# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Catherine E Housecroft' 'Edwin Constable' 'Markus Neuburger' 'Jennifer A Zampese' 'Guoqi Zhang.' _publ_contact_author_name 'Catherine E Housecroft' _publ_contact_author_email CATHERINE.HOUSECROFT@UNIBAS.CH _publ_section_title ; Assembling and dissembling zinc-containing coordination polymers of 4'-phenyl-4,2':6',4"-terpyridine ; # Attachment 'GQ87_2.CIF' data_gq87 _database_code_depnum_ccdc_archive 'CCDC 758783' #TrackingRef 'GQ87_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 N3, I4 Zn' _chemical_formula_sum 'C23 H21 I4 N3 Zn' _chemical_formula_weight 912.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc 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 7.8681(16) _cell_length_b 26.630(5) _cell_length_c 13.461(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.53(3) _cell_angle_gamma 90.00 _cell_volume 2773.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 5.354 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2559 _exptl_absorpt_correction_T_max 0.8559 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _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 34864 _diffrn_reflns_av_R_equivalents 0.0860 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5390 _reflns_number_gt 5190 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0135P)^2^+7.0644P] 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 5390 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.56885(6) 0.154733(18) 0.36780(4) 0.03135(11) Uani 1 1 d . . . I1 I 0.49097(3) 0.063661(10) 0.294743(19) 0.02983(7) Uani 1 1 d . . . I2 I 0.74407(4) 0.140235(12) 0.55181(2) 0.04229(9) Uani 1 1 d . . . I3 I 0.74679(4) 0.200998(11) 0.25128(2) 0.03556(8) Uani 1 1 d . . . I4 I 0.29213(4) 0.207044(12) 0.37059(3) 0.05003(10) Uani 1 1 d . . . N1 N 0.9708(5) -0.19553(14) -0.0091(3) 0.0386(8) Uani 1 1 d . . . N2 N 0.9318(4) -0.03459(13) 0.1667(2) 0.0263(6) Uani 1 1 d . . . N3 N 1.1868(4) 0.05125(14) 0.4878(2) 0.0298(7) Uani 1 1 d . . . C1 C 1.0241(8) -0.24592(18) -0.0374(4) 0.0580(15) Uani 1 1 d . . . H1A H 0.9433 -0.2579 -0.0969 0.087 Uiso 1 1 calc R . . H1B H 1.0236 -0.2692 0.0189 0.087 Uiso 1 1 calc R . . H1C H 1.1408 -0.2442 -0.0531 0.087 Uiso 1 1 calc R . . C2 C 0.8855(6) -0.16482(18) -0.0794(4) 0.0418(10) Uani 1 1 d . . . H2A H 0.8544 -0.1762 -0.1472 0.050 Uiso 1 1 calc R . . C3 C 0.8422(6) -0.11718(17) -0.0553(3) 0.0363(9) Uani 1 1 d . . . H3A H 0.7806 -0.0958 -0.1060 0.044 Uiso 1 1 calc R . . C4 C 0.8886(5) -0.09997(15) 0.0440(3) 0.0282(8) Uani 1 1 d . . . C5 C 0.9757(5) -0.13324(16) 0.1156(3) 0.0351(9) Uani 1 1 d . . . H5A H 1.0078 -0.1230 0.1841 0.042 Uiso 1 1 calc R . . C6 C 1.0149(6) -0.18029(17) 0.0877(3) 0.0391(9) Uani 1 1 d . . . H6A H 1.0742 -0.2027 0.1370 0.047 Uiso 1 1 calc R . . C7 C 0.8560(4) -0.04764(15) 0.0728(3) 0.0262(7) Uani 1 1 d . . . C8 C 0.7587(5) -0.01383(15) 0.0059(3) 0.0273(7) Uani 1 1 d . . . H8A H 0.7031 -0.0248 -0.0591 0.033 Uiso 1 1 calc R . . C9 C 0.7434(4) 0.03571(14) 0.0344(3) 0.0239(7) Uani 1 1 d . . . C10 C 0.8253(5) 0.04892(15) 0.1317(3) 0.0257(7) Uani 1 1 d . . . H10A H 0.8189 0.0825 0.1547 0.031 Uiso 1 1 calc R . . C11 C 0.9160(4) 0.01310(14) 0.1949(3) 0.0239(7) Uani 1 1 d . . . C12 C 1.1919(5) 0.00400(17) 0.4539(3) 0.0326(8) Uani 1 1 d . . . H12A H 1.2578 -0.0206 0.4953 0.039 Uiso 1 1 calc R . . C13 C 1.1032(5) -0.00927(16) 0.3600(3) 0.0294(8) Uani 1 1 d . . . H13A H 1.1077 -0.0429 0.3369 0.035 Uiso 1 1 calc R . . C14 C 1.0064(4) 0.02654(15) 0.2987(3) 0.0255(7) Uani 1 1 d . . . C15 C 1.0006(5) 0.07473(16) 0.3371(3) 0.0304(8) Uani 1 1 d . . . H15A H 0.9325 0.0998 0.2982 0.036 Uiso 1 1 calc R . . C16 C 1.0923(5) 0.08636(16) 0.4305(3) 0.0309(8) Uani 1 1 d . . . H16A H 1.0893 0.1197 0.4553 0.037 Uiso 1 1 calc R . . C17 C 1.2888(6) 0.06608(19) 0.5869(3) 0.0427(11) Uani 1 1 d . . . H17A H 1.3857 0.0873 0.5764 0.064 Uiso 1 1 calc R . . H17B H 1.3334 0.0360 0.6247 0.064 Uiso 1 1 calc R . . H17C H 1.2150 0.0848 0.6251 0.064 Uiso 1 1 calc R . . C18 C 0.6531(4) 0.07472(15) -0.0343(3) 0.0250(7) Uani 1 1 d . . . C19 C 0.6388(5) 0.07015(16) -0.1389(3) 0.0308(8) Uani 1 1 d . . . H19A H 0.6772 0.0405 -0.1671 0.037 Uiso 1 1 calc R . . C20 C 0.5682(6) 0.10909(19) -0.2014(3) 0.0389(10) Uani 1 1 d . . . H20A H 0.5598 0.1060 -0.2725 0.047 Uiso 1 1 calc R . . C21 C 0.5103(6) 0.15212(19) -0.1621(3) 0.0436(11) Uani 1 1 d . . . H21A H 0.4636 0.1787 -0.2058 0.052 Uiso 1 1 calc R . . C22 C 0.5202(6) 0.15672(18) -0.0587(3) 0.0402(10) Uani 1 1 d . . . H22A H 0.4792 0.1862 -0.0312 0.048 Uiso 1 1 calc R . . C23 C 0.5903(5) 0.11789(16) 0.0044(3) 0.0324(8) Uani 1 1 d . . . H23A H 0.5955 0.1208 0.0752 0.039 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 Zn1 0.0327(2) 0.0284(2) 0.0359(2) -0.00224(19) 0.01420(18) -0.00474(18) I1 0.03095(13) 0.02617(14) 0.03344(13) -0.00216(10) 0.00872(9) -0.00383(9) I2 0.06452(19) 0.03400(16) 0.02974(14) 0.00266(11) 0.01229(12) -0.01176(13) I3 0.04340(15) 0.03282(15) 0.03356(14) 0.00214(10) 0.01519(11) -0.00777(11) I4 0.03854(16) 0.03644(18) 0.0807(2) -0.01431(15) 0.02566(15) -0.00165(12) N1 0.050(2) 0.0219(18) 0.051(2) 0.0056(15) 0.0278(17) 0.0028(15) N2 0.0230(14) 0.0279(17) 0.0272(15) 0.0020(13) 0.0021(11) 0.0010(12) N3 0.0276(15) 0.0365(19) 0.0249(15) 0.0031(14) 0.0039(12) -0.0067(14) C1 0.098(4) 0.026(2) 0.065(3) 0.004(2) 0.055(3) 0.014(3) C2 0.056(3) 0.034(2) 0.040(2) -0.0024(19) 0.022(2) 0.002(2) C3 0.043(2) 0.028(2) 0.038(2) 0.0013(17) 0.0073(17) 0.0057(17) C4 0.0255(17) 0.0241(19) 0.036(2) 0.0009(15) 0.0069(14) -0.0007(14) C5 0.038(2) 