# 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_Compound-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 Co N O7' _chemical_formula_sum 'C14 H13 Co N O7' _chemical_formula_weight 366.18 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.6970(8) _cell_length_b 9.9490(14) _cell_length_c 15.105(2) _cell_angle_alpha 103.050(12) _cell_angle_beta 92.105(13) _cell_angle_gamma 96.701(13) _cell_volume 681.48(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 569 _cell_measurement_theta_min 3.8555 _cell_measurement_theta_max 29.1036 _exptl_crystal_description needle _exptl_crystal_colour pink _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 374 _exptl_absorpt_coefficient_mu 1.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7812 _exptl_absorpt_correction_T_max 0.8290 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4905 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.1132 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 29.17 _reflns_number_total 3077 _reflns_number_gt 2023 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^ > 2\s(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^)+(0.0224P)^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 3077 _refine_ls_number_parameters 224 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1116 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.086 _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 Co1 Co -0.24723(12) 0.11463(6) -0.30001(4) 0.02220(19) Uani 1 1 d . . . C1 C 0.4268(8) 0.1889(5) 0.3057(3) 0.0202(10) Uani 1 1 d . . . C2 C 0.2416(8) 0.2422(4) 0.3758(3) 0.0204(10) Uani 1 1 d . . . C3 C 0.2407(10) 0.3820(5) 0.4043(3) 0.0330(12) Uani 1 1 d . . . H3 H 0.1215 0.4151 0.4499 0.040 Uiso 1 1 calc R . . C4 C 0.4131(10) 0.4779(5) 0.3674(4) 0.0378(14) Uani 1 1 d . . . H4 H 0.4117 0.5732 0.3882 0.045 Uiso 1 1 calc R . . C5 C 0.5810(10) 0.4265(5) 0.3007(3) 0.0335(13) Uani 1 1 d . . . H5 H 0.6946 0.4879 0.2744 0.040 Uiso 1 1 calc R . . C6 C 0.0363(8) 0.1479(5) 0.4167(3) 0.0228(10) Uani 1 1 d . . . C7 C 0.7768(9) 0.2429(5) 0.1960(3) 0.0262(11) Uani 1 1 d . . . H7A H 0.8236 0.1510 0.1975 0.031 Uiso 1 1 calc R . . H7B H 0.9548 0.3059 0.2057 0.031 Uiso 1 1 calc R . . C8 C 0.6386(9) 0.2385(4) 0.1042(3) 0.0247(11) Uani 1 1 d . . . C9 C 0.3941(9) 0.1463(5) 0.0702(3) 0.0309(12) Uani 1 1 d . . . H9 H 0.3070 0.0915 0.1065 0.037 Uiso 1 1 calc R . . C10 C 0.2784(9) 0.1350(5) -0.0169(3) 0.0323(12) Uani 1 1 d . . . H10 H 0.1113 0.0745 -0.0379 0.039 Uiso 1 1 calc R . . C11 C 0.4072(9) 0.2121(4) -0.0731(3) 0.0232(11) Uani 1 1 d . . . C12 C 0.6456(10) 0.3059(5) -0.0397(3) 0.0331(12) Uani 1 1 d . . . H12 H 0.7325 0.3598 -0.0766 0.040 Uiso 1 1 calc R . . C13 C 0.7581(10) 0.3206(5) 0.0490(3) 0.0331(12) Uani 1 1 d . . . H13 H 0.9161 0.3866 0.0715 0.040 Uiso 1 1 calc R . . C14 C 0.2883(9) 0.1913(4) -0.1692(3) 0.0226(10) Uani 1 1 d . . . N1 N 0.5888(7) 0.2890(4) 0.2710(2) 0.0224(9) Uani 1 1 d . . . O1 O 0.4562(6) 0.0647(3) 0.2732(2) 0.0273(8) Uani 1 1 d . . . O2 O 0.0229(6) 0.0177(3) 0.3905(2) 0.0264(8) Uani 1 1 d . . . O3 O -0.1179(6) 0.2062(3) 0.4760(2) 0.0322(9) Uani 1 1 d . . . O4 O 0.0324(6) 0.1358(3) -0.1869(2) 0.0289(8) Uani 1 1 d . . . O5 O 0.4493(6) 0.2306(3) -0.2269(2) 0.0255(8) Uani 1 1 d . . . O1W O 0.0115(7) 0.2832(3) -0.3327(2) 0.0257(7) Uani 1 1 d D . . H1A H 0.182(5) 0.265(5) -0.313(3) 0.053(17) Uiso 1 1 d D . . H1B H 0.011(9) 0.273(4) -0.3934(8) 0.027(13) Uiso 1 1 d D . . O2W O -0.5134(6) 0.1269(3) -0.4127(2) 0.0289(8) Uani 1 1 d D . . H2A H -0.674(7) 0.065(5) -0.426(4) 0.070(19) Uiso 1 1 d D . . H2B H -0.439(13) 0.138(6) -0.465(2) 0.09(2) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0210(3) 0.0248(3) 0.0210(4) 0.0061(3) 0.0031(3) 0.0015(2) C1 0.016(2) 0.026(3) 0.017(2) 0.005(2) -0.0024(18) -0.0013(18) C2 0.018(2) 0.022(2) 0.019(2) 0.0012(19) -0.0018(18) 0.0018(17) C3 0.035(3) 0.035(3) 0.026(3) 0.002(2) 0.005(2) 0.002(2) C4 0.048(3) 0.020(3) 0.042(3) 0.002(2) 0.009(3) 0.002(2) C5 0.038(3) 0.029(3) 0.033(3) 0.008(2) 0.006(2) -0.005(2) C6 0.019(2) 0.031(3) 0.020(3) 0.011(2) -0.0011(19) 0.0019(19) C7 0.023(2) 0.035(3) 0.018(3) 0.004(2) 0.004(2) -0.004(2) C8 0.025(2) 0.028(3) 0.022(3) 0.007(2) 0.006(2) 0.0013(19) C9 0.026(2) 0.044(3) 0.020(3) 0.009(2) 0.000(2) -0.008(2) C10 0.026(2) 0.042(3) 0.027(3) 0.010(2) -0.005(2) -0.008(2) C11 0.026(2) 0.025(3) 0.020(3) 0.006(2) 0.005(2) 0.0037(19) C12 0.035(3) 0.041(3) 0.024(3) 0.012(2) 0.006(2) -0.003(2) C13 0.029(3) 0.040(3) 0.027(3) 0.011(2) -0.006(2) -0.011(2) C14 0.022(2) 0.026(3) 0.021(3) 0.005(2) 0.003(2) 0.0091(19) N1 0.0242(19) 0.024(2) 0.017(2) 0.0036(16) 0.0017(16) -0.0024(16) O1 0.0292(17) 0.0217(18) 0.031(2) 0.0051(15) 0.0110(15) 0.0018(13) O2 0.0286(16) 0.0241(18) 0.0267(19) 0.0069(15) 0.0100(15) 0.0007(13) O3 0.0345(18) 0.039(2) 0.026(2) 0.0081(16) 0.0177(16) 0.0092(15) O4 0.0198(16) 0.047(2) 0.0194(18) 0.0096(15) -0.0020(14) -0.0008(14) O5 0.0264(16) 0.0320(18) 0.0195(18) 0.0076(14) 0.0070(14) 0.0050(13) O1W 0.0252(18) 0.0285(18) 0.024(2) 0.0077(15) 0.0004(16) 0.0020(14) O2W 0.0231(17) 0.043(2) 0.0184(19) 0.0061(16) 0.0016(15) -0.0032(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Co1 O1 2.063(3) 2 ? Co1 O4 2.072(3) . ? Co1 O2 2.080(3) 2 ? Co1 O2W 2.109(4) . ? Co1 O1W 2.116(3) . ? Co1 O5 2.123(3) 1_455 ? C1 O1 1.248(5) . ? C1 N1 1.391(5) . ? C1 C2 1.443(5) . ? C2 C3 1.360(6) . ? C2 C6 1.512(5) . ? C3 C4 1.404(6) . ? C3 H3 0.9300 . ? C4 C5 1.349(6) . ? C4 H4 0.9300 . ? C5 N1 1.345(6) . ? C5 H5 0.9300 . ? C6 O3 1.255(5) . ? C6 O2 1.260(5) . ? C7 N1 1.485(5) . ? C7 C8 1.500(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.382(6) . ? C8 C9 1.386(6) . ? C9 C10 1.380(6) . ? C9 H9 0.9300 . ? C10 C11 1.378(6) . ? C10 H10 0.9300 . ? C11 C12 1.371(6) . ? C11 C14 1.497(6) . ? C12 C13 1.393(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O4 1.255(5) . ? C14 O5 1.271(4) . ? O1 Co1 2.063(3) 2 ? O2 Co1 2.080(3) 2 ? O5 Co1 2.123(3) 1_655 ? O1W H1A 0.899(10) . ? O1W H1B 0.900(10) . ? O2W H2A 0.898(10) . ? O2W H2B 0.896(10) . ? 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 O1 Co1 O4 89.53(13) 2 . ? O1 Co1 O2 85.52(11) 2 2 ? O4 Co1 O2 96.38(13) . 2 ? O1 Co1 O2W 98.80(13) 2 . ? O4 Co1 O2W 171.00(13) . . ? O2 Co1 O2W 87.71(13) 2 . ? O1 Co1 O1W 172.53(12) 2 . ? O4 Co1 O1W 88.11(13) . . ? O2 Co1 O1W 87.69(11) 2 . ? O2W Co1 O1W 84.04(13) . . ? O1 Co1 O5 89.68(11) 2 1_455 ? O4 Co1 O5 94.51(12) . 1_455 ? O2 Co1 O5 168.06(12) 2 1_455 ? O2W Co1 O5 82.21(12) . 1_455 ? O1W Co1 O5 97.57(12) . 1_455 ? O1 C1 N1 117.3(3) . . ? O1 C1 C2 127.5(3) . . ? N1 C1 C2 115.2(4) . . ? C3 C2 C1 119.6(4) . . ? C3 C2 C6 118.0(4) . . ? C1 C2 C6 122.4(4) . . ? C2 C3 C4 122.4(4) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C5 C4 C3 117.4(4) . . ? C5 C4 H4 121.3 . . ? C3 C4 H4 121.3 . . ? N1 C5 C4 122.0(4) . . ? N1 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? O3 C6 O2 123.0(3) . . ? O3 C6 C2 116.7(4) . . ? O2 C6 C2 120.3(4) . . ? N1 C7 C8 112.5(4) . . ? N1 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? N1 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C13 C8 C9 118.0(4) . . ? C13 C8 C7 121.3(4) . . ? C9 C8 C7 120.6(4) . . ? C10 C9 C8 120.7(4) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C9 120.9(4) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 119.0(4) . . ? C12 C11 C14 121.1(4) . . ? C10 C11 C14 119.9(4) . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C13 C12 121.0(4) . . ? C8 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? O4 C14 O5 124.5(4) . . ? O4 C14 C11 116.7(3) . . ? O5 C14 C11 118.8(4) . . ? C5 N1 C1 123.4(3) . . ? C5 N1 C7 117.8(3) . . ? C1 N1 C7 118.8(3) . . ? C1 O1 Co1 129.9(2) . 2 ? C6 O2 Co1 134.1(2) . 2 ? C14 O4 Co1 131.5(3) . . ? C14 O5 Co1 125.7(3) . 1_655 ? Co1 O1W H1A 97(3) . . ? Co1 O1W H1B 111(3) . . ? H1A O1W H1B 109(4) . . ? Co1 O2W H2A 116(4) . . ? Co1 O2W H2B 121(4) . . ? H2A O2W H2B 109(5) . . ? 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 O1 C1 C2 C3 178.8(5) . . . . ? N1 C1 C2 C3 -1.4(6) . . . . ? O1 C1 C2 C6 -3.9(7) . . . . ? N1 C1 C2 C6 175.9(4) . . . . ? C1 C2 C3 C4 0.5(8) . . . . ? C6 C2 C3 C4 -176.9(5) . . . . ? C2 C3 C4 C5 0.8(8) . . . . ? C3 C4 C5 N1 -1.1(8) . . . . ? C3 C2 C6 O3 -1.4(7) . . . . ? C1 C2 C6 O3 -178.7(4) . . . . ? C3 C2 C6 O2 177.8(5) . . . . ? C1 C2 C6 O2 0.5(7) . . . . ? N1 C7 C8 C13 118.6(4) . . . . ? N1 C7 C8 C9 -64.7(6) . . . . ? C13 C8 C9 C10 1.5(7) . . . . ? C7 C8 C9 C10 -175.3(4) . . . . ? C8 C9 C10 C11 1.8(8) . . . . ? C9 C10 C11 C12 -3.1(7) . . . . ? C9 C10 C11 C14 176.1(4) . . . . ? C10 C11 C12 C13 1.2(7) . . . . ? C14 C11 C12 C13 -178.0(4) . . . . ? C9 C8 C13 C12 -3.4(7) . . . . ? C7 C8 C13 C12 173.4(5) . . . . ? C11 C12 C13 C8 2.1(8) . . . . ? C12 C11 C14 O4 -160.5(4) . . . . ? C10 C11 C14 O4 20.3(6) . . . . ? C12 C11 C14 O5 19.4(7) . . . . ? C10 C11 C14 O5 -159.8(4) . . . . ? C4 C5 N1 C1 0.2(8) . . . . ? C4 C5 N1 C7 178.9(5) . . . . ? O1 C1 N1 C5 -179.1(4) . . . . ? C2 C1 N1 C5 1.1(7) . . . . ? O1 C1 N1 C7 2.2(6) . . . . ? C2 C1 N1 C7 -177.6(4) . . . . ? C8 C7 N1 C5 -81.4(5) . . . . ? C8 C7 N1 C1 97.4(5) . . . . ? N1 C1 O1 Co1 -176.8(3) . . . 2 ? C2 C1 O1 Co1 3.0(7) . . . 2 ? O3 C6 O2 Co1 -177.2(3) . . . 2 ? C2 C6 O2 Co1 3.7(7) . . . 2 ? O5 C14 O4 Co1 -11.4(7) . . . . ? C11 C14 O4 Co1 168.4(3) . . . . ? O1 Co1 O4 C14 151.7(4) 2 . . . ? O2 Co1 O4 C14 66.3(4) 2 . . . ? O2W Co1 O4 C14 -50.4(9) . . . . ? O1W Co1 O4 C14 -21.2(4) . . . . ? O5 Co1 O4 C14 -118.7(4) 1_455 . . . ? O4 C14 O5 Co1 -96.9(5) . . . 1_655 ? C11 C14 O5 Co1 83.3(4) . . . 1_655 ? 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 O1W H1A O5 0.899(10) 1.88(2) 2.728(5) 156(5) . O1W H1A O2W 0.899(10) 2.43(4) 3.003(4) 122(4) 1_655 O1W H1B O3 0.900(10) 1.982(18) 2.841(5) 159(4) 1_554 O2W H2A O2 0.898(10) 1.90(3) 2.717(4) 151(5) 2_455 O2W H2B O3 0.896(10) 1.92(3) 2.718(4) 148(5) 1_554 _diffrn_measured_fraction_theta_max 0.831 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.508 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 938794' ####################################################################### # # 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_Compound-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N Ni O8' _chemical_formula_sum 'C14 H15 N Ni O8' _chemical_formula_weight 383.98 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.9110(2) _cell_length_b 29.7570(11) _cell_length_c 10.1970(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.639(4) _cell_angle_gamma 90.00 _cell_volume 1448.13(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4899 _cell_measurement_theta_min 2.8998 _cell_measurement_theta_max 29.0933 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 1.387 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6892 _exptl_absorpt_correction_T_max 0.8190 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11801 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 29.16 _reflns_number_total 3502 _reflns_number_gt 3245 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2\s(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^)+(0.0171P)^2^+11.2548P] 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 3502 _refine_ls_number_parameters 260 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1683 _refine_ls_wR_factor_gt 0.1665 _refine_ls_goodness_of_fit_ref 1.251 _refine_ls_restrained_S_all 1.250 _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 Ni1 Ni 0.69700(14) 0.41378(2) 0.94687(7) 0.02190(19) Uani 1 1 d . . . C1 C 0.4863(11) 0.40958(17) 0.6559(5) 0.0226(10) Uani 1 1 d . A . C2 C 0.6774(11) 0.44338(17) 0.6295(5) 