# 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 ? _publ_contact_author_name 'Bo Xu' _publ_contact_author_email xubo@fjirsm.ac.cn _publ_author_name B.Xu data_f:\struct~1\10051907\01 _database_code_depnum_ccdc_archive 'CCDC 783373' #TrackingRef '- 1-cif.tex' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H34 Co N4 O8' _chemical_formula_weight 577.49 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 Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 11.290(3) _cell_length_b 12.609(4) _cell_length_c 10.281(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.231(6) _cell_angle_gamma 90.00 _cell_volume 1397.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3436 _cell_measurement_theta_min 2.4850 _cell_measurement_theta_max 27.4526 _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 0.666 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9067 _exptl_absorpt_correction_T_max 0.9243 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 Saturn _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10803 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5631 _reflns_number_gt 4423 _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^)+(0.0770P)^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 refxyz _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 0.075(19) _refine_ls_number_reflns 5631 _refine_ls_number_parameters 329 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 Co1 Co 0.76780(7) 0.25225(4) 0.14464(7) 0.03101(13) Uani 1 1 d . . . O1 O 0.6560(3) 0.3434(2) -0.0214(3) 0.0406(6) Uani 1 1 d . . . O2 O 0.7962(3) 0.2348(2) -0.0532(3) 0.0393(7) Uani 1 1 d . . . C4 C 0.6816(3) 0.3063(3) -0.4747(4) 0.0313(7) Uani 1 1 d . . . N1 N 0.6254(3) 0.1303(3) 0.0826(4) 0.0379(8) Uani 1 1 d . . . C9 C 0.5761(3) 0.4037(3) -0.2945(4) 0.0351(8) Uani 1 1 d . . . H9 H 0.5409 0.4357 -0.2332 0.042 Uiso 1 1 calc R . . O4 O 0.8166(3) 0.1831(2) -0.5343(3) 0.0478(7) Uani 1 1 d . . . C6 C 0.5883(4) 0.3829(3) -0.5192(4) 0.0370(8) Uani 1 1 d . . . H6 H 0.5617 0.4011 -0.6109 0.044 Uiso 1 1 calc R . . N3 N 0.2809(3) -0.1456(3) 0.0343(4) 0.0420(8) Uani 1 1 d . . . C7 C 0.5351(4) 0.4319(3) -0.4306(4) 0.0355(8) Uani 1 1 d . . . C2 C 0.6689(3) 0.3283(3) -0.2478(3) 0.0314(8) Uani 1 1 d . . . N2 N -0.0947(3) -0.6206(3) 0.1935(4) 0.0376(8) Uani 1 1 d . . . N4 N 0.2184(3) -0.3216(3) 0.1868(4) 0.0435(9) Uani 1 1 d . . . C10 C 0.5149(4) 0.1387(4) 0.1040(5) 0.0452(10) Uani 1 1 d . . . H10 H 0.5013 0.1974 0.1525 0.054 Uiso 1 1 calc R . . C1 C 0.7086(3) 0.3011(3) -0.0998(4) 0.0319(8) Uani 1 1 d . . . C14 C 0.6420(4) 0.0461(4) 0.0115(5) 0.0505(11) Uani 