# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_1 #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H19 Ag N2 O4' _chemical_formula_sum 'C24 H19 Ag N2 O4' _chemical_formula_weight 507.28 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7346(19) _cell_length_b 9.761(2) _cell_length_c 12.173(2) _cell_angle_alpha 103.67(3) _cell_angle_beta 102.74(3) _cell_angle_gamma 107.87(3) _cell_volume 1014.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 10429 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 1.028 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7148 _exptl_absorpt_correction_T_max 0.7616 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8814 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3611 _reflns_number_gt 3249 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics Diamond _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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^)+(0.0248P)^2^+0.9467P] 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 3611 _refine_ls_number_parameters 281 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0711 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.138 _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 Ag1 Ag 0.70875(3) 0.02442(3) 0.57035(2) 0.03905(10) Uani 1 1 d . . . N1 N 0.7576(3) 0.2031(3) 0.7419(2) 0.0346(6) Uani 1 1 d . . . N2 N 0.7340(3) 0.8469(3) 1.4337(2) 0.0305(6) Uani 1 1 d . . . O1 O 0.5555(2) 0.1500(3) 0.4450(2) 0.0403(6) Uani 1 1 d . . . O2 O 0.4890(2) 0.1972(3) 0.2739(2) 0.0382(5) Uani 1 1 d . . . O3 O 1.2833(3) 0.4049(3) 0.3644(2) 0.0467(6) Uani 1 1 d . . . O4 O 1.2227(2) 0.1587(3) 0.2718(2) 0.0384(6) Uani 1 1 d . . . H1A H 1.3172 0.1787 0.2839 0.096(18) Uiso 1 1 d R . . C1 C 0.7344(3) 0.1905(3) 0.3399(3) 0.0264(7) Uani 1 1 d . . . C2 C 0.8626(3) 0.2900(4) 0.4311(3) 0.0316(7) Uani 1 1 d . . . H2 H 0.8534 0.3416 0.5021 0.038 Uiso 1 1 calc R . . C3 C 1.0080(3) 0.3154(3) 0.4194(3) 0.0304(7) Uani 1 1 d . . . H3 H 1.0930 0.3874 0.4814 0.036 Uiso 1 1 calc R . . C4 C 1.0274(3) 0.2364(3) 0.3184(3) 0.0253(6) Uani 1 1 d . . . C5 C 0.8971(3) 0.1242(3) 0.2230(2) 0.0234(6) Uani 1 1 d . . . C6 C 0.7486(3) 0.1036(3) 0.2333(3) 0.0253(6) Uani 1 1 d . . . C7 C 0.6192(4) -0.0098(4) 0.1408(3) 0.0364(8) Uani 1 1 d . . . H7 H 0.5227 -0.0249 0.1474 0.044 Uiso 1 1 calc R . . C8 C 0.6343(4) -0.0971(4) 0.0420(3) 0.0416(8) Uani 1 1 d . . . H8 H 0.5482 -0.1709 -0.0180 0.050 Uiso 1 1 calc R . . C9 C 0.7789(4) -0.0762(4) 0.0303(3) 0.0371(8) Uani 1 1 d . . . H9 H 0.7880 -0.1363 -0.0373 0.045 Uiso 1 1 calc R . . C10 C 0.9064(4) 0.0316(4) 0.1176(3) 0.0307(7) Uani 1 1 d . . . H10 H 1.0012 0.0449 0.1079 0.037 Uiso 1 1 calc R . . C11 C 0.5805(3) 0.1768(3) 0.3548(3) 0.0288(7) Uani 1 1 d . . . C12 C 1.1907(3) 0.2750(4) 0.3189(3) 0.0283(7) Uani 1 1 d . . . C13 C 0.7299(5) 0.3284(4) 0.7400(3) 0.0465(9) Uani 1 1 d . . . H13 H 0.7083 0.3469 0.6678 0.056 Uiso 1 1 calc R . . C14 C 0.7319(5) 0.4317(4) 0.8402(3) 0.0549(11) Uani 1 1 d . . . H14 H 0.7112 0.5170 0.8342 0.066 Uiso 1 1 calc R . . C15 C 0.7643(5) 0.4098(4) 0.9491(3) 0.0492(10) Uani 1 1 d . . . C16 C 0.7958(5) 0.2818(4) 0.9520(3) 0.0468(9) Uani 1 1 d . . . H16 H 0.8196 0.2621 1.0235 0.056 Uiso 1 1 calc R . . C17 C 0.7919(4) 0.1830(4) 0.8480(3) 0.0412(8) Uani 1 1 d . . . H17 H 0.8144 0.0980 0.8521 0.049 Uiso 1 1 calc R . . C18 C 0.7567(7) 0.5214(5) 1.0554(4) 0.0790(13) Uani 1 1 d U . . H18A H 0.8303 0.6209 1.0668 0.095 Uiso 1 1 calc R . . H18B H 0.6569 0.5268 1.0333 0.095 Uiso 1 1 calc R . . C19 C 0.7815(6) 0.4989(4) 1.1691(3) 0.0610(10) Uani 1 1 d U . . H19A H 0.8830 0.4988 1.1957 0.073 Uiso 1 1 calc R . . H19B H 0.7094 0.3999 1.1604 0.073 Uiso 1 1 calc R . . C20 C 0.7649(4) 0.6197(4) 1.2627(3) 0.0424(8) Uani 1 1 d U . . C21 C 0.6539(4) 0.5856(4) 1.3174(3) 0.0389(8) Uani 1 1 d . . . H21 H 0.5871 0.4854 1.2971 0.047 Uiso 1 1 calc R . . C22 C 0.6424(4) 0.7002(4) 1.4020(3) 0.0345(7) Uani 1 1 d . . . H22 H 0.5682 0.6746 1.4384 0.041 Uiso 1 1 calc R . . C23 C 0.8411(4) 0.8801(4) 1.3805(3) 0.0325(7) Uani 1 1 d . . . H23 H 0.9059 0.9813 1.4016 0.039 Uiso 1 1 calc R . . C24 C 0.8598(4) 0.7716(4) 1.2962(3) 0.0372(8) Uani 1 1 d . . . H24 H 0.9358 0.8000 1.2617 0.045 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 Ag1 0.04913(18) 0.03618(15) 0.02996(15) -0.00026(11) 0.01931(12) 0.01728(12) N1 0.0404(16) 0.0373(15) 0.0241(14) 0.0018(12) 0.0104(12) 0.0183(13) N2 0.0399(15) 0.0334(15) 0.0210(13) 0.0064(11) 0.0118(12) 0.0181(13) O1 0.0332(13) 0.0612(16) 0.0348(13) 0.0188(12) 0.0195(11) 0.0203(12) O2 0.0275(12) 0.0586(15) 0.0417(13) 0.0209(12) 0.0170(11) 0.0261(12) O3 0.0305(13) 0.0347(14) 0.0717(18) 0.0161(13) 0.0181(13) 0.0078(11) O4 0.0230(12) 0.0434(13) 0.0465(14) 0.0033(11) 0.0133(11) 0.0164(10) C1 0.0243(16) 0.0310(16) 0.0291(16) 0.0107(13) 0.0122(13) 0.0140(14) C2 0.0317(17) 0.0354(17) 0.0280(16) 0.0041(14) 0.0124(14) 0.0161(15) C3 0.0247(16) 0.0311(17) 0.0309(17) 0.0037(13) 0.0078(14) 0.0103(14) C4 0.0230(15) 0.0271(15) 0.0299(16) 0.0116(13) 0.0103(13) 0.0117(13) C5 0.0252(15) 0.0284(15) 0.0235(15) 0.0119(13) 0.0113(13) 0.0140(13) C6 0.0227(15) 0.0327(16) 0.0242(15) 0.0101(13) 0.0093(13) 0.0133(13) C7 0.0232(16) 0.048(2) 0.0342(18) 0.0064(16) 0.0110(14) 0.0130(15) C8 0.0315(18) 0.046(2) 0.0303(18) -0.0026(15) 0.0048(15) 0.0075(16) C9 0.0380(19) 0.0431(19) 0.0263(17) 0.0025(15) 0.0115(15) 0.0159(16) C10 0.0291(17) 0.0405(18) 0.0295(16) 0.0120(14) 0.0166(14) 0.0167(15) C11 0.0258(16) 0.0311(16) 0.0311(17) 0.0057(14) 0.0140(14) 0.0127(14) C12 0.0266(16) 0.0366(18) 0.0275(16) 0.0158(14) 0.0100(14) 0.0145(15) C13 0.070(3) 0.050(2) 0.0266(18) 0.0099(16) 0.0156(18) 0.034(2) C14 0.099(3) 0.043(2) 0.039(2) 0.0126(17) 0.030(2) 0.045(2) C15 0.087(3) 0.039(2) 0.0294(19) 0.0080(16) 0.025(2) 0.032(2) C16 0.075(3) 0.046(2) 0.0236(17) 0.0081(16) 0.0147(18) 0.032(2) C17 0.059(2) 0.0362(19) 0.0309(18) 0.0047(15) 0.0138(17) 0.0272(18) C18 0.152(4) 0.054(2) 0.041(2) 0.0062(18) 0.033(2) 0.057(3) C19 0.107(3) 0.0455(19) 0.0403(18) 0.0064(15) 0.0368(19) 0.0380(19) C20 0.068(2) 0.0363(18) 0.0316(17) 0.0085(14) 0.0254(17) 0.0269(17) C21 0.048(2) 0.0306(17) 0.0298(18) 0.0044(14) 0.0123(16) 0.0074(16) C22 0.0380(19) 0.0348(18) 0.0305(17) 0.0073(14) 0.0161(15) 0.0123(15) C23 0.0388(19) 0.0298(17) 0.0250(16) 0.0047(13) 0.0097(15) 0.0112(15) C24 0.044(2) 0.0401(19) 0.0323(18) 0.0097(15) 0.0218(16) 0.0176(16) _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 Ag1 N2 2.215(2) 1_544 ? Ag1 N1 2.227(3) . ? Ag1 O1 2.550(2) 2_656 ? Ag1 O1 2.656(2) . ? N1 C13 1.335(4) . ? N1 C17 1.337(4) . ? N2 C22 1.341(4) . ? N2 C23 1.342(4) . ? N2 Ag1 2.215(2) 1_566 ? O1 C11 1.245(4) . ? O1 Ag1 2.549(2) 2_656 ? O2 C11 1.271(4) . ? O3 C12 1.214(4) . ? O4 C12 1.305(4) . ? O4 H1A 0.8500 . ? C1 C2 1.367(4) . ? C1 C6 1.433(4) . ? C1 C11 1.518(4) . ? C2 C3 1.406(4) . ? C2 H2 0.9300 . ? C3 C4 1.373(4) . ? C3 H3 0.9300 . ? C4 C5 1.433(4) . ? C4 C12 1.516(4) . ? C5 C10 1.423(4) . ? C5 C6 1.434(4) . ? C6 C7 1.418(4) . ? C7 C8 1.366(4) . ? C7 H7 0.9300 . ? C8 C9 1.403(5) . ? C8 H8 0.9300 . ? C9 C10 1.366(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C13 C14 1.379(5) . ? C13 H13 0.9300 . ? C14 C15 1.375(5) . ? C14 H14 0.9300 . ? C15 C16 1.381(5) . ? C15 C18 1.514(5) . ? C16 C17 1.383(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.432(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.510(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.386(5) . ? C20 C24 1.388(5) . ? C21 C22 1.381(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.377(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? 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 N2 Ag1 N1 160.63(10) 1_544 . ? N2 Ag1 O1 92.96(9) 1_544 2_656 ? N1 Ag1 O1 98.46(10) . 