0.0241(10) Uani 1 1 d . . . C3 C 0.7203(13) 0.44791(19) 0.5020(6) 0.0300(12) Uani 1 1 d . . . H3 H 0.8406 0.4701 0.4851 0.036 Uiso 1 1 calc R . . C4 C 0.5864(14) 0.4197(2) 0.3973(6) 0.0344(13) Uani 1 1 d . . . H4 H 0.6188 0.4227 0.3115 0.041 Uiso 1 1 calc R . . C5 C 0.4097(13) 0.38805(19) 0.4223(6) 0.0311(12) Uani 1 1 d . A . H5 H 0.3202 0.3692 0.3528 0.037 Uiso 1 1 calc R . . C6 C 0.8340(12) 0.47454(18) 0.7384(6) 0.0264(11) Uani 1 1 d . A . C7 C 0.1605(11) 0.34741(17) 0.5647(6) 0.0284(12) Uani 1 1 d . A . H7A H 0.0023 0.3471 0.4870 0.034 Uiso 1 1 calc R . . H7B H 0.0903 0.3541 0.6438 0.034 Uiso 1 1 calc R . . C8 C 0.2976(11) 0.30131(17) 0.5812(5) 0.0236(10) Uani 1 1 d . . . C9 C 0.272(3) 0.2726(4) 0.4654(11) 0.030(3) Uani 0.505(13) 1 d P A 1 H9 H 0.1781 0.2828 0.3806 0.036 Uiso 0.505(13) 1 calc PR A 1 C10 C 0.388(3) 0.2292(4) 0.4794(11) 0.027(3) Uani 0.505(13) 1 d P A 1 H10 H 0.3736 0.2108 0.4044 0.032 Uiso 0.505(13) 1 calc PR A 1 C12 C 0.555(3) 0.2411(4) 0.7155(12) 0.032(3) Uani 0.505(13) 1 d P A 1 H12 H 0.6493 0.2305 0.7997 0.039 Uiso 0.505(13) 1 calc PR A 1 C13 C 0.446(3) 0.2846(4) 0.7022(13) 0.033(3) Uani 0.505(13) 1 d P A 1 H13 H 0.4762 0.3029 0.7782 0.039 Uiso 0.505(13) 1 calc PR A 1 C9' C 0.131(2) 0.2660(4) 0.5284(15) 0.035(3) Uani 0.495(13) 1 d P A 2 H9' H -0.0579 0.2705 0.4891 0.042 Uiso 0.495(13) 1 calc PR A 2 C10' C 0.244(3) 0.2240(4) 0.5338(16) 0.039(4) Uani 0.495(13) 1 d P A 2 H10' H 0.1342 0.2008 0.4885 0.047 Uiso 0.495(13) 1 calc PR A 2 C12' C 0.559(3) 0.2949(4) 0.6546(15) 0.032(3) Uani 0.495(13) 1 d P A 2 H12' H 0.6646 0.3192 0.6959 0.038 Uiso 0.495(13) 1 calc PR A 2 C13' C 0.674(3) 0.2520(4) 0.6689(14) 0.031(3) Uani 0.495(13) 1 d P A 2 H13' H 0.8543 0.2480 0.7214 0.037 Uiso 0.495(13) 1 calc PR A 2 C11 C 0.5221(12) 0.21437(18) 0.6058(5) 0.0254(11) Uani 1 1 d . . . C14 C 0.6468(12) 0.16777(18) 0.6138(6) 0.0269(11) Uani 1 1 d . A . N1 N 0.3594(9) 0.38311(14) 0.5465(5) 0.0237(9) Uani 1 1 d . . . O1 O 0.4229(8) 0.40233(13) 0.7664(4) 0.0276(8) Uani 1 1 d . . . O2 O 0.8457(10) 0.46588(15) 0.8616(4) 0.0395(11) Uani 1 1 d . . . O3 O 0.9517(11) 0.50744(14) 0.7025(4) 0.0411(11) Uani 1 1 d . . . O4 O 0.8566(11) 0.15890(15) 0.7039(5) 0.0496(13) Uani 1 1 d . . . O5 O 0.5289(8) 0.14077(13) 0.5220(4) 0.0309(9) Uani 1 1 d . . . O1W O 0.9874(9) 0.37165(18) 0.8854(5) 0.0450(12) Uani 1 1 d . . . O2W O 0.4179(9) 0.45498(13) 1.0113(5) 0.0343(9) Uani 1 1 d . . . O3W O 0.9910(8) 0.42330(13) 1.1268(4) 0.0277(8) Uani 1 1 d D . . H3B H 0.993(15) 0.3969(12) 1.170(6) 0.042 Uiso 1 1 d D . . H3A H 1.005(15) 0.4431(18) 1.195(5) 0.042 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0203(3) 0.0238(3) 0.0214(3) -0.0019(3) 0.0045(2) -0.0044(3) C1 0.024(2) 0.020(2) 0.022(2) -0.0010(18) -0.0003(19) -0.001(2) C2 0.028(3) 0.019(2) 0.024(3) 0.0020(19) 0.004(2) -0.002(2) C3 0.040(3) 0.025(3) 0.026(3) 0.000(2) 0.009(2) -0.003(2) C4 0.047(4) 0.035(3) 0.022(3) 0.001(2) 0.010(2) -0.001(3) C5 0.039(3) 0.027(3) 0.022(3) -0.005(2) -0.002(2) 0.002(2) C6 0.030(3) 0.022(2) 0.027(3) -0.003(2) 0.007(2) -0.006(2) C7 0.024(3) 0.019(2) 0.038(3) -0.002(2) -0.001(2) -0.004(2) C8 0.027(3) 0.020(2) 0.023(3) 0.0002(19) 0.004(2) 0.000(2) C9 0.036(7) 0.025(5) 0.023(5) -0.003(4) -0.007(5) 0.005(5) C10 0.040(7) 0.021(5) 0.018(5) -0.004(4) 0.003(5) -0.003(5) C12 0.043(7) 0.025(6) 0.023(6) -0.001(4) -0.004(5) 0.003(5) C13 0.042(8) 0.024(6) 0.025(6) -0.009(5) -0.007(5) 0.012(6) C9' 0.015(5) 0.030(6) 0.057(8) -0.008(6) 0.000(5) 0.001(5) C10' 0.033(7) 0.016(5) 0.059(9) -0.012(5) -0.007(7) -0.008(5) C12' 0.036(7) 0.016(5) 0.041(8) -0.006(5) 0.004(6) -0.008(5) C13' 0.028(6) 0.020(5) 0.037(7) 0.005(5) -0.006(5) 0.002(5) C11 0.028(3) 0.022(2) 0.026(3) 0.002(2) 0.005(2) 0.001(2) C14 0.032(3) 0.022(2) 0.028(3) 0.000(2) 0.009(2) -0.004(2) N1 0.024(2) 0.0178(19) 0.027(2) -0.0023(16) 0.0004(17) -0.0004(17) O1 0.0286(19) 0.029(2) 0.0233(19) -0.0008(15) 0.0013(15) -0.0090(16) O2 0.051(3) 0.044(3) 0.023(2) -0.0037(18) 0.0087(18) -0.027(2) O3 0.064(3) 0.031(2) 0.032(2) -0.0057(18) 0.018(2) -0.025(2) O4 0.054(3) 0.032(2) 0.048(3) -0.008(2) -0.018(2) 0.016(2) O5 0.028(2) 0.0215(19) 0.040(2) -0.0078(16) 0.0004(17) 0.0003(16) O1W 0.024(2) 0.068(3) 0.042(3) -0.023(2) 0.0047(18) 0.005(2) O2W 0.033(2) 0.0242(19) 0.048(3) -0.0040(18) 0.0146(19) 0.0007(17) O3W 0.032(2) 0.027(2) 0.0227(19) -0.0036(15) 0.0044(16) -0.0077(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Ni1 O2 1.998(4) . ? Ni1 O1 2.036(4) . ? Ni1 O5 2.050(4) 4_566 ? Ni1 O2W 2.058(4) . ? Ni1 O3W 2.069(4) . ? Ni1 O1W 2.102(4) . ? C1 O1 1.256(6) . ? C1 N1 1.388(6) . ? C1 C2 1.444(7) . ? C2 C3 1.372(8) . ? C2 C6 1.510(7) . ? C3 C4 1.395(8) . ? C3 H3 0.9300 . ? C4 C5 1.345(9) . ? C4 H4 0.9300 . ? C5 N1 1.355(7) . ? C5 H5 0.9300 . ? C6 O3 1.236(7) . ? C6 O2 1.270(7) . ? C7 N1 1.484(7) . ? C7 C8 1.520(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C12' 1.340(14) . ? C8 C9' 1.362(13) . ? C8 C13 1.371(13) . ? C8 C9 1.439(12) . ? C9 C10 1.404(15) . ? C9 H9 0.9300 . ? C10 C11 1.376(12) . ? C10 H10 0.9300 . ? C12 C11 1.350(13) . ? C12 C13 1.395(16) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C9' C10' 1.363(16) . ? C9' H9' 0.9300 . ? C10' C11 1.420(14) . ? C10' H10' 0.9300 . ? C12' C13' 1.387(16) . ? C12' H12' 0.9300 . ? C13' C11 1.413(13) . ? C13' H13' 0.9300 . ? C11 C14 1.510(7) . ? C14 O4 1.236(7) . ? C14 O5 1.265(6) . ? O5 Ni1 2.050(4) 4_565 ? O3W H3B 0.903(10) . ? O3W H3A 0.901(10) . ? 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 Ni1 O1 88.18(16) . . ? O2 Ni1 O5 176.24(17) . 4_566 ? O1 Ni1 O5 88.09(16) . 4_566 ? O2 Ni1 O2W 90.91(19) . . ? O1 Ni1 O2W 92.29(17) . . ? O5 Ni1 O2W 89.73(17) 4_566 . ? O2 Ni1 O3W 91.68(16) . . ? O1 Ni1 O3W 176.93(17) . . ? O5 Ni1 O3W 92.02(16) 4_566 . ? O2W Ni1 O3W 90.77(17) . . ? O2 Ni1 O1W 89.4(2) . . ? O1 Ni1 O1W 88.92(17) . . ? O5 Ni1 O1W 90.03(19) 4_566 . ? O2W Ni1 O1W 178.76(19) . . ? O3W Ni1 O1W 88.02(17) . . ? O1 C1 N1 117.7(5) . . ? O1 C1 C2 126.6(5) . . ? N1 C1 C2 115.7(5) . . ? C3 C2 C1 119.8(5) . . ? C3 C2 C6 118.1(5) . . ? C1 C2 C6 122.1(5) . . ? C2 C3 C4 121.1(5) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.0(5) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 N1 121.4(5) . . ? C4 C5 H5 119.3 . . ? N1 C5 H5 119.3 . . ? O3 C6 O2 122.6(5) . . ? O3 C6 C2 117.5(5) . . ? O2 C6 C2 119.9(5) . . ? N1 C7 C8 111.9(4) . . ? N1 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C12' C8 C9' 121.3(8) . . ? C12' C8 C13 37.6(7) . . ? C9' C8 C13 102.7(9) . . ? C12' C8 C9 105.1(8) . . ? C9' C8 C9 44.7(7) . . ? C13 C8 C9 116.6(7) . . ? C12' C8 C7 122.1(6) . . ? C9' C8 C7 116.3(6) . . ? C13 C8 C7 123.7(6) . . ? C9 C8 C7 119.6(6) . . ? C10 C9 C8 120.5(9) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 118.9(9) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C11 C12 C13 119.9(10) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C8 C13 C12 122.3(10) . . ? C8 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C8 C9' C10' 119.4(10) . . ? C8 C9' H9' 120.3 . . ? C10' C9' H9' 120.3 . . ? C9' C10' C11 122.6(10) . . ? C9' C10' H10' 118.7 . . ? C11 C10' H10' 118.7 . . ? C8 C12' C13' 120.0(10) . . ? C8 C12' H12' 120.0 . . ? C13' C12' H12' 120.0 . . ? C12' C13' C11 121.7(10) . . ? C12' C13' H13' 119.2 . . ? C11 C13' H13' 119.2 . . ? C12 C11 C10 121.6(8) . . ? C12 C11 C13' 37.8(7) . . ? C10 C11 C13' 104.9(8) . . ? C12 C11 C10' 102.8(9) . . ? C10 C11 C10' 42.2(8) . . ? C13' C11 C10' 114.5(7) . . ? C12 C11 C14 121.9(7) . . ? C10 C11 C14 116.4(6) . . ? C13' C11 C14 122.7(6) . . ? C10' C11 C14 122.8(6) . . ? O4 C14 O5 124.7(5) . . ? O4 C14 C11 119.5(5) . . ? O5 C14 C11 115.7(5) . . ? C5 N1 C1 122.9(5) . . ? C5 N1 C7 117.7(5) . . ? C1 N1 C7 119.3(5) . . ? C1 O1 Ni1 122.1(3) . . ? C6 O2 Ni1 130.7(4) . . ? C14 O5 Ni1 128.7(4) . 4_565 ? Ni1 O3W H3B 104(5) . . ? Ni1 O3W H3A 133(5) . . ? H3B O3W H3A 102(6) . . ? 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 O1 C1 C2 C3 -178.4(5) . . . . ? N1 C1 C2 C3 0.7(8) . . . . ? O1 C1 C2 C6 1.4(9) . . . . ? N1 C1 C2 C6 -179.4(5) . . . . ? C1 C2 C3 C4 -1.3(9) . . . . ? C6 C2 C3 C4 178.8(5) . . . . ? C2 C3 C4 C5 0.9(9) . . . . ? C3 C4 C5 N1 0.1(9) . . . . ? C3 C2 C6 O3 12.8(8) . . . . ? C1 C2 C6 O3 -167.0(5) . . . . ? C3 C2 C6 O2 -165.7(6) . . . . ? C1 C2 C6 O2 14.4(8) . . . . ? N1 C7 C8 C12' 40.3(11) . . . . ? N1 C7 C8 C9' -146.0(8) . . . . ? N1 C7 C8 C13 85.4(11) . . . . ? N1 C7 C8 C9 -95.1(8) . . . . ? C12' C8 C9 C10 40.6(14) . . . . ? C9' C8 C9 C10 -78.8(14) . . . . ? C13 C8 C9 C10 2.1(17) . . . . ? C7 C8 C9 C10 -177.5(9) . . . . ? C8 C9 C10 C11 1.0(18) . . . . ? C12' C8 C13 C12 -83.7(17) . . . . ? C9' C8 C13 C12 41.7(17) . . . . ? C9 C8 C13 C12 -3.7(19) . . . . ? C7 C8 C13 C12 175.9(11) . . . . ? C11 C12 C13 C8 2(2) . . . . ? C12' C8 C9' C10' -9.3(19) . . . . ? C13 C8 C9' C10' -44.9(16) . . . . ? C9 C8 C9' C10' 70.3(14) . . . . ? C7 C8 C9' C10' 176.8(12) . . . . ? C8 C9' C10' C11 7(2) . . . . ? C9' C8 C12' C13' 5.2(19) . . . . ? C13 C8 C12' C13' 73.7(15) . . . . ? C9 C8 C12' C13' -40.6(16) . . . . ? C7 C8 C12' C13' 178.7(11) . . . . ? C8 C12' C13' C11 1(2) . . . . ? C13 C12 C11 C10 1.1(19) . . . . ? C13 C12 C11 C13' 73.5(15) . . . . ? C13 C12 C11 C10' -40.1(16) . . . . ? C13 C12 C11 C14 177.2(11) . . . . ? C9 C10 C11 C12 -2.6(17) . . . . ? C9 C10 C11 C13' -39.8(14) . . . . ? C9 C10 C11 C10' 70.4(13) . . . . ? C9 C10 C11 C14 -178.9(9) . . . . ? C12' C13' C11 C12 -82.0(17) . . . . ? C12' C13' C11 C10 40.9(16) . . . . ? C12' C13' C11 C10' -3.0(18) . . . . ? C12' C13' C11 C14 176.7(11) . . . . ? C9' C10' C11 C12 36.8(18) . . . . ? C9' C10' C11 C10 -86.6(17) . . . . ? C9' C10' C11 C13' -1(2) . . . . ? C9' C10' C11 C14 179.1(12) . . . . ? C12 C11 C14 O4 -25.8(12) . . . . ? C10 C11 C14 O4 150.4(8) . . . . ? C13' C11 C14 O4 19.2(11) . . . . ? C10' C11 C14 O4 -161.2(10) . . . . ? C12 C11 C14 O5 156.5(10) . . . . ? C10 C11 C14 O5 -27.3(9) . . . . ? C13' C11 C14 O5 -158.5(9) . . . . ? C10' C11 C14 O5 21.1(11) . . . . ? C4 C5 N1 C1 -0.7(9) . . . . ? C4 C5 N1 C7 179.8(5) . . . . ? O1 C1 N1 C5 179.5(5) . . . . ? C2 C1 N1 C5 0.2(7) . . . . ? O1 C1 N1 C7 -1.0(7) . . . . ? C2 C1 N1 C7 179.8(4) . . . . ? C8 C7 N1 C5 79.8(6) . . . . ? C8 C7 N1 C1 -99.8(6) . . . . ? N1 C1 O1 Ni1 150.1(4) . . . . ? C2 C1 O1 Ni1 -30.7(7) . . . . ? O2 Ni1 O1 C1 34.3(4) . . . . ? O5 Ni1 O1 C1 -145.2(4) 4_566 . . . ? O2W Ni1 O1 C1 125.1(4) . . . . ? O3W Ni1 O1 C1 -53(3) . . . . ? O1W Ni1 O1 C1 -55.2(4) . . . . ? O3 C6 O2 Ni1 -175.8(5) . . . . ? C2 C6 O2 Ni1 2.7(9) . . . . ? O1 Ni1 O2 C6 -21.5(6) . . . . ? O5 Ni1 O2 C6 -14(3) 4_566 . . . ? O2W Ni1 O2 C6 -113.8(6) . . . . ? O3W Ni1 O2 C6 155.4(6) . . . . ? O1W Ni1 O2 C6 67.4(6) . . . . ? O4 C14 O5 Ni1 -24.1(9) . . . 4_565 ? C11 C14 O5 Ni1 153.5(4) . . . 4_565 ? 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 O3W H3B O4 0.903(10) 1.85(3) 2.699(6) 156(7) 4_566 O3W H3A O3 0.901(10) 1.79(2) 2.669(6) 165(7) 3_767 _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.714 _refine_diff_density_min -0.798 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 938795' ####################################################################### # # 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_Compound-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Cu N O5' _chemical_formula_sum 'C14 H9 Cu N O5' _chemical_formula_weight 334.