# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Vigroux, Alain' _publ_contact_author_email vigroux@chimie.ups-tlse.fr _publ_section_title ; A Free-Base Dipyrrin Capable of Forming Extended Architectures Comparable to Those of Its Metal(II) Complex Counterparts ; loop_ _publ_author_name A.Vigroux M.Artigau A.Bonnet S.Ladeira P.Hoffmann #============================================================================= # 2. TITLE AND AUTHOR LIST data_LH _database_code_depnum_ccdc_archive 'CCDC 792154' #TrackingRef '- Cif Global CrystEngComm_vigroux.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H14 N2 O2' _chemical_formula_sum 'C17 H14 N2 O2' _chemical_formula_weight 278.30 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.4997(3) _cell_length_b 11.1220(4) _cell_length_c 22.5876(6) _cell_angle_alpha 90 _cell_angle_beta 91.285(2) _cell_angle_gamma 90 _cell_volume 2888.22(15) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2744 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 23.2 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.28 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.990 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_unetI/netI 0.0628 _diffrn_reflns_number 18848 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 5283 _reflns_number_gt 3150 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0645P)^2^+0.1166P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5283 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1025 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1377 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.576 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.0375(3) 0.6230(2) 0.17128(11) 0.0535(8) Uani 1 1 d . . . H1A H -0.0454 0.6036 0.1674 0.08 Uiso 1 1 calc R . . H1B H 0.0467 0.7041 0.1878 0.08 Uiso 1 1 calc R . . H1C H 0.0759 0.5647 0.1977 0.08 Uiso 1 1 calc R . . C2 C 0.0885(2) 0.5082(2) 0.08783(10) 0.0320(6) Uani 1 1 d . . . C3 C 0.14687(19) 0.5068(2) 0.03001(9) 0.0287(6) Uani 1 1 d . . . C4 C 0.1897(2) 0.6099(2) 0.00282(10) 0.0328(6) Uani 1 1 d . . . H4 H 0.1784 0.6864 0.0205 0.039 Uiso 1 1 calc R . . C5 C 0.2485(2) 0.6011(2) -0.04975(10) 0.0339(6) Uani 1 1 d . . . H5 H 0.2771 0.6717 -0.068 0.041 Uiso 1 1 calc R . . C6 C 0.2662(2) 0.4894(2) -0.07621(9) 0.0304(6) Uani 1 1 d . . . C7 C 0.2200(2) 0.3874(2) -0.04968(10) 0.0341(6) Uani 1 1 d . . . H7 H 0.2293 0.311 -0.0678 0.041 Uiso 1 1 calc R . . C8 C 0.1611(2) 0.3962(2) 0.00253(9) 0.0326(6) Uani 1 1 d . . . H8 H 0.1299 0.3259 0.02 0.039 Uiso 1 1 calc R . . C9 C 0.3341(2) 0.4778(2) -0.13174(10) 0.0307(6) Uani 1 1 d . . . C10 C 0.2895(2) 0.5396(2) -0.18265(10) 0.0334(6) Uani 1 1 d . . . C11 C 0.1898(2) 0.6115(2) -0.18905(11) 0.0400(7) Uani 1 1 d . . . H11 H 0.1358 0.6292 -0.1591 0.048 Uiso 1 1 calc R . . C12 C 0.1846(2) 0.6517(3) -0.24668(11) 0.0536(8) Uani 1 1 d . . . H12 H 0.1271 0.7034 -0.2636 0.064 Uiso 1 1 calc R . . C13 C 0.2785(3) 0.6026(3) -0.27533(11) 0.0544(8) Uani 1 1 d . . . H13 H 0.2961 0.6146 -0.3158 0.065 Uiso 1 1 calc R . . C14 C 0.4347(2) 0.4086(2) -0.13011(10) 0.0349(6) Uani 1 1 d . . . C15 C 0.4852(2) 0.3435(3) -0.08155(11) 0.0501(8) Uani 1 1 d . . . H15 H 0.4569 0.3395 -0.0424 0.06 Uiso 1 1 calc R . . C16 C 0.5825(2) 0.2877(3) -0.10233(12) 0.0582(9) Uani 1 1 d . . . H16 H 0.6344 0.2369 -0.0806 0.07 Uiso 1 1 calc R . . C17 C 0.5902(2) 0.3210(3) -0.16237(12) 0.0550(8) Uani 1 1 d . . . H17 H 0.6504 0.2953 -0.1875 0.066 Uiso 1 1 calc R . . C18 C -0.3578(2) 0.0606(3) 0.02061(14) 0.0632(9) Uani 1 1 d . . . H18A H -0.3546 0.0379 -0.0212 0.095 Uiso 1 1 calc R . . H18B H -0.4047 0.1337 0.0245 0.095 Uiso 1 1 calc R . . H18C H -0.3932 -0.0047 0.0431 0.095 Uiso 1 1 calc R . . C19 C -0.1720(2) -0.0144(2) 0.04437(10) 0.0329(6) Uani 1 1 d . . . C20 C -0.0570(2) 0.0070(2) 0.07361(9) 0.0279(6) Uani 1 1 d . . . C21 C -0.0211(2) 0.1193(2) 0.09410(10) 0.0330(6) Uani 1 1 d . . . H21 H -0.0691 0.1877 0.0875 0.04 Uiso 1 1 calc R . . C22 C 0.0847(2) 0.1317(2) 0.12417(10) 0.0340(6) Uani 1 1 d . . . H22 H 0.1092 0.2089 0.1374 0.041 Uiso 1 1 calc R . . C23 C 0.1557(2) 0.0315(2) 0.13523(9) 0.0287(6) Uani 1 1 d . . . C24 C 0.1206(2) -0.0799(2) 0.11281(10) 0.0310(6) Uani 1 1 d . . . H24 H 0.1689 -0.1482 0.1189 0.037 Uiso 1 1 calc R . . C25 C 0.0162(2) -0.0918(2) 0.08193(10) 0.0311(6) Uani 1 1 d . . . H25 H -0.0058 -0.1679 0.0662 0.037 Uiso 1 1 calc R . . C26 C 0.26487(19) 0.0415(2) 0.17185(10) 0.0306(6) Uani 1 1 d . . . C27 C 0.3508(2) 0.1229(2) 0.15426(10) 0.0316(6) Uani 1 1 d . . . C28 C 0.3550(2) 0.1936(2) 0.10181(10) 0.0382(6) Uani 1 1 d . . . H28 H 0.2992 0.1937 0.0702 0.046 Uiso 1 1 calc R . . C29 C 0.4540(2) 0.2613(3) 0.10535(11) 0.0457(7) Uani 1 1 d . . . H29 H 0.4805 0.3171 0.0768 0.055 Uiso 1 1 calc R . . C30 C 0.5089(2) 0.2319(3) 0.15968(11) 0.0497(8) Uani 1 1 d . . . H30 H 0.5801 0.2661 0.1736 0.06 Uiso 1 1 calc R . . C31 C 0.2724(2) -0.0323(2) 0.22253(10) 0.0336(6) Uani 1 1 d . . . C32 C 0.1814(2) -0.0952(3) 0.25043(11) 0.0473(7) Uani 1 1 d . . . H32 H 0.1026 -0.0991 0.237 0.057 Uiso 1 1 calc R . . C33 C 0.2276(2) -0.1494(3) 0.30025(12) 0.0567(8) Uani 1 1 d . . . H33 H 0.1871 -0.1967 0.3281 0.068 Uiso 1 1 calc R . . C34 C 0.3455(2) -0.1210(3) 0.30182(11) 0.0521(8) Uani 1 1 d . . . H34 H 0.3995 -0.1478 0.3314 0.062 Uiso 1 1 calc R . . N1 N 0.3402(2) 0.5361(2) -0.23719(10) 0.0459(6) Uani 1 1 d . . . H101 H 0.406(2) 0.516(3) -0.2417(13) 0.055 Uiso 1 1 d . . . N2 N 0.50365(19) 0.3923(2) -0.17962(9) 0.0470(6) Uani 1 1 d . . . N3 N 0.44922(17) 0.1506(2) 0.18906(9) 0.0417(6) Uani 1 1 d . . . N4 N 0.37220(19) -0.0514(2) 0.25640(10) 0.0444(6) Uani 1 1 d . . . H104 H 0.435(2) -0.018(2) 0.2487(12) 0.053 Uiso 1 1 d . . . O1 O 0.08978(15) 0.61812(15) 0.11364(7) 0.0428(5) Uani 1 1 d . . . O2 O 0.04501(16) 0.42182(16) 0.11042(7) 0.0466(5) Uani 1 1 d . . . O3 O -0.24049(14) 0.08289(16) 0.04362(8) 0.0459(5) Uani 1 1 d . . . O4 O -0.20234(15) -0.11013(16) 0.02402(8) 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 C1 0.082(2) 0.0401(18) 0.0397(15) -0.0075(13) 0.0259(15) -0.0028(16) C2 0.0344(14) 0.0277(15) 0.0340(13) 0.0006(11) 0.0024(11) 0.0008(13) C3 0.0273(13) 0.0272(15) 0.0316(12) -0.0002(10) -0.0005(10) 0.0007(12) C4 0.0390(15) 0.0253(15) 0.0343(13) -0.0039(11) 0.0053(11) -0.0048(12) C5 0.0427(15) 0.0255(15) 0.0339(13) 0.0027(11) 0.0048(11) -0.0064(12) C6 0.0348(14) 0.0302(15) 0.0262(12) -0.0017(10) 0.0008(10) -0.0022(12) C7 0.0445(15) 0.0242(14) 0.0338(13) -0.0019(11) 0.0024(11) -0.0028(12) C8 0.0411(15) 0.0241(15) 0.0328(13) 0.0049(11) 0.0029(11) -0.0048(12) C9 0.0359(14) 0.0250(14) 0.0312(13) -0.0032(10) 0.0005(11) -0.0087(12) C10 0.0393(15) 0.0305(15) 0.0304(13) 0.0004(11) 0.0065(11) -0.0031(13) C11 0.0422(16) 0.0400(17) 0.0381(14) 0.0032(12) 0.0087(12) 0.0006(14) C12 0.0537(18) 0.062(2) 0.0451(16) 0.0190(15) 0.0040(14) 0.0140(16) C13 0.062(2) 0.068(2) 0.0332(14) 0.0167(14) 0.0063(14) 0.0119(17) C14 0.0330(14) 0.0395(17) 0.0323(13) -0.0017(11) 0.0024(11) -0.0013(13) C15 0.0475(17) 0.069(2) 0.0339(14) 0.0035(14) -0.0051(13) 0.0098(16) C16 0.0460(18) 0.076(2) 0.0522(18) 0.0130(16) -0.0083(14) 0.0157(17) C17 0.0429(17) 0.066(2) 0.0565(18) 0.0054(16) 0.0120(14) 0.0084(17) C18 0.0372(16) 0.057(2) 0.094(2) -0.0126(17) -0.0277(16) 0.0080(16) C19 0.0367(15) 0.0254(15) 0.0362(13) 0.0020(11) -0.0074(11) -0.0012(13) C20 0.0294(13) 0.0261(15) 0.0282(12) -0.0013(10) -0.0031(10) -0.0021(12) C21 0.0343(14) 0.0252(15) 0.0392(13) -0.0016(11) -0.0077(11) 0.0044(12) C22 0.0371(14) 0.0260(15) 0.0384(13) -0.0046(11) -0.0085(11) -0.0025(12) C23 0.0269(13) 0.0271(15) 0.0320(13) 0.0022(10) -0.0021(10) -0.0013(12) C24 0.0312(14) 0.0239(14) 0.0378(13) -0.0003(11) -0.0028(11) 0.0012(12) C25 0.0353(14) 0.0221(14) 0.0356(13) -0.0035(10) -0.0036(11) -0.0015(12) C26 0.0258(13) 0.0321(15) 0.0337(13) -0.0036(11) -0.0012(10) 0.0039(12) C27 0.0280(13) 0.0354(16) 0.0313(12) -0.0005(11) -0.0033(10) -0.0030(12) C28 0.0383(15) 0.0429(17) 0.0332(13) -0.0014(12) -0.0049(11) -0.0047(14) C29 0.0450(17) 0.053(2) 0.0392(15) 0.0040(13) 0.0032(13) -0.0180(15) C30 0.0350(15) 0.064(2) 0.0498(16) 0.0065(15) -0.0031(13) -0.0197(15) C31 0.0254(13) 0.0386(16) 0.0365(13) 0.0014(11) -0.0049(11) -0.0014(12) C32 0.0319(15) 0.064(2) 0.0461(16) 0.0102(14) -0.0032(12) -0.0046(15) C33 0.0463(18) 0.073(2) 0.0509(17) 0.0257(16) 0.0008(14) -0.0088(17) C34 0.0478(18) 0.066(2) 0.0422(15) 0.0196(15) -0.0099(13) -0.0001(16) N1 0.0462(14) 0.0583(17) 0.0336(12) 0.0067(11) 0.0082(11) 0.0097(14) N2 0.0443(14) 0.0550(16) 0.0422(13) 0.0079(11) 0.0129(11) 0.0076(13) N3 0.0310(12) 0.0519(15) 0.0419(12) 0.0042(11) -0.0054(10) -0.0111(11) N4 0.0294(12) 0.0557(17) 0.0476(13) 0.0130(11) -0.0079(11) -0.0091(12) O1 0.0594(12) 0.0312(11) 0.0384(10) -0.0044(8) 0.0160(9) -0.0043(9) O2 0.0643(13) 0.0301(11) 0.0464(11) 0.0032(8) 0.0216(9) -0.0040(10) O3 0.0329(10) 0.0383(12) 0.0658(12) -0.0111(9) -0.0167(9) 0.0070(9) O4 0.0484(12) 0.0307(12) 0.0629(12) -0.0028(9) -0.0246(9) -0.0040(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O1 1.447(3) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 O2 1.202(3) . ? C2 O1 1.355(3) . ? C2 C3 1.482(3) . ? C3 C8 1.389(3) . ? C3 C4 1.395(3) . ? C4 C5 1.383(3) . ? C4 H4 0.95 . ? C5 C6 1.396(3) . ? C5 H5 0.95 . ? C6 C7 1.394(3) . ? C6 C9 1.497(3) . ? C7 C8 1.377(3) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C14 1.390(3) . ? C9 C10 1.425(3) . ? C10 N1 1.375(3) . ? C10 C11 1.403(3) . ? C11 C12 1.376(3) . ? C11 H11 0.95 . ? C12 C13 1.384(4) . ? C12 H12 0.95 . ? C13 N1 1.329(3) . ? C13 H13 0.95 . ? C14 N2 1.397(3) . ? C14 C15 1.427(3) . ? C15 C16 1.372(4) . ? C15 H15 0.95 . ? C16 C17 1.410(4) . ? C16 H16 0.95 . ? C17 N2 1.324(3) . ? C17 H17 0.95 . ? C18 O3 1.456(3) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 O4 1.208(3) . ? C19 O3 1.338(3) . ? C19 C20 1.484(3) . ? C20 C21 1.391(3) . ? C20 C25 1.395(3) . ? C21 C22 1.387(3) . ? C21 H21 0.95 . ? C22 C23 1.401(3) . ? C22 H22 0.95 . ? C23 C24 1.394(3) . ? C23 C26 1.492(3) . ? C24 C25 1.381(3) . ? C24 H24 0.95 . ? C25 H25 0.95 . ? C26 C27 1.404(3) . ? C26 C31 1.410(3) . ? C27 N3 1.398(3) . ? C27 C28 1.424(3) . ? C28 C29 1.366(3) . ? C28 H28 0.95 . ? C29 C30 1.406(3) . ? C29 H29 0.95 . ? C30 N3 1.323(3) . ? C30 H30 0.95 . ? C31 N4 1.381(3) . ? C31 C32 1.418(3) . ? C32 C33 1.373(4) . ? C32 H32 0.95 . ? C33 C34 1.392(4) . ? C33 H33 0.95 . ? C34 N4 1.327(3) . ? C34 H34 0.95 . ? N1 H101 0.79(3) . ? N4 H104 0.83(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 122.6(2) . . ? O2 C2 C3 124.6(2) . . ? O1 C2 C3 112.8(2) . . ? C8 C3 C4 119.0(2) . . ? C8 C3 C2 117.6(2) . . ? C4 C3 C2 123.4(2) . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 118.7(2) . . ? C7 C6 C9 120.1(2) . . ? C5 C6 C9 121.3(2) . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C3 120.8(2) . . ? C7 C8 H8 119.6 . . ? C3 C8 H8 119.6 . . ? C14 C9 C10 124.9(2) . . ? C14 C9 C6 118.3(2) . . ? C10 C9 C6 116.8(2) . . ? N1 C10 C11 106.6(2) . . ? N1 C10 C9 123.9(2) . . ? C11 C10 C9 129.5(2) . . ? C12 C11 C10 107.5(2) . . ? C12 C11 H11 126.2 . . ? C10 C11 H11 126.2 . . ? C11 C12 C13 107.2(3) . . ? C11 C12 H12 126.4 . . ? C13 C12 H12 126.4 . . ? N1 C13 C12 109.1(2) . . ? N1 C13 H13 125.4 . . ? C12 C13 H13 125.4 . . ? C9 C14 N2 122.6(2) . . ? C9 C14 C15 128.7(2) . . ? N2 C14 C15 108.7(2) . . ? C16 C15 C14 106.7(2) . . ? C16 C15 H15 126.6 . . ? C14 C15 H15 126.6 . . ? C15 C16 C17 106.2(3) . . ? C15 C16 H16 126.9 . . ? C17 C16 H16 126.9 . . ? N2 C17 C16 112.2(2) . . ? N2 C17 H17 123.9 . . ? C16 C17 H17 123.9 . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 C19 O3 122.9(2) . . ? O4 C19 C20 123.9(2) . . ? O3 C19 C20 113.2(2) . . ? C21 C20 C25 119.2(2) . . ? C21 C20 C19 123.2(2) . . ? C25 C20 C19 117.6(2) . . ? C22 C21 C20 120.2(2) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 120.6(2) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 118.6(2) . . ? C24 C23 C26 120.1(2) . . ? C22 C23 C26 121.3(2) . . ? C25 C24 C23 120.7(2) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C20 120.5(2) . . ? C24 C25 H25 119.8 . . ? C20 C25 H25 119.8 . . ? C27 C26 C31 125.1(2) . . ? C27 C26 C23 118.7(2) . . ? C31 C26 C23 116.3(2) . . ? N3 C27 C26 123.3(2) . . ? N3 C27 C28 107.7(2) . . ? C26 C27 C28 129.0(2) . . ? C29 C28 C27 107.5(2) . . ? C29 C28 H28 126.3 . . ? C27 C28 H28 126.3 . . ? C28 C29 C30 106.3(2) . . ? C28 C29 H29 126.9 . . ? C30 C29 H29 126.9 . . ? N3 C30 C29 111.7(2) . . ? N3 C30 H30 124.2 . . ? C29 C30 H30 124.2 . . ? N4 C31 C26 125.1(2) . . ? N4 C31 C32 106.9(2) . . ? C26 C31 C32 128.0(2) . . ? C33 C32 C31 107.8(2) . . ? C33 C32 H32 126.1 . . ? C31 C32 H32 126.1 . . ? C32 C33 C34 106.3(2) . . ? C32 C33 H33 126.9 . . ? C34 C33 H33 126.9 . . ? N4 C34 C33 110.8(2) . . ? N4 C34 H34 124.6 . . ? C33 C34 H34 124.6 . . ? C13 N1 C10 109.5(2) . . ? C13 N1 H101 125(2) . . ? C10 N1 H101 123(2) . . ? C17 N2 C14 106.2(2) . . ? C30 N3 C27 106.9(2) . . ? C34 N4 C31 108.3(2) . . ? C34 N4 H104 129.4(19) . . ? C31 N4 H104 122.1(19) . . ? C2 O1 C1 114.85(18) . . ? C19 O3 C18 114.0(2) . . ? _vrf_PLAT417_LH ; PROBLEM: Short Inter D-H..H-D H104 .. H104 .. 1.50 Ang. RESPONSE: The hydrogen atoms were found fully delocalized between the two nitrogen atoms of each molecule. For symmetry reason, placing the hydrogen atom to a single pyrrole ring generates a short non-bonding inter D-H. .H-D contact. ; #===END data_Ni[L]2 _database_code_depnum_ccdc_archive 'CCDC 792155' #TrackingRef '- Cif Global CrystEngComm_vigroux.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H26 N4 Ni O4' _chemical_formula_sum 'C34 H26 N4 Ni O4' _chemical_formula_weight 613.28 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 22.9274(8) _cell_length_b 21.1264(8) _cell_length_c 23.1730(9) _cell_angle_alpha 90 _cell_angle_beta 90.436(2) _cell_angle_gamma 90 _cell_volume 11224.1(7) _cell_formula_units_Z 16 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 5214 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 28.3 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description stick _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5088 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_absorpt_correction_T_min 0.900 _exptl_absorpt_correction_T_max 0.985 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.1809 _diffrn_reflns_av_unetI/netI 0.3238 _diffrn_reflns_number 67647 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 30.39 _diffrn_reflns_theta_full 30.39 _diffrn_measured_fraction_theta_full 0.963 _diffrn_measured_fraction_theta_max 0.963 _reflns_number_total 16339 _reflns_number_gt 5365 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0301P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 16339 _refine_ls_number_parameters 781 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2078 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.123 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 0.745 _refine_ls_restrained_S_all 0.745 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.05 _refine_diff_density_min -0.666 _refine_diff_density_rms 0.077 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C -0.42578(13) 0.2135(3) 0.00762(16) 0.0481(13) Uani 1 1 d . . . H1A H -0.4472 0.2474 0.0271 0.072 Uiso 1 1 calc R . . H1B H -0.4488 0.1744 0.0087 0.072 Uiso 1 1 calc R . . H1C H -0.4189 0.2255 -0.0326 0.072 Uiso 1 1 calc R . . C2 C -0.33455(15) 0.2538(2) 0.03551(14) 0.0262(9) Uani 1 1 d . . . C3 C -0.27964(12) 0.24494(19) 0.06993(13) 0.0220(9) Uani 1 1 d . . . C4 C -0.26511(13) 0.1883(2) 0.09695(14) 0.0274(9) Uani 1 1 d . . . H4 H -0.29 0.1526 0.0932 0.033 Uiso 1 1 calc R . . C5 C -0.21416(13) 0.18408(19) 0.12943(13) 0.0250(9) Uani 1 1 d . . . H5 H -0.2041 0.1451 0.1474 0.03 Uiso 1 1 calc R . . C6 C -0.17765(12) 0.23602(19) 0.13607(13) 0.0206(8) Uani 1 1 d . . . C7 C -0.19265(12) 0.29318(19) 0.10783(13) 0.0227(9) Uani 1 1 d . . . H7 H -0.1679 0.3291 0.1113 0.027 Uiso 1 1 calc R . . C8 C -0.24306(12) 0.29683(19) 0.07540(13) 0.0242(9) Uani 1 1 d . . . H8 H -0.2529 0.3353 0.0565 0.029 Uiso 1 1 calc R . . C9 C -0.12325(12) 0.23314(19) 0.17241(13) 0.0216(8) Uani 1 1 d . . . C10 C -0.08475(13) 0.18379(19) 0.16354(13) 0.0218(8) Uani 1 1 d . . . C11 C -0.08332(14) 0.1387(2) 0.11819(14) 0.0300(9) Uani 1 1 d . . . H11 H -0.1106 0.1351 0.0873 0.036 Uiso 1 1 calc R . . C12 C -0.03477(14) 0.1007(2) 0.12720(15) 0.0351(10) Uani 1 1 d . . . H12 H -0.0219 0.0667 0.1036 0.042 Uiso 1 1 calc R . . C13 C -0.00838(14) 0.1227(2) 0.17843(16) 0.0361(11) Uani 1 1 d . . . H13 H 0.0257 0.1047 0.1952 0.043 Uiso 1 1 calc R . . C14 C -0.11378(12) 0.28149(19) 0.21238(13) 0.0223(9) Uani 1 1 d . . . C15 C -0.15363(14) 0.3264(2) 0.23369(14) 0.0272(9) Uani 1 1 d . . . H15 H -0.1933 0.3309 0.2223 0.033 Uiso 1 1 calc R . . C16 C -0.12448(14) 0.3624(2) 0.27400(15) 0.0328(10) Uani 1 1 d . . . H16 H -0.1402 0.3963 0.2959 0.039 Uiso 1 1 calc R . . C17 C -0.06731(15) 0.3396(2) 0.27650(15) 0.0316(10) Uani 1 1 d . . . H17 H -0.0375 0.3563 0.3007 0.038 Uiso 1 1 calc R . . C18 C 0.95899(15) 0.2495(3) 0.41777(19) 0.0646(18) Uani 1 1 d . . . H18A H 0.9629 0.2946 0.427 0.097 Uiso 1 1 calc R . . H18B H 0.9897 0.237 0.3909 0.097 Uiso 1 1 calc R . . H18C H 0.9626 0.2245 0.4533 0.097 Uiso 1 1 calc R . . C19 C 0.85630(16) 0.2500(2) 0.42437(18) 0.0434(12) Uani 1 1 d . . . C20 C 0.79981(14) 0.2421(2) 0.39312(15) 0.0348(11) Uani 1 1 d . . . C21 C 0.79614(14) 0.2164(2) 0.33767(15) 0.0352(10) Uani 1 1 d . . . H21 H 0.8307 0.2039 0.3184 0.042 Uiso 1 1 calc R . . C22 C 0.74275(13) 0.2092(2) 0.31068(14) 0.0329(10) Uani 1 1 d . . . H22 H 0.7407 0.1922 0.2728 0.039 Uiso 1 1 calc R . . C23 C 0.69111(13) 0.2271(2) 0.33920(14) 0.0291(9) Uani 1 1 d . . . C24 C 0.69552(15) 0.2523(2) 0.39499(15) 0.0387(12) Uani 1 1 d . . . H24 H 0.6612 0.2642 0.415 0.046 Uiso 1 1 calc R . . C25 C 0.74965(15) 0.2598(2) 0.42101(15) 0.0430(13) Uani 1 1 d . . . H25 H 0.7522 0.2775 0.4586 0.052 Uiso 1 1 calc R . . C26 C 0.63280(13) 0.2193(2) 0.31095(14) 0.0280(9) Uani 1 1 d . . . C27 C 0.62496(13) 0.2438(2) 0.25533(14) 0.0290(10) Uani 1 1 d . . . C28 C 0.66168(13) 0.2856(2) 0.22438(14) 0.0341(10) Uani 1 1 d . . . H28 H 0.6996 0.2991 0.2358 0.041 Uiso 1 1 calc R . . C29 C 0.63290(14) 0.3026(2) 0.17549(15) 0.0384(12) Uani 1 1 d . . . H29 H 0.6461 0.3314 0.1469 0.046 Uiso 1 1 calc R . . C30 C 0.58005(14) 0.2699(2) 0.17526(14) 0.0389(12) Uani 1 1 d . . . H30 H 0.5519 0.2721 0.145 0.047 Uiso 1 1 calc R . . C31 C 0.58853(13) 0.1897(2) 0.34255(14) 0.0279(10) Uani 1 1 d . . . C32 C 0.59287(15) 0.1533(2) 0.39312(15) 0.0370(11) Uani 1 1 d . . . H32 H 0.6271 0.1482 0.4161 0.044 Uiso 1 1 calc R . . C33 C 0.53914(15) 0.1260(2) 0.40411(15) 0.0402(12) Uani 1 1 d . . . H33 H 0.5294 0.0979 0.4345 0.048 Uiso 1 1 calc R . . C34 C 0.50181(15) 0.1495(2) 0.35970(15) 0.0391(12) Uani 1 1 d . . . H34 H 0.4615 0.1395 0.3562 0.047 Uiso 1 1 calc R . . C35 C 0.27843(19) 0.5898(3) 0.65993(17) 0.0617(15) Uani 1 1 d . . . H35A H 0.245 0.5613 0.6641 0.092 Uiso 1 1 calc R . . H35B H 0.2653 0.6338 0.6629 0.092 Uiso 1 1 calc R . . H35C H 0.3071 0.581 0.6905 0.092 Uiso 1 1 calc R . . C36 C 0.30506(15) 0.5188(3) 0.58594(16) 0.0353(11) Uani 1 1 d . . . C37 C 0.33536(14) 0.5111(2) 0.52877(14) 0.0301(10) Uani 1 1 d . . . C38 C 0.36382(16) 0.5609(2) 0.50022(16) 0.0432(12) Uani 1 1 d . . . H38 H 0.3627 0.6027 0.5153 0.052 Uiso 1 1 calc R . . C39 C 0.39388(16) 0.5480(2) 0.44909(17) 0.0429(12) Uani 1 1 d . . . H39 H 0.413 0.5814 0.4294 0.051 Uiso 1 1 calc R . . C40 C 0.39611(13) 0.4875(2) 0.42707(14) 0.0285(10) Uani 1 1 d . . . C41 C 0.36601(13) 0.4398(2) 0.45513(14) 0.0292(9) Uani 1 1 d . . . H41 H 0.3663 0.3982 0.4395 0.035 Uiso 1 1 calc R . . C42 C 0.33561(14) 0.4513(2) 0.50518(14) 0.0291(10) Uani 1 1 d . . . H42 H 0.3149 0.4179 0.5234 0.035 Uiso 1 1 calc R . . C43 C 0.42883(14) 0.4718(2) 0.37243(14) 0.0287(9) Uani 1 1 d . . . C44 C 0.40910(14) 0.5010(2) 0.32186(15) 0.0331(10) Uani 1 1 d . . . C45 C 0.36248(15) 0.5439(2) 0.31393(16) 0.0390(11) Uani 1 1 d . . . H45 H 0.3396 0.5623 0.3435 0.047 Uiso 1 1 calc R . . C46 C 0.35630(17) 0.5541(3) 0.25606(17) 0.0520(14) Uani 1 1 d . . . H46 H 0.3284 0.5807 0.2377 0.062 Uiso 1 1 calc R . . C47 C 0.39918(15) 0.5175(2) 0.22913(17) 0.0478(14) Uani 1 1 d . . . H47 H 0.4048 0.5163 0.1886 0.057 Uiso 1 1 calc R . . C48 C 0.47355(14) 0.4267(2) 0.37738(15) 0.0346(11) Uani 1 1 d . . . C49 C 0.49393(15) 0.3937(2) 0.42640(16) 0.0431(12) Uani 1 1 d . . . H49 H 0.4794 0.3984 0.4644 0.052 Uiso 1 1 calc R . . C50 C 0.53804(16) 0.3536(3) 0.41058(17) 0.0490(13) Uani 1 1 d . . . H50 H 0.5592 0.3251 0.4345 0.059 Uiso 1 1 calc R . . C51 C 0.54511(16) 0.3640(3) 0.35114(17) 0.0465(12) Uani 1 1 d . . . H51 H 0.5736 0.343 0.3285 0.056 Uiso 1 1 calc R . . C52 C 0.74782(16) 1.0528(2) -0.15772(14) 0.0426(12) Uani 1 1 d . . . H52A H 0.7875 1.0361 -0.1537 0.064 Uiso 1 1 calc R . . H52B H 0.7495 1.097 -0.1704 0.064 Uiso 1 1 calc R . . H52C H 0.7263 1.0276 -0.1863 0.064 Uiso 1 1 calc R . . C53 C 0.71697(14) 0.9919(2) -0.07799(15) 0.0297(10) Uani 1 1 d . . . C54 C 0.68617(13) 0.9938(2) -0.02134(13) 0.0246(9) Uani 1 1 d . . . C55 C 0.66724(13) 1.0505(2) 0.00202(14) 0.0285(9) Uani 1 1 d . . . H55 H 0.6759 1.0893 -0.0167 0.034 Uiso 1 1 calc R . . C56 C 0.63535(13) 1.0506(2) 0.05321(14) 0.0275(9) Uani 1 1 d . . . H56 H 0.6224 1.0896 0.0691 0.033 Uiso 1 1 calc R . . C57 C 0.62249(13) 0.9938(2) 0.08094(13) 0.0242(9) Uani 1 1 d . . . C58 C 0.64340(14) 0.9375(2) 0.05813(15) 0.0321(10) Uani 1 1 d . . . H58 H 0.6356 0.8987 0.0773 0.039 Uiso 1 1 calc R . . C59 C 0.67567(13) 0.9373(2) 