2_656 ? N2 Ag1 O1 104.21(8) 1_544 . ? N1 Ag1 O1 92.60(9) . . ? O1 Ag1 O1 83.74(8) 2_656 . ? C13 N1 C17 116.6(3) . . ? C13 N1 Ag1 119.3(2) . . ? C17 N1 Ag1 123.4(2) . . ? C22 N2 C23 117.2(3) . . ? C22 N2 Ag1 120.6(2) . 1_566 ? C23 N2 Ag1 122.2(2) . 1_566 ? C11 O1 Ag1 119.8(2) . 2_656 ? C11 O1 Ag1 122.88(19) . . ? Ag1 O1 Ag1 96.26(8) 2_656 . ? C12 O4 H1A 114.2 . . ? C2 C1 C6 119.5(3) . . ? C2 C1 C11 118.5(3) . . ? C6 C1 C11 122.0(3) . . ? C1 C2 C3 121.1(3) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 121.5(3) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 C12 115.6(3) . . ? C5 C4 C12 124.9(3) . . ? C10 C5 C4 123.6(3) . . ? C10 C5 C6 117.8(3) . . ? C4 C5 C6 118.6(2) . . ? C7 C6 C1 121.2(3) . . ? C7 C6 C5 119.1(3) . . ? C1 C6 C5 119.6(3) . . ? C8 C7 C6 120.8(3) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 120.4(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 120.5(3) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C5 121.4(3) . . ? C9 C10 H10 119.3 . . ? C5 C10 H10 119.3 . . ? O1 C11 O2 125.7(3) . . ? O1 C11 C1 118.0(3) . . ? O2 C11 C1 116.3(3) . . ? O3 C12 O4 124.1(3) . . ? O3 C12 C4 120.9(3) . . ? O4 C12 C4 115.0(3) . . ? N1 C13 C14 122.9(3) . . ? N1 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 116.7(3) . . ? C14 C15 C18 118.8(3) . . ? C16 C15 C18 124.4(3) . . ? C15 C16 C17 119.7(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? N1 C17 C16 123.5(3) . . ? N1 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? C19 C18 C15 120.9(4) . . ? C19 C18 H18A 107.1 . . ? C15 C18 H18A 107.1 . . ? C19 C18 H18B 107.1 . . ? C15 C18 H18B 107.1 . . ? H18A C18 H18B 106.8 . . ? C18 C19 C20 113.0(3) . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? C18 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C24 117.0(3) . . ? C21 C20 C19 122.2(3) . . ? C24 C20 C19 120.7(3) . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? N2 C22 C21 122.7(3) . . ? N2 C22 H22 118.7 . . ? C21 C22 H22 118.7 . . ? N2 C23 C24 123.2(3) . . ? N2 C23 H23 118.4 . . ? C24 C23 H23 118.4 . . ? C23 C24 C20 119.8(3) . . ? C23 C24 H24 120.1 . . ? C20 C24 H24 120.1 . . ? 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 O4 H1A O2 0.85 1.66 2.496(3) 166.7 1_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.636 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.063 #===END _database_code_depnum_ccdc_archive 'CCDC 958708' ####################################################################### # # 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_2 #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 Ag N2, C12 H7 O4' _chemical_formula_sum 'C25 H21 Ag N2 O4' _chemical_formula_weight 521.31 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.812(2) _cell_length_b 9.6182(19) _cell_length_c 19.060(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.55(3) _cell_angle_gamma 90.00 _cell_volume 2105.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 52006 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 28.36 _exptl_crystal_description blcok _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6803 _exptl_absorpt_correction_T_max 0.7224 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 27740 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.36 _reflns_number_total 5232 _reflns_number_gt 4343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics Diamond _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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^)+(0.0422P)^2^+1.0919P] 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 5232 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 Ag1 Ag 0.564057(17) 0.14093(2) 0.508410(12) 0.06780(9) Uani 1 1 d . . . N1 N 0.43413(14) 0.27741(18) 0.44612(9) 0.0434(4) Uani 1 1 d . . . N2 N -0.29099(15) 0.45715(19) 0.08225(10) 0.0466(4) Uani 1 1 d . . . O1 O 0.32294(18) -0.01560(15) 0.67922(10) 0.0653(5) Uani 1 1 d . . . O2 O 0.44427(15) 0.02529(16) 0.60927(10) 0.0588(4) Uani 1 1 d . . . O3 O 0.34357(16) 0.72859(15) 0.68654(8) 0.0570(4) Uani 1 1 d . . . H1A H 0.3338 0.8147 0.6771 0.085 Uiso 1 1 d R . . O4 O 0.2426(2) 0.7102(2) 0.57379(11) 0.0942(8) Uani 1 1 d . . . C1 C 0.39828(17) 0.2641(2) 0.37440(11) 0.0418(4) Uani 1 1 d . . . H1 H 0.4268 0.1903 0.3521 0.050 Uiso 1 1 calc R . . C2 C 0.32116(18) 0.3547(2) 0.33224(10) 0.0390(4) Uani 1 1 d . . . H2 H 0.2975 0.3401 0.2827 0.047 Uiso 1 1 calc R . . C3 C 0.27848(15) 0.46793(19) 0.36341(10) 0.0347(4) Uani 1 1 d . . . C4 C 0.31417(18) 0.4798(2) 0.43766(11) 0.0452(4) Uani 1 1 d . . . H4 H 0.2868 0.5526 0.4612 0.054 Uiso 1 1 calc R . . C5 C 0.3902(2) 0.3840(3) 0.47671(12) 0.0497(5) Uani 1 1 d . . . H5 H 0.4121 0.3935 0.5266 0.060 Uiso 1 1 calc R . . C6 C 0.20027(16) 0.5742(2) 0.31847(10) 0.0385(4) Uani 1 1 d . . . H6A H 0.2441 0.6234 0.2891 0.046 Uiso 1 1 calc R . . H6B H 0.1772 0.6414 0.3504 0.046 Uiso 1 1 calc R . . C7 C 0.09077(16) 0.5133(2) 0.26909(11) 0.0400(4) Uani 1 1 d . . . H7A H 0.1130 0.4496 0.2352 0.048 Uiso 1 1 calc R . . H7B H 0.0478 0.4610 0.2978 0.048 Uiso 1 1 calc R . . C8 C 0.01281(19) 0.6265(2) 0.22763(13) 0.0488(5) Uani 1 1 d . . . H8A H -0.0106 0.6885 0.2618 0.059 Uiso 1 1 calc R . . H8B H 0.0572 0.6805 0.2004 0.059 Uiso 1 1 calc R . . C9 C -0.09444(16) 0.5708(2) 0.17658(11) 0.0397(4) Uani 1 1 d . . . C10 C -0.17519(19) 0.4915(2) 0.20091(12) 0.0485(5) Uani 1 1 d . . . H10 H -0.1646 0.4742 0.2500 0.058 Uiso 1 1 calc R . . C11 C -0.27069(18) 0.4381(2) 0.15326(12) 0.0493(5) Uani 1 1 d . . . H11 H -0.3238 0.3861 0.1714 0.059 Uiso 1 1 calc R . . C12 C -0.2151(2) 0.5366(3) 0.05857(12) 0.0543(5) Uani 1 1 d . . . H12 H -0.2285 0.5536 0.0093 0.065 Uiso 1 1 calc R . . C13 C -0.11782(19) 0.5947(3) 0.10337(12) 0.0507(5) Uani 1 1 d . . . H13 H -0.0680 0.6501 0.0841 0.061 Uiso 1 1 calc R . . C14 C 0.34621(16) 0.21601(17) 0.64505(9) 0.0334(3) Uani 1 1 d . . . C15 C 0.43413(16) 0.30730(19) 0.67172(11) 0.0384(4) Uani 1 1 d . . . H15 H 0.5091 0.2741 0.6903 0.046 Uiso 1 1 calc R . . C16 C 0.41260(17) 0.45144(19) 0.67149(10) 0.0395(4) Uani 1 1 d . . . H16 H 0.4725 0.5117 0.6926 0.047 Uiso 1 1 calc R . . C17 C 0.30519(17) 0.50364(18) 0.64070(10) 0.0373(4) Uani 1 1 d . . . C18 C 0.20974(16) 0.4117(2) 0.61474(9) 0.0355(4) Uani 1 1 d . . . C19 C 0.22994(16) 0.26549(18) 0.61865(9) 0.0334(4) Uani 1 1 d . . . C20 C 0.1339(2) 0.1747(2) 0.59470(11) 0.0480(5) Uani 1 1 d . . . H20 H 0.1456 0.0790 0.5970 0.058 Uiso 1 1 calc R . . C21 C 0.0244(2) 0.2262(3) 0.56838(13) 0.0626(7) Uani 1 1 d . . . H21 H -0.0375 0.1655 0.5523 0.075 Uiso 1 1 calc R . . C22 C 0.0048(2) 0.3696(3) 0.56547(14) 0.0618(7) Uani 1 1 d . . . H22 H -0.0702 0.4036 0.5480 0.074 Uiso 1 1 calc R . . C23 C 0.09425(18) 0.4595(3) 0.58795(11) 0.0499(5) Uani 1 1 d . . . H23 H 0.0795 0.5545 0.5858 0.060 Uiso 1 1 calc R . . C24 C 0.37466(17) 0.06246(18) 0.64380(10) 0.0371(4) Uani 1 1 d . . . C25 C 0.2912(2) 0.6587(2) 0.63098(12) 0.0477(5) 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 Ag1 0.05508(13) 0.05118(12) 0.07987(16) 0.01613(9) -0.01900(10) 0.00446(8) N1 0.0386(8) 0.0438(9) 0.0455(9) 0.0092(7) 0.0053(7) 0.0028(7) N2 0.0394(8) 0.0447(9) 0.0497(10) -0.0064(8) -0.0017(7) 0.0018(7) O1 0.1120(15) 0.0248(7) 0.0739(11) 0.0006(7) 0.0517(11) 0.0002(8) O2 0.0621(10) 0.0404(8) 0.0831(12) -0.0005(8) 0.0353(9) 0.0115(7) O3 0.0853(12) 0.0267(6) 0.0534(9) -0.0023(6) 0.0050(8) -0.0023(7) O4 0.140(2) 0.0428(10) 0.0730(13) 0.0102(9) -0.0288(13) 0.0047(11) C1 0.0418(10) 0.0383(9) 0.0468(11) 0.0034(8) 0.0137(8) 0.0036(8) C2 0.0429(10) 0.0407(10) 0.0339(9) 0.0017(7) 0.0098(8) 0.0029(8) C3 0.0283(8) 0.0363(9) 0.0386(9) 0.0022(7) 0.0058(7) -0.0006(7) C4 0.0425(10) 0.0518(11) 0.0386(10) -0.0075(9) 0.0043(8) 0.0076(9) C5 0.0477(11) 0.0603(13) 0.0363(10) -0.0002(9) 0.0004(9) 0.0057(10) C6 0.0352(9) 0.0355(9) 0.0419(10) 0.0012(8) 0.0029(7) 0.0011(7) C7 0.0366(9) 0.0352(9) 0.0438(10) -0.0012(8) 0.0004(8) 