# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name C.Y.Wang Z.M.Wilseck R.Supkowski R.L.LaDuca _publ_contact_author_name 'Robert L. LaDuca' _publ_contact_author_email laduca@msu.edu data_p21n _database_code_depnum_ccdc_archive 'CCDC 783827' #TrackingRef '0cdpht4bpfpfinal.cif' _audit_update_record ; 2010-07-01 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H28 Cd2 N4 O12' _chemical_formula_weight 885.38 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(1)/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 6.9659(7) _cell_length_b 29.074(3) _cell_length_c 7.8570(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.268(1) _cell_angle_gamma 90.00 _cell_volume 1535.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7173 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 25.28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.915 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 1.461 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6326 _exptl_absorpt_correction_T_max 0.8535 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9278 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 25.28 _reflns_number_total 2780 _reflns_number_gt 2615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0525P)^2^+1.3915P] 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 2780 _refine_ls_number_parameters 232 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.110 _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 0.48674(4) 0.235539(8) 0.86846(3) 0.03211(14) Uani 1 1 d . . . O1 O 0.8709(4) 0.03358(9) 1.3043(4) 0.0484(7) Uani 1 1 d . . . O2 O -0.1347(4) 0.21016(9) 0.5277(3) 0.0388(6) Uani 1 1 d . . . O3 O 0.0296(4) 0.20564(9) 1.1959(3) 0.0385(6) Uani 1 1 d . . . O4 O 0.1523(4) 0.22927(8) 0.7104(4) 0.0391(6) Uani 1 1 d . . . O5 O -0.1550(4) 0.23244(7) 0.9358(3) 0.0355(6) Uani 1 1 d . . . O6 O 0.5044(4) 0.19064(10) 0.6126(3) 0.0373(6) Uani 1 1 d D . . H6A H 0.423(5) 0.2096(12) 0.549(5) 0.045 Uiso 1 1 d D . . H6B H 0.619(3) 0.1974(14) 0.604(5) 0.045 Uiso 1 1 d D . . N1 N 0.5793(5) 0.01406(10) 1.3615(4) 0.0384(7) Uani 1 1 d . . . N2 N 0.4997(4) 0.16633(10) 1.0135(4) 0.0344(6) Uani 1 1 d . . . C1 C 0.6646(6) -0.02590(12) 1.4692(5) 0.0411(8) Uani 1 1 d . . . H1A H 0.8092 -0.0277 1.4795 0.049 Uiso 1 1 calc R . . H1B H 0.6018 -0.0544 1.4117 0.049 Uiso 1 1 calc R . . C2 C 0.5936(6) 0.12420(13) 1.2837(5) 0.0406(8) Uani 1 1 d . . . H2 H 0.6221 0.1243 1.4088 0.049 Uiso 1 1 calc R . . C3 C 0.0162(6) 0.07643(13) 0.9482(5) 0.0408(8) Uani 1 1 d . . . H3 H 0.0237 0.0482 1.0103 0.049 Uiso 1 1 calc R . . C4 C 0.6949(6) 0.04139(12) 1.2915(5) 0.0365(8) Uani 1 1 d . . . C5 C 0.5473(6) 0.08493(12) 1.0108(5) 0.0380(8) Uani 1 1 d . . . H5 H 0.5432 0.0574 0.9449 0.046 Uiso 1 1 calc R . . C6 C 0.4985(5) 0.12659(12) 0.9260(5) 0.0376(8) Uani 1 1 d . . . H6 H 0.4626 0.1272 0.8006 0.045 Uiso 1 1 calc R . . C7 C 0.6025(5) 0.08392(12) 1.1939(5) 0.0348(7) Uani 1 1 d . . . C8 C 0.0065(5) 0.11765(12) 1.0336(5) 0.0365(8) Uani 1 1 d . . . H8 H 0.0087 0.1175 1.1550 0.044 Uiso 1 1 calc R . . C9 C 0.5424(6) 0.16464(13) 1.1893(5) 0.0408(9) Uani 1 1 d . . . H9 H 0.5375 0.1923 1.2523 0.049 Uiso 1 1 calc R . . C10 C 0.0147(6) 0.07658(12) 0.7712(5) 0.0399(8) Uani 1 1 d . . . H10 H 0.0175 0.0483 0.7112 0.048 Uiso 1 1 calc R . . C11 C 0.3696(5) 0.02174(13) 1.3490(5) 0.0397(8) Uani 1 1 d . . . H11A H 0.2903 -0.0042 1.2851 0.048 Uiso 1 1 calc R . . H11B H 0.3248 0.0503 1.2813 0.048 Uiso 1 1 calc R . . C12 C -0.0063(5) 0.15928(12) 0.9436(5) 0.0328(7) Uani 1 1 d . . . C13 C 0.0093(5) 0.11768(13) 0.6818(5) 0.0365(8) Uani 1 1 d . . . H13 H 0.0123 0.1175 0.5616 0.044 Uiso 1 1 calc R . . C14 C -0.0007(5) 0.15944(11) 0.7668(4) 0.0320(7) Uani 1 1 d . . . C15 C 0.0055(5) 0.20327(13) 0.6654(5) 0.0334(8) Uani 1 1 d . . . C16 C -0.0450(5) 0.20263(12) 1.0326(5) 0.0320(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 0.0327(2) 0.0306(2) 0.0333(2) 0.00161(8) 0.00934(13) 0.00078(8) O1 0.0399(16) 0.0464(15) 0.0629(18) 0.0144(13) 0.0204(13) 0.0076(12) O2 0.0381(14) 0.0416(14) 0.0342(13) 