# 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_a #TrackingRef '(1)Co(Cl-BDC).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 Cl2 Co N4 O4.50' _chemical_formula_weight 503.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M c2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.662(7) _cell_length_b 13.469(4) _cell_length_c 19.049(7) _cell_angle_alpha 90.00 _cell_angle_beta 119.676(4) _cell_angle_gamma 90.00 _cell_volume 4383(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 1.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8156 _exptl_absorpt_correction_T_max 0.8569 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16855 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5013 _reflns_number_gt 4240 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0972P)^2^+9.1199P] 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 SHELXL _refine_ls_extinction_coef 0.0018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5013 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1874 _refine_ls_wR_factor_gt 0.1760 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Co1 Co 0.54868(3) 0.76305(4) 0.04765(3) 0.0441(2) Uani 1 1 d . . . N4 N 0.89098(18) 0.3577(2) 0.36210(17) 0.0471(7) Uani 1 1 d . . . N3 N 0.60777(17) 0.6345(2) 0.07935(18) 0.0485(7) Uani 1 1 d . . . C3 C 0.8246(2) 0.4429(3) 0.2463(2) 0.0468(8) Uani 1 1 d . . . N2 N 0.58545(18) 0.5565(2) 0.1079(2) 0.0532(8) Uani 1 1 d . . . H2A H 0.5409 0.5525 0.1060 0.064 Uiso 1 1 calc R . . C2 C 0.7032(2) 0.5195(3) 0.1309(2) 0.0472(8) Uani 1 1 d . . . N1 N 0.8821(2) 0.4534(2) 0.37826(18) 0.0538(8) Uani 1 1 d . . . H1A H 0.9001 0.4770 0.4262 0.065 Uiso 1 1 calc R . . C9 C 0.6801(2) 0.6123(3) 0.0935(2) 0.0484(8) Uani 1 1 d . . . C1 C 0.85679(19) 0.3514(3) 0.28106(19) 0.0449(8) Uani 1 1 d . . . C4 C 0.7803(2) 0.4679(3) 0.1577(2) 0.0562(10) Uani 1 1 d . . . H4A H 0.8128 0.5103 0.1453 0.067 Uiso 1 1 calc R . . H4B H 0.7707 0.4072 0.1269 0.067 Uiso 1 1 calc R . . C6 C 0.8421(2) 0.5065(3) 0.3107(2) 0.0527(9) Uani 1 1 d . . . C5 C 0.8588(3) 0.2567(3) 0.2414(3) 0.0586(10) Uani 1 1 d . . . H5A H 0.8853 0.2067 0.2818 0.088 Uiso 1 1 calc R . . H5B H 0.8862 0.2672 0.2120 0.088 Uiso 1 1 calc R . . H5C H 0.8063 0.2354 0.2049 0.088 Uiso 1 1 calc R . . C10 C 0.6409(2) 0.4863(3) 0.1394(2) 0.0519(9) Uani 1 1 d . . . C8 C 0.7238(3) 0.6831(4) 0.0698(3) 0.0727(13) Uani 1 1 d . . . H8A H 0.6922 0.7409 0.0454 0.109 Uiso 1 1 calc R . . H8B H 0.7356 0.6516 0.0320 0.109 Uiso 1 1 calc R . . H8C H 0.7716 0.7024 0.1170 0.109 Uiso 1 1 calc R . . C11 C 0.6295(3) 0.3931(4) 0.1747(4) 0.0808(15) Uani 1 1 d . . . H11A H 0.5790 0.3944 0.1712 0.121 Uiso 1 1 calc R . . H11B H 0.6695 0.3880 0.2304 0.121 Uiso 1 1 calc R . . H11C H 0.6325 0.3370 0.1454 0.121 Uiso 1 1 calc R . . C7 C 0.8272(3) 0.6143(4) 0.3136(3) 0.0805(15) Uani 1 1 d . . . H7A H 0.8473 0.6344 0.3688 0.121 Uiso 1 1 calc R . . H7B H 0.7719 0.6266 0.2837 0.121 Uiso 1 1 calc R . . H7C H 0.8527 0.6515 0.2902 0.121 Uiso 1 1 calc R . . O1 O 0.43835(19) 0.7516(3) 0.0114(2) 0.0748(9) Uani 1 1 d . B . C14 C 0.3280(2) 0.7239(4) 0.0249(2) 0.0611(11) Uani 1 1 d . . . C13 C 0.4129(2) 0.7029(5) 0.0500(3) 0.0719(14) Uani 1 1 d . . . C12 C 0.2781(2) 0.6571(4) 0.0329(2) 0.0635(11) Uani 1 1 d . . . Cl1 Cl 0.30642(9) 0.53886(13) 0.07231(10) 0.0941(5) Uani 1 1 d . B . Cl2 Cl 0.54222(12) 1.09507(15) -0.16889(11) 0.0546(4) Uani 0.50 1 d P . . Cl3 Cl 0.56914(15) 0.68642(17) -0.15822(14) 0.0709(6) Uani 0.50 1 d P . . O4 O 0.5432(2) 0.8081(3) -0.05094(18) 0.0754(9) Uani 1 1 d . . . C19 C 0.5511(2) 0.8891(3) -0.0771(2) 0.0551(9) Uani 1 1 d . . . C18 C 0.5130(2) 0.9777(3) -0.2088(2) 0.0474(8) Uani 1 1 d . . . C15 C 0.2011(2) 0.6837(4) 0.0075(2) 0.0619(11) Uani 1 1 d . . . H15A H 0.1682 0.6380 0.0123 0.074 Uiso 1 1 calc R . . C17 C 0.5266(2) 0.8901(3) -0.1661(2) 0.0534(9) Uani 1 1 d . . . O3 O 0.5738(3) 0.9658(3) -0.03825(19) 0.1210(19) Uani 1 1 d . . . C16 C 0.5338(15) 0.8009(6) -0.2047(6) 0.045(4) Uani 0.48(4) 1 d P . 1 C16' C 0.4932(16) 0.8051(9) -0.2117(5) 0.056(4) Uani 0.52(4) 1 d P . 2 O1W O 0.5000 0.5354(9) 0.2500 0.242(6) Uani 1 2 d S A 2 H1WA H 0.4865 0.5722 0.2090 0.291 Uiso 0.50 1 d PR A 2 H1WB H 0.5135 0.5722 0.2910 0.291 Uiso 0.50 1 d PR A 2 O2 O 0.4524(2) 0.6481(5) 0.1056(3) 0.140(2) Uani 1 1 d . B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0425(3) 0.0514(3) 0.0369(3) 0.00227(19) 0.0185(2) -0.0009(2) N4 0.0512(16) 0.0517(17) 0.0356(14) -0.0011(12) 0.0194(12) 0.0060(13) N3 0.0458(15) 0.0500(17) 0.0507(17) 0.0083(13) 0.0246(13) 0.0015(13) C3 0.0436(17) 0.062(2) 0.0353(16) 0.0016(15) 0.0200(14) 0.0074(16) N2 0.0435(15) 0.0552(18) 0.0621(19) 0.0101(15) 0.0271(14) -0.0014(14) C2 0.0464(18) 0.056(2) 0.0361(16) 0.0036(14) 0.0182(14) 0.0058(16) N1 0.0636(19) 0.0577(19) 0.0341(14) -0.0037(13) 0.0196(14) 0.0125(15) C9 0.0475(18) 0.058(2) 0.0430(18) 0.0042(15) 0.0246(15) -0.0002(16) C1 0.0416(16) 0.056(2) 0.0337(16) -0.0039(14) 0.0163(13) -0.0013(15) C4 0.055(2) 0.076(3) 0.0366(18) 0.0080(17) 0.0226(16) 0.0183(19) C6 0.054(2) 0.061(2) 0.0414(18) 0.0006(16) 0.0221(16) 0.0150(17) C5 0.070(3) 0.056(2) 0.044(2) -0.0076(16) 0.0233(19) -0.0014(19) C10 0.052(2) 0.051(2) 0.050(2) 0.0031(16) 0.0233(17) -0.0018(16) C8 0.063(2) 0.082(3) 0.086(3) 0.024(3) 0.047(2) 0.002(2) C11 0.078(3) 0.063(3) 0.105(4) 0.024(3) 0.048(3) -0.002(2) C7 0.105(4) 0.066(3) 0.054(2) -0.002(2) 0.028(2) 0.033(3) O1 0.0492(16) 0.091(2) 0.091(2) -0.0134(18) 0.0399(17) -0.0065(15) C14 0.0394(18) 0.104(4) 0.0389(19) -0.019(2) 0.0184(15) -0.007(2) C13 0.0400(19) 0.132(4) 0.043(2) -0.010(2) 0.0196(17) 0.000(2) C12 0.051(2) 0.096(3) 0.0398(19) -0.015(2) 0.0196(17) -0.001(2) Cl1 0.0794(9) 0.1045(11) 0.0903(10) 0.0005(8) 0.0358(7) 0.0090(8) Cl2 0.0608(10) 0.0584(11) 0.0470(9) -0.0107(8) 0.0284(8) -0.0024(8) Cl3 0.0926(16) 0.0546(12) 0.0671(13) 0.0121(10) 0.0408(12) 0.0197(11) O4 0.111(3) 0.070(2) 0.0475(16) 0.0049(15) 0.0412(17) -0.0127(19) C19 0.064(2) 0.066(2) 0.0368(18) 0.0031(17) 0.0260(17) -0.0020(19) C18 0.0453(18) 0.053(2) 0.0416(18) -0.0020(15) 0.0198(14) 0.0010(15) C15 0.0446(19) 0.097(3) 0.043(2) -0.013(2) 0.0214(16) -0.011(2) C17 0.065(2) 0.060(2) 0.0395(18) -0.0050(16) 0.0290(17) -0.0118(18) O3 0.225(6) 0.080(3) 0.0395(17) -0.0077(16) 0.052(3) -0.041(3) C16 0.054(10) 0.042(4) 0.046(4) -0.001(3) 0.030(5) 0.002(4) C16' 0.060(11) 0.070(5) 0.044(4) 0.004(4) 0.029(5) -0.009(5) O1W 0.300(16) 0.173(10) 0.173(11) 0.000 0.056(10) 0.000 O2 0.063(2) 0.274(7) 0.091(3) 0.076(4) 0.044(2) 0.054(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O4 1.925(3) . ? Co1 O1 1.930(3) . ? Co1 N4 1.992(3) 4_655 ? Co1 N3 2.004(3) . ? N4 C1 1.347(4) . ? N4 N1 1.356(4) . ? N4 Co1 1.992(3) 4_645 ? N3 C9 1.343(5) . ? N3 N2 1.351(4) . ? C3 C6 1.393(5) . ? C3 C1 1.394(5) . ? C3 C4 1.504(5) . ? N2 C10 1.340(5) . ? C2 C10 1.388(5) . ? C2 C9 1.399(5) . ? C2 C4 1.508(5) . ? N1 C6 1.336(5) . ? C9 C8 1.495(5) . ? C1 C5 1.493(5) . ? C6 C7 1.488(6) . ? C10 C11 1.492(6) . ? O1 C13 1.259(6) . ? C14 C15 1.381(7) 7_565 ? C14 C12 1.394(6) . ? C14 C13 1.519(6) . ? C13 O2 1.206(7) . ? C12 C15 1.389(6) . ? C12 Cl1 1.731(5) . ? Cl2 C18 1.724(4) . ? Cl3 C16 1.742(9) . ? Cl3 C16' 2.08(2) . ? O4 C19 1.241(5) . ? C19 O3 1.220(5) . ? C19 C17 1.517(5) . ? C18 C17 1.383(5) . ? C18 C18 1.388(7) 2_654 ? C15 C14 1.381(7) 7_565 ? C17 C16' 1.389(10) . ? C17 C16 1.451(10) . ? C16 C16 1.57(3) 2_654 ? C16' C16' 1.61(3) 2_654 ? 