0.0017(7) C8 0.0441(11) 0.0383(10) 0.0550(12) 0.0025(9) -0.0066(9) -0.0002(8) C9 0.0366(9) 0.0337(9) 0.0437(10) 0.0008(8) -0.0010(8) 0.0043(7) C10 0.0453(11) 0.0567(12) 0.0397(10) 0.0056(9) 0.0025(8) -0.0009(9) C11 0.0401(10) 0.0488(12) 0.0566(13) 0.0058(10) 0.0063(9) -0.0033(9) C12 0.0494(12) 0.0724(15) 0.0368(10) 0.0012(10) 0.0016(9) -0.0022(11) C13 0.0432(11) 0.0585(13) 0.0476(11) 0.0100(10) 0.0049(9) -0.0041(10) C14 0.0420(9) 0.0258(8) 0.0338(8) 0.0008(6) 0.0117(7) 0.0001(7) C15 0.0351(9) 0.0311(8) 0.0466(10) 0.0002(8) 0.0046(8) 0.0025(7) C16 0.0429(10) 0.0285(8) 0.0443(10) -0.0034(7) 0.0044(8) -0.0053(7) C17 0.0481(10) 0.0263(8) 0.0367(9) -0.0024(7) 0.0083(8) 0.0019(7) C18 0.0401(9) 0.0354(9) 0.0311(8) 0.0012(7) 0.0089(7) 0.0034(7) C19 0.0376(9) 0.0328(8) 0.0301(8) -0.0008(7) 0.0084(7) -0.0033(7) C20 0.0516(12) 0.0487(11) 0.0431(11) 0.0001(9) 0.0099(9) -0.0166(9) C21 0.0450(12) 0.0865(19) 0.0523(13) 0.0085(13) 0.0031(10) -0.0243(12) C22 0.0354(11) 0.094(2) 0.0536(13) 0.0211(13) 0.0065(10) 0.0049(11) C23 0.0458(11) 0.0572(13) 0.0466(11) 0.0086(10) 0.0107(9) 0.0127(10) C24 0.0466(10) 0.0258(8) 0.0376(9) -0.0027(7) 0.0076(8) 0.0018(7) C25 0.0615(13) 0.0295(9) 0.0484(11) 0.0001(8) 0.0056(10) 0.0063(8) _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 Ag1 N1 2.1526(17) . ? Ag1 N2 2.1616(18) 4_666 ? Ag1 Ag1 3.0846(6) 3_656 ? N1 C1 1.339(3) . ? N1 C5 1.342(3) . ? N2 C11 1.331(3) . ? N2 C12 1.334(3) . ? N2 Ag1 2.1617(18) 4_465 ? O1 C24 1.259(2) . ? O2 C24 1.221(2) . ? O3 C25 1.284(3) . ? O3 H1A 0.8499 . ? O4 C25 1.213(3) . ? C1 C2 1.375(3) . ? C1 H1 0.9300 . ? C2 C3 1.391(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(3) . ? C3 C6 1.503(3) . ? C4 C5 1.377(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.527(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.522(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.504(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C13 1.377(3) . ? C9 C10 1.383(3) . ? C10 C11 1.371(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.379(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.364(3) . ? C14 C19 1.429(3) . ? C14 C24 1.516(2) . ? C15 C16 1.409(3) . ? C15 H15 0.9300 . ? C16 C17 1.363(3) . ? C16 H16 0.9300 . ? C17 C18 1.427(3) . ? C17 C25 1.507(3) . ? C18 C23 1.416(3) . ? C18 C19 1.425(3) . ? C19 C20 1.420(3) . ? C20 C21 1.366(4) . ? C20 H20 0.9300 . ? C21 C22 1.397(4) . ? C21 H21 0.9300 . ? C22 C23 1.354(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 N1 Ag1 N2 168.16(7) . 4_666 ? N1 Ag1 Ag1 102.10(5) . 3_656 ? N2 Ag1 Ag1 88.77(5) 4_666 3_656 ? C1 N1 C5 117.04(17) . . ? C1 N1 Ag1 121.24(14) . . ? C5 N1 Ag1 121.63(14) . . ? C11 N2 C12 116.60(19) . . ? C11 N2 Ag1 121.90(15) . 4_465 ? C12 N2 Ag1 121.47(15) . 4_465 ? C25 O3 H1A 108.7 . . ? N1 C1 C2 122.92(18) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 120.23(18) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 116.58(17) . . ? C4 C3 C6 121.74(17) . . ? C2 C3 C6 121.66(17) . . ? C5 C4 C3 120.10(19) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? N1 C5 C4 123.08(19) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C3 C6 C7 114.16(16) . . ? C3 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C3 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 111.58(16) . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C7 113.36(17) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C13 C9 C10 116.20(19) . . ? C13 C9 C8 122.32(19) . . ? C10 C9 C8 121.47(19) . . ? C11 C10 C9 120.6(2) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? N2 C11 C10 123.1(2) . . ? N2 C11 H11 118.5 . . ? C10 C11 H11 118.5 . . ? N2 C12 C13 123.4(2) . . ? N2 C12 H12 118.3 . . ? C13 C12 H12 118.3 . . ? C9 C13 C12 120.0(2) . . ? C9 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C19 120.12(16) . . ? C15 C14 C24 118.74(16) . . ? C19 C14 C24 121.14(16) . . ? C14 C15 C16 120.73(17) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 120.86(17) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 120.06(16) . . ? C16 C17 C25 118.78(18) . . ? C18 C17 C25 121.07(18) . . ? C23 C18 C19 118.31(18) . . ? C23 C18 C17 122.66(19) . . ? C19 C18 C17 118.98(16) . . ? C20 C19 C18 118.60(18) . . ? C20 C19 C14 122.55(18) . . ? C18 C19 C14 118.84(16) . . ? C21 C20 C19 120.7(2) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 120.4(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C23 C22 C21 120.5(2) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C18 121.4(2) . . ? C22 C23 H23 119.3 . . ? C18 C23 H23 119.3 . . ? O2 C24 O1 125.95(18) . . ? O2 C24 C14 118.26(17) . . ? O1 C24 C14 115.80(16) . . ? O4 C25 O3 124.3(2) . . ? O4 C25 C17 122.0(2) . . ? O3 C25 C17 113.52(18) . . ? 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 O3 H1A O1 0.85 1.64 2.473(2) 166.7 1_565 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.464 _refine_diff_density_min -0.935 _refine_diff_density_rms 0.069 #===END _database_code_depnum_ccdc_archive 'CCDC 958709' ####################################################################### # # 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_3 #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 Cd N O4' _chemical_formula_sum 'C18 H12 Cd N O4' _chemical_formula_weight 418.70 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 15.720(3) _cell_length_b 16.120(3) _cell_length_c 13.476(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.42(3) _cell_angle_gamma 90.00 _cell_volume 3058.2(13) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 15909 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 1.450 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6308 _exptl_absorpt_correction_T_max 0.6701 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12935 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2703 _reflns_number_gt 2612 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics Diamond _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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^)+(0.0247P)^2^+5.4091P] 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 2703 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0628 _refine_ls_wR_factor_gt 0.0622 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _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 Cd1 Cd -0.545576(12) -0.024372(11) 0.105928(16) 0.02593(9) Uani 1 1 d . . . N1 N -0.68949(16) 0.03598(15) -0.01729(19) 0.0295(5) Uani 1 1 d . . . O1 O -0.45847(13) 0.07287(12) 0.06701(16) 0.0324(4) Uani 1 1 d . . . O2 O -0.40989(15) 0.06141(14) 0.24710(18) 0.0393(5) Uani 1 1 d . . . O3 O -0.07159(15) 0.37543(13) 0.31601(18) 0.0408(5) Uani 1 1 d . . . O4 O -0.13456(15) 0.38157(14) 0.13090(18) 0.0437(6) Uani 1 1 d . . . C1 C -0.32477(17) 0.15385(15) 0.1844(2) 0.0213(5) Uani 1 1 d . . . C2 C -0.34806(18) 0.21895(17) 0.1112(2) 0.0271(6) Uani 1 1 d . . . H2 H -0.4093 0.2217 0.0518 0.033 Uiso 1 1 calc R . . C3 C -0.28191(19) 0.28139(17) 0.1237(2) 0.0300(6) Uani 1 1 d . . . H3 H -0.3001 0.3261 0.0737 0.036 Uiso 1 1 calc R . . C4 C -0.19082(18) 0.27839(16) 0.2080(2) 0.0238(5) Uani 1 1 d . . . C5 C -0.16170(18) 0.20835(16) 0.2806(2) 0.0217(5) Uani 1 1 d . . . C6 C -0.23001(17) 0.14605(15) 0.2712(2) 0.0203(5) Uani 1 1 d . . . C7 C -0.19949(19) 0.07625(17) 0.3430(2) 0.0266(6) Uani 1 1 d . . . H7 H -0.2438 0.0355 0.3385 0.032 Uiso 1 1 calc R . . C8 C -0.1063(2) 0.06768(18) 0.4186(2) 0.0342(6) Uani 1 1 d . . . H8 H -0.0873 0.0214 0.4659 0.041 Uiso 1 1 calc R . . C9 C -0.0385(2) 0.1280(2) 0.4261(2) 0.0376(7) Uani 1 1 d . . . H9 H 0.0256 0.1208 0.4769 0.045 Uiso 1 1 calc R . . C10 C -0.06548(19) 0.19636(18) 0.3600(2) 0.0305(6) Uani 1 1 d . . . H10 H -0.0198 0.2365 0.3669 0.037 Uiso 1 1 calc R . . C11 C -0.40159(18) 0.09141(15) 0.1671(2) 0.0241(5) Uani 1 1 d . . . C12 C -0.12536(18) 0.35123(16) 