0.027(2) 0.040(2) 0.0055(17) 0.0065(17) 0.0023(16) C6 0.047(2) 0.029(2) 0.044(2) 0.0095(18) 0.0156(19) 0.0059(18) C7 0.0238(16) 0.0237(19) 0.0319(18) 0.0007(15) 0.0076(14) -0.0016(14) C8 0.0279(18) 0.0274(19) 0.0262(17) -0.0003(15) 0.0038(14) -0.0012(15) C9 0.0201(15) 0.0253(19) 0.0274(17) 0.0009(14) 0.0069(13) -0.0013(13) C10 0.0285(17) 0.0234(18) 0.0268(17) 0.0010(14) 0.0090(14) 0.0019(14) C11 0.0224(16) 0.0247(18) 0.0251(17) 0.0023(14) 0.0053(13) -0.0013(13) C12 0.0337(19) 0.034(2) 0.0287(19) 0.0071(16) 0.0022(15) -0.0037(16) C13 0.0297(18) 0.027(2) 0.0309(19) 0.0044(15) 0.0044(14) -0.0037(15) C14 0.0203(16) 0.028(2) 0.0296(18) 0.0028(15) 0.0069(13) -0.0007(14) C15 0.0296(18) 0.030(2) 0.0305(19) 0.0013(16) 0.0017(14) 0.0031(15) C16 0.0346(19) 0.027(2) 0.0309(19) -0.0006(16) 0.0055(15) -0.0031(16) C17 0.046(2) 0.047(3) 0.029(2) -0.0011(19) -0.0071(18) -0.013(2) C18 0.0248(16) 0.0259(19) 0.0244(17) 0.0017(14) 0.0045(13) -0.0017(14) C19 0.0313(19) 0.033(2) 0.0259(18) -0.0009(16) 0.0008(14) -0.0039(16) C20 0.041(2) 0.048(3) 0.0248(19) 0.0055(18) -0.0033(16) -0.007(2) C21 0.046(2) 0.043(3) 0.037(2) 0.014(2) -0.0079(18) 0.001(2) C22 0.045(2) 0.030(2) 0.044(2) 0.0049(19) 0.0039(18) 0.0089(18) C23 0.038(2) 0.031(2) 0.0277(19) 0.0016(16) 0.0044(15) 0.0051(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 I4 2.5909(7) . ? Zn1 I3 2.5963(7) . ? Zn1 I2 2.6340(10) . ? Zn1 I1 2.6465(7) . ? N1 C2 1.335(6) . ? N1 C6 1.348(6) . ? N1 C1 1.476(6) . ? N2 C11 1.338(5) . ? N2 C7 1.341(5) . ? N3 C12 1.342(6) . ? N3 C16 1.347(5) . ? N3 C17 1.478(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.368(6) . ? C2 H2A 0.9500 . ? C3 C4 1.397(6) . ? C3 H3A 0.9500 . ? C4 C5 1.394(6) . ? C4 C7 1.481(5) . ? C5 C6 1.360(6) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.399(5) . ? C8 C9 1.385(5) . ? C8 H8A 0.9500 . ? C9 C10 1.396(5) . ? C9 C18 1.483(5) . ? C10 C11 1.386(5) . ? C10 H10A 0.9500 . ? C11 C14 1.490(5) . ? C12 C13 1.374(5) . ? C12 H12A 0.9500 . ? C13 C14 1.393(5) . ? C13 H13A 0.9500 . ? C14 C15 1.387(6) . ? C15 C16 1.366(5) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C23 1.389(6) . ? C18 C19 1.397(5) . ? C19 C20 1.386(6) . ? C19 H19A 0.9500 . ? C20 C21 1.374(7) . ? C20 H20A 0.9500 . ? C21 C22 1.386(7) . ? C21 H21A 0.9500 . ? C22 C23 1.387(6) . ? C22 H22A 0.9500 . ? C23 H23A 0.9500 . ? 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 I4 Zn1 I3 107.52(3) . . ? I4 Zn1 I2 111.22(3) . . ? I3 Zn1 I2 112.97(2) . . ? I4 Zn1 I1 111.10(2) . . ? I3 Zn1 I1 108.91(2) . . ? I2 Zn1 I1 105.13(2) . . ? C2 N1 C6 120.5(4) . . ? C2 N1 C1 120.2(4) . . ? C6 N1 C1 119.2(4) . . ? C11 N2 C7 117.7(3) . . ? C12 N3 C16 120.2(3) . . ? C12 N3 C17 120.8(4) . . ? C16 N3 C17 118.9(4) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.0(4) . . ? N1 C2 H2A 119.5 . . ? C3 C2 H2A 119.5 . . ? C2 C3 C4 119.9(4) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 117.6(4) . . ? C5 C4 C7 120.2(4) . . ? C3 C4 C7 122.1(4) . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? N1 C6 C5 120.9(4) . . ? N1 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? N2 C7 C8 122.5(4) . . ? N2 C7 C4 115.0(3) . . ? C8 C7 C4 122.5(3) . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C8 C9 C10 116.9(3) . . ? C8 C9 C18 123.4(3) . . ? C10 C9 C18 119.7(3) . . ? C11 C10 C9 120.0(4) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? N2 C11 C10 122.9(3) . . ? N2 C11 C14 116.2(3) . . ? C10 C11 C14 120.9(3) . . ? N3 C12 C13 120.9(4) . . ? N3 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C12 C13 C14 120.0(4) . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C15 C14 C13 117.6(3) . . ? C15 C14 C11 121.9(3) . . ? C13 C14 C11 120.4(4) . . ? C16 C15 C14 120.3(4) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? N3 C16 C15 120.9(4) . . ? N3 C16 H16A 119.5 . . ? C15 C16 H16A 119.5 . . ? N3 C17 H17A 109.5 . . ? N3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 118.7(4) . . ? C23 C18 C9 120.6(3) . . ? C19 C18 C9 120.6(4) . . ? C20 C19 C18 119.8(4) . . ? C20 C19 H19A 120.1 . . ? C18 C19 H19A 120.1 . . ? C21 C20 C19 121.0(4) . . ? C21 C20 H20A 119.5 . . ? C19 C20 H20A 119.5 . . ? C20 C21 C22 119.9(4) . . ? C20 C21 H21A 120.0 . . ? C22 C21 H21A 120.0 . . ? C21 C22 C23 119.5(4) . . ? C21 C22 H22A 120.3 . . ? C23 C22 H22A 120.3 . . ? C22 C23 C18 121.1(4) . . ? C22 C23 H23A 119.5 . . ? C18 C23 H23A 119.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.246 _refine_diff_density_min -1.688 _refine_diff_density_rms 0.101 # Attachment 'GQ89R.CIF' data_gq89 _database_code_depnum_ccdc_archive 'CCDC 758784' #TrackingRef 'GQ89R.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H25 N3, C2 H3 N, I4 Zn' _chemical_formula_sum 'C27 H28 I4 N4 Zn' _chemical_formula_weight 981.52 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9794(5) _cell_length_b 16.8570(13) _cell_length_c 23.6586(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.413(5) _cell_angle_gamma 90.00 _cell_volume 3168.