . . . ? N1 C15 N4 Zn2 -179.1(3) . . . . ? C12 C15 N4 Zn2 -0.4(6) . . . . ? N2 N3 N4 C15 -0.5(4) . . . . ? N2 N3 N4 Zn2 179.3(3) . . . . ? O3 C1 O2 Zn1 -1.2(3) . . . . ? C2 C1 O2 Zn1 178.5(3) . . . . ? O2 C1 O3 Zn1 1.5(4) . . . . ? C2 C1 O3 Zn1 -178.3(3) . . . . ? O5 C8 O4 Zn1 171.5(11) . . . 2_646 ? C4 C8 O4 Zn1 -7.7(16) . . . 2_646 ? O4 C8 O5 Zn2 1.1(5) . . . 1_546 ? C4 C8 O5 Zn2 -179.7(2) . . . 1_546 ? C14 C9 O6 C6 -144.1(3) . . . . ? C10 C9 O6 C6 41.3(5) . . . . ? C5 C6 O6 C9 -154.9(3) . . . . ? C7 C6 O6 C9 30.1(5) . . . . ? Zn2 O1 Zn1 O3 30.1(4) 1_545 . . . ? Zn2 O1 Zn1 O4 142.9(3) 1_545 . . 2_646 ? Zn2 O1 Zn1 N1 -110.9(3) 1_545 . . 1_645 ? Zn2 O1 Zn1 O2 -19.6(3) 1_545 . . . ? C1 O3 Zn1 O1 -63.2(3) . . . . ? C1 O3 Zn1 O4 -171.6(2) . . . 2_646 ? C1 O3 Zn1 N1 76.5(2) . . . 1_645 ? C1 O3 Zn1 O2 -0.8(2) . . . . ? C1 O2 Zn1 O1 135.1(2) . . . . ? C1 O2 Zn1 O3 0.8(2) . . . . ? C1 O2 Zn1 O4 30.5(5) . . . 2_646 ? C1 O2 Zn1 N1 -115.5(2) . . . 1_645 ? C15 N4 Zn2 O1 33.8(4) . . . 1_565 ? N3 N4 Zn2 O1 -145.9(2) . . . 1_565 ? C15 N4 Zn2 O5 168.1(4) . . . 1_564 ? N3 N4 Zn2 O5 -11.6(3) . . . 1_564 ? C15 N4 Zn2 O7 -86.0(4) . . . . ? N3 N4 Zn2 O7 94.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.793 _refine_diff_density_min -0.758 _refine_diff_density_rms 0.118 _database_code_depnum_ccdc_archive 'CCDC 958312' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H7 Cd2 N4 O8, O' _chemical_formula_sum 'C15 H7 Cd2 N4 O9' _chemical_formula_weight 612.07 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' Cd Cd -0.8075 1.2024 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1794(9) _cell_length_b 9.4600(9) _cell_length_c 11.1538(10) _cell_angle_alpha 90.7260(10) _cell_angle_beta 100.2520(10) _cell_angle_gamma 105.2650(10) _cell_volume 917.66(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 586 _exptl_absorpt_coefficient_mu 2.377 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6478 _exptl_absorpt_correction_T_max 0.7169 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4689 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3216 _reflns_number_gt 2763 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0267P)^2^+1.2243P] 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 3216 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0244 _refine_ls_wR_factor_ref 0.0604 _refine_ls_wR_factor_gt 0.0570 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.0761(5) -0.2357(4) 0.3034(4) 0.0255(9) Uani 1 1 d . . . C2 C 0.1338(4) -0.1375(4) 0.4176(3) 0.0206(8) Uani 1 1 d . . . C3 C 0.1479(4) -0.1952(4) 0.5301(3) 0.0236(8) Uani 1 1 d . . . H3 H 0.1260 -0.2964 0.5352 0.028 Uiso 1 1 calc R . . C4 C 0.1945(4) -0.1039(4) 0.6368(3) 0.0226(8) Uani 1 1 d . . . C5 C 0.2286(4) 0.0471(4) 0.6288(3) 0.0232(8) Uani 1 1 d . . . H5 H 0.2594 0.1092 0.6992 0.028 Uiso 1 1 calc R . . C6 C 0.2163(4) 0.1046(4) 0.5153(4) 0.0233(8) Uani 1 1 d . . . C7 C 0.1675(4) 0.0143(4) 0.4099(3) 0.0249(8) Uani 1 1 d . . . H7 H 0.1572 0.0543 0.3341 0.030 Uiso 1 1 calc R . . C8 C 0.1993(4) -0.1691(4) 0.7594(3) 0.0246(8) Uani 1 1 d . . . C9 C 0.3537(4) 0.3536(4) 0.5791(3) 0.0239(8) Uani 1 1 d . . . C10 C 0.3260(5) 0.4855(4) 0.6033(4) 0.0381(11) Uani 1 1 d . . . H10 H 0.2314 0.5017 0.5714 0.046 Uiso 1 1 calc R . . C11 C 0.4400(5) 0.5944(5) 0.6755(4) 0.0388(11) Uani 1 1 d . . . H11 H 0.4220 