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_space_group_name_hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4130(12) _cell_length_b 5.3340(7) _cell_length_c 13.2840(14) _cell_angle_alpha 90.00 _cell_angle_beta 97.520(13) _cell_angle_gamma 90.00 _cell_volume 590.99(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 664 _cell_measurement_theta_min 3.6755 _cell_measurement_theta_max 29.1709 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.881 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 338 _exptl_absorpt_coefficient_mu 1.871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6623 _exptl_absorpt_correction_T_max 0.7060 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2623 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0958 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 29.23 _reflns_number_total 1976 _reflns_number_gt 1581 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^ > 2\s(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^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(3) _refine_ls_number_reflns 1976 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 -0.04429(8) 0.37199(19) 0.86590(5) 0.0279(2) Uani 1 1 d . . . C6 C 0.1854(8) 0.7016(14) 0.9794(4) 0.0253(16) Uani 1 1 d . . . C1 C 0.2731(8) 0.4871(14) 0.8260(5) 0.0273(16) Uani 1 1 d . . . C2 C 0.2982(8) 0.6783(13) 0.9029(4) 0.0241(16) Uani 1 1 d . . . C3 C 0.4324(8) 0.8262(17) 0.9111(5) 0.033(2) Uani 1 1 d . . . H3 H 0.4438 0.9556 0.9584 0.039 Uiso 1 1 calc R . . C4 C 0.5539(8) 0.7852(14) 0.8487(4) 0.034(2) Uani 1 1 d . . . H4 H 0.6439 0.8880 0.8529 0.041 Uiso 1 1 calc R . . C5 C 0.5344(9) 0.5893(15) 0.7819(5) 0.0357(19) Uani 1 1 d . . . H5 H 0.6163 0.5502 0.7439 0.043 Uiso 1 1 calc R . . C7 C 0.3822(9) 0.2472(14) 0.6954(4) 0.0307(17) Uani 1 1 d . . . H7A H 0.3170 0.1156 0.7193 0.037 Uiso 1 1 calc R . . H7B H 0.4876 0.1775 0.6911 0.037 Uiso 1 1 calc R . . C8 C 0.3080(8) 0.3265(15) 0.5902(4) 0.0276(19) Uani 1 1 d . . . C9 C 0.1996(9) 0.1707(15) 0.5352(5) 0.0348(18) Uani 1 1 d . . . H9 H 0.1647 0.0282 0.5663 0.042 Uiso 1 1 calc R . . C10 C 0.1402(9) 0.2191(14) 0.4347(5) 0.0347(19) Uani 1 1 d . . . H10 H 0.0700 0.1079 0.3979 0.042 Uiso 1 1 calc R . . C11 C 0.1883(8) 0.4378(12) 0.3902(5) 0.0283(19) Uani 1 1 d . . . C12 C 0.2928(8) 0.6011(14) 0.4466(4) 0.0263(16) Uani 1 1 d . . . H12 H 0.3218 0.7506 0.4180 0.032 Uiso 1 1 calc R . . C13 C 0.3537(8) 0.5418(14) 0.5449(5) 0.0306(17) Uani 1 1 d . . . H13 H 0.4269 0.6494 0.5814 0.037 Uiso 1 1 calc R . . C14 C 0.1252(9) 0.5015(15) 0.2794(5) 0.0316(17) Uani 1 1 d . . . N1 N 0.3982(6) 0.4508(10) 0.7701(4) 0.0242(14) Uani 1 1 d . . . O2 O 0.0585(5) 0.5753(9) 0.9749(3) 0.0291(12) Uani 1 1 d . . . O3 O 0.2255(5) 0.8495(15) 1.0537(3) 0.0303(11) Uani 1 1 d . . . O1 O 0.1531(5) 0.3516(15) 0.8051(3) 0.0343(12) Uani 1 1 d . . . O4 O 0.0496(7) 0.3456(16) 0.2265(3) 0.0594(17) Uani 1 1 d . . . O5 O 0.1611(6) 0.7215(10) 0.2511(3) 0.0329(12) 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 Cu1 0.0278(4) 0.0373(5) 0.0189(3) -0.0036(5) 0.0048(3) -0.0020(6) C6 0.030(4) 0.031(4) 0.016(3) 0.007(3) 0.004(3) 0.005(4) C1 0.031(4) 0.032(4) 0.018(3) 0.012(3) 0.005(3) 0.007(3) C2 0.024(4) 0.032(4) 0.014(3) 0.005(3) -0.003(3) 0.008(3) C3 0.033(4) 0.040(6) 0.024(3) 0.003(4) 0.001(2) -0.002(4) C4 0.028(4) 0.050(6) 0.024(3) 0.012(3) -0.001(3) -0.005(3) C5 0.033(4) 0.054(5) 0.022(3) 0.011(4) 0.008(3) 0.010(4) C7 0.039(4) 0.031(4) 0.024(3) 0.001(3) 0.011(3) 0.008(4) C8 0.030(3) 0.037(6) 0.017(3) 0.003(3) 0.008(2) 0.005(4) C9 0.046(5) 0.033(5) 0.028(4) 0.004(4) 0.014(3) -0.001(4) C10 0.040(5) 0.027(4) 0.035(4) 0.001(4) -0.007(3) -0.009(4) C11 0.038(4) 0.026(5) 0.020(3) -0.001(3) 0.001(3) 0.014(3) C12 0.031(4) 0.028(4) 0.021(3) 0.000(3) 0.010(3) -0.001(3) C13 0.033(4) 0.036(5) 0.023(3) -0.001(3) 0.005(3) -0.002(4) C14 0.033(4) 0.041(5) 0.022(3) -0.004(4) 0.006(3) 0.004(4) N1 0.021(3) 0.033(4) 0.019(3) 0.006(2) 0.005(2) 0.004(3) O2 0.031(3) 0.035(3) 0.022(2) -0.007(2) 0.0074(19) -0.003(3) O3 0.027(2) 0.046(3) 0.0188(19) -0.011(3) 0.0046(15) -0.003(3) O1 0.027(2) 0.046(3) 0.032(2) -0.012(3) 0.0122(17) -0.009(4) O4 0.093(4) 0.046(4) 0.032(2) 0.001(4) -0.019(3) -0.015(5) O5 0.037(3) 0.037(3) 0.023(2) 0.011(2) -0.002(2) 0.000(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O5 1.904(4) 2_546 ? Cu1 O2 1.922(5) . ? Cu1 O1 1.943(4) . ? Cu1 O3 1.977(4) 2_547 ? C6 O2 1.257(8) . ? C6 O3 1.274(8) . ? C6 C2 1.483(9) . ? C1 O1 1.243(8) . ? C1 N1 1.379(8) . ? C1 C2 1.439(9) . ? C2 C3 1.370(10) . ? C3 C4 1.415(9) . ? C3 H3 0.9300 . ? C4 C5 1.366(10) . ? C4 H4 0.9300 . ? C5 N1 1.356(9) . ? C5 H5 0.9300 . ? C7 N1 1.464(8) . ? C7 C8 1.515(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.372(10) . ? C8 C13 1.374(10) . ? C9 C10 1.387(8) . ? C9 H9 0.9300 . ? C10 C11 1.392(9) . ? C10 H10 0.9300 . ? C11 C12 1.386(9) . ? C11 C14 1.536(9) . ? C12 C13 1.376(8) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O4 1.214(9) . ? C14 O5 1.281(9) . ? O3 Cu1 1.977(4) 2_557 ? O5 Cu1 1.904(4) 2_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 O5 Cu1 O2 170.5(2) 2_546 . ? O5 Cu1 O1 90.9(2) 2_546 . ? O2 Cu1 O1 91.1(2) . . ? O5 Cu1 O3 93.6(2) 2_546 2_547 ? O2 Cu1 O3 86.0(2) . 2_547 ? O1 Cu1 O3 169.5(3) . 2_547 ? O2 C6 O3 120.4(6) . . ? O2 C6 C2 122.6(6) . . ? O3 C6 C2 117.0(6) . . ? O1 C1 N1 116.9(6) . . ? O1 C1 C2 127.6(6) . . ? N1 C1 C2 115.5(6) . . ? C3 C2 C1 120.4(7) . . ? C3 C2 C6 119.5(6) . . ? C1 C2 C6 119.9(6) . . ? C2 C3 C4 121.1(7) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 117.6(7) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? N1 C5 C4 121.3(7) . . ? N1 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? N1 C7 C8 114.1(6) . . ? N1 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N1 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C13 118.5(6) . . ? C9 C8 C7 119.2(7) . . ? C13 C8 C7 122.2(7) . . ? C8 C9 C10 122.0(7) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C9 C10 C11 118.5(7) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C12 C11 C10 119.7(6) . . ? C12 C11 C14 119.6(6) . . ? C10 C11 C14 120.6(6) . . ? C13 C12 C11 120.0(7) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C8 C13 C12 121.1(7) . . ? C8 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? O4 C14 O5 125.7(6) . . ? O4 C14 C11 119.5(7) . . ? O5 C14 C11 114.7(6) . . ? C5 N1 C1 123.7(6) . . ? C5 N1 C7 118.9(6) . . ? C1 N1 C7 117.4(5) . . ? C6 O2 Cu1 129.3(4) . . ? C6 O3 Cu1 108.1(4) . 2_557 ? C1 O1 Cu1 126.0(5) . . ? C14 O5 Cu1 120.6(4) . 2_556 ? 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 O1 C1 C2 C3 -174.6(7) . . . . ? N1 C1 C2 C3 5.9(9) . . . . ? O1 C1 C2 C6 10.6(10) . . . . ? N1 C1 C2 C6 -168.9(5) . . . . ? O2 C6 C2 C3 178.4(6) . . . . ? O3 C6 C2 C3 -4.4(10) . . . . ? O2 C6 C2 C1 -6.7(9) . . . . ? O3 C6 C2 C1 170.4(6) . . . . ? C1 C2 C3 C4 -3.9(10) . . . . ? C6 C2 C3 C4 170.9(6) . . . . ? C2 C3 C4 C5 -1.6(10) . . . . ? C3 C4 C5 N1 5.0(9) . . . . ? N1 C7 C8 C9 -139.5(7) . . . . ? N1 C7 C8 C13 45.0(9) . . . . ? C13 C8 C9 C10 2.7(11) . . . . ? C7 C8 C9 C10 -173.0(6) . . . . ? C8 C9 C10 C11 -2.5(11) . . . . ? C9 C10 C11 C12 -0.2(11) . . . . ? C9 C10 C11 C14 -179.5(7) . . . . ? C10 C11 C12 C13 2.6(11) . . . . ? C14 C11 C12 C13 -178.1(6) . . . . ? C9 C8 C13 C12 -0.1(11) . . . . ? C7 C8 C13 C12 175.4(6) . . . . ? C11 C12 C13 C8 -2.5(11) . . . . ? C12 C11 C14 O4 171.1(7) . . . . ? C10 C11 C14 O4 -9.5(11) . . . . ? C12 C11 C14 O5 -8.0(10) . . . . ? C10 C11 C14 O5 171.4(6) . . . . ? C4 C5 N1 C1 -2.9(9) . . . . ? C4 C5 N1 C7 178.4(5) . . . . ? O1 C1 N1 C5 177.8(6) . . . . ? C2 C1 N1 C5 -2.6(8) . . . . ? O1 C1 N1 C7 -3.4(8) . . . . ? C2 C1 N1 C7 176.1(5) . . . . ? C8 C7 N1 C5 -89.8(7) . . . . ? C8 C7 N1 C1 91.3(7) . . . . ? O3 C6 O2 Cu1 171.5(5) . . . . ? C2 C6 O2 Cu1 -11.4(9) . . . . ? O5 Cu1 O2 C6 -82.8(14) 2_546 . . . ? O1 Cu1 O2 C6 19.3(6) . . . . ? O3 Cu1 O2 C6 -170.8(6) 2_547 . . . ? O2 C6 O3 Cu1 -9.0(8) . . . 2_557 ? C2 C6 O3 Cu1 173.8(5) . . . 2_557 ? N1 C1 O1 Cu1 -176.6(4) . . . . ? C2 C1 O1 Cu1 3.9(10) . . . . ? O5 Cu1 O1 C1 155.5(6) 2_546 . . . ? O2 Cu1 O1 C1 -15.2(6) . . . . ? O3 Cu1 O1 C1 -89(2) 2_547 . . . ? O4 C14 O5 Cu1 19.9(10) . . . 2_556 ? C11 C14 O5 Cu1 -161.0(5) . . . 2_556 ? _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.604 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 938796' ####################################################################### # # 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_Compound-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cd N O5.50' _chemical_formula_sum 'C14 H10 Cd N O5.50' _chemical_formula_weight 392.63 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3 c' _symmetry_space_group_name_hall '-R 3 2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+5/6' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+7/6' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z-1/6' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+1/6' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' _cell_length_a 18.4215(3) _cell_length_b 18.4215(3) _cell_length_c 47.8464(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 14061.4(5) _cell_formula_units_Z 36 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13672 _cell_measurement_theta_min 3.2359 _cell_measurement_theta_max 29.1944 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6948 _exptl_absorpt_coefficient_mu 1.420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7842 _exptl_absorpt_correction_T_max 0.8152 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32184 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -56 _diffrn_reflns_limit_l_max 63 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 29.26 _reflns_number_total 4062 _reflns_number_gt 3016 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2\s(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. For o2w, some anisotropic displacement ellipsoids were rather elongated which led us to use the DELU restraints. For c3 and c5, some anisotropic displacement ellipsoids were rather elongated which led us to use the ISOR restraints. For C3, C4 and c5, some anisotropic displacement ellipsoids were rather elongated which led us to use the SIMU restraints. ; _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^)+(0.0533P)^2^+72.7064P] 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 4062 _refine_ls_number_parameters 221 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.154 _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 Cd1 Cd 0.882770(19) 0.089106(19) 0.017805(6) 0.03168(12) Uani 1 1 d . . . C1 C 0.7982(3) 0.0024(3) 0.07567(9) 0.0373(10) Uani 1 1 d . A . C2 C 0.8129(4) -0.0667(3) 0.07219(10) 0.0553(11) Uani 1 1 d U . . C3 C 0.7870(4) -0.1264(4) 0.09289(12) 0.0688(12) Uani 1 1 d U . . H3 H 0.7976 -0.1705 0.0910 0.083 Uiso 1 1 calc R . . C4 C 0.7447(5) -0.1222(4) 0.11685(13) 0.0796(13) Uani 1 1 d U . . H4 H 0.7238 -0.1651 0.1300 0.096 Uiso 1 1 calc R . . C5 C 0.7354(5) -0.0558(4) 0.12030(13) 0.0801(15) Uani 1 1 d U A . H5 H 0.7097 -0.0515 0.1364 0.096 Uiso 1 1 calc R . . C6 C 0.8484(3) -0.0817(3) 0.04609(8) 0.0348(9) Uani 1 1 d . A . C7 C 0.7508(3) 0.0775(3) 0.10608(11) 0.0544(14) Uani 1 1 d . A . H7A H 0.7051 0.0613 0.1192 0.065 Uiso 1 1 calc R . . H7B H 0.7350 0.0927 0.0887 0.065 Uiso 1 1 calc R . . C8 C 0.8279(3) 0.1533(3) 0.11745(10) 0.0432(11) Uani 1 1 d . . . C9 C 0.8307(14) 0.2289(13) 0.1153(6) 0.050(5) Uani 0.46(6) 1 d P A 1 H9 H 0.7877 0.2323 0.1064 0.060 Uiso 0.46(6) 1 calc PR A 1 C10 C 0.8977(15) 0.3001(17) 0.1265(6) 0.055(6) Uani 0.46(6) 1 d P A 1 H10 H 0.8979 0.3506 0.1254 0.066 Uiso 0.46(6) 1 calc PR A 1 C9' C 0.856(2) 0.2289(13) 0.1039(9) 0.087(9) Uani 0.54(6) 1 d P A 2 H9' H 0.8312 0.2305 0.0872 0.104 Uiso 0.54(6) 1 calc PR A 2 C10' C 0.921(3) 0.3033(14) 0.1151(10) 0.099(13) Uani 0.54(6) 1 d P A 2 H10' H 0.9368 0.3547 0.1068 0.119 Uiso 0.54(6) 1 calc PR A 2 C11 C 0.9630(3) 0.2991(3) 0.13906(10) 0.0404(10) Uani 1 1 d . . . C12 C 0.9475(4) 0.2231(3) 0.14738(13) 0.0607(15) Uani 1 1 d . A . H12 H 0.9825 0.2189 0.1605 0.073 Uiso 1 1 calc R . . C13 C 0.8796(4) 0.1501(3) 0.13671(14) 0.0682(17) Uani 1 1 d . A . H13 H 0.8699 0.0982 0.1430 0.082 Uiso 1 1 calc R . . C14 C 1.0355(3) 0.3789(3) 0.15018(10) 0.0406(10) Uani 1 1 d . A . N1 N 0.7621(3) 0.0053(2) 0.10107(8) 0.0500(11) Uani 1 1 d . . . O1 O 0.8126(2) 0.0590(2) 0.05886(6) 0.0417(7) Uani 1 1 d . . . O2 O 0.8438(2) -0.04825(18) 0.02347(6) 0.0383(7) Uani 1 1 d . . . O3 O 0.8772(3) -0.1293(2) 0.04777(7) 0.0555(9) Uani 1 1 d . . . O4 O 1.0291(2) 0.4438(2) 0.14797(8) 0.0574(10) Uani 1 1 d . . . O5 O 1.0945(2) 0.3738(2) 0.16137(8) 0.0511(8) Uani 1 1 d . . . O1W O 0.8883(12) 0.4814(12) 0.1284(5) 0.114(6) Uani 0.33 1 d P . . O2W O 1.0000 0.0000 0.147(2) 0.46(7) Uani 0.50 3 d SP . . 