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.058 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 4.695 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2553 _exptl_absorpt_correction_T_max 0.7346 _exptl_absorpt_process_details '(Blessing, 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _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 86633 _diffrn_reflns_av_R_equivalents 0.0865 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 30.00 _reflns_number_total 9054 _reflns_number_gt 8937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0251P)^2^+6.4834P] 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 9054 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 Zn1 Zn 0.49258(5) 0.23267(2) 0.190109(15) 0.02789(8) Uani 1 1 d . . . I1 I 0.54526(2) 0.380648(11) 0.161348(8) 0.02785(5) Uani 1 1 d . . . I2 I 0.78211(3) 0.158897(12) 0.201747(10) 0.03582(6) Uani 1 1 d . . . I3 I 0.30152(3) 0.165483(13) 0.107232(10) 0.03930(6) Uani 1 1 d . . . I4 I 0.35438(4) 0.232394(17) 0.284826(10) 0.04778(7) Uani 1 1 d . . . N1 N -0.0619(3) 0.41597(16) 0.24038(10) 0.0286(5) Uani 1 1 d . . . N2 N 0.1244(3) 0.55085(14) 0.07219(10) 0.0255(4) Uani 1 1 d . . . N3 N 0.1307(4) 0.82094(15) -0.00964(12) 0.0355(6) Uani 1 1 d . . . C1 C -0.0355(6) 0.4288(3) 0.34497(15) 0.0500(10) Uani 1 1 d . . . H1A H -0.0886 0.4140 0.3792 0.075 Uiso 1 1 calc R . . H1B H -0.0283 0.4867 0.3426 0.075 Uiso 1 1 calc R . . H1C H 0.0778 0.4060 0.3468 0.075 Uiso 1 1 calc R . . C2 C -0.1397(4) 0.3974(2) 0.29322(14) 0.0380(7) Uani 1 1 d . . . H2A H -0.1517 0.3392 0.2967 0.046 Uiso 1 1 calc R . . H2B H -0.2536 0.4211 0.2912 0.046 Uiso 1 1 calc R . . C3 C -0.0686(5) 0.4907(2) 0.22057(14) 0.0367(7) Uani 1 1 d . . . H3A H -0.1191 0.5308 0.2415 0.044 Uiso 1 1 calc R . . C4 C -0.0039(4) 0.51010(18) 0.17083(13) 0.0330(6) Uani 1 1 d . . . H4A H -0.0092 0.5633 0.1576 0.040 Uiso 1 1 calc R . . C5 C 0.0696(3) 0.45182(16) 0.13958(12) 0.0247(5) Uani 1 1 d . . . C6 C 0.0743(4) 0.37483(17) 0.16108(13) 0.0279(5) Uani 1 1 d . . . H6A H 0.1236 0.3335 0.1409 0.033 Uiso 1 1 calc R . . C7 C 0.0077(4) 0.35843(18) 0.21127(13) 0.0298(6) Uani 1 1 d . . . H7A H 0.0110 0.3057 0.2255 0.036 Uiso 1 1 calc R . . C8 C 0.1378(3) 0.47375(16) 0.08548(12) 0.0240(5) Uani 1 1 d . . . C9 C 0.2090(4) 0.41825(16) 0.05129(12) 0.0254(5) Uani 1 1 d . . . H9A H 0.2162 0.3641 0.0624 0.030 Uiso 1 1 calc R . . C10 C 0.2697(4) 0.44224(16) 0.00078(12) 0.0249(5) Uani 1 1 d . . . C11 C 0.2571(4) 0.52281(17) -0.01225(12) 0.0269(5) Uani 1 1 d . . . H11A H 0.2990 0.5424 -0.0458 0.032 Uiso 1 1 calc R . . C12 C 0.1833(4) 0.57461(16) 0.02395(12) 0.0256(5) Uani 1 1 d . . . C13 C 0.0789(5) 0.7901(2) 0.03784(16) 0.0409(8) Uani 1 1 d . . . H13A H 0.0315 0.8240 0.0642 0.049 Uiso 1 1 calc R . . C14 C 0.0929(5) 0.71066(19) 0.04918(15) 0.0378(7) Uani 1 1 d . . . H14A H 0.0543 0.6898 0.0830 0.045 Uiso 1 1 calc R . . C15 C 0.1633(4) 0.66043(17) 0.01140(12) 0.0286(5) Uani 1 1 d . . . C16 C 0.2124(6) 0.6937(2) -0.03774(15) 0.0476(10) Uani 1 1 d . . . H16A H 0.2589 0.6611 -0.0651 0.057 Uiso 1 1 calc R . . C17 C 0.1943(7) 0.7735(2) -0.04719(16) 0.0512(11) Uani 1 1 d . . . H17A H 0.2280 0.7956 -0.0813 0.061 Uiso 1 1 calc R . . C18 C 0.1190(5) 0.90735(19) -0.02117(17) 0.0435(8) Uani 1 1 d . . . H18A H 0.0330 0.9309 0.0013 0.052 Uiso 1 1 calc R . . H18B H 0.0826 0.9160 -0.0619 0.052 Uiso 1 1 calc R . . C19 C 0.2838(6) 0.9479(2) -0.0065(2) 0.0580(11) Uani 1 1 d . . . H19A H 0.3179 0.9413 0.0342 0.087 Uiso 1 1 calc R . . H19B H 0.2724 1.0045 -0.0154 0.087 Uiso 1 1 calc R . . H19C H 0.3693 0.9245 -0.0285 0.087 Uiso 1 1 calc R . . C20 C 0.3423(4) 0.38539(17) -0.03766(12) 0.0267(5) Uani 1 1 d . . . C21 C 0.3655(7) 0.3063(2) -0.02273(19) 0.0536(11) Uani 1 1 d . . . H21A H 0.3340 0.2884 0.0128 0.064 Uiso 1 1 calc R . . C22 C 0.4342(7) 0.2528(2) -0.0589(2) 0.0591(12) Uani 1 1 d . . . H22A H 0.4474 0.1987 -0.0481 0.071 Uiso 1 1 calc R . . C23 C 0.4829(5) 0.2777(2) -0.11010(16) 0.0435(8) Uani 1 1 d . . . H23A H 0.5285 0.2410 -0.1350 0.052 Uiso 1 1 calc R . . C24 C 0.4652(7) 0.3560(2) -0.12492(16) 0.0528(11) Uani 1 1 d . . . H24A H 0.5017 0.3741 -0.1598 0.063 Uiso 1 1 calc R . . C25 C 0.3943(6) 0.4087(2) -0.08936(15) 0.0473(9) Uani 1 1 d . . . H25A H 0.3808 0.4626 -0.1007 0.057 Uiso 1 1 calc R . . C100 C 0.4462(5) 0.4718(2) 0.34193(18) 0.0450(9) Uani 1 1 d . . . N100 N 0.5111(6) 0.4493(2) 0.38390(18) 0.0609(10) Uani 1 1 d . . . C101 C 0.3670(5) 0.4998(3) 0.28839(17) 0.0505(9) Uani 1 1 d . . . H10A H 0.4469 0.5325 0.2696 0.076 Uiso 1 1 calc R . . H10B H 0.2679 0.5317 0.2950 0.076 Uiso 1 1 calc R . . H10C H 0.3324 0.4544 0.2642 0.076 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 Zn1 0.03132(17) 0.02503(16) 0.02800(16) 0.00379(12) 0.00635(12) -0.00012(12) I1 0.02939(9) 0.02274(9) 0.03146(9) 0.00379(6) 0.00314(7) -0.00032(6) I2 0.03290(10) 0.02810(10) 0.04743(12) 0.01193(8) 0.00893(8) 0.00378(7) I3 0.04631(13) 0.03177(11) 0.03875(11) 0.00090(8) -0.00155(9) -0.00972(9) I4 0.05821(15) 0.05430(15) 0.03395(11) 0.01458(10) 0.02077(10) 0.01688(12) N1 0.0275(11) 0.0313(12) 0.0275(11) 0.0009(9) 0.0052(9) -0.0005(9) N2 0.0277(11) 0.0209(10) 0.0281(11) 0.0005(8) 0.0027(9) 0.0029(8) N3 0.0498(16) 0.0188(11) 0.0371(13) 0.0025(10) -0.0004(12) 0.0020(11) C1 0.077(3) 0.043(2) 0.0300(16) 0.0024(14) 0.0062(17) -0.0071(19) C2 0.0373(16) 0.0472(19) 0.0308(14) 0.0040(13) 0.0104(12) -0.0005(14) C3 0.0460(18) 0.0290(14) 0.0370(15) -0.0018(12) 0.0147(13) 0.0081(13) C4 0.0426(16) 0.0238(13) 0.0342(14) 0.0005(11) 0.0121(12) 0.0047(12) C5 0.0243(11) 0.0215(11) 0.0285(12) 0.0002(9) 0.0037(9) -0.0001(9) C6 0.0270(12) 0.0223(12) 0.0350(14) 0.0005(10) 0.0067(10) 0.0023(10) C7 0.0323(14) 0.0237(12) 0.0345(14) 0.0019(11) 0.0083(11) 0.0003(11) C8 0.0245(11) 0.0204(11) 0.0268(12) 0.0013(9) 0.0001(9) 0.0016(9) C9 0.0272(12) 0.0212(11) 0.0272(12) 0.0003(9) 0.0006(10) 0.0020(10) C10 0.0257(12) 0.0223(12) 0.0264(12) -0.0024(9) 0.0003(9) 0.0008(10) C11 0.0333(13) 0.0209(11) 0.0264(12) 0.0019(9) 0.0028(10) 0.0007(10) C12 0.0289(12) 0.0199(11) 0.0275(12) 0.0016(9) 0.0004(10) 0.0012(10) C13 0.054(2) 0.0234(14) 0.0469(18) 0.0004(13) 0.0159(16) 