data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address J.L.Cryder ; Department of Chemistry and Biochemistry University of San Diego San Diego, CA 92110 ; A.J.Killgore ; Department of Chemistry Western Washington University Bellingham, WA 98225-9150 ; C.Moore ; Department of Chemistry and Biochemistry University of California, San Diego La Jolla, CA 92093 ; J.A.Golen ; Department of Chemistry and Biochemistry University of Massachusetts Dartmouth North Dartmouth, MA 02747 ; A.L.Rheingold ; Department of Chemistry and Biochemistry University of California, San Diego La Jolla, CA 92093 ; ; C.J.A.Daley ; ; Department of Chemistry and Biochemistry University of San Diego San Diego, CA 92110 ; _publ_contact_author_address ; Department of Chemistry and Biochemistry University of San Diego San Diego, CA 92110 ; _publ_contact_author_email cjdaley@sandiego.edu #TrackingRef '1723_web_deposit_cif_file_0_ChristopherJ.A.Daley_1278646485.cif' #------------------ SUBMISSION DETAILS --------------------------------------# # Name and address of author for correspondence _publ_contact_author_name 'Daley, Christopher J.A.' _publ_section_title ; Novel Metal Complexes Containing a Chiral Trinitrogen Isoindoline-based Pincer Ligand: In-Situ Synthesis and Structural Characterization. ; data_daley02b/Zn((R,R)-5)2 _database_code_depnum_ccdc_archive 'CCDC 783916' _publ_section_title_footnote ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C57 H50 N10 O5.67 Zn' _chemical_formula_weight 1031.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P3(1)21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' 'y, x, -z' _cell_length_a 19.3476(6) _cell_length_b 19.3476(6) _cell_length_c 11.5041(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3729.4(2) _cell_formula_units_Z 3 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9869 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 65.45 _exptl_crystal_description Rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1612 _exptl_absorpt_coefficient_mu 1.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6206 _exptl_absorpt_correction_T_max 0.8695 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 22080 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 65.78 _reflns_number_total 4172 _reflns_number_gt 4021 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; SQUEEZE found one void containing 5 disordered acetone molecules. Their formula was added to the formula for the unit-cell and the electron density removed. 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^)+(0.0357P)^2^+0.3966P] 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 _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.003(17) _refine_ls_number_reflns 4172 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.016 609 141 ' ' _platon_squeeze_details ; SQUEEZE found one void containing 5 disordered acetone molecules. Their formula was added to the formula for the unit-cell and the electron density removed. ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.0000 0.449165(16) 0.1667 0.02957(10) Uani 1 2 d S . . N1 N 0.09049(10) 0.56761(9) 0.22572(13) 0.0410(4) Uani 1 1 d . . . N2 N 0.17804(10) 0.61415(9) 0.06013(13) 0.0368(4) Uani 1 1 d . . . N3 N 0.06664(8) 0.48509(9) 0.00997(11) 0.0292(3) Uani 1 1 d . . . N4 N -0.01307(9) 0.37185(10) -0.11529(13) 0.0345(4) Uani 1 1 d . . . N5 N -0.07228(9) 0.33841(9) 0.07624(13) 0.0333(3) Uani 1 1 d . . . O1 O 0.21904(9) 0.66418(8) 0.23975(11) 0.0463(4) Uani 1 1 d . . . O2 O -0.13379(8) 0.26546(8) -0.08226(11) 0.0465(4) Uani 1 1 d . . . C1 C 0.0931(6) 0.5938(9) 0.3432(11) 0.0378(18) Uani 0.609(10) 1 d P A 1 H1 H 0.0706 0.5472 0.3975 0.045 Uiso 0.609(10) 1 calc PR A 1 C1B C 0.1129(10) 0.5950(15) 0.3549(19) 0.0378(18) Uani 0.391(10) 1 d P A 2 H1B H 0.1022 0.5476 0.4029 0.045 Uiso 0.391(10) 1 calc PR A 2 C2 C 0.19146(14) 0.64807(14) 0.35870(17) 0.0491(5) Uani 1 1 d . A . H2A H 0.2070 0.6981 0.4016 0.059 Uiso 0.609(10) 1 calc PR A 1 H2B H 0.2128 0.6178 0.3999 0.059 Uiso 0.609(10) 1 calc PR A 1 H2C H 0.2230 0.6300 0.4038 0.059 Uiso 0.391(10) 1 d PR A 2 H2D H 0.1972 0.6969 0.3957 0.059 Uiso 0.391(10) 1 d PR A 2 C3 C 0.15681(13) 0.61006(11) 0.17422(16) 0.0383(5) Uani 1 1 d . A . C4 C 0.13424(11) 0.55654(11) -0.01101(15) 0.0310(4) Uani 1 1 d . A . C5 C 0.15751(11) 0.56191(11) -0.13431(16) 0.0323(4) Uani 1 1 d . . . C6 C 0.21896(12) 0.62288(12) -0.19674(16) 0.0378(4) Uani 1 1 d . A . H6 H 0.2557 0.6721 -0.1611 0.045 Uiso 1 1 calc R . . C7 C 0.22442(13) 0.60882(13) -0.31412(17) 0.0416(5) Uani 1 1 d . . . H7 H 0.2651 0.6495 -0.3605 0.050 Uiso 1 1 calc R A . C8 C 0.17101(11) 0.53596(13) -0.36417(15) 0.0394(4) Uani 1 1 d . A . H8 H 0.1767 0.5275 -0.4441 0.047 Uiso 1 1 calc R . . C9 C 0.10967(11) 0.47527(12) -0.30096(15) 0.0354(4) Uani 1 1 d . . . H9 H 0.0730 0.4257 -0.3357 0.042 Uiso 1 1 calc R A . C10 C 0.10451(10) 0.49072(11) -0.18404(15) 0.0312(4) Uani 1 1 d . A . C11 C 0.04689(10) 0.44241(11) -0.09238(14) 0.0298(4) Uani 1 1 d . A . C12 C -0.06985(11) 0.32864(11) -0.03459(16) 0.0346(4) Uani 1 1 d . A . C13 C -0.19015(13) 0.22494(13) 0.01064(17) 0.0462(5) Uani 1 1 d . A . H13A H -0.2002 0.1698 0.0203 0.055 Uiso 1 1 calc R . . H13B H -0.2415 0.2229 -0.0051 0.055 Uiso 1 1 calc R . . C14 C -0.14999(11) 0.27512(12) 0.11922(16) 0.0384(4) Uani 1 1 d . A . H14 H -0.1816 0.3000 0.1465 0.046 Uiso 1 1 calc R . . C21 C -0.14228(12) 0.22828(12) 0.21809(17) 0.0410(5) Uani 1 1 d . . . C22 C -0.09631(14) 0.19356(15) 0.2050(2) 0.0545(6) Uani 1 1 d . A . H22 H -0.0683 0.2004 0.1342 0.065 Uiso 1 1 calc R . . C23 C -0.08985(16) 0.14850(19) 0.2932(3) 0.0721(8) Uani 1 1 d . . . H23 H -0.0582 0.1241 0.2833 0.087 Uiso 1 1 calc R A . C24 C -0.13114(16) 0.13957(17) 0.3979(2) 0.0687(8) Uani 1 1 d . A . H24 H -0.1266 0.1096 0.4598 0.082 Uiso 1 1 calc R . . C25 C -0.17664(16) 0.17306(15) 0.4107(2) 0.0601(7) Uani 1 1 d . . . H25 H -0.2051 0.1657 0.4812 0.072 Uiso 1 1 calc R A . C26 C -0.18272(14) 0.21830(13) 0.32233(18) 0.0492(5) Uani 1 1 d . A . H26 H -0.2145 0.2426 0.3329 0.059 Uiso 1 1 calc R . . C15 C 0.0527(2) 0.6438(2) 0.3630(3) 