# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 N5' _chemical_formula_sum 'C18 H13 N5' _chemical_formula_weight 299.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.697(4) _cell_length_b 18.417(3) _cell_length_c 19.169(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.498(13) _cell_angle_gamma 90.00 _cell_volume 2928.3(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14669 _cell_measurement_theta_min 1.57 _cell_measurement_theta_max 25.06 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9839 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details 'SADABS(Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14669 _diffrn_reflns_av_R_equivalents 0.0980 _diffrn_reflns_av_sigmaI/netI 0.0967 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.06 _reflns_number_total 5174 _reflns_number_gt 3227 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97(Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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^ > 2\s(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^)+(0.0417P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0069(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5174 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.8935(2) 0.41636(10) 0.29271(9) 0.0574(5) Uani 1 1 d . . . N2 N -0.0661(2) 0.29850(10) -0.15204(9) 0.0611(5) Uani 1 1 d . . . N3 N 0.4654(2) 0.74056(8) 0.12367(8) 0.0485(5) Uani 1 1 d . . . N4 N 0.39041(16) 0.39521(7) 0.07099(7) 0.0360(4) Uani 1 1 d . . . H4A H 0.4112 0.3500 0.0807 0.043 Uiso 1 1 d R . . N5 N 0.26954(18) 0.49367(7) 0.01421(8) 0.0381(4) Uani 1 1 d . . . C1 C 0.4948(2) 0.69044(10) 0.17636(10) 0.0479(5) Uani 1 1 d . . . H1 H 0.5310 0.7063 0.2246 0.057 Uiso 1 1 calc R . . C2 C 0.4753(2) 0.61712(9) 0.16403(9) 0.0419(5) Uani 1 1 d . . . H2 H 0.4988 0.5849 0.2031 0.050 Uiso 1 1 calc R . . C3 C 0.4200(2) 0.59146(9) 0.09256(9) 0.0353(4) Uani 1 1 d . . . C4 C 0.4088(2) 0.71520(10) 0.05526(10) 0.0491(6) Uani 1 1 d . . . H4 H 0.3855 0.7487 0.0172 0.059 Uiso 1 1 calc R . . C5 C 0.3828(2) 0.64313(9) 0.03746(10) 0.0413(5) Uani 1 1 d . . . H5 H 0.3406 0.6291 -0.0112 0.050 Uiso 1 1 calc R . . C6 C 0.3936(2) 0.51360(9) 0.07496(9) 0.0342(4) Uani 1 1 d . . . C7 C 0.4718(2) 0.45295(9) 0.11062(9) 0.0332(4) Uani 1 1 d . . . C8 C 0.2715(2) 0.42214(9) 0.01388(9) 0.0347(4) Uani 1 1 d . . . C9 C 0.1580(2) 0.37785(10) -0.04208(9) 0.0361(4) Uani 1 1 d . . . C10 C 0.1684(2) 0.30334(10) -0.04653(10) 0.0498(6) Uani 1 1 d . . . H10 H 0.2511 0.2781 -0.0132 0.060 Uiso 1 1 calc R . . C11 C 0.0541(3) 0.26649(12) -0.10120(11) 0.0591(6) Uani 1 1 d . . . H11 H 0.0617 0.2162 -0.1025 0.071 Uiso 1 1 calc R . . C12 C -0.0730(3) 0.37050(12) -0.14768(11) 0.0574(6) Uani 1 1 d . . . H12 H -0.1543 0.3946 -0.1828 0.069 Uiso 1 1 calc R . . C13 C 0.0329(2) 0.41140(11) -0.09441(10) 0.0482(5) Uani 1 1 d . . . H13 H 0.0204 0.4615 -0.0936 0.058 Uiso 1 1 calc R . . C14 C 0.6150(2) 0.44170(9) 0.17407(9) 0.0347(4) Uani 1 1 d . . . C15 C 0.7415(2) 0.49108(11) 0.19354(10) 0.0468(5) Uani 1 1 d . . . H15 H 0.7372 0.5336 0.1669 0.056 Uiso 1 1 calc R . . C16 C 0.8735(2) 0.47625(12) 0.25277(11) 0.0562(6) Uani 1 1 d . . . H16 H 0.9547 0.5110 0.2657 0.067 Uiso 1 1 calc R . . C17 C 0.7738(3) 0.36862(12) 0.27256(10) 0.0518(6) Uani 1 1 d . . . H17 H 0.7848 0.3253 0.2985 0.062 Uiso 1 1 calc R . . C18 C 0.6341(2) 0.37906(10) 0.21575(9) 0.0432(5) Uani 1 1 d . . . H18 H 0.5531 0.3442 0.2055 0.052 Uiso 1 1 calc R . . N6 N -0.0259(2) 0.29471(10) 0.13247(9) 0.0590(5) Uani 1 1 d . . . N7 N 0.45264(17) 0.39418(7) 0.34565(7) 0.0357(4) Uani 1 1 d . . . H7 H 0.4724 0.3493 0.3573 0.043 Uiso 1 1 d R . . N8 N 0.33209(17) 0.49159(7) 0.28582(7) 0.0359(4) Uani 1 1 d . . . N9 N 0.5485(2) 0.73925(8) 0.38723(8) 0.0439(4) Uani 1 1 d . . . N10 N 0.9452(2) 0.42959(10) 0.57372(9) 0.0589(5) Uani 1 1 d . . . C19 C 0.1327(2) 0.40240(10) 0.16716(10) 0.0434(5) Uani 1 1 d . . . H19 H 0.1573 0.4486 0.1542 0.052 Uiso 1 1 calc R . . C20 C 0.0159(2) 0.36153(12) 0.11876(11) 0.0526(6) Uani 1 1 d . . . H20 H -0.0373 0.3819 0.0735 0.063 Uiso 1 1 calc R . . C21 C 0.0540(2) 0.26803(11) 0.19787(12) 0.0562(6) Uani 1 1 d . . . H21 H 0.0281 0.2214 0.2091 0.067 Uiso 1 1 calc R . . C22 C 0.1729(2) 0.30486(10) 0.25023(10) 0.0441(5) Uani 1 1 d . . . H22 H 0.2247 0.2831 0.2949 0.053 Uiso 1 1 calc R . . C23 C 0.2137(2) 0.37431(9) 0.23542(9) 0.0345(4) Uani 1 1 d . . . C24 C 0.3308(2) 0.41980(9) 0.28829(9) 0.0337(4) Uani 1 1 d . . . C25 C 0.4605(2) 0.51296(9) 0.34351(9) 0.0332(4) Uani 1 1 d . . . C26 C 0.5386(2) 0.45297(9) 0.38177(9) 0.0333(4) Uani 1 1 d . . . C27 C 0.6771(2) 0.44517(9) 0.44738(9) 0.0352(4) Uani 1 1 d . . . C28 C 0.7762(2) 0.38439(10) 0.45867(10) 0.0464(5) Uani 1 1 d . . . H28 H 0.7569 0.3476 0.4239 0.056 Uiso 1 1 calc R . . C29 C 0.9039(2) 0.37924(12) 0.52215(11) 0.0608(6) Uani 1 1 d . . . H29 H 0.9656 0.3371 0.5292 0.073 Uiso 1 1 calc R . . C30 C 0.8508(2) 0.48811(12) 0.56234(10) 0.0500(6) Uani 1 1 d . . . H30 H 0.8763 0.5249 0.5972 0.060 Uiso 1 1 calc R . . C31 C 0.7176(2) 0.49757(10) 0.50205(9) 0.0420(5) Uani 1 1 d . . . H31 H 0.6547 0.5391 0.4980 0.050 Uiso 1 1 calc R . . C32 C 0.4934(2) 0.59070(9) 0.35756(9) 0.0328(4) Uani 1 1 d . . . C33 C 0.3678(2) 0.63835(9) 0.35418(9) 0.0395(5) Uani 1 1 d . . . H33 H 0.2622 0.6215 0.3416 0.047 Uiso 1 1 calc R . . C34 C 0.4003(2) 0.71053(10) 0.36955(10) 0.0442(5) Uani 1 1 d . . . H34 H 0.3143 0.7413 0.3676 0.053 Uiso 1 1 calc R . . C35 C 0.6679(2) 0.69319(10) 0.38785(9) 0.0430(5) Uani 1 1 d . . . H35 H 0.7718 0.7119 0.3986 0.052 Uiso 1 1 calc R . . C36 C 0.6471(2) 0.62003(9) 0.37363(9) 0.0382(5) Uani 1 1 d . . . H36 H 0.7348 0.5906 0.3748 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0449(11) 0.0668(13) 0.0468(10) -0.0023(10) -0.0068(9) 0.0084(10) N2 0.0537(12) 0.0629(13) 0.0542(11) -0.0156(10) -0.0024(9) -0.0093(10) N3 0.0597(12) 0.0331(9) 0.0432(10) -0.0015(8) 0.0013(9) -0.0050(8) N4 0.0368(9) 0.0262(8) 0.0360(8) -0.0008(7) -0.0024(7) 0.0028(7) N5 0.0402(10) 0.0318(9) 0.0326(8) -0.0020(7) -0.0038(7) 0.0000(7) C1 0.0592(14) 0.0391(12) 0.0357(11) -0.0041(10) -0.0002(10) -0.0053(10) C2 0.0531(13) 0.0325(11) 0.0315(10) 0.0007(8) 0.0000(9) -0.0029(9) C3 0.0319(11) 0.0325(10) 0.0358(10) -0.0005(8) 0.0018(8) -0.0018(8) C4 0.0631(15) 0.0367(12) 0.0411(12) 0.0064(9) 0.0058(11) -0.0017(10) C5 0.0467(13) 0.0354(11) 0.0341(10) -0.0002(9) 0.0005(9) -0.0020(9) C6 0.0346(11) 0.0306(10) 0.0324(10) -0.0024(8) 0.0024(8) -0.0019(8) C7 0.0315(10) 0.0300(10) 0.0324(9) -0.0030(8) 0.0009(8) 0.0000(8) C8 0.0349(11) 0.0317(11) 0.0305(10) -0.0018(8) -0.0008(8) 0.0014(8) C9 0.0362(11) 0.0352(11) 0.0322(10) -0.0024(8) 0.0032(8) -0.0023(9) C10 0.0546(14) 0.0395(12) 0.0423(11) -0.0026(9) -0.0053(10) -0.0039(10) C11 0.0711(17) 0.0427(13) 0.0542(13) -0.0113(11) 0.0048(13) -0.0088(12) C12 0.0451(14) 0.0653(16) 0.0477(13) -0.0095(11) -0.0076(10) -0.0006(12) C13 0.0406(12) 0.0452(12) 0.0464(12) -0.0047(10) -0.0056(10) 0.0026(10) C14 0.0327(11) 0.0338(11) 0.0322(10) -0.0032(8) 0.0014(8) 0.0042(8) C15 0.0373(12) 0.0475(12) 0.0467(12) 0.0013(10) -0.0006(10) -0.0033(10) C16 0.0381(13) 0.0635(15) 0.0551(13) -0.0080(12) -0.0042(11) -0.0064(11) C17 0.0530(14) 0.0533(14) 0.0386(11) 0.0021(10) -0.0020(11) 0.0137(11) C18 0.0439(12) 0.0386(11) 0.0388(11) -0.0020(9) -0.0004(9) 0.0044(9) N6 0.0477(12) 0.0646(13) 0.0544(11) -0.0136(10) -0.0002(9) -0.0133(10) N7 0.0352(9) 0.0253(8) 0.0379(8) 0.0021(7) -0.0022(7) 0.0014(7) N8 0.0338(9) 0.0287(9) 0.0365(8) 0.0011(7) -0.0023(7) 0.0018(7) N9 0.0414(10) 0.0301(9) 0.0491(10) -0.0015(7) -0.0032(8) -0.0016(8) N10 0.0474(11) 0.0696(13) 0.0449(10) 0.0000(10) -0.0086(9) 0.0047(10) C19 0.0333(11) 0.0450(12) 0.0431(11) 0.0010(9) -0.0019(9) -0.0013(9) C20 0.0386(12) 0.0642(15) 0.0441(12) -0.0040(11) -0.0040(10) -0.0035(11) C21 0.0498(14) 0.0452(13) 0.0679(15) -0.0096(11) 0.0091(12) -0.0144(11) C22 0.0406(12) 0.0360(11) 0.0482(11) -0.0005(9) 0.0021(10) -0.0028(9) C23 0.0273(10) 0.0347(11) 0.0373(10) -0.0036(8) 0.0031(8) 0.0020(8) C24 0.0288(10) 0.0328(11) 0.0332(10) 0.0007(8) -0.0003(8) 0.0029(8) C25 0.0288(10) 0.0324(10) 0.0317(10) -0.0005(8) -0.0010(8) 0.0003(8) C26 0.0311(10) 0.0292(10) 0.0337(10) -0.0020(8) 0.0012(8) -0.0004(8) C27 0.0335(11) 0.0337(11) 0.0315(10) 0.0042(8) -0.0007(8) -0.0025(8) C28 0.0422(12) 0.0436(12) 0.0414(11) -0.0015(9) -0.0055(9) 0.0084(10) C29 0.0504(14) 0.0591(14) 0.0563(14) 0.0054(12) -0.0088(11) 0.0170(12) C30 0.0474(13) 0.0572(14) 0.0357(11) -0.0021(10) -0.0025(10) -0.0080(11) C31 0.0440(12) 0.0386(11) 0.0357(11) 0.0015(9) 0.0005(9) -0.0007(9) C32 0.0348(11) 0.0296(10) 0.0267(9) 0.0018(8) -0.0016(8) 0.0010(8) C33 0.0323(11) 0.0334(11) 0.0456(11) 0.0021(9) 0.0007(9) -0.0011(9) C34 0.0397(12) 0.0338(11) 0.0517(12) -0.0016(9) 0.0027(10) 0.0042(9) C35 0.0348(12) 0.0391(12) 0.0456(11) 0.0016(9) -0.0021(9) -0.0077(9) C36 0.0341(11) 0.0328(10) 0.0415(11) 0.0018(9) 0.0019(9) 0.0009(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 C16 1.324(2) . ? N1 C17 1.329(3) . ? N2 C12 1.331(3) . ? N2 C11 1.333(2) . ? N3 C1 1.335(2) . ? N3 C4 1.339(2) . ? N4 C8 1.354(2) . ? N4 C7 1.3732(19) . ? N4 H4A 0.8600 . ? N5 C8 1.318(2) . ? N5 C6 1.378(2) . ? C1 C2 1.373(2) . ? C1 H1 0.9300 . ? C2 C3 1.391(2) . ? C2 H2 0.9300 . ? C3 C5 1.386(2) . ? C3 C6 1.475(2) . ? C4 C5 1.372(2) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.378(2) . ? C7 C14 1.470(2) . ? C8 C9 1.468(2) . ? C9 C10 1.380(2) . ? C9 C13 1.384(2) . ? C10 C11 1.386(2) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.376(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C18 