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 Cd1 0.03346(19) 0.02857(18) 0.02887(18) 0.00103(11) 0.00240(11) 0.01241(13) C1 0.034(2) 0.034(2) 0.032(2) -0.0044(17) 0.0106(17) 0.0081(18) C2 0.093(3) 0.0356(18) 0.0351(19) 0.0043(16) 0.0196(19) 0.0307(19) C3 0.106(3) 0.0427(17) 0.0444(18) 0.0072(15) 0.0231(18) 0.0271(18) C4 0.115(3) 0.0493(18) 0.0489(19) 0.0067(16) 0.029(2) 0.022(2) C5 0.114(3) 0.051(2) 0.047(2) 0.0026(19) 0.036(2) 0.020(2) C6 0.046(3) 0.031(2) 0.029(2) -0.0054(16) -0.0033(18) 0.020(2) C7 0.038(3) 0.049(3) 0.059(3) -0.023(2) 0.013(2) 0.009(2) C8 0.033(2) 0.042(3) 0.048(3) -0.013(2) 0.004(2) 0.014(2) C9 0.043(8) 0.047(7) 0.054(11) -0.008(7) -0.016(7) 0.018(6) C10 0.047(9) 0.034(8) 0.078(14) -0.005(9) -0.009(9) 0.017(7) C9' 0.091(17) 0.065(9) 0.082(17) -0.006(10) -0.048(15) 0.021(10) C10' 0.10(2) 0.036(7) 0.12(2) 0.017(12) -0.074(17) 0.002(10) C11 0.038(2) 0.031(2) 0.047(3) -0.0062(19) -0.0024(19) 0.0132(19) C12 0.064(4) 0.043(3) 0.072(4) -0.008(3) -0.026(3) 0.024(3) C13 0.072(4) 0.032(3) 0.088(4) -0.004(3) -0.021(3) 0.016(3) C14 0.040(2) 0.035(2) 0.041(2) -0.0079(19) 0.0048(19) 0.014(2) N1 0.049(2) 0.033(2) 0.043(2) -0.0109(17) 0.0190(18) 0.0022(18) O1 0.0501(19) 0.0435(18) 0.0377(16) 0.0022(14) 0.0117(14) 0.0279(16) O2 0.058(2) 0.0329(15) 0.0254(14) -0.0010(12) 0.0032(13) 0.0241(15) O3 0.084(3) 0.063(2) 0.0415(19) -0.0011(16) -0.0029(18) 0.053(2) O4 0.047(2) 0.0327(18) 0.083(3) -0.0076(17) -0.0052(18) 0.0123(16) O5 0.0430(19) 0.051(2) 0.058(2) -0.0168(17) -0.0118(16) 0.0227(17) O1W 0.114(14) 0.079(11) 0.154(18) -0.011(11) -0.015(12) 0.052(10) O2W 0.15(2) 0.15(2) 1.1(2) 0.000 0.000 0.076(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cd1 O4 2.209(3) 17_554 ? Cd1 O1 2.263(3) . ? Cd1 O2 2.275(3) . ? Cd1 O2 2.279(3) 20_665 ? Cd1 O5 2.282(3) 30_445 ? Cd1 O3 2.311(3) 3_765 ? C1 O1 1.235(5) . ? C1 N1 1.399(5) . ? C1 C2 1.436(7) . ? C2 C3 1.376(7) . ? C2 C6 1.498(6) . ? C3 C4 1.409(8) . ? C3 H3 0.9300 . ? C4 C5 1.327(9) . ? C4 H4 0.9300 . ? C5 N1 1.342(7) . ? C5 H5 0.9300 . ? C6 O3 1.233(5) . ? C6 O2 1.268(5) . ? C7 N1 1.464(7) . ? C7 C8 1.510(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.348(8) . ? C8 C9 1.37(2) . ? C8 C9' 1.38(2) . ? C9 C10 1.38(3) . ? C9 H9 0.9300 . ? C10 C11 1.35(3) . ? C10 H10 0.9300 . ? C9' C10' 1.40(3) . ? C9' H9' 0.9300 . ? C10' C11 1.40(2) . ? C10' H10' 0.9300 . ? C11 C12 1.342(7) . ? C11 C14 1.505(6) . ? C12 C13 1.397(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O5 1.256(6) . ? C14 O4 1.264(6) . ? O2 Cd1 2.279(3) 21_545 ? O3 Cd1 2.311(3) 2_645 ? O4 Cd1 2.209(3) 17_554 ? O5 Cd1 2.282(3) 36_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 O4 Cd1 O1 94.17(13) 17_554 . ? O4 Cd1 O2 171.99(12) 17_554 . ? O1 Cd1 O2 78.44(10) . . ? O4 Cd1 O2 90.78(13) 17_554 20_665 ? O1 Cd1 O2 175.01(11) . 20_665 ? O2 Cd1 O2 96.58(14) . 20_665 ? O4 Cd1 O5 91.67(13) 17_554 30_445 ? O1 Cd1 O5 89.53(13) . 30_445 ? O2 Cd1 O5 91.36(12) . 30_445 ? O2 Cd1 O5 90.97(12) 20_665 30_445 ? O4 Cd1 O3 87.51(15) 17_554 3_765 ? O1 Cd1 O3 81.17(12) . 3_765 ? O2 Cd1 O3 88.30(13) . 3_765 ? O2 Cd1 O3 98.43(11) 20_665 3_765 ? O5 Cd1 O3 170.57(13) 30_445 3_765 ? O1 C1 N1 116.0(4) . . ? O1 C1 C2 128.0(4) . . ? N1 C1 C2 116.0(4) . . ? C3 C2 C1 118.7(5) . . ? C3 C2 C6 117.5(5) . . ? C1 C2 C6 123.6(4) . . ? C2 C3 C4 121.5(6) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 118.7(6) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 N1 121.7(5) . . ? C4 C5 H5 119.1 . . ? N1 C5 H5 119.1 . . ? O3 C6 O2 123.9(4) . . ? O3 C6 C2 117.3(4) . . ? O2 C6 C2 118.7(4) . . ? N1 C7 C8 113.9(4) . . ? N1 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N1 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C13 C8 C9 115.3(10) . . ? C13 C8 C9' 116.6(10) . . ? C9 C8 C9' 30.2(14) . . ? C13 C8 C7 124.3(5) . . ? C9 C8 C7 117.0(9) . . ? C9' C8 C7 118.0(9) . . ? C8 C9 C10 119.8(19) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 122(2) . . ? C11 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C8 C9' C10' 120.9(17) . . ? C8 C9' H9' 119.5 . . ? C10' C9' H9' 119.5 . . ? C9' C10' C11 118.9(17) . . ? C9' C10' H10' 120.5 . . ? C11 C10' H10' 120.5 . . ? C12 C11 C10 114.8(13) . . ? C12 C11 C10' 117.6(11) . . ? C10 C11 C10' 28.6(19) . . ? C12 C11 C14 122.4(5) . . ? C10 C11 C14 120.4(12) . . ? C10' C11 C14 118.6(10) . . ? C11 C12 C13 121.2(5) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C8 C13 C12 121.3(5) . . ? C8 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? O5 C14 O4 126.9(4) . . ? O5 C14 C11 117.2(4) . . ? O4 C14 C11 115.9(4) . . ? C5 N1 C1 123.0(5) . . ? C5 N1 C7 119.4(4) . . ? C1 N1 C7 117.6(4) . . ? C1 O1 Cd1 128.9(3) . . ? C6 O2 Cd1 125.5(3) . . ? C6 O2 Cd1 125.1(3) . 21_545 ? Cd1 O2 Cd1 109.36(12) . 21_545 ? C6 O3 Cd1 137.7(3) . 2_645 ? C14 O4 Cd1 130.1(3) . 17_554 ? C14 O5 Cd1 137.6(3) . 36_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 O1 C1 C2 C3 -175.6(6) . . . . ? N1 C1 C2 C3 3.5(8) . . . . ? O1 C1 C2 C6 -1.2(9) . . . . ? N1 C1 C2 C6 177.9(5) . . . . ? C1 C2 C3 C4 1.7(10) . . . . ? C6 C2 C3 C4 -173.1(6) . . . . ? C2 C3 C4 C5 -4.9(12) . . . . ? C3 C4 C5 N1 2.7(12) . . . . ? C3 C2 C6 O3 -22.9(8) . . . . ? C1 C2 C6 O3 162.6(5) . . . . ? C3 C2 C6 O2 154.0(6) . . . . ? C1 C2 C6 O2 -20.5(8) . . . . ? N1 C7 C8 C13 -39.8(7) . . . . ? N1 C7 C8 C9 162.2(15) . . . . ? N1 C7 C8 C9' 128(3) . . . . ? C13 C8 C9 C10 17(2) . . . . ? C9' C8 C9 C10 -83(3) . . . . ? C7 C8 C9 C10 176.9(13) . . . . ? C8 C9 C10 C11 2(3) . . . . ? C13 C8 C9' C10' -18(3) . . . . ? C9 C8 C9' C10' 77(3) . . . . ? C7 C8 C9' C10' 172.9(17) . . . . ? C8 C9' C10' C11 5(3) . . . . ? C9 C10 C11 C12 -19(2) . . . . ? C9 C10 C11 C10' 83(4) . . . . ? C9 C10 C11 C14 178.2(13) . . . . ? C9' C10' C11 C12 11(4) . . . . ? C9' C10' C11 C10 -81(4) . . . . ? C9' C10' C11 C14 177.4(16) . . . . ? C10 C11 C12 C13 17.8(15) . . . . ? C10' C11 C12 C13 -14(3) . . . . ? C14 C11 C12 C13 180.0(6) . . . . ? C9 C8 C13 C12 -18.3(16) . . . . ? C9' C8 C13 C12 15(3) . . . . ? C7 C8 C13 C12 -176.6(6) . . . . ? C11 C12 C13 C8 0.8(10) . . . . ? C12 C11 C14 O5 19.4(7) . . . . ? C10 C11 C14 O5 -179.4(14) . . . . ? C10' C11 C14 O5 -146(3) . . . . ? C12 C11 C14 O4 -158.5(5) . . . . ? C10 C11 C14 O4 2.7(15) . . . . ? C10' C11 C14 O4 36(3) . . . . ? C4 C5 N1 C1 2.8(11) . . . . ? C4 C5 N1 C7 -179.5(7) . . . . ? O1 C1 N1 C5 173.4(6) . . . . ? C2 C1 N1 C5 -5.8(8) . . . . ? O1 C1 N1 C7 -4.4(6) . . . . ? C2 C1 N1 C7 176.4(5) . . . . ? C8 C7 N1 C5 98.1(6) . . . . ? C8 C7 N1 C1 -84.1(6) . . . . ? N1 C1 O1 Cd1 172.3(3) . . . . ? C2 C1 O1 Cd1 -8.6(7) . . . . ? O4 Cd1 O1 C1 -154.5(4) 17_554 . . . ? O2 Cd1 O1 C1 22.4(4) . . . . ? O2 Cd1 O1 C1 18.1(16) 20_665 . . . ? O5 Cd1 O1 C1 113.9(4) 30_445 . . . ? O3 Cd1 O1 C1 -67.7(4) 3_765 . . . ? O3 C6 O2 Cd1 -133.6(4) . . . . ? C2 C6 O2 Cd1 49.8(6) . . . . ? O3 C6 O2 Cd1 47.1(6) . . . 21_545 ? C2 C6 O2 Cd1 -129.5(4) . . . 21_545 ? O4 Cd1 O2 C6 -21.0(11) 17_554 . . . ? O1 Cd1 O2 C6 -43.9(4) . . . . ? O2 Cd1 O2 C6 135.8(3) 20_665 . . . ? O5 Cd1 O2 C6 -133.1(4) 30_445 . . . ? O3 Cd1 O2 C6 37.5(4) 3_765 . . . ? O4 Cd1 O2 Cd1 158.4(8) 17_554 . . 21_545 ? O1 Cd1 O2 Cd1 135.51(16) . . . 21_545 ? O2 Cd1 O2 Cd1 -44.86(18) 20_665 . . 21_545 ? O5 Cd1 O2 Cd1 46.27(16) 30_445 . . 21_545 ? O3 Cd1 O2 Cd1 -143.15(15) 3_765 . . 21_545 ? O2 C6 O3 Cd1 -15.1(8) . . . 2_645 ? C2 C6 O3 Cd1 161.6(4) . . . 2_645 ? O5 C14 O4 Cd1 22.6(8) . . . 17_554 ? C11 C14 O4 Cd1 -159.7(3) . . . 17_554 ? O4 C14 O5 Cd1 2.4(8) . . . 36_545 ? C11 C14 O5 Cd1 -175.2(3) . . . 36_545 ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.101 _refine_diff_density_min -0.885 _refine_diff_density_rms 0.127 _database_code_depnum_ccdc_archive 'CCDC 938797' ####################################################################### # # 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_compound-5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Mn N O5.50' _chemical_formula_sum 'C14 H10 Mn N O5.50' _chemical_formula_weight 335.17 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3 c' _symmetry_space_group_name_hall '-R 3 2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 18.2630(14) _cell_length_b 18.2630(14) _cell_length_c 47.393(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 13689.5(17) _cell_formula_units_Z 36 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1491 _cell_measurement_theta_min 3.2665 _cell_measurement_theta_max 24.9737 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6120 _exptl_absorpt_coefficient_mu 0.890 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8420 _exptl_absorpt_correction_T_max 0.8634 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8116 _diffrn_reflns_av_R_equivalents 0.1030 _diffrn_reflns_av_sigmaI/netI 0.1446 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -56 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2667 _reflns_number_gt 1424 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2\s(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. For C12, c3, c4 and c5, some anisotropic displacement ellipsoids were rather elongated which led us to use the SIMU restraints. ; _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^)+(0.0930P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2667 _refine_ls_number_parameters 218 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1583 _refine_ls_R_factor_gt 0.0781 _refine_ls_wR_factor_ref 0.2293 _refine_ls_wR_factor_gt 0.1788 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Mn1 Mn 0.88307(7) 0.08733(7) 0.01751(2) 0.0321(4) Uani 1 1 d . . . C1 C 0.4673(5) 0.1300(5) -0.09254(14) 0.0351(18) Uani 1 1 d . A . C2 C 0.4816(7) 0.2130(7) -0.09570(17) 0.070(2) Uani 1 1 d U . . C3 C 0.4569(7) 0.2480(7) -0.07443(17) 0.0763(19) Uani 1 1 d U . . H3 H 0.4675 0.3032 -0.0763 0.092 Uiso 1 1 calc R . . C4 C 0.4162(8) 0.2016(7) -0.05020(18) 0.081(2) Uani 1 1 d U . . H4 H 0.3971 0.2243 -0.0364 0.097 Uiso 1 1 calc R . . C5 C 0.4056(7) 0.1249(7) -0.04733(19) 0.080(2) Uani 1 1 d U A . H5 H 0.3787 0.0939 -0.0312 0.096 Uiso 1 1 calc R . . C6 C 0.5189(5) 0.2659(5) -0.12210(14) 0.0367(19) Uani 1 1 d . . . C7 C 0.4203(5) 0.0065(6) -0.06180(17) 0.056(3) Uani 1 1 d . A . H7A H 0.4059 -0.0240 -0.0796 0.067 Uiso 1 1 calc R . . H7B H 0.3731 -0.0240 -0.0490 0.067 Uiso 1 1 calc R . . C8 C 0.4978(5) 0.0077(6) -0.04953(16) 0.044(2) Uani 1 1 d . . . C9 C 0.5489(7) 0.0620(7) -0.0305(2) 0.079(3) Uani 1 1 d . A . H9 H 0.5386 0.1043 -0.0243 0.094 Uiso 1 1 calc R . . C10 C 0.6163(6) 0.0587(6) -0.0196(2) 0.062(3) Uani 1 1 d . . . H10 H 0.6511 0.0990 -0.0065 0.074 Uiso 1 1 calc R A . C11 C 0.6331(5) -0.0030(5) -0.02757(16) 0.0412(19) Uani 1 1 d U A . C12 C 0.563(2) -0.076(2) -0.0359(7) 0.043(2) Uani 0.32(4) 1 d PU A 1 H12 H 0.5589 -0.1286 -0.0330 0.051 Uiso 0.32(4) 1 calc PR A 1 C13 C 0.497(2) -0.071(2) -0.0486(8) 0.043(3) Uani 0.32(4) 1 d PU A 1 H13 H 0.4519 -0.1191 -0.0566 0.051 Uiso 0.32(4) 1 calc PR A 1 C12' C 0.5877(19) -0.0520(17) -0.0501(7) 0.092(12) Uani 0.68(4) 1 d P A 2 H12' H 0.6012 -0.0907 -0.0578 0.111 Uiso 0.68(4) 1 calc PR A 2 C13' C 0.522(2) -0.0442(19) -0.0614(7) 0.095(11) Uani 0.68(4) 1 d P A 2 H13' H 0.4948 -0.0749 -0.0775 0.114 Uiso 0.68(4) 1 calc PR A 2 C14 C 0.7066(5) -0.0101(5) -0.01618(15) 0.0385(19) Uani 1 1 d . . . N1 N 0.4320(4) 0.0906(5) -0.06662(12) 0.0514(19) Uani 1 1 d . . . O1 O 0.4824(3) 0.0883(3) -0.10965(10) 0.0403(13) Uani 1 1 d . . . O2 O 0.5130(3) 0.2254(3) -0.14499(9) 0.0358(12) Uani 1 1 d . . . O3 O 0.5474(4) 0.3427(3) -0.12082(10) 0.0474(15) Uani 1 1 d . . . O4 O 0.7015(3) -0.0817(3) -0.01820(11) 0.0495(15) Uani 1 1 d . . . O5 O 0.7673(3) 0.0550(3) -0.00527(10) 0.0450(14) Uani 1 1 d . A . O1W O 0.7416(11) 0.1876(12) 0.0356(4) 0.123(6) Uani 0.50 1 d P . . 