0.00737(14) 0.0290(9) Uani 1 1 d . . . H59 H 0.6904 0.8986 -0.0075 0.035 Uiso 1 1 calc R . . C60 C 0.58504(13) 0.99507(19) 0.13353(13) 0.0242(9) Uani 1 1 d . . . C61 C 0.60898(13) 1.0191(2) 0.18391(14) 0.0261(9) Uani 1 1 d . . . C62 C 0.66492(14) 1.0474(2) 0.19348(15) 0.0322(10) Uani 1 1 d . . . H62 H 0.6949 1.0523 0.1658 0.039 Uiso 1 1 calc R . . C63 C 0.66713(15) 1.0658(2) 0.24971(15) 0.0369(11) Uani 1 1 d . . . H63 H 0.6988 1.0863 0.2686 0.044 Uiso 1 1 calc R . . C64 C 0.61349(14) 1.0487(2) 0.27450(15) 0.0361(11) Uani 1 1 d . . . H64 H 0.6034 1.0565 0.3135 0.043 Uiso 1 1 calc R . . C65 C 0.52840(13) 0.9720(2) 0.12737(13) 0.0257(9) Uani 1 1 d . . . C66 C 0.50276(14) 0.9409(2) 0.08016(14) 0.0363(11) Uani 1 1 d . . . H66 H 0.5203 0.9336 0.0437 0.044 Uiso 1 1 calc R . . C67 C 0.44815(15) 0.9231(2) 0.09605(15) 0.0426(13) Uani 1 1 d . . . H67 H 0.4206 0.9006 0.073 0.051 Uiso 1 1 calc R . . C68 C 0.44027(14) 0.9439(2) 0.15215(14) 0.0331(10) Uani 1 1 d . . . H68 H 0.4058 0.9371 0.1737 0.04 Uiso 1 1 calc R . . N1 N -0.03683(11) 0.17199(16) 0.20054(12) 0.0264(8) Uani 1 1 d . . . N2 N -0.06023(10) 0.29108(17) 0.24023(11) 0.0263(7) Uani 1 1 d . . . N3 N 0.57399(11) 0.23502(18) 0.22290(12) 0.0336(9) Uani 1 1 d . . . N4 N 0.53084(11) 0.18777(17) 0.32302(12) 0.0322(9) Uani 1 1 d . . . N5 N 0.43130(12) 0.48456(19) 0.26699(12) 0.0400(10) Uani 1 1 d . . . N6 N 0.50752(12) 0.40636(19) 0.32988(13) 0.0400(9) Uani 1 1 d . . . N7 N 0.57871(11) 1.02006(17) 0.23610(11) 0.0295(8) Uani 1 1 d . . . N8 N 0.48746(10) 0.97476(17) 0.17234(11) 0.0272(8) Uani 1 1 d . . . O1 O -0.36995(9) 0.20330(14) 0.03696(10) 0.0347(7) Uani 1 1 d . . . O2 O -0.34625(9) 0.30196(14) 0.00966(10) 0.0349(7) Uani 1 1 d . . . O3 O 0.90253(10) 0.23813(17) 0.39154(12) 0.0569(10) Uani 1 1 d . . . O4 O 0.86082(11) 0.2681(2) 0.47273(13) 0.0949(16) Uani 1 1 d . . . O5 O 0.30520(11) 0.57965(16) 0.60349(11) 0.0484(8) Uani 1 1 d . . . O6 O 0.28360(11) 0.47673(16) 0.61149(11) 0.0441(8) Uani 1 1 d . . . O7 O 0.71857(10) 1.04918(15) -0.10275(10) 0.0355(7) Uani 1 1 d . . . O8 O 0.73691(12) 0.94498(16) -0.09931(11) 0.0497(8) Uani 1 1 d . . . Ni1 Ni 0 0.23076(4) 0.25 0.02546(18) Uani 1 2 d S . . Ni2 Ni 0.5 0.20957(4) 0.25 0.0311(2) Uani 1 2 d S . . Ni3 Ni 0.5 0.43265(5) 0.25 0.0495(3) Uani 1 2 d S . . Ni4 Ni 0.5 0.99862(4) 0.25 0.02774(19) Uani 1 2 d S . . 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 C1 0.0241(17) 0.069(4) 0.051(2) 0.002(3) -0.0168(16) -0.010(2) C2 0.0300(18) 0.024(3) 0.0244(17) -0.0035(18) -0.0008(14) 0.0007(19) C3 0.0185(15) 0.026(3) 0.0212(16) -0.0008(17) -0.0028(12) 0.0036(16) C4 0.0242(17) 0.025(3) 0.0330(19) -0.0033(19) -0.0050(14) -0.0047(17) C5 0.0277(17) 0.016(2) 0.0313(18) 0.0023(18) -0.0048(14) 0.0027(17) C6 0.0161(14) 0.021(2) 0.0251(16) -0.0022(17) -0.0018(12) 0.0020(16) C7 0.0184(15) 0.024(3) 0.0261(16) -0.0004(18) -0.0033(12) -0.0022(17) C8 0.0249(16) 0.022(3) 0.0260(17) 0.0036(18) -0.0013(13) 0.0008(17) C9 0.0168(14) 0.022(2) 0.0260(16) 0.0041(18) -0.0026(12) -0.0014(16) C10 0.0214(15) 0.020(2) 0.0234(16) -0.0017(17) -0.0073(12) -0.0005(17) C11 0.0300(18) 0.030(3) 0.0302(18) -0.004(2) -0.0065(14) 0.0004(19) C12 0.0362(19) 0.027(3) 0.042(2) -0.013(2) -0.0033(16) 0.008(2) C13 0.0262(18) 0.029(3) 0.053(2) -0.001(2) -0.0129(16) 0.0064(19) C14 0.0202(15) 0.024(3) 0.0232(16) 0.0040(18) -0.0011(12) -0.0046(17) C15 0.0247(17) 0.026(3) 0.0309(18) 0.0010(19) 0.0024(14) 0.0028(18) C16 0.038(2) 0.026(3) 0.0350(19) -0.012(2) 0.0019(15) 0.002(2) C17 0.038(2) 0.025(3) 0.0318(19) -0.008(2) -0.0085(15) 0.0026(19) C18 0.032(2) 0.097(6) 0.064(3) -0.023(3) -0.0155(19) 0.000(2) C19 0.038(2) 0.050(4) 0.042(2) 0.004(2) -0.0089(18) -0.006(2) C20 0.0315(19) 0.037(3) 0.0354(19) 0.001(2) -0.0046(15) -0.0037(19) C21 0.0274(17) 0.039(3) 0.039(2) 0.004(2) -0.0016(14) 0.000(2) C22 0.0324(18) 0.035(3) 0.0317(18) -0.006(2) -0.0028(14) -0.001(2) C23 0.0298(17) 0.027(3) 0.0303(18) -0.0001(19) -0.0018(14) 0.0003(19) C24 0.034(2) 0.050(4) 0.033(2) -0.007(2) 0.0033(16) 0.000(2) C25 0.037(2) 0.060(4) 0.032(2) -0.007(2) -0.0089(16) -0.006(2) C26 0.0255(16) 0.029(3) 0.0294(17) -0.0042(19) -0.0011(13) 0.0000(18) C27 0.0226(16) 0.036(3) 0.0285(18) -0.0013(19) 0.0021(14) 0.0054(17) C28 0.0233(16) 0.039(3) 0.040(2) 0.000(2) 0.0074(14) -0.0055(19) C29 0.0332(19) 0.046(4) 0.036(2) 0.014(2) 0.0057(15) 0.000(2) C30 0.0302(18) 0.060(4) 0.0269(18) 0.006(2) 0.0022(14) 0.005(2) C31 0.0260(17) 0.032(3) 0.0253(17) 0.0003(18) -0.0029(13) -0.0004(18) C32 0.039(2) 0.041(3) 0.0306(19) 0.001(2) -0.0088(16) 0.004(2) C33 0.044(2) 0.048(4) 0.030(2) 0.008(2) 0.0085(16) -0.003(2) C34 0.0323(19) 0.052(4) 0.033(2) 0.005(2) 0.0039(16) -0.008(2) C35 0.080(3) 0.054(4) 0.052(3) -0.022(3) 0.030(2) 0.001(3) C36 0.0324(19) 0.037(3) 0.037(2) -0.007(2) 0.0024(16) -0.001(2) C37 0.0300(18) 0.031(3) 0.0294(18) -0.001(2) 0.0016(14) -0.0068(19) C38 0.053(2) 0.029(3) 0.048(2) -0.013(2) 0.0141(19) -0.012(2) C39 0.044(2) 0.036(3) 0.048(2) -0.009(2) 0.0142(18) -0.018(2) C40 0.0271(17) 0.029(3) 0.0298(18) -0.0029(19) 0.0053(14) -0.0074(19) C41 0.0319(18) 0.023(3) 0.0329(19) -0.0025(19) -0.0024(15) -0.0001(18) C42 0.0287(18) 0.030(3) 0.0289(18) 0.0061(19) 0.0016(14) -0.0067(18) C43 0.0292(17) 0.029(3) 0.0281(18) -0.0070(19) 0.0051(14) -0.013(2) C44 0.0240(17) 0.039(3) 0.036(2) 0.000(2) 0.0094(14) -0.0067(19) C45 0.038(2) 0.036(3) 0.043(2) 0.005(2) 0.0098(17) -0.007(2) C46 0.039(2) 0.066(4) 0.051(3) 0.027(3) 0.0047(19) 0.000(2) C47 0.039(2) 0.066(4) 0.038(2) 0.009(2) 0.0079(18) 0.000(2) C48 0.0244(17) 0.045(3) 0.034(2) -0.006(2) 0.0076(15) -0.002(2) C49 0.035(2) 0.058(4) 0.036(2) -0.006(2) 0.0005(16) 0.001(2) C50 0.044(2) 0.054(4) 0.049(3) -0.007(3) -0.0001(19) 0.004(2) C51 0.036(2) 0.051(4) 0.053(3) -0.001(3) 0.0092(19) 0.010(2) C52 0.053(2) 0.049(4) 0.0261(19) 0.005(2) 0.0146(17) 0.007(2) C53 0.0280(18) 0.035(3) 0.0264(18) -0.003(2) -0.0001(14) 0.001(2) C54 0.0246(16) 0.026(3) 0.0227(16) -0.0028(19) -0.0001(13) 0.0043(18) C55 0.0291(18) 0.027(3) 0.0294(19) 0.0065(19) 0.0002(14) -0.0058(18) C56 0.0291(18) 0.024(3) 0.0292(18) -0.0018(19) 0.0051(14) 0.0012(18) C57 0.0246(16) 0.027(3) 0.0213(16) -0.0004(18) 0.0031(13) 0.0020(18) C58 0.0362(19) 0.028(3) 0.0324(19) 0.005(2) 0.0043(15) -0.0007(19) C59 0.0315(18) 0.025(3) 0.0305(19) -0.0048(19) 0.0016(15) 0.0051(18) C60 0.0295(17) 0.017(2) 0.0266(17) 0.0050(17) 0.0047(13) 0.0058(17) C61 0.0258(16) 0.025(3) 0.0277(17) -0.0030(18) 0.0033(13) 0.0037(17) C62 0.0283(18) 0.030(3) 0.038(2) 0.002(2) 0.0042(15) -0.0048(18) C63 0.0328(19) 0.037(3) 0.040(2) -0.009(2) -0.0009(16) -0.011(2) C64 0.035(2) 0.043(3) 0.0304(19) -0.010(2) 0.0045(16) -0.004(2) C65 0.0248(16) 0.031(3) 0.0218(16) 0.0027(18) 0.0002(13) 0.0018(18) C66 0.0330(19) 0.052(4) 0.0241(18) -0.009(2) 0.0029(14) -0.004(2) C67 0.036(2) 0.060(4) 0.032(2) -0.006(2) -0.0082(16) -0.013(2) C68 0.0241(17) 0.041(3) 0.0341(19) 0.001(2) -0.0028(15) -0.0049(19) N1 0.0208(13) 0.021(2) 0.0376(17) -0.0053(16) -0.0051(12) 0.0046(14) N2 0.0236(13) 0.025(2) 0.0299(15) 0.0008(16) -0.0064(11) -0.0003(15) N3 0.0286(15) 0.044(3) 0.0277(15) 0.0072(17) -0.0026(12) 0.0004(16) N4 0.0294(15) 0.037(3) 0.0297(15) 0.0043(17) 0.0029(12) -0.0033(16) N5 0.0366(16) 0.052(3) 0.0319(17) 0.0031(18) 0.0073(13) -0.0086(18) N6 0.0365(17) 0.046(3) 0.0379(18) -0.0043(19) 0.0094(14) -0.0010(18) N7 0.0279(14) 0.035(2) 0.0257(14) -0.0026(16) 0.0073(11) -0.0044(15) N8 0.0234(13) 0.033(2) 0.0253(14) 0.0026(16) 0.0028(11) -0.0015(15) O1 0.0261(12) 0.035(2) 0.0429(14) 0.0084(14) -0.0144(10) -0.0040(13) O2 0.0336(13) 0.028(2) 0.0433(15) 0.0019(14) -0.0122(11) 0.0063(13) O3 0.0298(14) 0.078(3) 0.0624(19) -0.0141(19) -0.0091(13) 0.0013(16) O4 0.0420(17) 0.193(5) 0.0496(19) -0.029(3) -0.0118(14) -0.014(2) O5 0.0640(18) 0.037(2) 0.0448(16) -0.0144(17) 0.0208(13) -0.0067(17) O6 0.0594(17) 0.031(2) 0.0419(16) 0.0009(16) 0.0204(13) 0.0032(16) O7 0.0378(14) 0.039(2) 0.0295(13) 0.0057(14) 0.0095(11) 0.0053(14) O8 0.0701(19) 0.037(2) 0.0418(16) -0.0047(16) 0.0232(14) 0.0067(17) Ni1 0.0216(3) 0.0250(5) 0.0296(3) 0 -0.0098(2) 0 Ni2 0.0241(3) 0.0430(6) 0.0261(3) 0 -0.0001(2) 0 Ni3 0.0394(4) 0.0710(8) 0.0383(4) 0 0.0142(3) 0 Ni4 0.0241(3) 0.0353(6) 0.0238(3) 0 0.0037(2) 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O1 1.461(3) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 O2 1.209(4) . ? C2 O1 1.342(4) . ? C2 C3 1.497(4) . ? C3 C8 1.385(5) . ? C3 C4 1.390(5) . ? C4 C5 1.388(4) . ? C4 H4 0.95 . ? C5 C6 1.388(5) . ? C5 H5 0.95 . ? C6 C7 1.415(5) . ? C6 C9 1.501(4) . ? C7 C8 1.376(4) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C10 1.382(5) . ? C9 C14 1.395(5) . ? C10 N1 1.411(4) . ? C10 C11 1.420(5) . ? C11 C12 1.387(5) . ? C11 H11 0.95 . ? C12 C13 1.408(5) . ? C12 H12 0.95 . ? C13 N1 1.333(5) . ? C13 H13 0.95 . ? C14 N2 1.397(4) . ? C14 C15 1.409(5) . ? C15 C16 1.375(5) . ? C15 H15 0.95 . ? C16 C17 1.397(5) . ? C16 H16 0.95 . ? C17 N2 1.336(5) . ? C17 H17 0.95 . ? C18 O3 1.446(4) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 O4 1.188(5) . ? C19 O3 1.333(4) . ? C19 C20 1.489(5) . ? C20 C25 1.376(5) . ? C20 C21 1.396(5) . ? C21 C22 1.379(4) . ? C21 H21 0.95 . ? C22 C23 1.411(4) . ? C22 H22 0.95 . ? C23 C24 1.401(5) . ? C23 C26 1.493(4) . ? C24 C25 1.385(5) . ? C24 H24 0.95 . ? C25 H25 0.95 . ? C26 C27 1.399(5) . ? C26 C31 1.404(5) . ? C27 N3 1.397(4) . ? C27 C28 1.418(5) . ? C28 C29 1.356(5) . ? C28 H28 0.95 . ? C29 C30 1.395(5) . ? C29 H29 0.95 . ? C30 N3 1.335(5) . ? C30 H30 0.95 . ? C31 N4 1.395(4) . ? C31 C32 1.404(5) . ? C32 C33 1.385(5) . ? C32 H32 0.95 . ? C33 C34 1.423(5) . ? C33 H33 0.95 . ? C34 N4 1.352(5) . ? C34 H34 0.95 . ? C35 O5 1.465(4) . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? C36 O6 1.177(5) . ? C36 O5 1.349(5) . ? C36 C37 1.509(5) . ? C37 C42 1.378(6) . ? C37 C38 1.406(6) . ? C38 C39 1.402(5) . ? C38 H38 0.95 . ? C39 C40 1.376(6) . ? C39 H39 0.95 . ? C40 C41 1.387(5) . ? C40 C43 1.514(4) . ? C41 C42 1.379(4) . ? C41 H41 0.95 . ? C42 H42 0.95 . ? C43 C44 1.396(5) . ? C43 C48 1.404(5) . ? C44 C45 1.412(5) . ? C44 N5 1.416(4) . ? C45 C46 1.364(5) . ? C45 H45 0.95 . ? C46 C47 1.400(6) . ? C46 H46 0.95 . ? C47 N5 1.337(5) . ? C47 H47 0.95 . ? C48 C49 1.410(5) . ? C48 N6 1.419(4) . ? C49 C50 1.371(6) . ? C49 H49 0.95 . ? C50 C51 1.405(5) . ? C50 H50 0.95 . ? C51 N6 1.334(5) . ? C51 H51 0.95 . ? C52 O7 1.446(4) . ? C52 H52A 0.98 . ? C52 H52B 0.98 . ? C52 H52C 0.98 . ? C53 O8 1.200(5) . ? C53 O7 1.339(5) . ? C53 C54 1.496(5) . ? C54 C55 1.386(5) . ? C54 C59 1.388(5) . ? C55 C56 1.398(4) . ? C55 H55 0.95 . ? C56 C57 1.394(5) . ? C56 H56 0.95 . ? C57 C58 1.388(5) . ? C57 C60 1.496(4) . ? C58 C59 1.394(4) . ? C58 H58 0.95 . ? C59 H59 0.95 . ? C60 C61 1.383(4) . ? C60 C65 1.393(4) . ? C61 N7 1.399(4) . ? C61 C62 1.430(5) . ? C62 C63 1.360(5) . ? C62 H62 0.95 . ? C63 C64 1.409(5) . ? C63 H63 0.95 . ? C64 N7 1.335(4) . ? C64 H64 0.95 . ? C65 C66 1.402(5) . ? C65 N8 1.409(4) . ? C66 C67 1.361(4) . ? C66 H66 0.95 . ? C67 C68 1.385(5) . ? C67 H67 0.95 . ? C68 N8 1.345(4) . ? C68 H68 0.95 . ? N1 Ni1 1.885(3) . ? N2 Ni1 1.891(3) . ? N3 Ni2 1.891(3) . ? N4 Ni2 1.886(3) . ? N5 Ni3 1.962(3) . ? N6 Ni3 1.939(3) . ? N7 Ni4 1.891(3) . ? N8 Ni4 1.889(3) . ? Ni1 N1 1.885(3) 2 ? Ni1 N2 1.891(3) 2 ? Ni2 N4 1.886(3) 2_655 ? Ni2 N3 1.891(3) 2_655 ? Ni3 N6 1.939(3) 2_655 ? Ni3 N5 1.962(3) 2_655 ? Ni4 N8 1.889(3) 2_655 ? Ni4 N7 1.891(3) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 123.3(3) . . ? O2 C2 C3 123.5(4) . . ? O1 C2 C3 113.1(3) . . ? C8 C3 C4 119.8(3) . . ? C8 C3 C2 117.1(3) . . ? C4 C3 C2 123.1(3) . . ? C5 C4 C3 119.9(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.9(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C7 118.6(3) . . ? C5 C6 C9 121.9(3) . . ? C7 C6 C9 119.5(3) . . ? C8 C7 C6 120.0(3) . . ? C8 C7 H7 120 . . ? C6 C7 H7 120 . . ? C7 C8 C3 120.7(4) . . ? C7 C8 H8 119.6 . . ? C3 C8 H8 119.6 . . ? C10 C9 C14 123.7(3) . . ? C10 C9 C6 118.4(3) . . ? C14 C9 C6 117.9(3) . . ? C9 C10 N1 122.5(3) . . ? C9 C10 C11 129.4(3) . . ? N1 C10 C11 108.0(3) . . ? C12 C11 C10 107.5(3) . . ? C12 C11 H11 126.3 . . ? C10 C11 H11 126.3 . . ? C11 C12 C13 105.9(3) . . ? C11 C12 H12 127 . . ? C13 C12 H12 127 . . ? N1 C13 C12 112.0(3) . . ? N1 C13 H13 124 . . ? C12 C13 H13 124 . . ? C9 C14 N2 123.0(3) . . ? C9 C14 C15 128.9(3) . . ? N2 C14 C15 108.1(3) . . ? C16 C15 C14 107.3(3) . . ? C16 C15 H15 126.3 . . ? C14 C15 H15 126.3 . . ? C15 C16 C17 106.7(3) . . ? C15 C16 H16 126.6 . . ? C17 C16 H16 126.6 . . ? N2 C17 C16 110.9(3) . . ? N2 C17 H17 124.5 . . ? C16 C17 H17 124.5 . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 C19 O3 122.3(4) . . ? O4 C19 C20 124.4(4) . . ? O3 C19 C20 113.2(3) . . ? C25 C20 C21 119.6(3) . . ? C25 C20 C19 117.9(3) . . ? C21 C20 C19 122.5(3) . . ? C22 C21 C20 120.5(3) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 120.2(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 118.6(3) . . ? C24 C23 C26 120.3(3) . . ? C22 C23 C26 121.1(3) . . ? C25 C24 C23 120.2(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C20 C25 C24 120.9(4) . . ? C20 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C27 C26 C31 123.9(3) . . ? C27 C26 C23 118.1(3) . . ? C31 C26 C23 117.9(3) . . ? N3 C27 C26 123.2(3) . . ? N3 C27 C28 108.0(3) . . ? C26 C27 C28 128.6(3) . . ? C29 C28 C27 107.5(3) . . ? C29 C28 H28 126.2 . . ? C27 C28 H28 126.2 . . ? C28 C29 C30 106.8(3) . . ? C28 C29 H29 126.6 . . ? C30 C29 H29 126.6 . . ? N3 C30 C29 111.5(3) . . ? N3 C30 H30 124.3 . . ? C29 C30 H30 124.3 . . ? N4 C31 C26 122.1(3) . . ? N4 C31 C32 108.4(3) . . ? C26 C31 C32 129.3(3) . . ? C33 C32 C31 108.9(3) . . ? C33 C32 H32 125.6 . . ? C31 C32 H32 125.6 . . ? C32 C33 C34 104.7(4) . . ? C32 C33 H33 127.7 . . ? C34 C33 H33 127.7 . . ? N4 C34 C33 111.5(3) . . ? N4 C34 H34 124.2 . . ? C33 C34 H34 124.2 . . ? O5 C35 H35A 109.5 . . ? O5 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O5 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O6 C36 O5 124.6(4) . . ? O6 C36 C37 123.9(4) . . ? O5 C36 C37 111.5(4) . . ? C42 C37 C38 119.8(3) . . ? C42 C37 C36 116.7(4) . . ? C38 C37 C36 123.5(4) . . ? C39 C38 C37 119.0(4) . . ? C39 C38 H38 120.5 . . ? C37 C38 H38 120.5 . . ? C40 C39 C38 121.0(4) . . ? C40 C39 H39 119.5 . . ? C38 C39 H39 119.5 . . ? C39 C40 C41 118.7(3) . . ? C39 C40 C43 122.3(4) . . ? C41 C40 C43 118.9(4) . . ? C42 C41 C40 121.5(4) . . ? C42 C41 H41 119.2 . . ? C40 C41 H41 119.2 . . ? C37 C42 C41 119.9(4) . . ? C37 C42 H42 120 . . ? C41 C42 H42 120 . . ? C44 C43 C48 126.9(3) . . ? C44 C43 C40 116.5(3) . . ? C48 C43 C40 116.6(3) . . ? C43 C44 C45 129.2(3) . . ? C43 C44 N5 122.0(4) . . ? C45 C44 N5 108.5(3) . . ? C46 C45 C44 107.6(4) . . ? C46 C45 H45 126.2 . . ? C44 C45 H45 126.2 . . ? C45 C46 C47 106.4(4) . . ? C45 C46 H46 126.8 . . ? C47 C46 H46 126.8 . . ? N5 C47 C46 112.3(4) . . ? N5 C47 H47 123.8 . . ? C46 C47 H47 123.8 . . ? C43 C48 C49 129.7(3) . . ? C43 C48 N6 123.1(3) . . ? C49 C48 N6 107.2(3) . . ? C50 C49 C48 109.3(3) . . ? C50 C49 H49 125.4 . . ? C48 C49 H49 125.4 . . ? C49 C50 C51 104.9(4) . . ? C49 C50 H50 127.6 . . ? C51 C50 H50 127.6 . . ? N6 C51 C50 112.8(4) . . ? N6 C51 H51 123.6 . . ? C50 C51 H51 123.6 . . ? O7 C52 H52A 109.5 . . ? O7 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? O7 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O8 C53 O7 123.9(3) . . ? O8 C53 C54 124.5(4) . . ? O7 C53 C54 111.5(4) . . ? C55 C54 C59 120.0(3) . . ? C55 C54 C53 121.1(4) . . ? C59 C54 C53 118.9(4) . . ? C54 C55 C56 120.0(4) . . ? C54 C55 H55 120 . . ? C56 C55 H55 120 . . ? C57 C56 C55 120.2(4) . . ? C57 C56 H56 119.9 . . ? C55 C56 H56 119.9 . . ? C58 C57 C56 119.2(3) . . ? C58 C57 C60 121.8(4) . . ? C56 C57 C60 119.0(4) . . ? C57 C58 C59 120.7(4) . . ? C57 C58 H58 119.6 . . ? C59 C58 H58 119.6 . . ? C54 C59 C58 119.8(4) . . ? C54 C59 H59 120.1 . . ? C58 C59 H59 120.1 . . ? C61 C60 C65 125.3(3) . . ? C61 C60 C57 117.9(3) . . ? C65 C60 C57 116.8(3) . . ? C60 C61 N7 122.6(3) . . ? C60 C61 C62 129.3(3) . . ? N7 C61 C62 108.1(3) . . ? C63 C62 C61 107.1(3) . . ? C63 C62 H62 126.4 . . ? C61 C62 H62 126.4 . . ? C62 C63 C64 106.9(3) . . ? C62 C63 H63 126.5 . . ? C64 C63 H63 126.5 . . ? N7 C64 C63 111.3(3) . . ? N7 C64 H64 124.3 . . ? C63 C64 H64 124.3 . . ? C60 C65 C66 129.0(3) . . ? C60 C65 N8 122.4(3) . . ? C66 C65 N8 108.6(3) . . ? C67 C66 C65 107.4(3) . . ? C67 C66 H66 126.3 . . ? C65 C66 H66 126.3 . . ? C66 C67 C68 107.0(3) . . ? C66 C67 H67 126.5 . . ? C68 C67 H67 126.5 . . ? N8 C68 C67 111.7(3) . . ? N8 C68 H68 124.1 . . ? C67 C68 H68 124.1 . . ? C13 N1 C10 106.6(3) . . ? C13 N1 Ni1 122.0(2) . . ? C10 N1 Ni1 126.6(3) . . ? C17 N2 C14 106.9(3) . . ? C17 N2 Ni1 122.2(2) . . ? C14 N2 Ni1 126.6(3) . . ? C30 N3 C27 106.2(3) . . ? C30 N3 Ni2 122.0(2) . . ? C27 N3 Ni2 127.4(2) . . ? C34 N4 C31 106.4(3) . . ? C34 N4 Ni2 121.8(2) . . ? C31 N4 Ni2 129.2(2) . . ? C47 N5 C44 105.2(3) . . ? C47 N5 Ni3 126.8(3) . . ? C44 N5 Ni3 127.7(3) . . ? C51 N6 C48 105.9(3) . . ? C51 N6 Ni3 126.7(3) . . ? C48 N6 Ni3 127.5(3) . . ? C64 N7 C61 106.6(3) . . ? C64 N7 Ni4 124.1(2) . . ? C61 N7 Ni4 128.6(2) . . ? C68 N8 C65 105.2(3) . . ? C68 N8 Ni4 125.3(2) . . ? C65 N8 Ni4 128.2(2) . . ? C2 O1 C1 113.5(3) . . ? C19 O3 C18 116.2(3) . . ? C36 O5 C35 114.1(4) . . ? C53 O7 C52 116.0(3) . . ? N1 Ni1 N1 97.61(19) . 2 ? N1 Ni1 N2 147.12(12) . 2 ? N1 Ni1 N2 92.73(12) 2 2 ? N1 Ni1 N2 92.73(12) . . ? N1 Ni1 N2 147.12(11) 2 . ? N2 Ni1 N2 95.29(19) 2 . ? N4 Ni2 N4 151.7(2) 2_655 . ? N4 Ni2 N3 95.89(12) 2_655 . ? N4 Ni2 N3 92.08(11) . . ? N4 Ni2 N3 92.08(11) 2_655 2_655 ? N4 Ni2 N3 95.89(12) . 2_655 ? N3 Ni2 N3 147.0(2) . 2_655 ? N6 Ni3 N6 146.7(2) 2_655 . ? N6 Ni3 N5 91.96(13) 2_655 2_655 ? N6 Ni3 N5 106.62(13) . 2_655 ? N6 Ni3 N5 106.62(13) 2_655 . ? N6 Ni3 N5 91.96(13) . . ? N5 Ni3 N5 112.0(2) 2_655 . ? N8 Ni4 N8 149.1(2) . 2_655 ? N8 Ni4 N7 92.30(11) . . ? N8 Ni4 N7 95.03(11) 2_655 . ? N8 Ni4 N7 95.03(11) . 2_655 ? N8 Ni4 N7 92.30(11) 2_655 2_655 ? N7 Ni4 N7 152.3(2) . 2_655 ? #===END data_Zn[L]2 _database_code_depnum_ccdc_archive 'CCDC 835356' #TrackingRef '- Cif Global CrystEngComm_vigroux.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H26 N4 O4 Zn' _chemical_formula_sum 'C34 H26 N4 O4 Zn' _chemical_formula_weight 619.98 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.5320(13) _cell_length_b 11.0426(10) _cell_length_c 22.891(3) _cell_angle_alpha 90 _cell_angle_beta 90.073(4) _cell_angle_gamma 90 _cell_volume 2915.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2125 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 23.63 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.889 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_T_max 0.9653 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'microfocus sealed tube' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'Bruker Kappa APEX II Quazar' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0739 _diffrn_reflns_av_unetI/netI 0.0937 _diffrn_reflns_number 19463 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 5902 _reflns_number_gt 3518 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0453P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5902 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1044 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.348 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.073 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 Zn2 Zn 0.5 0.44611(5) 0.25 0.02613(17) Uani 1 2 d S . . Zn1 Zn 0.5 0.95867(5) 0.25 0.02758(18) Uani 1 2 d S . . N4 N 0.6463(2) 0.5370(2) 0.24014(13) 0.0259(7) Uani 1 1 d . . . N1 N 0.6446(2) 1.0468(2) 0.23127(12) 0.0253(7) Uani 1 1 d . . . C26 C 0.7435(3) 0.4566(3) 0.32921(15) 0.0233(8) Uani 1 1 d . . . C28 C 0.3386(3) 0.3012(3) 0.10094(15) 0.0295(8) Uani 1 1 d . . . H28 H 0.2772 0.2963 0.0733 0.035 Uiso 1 1 calc R . . C29 C 0.4406(3) 0.2357(3) 0.10019(17) 0.0339(9) Uani 1 1 d . . . H29 H 0.4624 0.1763 0.0722 0.041 Uiso 1 1 calc R . . O1 O 0.8961(2) 1.1076(2) -0.11702(11) 0.0447(8) Uani 1 1 d . . . C16 C 0.4373(4) 0.7505(4) 0.10086(18) 0.0479(12) Uani 1 1 d . . . H16 H 0.3939 0.693 0.079 0.057 Uiso 1 1 calc R . . C22 C 0.9281(3) 0.3722(3) 0.37071(17) 0.0322(9) Uani 1 1 d . . . H22 H 0.9089 0.2958 0.3543 0.039 Uiso 1 1 calc R . . C9 C 0.6626(3) 0.9702(3) 0.13015(15) 0.0242(8) Uani 1 1 d . . . C23 C 0.8514(3) 0.4675(3) 0.36486(15) 0.0232(8) Uani 1 1 d . . . N2 N 0.4951(2) 0.8685(2) 0.17616(13) 0.0286(7) Uani 1 1 d . . . O2 O 0.9552(2) 0.9156(2) -0.11013(12) 0.0439(8) Uani 1 1 d . . . C19 C 1.1735(3) 0.5203(3) 0.45456(16) 0.0269(8) Uani 1 1 d . . . N3 N 0.4488(2) 0.3577(2) 0.17972(12) 0.0253(7) Uani 1 1 d . . . O4 O 1.1974(2) 0.6136(2) 0.47856(12) 0.0410(7) Uani 1 1 d . . . C31 C 0.7409(3) 0.5276(3) 0.27796(15) 0.0235(8) Uani 1 1 d . . . C8 C 0.8508(3) 0.8939(3) 0.00001(15) 0.0261(8) Uani 1 1 d . . . H8 H 0.8927 0.8263 -0.0145 0.031 Uiso 1 1 calc R . . C10 C 0.7003(3) 1.0414(3) 0.17743(15) 0.0255(8) Uani 1 1 d . . . C32 C 0.8327(3) 0.5986(3) 0.25484(16) 0.0309(9) Uani 1 1 d . . . H32 H 0.9078 0.6079 0.2713 0.037 Uiso 1 1 calc R . . C25 C 0.9810(3) 0.5915(3) 0.42177(15) 0.0266(8) Uani 1 1 d . . . H25 H 0.9978 0.6666 0.4402 0.032 Uiso 1 1 calc R . . C20 C 1.0598(3) 0.4965(3) 0.42544(15) 0.0251(8) Uani 1 1 d . . . O3 O 1.2480(2) 0.4274(2) 0.45007(12) 0.0400(7) Uani 1 1 d . . . C27 C 0.3431(3) 0.3778(3) 0.15099(15) 0.0236(8) Uani 1 1 d . . . C2 C 0.9059(3) 1.0009(3) -0.08957(16) 0.0311(9) Uani 1 1 d . . . C7 C 0.7921(3) 0.8847(3) 0.05279(15) 0.0288(9) Uani 1 1 d . . . H7 H 