1.385(2) . ? C14 C15 1.389(2) . ? C15 C16 1.377(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.379(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N6 C21 1.331(2) . ? N6 C20 1.332(3) . ? N7 C24 1.3617(19) . ? N7 C26 1.378(2) . ? N7 H7 0.8601 . ? N8 C24 1.323(2) . ? N8 C25 1.372(2) . ? N9 C35 1.339(2) . ? N9 C34 1.339(2) . ? N10 C29 1.324(2) . ? N10 C30 1.333(2) . ? C19 C20 1.376(2) . ? C19 C23 1.386(2) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.383(2) . ? C21 H21 0.9300 . ? C22 C23 1.380(2) . ? C22 H22 0.9300 . ? C23 C24 1.464(2) . ? C25 C26 1.386(2) . ? C25 C32 1.469(2) . ? C26 C27 1.463(2) . ? C27 C28 1.390(2) . ? C27 C31 1.390(2) . ? C28 C29 1.382(2) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 C31 1.379(2) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C33 1.388(2) . ? C32 C36 1.388(2) . ? C33 C34 1.373(2) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 C36 1.376(2) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N1 C17 115.32(17) . . ? C12 N2 C11 115.78(17) . . ? C1 N3 C4 115.48(16) . . ? C8 N4 C7 107.77(13) . . ? C8 N4 H4A 126.1 . . ? C7 N4 H4A 126.1 . . ? C8 N5 C6 105.21(14) . . ? N3 C1 C2 124.35(17) . . ? N3 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C1 C2 C3 119.48(17) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C5 C3 C2 116.72(16) . . ? C5 C3 C6 120.57(15) . . ? C2 C3 C6 122.64(16) . . ? N3 C4 C5 124.45(17) . . ? N3 C4 H4 117.8 . . ? C5 C4 H4 117.8 . . ? C4 C5 C3 119.44(16) . . ? C4 C5 H5 120.3 . . ? C3 C5 H5 120.3 . . ? C7 C6 N5 110.35(14) . . ? C7 C6 C3 130.91(15) . . ? N5 C6 C3 118.73(15) . . ? N4 C7 C6 104.94(14) . . ? N4 C7 C14 121.07(15) . . ? C6 C7 C14 133.92(16) . . ? N5 C8 N4 111.73(15) . . ? N5 C8 C9 123.53(15) . . ? N4 C8 C9 124.74(15) . . ? C10 C9 C13 116.80(17) . . ? C10 C9 C8 123.78(16) . . ? C13 C9 C8 119.41(16) . . ? C9 C10 C11 119.24(19) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? N2 C11 C10 124.25(19) . . ? N2 C11 H11 117.9 . . ? C10 C11 H11 117.9 . . ? N2 C12 C13 124.01(19) . . ? N2 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? C12 C13 C9 119.89(19) . . ? C12 C13 H13 120.1 . . ? C9 C13 H13 120.1 . . ? C18 C14 C15 116.27(16) . . ? C18 C14 C7 121.29(16) . . ? C15 C14 C7 122.37(16) . . ? C16 C15 C14 119.20(19) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? N1 C16 C15 125.0(2) . . ? N1 C16 H16 117.5 . . ? C15 C16 H16 117.5 . . ? N1 C17 C18 124.37(19) . . ? N1 C17 H17 117.8 . . ? C18 C17 H17 117.8 . . ? C17 C18 C14 119.74(19) . . ? C17 C18 H18 120.1 . . ? C14 C18 H18 120.1 . . ? C21 N6 C20 115.50(17) . . ? C24 N7 C26 107.84(14) . . ? C24 N7 H7 126.1 . . ? C26 N7 H7 126.1 . . ? C24 N8 C25 105.76(14) . . ? C35 N9 C34 115.94(16) . . ? C29 N10 C30 115.39(17) . . ? C20 C19 C23 119.67(18) . . ? C20 C19 H19 120.2 . . ? C23 C19 H19 120.2 . . ? N6 C20 C19 124.25(19) . . ? N6 C20 H20 117.9 . . ? C19 C20 H20 117.9 . . ? N6 C21 C22 124.56(19) . . ? N6 C21 H21 117.7 . . ? C22 C21 H21 117.7 . . ? C21 C22 C23 119.20(18) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C22 C23 C19 116.81(17) . . ? C22 C23 C24 123.80(16) . . ? C19 C23 C24 119.33(16) . . ? N8 C24 N7 111.23(15) . . ? N8 C24 C23 123.95(15) . . ? N7 C24 C23 124.81(15) . . ? N8 C25 C26 110.39(15) . . ? N8 C25 C32 119.60(14) . . ? C26 C25 C32 129.98(15) . . ? N7 C26 C25 104.78(14) . . ? N7 C26 C27 122.45(15) . . ? C25 C26 C27 132.74(16) . . ? C28 C27 C31 115.91(16) . . ? C28 C27 C26 121.65(16) . . ? C31 C27 C26 122.44(16) . . ? C29 C28 C27 119.27(18) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? N10 C29 C28 125.1(2) . . ? N10 C29 H29 117.4 . . ? C28 C29 H29 117.4 . . ? N10 C30 C31 124.07(19) . . ? N10 C30 H30 118.0 . . ? C31 C30 H30 118.0 . . ? C30 C31 C27 120.18(18) . . ? C30 C31 H31 119.9 . . ? C27 C31 H31 119.9 . . ? C33 C32 C36 117.18(16) . . ? C33 C32 C25 120.02(16) . . ? C36 C32 C25 122.81(16) . . ? C34 C33 C32 119.58(17) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? N9 C34 C33 123.90(18) . . ? N9 C34 H34 118.1 . . ? C33 C34 H34 118.1 . . ? N9 C35 C36 124.29(18) . . ? N9 C35 H35 117.9 . . ? C36 C35 H35 117.9 . . ? C35 C36 C32 119.05(18) . . ? C35 C36 H36 120.5 . . ? C32 C36 H36 120.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.262 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 909296' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H45 N12 O15.50 Zn' _chemical_formula_sum 'C36 H45 N12 O15.50 Zn' _chemical_formula_weight 959.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.548(4) _cell_length_b 10.060(5) _cell_length_c 30.328(3) _cell_angle_alpha 85.046(4) _cell_angle_beta 87.380(2) _cell_angle_gamma 77.3180(10) _cell_volume 2237.5(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9896 _cell_measurement_theta_min 1.35 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 998 _exptl_absorpt_coefficient_mu 0.629 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8688 _exptl_absorpt_correction_T_max 0.8898 _exptl_absorpt_process_details 'SADABS(Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9896 _diffrn_reflns_av_R_equivalents 0.1014 _diffrn_reflns_av_sigmaI/netI 0.1093 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7538 _reflns_number_gt 5115 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97(Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _refine_special_details ; During the refinement, the command 'omit -3 50' was used to omit the weak reflections above 50 degree.During the refinement, the command 'ISOR' was used to restrain some non-H atoms with NPD and/or ADP problems. These atoms are as follows:O1 O9WA O2A O9WB o2b O5W O6W O8W. The restraint command 'PART' was refined the atoms O3, O9w and O2. All above refinement led to a relatively high restraint value (48). 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^ > 2\s(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^)+(0.1118P)^2^+11.5134P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7538 _refine_ls_number_parameters 611 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.1422 _refine_ls_R_factor_gt 0.1039 _refine_ls_wR_factor_ref 0.2826 _refine_ls_wR_factor_gt 0.2595 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2680(15) -0.0865(11) -0.0816(3) 0.058(3) Uani 1 1 d . . . H1 H 0.2568 -0.1554 -0.0991 0.070 Uiso 1 1 calc R . . C2 C 0.2443(14) -0.1066(10) -0.0372(3) 0.053(2) Uani 1 1 d . . . H2 H 0.2175 -0.1884 -0.0251 0.064 Uiso 1 1 calc R . . C3 C 0.3247(14) 0.1259(11) -0.0751(3) 0.056(3) Uani 1 1 d . . . H3 H 0.3564 0.2050 -0.0880 0.067 Uiso 1 1 calc R . . C4 C 0.2982(13) 0.1140(10) -0.0298(3) 0.049(2) Uani 1 1 d . . . H4 H 0.3061 0.1854 -0.0130 0.059 Uiso 1 1 calc R . . C5 C 0.2591(12) -0.0075(9) -0.0092(3) 0.0394(19) Uani 1 1 d . . . C6 C 0.1837(11) -0.1145(8) 0.1047(2) 0.0352(18) Uani 1 1 d . . . C7 C 0.2312(11) -0.0251(8) 0.0384(2) 0.0365(19) Uani 1 1 d . . . C8 C 0.1935(11) 0.0196(8) 0.1077(2) 0.0365(19) Uani 1 1 d . . . C9 C 0.1587(12) -0.2189(8) 0.1398(3) 0.0375(19) Uani 1 1 d . . . C10 C 0.0732(12) -0.3244(9) 0.1323(3) 0.042(2) Uani 1 1 d . . . H10 H 0.0327 -0.3311 0.1042 0.050 Uiso 1 1 calc R . . C11 C 0.0495(12) -0.4179(8) 0.1664(3) 0.040(2) Uani 1 1 d . . . H11 H -0.0108 -0.4857 0.1608 0.048 Uiso 1 1 calc R . . C12 C 0.1947(12) -0.3186(8) 0.2145(3) 0.040(2) Uani 1 1 d . . . H12 H 0.2377 -0.3168 0.2426 0.048 Uiso 1 1 calc R . . C13 C 0.2229(12) -0.2193(9) 0.1820(3) 0.040(2) Uani 1 1 d . . . H13 H 0.2845 -0.1531 0.1885 0.047 Uiso 1 1 calc R . . C14 C 0.1693(12) 0.1044(8) 0.1458(3) 0.0376(19) Uani 1 1 d . . . C15 C 0.0199(11) 0.1103(8) 0.1751(3) 0.0368(19) Uani 1 1 d . . . H15 H -0.0630 0.0555 0.1725 0.044 Uiso 1 1 calc R . . C16 C -0.0015(12) 0.1992(8) 0.2081(3) 0.0385(19) Uani 1 1 d . . . H16 H -0.1026 0.2044 0.2271 0.046 Uiso 1 1 calc R . . C17 C 0.2603(11) 0.2694(8) 0.1867(3) 0.040(2) Uani 1 1 d . . . H17 H 0.3443 0.3219 0.1910 0.049 Uiso 1 1 calc R . . C18 C 0.2899(12) 0.1863(8) 0.1525(3) 0.040(2) Uani 1 1 d . . . H18 H 0.3910 0.1846 0.1337 0.049 Uiso 1 1 calc R . . C19 C -0.0954(10) 0.7128(8) 0.3019(3) 0.0316(17) Uani 1 1 d . . . H19 H -0.1450 0.7391 0.2741 0.038 Uiso 1 1 calc R . . C20 C -0.1361(11) 0.8041(8) 0.3342(3) 0.0357(18) Uani 1 1 d . . . H20 H -0.2105 0.8899 0.3281 0.043 Uiso 1 1 calc R . . C21 C -0.0649(10) 0.7667(8) 0.3760(2) 0.0309(17) Uani 1 1 d . . . C22 C 0.0829(11) 0.5524(8) 0.3488(3) 0.0358(18) Uani 1 1 d . . . H22 H 0.1597 0.4669 0.3538 0.043 Uiso 1 1 calc R . . C23 C 0.0468(11) 0.6369(8) 0.3828(3) 0.0370(19) Uani 1 1 d . . . H23 H 0.0967 0.6076 0.4104 0.044 Uiso 1 1 calc R . . C24 C -0.1085(11) 0.8566(8) 0.4128(2) 0.0322(17) Uani 1 1 d . . . C25 C -0.1171(10) 0.9943(8) 0.4135(2) 0.0294(16) Uani 1 1 d . . . C26 C -0.2042(11) 0.9124(8) 0.4786(2) 0.0339(18) Uani 1 1 d . . . C27 C -0.2784(11) 0.9041(8) 0.5239(2) 0.0343(18) Uani 1 1 d . . . C28 C -0.2926(13) 0.7782(9) 0.5452(3) 0.047(2) Uani 1 1 d . . . H28 H -0.2496 0.6978 0.5315 0.057 Uiso 1 1 calc R . . C29 C -0.3714(14) 0.7750(11) 0.5872(3) 0.054(2) Uani 1 1 d . . . H29 H -0.3780 0.6899 0.6010 0.065 Uiso 1 1 calc R . . C30 C -0.4202(12) 1.0040(10) 0.5887(3) 0.048(2) Uani 1 1 d . . . H30 H -0.4628 1.0824 0.6036 0.058 Uiso 1 1 calc R . . C31 C -0.3425(12) 1.0189(9) 0.5469(3) 0.042(2) Uani 1 1 d . . . H31 H -0.3333 1.1049 0.5344 0.050 Uiso 1 1 calc R . . C32 C -0.0749(10) 1.0953(8) 0.3797(2) 0.0296(17) Uani 1 1 d . . . C33 C 0.0590(10) 1.0574(8) 0.3469(2) 0.0313(17) Uani 1 1 d . . . H33 H 0.1253 0.9677 0.3470 0.038 Uiso 1 1 calc R . . C34 C 0.0911(10) 1.1546(7) 0.3144(2) 0.0293(16) Uani 1 1 d . . . H34 H 0.1813 1.1277 0.2931 0.035 Uiso 1 