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 Co1 O1 99.57(17) . . ? O4 Co1 N4 111.21(13) . 4_655 ? O1 Co1 N4 116.34(14) . 4_655 ? O4 Co1 N3 108.08(14) . . ? O1 Co1 N3 114.83(14) . . ? N4 Co1 N3 106.51(13) 4_655 . ? C1 N4 N1 105.8(3) . . ? C1 N4 Co1 134.0(3) . 4_645 ? N1 N4 Co1 120.1(2) . 4_645 ? C9 N3 N2 105.6(3) . . ? C9 N3 Co1 130.6(3) . . ? N2 N3 Co1 122.5(2) . . ? C6 C3 C1 105.6(3) . . ? C6 C3 C4 127.1(4) . . ? C1 C3 C4 127.3(3) . . ? C10 N2 N3 112.0(3) . . ? C10 C2 C9 105.3(3) . . ? C10 C2 C4 127.6(4) . . ? C9 C2 C4 127.1(3) . . ? C6 N1 N4 111.7(3) . . ? N3 C9 C2 110.2(3) . . ? N3 C9 C8 120.5(4) . . ? C2 C9 C8 129.3(4) . . ? N4 C1 C3 109.9(3) . . ? N4 C1 C5 120.7(3) . . ? C3 C1 C5 129.4(3) . . ? C2 C4 C3 114.3(3) . . ? N1 C6 C3 106.9(3) . . ? N1 C6 C7 121.3(4) . . ? C3 C6 C7 131.8(4) . . ? N2 C10 C2 106.8(3) . . ? N2 C10 C11 121.7(4) . . ? C2 C10 C11 131.5(4) . . ? C13 O1 Co1 122.3(3) . . ? C15 C14 C12 118.2(4) 7_565 . ? C15 C14 C13 117.1(4) 7_565 . ? C12 C14 C13 124.7(5) . . ? O2 C13 O1 124.2(4) . . ? O2 C13 C14 121.3(4) . . ? O1 C13 C14 114.3(5) . . ? C15 C12 C14 120.0(5) . . ? C15 C12 Cl1 116.7(4) . . ? C14 C12 Cl1 123.3(4) . . ? C16 Cl3 C16' 20.1(4) . . ? C19 O4 Co1 135.3(3) . . ? O3 C19 O4 125.6(4) . . ? O3 C19 C17 119.3(4) . . ? O4 C19 C17 115.0(4) . . ? C17 C18 C18 121.4(2) . 2_654 ? C17 C18 Cl2 126.7(3) . . ? C18 C18 Cl2 110.77(15) 2_654 . ? C14 C15 C12 121.8(4) 7_565 . ? C18 C17 C16' 116.2(5) . . ? C18 C17 C16 116.6(5) . . ? C16' C17 C16 30.3(4) . . ? C18 C17 C19 121.8(4) . . ? C16' C17 C19 118.8(5) . . ? C16 C17 C19 120.2(5) . . ? C17 C16 C16 108.3(15) . 2_654 ? C17 C16 Cl3 126.1(5) . . ? C16 C16 Cl3 117.7(5) 2_654 . ? C17 C16' C16' 109.1(16) . 2_654 ? C17 C16' Cl3 109.0(12) . . ? C16' C16' Cl3 92.5(16) 2_654 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.502 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 881876' ####################################################################### # # 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_a2 #TrackingRef '(2)Cd(Cl-BDC).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 Cd Cl2 N4 O4' _chemical_formula_weight 549.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.911(3) _cell_length_b 10.115(3) _cell_length_c 12.281(4) _cell_angle_alpha 83.369(14) _cell_angle_beta 67.120(12) _cell_angle_gamma 69.755(12) _cell_volume 1063.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 1.311 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7795 _exptl_absorpt_correction_T_max 0.8177 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9134 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0951 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4750 _reflns_number_gt 3152 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1503P)^2^+1.5000P] 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 4750 _refine_ls_number_parameters 271 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.2407 _refine_ls_wR_factor_gt 0.1604 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.006 _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 Cd1 Cd -0.45061(6) 0.02506(5) 0.81292(5) 0.0341(2) Uani 1 1 d . . . N4 N -0.2106(7) 0.0038(7) 0.8070(5) 0.0363(15) Uani 1 1 d . . . C6 C 0.1888(10) 0.0160(9) 0.7037(7) 0.0407(18) Uani 1 1 d . . . H6A H 0.1674 0.1171 0.7029 0.049 Uiso 1 1 calc R . . H6B H 0.2509 -0.0235 0.7516 0.049 Uiso 1 1 calc R . . N3 N 0.4074(8) -0.0545(7) 0.3839(6) 0.0377(15) Uani 1 1 d . . . N2 N 0.4255(8) -0.1844(7) 0.4266(6) 0.0390(15) Uani 1 1 d . . . H2A H 0.4723 -0.2604 0.3837 0.047 Uiso 1 1 calc R . . C3 C 0.0385(9) -0.0108(9) 0.7637(6) 0.0327(16) Uani 1 1 d . . . N1 N -0.1549(8) -0.0813(7) 0.8845(6) 0.0451(18) Uani 1 1 d . . . H1A H -0.2071 -0.1237 0.9410 0.054 Uiso 1 1 calc R . . O2 O -0.4760(10) -0.1421(7) 0.9658(6) 0.0646(15) Uani 1 1 d U . . C10 C 0.3153(9) 0.0356(9) 0.4772(7) 0.0378(17) Uani 1 1 d . . . C2 C -0.0961(8) 0.0445(8) 0.7319(6) 0.0330(16) Uani 1 1 d . . . C5 C 0.0791(12) -0.1752(10) 0.9362(8) 0.050(2) Uani 1 1 d . . . H5A H 0.0158 -0.2196 0.9983 0.076 Uiso 1 1 calc R . . H5B H 0.1086 -0.1139 0.9699 0.076 Uiso 1 1 calc R . . H5C H 0.1704 -0.2461 0.8872 0.076 Uiso 1 1 calc R . . C9 C 0.3599(8) -0.1806(9) 0.5473(7) 0.0388(19) Uani 1 1 d . . . C8 C 0.3646(14) -0.3102(11) 0.6151(9) 0.066(3) Uani 1 1 d . . . H8A H 0.3158 -0.2868 0.6981 0.099 Uiso 1 1 calc R . . H8B H 0.4705 -0.3689 0.5971 0.099 Uiso 1 1 calc R . . H8C H 0.3105 -0.3597 0.5947 0.099 Uiso 1 1 calc R . . C4 C -0.0116(10) -0.0903(9) 0.8621(6) 0.0374(18) Uani 1 1 d . . . O1 O -0.5128(10) -0.1823(7) 0.8122(6) 0.0655(16) Uani 1 1 d U . . C11 C 0.2671(11) 0.1918(9) 0.4630(8) 0.052(2) Uani 1 1 d . . . H11A H 0.3013 0.2130 0.3805 0.078 Uiso 1 1 calc R . . H11B H 0.3128 0.2316 0.5012 0.078 Uiso 1 1 calc R . . H11C H 0.1562 0.2313 0.4984 0.078 Uiso 1 1 calc R . . C1 C -0.1139(11) 0.1414(10) 0.6339(7) 0.045(2) Uani 1 1 d . . . H1B H -0.2152 0.1608 0.6327 0.067 Uiso 1 1 calc R . . H1C H -0.0366 0.0981 0.5600 0.067 Uiso 1 1 calc R . . H1D H -0.1014 0.2279 0.6458 0.067 Uiso 1 1 calc R . . C12 C -0.4958(14) -0.2231(11) 0.9027(9) 0.0595(15) Uani 1 1 d U . . C7 C 0.2841(8) -0.0393(9) 0.5816(7) 0.0349(17) Uani 1 1 d . . . Cl1 Cl -1.0738(3) 0.5409(3) 1.26652(19) 0.0638(8) Uani 1 1 d . . . O4 O -0.6093(7) 0.3444(7) 0.7787(6) 0.0519(16) Uani 1 1 d . . . O3 O -0.6858(7) 0.1750(7) 0.8858(6) 0.0573(19) Uani 1 1 d . . . C14 C -0.8548(8) 0.4095(8) 0.9293(6) 0.0316(15) Uani 1 1 d . . . C16 C -1.0358(10) 0.5186(8) 1.1183(7) 0.0391(18) Uani 1 1 d . . . C15 C -0.8923(9) 0.4281(8) 1.0486(7) 0.0386(19) Uani 1 1 d . . . H15A H -0.8204 0.3794 1.0825 0.046 Uiso 1 1 calc R . . C13 C -0.7010(8) 0.3039(9) 0.8583(7) 0.0388(19) Uani 1 1 d . . . C19 C -0.5001(10) -0.3673(9) 0.9500(7) 0.0382(17) Uani 1 1 d . . . C18 C -0.5789(9) -0.3794(8) 1.0695(7) 0.0342(16) Uani 1 1 d . . . H18A H -0.6311 -0.2993 1.1184 0.041 Uiso 1 1 calc R . . C17 C -0.4197(10) -0.4890(8) 0.8830(7) 0.0363(17) Uani 1 1 d . . . Cl2 Cl -0.3126(3) -0.4868(2) 0.7316(2) 0.0594(7) 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 Cd1 0.0302(4) 0.0215(3) 0.0371(3) 