0.794 0.8108 0.074 0.035 Uiso 1 1 calc R . . C6 C 0.7309(3) 0.9822(3) 0.07476(15) 0.0269(9) Uani 1 1 d . . . C11 C 0.7998(3) 1.1179(3) 0.17965(18) 0.0376(10) Uani 1 1 d . . . H11 H 0.8539 1.1309 0.149 0.045 Uiso 1 1 calc R . . C3 C 0.8486(3) 1.0002(3) -0.03132(15) 0.0266(8) Uani 1 1 d . . . C15 C 0.5309(3) 0.8146(3) 0.08190(17) 0.0406(10) Uani 1 1 d . . . H15 H 0.5647 0.8102 0.0442 0.049 Uiso 1 1 calc R . . C4 C 0.7912(3) 1.1000(3) -0.00834(17) 0.0413(11) Uani 1 1 d . . . H4 H 0.7915 1.1746 -0.029 0.05 Uiso 1 1 calc R . . C17 C 0.4176(3) 0.7858(3) 0.15867(17) 0.0372(10) Uani 1 1 d . . . H17 H 0.3569 0.755 0.1825 0.045 Uiso 1 1 calc R . . C24 C 0.8786(3) 0.5770(3) 0.39151(15) 0.0241(8) Uani 1 1 d . . . H24 H 0.8259 0.6428 0.3888 0.029 Uiso 1 1 calc R . . C30 C 0.5058(3) 0.2736(3) 0.14876(16) 0.0297(9) Uani 1 1 d . . . H30 H 0.5806 0.2436 0.1584 0.036 Uiso 1 1 calc R . . C14 C 0.5687(3) 0.8892(3) 0.12868(15) 0.0261(8) Uani 1 1 d . . . C21 C 1.0317(3) 0.3859(3) 0.39982(16) 0.0333(9) Uani 1 1 d . . . H21 H 1.0841 0.3197 0.4025 0.04 Uiso 1 1 calc R . . C34 C 0.6786(3) 0.6108(3) 0.19715(16) 0.0360(9) Uani 1 1 d . . . H34 H 0.6302 0.6335 0.1654 0.043 Uiso 1 1 calc R . . C5 C 0.7334(3) 1.0910(3) 0.04468(17) 0.0412(11) Uani 1 1 d . . . H5 H 0.6953 1.1599 0.0604 0.049 Uiso 1 1 calc R . . C18 C 1.3627(3) 0.4527(4) 0.4730(2) 0.0499(12) Uani 1 1 d . . . H18A H 1.4011 0.5128 0.4481 0.075 Uiso 1 1 calc R . . H18B H 1.4084 0.378 0.4735 0.075 Uiso 1 1 calc R . . H18C H 1.356 0.4846 0.5128 0.075 Uiso 1 1 calc R . . C13 C 0.7064(3) 1.1225(3) 0.26461(18) 0.0364(10) Uani 1 1 d . . . H13 H 0.6879 1.1425 0.3039 0.044 Uiso 1 1 calc R . . C12 C 0.8029(3) 1.1689(3) 0.23377(19) 0.0432(11) Uani 1 1 d . . . H12 H 0.8589 1.2247 0.248 0.052 Uiso 1 1 calc R . . C1 C 0.9460(4) 1.1111(4) -0.17509(18) 0.0565(14) Uani 1 1 d . . . H1A H 1.0288 1.0915 -0.1728 0.085 Uiso 1 1 calc R . . H1B H 0.9364 1.1924 -0.1916 0.085 Uiso 1 1 calc R . . H1C H 0.9067 1.0519 -0.2001 0.085 Uiso 1 1 calc R . . C33 C 0.7929(4) 0.6509(4) 0.20469(19) 0.0454(11) Uani 1 1 d . . . H33 H 0.8345 0.7041 0.1798 0.055 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 Zn2 0.0217(3) 0.0309(3) 0.0259(4) 0 -0.0042(3) 0 Zn1 0.0289(4) 0.0320(3) 0.0219(4) 0 0.0103(3) 0 N4 0.0245(16) 0.0296(15) 0.0236(18) 0.0039(14) -0.0039(13) 0.0006(13) N1 0.0260(16) 0.0266(15) 0.0235(18) -0.0033(13) 0.0069(13) 0.0007(13) C26 0.0222(18) 0.0207(17) 0.027(2) -0.0084(16) -0.0059(15) 0.0041(15) C28 0.038(2) 0.0274(19) 0.024(2) 0.0000(17) -0.0063(17) -0.0027(17) C29 0.041(3) 0.031(2) 0.029(2) -0.0035(17) -0.0025(19) 0.0089(17) O1 0.069(2) 0.0321(14) 0.0335(17) 0.0092(12) 0.0255(15) 0.0117(13) C16 0.043(3) 0.064(3) 0.037(3) -0.017(2) 0.001(2) -0.017(2) C22 0.033(2) 0.0223(18) 0.042(3) -0.0083(17) -0.0131(19) 0.0001(15) C9 0.028(2) 0.0204(17) 0.024(2) 0.0059(15) 0.0107(16) 0.0090(14) C23 0.0219(18) 0.0240(17) 0.024(2) -0.0011(15) -0.0022(15) -0.0012(14) N2 0.0280(18) 0.0299(16) 0.0280(19) 0.0009(13) 0.0095(14) 0.0013(13) O2 0.063(2) 0.0279(14) 0.0409(18) -0.0010(12) 0.0294(15) 0.0047(13) C19 0.033(2) 0.0234(19) 0.024(2) 0.0035(16) -0.0053(17) -0.0005(16) N3 0.0261(17) 0.0285(16) 0.0212(18) 0.0001(13) -0.0017(14) 0.0039(13) O4 0.0424(17) 0.0244(14) 0.056(2) -0.0035(13) -0.0240(14) -0.0014(11) C31 0.0194(18) 0.0270(18) 0.024(2) -0.0036(16) 0.0005(15) 0.0024(14) C8 0.032(2) 0.0206(18) 0.026(2) -0.0022(16) 0.0068(17) 0.0053(15) C10 0.0281(19) 0.0227(17) 0.026(2) 0.0015(16) 0.0103(16) 0.0060(15) C32 0.022(2) 0.039(2) 0.032(2) -0.0017(18) 0.0012(17) -0.0089(16) C25 0.030(2) 0.0219(18) 0.028(2) -0.0049(16) -0.0029(17) -0.0002(15) C20 0.026(2) 0.0263(18) 0.023(2) -0.0010(16) -0.0056(16) -0.0029(15) O3 0.0296(15) 0.0366(15) 0.0538(19) -0.0116(13) -0.0133(13) 0.0054(12) C27 0.0227(19) 0.0230(18) 0.025(2) 0.0051(16) -0.0054(16) -0.0004(14) C2 0.037(2) 0.0267(19) 0.029(2) 0.0024(18) 0.0089(19) -0.0015(17) C7 0.038(2) 0.0219(18) 0.027(2) 0.0060(16) 0.0081(18) 0.0030(15) C6 0.030(2) 0.0258(19) 0.025(2) 0.0046(16) 0.0090(17) 0.0021(15) C11 0.036(2) 0.029(2) 0.048(3) -0.0023(19) 0.019(2) -0.0064(17) C3 0.033(2) 0.0234(17) 0.024(2) 0.0000(16) 0.0105(17) 0.0029(15) C15 0.037(2) 0.062(3) 0.023(2) -0.006(2) 0.0054(18) -0.003(2) C4 0.059(3) 0.028(2) 0.037(3) 0.0129(18) 0.023(2) 0.0125(19) C17 0.033(2) 0.044(2) 0.034(3) -0.004(2) 0.0062(19) -0.0061(18) C24 0.0222(19) 0.0224(17) 0.028(2) -0.0030(15) -0.0044(16) 0.0015(14) C30 0.026(2) 0.034(2) 0.029(2) 0.0012(17) 0.0001(17) 0.0067(16) C14 0.029(2) 0.0318(19) 0.017(2) 0.0000(16) 0.0027(16) 0.0033(16) C21 0.030(2) 0.0256(19) 0.044(3) -0.0079(18) -0.0119(19) 0.0073(16) C34 0.040(2) 0.044(2) 0.025(2) 0.0063(19) -0.0044(19) -0.0018(19) C5 0.053(3) 0.031(2) 0.040(3) 0.0066(19) 0.024(2) 0.0148(18) C18 0.032(2) 0.055(3) 0.063(3) -0.007(2) -0.019(2) 0.007(2) C13 0.036(2) 0.037(2) 0.036(3) -0.0089(19) 0.0100(19) -0.0007(17) C12 0.037(2) 0.042(2) 0.050(3) -0.017(2) 0.011(2) -0.0128(18) C1 0.087(4) 0.049(2) 0.034(3) 0.014(2) 0.033(3) 0.010(2) C33 0.047(3) 0.052(2) 0.037(3) 0.012(2) 0.004(2) -0.017(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Zn2 N3 1.972(3) . ? Zn2 N3 1.972(3) 2_655 ? Zn2 N4 1.976(3) 2_655 ? Zn2 N4 1.976(3) . ? Zn1 N2 1.962(3) 2_655 ? Zn1 N2 1.962(3) . ? Zn1 N1 1.978(3) . ? Zn1 N1 1.978(3) 2_655 ? N4 C34 1.331(4) . ? N4 C31 1.396(4) . ? N1 C13 1.337(4) . ? N1 C10 1.392(4) . ? C26 C27 1.401(4) 2_655 ? C26 C31 1.411(5) . ? C26 C23 1.492(4) . ? C28 C29 1.381(5) . ? C28 C27 1.425(5) . ? C28 H28 0.95 . ? C29 C30 1.405(5) . ? C29 H29 0.95 . ? O1 C2 1.341(4) . ? O1 C1 1.450(4) . ? C16 C15 1.362(5) . ? C16 C17 1.399(5) . ? C16 H16 0.95 . ? C22 C21 1.375(5) . ? C22 C23 1.381(4) . ? C22 H22 0.95 . ? C9 C14 1.405(5) . ? C9 C10 1.406(5) . ? C9 C6 1.500(4) . ? C23 C24 1.390(4) . ? N2 C17 1.339(4) . ? N2 C14 1.399(4) . ? O2 C2 1.197(4) . ? C19 O4 1.199(4) . ? C19 O3 1.342(4) . ? C19 C20 1.493(5) . ? N3 C30 1.341(4) . ? N3 C27 1.401(4) . ? C31 C32 1.420(4) . ? C8 C3 1.375(4) . ? C8 C7 1.389(4) . ? C8 H8 0.95 . ? C10 C11 1.425(5) . ? C32 C33 1.364(5) . ? C32 H32 0.95 . ? C25 C24 1.377(5) . ? C25 C20 1.391(4) . ? C25 H25 0.95 . ? C20 C21 1.394(4) . ? O3 C18 1.449(4) . ? C27 C26 1.401(4) 2_655 ? C2 C3 1.489(5) . ? C7 C6 1.381(4) . ? C7 H7 0.95 . ? C6 C5 1.385(4) . ? C11 C12 1.361(5) . ? C11 H11 0.95 . ? C3 C4 1.389(4) . ? C15 C14 1.419(5) . ? C15 H15 0.95 . ? C4 C5 1.389(5) . ? C4 H4 0.95 . ? C17 H17 0.95 . ? C24 H24 0.95 . ? C30 H30 0.95 . ? C21 H21 0.95 . ? C34 C33 1.401(5) . ? C34 H34 0.95 . ? C5 H5 0.95 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C13 C12 1.415(5) . ? C13 H13 0.95 . ? C12 H12 0.95 . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C33 H33 0.95 . ? 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 N3 Zn2 N3 120.63(15) . 2_655 ? N3 Zn2 N4 95.16(11) . 2_655 ? N3 Zn2 N4 114.41(11) 2_655 2_655 ? N3 Zn2 N4 114.41(11) . . ? N3 Zn2 N4 95.16(11) 2_655 . ? N4 Zn2 N4 118.94(15) 2_655 . ? N2 Zn1 N2 119.02(16) 2_655 . ? N2 Zn1 N1 114.39(12) 2_655 . ? N2 Zn1 N1 94.96(11) . . ? N2 Zn1 N1 94.96(11) 2_655 2_655 ? N2 Zn1 N1 114.39(12) . 2_655 ? N1 Zn1 N1 121.04(15) . 2_655 ? C34 N4 C31 106.6(3) . . ? C34 N4 Zn2 129.4(3) . . ? C31 N4 Zn2 123.9(2) . . ? C13 N1 C10 106.6(3) . . ? C13 N1 Zn1 129.3(2) . . ? C10 N1 Zn1 124.1(2) . . ? C27 C26 C31 126.9(3) 2_655 . ? C27 C26 C23 117.9(3) 2_655 . ? C31 C26 C23 115.2(3) . . ? C29 C28 C27 106.9(3) . . ? C29 C28 H28 126.5 . . ? C27 C28 H28 126.5 . . ? C28 C29 C30 106.8(3) . . ? C28 C29 H29 126.6 . . ? C30 C29 H29 126.6 . . ? C2 O1 C1 114.8(3) . . ? C15 C16 C17 106.6(4) . . ? C15 C16 H16 126.7 . . ? C17 C16 H16 126.7 . . ? C21 C22 C23 121.3(3) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C14 C9 C10 127.8(3) . . ? C14 C9 C6 116.2(3) . . ? C10 C9 C6 116.0(3) . . ? C22 C23 C24 118.4(3) . . ? C22 C23 C26 121.7(3) . . ? C24 C23 C26 119.9(3) . . ? C17 N2 C14 106.5(3) . . ? C17 N2 Zn1 128.5(2) . . ? C14 N2 Zn1 124.7(2) . . ? O4 C19 O3 123.0(3) . . ? O4 C19 C20 123.9(3) . . ? O3 C19 C20 113.1(3) . . ? C30 N3 C27 106.7(3) . . ? C30 N3 Zn2 128.9(3) . . ? C27 N3 Zn2 124.3(2) . . ? N4 C31 C26 124.9(3) . . ? N4 C31 C32 108.1(3) . . ? C26 C31 C32 127.0(3) . . ? C3 C8 C7 120.5(3) . . ? C3 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? N1 C10 C9 124.2(3) . . ? N1 C10 C11 108.4(3) . . ? C9 C10 C11 127.4(3) . . ? C33 C32 C31 107.3(3) . . ? C33 C32 H32 126.4 . . ? C31 C32 H32 126.4 . . ? C24 C25 C20 120.2(3) . . ? C24 C25 H25 119.9 . . ? C20 C25 H25 119.9 . . ? C25 C20 C21 119.0(3) . . ? C25 C20 C19 117.9(3) . . ? C21 C20 C19 123.1(3) . . ? C19 O3 C18 114.1(3) . . ? C26 C27 N3 124.5(3) 2_655 . ? C26 C27 C28 127.1(3) 2_655 . ? N3 C27 C28 108.3(3) . . ? O2 C2 O1 123.2(3) . . ? O2 C2 C3 124.0(3) . . ? O1 C2 C3 112.7(3) . . ? C6 C7 C8 120.6(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C6 C5 119.0(3) . . ? C7 C6 C9 120.5(3) . . ? C5 C6 C9 120.5(3) . . ? C12 C11 C10 107.4(3) . . ? C12 C11 H11 126.3 . . ? C10 C11 H11 126.3 . . ? C8 C3 C4 119.2(3) . . ? C8 C3 C2 117.6(3) . . ? C4 C3 C2 123.2(3) . . ? C16 C15 C14 107.7(3) . . ? C16 C15 H15 126.1 . . ? C14 C15 H15 126.1 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? N2 C17 C16 111.3(3) . . ? N2 C17 H17 124.3 . . ? C16 C17 H17 124.3 . . ? C25 C24 C23 121.0(3) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? N3 C30 C29 111.3(3) . . ? N3 C30 H30 124.4 . . ? C29 C30 H30 124.4 . . ? N2 C14 C9 123.6(3) . . ? N2 C14 C15 107.8(3) . . ? C9 C14 C15 128.6(3) . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? N4 C34 C33 111.5(3) . . ? N4 C34 H34 124.3 . . ? C33 C34 H34 124.3 . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C13 C12 111.2(3) . . ? N1 C13 H13 124.4 . . ? C12 C13 H13 124.4 . . ? C11 C12 C13 106.5(3) . . ? C11 C12 H12 126.8 . . ? C13 C12 H12 126.8 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C32 C33 C34 106.6(3) . . ? C32 C33 H33 126.7 . . ? C34 C33 H33 126.7 . . ? #===END data_Cu[L]2 _database_code_depnum_ccdc_archive 'CCDC 835357' #TrackingRef '- Cif Global CrystEngComm_vigroux.