0.6846 0.6905 0.047 Uiso 1 1 calc R . . C12 C 0.5794(4) 0.5713(4) 0.7253(3) 0.0236(8) Uani 1 1 d . . . C13 C 0.6041(5) 0.4372(4) 0.6990(4) 0.0360(11) Uani 1 1 d . . . H13 H 0.6979 0.4198 0.7315 0.043 Uiso 1 1 calc R . . C14 C 0.4919(5) 0.3281(5) 0.6252(4) 0.0379(11) Uani 1 1 d . . . H14 H 0.5105 0.2388 0.6073 0.046 Uiso 1 1 calc R . . C15 C 0.6978(4) 0.6869(4) 0.8040(3) 0.0227(8) Uani 1 1 d . . . Cd1 Cd 0.16276(3) -0.13385(3) 0.03213(2) 0.02312(9) Uani 1 1 d . . . Cd2 Cd -0.00304(3) -0.52291(3) 0.15004(2) 0.02529(9) Uani 1 1 d . . . N1 N 0.6724(4) 0.8115(3) 0.8424(3) 0.0267(7) Uani 1 1 d . . . N2 N 0.8067(4) 0.8872(3) 0.9112(3) 0.0254(7) Uani 1 1 d . . . N3 N 0.9077(4) 0.8117(3) 0.9152(3) 0.0250(7) Uani 1 1 d . . . N4 N 0.8424(4) 0.6844(3) 0.8473(3) 0.0235(7) Uani 1 1 d . . . O1 O 0.0406(3) -0.1795(3) 0.2039(2) 0.0341(7) Uani 1 1 d . . . O2 O 0.0626(3) -0.3709(3) 0.3140(2) 0.0320(7) Uani 1 1 d . . . O3 O 0.1556(3) -0.3061(3) 0.7580(3) 0.0354(7) Uani 1 1 d . . . O4 O 0.2464(4) -0.0823(3) 0.8535(3) 0.0387(7) Uani 1 1 d . . . O5 O 0.2374(3) 0.2536(3) 0.5000(3) 0.0325(7) Uani 1 1 d . . . O6 O 0.4065(4) -0.0944(4) 0.1516(4) 0.0669(11) Uani 1 1 d . . . O7 O 0.1416(3) -0.3749(3) 0.0313(2) 0.0230(6) Uani 1 1 d . . . O8 O -0.2412(4) -0.3904(4) 0.1247(4) 0.0651(11) Uani 1 1 d . . . O9 O 0.4773(5) 0.6854(6) 0.0264(4) 0.0927(16) 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 C1 0.030(2) 0.022(2) 0.024(2) -0.0043(16) 0.0068(17) 0.0047(16) C2 0.0221(19) 0.0171(18) 0.020(2) -0.0027(15) 0.0038(15) 0.0007(15) C3 0.026(2) 0.0208(19) 0.024(2) -0.0023(15) 0.0054(16) 0.0057(16) C4 0.023(2) 0.023(2) 0.021(2) 0.0019(15) 0.0042(16) 0.0051(16) C5 0.024(2) 0.0204(19) 0.023(2) -0.0054(15) 0.0037(16) 0.0030(16) C6 0.024(2) 0.0151(18) 0.028(2) 0.0006(15) 0.0013(16) 0.0025(15) C7 0.027(2) 0.025(2) 0.020(2) 0.0027(16) 0.0039(16) 0.0031(16) C8 0.024(2) 0.027(2) 0.022(2) 0.0039(16) 0.0067(16) 0.0029(16) C9 0.027(2) 0.0153(18) 0.022(2) -0.0006(15) -0.0025(16) -0.0037(15) C10 0.027(2) 0.025(2) 0.056(3) -0.004(2) -0.010(2) 0.0086(18) C11 0.032(2) 0.022(2) 0.058(3) -0.015(2) -0.005(2) 0.0090(18) C12 0.026(2) 0.0173(18) 0.024(2) -0.0019(15) 0.0029(16) 0.0015(15) C13 0.025(2) 0.026(2) 0.050(3) -0.0085(19) -0.0101(19) 0.0054(18) C14 0.037(3) 0.021(2) 0.052(3) -0.0135(19) -0.002(2) 0.0086(19) C15 0.028(2) 0.0171(19) 0.021(2) 0.0009(15) 0.0038(16) 0.0032(16) Cd1 0.03149(17) 0.01528(15) 0.01895(16) -0.00100(10) 0.00117(12) 0.00246(11) Cd2 0.03736(18) 0.01671(15) 0.01849(16) -0.00163(11) 0.00566(12) 0.00140(12) N1 0.0276(18) 0.0192(16) 0.0284(19) -0.0067(14) -0.0001(14) 0.0016(14) N2 0.0299(18) 0.0189(16) 0.0244(18) -0.0024(13) 0.0007(14) 0.0043(14) N3 0.0291(18) 0.0190(16) 0.0231(18) -0.0025(13) 0.0016(14) 0.0023(14) N4 0.0286(18) 0.0134(15) 0.0244(18) -0.0030(13) -0.0006(14) 0.0028(13) O1 0.0491(19) 0.0301(16) 0.0207(15) 0.0005(12) 0.0041(13) 0.0086(14) O2 0.0488(18) 0.0219(15) 0.0227(15) -0.0060(11) 0.0029(13) 0.0083(13) O3 0.0505(19) 0.0241(16) 0.0328(17) 0.0078(12) 0.0165(14) 0.0061(13) O4 0.054(2) 0.0365(17) 0.0208(15) -0.0004(13) 0.0101(14) 0.0014(14) O5 0.0409(17) 0.0147(13) 0.0311(16) 0.0000(11) -0.0110(13) 0.0007(12) O6 0.051(2) 0.053(2) 0.079(3) 0.007(2) -0.026(2) 0.0088(18) O7 0.0290(14) 0.0155(13) 0.0217(14) 0.0009(10) 0.0038(11) 0.0017(11) O8 0.064(3) 0.061(2) 0.064(3) 