0.0399(15) Uani 0.609(10) 1 d PG A 1 C16 C 0.00865(19) 0.6315(3) 0.4641(3) 0.0455(13) Uani 0.609(10) 1 d PG A 1 H16 H 0.0013 0.5906 0.5169 0.055 Uiso 0.609(10) 1 calc PR A 1 C17 C -0.02469(19) 0.6791(3) 0.4880(4) 0.057(2) Uani 0.609(10) 1 d PG A 1 H17 H -0.0548 0.6707 0.5571 0.068 Uiso 0.609(10) 1 calc PR A 1 C18 C -0.01400(19) 0.7389(3) 0.4109(4) 0.0564(15) Uani 0.609(10) 1 d PG A 1 H18 H -0.0368 0.7714 0.4272 0.068 Uiso 0.609(10) 1 calc PR A 1 C19 C 0.0300(2) 0.7512(3) 0.3098(4) 0.0607(14) Uani 0.609(10) 1 d PG A 1 H19 H 0.0373 0.7921 0.2571 0.073 Uiso 0.609(10) 1 calc PR A 1 C20 C 0.0634(3) 0.7037(3) 0.2859(3) 0.0575(16) Uani 0.609(10) 1 d PG A 1 H20 H 0.0935 0.7121 0.2168 0.069 Uiso 0.609(10) 1 calc PR A 1 C15B C 0.0593(3) 0.6231(4) 0.3923(5) 0.041(2) Uani 0.391(10) 1 d PG A 2 C16B C 0.0226(4) 0.6012(4) 0.5005(5) 0.055(2) Uani 0.391(10) 1 d PG A 2 H16B H 0.0269 0.5625 0.5459 0.066 Uiso 0.391(10) 1 calc PR A 2 C17B C -0.0204(3) 0.6359(5) 0.5421(6) 0.066(3) Uani 0.391(10) 1 d PG A 2 H17B H -0.0455 0.6210 0.6161 0.080 Uiso 0.391(10) 1 calc PR A 2 C18B C -0.0268(4) 0.6925(6) 0.4756(8) 0.066(5) Uani 0.391(10) 1 d PG A 2 H18B H -0.0561 0.7162 0.5041 0.080 Uiso 0.391(10) 1 calc PR A 2 C19B C 0.0099(4) 0.7143(5) 0.3674(7) 0.070(3) Uani 0.391(10) 1 d PG A 2 H19B H 0.0056 0.7530 0.3219 0.084 Uiso 0.391(10) 1 calc PR A 2 C20B C 0.0530(4) 0.6796(5) 0.3257(5) 0.055(3) Uani 0.391(10) 1 d PG A 2 H20B H 0.0780 0.6946 0.2518 0.066 Uiso 0.391(10) 1 calc PR 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 Zn1 0.03206(18) 0.03495(14) 0.02073(15) 0.00130(6) 0.00259(13) 0.01603(9) N1 0.0487(10) 0.0324(8) 0.0253(8) -0.0063(6) 0.0069(7) 0.0078(7) N2 0.0451(9) 0.0323(8) 0.0250(8) 0.0004(6) 0.0064(7) 0.0134(7) N3 0.0305(7) 0.0326(8) 0.0247(7) 0.0003(6) 0.0014(6) 0.0159(7) N4 0.0318(8) 0.0419(9) 0.0241(7) -0.0018(7) -0.0007(6) 0.0141(7) N5 0.0320(8) 0.0374(8) 0.0245(7) 0.0003(6) -0.0001(6) 0.0130(7) O1 0.0520(8) 0.0400(7) 0.0252(7) -0.0048(6) 0.0043(6) 0.0067(7) O2 0.0378(7) 0.0503(8) 0.0297(7) -0.0005(6) -0.0017(6) 0.0058(7) C1 0.029(5) 0.0433(12) 0.022(3) -0.0079(17) -0.005(3) 0.004(4) C1B 0.029(5) 0.0433(12) 0.022(3) -0.0079(17) -0.005(3) 0.004(4) C2 0.0593(14) 0.0556(13) 0.0207(9) -0.0034(9) 0.0043(9) 0.0200(11) C3 0.0470(11) 0.0299(10) 0.0283(10) -0.0031(8) 0.0008(8) 0.0120(9) C4 0.0355(10) 0.0328(9) 0.0257(9) 0.0022(8) 0.0043(7) 0.0179(8) C5 0.0368(10) 0.0400(10) 0.0232(9) 0.0021(7) 0.0025(7) 0.0217(9) C6 0.0462(11) 0.0367(10) 0.0296(10) 0.0028(8) 0.0071(8) 0.0200(9) C7 0.0459(11) 0.0503(12) 0.0298(9) 0.0095(9) 0.0124(8) 0.0248(10) C8 0.0414(10) 0.0568(12) 0.0227(8) 0.0015(9) 0.0050(7) 0.0265(10) C9 0.0344(9) 0.0498(11) 0.0223(8) -0.0032(8) -0.0027(7) 0.0214(9) C10 0.0312(9) 0.0424(10) 0.0233(8) 0.0027(7) 0.0020(7) 0.0209(8) C11 0.0306(9) 0.0386(10) 0.0210(8) -0.0013(7) -0.0023(7) 0.0180(8) C12 0.0316(10) 0.0375(10) 0.0294(9) -0.0026(8) -0.0052(8) 0.0133(8) C13 0.0371(11) 0.0488(12) 0.0310(10) 0.0052(9) -0.0020(8) 0.0050(10) C14 0.0306(10) 0.0445(11) 0.0294(9) 0.0025(8) -0.0005(8) 0.0107(9) C21 0.0367(10) 