1 1 d . . . H14 H 0.7174 0.0383 -0.0068 0.061 Uiso 1 1 calc R . . C25 C 0.0101(4) -0.6207(4) 0.1563(5) 0.0491(11) Uani 1 1 d . . . H25 H 0.0275 -0.6798 0.1110 0.059 Uiso 1 1 calc R . . C3 C 0.7201(3) 0.2783(3) -0.3376(4) 0.0317(8) Uani 1 1 d . . . H3 H 0.7800 0.2260 -0.3068 0.038 Uiso 1 1 calc R . . C5 C 0.7397(4) 0.2560(3) -0.5748(4) 0.0303(8) Uani 1 1 d . . . C21 C 0.0701(4) -0.4479(3) 0.2484(4) 0.0396(9) Uani 1 1 d . . . C12 C 0.4378(4) -0.0224(3) -0.0109(5) 0.0436(10) Uani 1 1 d . . . C23 C -0.1156(4) -0.5338(4) 0.2586(6) 0.0529(12) Uani 1 1 d . . . H23 H -0.1866 -0.5315 0.2867 0.063 Uiso 1 1 calc R . . C15 C 0.3400(4) -0.1067(4) -0.0655(5) 0.0543(12) Uani 1 1 d . . . H15A H 0.2765 -0.0778 -0.1429 0.065 Uiso 1 1 calc R . . H15B H 0.3780 -0.1661 -0.0978 0.065 Uiso 1 1 calc R . . C22 C -0.0373(4) -0.4486(3) 0.2856(6) 0.0518(11) Uani 1 1 d . . . H22 H -0.0570 -0.3899 0.3301 0.062 Uiso 1 1 calc R . . C13 C 0.5518(4) -0.0299(4) -0.0359(5) 0.0502(11) Uani 1 1 d . . . H13 H 0.5675 -0.0871 -0.0855 0.060 Uiso 1 1 calc R . . C11 C 0.4201(4) 0.0671(4) 0.0599(5) 0.0515(11) Uani 1 1 d . . . H11 H 0.3447 0.0783 0.0771 0.062 Uiso 1 1 calc R . . C18 C 0.1905(5) -0.2293(4) -0.0317(6) 0.0517(12) Uani 1 1 d . . . H18A H 0.2330 -0.2857 -0.0640 0.062 Uiso 1 1 calc R . . H18B H 0.1283 -0.1996 -0.1096 0.062 Uiso 1 1 calc R . . C24 C 0.0921(4) -0.5379(4) 0.1819(6) 0.0528(12) Uani 1 1 d . . . H24 H 0.1634 -0.5421 0.1544 0.063 Uiso 1 1 calc R . . C16 C 0.3729(4) -0.1936(3) 0.1515(5) 0.0476(11) Uani 1 1 d . . . H16A H 0.4320 -0.1400 0.1980 0.057 Uiso 1 1 calc R . . H16B H 0.4179 -0.2486 0.1200 0.057 Uiso 1 1 calc R . . C20 C 0.1579(4) -0.3541(3) 0.2863(5) 0.0482(11) Uani 1 1 d . . . H20A H 0.1117 -0.2940 0.3049 0.058 Uiso 1 1 calc R . . H20B H 0.2216 -0.3712 0.3703 0.058 Uiso 1 1 calc R . . C8 C 0.4306(4) 0.5103(4) -0.4812(5) 0.0540(12) Uani 1 1 d . . . H9E H 0.4585 0.5797 -0.4473 0.081 Uiso 1 1 calc R . . H8D H 0.3620 0.4898 -0.4496 0.081 Uiso 1 1 calc R . . H8C H 0.4048 0.5113 -0.5790 0.081 Uiso 1 1 calc R . . C19 C 0.1279(4) -0.2741(3) 0.0691(5) 0.0492(11) Uani 1 1 d . . . H19A H 0.0840 -0.2178 0.0996 0.059 Uiso 1 1 calc R . . H19B H 0.0677 -0.3274 0.0240 0.059 Uiso 1 1 calc R . . C17 C 0.3106(5) -0.2407(3) 0.2494(6) 0.0471(11) Uani 1 1 d . . . H17A H 0.3733 -0.2720 0.3255 0.057 Uiso 1 1 calc R . . H17B H 0.2704 -0.1844 0.2850 0.057 Uiso 1 1 calc R . . O3 O 0.7057(3) 0.2922(2) -0.6940(3) 0.0389(6) Uani 1 1 d . . . O5 O 0.9006(2) 0.1453(2) 0.2528(3) 0.0407(7) Uani 1 1 d . . . H5A H 0.9012 0.1449 0.3357 0.061 Uiso 1 1 d R . . H5B H 0.8828 0.0837 0.2191 0.061 