0.0042(2) -0.0020(2) -0.0058(2) N4 0.033(3) 0.036(4) 0.030(3) -0.005(3) -0.004(3) -0.008(3) C6 0.046(5) 0.038(5) 0.036(4) -0.002(3) -0.009(3) -0.017(4) N3 0.040(4) 0.033(4) 0.034(3) 0.003(3) -0.007(3) -0.013(3) N2 0.040(4) 0.037(4) 0.036(3) 0.003(3) -0.012(3) -0.011(3) C3 0.032(4) 0.040(4) 0.025(3) -0.002(3) -0.009(3) -0.011(3) N1 0.045(4) 0.032(4) 0.039(3) 0.011(3) 0.000(3) -0.011(3) O2 0.099(4) 0.041(3) 0.063(3) 0.016(2) -0.038(3) -0.029(3) C10 0.030(4) 0.031(4) 0.042(4) -0.005(3) -0.004(3) -0.006(3) C2 0.025(4) 0.041(4) 0.029(3) 0.000(3) -0.004(3) -0.013(3) C5 0.065(6) 0.051(6) 0.049(5) 0.013(4) -0.031(5) -0.028(5) C9 0.015(3) 0.044(5) 0.042(4) 0.008(3) 0.003(3) -0.010(3) C8 0.090(8) 0.041(6) 0.051(5) 0.005(4) -0.025(5) -0.004(5) C4 0.043(4) 0.036(4) 0.028(3) -0.007(3) -0.010(3) -0.007(3) O1 0.101(4) 0.040(3) 0.060(3) 0.017(2) -0.036(3) -0.025(3) C11 0.061(6) 0.031(5) 0.046(5) -0.002(4) 0.002(4) -0.019(4) C1 0.056(5) 0.053(5) 0.035(4) 0.009(4) -0.022(4) -0.025(4) C12 0.096(4) 0.038(3) 0.058(3) 0.017(2) -0.040(3) -0.029(3) C7 0.022(3) 0.048(5) 0.033(4) 0.002(3) -0.012(3) -0.010(3) Cl1 0.0695(16) 0.0743(18) 0.0350(11) -0.0152(11) -0.0216(11) -0.0012(13) O4 0.036(3) 0.053(4) 0.055(4) -0.019(3) 0.006(3) -0.020(3) O3 0.043(4) 0.035(3) 0.051(3) -0.003(3) -0.001(3) 0.019(3) C14 0.022(3) 0.028(4) 0.037(4) -0.006(3) -0.002(3) -0.008(3) C16 0.052(5) 0.028(4) 0.031(3) -0.006(3) -0.014(3) -0.005(3) C15 0.028(4) 0.027(4) 0.038(4) -0.004(3) -0.004(3) 0.009(3) C13 0.016(3) 0.039(5) 0.045(4) -0.002(3) -0.002(3) 0.000(3) C19 0.041(4) 0.030(4) 0.044(4) 0.009(3) -0.019(4) -0.012(3) C18 0.036(4) 0.025(4) 0.039(4) 0.005(3) -0.013(3) -0.008(3) C17 0.045(4) 0.022(4) 0.035(4) 0.010(3) -0.015(3) -0.007(3) Cl2 0.0712(16) 0.0356(12) 0.0447(11) 0.0063(9) 0.0003(11) -0.0132(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O3 2.186(5) . ? Cd1 N4 2.286(7) . ? Cd1 N3 2.288(7) 2_556 ? Cd1 O2 2.375(7) . ? Cd1 O1 2.384(8) . ? Cd1 C12 2.733(10) . ? N4 C2 1.315(10) . ? N4 N1 1.357(9) . ? C6 C7 1.476(10) . ? C6 C3 1.488(11) . ? N3 N2 1.336(9) . ? N3 C10 1.352(10) . ? N3 Cd1 2.288(7) 2_556 ? N2 C9 1.367(10) . ? C3 C4 1.393(11) . ? C3 C2 1.444(10) . ? N1 C4 1.309(11) . ? O2 C12 1.299(13) . ? C10 C7 1.394(11) . ? C10 C11 1.494(11) . ? C2 C1 1.488(11) . ? C5 C4 1.515(11) . ? C9 C7 1.391(12) . ? C9 C8 1.467(12) . ? O1 C12 1.193(11) . ? C12 C19 1.515(12) . ? Cl1 C16 1.735(8) . ? O4 C13 1.194(10) . ? O3 C13 1.280(11) . ? C14 C16 1.377(11) 2_367 ? C14 C15 1.382(10) . ? C14 C13 1.510(9) . ? C16 C14 1.377(11) 2_367 ? C16 C15 1.388(10) . ? C19 C17 1.368(11) . ? C19 C18 1.383(11) . ? C18 C17 1.393(10) 2_447 ? C17 C18 1.393(10) 2_447 ? C17 Cl2 1.749(8) . ? 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 O3 Cd1 N4 137.0(3) . . ? O3 Cd1 N3 98.9(2) . 2_556 ? N4 Cd1 N3 99.3(2) . 2_556 ? O3 Cd1 O2 97.7(3) . . ? N4 Cd1 O2 90.4(3) . . ? N3 Cd1 O2 143.0(3) 2_556 . ? O3 Cd1 O1 98.9(3) . . ? N4 Cd1 O1 119.3(3) . . ? N3 Cd1 O1 90.8(2) 2_556 . ? O2 Cd1 O1 54.0(3) . . ? O3 Cd1 C12 101.7(3) . . ? N4 Cd1 C12 105.0(3) . . ? N3 Cd1 C12 115.4(3) 2_556 . ? O2 Cd1 C12 28.4(3) . . ? O1 Cd1 C12 25.8(3) . . ? C2 N4 N1 106.5(7) . . ? C2 N4 Cd1 133.4(5) . . ? N1 N4 Cd1 119.5(5) . . ? C7 C6 C3 117.7(7) . . ? N2 N3 C10 106.6(6) . . ? N2 N3 Cd1 118.4(5) . 2_556 ? C10 N3 Cd1 130.6(6) . 2_556 ? N3 N2 C9 111.0(7) . . ? C4 C3 C2 102.1(7) . . ? C4 C3 C6 131.0(7) . . ? C2 C3 C6 126.9(7) . . ? C4 N1 N4 111.3(6) . . ? C12 O2 Cd1 91.3(6) . . ? N3 C10 C7 110.0(7) . . ? N3 C10 C11 121.9(7) . . ? C7 C10 C11 128.0(7) . . ? N4 C2 C3 110.5(7) . . ? N4 C2 C1 122.3(7) . . ? C3 C2 C1 127.1(7) . . ? N2 C9 C7 106.6(7) . . ? N2 C9 C8 121.4(8) . . ? C7 C9 C8 131.7(8) . . ? N1 C4 C3 109.6(7) . . ? N1 C4 C5 123.0(8) . . ? C3 C4 C5 127.5(8) . . ? C12 O1 Cd1 93.7(7) . . ? O1 C12 O2 120.2(9) . . ? O1 C12 C19 122.3(9) . . ? O2 C12 C19 117.5(8) . . ? O1 C12 Cd1 60.5(6) . . ? O2 C12 Cd1 60.3(5) . . ? C19 C12 Cd1 173.1(8) . . ? C9 C7 C10 105.5(7) . . ? C9 C7 C6 126.1(7) . . ? C10 C7 C6 128.4(8) . . ? C13 O3 Cd1 116.0(5) . . ? C16 C14 C15 118.4(6) 2_367 . ? C16 C14 C13 122.4(7) 2_367 . ? C15 C14 C13 119.0(7) . . ? C14 C16 C15 120.8(7) 2_367 . ? C14 C16 Cl1 120.6(6) 2_367 . ? C15 C16 Cl1 118.6(6) . . ? C14 C15 C16 120.9(7) . . ? O4 C13 O3 125.7(7) . . ? O4 C13 C14 118.9(8) . . ? O3 C13 C14 115.2(7) . . ? C17 C19 C18 117.5(7) . . ? C17 C19 C12 123.7(8) . . ? C18 C19 C12 118.7(8) . . ? C19 C18 C17 120.3(7) . 2_447 ? C19 C17 C18 122.2(7) . 2_447 ? C19 C17 Cl2 121.5(6) . . ? C18 C17 Cl2 116.3(6) 2_447 . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.808 _refine_diff_density_min -1.023 _refine_diff_density_rms 0.225 _database_code_depnum_ccdc_archive 'CCDC 881877' ####################################################################### # # 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_a3 #TrackingRef '(3)Cd(OH-BDC).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 Cd N8 O6' _chemical_formula_weight 719.08 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 monoclinic _symmetry_space_group_name_H-M p2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 20.3721(8) _cell_length_b 9.4647(2) _cell_length_c 17.2551(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.434(3) _cell_angle_gamma 90.00 _cell_volume 3299.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.715 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8701 _exptl_absorpt_correction_T_max 0.8941 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27246 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7472 _reflns_number_gt 6014 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0801P)^2^+1.3970P] 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 7472 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1090 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.007 _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 0.5000 0.54739(4) 0.2500 0.02398(12) Uani 1 2 d S . . Cd2 Cd 1.0000 0.71392(4) 0.2500 0.02381(12) Uani 1 2 d S . . O4 O 0.88623(13) 0.7188(3) 0.19166(16) 0.0319(6) Uani 1 1 d . . . N2 N 1.05396(17) 1.5195(3) 0.39285(19) 0.0327(7) Uani 1 1 d . . . H2D H 1.0861 1.5790 0.3958 0.039 Uiso 1 1 calc R . . O3 O 0.57989(14) 0.5725(3) 0.16705(17) 0.0362(7) Uani 1 1 d . . . O5 O 0.76637(15) 0.6404(3) -0.07194(16) 0.0393(7) Uani 1 1 d . . . H5D H 0.7535 0.5694 -0.0966 0.059 Uiso 1 1 calc R . . N8 N 0.53605(16) 1.3298(3) 0.39379(19) 0.0307(7) Uani 1 1 d . . . H8C H 0.5063 1.3742 0.4153 0.037 Uiso 1 1 calc R . . N1 N 0.91017(15) 0.8906(3) 0.35080(18) 0.0277(7) Uani 1 1 d . . . H1D H 0.8813 0.8266 0.3359 0.033 Uiso 1 1 calc R . . N6 N 0.58316(18) 0.7017(3) 0.4079(2) 0.0332(8) Uani 1 1 d . . . H6A H 0.5727 0.6301 0.4344 0.040 Uiso 1 1 calc R . . O2 O 0.81013(15) 0.7298(3) 0.27320(16) 0.0397(7) Uani 1 1 d . . . O1 