0.003(2) 0.007(2) 0.009(2) O9 0.071(3) 0.142(5) 0.080(3) 0.031(3) 0.032(3) 0.042(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.262(4) . ? C1 O1 1.264(5) . ? C1 C2 1.496(5) . ? C2 C3 1.374(5) . ? C2 C7 1.394(5) . ? C3 C4 1.394(5) . ? C3 H3 0.9300 . ? C4 C5 1.387(5) . ? C4 C8 1.505(5) . ? C5 C6 1.382(5) . ? C5 H5 0.9300 . ? C6 C7 1.377(5) . ? C6 O5 1.388(4) . ? C7 H7 0.9300 . ? C8 O3 1.251(5) . ? C8 O4 1.262(5) . ? C9 C14 1.365(6) . ? C9 C10 1.370(5) . ? C9 O5 1.387(4) . ? C10 C11 1.384(6) . ? C10 H10 0.9300 . ? C11 C12 1.375(6) . ? C11 H11 0.9300 . ? C12 C13 1.383(5) . ? C12 C15 1.469(5) . ? C13 C14 1.386(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 N4 1.336(5) . ? C15 N1 1.339(5) . ? Cd1 O7 2.237(2) . ? Cd1 O4 2.274(3) 1_554 ? Cd1 O6 2.326(3) . ? Cd1 N2 2.340(3) 2_666 ? Cd1 O1 2.376(3) . ? Cd1 N3 2.389(3) 1_444 ? Cd1 Cd2 3.6176(4) 2_545 ? Cd2 O2 2.205(3) . ? Cd2 O3 2.234(3) 2_546 ? Cd2 O7 2.243(2) 2_545 ? Cd2 O7 2.274(2) . ? Cd2 N4 2.383(3) 2_656 ? Cd2 O8 2.768(4) . ? Cd2 Cd2 3.3888(6) 2_545 ? Cd2 Cd1 3.6176(4) 2_545 ? N1 N2 1.344(4) . ? N2 N3 1.306(4) . ? N2 Cd1 2.340(3) 2_666 ? N3 N4 1.349(4) . ? N3 Cd1 2.389(3) 1_666 ? N4 Cd2 2.383(3) 2_656 ? O3 Cd2 2.234(3) 2_546 ? O4 Cd1 2.274(3) 1_556 ? O7 Cd2 2.243(2) 2_545 ? 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 O2 C1 O1 124.4(4) . . ? O2 C1 C2 117.0(3) . . ? O1 C1 C2 118.5(3) . . ? C3 C2 C7 119.6(3) . . ? C3 C2 C1 120.8(3) . . ? C7 C2 C1 119.6(3) . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.4(3) . . ? C5 C4 C8 120.4(3) . . ? C3 C4 C8 120.1(3) . . ? C6 C5 C4 119.5(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C7 C6 C5 121.1(3) . . ? C7 C6 O5 115.9(3) . . ? C5 C6 O5 122.8(3) . . ? C6 C7 C2 119.6(4) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? O3 C8 O4 125.9(4) . . ? O3 C8 C4 116.2(3) . . ? O4 C8 C4 117.9(3) . . ? C14 C9 C10 121.0(3) . . ? C14 C9 O5 123.0(3) . . ? C10 C9 O5 115.9(3) . . ? C9 C10 C11 119.4(4) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 121.1(4) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 118.1(4) . . ? C11 C12 C15 120.4(3) . . ? C13 C12 C15 121.5(4) . . ? C12 C13 C14 121.4(4) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C9 C14 C13 119.0(4) . . ? C9 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? N4 C15 N1 110.7(3) . . ? N4 C15 C12 126.2(3) . . ? N1 C15 C12 123.2(3) . . ? O7 Cd1 O4 99.99(10) . 1_554 ? O7 Cd1 O6 88.32(11) . . ? O4 Cd1 O6 95.49(13) 1_554 . ? O7 Cd1 N2 164.82(10) . 2_666 ? O4 Cd1 N2 93.73(11) 1_554 2_666 ? O6 Cd1 N2 83.91(12) . 2_666 ? O7 Cd1 O1 83.43(9) . . ? O4 Cd1 O1 171.30(11) 1_554 . ? O6 Cd1 O1 92.60(13) . . ? N2 Cd1 O1 83.92(10) 2_666 . ? O7 Cd1 N3 88.70(10) . 1_444 ? O4 Cd1 N3 86.87(11) 1_554 1_444 ? O6 Cd1 N3 176.48(12) . 1_444 ? N2 Cd1 N3 98.57(10) 2_666 1_444 ? O1 Cd1 N3 85.20(10) . 1_444 ? O7 Cd1 Cd2 36.20(6) . 2_545 ? O4 Cd1 Cd2 76.85(7) 1_554 2_545 ? O6 Cd1 Cd2 117.80(10) . 2_545 ? N2 Cd1 Cd2 156.74(8) 2_666 2_545 ? O1 Cd1 Cd2 102.16(7) . 2_545 ? N3 Cd1 Cd2 60.17(7) 1_444 2_545 ? O2 Cd2 O3 91.66(10) . 2_546 ? O2 Cd2 O7 156.38(10) . 2_545 ? O3 Cd2 O7 89.18(10) 2_546 2_545 ? O2 Cd2 O7 97.25(10) . . ? O3 Cd2 O7 171.08(10) 2_546 . ? O7 Cd2 O7 82.77(9) 2_545 . ? O2 Cd2 N4 112.58(10) . 2_656 ? O3 Cd2 N4 87.19(11) 2_546 2_656 ? O7 Cd2 N4 91.04(10) 2_545 2_656 ? O7 Cd2 N4 89.10(10) . 