Uiso 1 1 d R . . O6 O 0.9361(3) -0.0551(3) 0.1777(3) 0.0535(8) Uiso 1 1 d . . . H6A H 0.9641 -0.0968 0.1289 0.080 Uiso 1 1 d R . . H6B H 0.9939 -0.0390 0.2492 0.080 Uiso 1 1 d R . . O7 O 1.0128(3) 0.1572(3) -0.0841(4) 0.0666(9) Uiso 1 1 d . . . H7A H 1.0010 0.2118 -0.0412 0.100 Uiso 1 1 d R . . H7B H 0.9918 0.1705 -0.1689 0.100 Uiso 1 1 d R . . O8 O 0.1449(3) 0.0206(3) 0.1113(4) 0.0597(9) Uiso 1 1 d . . . H8A H 0.0733 0.0393 0.1138 0.090 Uiso 1 1 d R . . H8B H 0.1416 -0.0420 0.0798 0.090 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 0.0361(2) 0.0366(2) 0.0217(2) -0.00047(19) 0.01064(17) -0.00251(19) O1 0.0505(16) 0.0495(16) 0.0236(13) 0.0011(12) 0.0138(12) 0.0097(13) O2 0.0410(16) 0.0524(18) 0.0267(17) 0.0026(12) 0.0133(14) 0.0052(13) C4 0.0410(19) 0.0309(19) 0.0248(17) -0.0003(14) 0.0141(15) -0.0019(15) N1 0.0376(17) 0.0372(18) 0.040(2) 0.0004(15) 0.0136(16) -0.0056(14) C9 0.0434(19) 0.0341(19) 0.0324(19) 0.0006(15) 0.0184(16) 0.0003(15) O4 0.0621(18) 0.0559(19) 0.0304(15) 0.0044(13) 0.0216(14) 0.0202(15) C6 0.046(2) 0.036(2) 0.0309(19) 0.0071(16) 0.0154(17) -0.0010(16) N3 0.0354(16) 0.0339(17) 0.049(2) 0.0009(15) 0.0002(15) -0.0054(13) C7 0.044(2) 0.0260(18) 0.042(2) 0.0097(15) 0.0207(18) 0.0013(15) C2 0.0414(19) 0.0334(18) 0.0220(17) -0.0001(14) 0.0133(15) -0.0031(15) N2 0.0438(18) 0.0345(18) 0.0342(17) -0.0027(14) 0.0113(15) -0.0041(14) N4 0.0366(17) 0.0306(17) 0.055(2) 0.0017(15) 0.0010(16) -0.0050(13) C10 0.052(2) 0.042(2) 0.047(3) -0.0029(19) 0.024(2) -0.0104(19) C1 0.0370(19) 0.0347(19) 0.0251(18) -0.0039(15) 0.0110(16) -0.0027(15) C14 0.042(2) 0.050(3) 0.061(3) -0.013(2) 0.016(2) -0.0020(19) C25 0.057(3) 0.042(2) 0.055(3) -0.012(2) 0.026(2) -0.0085(19) C3 0.0379(19) 0.0322(18) 0.0261(18) -0.0010(13) 0.0112(16) 0.0026(15) C5 0.0360(19) 0.0322(19) 0.025(2) -0.0013(14) 0.0132(16) -0.0006(14) C21 0.040(2) 0.0314(19) 0.042(2) 0.0006(17) 0.0039(18) -0.0024(16) C12 0.044(2) 0.040(2) 0.040(2) 0.0042(18) 0.0024(18) -0.0081(18) C23 0.046(2) 0.043(2) 0.074(3) -0.013(2) 0.024(2) 0.0001(19) C15 0.054(3) 0.049(3) 0.052(3) -0.004(2) 0.003(2) -0.015(2) C22 0.052(3) 0.031(2) 0.075(3) -0.008(2) 0.023(2) 0.0034(18) C13 0.048(2) 0.041(2) 0.059(3) -0.015(2) 0.011(2) -0.0015(19) C11 0.046(2) 0.053(3) 0.060(3) -0.003(2) 0.022(2) -0.003(2) C18 0.042(2) 0.047(2) 0.052(3) 0.002(2) -0.007(2) -0.0120(18) C24 0.045(2) 0.043(2) 0.079(3) -0.010(2) 0.032(2) -0.0099(18) C16 0.035(2) 0.036(2) 0.061(3) 0.003(2) -0.003(2) 0.0000(17) C20 0.047(2) 0.035(2) 0.058(3) -0.0022(19) 0.008(2) -0.0065(17) C8 0.059(3) 0.049(3) 0.057(3) 0.016(2) 0.022(2) 0.019(2) C19 0.037(2) 