0.0007(10) 0.0055(11) -0.0022(11) O3 0.0444(15) 0.0384(14) 0.0319(13) -0.0017(11) 0.0086(11) 0.0047(11) O4 0.0350(15) 0.0351(13) 0.0478(16) 0.0034(10) 0.0121(12) -0.0034(11) O5 0.0353(14) 0.0328(13) 0.0396(14) 0.0001(9) 0.0121(11) 0.0020(9) O6 0.0353(15) 0.0389(15) 0.0378(14) 0.0040(10) 0.0099(12) 0.0028(10) N1 0.0366(17) 0.0375(16) 0.0431(17) 0.0104(13) 0.0137(13) 0.0062(13) N2 0.0321(15) 0.0353(15) 0.0360(16) 0.0012(12) 0.0091(12) -0.0004(12) C1 0.043(2) 0.0350(18) 0.049(2) 0.0098(15) 0.0179(17) 0.0075(15) C2 0.048(2) 0.0375(19) 0.0349(18) 0.0017(14) 0.0086(16) -0.0019(16) C3 0.041(2) 0.0334(19) 0.050(2) 0.0037(16) 0.0142(17) 0.0008(15) C4 0.041(2) 0.0346(18) 0.0351(17) 0.0010(14) 0.0124(15) 0.0013(15) C5 0.043(2) 0.0325(18) 0.0397(19) 0.0001(14) 0.0131(16) 0.0003(15) C6 0.039(2) 0.039(2) 0.0341(18) 0.0003(15) 0.0088(14) -0.0025(15) C7 0.0316(18) 0.0350(18) 0.0395(18) 0.0048(14) 0.0124(15) -0.0006(14) C8 0.0356(19) 0.0372(19) 0.0377(18) 0.0018(14) 0.0116(15) 0.0004(15) C9 0.050(2) 0.035(2) 0.038(2) -0.0013(16) 0.0136(16) -0.0017(17) C10 0.038(2) 0.0330(19) 0.050(2) -0.0049(15) 0.0147(17) -0.0021(15) C11 0.0345(19) 0.0369(19) 0.047(2) 0.0103(15) 0.0100(16) 0.0013(15) C12 0.0281(17) 0.0340(18) 0.0358(18) -0.0020(14) 0.0077(14) -0.0027(14) C13 0.0349(19) 0.039(2) 0.0362(17) -0.0049(15) 0.0103(14) -0.0006(15) C14 0.0275(17) 0.0318(17) 0.0365(18) 0.0006(14) 0.0080(14) -0.0007(13) C15 0.0327(19) 0.0360(19) 0.0350(17) -0.0021(14) 0.0150(15) 0.0012(14) C16 0.0268(17) 0.0332(18) 0.0378(18) 0.0019(14) 0.0119(14) 0.0012(14) _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 2.251(2) 4_665 ? Cd1 N2 2.303(3) . ? Cd1 O2 2.309(2) 4_666 ? Cd1 O4 2.341(3) . ? Cd1 O5 2.412(3) 1_655 ? Cd1 O6 2.427(3) . ? O1 C4 1.224(4) . ? O2 C15 1.268(4) . ? O2 Cd1 2.309(2) 4_565 ? O3 C16 1.254(5) . ? O3 Cd1 2.251(2) 4_566 ? O4 C15 1.246(4) . ? O5 C16 1.269(4) . ? O5 Cd1 2.412(3) 1_455 ? N1 C4 1.347(5) . ? N1 C11 1.455(5) . ? N1 C1 1.468(4) . ? N2 C9 1.335(5) . ? N2 C6 1.343(5) . ? C1 C11 1.514(5) 3_658 ? C2 C7 1.377(5) . ? C2 C9 1.386(5) . ? C3 C8 1.384(5) . ? C3 C10 1.388(6) . ? C4 C7 1.507(5) . ? C5 C6 1.381(5) . ? C5 C7 1.388(5) . ? C8 C12 1.393(5) . ? C10 C13 1.381(5) . ? C11 C1 1.514(5) 3_658 ? C12 C14 1.400(5) . ? C12 C16 1.499(5) . ? C13 C14 1.396(5) . ? C14 C15 1.510(5) . ? 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 N2 165.47(10) 4_665 . ? O3 Cd1 O2 86.14(9) 4_665 4_666 ? N2 Cd1 O2 107.55(9) . 4_666 ? O3 Cd1 O4 90.63(9) 4_665 . ? N2 Cd1 O4 95.65(9) . . ? O2 Cd1 O4 83.42(9) 4_666 . ? O3 Cd1 O5 82.34(9) 4_665 1_655 ? N2 Cd1 O5 87.44(9) . 1_655 ? O2 Cd1 O5 114.33(8) 4_666 1_655 ? O4 Cd1 O5 160.21(10) . 1_655 ? O3 Cd1 O6 82.29(8) 4_665 . ? N2 Cd1 O6 86.33(9) . . ? O2 Cd1 O6 157.28(9) 4_666 . ? O4 Cd1 O6 77.24(9) . . ? O5 Cd1 O6 83.48(8) 1_655 . ? C15 O2 Cd1 105.1(2) . 4_565 ? C16 O3 Cd1 125.8(2) . 4_566 ? C15 O4 Cd1 145.7(2) . . ? C16 O5 Cd1 125.7(2) . 1_455 ? C4 N1 C11 125.4(3) . . ? C4 N1 C1 120.5(3) . . ? C11 N1 C1 114.0(3) . . ? C9 N2 C6 117.9(3) . . ? C9 N2 Cd1 120.9(2) . . ? C6 N2 Cd1 120.3(2) . . ? N1 C1 C11 109.9(3) . 3_658 ? C7 C2 C9 119.1(3) . . ? C8 C3 C10 119.7(3) . . ? O1 C4 N1 123.4(3) . . ? O1 C4 C7 118.6(3) . . ? N1 C4 C7 118.1(3) . . ? C6 C5 C7 119.0(3) . . ? N2 C6 C5 122.6(3) . . ? C2 C7 C5 118.4(3) . . ? C2 C7 C4 120.5(3) . . ? C5 C7 C4 120.6(3) . . ? C3 C8 C12 120.8(3) . . ? N2 C9 C2 122.7(3) . . ? C13 C10 C3 120.3(3) . . ? N1 C11 C1 110.7(3) . 3_658 ? C8 C12 C14 119.4(3) . . ? C8 C12 C16 119.3(3) . . ? C14 C12 C16 121.0(3) . . ? C10 C13 C14 120.5(3) . . ? C13 C14 C12 119.3(3) . . ? C13 C14 C15 118.0(3) . . ? C12 C14 C15 122.6(3) . . ? O4 C15 O2 122.4(3) . . ? O4 C15 C14 119.9(3) . . ? O2 C15 C14 117.5(3) . . ? O3 C16 O5 126.0(3) . . ? O3 C16 C12 117.3(3) . . ? O5 C16 C12 116.7(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 O3 Cd1 O4 C15 154.8(4) 4_665 . . . ? N2 Cd1 O4 C15 -12.1(4) . . . . ? O2 Cd1 O4 C15 -119.1(4) 4_666 . . . ? O5 Cd1 O4 C15 86.1(5) 1_655 . . . ? O6 Cd1 O4 C15 72.9(4) . . . . ? O3 Cd1 N2 C9 125.7(4) 4_665 . . . ? O2 Cd1 N2 C9 -34.2(3) 4_666 . . . ? O4 Cd1 N2 C9 -119.1(3) . . . . ? O5 Cd1 N2 C9 80.5(3) 1_655 . . . ? O6 Cd1 N2 C9 164.2(3) . . . . ? O3 Cd1 N2 C6 -42.8(5) 4_665 . . . ? O2 Cd1 N2 C6 157.3(2) 4_666 . . . ? O4 Cd1 N2 C6 72.4(3) . . . . ? O5 Cd1 N2 C6 -88.0(3) 1_655 . . . ? O6 Cd1 N2 C6 -4.3(3) . . . . ? C4 N1 C1 C11 121.7(4) . . . 