O 0.56487(14) 0.4720(3) 0.04948(17) 0.0374(7) Uani 1 1 d . . . C27 C 0.77512(18) 0.6777(4) 0.1388(2) 0.0258(8) Uani 1 1 d . . . C25 C 0.61059(18) 1.1727(4) 0.3739(2) 0.0267(8) Uani 1 1 d . . . C24 C 0.56714(19) 1.2139(4) 0.4239(2) 0.0288(8) Uani 1 1 d . . . C23 C 0.71210(18) 0.6342(4) 0.1515(2) 0.0271(8) Uani 1 1 d . . . H23A H 0.7003 0.6355 0.2018 0.032 Uiso 1 1 calc R . . C22 C 0.65717(19) 1.0492(4) 0.3837(2) 0.0300(8) Uani 1 1 d . . . H22A H 0.6847 1.0578 0.4337 0.036 Uiso 1 1 calc R . . H22B H 0.6860 1.0536 0.3432 0.036 Uiso 1 1 calc R . . C21 C 0.89807(19) 1.0038(4) 0.3948(2) 0.0282(8) Uani 1 1 d . . . N4 N 0.97246(16) 0.8902(3) 0.33329(18) 0.0286(7) Uani 1 1 d . . . C20 C 0.59841(18) 0.5397(4) 0.1029(2) 0.0249(7) Uani 1 1 d . . . C19 C 0.62397(19) 0.9070(4) 0.3800(2) 0.0275(8) Uani 1 1 d . . . C18 C 0.79154(18) 0.6805(4) 0.0633(2) 0.0273(8) Uani 1 1 d . . . H18A H 0.8329 0.7135 0.0544 0.033 Uiso 1 1 calc R . . C17 C 0.5906(2) 0.8422(4) 0.3122(2) 0.0311(8) Uani 1 1 d . . . C16 C 0.82700(18) 0.7113(4) 0.2068(2) 0.0272(8) Uani 1 1 d . . . N3 N 0.99877(17) 1.5297(3) 0.3403(2) 0.0325(7) Uani 1 1 d . . . C15 C 0.68442(17) 0.5861(4) 0.0140(2) 0.0251(7) Uani 1 1 d . . . H15A H 0.6548 0.5523 -0.0274 0.030 Uiso 1 1 calc R . . C28 C 0.95595(19) 1.0802(4) 0.4071(2) 0.0262(8) Uani 1 1 d . . . C14 C 0.9938(2) 1.3395(4) 0.4182(2) 0.0303(8) Uani 1 1 d . . . N5 N 0.56541(17) 0.7177(3) 0.3295(2) 0.0322(7) Uani 1 1 d . . . C13 C 1.0533(2) 1.4066(4) 0.4400(2) 0.0310(8) Uani 1 1 d . . . C12 C 0.74686(19) 0.6345(4) 0.0010(2) 0.0280(8) Uani 1 1 d . . . C11 C 0.6033(2) 1.2728(4) 0.3132(2) 0.0302(8) Uani 1 1 d . . . C10 C 1.00081(19) 1.0059(4) 0.3669(2) 0.0279(8) Uani 1 1 d . . . C9 C 0.66666(18) 0.5889(4) 0.0893(2) 0.0242(7) Uani 1 1 d . . . C8 C 0.9679(2) 1.2108(4) 0.4567(2) 0.0345(9) Uani 1 1 d . . . H8A H 0.9991 1.1872 0.5021 0.041 Uiso 1 1 calc R . . H8B H 0.9266 1.2364 0.4754 0.041 Uiso 1 1 calc R . . C7 C 0.5554(2) 1.1560(5) 0.5019(3) 0.0412(10) Uani 1 1 d . . . H7A H 0.5196 1.2065 0.5204 0.062 Uiso 1 1 calc R . . H7B H 0.5948 1.1668 0.5384 0.062 Uiso 1 1 calc R . . H7C H 0.5442 1.0576 0.4966 0.062 Uiso 1 1 calc R . . C6 C 0.9615(2) 1.4184(4) 0.3552(2) 0.0331(9) Uani 1 1 d . . . C5 C 0.5846(3) 0.8984(5) 0.2301(3) 0.0445(11) Uani 1 1 d . . . H5A H 0.5594 0.8335 0.1954 0.067 Uiso 1 1 calc R . . H5B H 0.6280 0.9094 0.2148 0.067 Uiso 1 1 calc R . . H5C H 0.5627 0.9884 0.2279 0.067 Uiso 1 1 calc R . . C4 C 0.6479(3) 0.8157(5) 0.5242(3) 0.0528(13) Uani 1 1 d . . . H4A H 0.6353 0.7311 0.5493 0.079 Uiso 1 1 calc R . . H4B H 0.6311 0.8965 0.5489 0.079 Uiso 1 1 calc R . . H4C H 0.6953 0.8211 0.5286 0.079 Uiso 1 1 calc R . . C3 C 0.6194(2) 0.8129(4) 0.4390(2) 0.0339(9) Uani 1 1 d . . . C2 C 0.8968(2) 1.3899(5) 0.3072(3) 0.0463(11) Uani 1 1 d . . . H2A H 0.8879 1.4623 0.2683 0.070 Uiso 1 1 calc R . . H2B H 0.8623 1.3893 0.3403 0.070 Uiso 1 1 calc R . . H2C H 0.8983 1.2996 0.2821 0.070 Uiso 1 1 calc R . . C1 C 1.0711(2) 1.0422(5) 0.3594(3) 0.0494(12) Uani 1 1 d . . . H1A H 1.0893 0.9719 0.3283 0.074 Uiso 1 1 calc R . . H1B H 1.0963 1.0452 0.4104 0.074 Uiso 1 1 calc R . . H1C H 1.0728 1.1329 0.3348 0.074 Uiso 1 1 calc R . . O1W O 0.7210(2) 0.4062(5) -0.1443(3) 0.0713(13) Uani 1 1 d . . . N7 N 0.55664(17) 1.3690(3) 0.3258(2) 0.0335(8) Uani 1 1 d . . . C32 C 0.6391(3) 1.2806(5) 0.2432(3) 0.0494(12) Uani 1 1 d . . . H32A H 0.6233 1.3604 0.2118 0.074 Uiso 1 1 calc R . . H32B H 0.6313 1.1956 0.2130 0.074 Uiso 1 1 calc R . . H32C H 0.6857 1.2908 0.2597 0.074 Uiso 1 1 calc R . . C29 C 0.8320(2) 1.0258(5) 0.4199(4) 0.0547(13) Uani 1 1 d . . . H29A H 0.8029 0.9509 0.3998 0.082 Uiso 1 1 calc R . . H29B H 0.8143 1.1147 0.4002 0.082 Uiso 1 1 calc R . . H29C H 0.8360 1.0260 0.4760 0.082 Uiso 1 1 calc R . . C30 C 1.1100(2) 1.3745(5) 0.5006(3) 0.0478(12) Uani 1 1 d . . . H30A H 1.1436 1.4454 0.4995 0.072 Uiso 1 1 calc R . . H30B H 1.1280 1.2836 0.4904 0.072 Uiso 1 1 calc R . . H30C H 1.0951 1.3737 0.5512 0.072 Uiso 1 1 calc R . . H1W H 0.754(3) 0.369(6) -0.173(3) 0.072(18) Uiso 1 1 d . . . H2W H 0.683(4) 0.376(7) -0.169(4) 0.10(2) Uiso 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 Cd1 0.0225(2) 0.0227(2) 0.0276(2) 0.000 0.00634(14) 0.000 Cd2 0.0244(2) 0.0214(2) 0.0259(2) 0.000 0.00430(14) 0.000 O4 0.0204(13) 0.0378(15) 0.0374(16) -0.0054(12) 0.0029(11) -0.0025(11) N2 0.0358(18) 0.0287(17) 0.0321(18) 0.0035(14) -0.0008(14) -0.0060(14) O3 0.0348(16) 0.0380(15) 0.0391(16) -0.0063(13) 0.0165(13) -0.0046(13) O5 0.0369(16) 0.0577(19) 0.0251(14) -0.0009(13) 0.0109(12) -0.0095(14) N8 0.0277(16) 0.0281(16) 0.0363(19) -0.0038(14) 0.0040(14) 0.0074(13) N1 0.0244(15) 0.0262(16) 0.0337(17) -0.0048(13) 0.0079(13) -0.0046(13) N6 0.041(2) 0.0260(17) 0.0342(19) 0.0049(14) 0.0089(15) 0.0001(14) O2 0.0339(15) 0.0587(19) 0.0281(15) -0.0142(13) 0.0095(12) -0.0166(14) O1 0.0263(14) 0.0511(18) 0.0345(16) -0.0054(13) 0.0025(12) -0.0142(13) C27 0.0211(17) 0.0296(18) 0.0273(19) 0.0004(15) 0.0051(14) -0.0038(15) C25 0.0247(18) 0.0206(17) 0.034(2) -0.0040(15) 0.0002(15) 0.0026(14) C24 0.0284(19) 0.0249(19) 0.033(2) -0.0026(15) 0.0025(16) -0.0015(15) C23 0.0249(18) 0.0306(19) 0.0260(18) -0.0033(15) 0.0048(14) -0.0032(15) C22 0.0249(18) 0.029(2) 0.036(2) 0.0007(16) 0.0012(16) 0.0047(15) C21 0.0288(19) 0.0286(19) 0.0276(19) -0.0050(16) 0.0055(15) 0.0017(16) N4 0.0320(17) 0.0261(16) 0.0278(16) -0.0042(13) 0.0042(13) -0.0014(13) C20 0.0222(17) 0.0239(18) 0.0293(19) 0.0001(14) 0.0060(14) 0.0012(14) C19 0.0301(19) 0.0215(17) 0.0299(19) -0.0010(15) 0.0008(15) 0.0061(15) C18 0.0202(17) 0.0300(19) 0.033(2) -0.0011(16) 0.0076(15) -0.0025(15) C17 0.035(2) 0.0260(19) 0.031(2) -0.0035(16) 0.0006(16) 0.0009(16) C16 0.0256(18) 0.0267(19) 0.0284(19) -0.0016(15) 0.0004(15) -0.0055(15) N3 0.0342(18) 0.0271(17) 0.0369(19) 0.0057(14) 0.0068(14) -0.0023(14) C15 0.0223(17) 0.0286(18) 0.0241(18) 0.0001(15) 0.0019(14) -0.0007(14) C28 0.032(2) 0.0213(17) 0.0252(18) 0.0033(14) 0.0044(15) 0.0015(15) C14 0.042(2) 0.0221(18) 0.0289(19) -0.0003(15) 0.0107(16) -0.0020(16) N5 0.0377(19) 0.0280(17) 0.0311(18) -0.0058(13) 0.0054(14) -0.0031(14) C13 0.044(2) 0.0230(18) 0.0263(19) 0.0008(15) 0.0067(17) -0.0030(17) C12 0.0291(19) 0.0311(19) 0.0247(18) 0.0035(15) 0.0069(15) -0.0001(15) C11 0.035(2) 0.0253(19) 0.030(2) -0.0029(15) 0.0067(16) 0.0061(16) C10 0.0291(19) 0.0242(18) 0.0299(19) 0.0000(15) 0.0022(15) -0.0055(15) C9 0.0226(17) 0.0226(17) 0.0274(18) -0.0015(14) 0.0026(14) 0.0001(14) C8 0.051(3) 0.0243(19) 0.031(2) -0.0004(16) 0.0155(18) -0.0091(17) C7 0.050(3) 0.036(2) 0.040(2) 0.0018(19) 0.014(2) 0.003(2) C6 0.036(2) 0.0255(19) 0.038(2) 0.0013(17) 0.0070(17) 0.0024(16) C5 0.054(3) 0.038(2) 0.041(3) 0.0010(19) 0.004(2) -0.017(2) C4 0.077(4) 0.044(3) 0.034(2) 0.006(2) -0.007(2) -0.004(3) C3 