2_656 ? O2 Cd2 O8 77.57(11) . . ? O3 Cd2 O8 84.60(11) 2_546 . ? O7 Cd2 O8 79.02(10) 2_545 . ? O7 Cd2 O8 97.58(10) . . ? N4 Cd2 O8 167.17(11) 2_656 . ? O2 Cd2 Cd2 133.72(7) . 2_545 ? O3 Cd2 Cd2 130.80(8) 2_546 2_545 ? O7 Cd2 Cd2 41.73(6) 2_545 2_545 ? O7 Cd2 Cd2 41.04(6) . 2_545 ? N4 Cd2 Cd2 90.09(8) 2_656 2_545 ? O8 Cd2 Cd2 87.85(8) . 2_545 ? O2 Cd2 Cd1 157.92(7) . 2_545 ? O3 Cd2 Cd1 66.96(7) 2_546 2_545 ? O7 Cd2 Cd1 36.10(6) 2_545 2_545 ? O7 Cd2 Cd1 104.14(6) . 2_545 ? N4 Cd2 Cd1 63.01(7) 2_656 2_545 ? O8 Cd2 Cd1 104.57(8) . 2_545 ? Cd2 Cd2 Cd1 68.230(10) 2_545 2_545 ? C15 N1 N2 105.1(3) . . ? N3 N2 N1 109.7(3) . . ? N3 N2 Cd1 130.8(2) . 2_666 ? N1 N2 Cd1 118.2(2) . 2_666 ? N2 N3 N4 109.1(3) . . ? N2 N3 Cd1 128.8(2) . 1_666 ? N4 N3 Cd1 122.0(2) . 1_666 ? C15 N4 N3 105.4(3) . . ? C15 N4 Cd2 139.6(2) . 2_656 ? N3 N4 Cd2 114.8(2) . 2_656 ? C1 O1 Cd1 131.7(3) . . ? C1 O2 Cd2 120.0(2) . . ? C8 O3 Cd2 138.1(3) . 2_546 ? C8 O4 Cd1 122.8(3) . 1_556 ? C9 O5 C6 119.0(3) . . ? Cd1 O7 Cd2 107.70(10) . 2_545 ? Cd1 O7 Cd2 121.41(11) . . ? Cd2 O7 Cd2 97.23(9) 2_545 . ? 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 O2 C1 C2 C3 -9.9(6) . . . . ? O1 C1 C2 C3 168.3(4) . . . . ? O2 C1 C2 C7 172.8(4) . . . . ? O1 C1 C2 C7 -9.0(6) . . . . ? C7 C2 C3 C4 0.4(6) . . . . ? C1 C2 C3 C4 -176.9(4) . . . . ? C2 C3 C4 C5 -0.7(6) . . . . ? C2 C3 C4 C8 175.9(3) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C8 C4 C5 C6 -176.8(3) . . . . ? C4 C5 C6 C7 1.4(6) . . . . ? C4 C5 C6 O5 175.1(3) . . . . ? C5 C6 C7 C2 -1.7(6) . . . . ? O5 C6 C7 C2 -175.8(3) . . . . ? C3 C2 C7 C6 0.8(6) . . . . ? C1 C2 C7 C6 178.1(4) . . . . ? C5 C4 C8 O3 174.6(4) . . . . ? C3 C4 C8 O3 -1.9(5) . . . . ? C5 C4 C8 O4 -5.4(6) . . . . ? C3 C4 C8 O4 178.0(4) . . . . ? C14 C9 C10 C11 0.0(7) . . . . ? O5 C9 C10 C11 -176.1(4) . . . . ? C9 C10 C11 C12 -1.3(8) . . . . ? C10 C11 C12 C13 1.5(7) . . . . ? C10 C11 C12 C15 -178.6(4) . . . . ? C11 C12 C13 C14 -0.4(7) . . . . ? C15 C12 C13 C14 179.7(4) . . . . ? C10 C9 C14 C13 1.1(7) . . . . ? O5 C9 C14 C13 176.9(4) . . . . ? C12 C13 C14 C9 -0.9(7) . . . . ? C11 C12 C15 N4 -172.5(4) . . . . ? C13 C12 C15 N4 7.4(6) . . . . ? C11 C12 C15 N1 7.7(6) . . . . ? C13 C12 C15 N1 -172.4(4) . . . . ? N4 C15 N1 N2 0.2(4) . . . . ? C12 C15 N1 N2 180.0(3) . . . . ? C15 N1 N2 N3 -0.6(4) . . . . ? C15 N1 N2 Cd1 167.9(2) . . . 2_666 ? N1 N2 N3 N4 0.9(4) . . . . ? Cd1 N2 N3 N4 -165.8(2) 2_666 . . . ? N1 N2 N3 Cd1 -174.4(2) . . . 1_666 ? Cd1 N2 N3 Cd1 19.0(5) 2_666 . . 1_666 ? N1 C15 N4 N3 0.3(4) . . . . ? C12 C15 N4 N3 -179.5(4) . . . . ? N1 C15 N4 Cd2 175.1(3) . . . 2_656 ? C12 C15 N4 Cd2 -4.7(6) . . . 2_656 ? N2 N3 N4 C15 -0.7(4) . . . . ? Cd1 N3 N4 C15 174.9(2) 1_666 . . . ? N2 N3 N4 Cd2 -177.0(2) . . . 2_656 ? Cd1 N3 N4 Cd2 -1.4(3) 1_666 . . 2_656 ? O2 C1 O1 Cd1 -74.2(5) . . . . ? C2 C1 O1 Cd1 107.7(4) . . . . ? O7 Cd1 O1 C1 56.3(3) . . . . ? O4 Cd1 O1 C1 169.9(6) 1_554 . . . ? O6 Cd1 O1 C1 -31.7(3) . . . . ? N2 Cd1 O1 C1 -115.3(3) 2_666 . . . ? N3 Cd1 O1 C1 145.5(3) 1_444 . . . ? Cd2 Cd1 O1 C1 87.4(3) 2_545 . . . ? O1 C1 O2 Cd2 6.9(5) . . . . ? C2 C1 O2 Cd2 -175.0(2) . . . . ? O3 Cd2 O2 C1 -140.1(3) 2_546 . . . ? O7 Cd2 O2 C1 -48.3(4) 2_545 . . . ? O7 Cd2 O2 C1 40.2(3) . . . . ? N4 Cd2 O2 C1 132.3(3) 2_656 . . . ? O8 Cd2 O2 C1 -56.0(3) . . . . ? Cd2 Cd2 O2 C1 18.7(3) 2_545 . . . ? Cd1 Cd2 O2 C1 -154.1(2) 2_545 . . . ? O4 C8 O3 Cd2 46.3(7) . . . 