3_658 ? C11 N1 C1 C11 -55.1(5) . . . 3_658 ? C11 N1 C4 O1 -179.6(4) . . . . ? C1 N1 C4 O1 4.1(5) . . . . ? C11 N1 C4 C7 0.9(5) . . . . ? C1 N1 C4 C7 -175.4(3) . . . . ? C9 N2 C6 C5 -2.7(5) . . . . ? Cd1 N2 C6 C5 166.1(3) . . . . ? C7 C5 C6 N2 -0.9(5) . . . . ? C9 C2 C7 C5 -4.1(5) . . . . ? C9 C2 C7 C4 168.1(3) . . . . ? C6 C5 C7 C2 4.3(5) . . . . ? C6 C5 C7 C4 -167.9(3) . . . . ? O1 C4 C7 C2 -94.0(4) . . . . ? N1 C4 C7 C2 85.5(4) . . . . ? O1 C4 C7 C5 78.1(5) . . . . ? N1 C4 C7 C5 -102.4(4) . . . . ? C10 C3 C8 C12 0.6(6) . . . . ? C6 N2 C9 C2 3.0(6) . . . . ? Cd1 N2 C9 C2 -165.8(3) . . . . ? C7 C2 C9 N2 0.5(6) . . . . ? C8 C3 C10 C13 1.8(6) . . . . ? C4 N1 C11 C1 -121.0(4) . . . 3_658 ? C1 N1 C11 C1 55.5(4) . . . 3_658 ? C3 C8 C12 C14 -2.8(5) . . . . ? C3 C8 C12 C16 171.6(3) . . . . ? C3 C10 C13 C14 -1.8(6) . . . . ? C10 C13 C14 C12 -0.4(5) . . . . ? C10 C13 C14 C15 176.6(3) . . . . ? C8 C12 C14 C13 2.7(5) . . . . ? C16 C12 C14 C13 -171.6(3) . . . . ? C8 C12 C14 C15 -174.2(3) . . . . ? C16 C12 C14 C15 11.6(5) . . . . ? Cd1 O4 C15 O2 -155.4(3) . . . . ? Cd1 O4 C15 C14 18.9(6) . . . . ? Cd1 O2 C15 O4 13.7(4) 4_565 . . . ? Cd1 O2 C15 C14 -160.7(2) 4_565 . . . ? C13 C14 C15 O4 -112.2(4) . . . . ? C12 C14 C15 O4 64.7(5) . . . . ? C13 C14 C15 O2 62.4(4) . . . . ? C12 C14 C15 O2 -120.7(4) . . . . ? Cd1 O3 C16 O5 1.1(5) 4_566 . . . ? Cd1 O3 C16 C12 -176.9(2) 4_566 . . . ? Cd1 O5 C16 O3 -90.4(4) 1_455 . . . ? Cd1 O5 C16 C12 87.6(3) 1_455 . . . ? C8 C12 C16 O3 34.7(5) . . . . ? C14 C12 C16 O3 -151.0(3) . . . . ? C8 C12 C16 O5 -143.5(3) . . . . ? C14 C12 C16 O5 30.8(5) . . . . ? 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 O6 H6A O5 0.851(18) 1.92(3) 2.711(4) 155(4) 4_665 O6 H6B O2 0.841(18) 2.00(2) 2.823(3) 168(4) 1_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.830 _refine_diff_density_min -1.212 _refine_diff_density_rms 0.101 # Attachment '0copht4bpfpfinal.cif' data_p21 _database_code_depnum_ccdc_archive 'CCDC 783828' #TrackingRef '0copht4bpfpfinal.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 Co N4 O9' _chemical_formula_weight 573.42 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.2140(9) _cell_length_b 10.5245(9) _cell_length_c 11.2450(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.857(1) _cell_angle_gamma 90.00 _cell_volume 1197.46(18) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6420 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 25.34 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 594 _exptl_absorpt_coefficient_mu 0.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7756 _exptl_absorpt_correction_T_max 0.8093 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7396 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4118 _reflns_number_gt 4002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0500P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.023(15) _refine_ls_number_reflns 4118 _refine_ls_number_parameters 361 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.177 _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 0.57121(4) 0.69092(4) 0.07520(3) 0.03560(14) Uani 1 1 d . . . O1W O 0.9230(3) 0.4261(3) 0.2626(3) 0.0662(8) Uani 1 1 d D . . H1WA H 0.883(4) 0.492(3) 0.287(4) 0.079 Uiso 1 1 d D . . H1WB H 0.858(4) 0.380(4) 0.233(5) 0.079 Uiso 1 1 d D . . O1 O 0.6728(3) 0.5432(2) 0.3412(2) 0.0489(6) Uani 1 1 d . . . O2 O 0.5685(2) 0.5086(2) 0.15551(19) 0.0390(5) Uani 1 1 d . . . O3 O 0.5515(2) 0.1364(3) 0.0770(2) 0.0422(6) Uani 1 1 d . . . O4 O 0.7161(2) 0.2643(2) 0.1557(2) 0.0444(6) Uani 1 1 d . . . O5 O 0.6856(2) 0.7623(2) 0.2301(2) 0.0429(6) Uani 1 1 d D . . H5A H 0.749(3) 0.803(3) 0.214(3) 0.052 Uiso 1 1 d D . . H5B H 0.697(4) 0.701(3) 0.278(3) 0.052 Uiso 1 1 d D . . O6 