0.044(2) 0.0254(19) 0.031(2) 0.0036(16) 0.0014(17) 0.0056(17) C2 0.036(2) 0.044(3) 0.058(3) 0.008(2) 0.001(2) -0.006(2) C1 0.036(2) 0.043(3) 0.071(4) -0.016(2) 0.016(2) -0.010(2) O1W 0.055(3) 0.090(3) 0.074(3) -0.043(2) 0.030(2) -0.018(2) N7 0.0388(19) 0.0281(17) 0.0334(18) 0.0019(14) 0.0033(15) 0.0078(14) C32 0.065(3) 0.044(3) 0.045(3) 0.012(2) 0.027(2) 0.015(2) C29 0.034(2) 0.049(3) 0.083(4) -0.019(3) 0.017(2) -0.003(2) C30 0.051(3) 0.040(3) 0.049(3) 0.007(2) -0.007(2) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O3 2.314(3) 2_655 ? Cd1 O3 2.314(3) . ? Cd1 N7 2.345(3) 2_645 ? Cd1 N7 2.345(3) 1_545 ? Cd1 N5 2.405(3) . ? Cd1 N5 2.405(3) 2_655 ? Cd2 N4 2.318(3) . ? Cd2 N4 2.318(3) 2_755 ? Cd2 N3 2.340(3) 1_545 ? Cd2 N3 2.340(3) 2_745 ? Cd2 O4 2.405(3) 2_755 ? Cd2 O4 2.405(3) . ? O4 C16 1.269(5) . ? N2 C13 1.344(5) . ? N2 N3 1.354(5) . ? O3 C20 1.254(5) . ? O5 C12 1.370(4) . ? N8 C24 1.337(5) . ? N8 N7 1.349(5) . ? N1 N4 1.342(4) . ? N1 C21 1.354(5) . ? N6 C3 1.355(5) . ? N6 N5 1.363(5) . ? O2 C16 1.250(5) . ? O1 C20 1.251(4) . ? C27 C18 1.386(5) . ? C27 C23 1.393(5) . ? C27 C16 1.509(5) . ? C25 C24 1.370(6) . ? C25 C11 1.405(5) . ? C25 C22 1.502(5) . ? C24 C7 1.501(6) . ? C23 C9 1.391(5) . ? C22 C19 1.504(5) . ? C21 C28 1.376(5) . ? C21 C29 1.481(6) . ? N4 C10 1.336(5) . ? C20 C9 1.513(5) . ? C19 C3 1.365(5) . ? C19 C17 1.414(5) . ? C18 C12 1.386(5) . ? C17 N5 1.334(5) . ? C17 C5 1.503(6) . ? N3 C6 1.343(5) . ? N3 Cd2 2.340(3) 1_565 ? C15 C9 1.394(5) . ? C15 C12 1.397(5) . ? C28 C10 1.405(5) . ? C28 C8 1.505(5) . ? C14 C13 1.378(6) . ? C14 C6 1.410(5) . ? C14 C8 1.514(5) . ? C13 C30 1.486(6) . ? C11 N7 1.354(5) . ? C11 C32 1.492(6) . ? C10 C1 1.494(6) . ? C6 C2 1.487(6) . ? C4 C3 1.510(6) . ? N7 Cd1 2.345(3) 1_565 ? 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 O3 Cd1 O3 168.19(14) 2_655 . ? O3 Cd1 N7 94.82(12) 2_655 2_645 ? O3 Cd1 N7 93.67(11) . 2_645 ? O3 Cd1 N7 93.67(11) 2_655 1_545 ? O3 Cd1 N7 94.82(12) . 1_545 ? N7 Cd1 N7 87.92(16) 2_645 1_545 ? O3 Cd1 N5 87.73(11) 2_655 . ? O3 Cd1 N5 84.36(11) . . ? N7 Cd1 N5 175.47(12) 2_645 . ? N7 Cd1 N5 88.18(12) 1_545 . ? O3 Cd1 N5 84.36(11) 2_655 2_655 ? O3 Cd1 N5 87.73(11) . 2_655 ? N7 Cd1 N5 88.18(12) 2_645 2_655 ? N7 Cd1 N5 175.47(12) 1_545 2_655 ? N5 Cd1 N5 95.81(16) . 2_655 ? N4 Cd2 N4 87.92(16) . 2_755 ? N4 Cd2 N3 95.70(12) . 1_545 ? N4 Cd2 N3 166.72(12) 2_755 1_545 ? N4 Cd2 N3 166.72(12) . 2_745 ? N4 Cd2 N3 95.70(12) 2_755 2_745 ? N3 Cd2 N3 83.69(17) 1_545 2_745 ? N4 Cd2 O4 91.39(10) . 2_755 ? N4 Cd2 O4 87.03(10) 2_755 2_755 ? N3 Cd2 O4 80.12(11) 1_545 2_755 ? N3 Cd2 O4 101.54(11) 2_745 2_755 ? N4 Cd2 O4 87.03(10) . . ? N4 Cd2 O4 91.39(10) 2_755 . ? N3 Cd2 O4 101.54(11) 1_545 . ? N3 Cd2 O4 80.12(11) 2_745 . ? O4 Cd2 O4 177.81(13) 2_755 . ? C16 O4 Cd2 143.4(3) . . ? C13 N2 N3 113.0(3) . . ? C20 O3 Cd1 146.8(3) . . ? C24 N8 N7 112.3(3) . . ? N4 N1 C21 112.0(3) . . ? C3 N6 N5 111.5(3) . . ? C18 C27 C23 119.6(3) . . ? C18 C27 C16 119.8(3) . . ? C23 C27 C16 120.4(3) . . ? C24 C25 C11 105.2(3) . . ? C24 C25 C22 127.0(4) . . ? C11 C25 C22 127.8(4) . . ? N8 C24 C25 107.5(4) . . ? N8 C24 C7 121.7(4) . . ? C25 C24 C7 130.7(4) . . ? C9 C23 C27 120.3(4) . . ? C25 C22 C19 114.7(3) . . ? N1 C21 C28 106.7(3) . . ? N1 C21 C29 120.9(4) . . ? C28 C21 C29 132.4(4) . . ? C10 N4 N1 105.6(3) . . ? C10 N4 Cd2 137.2(3) . . ? N1 N4 Cd2 117.0(2) . . ? O1 C20 O3 125.4(4) . . ? O1 C20 C9 118.0(3) . . ? O3 C20 C9 116.6(3) . . ? C3 C19 C17 105.2(3) . . ? C3 C19 C22 128.7(4) . . ? C17 C19 C22 126.1(4) . . ? C27 C18 C12 120.6(3) . . ? N5 C17 C19 110.8(4) . . ? N5 C17 C5 122.5(3) . . ? C19 C17 C5 126.7(4) . . ? O2 C16 O4 124.2(3) . . ? O2 C16 C27 119.7(3) . . ? O4 C16 C27 116.1(3) . . ? C6 N3 N2 104.9(3) . . ? C6 N3 Cd2 140.1(3) . 1_565 ? N2 N3 Cd2 114.8(2) . 1_565 ? C9 C15 C12 119.7(3) . . ? C21 C28 C10 105.1(3) . . ? C21 C28 C8 126.3(4) . . ? C10 C28 C8 128.6(4) . . ? C13 C14 C6 105.8(3) . . ? C13 C14 C8 126.5(4) . . ? C6 C14 C8 127.6(4) . . ? C17 N5 N6 105.1(3) . . ? C17 N5 Cd1 131.7(3) . . ? N6 N5 Cd1 123.2(2) . . ? N2 C13 C14 106.2(3) . . ? N2 C13 C30 121.4(4) . . ? C14 C13 C30 132.4(4) . . ? O5 C12 C18 117.4(3) . . ? O5 C12 C15 122.7(3) . . ? C18 C12 C15 119.9(3) . . ? N7 C11 C25 110.1(4) . . ? N7 C11 C32 121.5(4) . . ? C25 C11 C32 128.4(4) . . ? N4 C10 C28 110.6(3) . . ? N4 C10 C1 121.1(4) . . ? C28 C10 C1 128.3(4) . . ? C23 C9 C15 119.9(3) . . ? C23 C9 C20 120.6(3) . . ? C15 C9 C20 119.6(3) . . ? C28 C8 C14 116.8(3) . . ? N3 C6 C14 110.1(4) . . ? N3 C6 C2 121.2(4) . . ? C14 C6 C2 128.6(4) . . ? N6 C3 C19 107.3(3) . . ? N6 C3 C4 121.3(4) . . ? C19 C3 C4 131.4(4) . . ? N8 N7 C11 104.9(3) . . ? N8 N7 Cd1 119.8(2) . 1_565 ? C11 N7 Cd1 134.5(3) . 1_565 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.699 _refine_diff_density_min -0.813 _refine_diff_density_rms 0.140 _database_code_depnum_ccdc_archive 'CCDC 881878' ####################################################################### # # 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_a4 #TrackingRef '(4)CuBTEC.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 Cu N4 O4' _chemical_formula_weight 392.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 12.412(5) _cell_length_b 16.372(7) _cell_length_c 31.497(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6401(4) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3232 _exptl_absorpt_coefficient_mu 1.396 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7396 _exptl_absorpt_correction_T_max 0.8076 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11957 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1836 _reflns_number_gt 1667 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1108P)^2^+3.2560P] 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 1836 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.3750 0.3750 0.679761(12) 0.0164(2) Uani 1 2 d S . . N2 N 0.59838(17) 0.44835(13) 0.67987(7) 0.0220(5) Uani 1 1 d . . . H2D H 0.6199 0.4152 0.6605 0.026 Uiso 1 1 calc R . . N1 N 0.50161(16) 0.44241(12) 0.70001(7) 0.0202(4) Uani 1 1 d . . . C5 C 0.5945(2) 0.55112(14) 0.72485(7) 0.0187(5) Uani 1 1 d . . . C4 C 0.49855(19) 0.50533(15) 0.72747(8) 0.0194(5) Uani 1 1 d . . . C3 C 0.6560(2) 0.51200(15) 0.69391(8) 0.0217(5) Uani 1 1 d . . . C2 C 0.4044(2) 0.51843(19) 0.75564(10) 0.0356(7) Uani 1 1 d . . . H2A H 0.3512 0.4772 0.7502 0.053 Uiso 1 1 calc R . . H2B H 0.3740 0.5713 0.7502 0.053 Uiso 1 1 calc R . . H2C H 0.4269 0.5153 0.7847 0.053 Uiso 1 1 calc R . . C1 C 0.7648(2) 0.53161(19) 0.67625(10) 0.0361(7) Uani 1 1 d . . . H1A H 0.7839 0.4916 0.6553 0.054 Uiso 1 1 calc R . . H1B H 0.8170 0.5310 0.6987 0.054 Uiso 1 1 calc R . . H1C H 0.7632 0.5848 0.6634 0.054 Uiso 1 1 calc R . . O2 O 0.45232(15) 0.27585(11) 0.66817(6) 