1 calc R . . C35 C -0.1704(11) 1.2312(8) 0.3763(3) 0.0358(19) Uani 1 1 d . . . H35 H -0.2619 1.2609 0.3971 0.043 Uiso 1 1 calc R . . C36 C -0.1312(11) 1.3204(8) 0.3431(3) 0.0364(19) Uani 1 1 d . . . H36 H -0.1980 1.4100 0.3418 0.044 Uiso 1 1 calc R . . N1 N 0.1146(9) 0.2780(7) 0.2142(2) 0.0364(16) Uani 1 1 d . . . N2 N 0.1080(9) -0.4174(6) 0.2071(2) 0.0320(14) Uani 1 1 d . . . N3 N 0.3073(11) 0.0296(9) -0.1016(2) 0.057(2) Uani 1 1 d . . . N4 N 0.2088(10) -0.1409(7) 0.0607(2) 0.0389(16) Uani 1 1 d . . . N5 N 0.2217(10) 0.0741(7) 0.0658(2) 0.0405(17) Uani 1 1 d . . . H5 H 0.2316 0.1566 0.0584 0.049 Uiso 1 1 calc R . . N6 N 0.0123(9) 0.5878(6) 0.3085(2) 0.0322(15) Uani 1 1 d . . . N7 N 0.0009(9) 1.2849(6) 0.3117(2) 0.0322(15) Uani 1 1 d . . . N8 N -0.1625(9) 0.8074(7) 0.4535(2) 0.0350(15) Uani 1 1 d . . . H8 H -0.1683 0.7242 0.4613 0.042 Uiso 1 1 calc R . . N9 N -0.1806(9) 1.0285(6) 0.4559(2) 0.0333(15) Uani 1 1 d . . . N10 N -0.4383(11) 0.8839(9) 0.6093(2) 0.052(2) Uani 1 1 d . . . N11 N 0.4697(11) 0.6458(9) 0.3360(3) 0.055(2) Uani 1 1 d . . . N12 N -0.3907(19) 0.4706(14) 0.1374(5) 0.109(4) Uani 1 1 d . . . O1 O -0.368(2) 0.4044(15) 0.1734(5) 0.151(5) Uani 1 1 d U C . O1W O -0.2260(9) 0.4907(7) 0.2440(2) 0.0581(18) Uani 1 1 d . . . H1A H -0.2819 0.4105 0.2508 0.070 Uiso 1 1 d R . . H1B H -0.2885 0.5664 0.2618 0.070 Uiso 1 1 d R . . O2W O 0.3425(8) 0.3900(6) 0.27694(19) 0.0434(14) Uani 1 1 d . . . H2A H 0.4175 0.4049 0.2500 0.052 Uiso 1 1 d R . . H2B H 0.3607 0.4516 0.2994 0.052 Uiso 1 1 d R . . O4 O 0.5124(13) 0.5479(11) 0.3639(4) 0.109(3) Uani 1 1 d . . . O5 O 0.4862(10) 0.6224(9) 0.2967(3) 0.079(2) Uani 1 1 d . . . O6 O 0.4195(14) 0.7592(9) 0.3469(4) 0.111(4) Uani 1 1 d . . . O11W O -0.2529(18) 1.3081(10) 0.4856(3) 0.118(4) Uani 1 1 d . . . O12W O 0.6690(12) 0.8416(9) 0.1895(2) 0.080(2) Uani 1 1 d . . . Zn1 Zn 0.06143(13) 0.43406(9) 0.26026(3) 0.0321(3) Uani 1 1 d . . . O3A O -0.176(6) 0.493(4) 0.0401(12) 0.136(15) Uani 0.30 1 d P A 1 O9WA O 0.067(4) 0.370(3) 0.0502(9) 0.142(9) Uani 0.50 1 d PU B 1 O2A O -0.373(2) 0.5857(19) 0.1388(5) 0.137(5) Uani 0.80 1 d PU C 1 O3B O -0.455(3) 0.4202(18) 0.1097(5) 0.130(6) Uani 0.70 1 d P C 2 O9WB O 0.213(3) 0.353(2) 0.0488(7) 0.117(7) Uani 0.50 1 d PU D 2 O2B O -0.303(8) 0.504(6) 0.093(2) 0.121(16) Uani 0.20 1 d PU C 2 O3W O 0.4524(11) 0.9385(8) 0.2607(3) 0.076(2) Uani 1 1 d . E 2 O4W O 0.5586(9) 0.1458(6) 0.3002(2) 0.0525(16) Uani 1 1 d . F 2 O5W O -0.415(2) 0.6121(16) 0.4525(5) 0.173(5) Uani 1 1 d U G 2 O6W O -0.631(3) 0.5873(19) 0.0389(6) 0.207(7) Uani 1 1 d U H 2 O8W O 0.0000 0.5000 0.5000 0.201(9) Uani 1 2 d SU I 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.074(7) 0.067(7) 0.035(5) -0.013(5) 0.006(5) -0.017(6) C2 0.070(7) 0.061(6) 0.031(5) 0.000(4) -0.001(4) -0.019(5) C3 0.073(7) 0.058(6) 0.041(5) 0.006(5) 0.011(5) -0.029(5) C4 0.059(6) 0.058(6) 0.034(5) 0.000(4) 0.001(4) -0.022(5) C5 0.049(5) 0.042(5) 0.028(4) -0.005(4) 0.002(4) -0.011(4) C6 0.047(5) 0.038(4) 0.023(4) -0.004(3) -0.002(3) -0.015(4) C7 0.048(5) 0.040(5) 0.024(4) -0.003(3) -0.002(4) -0.015(4) C8 0.049(5) 0.037(4) 0.026(4) -0.002(3) 0.002(4) -0.013(4) C9 0.054(5) 0.031(4) 0.028(4) -0.001(3) 0.004(4) -0.011(4) C10 0.058(6) 0.043(5) 0.029(4) -0.005(4) -0.003(4) -0.019(4) C11 0.053(5) 0.038(5) 0.034(4) -0.006(4) 0.003(4) -0.019(4) C12 0.063(6) 0.041(5) 0.021(4) -0.004(3) -0.001(4) -0.021(4) C13 0.046(5) 0.043(5) 0.036(5) -0.006(4) 0.003(4) -0.025(4) C14 0.056(5) 0.030(4) 0.027(4) -0.002(3) 0.009(4) -0.014(4) C15 0.040(5) 0.044(5) 0.033(4) -0.007(4) 0.004(3) -0.023(4) C16 0.045(5) 0.042(5) 0.032(4) -0.005(4) 0.009(4) -0.021(4) C17 0.041(5) 0.041(5) 0.045(5) -0.017(4) 0.016(4) -0.020(4) C18 0.042(5) 0.042(5) 0.043(5) -0.008(4) 0.015(4) -0.023(4) C19 0.032(4) 0.032(4) 0.033(4) 0.000(3) 0.000(3) -0.011(3) C20 0.042(5) 0.030(4) 0.034(4) -0.003(3) 0.002(4) -0.005(3) C21 0.036(4) 0.031(4) 0.029(4) -0.003(3) 0.004(3) -0.012(3) C22 0.035(4) 0.029(4) 0.040(5) 0.000(3) -0.004(4) 0.000(3) C23 0.048(5) 0.037(4) 0.024(4) 0.001(3) -0.003(4) -0.007(4) C24 0.037(4) 0.030(4) 0.028(4) -0.002(3) 0.007(3) -0.007(3) C25 0.027(4) 0.035(4) 0.027(4) -0.007(3) 0.005(3) -0.008(3) C26 0.037(5) 0.035(4) 0.030(4) -0.001(3) 0.003(3) -0.009(3) C27 0.040(5) 0.040(4) 0.025(4) -0.004(3) 0.003(3) -0.011(4) C28 0.057(6) 0.043(5) 0.039(5) 0.001(4) 0.009(4) -0.005(4) C29 0.060(6) 0.059(6) 0.040(5) 0.013(5) 0.007(5) -0.016(5) C30 0.048(5) 0.067(6) 0.035(5) -0.015(4) 0.005(4) -0.019(5) C31 0.051(5) 0.045(5) 0.034(4) -0.003(4) 0.007(4) -0.020(4) C32 0.029(4) 0.033(4) 0.030(4) -0.007(3) 0.007(3) -0.014(3) C33 0.029(4) 0.031(4) 0.035(4) -0.007(3) 0.008(3) -0.008(3) C34 0.021(4) 0.033(4) 0.037(4) -0.009(3) 0.009(3) -0.011(3) C35 0.041(5) 0.032(4) 0.036(4) -0.012(3) 0.020(4) -0.012(4) C36 0.037(5) 0.027(4) 0.046(5) -0.008(3) 0.016(4) -0.011(3) N1 0.047(4) 0.036(4) 0.033(4) -0.008(3) 0.008(3) -0.024(3) N2 0.036(4) 0.033(3) 0.029(3) -0.003(3) 0.000(3) -0.011(3) N3 0.064(6) 0.070(6) 0.035(4) -0.003(4) 0.009(4) -0.012(4) N4 0.051(4) 0.041(4) 0.027(3) -0.007(3) 0.005(3) -0.016(3) N5 0.054(5) 0.042(4) 0.029(4) -0.003(3) 0.003(3) -0.020(3) N6 0.044(4) 0.025(3) 0.028(3) -0.001(3) 0.002(3) -0.008(3) N7 0.035(4) 0.025(3) 0.039(4) -0.004(3) 0.005(3) -0.011(3) N8 0.045(4) 0.030(3) 0.031(4) -0.003(3) 0.009(3) -0.012(3) N9 0.040(4) 0.034(4) 0.026(3) -0.003(3) 0.006(3) -0.011(3) N10 0.051(5) 0.078(6) 0.028(4) -0.001(4) 0.002(3) -0.020(4) N11 0.044(5) 0.059(6) 0.066(6) -0.020(5) 0.002(4) -0.014(4) N12 0.134(12) 0.099(10) 0.100(10) 0.027(8) -0.039(8) -0.047(8) O1 0.151(5) 0.152(5) 0.152(5) -0.0114(11) -0.0048(10) -0.0335(14) O1W 0.045(4) 0.070(5) 0.061(4) -0.018(3) 0.010(3) -0.014(3) O2W 0.044(3) 0.043(3) 0.047(3) -0.014(3) 0.006(3) -0.014(3) O4 0.083(7) 0.108(8) 0.114(8) 0.007(7) 0.008(6) 0.018(6) O5 0.063(5) 0.107(7) 0.074(5) -0.039(5) 0.000(4) -0.020(4) O6 0.113(8) 0.069(6) 0.160(10) -0.069(6) 0.043(7) -0.029(5) O11W 0.193(12) 0.092(7) 0.075(6) -0.017(5) 0.013(7) -0.045(7) O12W 0.097(6) 0.091(6) 0.046(4) -0.007(4) 0.023(4) -0.008(5) Zn1 0.0408(6) 0.0285(5) 0.0301(5) -0.0069(4) 0.0075(4) -0.0146(4) O3A 0.17(4) 0.12(3) 0.10(3) 0.01(2) 0.05(3) -0.02(3) O9WA 0.142(9) 0.142(9) 0.142(9) -0.0111(12) -0.0041(11) -0.031(2) O2A 0.137(5) 0.137(5) 0.138(5) -0.0105(11) -0.0038(10) -0.0301(15) O3B 0.180(17) 0.148(15) 0.094(11) -0.041(10) -0.034(11) -0.087(13) O9WB 0.117(7) 0.117(7) 0.117(7) -0.0091(12) -0.0030(11) -0.0253(18) O2B 0.121(16) 0.121(16) 0.121(16) -0.0094(16) -0.0033(11) -0.026(4) O3W 0.090(6) 0.071(5) 0.072(5) -0.026(4) 0.014(4) -0.020(4) O4W 0.053(4) 0.051(4) 0.049(4) -0.003(3) 0.002(3) -0.003(3) O5W 0.174(6) 0.173(6) 0.173(6) -0.0135(11) -0.0047(10) -0.0380(16) O6W 0.208(7) 0.207(7) 0.207(7) -0.0165(12) -0.0057(11) -0.0446(18) O8W 0.201(9) 0.201(9) 0.201(9) -0.0158(13) -0.0052(11) -0.043(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N3 1.354(13) . ? C1 C2 1.355(12) . ? C2 C5 1.389(12) . ? C3 N3 1.342(12) . ? C3 C4 1.379(12) . ? C4 C5 1.407(12) . ? C5 C7 1.452(11) . ? C6 C8 1.378(11) . ? C6 N4 1.380(9) . ? C6 C9 1.467(11) . ? C7 N4 1.334(10) . ? C7 N5 1.340(10) . ? C8 N5 1.366(10) . ? C8 C14 1.476(11) . ? C9 C13 1.388(11) . ? C9 C10 1.397(11) . ? C10 C11 1.370(11) . ? C11 N2 1.330(10) . ? C12 N2 1.344(10) . ? C12 C13 1.384(11) . ? C14 C18 1.386(11) . ? C14 C15 1.398(11) . ? C15 C16 1.380(11) . ? C16 N1 1.333(10) . ? C17 N1 1.343(10) . ? C17 C18 1.368(11) . ? C19 N6 1.344(10) . ? C19 C20 1.379(11) . ? C20 C21 1.389(11) . ? C21 C23 1.394(11) . ? C21 C24 1.478(10) . ? C22 N6 1.342(10) . ? C22 C23 1.375(11) . ? C24 N8 1.366(9) . ? C24 C25 1.375(10) . ? C25 N9 1.396(9) . ? C25 C32 1.454(10) . ? C26 N8 1.329(10) . ? C26 N9 1.345(10) . ? C26 C27 1.463(10) . ? C27 C31 1.385(11) . ? C27 C28 1.395(12) . ? C28 C29 1.380(12) . ? C29 N10 1.326(12) . ? C30 N10 1.342(12) . ? C30 C31 1.383(12) . ? C32 C35 1.395(11) . ? C32 C33 1.402(10) . ? C33 C34 1.378(10) . ? C34 N7 1.336(9) . ? C35 C36 1.357(11) . ? C36 N7 1.358(9) . ? N1 Zn1 2.150(6) . ? N2 Zn1 2.173(6) 1_545 ? N6 Zn1 2.181(6) . ? N7 Zn1 2.174(6) 1_565 ? N11 O6 1.191(11) . ? N11 O5 1.231(10) . ? N11 O4 1.237(12) . ? N12 O3B 1.189(16) . ? N12 O2A 1.199(18) . ? N12 O1 1.230(16) . ? N12 O2B 1.51(6) . ? O1W Zn1 2.187(7) . ? O2W Zn1 2.144(6) . ? Zn1 N2 2.173(6) 1_565 ? Zn1 N7 2.174(6) 1_545 ? O3B O2B 1.60(6) . ? 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 C1 C2 122.9(9) . . ? C1 C2 C5 121.3(9) . . ? N3 C3 C4 123.6(9) . . ? C3 C4 C5 119.3(9) . . ? C2 C5 C4 116.2(8) . . ? C2 C5 C7 122.5(8) . . ? C4 C5 C7 121.3(7) . . ? C8 C6 N4 107.6(7) . . ? C8 C6 C9 129.6(7) . . ? N4 C6 C9 122.8(7) . . ? N4 C7 N5 111.1(7) . . ? N4 C7 C5 124.7(7) . . ? N5 C7 C5 124.1(7) . . ? N5 C8 C6 107.4(7) . . ? N5 C8 C14 121.0(7) . . ? C6 C8 C14 131.5(7) . . ? C13 C9 C10 116.8(7) . . ? C13 C9 C6 121.4(7) . . ? C10 C9 C6 121.7(7) . . ? C11 C10 C9 119.6(7) . . ? N2 C11 C10 123.8(7) . . ? N2 C12 C13 122.8(7) . . ? C12 C13 C9 119.7(7) . . ? C18 C14 C15 117.6(7) . . ? C18 C14 C8 121.0(7) . . ? C15 C14 C8 121.4(7) . . ? C16 C15 C14 118.4(7) . . ? N1 C16 C15 123.6(7) . . ? N1 C17 C18 122.5(7) . . ? C17 C18 C14 120.1(7) . . ? N6 C19 C20 123.2(7) . . ? C19 C20 C21 119.4(7) . . ? C20 C21 C23 117.3(7) . . ? C20 C21 C24 122.5(7) . . ? C23 C21 C24 120.2(7) . . ? N6 C22 C23 122.9(7) . . ? C22 C23 C21 119.9(7) . . ? N8 C24 C25 108.9(6) . . ? N8 C24 C21 120.6(7) . . ? C25 C24 C21 130.4(7) . . ? C24 C25 N9 106.1(6) . . ? C24 C25 C32 131.8(7) . . ? N9 C25 C32 122.1(6) . . ? N8 C26 N9 111.1(7) . . ? N8 C26 C27 124.1(7) . . ? N9 C26 C27 124.6(7) . . ? C31 C27 C28 117.1(7) . . ? C31 C27 C26 122.3(7) . . ? C28 C27 C26 120.5(7) . . ? C29 C28 C27 118.9(9) . . ? N10 C29 C28 125.0(9) . . ? N10 C30 C31 124.3(9) . . ? C30 C31 C27 119.2(8) . . ? C35 C32 C33 116.4(7) . . ? C35 C32 C25 122.9(7) . . ? C33 C32 C25 120.6(7) . . ? C34 C33 C32 119.1(7) . . ? N7 C34 C33 124.2(7) . . ? C36 C35 C32 120.7(7) . . ? C35 C36 N7 123.1(7) . . ? C16 N1 C17 117.7(7) . . ? C16 N1 Zn1 122.9(5) . . ? C17 N1 Zn1 118.9(5) . . ? C11 N2 C12 117.2(7) . . ? C11 N2 Zn1 122.1(5) . 