2_546 ? C4 C8 O3 Cd2 -133.8(3) . . . 2_546 ? O3 C8 O4 Cd1 -30.1(6) . . . 1_556 ? C4 C8 O4 Cd1 149.9(3) . . . 1_556 ? C14 C9 O5 C6 35.7(6) . . . . ? C10 C9 O5 C6 -148.2(4) . . . . ? C7 C6 O5 C9 -146.2(4) . . . . ? C5 C6 O5 C9 39.8(5) . . . . ? O4 Cd1 O7 Cd2 -50.81(13) 1_554 . . 2_545 ? O6 Cd1 O7 Cd2 -146.09(14) . . . 2_545 ? N2 Cd1 O7 Cd2 154.8(3) 2_666 . . 2_545 ? O1 Cd1 O7 Cd2 121.10(12) . . . 2_545 ? N3 Cd1 O7 Cd2 35.78(12) 1_444 . . 2_545 ? O4 Cd1 O7 Cd2 -161.27(13) 1_554 . . . ? O6 Cd1 O7 Cd2 103.45(16) . . . . ? N2 Cd1 O7 Cd2 44.4(4) 2_666 . . . ? O1 Cd1 O7 Cd2 10.64(13) . . . . ? N3 Cd1 O7 Cd2 -74.68(14) 1_444 . . . ? Cd2 Cd1 O7 Cd2 -110.46(17) 2_545 . . . ? O2 Cd2 O7 Cd1 -40.31(14) . . . . ? O3 Cd2 O7 Cd1 141.6(6) 2_546 . . . ? O7 Cd2 O7 Cd1 115.88(16) 2_545 . . . ? N4 Cd2 O7 Cd1 -152.96(13) 2_656 . . . ? O8 Cd2 O7 Cd1 38.03(14) . . . . ? Cd2 Cd2 O7 Cd1 115.88(16) 2_545 . . . ? Cd1 Cd2 O7 Cd1 145.20(10) 2_545 . . . ? O2 Cd2 O7 Cd2 -156.19(10) . . . 2_545 ? O3 Cd2 O7 Cd2 25.8(7) 2_546 . . 2_545 ? O7 Cd2 O7 Cd2 0.0 2_545 . . 2_545 ? N4 Cd2 O7 Cd2 91.16(10) 2_656 . . 2_545 ? O8 Cd2 O7 Cd2 -77.85(11) . . . 2_545 ? Cd1 Cd2 O7 Cd2 29.32(9) 2_545 . . 2_545 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.546 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 958313' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H7 Co2 N4 O7, 2(O)' _chemical_formula_sum 'C15 H7 Co2 N4 O9' _chemical_formula_weight 505.11 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' Co Co 0.3494 0.9721 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.117(16) _cell_length_b 9.452(16) _cell_length_c 10.914(19) _cell_angle_alpha 97.53(3) _cell_angle_beta 92.11(2) _cell_angle_gamma 103.25(3) _cell_volume 905(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour PURPLE _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 502 _exptl_absorpt_coefficient_mu 1.893 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6006 _exptl_absorpt_correction_T_max 0.8333 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4160 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0880 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3102 _reflns_number_gt 2259 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1121P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3102 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1768 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6906(6) 0.3161(7) 0.2322(5) 0.0343(14) Uani 1 1 d . . . C2 C 0.6178(6) 0.3117(6) 0.3558(5) 0.0308(14) Uani 1 1 d . . . C3 C 0.4580(6) 0.2674(6) 0.3554(5) 0.0316(14) Uani 1 1 d . . . H3 H 0.3985 0.2335 0.2818 0.038 Uiso 1 1 calc R . . C4 C 0.3932(5) 0.2765(6) 0.4692(5) 0.0341(14) Uani 1 1 d . . . C5 C 0.4798(6) 0.3268(6) 0.5809(5) 0.0320(13) Uani 1 1 d . . . H5 H 0.4332 0.3334 0.6552 0.038 Uiso 1 1 calc R . . C6 C 0.6382(6) 0.3676(6) 0.5805(5) 0.0303(14) Uani 1 1 d . . . C7 C 0.7076(6) 0.3627(6) 0.4682(5) 0.0318(14) Uani 1 1 d . . . H7 H 0.8121 0.3927 0.4676 0.038 Uiso 1 1 calc R . . C8 C 0.7305(6) 0.4234(6) 0.7031(5) 0.0317(14) Uani 1 1 d . . . C9 C 0.1397(6) 0.1293(7) 0.4047(5) 0.0344(15) Uani 1 1 d . . . C10 C 0.1784(6) -0.0008(7) 0.3578(6) 0.0426(17) Uani 1 1 d . . . H10 H 0.2757 -0.0121 0.3737 0.051 Uiso 1 1 calc