0.039(2) 0.061(3) 0.003(2) -0.001(2) -0.0079(17) C17 0.042(2) 0.037(2) 0.050(3) 0.0019(18) -0.005(2) -0.0094(17) O3 0.0501(16) 0.0432(16) 0.0276(15) -0.0004(13) 0.0181(13) 0.0027(13) O5 0.0459(16) 0.0411(16) 0.0352(16) -0.0006(12) 0.0121(13) 0.0031(12) _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 2.046(3) 1_556 ? Co1 O5 2.077(3) . ? Co1 O1 2.133(3) . ? Co1 O2 2.162(3) . ? Co1 N1 2.179(3) . ? Co1 N2 2.185(3) 1_665 ? Co1 C1 2.479(4) . ? O1 C1 1.252(4) . ? O2 C1 1.276(5) . ? C4 C3 1.392(5) . ? C4 C6 1.402(5) . ? C4 C5 1.515(5) . ? N1 C10 1.333(5) . ? N1 C14 1.334(6) . ? C9 C7 1.384(5) . ? C9 C2 1.391(5) . ? C9 H9 0.9300 . ? O4 C5 1.248(5) . ? C6 C7 1.377(5) . ? C6 H6 0.9300 . ? N3 C15 1.464(6) . ? N3 C16 1.468(5) . ? N3 C18 1.485(5) . ? C7 C8 1.509(6) . ? C2 C3 1.378(5) . ? C2 C1 1.493(5) . ? N2 C23 1.339(6) . ? N2 C25 1.347(6) . ? N2 Co1 2.185(3) 1_445 ? N4 C20 1.447(6) . ? N4 C19 1.460(6) . ? N4 C17 1.463(5) . ? C10 C11 1.371(6) . ? C10 H10 0.9300 . ? C14 C13 1.378(6) . ? C14 H14 0.9300 . ? C25 C24 1.368(6) . ? C25 H25 0.9300 . ? C3 H3 0.9300 . ? C5 O3 1.256(5) . ? C21 C22 1.375(6) . ? C21 C24 1.385(6) . ? C21 C20 1.518(5) . ? C12 C13 1.388(6) . ? C12 C11 1.389(7) . ? C12 C15 1.516(6) . ? C23 C22 1.367(6) . ? C23 H23 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C22 H22 0.9300 . ? C13 H13 0.9300 . ? C11 H11 0.9300 . ? C18 C19 1.526(8) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C24 H24 0.9300 . ? C16 C17 1.511(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C8 H9E 0.9600 . ? C8 H8D 0.9600 . ? C8 H8C 0.9600 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? O3 Co1 2.046(3) 1_554 ? O5 H5A 0.8500 . ? O5 H5B 0.8501 . ? O6 H6A 0.8500 . ? O6 H6B 0.8500 . ? O7 H7A 0.8500 . ? O7 H7B 0.8500 . ? O8 H8A 0.8499 . ? O8 H8B 0.8499 . ? 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 O5 95.29(12) 1_556 . ? O3 Co1 O1 104.63(11) 1_556 . ? O5 Co1 O1 160.07(11) . . ? O3 Co1 O2 165.86(11) 1_556 . ? O5 Co1 O2 98.79(11) . . ? O1 Co1 O2 61.28(11) . . ? O3 Co1 N1 90.62(13) 1_556 . ? O5 Co1 N1 92.98(12) . . ? O1 Co1 N1 86.30(13) . . ? O2 Co1 N1 87.41(13) . . ? O3 Co1 N2 91.36(13) 1_556 1_665 ? O5 Co1 N2 90.12(13) . 1_665 ? O1 Co1 N2 90.00(13) . 1_665 ? O2 Co1 N2 89.87(13) . 1_665 ? N1 Co1 N2 176.15(16) . 