O -0.0435(3) 0.7382(3) 0.2988(2) 0.0601(8) Uani 1 1 d . . . O7 O 0.5785(3) 0.8768(2) 0.0148(2) 0.0433(6) Uani 1 1 d D . . H7A H 0.623(4) 0.930(3) 0.057(3) 0.052 Uiso 1 1 d D . . H7B H 0.532(4) 0.905(4) -0.047(3) 0.052 Uiso 1 1 d D . . O8 O 0.1663(3) 0.4739(3) 0.8694(2) 0.0466(6) Uani 1 1 d . . . N1 N 0.3939(3) 0.7172(3) 0.1629(2) 0.0391(7) Uani 1 1 d . . . N2 N 0.0728(2) 0.6822(3) 0.4767(2) 0.0425(6) Uani 1 1 d . . . N3 N 0.0609(3) 0.5502(3) 0.6925(3) 0.0425(7) Uani 1 1 d . . . N4 N -0.2552(3) 0.6373(3) 0.9941(2) 0.0415(7) Uani 1 1 d . . . C1 C 0.3947(3) 0.7862(3) 0.2632(3) 0.0409(8) Uani 1 1 d . . . H1 H 0.4693 0.8385 0.2882 0.049 Uiso 1 1 calc R . . C2 C 0.2926(3) 0.7850(4) 0.3321(3) 0.0424(8) Uani 1 1 d . . . H2 H 0.2973 0.8357 0.4025 0.051 Uiso 1 1 calc R . . C3 C 0.1833(3) 0.7092(4) 0.2976(3) 0.0411(8) Uani 1 1 d . . . C4 C 0.1799(4) 0.6385(4) 0.1916(3) 0.0423(8) Uani 1 1 d . . . H4 H 0.1058 0.5867 0.1637 0.051 Uiso 1 1 calc R . . C5 C 0.2862(4) 0.6457(4) 0.1290(3) 0.0438(8) Uani 1 1 d . . . H5 H 0.2834 0.5972 0.0575 0.053 Uiso 1 1 calc R . . C6 C 0.0620(3) 0.7106(4) 0.3591(3) 0.0411(8) Uani 1 1 d . . . C7 C 0.1950(3) 0.6469(4) 0.5545(3) 0.0449(8) Uani 1 1 d . . . H7C H 0.2240 0.7185 0.6089 0.054 Uiso 1 1 calc R . . H7D H 0.2656 0.6297 0.5045 0.054 Uiso 1 1 calc R . . C8 C 0.1737(3) 0.5305(4) 0.6280(3) 0.0441(8) Uani 1 1 d . . . H8A H 0.1576 0.4558 0.5746 0.053 Uiso 1 1 calc R . . H8B H 0.2539 0.5138 0.6860 0.053 Uiso 1 1 calc R . . C9 C -0.0440(3) 0.6953(5) 0.5398(3) 0.0455(7) Uani 1 1 d . . . H9A H -0.1239 0.7082 0.4805 0.055 Uiso 1 1 calc R . . H9B H -0.0332 0.7706 0.5931 0.055 Uiso 1 1 calc R . . C10 C -0.0611(4) 0.5779(4) 0.6134(3) 0.0474(8) Uani 1 1 d . . . H10A H -0.1339 0.5915 0.6619 0.057 Uiso 1 1 calc R . . H10B H -0.0848 0.5048 0.5594 0.057 Uiso 1 1 calc R . . C11 C 0.0699(3) 0.5247(3) 0.8112(3) 0.0405(8) Uani 1 1 d . . . C12 C -0.2227(4) 0.5156(3) 0.9843(3) 0.0421(8) Uani 1 1 d . . . H12 H -0.2733 0.4533 1.0187 0.051 Uiso 1 1 calc R . . C13 C -0.1185(4) 0.4751(3) 0.9263(3) 0.0435(8) Uani 1 1 d . . . H13 H -0.0977 0.3873 0.9230 0.052 Uiso 1 1 calc R . . C14 C -0.0455(3) 0.5643(3) 0.8733(3) 0.0398(7) Uani 1 1 d . . . C15 C -0.0781(3) 0.6905(5) 0.8837(3) 0.0483(8) Uani 1 1 d . . . H15 H -0.0297 0.7546 0.8492 0.058 Uiso 1 1 calc R . . C16 C -0.1827(4) 0.7233(3) 0.9453(3) 0.0483(9) Uani 1 1 d . . . H16 H -0.2032 0.8107 0.9528 0.058 Uiso 1 1 calc R . . C20 C 0.5303(3) 0.3668(3) 0.3102(3) 0.0397(7) Uani 1 1 d . . . C21 C 0.4625(4) 0.3848(4) 0.4097(3) 0.0445(8) Uani 1 1 d . . . H21 H 0.4622 0.4664 0.4458 0.053 Uiso 1 1 calc R . . C22 C 0.3968(4) 0.2858(4) 0.4555(3) 0.0487(9) Uani 1 1 d . . . H22 H 0.3517 0.2994 0.5229 0.058 Uiso 1 1 calc R . . C23 C 0.3962(4) 0.1665(4) 0.4035(3) 0.0478(9) Uani 1 1 d . . . H23 H 0.3535 0.0975 0.4367 0.057 Uiso 1 1 calc R . . C24 C 0.4584(4) 0.1484(4) 0.3030(3) 0.0456(8) Uani 1 1 d . . . H24 H 0.4534 0.0676 0.2649 0.055 Uiso 1 1 calc R . . C25 C 0.5280(3) 0.2460(3) 0.2563(3) 0.0398(7) Uani 1 1 d . . . C26 C 0.5968(3) 0.4808(3) 0.2659(3) 0.0390(7) Uani 1 1 d . . . C27 C 0.6051(3) 0.2161(3) 0.1547(3) 0.0390(8) 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 Co1 0.0353(2) 0.0354(2) 0.0371(2) -0.00031(18) 0.00820(16) -0.0012(2) O1W 0.0488(16) 0.0577(19) 0.091(2) -0.0110(17) 0.0068(16) -0.0019(15) O1 0.0532(14) 0.0477(14) 0.0446(13) -0.0005(11) 0.0020(12) -0.0077(13) O2 0.0410(12) 0.0401(12) 0.0362(12) -0.0018(9) 0.0066(10) -0.0001(11) O3 0.0428(13) 0.0406(12) 0.0422(14) -0.0007(10) 0.0029(11) 0.0051(11) O4 0.0447(13) 0.0411(14) 0.0491(13) -0.0035(10) 0.0121(11) -0.0043(12) O5 0.0367(12) 0.0431(14) 0.0505(15) -0.0003(11) 0.0113(12) -0.0063(11) O6 0.0382(13) 0.095(2) 0.0473(14) 0.0107(14) 0.0072(12) 0.0074(14) O7 0.0479(14) 0.0351(13) 0.0455(14) 0.0001(10) 0.0017(11) -0.0006(11) O8 0.0416(13) 0.0525(15) 0.0459(14) 0.0039(11) 0.0069(12) 0.0058(12) N1 0.0388(14) 0.0364(18) 0.0419(14) 0.0027(11) 0.0047(12) -0.0001(12) N2 0.0325(12) 0.0546(17) 0.0416(13) 0.0025(15) 0.0096(11) 0.0053(17) N3 0.0369(15) 0.0515(18) 