0.0069(14) C14 0.054(2) 0.0233(13) 0.0386(16) 0.0043(12) 0.0161(14) 0.0052(13) C15 0.0380(15) 0.0212(12) 0.0266(12) 0.0002(9) 0.0033(11) 0.0012(11) C16 0.088(3) 0.0246(15) 0.0331(16) 0.0005(12) 0.0207(18) 0.0037(17) C17 0.094(3) 0.0266(15) 0.0351(17) 0.0063(13) 0.0181(19) 0.0040(18) C18 0.061(2) 0.0188(13) 0.0499(19) 0.0083(13) 0.0004(17) 0.0051(14) C19 0.060(3) 0.0305(18) 0.082(3) 0.0068(19) -0.001(2) -0.0035(17) C20 0.0300(13) 0.0232(12) 0.0268(12) -0.0022(9) 0.0018(10) -0.0003(10) C21 0.088(3) 0.0271(16) 0.052(2) 0.0056(15) 0.039(2) 0.0135(18) C22 0.093(4) 0.0301(17) 0.060(3) 0.0002(17) 0.037(2) 0.012(2) C23 0.058(2) 0.0345(16) 0.0394(17) -0.0141(14) 0.0150(16) 0.0010(16) C24 0.089(3) 0.0397(19) 0.0327(17) -0.0043(14) 0.0218(19) 0.005(2) C25 0.084(3) 0.0277(15) 0.0323(16) 0.0007(12) 0.0176(17) 0.0070(17) C100 0.051(2) 0.0353(17) 0.052(2) -0.0152(15) 0.0202(17) -0.0125(15) N100 0.087(3) 0.0401(18) 0.057(2) -0.0049(16) 0.014(2) -0.0111(19) C101 0.047(2) 0.058(2) 0.048(2) -0.0159(18) 0.0094(16) -0.0109(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 I4 2.5892(4) . ? Zn1 I2 2.6152(4) . ? Zn1 I3 2.6244(4) . ? Zn1 I1 2.6299(4) . ? N1 C7 1.340(4) . ? N1 C3 1.343(4) . ? N1 C2 1.481(4) . ? N2 C12 1.336(4) . ? N2 C8 1.339(3) . ? N3 C17 1.331(5) . ? N3 C13 1.338(5) . ? N3 C18 1.483(4) . ? C1 C2 1.509(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.368(4) . ? C3 H3A 0.9500 . ? C4 C5 1.392(4) . ? C4 H4A 0.9500 . ? C5 C6 1.393(4) . ? C5 C8 1.484(4) . ? C6 C7 1.374(4) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 C9 1.392(4) . ? C9 C10 1.391(4) . ? C9 H9A 0.9500 . ? C10 C11 1.394(4) . ? C10 C20 1.477(4) . ? C11 C12 1.392(4) . ? C11 H11A 0.9500 . ? C12 C15 1.482(4) . ? C13 C14 1.368(4) . ? C13 H13A 0.9500 . ? C14 C15 1.388(4) . ? C14 H14A 0.9500 . ? C15 C16 1.380(4) . ? C16 C17 1.370(5) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19 1.494(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.385(4) . ? C20 C21 1.387(4) . ? C21 C22 1.391(5) . ? C21 H21A 0.9500 . ? C22 C23 1.372(6) . ? C22 H22A 0.9500 . ? C23 C24 1.370(6) . ? C23 H23A 0.9500 . ? C24 C25 1.381(5) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C100 N100 1.141(6) . ? C100 C101 1.441(6) . ? C101 H10A 0.9800 . ? C101 H10B 0.9800 . ? C101 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I4 Zn1 I2 110.621(15) . . ? I4 Zn1 I3 112.397(16) . . ? I2 Zn1 I3 108.578(15) . . ? I4 Zn1 I1 108.490(15) . . ? I2 Zn1 I1 108.487(14) . . ? I3 Zn1 I1 108.167(14) . . ? C7 N1 C3 120.3(3) . . ? C7 N1 C2 120.5(3) . . ? C3 N1 C2 119.1(3) . . ? C12 N2 C8 117.7(2) . . ? C17 N3 C13 119.7(3) . . ? C17 N3 C18 119.2(3) . . ? C13 N3 C18 121.1(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C1 111.6(3) . . ? N1 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? N1 C3 C4 121.2(3) . . ? N1 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C4 C5 C6 117.5(3) . . ? C4 C5 C8 119.3(3) . . ? C6 C5 C8 123.2(3) . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? N1 C7 C6 120.7(3) . . ? N1 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? N2 C8 C9 122.9(3) . . ? N2 C8 C5 114.6(2) . . ? C9 C8 C5 122.5(2) . . ? C10 C9 C8 119.9(3) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? C9 C10 C11 116.7(3) . . ? C9 C10 C20 121.9(3) . . ? C11 C10 C20 121.3(3) . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? N2 C12 C11 122.7(3) . . ? N2 C12 C15 115.1(2) . . ? C11 C12 C15 122.2(3) . . ? N3 C13 C14 121.3(3) . . ? N3 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C16 C15 C14 117.3(3) . . ? C16 C15 C12 122.1(3) . . ? C14 C15 C12 120.6(3) . . ? C17 C16 C15 120.2(3) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? N3 C17 C16 121.5(3) . . ? N3 C17 H17A 119.3 . . ? C16 C17 H17A 119.3 . . ? N3 C18 C19 111.6(3) . . ? N3 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? N3 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 117.0(3) . . ? C25 C20 C10 121.8(3) . . ? C21 C20 C10 121.2(3) . . ? C20 C21 C22 121.2(4) . . ? C20 C21 H21A 119.4 . . ? C22 C21 H21A 119.4 . . ? C23 C22 C21 120.4(4) . . ? C23 C22 H22A 119.8 . . ? C21 C22 H22A 119.8 . . ? C24 C23 C22 119.3(3) . . ? C24 C23 H23A 120.3 . . ? C22 C23 H23A 120.3 . . ? C23 C24 C25 120.2(4) . . ? C23 C24 H24A 119.9 . . ? C25 C24 H24A 119.9 . . ? C24 C25 C20 122.0(3) . . ? C24 C25 H25A 119.0 . . ? C20 C25 H25A 119.0 . . ? N100 C100 C101 178.9(5) . . ? C100 C101 H10A 109.5 . . ? C100 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? C100 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.009 _refine_diff_density_min -1.442 _refine_diff_density_rms 0.107 # Attachment 'GQ94.CIF' data_gq94 _database_code_depnum_ccdc_archive 'CCDC 758785' #TrackingRef 'GQ94.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H21 N3 O4 Zn' _chemical_formula_sum 'C25 H21 N3 O4 Zn' _chemical_formula_weight 492.84 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.1857(16) _cell_length_b 19.653(4) _cell_length_c 13.625(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.45(3) _cell_angle_gamma 90.00 _cell_volume 2155.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 1.