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 Mn1 0.0331(7) 0.0312(7) 0.0295(6) 0.0003(5) 0.0031(5) 0.0143(6) C1 0.034(4) 0.049(5) 0.034(4) 0.018(4) 0.008(3) 0.030(4) C2 0.119(5) 0.105(5) 0.040(3) 0.027(3) 0.031(3) 0.097(4) C3 0.124(5) 0.108(5) 0.045(3) 0.026(3) 0.034(3) 0.094(4) C4 0.128(5) 0.111(5) 0.047(3) 0.026(3) 0.038(3) 0.092(4) C5 0.128(5) 0.110(5) 0.047(3) 0.028(3) 0.039(3) 0.092(5) C6 0.042(5) 0.050(6) 0.032(4) 0.009(4) 0.003(4) 0.034(5) C7 0.034(5) 0.075(7) 0.060(5) 0.042(5) 0.015(4) 0.029(5) C8 0.043(5) 0.052(6) 0.043(4) 0.016(4) -0.004(4) 0.029(5) C9 0.087(8) 0.078(8) 0.104(8) -0.040(7) -0.048(7) 0.066(7) C10 0.061(6) 0.051(6) 0.083(7) -0.016(5) -0.022(5) 0.035(5) C11 0.042(4) 0.041(4) 0.045(4) 0.007(4) -0.003(4) 0.023(4) C12 0.042(5) 0.041(5) 0.046(5) 0.007(4) -0.003(4) 0.022(4) C13 0.042(5) 0.041(5) 0.046(5) 0.007(5) -0.003(5) 0.021(4) C12' 0.109(19) 0.103(18) 0.11(2) -0.067(17) -0.086(19) 0.090(17) C13' 0.12(2) 0.10(2) 0.099(18) -0.068(17) -0.077(18) 0.084(19) C14 0.035(5) 0.042(5) 0.045(4) 0.008(4) 0.007(4) 0.024(4) N1 0.059(5) 0.080(5) 0.038(3) 0.025(4) 0.019(3) 0.052(5) O1 0.047(3) 0.037(3) 0.038(3) 0.012(3) 0.010(3) 0.022(3) O2 0.046(3) 0.044(3) 0.024(2) 0.004(2) 0.000(2) 0.027(3) O3 0.066(4) 0.033(3) 0.041(3) -0.003(3) -0.004(3) 0.023(3) O4 0.040(3) 0.041(3) 0.077(4) 0.002(3) -0.004(3) 0.027(3) O5 0.035(3) 0.039(3) 0.056(3) 0.004(3) -0.006(3) 0.015(3) O1W 0.099(13) 0.114(15) 0.147(15) -0.052(13) -0.024(12) 0.046(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Mn1 O4 2.118(5) 20_665 ? Mn1 O1 2.158(5) 35_545 ? Mn1 O5 2.177(5) . ? Mn1 O2 2.182(5) 35_545 ? Mn1 O2 2.189(4) 10_554 ? Mn1 O3 2.203(5) 36_655 ? C1 O1 1.235(8) . ? C1 N1 1.406(9) . ? C1 C2 1.411(12) . ? C2 C3 1.385(12) . ? C2 C6 1.518(11) . ? C3 C4 1.400(12) . ? C3 H3 0.9300 . ? C4 C5 1.322(13) . ? C4 H4 0.9300 . ? C5 N1 1.328(10) . ? C5 H5 0.9300 . ? C6 O3 1.231(9) . ? C6 O2 1.287(8) . ? C7 N1 1.459(11) . ? C7 C8 1.521(10) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.320(12) . ? C8 C13' 1.36(2) . ? C8 C13 1.43(4) . ? C9 C10 1.364(11) . ? C9 H9 0.9300 . ? C10 C11 1.361(11) . ? C10 H10 0.9300 . ? C11 C12 1.37(4) . ? C11 C12' 1.375(17) . ? C11 C14 1.512(11) . ? C12 C13 1.39(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C12' C13' 1.38(2) . ? C12' H12' 0.9300 . ? C13' H13' 0.9300 . ? C14 O5 1.261(9) . ? C14 O4 1.267(9) . ? O1 Mn1 2.158(5) 29_445 ? O2 Mn1 2.182(5) 29_445 ? O2 Mn1 2.189(4) 10_454 ? O3 Mn1 2.203(5) 30_565 ? O4 Mn1 2.118(5) 21_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 O4 Mn1 O1 93.3(2) 20_665 35_545 ? O4 Mn1 O5 91.3(2) 20_665 . ? O1 Mn1 O5 90.1(2) 35_545 . ? O4 Mn1 O2 173.92(19) 20_665 35_545 ? O1 Mn1 O2 81.27(18) 35_545 35_545 ? O5 Mn1 O2 91.53(19) . 35_545 ? O4 Mn1 O2 89.9(2) 20_665 10_554 ? O1 Mn1 O2 176.0(2) 35_545 10_554 ? O5 Mn1 O2 92.25(18) . 10_554 ? O2 Mn1 O2 95.4(2) 35_545 10_554 ? O4 Mn1 O3 87.8(2) 20_665 36_655 ? O1 Mn1 O3 82.12(19) 35_545 36_655 ? O5 Mn1 O3 172.12(19) . 36_655 ? O2 Mn1 O3 88.7(2) 35_545 36_655 ? O2 Mn1 O3 95.58(18) 10_554 36_655 ? O1 C1 N1 116.4(7) . . ? O1 C1 C2 127.9(6) . . ? N1 C1 C2 115.7(7) . . ? C3 C2 C1 119.4(8) . . ? C3 C2 C6 116.9(8) . . ? C1 C2 C6 123.6(7) . . ? C2 C3 C4 121.0(10) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 118.6(9) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 N1 122.2(9) . . ? C4 C5 H5 118.9 . . ? N1 C5 H5 118.9 . . ? O3 C6 O2 124.3(7) . . ? O3 C6 C2 119.0(7) . . ? O2 C6 C2 116.6(7) . . ? N1 C7 C8 113.5(7) . . ? N1 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N1 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C13' 116.9(11) . . ? C9 C8 C13 112.6(17) . . ? C13' C8 C13 32.1(16) . . ? C9 C8 C7 125.1(9) . . ? C13' C8 C7 117.5(10) . . ? C13 C8 C7 117.0(17) . . ? C8 C9 C10 122.7(9) . . ? C8 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C11 C10 C9 120.8(9) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 113.5(17) . . ? C10 C11 C12' 116.4(10) . . ? C12 C11 C12' 34.4(14) . . ? C10 C11 C14 123.3(7) . . ? C12 C11 C14 117.2(17) . . ? C12' C11 C14 119.6(10) . . ? C11 C12 C13 118(3) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C12 C13 C8 120(3) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? C11 C12' C13' 120.3(15) . . ? C11 C12' H12' 119.8 . . ? C13' C12' H12' 119.8 . . ? C8 C13' C12' 121.1(13) . . ? C8 C13' H13' 119.5 . . ? C12' C13' H13' 119.5 . . ? O5 C14 O4 125.5(7) . . ? O5 C14 C11 117.7(7) . . ? O4 C14 C11 116.8(7) . . ? C5 N1 C1 122.8(8) . . ? C5 N1 C7 119.5(7) . . ? C1 N1 C7 117.7(6) . . ? C1 O1 Mn1 128.4(4) . 29_445 ? C6 O2 Mn1 124.6(4) . 29_445 ? C6 O2 Mn1 122.5(4) . 10_454 ? Mn1 O2 Mn1 112.9(2) 29_445 10_454 ? C6 O3 Mn1 139.4(5) . 30_565 ? C14 O4 Mn1 131.3(5) . 21_545 ? C14 O5 Mn1 137.3(5) . . ? 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 O1 C1 C2 C3 177.3(9) . . . . ? N1 C1 C2 C3 -3.2(14) . . . . ? O1 C1 C2 C6 0.6(16) . . . . ? N1 C1 C2 C6 -179.9(8) . . . . ? C1 C2 C3 C4 -1.6(17) . . . . ? C6 C2 C3 C4 175.3(10) . . . . ? C2 C3 C4 C5 3.4(18) . . . . ? C3 C4 C5 N1 -0.1(19) . . . . ? C3 C2 C6 O3 20.1(13) . . . . ? C1 C2 C6 O3 -163.1(8) . . . . ? C3 C2 C6 O2 -155.2(9) . . . . ? C1 C2 C6 O2 21.6(13) . . . . ? N1 C7 C8 C9 38.1(12) . . . . ? N1 C7 C8 C13' -133(2) . . . . ? N1 C7 C8 C13 -169.8(17) . . . . ? C13' C8 C9 C10 -10(2) . . . . ? C13 C8 C9 C10 25(2) . . . . ? C7 C8 C9 C10 177.9(9) . . . . ? C8 C9 C10 C11 -1.2(17) . . . . ? C9 C10 C11 C12 -28(2) . . . . ? C9 C10 C11 C12' 10(2) . . . . ? C9 C10 C11 C14 -179.9(9) . . . . ? C10 C11 C12 C13 31(3) . . . . ? C12' C11 C12 C13 -71(3) . . . . ? C14 C11 C12 C13 -175(2) . . . . ? C11 C12 C13 C8 -8(4) . . . . ? C9 C8 C13 C12 -20(3) . . . . ? C13' C8 C13 C12 85(4) . . . . ? C7 C8 C13 C12 -175(2) . . . . ? C10 C11 C12' C13' -7(3) . . . . ? C12 C11 C12' C13' 86(4) . . . . ? C14 C11 C12' C13' -177.6(15) . . . . ? C9 C8 C13' C12' 13(3) . . . . ? C13 C8 C13' C12' -77(4) . . . . ? C7 C8 C13' C12' -174.6(16) . . . . ? C11 C12' C13' C8 -4(3) . . . . ? C10 C11 C14 O5 -20.3(12) . . . . ? C12 C11 C14 O5 -171.3(17) . . . . ? C12' C11 C14 O5 149(2) . . . . ? C10 C11 C14 O4 159.0(8) . . . . ? C12 C11 C14 O4 7.9(19) . . . . ? C12' C11 C14 O4 -31(2) . . . . ? C4 C5 N1 C1 -5.1(17) . . . . ? C4 C5 N1 C7 178.4(11) . . . . ? O1 C1 N1 C5 -173.8(9) . . . . ? C2 C1 N1 C5 6.6(13) . . . . ? O1 C1 N1 C7 2.7(10) . . . . ? C2 C1 N1 C7 -176.8(8) . . . . ? C8 C7 N1 C5 -96.4(10) . . . . ? C8 C7 N1 C1 86.9(9) . . . . ? N1 C1 O1 Mn1 -171.7(5) . . . 29_445 ? C2 C1 O1 Mn1 7.9(12) . . . 29_445 ? O3 C6 O2 Mn1 134.8(6) . . . 29_445 ? C2 C6 O2 Mn1 -50.2(9) . . . 29_445 ? O3 C6 O2 Mn1 -46.1(10) . . . 10_454 ? C2 C6 O2 Mn1 129.0(6) . . . 10_454 ? O2 C6 O3 Mn1 14.6(13) . . . 30_565 ? C2 C6 O3 Mn1 -160.4(6) . . . 30_565 ? O5 C14 O4 Mn1 -21.8(12) . . . 21_545 ? C11 C14 O4 Mn1 158.9(5) . . . 21_545 ? O4 C14 O5 Mn1 -5.6(12) . . . . ? C11 C14 O5 Mn1 173.6(5) . . . . ? O4 Mn1 O5 C14 175.9(7) 20_665 . . . ? O1 Mn1 O5 C14 -90.8(7) 35_545 . . . ? O2 Mn1 O5 C14 -9.5(7) 35_545 . . . ? O2 Mn1 O5 C14 85.9(7) 10_554 . . . ? O3 Mn1 O5 C14 -101.0(16) 36_655 . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.933 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 938798' ####################################################################### # # 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_Compound-6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H30 Cu2 N4 O12' _chemical_formula_sum 'C38 H30 Cu2 N4 O12' _chemical_formula_weight 861.74 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' 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/c' _symmetry_space_group_name_hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.8430(4) _cell_length_b 9.5300(3) _cell_length_c 12.6580(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.631(3) _cell_angle_gamma 90.00 _cell_volume 1740.09(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2823 _cell_measurement_theta_min 3.2736 _cell_measurement_theta_max 29.0840 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 1.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7815 _exptl_absorpt_correction_T_max 0.8193 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7396 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 29.15 _reflns_number_total 3970 _reflns_number_gt 3298 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^ > 2\s(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^)+(0.0463P)^2^+0.8022P] 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 3970 _refine_ls_number_parameters 259 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.817576(18) -0.00559(2) 0.48507(2) 0.02760(10) Uani 1 1 d . . . C14 C 0.34754(16) -0.0921(2) 0.5612(2) 0.0349(5) Uani 1 1 d . . . C11 C 0.43628(15) -0.1678(2) 0.56233(19) 0.0319(5) Uani 1 1 d . . . C12 C 0.48867(18) -0.2226(3) 0.6585(2) 0.0473(6) Uani 1 1 d . . . H12 H 0.4701 -0.2079 0.7228 0.057 Uiso 1 1 calc R . . C13 C 0.56816(18) -0.2988(3) 0.6605(2) 0.0469(6) Uani 1 1 d . . . H13 H 0.6015 -0.3368 0.7257 0.056 Uiso 1 1 calc R . . C8 C 0.59866(15) -0.3193(2) 0.56688(18) 0.0316(5) Uani 1 1 d . . . C9 C 0.54732(19) -0.2627(4) 0.4711(2) 0.0531(8) Uani 1 1 d . . . H9 H 0.5672 -0.2742 0.4072 0.064 Uiso 1 1 calc R . . C10 C 0.46688(19) -0.1890(3) 0.4691(2) 0.0512(7) Uani 1 1 d . . . H10 H 0.4327 -0.1531 0.4036 0.061 Uiso 1 1 calc R . . C7 C 0.68611(16) -0.4036(2) 0.5734(2) 0.0359(5) Uani 1 1 d . . . H7A H 0.7351 -0.3653 0.6308 0.043 Uiso 1 1 calc R . . H7B H 0.6753 -0.4995 0.5929 0.043 Uiso 1 1 calc R . . C5 C 0.69290(18) -0.5126(2) 0.3997(2) 0.0422(6) Uani 1 1 d . . . H5 H 0.6577 -0.5861 0.4169 0.051 Uiso 1 1 calc R . . C4 C 0.7183(2) -0.5149(3) 0.3044(3) 0.0478(7) Uani 1 1 d . . . H4 H 0.6993 -0.5874 0.2549 0.057 Uiso 1 1 calc R . . C3 C 0.77371(17) -0.4068(3) 0.2814(2) 0.0402(6) Uani 1 1 d . . . H3 H 0.7920 -0.4080 0.2160 0.048 Uiso 1 1 calc R . . C2 C 0.80207(14) -0.2984(2) 0.35292(17) 0.0279(4) Uani 1 1 d . . . C1 C 0.76866(14) -0.2917(2) 0.44981(18) 0.0272(4) Uani 1 1 d . . . C6 C 0.87056(14) -0.1925(2) 0.32844(17) 0.0284(4) Uani 1 1 d . . . C15 C 0.87744(17) 0.2722(2) 0.56378(19) 0.0366(5) Uani 1 1 d . . . H15 H 0.8488 0.2464 0.6187 0.044 Uiso 1 1 calc R . . C16 C 0.92637(17) 0.3958(2) 0.57456(19) 0.0355(5) Uani 1 1 d . . . H16 H 0.9297 0.4522 0.6353 0.043 Uiso 1 1 calc R . . C17 C 0.97074(15) 0.4362(2) 0.49450(17) 0.0269(4) Uani 1 1 d . . . C18 C 0.95730(18) 0.3514(2) 0.4028(2) 0.0380(5) Uani 1 1 d . . . H18 H 0.9826 0.3766 0.3450 0.046 Uiso 1 1 calc R . . C19 C 