1_545 ? C12 N2 Zn1 120.7(5) . 1_545 ? C3 N3 C1 116.7(8) . . ? C7 N4 C6 106.6(6) . . ? C7 N5 C8 107.2(7) . . ? C22 N6 C19 117.3(6) . . ? C22 N6 Zn1 118.1(5) . . ? C19 N6 Zn1 124.4(5) . . ? C34 N7 C36 116.4(6) . . ? C34 N7 Zn1 122.3(5) . 1_565 ? C36 N7 Zn1 121.3(5) . 1_565 ? C26 N8 C24 107.0(6) . . ? C26 N9 C25 106.8(6) . . ? C29 N10 C30 115.5(8) . . ? O6 N11 O5 121.2(11) . . ? O6 N11 O4 121.0(11) . . ? O5 N11 O4 117.8(10) . . ? O3B N12 O2A 130.1(17) . . ? O3B N12 O1 116.0(16) . . ? O2A N12 O1 112.5(16) . . ? O3B N12 O2B 72(2) . . ? O2A N12 O2B 75(2) . . ? O1 N12 O2B 145(3) . . ? O2W Zn1 N1 90.9(2) . . ? O2W Zn1 N2 91.1(2) . 1_565 ? N1 Zn1 N2 89.5(2) . 1_565 ? O2W Zn1 N7 91.9(2) . 1_545 ? N1 Zn1 N7 89.4(2) . 1_545 ? N2 Zn1 N7 176.8(2) 1_565 1_545 ? O2W Zn1 N6 87.9(2) . . ? N1 Zn1 N6 178.2(3) . . ? N2 Zn1 N6 91.9(2) 1_565 . ? N7 Zn1 N6 89.3(2) 1_545 . ? O2W Zn1 O1W 176.8(2) . . ? N1 Zn1 O1W 91.8(3) . . ? N2 Zn1 O1W 87.3(3) 1_565 . ? N7 Zn1 O1W 89.8(3) 1_545 . ? N6 Zn1 O1W 89.4(2) . . ? N12 O3B O2B 63(2) . . ? N12 O2B O3B 44.8(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C1 C2 C5 0.0(17) . . . . ? N3 C3 C4 C5 3.1(16) . . . . ? C1 C2 C5 C4 0.5(14) . . . . ? C1 C2 C5 C7 178.9(9) . . . . ? C3 C4 C5 C2 -2.0(14) . . . . ? C3 C4 C5 C7 179.6(9) . . . . ? C2 C5 C7 N4 7.6(14) . . . . ? C4 C5 C7 N4 -174.1(8) . . . . ? C2 C5 C7 N5 -171.2(9) . . . . ? C4 C5 C7 N5 7.0(14) . . . . ? N4 C6 C8 N5 0.8(10) . . . . ? C9 C6 C8 N5 178.6(8) . . . . ? N4 C6 C8 C14 177.1(9) . . . . ? C9 C6 C8 C14 -5.1(16) . . . . ? C8 C6 C9 C13 -30.7(14) . . . . ? N4 C6 C9 C13 146.8(8) . . . . ? C8 C6 C9 C10 150.8(9) . . . . ? N4 C6 C9 C10 -31.6(13) . . . . ? C13 C9 C10 C11 2.9(13) . . . . ? C6 C9 C10 C11 -178.6(8) . . . . ? C9 C10 C11 N2 -1.9(14) . . . . ? N2 C12 C13 C9 0.5(13) . . . . ? C10 C9 C13 C12 -2.3(13) . . . . ? C6 C9 C13 C12 179.2(8) . . . . ? N5 C8 C14 C18 -49.5(12) . . . . ? C6 C8 C14 C18 134.7(10) . . . . ? N5 C8 C14 C15 127.5(9) . . . . ? C6 C8 C14 C15 -48.4(14) . . . . ? C18 C14 C15 C16 1.7(12) . . . . ? C8 C14 C15 C16 -175.3(8) . . . . ? C14 C15 C16 N1 -1.5(13) . . . . ? N1 C17 C18 C14 -1.4(14) . . . . ? C15 C14 C18 C17 -0.3(13) . . . . ? C8 C14 C18 C17 176.7(8) . . . . ? N6 C19 C20 C21 -0.5(12) . . . . ? C19 C20 C21 C23 0.5(11) . . . . ? C19 C20 C21 C24 -177.3(7) . . . . ? N6 C22 C23 C21 -1.3(12) . . . . ? C20 C21 C23 C22 0.4(12) . . . . ? C24 C21 C23 C22 178.3(7) . . . . ? C20 C21 C24 N8 130.7(8) . . . . ? C23 C21 C24 N8 -47.0(11) . . . . ? C20 C21 C24 C25 -44.3(13) . . . . ? C23 C21 C24 C25 138.0(9) . . . . ? N8 C24 C25 N9 -0.7(9) . . . . ? C21 C24 C25 N9 174.7(8) . . . . ? N8 C24 C25 C32 179.7(8) . . . . ? C21 C24 C25 C32 -4.8(15) . . . . ? N8 C26 C27 C31 -171.2(8) . . . . ? N9 C26 C27 C31 4.1(13) . . . . ? N8 C26 C27 C28 6.7(13) . . . . ? N9 C26 C27 C28 -178.0(8) . . . . ? C31 C27 C28 C29 1.1(13) . . . . ? C26 C27 C28 C29 -176.9(8) . . . . ? C27 C28 C29 N10 0.9(15) . . . . ? N10 C30 C31 C27 0.2(14) . . . . ? C28 C27 C31 C30 -1.6(12) . . . . ? C26 C27 C31 C30 176.4(8) . . . . ? C24 C25 C32 C35 145.9(9) . . . . ? N9 C25 C32 C35 -33.5(11) . . . . ? C24 C25 C32 C33 -30.0(13) . . . . ? N9 C25 C32 C33 150.5(7) . . . . ? C35 C32 C33 C34 1.5(11) . . . . ? C25 C32 C33 C34 177.7(7) . . . . ? C32 C33 C34 N7 -0.6(11) . . . . ? C33 C32 C35 C36 -1.0(11) . . . . ? C25 C32 C35 C36 -177.1(7) . . . . ? C32 C35 C36 N7 -0.3(13) . . . . ? C15 C16 N1 C17 -0.2(13) . . . . ? C15 C16 N1 Zn1 171.9(6) . . . . ? C18 C17 N1 C16 1.7(13) . . . . ? C18 C17 N1 Zn1 -170.7(7) . . . . ? C10 C11 N2 C12 0.1(12) . . . . ? C10 C11 N2 Zn1 178.7(7) . . . 1_545 ? C13 C12 N2 C11 0.6(12) . . . . ? C13 C12 N2 Zn1 -178.0(7) . . . 1_545 ? C4 C3 N3 C1 -2.5(16) . . . . ? C2 C1 N3 C3 0.9(16) . . . . ? N5 C7 N4 C6 0.0(10) . . . . ? C5 C7 N4 C6 -179.0(8) . . . . ? C8 C6 N4 C7 -0.5(9) . . . . ? C9 C6 N4 C7 -178.5(8) . . . . ? N4 C7 N5 C8 0.5(10) . . . . ? C5 C7 N5 C8 179.6(8) . . . . ? C6 C8 N5 C7 -0.8(9) . . . . ? C14 C8 N5 C7 -177.6(8) . . . . ? C23 C22 N6 C19 1.2(11) . . . . ? C23 C22 N6 Zn1 -173.9(6) . . . . ? C20 C19 N6 C22 -0.3(11) . . . . ? C20 C19 N6 Zn1 174.5(6) . . . . ? C33 C34 N7 C36 -0.7(11) . . . . ? C33 C34 N7 Zn1 178.9(5) . . . 1_565 ? C35 C36 N7 C34 1.2(11) . . . . ? C35 C36 N7 Zn1 -178.5(6) . . . 1_565 ? N9 C26 N8 C24 0.3(9) . . . . ? C27 C26 N8 C24 176.2(7) . . . . ? C25 C24 N8 C26 0.3(9) . . . . ? C21 C24 N8 C26 -175.7(7) . . . . ? N8 C26 N9 C25 -0.8(9) . . . . ? C27 C26 N9 C25 -176.7(7) . . . . ? C24 C25 N9 C26 0.9(9) . . . . ? C32 C25 N9 C26 -179.5(7) . . . . ? C28 C29 N10 C30 -2.2(14) . . . . ? C31 C30 N10 C29 1.7(14) . . . . ? C16 N1 Zn1 O2W 143.5(7) . . . . ? C17 N1 Zn1 O2W -44.6(7) . . . . ? C16 N1 Zn1 N2 -125.4(7) . . . 1_565 ? C17 N1 Zn1 N2 46.5(7) . . . 1_565 ? C16 N1 Zn1 N7 51.6(7) . . . 1_545 ? C17 N1 Zn1 N7 -136.5(7) . . . 1_545 ? C16 N1 Zn1 N6 95(8) . . . . ? C17 N1 Zn1 N6 -93(8) . . . . ? C16 N1 Zn1 O1W -38.2(7) . . . . ? C17 N1 Zn1 O1W 133.8(7) . . . . ? C22 N6 Zn1 O2W -47.7(6) . . . . ? C19 N6 Zn1 O2W 137.5(6) . . . . ? C22 N6 Zn1 N1 0(8) . . . . ? C19 N6 Zn1 N1 -174(8) . . . . ? C22 N6 Zn1 N2 -138.8(6) . . . 1_565 ? C19 N6 Zn1 N2 46.5(6) . . . 1_565 ? C22 N6 Zn1 N7 44.2(6) . . . 1_545 ? C19 N6 Zn1 N7 -130.5(6) . . . 1_545 ? C22 N6 Zn1 O1W 134.0(6) . . . . ? C19 N6 Zn1 O1W -40.8(6) . . . . ? O2A N12 O3B O2B 51(3) . . . . ? O1 N12 O3B O2B -143(3) . . . . ? O2A N12 O2B O3B -142(2) . . . . ? O1 N12 O2B O3B 110(4) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 1.077 _refine_diff_density_min -1.054 _refine_diff_density_rms 0.142 _database_code_depnum_ccdc_archive 'CCDC 909297' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H46 N10 O11 Zn' _chemical_formula_sum 'C40 H46 N10 O11 Zn' _chemical_formula_weight 907.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2840 1.4300 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.642(3) _cell_length_b 10.284(5) _cell_length_c 19.916(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.706(16) _cell_angle_gamma 90.00 _cell_volume 2166.2(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7251 _cell_measurement_theta_min 1.93 _cell_measurement_theta_max 20.89 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 0.637 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9274 _exptl_absorpt_correction_T_max 0.9567 _exptl_absorpt_process_details 'SADABS(Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7251 _diffrn_reflns_av_R_equivalents 0.1425 _diffrn_reflns_av_sigmaI/netI 0.1781 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 20.89 _reflns_number_total 2290 _reflns_number_gt 1107 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97(Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _refine_special_details ; The crystal was small and weakly scattering, which leads to that value of theta max is low. During the refinement, the command 'omit -3 50' was used to omit the weak reflections above 50 degree.During the refinement, the command 'ISOR' was used to restrain some non-H atoms with NPD and/or ADP problems. These atoms are as follows: O3W O4W. 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^ > 2\s(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^)+(0.0487P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2290 _refine_ls_number_parameters 285 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1260 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.867 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5650(7) 1.3079(7) 0.3369(4) 0.0379(19) Uani 1 1 d . . . C11 C 0.4963(7) 1.2027(8) 0.3333(4) 0.039(2) Uani 1 1 d . . . C12 C 0.6748(8) 1.3191(8) 0.3958(5) 0.044(3) Uani 1 1 d . . . Zn1 Zn 0.5000 0.45675(14) 0.2500 0.0344(5) Uani 1 2 d S . . O1W O 0.6813(4) 0.4529(5) 0.2511(3) 0.0444(15) Uani 1 1 d . . . H1A H 0.6796 0.4070 0.2051 0.053 Uiso 1 1 d R . . H1B H 0.7128 0.5435 0.2499 0.053 Uiso 1 1 d R . . N2 N 0.7422(6) 1.0707(6) 0.5819(4) 0.0343(18) Uani 1 1 d . . . N3 N 0.7249(5) 0.8548(6) 0.5810(3) 0.0324(18) Uani 1 1 d . . . H3 H 0.7288 0.7780 0.5969 0.039 Uiso 1 1 d R . . N4 N 0.5575(6) 0.6078(6) 0.3357(4) 0.0320(18) Uani 1 1 d . . . N5 N 0.9224(7) 0.9746(9) 0.8589(4) 0.061(2) Uani 1 1 d . . . C1 C 0.5293(8) 0.5989(8) 0.3955(5) 0.045(2) Uani 1 1 d . . . H1 H 0.4821 0.5278 0.3983 0.054 Uiso 1 1 calc R . . C2 C 0.5660(8) 0.6873(8) 0.4512(4) 0.042(2) Uani 1 1 d . . . H2 H 0.5468 0.6734 0.4915 0.050 Uiso 1 1 calc R . . C3 C 0.6314(7) 0.7974(8) 0.4485(4) 0.030(2) Uani 1 1 d . . . C4 C 0.6582(7) 0.8091(7) 0.3869(4) 0.031(2) Uani 1 1 d . . . H4 H 0.7028 0.8810 0.3823 0.037 Uiso 1 1 calc R . . C5 C 0.6194(7) 0.7160(8) 0.3329(4) 0.037(2) Uani 1 1 d . . . H5 H 0.6371 0.7285 0.2920 0.044 Uiso 1 1 calc R . . C6 C 0.6758(7) 0.8929(8) 0.5077(4) 0.031(2) Uani 1 1 d . . . C8 C 0.6874(7) 1.0259(8) 0.5098(4) 0.029(2) Uani 1 1 d . . . C9 C 0.6454(8) 1.1197(8) 0.4491(4) 0.025(2) Uani 1 1 d . . . C10 C 0.5346(7) 1.1071(7) 0.3875(4) 0.034(2) Uani 1 1 d . . . H10 H 0.4843 1.0341 0.3818 0.040 Uiso 1 1 calc R . . H11 H 0.4188 1.1932 0.2930 0.040 Uiso 1 1 d R . . H12 H 0.7245 1.3922 0.3994 0.040 Uiso 1 1 d R . . C13 C 0.7179(8) 1.2288(8) 0.4527(4) 0.044(2) Uani 1 1 d . . . H13 H 0.7949 1.2412 0.4931 0.053 Uiso 1 1 calc R . . C14 C 0.7649(7) 0.9633(9) 0.6225(4) 0.0303(19) Uani 1 1 d . . . C15 C 0.8199(7) 0.9643(9) 0.7046(4) 0.035(2) Uani 1 1 d . . . C16 C 0.8497(8) 0.8523(8) 0.7464(5) 0.048(3) Uani 1 1 d . . . H16 H 0.8371 0.7711 0.7239 0.057 Uiso 1 1 calc R . . C17 C 0.8990(9) 0.8632(10) 0.8225(5) 0.063(3) Uani 1 1 d . . . H17 H 0.9168 0.7869 0.8500 0.076 Uiso 1 1 calc R . . C18 C 0.8945(9) 1.0820(9) 0.8178(6) 0.056(3) Uani 1 1 d . . . H18 H 0.9112 1.1619 0.8418 0.068 Uiso 1 1 calc R . . C19 C 0.8427(8) 1.0814(8) 0.7421(5) 0.052(3) Uani 1 1 d . . . H19 H 0.8228 1.1593 0.7160 0.063 Uiso 1 1 calc R . . O1 O 0.7281(6) 0.6028(5) 0.6317(3) 0.0488(17) Uani 1 1 d . . . O2 O 0.8950(6) 0.5796(6) 0.6054(4) 0.092(3) Uani 1 1 d . . . C39 C 0.8169(10) 0.5373(10) 0.6274(5) 0.049(2) Uani 1 1 d . . . C40 C 0.8297(9) 0.3964(9) 0.6510(5) 0.085(4) Uani 1 1 d . . . H40A H 0.7651 0.3752 0.6673 0.127 Uiso 1 1 calc R . . H40B H 0.9114 0.3825 0.6907 0.127 Uiso 1 1 calc R . . H40C H 0.8207 0.3419 0.6099 0.127 Uiso 1 1 calc R . . O2W O 0.1124(5) 0.4494(6) 0.6374(3) 0.082(2) Uani 1 1 d . . . O3W O 0.0603(7) 0.3166(8) 0.5076(4) 0.129(3) Uani 1 1 d U . . O4W O 0.0303(13) 0.0736(13) 0.5055(8) 0.118(6) Uani 0.50 1 d PU . . 