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6501 _exptl_absorpt_correction_T_max 0.8431 _exptl_absorpt_process_details '(Blessing, 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _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 52782 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4906 _reflns_number_gt 4829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+1.2882P] 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 4906 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0701 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.805527(19) 0.796728(8) 0.588827(11) 0.01814(6) Uani 1 1 d . . . N1 N 0.93324(14) 0.71432(6) 0.54875(9) 0.0191(2) Uani 1 1 d . . . N2 N 1.25564(14) 0.50036(6) 0.53821(9) 0.0189(2) Uani 1 1 d . . . N3 N 1.55889(14) 0.33426(6) 0.78043(9) 0.0196(2) Uani 1 1 d . . . C1 C 1.00993(18) 0.66956(7) 0.61619(10) 0.0217(3) Uani 1 1 d . . . H1A H 1.0093 0.6775 0.6849 0.026 Uiso 1 1 calc R . . C2 C 1.08948(18) 0.61256(7) 0.58971(10) 0.0217(3) Uani 1 1 d . . . H2A H 1.1410 0.5818 0.6397 0.026 Uiso 1 1 calc R . . C3 C 1.09465(16) 0.59985(7) 0.48981(10) 0.0178(2) Uani 1 1 d . . . C4 C 1.01671(18) 0.64672(7) 0.41998(10) 0.0227(3) Uani 1 1 d . . . H4A H 1.0180 0.6405 0.3510 0.027 Uiso 1 1 calc R . . C5 C 0.93763(19) 0.70230(7) 0.45200(11) 0.0227(3) Uani 1 1 d . . . H5A H 0.8838 0.7335 0.4035 0.027 Uiso 1 1 calc R . . C6 C 1.17922(16) 0.53784(7) 0.46166(10) 0.0182(2) Uani 1 1 d . . . C7 C 1.17577(17) 0.51986(7) 0.36239(10) 0.0201(3) Uani 1 1 d . . . H7A H 1.1185 0.5475 0.3101 0.024 Uiso 1 1 calc R . . C8 C 1.25700(17) 0.46102(7) 0.34047(10) 0.0191(3) Uani 1 1 d . . . C9 C 1.33931(17) 0.42288(7) 0.42115(10) 0.0196(3) Uani 1 1 d . . . H9A H 1.3988 0.3830 0.4098 0.024 Uiso 1 1 calc R . . C10 C 1.33378(16) 0.44351(7) 0.51804(10) 0.0182(2) Uani 1 1 d . . . C11 C 1.48995(19) 0.39574(8) 0.78533(11) 0.0259(3) Uani 1 1 d . . . H11A H 1.4916 0.4156 0.8491 0.031 Uiso 1 1 calc R . . C12 C 1.4170(2) 0.43137(8) 0.70192(11) 0.0265(3) Uani 1 1 d . . . H12A H 1.3690 0.4747 0.7089 0.032 Uiso 1 1 calc R . . C13 C 1.41317(16) 0.40416(7) 0.60748(10) 0.0183(2) Uani 1 1 d . . . C14 C 1.48232(18) 0.33997(7) 0.60212(10) 0.0230(3) Uani 1 1 d . . . H14A H 1.4810 0.3188 0.5393 0.028 Uiso 1 1 calc R . . C15 C 1.55307(19) 0.30738(7) 0.68961(11) 0.0235(3) Uani 1 1 d . . . H15A H 1.6000 0.2636 0.6849 0.028 Uiso 1 1 calc R . . C16 C 1.25232(17) 0.43902(7) 0.23559(10) 0.0207(3) Uani 1 1 d . . . C17 C 1.2051(2) 0.48416(8) 0.15639(11) 0.0289(3) Uani 1 1 d . . . H17A H 1.1768 0.5297 0.1696 0.035 Uiso 1 1 calc R . . C18 C 1.1993(2) 0.46313(9) 0.05871(12) 0.0359(4) Uani 1 1 d . . . H18A H 1.1664 0.4943 0.0055 0.043 Uiso 1 1 calc R . . C19 C 1.2408(2) 0.39727(9) 0.03795(12) 0.0349(4) Uani 1 1 d . . . H19A H 1.2374 0.3831 -0.0291 0.042 Uiso 1 1 calc R . . C20 C 1.2875(2) 0.35217(9) 0.11577(13) 0.0347(4) Uani 1 1 d . . . H20A H 1.3160 0.3067 0.1020 0.042 Uiso 1 1 calc R . . C21 C 1.2931(2) 0.37255(8) 0.21375(11) 0.0278(3) Uani 1 1 d . . . H21A H 1.3250 0.3409 0.2665 0.033 Uiso 1 1 calc R . . C100 C 0.76168(19) 0.86979(7) 0.41056(11) 0.0251(3) Uani 1 1 d . . . C101 C 0.7904(3) 0.93173(9) 0.35079(12) 0.0378(4) Uani 1 1 d . . . H10A H 0.8418 0.9180 0.2943 0.057 Uiso 1 1 calc R . . H10B H 0.8641 0.9634 0.3933 0.057 Uiso 1 1 calc R . . H10C H 0.6839 0.9541 0.3259 0.057 Uiso 1 1 calc R . . O100 O 0.82756(15) 0.87240(5) 0.50331(8) 0.0282(2) Uani 1 1 d . . . O101 O 0.68317(17) 0.82139(6) 0.36992(10) 0.0400(3) Uani 1 1 d . . . C200 C 0.51203(18) 0.79444(7) 0.65394(11) 0.0218(3) Uani 1 1 d . . . C201 C 0.3498(2) 0.76470(10) 0.66931(15) 0.0380(4) Uani 1 1 d . . . H20B H 0.2888 0.7985 0.7013 0.057 Uiso 1 1 calc R . . H20C H 0.3709 0.7244 0.7120 0.057 Uiso 1 1 calc R . . H20D H 0.2838 0.7518 0.6046 0.057 Uiso 1 1 calc R . . O200 O 0.60270(13) 0.75412(5) 0.61196(8) 0.0241(2) Uani 1 1 d . . . O201 O 0.55237(14) 0.85267(6) 0.68002(9) 0.0306(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02204(9) 0.01492(9) 0.01730(9) -0.00154(5) 0.00311(6) -0.00058(5) N1 0.0203(5) 0.0155(5) 0.0217(6) -0.0023(4) 0.0047(4) -0.0005(4) N2 0.0205(5) 0.0159(5) 0.0199(5) 0.0001(4) 0.0028(4) 0.0008(4) N3 0.0205(5) 0.0184(5) 0.0192(5) 0.0011(4) 0.0014(4) 0.0008(4) C1 0.0260(7) 0.0207(6) 0.0185(6) -0.0011(5) 0.0039(5) 0.0002(5) C2 0.0261(7) 0.0193(6) 0.0188(6) 0.0012(5) 0.0017(5) 0.0032(5) C3 0.0186(6) 0.0146(6) 0.0201(6) 0.0001(5) 0.0030(5) -0.0003(5) C4 0.0316(7) 0.0197(6) 0.0173(6) 0.0020(5) 0.0059(5) 0.0052(5) C5 0.0294(7) 0.0181(6) 0.0205(7) 0.0024(5) 0.0042(5) 0.0049(5) C6 0.0196(6) 0.0145(6) 0.0205(6) 0.0010(5) 0.0040(5) -0.0001(5) C7 0.0239(6) 0.0167(6) 0.0193(6) 0.0024(5) 0.0034(5) 0.0018(5) C8 0.0217(6) 0.0158(6) 0.0201(6) 0.0007(5) 0.0043(5) -0.0014(5) C9 0.0214(6) 0.0154(6) 0.0220(6) 0.0000(5) 0.0038(5) 0.0019(5) C10 0.0181(6) 0.0152(6) 0.0207(6) 0.0007(5) 0.0023(5) -0.0005(5) C11 0.0340(7) 0.0233(7) 0.0195(6) -0.0019(5) 0.0029(6) 0.0075(6) C12 0.0355(8) 0.0207(6) 0.0222(7) -0.0016(5) 0.0023(6) 0.0095(6) C13 0.0176(6) 0.0167(6) 0.0199(6) 0.0004(5) 0.0012(5) -0.0001(5) C14 0.0297(7) 0.0192(6) 0.0191(6) -0.0021(5) 0.0017(5) 0.0043(5) C15 0.0297(7) 0.0173(6) 0.0223(7) -0.0007(5) 0.0020(6) 0.0056(5) C16 0.0238(6) 0.0180(6) 0.0204(6) 0.0002(5) 0.0046(5) -0.0012(5) C17 0.0416(8) 0.0218(7) 0.0231(7) 0.0023(6) 0.0055(6) 0.0035(6) C18 0.0508(10) 0.0346(9) 0.0215(7) 0.0043(6) 0.0048(7) 0.0018(7) C19 0.0481(10) 0.0367(9) 0.0209(7) -0.0061(6) 0.0089(7) -0.0050(7) C20 0.0516(10) 0.0240(7) 0.0309(8) -0.0059(6) 0.0137(7) 0.0005(7) C21 0.0388(8) 0.0210(7) 0.0246(7) 0.0010(6) 0.0088(6) 0.0038(6) C100 0.0322(7) 0.0212(7) 0.0216(7) 0.0006(5) 0.0038(6) 0.0049(6) C101 0.0596(11) 0.0307(8) 0.0227(7) 0.0070(6) 0.0066(7) 0.0009(8) O100 0.0414(6) 0.0235(5) 0.0191(5) 0.0031(4) 0.0038(4) -0.0040(4) O101 0.0485(7) 0.0271(6) 0.0381(7) -0.0039(5) -0.0092(5) -0.0006(5) C200 0.0227(6) 0.0235(7) 0.0187(6) 0.0020(5) 0.0028(5) -0.0001(5) C201 0.0284(8) 0.0421(10) 0.0465(10) 0.0024(8) 0.0149(7) -0.0054(7) O200 0.0256(5) 0.0198(5) 