0.0283(4) Uani 1 1 d . . . O1 O 0.51303(15) 0.33532(10) 0.60955(6) 0.0282(4) Uani 1 1 d . . . C9 C 0.56854(19) 0.19859(15) 0.62673(7) 0.0162(5) Uani 1 1 d . . . C8 C 0.50769(18) 0.27704(14) 0.63415(8) 0.0177(5) Uani 1 1 d . . . C7 C 0.5140(3) 0.1250 0.6250 0.0188(7) Uani 1 2 d S . . H7A H 0.4391 0.1250 0.6250 0.023 Uiso 1 2 calc SR . . C6 C 0.6250 0.6250 0.75043(12) 0.0255(8) Uani 1 2 d S . . H6A H 0.681(3) 0.611(2) 0.7692(12) 0.046(10) Uiso 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 0.0142(3) 0.0101(3) 0.0249(3) 0.000 0.000 0.00050(12) N2 0.0180(10) 0.0175(10) 0.0306(11) -0.0046(8) 0.0066(8) -0.0011(8) N1 0.0155(10) 0.0185(10) 0.0266(10) -0.0020(8) 0.0010(8) -0.0019(7) C5 0.0201(11) 0.0162(11) 0.0199(11) -0.0005(9) 0.0003(9) -0.0041(9) C4 0.0184(11) 0.0189(11) 0.0211(11) -0.0026(9) -0.0004(8) -0.0024(9) C3 0.0178(11) 0.0195(12) 0.0280(12) 0.0028(10) 0.0031(10) -0.0031(9) C2 0.0289(14) 0.0397(17) 0.0384(15) -0.0149(13) 0.0115(13) -0.0078(12) C1 0.0240(14) 0.0343(16) 0.0501(18) -0.0025(13) 0.0100(12) -0.0093(12) O2 0.0311(10) 0.0163(8) 0.0374(10) 0.0019(8) 0.0157(8) 0.0070(7) O1 0.0322(10) 0.0159(9) 0.0365(10) 0.0057(8) 0.0050(8) 0.0064(7) C9 0.0140(12) 0.0112(11) 0.0236(11) -0.0007(8) 0.0026(8) 0.0020(9) C8 0.0124(10) 0.0115(10) 0.0291(12) -0.0021(9) -0.0015(9) -0.0010(8) C7 0.0119(15) 0.0155(16) 0.0291(17) 0.0019(12) 0.000 0.000 C6 0.038(2) 0.0195(18) 0.0189(17) 0.000 0.000 -0.0091(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.9208(18) 2 ? Cu1 O2 1.9208(18) . ? Cu1 N1 2.024(2) . ? Cu1 N1 2.024(2) 2 ? N2 C3 1.339(3) . ? N2 N1 1.362(3) . ? N1 C4 1.345(3) . ? C5 C3 1.394(3) . ? C5 C4 1.410(3) . ? C5 C6 1.502(3) . ? C4 C2 1.483(3) . ? C3 C1 1.495(4) . ? O2 C8 1.273(3) . ? O1 C8 1.231(3) . ? C9 C7 1.383(3) . ? C9 C9 1.406(5) 11 ? C9 C8 1.508(3) . ? C7 C9 1.383(3) 8_545 ? C6 C5 1.502(3) 14 ? 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 Cu1 O2 158.09(12) 2 . ? O2 Cu1 N1 89.26(8) 2 . ? O2 Cu1 N1 97.63(8) . . ? O2 Cu1 N1 97.63(8) 2 2 ? O2 Cu1 N1 89.26(8) . 2 ? N1 Cu1 N1 143.25(12) . 2 ? C3 N2 N1 111.9(2) . . ? C4 N1 N2 105.64(19) . . ? C4 N1 Cu1 126.74(16) . . ? N2 N1 Cu1 125.25(16) . . ? C3 C5 C4 105.0(2) . . ? C3 C5 C6 127.4(2) . . ? C4 C5 C6 127.6(2) . . ? N1 C4 C5 110.2(2) . . ? N1 C4 C2 121.2(2) . . ? C5 C4 C2 128.6(2) . . ? N2 C3 C5 107.2(2) . . ? N2 C3 C1 121.8(2) . . ? C5 C3 C1 131.0(2) . . ? C8 O2 Cu1 114.63(15) . . ? C7 C9 C9 119.01(16) . 11 ? C7 C9 C8 120.2(2) . . ? C9 C9 C8 120.75(13) 11 . ? O1 C8 O2 124.8(2) . . ? O1 C8 C9 122.4(2) . . ? O2 C8 C9 112.8(2) . . ? C9 C7 C9 121.4(3) . 8_545 ? C5 C6 C5 115.1(3) . 14 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.939 _refine_diff_density_min -0.916 _refine_diff_density_rms 0.373 _database_code_depnum_ccdc_archive 'CCDC 881879' ####################################################################### # # 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_a5 #TrackingRef '(5)CoBTEC.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 Co N4 O5' _chemical_formula_weight 406.28 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 monoclinic _symmetry_space_group_name_H-M c2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.489(3) _cell_length_b 7.1038(8) _cell_length_c 23.022(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.150(13) _cell_angle_gamma 90.00 _cell_volume 3511.9(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 1.013 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7509 _exptl_absorpt_correction_T_max 0.7858 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13089 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.44 _reflns_number_total 3987 _reflns_number_gt 3356 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+3.1757P] 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 3987 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 0.112920(16) 0.76842(5) 0.114654(16) 0.02512(15) Uani 1 1 d . . . N1 N -0.00709(10) 0.9689(3) 0.08627(11) 0.0304(5) Uani 1 1 d . . . H1A H 0.0136 1.0558 0.0696 0.036 Uiso 1 1 calc R . . C1 C -0.01628(16) 0.5271(5) 0.16038(16) 0.0447(8) Uani 1 1 d . . . H1B H 0.0274 0.4988 0.1597 0.067 Uiso 1 1 calc R . . H1C H -0.0395 0.4302 0.1402 0.067 Uiso 1 1 calc R . . H1D H -0.0288 0.5336 0.1999 0.067 Uiso 1 1 calc R . . C2 C -0.02855(13) 0.7121(4) 0.13119(13) 0.0309(6) Uani 1 1 d . . . N2 N 0.01882(11) 0.8106(4) 0.10959(11) 0.0315(5) Uani 1 1 d . . . N3 N -0.16588(11) 0.5456(3) 0.28541(11) 0.0312(5) Uani 1 1 d . . . H3A H -0.1776 0.4602 0.3092 0.037 Uiso 1 1 calc R . . C3 C -0.06934(13) 0.9734(4) 0.09234(12) 0.0320(6) Uani 1 1 d . . . N4 N -0.13447(11) 0.7044(4) 0.30166(11) 0.0307(5) Uani 1 1 d . . . C4 C -0.10828(15) 1.1319(5) 0.06766(16) 0.0449(8) Uani 1 1 d . . . H4A H -0.0817 1.2241 0.0508 0.067 Uiso 1 1 calc R . . H4B H -0.1310 1.1892 0.0981 0.067 Uiso 1 1 calc R . . H4C H -0.1370 1.0838 0.0383 0.067 Uiso 1 1 calc R . . C5 C -0.08498(13) 0.8102(5) 0.12157(13) 0.0323(6) Uani 1 1 d . . . C6 C -0.14903(14) 0.7538(5) 0.14090(14) 0.0404(8) Uani 1 1 d . . . H6A H -0.1775 0.8579 0.1338 0.049 Uiso 1 1 calc R . . H6B H -0.1638 0.6483 0.1175 0.049 Uiso 1 1 calc R . . C7 C -0.15023(13) 0.6995(5) 0.20442(13) 0.0318(6) Uani 1 1 d . . . C8 C -0.17640(12) 0.5389(4) 0.22729(13) 0.0321(6) Uani 1 1 d . . . C9 C -0.21116(16) 0.3788(5) 0.19895(16) 0.0497(9) Uani 1 1 d . . . H9A H -0.2228 0.2902 0.2281 0.075 Uiso 1 1 calc R . . H9B H -0.1851 0.3178 0.1717 0.075 Uiso 1 1 calc R . . H9C H -0.2479 0.4259 0.1789 0.075 Uiso 1 1 calc R . . C10 C -0.12498(13) 0.7990(4) 0.25238(13) 0.0301(6) Uani 1 1 d . . . C11 C -0.09241(16) 0.9851(5) 0.25434(15) 0.0444(8) Uani 1 1 d . . . H11A H -0.0807 1.0156 0.2939 0.067 Uiso 1 1 calc R . . H11B H -0.1198 1.0806 0.2386 0.067 Uiso 1 1 calc R . . H11C H -0.0558 0.9787 0.2318 0.067 Uiso 1 1 calc R . . O4 O 0.13227(9) 0.0107(3) 0.08296(10) 0.0377(5) Uani 1 1 d . . . O3 O 0.12963(9) 0.5407(3) 0.06666(10) 0.0351(5) Uani 1 1 d . . . O2 O 0.18020(13) 0.2201(3) 0.14264(10) 0.0463(6) Uani 1 1 d . . . O1 O 0.22094(10) 0.6679(3) 0.08965(10) 0.0388(5) Uani 1 1 d . . . C15 C 0.22071(12) 0.3902(4) 0.03175(12) 0.0242(5) Uani 1 1 d . . . C14 C 0.21066(12) 0.1992(4) 0.04459(12) 0.0244(5) Uani 1 1 d . . . C13 C 0.17172(12) 0.1427(4) 0.09496(13) 0.0282(6) Uani 1 1 d . . . C12 C 0.18998(12) 0.5429(4) 0.06515(12) 0.0261(6) Uani 1 1 d . . . C16 C 0.23968(12) 0.0614(4) 0.01259(12) 0.0256(6) Uani 1 1 d . . . H16A H 0.2327 -0.0649 0.0208 0.031 Uiso 1 1 calc R . . O1W O 0.03147(12) 0.3119(4) 0.02701(13) 0.0583(7) Uani 1 1 d . . . H1WC H 0.0335 0.2476 -0.0040 0.070 Uiso 1 1 d R . . H1WD H 0.0653 0.3726 0.0323 0.070 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0255(2) 0.0246(2) 0.0257(2) -0.00038(14) 0.00587(15) -0.00072(13) N1 0.0259(11) 0.0334(13) 0.0322(13) 