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 N1 0.052(5) 0.032(5) 0.026(5) 0.005(4) 0.012(4) 0.001(4) C11 0.044(6) 0.031(6) 0.030(6) -0.004(5) 0.004(5) -0.007(5) C12 0.054(7) 0.034(6) 0.039(7) 0.006(5) 0.015(6) -0.010(5) Zn1 0.0524(10) 0.0281(9) 0.0210(9) 0.000 0.0136(7) 0.000 O1W 0.058(4) 0.041(3) 0.044(4) -0.007(3) 0.032(3) 0.002(3) N2 0.062(5) 0.017(5) 0.021(5) 0.003(4) 0.014(4) -0.002(4) N3 0.053(5) 0.021(4) 0.022(5) 0.003(4) 0.015(4) 0.002(4) N4 0.043(5) 0.026(5) 0.030(5) 0.001(3) 0.018(4) -0.001(4) N5 0.081(6) 0.065(6) 0.032(5) -0.006(6) 0.019(4) -0.010(6) C1 0.060(6) 0.042(6) 0.039(6) -0.001(5) 0.025(6) -0.018(5) C2 0.062(7) 0.039(6) 0.026(6) -0.007(5) 0.021(5) -0.014(5) C3 0.049(6) 0.020(5) 0.018(6) -0.003(4) 0.012(5) -0.002(5) C4 0.054(6) 0.016(5) 0.029(6) -0.003(4) 0.023(5) -0.008(4) C5 0.048(6) 0.039(6) 0.027(6) -0.001(5) 0.020(5) -0.004(5) C6 0.039(6) 0.031(6) 0.024(6) 0.004(5) 0.015(5) 0.004(5) C8 0.036(5) 0.021(6) 0.027(6) 0.002(5) 0.011(4) 0.001(5) C9 0.035(6) 0.019(5) 0.020(6) 0.002(4) 0.010(5) 0.002(5) C10 0.039(6) 0.030(5) 0.030(6) 0.006(5) 0.013(5) 0.001(5) C13 0.062(7) 0.038(6) 0.027(6) 0.007(5) 0.014(5) 0.003(6) C14 0.043(5) 0.023(5) 0.026(5) -0.006(6) 0.016(4) -0.001(5) C15 0.047(5) 0.036(5) 0.021(5) -0.005(5) 0.014(4) -0.005(6) C16 0.084(7) 0.026(6) 0.031(7) 0.008(5) 0.022(6) -0.003(5) C17 0.101(8) 0.051(8) 0.029(7) 0.005(6) 0.019(6) -0.013(6) C18 0.087(8) 0.039(7) 0.045(8) -0.008(5) 0.029(7) -0.003(6) C19 0.091(8) 0.040(7) 0.026(7) 0.005(5) 0.025(6) 0.003(5) O1 0.076(5) 0.038(4) 0.041(4) 0.008(3) 0.033(4) 0.011(4) O2 0.092(5) 0.082(6) 0.137(7) 0.033(5) 0.081(5) 0.007(5) C39 0.063(7) 0.039(7) 0.045(6) 0.000(6) 0.022(6) -0.003(7) C40 0.125(10) 0.049(7) 0.101(10) 0.014(6) 0.067(8) 0.011(7) O2W 0.053(4) 0.104(5) 0.083(5) -0.018(5) 0.022(4) -0.001(4) O3W 0.129(3) 0.131(3) 0.128(3) 0.0006(10) 0.0543(16) 0.0003(10) O4W 0.118(6) 0.118(6) 0.117(6) 0.0002(11) 0.049(3) -0.0003(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 C11 1.329(9) . ? N1 C12 1.331(9) . ? N1 Zn1 2.195(6) 1_565 ? C11 C10 1.389(10) . ? C11 H11 0.9289 . ? C12 C13 1.387(10) . ? C12 H12 0.9336 . ? Zn1 O1W 2.102(4) . ? Zn1 O1W 2.102(4) 2_655 ? Zn1 N1 2.195(6) 2_645 ? Zn1 N1 2.195(6) 1_545 ? Zn1 N4 2.196(6) . ? Zn1 N4 2.196(6) 2_655 ? O1W H1A 1.0235 . ? O1W H1B 1.0057 . ? N2 C14 1.328(9) . ? N2 C8 1.385(9) . ? N3 C14 1.351(8) . ? N3 C6 1.382(9) . ? N3 H3 0.8450 . ? N4 C5 1.340(8) . ? N4 C1 1.363(8) . ? N5 C17 1.321(10) . ? N5 C18 1.332(10) . ? C1 C2 1.358(10) . ? C1 H1 0.9300 . ? C2 C3 1.378(9) . ? C2 H2 0.9300 . ? C3 C4 1.393(9) . ? C3 C6 1.454(10) . ? C4 C5 1.367(9) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C8 1.373(9) . ? C8 C9 1.461(10) . ? C9 C10 1.364(9) . ? C9 C13 1.388(9) . ? C10 H10 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.486(9) . ? C15 C16 1.377(10) . ? C15 C19 1.383(10) . ? C16 C17 1.384(10) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.369(11) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? O1 C39 1.267(10) . ? O2 C39 1.242(9) . ? C39 C40 1.511(11) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? O4W O4W 1.65(3) 3_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 C11 N1 C12 116.9(7) . . ? C11 N1 Zn1 121.6(6) . 1_565 ? C12 N1 Zn1 121.5(6) . 1_565 ? N1 C11 C10 123.0(7) . . ? N1 C11 H11 118.6 . . ? C10 C11 H11 118.5 . . ? N1 C12 C13 123.3(8) . . ? N1 C12 H12 118.3 . . ? C13 C12 H12 118.4 . . ? O1W Zn1 O1W 177.8(3) . 2_655 ? O1W Zn1 N1 90.5(2) . 2_645 ? O1W Zn1 N1 88.0(2) 2_655 2_645 ? O1W Zn1 N1 88.0(2) . 1_545 ? O1W Zn1 N1 90.5(2) 2_655 1_545 ? N1 Zn1 N1 91.5(4) 2_645 1_545 ? O1W Zn1 N4 91.6(2) . . ? O1W Zn1 N4 90.0(2) 2_655 . ? N1 Zn1 N4 177.8(3) 2_645 . ? N1 Zn1 N4 89.3(2) 1_545 . ? O1W Zn1 N4 90.0(2) . 2_655 ? O1W Zn1 N4 91.6(2) 2_655 2_655 ? N1 Zn1 N4 89.3(2) 2_645 2_655 ? N1 Zn1 N4 177.8(3) 1_545 2_655 ? N4 Zn1 N4 89.9(4) . 2_655 ? Zn1 O1W H1A 110.9 . . ? Zn1 O1W H1B 110.9 . . ? H1A O1W H1B 106.1 . . ? C14 N2 C8 104.1(6) . . ? C14 N3 C6 107.3(6) . . ? C14 N3 H3 126.2 . . ? C6 N3 H3 126.6 . . ? C5 N4 C1 115.0(7) . . ? C5 N4 Zn1 123.3(5) . . ? C1 N4 Zn1 121.6(6) . . ? C17 N5 C18 116.1(7) . . ? C2 C1 N4 124.0(8) . . ? C2 C1 H1 118.0 . . ? N4 C1 H1 118.0 . . ? C1 C2 C3 120.6(8) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 C4 115.8(7) . . ? C2 C3 C6 122.6(8) . . ? C4 C3 C6 121.5(8) . . ? C5 C4 C3 120.7(7) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? N4 C5 C4 123.7(7) . . ? N4 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C8 C6 N3 105.0(7) . . ? C8 C6 C3 133.9(8) . . ? N3 C6 C3 121.0(8) . . ? C6 C8 N2 111.0(7) . . ? C6 C8 C9 129.7(8) . . ? N2 C8 C9 119.2(8) . . ? C10 C9 C13 116.7(7) . . ? C10 C9 C8 123.0(8) . . ? C13 C9 C8 120.3(8) . . ? C9 C10 C11 120.5(8) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C13 C9 119.7(8) . . ? C12 C13 H13 120.2 . . ? C9 C13 H13 120.2 . . ? N2 C14 N3 112.6(6) . . ? N2 C14 C15 123.3(8) . . ? N3 C14 C15 124.0(8) . . ? C16 C15 C19 117.3(7) . . ? C16 C15 C14 122.9(9) . . ? C19 C15 C14 119.8(8) . . ? C15 C16 C17 118.6(8) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? N5 C17 C16 124.6(9) . . ? N5 C17 H17 117.7 . . ? C16 C17 H17 117.7 . . ? N5 C18 C19 123.7(8) . . ? N5 C18 H18 118.1 . . ? C19 C18 H18 118.1 . . ? C18 C19 C15 119.7(8) . . ? C18 C19 H19 120.2 . . ? C15 C19 H19 120.2 . . ? O2 C39 O1 125.2(10) . . ? O2 C39 C40 117.0(10) . . ? O1 C39 C40 117.8(9) . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 N1 C11 C10 0.0(12) . . . . ? Zn1 N1 C11 C10 -179.7(6) 1_565 . . . ? C11 N1 C12 C13 -1.2(13) . . . . ? Zn1 N1 C12 C13 178.5(6) 1_565 . . . ? O1W Zn1 N4 C5 48.4(6) . . . . ? O1W Zn1 N4 C5 -133.1(6) 2_655 . . . ? N1 Zn1 N4 C5 -111(7) 2_645 . . . ? N1 Zn1 N4 C5 136.4(6) 1_545 . . . ? N4 Zn1 N4 C5 -41.6(5) 2_655 . . . ? O1W Zn1 N4 C1 -133.2(6) . . . . ? O1W Zn1 N4 C1 45.3(6) 2_655 . . . ? N1 Zn1 N4 C1 67(7) 2_645 . . . ? N1 Zn1 N4 C1 -45.2(6) 1_545 . . . ? N4 Zn1 N4 C1 136.8(7) 2_655 . . . ? C5 N4 C1 C2 -3.7(12) . . . . ? Zn1 N4 C1 C2 177.8(6) . . . . ? N4 C1 C2 C3 2.9(13) . . . . ? C1 C2 C3 C4 -1.2(12) . . . . ? C1 C2 C3 C6 -178.2(8) . . . . ? C2 C3 C4 C5 0.6(12) . . . . ? C6 C3 C4 C5 177.7(7) . . . . ? C1 N4 C5 C4 3.1(11) . . . . ? Zn1 N4 C5 C4 -178.4(6) . . . . ? C3 C4 C5 N4 -1.7(13) . . . . ? C14 N3 C6 C8 -1.1(9) . . . . ? C14 N3 C6 C3 176.2(7) . . . . ? C2 C3 C6 C8 -144.3(9) . . . . ? C4 C3 C6 C8 38.8(14) . . . . ? C2 C3 C6 N3 39.3(11) . . . . ? C4 C3 C6 N3 -137.5(8) . . . . ? N3 C6 C8 N2 0.0(9) . . . . ? C3 C6 C8 N2 -176.7(8) . . . . ? N3 C6 C8 C9 -176.4(7) . . . . ? C3 C6 C8 C9 6.8(16) . . . . ? C14 N2 C8 C6 1.0(9) . . . . ? C14 N2 C8 C9 177.9(7) . . . . ? C6 C8 C9 C10 37.4(13) . . . . ? N2 C8 C9 C10 -138.8(8) . . . . ? C6 C8 C9 C13 -143.6(9) . . . . ? N2 C8 C9 C13 40.2(11) . . . . ? C13 C9 C10 C11 -2.3(11) . . . . ? C8 C9 C10 C11 176.7(7) . . . . ? N1 C11 C10 C9 1.8(13) . . . . ? N1 C12 C13 C9 0.6(13) . . . . ? C10 C9 C13 C12 1.1(12) . . . . ? C8 C9 C13 C12 -177.9(7) . . . . ? C8 N2 C14 N3 -1.8(8) . . . . ? C8 N2 C14 C15 -177.7(6) . . . . ? C6 N3 C14 N2 1.8(8) . . . . ? C6 N3 C14 C15 177.7(6) . . . . ? N2 C14 C15 C16 -176.2(7) . . . . ? N3 C14 C15 C16 8.3(12) . . . . ? N2 C14 C15 C19 4.0(11) . . . . ? N3 C14 C15 C19 -171.5(7) . . . . ? C19 C15 C16 C17 0.7(12) . . . . ? C14 C15 C16 C17 -179.1(7) . . . . ? C18 N5 C17 C16 0.7(14) . . . . ? C15 C16 C17 N5 -1.6(15) . . . . ? C17 N5 C18 C19 1.0(14) . . . . ? N5 C18 C19 C15 -1.8(14) . . . . ? C16 C15 C19 C18 0.9(12) . . . . ? C14 C15 C19 C18 -179.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 20.89 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.553 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 909298' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H44 Cd N12 O15' _chemical_formula_sum 'C36 H44 Cd N12 O15' _chemical_formula_weight 997.