0.0280(5) -0.0031(4) 0.0080(4) -0.0023(4) O201 0.0346(6) 0.0244(5) 0.0339(6) -0.0064(4) 0.0088(5) -0.0010(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O100 1.9179(11) . ? Zn1 O200 1.9357(11) . ? Zn1 N1 2.0545(12) . ? Zn1 N3 2.0572(13) 2_756 ? N1 C1 1.3428(18) . ? N1 C5 1.3461(18) . ? N2 C6 1.3360(17) . ? N2 C10 1.3404(17) . ? N3 C15 1.3384(18) . ? N3 C11 1.3404(18) . ? N3 Zn1 2.0572(13) 2_746 ? C1 C2 1.3764(19) . ? C1 H1A 0.9500 . ? C2 C3 1.3919(19) . ? C2 H2A 0.9500 . ? C3 C4 1.3930(19) . ? C3 C6 1.4859(18) . ? C4 C5 1.3803(19) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.3932(19) . ? C7 C8 1.3930(19) . ? C7 H7A 0.9500 . ? C8 C9 1.3984(19) . ? C8 C16 1.4868(19) . ? C9 C10 1.3895(19) . ? C9 H9A 0.9500 . ? C10 C13 1.4895(18) . ? C11 C12 1.376(2) . ? C11 H11A 0.9500 . ? C12 C13 1.3885(19) . ? C12 H12A 0.9500 . ? C13 C14 1.3900(19) . ? C14 C15 1.384(2) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C21 1.394(2) . ? C16 C17 1.396(2) . ? C17 C18 1.386(2) . ? C17 H17A 0.9500 . ? C18 C19 1.380(3) . ? C18 H18A 0.9500 . ? C19 C20 1.382(2) . ? C19 H19A 0.9500 . ? C20 C21 1.387(2) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C100 O101 1.223(2) . ? C100 O100 1.2818(18) . ? C100 C101 1.507(2) . ? C101 H10A 0.9800 . ? C101 H10B 0.9800 . ? C101 H10C 0.9800 . ? C200 O201 1.2256(18) . ? C200 O200 1.2884(18) . ? C200 C201 1.500(2) . ? C201 H20B 0.9800 . ? C201 H20C 0.9800 . ? C201 H20D 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O100 Zn1 O200 127.76(5) . . ? O100 Zn1 N1 109.96(5) . . ? O200 Zn1 N1 101.25(5) . . ? O100 Zn1 N3 98.78(5) . 2_756 ? O200 Zn1 N3 110.98(5) . 2_756 ? N1 Zn1 N3 106.99(5) . 2_756 ? C1 N1 C5 117.58(12) . . ? C1 N1 Zn1 122.13(9) . . ? C5 N1 Zn1 120.26(9) . . ? C6 N2 C10 118.22(12) . . ? C15 N3 C11 117.21(12) . . ? C15 N3 Zn1 125.61(10) . 2_746 ? C11 N3 Zn1 116.49(10) . 2_746 ? N1 C1 C2 122.58(13) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? C1 C2 C3 120.14(13) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C2 C3 C4 117.25(12) . . ? C2 C3 C6 119.85(12) . . ? C4 C3 C6 122.89(12) . . ? C5 C4 C3 119.36(13) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? N1 C5 C4 123.08(13) . . ? N1 C5 H5A 118.5 . . ? C4 C5 H5A 118.5 . . ? N2 C6 C7 122.83(12) . . ? N2 C6 C3 115.13(12) . . ? C7 C6 C3 122.02(12) . . ? C8 C7 C6 119.49(13) . . ? C8 C7 H7A 120.3 . . ? C6 C7 H7A 120.3 . . ? C7 C8 C9 117.20(12) . . ? C7 C8 C16 121.16(12) . . ? C9 C8 C16 121.62(12) . . ? C10 C9 C8 119.76(12) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? N2 C10 C9 122.47(12) . . ? N2 C10 C13 114.76(12) . . ? C9 C10 C13 122.77(12) . . ? N3 C11 C12 122.78(13) . . ? N3 C11 H11A 118.6 . . ? C12 C11 H11A 118.6 . . ? C11 C12 C13 120.18(13) . . ? C11 C12 H12A 119.9 . . ? C13 C12 H12A 119.9 . . ? C12 C13 C14 117.22(12) . . ? C12 C13 C10 119.42(12) . . ? C14 C13 C10 123.35(12) . . ? C15 C14 C13 119.04(13) . . ? C15 C14 H14A 120.5 . . ? C13 C14 H14A 120.5 . . ? N3 C15 C14 123.55(13) . . ? N3 C15 H15A 118.2 . . ? C14 C15 H15A 118.2 . . ? C21 C16 C17 118.29(13) . . ? C21 C16 C8 120.82(13) . . ? C17 C16 C8 120.88(13) . . ? C18 C17 C16 120.61(15) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C19 C18 C17 120.62(15) . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C18 C19 C20 119.23(15) . . ? C18 C19 H19A 120.4 . . ? C20 C19 H19A 120.4 . . ? C19 C20 C21 120.65(15) . . ? C19 C20 H20A 119.7 . . ? C21 C20 H20A 119.7 . . ? C20 C21 C16 120.60(14) . . ? C20 C21 H21A 119.7 . . ? C16 C21 H21A 119.7 . . ? O101 C100 O100 124.76(15) . . ? O101 C100 C101 120.29(14) . . ? O100 C100 C101 114.94(14) . . ? C100 C101 H10A 109.5 . . ? C100 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? C100 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? C100 O100 Zn1 119.92(10) . . ? O201 C200 O200 123.80(14) . . ? O201 C200 C201 121.48(14) . . ? O200 C200 C201 114.72(13) . . ? C200 C201 H20B 109.5 . . ? C200 C201 H20C 109.5 . . ? H20B C201 H20C 109.5 . . ? C200 C201 H20D 109.5 . . ? H20B C201 H20D 109.5 . . ? H20C C201 H20D 109.5 . . ? C200 O200 Zn1 112.73(9) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.354 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.049 # Attachment 'Gq85.cif' data_Gq85 _database_code_depnum_ccdc_archive 'CCDC 758786' #TrackingRef 'Gq85.cif' _audit_creation_date 09-11-11 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 'gq85_123k_0ma in C2/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 26.1802(6) _cell_length_b 15.2942(6) _cell_length_c 8.0478(2) _cell_angle_alpha 90 _cell_angle_beta 107.449(2) _cell_angle_gamma 90 _cell_volume 3074.10(16) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zn 0.2839 1.4301 14.0743 3.2655 7.0318 0.2333 5.1652 10.3163 2.4100 58.7097 1.3041 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C25 H21 Cl1 N3 O4 Zn1 # Dc = 1.14 Fooo = 1434.40 Mu = 9.14 M = 264.15 # Found Formula = C29.30 H27.60 Cl0.60 N3 O8 Zn2 # Dc = 1.52 FOOO = 1434.40 Mu = 16.65 M = 350.89 _chemical_formula_sum 'C29.30 H27.60 Cl0.60 N3 O8 Zn2' _chemical_formula_moiety 'C29 H27 N3 O8 Zn2, 0.3(C H2 Cl2)' _chemical_compound_source ? _chemical_formula_weight 701.79 _cell_measurement_reflns_used 9270 _cell_measurement_theta_min 4 _cell_measurement_theta_max 30 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.26 _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1434.400 _exptl_absorpt_coefficient_mu 1.665 # Sheldrick geometric approximatio 0.77 0.86 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.86 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 27652 _reflns_number_total 