0.0047(10) 0.0057(9) -0.0032(10) C1 0.0393(17) 0.0442(18) 0.051(2) 0.0129(16) 0.0076(14) -0.0063(14) C2 0.0279(14) 0.0386(16) 0.0266(15) 0.0000(12) 0.0041(11) -0.0037(12) N2 0.0274(12) 0.0322(12) 0.0353(14) 0.0021(11) 0.0080(10) -0.0010(10) N3 0.0330(12) 0.0315(12) 0.0296(13) 0.0008(10) 0.0068(10) -0.0031(10) C3 0.0274(13) 0.0425(16) 0.0261(15) -0.0020(12) 0.0022(11) 0.0004(12) N4 0.0305(12) 0.0331(13) 0.0289(13) -0.0015(10) 0.0051(10) -0.0011(10) C4 0.0347(16) 0.050(2) 0.050(2) 0.0047(16) 0.0022(14) 0.0080(14) C5 0.0240(13) 0.0498(17) 0.0234(14) -0.0008(13) 0.0032(10) -0.0053(12) C6 0.0247(15) 0.071(2) 0.0259(16) 0.0041(14) 0.0019(11) -0.0110(13) C7 0.0205(12) 0.0485(17) 0.0267(15) 0.0006(13) 0.0036(10) -0.0013(12) C8 0.0236(13) 0.0427(16) 0.0301(15) -0.0044(13) 0.0046(11) -0.0027(12) C9 0.0464(19) 0.056(2) 0.047(2) -0.0112(17) 0.0009(15) -0.0164(17) C10 0.0256(13) 0.0367(15) 0.0285(15) 0.0005(12) 0.0070(11) 0.0001(11) C11 0.052(2) 0.0418(18) 0.0397(19) 0.0008(15) 0.0094(15) -0.0121(15) O4 0.0311(11) 0.0319(11) 0.0509(14) 0.0097(10) 0.0111(9) -0.0072(9) O3 0.0273(10) 0.0336(11) 0.0450(13) -0.0094(10) 0.0097(9) 0.0025(8) O2 0.0686(17) 0.0406(13) 0.0310(13) -0.0019(10) 0.0188(11) -0.0025(11) O1 0.0416(12) 0.0314(11) 0.0440(13) -0.0116(10) 0.0100(9) -0.0070(9) C15 0.0242(12) 0.0220(12) 0.0266(14) -0.0002(10) 0.0043(10) 0.0008(10) C14 0.0226(12) 0.0244(13) 0.0263(14) 0.0017(11) 0.0039(10) -0.0012(10) C13 0.0282(13) 0.0240(13) 0.0333(16) 0.0042(11) 0.0114(11) 0.0047(11) C12 0.0320(14) 0.0233(12) 0.0235(14) 0.0006(10) 0.0071(10) 0.0018(11) C16 0.0257(12) 0.0210(12) 0.0303(15) 0.0017(10) 0.0054(10) -0.0003(10) O1W 0.0561(16) 0.0603(16) 0.0578(18) -0.0042(14) -0.0071(13) -0.0136(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O4 1.921(2) 1_565 ? Co1 O3 1.999(2) . ? Co1 N4 2.016(3) 2 ? Co1 N2 2.043(2) . ? N1 C3 1.351(3) . ? N1 N2 1.356(3) . ? C1 C2 1.495(4) . ? C2 N2 1.346(4) . ? C2 C5 1.409(4) . ? N3 C8 1.349(4) . ? N3 N4 1.360(3) . ? C3 C5 1.388(4) . ? C3 C4 1.502(4) . ? N4 C10 1.341(4) . ? N4 Co1 2.016(3) 2 ? C5 C6 1.516(4) . ? C6 C7 1.513(4) . ? C7 C8 1.385(4) . ? C7 C10 1.403(4) . ? C8 C9 1.497(4) . ? C10 C11 1.496(4) . ? O4 C13 1.287(3) . ? O4 Co1 1.921(2) 1_545 ? O3 C12 1.299(3) . ? O2 C13 1.235(4) . ? O1 C12 1.233(3) . ? C15 C16 1.397(4) 7 ? C15 C14 1.407(4) . ? C15 C12 1.498(4) . ? C14 C16 1.387(4) . ? C14 C13 1.510(4) . ? C16 C15 1.397(4) 7 ? 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 Co1 O3 117.98(10) 1_565 . ? O4 Co1 N4 121.32(10) 1_565 2 ? O3 Co1 N4 107.81(10) . 2 ? O4 Co1 N2 94.28(9) 1_565 . ? O3 Co1 N2 106.57(9) . . ? N4 Co1 N2 106.20(10) 2 . ? C3 N1 N2 111.9(2) . . ? N2 C2 C5 110.1(3) . . ? N2 C2 C1 120.0(3) . . ? C5 C2 C1 129.9(3) . . ? C2 N2 N1 105.8(2) . . ? C2 N2 Co1 131.5(2) . . ? N1 N2 Co1 122.35(18) . . ? C8 N3 N4 111.4(2) . . ? N1 C3 C5 106.8(3) . . ? N1 C3 C4 121.3(3) . . ? C5 C3 C4 131.9(3) . . ? C10 N4 N3 105.8(2) . . ? C10 N4 Co1 131.2(2) . 2 ? N3 N4 Co1 122.95(19) . 2 ? C3 C5 C2 105.5(2) . . ? C3 C5 C6 127.0(3) . . ? C2 C5 C6 127.5(3) . . ? C7 C6 C5 113.5(2) . . ? C8 C7 C10 105.4(3) . . ? C8 C7 C6 126.8(3) . . ? C10 C7 C6 127.7(3) . . ? N3 C8 C7 107.0(3) . . ? N3 C8 C9 121.4(3) . . ? C7 C8 C9 131.6(3) . . ? N4 C10 C7 110.3(3) . . ? N4 C10 C11 120.2(3) . . ? C7 C10 C11 129.5(3) . . ? C13 O4 Co1 136.2(2) . 1_545 ? C12 O3 Co1 101.84(17) . . ? C16 C15 C14 119.6(2) 7 . ? C16 C15 C12 119.3(2) 7 . ? C14 C15 C12 121.1(2) . . ? C16 C14 C15 119.6(2) . . ? C16 C14 C13 119.6(2) . . ? C15 C14 C13 120.8(2) . . ? O2 C13 O4 126.1(3) . . ? O2 C13 C14 119.8(3) . . ? O4 C13 C14 114.1(3) . . ? O1 C12 O3 121.2(3) . . ? O1 C12 C15 121.1(2) . . ? O3 C12 C15 117.7(2) . . ? C14 C16 C15 120.9(2) . 7 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.379 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 881880' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a #TrackingRef '(4)__ [Mn(NO2-BDC)(H2MDP)(H2O)].CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H21 Mn N5 O7' _chemical_formula_weight 486.35 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 monoclinic _symmetry_space_group_name_H-M p21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.3734(2) _cell_length_b 11.2005(2) _cell_length_c 15.8979(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.179(2) _cell_angle_gamma 90.00 _cell_volume 2080.97(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1004 _exptl_absorpt_coefficient_mu 0.688 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8524 _exptl_absorpt_correction_T_max 0.9039 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7966 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.36 _reflns_number_total 4134 _reflns_number_gt 3789 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+3.5810P] 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 4134 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1315 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Mn1 Mn 0.20256(3) 0.41564(4) 0.10699(3) 0.02567(15) Uani 1 1 d . . . O6 O -0.21696(17) 0.07869(19) -0.25212(13) 0.0318(5) Uani 1 1 d . . . O1W O 0.04549(17) 0.5099(2) 0.11874(15) 0.0277(4) Uani 1 1 d . . . O2 O 0.07313(17) 0.31305(18) -0.01239(13) 0.0315(4) Uani 1 1 d . . . N4 N 0.6382(2) 0.6659(2) -0.09887(17) 0.0321(5) Uani 1 1 d . . . O1 O 0.11414(18) 0.2496(2) 0.12559(14) 0.0361(5) Uani 1 1 d . . . N3 N 0.17502(19) 0.5938(2) -0.04985(16) 0.0273(5) Uani 1 1 d . . . H3 H 0.1134 0.5569 -0.0798 0.033 Uiso 1 1 calc R . . N2 N 0.22808(19) 0.5798(2) 0.03910(16) 0.0270(5) Uani 1 1 d . . . C19 C 0.2299(2) 0.6718(3) -0.08541(19) 0.0270(6) Uani 1 1 d . . . C18 C -0.0659(2) 0.0881(2) 0.08023(18) 0.0262(6) Uani 1 1 d . . . H18 H -0.0232 0.0962 0.1402 0.031 Uiso 1 1 calc R . . C17 C 0.3246(2) 0.7117(2) -0.01680(19) 0.0254(5) Uani 1 1 d . . . C16 C 0.0554(2) 0.2441(2) 0.04490(18) 0.0251(5) Uani 1 1 d . . . C15 C 0.4912(2) 0.7582(3) -0.0713(2) 0.0288(6) Uani 1 1 d . . . C14 C -0.0396(2) 0.1543(2) 0.01628(18) 0.0240(5) Uani 1 1 d . . . C13 C 0.5858(2) 0.6817(2) -0.03839(19) 0.0271(6) Uani 1 1 d . . . C12 C 0.3190(2) 0.6522(3) 0.05969(19) 0.0276(6) Uani 1 1 d . . . C11 C -0.2214(2) -0.0073(3) -0.03475(18) 0.0271(6) Uani 1 1 d . . . H11 H -0.2828 -0.0600 -0.0507 0.032 Uiso 1 1 calc R . . N5 N -0.1874(2) -0.0566(3) 0.12232(18) 0.0389(6) Uani 1 1 d . . . C10 C -0.2577(2) 0.0353(3) -0.19612(18) 0.0298(6) Uani 1 1 d . . . C9 C 0.4124(2) 0.8010(2) -0.0232(2) 0.0312(6) Uani 1 1 d . . . H9A H 0.3728 0.8716 -0.0534 0.037 Uiso 1 1 calc R . . H9B H 0.4582 0.8245 0.0366 0.037 Uiso 1 1 calc R . . C8 C -0.1922(2) 0.0564(3) -0.09912(17) 0.0250(5) Uani 1 1 d . . . N1 N 0.5766(2) 0.7314(3) -0.17014(18) 0.0402(7) Uani 1 1 d . . . H1 H 0.5920 0.7358 -0.2190 0.048 Uiso 1 1 calc R . . C7 C -0.1026(2) 0.1377(2) -0.07332(17) 