0.0412(15) 0.0031(13) 0.0131(13) 0.0043(14) N4 0.0408(15) 0.0439(15) 0.0400(15) 0.0031(12) 0.0063(13) -0.0033(13) C1 0.0402(18) 0.0417(18) 0.0417(18) 0.0001(14) 0.0091(15) -0.0023(15) C2 0.0419(18) 0.049(2) 0.0372(17) -0.0028(14) 0.0088(15) 0.0005(16) C3 0.0374(16) 0.047(2) 0.0401(16) 0.0059(15) 0.0074(13) 0.0035(17) C4 0.0380(17) 0.0467(18) 0.0426(18) -0.0007(14) 0.0068(15) -0.0037(16) C5 0.0452(19) 0.0451(19) 0.0421(18) -0.0026(14) 0.0100(16) -0.0037(16) C6 0.0393(16) 0.043(2) 0.0409(16) 0.0001(14) 0.0062(14) -0.0001(16) C7 0.0349(16) 0.056(2) 0.0443(18) 0.0028(15) 0.0079(15) 0.0010(16) C8 0.0394(17) 0.050(2) 0.0454(18) 0.0027(15) 0.0149(15) 0.0079(17) C9 0.0369(15) 0.058(2) 0.0440(16) 0.005(2) 0.0131(13) 0.010(2) C10 0.0391(19) 0.061(2) 0.0432(19) 0.0015(16) 0.0094(16) -0.0014(18) C11 0.0391(18) 0.0397(18) 0.0445(19) -0.0006(14) 0.0121(16) -0.0029(16) C12 0.0440(18) 0.0392(19) 0.0452(18) 0.0031(14) 0.0135(16) -0.0022(16) C13 0.0464(19) 0.0384(19) 0.048(2) -0.0007(14) 0.0137(16) 0.0018(16) C14 0.0394(17) 0.0438(19) 0.0374(17) 0.0007(13) 0.0091(14) 0.0023(16) C15 0.0513(18) 0.0419(17) 0.0566(18) 0.007(2) 0.0252(16) -0.006(2) C16 0.054(2) 0.039(2) 0.056(2) -0.0004(14) 0.0209(18) 0.0026(16) C20 0.0378(17) 0.0449(18) 0.0369(17) 0.0000(14) 0.0071(14) 0.0028(16) C21 0.0428(18) 0.051(2) 0.0406(18) -0.0029(14) 0.0081(16) 0.0043(17) C22 0.0419(18) 0.067(2) 0.0389(18) 0.0033(17) 0.0106(16) 0.0021(19) C23 0.0426(17) 0.057(3) 0.0437(18) 0.0130(16) 0.0046(15) -0.0087(18) C24 0.0404(18) 0.046(2) 0.048(2) 0.0042(14) -0.0015(16) -0.0030(16) C25 0.0360(17) 0.0443(17) 0.0388(16) 0.0034(14) 0.0045(15) 0.0042(15) C26 0.0345(16) 0.0460(19) 0.0379(18) -0.0047(14) 0.0107(15) 0.0034(15) C27 0.0415(17) 0.036(2) 0.0380(15) 0.0020(12) 0.0021(14) 0.0028(15) _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 O3 2.060(2) 2_655 ? Co1 O7 2.075(2) . ? Co1 O5 2.099(2) . ? Co1 O2 2.122(2) . ? Co1 N4 2.176(3) 1_654 ? Co1 N1 2.195(3) . ? O1W H1WA 0.868(19) . ? O1W H1WB 0.858(19) . ? O1 C26 1.252(4) . ? O2 C26 1.270(4) . ? O3 C27 1.279(4) . ? O3 Co1 2.060(2) 2_645 ? O4 C27 1.240(4) . ? O5 H5A 0.820(18) . ? O5 H5B 0.842(18) . ? O6 C6 1.228(4) . ? O7 H7A 0.831(19) . ? O7 H7B 0.839(18) . ? O8 C11 1.228(4) . ? N1 C1 1.341(4) . ? N1 C5 1.344(4) . ? N2 C6 1.346(4) . ? N2 C7 1.470(4) . ? N2 C9 1.476(4) . ? N3 C11 1.352(4) . ? N3 C10 1.458(5) . ? N3 C8 1.458(4) . ? N4 C12 1.331(5) . ? N4 C16 1.335(5) . ? N4 Co1 2.176(3) 1_456 ? C1 C2 1.382(5) . ? C1 H1 0.9500 . ? C2 C3 1.384(5) . ? C2 H2 0.9500 . ? C3 C4 1.401(5) . ? C3 C6 1.499(5) . ? C4 C5 1.374(5) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C7 C8 1.510(5) . ? C7 H7C 0.9900 . ? C7 H7D 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.510(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C14 1.509(5) . ? C12 C13 1.389(5) . ? C12 H12 0.9500 . ? C13 C14 1.383(5) . ? C13 H13 0.9500 . ? C14 C15 1.379(6) . ? C15 C16 1.393(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C20 C21 1.406(5) . ? C20 C25 1.407(5) . ? C20 C26 1.497(5) . ? C21 C22 1.377(6) . ? C21 H21 0.9500 . ? C22 C23 1.385(6) . ? C22 H22 0.9500 . ? C23 C24 1.383(5) . ? C23 H23 0.9500 . ? C24 C25 1.392(5) . ? C24 H24 0.9500 . ? C25 C27 1.507(5) . ? 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 Co1 O7 92.01(10) 2_655 . ? O3 Co1 O5 174.57(10) 2_655 . ? O7 Co1 O5 83.88(10) . . ? O3 Co1 O2 93.45(9) 2_655 . ? O7 Co1 O2 174.00(9) . . ? O5 Co1 O2 90.51(10) . . ? O3 Co1 N4 91.01(10) 2_655 1_654 ? O7 Co1 N4 92.26(11) . 1_654 ? O5 Co1 N4 92.70(10) . 1_654 ? O2 Co1 N4 90.15(10) . 1_654 ? O3 Co1 N1 87.86(10) 2_655 . ? O7 Co1 N1 95.57(10) . . ? O5 Co1 N1 89.00(9) . . ? O2 Co1 N1 82.14(9) . . ? N4 Co1 N1 172.12(11) 1_654 . ? H1WA O1W H1WB 102(3) . . ? C26 O2 Co1 127.6(2) . . ? C27 O3 Co1 122.7(2) . 2_645 ? Co1 O5 H5A 112(3) . . ? Co1 O5 H5B 105(3) . . ? H5A O5 H5B 120(3) . . ? Co1 O7 H7A 119(3) . . ? Co1 O7 H7B 125(3) . . ? H7A O7 H7B 116(4) . . ? C1 N1 C5 116.9(3) . . ? C1 N1 Co1 122.3(2) . . ? C5 N1 Co1 119.7(2) . . ? C6 N2 C7 126.1(3) . . ? C6 N2 C9 119.3(3) . . ? C7 N2 C9 114.5(3) . . ? C11 N3 C10 125.4(3) . . ? C11 N3 C8 120.7(3) . . ? C10 N3 C8 113.2(3) . . ? C12 N4 C16 117.3(3) . . ? C12 N4 Co1 120.7(2) . 