1_665 ? O3 Co1 C1 134.93(12) 1_556 . ? O5 Co1 C1 129.73(12) . . ? O1 Co1 C1 30.34(11) . . ? O2 Co1 C1 30.95(12) . . ? N1 Co1 C1 85.67(13) . . ? N2 Co1 C1 90.60(13) 1_665 . ? C1 O1 Co1 90.3(2) . . ? C1 O2 Co1 88.4(2) . . ? C3 C4 C6 119.0(3) . . ? C3 C4 C5 120.9(3) . . ? C6 C4 C5 120.1(3) . . ? C10 N1 C14 116.4(4) . . ? C10 N1 Co1 122.7(3) . . ? C14 N1 Co1 120.7(3) . . ? C7 C9 C2 121.1(3) . . ? C7 C9 H9 119.5 . . ? C2 C9 H9 119.5 . . ? C7 C6 C4 121.7(3) . . ? C7 C6 H6 119.1 . . ? C4 C6 H6 119.1 . . ? C15 N3 C16 110.8(3) . . ? C15 N3 C18 108.2(4) . . ? C16 N3 C18 107.8(3) . . ? C6 C7 C9 118.2(3) . . ? C6 C7 C8 121.0(4) . . ? C9 C7 C8 120.7(4) . . ? C3 C2 C9 120.3(3) . . ? C3 C2 C1 121.3(3) . . ? C9 C2 C1 118.4(3) . . ? C23 N2 C25 116.3(4) . . ? C23 N2 Co1 119.7(3) . 1_445 ? C25 N2 Co1 123.9(3) . 1_445 ? C20 N4 C19 109.9(3) . . ? C20 N4 C17 108.1(4) . . ? C19 N4 C17 108.1(3) . . ? N1 C10 C11 124.7(4) . . ? N1 C10 H10 117.6 . . ? C11 C10 H10 117.6 . . ? O1 C1 O2 120.0(3) . . ? O1 C1 C2 120.1(3) . . ? O2 C1 C2 119.9(3) . . ? O1 C1 Co1 59.38(19) . . ? O2 C1 Co1 60.6(2) . . ? C2 C1 Co1 178.0(3) . . ? N1 C14 C13 122.5(4) . . ? N1 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? N2 C25 C24 123.1(4) . . ? N2 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? O4 C5 O3 125.0(4) . . ? O4 C5 C4 118.7(4) . . ? O3 C5 C4 116.2(3) . . ? C22 C21 C24 115.8(4) . . ? C22 C21 C20 119.7(4) . . ? C24 C21 C20 124.5(4) . . ? C13 C12 C11 116.0(4) . . ? C13 C12 C15 119.8(4) . . ? C11 C12 C15 124.1(4) . . ? N2 C23 C22 123.0(4) . . ? N2 C23 H23 118.5 . . ? C22 C23 H23 118.5 . . ? N3 C15 C12 114.1(4) . . ? N3 C15 H15A 108.7 . . ? C12 C15 H15A 108.7 . . ? N3 C15 H15B 108.7 . . ? C12 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C23 C22 C21 121.2(4) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C14 C13 C12 121.1(4) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C10 C11 C12 119.3(4) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N3 C18 C19 110.3(4) . . ? N3 C18 H18A 109.6 . . ? C19 C18 H18A 109.6 . . ? N3 C18 H18B 109.6 . . ? C19 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? C25 C24 C21 120.6(4) . . ? C25 C24 H24 119.7 . . ? C21 C24 H24 119.7 . . ? N3 C16 C17 110.7(3) . . ? N3 C16 H16A 109.5 . . ? C17 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? N4 C20 C21 116.7(4) . . ? N4 C20 H20A 108.1 . . ? C21 C20 H20A 108.1 . . ? N4 C20 H20B 108.1 . . ? C21 C20 H20B 108.1 . . ? H20A C20 H20B 107.3 . . ? C7 C8 H9E 109.5 . . ? C7 C8 H8D 109.5 . . ? H9E C8 H8D 109.5 . . ? C7 C8 H8C 109.5 . . ? H9E C8 H8C 109.5 . . ? H8D C8 H8C 109.5 . . ? N4 C19 C18 111.4(4) . . ? N4 C19 H19A 109.4 . . ? C18 C19 H19A 109.4 . . ? N4 C19 H19B 109.4 . . ? C18 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? N4 C17 C16 113.1(4) . . ? N4 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? N4 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C5 O3 Co1 128.5(3) . 