0.2208(2) 0.0275(6) Uani 1 1 d . . . C13 C -0.7026(2) 0.1167(2) -0.0444(3) 0.0381(7) Uani 1 1 d . . . H13 H -0.6514 0.1535 -0.0090 0.046 Uiso 1 1 calc R . . C14 C -0.7885(2) 0.1482(2) -0.1224(3) 0.0411(7) Uani 1 1 d . . . H14 H -0.7950 0.2054 -0.1382 0.049 Uiso 1 1 calc R . . C15 C -0.8648(2) 0.0956(2) -0.1771(2) 0.0348(7) Uani 1 1 d . . . C16 C -0.8513(2) 0.0124(2) -0.1478(2) 0.0368(7) Uani 1 1 d . . . H16 H -0.9014 -0.0256 -0.1819 0.044 Uiso 1 1 calc R . . C17 C -0.7644(2) -0.01436(18) -0.0687(2) 0.0318(6) Uani 1 1 d . . . H17 H -0.7571 -0.0709 -0.0497 0.038 Uiso 1 1 calc R . . C18 C -0.9599(2) 0.1237(3) -0.2682(3) 0.0504(9) Uani 1 1 d . . . H18A H -0.9779 0.0869 -0.3324 0.060 Uiso 1 1 calc R . . H18B H -0.9530 0.1799 -0.2916 0.060 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 Cd1 0.01782(12) 0.02196(13) 0.03381(14) 0.01033(7) 0.00770(9) -0.00331(7) N1 0.0235(12) 0.0380(13) 0.0270(12) 0.0037(10) 0.0111(10) -0.0008(10) O1 0.0238(9) 0.0294(10) 0.0387(11) -0.0061(8) 0.0091(8) -0.0111(8) O2 0.0371(11) 0.0405(12) 0.0471(13) 0.0041(10) 0.0249(10) -0.0120(10) O3 0.0389(12) 0.0339(11) 0.0416(12) -0.0063(9) 0.0107(10) -0.0197(10) O4 0.0368(11) 0.0454(13) 0.0426(12) 0.0134(10) 0.0120(10) -0.0201(10) C1 0.0198(12) 0.0200(12) 0.0242(13) -0.0009(10) 0.0097(10) -0.0038(10) C2 0.0182(12) 0.0264(14) 0.0274(14) 0.0048(11) 0.0017(10) -0.0042(11) C3 0.0267(14) 0.0239(14) 0.0317(15) 0.0097(11) 0.0060(11) -0.0040(11) C4 0.0234(13) 0.0214(13) 0.0248(13) 0.0010(10) 0.0092(11) -0.0062(10) C5 0.0220(12) 0.0215(12) 0.0203(12) -0.0013(10) 0.0083(10) -0.0056(10) C6 0.0225(12) 0.0186(12) 0.0203(12) -0.0018(9) 0.0100(10) -0.0034(10) C7 0.0296(14) 0.0230(13) 0.0291(14) 0.0060(11) 0.0150(11) -0.0018(11) C8 0.0360(16) 0.0293(15) 0.0315(15) 0.0111(12) 0.0098(12) 0.0024(12) C9 0.0261(14) 0.0415(17) 0.0311(15) 0.0072(13) 0.0002(12) -0.0008(13) C10 0.0222(13) 0.0329(15) 0.0303(15) 0.0020(12) 0.0062(11) -0.0088(11) C11 0.0190(12) 0.0170(12) 0.0364(15) 0.0001(11) 0.0122(11) -0.0004(10) C12 0.0206(13) 0.0208(13) 0.0392(16) 0.0042(11) 0.0116(12) -0.0042(10) C13 0.0258(14) 0.0396(17) 0.0400(17) 0.0070(13) 0.0065(13) -0.0056(13) C14 0.0306(16) 0.0397(17) 0.0463(18) 0.0150(14) 0.0111(14) 0.0022(13) C15 0.0236(14) 0.0535(19) 0.0256(14) 0.0059(13) 0.0093(11) 0.0005(13) C16 0.0282(16) 0.0467(18) 0.0315(16) -0.0056(13) 0.0097(13) -0.0089(13) C17 0.0306(15) 0.0335(16) 0.0311(15) -0.0039(12) 0.0136(12) -0.0019(12) C18 0.0254(16) 0.076(3) 0.0425(19) 0.0178(17) 0.0082(14) 0.0005(16) _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 O4 2.1880(19) 3_445 ? Cd1 O1 2.2905(19) . ? Cd1 O3 2.320(2) 4_445 ? Cd1 N1 2.341(2) . ? Cd1 O1 2.486(2) 5_455 ? Cd1 O2 2.544(2) . ? N1 C17 1.341(4) . ? N1 C13 1.343(4) . ? O1 C11 1.278(3) . ? O1 Cd1 2.486(2) 5_455 ? O2 C11 1.241(3) . ? O3 C12 1.244(3) . ? O3 Cd1 2.320(2) 4_455 ? O4 C12 1.254(3) . ? O4 Cd1 2.1881(19) 3 ? C1 C2 1.373(4) . ? C1 C6 1.433(4) . ? C1 C11 1.508(3) . ? C2 C3 1.402(4) . ? C2 H2 0.9400 . ? C3 C4 1.377(4) . ? C3 H3 0.9400 . ? C4 C5 1.429(4) . ? C4 C12 1.520(3) . ? C5 C10 1.425(4) . ? C5 C6 1.434(3) . ? C6 C7 1.421(4) . ? C7 C8 1.370(4) . ? C7 H7 0.9400 . ? C8 C9 1.413(4) . ? C8 H8 0.9400 . ? C9 C10 1.361(4) . ? C9 H9 0.9400 . ? C10 H10 0.9400 . ? C13 C14 1.388(4) . ? C13 H13 0.9400 . ? C14 C15 1.384(4) . ? C14 H14 0.9400 . ? C15 C16 1.387(5) . ? C15 C18 1.522(4) . ? C16 C17 1.376(4) . ? C16 H16 0.9400 . ? C17 H17 0.9400 . ? C18 C18 1.544(7) 2_354 ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cd1 O1 176.08(7) 3_445 . ? O4 Cd1 O3 83.15(9) 3_445 4_445 ? O1 Cd1 O3 98.36(8) . 4_445 ? O4 Cd1 N1 85.12(8) 3_445 . ? O1 Cd1 N1 92.33(8) . . ? O3 Cd1 N1 158.85(8) 4_445 . ? O4 Cd1 O1 102.18(8) 3_445 5_455 ? O1 Cd1 O1 74.53(7) . 5_455 ? O3 Cd1 O1 81.94(7) 4_445 5_455 ? N1 Cd1 O1 83.42(8) . 5_455 ? O4 Cd1 O2 129.97(7) 3_445 . ? O1 Cd1 O2 53.94(7) . . ? O3 Cd1 O2 78.87(8) 4_445 . ? N1 Cd1 O2 121.92(8) . . ? O1 Cd1 O2 120.63(6) 5_455 . ? C17 N1 C13 116.9(3) . . ? C17 N1 Cd1 117.66(19) . . ? C13 N1 Cd1 125.34(19) . . ? C11 O1 Cd1 97.32(16) . . ? C11 O1 Cd1 139.89(17) . 5_455 ? Cd1 O1 Cd1 105.47(7) . 5_455 ? C11 O2 Cd1 86.52(16) . . ? C12 O3 Cd1 136.38(19) . 4_455 ? C12 O4 Cd1 127.74(18) . 3 ? C2 C1 C6 120.1(2) . . ? C2 C1 C11 117.4(2) . . ? C6 C1 C11 122.5(2) . . ? C1 C2 C3 121.0(2) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.4(2) . . ? C3 C4 C12 118.0(2) . . ? C5 C4 C12 122.6(2) . . ? C10 C5 C4 122.1(2) . . ? C10 C5 C6 118.3(2) . . ? C4 C5 C6 119.6(2) . . ? C7 C6 C1 122.6(2) . . ? C7 C6 C5 118.8(2) . . ? C1 C6 C5 118.5(2) . . ? C8 C7 C6 120.8(2) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 120.5(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 120.3(3) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C5 121.3(3) . . ? C9 C10 H10 119.4 . . ? C5 C10 H10 119.4 . . ? O2 C11 O1 122.1(2) . . ? O2 C11 C1 120.8(2) . . ? O1 C11 C1 117.1(2) . . ? O3 C12 O4 127.4(2) . . ? O3 C12 C4 118.3(2) . . ? O4 C12 C4 114.2(2) . . ? N1 C13 C14 122.7(3) . . ? N1 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 117.1(3) . . ? C14 C15 C18 123.6(3) . . ? C16 C15 C18 119.3(3) . . ? C17 C16 C15 119.8(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? N1 C17 C16 123.5(3) . . ? N1 C17 H17 118.3 . . ? C16 C17 H17 118.3 . . ? C15 C18 C18 113.0(3) . 2_354 ? C15 C18 H18A 109.0 . . ? C18 C18 H18A 109.0 2_354 . ? C15 C18 H18B 109.0 . . ? C18 C18 H18B 109.0 2_354 . ? H18A C18 H18B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.427 _refine_diff_density_min -0.871 _refine_diff_density_rms 0.079 #===END _database_code_depnum_ccdc_archive 'CCDC 958710' ####################################################################### # # 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_4 #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H26 Cd2 N2 O8' _chemical_formula_sum 'C37 H26 Cd2 N2 O8' _chemical_formula_weight 851.42 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 16.616(3) _cell_length_b 15.383(3) _cell_length_c 14.774(3) _cell_angle_alpha 90.00 _cell_angle_beta 120.63(3) _cell_angle_gamma 90.00 _cell_volume 3249.4(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 27908 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 1.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6846 _exptl_absorpt_correction_T_max 0.7440 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13829 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2892 _reflns_number_gt 2585 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics Diamond _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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^)+(0.0236P)^2^+3.0057P] 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 2892 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0580 _refine_ls_wR_factor_gt 0.0560 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _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 0.959968(13) -0.517764(13) 0.605544(16) 0.02700(8) Uani 1 1 d . . . N1 N 0.83064(16) -0.43003(16) 0.51292(19) 0.0343(6) Uani 1 1 d . . . O1 O 1.04150(15) -0.42328(15) 0.53976(18) 0.0493(6) Uani 1 1 d . . . O2 O 1.08724(17) -0.42436(16) 0.70639(18) 0.0560(7) Uani 1 1 d . . . O3 O 1.44071(17) -0.12952(15) 0.8125(2) 0.0501(6) Uani 1 1 d . . . O4 O 1.36728(16) -0.09559(15) 0.6413(2) 0.0545(7) Uani 1 1 d . . . C1 C 1.1769(2) -0.3420(2) 0.6517(2) 0.0339(7) Uani 1 1 d . . . C2 C 1.1541(2) -0.2660(2) 0.5960(3) 0.0504(10) Uani 1 1 d . . . H2 H 1.0923 -0.2552 0.5445 0.060 Uiso 1 1 calc R . . C3 C 1.2235(2) -0.2040(2) 0.6160(3) 0.0480(9) Uani 1 1 d . . . H3 H 1.2070 -0.1532 0.5765 0.058 Uiso 1 1 calc R . . C4 C 1.3146(2) -0.21717(19) 0.6923(2) 0.0341(7) Uani 1 1 d . . . C5 C 1.34266(19) -0.29855(19) 0.7470(2) 0.0293(6) Uani 1 1 d . . . C6 C 1.2727(2) -0.36243(18) 0.7253(2) 0.0291(6) Uani 