1_456 ? C16 N4 Co1 121.8(3) . 1_456 ? N1 C1 C2 123.2(3) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 118.0(3) . . ? C2 C3 C6 123.4(3) . . ? C4 C3 C6 118.1(3) . . ? C5 C4 C3 118.5(3) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 124.0(3) . . ? N1 C5 H5 118.0 . . ? C4 C5 H5 118.0 . . ? O6 C6 N2 122.9(3) . . ? O6 C6 C3 117.8(3) . . ? N2 C6 C3 119.3(3) . . ? N2 C7 C8 110.9(3) . . ? N2 C7 H7C 109.5 . . ? C8 C7 H7C 109.5 . . ? N2 C7 H7D 109.5 . . ? C8 C7 H7D 109.5 . . ? H7C C7 H7D 108.1 . . ? N3 C8 C7 109.9(3) . . ? N3 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? N3 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N2 C9 C10 110.4(3) . . ? N2 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? N2 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? N3 C10 C9 110.1(3) . . ? N3 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N3 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O8 C11 N3 123.7(3) . . ? O8 C11 C14 119.6(3) . . ? N3 C11 C14 116.7(3) . . ? N4 C12 C13 123.4(3) . . ? N4 C12 H12 118.3 . . ? C13 C12 H12 118.3 . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C15 C14 C13 117.8(3) . . ? C15 C14 C11 121.3(3) . . ? C13 C14 C11 120.8(3) . . ? C14 C15 C16 119.4(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N4 C16 C15 122.9(4) . . ? N4 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? C21 C20 C25 118.9(3) . . ? C21 C20 C26 116.9(3) . . ? C25 C20 C26 124.2(3) . . ? C22 C21 C20 120.9(4) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C23 120.2(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 119.6(3) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 121.4(4) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C24 C25 C20 118.9(3) . . ? C24 C25 C27 118.6(3) . . ? C20 C25 C27 122.4(3) . . ? O1 C26 O2 125.2(3) . . ? O1 C26 C20 117.6(3) . . ? O2 C26 C20 117.2(3) . . ? O4 C27 O3 125.4(3) . . ? O4 C27 C25 118.7(3) . . ? O3 C27 C25 115.8(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O1 0.868(19) 2.37(4) 3.074(4) 138(4) . O1W H1WA O6 0.868(19) 2.70(4) 3.322(5) 130(4) 1_655 O1W H1WB O4 0.858(19) 1.99(2) 2.850(4) 175(5) . O5 H5A O8 0.820(18) 2.25(2) 2.993(4) 150(4) 2_656 O5 H5A O6 0.820(18) 2.30(4) 2.780(4) 118(3) 1_655 O5 H5B O1 0.842(18) 1.83(2) 2.635(4) 159(4) . O7 H7A O3 0.831(19) 2.31(4) 2.844(4) 122(3) 1_565 O7 H7A O8 0.831(19) 2.24(3) 2.934(4) 140(4) 2_656 O7 H7B O2 0.839(18) 1.84(2) 2.657(3) 164(4) 2_655 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.522 _refine_diff_density_min -0.796 _refine_diff_density_rms 0.058 # Attachment '0cupht4bpfpfinal.cif' data_p1b _database_code_depnum_ccdc_archive 'CCDC 783829' #TrackingRef '0cupht4bpfpfinal.cif' _audit_update_record ; 2010-07-08 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H28 Cu2 N4 O12' _chemical_formula_weight 787.66 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2812(10) _cell_length_b 10.7032(14) _cell_length_c 10.8333(14) _cell_angle_alpha 95.672(2) _cell_angle_beta 103.322(2) _cell_angle_gamma 109.235(2) _cell_volume 761.52(17) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7241 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.32 _exptl_crystal_description chunk _exptl_crystal_colour blue _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 1.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6390 _exptl_absorpt_correction_T_max 0.7632 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11045 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2759 _reflns_number_gt 2521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0368P)^2^+0.3685P] 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 2759 _refine_ls_number_parameters 232 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.150 _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 0.23907(5) 0.59722(3) 0.22764(3) 0.03231(16) Uani 1 1 d . . . O1 O 0.6201(3) 0.6184(2) 0.1123(2) 0.0493(6) Uani 1 1 d . . . O2 