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H26 Cu N4 O4' _chemical_formula_sum 'C34 H26 Cu N4 O4' _chemical_formula_weight 618.14 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 23.0164(6) _cell_length_b 20.7890(6) _cell_length_c 23.3891(7) _cell_angle_alpha 90 _cell_angle_beta 90.592(2) _cell_angle_gamma 90 _cell_volume 11190.8(5) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7572 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 23.72 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5104 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.829 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_T_max 0.975 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEX II' _diffrn_measurement_method \w-\f _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.1145 _diffrn_reflns_av_unetI/netI 0.1321 _diffrn_reflns_number 78344 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 11351 _reflns_number_gt 5702 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0584P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 11351 _refine_ls_number_parameters 781 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.123 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.125 _refine_ls_wR_factor_gt 0.108 _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_restrained_S_all 0.878 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.236 _refine_diff_density_min -0.909 _refine_diff_density_rms 0.079 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C61 C 0.10806(16) 0.51877(16) 0.68262(16) 0.0196(9) Uani 1 1 d . . . C60 C 0.08374(15) 0.49148(16) 0.63332(16) 0.0188(9) Uani 1 1 d . . . C57 C 0.12051(15) 0.49007(17) 0.58107(16) 0.0185(9) Uani 1 1 d . . . C56 C 0.13320(16) 0.54847(17) 0.55424(16) 0.0218(9) Uani 1 1 d . . . H56 H 0.1206 0.5878 0.5706 0.026 Uiso 1 1 calc R . . C55 C 0.16402(16) 0.54890(17) 0.50398(17) 0.0226(9) Uani 1 1 d . . . H55 H 0.1723 0.5887 0.4858 0.027 Uiso 1 1 calc R . . C54 C 0.18290(15) 0.49214(17) 0.47982(16) 0.0203(9) Uani 1 1 d . . . C53 C 0.21226(16) 0.49065(19) 0.42287(17) 0.0230(9) Uani 1 1 d . . . C52 C 0.24129(19) 0.5531(2) 0.34397(17) 0.0366(11) Uani 1 1 d . . . H52A H 0.2817 0.5385 0.3474 0.055 Uiso 1 1 calc R . . H52B H 0.2406 0.5978 0.3305 0.055 Uiso 1 1 calc R . . H52C H 0.2203 0.5257 0.3166 0.055 Uiso 1 1 calc R . . C59 C 0.17250(16) 0.43383(17) 0.50821(16) 0.0224(9) Uani 1 1 d . . . H59 H 0.187 0.3946 0.4932 0.027 Uiso 1 1 calc R . . C58 C 0.14118(16) 0.43374(17) 0.55787(17) 0.0233(9) Uani 1 1 d . . . H58 H 0.1336 0.3941 0.5766 0.028 Uiso 1 1 calc R . . C65 C 0.02803(16) 0.46494(16) 0.62765(16) 0.0200(9) Uani 1 1 d . . . C68 C -0.05928(17) 0.43479(19) 0.65060(18) 0.0291(10) Uani 1 1 d . . . H68 H -0.0937 0.4273 0.6716 0.035 Uiso 1 1 calc R . . C67 C -0.05191(18) 0.4165(2) 0.59462(19) 0.0369(11) Uani 1 1 d . . . H67 H -0.0793 0.3943 0.5712 0.044 Uiso 1 1 calc R . . C66 C 0.00271(17) 0.43632(18) 0.57899(17) 0.0287(10) Uani 1 1 d . . . H66 H 0.0199 0.4316 0.5425 0.034 Uiso 1 1 calc R . . C62 C 0.16485(16) 0.54490(16) 0.69037(17) 0.0236(9) Uani 1 1 d . . . H62 H 0.1943 0.5483 0.6623 0.028 Uiso 1 1 calc R . . C63 C 0.16854(17) 0.56398(18) 0.74596(18) 0.0310(10) Uani 1 1 d . . . H63 H 0.2011 0.5837 0.7641 0.037 Uiso 1 1 calc R . . C64 C 0.11521(17) 0.54904(18) 0.77140(18) 0.0289(10) Uani 1 1 d . . . H64 H 0.1063 0.5574 0.8103 0.035 Uiso 1 1 calc R . . C10 C 0.41582(15) 0.67964(16) 0.66014(16) 0.0184(8) Uani 1 1 d . . . C9 C 0.37687(14) 0.72957(16) 0.67119(15) 0.0164(8) Uani 1 1 d . . . C6 C 0.32321(14) 0.73356(15) 0.63522(15) 0.0161(8) Uani 1 1 d . . . C5 C 0.28601(16) 0.68129(16) 0.62863(17) 0.0228(9) Uani 1 1 d . . . H5 H 0.2958 0.6414 0.646 0.027 Uiso 1 1 calc R . . C4 C 0.23479(16) 0.68653(17) 0.59701(16) 0.0234(9) Uani 1 1 d . . . H4 H 0.2093 0.6507 0.5935 0.028 Uiso 1 1 calc R . . C3 C 0.22107(15) 0.74410(16) 0.57065(15) 0.0181(8) Uani 1 1 d . . . C2 C 0.16587(16) 0.75462(18) 0.53760(16) 0.0208(9) Uani 1 1 d . . . C1 C 0.07346(17) 0.7160(2) 0.5132(2) 0.0419(12) Uani 1 1 d . . . H1A H 0.0546 0.7533 0.5307 0.063 Uiso 1 1 calc R . . H1B H 0.0488 0.6779 0.5177 0.063 Uiso 1 1 calc R . . H1C H 0.0793 0.7243 0.4724 0.063 Uiso 1 1 calc R . . C8 C 0.25867(16) 0.79600(16) 0.57533(15) 0.0181(9) Uani 1 1 d . . . H8 H 0.2498 0.8352 0.5563 0.022 Uiso 1 1 calc R . . C7 C 0.30892(15) 0.79071(16) 0.60754(15) 0.0167(8) Uani 1 1 d . . . H7 H 0.3342 0.8267 0.6109 0.02 Uiso 1 1 calc R . . C14 C 0.38458(14) 0.77662(16) 0.71326(15) 0.0174(8) Uani 1 1 d . . . C17 C 0.42790(17) 0.83458(17) 0.77900(17) 0.0250(9) Uani 1 1 d . . . H17 H 0.4567 0.8512 0.8044 0.03 Uiso 1 1 calc R . . C16 C 0.37085(17) 0.85831(18) 0.77447(17) 0.0255(9) Uani 1 1 d . . . H16 H 0.3543 0.8925 0.7959 0.031 Uiso 1 1 calc R . . C15 C 0.34399(16) 0.82236(16) 0.73312(16) 0.0210(9) Uani 1 1 d . . . H15 H 0.305 0.8272 0.72 0.025 Uiso 1 1 calc R . . C11 C 0.41642(17) 0.63570(17) 0.61397(17) 0.0249(9) Uani 1 1 d . . . H11 H 0.389 0.6339 0.5834 0.03 Uiso 1 1 calc R . . C12 C 0.46332(17) 0.59635(17) 0.62109(18) 0.0286(10) Uani 1 1 d . . . H12 H 0.4747 0.5621 0.5967 0.034 Uiso 1 1 calc R . . C13 C 0.49147(17) 0.61655(17) 0.67175(18) 0.0266(10) Uani 1 1 d . . . H13 H 0.5256 0.5972 0.6871 0.032 Uiso 1 1 calc R . . C44 C 0.40074(16) 0.49846(17) 0.31763(17) 0.0231(9) Uani 1 1 d . . . C43 C 0.42303(16) 0.52296(17) 0.36910(17) 0.0227(9) Uani 1 1 d . . . C40 C 0.39002(16) 0.50846(17) 0.42222(16) 0.0209(9) Uani 1 1 d . . . C39 C 0.38560(17) 0.44621(18) 0.44433(18) 0.0294(10) Uani 1 1 d . . . H39 H 0.4032 0.4114 0.4247 0.035 Uiso 1 1 calc R . . C38 C 0.35621(17) 0.43459(18) 0.49404(17) 0.0275(10) Uani 1 1 d . . . H38 H 0.3533 0.3919 0.5083 0.033 Uiso 1 1 calc R . . C37 C 0.33078(15) 0.48503(17) 0.52348(16) 0.0208(9) Uani 1 1 d . . . C36 C 0.30145(16) 0.47739(19) 0.57955(18) 0.0249(10) Uani 1 1 d . . . C35 C 0.2728(2) 0.4068(2) 0.65246(18) 0.0418(12) Uani 1 1 d . . . H35A H 0.2945 0.4301 0.6822 0.063 Uiso 1 1 calc R . . H35B H 0.2725 0.3608 0.6616 0.063 Uiso 1 1 calc R . . H35C H 0.2328 0.4229 0.6506 0.063 Uiso 1 1 calc R . . C42 C 0.33376(16) 0.54662(17) 0.50127(16) 0.0223(9) Uani 1 1 d . . . H42 H 0.3154 0.5812 0.5205 0.027 Uiso 1 1 calc R . . C41 C 0.36329(16) 0.55803(17) 0.45134(16) 0.0214(9) Uani 1 1 d . . . H41 H 0.3653 0.6006 0.4367 0.026 Uiso 1 1 calc R . . C48 C 0.47204(16) 0.56259(18) 0.37432(17) 0.0258(9) Uani 1 1 d . . . C51 C 0.54994(18) 0.6169(2) 0.34881(19) 0.0365(11) Uani 1 1 d . . . H51 H 0.5807 0.634 0.3268 0.044 Uiso 1 1 calc R . . C50 C 0.54125(19) 0.6298(2) 0.4071(2) 0.0426(12) Uani 1 1 d . . . H50 H 0.5642 0.6573 0.4307 0.051 Uiso 1 1 calc R . . C49 C 0.49339(18) 0.5953(2) 0.42336(18) 0.0351(11) Uani 1 1 d . . . H49 H 0.4775 0.5936 0.4607 0.042 Uiso 1 1 calc R . . C45 C 0.35281(17) 0.45687(18) 0.30936(18) 0.0299(10) Uani 1 1 d . . . H45 H 0.3297 0.4383 0.3384 0.036 Uiso 1 1 calc R . . C46 C 0.34586(18) 0.4484(2) 0.2519(2) 0.0402(12) Uani 1 1 d . . . H46 H 0.3172 0.4228 0.2332 0.048 Uiso 1 1 calc R . . C47 C 0.38914(18) 0.4849(2) 0.22582(19) 0.0365(11) Uani 1 1 d . . . H47 H 0.3941 0.4879 0.1856 0.044 Uiso 1 1 calc R . . C31 C 0.08947(18) 0.69000(19) 0.84126(18) 0.0294(10) Uani 1 1 d . . . C26 C 0.13290(17) 0.72185(19) 0.81164(17) 0.0291(10) Uani 1 1 d . . . C23 C 0.19108(16) 0.72648(18) 0.83978(18) 0.0291(10) Uani 1 1 d . . . C22 C 0.24244(16) 0.70952(17) 0.81137(18) 0.0272(10) Uani 1 1 d . . . H22 H 0.2406 0.6943 0.7731 0.033 Uiso 1 1 calc R . . C21 C 0.29492(18) 0.71495(18) 0.83870(19) 0.0342(10) Uani 1 1 d . . . H21 H 0.3293 0.7024 0.8195 0.041 Uiso 1 1 calc R . . C20 C 0.29894(18) 0.73853(19) 0.89417(19) 0.0333(11) Uani 1 1 d . . . C19 C 0.3555(2) 0.7459(2) 0.9261(2) 0.0411(12) Uani 1 1 d . . . C18 C 0.45656(19) 0.7437(2) 0.9211(2) 0.0561(14) Uani 1 1 d . . . H18A H 0.4507 0.7708 0.9548 0.084 Uiso 1 1 calc R . . H18B H 0.4833 0.7651 0.8949 0.084 Uiso 1 1 calc R . . H18C H 0.4731 0.7023 0.933 0.084 Uiso 1 1 calc R . . C24 C 0.19579(19) 0.7507(2) 0.89588(19) 0.0372(11) Uani 1 1 d . . . H24 H 0.1617 0.7628 0.9157 0.045 Uiso 1 1 calc R . . C27 C 0.12587(17) 0.75123(18) 0.75844(18) 0.0300(10) Uani 1 1 d . . . C30 C 0.08284(18) 0.7843(2) 0.67921(18) 0.0348(10) Uani 1 1 d . . . H30 H 0.0552 0.7897 0.6491 0.042 Uiso 1 1 calc R . . C29 C 0.13659(19) 0.8149(2) 0.6816(2) 0.0384(12) Uani 1 1 d . . . H29 H 0.1508 0.8453 0.6548 0.046 Uiso 1 1 calc R . . C28 C 0.16481(19) 0.7936(2) 0.72866(19) 0.0362(11) Uani 1 1 d . . . H28 H 0.2033 0.8045 0.7401 0.043 Uiso 1 1 calc R . . C32 C 0.0950(2) 0.64983(19) 0.89063(19) 0.0376(11) Uani 1 1 d . . . H32 H 0.1299 0.6438 0.912 0.045 Uiso 1 1 calc R . . C33 C 0.04206(18) 0.6207(2) 0.90295(18) 0.0323(10) Uani 1 1 d . . . H33 H 0.0331 0.5913 0.9327 0.039 Uiso 1 1 calc R . . C34 C 0.0044(2) 0.6466(2) 0.8590(2) 0.0418(12) Uani 1 1 d . . . H34 H -0.0358 0.6366 0.8562 0.05 Uiso 1 1 calc R . . C25 C 0.24858(19) 0.7569(2) 0.92204(19) 0.0373(11) Uani 1 1 d . . . H25 H 0.251 0.7739 0.9597 0.045 Uiso 1 1 calc R . . N7 N 0.07899(13) 0.52179(14) 0.73442(14) 0.0234(8) Uani 1 1 d . . . N8 N -0.01216(13) 0.46446(13) 0.67195(13) 0.0212(7) Uani 1 1 d . . . N1 N 0.46408(13) 0.66623(14) 0.69549(14) 0.0220(7) Uani 1 1 d . . . N2 N 0.43648(12) 0.78565(13) 0.74305(13) 0.0208(7) Uani 1 1 d . . . N5 N 0.42264(13) 0.51478(15) 0.26421(14) 0.0254(8) Uani 1 1 d . . . N6 N 0.50871(13) 0.57704(15) 0.32862(14) 0.0280(8) Uani 1 1 d . . . N4 N 0.03147(14) 0.68638(16) 0.82224(15) 0.0323(9) Uani 1 1 d . . . N3 N 0.07481(14) 0.74596(16) 0.72507(15) 0.0329(9) Uani 1 1 d . . . O7 O 0.21360(11) 0.54918(12) 0.39945(11) 0.0296(7) Uani 1 1 d . . . O8 O 0.23180(13) 0.44314(13) 0.40139(12) 0.0381(8) Uani 1 1 d . . . O1 O 0.12925(11) 0.70493(12) 0.54094(12) 0.0307(7) Uani 1 1 d . . . O2 O 0.15488(11) 0.80287(12) 0.51148(12) 0.0289(7) Uani 1 1 d . . . O5 O 0.30041(12) 0.41655(12) 0.59791(12) 0.0339(7) Uani 1 1 d . . . O6 O 0.28099(13) 0.52105(13) 0.60612(12) 0.0362(7) Uani 1 1 d . . . O3 O 0.40094(13) 0.73290(15) 0.89213(14) 0.0527(9) Uani 1 1 d . . . O4 O 0.35938(15) 0.7628(2) 0.97470(16) 0.0814(13) Uani 1 1 d . . . Cu4 Cu 0 0.49385(3) 0.75 0.02233(18) Uani 1 2 d S . . Cu1 Cu 0.5 0.72500(3) 0.75 0.02100(17) Uani 1 2 d S . . Cu3 Cu 0.5 0.55019(3) 0.25 0.0296(2) Uani 1 2 d S . . Cu2 Cu 0 0.71475(3) 0.75 0.0326(2) Uani 1 2 d S . . 