4315 _diffrn_reflns_av_R_equivalents 0.036 # Number of reflections with Friedels Law is 4315 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4313 _diffrn_reflns_theta_min 1.631 _diffrn_reflns_theta_max 29.578 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.578 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -36 _reflns_limit_h_max 34 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 1.69 _oxford_diffrn_Wilson_scale 432.24 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.42 _refine_diff_density_max 0.63 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 2956 _refine_ls_number_restraints 413 _refine_ls_number_parameters 245 _oxford_refine_ls_R_factor_ref 0.0300 _refine_ls_wR_factor_ref 0.0300 _refine_ls_goodness_of_fit_ref 1.0449 _refine_ls_shift/su_max 0.000601 # The values computed from all data _oxford_reflns_number_all 4306 _refine_ls_R_factor_all 0.0489 _refine_ls_wR_factor_all 0.0566 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3358 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_gt 0.0323 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.157 0.124 0.625E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint # start Validation Reply Form _vrf_PLAT220_1 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 7.83 Ratio RESPONSE: Disorder model with split atoms applied, this improved the model, but the U-values are still high. ; _vrf_PLAT432_1 ; PROBLEM: Short Inter X...Y Contact C16 .. C19 .. 2.71 Ang. RESPONSE: Atoms involved are partially occupied. ; # end Validation Reply Form 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Zn1 Zn 0.289767(9) -0.192710(14) -0.38724(3) 0.0215 1.0000 Uani . . . . . . . O1 O 0.25085(6) -0.10334(9) -0.56732(19) 0.0307 1.0000 Uani . . . . . . . O2 O 0.18799(7) -0.18996(10) -0.73349(19) 0.0391 1.0000 Uani . . . . . . . C1 C 0.21079(8) -0.11769(13) -0.6959(3) 0.0266 1.0000 Uani . . . . . . . C2 C 0.18874(11) -0.04155(15) -0.8154(3) 0.0457 1.0000 Uani . . . . . . . O3 O 0.33287(6) -0.22689(10) -0.5533(2) 0.0298 1.0000 Uani . . . . . . . O4 O 0.27105(6) -0.31398(12) -0.7221(2) 0.0399 1.0000 Uani . . . . . . . C3 C 0.31561(9) -0.27716(14) -0.6811(3) 0.0295 1.0000 Uani . . . . . . . C4 C 0.35203(13) -0.2962(2) -0.7902(4) 0.0621 1.0000 Uani . . . . . . . N1 N 0.34372(6) -0.11406(10) -0.21812(19) 0.0198 1.0000 Uani . . . . . . . N2 N 0.5000 0.00134(13) 0.2500 0.0153 1.0000 Uani S T . . . . . C5 C 0.38627(8) -0.14910(12) -0.0995(2) 0.0233 1.0000 Uani . . . . . . . C6 C 0.42458(7) -0.09898(12) 0.0163(2) 0.0216 1.0000 Uani . . . . . . . C7 C 0.41952(6) -0.00819(12) 0.0123(2) 0.0150 1.0000 Uani . . . . . . . C8 C 0.37461(7) 0.02747(12) -0.1083(2) 0.0190 1.0000 Uani . . . . . . . C9 C 0.33813(7) -0.02715(12) -0.2204(2) 0.0202 1.0000 Uani . . . . . . . C10 C 0.46127(6) 0.04618(11) 0.1348(2) 0.0154 1.0000 Uani . . . . . . . C11 C 0.45998(7) 0.13723(12) 0.1300(2) 0.0227 1.0000 Uani . . . . . . . C12 C 0.5000 0.18436(18) 0.2500 0.0261 1.0000 Uani DS TU . . . . . C13 C 0.49919(16) 0.28188(16) 0.2646(11) 0.0449 0.5000 Uani D U . . . . . C14 C 0.4507(2) 0.3271(3) 0.2074(8) 0.0386 0.5000 Uani D U . . . . . C15 C 0.4499(3) 0.4176(4) 0.2210(9) 0.0749 0.5000 Uani D U . . . . . C16 C 0.4975(4) 0.4631(2) 0.2895(10) 0.1185 0.5000 Uani D U . . . . . C17 C 0.5460(3) 0.4181(4) 0.3449(10) 0.1263 0.5000 Uani D U . . . . . C18 C 0.5467(2) 0.3275(4) 0.3317(10) 0.0871 0.5000 Uani D U . . . . . Cl1 Cl 0.5510(3) -0.3826(4) 0.4825(8) 0.0713 0.1500 Uani D U . . . . . C19 C 0.4838(3) -0.3649(14) 0.3573(17) 0.0701 0.1500 Uani D U . . . . . Cl2 Cl 0.4824(3) -0.3141(4) 0.1598(7) 0.0706 0.1500 Uani D U . . . . . H21 H 0.1505 -0.0439 -0.8524 0.0621 1.0000 Uiso R . . . . . . H22 H 0.2001 0.0117 -0.7538 0.0620 1.0000 Uiso R . . . . . . H23 H 0.2016 -0.0440 -0.9150 0.0622 1.0000 Uiso R . . . . . . H41 H 0.3319 -0.2908 -0.9114 0.1029 1.0000 Uiso R . . . . . . H42 H 0.3804 -0.2545 -0.7600 0.1029 1.0000 Uiso R . . . . . . H43 H 0.3654 -0.3547 -0.7645 0.1032 1.0000 Uiso R . . . . . . H51 H 0.3901 -0.2094 -0.0989 0.0252 1.0000 Uiso R . . . . . . H61 H 0.4535 -0.1251 0.0977 0.0251 1.0000 Uiso R . . . . . . H81 H 0.3693 0.0883 -0.1161 0.0221 1.0000 Uiso R . . . . . . H91 H 0.3082 -0.0025 -0.3007 0.0228 1.0000 Uiso R . . . . . . H111 H 0.4326 0.1659 0.0470 0.0243 1.0000 Uiso R . . . . . . H141 H 0.4184 0.2963 0.1627 0.0430 0.5000 Uiso R . . . . . . H151 H 0.4173 0.4480 0.1851 0.0684 0.5000 Uiso R . . . . . . H161 H 0.4971 0.5244 0.2987 0.0916 0.5000 Uiso R . . . . . . H171 H 0.5783 0.4490 0.3885 0.0938 0.5000 Uiso R . . . . . . H181 H 0.5794 0.2971 0.3673 0.0686 0.5000 Uiso R . . . . . . H191 H 0.4664 -0.3289 0.4198 0.0932 0.1500 Uiso R . . . . . . H192 H 0.4661 -0.4197 0.3337 0.0932 0.1500 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02134(10) 0.01849(10) 0.01774(9) -0.00082(9) -0.00465(7) -0.00754(9) O1 0.0275(7) 0.0241(7) 0.0303(7) 0.0039(6) -0.0068(6) -0.0038(6) O2 0.0454(9) 0.0248(7) 0.0302(7) 0.0069(7) -0.0146(6) -0.0112(7) C1 0.0273(9) 0.0212(9) 0.0239(9) 0.0048(7) -0.0036(7) -0.0022(7) C2 0.0459(13) 0.0280(11) 0.0451(13) 0.0154(10) -0.0137(11) -0.0065(10) O3 0.0289(7) 0.0262(7) 0.0315(7) -0.0081(6) 0.0048(6) -0.0072(6) O4 0.0393(8) 0.0481(10) 0.0328(8) -0.0144(7) 0.0118(7) -0.0253(8) C3 0.0352(11) 0.0270(9) 0.0262(9) -0.0031(8) 0.0089(8) -0.0117(8) C4 0.0711(18) 0.071(2) 0.0609(17) -0.0336(16) 0.0449(15) -0.0416(16) N1 0.0190(7) 0.0200(7) 0.0165(7) -0.0005(6) -0.0006(6) -0.0038(6) N2 0.0128(9) 0.0175(9) 0.0136(9) 0.0000 0.0010(7) 0.0000 C5 0.0259(9) 0.0142(8) 0.0223(8) 