0.90631(17) 0.2298(2) 0.39794(19) 0.0353(5) Uani 1 1 d . . . H19 H 0.8976 0.1750 0.3356 0.042 Uiso 1 1 calc R . . N1 N 0.71772(12) -0.40475(18) 0.47143(16) 0.0312(4) Uani 1 1 d . . . N2 N 0.86906(12) 0.18706(18) 0.47774(15) 0.0279(4) Uani 1 1 d . . . O4 O 0.33056(13) -0.0520(3) 0.64797(15) 0.0559(5) Uani 1 1 d . . . O5 O 0.29052(11) -0.07556(17) 0.46932(13) 0.0342(4) Uani 1 1 d . . . O3 O 0.90689(13) -0.21695(19) 0.25264(14) 0.0467(4) Uani 1 1 d . . . O2 O 0.89016(11) -0.08284(15) 0.38761(13) 0.0337(4) Uani 1 1 d . . . O1 O 0.78073(11) -0.19347(15) 0.51776(12) 0.0339(4) Uani 1 1 d . . . O1W O 0.93026(13) -0.0207(2) 0.64954(16) 0.0399(4) Uani 1 1 d D . . H1A H 0.933(2) -0.092(4) 0.673(3) 0.060 Uiso 1 1 d D . . H1B H 0.975(3) 0.002(3) 0.646(3) 0.060 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.03067(17) 0.02318(15) 0.03275(17) -0.00293(10) 0.01512(12) -0.00350(10) C14 0.0291(11) 0.0353(12) 0.0422(13) -0.0053(10) 0.0120(10) -0.0065(9) C11 0.0264(11) 0.0350(11) 0.0355(12) -0.0015(9) 0.0093(9) -0.0065(9) C12 0.0375(14) 0.0744(19) 0.0310(12) -0.0032(12) 0.0101(10) 0.0045(13) C13 0.0378(14) 0.0712(18) 0.0303(12) 0.0091(12) 0.0052(10) 0.0050(13) C8 0.0272(11) 0.0332(11) 0.0355(12) 0.0048(9) 0.0091(9) -0.0056(9) C9 0.0453(15) 0.086(2) 0.0325(13) 0.0132(14) 0.0171(11) 0.0239(15) C10 0.0431(15) 0.077(2) 0.0351(13) 0.0175(13) 0.0124(11) 0.0197(14) C7 0.0335(12) 0.0349(12) 0.0405(13) 0.0107(10) 0.0114(10) -0.0010(10) C5 0.0368(14) 0.0274(11) 0.0631(18) -0.0056(11) 0.0134(12) -0.0085(10) C4 0.0421(15) 0.0411(14) 0.0606(18) -0.0225(12) 0.0128(13) -0.0119(11) C3 0.0352(13) 0.0417(13) 0.0451(14) -0.0140(11) 0.0126(11) -0.0037(10) C2 0.0239(10) 0.0279(10) 0.0320(11) -0.0034(9) 0.0067(8) 0.0004(8) C1 0.0235(10) 0.0230(9) 0.0339(11) 0.0004(9) 0.0047(8) 0.0004(8) C6 0.0251(10) 0.0315(11) 0.0291(11) -0.0018(9) 0.0078(8) 0.0017(8) C15 0.0469(14) 0.0342(12) 0.0342(12) -0.0043(10) 0.0202(10) -0.0099(10) C16 0.0473(14) 0.0325(11) 0.0304(11) -0.0064(9) 0.0165(10) -0.0093(10) C17 0.0298(10) 0.0219(9) 0.0305(11) 0.0019(8) 0.0103(8) 0.0021(9) C18 0.0569(15) 0.0271(11) 0.0382(13) -0.0031(10) 0.0279(11) -0.0067(10) C19 0.0508(14) 0.0268(11) 0.0339(12) -0.0050(9) 0.0210(10) -0.0049(10) N1 0.0272(9) 0.0264(9) 0.0412(11) 0.0024(8) 0.0101(8) -0.0012(7) N2 0.0287(9) 0.0234(8) 0.0331(10) -0.0003(7) 0.0106(7) -0.0025(7) O4 0.0438(11) 0.0822(14) 0.0422(11) -0.0196(10) 0.0111(8) 0.0080(10) O5 0.0291(8) 0.0376(9) 0.0379(9) -0.0006(7) 0.0120(7) 0.0018(7) O3 0.0486(11) 0.0538(10) 0.0468(10) -0.0195(8) 0.0294(8) -0.0158(8) O2 0.0366(9) 0.0271(8) 0.0434(9) -0.0076(7) 0.0211(7) -0.0057(6) O1 0.0453(9) 0.0277(7) 0.0324(8) -0.0034(6) 0.0169(7) -0.0088(7) O1W 0.0340(10) 0.0406(10) 0.0446(10) 0.0091(8) 0.0081(8) -0.0051(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.9449(15) . ? Cu1 O2 1.9624(15) . ? Cu1 O5 1.9854(15) 3_656 ? Cu1 N2 1.9992(17) . ? Cu1 O1W 2.348(2) . ? C14 O4 1.244(3) . ? C14 O5 1.276(3) . ? C14 C11 1.499(3) . ? C11 C10 1.375(3) . ? C11 C12 1.383(3) . ? C12 C13 1.381(4) . ? C12 H12 0.9300 . ? C13 C8 1.378(3) . ? C13 H13 0.9300 . ? C8 C9 1.381(3) . ? C8 C7 1.512(3) . ? C9 C10 1.380(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C7 N1 1.473(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C5 C4 1.346(4) . ? C5 N1 1.364(3) . ? C5 H5 0.9300 . ? C4 C3 1.391(4) . ? C4 H4 0.9300 . ? C3 C2 1.373(3) . ? C3 H3 0.9300 . ? C2 C1 1.429(3) . ? C2 C6 1.515(3) . ? C1 O1 1.255(2) . ? C1 N1 1.380(3) . ? C6 O3 1.229(3) . ? C6 O2 1.278(3) . ? C15 N2 1.340(3) . ? C15 C16 1.374(3) . ? C15 H15 0.9300 . ? C16 C17 1.387(3) . ? C16 H16 0.9300 . ? C17 C18 1.390(3) . ? C17 C17 1.482(4) 3_766 ? C18 C19 1.377(3) . ? C18 H18 0.9300 . ? C19 N2 1.325(3) . ? C19 H19 0.9300 . ? O5 Cu1 1.9854(15) 3_656 ? O1W H1A 0.74(4) . ? O1W H1B 0.71(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 O1 Cu1 O2 90.68(6) . . ? O1 Cu1 O5 90.56(7) . 3_656 ? O2 Cu1 O5 158.41(7) . 3_656 ? O1 Cu1 N2 170.07(7) . . ? O2 Cu1 N2 92.46(7) . . ? O5 Cu1 N2 89.98(7) 3_656 . ? O1 Cu1 O1W 86.11(7) . . ? O2 Cu1 O1W 98.77(7) . . ? O5 Cu1 O1W 102.82(7) 3_656 . ? N2 Cu1 O1W 84.11(7) . . ? O4 C14 O5 122.5(2) . . ? O4 C14 C11 120.0(2) . . ? O5 C14 C11 117.4(2) . . ? C10 C11 C12 117.9(2) . . ? C10 C11 C14 122.0(2) . . ? C12 C11 C14 120.1(2) . . ? C13 C12 C11 121.0(2) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C8 C13 C12 120.8(2) . . ? C8 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C8 C9 118.3(2) . . ? C13 C8 C7 118.7(2) . . ? C9 C8 C7 123.0(2) . . ? C10 C9 C8 120.7(2) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 121.3(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? N1 C7 C8 113.76(19) . . ? N1 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N1 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C4 C5 N1 121.3(2) . . ? C4 C5 H5 119.3 . . ? N1 C5 H5 119.3 . . ? C5 C4 C3 118.7(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C2 C3 C4 121.6(2) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C2 C1 119.0(2) . . ? C3 C2 C6 118.9(2) . . ? C1 C2 C6 122.10(18) . . ? O1 C1 N1 116.28(19) . . ? O1 C1 C2 126.78(19) . . ? N1 C1 C2 116.94(18) . . ? O3 C6 O2 122.1(2) . . ? O3 C6 C2 118.17(19) . . ? O2 C6 C2 119.70(18) . . ? N2 C15 C16 123.1(2) . . ? N2 C15 H15 118.5 . . ? C16 C15 H15 118.5 . . ? C15 C16 C17 119.8(2) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C18 116.7(2) . . ? C16 C17 C17 121.9(2) . 3_766 ? C18 C17 C17 121.4(2) . 3_766 ? C19 C18 C17 119.7(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? N2 C19 C18 123.2(2) . . ? N2 C19 H19 118.4 . . ? C18 C19 H19 118.4 . . ? C5 N1 C1 122.1(2) . . ? C5 N1 C7 119.81(19) . . ? C1 N1 C7 118.06(18) . . ? C19 N2 C15 117.26(18) . . ? C19 N2 Cu1 123.40(14) . . ? C15 N2 Cu1 118.79(15) . . ? C14 O5 Cu1 101.01(13) . 3_656 ? C6 O2 Cu1 126.30(14) . . ? C1 O1 Cu1 122.88(14) . . ? Cu1 O1W H1A 112(3) . . ? Cu1 O1W H1B 114(3) . . ? H1A O1W H1B 110(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 C14 C11 C10 -166.6(3) . . . . ? O5 C14 C11 C10 15.6(3) . . . . ? O4 C14 C11 C12 15.4(3) . . . . ? O5 C14 C11 C12 -162.4(2) . . . . ? C10 C11 C12 C13 -1.3(4) . . . . ? C14 C11 C12 C13 176.7(2) . . . . ? C11 C12 C13 C8 1.6(4) . . . . ? C12 C13 C8 C9 -0.5(4) . . . . ? C12 C13 C8 C7 180.0(2) . . . . ? C13 C8 C9 C10 -0.9(4) . . . . ? C7 C8 C9 C10 178.6(3) . . . . ? C12 C11 C10 C9 0.0(4) . . . . ? C14 C11 C10 C9 -178.0(3) . . . . ? C8 C9 C10 C11 1.1(5) . . . . ? C13 C8 C7 N1 -173.3(2) . . . . ? C9 C8 C7 N1 7.2(3) . . . . ? N1 C5 C4 C3 2.2(4) . . . . ? C5 C4 C3 C2 -0.5(4) . . . . ? C4 C3 C2 C1 -4.3(4) . . . . ? C4 C3 C2 C6 173.5(2) . . . . ? C3 C2 C1 O1 -172.8(2) . . . . ? C6 C2 C1 O1 9.5(3) . . . . ? C3 C2 C1 N1 7.2(3) . . . . ? C6 C2 C1 N1 -170.55(18) . . . . ? C3 C2 C6 O3 -8.8(3) . . . . ? C1 C2 C6 O3 169.0(2) . . . . ? C3 C2 C6 O2 172.5(2) . . . . ? C1 C2 C6 O2 -9.7(3) . . . . ? N2 C15 C16 C17 -0.8(4) . . . . ? C15 C16 C17 C18 4.3(4) . . . . ? C15 C16 C17 C17 -176.1(3) . . . 3_766 ? C16 C17 C18 C19 -3.6(4) . . . . ? C17 C17 C18 C19 176.7(3) 3_766 . . . ? C17 C18 C19 N2 -0.6(4) . . . . ? C4 C5 N1 C1 1.0(4) . . . . ? C4 C5 N1 C7 178.1(2) . . . . ? O1 C1 N1 C5 174.3(2) . . . . ? C2 C1 N1 C5 -5.7(3) . . . . ? O1 C1 N1 C7 -2.8(3) . . . . ? C2 C1 N1 C7 177.22(18) . . . . ? C8 C7 N1 C5 -95.1(2) . . . . ? C8 C7 N1 C1 82.1(2) . . . . ? C18 C19 N2 C15 4.2(4) . . . . ? C18 C19 N2 Cu1 -167.14(19) . . . . ? C16 C15 N2 C19 -3.5(4) . . . . ? C16 C15 N2 Cu1 168.2(2) . . . . ? O1 Cu1 N2 C19 129.6(4) . . . . ? O2 Cu1 N2 C19 21.28(19) . . . . ? O5 Cu1 N2 C19 -137.26(19) 3_656 . . . ? O1W Cu1 N2 C19 119.85(19) . . . . ? O1 Cu1 N2 C15 -41.6(5) . . . . ? O2 Cu1 N2 C15 -149.94(18) . . . . ? O5 Cu1 N2 C15 51.52(18) 3_656 . . . ? O1W Cu1 N2 C15 -51.37(18) . . . . ? O4 C14 O5 Cu1 -4.5(3) . . . 3_656 ? C11 C14 O5 Cu1 173.27(16) . . . 3_656 ? O3 C6 O2 Cu1 163.49(17) . . . . ? C2 C6 O2 Cu1 -17.9(3) . . . . ? O1 Cu1 O2 C6 33.59(18) . . . . ? O5 Cu1 O2 C6 -59.7(3) 3_656 . . . ? N2 Cu1 O2 C6 -155.83(18) . . . . ? O1W Cu1 O2 C6 119.75(18) . . . . ? N1 C1 O1 Cu1 -161.73(14) . . . . ? C2 C1 O1 Cu1 18.2(3) . . . . ? O2 Cu1 O1 C1 -32.77(17) . . . . ? O5 Cu1 O1 C1 125.68(17) 3_656 . . . ? N2 Cu1 O1 C1 -141.2(4) . . . . ? O1W Cu1 O1 C1 -131.51(17) . . . . ? _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.763 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 938799' ####################################################################### # # 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_Compound-7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H30 Cd2 N4 O12' _chemical_formula_sum 'C38 H30 Cd2 N4 O12' _chemical_formula_weight 959.46 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9160(6) _cell_length_b 9.8470(6) _cell_length_c 12.3770(9) _cell_angle_alpha 103.997(6) _cell_angle_beta 94.233(6) _cell_angle_gamma 107.480(6) _cell_volume 881.65(11) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1830 _cell_measurement_theta_min 3.1877 _cell_measurement_theta_max 29.2046 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 478 _exptl_absorpt_coefficient_mu 1.280 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7660 _exptl_absorpt_correction_T_max 0.7930 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6342 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0896 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 29.27 _reflns_number_total 3998 _reflns_number_gt 3011 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^ > 2\s(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^)+(0.0108P)^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 3998 _refine_ls_number_parameters 259 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 Cd1 Cd 0.65083(4) 0.05839(3) 0.89914(3) 0.02889(10) Uani 1 1 d . . . C14 C 0.3432(7) -0.1951(5) 0.7008(4) 0.0373(11) Uani 1 1 d . . . C11 C 0.3539(6) -0.2730(5) 0.5808(4) 0.0360(11) Uani 1 1 d . . . C10 C 0.2391(7) -0.4138(5) 0.5296(4) 0.0518(15) Uani 1 1 d . . . H10 H 0.1607 -0.4637 0.5704 0.062 Uiso 1 1 calc R . . C9 C 0.2387(7) -0.4821(5) 0.4180(4) 0.0592(17) Uani 1 1 d . . . H9 H 0.1569 -0.5761 0.3840 0.071 Uiso 1 1 calc R . . C8 C 0.3567(6) -0.4140(4) 0.3566(4) 0.0335(11) Uani 1 1 d . . . C13 C 0.4749(6) -0.2757(5) 0.4080(4) 0.0481(14) Uani 1 1 d . . . H13 H 0.5568 -0.2279 0.3680 0.058 Uiso 1 1 calc R . . C12 C 0.4739(6) -0.2052(5) 0.5203(4) 0.0480(14) Uani 1 1 d . . . H12 H 0.5556 -0.1112 0.5543 0.058 Uiso 1 1 calc R . . C7 C 0.3378(6) -0.4915(4) 0.2327(4) 0.0400(12) Uani 1 1 d . . . H7A H 0.3115 -0.5968 0.2236 0.048 Uiso 1 1 calc R . . H7B H 0.2363 -0.4788 0.1923 0.048 Uiso 1 1 calc R . . C5 C 0.6272(7) -0.5012(5) 0.1838(4) 0.0420(12) Uani 1 1 d . . . H5 H 0.6167 -0.5731 0.2220 0.050 Uiso 1 1 calc R . . C4 C 0.7709(7) -0.4621(5) 0.1322(4) 0.0447(13) Uani 1 1 d . . . H4 H 0.8599 -0.5056 0.1350 0.054 Uiso 1 1 calc R . . C3 C 0.7833(6) -0.3548(4) 0.0746(4) 0.0368(11) Uani 1 1 d . . . H3 H 0.8820 -0.3275 0.0386 0.044 Uiso 1 1 calc R . . C2 C 0.6546(5) -0.2880(4) 0.0691(3) 0.0245(9) Uani 1 1 d . . . C1 C 0.5026(6) -0.3261(4) 0.1276(3) 0.0280(10) Uani 1 1 d . . . C6 C 0.6747(5) -0.1808(4) -0.0006(3) 0.0266(10) Uani 1 1 d . . . C15 C 0.8562(7) 0.1507(5) 0.7005(4) 0.0519(15) Uani 1 1 d . . . H15 H 0.8187 0.2321 0.7259 0.062 Uiso 1 1 calc R . . C16 C 0.9132(7) 0.1314(5) 0.5979(4) 0.0478(14) Uani 1 1 d . . . H16 H 0.9122 0.1980 0.5561 0.057 Uiso 1 1 calc R . . C17 C 0.9715(5) 0.0143(4) 0.5568(4) 0.0309(10) Uani 1 1 d . . . C18 C 0.9766(7) -0.0741(6) 0.6266(4) 0.0562(16) Uani 1 1 d . . . H18 H 1.0224 -0.1515 0.6056 0.067 Uiso 1 1 calc R . . C19 C 0.9134(7) -0.0477(6) 