O -0.4589(3) 0.3295(2) 0.5380(2) 0.0398(5) Uani 1 1 d . . . O3 O 1.1261(3) 0.73769(19) 0.26864(18) 0.0325(4) Uani 1 1 d . . . O4 O 1.0112(3) 0.6750(2) 0.05587(19) 0.0374(5) Uani 1 1 d . . . O5 O 0.4552(3) 0.73746(19) 0.1872(2) 0.0364(5) Uani 1 1 d . . . O6 O 0.3046(3) 0.4499(2) 0.1503(2) 0.0344(4) Uani 1 1 d D . . H6C H 0.404(4) 0.490(3) 0.121(3) 0.041 Uiso 1 1 d D . . H6D H 0.210(4) 0.403(3) 0.081(2) 0.041 Uiso 1 1 d D . . N1 N -0.4953(4) 0.1175(2) 0.4521(2) 0.0348(5) Uani 1 1 d . . . N2 N 0.0347(4) 0.4621(2) 0.2910(2) 0.0340(5) Uani 1 1 d . . . C1 C 1.0527(5) 1.1055(3) 0.1529(3) 0.0390(7) Uani 1 1 d . . . H1 H 1.1542 1.1911 0.1607 0.047 Uiso 1 1 calc R . . C2 C -0.4216(5) 0.0232(3) 0.3909(3) 0.0362(6) Uani 1 1 d . . . H2A H -0.3103 0.0734 0.3561 0.043 Uiso 1 1 calc R . . H2B H -0.5325 -0.0409 0.3180 0.043 Uiso 1 1 calc R . . C3 C -0.2510(4) 0.3136(3) 0.4047(3) 0.0345(6) Uani 1 1 d . . . C4 C 0.8519(5) 1.0931(3) 0.1319(3) 0.0385(7) Uani 1 1 d . . . H4 H 0.8140 1.1690 0.1211 0.046 Uiso 1 1 calc R . . C5 C 1.0314(4) 0.7494(3) 0.1582(3) 0.0323(6) Uani 1 1 d . . . C6 C -0.6549(4) 0.0540(3) 0.5112(3) 0.0368(6) Uani 1 1 d . . . H6A H -0.7766 -0.0084 0.4438 0.044 Uiso 1 1 calc R . . H6B H -0.6926 0.1237 0.5548 0.044 Uiso 1 1 calc R . . C7 C 0.0889(4) 0.4009(3) 0.3889(3) 0.0357(6) Uani 1 1 d . . . H7 H 0.2265 0.4093 0.4184 0.043 Uiso 1 1 calc R . . C8 C 0.9594(4) 0.8664(3) 0.1548(3) 0.0312(6) Uani 1 1 d . . . C9 C -0.0490(4) 0.3263(3) 0.4482(3) 0.0353(6) Uani 1 1 d . . . H9 H -0.0063 0.2848 0.5172 0.042 Uiso 1 1 calc R . . C10 C 1.1050(4) 0.9930(3) 0.1626(3) 0.0359(6) Uani 1 1 d . . . H10 H 1.2425 1.0019 0.1748 0.043 Uiso 1 1 calc R . . C11 C 0.7068(5) 0.9687(3) 0.1268(3) 0.0356(6) Uani 1 1 d . . . H11 H 0.5693 0.9603 0.1135 0.043 Uiso 1 1 calc R . . C12 C 0.5992(4) 0.7260(3) 0.1455(3) 0.0336(6) Uani 1 1 d . . . C13 C -0.4085(4) 0.2528(3) 0.4727(3) 0.0345(6) Uani 1 1 d . . . C14 C 0.7589(4) 0.8560(3) 0.1407(3) 0.0323(6) Uani 1 1 d . . . C15 C -0.1608(5) 0.4438(3) 0.2467(3) 0.0376(7) Uani 1 1 d . . . H15 H -0.2010 0.4826 0.1748 0.045 Uiso 1 1 calc R . . C16 C -0.3082(5) 0.3712(3) 0.3002(3) 0.0384(7) Uani 1 1 d . . . H16 H -0.4458 0.3611 0.2660 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0336(2) 0.0279(2) 0.0373(2) 0.00798(16) 0.01425(17) 0.01008(17) O1 0.0434(13) 0.0299(11) 0.0787(16) 0.0061(11) 0.0309(12) 0.0104(10) O2 0.0426(12) 0.0331(11) 0.0482(12) 0.0096(9) 0.0201(10) 0.0138(9) O3 0.0336(10) 0.0315(10) 0.0348(10) 0.0089(8) 0.0117(8) 0.0128(8) O4 0.0374(11) 0.0347(11) 0.0382(11) 0.0028(9) 0.0095(9) 0.0124(9) O5 0.0362(11) 0.0312(11) 0.0464(12) 0.0090(9) 0.0197(9) 0.0123(9) O6 0.0341(11) 0.0294(10) 0.0395(11) 0.0059(9) 0.0132(9) 0.0094(9) N1 0.0378(13) 0.0309(12) 0.0354(13) 0.0081(10) 0.0146(11) 0.0086(11) N2 0.0366(13) 0.0270(12) 0.0377(13) 0.0050(10) 0.0128(11) 0.0091(10) C1 0.0446(17) 0.0290(14) 0.0396(16) 0.0083(12) 0.0124(13) 0.0077(13) C2 0.0401(16) 0.0317(15) 0.0369(15) 0.0073(12) 0.0166(13) 0.0089(13) C3 0.0387(15) 0.0284(14) 0.0355(15) 0.0060(12) 0.0130(12) 0.0093(12) C4 0.0501(18) 0.0323(15) 0.0395(16) 0.0110(13) 0.0179(14) 0.0185(14) C5 0.0293(14) 0.0278(14) 0.0395(16) 0.0089(12) 0.0130(12) 0.0070(11) C6 0.0353(15) 0.0353(15) 0.0388(16) 0.0073(13) 0.0152(13) 0.0081(13) C7 0.0369(15) 0.0292(14) 0.0396(16) 0.0050(12) 0.0105(12) 0.0108(12) C8 0.0355(14) 0.0300(14) 0.0281(13) 0.0071(11) 0.0094(11) 0.0113(12) C9 0.0395(16) 0.0321(15) 0.0356(15) 0.0082(12) 0.0115(12) 0.0137(13) C10 0.0344(15) 0.0350(15) 0.0357(15) 0.0081(12) 0.0099(12) 0.0088(12) C11 0.0413(16) 0.0364(16) 0.0357(15) 0.0109(12) 0.0155(12) 0.0183(13) C12 0.0328(15) 0.0345(15) 0.0344(15) 0.0090(12) 0.0114(12) 0.0115(12) C13 0.0347(15) 0.0332(15) 0.0350(15) 0.0103(12) 0.0091(12) 0.0110(12) C14 0.0367(15) 0.0299(14) 0.0311(14) 0.0072(11) 0.0127(12) 0.0106(12) C15 0.0378(16) 0.0353(15) 0.0403(16) 0.0127(13) 0.0121(13) 0.0119(13) C16 0.0346(15) 0.0364(16) 0.0433(17) 0.0126(13) 0.0100(13) 0.0110(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 O5 1.953(2) . ? Cu1 O6 1.958(2) . ? Cu1 O3 1.9962(19) 1_455 ? Cu1 N2 2.006(2) . ? Cu1 O2 2.555(2) 2_566 ? O1 C12 1.240(3) . ? O2 C13 1.231(3) . ? O3 C5 1.277(3) . ? O3 Cu1 1.9962(19) 1_655 ? O4 C5 1.248(3) . ? O5 C12 1.269(3) . ? N1 C13 1.347(4) . ? N1 C6 1.460(4) . ? N1 C2 1.461(4) . ? N2 C15 1.334(4) . ? N2 C7 1.351(4) . ? C1 C10 1.384(4) . ? C1 C4 1.385(4) . ? C2 C6 1.524(4) 2_456 ? C3 C16 1.388(4) . ? C3 C9 1.392(4) . ? C3 C13 1.508(4) . ? C4 C11 1.387(4) . ? C5 C8 1.509(4) . ? C6 C2 1.524(4) 2_456 ? C7 C9 1.389(4) . ? C8 C14 1.398(4) . ? C8 C10 1.399(4) . ? C11 C14 1.390(4) . ? C12 C14 1.506(4) . ? C15 C16 1.385(5) . ? 