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.036(3) _cell_length_b 10.259(3) _cell_length_c 17.392(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.406(4) _cell_angle_gamma 90.00 _cell_volume 2089.0(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9955 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 24.81 _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.607 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8933 _exptl_absorpt_correction_T_max 0.9144 _exptl_absorpt_process_details 'SADABS(Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9955 _diffrn_reflns_av_R_equivalents 0.1225 _diffrn_reflns_av_sigmaI/netI 0.1453 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 24.81 _reflns_number_total 3570 _reflns_number_gt 1809 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97(Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _refine_special_details ; During the refinement, the command 'ISOR' was used to restrain some non-H atoms with NPD and/or ADP problems. These atoms are as follows: O3B O2WB O3A O2WA o2 o4wa o4wb The restraint order 'EADP' was refined the atoms N6 and O1. The 'DFIX' command was used to bind O1 and N6, O2 and N6. The restraint command 'PART' was refined the atoms O3, O2w and O4w. 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^ > 2\s(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^)+(0.1627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3570 _refine_ls_number_parameters 308 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.1510 _refine_ls_R_factor_gt 0.0965 _refine_ls_wR_factor_ref 0.2930 _refine_ls_wR_factor_gt 0.2650 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.5000 0.49050(10) 0.7500 0.0486(5) Uani 1 2 d S . . N3 N 0.9474(7) 0.8797(8) 0.6393(5) 0.044(2) Uani 1 1 d . . . N4 N 0.9391(7) 1.0913(8) 0.6263(5) 0.050(2) Uani 1 1 d . . . H4 H 0.9568 1.1692 0.6152 0.060 Uiso 1 1 calc R . . N1 N 0.6232(7) 0.6479(8) 0.7237(5) 0.045(2) Uani 1 1 d . . . C9 C 1.1032(9) 0.9835(11) 0.5916(6) 0.048(3) Uani 1 1 d . . . N2 N 0.3838(8) 0.3329(8) 0.7871(5) 0.056(3) Uani 1 1 d . . . C7 C 0.8451(8) 1.0566(10) 0.6541(6) 0.044(3) Uani 1 1 d . . . C2 C 0.8105(8) 0.7214(10) 0.7232(6) 0.048(3) Uani 1 1 d . . . H2 H 0.8885 0.7045 0.7380 0.057 Uiso 1 1 calc R . . C6 C 0.8526(9) 0.9222(10) 0.6614(6) 0.046(3) Uani 1 1 d . . . C4 C 0.6552(9) 0.8477(10) 0.6610(6) 0.046(3) Uani 1 1 d . . . H4A H 0.6239 0.9211 0.6327 0.055 Uiso 1 1 calc R . . C3 C 0.7732(9) 0.8307(9) 0.6831(6) 0.039(2) Uani 1 1 d . . . C8 C 0.9978(9) 0.9833(9) 0.6194(6) 0.044(2) Uani 1 1 d . . . C1 C 0.7350(9) 0.6341(10) 0.7429(6) 0.049(3) Uani 1 1 d . . . H1 H 0.7648 0.5605 0.7716 0.058 Uiso 1 1 calc R . . C5 C 0.5869(8) 0.7554(10) 0.6814(6) 0.049(3) Uani 1 1 d . . . H5 H 0.5084 0.7676 0.6647 0.059 Uiso 1 1 calc R . . C18 C 0.3553(9) 0.2236(10) 0.7458(6) 0.049(3) Uani 1 1 d . . . H18 H 0.3864 0.2085 0.7023 0.059 Uiso 1 1 calc R . . C16 C 0.2365(9) 0.1506(10) 0.8276(7) 0.049(3) Uani 1 1 d . . . C17 C 0.2838(10) 0.1341(10) 0.7640(6) 0.052(3) Uani 1 1 d . . . H17 H 0.2663 0.0598 0.7328 0.062 Uiso 1 1 calc R . . O1 O 0.5918(11) 0.5215(11) 0.8838(7) 0.113(3) Uani 1 1 d D D . C13 C 1.1489(11) 1.0950(12) 0.5673(6) 0.060(3) Uani 1 1 d . . . H13 H 1.1113 1.1743 0.5667 0.073 Uiso 1 1 calc R . . C14 C 0.3341(10) 0.3524(11) 0.8485(7) 0.060(3) Uani 1 1 d . . . H14 H 0.3503 0.4291 0.8774 0.072 Uiso 1 1 calc R . . C10 C 1.1607(9) 0.8694(13) 0.5899(7) 0.059(3) Uani 1 1 d . . . H10 H 1.1315 0.7911 0.6037 0.071 Uiso 1 1 calc R . . N5 N 1.3066(9) 0.9793(13) 0.5443(7) 0.081(4) Uani 1 1 d . . . C15 C 0.2633(10) 0.2674(11) 0.8693(7) 0.063(3) Uani 1 1 d . . . H15 H 0.2314 0.2856 0.9120 0.076 Uiso 1 1 calc R . . C11 C 1.2622(11) 0.8725(16) 0.5674(7) 0.073(4) Uani 1 1 d . . . H11 H 1.3024 0.7949 0.5684 0.088 Uiso 1 1 calc R . . C12 C 1.2499(13) 1.0885(15) 0.5439(8) 0.076(4) Uani 1 1 d . . . H12 H 1.2794 1.1644 0.5272 0.091 Uiso 1 1 calc R . . N6 N 0.6615(14) 0.4723(14) 0.9237(10) 0.113(3) Uani 1 1 d D . . O1W O 0.9423(14) 0.6200(12) 0.5682(9) 0.155(6) Uani 1 1 d . . . O3W O 0.5057(15) 1.1130(19) 0.5326(12) 0.205(7) Uani 1 1 d . . . O5W O 0.5495(18) 0.364(2) 1.0003(10) 0.220(8) Uani 1 1 d . . . O2WA O 1.0000 1.470(5) 0.7500 0.104(14) Uani 0.30 2 d SPU A 1 O3A O 0.825(4) 0.535(3) 0.943(2) 0.166(13) Uani 0.43 1 d PU B 1 O4WA O 0.9902(18) 1.351(2) 0.5875(13) 0.100(6) Uani 0.50 1 d PU C 1 O2WB O 1.0000 1.322(3) 0.7500 0.141(9) Uani 0.70 2 d SPU . 2 O3B O 0.717(2) 0.391(3) 0.8881(16) 0.161(9) Uani 0.57 1 d PU D 2 O4WB O 1.0061(19) 1.368(2) 0.6655(13) 0.115(7) Uani 0.50 1 d PU E 2 O2 O 0.703(3) 0.474(2) 0.9965(13) 0.266(11) Uani 1 1 d DU D . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0529(8) 0.0361(7) 0.0634(8) 0.000 0.0270(6) 0.000 N3 0.038(5) 0.045(5) 0.052(5) -0.002(4) 0.017(4) -0.008(4) N4 0.050(6) 0.041(5) 0.062(6) 0.007(4) 0.020(5) -0.006(4) N1 0.030(5) 0.040(5) 0.068(6) 0.004(4) 0.019(4) 0.001(4) C9 0.040(6) 0.068(8) 0.037(5) 0.003(6) 0.011(5) -0.012(6) N2 0.084(7) 0.042(5) 0.049(6) -0.006(4) 0.031(5) -0.017(5) C7 0.035(6) 0.046(6) 0.047(6) 0.000(5) 0.004(5) 0.005(5) C2 0.025(5) 0.056(7) 0.061(7) 0.005(6) 0.009(5) 0.002(5) C6 0.053(7) 0.038(6) 0.051(7) 0.005(5) 0.021(6) 0.003(5) C4 0.037(6) 0.043(6) 0.056(7) -0.005(5) 0.011(5) -0.008(5) C3 0.045(6) 0.036(5) 0.038(6) -0.004(5) 0.013(5) -0.002(5) C8 0.041(6) 0.045(6) 0.046(6) -0.005(5) 0.011(5) -0.005(5) C1 0.048(7) 0.037(6) 0.063(7) 0.007(5) 0.019(6) 0.003(5) C5 0.026(5) 0.053(7) 0.068(8) -0.001(6) 0.009(5) -0.001(5) C18 0.052(7) 0.050(6) 0.049(7) -0.009(5) 0.020(6) -0.010(5) C16 0.038(6) 0.048(6) 0.061(7) 0.004(5) 0.013(6) -0.004(5) C17 0.065(8) 0.045(6) 0.046(7) -0.008(5) 0.013(6) -0.012(5) O1 0.112(9) 0.113(8) 0.099(8) 0.026(5) -0.007(6) 0.009(6) C13 0.069(9) 0.067(8) 0.048(7) 0.004(6) 0.018(6) -0.025(6) C14 0.072(8) 0.052(7) 0.062(8) -0.019(6) 0.029(7) -0.016(6) C10 0.040(7) 0.071(8) 0.065(8) 0.001(6) 0.008(6) -0.009(6) N5 0.050(6) 0.126(12) 0.067(7) -0.002(8) 0.012(6) -0.031(7) C15 0.070(8) 0.058(7) 0.073(8) -0.024(6) 0.039(7) -0.016(6) C11 0.050(8) 0.114(11) 0.060(8) 0.012(8) 0.022(7) 0.005(8) C12 0.085(11) 0.087(11) 0.056(8) 0.002(8) 0.019(8) -0.034(9) N6 0.112(9) 0.113(8) 0.099(8) 0.026(5) -0.007(6) 0.009(6) O1W 0.219(16) 0.091(8) 0.189(14) -0.033(9) 0.115(12) -0.023(9) O3W 0.206(17) 0.175(17) 0.271(19) 0.002(15) 0.131(15) -0.002(12) O5W 0.234(18) 0.22(2) 0.210(18) 0.049(14) 0.058(14) -0.046(17) O2WA 0.104(14) 0.104(14) 0.104(14) 0.000 0.024(3) 0.000 O3A 0.166(13) 0.167(13) 0.166(13) 0.0003(10) 0.039(3) -0.0001(10) O4WA 0.100(6) 0.100(6) 0.101(6) 0.0002(10) 0.0234(18) -0.0001(10) O2WB 0.141(9) 0.141(9) 0.141(9) 0.000 0.032(2) 0.000 O3B 0.161(9) 0.161(9) 0.161(9) -0.0004(10) 0.038(2) 0.0005(10) O4WB 0.115(7) 0.115(7) 0.116(7) 0.0005(10) 0.027(2) -0.0004(10) O2 0.266(11) 0.266(11) 0.266(11) -0.0001(10) 0.062(3) 0.0002(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N1 2.309(8) 2_656 ? Cd1 N1 2.309(8) . ? Cd1 N2 2.325(8) . ? Cd1 N2 2.325(8) 2_656 ? Cd1 O1 2.355(12) . ? Cd1 O1 2.355(12) 2_656 ? N3 C8 1.310(12) . ? N3 C6 1.358(12) . ? N4 C8 1.334(12) . ? N4 C7 1.376(12) . ? N1 C1 1.317(12) . ? N1 C5 1.341(13) . ? C9 C10 1.364(15) . ? C9 C13 1.377(14) . ? C9 C8 1.459(14) . ? N2 C18 1.332(12) . ? N2 C14 1.355(13) . ? C7 C6 1.385(15) . ? C7 C16 1.464(13) 2_666 ? C2 C3 1.342(13) . ? C2 C1 1.375(13) . ? C6 C3 1.450(13) . ? C4 C5 1.353(13) . ? C4 C3 1.394(14) . ? C18 C17 1.346(14) . ? C16 C17 1.367(14) . ? C16 C15 1.400(14) . ? C16 C7 1.464(13) 2_646 ? O1 N6 1.081(13) . ? C13 C12 1.370(17) . ? C14 C15 1.327(14) . ? C10 C11 1.366(15) . ? N5 C12 1.311(18) . ? N5 C11 1.322(17) . ? N6 O2 1.249(17) . ? N6 O3B 1.31(3) . ? O2WB O4WB 1.56(2) 2_756 ? O2WB O4WB 1.56(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 N1 Cd1 N1 91.2(4) 2_656 . ? N1 Cd1 N2 88.6(3) 2_656 . ? N1 Cd1 N2 175.4(3) . . ? N1 Cd1 N2 175.4(3) 2_656 2_656 ? N1 Cd1 N2 88.6(3) . 2_656 ? N2 Cd1 N2 91.9(5) . 2_656 ? N1 Cd1 O1 83.4(4) 2_656 . ? N1 Cd1 O1 85.7(4) . . ? N2 Cd1 O1 89.7(4) . . ? N2 Cd1 O1 101.1(4) 2_656 . ? N1 Cd1 O1 85.7(4) 2_656 2_656 ? N1 Cd1 O1 83.4(4) . 2_656 ? N2 Cd1 O1 101.1(4) . 2_656 ? N2 Cd1 O1 89.7(4) 2_656 2_656 ? O1 Cd1 O1 164.5(5) . 2_656 ? C8 N3 C6 106.6(8) . . ? C8 N4 C7 108.2(8) . . ? C1 N1 C5 114.3(8) . . ? C1 N1 Cd1 122.6(7) . . ? C5 N1 Cd1 122.8(6) . . ? C10 C9 C13 117.8(11) . . ? C10 C9 C8 119.4(10) . . ? C13 C9 C8 122.9(11) . . ? C18 N2 C14 116.3(9) . . ? C18 N2 Cd1 122.1(7) . . ? C14 N2 Cd1 121.3(7) . . ? N4 C7 C6 104.4(9) . . ? N4 C7 C16 123.6(10) . 2_666 ? C6 C7 C16 131.9(10) . 2_666 ? C3 C2 C1 120.8(10) . . ? N3 C6 C7 109.5(9) . . ? N3 C6 C3 120.9(9) . . ? C7 C6 C3 129.5(10) . . ? C5 C4 C3 118.8(10) . . ? C2 C3 C4 116.4(9) . . ? C2 C3 C6 121.0(9) . . ? C4 C3 C6 122.5(9) . . ? N3 C8 N4 111.3(9) . . ? N3 C8 C9 125.5(10) . . ? N4 C8 C9 123.2(10) . . ? N1 C1 C2 124.2(10) . . ? N1 C5 C4 125.3(10) . . ? N2 C18 C17 123.1(10) . . ? C17 C16 C15 115.9(10) . . ? C17 C16 C7 121.4(10) . 2_646 ? C15 C16 C7 122.5(10) . 2_646 ? C18 C17 C16 121.0(10) . . ? N6 O1 Cd1 133.5(14) . . ? C12 C13 C9 119.7(13) . . ? C15 C14 N2 123.2(10) . . ? C9 C10 C11 118.5(12) . . ? C12 N5 C11 117.6(12) . . ? C14 C15 C16 120.4(10) . . ? N5 C11 C10 123.9(14) . . ? N5 C12 C13 122.4(13) . . ? O1 N6 O2 135(2) . . ? O1 N6 O3B 113(2) . . ? O2 N6 O3B 111(2) . . ? O4WB O2WB O4WB 145(3) 2_756 . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.81 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.917 _refine_diff_density_min -1.572 _refine_diff_density_rms 0.166 _database_code_depnum_ccdc_archive 'CCDC 909299' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H40 Cd N10 O7' _chemical_formula_sum 'C40 H40 Cd N10 O7' _chemical_formula_weight 885.