0.7281(4) 0.0567(16) Uani 1 1 d . . . H19 H 0.9150 -0.1112 0.7725 0.068 Uiso 1 1 calc R . . N1 N 0.4975(5) -0.4378(3) 0.1809(3) 0.0337(9) Uani 1 1 d . . . N2 N 0.8504(5) 0.0627(4) 0.7662(3) 0.0371(9) Uani 1 1 d . . . O4 O 0.4552(5) -0.0676(4) 0.7415(3) 0.0633(11) Uani 1 1 d . . . O5 O 0.2229(4) -0.2582(3) 0.7469(3) 0.0465(9) Uani 1 1 d . . . O3 O 0.8027(4) -0.1576(3) -0.0536(3) 0.0423(8) Uani 1 1 d . . . O2 O 0.5561(4) -0.1190(3) -0.0078(2) 0.0344(7) Uani 1 1 d . . . O1 O 0.3782(4) -0.2747(3) 0.1334(2) 0.0374(8) Uani 1 1 d . . . O1W O 0.8667(4) 0.1986(3) 1.0493(3) 0.0345(8) Uani 1 1 d D . . H1B H 0.828(6) 0.203(5) 1.104(4) 0.052 Uiso 1 1 d . . . H1A H 0.966(3) 0.174(5) 1.059(4) 0.052 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.03294(18) 0.03506(17) 0.02205(19) 0.00941(13) 0.01110(14) 0.01328(14) C14 0.046(3) 0.047(3) 0.024(3) 0.012(2) 0.004(2) 0.022(3) C11 0.040(3) 0.040(3) 0.026(3) 0.005(2) 0.006(2) 0.013(2) C10 0.065(4) 0.042(3) 0.041(3) 0.009(2) 0.030(3) 0.002(3) C9 0.087(4) 0.031(2) 0.041(4) 0.002(2) 0.033(3) -0.006(3) C8 0.047(3) 0.036(2) 0.022(3) 0.011(2) 0.011(2) 0.017(2) C13 0.046(3) 0.054(3) 0.026(3) 0.007(2) 0.014(2) -0.009(3) C12 0.045(3) 0.046(3) 0.027(3) -0.001(2) 0.004(2) -0.013(2) C7 0.052(3) 0.032(2) 0.032(3) 0.011(2) 0.016(2) 0.005(2) C5 0.067(3) 0.033(2) 0.035(3) 0.019(2) 0.013(3) 0.021(3) C4 0.052(3) 0.042(3) 0.051(4) 0.019(2) 0.006(3) 0.026(3) C3 0.041(3) 0.034(2) 0.038(3) 0.011(2) 0.010(2) 0.014(2) C2 0.028(2) 0.025(2) 0.019(2) 0.0038(18) 0.0004(18) 0.0101(19) C1 0.042(3) 0.023(2) 0.018(2) 0.0047(18) 0.008(2) 0.010(2) C6 0.031(2) 0.024(2) 0.024(3) 0.0028(18) 0.006(2) 0.012(2) C15 0.095(4) 0.051(3) 0.031(3) 0.021(2) 0.026(3) 0.044(3) C16 0.084(4) 0.049(3) 0.039(3) 0.030(2) 0.036(3) 0.043(3) C17 0.035(2) 0.040(2) 0.027(3) 0.015(2) 0.014(2) 0.018(2) C18 0.087(4) 0.078(4) 0.042(3) 0.033(3) 0.038(3) 0.063(3) C19 0.079(4) 0.082(4) 0.041(4) 0.040(3) 0.035(3) 0.048(3) N1 0.048(2) 0.0297(18) 0.025(2) 0.0093(17) 0.0137(19) 0.0128(18) N2 0.046(2) 0.049(2) 0.022(2) 0.0069(18) 0.0138(19) 0.023(2) O4 0.071(3) 0.063(2) 0.026(2) -0.0022(18) -0.0003(19) -0.007(2) O5 0.058(2) 0.0507(19) 0.029(2) 0.0080(16) 0.0186(18) 0.0143(18) O3 0.0410(19) 0.060(2) 0.047(2) 0.0308(17) 0.0270(17) 0.0299(17) O2 0.0397(18) 0.0424(16) 0.036(2) 0.0221(15) 0.0160(15) 0.0241(15) O1 0.0449(19) 0.0421(17) 0.035(2) 0.0155(15) 0.0201(16) 0.0206(16) O1W 0.0331(18) 0.0537(18) 0.0207(19) 0.0080(15) 0.0074(15) 0.0214(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cd1 O4 2.230(4) . ? Cd1 O1W 2.270(3) . ? Cd1 O2 2.292(3) 1_556 ? Cd1 O2 2.317(2) 2_656 ? Cd1 O1 2.334(3) 2_656 ? Cd1 N2 2.363(3) . ? C14 O5 1.230(5) . ? C14 O4 1.255(5) . ? C14 C11 1.519(6) . ? C11 C12 1.369(6) . ? C11 C10 1.372(6) . ? C10 C9 1.381(6) . ? C10 H10 0.9300 . ? C9 C8 1.369(6) . ? C9 H9 0.9300 . ? C8 C13 1.365(6) . ? C8 C7 1.513(6) . ? C13 C12 1.397(6) . ? C13 H13 0.9300 . ? C12 H12 0.9300 . ? C7 N1 1.473(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C5 C4 1.346(6) . ? C5 N1 1.355(5) . ? C5 H5 0.9300 . ? C4 C3 1.396(6) . ? C4 H4 0.9300 . ? C3 C2 1.374(5) . ? C3 H3 0.9300 . ? C2 C1 1.450(5) . ? C2 C6 1.497(5) . ? C1 O1 1.235(4) . ? C1 N1 1.406(5) . ? C6 O3 1.242(4) . ? C6 O2 1.272(4) . ? C15 N2 1.317(6) . ? C15 C16 1.368(6) . ? C15 H15 0.9300 . ? C16 C17 1.369(5) . ? C16 H16 0.9300 . ? C17 C18 1.373(6) . ? C17 C17 1.495(8) 2_756 ? C18 C19 1.381(6) . ? C18 H18 0.9300 . ? C19 N2 1.328(5) . ? C19 H19 0.9300 . ? O2 Cd1 2.292(3) 1_554 ? O2 Cd1 2.317(2) 2_656 ? O1 Cd1 2.334(3) 2_656 ? O1W H1B 0.75(4) . ? O1W H1A 0.897(10) . ? 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 Cd1 O1W 174.45(12) . . ? O4 Cd1 O2 95.25(12) . 1_556 ? O1W Cd1 O2 89.85(11) . 1_556 ? O4 Cd1 O2 96.19(11) . 2_656 ? O1W Cd1 O2 87.45(10) . 2_656 ? O2 Cd1 O2 72.17(10) 1_556 2_656 ? O4 Cd1 O1 87.69(12) . 2_656 ? O1W Cd1 O1 89.34(11) . 2_656 ? O2 Cd1 O1 145.68(9) 1_556 2_656 ? O2 Cd1 O1 73.52(9) 2_656 2_656 ? O4 Cd1 N2 80.32(13) . . ? O1W Cd1 N2 94.87(12) . . ? O2 Cd1 N2 126.88(11) 1_556 . ? O2 Cd1 N2 160.73(11) 2_656 . ? O1 Cd1 N2 87.36(11) 2_656 . ? O5 C14 O4 126.2(4) . . ? O5 C14 C11 118.1(4) . . ? O4 C14 C11 115.6(4) . . ? C12 C11 C10 118.3(4) . . ? C12 C11 C14 121.7(4) . . ? C10 C11 C14 120.0(4) . . ? C11 C10 C9 120.7(4) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C8 C9 C10 121.3(4) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C13 C8 C9 118.3(4) . . ? C13 C8 C7 123.7(4) . . ? C9 C8 C7 117.8(4) . . ? C8 C13 C12 120.6(4) . . ? C8 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C11 C12 C13 120.7(4) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? N1 C7 C8 114.3(4) . . ? N1 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N1 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C4 C5 N1 121.2(4) . . ? C4 C5 H5 119.4 . . ? N1 C5 H5 119.4 . . ? C5 C4 C3 118.5(4) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C2 C3 C4 122.3(4) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C3 C2 C1 119.4(4) . . ? C3 C2 C6 118.2(3) . . ? C1 C2 C6 122.3(3) . . ? O1 C1 N1 117.5(3) . . ? O1 C1 C2 127.7(4) . . ? N1 C1 C2 114.7(3) . . ? O3 C6 O2 120.9(4) . . ? O3 C6 C2 119.8(3) . . ? O2 C6 C2 119.2(3) . . ? N2 C15 C16 125.0(4) . . ? N2 C15 H15 117.5 . . ? C16 C15 H15 117.5 . . ? C15 C16 C17 120.1(4) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 115.9(4) . . ? C16 C17 C17 121.9(5) . 2_756 ? C18 C17 C17 122.1(5) . 2_756 ? C17 C18 C19 119.8(4) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? N2 C19 C18 124.2(5) . . ? N2 C19 H19 117.9 . . ? C18 C19 H19 117.9 . . ? C5 N1 C1 123.8(3) . . ? C5 N1 C7 118.9(4) . . ? C1 N1 C7 117.3(4) . . ? C15 N2 C19 114.8(4) . . ? C15 N2 Cd1 118.6(3) . . ? C19 N2 Cd1 123.1(3) . . ? C14 O4 Cd1 137.7(3) . . ? C6 O2 Cd1 109.0(2) . 1_554 ? C6 O2 Cd1 136.7(3) . 2_656 ? Cd1 O2 Cd1 107.83(10) 1_554 2_656 ? C1 O1 Cd1 131.9(3) . 2_656 ? Cd1 O1W H1B 111(4) . . ? Cd1 O1W H1A 119(3) . . ? H1B O1W H1A 107(5) . . ? 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 O5 C14 C11 C12 174.3(5) . . . . ? O4 C14 C11 C12 -2.4(7) . . . . ? O5 C14 C11 C10 -4.3(7) . . . . ? O4 C14 C11 C10 178.9(5) . . . . ? C12 C11 C10 C9 -3.2(8) . . . . ? C14 C11 C10 C9 175.5(5) . . . . ? C11 C10 C9 C8 2.4(9) . . . . ? C10 C9 C8 C13 -0.4(8) . . . . ? C10 C9 C8 C7 -175.4(5) . . . . ? C9 C8 C13 C12 -0.6(8) . . . . ? C7 C8 C13 C12 174.1(5) . . . . ? C10 C11 C12 C13 2.2(8) . . . . ? C14 C11 C12 C13 -176.5(5) . . . . ? C8 C13 C12 C11 -0.3(8) . . . . ? C13 C8 C7 N1 23.1(7) . . . . ? C9 C8 C7 N1 -162.2(4) . . . . ? N1 C5 C4 C3 -0.5(7) . . . . ? C5 C4 C3 C2 0.2(7) . . . . ? C4 C3 C2 C1 1.8(6) . . . . ? C4 C3 C2 C6 -176.4(4) . . . . ? C3 C2 C1 O1 178.3(4) . . . . ? C6 C2 C1 O1 -3.5(7) . . . . ? C3 C2 C1 N1 -3.4(6) . . . . ? C6 C2 C1 N1 174.7(3) . . . . ? C3 C2 C6 O3 1.8(6) . . . . ? C1 C2 C6 O3 -176.4(4) . . . . ? C3 C2 C6 O2 179.2(4) . . . . ? C1 C2 C6 O2 1.1(6) . . . . ? N2 C15 C16 C17 -0.6(9) . . . . ? C15 C16 C17 C18 -3.1(8) . . . . ? C15 C16 C17 C17 177.7(5) . . . 2_756 ? C16 C17 C18 C19 4.2(8) . . . . ? C17 C17 C18 C19 -176.5(5) 2_756 . . . ? C17 C18 C19 N2 -2.0(9) . . . . ? C4 C5 N1 C1 -1.4(7) . . . . ? C4 C5 N1 C7 176.2(4) . . . . ? O1 C1 N1 C5 -178.2(4) . . . . ? C2 C1 N1 C5 3.3(6) . . . . ? O1 C1 N1 C7 4.1(5) . . . . ? C2 C1 N1 C7 -174.4(4) . . . . ? C8 C7 N1 C5 88.6(5) . . . . ? C8 C7 N1 C1 -93.6(5) . . . . ? C16 C15 N2 C19 3.0(8) . . . . ? C16 C15 N2 Cd1 -156.5(5) . . . . ? C18 C19 N2 C15 -1.7(8) . . . . ? C18 C19 N2 Cd1 156.8(4) . . . . ? O4 Cd1 N2 C15 74.0(4) . . . . ? O1W Cd1 N2 C15 -103.3(4) . . . . ? O2 Cd1 N2 C15 163.3(3) 1_556 . . . ? O2 Cd1 N2 C15 -7.0(6) 2_656 . . . ? O1 Cd1 N2 C15 -14.1(4) 2_656 . . . ? O4 Cd1 N2 C19 -83.7(4) . . . . ? O1W Cd1 N2 C19 99.1(4) . . . . ? O2 Cd1 N2 C19 5.6(4) 1_556 . . . ? O2 Cd1 N2 C19 -164.7(4) 2_656 . . . ? O1 Cd1 N2 C19 -171.8(4) 2_656 . . . ? O5 C14 O4 Cd1 52.7(8) . . . . ? C11 C14 O4 Cd1 -130.8(4) . . . . ? O1W Cd1 O4 C14 148.3(11) . . . . ? O2 Cd1 O4 C14 -8.3(5) 1_556 . . . ? O2 Cd1 O4 C14 -80.9(5) 2_656 . . . ? O1 Cd1 O4 C14 -154.0(5) 2_656 . . . ? N2 Cd1 O4 C14 118.2(5) . . . . ? O3 C6 O2 Cd1 -10.0(5) . . . 1_554 ? C2 C6 O2 Cd1 172.6(3) . . . 1_554 ? O3 C6 O2 Cd1 -157.0(3) . . . 2_656 ? C2 C6 O2 Cd1 25.6(6) . . . 2_656 ? N1 C1 O1 Cd1 163.3(3) . . . 2_656 ? C2 C1 O1 Cd1 -18.4(6) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.832 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.942 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.120 _database_code_depnum_ccdc_archive 'CCDC 938800' ####################################################################### # # 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_Compound-8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H19 Mn N3 O6' _chemical_formula_sum 'C24 H19 Mn N3 O6' _chemical_formula_weight 500.36 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2290(4) _cell_length_b 9.7350(5) _cell_length_c 14.8300(8) _cell_angle_alpha 89.604(4) _cell_angle_beta 76.115(4) _cell_angle_gamma 65.898(5) _cell_volume 1047.19(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2384 _cell_measurement_theta_min 2.7826 _cell_measurement_theta_max 29.0861 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 0.680 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8760 _exptl_absorpt_correction_T_max 0.9351 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7615 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 29.15 _reflns_number_total 4731 _reflns_number_gt 3608 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^ > 2\s(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^)+(0.0342P)^2^+0.3390P] 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 4731 _refine_ls_number_parameters 313 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Mn1 Mn 0.08666(4) 0.36185(4) 0.16090(2) 0.02884(11) Uani 1 1 d . . . C1 C -0.2430(3) 0.3301(2) 0.29063(15) 0.0249(5) Uani 1 1 d . . . C2 C -0.3800(3) 0.4369(2) 0.25042(15) 0.0261(5) Uani 1 1 d . . . C3 C -0.5604(3) 0.4991(3) 0.30074(17) 0.0331(5) Uani 1 1 d . . . H3 H -0.6492 0.5658 0.2738 0.040 Uiso 1 1 calc R . . C4 C -0.6153(3) 0.4649(3) 0.39190(16) 0.0333(5) Uani 1 1 d . . . H4 H -0.7386 0.5080 0.4253 0.040 Uiso 1 1 calc R . . C5 C -0.4847(3) 0.3682(3) 0.42983(16) 0.0304(5) Uani 1 1 d . . . H5 H -0.5186 0.3461 0.4907 0.036 Uiso 1 1 calc R . . C6 C -0.3255(3) 0.4806(3) 0.15382(16) 0.0308(5) Uani 1 1 d . . . C7 C -0.1647(3) 0.2002(3) 0.42686(16) 0.0293(5) Uani 1 1 d . . . H7A H -0.2076 0.2286 0.4937 0.035 Uiso 1 1 calc R . . H7B H -0.0507 0.2119 0.4043 0.035 Uiso 1 1 calc R . . C8 C -0.1282(3) 0.0368(2) 0.40746(15) 0.0260(5) Uani 1 1 d . . . C9 C -0.2136(3) -0.0320(3) 0.47171(16) 0.0328(5) Uani 1 1 d . . . H9 H -0.2884 0.0211 0.5291 0.039 Uiso 1 1 calc R . . C10 C -0.1899(3) -0.1788(3) 0.45213(16) 0.0330(5) Uani 1 1 d . . . H10 H -0.2488 -0.2230 0.4964 0.040 Uiso 1 1 calc R . . C11 C -0.0792(3) -0.2605(2) 0.36727(15) 0.0263(5) Uani 1 1 d . . . C12 C 0.0106(3) -0.1931(3) 0.30386(16) 0.0318(5) Uani 1 1 d . . . H12 H 0.0874 -0.2470 0.2470 0.038 Uiso 1 1 calc R . . C13 C -0.0120(3) -0.0467(3) 0.32372(17) 0.0346(5) Uani 1 1 d . . . H13 H 0.0511 -0.0039 0.2806 0.042 Uiso 1 1 calc R . . C14 C -0.0615(3) -0.4175(3) 0.34301(17) 0.0340(5) Uani 1 1 d . . . C20 C 0.3548(3) 0.0185(3) 0.14676(16) 0.0290(5) Uani 1 1 d . . . C21 C 0.4623(3) -0.1176(3) 0.17411(19) 0.0411(6) Uani 1 1 d . . . H21 H 0.4884 -0.2085 0.1414 0.049 Uiso 1 1 calc R . . C22 C 0.5303(4) -0.1174(3) 0.2502(2) 0.0506(7) Uani 1 1 d . . . H22 H 0.6020 -0.2081 0.2697 0.061 Uiso 1 1 calc R . . C23 C 0.4915(3) 0.0174(3) 