1 1 d . . . C7 C 1.3002(2) -0.4455(2) 0.7726(3) 0.0392(7) Uani 1 1 d . . . H7 H 1.2549 -0.4876 0.7577 0.047 Uiso 1 1 calc R . . C8 C 1.3924(2) -0.4648(2) 0.8398(3) 0.0504(9) Uani 1 1 d . . . H8 H 1.4097 -0.5198 0.8699 0.060 Uiso 1 1 calc R . . C9 C 1.4610(2) -0.4012(2) 0.8631(3) 0.0537(10) Uani 1 1 d . . . H9 H 1.5236 -0.4144 0.9092 0.064 Uiso 1 1 calc R . . C10 C 1.4376(2) -0.3207(2) 0.8195(3) 0.0407(8) Uani 1 1 d . . . H10 H 1.4842 -0.2794 0.8372 0.049 Uiso 1 1 calc R . . C11 C 1.0983(2) -0.40139(18) 0.6327(2) 0.0325(7) Uani 1 1 d . . . C12 C 1.3805(2) -0.1417(2) 0.7173(3) 0.0367(7) Uani 1 1 d . . . C13 C 0.7595(2) -0.4325(3) 0.5304(3) 0.0552(10) Uani 1 1 d . . . H13 H 0.7643 -0.4690 0.5831 0.066 Uiso 1 1 calc R . . C14 C 0.6794(2) -0.3839(3) 0.4748(3) 0.0594(11) Uani 1 1 d . . . H14 H 0.6320 -0.3880 0.4907 0.071 Uiso 1 1 calc R . . C15 C 0.6689(2) -0.3289(2) 0.3953(2) 0.0363(7) Uani 1 1 d . . . C16 C 0.7432(2) -0.3253(2) 0.3797(3) 0.0433(8) Uani 1 1 d . . . H16 H 0.7405 -0.2883 0.3283 0.052 Uiso 1 1 calc R . . C17 C 0.8219(2) -0.3751(2) 0.4383(3) 0.0414(8) Uani 1 1 d . . . H17 H 0.8711 -0.3703 0.4256 0.050 Uiso 1 1 calc R . . C18 C 0.5816(2) -0.2760(2) 0.3308(3) 0.0451(8) Uani 1 1 d . . . H18A H 0.5947 -0.2303 0.2948 0.054 Uiso 1 1 calc R . . H18B H 0.5642 -0.2485 0.3774 0.054 Uiso 1 1 calc R . . C19 C 0.5000 -0.3299(3) 0.2500 0.0503(13) Uani 1 2 d S . . H19A H 0.4784 -0.3671 0.2863 0.060 Uiso 0.50 1 calc PR . . H19B H 0.5216 -0.3671 0.2137 0.060 Uiso 0.50 1 calc PR . . 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 0.02127(12) 0.02506(13) 0.03143(13) 0.00460(9) 0.01107(9) -0.00214(9) N1 0.0260(13) 0.0392(16) 0.0366(14) 0.0079(12) 0.0153(11) 0.0024(11) O1 0.0421(13) 0.0578(16) 0.0463(14) -0.0204(12) 0.0214(12) -0.0227(11) O2 0.0569(15) 0.0620(17) 0.0458(15) -0.0038(12) 0.0238(13) -0.0318(13) O3 0.0515(14) 0.0418(14) 0.0596(16) -0.0177(12) 0.0303(13) -0.0248(11) O4 0.0387(13) 0.0463(15) 0.0775(18) 0.0275(13) 0.0289(13) -0.0036(11) C1 0.0311(16) 0.0329(18) 0.0323(17) -0.0012(13) 0.0123(14) -0.0120(13) C2 0.0332(18) 0.048(2) 0.045(2) 0.0115(17) 0.0020(16) -0.0152(15) C3 0.043(2) 0.039(2) 0.049(2) 0.0149(16) 0.0139(17) -0.0108(15) C4 0.0363(17) 0.0300(17) 0.0383(18) -0.0016(14) 0.0208(15) -0.0106(13) C5 0.0295(16) 0.0299(16) 0.0315(16) -0.0040(13) 0.0178(13) -0.0077(12) C6 0.0320(16) 0.0270(16) 0.0286(16) -0.0028(12) 0.0156(13) -0.0056(12) C7 0.0431(19) 0.0281(17) 0.050(2) -0.0022(15) 0.0267(16) -0.0069(14) C8 0.049(2) 0.034(2) 0.066(2) 0.0123(17) 0.0278(19) 0.0088(15) C9 0.0316(19) 0.057(2) 0.065(2) 0.0096(19) 0.0186(18) 0.0090(16) C10 0.0302(17) 0.041(2) 0.051(2) -0.0006(16) 0.0206(15) -0.0059(14) C11 0.0272(16) 0.0250(16) 0.0396(18) -0.0042(14) 0.0129(14) -0.0039(12) C12 0.0319(17) 0.0304(18) 0.054(2) -0.0021(16) 0.0265(17) -0.0049(13) C13 0.042(2) 0.065(3) 0.066(3) 0.036(2) 0.0334(19) 0.0182(18) C14 0.0357(19) 0.077(3) 0.075(3) 0.031(2) 0.0349(19) 0.0144(18) C15 0.0271(16) 0.0334(18) 0.0359(17) 0.0023(14) 0.0071(14) -0.0008(13) C16 0.0371(19) 0.050(2) 0.0417(19) 0.0178(16) 0.0197(16) 0.0071(15) C17 0.0340(17) 0.050(2) 0.0453(19) 0.0132(16) 0.0239(16) 0.0044(15) C18 0.0312(18) 0.037(2) 0.051(2) 0.0025(15) 0.0094(16) 0.0010(14) C19 0.033(3) 0.038(3) 0.055(3) 0.000 0.005(2) 0.000 _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 O4 2.217(2) 3_445 ? Cd1 O3 2.260(2) 4_746 ? Cd1 N1 2.305(2) . ? Cd1 O1 2.319(2) 5_746 ? Cd1 O2 2.355(2) . ? Cd1 O1 2.497(2) . ? N1 C13 1.334(4) . ? N1 C17 1.337(4) . ? O1 C11 1.253(4) . ? O1 Cd1 2.319(2) 5_746 ? O2 C11 1.243(4) . ? O3 C12 1.257(4) . ? O3 Cd1 2.260(2) 4_756 ? O4 C12 1.248(4) . ? O4 Cd1 2.217(2) 3 ? C1 C2 1.368(4) . ? C1 C6 1.432(4) . ? C1 C11 1.499(4) . ? C2 C3 1.406(4) . ? C2 H2 0.9300 . ? C3 C4 1.365(4) . ? C3 H3 0.9300 . ? C4 C5 1.433(4) . ? C4 C12 1.509(4) . ? C5 C10 1.425(4) . ? C5 C6 1.428(4) . ? C6 C7 1.416(4) . ? C7 C8 1.368(5) . ? C7 H7 0.9300 . ? C8 C9 1.406(5) . ? C8 H8 0.9300 . ? C9 C10 1.358(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C13 C14 1.375(5) . ? C13 H13 0.9300 . ? C14 C15 1.385(5) . ? C14 H14 0.9300 . ? C15 C16 1.367(4) . ? C15 C18 1.506(4) . ? C16 C17 1.376(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.518(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C18 1.518(4) 2_655 ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cd1 O3 82.40(9) 3_445 4_746 ? O4 Cd1 N1 84.66(9) 3_445 . ? O3 Cd1 N1 165.59(9) 4_746 . ? O4 Cd1 O1 109.18(9) 3_445 5_746 ? O3 Cd1 O1 81.90(9) 4_746 5_746 ? N1 Cd1 O1 96.46(9) . 5_746 ? O4 Cd1 O2 133.46(9) 3_445 . ? O3 Cd1 O2 87.13(10) 4_746 . ? N1 Cd1 O2 106.46(10) . . ? O1 Cd1 O2 114.00(8) 5_746 . ? O4 Cd1 O1 171.06(8) 3_445 . ? O3 Cd1 O1 104.98(8) 4_746 . ? N1 Cd1 O1 87.41(8) . . ? O1 Cd1 O1 67.62(9) 5_746 . ? O2 Cd1 O1 53.18(8) . . ? C13 N1 C17 116.3(3) . . ? C13 N1 Cd1 121.3(2) . . ? C17 N1 Cd1 122.4(2) . . ? C11 O1 Cd1 140.1(2) . 5_746 ? C11 O1 Cd1 89.11(18) . . ? Cd1 O1 Cd1 112.38(9) 5_746 . ? C11 O2 Cd1 96.02(18) . . ? C12 O3 Cd1 131.3(2) . 4_756 ? C12 O4 Cd1 134.0(2) . 3 ? C2 C1 C6 120.3(3) . . ? C2 C1 C11 117.5(3) . . ? C6 C1 C11 122.3(3) . . ? C1 C2 C3 120.5(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 C12 116.7(3) . . ? C5 C4 C12 123.2(3) . . ? C10 C5 C6 117.9(3) . . ? C10 C5 C4 123.4(3) . . ? C6 C5 C4 118.7(3) . . ? C7 C6 C5 119.3(3) . . ? C7 C6 C1 121.8(3) . . ? C5 C6 C1 118.8(3) . . ? C8 C7 C6 121.0(3) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 119.7(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 121.2(3) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C5 121.0(3) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? O2 C11 O1 121.3(3) . . ? O2 C11 C1 120.8(3) . . ? O1 C11 C1 117.8(3) . . ? O4 C12 O3 126.7(3) . . ? O4 C12 C4 116.4(3) . . ? O3 C12 C4 116.9(3) . . ? N1 C13 C14 123.6(3) . . ? N1 C13 H13 118.2 . . ? C14 C13 H13 118.2 . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 115.8(3) . . ? C16 C15 C18 122.2(3) . . ? C14 C15 C18 122.1(3) . . ? C15 C16 C17 121.4(3) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? N1 C17 C16 122.7(3) . . ? N1 C17 H17 118.6 . . ? C16 C17 H17 118.6 . . ? C15 C18 C19 112.9(3) . . ? C15 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C15 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C18 C19 C18 113.7(4) . 2_655 ? C18 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 2_655 . ? C18 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 2_655 . ? H19A C19 H19B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.464 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.065 #===END _database_code_depnum_ccdc_archive 'CCDC 958711' ####################################################################### # # 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_5 #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 N O4 Zn' _chemical_formula_sum 'C18 H12 N O4 Zn' _chemical_formula_weight 371.68 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 Orthorhombic _symmetry_space_group_name_H-M 'C m c a' _symmetry_space_group_name_HALL '-C 2bc 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x, -y, -z' '-x, y+1/2, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x, y, z' 'x, -y-1/2, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y, z-1/2' _cell_length_a 18.884(4) _cell_length_b 16.206(3) _cell_length_c 10.375(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3175.1(11) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 17271 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 28.36 _exptl_crystal_description block _exptl_crystal_colour colorless _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 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 1.568 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6505 _exptl_absorpt_correction_T_max 0.6952 