1_554 ? Co1 O5 H5A 109.3 . . ? Co1 O5 H5B 109.2 . . ? H5A O5 H5B 109.5 . . ? H6A O6 H6B 109.5 . . ? H7A O7 H7B 109.5 . . ? H8A O8 H8B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.579 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.155 # Attachment '- 2-cif.tex' data_f:\struct~1\10051910\01 _database_code_depnum_ccdc_archive 'CCDC 783374' #TrackingRef '- 2-cif.tex' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H35 N4 O8 Zn' _chemical_formula_weight 584.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 18.105(6) _cell_length_b 15.467(5) _cell_length_c 10.115(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.760(5) _cell_angle_gamma 90.00 _cell_volume 2806.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3656 _cell_measurement_theta_min 2.5551 _cell_measurement_theta_max 27.4797 _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 0.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8362 _exptl_absorpt_correction_T_max 0.8889 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 Saturn _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10699 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3204 _reflns_number_gt 2857 _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^)+(0.0976P)^2^+1.9473P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3204 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1484 _refine_ls_wR_factor_gt 0.1339 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 Zn1 Zn 0.0000 0.16493(2) 0.2500 0.02609(16) Uani 1 2 d S . . O1 O 0.00836(11) 0.25055(12) 0.39783(17) 0.0349(4) Uani 1 1 d . . . O2 O -0.00674(14) 0.12950(13) 0.50725(19) 0.0453(5) Uani 1 1 d . . . N1 N 0.09140(12) 0.08690(13) 0.2783(2) 0.0294(4) Uani 1 1 d . . . N2 N 0.24958(13) -0.17647(14) 0.4106(2) 0.0353(5) Uani 1 1 d . . . C1 C 0.00089(14) 0.20820(17) 0.5053(2) 0.0311(5) Uani 1 1 d . . . C2 C 0.00123(14) 0.26023(17) 0.6316(2) 0.0303(5) Uani 1 1 d . . . C3 C 0.0000 0.2153(2) 0.7500 0.0291(7) Uani 1 2 d S . . H3 H 0.0000 0.1551 0.7500 0.035 Uiso 1 2 calc SR . . C4 C 0.00136(18) 0.34913(18) 0.6322(3) 0.0403(7) Uani 1 1 d . . . H6 H 0.0024 0.3788 0.5525 0.048 Uiso 1 1 calc R . . C5 C 0.0000 0.3960(3) 0.7500 0.0493(11) Uani 1 2 d S . . C6 C 0.0000 0.4932(3) 0.7500 0.091(3) Uani 1 2 d S . . H9A H 0.0129 0.5166 0.6773 0.110 Uiso 1 1 d R . . H9B H 0.0565 0.5094 0.7959 0.110 Uiso 1 1 d R . . C7 C 0.14681(16) 0.10425(17) 0.3763(3) 0.0376(6) Uani 1 1 d . . . H10 H 0.1454 0.1558 0.4232 0.045 Uiso 1 1 calc R . . C8 C 0.20579(16) 0.04891(18) 0.4105(3) 0.0409(6) Uani 1 1 d . . . H11 H 0.2433 0.0635 0.4790 0.049 Uiso 1 1 calc R . . C9 C 