0.0018(7) -0.0042(7) -0.0019(7) C6 0.0202(8) 0.0182(8) 0.0193(8) 0.0023(6) -0.0049(7) -0.0010(6) C7 0.0127(7) 0.0188(8) 0.0118(7) -0.0004(6) 0.0010(6) -0.0016(6) C8 0.0158(8) 0.0181(8) 0.0186(8) -0.0022(6) -0.0017(6) 0.0014(6) C9 0.0141(7) 0.0229(9) 0.0184(8) -0.0018(7) -0.0028(6) 0.0000(6) C10 0.0131(7) 0.0179(8) 0.0124(7) -0.0012(6) -0.0005(6) -0.0006(6) C11 0.0179(8) 0.0188(8) 0.0231(9) 0.0018(7) -0.0064(7) 0.0008(7) C12 0.0219(11) 0.0164(12) 0.0304(13) 0.0000 -0.0069(10) 0.0000 C13 0.0387(18) 0.0205(14) 0.052(3) -0.007(3) -0.0223(18) 0.014(4) C14 0.039(3) 0.019(3) 0.045(3) -0.012(2) -0.007(2) 0.015(2) C15 0.073(4) 0.025(3) 0.091(4) -0.017(3) -0.028(4) 0.032(3) C16 0.099(4) 0.027(2) 0.165(7) -0.036(4) -0.057(5) 0.023(4) C17 0.087(4) 0.035(4) 0.178(7) -0.032(4) -0.080(5) 0.014(4) C18 0.060(4) 0.033(4) 0.116(6) -0.019(4) -0.052(4) 0.004(3) Cl1 0.090(3) 0.065(2) 0.067(2) 0.009(2) 0.035(2) 0.020(2) C19 0.091(3) 0.063(2) 0.067(2) 0.016(2) 0.038(2) 0.027(2) Cl2 0.092(3) 0.061(2) 0.069(2) 0.020(2) 0.040(2) 0.036(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.05083(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zn1 . Zn1 4_544 2.9042(4) yes Zn1 . O2 4_544 2.0405(15) yes Zn1 . O4 4_544 2.0396(16) yes Zn1 . O1 . 2.0301(14) yes Zn1 . O3 . 2.0585(16) yes Zn1 . N1 . 2.0351(14) yes O1 . C1 . 1.252(2) yes O2 . C1 . 1.250(2) yes C1 . C2 . 1.510(3) yes C2 . H21 . 0.956 no C2 . H22 . 0.954 no C2 . H23 . 0.959 no O3 . C3 . 1.255(2) yes O4 . C3 . 1.247(2) yes C3 . C4 . 1.505(3) yes C4 . H41 . 0.963 no C4 . H42 . 0.953 no C4 . H43 . 0.960 no N1 . C5 . 1.342(2) yes N1 . C9 . 1.337(2) yes N2 . C10 5_655 1.3396(19) yes N2 . C10 . 1.3396(19) yes C5 . C6 . 1.379(2) yes C5 . H51 . 0.927 no C6 . C7 . 1.394(3) yes C6 . H61 . 0.929 no C7 . C8 . 1.392(2) yes C7 . C10 . 1.487(2) yes C8 . C9 . 1.381(2) yes C8 . H81 . 0.939 no C9 . H91 . 0.933 no C10 . C11 . 1.393(2) yes C11 . C12 . 1.394(2) yes C11 . H111 . 0.930 no C12 . C13 . 1.497(4) yes C13 . C14 . 1.398(5) yes C13 . C18 . 1.387(6) yes C14 . C15 . 1.388(5) yes C14 . H141 . 0.940 no C15 . C16 . 1.389(6) yes C15 . H151 . 0.940 no C16 . C17 . 1.394(6) yes C16 . H161 . 0.940 no C17 . C18 . 1.389(5) yes C17 . H171 . 0.940 no C18 . H181 . 0.940 no Cl1 . C19 . 1.765(8) yes C19 . Cl2 . 1.760(8) yes C19 . H191 . 0.950 no C19 . H192 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Zn1 4_544 Zn1 . O2 4_544 79.38(4) yes Zn1 4_544 Zn1 . O4 4_544 78.09(4) yes O2 4_544 Zn1 . O4 4_544 89.25(8) yes Zn1 4_544 Zn1 . O1 . 81.25(4) yes O2 4_544 Zn1 . O1 . 160.47(6) yes O4 4_544 Zn1 . O1 . 89.12(7) yes Zn1 4_544 Zn1 . O3 . 82.58(4) yes O2 4_544 Zn1 . O3 . 87.26(7) yes O4 4_544 Zn1 . O3 . 160.67(6) yes O1 . Zn1 . O3 . 87.88(6) yes Zn1 4_544 Zn1 . N1 . 176.76(5) yes O2 4_544 Zn1 . N1 . 99.18(6) yes O4 4_544 Zn1 . N1 . 99.03(6) yes O1 . Zn1 . N1 . 100.29(6) yes O3 . Zn1 . N1 . 100.29(6) yes Zn1 . O1 . C1 . 126.07(13) yes Zn1 4_544 O2 . C1 . 127.98(12) yes O1 . C1 . O2 . 125.16(18) yes O1 . C1 . C2 . 117.17(18) yes O2 . C1 . C2 . 117.67(17) yes C1 . C2 . H21 . 109.5 no C1 . C2 . H22 . 109.1 no H21 . C2 . H22 . 109.2 no C1 . C2 . H23 . 109.8 no H21 . C2 . H23 . 109.7 no H22 . C2 . H23 . 109.5 no Zn1 . O3 . C3 . 123.71(14) yes Zn1 4_544 O4 . C3 . 130.73(15) yes O3 . C3 . O4 . 124.9(2) yes O3 . C3 . C4 . 117.5(2) yes O4 . C3 . C4 . 117.7(2) yes C3 . C4 . H41 . 109.0 no C3 . C4 . H42 . 107.7 no H41 . C4 . H42 . 110.3 no C3 . C4 . H43 . 108.0 no H41 . C4 . H43 . 110.6 no H42 . C4 . H43 . 111.2 no Zn1 . N1 . C5 . 120.09(12) yes Zn1 . N1 . C9 . 121.81(12) yes C5 . N1 . C9 . 118.10(15) yes C10 5_655 N2 . C10 . 118.4(2) yes N1 . C5 . C6 . 122.62(17) yes N1 . C5 . H51 . 117.7 no C6 . C5 . H51 . 119.6 no C5 . C6 . C7 . 119.55(15) yes C5 . C6 . H61 . 120.7 no C7 . C6 . H61 . 119.7 no C6 . C7 . C8 . 117.43(15) yes C6 . C7 . C10 . 119.72(14) yes C8 . C7 . C10 . 122.85(16) yes C7 . C8 . C9 . 119.53(17) yes C7 . C8 . H81 . 120.7 no C9 . C8 . H81 . 119.7 no C8 . C9 . N1 . 122.74(16) yes C8 . C9 . H91 . 118.7 no N1 . C9 . H91 . 118.5 no C7 . C10 . N2 . 115.21(15) yes C7 . C10 . C11 . 122.25(15) yes N2 . C10 . C11 . 122.54(16) yes C10 . C11 . C12 . 119.38(17) yes C10 . C11 . H111 . 119.9 no C12 . C11 . H111 . 120.7 no C11 . C12 . C13 . 123.0(2) yes C12 . C13 . C14 . 120.02(8) yes C12 . C13 . C18 . 120.01(8) yes C14 . C13 . C18 . 119.96(7) yes C13 . C14 . C15 . 119.98(8) yes C13 . C14 . H141 . 120.1 no C15 . C14 . H141 . 119.9 no C14 . C15 . C16 . 119.98(8) yes C14 . C15 . H151 . 120.1 no C16 . C15 . H151 . 119.9 no C15 . C16 . C17 . 120.03(8) yes C15 . C16 . H161 . 120.1 no C17 . C16 . H161 . 119.8 no C16 . C17 . C18 . 120.02(8) yes C16 . C17 . H171 . 120.1 no C18 . C17 . H171 . 119.8 no C17 . C18 . C13 . 120.01(8) yes C17 . C18 . H181 . 120.2 no C13 . C18 . H181 . 119.8 no Cl1 . C19 . Cl2 . 109.3(4) yes Cl1 . C19 . H191 . 109.9 no Cl2 . C19 . H191 . 109.8 no Cl1 . C19 . H192 . 108.8 no Cl2 . C19 . H192 . 109.4 no H191 . C19 . H192 . 109.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C5 . H51 . O2 4_544 121 0.93 2.59 3.175(6) yes C8 . H81 . O3 6_555 155 0.94 2.44 3.314(6) yes C16 . H161 . C19 1_565 163 0.94 1.82 2.731(6) yes C16 . H161 . C19 5_665 134 0.94 2.25 2.983(6) yes C14 5_655 H181 . O3 2_655 173 0.95 2.57 3.519(6) yes C18 . H181 . O3 2_655 163 0.94 2.57 3.481(6) yes C19 . H191 . C13 2_656 128 0.95 2.53 3.203(6) yes C19 . H191 . C14 6_555 138 0.95 2.47 3.240(6) yes C19 . H191 . C18 2_656 138 0.95 2.13 2.903(6) yes C19 . H192 . C16 1_545 128 0.95 2.05 2.731(6) yes C19 . H192 . C16 5_645 121 0.95 2.38 2.983(6) yes