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.395(3) _cell_length_b 11.295(4) _cell_length_c 17.949(2) _cell_angle_alpha 74.140(4) _cell_angle_beta 84.051(4) _cell_angle_gamma 77.807(3) _cell_volume 1979.1(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6920 _cell_measurement_theta_min 1.18 _cell_measurement_theta_max 20.94 _exptl_crystal_description block _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 0.615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8817 _exptl_absorpt_correction_T_max 0.9026 _exptl_absorpt_process_details 'SADABS(Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6920 _diffrn_reflns_av_R_equivalents 0.0998 _diffrn_reflns_av_sigmaI/netI 0.1665 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 20.94 _reflns_number_total 4197 _reflns_number_gt 2430 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97(Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _refine_special_details ; The crystal is small and weakly scattering, which leads to that value of theta max is low. During the refinement, the command 'ISOR' was used to restrain some non-H atoms with NPD and/or ADP problems. These atoms are as follows: O1 O3 O3W C39 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^ > 2\s(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^)+(0.0220P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4197 _refine_ls_number_parameters 522 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0996 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.857 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2038(9) 0.8856(8) 0.1532(5) 0.035(2) Uani 1 1 d . . . H1 H -0.1718 0.7999 0.1622 0.042 Uiso 1 1 calc R . . C2 C -0.1214(8) 0.9688(9) 0.1152(4) 0.033(3) Uani 1 1 d . . . H2 H -0.0344 0.9380 0.1019 0.040 Uiso 1 1 calc R . . C3 C -0.3695(8) 1.0484(9) 0.1606(5) 0.042(3) Uani 1 1 d . . . H3 H -0.4555 1.0777 0.1766 0.050 Uiso 1 1 calc R . . C4 C -0.2960(9) 1.1360(8) 0.1217(5) 0.040(3) Uani 1 1 d . . . H4 H -0.3322 1.2211 0.1119 0.048 Uiso 1 1 calc R . . C5 C -0.1687(9) 1.0967(9) 0.0974(5) 0.033(3) Uani 1 1 d . . . C6 C -0.0921(9) 1.1878(9) 0.0498(5) 0.036(3) Uani 1 1 d . . . C7 C 0.0417(9) 1.1831(8) 0.0413(5) 0.031(2) Uani 1 1 d . . . C8 C -0.0635(10) 1.3480(9) -0.0395(5) 0.038(3) Uani 1 1 d . . . C9 C -0.2195(10) 1.5137(9) -0.1183(5) 0.053(3) Uani 1 1 d . . . H9 H -0.2852 1.4702 -0.0935 0.064 Uiso 1 1 calc R . . C10 C -0.2518(10) 1.6264(10) -0.1742(6) 0.060(3) Uani 1 1 d . . . H10 H -0.3400 1.6569 -0.1850 0.072 Uiso 1 1 calc R . . C11 C 0.0002(10) 1.5337(9) -0.1379(5) 0.055(3) Uani 1 1 d . . . H11 H 0.0885 1.5058 -0.1267 0.066 Uiso 1 1 calc R . . C12 C -0.0407(12) 1.6449(9) -0.1940(5) 0.059(3) Uani 1 1 d . . . H12 H 0.0237 1.6890 -0.2202 0.071 Uiso 1 1 calc R . . C13 C 0.1524(9) 1.0953(8) 0.0831(5) 0.030(2) Uani 1 1 d . . . C14 C 0.1365(8) 1.0480(8) 0.1619(5) 0.033(3) Uani 1 1 d . . . H14 H 0.0579 1.0722 0.1885 0.040 Uiso 1 1 calc R . . C15 C 0.2406(10) 0.9630(9) 0.2012(5) 0.038(3) Uani 1 1 d . . . H15 H 0.2289 0.9293 0.2543 0.046 Uiso 1 1 calc R . . C16 C 0.2717(9) 1.0611(9) 0.0479(5) 0.044(3) Uani 1 1 d . . . H16 H 0.2874 1.0963 -0.0047 0.053 Uiso 1 1 calc R . . C17 C 0.3686(9) 0.9748(10) 0.0899(5) 0.057(3) Uani 1 1 d . . . H17 H 0.4467 0.9476 0.0639 0.068 Uiso 1 1 calc R . . C20 C 0.7934(9) 0.6808(9) 0.3291(5) 0.040(3) Uani 1 1 d . . . H20 H 0.7844 0.7663 0.3242 0.048 Uiso 1 1 calc R . . C21 C 0.8992(8) 0.6003(9) 0.3669(5) 0.034(2) Uani 1 1 d . . . H21 H 0.9630 0.6310 0.3848 0.040 Uiso 1 1 calc R . . C22 C 0.9092(8) 0.4714(9) 0.3779(5) 0.032(2) Uani 1 1 d . . . C23 C 0.8144(9) 0.4345(9) 0.3471(5) 0.043(3) Uani 1 1 d . . . H23 H 0.8179 0.3497 0.3521 0.052 Uiso 1 1 calc R . . C24 C 0.7148(8) 0.5213(9) 0.3090(5) 0.045(3) Uani 1 1 d . . . H24 H 0.6517 0.4930 0.2889 0.054 Uiso 1 1 calc R . . C25 C 1.0152(8) 0.3805(8) 0.4239(5) 0.033(3) Uani 1 1 d . . . C26 C 1.1432(9) 0.3856(9) 0.4283(5) 0.033(3) Uani 1 1 d . . . C27 C 1.0976(9) 0.2126(8) 0.5079(5) 0.031(3) Uani 1 1 d . . . C28 C 1.2261(8) 0.4802(9) 0.3877(5) 0.033(3) Uani 1 1 d . . . C29 C 1.2109(8) 0.5397(8) 0.3099(5) 0.038(3) Uani 1 1 d . . . H29 H 1.1479 0.5237 0.2828 0.046 Uiso 1 1 calc R . . C30 C 1.2910(9) 0.6231(8) 0.2738(5) 0.041(3) Uani 1 1 d . . . H30 H 1.2811 0.6614 0.2213 0.049 Uiso 1 1 calc R . . C31 C 1.3918(8) 0.5969(9) 0.3827(5) 0.043(3) Uani 1 1 d . . . H31 H 1.4534 0.6171 0.4089 0.052 Uiso 1 1 calc R . . C32 C 1.3183(9) 0.5111(9) 0.4241(5) 0.043(3) Uani 1 1 d . . . H32 H 1.3311 0.4742 0.4766 0.051 Uiso 1 1 calc R . . C33 C 1.1077(9) 0.0982(8) 0.5686(5) 0.029(2) Uani 1 1 d . . . C34 C 1.2183(9) 0.0430(9) 0.6103(5) 0.044(3) Uani 1 1 d . . . H34 H 1.2940 0.0775 0.5984 0.053 Uiso 1 1 calc R . . C35 C 1.2165(10) -0.0625(10) 0.6691(5) 0.052(3) Uani 1 1 d . . . H35 H 1.2923 -0.0954 0.6969 0.063 Uiso 1 1 calc R . . C36 C 1.0137(11) -0.0722(10) 0.6494(6) 0.058(3) Uani 1 1 d . . . H36 H 0.9423 -0.1129 0.6612 0.070 Uiso 1 1 calc R . . C37 C 1.0016(9) 0.0381(9) 0.5890(5) 0.043(3) Uani 1 1 d . . . H37 H 0.9236 0.0702 0.5633 0.051 Uiso 1 1 calc R . . C38 C 0.4752(10) 0.7892(10) 0.5289(7) 0.057(3) Uani 1 1 d . . . C39 C 0.3317(9) 0.8190(10) 0.5091(6) 0.083(4) Uani 1 1 d U . . H39A H 0.3261 0.8278 0.4548 0.124 Uiso 1 1 calc R . . H39B H 0.2892 0.8959 0.5215 0.124 Uiso 1 1 calc R . . H39C H 0.2889 0.7522 0.5385 0.124 Uiso 1 1 calc R . . C40 C -0.0924(9) 1.4675(9) -0.1000(5) 0.036(3) Uani 1 1 d . . . N1 N 0.7027(7) 0.6411(7) 0.2992(4) 0.038(2) Uani 1 1 d . . . N2 N 1.1938(6) 0.2794(6) 0.4839(4) 0.030(2) Uani 1 1 d . . . H2A H 1.2724 0.2596 0.5002 0.037 Uiso 1 1 calc R . . N3 N 0.9856(7) 0.2725(7) 0.4723(4) 0.036(2) Uani 1 1 d . . . N4 N 1.3809(7) 0.6524(7) 0.3084(4) 0.040(2) Uani 1 1 d . . . N5 N 1.1181(9) -0.1221(8) 0.6902(4) 0.054(3) Uani 1 1 d . . . N6 N 0.3558(7) 0.9278(7) 0.1663(4) 0.041(2) Uani 1 1 d . . . N7 N 0.0588(7) 1.2863(7) -0.0172(4) 0.035(2) Uani 1 1 d . . . H7 H 0.1325 1.3079 -0.0360 0.042 Uiso 1 1 calc R . . N8 N -0.1568(7) 1.2921(7) 0.0000(4) 0.036(2) Uani 1 1 d . . . N9 N -0.1644(10) 1.6923(8) -0.2127(4) 0.058(3) Uani 1 1 d . . . N10 N -0.3280(7) 0.9264(8) 0.1770(4) 0.038(2) Uani 1 1 d . . . O1W O 0.4864(5) 0.8860(6) 0.3298(3) 0.056(2) Uani 1 1 d . . . H1A H 0.5652 0.9195 0.3348 0.067 Uiso 1 1 d R . . H1B H 0.4106 0.9564 0.3155 0.067 Uiso 1 1 d R . . O3 O 0.5044(7) 0.7735(8) 0.5980(4) 0.087(3) Uani 1 1 d U . . O4 O 0.5575(6) 0.7802(6) 0.4719(4) 0.054(2) Uani 1 1 d . . . Cd1 Cd 0.52978(7) 0.78041(7) 0.23393(4) 0.0365(3) Uani 1 1 d . . . O2W O 0.6565(8) 0.8762(6) 0.6732(4) 0.095(3) Uani 1 1 d . . . O3W O 0.5566(12) 0.3397(12) 0.2438(6) 0.205(5) Uani 1 1 d U . . O1 O 0.5190(6) 0.6676(7) 0.1501(4) 0.069(2) Uani 1 1 d U A . O2 O 0.7104(7) 0.6830(6) 0.0983(3) 0.063(2) Uani 1 1 d . A . C18 C 0.6109(11) 0.6438(11) 0.1027(6) 0.057(3) Uani 1 1 d . . . C19A C 0.6045(16) 0.5460(17) 0.0596(10) 0.078(6) Uiso 0.70 1 d P A 1 C19B C 0.565(3) 0.620(3) 0.0280(17) 0.039(9) Uiso 0.30 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(7) 0.017(6) 0.049(6) 0.000(5) -0.002(5) -0.008(5) C2 0.018(6) 0.047(8) 0.029(6) 0.001(5) -0.005(4) -0.009(5) C3 0.027(6) 0.039(8) 0.047(7) 0.001(6) 0.000(5) 0.004(5) C4 0.034(7) 0.027(7) 0.043(6) 0.013(5) 0.008(5) -0.004(5) C5 0.023(6) 0.036(8) 0.030(6) 0.006(5) -0.004(5) 0.000(5) C6 0.033(7) 0.035(7) 0.036(6) 0.007(6) -0.003(5) -0.017(6) C7 0.026(7) 0.035(7) 0.024(6) 0.008(5) 0.001(5) -0.008(5) C8 0.035(7) 0.041(8) 0.038(6) -0.002(6) -0.003(5) -0.015(6) C9 0.050(8) 0.040(8) 0.050(7) 0.017(6) -0.005(6) 0.000(6) C10 0.047(8) 0.059(9) 0.064(8) -0.001(7) -0.010(6) -0.004(7) C11 0.050(7) 0.041(8) 0.057(7) 0.014(6) -0.004(6) -0.008(6) C12 0.083(10) 0.032(8) 0.052(8) 0.011(6) 0.013(7) -0.027(7) C13 0.028(7) 0.034(7) 0.027(6) 0.004(5) -0.007(5) -0.014(5) C14 0.015(6) 0.036(7) 0.037(6) 0.004(5) -0.007(5) 0.006(5) C15 0.043(7) 0.041(7) 0.032(6) -0.008(5) 0.006(6) -0.018(6) C16 0.035(7) 0.057(8) 0.030(6) 0.009(6) -0.005(6) -0.014(6) C17 0.037(7) 0.080(9) 0.035(7) 0.014(6) -0.004(5) -0.008(6) C20 0.035(7) 0.037(7) 0.047(6) -0.004(5) -0.006(5) -0.014(6) C21 0.017(6) 0.039(7) 0.044(6) -0.005(5) -0.016(5) -0.003(5) C22 0.025(6) 0.034(7) 0.031(6) 0.002(5) 0.005(5) -0.009(5) C23 0.035(7) 0.031(7) 0.063(7) -0.003(6) -0.015(6) -0.013(6) C24 0.030(7) 0.030(7) 0.072(8) 0.004(6) -0.034(5) -0.007(5) C25 0.019(6) 0.032(7) 0.046(6) 0.001(5) -0.007(5) -0.014(5) C26 0.027(6) 0.044(8) 0.028(6) -0.002(5) -0.010(5) -0.010(5) C27 0.025(6) 0.027(7) 0.040(6) 0.006(5) -0.009(5) -0.019(5) C28 0.021(6) 0.038(7) 0.044(7) -0.013(6) -0.001(5) -0.013(5) C29 0.040(6) 0.053(8) 0.023(6) -0.002(5) -0.004(5) -0.018(6) C30 0.041(7) 0.047(7) 0.034(6) 0.006(5) -0.010(5) -0.025(6) C31 0.031(6) 0.049(7) 0.050(7) 0.000(6) -0.012(5) -0.020(5) C32 0.046(7) 0.054(8) 0.024(6) 0.006(5) -0.006(5) -0.020(6) C33 0.029(6) 0.023(6) 0.030(6) 0.009(5) -0.004(5) -0.012(5) C34 0.042(7) 0.042(8) 0.039(6) 0.008(6) -0.007(5) -0.011(6) C35 0.044(8) 0.056(9) 0.044(7) 0.003(6) -0.012(5) 0.004(6) C36 0.069(9) 0.049(8) 0.054(7) 0.007(6) 0.003(6) -0.036(7) C37 0.041(7) 0.033(7) 0.044(7) 0.004(6) -0.002(5) -0.003(5) C38 0.042(8) 0.049(8) 0.076(10) -0.008(7) -0.008(7) -0.011(6) C39 0.056(7) 0.101(8) 0.089(7) -0.027(6) -0.010(6) -0.006(6) C40 0.032(7) 0.030(7) 0.033(6) 0.011(5) -0.004(5) -0.001(5) N1 0.040(6) 0.021(6) 0.050(5) 0.003(4) -0.018(4) -0.004(4) N2 0.015(4) 0.029(5) 0.042(5) 0.005(4) -0.013(4) -0.005(4) N3 0.027(5) 0.036(6) 0.040(5) 0.004(4) -0.008(4) -0.012(4) N4 0.039(6) 0.040(6) 0.033(5) 0.018(4) -0.019(4) -0.013(4) N5 0.061(7) 0.039(6) 0.051(6) 0.015(5) -0.020(5) -0.012(5) N6 0.034(6) 0.049(6) 0.033(5) 0.003(5) -0.012(4) -0.004(4) N7 0.029(5) 0.033(6) 0.036(5) 0.006(4) -0.005(4) -0.012(4) N8 0.028(5) 0.036(6) 0.031(5) 0.018(4) -0.001(4) -0.013(4) N9 0.059(7) 0.045(7) 0.059(6) 0.000(5) -0.014(5) 0.007(6) N10 0.028(5) 0.034(6) 0.044(5) 0.002(5) 