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15622 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0118 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1435 _reflns_number_gt 1332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics Diamond _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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^)+(0.0854P)^2^+52.8839P] 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 1435 _refine_ls_number_parameters 163 _refine_ls_number_restraints 181 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.1840 _refine_ls_wR_factor_gt 0.1798 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.116 _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 0.41045(5) 0.53075(9) 0.0248(4) Uani 1 2 d SD . . O1 O 0.0766(3) 0.4297(3) 0.3929(6) 0.0512(13) Uani 1 1 d U B . C1 C 0.1053(4) 0.4922(4) 0.3454(8) 0.0479(14) Uani 1 1 d U . . O2 O 0.0780(3) 0.5625(3) 0.3422(6) 0.0603(15) Uani 1 1 d U . . C2 C 0.2146(4) 0.5519(4) 0.2714(9) 0.0504(17) Uani 1 1 d U . . H2 H 0.1886 0.6007 0.2727 0.061 Uiso 1 1 calc R A 1 C3 C 0.1866(9) 0.4846(13) 0.3081(18) 0.042(2) Uani 0.50 1 d PU B 1 C4 C 0.2288(7) 0.4119(7) 0.3316(14) 0.037(2) Uani 0.50 1 d PU B 1 C5 C 0.2020(8) 0.3389(8) 0.3901(16) 0.046(3) Uani 0.50 1 d PU B 1 H5 H 0.1547 0.3363 0.4150 0.056 Uiso 0.50 1 calc PR B 1 C6 C 0.2455(10) 0.2724(9) 0.4100(18) 0.061(4) Uani 0.50 1 d PU B 1 H6 H 0.2200 0.2294 0.4542 0.091 Uiso 0.50 1 d PR B 1 C3' C 0.1715(9) 0.4844(13) 0.2751(18) 0.041(2) Uani 0.50 1 d PU B 2 C4' C 0.1992(7) 0.4114(7) 0.2081(14) 0.036(2) Uani 0.50 1 d PU B 2 C5' C 0.1570(7) 0.3418(8) 0.1828(14) 0.042(2) Uani 0.50 1 d PU B 2 H5' H 0.1094 0.3425 0.2058 0.050 Uiso 0.50 1 calc PR B 2 C6' C 0.1844(9) 0.2732(9) 0.1251(17) 0.054(4) Uani 0.50 1 d PU B 2 H6' H 0.1497 0.2310 0.1232 0.082 Uiso 0.50 1 d PR B 2 N1 N 0.0000 0.2855(3) 0.5231(5) 0.051(2) Uani 1 2 d SGDU . . C7 C 0.0381(4) 0.2401(4) 0.4331(8) 0.068(3) Uani 0.50 1 d PGDU . . H7 H 0.0656 0.2671 0.3718 0.082 Uiso 0.50 1 calc PR . . C8 C 0.0351(5) 0.1544(4) 0.4346(9) 0.083(3) Uani 0.50 1 d PGDU . . H8 H 0.0606 0.1240 0.3744 0.099 Uiso 0.50 1 calc PR . . C9 C -0.0059(4) 0.1141(3) 0.5263(8) 0.093(3) Uani 0.50 1 d PGDU . . C10 C -0.0441(5) 0.1595(4) 0.6163(9) 0.083(3) Uani 0.50 1 d PGDU . . H10 H -0.0715 0.1325 0.6776 0.099 Uiso 0.50 1 calc PR . . C11 C -0.0411(4) 0.2452(4) 0.6147(8) 0.066(3) Uani 0.50 1 d PGDU . . H11 H -0.0666 0.2756 0.6750 0.079 Uiso 0.50 1 calc PR . . C12 C -0.0250(11) 0.0340(7) 0.5081(17) 0.101(5) Uani 0.50 1 d PDU . . H12A H -0.0553 0.0333 0.4326 0.121 Uiso 0.50 1 calc PR . . H12B H -0.0548 0.0194 0.5808 0.121 Uiso 0.50 1 calc PR . . 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 0.0195(5) 0.0155(5) 0.0393(6) 0.0004(3) 0.000 0.000 O1 0.032(2) 0.050(3) 0.071(3) 0.013(2) 0.025(2) 0.002(2) C1 0.040(3) 0.040(3) 0.063(3) 0.010(3) 0.025(3) 0.010(2) O2 0.059(3) 0.052(3) 0.069(3) 0.014(3) 0.033(3) 0.026(2) C2 0.034(3) 0.032(3) 0.086(5) 0.000(3) 0.008(3) 0.003(2) C3 0.031(4) 0.033(3) 0.062(5) 0.002(4) 0.018(4) 0.003(3) C4 0.028(4) 0.032(4) 0.053(5) 0.003(4) 0.013(4) 0.001(3) C5 0.034(5) 0.038(5) 0.067(7) 0.009(5) 0.014(5) 0.002(4) C6 0.051(8) 0.040(6) 0.090(10) 0.024(7) 0.022(8) 0.004(6) C3' 0.030(4) 0.031(3) 0.063(5) 0.004(4) 0.018(4) 0.005(3) C4' 0.026(4) 0.030(4) 0.052(5) 0.002(3) 0.012(4) 0.001(3) C5' 0.029(5) 0.038(5) 0.058(6) -0.002(5) 0.009(5) -0.004(4) C6' 0.046(7) 0.039(6) 0.078(9) -0.012(6) 0.005(7) -0.009(6) N1 0.094(6) 0.019(3) 0.041(4) -0.001(3) 0.000 0.000 C7 0.134(8) 0.021(4) 0.049(5) -0.001(4) 0.007(5) 0.001(5) C8 0.161(9) 0.027(5) 0.060(6) -0.007(4) 0.018(6) -0.004(6) C9 0.170(9) 0.037(4) 0.072(6) 0.002(4) 0.021(7) -0.007(6) C10 0.146(9) 0.035(5) 0.066(6) 0.008(5) 0.018(6) -0.014(6) C11 0.117(8) 0.026(4) 0.054(5) 0.006(4) 0.009(5) -0.008(5) C12 0.166(12) 0.051(6) 0.085(8) -0.002(6) 0.027(9) -0.011(8) _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 O2 2.025(5) 9_566 ? Zn1 O2 2.025(5) 3_566 ? Zn1 N1 2.027(5) . ? Zn1 O1 2.057(5) . ? Zn1 O1 2.057(5) 11 ? Zn1 Zn1 2.9718(18) 9_566 ? O1 C1 1.251(8) . ? C1 O2 1.251(8) . ? C1 C3' 1.453(19) . ? C1 C3 1.587(18) . ? O2 Zn1 2.025(5) 9_566 ? C2 C3 1.27(2) . ? C2 C3' 1.36(2) . ? C2 C2 1.408(14) 8_545 ? C2 H2 0.9300 . ? C3 C4 1.44(2) . ? C4 C5 1.424(17) . ? C5 C6 1.37(2) . ? C5 H5 0.9300 . ? C6 H6 0.9630 . ? C3' C4' 1.47(2) . ? C4' C5' 1.405(18) . ? C5' C6' 1.36(2) . ? C5' H5' 0.9300 . ? C6' H6' 0.9476 . ? N1 C7 1.390(8) 11 ? N1 C7 1.3900 . ? N1 C11 1.390(9) 11 ? N1 C11 1.3900 . ? C7 C8 1.3900 . ? C7 H7 0.9300 . ? C8 C9 1.3900 . ? C8 H8 0.9300 . ? C9 C9 0.224(15) 11 ? C9 C12 1.360(10) . ? C9 C10 1.3900 . ? C9 C12 1.436(12) 11 ? C10 C11 1.3900 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C12 1.46(4) 9_556 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? 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 Zn1 O2 93.4(4) 9_566 3_566 ? O2 Zn1 N1 104.01(19) 9_566 . ? O2 Zn1 N1 104.01(19) 3_566 . ? O2 Zn1 O1 158.6(2) 9_566 . ? O2 Zn1 O1 84.7(3) 3_566 . ? N1 Zn1 O1 97.12(17) . . ? O2 Zn1 O1 84.7(3) 9_566 11 ? O2 Zn1 O1 158.6(2) 3_566 11 ? N1 Zn1 O1 97.12(17) . 11 ? O1 Zn1 O1 89.3(3) . 11 ? O2 Zn1 Zn1 85.87(16) 9_566 9_566 ? O2 Zn1 Zn1 85.87(16) 3_566 9_566 ? N1 Zn1 Zn1 165.37(15) . 9_566 ? O1 Zn1 Zn1 72.72(14) . 9_566 ? O1 Zn1 Zn1 72.73(14) 11 9_566 ? C1 O1 Zn1 134.5(5) . . ? O2 C1 O1 124.7(6) . . ? O2 C1 C3' 114.9(10) . . ? O1 C1 C3' 120.1(10) . . ? O2 C1 C3 117.5(10) . . ? O1 C1 C3 116.9(9) . . ? C3' C1 C3 16.1(11) . . ? C1 O2 Zn1 118.7(5) . 9_566 ? C3 C2 C3' 19.1(12) . . ? C3 C2 C2 119.3(9) . 8_545 ? C3' C2 C2 125.1(8) . 8_545 ? C3 C2 H2 120.3 . . ? C3' C2 H2 111.5 . . ? C2 C2 H2 120.3 8_545 . ? C2 C3 C4 121.4(14) . . ? C2 C3 C1 114.2(14) . . ? C4 C3 C1 123.8(15) . . ? C5 C4 C3 123.6(13) . . ? C6 C5 C4 120.3(13) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 H6 109.9 . . ? C2 C3' C1 117.3(15) . . ? C2 C3' C4' 114.9(13) . . ? C1 C3' C4' 127.9(15) . . ? C5' C4' C3' 122.2(12) . . ? C6' C5' C4' 121.4(13) . . ? C6' C5' H5' 119.3 . . ? C4' C5' H5' 119.3 . . ? C5' C6' H6' 109.6 . . ? C7 N1 C7 62.4(5) 11 . ? C7 N1 C11 120.0(4) 11 11 ? C7 N1 C11 85.5(3) . 11 ? C7 N1 C11 85.5(3) 11 . ? C7 N1 C11 120.0 . . ? C11 N1 C11 67.9(6) 11 . ? C7 N1 Zn1 123.7(2) 11 . ? C7 N1 Zn1 123.7(2) . . ? C11 N1 Zn1 116.3(2) 11 . ? C11 N1 Zn1 116.3(2) . . ? N1 C7 C8 120.0 . . ? N1 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 120.0 . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C9 C9 C12 105.3(9) 11 . ? C9 C9 C10 121.2 11 . ? C12 C9 C10 117.5(5) . . ? C9 C9 C8 56.1 11 . ? C12 C9 C8 120.1(5) . . ? C10 C9 C8 120.0 . . ? C9 C9 C12 66.0(10) 11 11 ? C12 C9 C12 39.3(17) . 11 ? C10 C9 C12 141.0(10) . 11 ? C8 C9 C12 96.2(11) . 11 ? C11 C10 C9 120.0 . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 N1 120.0 . . ? C10 C11 H11 120.0 . . ? N1 C11 H11 120.0 . . ? C9 C12 C12 124(2) . 9_556 ? C9 C12 H12A 106.2 . . ? C12 C12 H12A 106.2 9_556 . ? C9 C12 H12B 106.2 . . ? C12 C12 H12B 106.2 9_556 . ? H12A C12 H12B 106.4 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.765 _refine_diff_density_min -1.845 _refine_diff_density_rms 0.147 #===END _database_code_depnum_ccdc_archive 'CCDC 958712' ####################################################################### # # 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_6 #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H28 Co2 N2 O9' _chemical_formula_sum 'C37 H28 Co2 N2 O9' _chemical_formula_weight 762.47 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 Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_HALL '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.466(3) _cell_length_b 15.188(3) _cell_length_c 25.146(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6289(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 77931 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 28.34 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3120 _exptl_absorpt_coefficient_mu 1.