R . . C11 C 0.0724(6) -0.1125(7) 0.2879(6) 0.0411(16) Uani 1 1 d . . . H11 H 0.0994 -0.1988 0.2571 0.049 Uiso 1 1 calc R . . C12 C -0.0749(6) -0.0992(6) 0.2623(5) 0.0311(13) Uani 1 1 d . . . C13 C -0.1136(6) 0.0304(7) 0.3126(6) 0.0463(18) Uani 1 1 d . . . H13 H -0.2116 0.0408 0.2984 0.056 Uiso 1 1 calc R . . C14 C -0.0063(6) 0.1451(7) 0.3843(6) 0.0421(17) Uani 1 1 d . . . H14 H -0.0330 0.2306 0.4177 0.051 Uiso 1 1 calc R . . C15 C -0.1894(6) -0.2181(6) 0.1843(5) 0.0305(14) Uani 1 1 d . . . Co1 Co 0.64360(7) 0.36245(8) -0.03379(6) 0.0302(3) Uani 1 1 d . . . Co2 Co 0.97779(7) 0.49263(9) 0.14119(6) 0.0332(3) Uani 1 1 d . . . N1 N -0.3250(5) -0.1977(5) 0.1472(4) 0.0364(12) Uani 1 1 d . . . N2 N -0.3988(4) -0.3274(5) 0.0777(4) 0.0312(12) Uani 1 1 d . . . N3 N -0.3120(5) -0.4209(5) 0.0730(4) 0.0319(12) Uani 1 1 d . . . N4 N -0.1777(4) -0.3565(5) 0.1404(4) 0.0309(12) Uani 1 1 d . . . O1 O 0.6127(5) 0.1441(5) -0.1430(4) 0.0536(13) Uani 1 1 d . . . O2 O 0.8755(4) 0.3807(4) -0.0285(3) 0.0316(9) Uani 1 1 d . . . O3 O 0.8340(4) 0.3652(5) 0.2408(4) 0.0399(11) Uani 1 1 d . . . O4 O 0.6079(4) 0.2749(5) 0.1320(3) 0.0396(11) Uani 1 1 d . . . O5 O 0.8727(4) 0.4358(5) 0.7034(3) 0.0379(11) Uani 1 1 d . . . O6 O 0.6622(4) 0.4598(5) 0.7988(3) 0.0408(11) Uani 1 1 d . . . O7 O 0.2363(4) 0.2488(5) 0.4787(4) 0.0420(12) Uani 1 1 d . . . O8 O 0.1050(5) 0.2779(6) 0.1236(4) 0.0659(15) Uani 1 1 d . . . O9 O 0.1901(9) 0.9797(8) 0.0267(7) 0.107(2) 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 C1 0.035(3) 0.045(4) 0.027(3) 0.002(3) 0.009(2) 0.017(3) C2 0.029(3) 0.036(3) 0.026(3) -0.006(3) 0.002(2) 0.010(2) C3 0.030(3) 0.036(3) 0.023(3) -0.008(3) 0.000(2) 0.005(2) C4 0.025(2) 0.040(4) 0.034(3) -0.005(3) 0.006(2) 0.007(2) C5 0.031(3) 0.040(3) 0.023(3) -0.002(2) 0.009(2) 0.007(3) C6 0.030(3) 0.037(3) 0.022(3) -0.007(3) 0.002(2) 0.011(3) C7 0.031(3) 0.038(4) 0.025(3) -0.005(3) 0.002(2) 0.013(3) C8 0.038(3) 0.039(4) 0.020(3) 0.000(3) 0.003(2) 0.014(3) C9 0.026(2) 0.045(4) 0.027(3) -0.008(3) 0.001(2) 0.005(3) C10 0.029(3) 0.051(4) 0.045(4) -0.007(3) -0.001(2) 0.013(3) C11 0.035(3) 0.041(4) 0.043(3) -0.013(3) 0.001(3) 0.010(3) C12 0.030(2) 0.037(3) 0.024(3) -0.003(3) 0.006(2) 0.007(2) C13 0.027(3) 0.052(4) 0.055(4) -0.015(3) -0.006(3) 0.013(3) C14 0.033(3) 0.041(4) 0.049(4) -0.012(3) 0.004(3) 0.014(3) C15 0.028(3) 0.037(3) 0.023(3) -0.004(3) 0.004(2) 0.005(2) Co1 0.0244(4) 0.0417(6) 0.0207(4) -0.0091(4) 0.0021(3) 0.0078(3) Co2 0.0254(4) 0.0502(6) 0.0200(4) -0.0059(4) 0.0021(3) 0.0068(4) N1 0.032(2) 0.035(3) 0.035(3) -0.011(2) 0.001(2) 0.005(2) N2 0.027(2) 0.035(3) 0.027(2) -0.009(2) 0.0025(18) 0.007(2) N3 0.027(2) 0.044(3) 0.022(2) -0.009(2) 0.0009(17) 0.012(2) N4 0.025(2) 0.040(3) 0.023(2) -0.008(2) 0.0018(17) 0.005(2) O1 0.042(2) 0.058(3) 0.055(3) -0.021(2) -0.001(2) 0.014(2) O2 0.0268(17) 0.047(2) 0.0188(18) -0.0032(18) 0.0051(14) 0.0083(17) O3 0.0292(19) 0.059(3) 0.029(2) 0.001(2) 0.0020(16) 0.0086(19) O4 0.038(2) 0.053(3) 0.021(2) -0.005(2) 0.0007(16) 0.004(2) O5 0.0300(19) 0.058(3) 0.024(2) -0.005(2) 0.0014(15) 0.0124(19) O6 0.035(2) 0.064(3) 0.025(2) -0.003(2) 0.0060(16) 0.019(2) O7 0.0228(17) 0.054(3) 0.038(2) -0.021(2) 0.0041(16) 0.0020(18) O8 0.059(3) 0.094(4) 0.042(3) 0.004(3) 0.005(2) 0.016(3) O9 0.132(6) 0.124(6) 0.088(5) 0.031(5) 0.029(4) 