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 O6 93.89(8) . . ? O5 Cu1 O3 87.79(8) . 1_455 ? O6 Cu1 O3 167.25(8) . 1_455 ? O5 Cu1 N2 173.31(9) . . ? O6 Cu1 N2 88.92(9) . . ? O3 Cu1 N2 90.81(9) 1_455 . ? O5 Cu1 O2 86.73(8) . 2_566 ? O6 Cu1 O2 106.25(8) . 2_566 ? O3 Cu1 O2 86.45(7) 1_455 2_566 ? N2 Cu1 O2 86.65(8) . 2_566 ? C5 O3 Cu1 104.02(17) . 1_655 ? C12 O5 Cu1 128.41(19) . . ? C13 N1 C6 120.2(2) . . ? C13 N1 C2 125.0(2) . . ? C6 N1 C2 114.0(2) . . ? C15 N2 C7 117.9(2) . . ? C15 N2 Cu1 119.1(2) . . ? C7 N2 Cu1 122.4(2) . . ? C10 C1 C4 119.9(3) . . ? N1 C2 C6 110.1(2) . 2_456 ? C16 C3 C9 118.7(3) . . ? C16 C3 C13 117.3(3) . . ? C9 C3 C13 123.7(3) . . ? C1 C4 C11 119.4(3) . . ? O4 C5 O3 122.5(3) . . ? O4 C5 C8 120.5(2) . . ? O3 C5 C8 116.8(2) . . ? N1 C6 C2 109.1(2) . 2_456 ? N2 C7 C9 122.5(3) . . ? C14 C8 C10 118.5(3) . . ? C14 C8 C5 124.7(2) . . ? C10 C8 C5 116.7(2) . . ? C7 C9 C3 118.8(3) . . ? C1 C10 C8 121.3(3) . . ? C4 C11 C14 121.2(3) . . ? O1 C12 O5 125.5(3) . . ? O1 C12 C14 118.6(3) . . ? O5 C12 C14 115.8(2) . . ? O2 C13 N1 123.5(3) . . ? O2 C13 C3 118.1(3) . . ? N1 C13 C3 118.2(3) . . ? C11 C14 C8 119.7(3) . . ? C11 C14 C12 119.2(3) . . ? C8 C14 C12 121.1(2) . . ? N2 C15 C16 123.3(3) . . ? C15 C16 C3 118.7(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 O6 Cu1 O5 C12 -10.1(2) . . . . ? O3 Cu1 O5 C12 -177.4(2) 1_455 . . . ? N2 Cu1 O5 C12 104.6(7) . . . . ? O2 Cu1 O5 C12 96.0(2) 2_566 . . . ? O5 Cu1 N2 C15 128.7(7) . . . . ? O6 Cu1 N2 C15 -116.4(2) . . . . ? O3 Cu1 N2 C15 50.8(2) 1_455 . . . ? O2 Cu1 N2 C15 137.2(2) 2_566 . . . ? O5 Cu1 N2 C7 -42.7(8) . . . . ? O6 Cu1 N2 C7 72.2(2) . . . . ? O3 Cu1 N2 C7 -120.6(2) 1_455 . . . ? O2 Cu1 N2 C7 -34.2(2) 2_566 . . . ? C13 N1 C2 C6 112.9(3) . . . 2_456 ? C6 N1 C2 C6 -57.0(3) . . . 2_456 ? C10 C1 C4 C11 3.0(4) . . . . ? Cu1 O3 C5 O4 5.3(3) 1_655 . . . ? Cu1 O3 C5 C8 -169.41(19) 1_655 . . . ? C13 N1 C6 C2 -114.0(3) . . . 2_456 ? C2 N1 C6 C2 56.5(3) . . . 2_456 ? C15 N2 C7 C9 -3.3(4) . . . . ? Cu1 N2 C7 C9 168.3(2) . . . . ? O4 C5 C8 C14 81.3(4) . . . . ? O3 C5 C8 C14 -103.9(3) . . . . ? O4 C5 C8 C10 -96.7(3) . . . . ? O3 C5 C8 C10 78.0(3) . . . . ? N2 C7 C9 C3 0.3(4) . . . . ? C16 C3 C9 C7 2.6(4) . . . . ? C13 C3 C9 C7 -170.9(3) . . . . ? C4 C1 C10 C8 -1.6(4) . . . . ? C14 C8 C10 C1 -1.9(4) . . . . ? C5 C8 C10 C1 176.3(3) . . . . ? C1 C4 C11 C14 -0.8(4) . . . . ? Cu1 O5 C12 O1 6.2(4) . . . . ? Cu1 O5 C12 C14 -171.94(18) . . . . ? C6 N1 C13 O2 -1.6(4) . . . . ? C2 N1 C13 O2 -171.0(3) . . . . ? C6 N1 C13 C3 -177.3(2) . . . . ? C2 N1 C13 C3 13.4(4) . . . . ? C16 C3 C13 O2 -71.0(4) . . . . ? C9 C3 C13 O2 102.7(3) . . . . ? C16 C3 C13 N1 104.9(3) . . . . ? C9 C3 C13 N1 -81.5(4) . . . . ? C4 C11 C14 C8 -2.7(4) . . . . ? C4 C11 C14 C12 175.0(3) . . . . ? C10 C8 C14 C11 4.0(4) . . . . ? C5 C8 C14 C11 -174.0(3) . . . . ? C10 C8 C14 C12 -173.6(3) . . . . ? C5 C8 C14 C12 8.4(4) . . . . ? O1 C12 C14 C11 154.7(3) . . . . ? O5 C12 C14 C11 -26.9(4) . . . . ? O1 C12 C14 C8 -27.7(4) . . . . ? O5 C12 C14 C8 150.6(3) . . . . ? C7 N2 C15 C16 3.3(5) . . . . ? Cu1 N2 C15 C16 -168.5(3) . . . . ? N2 C15 C16 C3 -0.4(5) . . . . ? C9 C3 C16 C15 -2.6(4) . . . . ? C13 C3 C16 C15 171.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6C O1 0.856(17) 1.75(2) 2.560(3) 158(3) . O6 H6D O4 0.870(18) 1.801(18) 2.661(3) 170(3) 2_665 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.427 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.073