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6955 _exptl_absorpt_correction_T_max 0.7447 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 64068 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.05 _reflns_number_total 5553 _reflns_number_gt 4878 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics Diamond _computing_publication_material 'SHELXTL and PLATON (Spek, 2009)' _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^)+(0.0333P)^2^+8.2934P] 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 5553 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 -0.085461(17) 0.46241(2) 0.075121(13) 0.02337(9) Uani 1 1 d . . . Co2 Co 0.090080(17) 0.57163(2) 0.102908(12) 0.02201(9) Uani 1 1 d . . . N1 N -0.19137(12) 0.53804(14) 0.10185(9) 0.0315(5) Uani 1 1 d . . . N2 N -0.79137(12) 0.58014(13) 0.13489(8) 0.0304(5) Uani 1 1 d . . . O1 O 0.00887(10) 0.38489(11) 0.04561(7) 0.0302(4) Uani 1 1 d . . . O2 O 0.11157(10) 0.43988(10) 0.09247(7) 0.0289(4) Uani 1 1 d . . . O3 O 0.33084(10) 0.13235(12) -0.05874(7) 0.0354(4) Uani 1 1 d . . . O4 O 0.36417(10) 0.08449(11) 0.02084(7) 0.0338(4) Uani 1 1 d . . . O5 O 0.03676(10) 0.53445(11) 0.17616(6) 0.0295(4) Uani 1 1 d . . . O6 O -0.05746(10) 0.43653(12) 0.15124(7) 0.0335(4) Uani 1 1 d . . . O7 O 0.06545(10) 0.20383(12) 0.38655(8) 0.0384(4) Uani 1 1 d . . . O8 O -0.06829(9) 0.20302(10) 0.37570(7) 0.0286(4) Uani 1 1 d . . . O9 O -0.02440(9) 0.57529(10) 0.06158(6) 0.0235(3) Uani 1 1 d . . . H1W H -0.0141 0.5865 0.0292 0.050(9) Uiso 1 1 d R . . H2W H -0.0421 0.6207 0.0776 0.089(14) Uiso 1 1 d R . . C1 C 0.13466(13) 0.30538(15) 0.04940(9) 0.0238(5) Uani 1 1 d . . . C2 C 0.21467(14) 0.31292(16) 0.06459(10) 0.0305(5) Uani 1 1 d . . . H2 H 0.2296 0.3588 0.0870 0.037 Uiso 1 1 calc R . . C3 C 0.27413(14) 0.25386(17) 0.04737(10) 0.0320(6) Uani 1 1 d . . . H3 H 0.3273 0.2595 0.0594 0.038 Uiso 1 1 calc R . . C4 C 0.25426(14) 0.18782(15) 0.01294(9) 0.0262(5) Uani 1 1 d . . . C5 C 0.17163(14) 0.17327(15) -0.00139(9) 0.0261(5) Uani 1 1 d . . . C6 C 0.10997(14) 0.23069(15) 0.01841(9) 0.0250(5) Uani 1 1 d . . . C7 C 0.02774(15) 0.20890(17) 0.00764(11) 0.0341(6) Uani 1 1 d . . . H7 H -0.0135 0.2450 0.0205 0.041 Uiso 1 1 calc R . . C8 C 0.00826(17) 0.13596(19) -0.02121(13) 0.0463(7) Uani 1 1 d . . . H8 H -0.0461 0.1222 -0.0271 0.056 Uiso 1 1 calc R . . C9 C 0.06880(18) 0.08147(19) -0.04210(14) 0.0488(8) Uani 1 1 d . . . H9 H 0.0547 0.0327 -0.0625 0.059 Uiso 1 1 calc R . . C10 C 0.14846(16) 0.09971(18) -0.03261(12) 0.0391(6) Uani 1 1 d . . . H10 H 0.1883 0.0633 -0.0469 0.047 Uiso 1 1 calc R . . C11 C 0.08028(13) 0.38150(15) 0.06414(9) 0.0230(5) Uani 1 1 d . . . C12 C 0.32097(13) 0.13107(15) -0.00917(10) 0.0263(5) Uani 1 1 d . . . C13 C 0.00187(14) 0.41546(15) 0.23414(9) 0.0254(5) Uani 1 1 d . . . C14 C -0.06629(15) 0.39706(19) 0.26256(11) 0.0391(7) Uani 1 1 d . . . H14 H -0.1155 0.4224 0.2527 0.047 Uiso 1 1 calc R . . C15 C -0.06339(15) 0.34045(19) 0.30654(11) 0.0384(6) Uani 1 1 d . . . H15 H -0.1111 0.3281 0.3249 0.046 Uiso 1 1 calc R . . C16 C 0.00786(14) 0.30270(15) 0.32326(10) 0.0270(5) Uani 1 1 d . . . C17 C 0.08217(14) 0.32607(15) 0.29697(10) 0.0263(5) Uani 1 1 d . . . C18 C 0.07763(13) 0.38081(15) 0.25071(9) 0.0252(5) Uani 1 1 d . . . C19 C 0.14907(14) 0.39600(18) 0.22048(10) 0.0340(6) Uani 1 1 d . . . H19 H 0.1459 0.4281 0.1891 0.041 Uiso 1 1 calc R . . C20 C 0.22194(15) 0.3643(2) 0.23676(12) 0.0449(7) Uani 1 1 d . . . H20 H 0.2681 0.3741 0.2163 0.054 Uiso 1 1 calc R . . C21 C 0.22796(16) 0.3169(2) 0.28433(13) 0.0465(7) Uani 1 1 d . . . H21 H 0.2787 0.2984 0.2962 0.056 Uiso 1 1 calc R . . C22 C 0.16066(15) 0.29741(18) 0.31347(11) 0.0375(6) Uani 1 1 d . . . H22 H 0.1660 0.2649 0.3446 0.045 Uiso 1 1 calc R . . C23 C -0.00600(13) 0.46758(15) 0.18317(9) 0.0251(5) Uani 1 1 d . . . C24 C 0.00122(14) 0.23232(15) 0.36510(9) 0.0261(5) Uani 1 1 d . . . C25 C -0.22798(17) 0.5085(2) 0.14538(13) 0.0523(8) Uani 1 1 d . . . H25 H -0.2069 0.4586 0.1618 0.063 Uiso 1 1 calc R . . C26 C -0.29556(18) 0.5476(2) 0.16757(13) 0.0568(9) Uani 1 1 d . . . H26 H -0.3191 0.5236 0.1979 0.068 Uiso 1 1 calc R . . C27 C -0.32823(15) 0.62195(19) 0.14493(12) 0.0408(7) Uani 1 1 d . . . C28 C -0.29100(17) 0.6520(2) 0.09967(13) 0.0465(7) Uani 1 1 d . . . H28 H -0.3111 0.7016 0.0824 0.056 Uiso 1 1 calc R . . C29 C -0.22392(16) 0.60895(19) 0.07966(11) 0.0396(6) Uani 1 1 d . . . H29 H -0.2001 0.6309 0.0488 0.048 Uiso 1 1 calc R . . C30 C -0.40133(16) 0.6659(3) 0.16882(15) 0.0602(10) Uani 1 1 d . . . H30A H -0.4047 0.7261 0.1561 0.072 Uiso 1 1 calc R . . H30B H -0.3956 0.6676 0.2072 0.072 Uiso 1 1 calc R . . C31 C -0.48069(17) 0.6161(3) 0.15407(14) 0.0590(9) Uani 1 1 d . . . H31A H -0.4916 0.6236 0.1164 0.071 Uiso 1 1 calc R . . H31B H -0.4735 0.5537 0.1608 0.071 Uiso 1 1 calc R . . C32 C -0.55017(19) 0.6484(3) 0.18485(16) 0.0752(12) Uani 1 1 d . . . H32A H -0.5504 0.7122 0.1829 0.090 Uiso 1 1 calc R . . H32B H -0.5417 0.6325 0.2218 0.090 Uiso 1 1 calc R . . C33 C -0.63362(18) 0.6156(2) 0.16833(12) 0.0511(8) Uani 1 1 d . . . C34 C -0.69907(19) 0.6418(2) 0.19727(13) 0.0569(9) Uani 1 1 d . . . H34 H -0.6915 0.6719 0.2291 0.068 Uiso 1 1 calc R . . C35 C -0.77597(17) 0.6239(2) 0.17974(11) 0.0451(7) Uani 1 1 d . . . H35 H -0.8196 0.6433 0.2001 0.054 Uiso 1 1 calc R . . C36 C -0.72795(15) 0.54982(18) 0.10785(11) 0.0356(6) Uani 1 1 d . . . H36 H -0.7373 0.5163 0.0775 0.043 Uiso 1 1 calc R . . C37 C -0.64856(16) 0.5661(2) 0.12293(12) 0.0472(7) Uani 1 1 d . . . H37 H -0.6056 0.5442 0.1029 0.057 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 Co1 0.01820(16) 0.02254(17) 0.02938(18) -0.00076(13) -0.00357(12) -0.00130(12) Co2 0.01737(15) 0.02140(16) 0.02728(18) -0.00129(12) -0.00102(12) 0.00009(12) N1 0.0244(10) 0.0326(11) 0.0375(12) 0.0025(9) -0.0007(9) -0.0028(9) N2 0.0244(10) 0.0307(11) 0.0362(12) 0.0015(9) -0.0036(9) -0.0025(9) O1 0.0243(8) 0.0322(9) 0.0342(9) -0.0095(7) -0.0066(7) 0.0093(7) O2 0.0253(8) 0.0243(8) 0.0370(9) -0.0060(7) -0.0029(7) 0.0037(7) O3 0.0303(9) 0.0438(10) 0.0320(10) -0.0077(8) 0.0007(7) 0.0126(8) O4 0.0242(9) 0.0352(9) 0.0419(10) 0.0048(8) 0.0033(8) 0.0103(7) O5 0.0327(9) 0.0289(9) 0.0267(9) 0.0022(7) 0.0014(7) -0.0022(7) O6 0.0258(9) 0.0456(10) 0.0291(9) 0.0061(8) -0.0054(7) -0.0046(8) O7 0.0235(8) 0.0426(10) 0.0491(11) 0.0222(9) -0.0061(8) -0.0044(8) O8 0.0215(8) 0.0262(8) 0.0381(10) 0.0070(7) 0.0030(7) -0.0005(7) O9 0.0226(8) 0.0236(8) 0.0244(9) -0.0027(7) 0.0005(7) -0.0013(6) C1 0.0231(11) 0.0257(11) 0.0224(11) -0.0018(9) 0.0000(9) 0.0058(9) C2 0.0264(12) 0.0294(12) 0.0356(14) -0.0108(11) -0.0067(10) 0.0057(10) C3 0.0228(12) 0.0350(13) 0.0383(14) -0.0077(11) -0.0062(10) 0.0068(11) C4 0.0231(11) 0.0266(12) 0.0290(12) -0.0015(10) 0.0009(10) 0.0064(10) C5 0.0252(12) 0.0247(11) 0.0285(12) -0.0027(10) 0.0007(10) 0.0040(9) C6 0.0234(11) 0.0241(11) 0.0274(12) 0.0001(9) -0.0006(9) 0.0034(9) C7 0.0226(12) 0.0306(13) 0.0490(16) -0.0042(12) 0.0008(11) 0.0021(10) C8 0.0255(13) 0.0404(16) 0.073(2) -0.0132(15) -0.0056(13) -0.0045(12) C9 0.0395(15) 0.0357(15) 0.071(2) -0.0249(15) -0.0058(15) -0.0032(13) C10 0.0313(14) 0.0329(14) 0.0532(17) -0.0152(13) 0.0013(12) 0.0037(11) C11 0.0229(11) 0.0253(12) 0.0208(11) 0.0003(9) 0.0006(9) 0.0045(9) C12 0.0195(11) 0.0241(11) 0.0354(14) -0.0057(10) 0.0011(10) -0.0001(9) C13 0.0214(11) 0.0280(12) 0.0268(12) 0.0028(10) -0.0022(9) -0.0008(9) C14 0.0192(12) 0.0542(17) 0.0438(16) 0.0211(13) 0.0006(11) 0.0056(12) C15 0.0233(12) 0.0497(16) 0.0421(15) 0.0198(13) 0.0059(11) 0.0016(12) C16 0.0235(11) 0.0279(12) 0.0296(13) 0.0043(10) -0.0005(10) -0.0005(10) C17 0.0237(12) 0.0257(12) 0.0295(13) 