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 C61 0.017(2) 0.018(2) 0.024(2) -0.0003(17) 0.0018(18) 0.0023(16) C60 0.020(2) 0.0154(19) 0.021(2) 0.0054(16) 0.0034(18) 0.0036(16) C57 0.014(2) 0.026(2) 0.016(2) -0.0026(17) 0.0005(17) -0.0005(16) C56 0.021(2) 0.023(2) 0.022(2) -0.0034(17) 0.0026(19) -0.0013(16) C55 0.021(2) 0.020(2) 0.027(3) 0.0016(18) -0.0017(19) -0.0041(16) C54 0.017(2) 0.027(2) 0.017(2) -0.0049(18) -0.0034(17) 0.0001(16) C53 0.016(2) 0.031(2) 0.022(2) -0.001(2) -0.0035(18) -0.0029(18) C52 0.043(3) 0.041(3) 0.026(3) 0.003(2) 0.014(2) 0.010(2) C59 0.022(2) 0.021(2) 0.024(2) -0.0074(18) 0.0017(19) 0.0009(16) C58 0.024(2) 0.020(2) 0.025(2) 0.0043(17) -0.0027(19) -0.0022(17) C65 0.018(2) 0.023(2) 0.019(2) 0.0038(17) 0.0025(18) 0.0007(16) C68 0.017(2) 0.043(3) 0.028(3) 0.009(2) 0.000(2) -0.0052(18) C67 0.031(3) 0.050(3) 0.030(3) -0.008(2) -0.002(2) -0.011(2) C66 0.028(2) 0.041(2) 0.017(2) -0.0044(19) 0.001(2) -0.0033(19) C62 0.020(2) 0.024(2) 0.026(3) -0.0011(18) 0.0089(19) -0.0028(16) C63 0.024(2) 0.033(2) 0.036(3) -0.006(2) 0.001(2) -0.0065(18) C64 0.031(3) 0.030(2) 0.026(3) -0.0085(19) 0.004(2) -0.0062(19) C10 0.015(2) 0.021(2) 0.018(2) 0.0034(17) -0.0060(17) -0.0023(16) C9 0.0136(19) 0.0159(19) 0.020(2) 0.0024(17) -0.0020(16) -0.0011(15) C6 0.0145(19) 0.017(2) 0.017(2) -0.0030(16) -0.0031(16) 0.0024(15) C5 0.021(2) 0.018(2) 0.030(3) 0.0044(17) -0.0094(19) 0.0002(16) C4 0.021(2) 0.020(2) 0.030(3) -0.0002(18) -0.0027(19) -0.0077(16) C3 0.016(2) 0.021(2) 0.017(2) -0.0034(16) -0.0042(17) 0.0049(15) C2 0.022(2) 0.022(2) 0.018(2) -0.0070(18) -0.0028(18) -0.0005(17) C1 0.022(2) 0.047(3) 0.056(3) 0.001(2) -0.021(2) -0.004(2) C8 0.023(2) 0.0125(19) 0.018(2) 0.0014(15) -0.0014(18) 0.0029(15) C7 0.0131(19) 0.017(2) 0.020(2) -0.0020(16) -0.0033(17) -0.0013(15) C14 0.0137(19) 0.0199(19) 0.019(2) 0.0027(18) -0.0031(16) -0.0005(16) C17 0.027(2) 0.025(2) 0.024(2) -0.0020(18) -0.0035(19) -0.0055(18) C16 0.027(2) 0.024(2) 0.026(2) -0.0083(18) 0.0035(19) 0.0030(18) C15 0.015(2) 0.020(2) 0.028(2) 0.0043(18) 0.0002(18) -0.0018(16) C11 0.025(2) 0.027(2) 0.023(2) -0.0092(18) -0.0057(19) 0.0010(18) C12 0.030(2) 0.022(2) 0.034(3) -0.0067(19) -0.005(2) 0.0075(18) C13 0.018(2) 0.025(2) 0.036(3) -0.0005(19) -0.009(2) 0.0072(17) C44 0.016(2) 0.025(2) 0.028(3) -0.0033(18) 0.0045(19) 0.0067(17) C43 0.018(2) 0.024(2) 0.026(2) 0.0028(18) 0.0054(18) 0.0119(17) C40 0.020(2) 0.021(2) 0.022(2) 0.0011(17) 0.0002(18) 0.0035(16) C39 0.031(2) 0.025(2) 0.031(3) -0.0014(19) 0.004(2) 0.0095(18) C38 0.031(2) 0.022(2) 0.030(3) 0.0033(19) 0.005(2) 0.0039(18) C37 0.016(2) 0.026(2) 0.020(2) 0.0013(18) -0.0011(18) -0.0006(16) C36 0.017(2) 0.025(2) 0.032(3) 0.001(2) -0.0005(19) -0.0045(17) C35 0.055(3) 0.037(3) 0.033(3) 0.012(2) 0.016(2) -0.007(2) C42 0.019(2) 0.023(2) 0.025(2) -0.0072(18) -0.0003(19) 0.0031(16) C41 0.026(2) 0.019(2) 0.019(2) 0.0039(17) -0.0006(19) 0.0046(17) C48 0.019(2) 0.034(2) 0.024(2) 0.0013(19) 0.0003(19) 0.0032(18) C51 0.020(2) 0.054(3) 0.035(3) -0.002(2) 0.003(2) -0.009(2) C50 0.030(3) 0.065(3) 0.032(3) -0.003(2) -0.010(2) -0.014(2) C49 0.031(3) 0.050(3) 0.024(3) -0.001(2) -0.002(2) 0.000(2) C45 0.026(2) 0.033(2) 0.031(3) -0.0064(19) 0.010(2) -0.0021(18) C46 0.026(3) 0.057(3) 0.038(3) -0.020(2) 0.004(2) -0.013(2) C47 0.024(2) 0.060(3) 0.026(3) -0.010(2) 0.008(2) 0.003(2) C31 0.028(3) 0.036(2) 0.024(3) 0.0032(19) 0.001(2) 0.0004(19) C26 0.027(2) 0.030(2) 0.030(3) 0.002(2) -0.004(2) 0.0053(19) C23 0.025(2) 0.026(2) 0.035(3) 0.009(2) -0.005(2) -0.0028(18) C22 0.024(2) 0.026(2) 0.032(3) -0.0032(18) -0.002(2) -0.0021(17) C21 0.031(3) 0.031(2) 0.040(3) 0.004(2) 0.000(2) 0.002(2) C20 0.027(2) 0.037(3) 0.035(3) 0.003(2) -0.006(2) -0.0026(19) C19 0.035(3) 0.045(3) 0.044(3) 0.006(2) -0.010(3) -0.008(2) C18 0.023(3) 0.073(3) 0.072(4) -0.015(3) -0.013(3) 0.000(2) C24 0.032(3) 0.047(3) 0.034(3) -0.006(2) 0.004(2) -0.004(2) C27 0.023(2) 0.033(2) 0.034(3) 0.001(2) -0.005(2) 0.0040(18) C30 0.031(3) 0.047(3) 0.027(3) 0.005(2) -0.002(2) 0.012(2) C29 0.030(3) 0.045(3) 0.040(3) 0.022(2) 0.007(2) 0.001(2) C28 0.027(2) 0.044(3) 0.037(3) 0.005(2) 0.007(2) -0.006(2) C32 0.038(3) 0.044(3) 0.031(3) 0.002(2) -0.007(2) 0.003(2) C33 0.030(3) 0.046(3) 0.021(3) 0.0021(19) 0.003(2) -0.002(2) C34 0.033(3) 0.047(3) 0.046(3) -0.006(2) 0.015(2) -0.009(2) C25 0.034(3) 0.052(3) 0.027(3) -0.001(2) 0.000(2) 0.003(2) N7 0.0194(18) 0.0271(18) 0.024(2) -0.0078(15) 0.0068(16) -0.0046(14) N8 0.0176(17) 0.0247(17) 0.0212(19) 0.0036(14) 0.0025(15) -0.0021(14) N1 0.0150(17) 0.0222(17) 0.029(2) -0.0029(15) -0.0058(15) 0.0026(14) N2 0.0193(17) 0.0204(17) 0.0225(18) -0.0028(15) -0.0062(14) 0.0002(13) N5 0.0184(18) 0.040(2) 0.018(2) -0.0035(16) 0.0041(15) 0.0009(15) N6 0.0194(18) 0.040(2) 0.025(2) -0.0015(16) 0.0028(16) -0.0011(15) N4 0.027(2) 0.042(2) 0.028(2) 0.0053(17) 0.0013(17) -0.0024(16) N3 0.025(2) 0.046(2) 0.028(2) 0.0082(17) -0.0017(17) -0.0016(16) O7 0.0311(17) 0.0337(17) 0.0241(17) 0.0009(13) 0.0092(14) 0.0034(12) O8 0.051(2) 0.0300(16) 0.0339(19) -0.0090(14) 0.0181(16) 0.0014(14) O1 0.0200(15) 0.0319(16) 0.0400(19) 0.0045(13) -0.0158(13) -0.0045(12) O2 0.0288(17) 0.0212(15) 0.0364(18) 0.0030(13) -0.0150(14) 0.0047(12) O5 0.0433(18) 0.0265(16) 0.0320(18) 0.0106(13) 0.0146(15) 0.0037(13) O6 0.049(2) 0.0298(16) 0.0305(19) -0.0004(14) 0.0147(15) -0.0001(14) O3 0.0232(18) 0.077(2) 0.058(2) -0.0007(18) 0.0023(17) 0.0073(16) O4 0.045(2) 0.158(4) 0.041(2) -0.020(2) -0.0127(19) -0.013(2) Cu4 0.0166(4) 0.0297(4) 0.0209(4) 0 0.0044(3) 0 Cu1 0.0155(3) 0.0208(4) 0.0265(4) 0 -0.0102(3) 0 Cu3 0.0186(4) 0.0484(5) 0.0220(4) 0 0.0054(3) 0 Cu2 0.0230(4) 0.0444(5) 0.0302(5) 0 -0.0006(3) 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C61 N7 1.392(5) . ? C61 C60 1.397(5) . ? C61 C62 1.425(5) . ? C60 C65 1.401(5) . ? C60 C57 1.494(5) . ? C57 C58 1.377(5) . ? C57 C56 1.399(5) . ? C56 C55 1.379(5) . ? C56 H56 0.95 . ? C55 C54 1.380(5) . ? C55 H55 0.95 . ? C54 C59 1.404(5) . ? C54 C53 1.500(5) . ? C53 O8 1.198(4) . ? C53 O7 1.335(4) . ? C52 O7 1.454(4) . ? C52 H52A 0.98 . ? C52 H52B 0.98 . ? C52 H52C 0.98 . ? C59 C58 1.373(5) . ? C59 H59 0.95 . ? C58 H58 0.95 . ? C65 N8 1.396(4) . ? C65 C66 1.405(5) . ? C68 N8 1.340(5) . ? C68 C67 1.376(5) . ? C68 H68 0.95 . ? C67 C66 1.376(5) . ? C67 H67 0.95 . ? C66 H66 0.95 . ? C62 C63 1.361(5) . ? C62 H62 0.95 . ? C63 C64 1.404(5) . ? C63 H63 0.95 . ? C64 N7 1.322(5) . ? C64 H64 0.95 . ? C10 C9 1.397(5) . ? C10 N1 1.406(4) . ? C10 C11 1.415(5) . ? C9 C14 1.398(5) . ? C9 C6 1.489(5) . ? C6 C7 1.391(5) . ? C6 C5 1.391(5) . ? C5 C4 1.389(5) . ? C5 H5 0.95 . ? C4 C3 1.381(5) . ? C4 H4 0.95 . ? C3 C8 1.387(5) . ? C3 C2 1.496(5) . ? C2 O2 1.200(4) . ? C2 O1 1.336(4) . ? C1 O1 1.451(4) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C8 C7 1.378(5) . ? C8 H8 0.95 . ? C7 H7 0.95 . ? C14 N2 1.389(4) . ? C14 C15 1.415(5) . ? C17 N2 1.336(5) . ? C17 C16 1.406(5) . ? C17 H17 0.95 . ? C16 C15 1.365(5) . ? C16 H16 0.95 . ? C15 H15 0.95 . ? C11 C12 1.363(5) . ? C11 H11 0.95 . ? C12 C13 1.409(5) . ? C12 H12 0.95 . ? C13 N1 1.334(4) . ? C13 H13 0.95 . ? C44 N5 1.394(5) . ? C44 C43 1.400(5) . ? C44 C45 1.413(5) . ? C43 C48 1.401(5) . ? C43 C40 1.494(5) . ? C40 C41 1.383(5) . ? C40 C39 1.398(5) . ? C39 C38 1.373(5) . ? C39 H39 0.95 . ? C38 C37 1.387(5) . ? C38 H38 0.95 . ? C37 C42 1.384(5) . ? C37 C36 1.490(5) . ? C36 O6 1.199(4) . ? C36 O5 1.336(4) . ? C35 O5 1.445(5) . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? C42 C41 1.378(5) . ? C42 H42 0.95 . ? C41 H41 0.95 . ? C48 N6 1.401(5) . ? C48 C49 1.417(5) . ? C51 N6 1.342(5) . ? C51 C50 1.406(6) . ? C51 H51 0.95 . ? C50 C49 1.372(6) . ? C50 H50 0.95 . ? C49 H49 0.95 . ? C45 C46 1.364(6) . ? C45 H45 0.95 . ? C46 C47 1.396(6) . ? C46 H46 0.95 . ? C47 N5 1.332(5) . ? C47 H47 0.95 . ? C31 C26 1.390(5) . ? C31 N4 1.405(5) . ? C31 C32 1.430(6) . ? C26 C27 1.394(5) . ? C26 C23 1.489(5) . ? C23 C22 1.407(5) . ? C23 C24 1.408(6) . ? C22 C21 1.365(5) . ? C22 H22 0.95 . ? C21 C20 1.389(6) . ? C21 H21 0.95 . ? C20 C25 1.389(6) . ? C20 C19 1.502(6) . ? C19 O4 1.193(5) . ? C19 O3 1.346(5) . ? C18 O3 1.459(5) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C24 C25 1.361(6) . ? C24 H24 0.95 . ? C27 N3 1.408(5) . ? C27 C28 1.441(6) . ? C30 N3 1.350(5) . ? C30 C29 1.392(6) . ? C30 H30 0.95 . ? C29 C28 1.348(6) . ? C29 H29 0.95 . ? C28 H28 0.95 . ? C32 C33 1.393(6) . ? C32 H32 0.95 . ? C33 C34 1.441(6) . ? C33 H33 0.95 . ? C34 N4 1.350(5) . ? C34 H34 0.95 . ? C25 H25 0.95 . ? N7 Cu4 1.947(3) . ? N8 Cu4 1.942(3) . ? N1 Cu1 1.944(3) . ? N2 Cu1 1.936(3) . ? N5 Cu3 1.958(3) . ? N6 Cu3 1.930(3) . ? N4 Cu2 1.924(3) . ? N3 Cu2 1.936(3) . ? Cu4 N8 1.942(3) 2_556 ? Cu4 N7 1.947(3) 2_556 ? Cu1 N2 1.936(3) 2_656 ? Cu1 N1 1.944(3) 2_656 ? Cu3 N6 1.930(3) 2_655 ? Cu3 N5 1.958(3) 2_655 ? Cu2 N4 1.924(3) 2_556 ? Cu2 N3 1.936(3) 2_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 C61 C60 123.0(3) . . ? N7 C61 C62 108.7(3) . . ? C60 C61 C62 128.2(4) . . ? C61 C60 C65 126.6(3) . . ? C61 C60 C57 117.2(3) . . ? C65 C60 C57 116.1(3) . . ? C58 C57 C56 119.1(3) . . ? C58 C57 C60 122.7(3) . . ? C56 C57 C60 118.2(3) . . ? C55 C56 C57 120.0(3) . . ? C55 C56 H56 120 . . ? C57 C56 H56 120 . . ? C56 C55 C54 120.7(3) . . ? C56 C55 H55 119.7 . . ? C54 C55 H55 119.7 . . ? C55 C54 C59 119.2(4) . . ? C55 C54 C53 121.8(3) . . ? C59 C54 C53 118.9(3) . . ? O8 C53 O7 124.7(4) . . ? O8 C53 C54 124.3(4) . . ? O7 C53 C54 111.0(3) . . ? O7 C52 H52A 109.5 . . ? O7 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? O7 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C58 C59 C54 119.7(3) . . ? C58 C59 H59 120.2 . . ? C54 C59 H59 120.2 . . ? C59 C58 C57 121.2(3) . . ? C59 C58 H58 119.4 . . ? C57 C58 H58 119.4 . . ? N8 C65 C60 123.0(3) . . ? N8 C65 C66 109.0(3) . . ? C60 C65 C66 127.9(4) . . ? N8 C68 C67 112.0(4) . . ? N8 C68 H68 124 . . ? C67 C68 H68 124 . . ? C68 C67 C66 107.0(4) . . ? C68 C67 H67 126.5 . . ? C66 C67 H67 126.5 . . ? C67 C66 C65 106.5(4) . . ? C67 C66 H66 126.7 . . ? C65 C66 H66 126.7 . . ? C63 C62 C61 106.3(3) . . ? C63 C62 H62 126.9 . . ? C61 C62 H62 126.9 . . ? C62 C63 C64 107.1(4) . . ? C62 C63 H63 126.4 . . ? C64 C63 H63 126.4 . . ? N7 C64 C63 111.4(4) . . ? N7 C64 H64 124.3 . . ? C63 C64 H64 124.3 . . ? C9 C10 N1 122.9(3) . . ? C9 C10 C11 129.2(3) . . ? N1 C10 C11 107.9(3) . . ? C10 C9 C14 125.0(3) . . ? C10 C9 C6 117.8(3) . . ? C14 C9 C6 117.2(3) . . ? C7 C6 C5 118.2(3) . . ? C7 C6 C9 120.1(3) . . ? C5 C6 C9 121.7(3) . . ? C4 C5 C6 121.0(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C3 C8 119.9(3) . . ? C4 C3 C2 123.1(3) . . ? C8 C3 C2 116.9(3) . . ? O2 C2 O1 123.1(3) . . ? O2 C2 C3 123.9(3) . . ? O1 C2 C3 112.9(3) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C8 C3 120.0(3) . . ? C7 C8 H8 120 . . ? C3 C8 H8 120 . . ? C8 C7 C6 121.0(3) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? N2 C14 C9 123.4(3) . . ? N2 C14 C15 108.2(3) . . ? C9 C14 C15 128.5(3) . . ? N2 C17 C16 111.3(3) . . ? N2 C17 H17 124.3 . . ? C16 C17 H17 124.3 . . ? C15 C16 C17 106.1(3) . . ? C15 C16 H16 127 . . ? C17 C16 H16 127 . . ? C16 C15 C14 107.7(3) . . ? C16 C15 H15 126.1 . . ? C14 C15 H15 126.1 . . ? C12 C11 C10 107.9(3) . . ? C12 C11 H11 126 . . ? C10 C11 H11 126 . . ? C11 C12 C13 106.3(3) . . ? C11 C12 H12 126.8 . . ? C13 C12 H12 126.8 . . ? N1 C13 C12 111.5(3) . . ? N1 C13 H13 124.3 . . ? C12 C13 H13 124.3 . . ? N5 C44 C43 123.3(3) . . ? N5 C44 C45 108.4(3) . . ? C43 C44 C45 128.2(4) . . ? C44 C43 C48 125.2(4) . . ? C44 C43 C40 117.2(3) . . ? C48 C43 C40 117.5(4) . . ? C41 C40 C39 118.2(4) . . ? C41 C40 C43 119.5(3) . . ? C39 C40 C43 122.3(3) . . ? C38 C39 C40 121.0(4) . . ? C38 C39 H39 119.5 . . ? C40 C39 H39 119.5 . . ? C39 C38 C37 120.1(4) . . ? C39 C38 H38 120 . . ? C37 C38 H38 120 . . ? C42 C37 C38 119.4(4) . . ? C42 C37 C36 117.0(3) . . ? C38 C37 C36 123.6(3) . . ? O6 C36 O5 122.8(4) . . ? O6 C36 C37 124.0(3) . . ? O5 C36 C37 113.2(3) . . ? O5 C35 H35A 109.5 . . ? O5 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O5 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C41 C42 C37 120.3(3) . . ? C41 C42 H42 119.9 . . ? C37 C42 H42 119.9 . . ? C42 C41 C40 121.0(3) . . ? C42 C41 H41 119.5 . . ? C40 C41 H41 119.5 . . ? C43 C48 N6 123.4(4) . . ? C43 C48 C49 128.7(4) . . ? N6 C48 C49 107.9(3) . . ? N6 C51 C50 110.6(4) . . ? N6 C51 H51 124.7 . . ? C50 C51 H51 124.7 . . ? C49 C50 C51 106.9(4) . . ? C49 C50 H50 126.5 . . ? C51 C50 H50 126.5 . . ? C50 C49 C48 107.4(4) . . ? C50 C49 H49 126.3 . . ? C48 C49 H49 126.3 . . ? C46 C45 C44 107.3(4) . . ? C46 C45 H45 126.4 . . ? C44 C45 H45 126.4 . . ? C45 C46 C47 106.4(4) . . ? C45 C46 H46 126.8 . . ? C47 C46 H46 126.8 . . ? N5 C47 C46 111.7(4) . . ? N5 C47 H47 124.1 . . ? C46 C47 H47 124.1 . . ? C26 C31 N4 123.6(4) . . ? C26 C31 C32 128.5(4) . . ? N4 C31 C32 107.5(4) . . ? C31 C26 C27 125.2(4) . . ? C31 C26 C23 117.3(4) . . ? C27 C26 C23 117.5(4) . . ? C22 C23 C24 118.2(4) . . ? C22 C23 C26 122.1(4) . . ? C24 C23 C26 119.7(4) . . ? C21 C22 C23 120.1(4) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C21 C20 121.1(4) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C20 C25 119.2(4) . . ? C21 C20 C19 123.3(4) . . ? C25 C20 C19 117.5(4) . . ? O4 C19 O3 124.8(4) . . ? O4 C19 C20 124.0(5) . . ? O3 C19 C20 111.2(4) . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C25 C24 C23 120.8(4) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C26 C27 N3 123.3(4) . . ? C26 C27 C28 129.2(4) . . ? N3 C27 C28 107.4(4) . . ? N3 C30 C29 111.5(4) . . ? N3 C30 H30 124.2 . . ? C29 C30 H30 124.2 . . ? C28 C29 C30 107.6(4) . . ? C28 C29 H29 126.2 . . ? C30 C29 H29 126.2 . . ? C29 C28 C27 107.4(4) . . ? C29 C28 H28 126.3 . . ? C27 C28 H28 126.3 . . ? C33 C32 C31 110.5(4) . . ? C33 C32 H32 124.8 . . ? C31 C32 H32 124.8 . . ? C32 C33 C34 102.2(4) . . ? C32 C33 H33 128.9 . . ? C34 C33 H33 128.9 . . ? N4 C34 C33 113.9(4) . . ? N4 C34 H34 123 . . ? C33 C34 H34 123 . . ? C24 C25 C20 120.6(4) . . ? C24 C25 H25 119.7 . . ? C20 C25 H25 119.7 . . ? C64 N7 C61 106.5(3) . . ? C64 N7 Cu4 126.1(3) . . ? C61 N7 Cu4 127.4(3) . . ? C68 N8 C65 105.5(3) . . ? C68 N8 Cu4 127.1(3) . . ? C65 N8 Cu4 127.2(2) . . ? C13 N1 C10 106.4(3) . . ? C13 N1 Cu1 124.1(2) . . ? C10 N1 Cu1 126.1(2) . . ? C17 N2 C14 106.7(3) . . ? C17 N2 Cu1 124.0(3) . . ? C14 N2 Cu1 126.8(2) . . ? C47 N5 C44 106.2(3) . . ? C47 N5 Cu3 125.6(3) . . ? C44 N5 Cu3 125.5(3) . . ? C51 N6 C48 107.0(3) . . ? C51 N6 Cu3 125.4(3) . . ? C48 N6 Cu3 127.4(3) . . ? C34 N4 C31 105.9(3) . . ? C34 N4 Cu2 125.2(3) . . ? C31 N4 Cu2 127.6(3) . . ? C30 N3 C27 105.9(3) . . ? C30 N3 Cu2 124.5(3) . . ? C27 N3 Cu2 126.8(3) . . ? C53 O7 C52 115.5(3) . . ? C2 O1 C1 114.0(3) . . ? C36 O5 C35 115.2(3) . . ? C19 O3 C18 112.2(4) . . ? N8 Cu4 N8 143.34(17) 2_556 . ? N8 Cu4 N7 92.51(13) 2_556 2_556 ? N8 Cu4 N7 98.28(13) . 2_556 ? N8 Cu4 N7 98.28(13) 2_556 . ? N8 Cu4 N7 92.51(13) . . ? N7 Cu4 N7 145.27(17) 2_556 . ? N2 Cu1 N2 98.73(17) 2_656 . ? N2 Cu1 N1 141.26(13) 2_656 . ? N2 Cu1 N1 92.21(12) . . ? N2 Cu1 N1 92.21(12) 2_656 2_656 ? N2 Cu1 N1 141.25(13) . 2_656 ? N1 Cu1 N1 102.13(18) . 2_656 ? N6 Cu3 N6 146.39(19) 2_655 . ? N6 Cu3 N5 100.64(13) 2_655 . ? N6 Cu3 N5 91.88(13) . . ? N6 Cu3 N5 91.88(13) 2_655 2_655 ? N6 Cu3 N5 100.64(13) . 2_655 ? N5 Cu3 N5 135.83(18) . 2_655 ? N4 Cu2 N4 144.3(2) 2_556 . ? N4 Cu2 N3 92.25(14) 2_556 2_556 ? N4 Cu2 N3 99.57(15) . 2_556 ? N4 Cu2 N3 99.57(15) 2_556 . ? N4 Cu2 N3 92.25(14) . . ? N3 Cu2 N3 140.8(2) 2_556 . ? #===END data_red-LH _database_code_depnum_ccdc_archive 'CCDC 835358' #TrackingRef '- Cif Global CrystEngComm_vigroux.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H16 N2 O2' _chemical_formula_sum 'C17 H16 N2 O2' _chemical_formula_weight 280.32 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6828(3) _cell_length_b 7.6675(4) _cell_length_c 16.4091(9) _cell_angle_alpha 96.408(4) _cell_angle_beta 95.194(4) _cell_angle_gamma 95.251(4) _cell_volume 703.87(6) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 986 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.8 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.998 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_unetI/netI 0.0736 _diffrn_reflns_number 5780 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.42 _diffrn_reflns_theta_full 28.42 _diffrn_measured_fraction_theta_full 0.901 _diffrn_measured_fraction_theta_max 0.901 _reflns_number_total 3201 _reflns_number_gt 1912 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0661P)^2^+0.4249P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3201 _refine_ls_number_parameters 197 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.114 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1763 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.264 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.8858(6) 0.4161(4) 1.15835(18) 0.0422(8) Uani 1 1 d . . . H1A H 0.8148 0.5228 1.1778 0.063 Uiso 1 1 calc R . . H1B H 1.0586 0.4425 1.1611 0.063 Uiso 1 1 calc R . . H1C H 0.848 0.3237 1.1932 0.063 Uiso 1 1 calc R . . C2 C 0.5632(5) 0.2896(4) 1.06242(17) 0.0291(6) Uani 1 1 d . . . C3 C 0.4825(5) 0.2311(4) 0.97378(16) 0.0275(6) Uani 1 1 d . . . C4 C 0.6299(5) 0.2518(4) 0.91145(17) 0.0287(6) Uani 1 1 d . . . H4 H 0.7857 0.3103 0.9246 0.034 Uiso 1 1 calc R . . C5 C 0.5502(5) 0.1874(4) 0.83009(17) 0.0290(6) Uani 1 1 d . . . H5 H 0.6518 0.2031 0.788 0.035 Uiso 1 1 calc R . . C6 C 0.3223(4) 0.0998(4) 0.80943(16) 0.0253(6) Uani 1 1 d . . . C7 C 0.1753(5) 0.0804(4) 0.87215(17) 0.0300(7) Uani 1 1 d . . . H7 H 0.0195 0.022 0.8592 0.036 Uiso 1 1 calc R . . C8 C 0.2540(5) 0.1456(4) 0.95329(17) 0.0315(7) Uani 1 1 d . . . H8 H 0.1514 0.1319 0.9952 0.038 Uiso 1 1 calc R . . C9 C 0.2310(4) 0.0325(4) 0.72044(16) 0.0269(6) Uani 1 1 d . . . H9 H 0.0834 -0.0484 0.7218 0.032 Uiso 1 1 calc R . . C10 C 0.4024(4) -0.0734(4) 0.67509(16) 0.0264(6) Uani 1 1 d . . . C11 C 0.4406(5) -0.0919(4) 0.59352(17) 0.0297(6) Uani 1 1 d . . . H11 H 0.3665 -0.0328 0.5518 0.036 Uiso 1 1 calc R . . C12 C 0.6097(5) -0.2146(4) 0.58227(18) 0.0349(7) Uani 1 1 d . . . H12 H 0.6709 -0.252 0.5319 0.042 Uiso 1 1 calc R . . C13 C 0.6688(5) -0.2693(4) 0.65731(18) 0.0319(7) Uani 1 1 d . . . H13 H 0.7778 -0.3525 0.6685 0.038 Uiso 1 1 calc R . . C14 C 0.1609(4) 0.1820(4) 0.67348(16) 0.0270(6) Uani 1 1 d . . . C15 C 0.2841(5) 0.3385(4) 0.66220(19) 0.0340(7) Uani 1 1 d . . . H15 H 0.4429 0.3783 0.684 0.041 Uiso 1 1 calc R . . C16 C 0.1344(5) 0.4300(4) 0.61264(18) 0.0339(7) Uani 1 1 d . . . H16 H 0.1738 0.5417 0.5948 0.041 Uiso 1 1 calc R . . C17 C -0.0755(6) 0.3289(4) 0.5954(2) 0.0404(8) Uani 1 1 d . . . H17 H -0.2108 0.3573 0.563 0.049 Uiso 1 1 calc R . . N1 N 0.5422(4) -0.1823(3) 0.71348(15) 0.0305(6) Uani 1 1 d D . . H1 H 0.541(5) -0.200(4) 0.7646(8) 0.037 Uiso 1 1 d D . . N2 N -0.0598(4) 0.1785(4) 0.63250(17) 0.0380(6) Uani 1 1 d D . . H2 H -0.165(4) 0.088(3) 0.628(2) 0.046 Uiso 1 1 d D . . O1 O 0.4372(4) 0.2774(3) 1.11752(12) 0.0412(6) Uani 1 1 d . . . O2 O 0.7913(3) 0.3557(3) 1.07374(12) 0.0372(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 C1 0.0528(19) 0.041(2) 0.0287(16) -0.0021(14) -0.0015(14) -0.0011(15) C2 0.0378(15) 0.0263(16) 0.0264(14) 0.0072(12) 0.0057(12) 0.0124(12) C3 0.0351(14) 0.0268(16) 0.0239(13) 0.0076(11) 0.0060(11) 0.0131(12) C4 0.0283(13) 0.0297(16) 0.0289(14) 0.0070(12) 0.0032(11) 0.0030(12) C5 0.0291(13) 0.0325(17) 0.0270(14) 0.0055(12) 0.0095(11) 0.0030(12) C6 0.0281(13) 0.0230(15) 0.0270(14) 0.0078(11) 0.0038(11) 0.0078(11) C7 0.0262(13) 0.0333(17) 0.0318(15) 0.0050(13) 0.0069(11) 0.0047(12) C8 0.0319(14) 0.0363(18) 0.0287(14) 0.0061(13) 0.0096(12) 0.0078(13) C9 0.0214(12) 0.0296(16) 0.0292(14) 0.0046(12) 0.0031(10) -0.0022(11) C10 0.0247(12) 0.0276(15) 0.0260(14) 0.0018(12) 0.0027(10) -0.0006(11) C11 0.0356(14) 0.0278(16) 0.0264(14) 0.0049(12) 0.0044(12) 0.0039(12) C12 0.0376(15) 0.0349(18) 0.0311(15) -0.0035(13) 0.0098(12) 0.0011(13) C13 0.0335(14) 0.0231(15) 0.0383(16) -0.0019(13) 0.0051(12) 0.0049(12) C14 0.0253(13) 0.0310(17) 0.0244(14) 0.0018(12) 0.0030(10) 0.0028(11) C15 0.0279(13) 0.0356(18) 0.0377(16) 0.0071(14) -0.0008(12) 0.0005(12) C16 0.0427(16) 0.0237(17) 0.0366(16) 0.0057(13) 0.0054(13) 0.0061(13) C17 0.0394(16) 0.045(2) 0.0378(17) 0.0100(15) -0.0068(13) 0.0129(15) N1 0.0334(12) 0.0330(14) 0.0260(12) 0.0040(11) 0.0024(10) 0.0075(10) N2 0.0294(13) 0.0394(17) 0.0438(15) 0.0103(13) -0.0055(11) -0.0018(11) O1 0.0425(11) 0.0578(15) 0.0263(10) 0.0078(10) 0.0099(9) 0.0115(11) O2 0.0390(11) 0.0451(13) 0.0263(11) 0.0025(9) 0.0024(9) 0.0008(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 O2 1.451(3) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 O1 1.209(3) . ? C2 O2 1.337(3) . ? C2 C3 1.491(4) . ? C3 C4 1.393(4) . ? C3 C8 1.394(4) . ? C4 C5 1.391(4) . ? C4 H4 0.95 . ? C5 C6 1.398(4) . ? C5 H5 0.95 . ? C6 C7 1.395(3) . ? C6 C9 1.521(4) . ? C7 C8 1.388(4) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C14 1.514(4) . ? C9 C10 1.518(3) . ? C9 H9 1 . ? C10 N1 1.369(4) . ? C10 C11 1.369(4) . ? C11 C12 1.415(4) . ? C11 H11 0.95 . ? C12 C13 1.368(4) . ? C12 H12 0.95 . ? C13 N1 1.372(3) . ? C13 H13 0.95 . ? C14 N2 1.365(3) . ? C14 C15 1.372(4) . ? C15 C16 1.410(4) . ? C15 H15 0.95 . ? C16 C17 1.351(4) . ? C16 H16 0.95 . ? C17 N2 1.369(4) . ? C17 H17 0.95 . ? N1 H1 0.865(10) . ? N2 H2 0.865(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 124.1(3) . . ? O1 C2 C3 123.9(3) . . ? O2 C2 C3 112.0(2) . . ? C4 C3 C8 119.0(3) . . ? C4 C3 C2 122.5(3) . . ? C8 C3 C2 118.4(2) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.8(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 118.5(2) . . ? C7 C6 C9 120.2(2) . . ? C5 C6 C9 121.3(2) . . ? C8 C7 C6 120.8(3) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C3 120.5(2) . . ? C7 C8 H8 119.7 . . ? C3 C8 H8 119.7 . . ? C14 C9 C10 110.7(2) . . ? C14 C9 C6 111.1(2) . . ? C10 C9 C6 113.7(2) . . ? C14 C9 H9 107 . . ? C10 C9 H9 107 . . ? C6 C9 H9 107 . . ? N1 C10 C11 107.3(2) . . ? N1 C10 C9 122.0(2) . . ? C11 C10 C9 130.6(3) . . ? C10 C11 C12 107.9(3) . . ? C10 C11 H11 126 . . ? C12 C11 H11 126 . . ? C13 C12 C11 107.3(2) . . ? C13 C12 H12 126.4 . . ? C11 C12 H12 126.4 . . ? C12 C13 N1 107.7(3) . . ? C12 C13 H13 126.2 . . ? N1 C13 H13 126.2 . . ? N2 C14 C15 106.6(3) . . ? N2 C14 C9 121.8(2) . . ? C15 C14 C9 131.6(2) . . ? C14 C15 C16 108.3(3) . . ? C14 C15 H15 125.9 . . ? C16 C15 H15 125.9 . . ? C17 C16 C15 107.1(3) . . ? C17 C16 H16 126.5 . . ? C15 C16 H16 126.5 . . ? C16 C17 N2 108.3(3) . . ? C16 C17 H17 125.9 . . ? N2 C17 H17 125.9 . . ? C10 N1 C13 109.8(2) . . ? C10 N1 H1 125(2) . . ? C13 N1 H1 125(2) . . ? C14 N2 C17 109.8(3) . . ? C14 N2 H2 122(2) . . ? C17 N2 H2 127(2) . . ? C2 O2 C1 116.0(2) . . ? #===END