0.061(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O4 1.268(7) . ? C1 O3 1.279(7) . ? C1 C2 1.526(8) . ? C2 C7 1.414(7) . ? C2 C3 1.420(8) . ? C3 C4 1.395(8) . ? C3 H3 0.9300 . ? C4 C5 1.393(8) . ? C4 O7 1.404(6) . ? C5 C6 1.407(8) . ? C5 H5 0.9300 . ? C6 C7 1.400(7) . ? C6 C8 1.518(7) . ? C7 H7 0.9300 . ? C8 O5 1.274(6) . ? C8 O6 1.284(6) . ? C9 C14 1.387(8) . ? C9 C10 1.394(8) . ? C9 O7 1.399(7) . ? C10 C11 1.378(8) . ? C10 H10 0.9300 . ? C11 C12 1.399(8) . ? C11 H11 0.9300 . ? C12 C13 1.402(8) . ? C12 C15 1.491(7) . ? C13 C14 1.407(8) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 N1 1.350(7) . ? C15 N4 1.363(7) . ? Co1 O2 2.080(5) . ? Co1 O4 2.093(5) . ? Co1 O6 2.146(5) 1_554 ? Co1 N3 2.163(5) 1_665 ? Co1 O1 2.196(5) . ? Co1 N2 2.204(6) 2 ? Co2 O3 2.019(5) . ? Co2 O5 2.073(5) 2_766 ? Co2 O2 2.080(4) . ? Co2 O2 2.123(4) 2_765 ? Co2 N4 2.230(5) 1_665 ? N1 N2 1.368(6) . ? N2 N3 1.312(6) . ? N2 Co1 2.204(6) 2 ? N3 N4 1.373(6) . ? N3 Co1 2.163(5) 1_445 ? N4 Co2 2.230(5) 1_445 ? O2 Co2 2.123(4) 2_765 ? O5 Co2 2.073(4) 2_766 ? O6 Co1 2.146(5) 1_556 ? 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 O4 C1 O3 125.6(5) . . ? O4 C1 C2 119.5(5) . . ? O3 C1 C2 114.9(5) . . ? C7 C2 C3 120.7(5) . . ? C7 C2 C1 120.2(5) . . ? C3 C2 C1 118.9(5) . . ? C4 C3 C2 117.9(5) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C5 C4 C3 122.2(5) . . ? C5 C4 O7 115.0(4) . . ? C3 C4 O7 122.5(5) . . ? C4 C5 C6 119.5(5) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 120.1(5) . . ? C7 C6 C8 121.1(5) . . ? C5 C6 C8 118.7(4) . . ? C6 C7 C2 119.6(5) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? O5 C8 O6 124.0(5) . . ? O5 C8 C6 117.5(4) . . ? O6 C8 C6 118.4(5) . . ? C14 C9 C10 120.3(5) . . ? C14 C9 O7 114.5(5) . . ? C10 C9 O7 125.1(5) . . ? C11 C10 C9 119.9(5) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 121.5(5) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C11 C12 C13 118.0(5) . . ? C11 C12 C15 121.9(5) . . ? C13 C12 C15 120.0(5) . . ? C12 C13 C14 120.9(5) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C9 C14 C13 119.3(5) . . ? C9 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? N1 C15 N4 110.5(4) . . ? N1 C15 C12 121.6(5) . . ? N4 C15 C12 127.9(5) . . ? O2 Co1 O4 96.42(14) . . ? O2 Co1 O6 88.26(14) . 1_554 ? O4 Co1 O6 174.80(14) . 1_554 ? O2 Co1 N3 88.28(15) . 1_665 ? O4 Co1 N3 88.2(2) . 1_665 ? O6 Co1 N3 89.7(2) 1_554 1_665 ? O2 Co1 O1 88.42(15) . . ? O4 Co1 O1 92.5(2) . . ? O6 Co1 O1 89.9(2) 1_554 . ? N3 Co1 O1 176.68(14) 1_665 . ? O2 Co1 N2 168.91(15) . 2 ? O4 Co1 N2 91.81(17) . 2 ? O6 Co1 N2 83.85(17) 1_554 2 ? N3 Co1 N2 99.42(15) 1_665 2 ? O1 Co1 N2 83.80(15) . 2 ? O3 Co2 O5 89.8(2) . 2_766 ? O3 Co2 O2 93.89(19) . . ? O5 Co2 O2 162.04(14) 2_766 . ? O3 Co2 O2 177.17(14) . 2_765 ? O5 Co2 O2 92.76(19) 2_766 2_765 ? O2 Co2 O2 83.32(19) . 2_765 ? O3 Co2 N4 89.7(2) . 1_665 ? O5 Co2 N4 108.09(17) 2_766 1_665 ? O2 Co2 N4 89.52(16) . 1_665 ? O2 Co2 N4 90.72(19) 2_765 1_665 ? C15 N1 N2 105.6(4) . . ? N3 N2 N1 109.5(4) . . ? N3 N2 Co1 130.8(3) . 2 ? N1 N2 Co1 117.9(3) . 2 ? N2 N3 N4 109.5(4) . . ? N2 N3 Co1 127.4(3) . 1_445 ? N4 N3 Co1 122.9(3) . 1_445 ? C15 N4 N3 104.9(4) . . ? C15 N4 Co2 142.5(3) . 1_445 ? N3 N4 Co2 112.6(3) . 1_445 ? Co1 O2 Co2 110.52(15) . . ? Co1 O2 Co2 123.6(2) . 2_765 ? Co2 O2 Co2 96.68(19) . 