0.0027(10) -0.0013(10) -0.0007(9) C18 0.0210(11) 0.0278(11) 0.0269(12) 0.0005(10) -0.0019(9) -0.0011(9) C19 0.0245(12) 0.0424(14) 0.0352(14) 0.0099(12) 0.0020(11) -0.0012(11) C20 0.0208(12) 0.0619(19) 0.0520(17) 0.0172(15) 0.0079(12) 0.0026(12) C21 0.0217(13) 0.0575(18) 0.0603(19) 0.0189(15) -0.0028(12) 0.0046(12) C22 0.0256(13) 0.0417(15) 0.0453(16) 0.0162(12) -0.0039(11) 0.0025(11) C23 0.0190(11) 0.0294(12) 0.0268(12) 0.0007(10) 0.0019(9) 0.0059(10) C24 0.0258(12) 0.0243(12) 0.0281(12) 0.0013(10) 0.0016(10) -0.0012(10) C25 0.0367(16) 0.063(2) 0.0573(19) 0.0253(16) 0.0089(14) 0.0085(15) C26 0.0357(16) 0.085(2) 0.0497(19) 0.0169(17) 0.0123(14) 0.0036(16) C27 0.0225(12) 0.0484(16) 0.0514(17) -0.0145(14) -0.0019(12) -0.0051(12) C28 0.0335(15) 0.0405(16) 0.065(2) 0.0087(14) 0.0015(14) 0.0071(13) C29 0.0330(14) 0.0441(15) 0.0418(15) 0.0101(13) 0.0049(12) 0.0010(12) C30 0.0224(14) 0.084(3) 0.074(2) -0.034(2) 0.0017(14) -0.0029(15) C31 0.0328(15) 0.087(3) 0.057(2) -0.0244(19) -0.0033(14) -0.0029(16) C32 0.0321(17) 0.113(3) 0.081(3) -0.035(2) -0.0067(17) -0.0093(19) C33 0.0358(16) 0.070(2) 0.0477(18) -0.0021(16) -0.0126(13) -0.0121(15) C34 0.0414(17) 0.084(2) 0.0456(18) -0.0186(17) -0.0064(14) -0.0108(17) C35 0.0373(15) 0.0604(19) 0.0374(15) -0.0093(14) -0.0047(12) -0.0038(14) C36 0.0258(13) 0.0408(15) 0.0403(15) -0.0020(12) -0.0045(11) -0.0018(11) C37 0.0234(13) 0.068(2) 0.0506(18) -0.0004(15) 0.0022(12) -0.0012(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 O6 2.0077(17) . ? Co1 O9 2.0164(16) . ? Co1 O3 2.0348(17) 4_455 ? Co1 O1 2.0855(16) . ? Co1 N1 2.194(2) . ? Co2 O2 2.0489(16) . ? Co2 O8 2.0976(16) 3 ? Co2 N2 2.115(2) 1_655 ? Co2 O5 2.1172(17) . ? Co2 O9 2.1532(15) . ? Co2 O4 2.2055(18) 8_665 ? N1 C29 1.326(3) . ? N1 C25 1.328(4) . ? N2 C36 1.329(3) . ? N2 C35 1.333(3) . ? N2 Co2 2.115(2) 1_455 ? O1 C11 1.266(3) . ? O2 C11 1.249(3) . ? O3 C12 1.257(3) . ? O3 Co1 2.0348(17) 4 ? O4 C12 1.255(3) . ? O4 Co2 2.2056(18) 8_655 ? O5 C23 1.248(3) . ? O6 C23 1.259(3) . ? O7 C24 1.264(3) . ? O8 C24 1.257(3) . ? O8 Co2 2.0977(16) 3_545 ? O9 H1W 0.8500 . ? O9 H2W 0.8500 . ? C1 C2 1.377(3) . ? C1 C6 1.435(3) . ? C1 C11 1.508(3) . ? C2 C3 1.397(3) . ? C2 H2 0.9300 . ? C3 C4 1.365(3) . ? C3 H3 0.9300 . ? C4 C5 1.425(3) . ? C4 C12 1.503(3) . ? C5 C10 1.418(3) . ? C5 C6 1.428(3) . ? C6 C7 1.420(3) . ? C7 C8 1.363(4) . ? C7 H7 0.9300 . ? C8 C9 1.398(4) . ? C8 H8 0.9300 . ? C9 C10 1.362(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C13 C14 1.359(3) . ? C13 C18 1.416(3) . ? C13 C23 1.512(3) . ? C14 C15 1.402(4) . ? C14 H14 0.9300 . ? C15 C16 1.372(3) . ? C15 H15 0.9300 . ? C16 C17 1.435(3) . ? C16 C24 1.504(3) . ? C17 C22 1.425(3) . ? C17 C18 1.432(3) . ? C18 C19 1.419(3) . ? C19 C20 1.356(4) . ? C19 H19 0.9300 . ? C20 C21 1.400(4) . ? C20 H20 0.9300 . ? C21 C22 1.361(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C25 C26 1.379(4) . ? C25 H25 0.9300 . ? C26 C27 1.374(4) . ? C26 H26 0.9300 . ? C27 C28 1.371(4) . ? C27 C30 1.502(4) . ? C28 C29 1.379(4) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 C31 1.555(4) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.466(4) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.520(4) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.360(4) . ? C33 C37 1.388(4) . ? C34 C35 1.368(4) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C37 1.383(4) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? 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 Co1 O9 102.30(7) . . ? O6 Co1 O3 102.13(7) . 4_455 ? O9 Co1 O3 154.80(7) . 4_455 ? O6 Co1 O1 93.31(7) . . ? O9 Co1 O1 92.78(7) . . ? O3 Co1 O1 91.89(7) 4_455 . ? O6 Co1 N1 89.59(8) . . ? O9 Co1 N1 90.17(7) . . ? O3 Co1 N1 83.92(8) 4_455 . ? O1 Co1 N1 175.33(7) . . ? O2 Co2 O8 172.50(7) . 3 ? O2 Co2 N2 87.08(7) . 1_655 ? O8 Co2 N2 90.12(7) 3 1_655 ? O2 Co2 O5 85.56(7) . . ? O8 Co2 O5 87.69(7) 3 . ? N2 Co2 O5 93.91(7) 1_655 . ? O2 Co2 O9 96.58(6) . . ? O8 Co2 O9 87.10(6) 3 . ? N2 Co2 O9 171.83(7) 1_655 . ? O5 Co2 O9 93.66(6) . . ? O2 Co2 O4 84.70(7) . 8_665 ? O8 Co2 O4 102.36(7) 3 8_665 ? N2 Co2 O4 92.02(7) 1_655 8_665 ? O5 Co2 O4 168.33(6) . 8_665 ? O9 Co2 O4 81.09(6) . 8_665 ? C29 N1 C25 116.0(2) . . ? C29 N1 Co1 128.14(18) . . ? C25 N1 Co1 115.87(18) . . ? C36 N2 C35 117.1(2) . . ? C36 N2 Co2 120.63(17) . 1_455 ? C35 N2 Co2 121.85(18) . 1_455 ? C11 O1 Co1 125.72(15) . . ? C11 O2 Co2 134.05(15) . . ? C12 O3 Co1 106.10(15) . 4 ? C12 O4 Co2 143.70(16) . 8_655 ? C23 O5 Co2 125.01(15) . . ? C23 O6 Co1 133.56(16) . . ? C24 O8 Co2 123.17(14) . 3_545 ? Co1 O9 Co2 109.45(7) . . ? Co1 O9 H1W 115.6 . . ? Co2 O9 H1W 107.1 . . ? Co1 O9 H2W 116.0 . . ? Co2 O9 H2W 95.3 . . ? H1W O9 H2W 111.0 . . ? C2 C1 C6 119.2(2) . . ? C2 C1 C11 115.9(2) . . ? C6 C1 C11 124.8(2) . . ? C1 C2 C3 122.1(2) . . ? C1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 C12 118.7(2) . . ? C5 C4 C12 121.0(2) . . ? C10 C5 C4 121.3(2) . . ? C10 C5 C6 118.9(2) . . ? C4 C5 C6 119.7(2) . . ? C7 C6 C5 118.0(2) . . ? C7 C6 C1 123.9(2) . . ? C5 C6 C1 118.1(2) . . ? C8 C7 C6 121.0(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 120.9(2) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 121.1(2) . . ? C9 C10 H10 119.4 . . ? C5 C10 H10 119.4 . . ? O2 C11 O1 124.4(2) . . ? O2 C11 C1 116.07(19) . . ? O1 C11 C1 119.5(2) . . ? O4 C12 O3 122.1(2) . . ? O4 C12 C4 121.0(2) . . ? O3 C12 C4 116.9(2) . . ? C14 C13 C18 119.7(2) . . ? C14 C13 C23 118.8(2) . . ? C18 C13 C23 121.3(2) . . ? C13 C14 C15 120.8(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 121.8(2) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C17 119.0(2) . . ? C15 C16 C24 116.7(2) . . ? C17 C16 C24 124.0(2) . . ? C22 C17 C18 117.5(2) . . ? C22 C17 C16 124.3(2) . . ? C18 C17 C16 118.2(2) . . ? C13 C18 C19 120.8(2) . . ? C13 C18 C17 120.0(2) . . ? C19 C18 C17 119.1(2) . . ? C20 C19 C18 120.9(2) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 120.2(2) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 121.0(2) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C17 121.0(2) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? O5 C23 O6 126.5(2) . . ? O5 C23 C13 119.8(2) . . ? O6 C23 C13 113.7(2) . . ? O8 C24 O7 123.4(2) . . ? O8 C24 C16 117.8(2) . . ? O7 C24 C16 118.8(2) . . ? N1 C25 C26 123.6(3) . . ? N1 C25 H25 118.2 . . ? C26 C25 H25 118.2 . . ? C27 C26 C25 120.1(3) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C28 C27 C26 116.3(3) . . ? C28 C27 C30 122.8(3) . . ? C26 C27 C30 120.9(3) . . ? C27 C28 C29 120.2(3) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? N1 C29 C28 123.7(3) . . ? N1 C29 H29 118.1 . . ? C28 C29 H29 118.1 . . ? C27 C30 C31 111.2(3) . . ? C27 C30 H30A 109.4 . . ? C31 C30 H30A 109.4 . . ? C27 C30 H30B 109.4 . . ? C31 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C32 C31 C30 111.5(3) . . ? C32 C31 H31A 109.3 . . ? C30 C31 H31A 109.3 . . ? C32 C31 H31B 109.3 . . ? C30 C31 H31B 109.3 . . ? H31A C31 H31B 108.0 . . ? C31 C32 C33 116.8(3) . . ? C31 C32 H32A 108.1 . . ? C33 C32 H32A 108.1 . . ? C31 C32 H32B 108.1 . . ? C33 C32 H32B 108.1 . . ? H32A C32 H32B 107.3 . . ? C34 C33 C37 117.3(3) . . ? C34 C33 C32 118.3(3) . . ? C37 C33 C32 124.2(3) . . ? C33 C34 C35 120.2(3) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? N2 C35 C34 123.2(3) . . ? N2 C35 H35 118.4 . . ? C34 C35 H35 118.4 . . ? N2 C36 C37 122.7(3) . . ? N2 C36 H36 118.6 . . ? C37 C36 H36 118.6 . . ? C36 C37 C33 119.3(3) . . ? C36 C37 H37 120.3 . . ? C33 C37 H37 120.3 . . ? 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 O9 H1W O1 0.85 1.93 2.774(2) 171.0 5_565 O9 H2W O7 0.85 1.60 2.443(2) 172.0 3 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.027 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.054 #===END _database_code_depnum_ccdc_archive 'CCDC 958713'