0.20928(15) -0.02826(17) 0.3431(3) 0.0350(6) Uani 1 1 d . . . C10 C 0.15151(17) -0.04606(18) 0.2416(3) 0.0399(6) Uani 1 1 d . . . H13 H 0.1513 -0.0975 0.1940 0.048 Uiso 1 1 calc R . . C11 C 0.09467(16) 0.01266(17) 0.2118(3) 0.0357(6) Uani 1 1 d . . . H14 H 0.0570 0.0002 0.1426 0.043 Uiso 1 1 calc R . . C12 C 0.27359(16) -0.0900(2) 0.3806(3) 0.0444(7) Uani 1 1 d . . . H15A H 0.3031 -0.0931 0.3076 0.053 Uiso 1 1 calc R . . H15B H 0.3052 -0.0673 0.4579 0.053 Uiso 1 1 calc R . . C14 C 0.20631(17) -0.17693(18) 0.5239(3) 0.0395(6) Uani 1 1 d . . . H16A H 0.1619 -0.1418 0.5024 0.047 Uiso 1 1 calc R . . H16B H 0.2359 -0.1521 0.6017 0.047 Uiso 1 1 calc R . . C13 C 0.31567(15) -0.23191(19) 0.4454(3) 0.0415(6) Uani 1 1 d . . . H17A H 0.3466 -0.2079 0.5225 0.050 Uiso 1 1 calc R . . H17B H 0.3448 -0.2328 0.3716 0.050 Uiso 1 1 calc R . . O3 O 0.14946(18) 0.34050(17) 0.4259(3) 0.0699(8) Uiso 1 1 d . . . H3A H 0.1046 0.3228 0.4121 0.084 Uiso 1 1 d R . . H3B H 0.1522 0.3868 0.3823 0.084 Uiso 1 1 d R . . O4 O 0.28485(17) 0.25908(19) 0.3582(3) 0.0760(8) Uiso 1 1 d . . . H4A H 0.3068 0.2592 0.2892 0.091 Uiso 1 1 d R . . H4B H 0.2468 0.2265 0.3425 0.091 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 Zn1 0.0311(2) 0.0259(2) 0.0207(2) 0.000 0.00135(15) 0.000 O1 0.0473(11) 0.0410(10) 0.0165(8) -0.0020(7) 0.0052(7) -0.0018(8) O2 0.0713(15) 0.0354(10) 0.0295(10) -0.0060(8) 0.0080(9) -0.0063(10) N1 0.0337(10) 0.0280(10) 0.0256(10) 0.0008(8) 0.0010(8) 0.0027(8) N2 0.0302(11) 0.0381(12) 0.0378(13) 0.0047(9) 0.0052(9) 0.0107(9) C1 0.0330(12) 0.0407(14) 0.0195(11) -0.0024(10) 0.0028(9) -0.0010(10) C2 0.0351(12) 0.0360(13) 0.0198(11) -0.0023(9) 0.0036(9) -0.0004(10) C3 0.0361(18) 0.0295(16) 0.0216(15) 0.000 0.0041(12) 0.000 C4 0.0627(19) 0.0371(14) 0.0216(13) 0.0043(10) 0.0076(12) 0.0005(13) C5 0.088(3) 0.0306(19) 0.030(2) 0.000 0.011(2) 0.000 C6 0.196(8) 0.032(2) 0.049(3) 0.000 0.027(4) 0.000 C7 0.0395(14) 0.0291(12) 0.0416(15) -0.0061(10) -0.0033(11) -0.0011(10) C8 0.0340(14) 0.0387(14) 0.0466(16) -0.0034(12) -0.0069(11) -0.0023(11) C9 0.0331(13) 0.0329(13) 0.0386(14) 0.0081(10) 0.0031(10) 0.0039(10) C10 0.0488(16) 0.0327(13) 0.0369(14) -0.0055(11) 0.0005(11) 0.0076(11) C11 0.0422(14) 0.0340(13) 0.0286(13) -0.0046(10) -0.0034(10) 0.0043(11) C12 0.0335(14) 0.0424(16) 0.0563(18) 0.0077(13) 0.0028(12) 0.0075(12) C14 0.0374(14) 0.0400(15) 0.0422(16) 0.0033(11) 0.0092(11) 0.0147(11) C13 0.0322(13) 0.0438(15) 0.0495(17) 0.0093(12) 0.0090(11) 0.0140(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 Zn1 O1 1.9878(18) . ? Zn1 O1 1.9878(18) 2 ? Zn1 N1 2.037(2) 2 ? Zn1 N1 