2_765 ? C1 O3 Co2 133.3(4) . . ? C1 O4 Co1 126.3(4) . . ? C8 O5 Co2 124.8(3) . 2_766 ? C8 O6 Co1 127.3(4) . 1_556 ? C9 O7 C4 120.5(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 O4 C1 C2 C7 -177.5(5) . . . . ? O3 C1 C2 C7 1.3(8) . . . . ? O4 C1 C2 C3 -2.7(9) . . . . ? O3 C1 C2 C3 176.1(5) . . . . ? C7 C2 C3 C4 0.3(9) . . . . ? C1 C2 C3 C4 -174.5(5) . . . . ? C2 C3 C4 C5 0.0(9) . . . . ? C2 C3 C4 O7 173.8(5) . . . . ? C3 C4 C5 C6 -1.2(9) . . . . ? O7 C4 C5 C6 -175.5(5) . . . . ? C4 C5 C6 C7 2.3(9) . . . . ? C4 C5 C6 C8 179.5(5) . . . . ? C5 C6 C7 C2 -2.1(9) . . . . ? C8 C6 C7 C2 -179.2(5) . . . . ? C3 C2 C7 C6 0.8(9) . . . . ? C1 C2 C7 C6 175.5(6) . . . . ? C7 C6 C8 O5 -14.6(9) . . . . ? C5 C6 C8 O5 168.3(5) . . . . ? C7 C6 C8 O6 163.1(6) . . . . ? C5 C6 C8 O6 -14.0(9) . . . . ? C14 C9 C10 C11 1.9(10) . . . . ? O7 C9 C10 C11 178.6(6) . . . . ? C9 C10 C11 C12 0.0(10) . . . . ? C10 C11 C12 C13 -1.6(10) . . . . ? C10 C11 C12 C15 178.5(6) . . . . ? C11 C12 C13 C14 1.5(10) . . . . ? C15 C12 C13 C14 -178.7(6) . . . . ? C10 C9 C14 C13 -2.0(10) . . . . ? O7 C9 C14 C13 -179.1(6) . . . . ? C12 C13 C14 C9 0.3(10) . . . . ? C11 C12 C15 N1 -171.6(6) . . . . ? C13 C12 C15 N1 8.5(9) . . . . ? C11 C12 C15 N4 8.2(9) . . . . ? C13 C12 C15 N4 -171.6(6) . . . . ? N4 C15 N1 N2 -0.3(6) . . . . ? C12 C15 N1 N2 179.6(5) . . . . ? C15 N1 N2 N3 -0.1(6) . . . . ? C15 N1 N2 Co1 166.1(4) . . . 2 ? N1 N2 N3 N4 0.5(6) . . . . ? Co1 N2 N3 N4 -163.3(4) 2 . . . ? N1 N2 N3 Co1 -174.7(3) . . . 1_445 ? Co1 N2 N3 Co1 21.4(7) 2 . . 1_445 ? N1 C15 N4 N3 0.6(6) . . . . ? C12 C15 N4 N3 -179.3(5) . . . . ? N1 C15 N4 Co2 -179.1(4) . . . 1_445 ? C12 C15 N4 Co2 1.0(10) . . . 1_445 ? N2 N3 N4 C15 -0.7(6) . . . . ? Co1 N3 N4 C15 174.8(3) 1_445 . . . ? N2 N3 N4 Co2 179.1(3) . . . 1_445 ? Co1 N3 N4 Co2 -5.4(5) 1_445 . . 1_445 ? O4 Co1 O2 Co2 -51.7(2) . . . . ? O6 Co1 O2 Co2 126.0(2) 1_554 . . . ? N3 Co1 O2 Co2 36.3(2) 1_665 . . . ? O1 Co1 O2 Co2 -144.0(2) . . . . ? N2 Co1 O2 Co2 170.6(8) 2 . . . ? O4 Co1 O2 Co2 -165.1(2) . . . 2_765 ? O6 Co1 O2 Co2 12.6(2) 1_554 . . 2_765 ? N3 Co1 O2 Co2 -77.1(3) 1_665 . . 2_765 ? O1 Co1 O2 Co2 102.5(3) . . . 2_765 ? N2 Co1 O2 Co2 57.2(10) 2 . . 2_765 ? O3 Co2 O2 Co1 50.8(2) . . . . ? O5 Co2 O2 Co1 152.1(4) 2_766 . . . ? O2 Co2 O2 Co1 -129.7(3) 2_765 . . . ? N4 Co2 O2 Co1 -38.9(2) 1_665 . . . ? O3 Co2 O2 Co2 -179.51(15) . . . 2_765 ? O5 Co2 O2 Co2 -78.2(6) 2_766 . . 2_765 ? O2 Co2 O2 Co2 0.0 2_765 . . 2_765 ? N4 Co2 O2 Co2 90.8(2) 1_665 . . 2_765 ? O4 C1 O3 Co2 36.4(9) . . . . ? C2 C1 O3 Co2 -142.4(4) . . . . ? O5 Co2 O3 C1 152.9(5) 2_766 . . . ? O2 Co2 O3 C1 -44.7(5) . . . . ? O2 Co2 O3 C1 -55(3) 2_765 . . . ? N4 Co2 O3 C1 44.8(5) 1_665 . . . ? O3 C1 O4 Co1 -33.1(8) . . . . ? C2 C1 O4 Co1 145.6(4) . . . . ? O2 Co1 O4 C1 42.1(4) . . . . ? O6 Co1 O4 C1 -112.0(16) 1_554 . . . ? N3 Co1 O4 C1 -45.9(4) 1_665 . . . ? O1 Co1 O4 C1 130.8(4) . . . . ? N2 Co1 O4 C1 -145.3(4) 2 . . . ? O6 C8 O5 Co2 3.0(9) . . . 2_766 ? C6 C8 O5 Co2 -179.4(4) . . . 2_766 ? O5 C8 O6 Co1 -64.7(8) . . . 1_556 ? C6 C8 O6 Co1 117.7(5) . . . 1_556 ? C14 C9 O7 C4 -155.2(6) . . . . ? C10 C9 O7 C4 27.9(9) . . . . ? C5 C4 O7 C9 -142.3(6) . . . . ? C3 C4 O7 C9 43.4(9) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.878 _refine_diff_density_min -0.918 _refine_diff_density_rms 0.165 _database_code_depnum_ccdc_archive 'CCDC 958314'