0.000(4) -0.008(4) O1W 0.037(4) 0.058(5) 0.064(5) 0.005(4) -0.022(3) -0.005(4) O3 0.077(5) 0.113(6) 0.067(5) -0.018(5) -0.018(4) -0.008(4) O4 0.022(4) 0.067(5) 0.056(5) 0.007(4) -0.007(3) -0.003(4) Cd1 0.0266(4) 0.0359(5) 0.0385(5) 0.0098(4) -0.0085(3) -0.0096(3) O2W 0.131(7) 0.039(5) 0.111(6) -0.016(5) -0.050(5) 0.013(5) O3W 0.221(9) 0.203(9) 0.206(8) -0.061(7) -0.019(7) -0.057(7) O1 0.044(4) 0.104(6) 0.072(5) -0.045(4) 0.007(4) -0.015(4) O2 0.060(5) 0.079(6) 0.059(5) -0.010(4) 0.004(4) -0.048(5) C18 0.038(8) 0.087(10) 0.056(8) -0.030(7) 0.005(6) -0.021(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N10 1.343(10) . ? C1 C2 1.396(10) . ? C2 C5 1.382(11) . ? C3 N10 1.314(10) . ? C3 C4 1.372(10) . ? C4 C5 1.370(11) . ? C5 C6 1.466(11) . ? C6 N8 1.361(10) . ? C6 C7 1.375(10) . ? C7 N7 1.368(9) . ? C7 C13 1.469(11) . ? C8 N8 1.308(9) . ? C8 N7 1.357(10) . ? C8 C40 1.479(11) . ? C9 C40 1.353(11) . ? C9 C10 1.389(12) . ? C10 N9 1.316(11) . ? C11 C40 1.356(11) . ? C11 C12 1.394(12) . ? C12 N9 1.324(11) . ? C13 C16 1.362(11) . ? C13 C14 1.376(10) . ? C14 C15 1.393(11) . ? C15 N6 1.328(10) . ? C16 C17 1.368(11) . ? C17 N6 1.333(9) . ? C20 N1 1.339(10) . ? C20 C21 1.376(10) . ? C21 C22 1.397(11) . ? C22 C23 1.365(11) . ? C22 C25 1.483(11) . ? C23 C24 1.361(11) . ? C24 N1 1.296(10) . ? C25 C26 1.355(10) . ? C25 N3 1.364(9) . ? C26 N2 1.378(10) . ? C26 C28 1.499(11) . ? C27 N2 1.344(9) . ? C27 N3 1.344(9) . ? C27 C33 1.438(10) . ? C28 C32 1.365(11) . ? C28 C29 1.383(10) . ? C29 C30 1.374(10) . ? C30 N4 1.316(9) . ? C31 N4 1.315(9) . ? C31 C32 1.370(10) . ? C33 C34 1.376(11) . ? C33 C37 1.381(10) . ? C34 C35 1.361(11) . ? C35 N5 1.309(10) . ? C36 N5 1.309(11) . ? C36 C37 1.402(11) . ? C38 O3 1.264(11) . ? C38 O4 1.275(11) . ? C38 C39 1.515(12) . ? N1 Cd1 2.305(7) . ? N4 Cd1 2.394(7) 1_655 ? N6 Cd1 2.365(7) . ? N10 Cd1 2.396(7) 1_455 ? O1W Cd1 2.307(6) . ? Cd1 O1 2.246(7) . ? Cd1 N4 2.394(7) 1_455 ? Cd1 N10 2.396(7) 1_655 ? O1 C18 1.248(11) . ? O2 C18 1.196(10) . ? C18 C19A 1.526(19) . ? C18 C19B 1.57(3) . ? 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 N10 C1 C2 121.7(9) . . ? C5 C2 C1 120.3(8) . . ? N10 C3 C4 125.2(9) . . ? C5 C4 C3 119.2(9) . . ? C4 C5 C2 116.9(8) . . ? C4 C5 C6 120.2(9) . . ? C2 C5 C6 122.7(9) . . ? N8 C6 C7 110.8(7) . . ? N8 C6 C5 118.5(8) . . ? C7 C6 C5 130.5(9) . . ? N7 C7 C6 105.3(7) . . ? N7 C7 C13 122.5(8) . . ? C6 C7 C13 132.1(8) . . ? N8 C8 N7 112.8(8) . . ? N8 C8 C40 122.2(9) . . ? N7 C8 C40 125.0(8) . . ? C40 C9 C10 119.9(9) . . ? N9 C10 C9 123.7(10) . . ? C40 C11 C12 118.2(9) . . ? N9 C12 C11 124.9(9) . . ? C16 C13 C14 118.1(8) . . ? C16 C13 C7 123.2(8) . . ? C14 C13 C7 118.6(8) . . ? C13 C14 C15 118.6(8) . . ? N6 C15 C14 123.0(8) . . ? C13 C16 C17 120.0(8) . . ? N6 C17 C16 122.9(9) . . ? N1 C20 C21 122.6(9) . . ? C20 C21 C22 118.7(8) . . ? C23 C22 C21 116.9(8) . . ? C23 C22 C25 122.4(9) . . ? C21 C22 C25 120.7(8) . . ? C24 C23 C22 120.2(9) . . ? N1 C24 C23 123.9(9) . . ? C26 C25 N3 110.7(8) . . ? C26 C25 C22 130.7(8) . . ? N3 C25 C22 118.6(8) . . ? C25 C26 N2 105.8(7) . . ? C25 C26 C28 132.8(9) . . ? N2 C26 C28 121.4(8) . . ? N2 C27 N3 111.0(8) . . ? N2 C27 C33 125.1(8) . . ? N3 C27 C33 123.7(8) . . ? C32 C28 C29 117.3(8) . . ? C32 C28 C26 122.8(8) . . ? C29 C28 C26 119.8(8) . . ? C30 C29 C28 118.5(8) . . ? N4 C30 C29 124.4(8) . . ? N4 C31 C32 124.2(8) . . ? C28 C32 C31 119.4(8) . . ? C34 C33 C37 116.0(8) . . ? C34 C33 C27 123.9(8) . . ? C37 C33 C27 120.1(8) . . ? C35 C34 C33 119.6(9) . . ? N5 C35 C34 126.1(9) . . ? N5 C36 C37 124.8(9) . . ? C33 C37 C36 118.8(9) . . ? O3 C38 O4 125.5(10) . . ? O3 C38 C39 119.6(11) . . ? O4 C38 C39 114.8(10) . . ? C11 C40 C9 118.1(9) . . ? C11 C40 C8 124.2(9) . . ? C9 C40 C8 117.7(8) . . ? C24 N1 C20 117.6(8) . . ? C24 N1 Cd1 121.2(6) . . ? C20 N1 Cd1 121.3(6) . . ? C27 N2 C26 107.3(7) . . ? C27 N3 C25 105.0(7) . . ? C31 N4 C30 116.1(7) . . ? C31 N4 Cd1 123.3(6) . 1_655 ? C30 N4 Cd1 120.1(6) . 1_655 ? C36 N5 C35 114.7(9) . . ? C15 N6 C17 117.2(8) . . ? C15 N6 Cd1 122.4(6) . . ? C17 N6 Cd1 120.3(7) . . ? C8 N7 C7 106.4(7) . . ? C8 N8 C6 104.8(7) . . ? C10 N9 C12 115.3(9) . . ? C3 N10 C1 116.6(7) . . ? C3 N10 Cd1 122.7(6) . 1_455 ? C1 N10 Cd1 120.4(6) . 1_455 ? O1 Cd1 N1 95.1(3) . . ? O1 Cd1 O1W 165.0(2) . . ? N1 Cd1 O1W 91.7(2) . . ? O1 Cd1 N6 85.8(3) . . ? N1 Cd1 N6 178.4(3) . . ? O1W Cd1 N6 87.7(2) . . ? O1 Cd1 N4 81.3(3) . 1_455 ? N1 Cd1 N4 89.5(3) . 1_455 ? O1W Cd1 N4 85.4(2) . 1_455 ? N6 Cd1 N4 91.9(3) . 1_455 ? O1 Cd1 N10 108.5(3) . 1_655 ? N1 Cd1 N10 90.4(3) . 1_655 ? O1W Cd1 N10 84.7(2) . 1_655 ? N6 Cd1 N10 88.0(3) . 1_655 ? N4 Cd1 N10 170.1(3) 1_455 1_655 ? C18 O1 Cd1 123.2(7) . . ? O2 C18 O1 121.1(11) . . ? O2 C18 C19A 119.4(11) . . ? O1 C18 C19A 118.8(11) . . ? O2 C18 C19B 118.6(13) . . ? O1 C18 C19B 114.2(14) . . ? C19A C18 C19B 34.2(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N10 C1 C2 C5 -3.5(13) . . . . ? N10 C3 C4 C5 -0.3(14) . . . . ? C3 C4 C5 C2 -1.0(13) . . . . ? C3 C4 C5 C6 174.5(8) . . . . ? C1 C2 C5 C4 2.8(12) . . . . ? C1 C2 C5 C6 -172.6(8) . . . . ? C4 C5 C6 N8 -31.9(13) . . . . ? C2 C5 C6 N8 143.4(9) . . . . ? C4 C5 C6 C7 153.9(10) . . . . ? C2 C5 C6 C7 -30.8(15) . . . . ? N8 C6 C7 N7 -1.7(11) . . . . ? C5 C6 C7 N7 172.9(9) . . . . ? N8 C6 C7 C13 176.4(10) . . . . ? C5 C6 C7 C13 -9.0(18) . . . . ? C40 C9 C10 N9 1.2(17) . . . . ? C40 C11 C12 N9 1.0(16) . . . . ? N7 C7 C13 C16 -38.1(14) . . . . ? C6 C7 C13 C16 144.0(11) . . . . ? N7 C7 C13 C14 139.9(9) . . . . ? C6 C7 C13 C14 -38.0(15) . . . . ? C16 C13 C14 C15 -3.1(13) . . . . ? C7 C13 C14 C15 178.8(8) . . . . ? C13 C14 C15 N6 1.7(14) . . . . ? C14 C13 C16 C17 4.7(14) . . . . ? C7 C13 C16 C17 -177.3(9) . . . . ? C13 C16 C17 N6 -5.1(16) . . . . ? N1 C20 C21 C22 -3.2(13) . . . . ? C20 C21 C22 C23 2.6(13) . . . . ? C20 C21 C22 C25 -174.9(7) . . . . ? C21 C22 C23 C24 -1.2(13) . . . . ? C25 C22 C23 C24 176.2(8) . . . . ? C22 C23 C24 N1 0.2(15) . . . . ? C23 C22 C25 C26 144.5(10) . . . . ? C21 C22 C25 C26 -38.2(15) . . . . ? C23 C22 C25 N3 -36.9(13) . . . . ? C21 C22 C25 N3 140.4(9) . . . . ? N3 C25 C26 N2 -2.5(11) . . . . ? C22 C25 C26 N2 176.1(9) . . . . ? N3 C25 C26 C28 179.0(9) . . . . ? C22 C25 C26 C28 -2.3(18) . . . . ? C25 C26 C28 C32 141.4(11) . . . . ? N2 C26 C28 C32 -36.8(14) . . . . ? C25 C26 C28 C29 -38.9(15) . . . . ? N2 C26 C28 C29 142.8(9) . . . . ? C32 C28 C29 C30 1.6(14) . . . . ? C26 C28 C29 C30 -178.0(8) . . . . ? C28 C29 C30 N4 -1.2(15) . . . . ? C29 C28 C32 C31 -0.8(14) . . . . ? C26 C28 C32 C31 178.9(9) . . . . ? N4 C31 C32 C28 -0.7(15) . . . . ? N2 C27 C33 C34 0.3(15) . . . . ? N3 C27 C33 C34 -173.5(9) . . . . ? N2 C27 C33 C37 179.2(8) . . . . ? N3 C27 C33 C37 5.5(14) . . . . ? C37 C33 C34 C35 -1.9(14) . . . . ? C27 C33 C34 C35 177.1(9) . . . . ? C33 C34 C35 N5 2.0(17) . . . . ? C34 C33 C37 C36 0.0(14) . . . . ? C27 C33 C37 C36 -179.0(9) . . . . ? N5 C36 C37 C33 2.0(16) . . . . ? C12 C11 C40 C9 -0.7(15) . . . . ? C12 C11 C40 C8 179.7(9) . . . . ? C10 C9 C40 C11 -0.3(15) . . . . ? C10 C9 C40 C8 179.3(9) . . . . ? N8 C8 C40 C11 174.4(9) . . . . ? N7 C8 C40 C11 -3.7(16) . . . . ? N8 C8 C40 C9 -5.2(14) . . . . ? N7 C8 C40 C9 176.7(9) . . . . ? C23 C24 N1 C20 -0.7(15) . . . . ? C23 C24 N1 Cd1 -179.9(7) . . . . ? C21 C20 N1 C24 2.2(13) . . . . ? C21 C20 N1 Cd1 -178.6(6) . . . . ? N3 C27 N2 C26 -2.1(10) . . . . ? C33 C27 N2 C26 -176.5(9) . . . . ? C25 C26 N2 C27 2.8(10) . . . . ? C28 C26 N2 C27 -178.6(8) . . . . ? N2 C27 N3 C25 0.5(10) . . . . ? C33 C27 N3 C25 175.1(9) . . . . ? C26 C25 N3 C27 1.3(11) . . . . ? C22 C25 N3 C27 -177.5(8) . . . . ? C32 C31 N4 C30 1.2(15) . . . . ? C32 C31 N4 Cd1 -171.4(7) . . . 1_655 ? C29 C30 N4 C31 -0.3(15) . . . . ? C29 C30 N4 Cd1 172.6(7) . . . 1_655 ? C37 C36 N5 C35 -2.0(16) . . . . ? C34 C35 N5 C36 0.0(16) . . . . ? C14 C15 N6 C17 -1.9(14) . . . . ? C14 C15 N6 Cd1 -178.8(7) . . . . ? C16 C17 N6 C15 3.6(15) . . . . ? C16 C17 N6 Cd1 -179.4(8) . . . . ? N8 C8 N7 C7 -0.1(11) . . . . ? C40 C8 N7 C7 178.1(9) . . . . ? C6 C7 N7 C8 1.1(10) . . . . ? C13 C7 N7 C8 -177.3(8) . . . . ? N7 C8 N8 C6 -0.9(11) . . . . ? C40 C8 N8 C6 -179.2(9) . . . . ? C7 C6 N8 C8 1.6(10) . . . . ? C5 C6 N8 C8 -173.7(8) . . . . ? C9 C10 N9 C12 -1.0(16) . . . . ? C11 C12 N9 C10 -0.1(16) . . . . ? C4 C3 N10 C1 -0.3(14) . . . . ? C4 C3 N10 Cd1 -173.7(7) . . . 1_455 ? C2 C1 N10 C3 2.1(13) . . . . ? C2 C1 N10 Cd1 175.8(6) . . . 1_455 ? C24 N1 Cd1 O1 -34.3(8) . . . . ? C20 N1 Cd1 O1 146.5(7) . . . . ? C24 N1 Cd1 O1W 132.4(7) . . . . ? C20 N1 Cd1 O1W -46.8(7) . . . . ? C24 N1 Cd1 N6 -159(10) . . . . ? C20 N1 Cd1 N6 21(11) . . . . ? C24 N1 Cd1 N4 47.0(8) . . . 1_455 ? C20 N1 Cd1 N4 -132.2(7) . . . 1_455 ? C24 N1 Cd1 N10 -142.9(7) . . . 1_655 ? C20 N1 Cd1 N10 37.9(7) . . . 1_655 ? C15 N6 Cd1 O1 121.7(7) . . . . ? C17 N6 Cd1 O1 -55.2(7) . . . . ? C15 N6 Cd1 N1 -113(10) . . . . ? C17 N6 Cd1 N1 70(11) . . . . ? C15 N6 Cd1 O1W -44.8(7) . . . . ? C17 N6 Cd1 O1W 138.3(7) . . . . ? C15 N6 Cd1 N4 40.5(7) . . . 1_455 ? C17 N6 Cd1 N4 -136.3(7) . . . 1_455 ? C15 N6 Cd1 N10 -129.6(7) . . . 1_655 ? C17 N6 Cd1 N10 53.5(7) . . . 1_655 ? N1 Cd1 O1 C18 -62.7(9) . . . . ? O1W Cd1 O1 C18 -179.5(8) . . . . ? N6 Cd1 O1 C18 116.0(9) . . . . ? N4 Cd1 O1 C18 -151.4(9) 1_455 . . . ? N10 Cd1 O1 C18 29.5(9) 1_655 . . . ? Cd1 O1 C18 O2 -1.7(15) . . . . ? Cd1 O1 C18 C19A 168.2(9) . . . . ? Cd1 O1 C18 C19B -153.7(14) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 20.94 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.531 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 909300'