0.0247(5) Uani 1 1 d . . . H7 H -0.0844 0.1817 -0.1164 0.030 Uiso 1 1 calc R . . C6 C 0.4890(2) 0.7885(3) -0.1560(2) 0.0384(7) Uani 1 1 d . . . C5 C -0.1567(2) 0.0097(2) 0.05355(18) 0.0259(5) Uani 1 1 d . . . O5 O -0.3475(2) -0.0234(3) -0.21378(16) 0.0626(9) Uani 1 1 d . . . C4 C 0.6288(3) 0.6231(3) 0.0505(2) 0.0388(7) Uani 1 1 d . . . H4A H 0.6947 0.5754 0.0541 0.058 Uiso 1 1 calc R . . H4B H 0.5700 0.5731 0.0586 0.058 Uiso 1 1 calc R . . H4C H 0.6496 0.6830 0.0962 0.058 Uiso 1 1 calc R . . C3 C 0.1864(3) 0.6994(3) -0.1825(2) 0.0414(7) Uani 1 1 d . . . H3A H 0.1168 0.6561 -0.2102 0.062 Uiso 1 1 calc R . . H3B H 0.2425 0.6765 -0.2091 0.062 Uiso 1 1 calc R . . H3C H 0.1717 0.7835 -0.1908 0.062 Uiso 1 1 calc R . . O4 O -0.1244(3) -0.0514(4) 0.19800(19) 0.0940(14) Uani 1 1 d . . . O3 O -0.2774(3) -0.1091(3) 0.10162(19) 0.0688(9) Uani 1 1 d . . . C2 C 0.3960(3) 0.6620(3) 0.1540(2) 0.0447(8) Uani 1 1 d . . . H2A H 0.3690 0.6101 0.1909 0.067 Uiso 1 1 calc R . . H2B H 0.3962 0.7429 0.1741 0.067 Uiso 1 1 calc R . . H2C H 0.4723 0.6394 0.1579 0.067 Uiso 1 1 calc R . . C1 C 0.4116(3) 0.8679(5) -0.2256(3) 0.0679(14) Uani 1 1 d . . . H1A H 0.4346 0.8670 -0.2777 0.102 Uiso 1 1 calc R . . H1B H 0.4162 0.9479 -0.2030 0.102 Uiso 1 1 calc R . . H1C H 0.3343 0.8397 -0.2407 0.102 Uiso 1 1 calc R . . H1WA H 0.028(3) 0.571(3) 0.099(2) 0.027(9) Uiso 1 1 d . . . H2WB H 0.076(4) 0.524(5) 0.175(4) 0.084(17) Uiso 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 Mn1 0.0220(2) 0.0283(2) 0.0279(2) 0.00141(16) 0.00985(17) -0.00080(16) O6 0.0263(10) 0.0437(13) 0.0242(10) 0.0007(8) 0.0069(8) -0.0048(8) O1W 0.0223(9) 0.0315(12) 0.0287(11) 0.0026(9) 0.0075(8) 0.0021(8) O2 0.0277(10) 0.0325(11) 0.0333(11) 0.0035(9) 0.0089(8) -0.0049(8) N4 0.0240(11) 0.0388(14) 0.0355(13) 0.0067(11) 0.0123(10) 0.0053(10) O1 0.0364(11) 0.0354(11) 0.0301(11) 0.0007(9) 0.0024(9) -0.0101(9) N3 0.0210(11) 0.0292(12) 0.0311(12) 0.0022(9) 0.0079(9) -0.0032(9) N2 0.0233(11) 0.0287(12) 0.0302(12) 0.0038(9) 0.0101(9) -0.0018(9) C19 0.0249(13) 0.0274(14) 0.0319(14) 0.0040(11) 0.0136(11) 0.0050(11) C18 0.0260(13) 0.0270(14) 0.0248(13) -0.0004(10) 0.0075(11) 0.0012(10) C17 0.0208(12) 0.0228(13) 0.0362(14) 0.0006(11) 0.0145(11) 0.0018(10) C16 0.0206(12) 0.0231(13) 0.0307(14) -0.0015(10) 0.0072(10) 0.0015(10) C15 0.0229(13) 0.0258(14) 0.0408(16) 0.0054(12) 0.0147(12) -0.0005(10) C14 0.0205(12) 0.0226(12) 0.0279(13) -0.0022(10) 0.0066(10) 0.0013(10) C13 0.0231(12) 0.0252(13) 0.0348(15) 0.0011(11) 0.0118(11) -0.0005(10) C12 0.0237(13) 0.0286(14) 0.0315(14) -0.0001(11) 0.0102(11) -0.0005(11) C11 0.0244(12) 0.0267(13) 0.0307(14) -0.0004(11) 0.0098(11) -0.0039(11) N5 0.0477(16) 0.0369(14) 0.0343(14) 0.0052(11) 0.0167(12) -0.0078(12) C10 0.0271(13) 0.0341(15) 0.0254(13) 0.0004(11) 0.0045(11) -0.0053(11) C9 0.0274(13) 0.0224(13) 0.0491(17) 0.0017(12) 0.0197(13) 0.0007(11) C8 0.0236(13) 0.0257(13) 0.0255(13) -0.0003(10) 0.0077(11) 0.0006(10) N1 0.0300(13) 0.0593(18) 0.0379(14) 0.0195(13) 0.0202(11) 0.0104(12) C7 0.0247(12) 0.0254(13) 0.0248(13) 0.0005(10) 0.0092(10) -0.0002(10) C6 0.0240(14) 0.0459(18) 0.0512(19) 0.0214(15) 0.0205(13) 0.0076(13) C5 0.0282(13) 0.0241(13) 0.0266(13) 0.0024(10) 0.0108(11) 0.0005(11) O5 0.0535(15) 0.093(2) 0.0310(12) 0.0070(13) -0.0005(11) -0.0476(16) C4 0.0401(17) 0.0432(18) 0.0347(16) 0.0056(14) 0.0145(13) 0.0117(14) C3 0.0452(18) 0.0466(19) 0.0324(16) 0.0062(14) 0.0129(14) -0.0004(15) O4 0.087(2) 0.143(4) 0.0349(15) 0.0323(18) -0.0021(15) -0.058(2) O3 0.0737(19) 0.084(2) 0.0512(16) 0.0048(15) 0.0235(15) -0.0456(17) C2 0.0432(18) 0.052(2) 0.0356(17) 0.0020(15) 0.0078(14) -0.0105(16) C1 0.041(2) 0.090(3) 0.080(3) 0.056(3) 0.030(2) 0.025(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O6 2.132(2) 4_666 ? Mn1 N2 2.207(2) . ? Mn1 N4 2.213(2) 3_665 ? Mn1 O1 2.226(2) . ? Mn1 O1W 2.273(2) . ? Mn1 O2 2.343(2) . ? Mn1 C16 2.608(3) . ? O6 C10 1.256(3) . ? O6 Mn1 2.132(2) 4_565 ? O2 C16 1.267(3) . ? N4 C13 1.337(4) . ? N4 N1 1.355(3) . ? N4 Mn1 2.213(2) 3_665 ? O1 C16 1.251(3) . ? N3 C19 1.340(4) . ? N3 N2 1.358(3) . ? N2 C12 1.338(4) . ? C19 C17 1.387(4) . ? C19 C3 1.491(4) . ? C18 C5 1.378(4) . ? C18 C14 1.381(4) . ? C17 C12 1.408(4) . ? C17 C9 1.505(4) . ? C16 C14 1.499(4) . ? C15 C6 1.380(4) . ? C15 C13 1.405(4) . ? C15 C9 1.502(4) . ? C14 C7 1.394(4) . ? C13 C4 1.489(4) . ? C12 C2 1.494(4) . ? C11 C5 1.381(4) . ? C11 C8 1.389(4) . ? N5 O4 1.201(4) . ? N5 O3 1.205(4) . ? N5 C5 1.471(4) . ? C10 O5 1.241(4) . ? C10 C8 1.507(4) . ? C8 C7 1.388(4) . ? N1 C6 1.340(4) . ? C6 C1 1.496(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 O6 Mn1 N2 113.35(9) 4_666 . ? O6 Mn1 N4 87.48(9) 4_666 3_665 ? N2 Mn1 N4 92.42(9) . 3_665 ? O6 Mn1 O1 88.03(8) 4_666 . ? N2 Mn1 O1 156.44(8) . . ? N4 Mn1 O1 98.55(9) 3_665 . ? O6 Mn1 O1W 90.96(8) 4_666 . ? N2 Mn1 O1W 85.22(8) . . ? N4 Mn1 O1W 176.41(9) 3_665 . ? O1 Mn1 O1W 84.62(8) . . ? O6 Mn1 O2 145.54(8) 4_666 . ? N2 Mn1 O2 100.49(8) . . ? N4 Mn1 O2 97.76(9) 3_665 . ? O1 Mn1 O2 57.52(7) . . ? O1W Mn1 O2 85.35(7) . . ? O6 Mn1 C16 116.53(9) 4_666 . ? N2 Mn1 C16 128.54(9) . . ? N4 Mn1 C16 101.43(9) 3_665 . ? O1 Mn1 C16 28.63(8) . . ? O1W Mn1 C16 82.16(8) . . ? O2 Mn1 C16 29.03(8) . . ? C10 O6 Mn1 126.75(18) . 4_565 ? C16 O2 Mn1 87.15(16) . . ? C13 N4 N1 104.9(2) . . ? C13 N4 Mn1 138.4(2) . 3_665 ? N1 N4 Mn1 116.21(18) . 3_665 ? C16 O1 Mn1 92.89(17) . . ? C19 N3 N2 112.1(2) . . ? C12 N2 N3 105.4(2) . . ? C12 N2 Mn1 129.02(19) . . ? N3 N2 Mn1 120.48(17) . . ? N3 C19 C17 107.0(2) . . ? N3 C19 C3 120.8(3) . . ? C17 C19 C3 132.2(3) . . ? C5 C18 C14 118.8(3) . . ? C19 C17 C12 105.0(2) . . ? C19 C17 C9 127.1(3) . . ? C12 C17 C9 127.9(3) . . ? O1 C16 O2 121.8(2) . . ? O1 C16 C14 118.5(2) . . ? O2 C16 C14 119.6(2) . . ? O1 C16 Mn1 58.48(14) . . ? O2 C16 Mn1 63.81(14) . . ? C14 C16 Mn1 171.60(19) . . ? C6 C15 C13 105.1(2) . . ? C6 C15 C9 127.5(3) . . ? C13 C15 C9 127.3(3) . . ? C18 C14 C7 119.5(2) . . ? C18 C14 C16 119.2(2) . . ? C7 C14 C16 121.3(2) . . ? N4 C13 C15 110.8(3) . . ? N4 C13 C4 121.2(3) . . ? C15 C13 C4 128.0(3) . . ? N2 C12 C17 110.6(2) . . ? N2 C12 C2 119.9(3) . . ? C17 C12 C2 129.6(3) . . ? C5 C11 C8 118.3(2) . . ? O4 N5 O3 122.3(3) . . ? O4 N5 C5 118.6(3) . . ? O3 N5 C5 119.0(3) . . ? O5 C10 O6 125.6(3) . . ? O5 C10 C8 117.1(3) . . ? O6 C10 C8 117.3(2) . . ? C15 C9 C17 115.2(2) . . ? C7 C8 C11 119.6(2) . . ? C7 C8 C10 120.9(2) . . ? C11 C8 C10 119.4(2) . . ? C6 N1 N4 112.5(2) . . ? C8 C7 C14 120.9(2) . . ? N1 C6 C15 106.8(3) . . ? N1 C6 C1 121.1(3) . . ? C15 C6 C1 132.1(3) . . ? C18 C5 C11 122.8(3) . . ? C18 C5 N5 118.4(2) . . ? C11 C5 N5 118.7(2) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.368 _refine_diff_density_min -0.616 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 917650'