0.29702(19) 0.0436(7) Uani 1 1 d . . . H23 H 0.5391 0.0203 0.3475 0.052 Uiso 1 1 calc R . . C24 C 0.3799(3) 0.1490(3) 0.26744(17) 0.0375(6) Uani 1 1 d . . . H24 H 0.3495 0.2406 0.3006 0.045 Uiso 1 1 calc R . . C15 C 0.2800(3) 0.0277(3) 0.06376(16) 0.0297(5) Uani 1 1 d . . . C16 C 0.3172(3) -0.0991(3) 0.00673(19) 0.0414(6) Uani 1 1 d . . . H16 H 0.3890 -0.1952 0.0200 0.050 Uiso 1 1 calc R . . C17 C 0.2464(4) -0.0812(4) -0.07000(19) 0.0500(7) Uani 1 1 d . . . H17 H 0.2700 -0.1652 -0.1091 0.060 Uiso 1 1 calc R . . C18 C 0.1410(4) 0.0613(4) -0.08824(19) 0.0494(7) Uani 1 1 d . . . H18 H 0.0926 0.0758 -0.1399 0.059 Uiso 1 1 calc R . . C19 C 0.1083(3) 0.1827(3) -0.02858(18) 0.0427(6) Uani 1 1 d . . . H19 H 0.0369 0.2793 -0.0413 0.051 Uiso 1 1 calc R . . N1 N -0.3044(2) 0.3020(2) 0.38106(13) 0.0259(4) Uani 1 1 d . . . N2 N 0.3132(2) 0.1510(2) 0.19329(13) 0.0291(4) Uani 1 1 d . . . N3 N 0.1740(2) 0.1687(2) 0.04686(13) 0.0314(4) Uani 1 1 d . . . O1 O -0.07660(19) 0.25885(17) 0.24949(11) 0.0305(4) Uani 1 1 d . . . O2 O -0.1675(2) 0.4784(2) 0.12389(11) 0.0397(4) Uani 1 1 d . . . O3 O -0.4449(2) 0.5239(2) 0.10893(12) 0.0431(4) Uani 1 1 d . . . O4 O -0.1636(3) -0.4637(3) 0.39505(15) 0.0752(7) Uani 1 1 d . . . O5 O 0.0603(2) -0.4885(2) 0.26881(12) 0.0408(4) Uani 1 1 d . . . O1W O 0.2645(3) 0.4583(2) 0.07526(12) 0.0459(5) Uani 1 1 d D . . H1B H 0.300(4) 0.460(4) 0.0138(8) 0.069 Uiso 1 1 d D . . H1A H 0.344(3) 0.483(4) 0.095(2) 0.069 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.02875(19) 0.0227(2) 0.0297(2) 0.00144(15) -0.00246(14) -0.00839(14) C1 0.0286(11) 0.0215(12) 0.0261(12) 0.0020(9) -0.0058(9) -0.0128(9) C2 0.0288(11) 0.0215(12) 0.0284(12) 0.0017(9) -0.0080(9) -0.0106(9) C3 0.0295(12) 0.0290(13) 0.0381(14) 0.0036(11) -0.0106(10) -0.0085(10) C4 0.0266(12) 0.0356(14) 0.0338(13) -0.0033(11) -0.0020(10) -0.0123(10) C5 0.0353(12) 0.0315(13) 0.0265(12) -0.0019(10) -0.0021(10) -0.0193(10) C6 0.0364(13) 0.0214(12) 0.0316(13) 0.0033(10) -0.0094(10) -0.0088(10) C7 0.0374(12) 0.0269(13) 0.0281(12) 0.0076(10) -0.0123(10) -0.0159(10) C8 0.0280(11) 0.0250(12) 0.0272(12) 0.0057(10) -0.0106(9) -0.0115(9) C9 0.0415(13) 0.0314(14) 0.0236(12) -0.0010(10) -0.0017(10) -0.0171(11) C10 0.0394(13) 0.0334(14) 0.0286(13) 0.0025(11) -0.0014(10) -0.0217(11) C11 0.0263(11) 0.0241(12) 0.0277(12) 0.0024(10) -0.0088(9) -0.0089(9) C12 0.0305(12) 0.0262(13) 0.0275(13) 0.0033(10) -0.0003(9) -0.0049(10) C13 0.0344(12) 0.0271(13) 0.0351(14) 0.0074(11) 0.0000(10) -0.0109(10) C14 0.0367(13) 0.0323(14) 0.0319(14) -0.0035(11) -0.0052(10) -0.0154(11) C20 0.0218(11) 0.0293(13) 0.0325(13) -0.0004(10) -0.0023(9) -0.0099(9) C21 0.0389(14) 0.0276(14) 0.0541(17) 0.0064(12) -0.0134(12) -0.0104(11) C22 0.0453(16) 0.0454(18) 0.0605(19) 0.0202(15) -0.0223(14) -0.0137(13) C23 0.0418(14) 0.0584(19) 0.0368(15) 0.0145(14) -0.0171(12) -0.0234(13) C24 0.0415(14) 0.0423(16) 0.0312(14) 0.0005(12) -0.0089(11) -0.0202(12) C15 0.0218(11) 0.0297(13) 0.0318(13) -0.0042(10) 0.0007(9) -0.0094(9) C16 0.0375(14) 0.0354(15) 0.0481(16) -0.0082(12) -0.0043(12) -0.0159(12) C17 0.0479(16) 0.060(2) 0.0447(17) -0.0183(15) -0.0007(13) -0.0313(15) C18 0.0468(16) 0.074(2) 0.0328(15) -0.0015(15) -0.0094(12) -0.0308(16) C19 0.0422(14) 0.0506(18) 0.0316(14) 0.0053(13) -0.0095(11) -0.0159(13) N1 0.0290(9) 0.0224(10) 0.0287(10) 0.0042(8) -0.0082(8) -0.0127(8) N2 0.0285(10) 0.0288(11) 0.0283(10) 0.0008(8) -0.0049(8) -0.0115(8) N3 0.0308(10) 0.0336(12) 0.0284(11) 0.0010(9) -0.0050(8) -0.0134(9) O1 0.0254(8) 0.0233(9) 0.0346(9) 0.0068(7) -0.0010(7) -0.0062(6) O2 0.0334(9) 0.0422(11) 0.0375(10) 0.0162(8) -0.0063(7) -0.0116(8) O3 0.0463(10) 0.0518(12) 0.0382(10) 0.0153(9) -0.0217(8) -0.0216(9) O4 0.1006(17) 0.0631(15) 0.0612(14) -0.0255(12) 0.0323(12) -0.0627(14) O5 0.0420(10) 0.0349(10) 0.0399(10) -0.0116(8) 0.0029(8) -0.0179(8) O1W 0.0557(11) 0.0594(13) 0.0317(10) 0.0100(10) -0.0044(9) -0.0369(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Mn1 O5 2.0824(17) 1_565 ? Mn1 O2 2.1373(16) . ? Mn1 O1 2.1843(14) . ? Mn1 O1W 2.2024(17) . ? Mn1 N2 2.2825(19) . ? Mn1 N3 2.296(2) . ? C1 O1 1.248(2) . ? C1 N1 1.382(3) . ? C1 C2 1.436(3) . ? C2 C3 1.367(3) . ? C2 C6 1.508(3) . ? C3 C4 1.402(3) . ? C3 H3 0.9300 . ? C4 C5 1.347(3) . ? C4 H4 0.9300 . ? C5 N1 1.360(3) . ? C5 H5 0.9300 . ? C6 O3 1.248(3) . ? C6 O2 1.260(3) . ? C7 N1 1.484(3) . ? C7 C8 1.509(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.380(3) . ? C8 C13 1.388(3) . ? C9 C10 1.384(3) . ? C9 H9 0.9300 . ? C10 C11 1.385(3) . ? C10 H10 0.9300 . ? C11 C12 1.384(3) . ? C11 C14 1.512(3) . ? C12 C13 1.384(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O4 1.223(3) . ? C14 O5 1.268(3) . ? C20 N2 1.340(3) . ? C20 C21 1.382(3) . ? C20 C15 1.490(3) . ? C21 C22 1.375(4) . ? C21 H21 0.9300 . ? C22 C23 1.367(4) . ? C22 H22 0.9300 . ? C23 C24 1.379(4) . ? C23 H23 0.9300 . ? C24 N2 1.338(3) . ? C24 H24 0.9300 . ? C15 N3 1.352(3) . ? C15 C16 1.384(3) . ? C16 C17 1.377(4) . ? C16 H16 0.9300 . ? C17 C18 1.370(4) . ? C17 H17 0.9300 . ? C18 C19 1.375(4) . ? C18 H18 0.9300 . ? C19 N3 1.338(3) . ? C19 H19 0.9300 . ? O5 Mn1 2.0824(17) 1_545 ? O1W H1B 0.890(10) . ? O1W H1A 0.891(10) . ? 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 O5 Mn1 O2 101.46(7) 1_565 . ? O5 Mn1 O1 94.52(6) 1_565 . ? O2 Mn1 O1 81.16(6) . . ? O5 Mn1 O1W 84.61(7) 1_565 . ? O2 Mn1 O1W 102.16(7) . . ? O1 Mn1 O1W 176.67(6) . . ? O5 Mn1 N2 98.00(7) 1_565 . ? O2 Mn1 N2 153.08(7) . . ? O1 Mn1 N2 78.92(6) . . ? O1W Mn1 N2 98.00(7) . . ? O5 Mn1 N3 168.28(7) 1_565 . ? O2 Mn1 N3 90.25(7) . . ? O1 Mn1 N3 87.69(6) . . ? O1W Mn1 N3 92.52(7) . . ? N2 Mn1 N3 71.10(7) . . ? O1 C1 N1 118.38(19) . . ? O1 C1 C2 125.2(2) . . ? N1 C1 C2 116.41(18) . . ? C3 C2 C1 119.3(2) . . ? C3 C2 C6 120.2(2) . . ? C1 C2 C6 120.44(19) . . ? C2 C3 C4 121.8(2) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 118.2(2) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C4 C5 N1 121.5(2) . . ? C4 C5 H5 119.3 . . ? N1 C5 H5 119.3 . . ? O3 C6 O2 123.3(2) . . ? O3 C6 C2 117.2(2) . . ? O2 C6 C2 119.49(19) . . ? N1 C7 C8 111.54(17) . . ? N1 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C13 118.4(2) . . ? C9 C8 C7 120.7(2) . . ? C13 C8 C7 120.9(2) . . ? C8 C9 C10 121.1(2) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C11 120.7(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 118.3(2) . . ? C12 C11 C14 120.7(2) . . ? C10 C11 C14 121.0(2) . . ? C11 C12 C13 121.0(2) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C8 120.5(2) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? O4 C14 O5 126.4(2) . . ? O4 C14 C11 118.3(2) . . ? O5 C14 C11 115.3(2) . . ? N2 C20 C21 121.6(2) . . ? N2 C20 C15 115.8(2) . . ? C21 C20 C15 122.6(2) . . ? C22 C21 C20 119.4(3) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C23 C22 C21 119.4(2) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 118.3(2) . . ? C22 C23 H23 120.9 . . ? C24 C23 H23 120.9 . . ? N2 C24 C23 123.1(2) . . ? N2 C24 H24 118.5 . . ? C23 C24 H24 118.5 . . ? N3 C15 C16 121.8(2) . . ? N3 C15 C20 115.8(2) . . ? C16 C15 C20 122.5(2) . . ? C17 C16 C15 119.1(3) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C18 C17 C16 119.4(3) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 118.6(3) . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? N3 C19 C18 123.3(3) . . ? N3 C19 H19 118.4 . . ? C18 C19 H19 118.4 . . ? C5 N1 C1 122.68(19) . . ? C5 N1 C7 119.53(18) . . ? C1 N1 C7 117.75(17) . . ? C24 N2 C20 118.2(2) . . ? C24 N2 Mn1 122.83(17) . . ? C20 N2 Mn1 117.70(14) . . ? C19 N3 C15 117.8(2) . . ? C19 N3 Mn1 124.53(17) . . ? C15 N3 Mn1 117.07(15) . . ? C1 O1 Mn1 123.36(14) . . ? C6 O2 Mn1 132.86(14) . . ? C14 O5 Mn1 136.14(15) . 1_545 ? Mn1 O1W H1B 132(2) . . ? Mn1 O1W H1A 124(2) . . ? H1B O1W H1A 102(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 O1 C1 C2 C3 175.2(2) . . . . ? N1 C1 C2 C3 -2.6(3) . . . . ? O1 C1 C2 C6 -5.1(3) . . . . ? N1 C1 C2 C6 177.17(19) . . . . ? C1 C2 C3 C4 1.9(3) . . . . ? C6 C2 C3 C4 -177.8(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 N1 -1.4(3) . . . . ? C3 C2 C6 O3 -26.7(3) . . . . ? C1 C2 C6 O3 153.5(2) . . . . ? C3 C2 C6 O2 150.2(2) . . . . ? C1 C2 C6 O2 -29.5(3) . . . . ? N1 C7 C8 C9 -98.0(2) . . . . ? N1 C7 C8 C13 80.3(2) . . . . ? C13 C8 C9 C10 -2.3(3) . . . . ? C7 C8 C9 C10 176.0(2) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C9 C10 C11 C12 1.7(3) . . . . ? C9 C10 C11 C14 -176.3(2) . . . . ? C10 C11 C12 C13 -1.3(3) . . . . ? C14 C11 C12 C13 176.8(2) . . . . ? C11 C12 C13 C8 -1.0(3) . . . . ? C9 C8 C13 C12 2.8(3) . . . . ? C7 C8 C13 C12 -175.5(2) . . . . ? C12 C11 C14 O4 -169.5(2) . . . . ? C10 C11 C14 O4 8.5(4) . . . . ? C12 C11 C14 O5 10.3(3) . . . . ? C10 C11 C14 O5 -171.7(2) . . . . ? N2 C20 C21 C22 -0.8(4) . . . . ? C15 C20 C21 C22 178.5(2) . . . . ? C20 C21 C22 C23 -0.5(4) . . . . ? C21 C22 C23 C24 2.0(4) . . . . ? C22 C23 C24 N2 -2.4(4) . . . . ? N2 C20 C15 N3 -2.0(3) . . . . ? C21 C20 C15 N3 178.7(2) . . . . ? N2 C20 C15 C16 177.5(2) . . . . ? C21 C20 C15 C16 -1.8(3) . . . . ? N3 C15 C16 C17 0.9(3) . . . . ? C20 C15 C16 C17 -178.6(2) . . . . ? C15 C16 C17 C18 0.0(4) . . . . ? C16 C17 C18 C19 -0.4(4) . . . . ? C17 C18 C19 N3 -0.2(4) . . . . ? C4 C5 N1 C1 0.6(3) . . . . ? C4 C5 N1 C7 178.0(2) . . . . ? O1 C1 N1 C5 -176.51(19) . . . . ? C2 C1 N1 C5 1.4(3) . . . . ? O1 C1 N1 C7 6.1(3) . . . . ? C2 C1 N1 C7 -176.02(18) . . . . ? C8 C7 N1 C5 94.1(2) . . . . ? C8 C7 N1 C1 -88.4(2) . . . . ? C23 C24 N2 C20 1.1(3) . . . . ? C23 C24 N2 Mn1 167.94(18) . . . . ? C21 C20 N2 C24 0.5(3) . . . . ? C15 C20 N2 C24 -178.82(19) . . . . ? C21 C20 N2 Mn1 -167.02(17) . . . . ? C15 C20 N2 Mn1 13.7(2) . . . . ? O5 Mn1 N2 C24 3.54(18) 1_565 . . . ? O2 Mn1 N2 C24 -132.51(18) . . . . ? O1 Mn1 N2 C24 -89.53(17) . . . . ? O1W Mn1 N2 C24 89.18(18) . . . . ? N3 Mn1 N2 C24 179.11(18) . . . . ? O5 Mn1 N2 C20 170.42(15) 1_565 . . . ? O2 Mn1 N2 C20 34.4(2) . . . . ? O1 Mn1 N2 C20 77.35(15) . . . . ? O1W Mn1 N2 C20 -103.94(16) . . . . ? N3 Mn1 N2 C20 -14.01(15) . . . . ? C18 C19 N3 C15 1.0(3) . . . . ? C18 C19 N3 Mn1 -169.73(18) . . . . ? C16 C15 N3 C19 -1.4(3) . . . . ? C20 C15 N3 C19 178.11(19) . . . . ? C16 C15 N3 Mn1 170.06(16) . . . . ? C20 C15 N3 Mn1 -10.4(2) . . . . ? O5 Mn1 N3 C19 -154.4(3) 1_565 . . . ? O2 Mn1 N3 C19 23.32(19) . . . . ? O1 Mn1 N3 C19 104.46(19) . . . . ? O1W Mn1 N3 C19 -78.87(19) . . . . ? N2 Mn1 N3 C19 -176.5(2) . . . . ? O5 Mn1 N3 C15 34.8(4) 1_565 . . . ? O2 Mn1 N3 C15 -147.49(15) . . . . ? O1 Mn1 N3 C15 -66.35(15) . . . . ? O1W Mn1 N3 C15 110.32(16) . . . . ? N2 Mn1 N3 C15 12.73(14) . . . . ? N1 C1 O1 Mn1 -139.17(16) . . . . ? C2 C1 O1 Mn1 43.1(3) . . . . ? O5 Mn1 O1 C1 63.17(17) 1_565 . . . ? O2 Mn1 O1 C1 -37.75(17) . . . . ? O1W Mn1 O1 C1 137.9(11) . . . . ? N2 Mn1 O1 C1 160.45(18) . . . . ? N3 Mn1 O1 C1 -128.36(17) . . . . ? O3 C6 O2 Mn1 -160.88(18) . . . . ? C2 C6 O2 Mn1 22.3(3) . . . . ? O5 Mn1 O2 C6 -87.4(2) 1_565 . . . ? O1 Mn1 O2 C6 5.5(2) . . . . ? O1W Mn1 O2 C6 -174.3(2) . . . . ? N2 Mn1 O2 C6 48.1(3) . . . . ? N3 Mn1 O2 C6 93.1(2) . . . . ? O4 C14 O5 Mn1 36.2(4) . . . 1_545 ? C11 C14 O5 Mn1 -143.53(18) . . . 1_545 ? 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 O1W H1B O3 0.890(10) 1.967(14) 2.820(2) 160(3) 2_565 O1W H1B O2 0.890(10) 2.50(2) 3.232(2) 140(2) 2_565 O1W H1A O3 0.891(10) 1.989(12) 2.863(2) 167(3) 1_655 _diffrn_measured_fraction_theta_max 0.837 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.277 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.060 #=========================END _database_code_depnum_ccdc_archive 'CCDC 938801'