2.037(2) . ? O1 C1 1.292(3) . ? O2 C1 1.225(4) . ? N1 C11 1.336(3) . ? N1 C7 1.339(3) . ? N2 C12 1.451(4) . ? N2 C14 1.473(4) . ? N2 C13 1.476(3) . ? C1 C2 1.509(3) . ? C2 C4 1.375(4) . ? C2 C3 1.388(3) . ? C3 C2 1.388(3) 2_556 ? C3 H3 0.9300 . ? C4 C5 1.397(3) . ? C4 H6 0.9300 . ? C5 C4 1.397(3) 2_556 ? C5 C6 1.503(6) . ? C6 H9A 0.8787 . ? C6 H9B 1.0941 . ? C7 C8 1.376(4) . ? C7 H10 0.9300 . ? C8 C9 1.380(4) . ? C8 H11 0.9300 . ? C9 C10 1.391(4) . ? C9 C12 1.514(4) . ? C10 C11 1.375(4) . ? C10 H13 0.9300 . ? C11 H14 0.9300 . ? C12 H15A 0.9700 . ? C12 H15B 0.9700 . ? C14 C13 1.509(4) 7_546 ? C14 H16A 0.9700 . ? C14 H16B 0.9700 . ? C13 C14 1.509(4) 7_546 ? C13 H17A 0.9700 . ? C13 H17B 0.9700 . ? O3 H3A 0.8511 . ? O3 H3B 0.8465 . ? O4 H4A 0.8484 . ? O4 H4B 0.8514 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 96.45(11) . 2 ? O1 Zn1 N1 118.58(8) . 2 ? O1 Zn1 N1 108.12(8) 2 2 ? O1 Zn1 N1 108.12(8) . . ? O1 Zn1 N1 118.58(8) 2 . ? N1 Zn1 N1 107.33(12) 2 . ? C1 O1 Zn1 106.80(16) . . ? C11 N1 C7 117.7(2) . . ? C11 N1 Zn1 121.92(18) . . ? C7 N1 Zn1 119.92(17) . . ? C12 N2 C14 111.9(2) . . ? C12 N2 C13 109.2(2) . . ? C14 N2 C13 108.1(2) . . ? O2 C1 O1 122.8(2) . . ? O2 C1 C2 120.2(2) . . ? O1 C1 C2 116.9(2) . . ? C4 C2 C3 119.8(2) . . ? C4 C2 C1 122.5(2) . . ? C3 C2 C1 117.7(2) . . ? C2 C3 C2 119.9(3) 2_556 . ? C2 C3 H3 120.1 2_556 . ? C2 C3 H3 120.1 . . ? C2 C4 C5 121.5(3) . . ? C2 C4 H6 119.3 . . ? C5 C4 H6 119.3 . . ? C4 C5 C4 117.5(4) 2_556 . ? C4 C5 C6 121.23(18) 2_556 . ? C4 C5 C6 121.23(18) . . ? C5 C6 H9A 114.4 . . ? C5 C6 H9B 103.2 . . ? H9A C6 H9B 85.5 . . ? N1 C7 C8 122.7(2) . . ? N1 C7 H10 118.7 . . ? C8 C7 H10 118.7 . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H11 120.0 . . ? C9 C8 H11 120.0 . . ? C8 C9 C10 117.1(2) . . ? C8 C9 C12 120.4(3) . . ? C10 C9 C12 122.5(3) . . ? C11 C10 C9 119.8(2) . . ? C11 C10 H13 120.1 . . ? C9 C10 H13 120.1 . . ? N1 C11 C10 122.7(2) . . ? N1 C11 H14 118.7 . . ? C10 C11 H14 118.7 . . ? N2 C12 C9 113.1(2) . . ? N2 C12 H15A 109.0 . . ? C9 C12 H15A 109.0 . . ? N2 C12 H15B 109.0 . . ? C9 C12 H15B 109.0 . . ? H15A C12 H15B 107.8 . . ? N2 C14 C13 110.3(2) . 7_546 ? N2 C14 H16A 109.6 . . ? C13 C14 H16A 109.6 7_546 . ? N2 C14 H16B 109.6 . . ? C13 C14 H16B 109.6 7_546 . ? H16A C14 H16B 108.1 . . ? N2 C13 C14 111.4(2) . 7_546 ? N2 C13 H17A 109.4 . . ? C14 C13 H17A 109.4 7_546 . ? N2 C13 H17B 109.4 . . ? C14 C13 H17B 109.4 7_546 . ? H17A C13 H17B 108.0 . . ? H3A O3 H3B 107.9 . . ? H4A O4 H4B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.454 _refine_diff_density_min -0.767 _refine_diff_density_rms 0.135