0.0362(10) 0.0322(9) 0.0030(8) -0.0031(8) 0.0047(8) C22 0.0444(12) 0.0606(14) 0.0493(12) 0.0148(11) 0.0026(10) 0.0192(11) C23 0.0566(15) 0.0798(18) 0.0743(18) 0.0264(15) -0.0007(13) 0.0298(14) C24 0.0628(16) 0.0649(16) 0.0509(14) 0.0209(13) -0.0072(12) 0.0112(14) C25 0.0637(15) 0.0528(14) 0.0344(11) 0.0075(10) 0.0029(10) 0.0070(13) C26 0.0509(13) 0.0411(11) 0.0328(10) -0.0026(9) 0.0026(9) 0.0059(10) C15 0.042(2) 0.041(3) 0.030(3) -0.007(2) 0.002(2) 0.016(2) C16 0.0347(19) 0.053(3) 0.038(2) -0.0030(18) 0.0043(17) 0.0132(18) C17 0.034(3) 0.076(4) 0.054(4) -0.013(4) 0.008(3) 0.023(3) C18 0.046(2) 0.064(3) 0.066(3) -0.022(3) -0.011(2) 0.032(2) C19 0.078(3) 0.054(3) 0.053(3) -0.004(2) 0.001(2) 0.035(2) C20 0.075(3) 0.057(3) 0.042(3) 0.002(2) 0.015(2) 0.034(3) C15B 0.041(3) 0.050(5) 0.027(4) -0.011(3) -0.006(3) 0.019(3) C16B 0.048(4) 0.059(5) 0.041(4) -0.009(3) 0.006(3) 0.014(3) C17B 0.045(4) 0.080(6) 0.062(5) -0.032(4) 0.007(3) 0.022(4) C18B 0.063(8) 0.101(10) 0.055(7) -0.037(8) -0.017(6) 0.056(7) C19B 0.076(5) 0.076(6) 0.077(6) -0.018(5) -0.024(5) 0.051(5) C20B 0.055(5) 0.076(8) 0.048(6) -0.012(6) 0.003(4) 0.043(5) _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 Zn1 N3 2.1210(13) 5 ? Zn1 N3 2.1210(13) . ? Zn1 N5 2.1525(15) 5 ? Zn1 N5 2.1525(15) . ? Zn1 N1 2.1832(15) . ? Zn1 N1 2.1832(15) 5 ? N1 C3 1.272(3) . ? N1 C1 1.436(13) . ? N1 C1B 1.56(2) . ? N2 C4 1.298(2) . ? N2 C3 1.366(2) . ? N3 C4 1.368(2) . ? N3 C11 1.378(2) . ? N4 C11 1.302(2) . ? N4 C12 1.360(2) . ? N5 C12 1.293(2) . ? N5 C14 1.471(2) . ? O1 C3 1.362(2) . ? O1 C2 1.445(2) . ? O2 C12 1.347(2) . ? O2 C13 1.446(2) . ? C1 C15 1.534(13) . ? C1 C2 1.661(10) . ? C1 H1 1.0000 . ? C1B C2 1.343(18) . ? C1B C15B 1.46(2) . ? C1B H1B 1.0000 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 H2C 0.9900 . ? C2 H2D 0.9900 . ? C4 C5 1.476(2) . ? C5 C10 1.365(3) . ? C5 C6 1.385(3) . ? C6 C7 1.392(3) . ? C6 H6 0.9500 . ? C7 C8 1.389(3) . ? C7 H7 0.9500 . ? C8 C9 1.386(3) . ? C8 H8 0.9500 . ? C9 C10 1.392(3) . ? C9 H9 0.9500 . ? C10 C11 1.479(2) . ? C13 C14 1.534(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C21 1.507(3) . ? C14 H14 1.0000 . ? C21 C22 1.365(3) . ? C21 C26 1.392(3) . ? C22 C23 1.383(4) . ? C22 H22 0.9500 . ? C23 C24 1.408(4) . ? C23 H23 0.9500 . ? C24 C25 1.337(4) . ? C24 H24 0.9500 . ? C25 C26 1.384(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C15 C16 1.3900 . ? C15 C20 1.3900 . ? C16 C17 1.3900 . ? C16 H16 0.9500 . ? C17 C18 1.3900 . ? C17 H17 0.9500 . ? C18 C19 1.3900 . ? C18 H18 0.9500 . ? C19 C20 1.3900 . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C15B C16B 1.3900 . ? C15B C20B 1.3900 . ? C16B C17B 1.3900 . ? C16B H16B 0.9500 . ? C17B C18B 1.3900 . ? C17B H17B 0.9500 . ? C18B C19B 1.3900 . ? C18B H18B 0.9500 . ? C19B C20B 1.3900 . ? C19B H19B 0.9500 . ? C20B H20B 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 N3 Zn1 N3 177.27(8) 5 . ? N3 Zn1 N5 84.34(5) 5 5 ? N3 Zn1 N5 97.50(5) . 5 ? N3 Zn1 N5 97.50(5) 5 . ? N3 Zn1 N5 84.34(5) . . ? N5 Zn1 N5 95.76(8) 5 . ? N3 Zn1 N1 94.92(6) 5 . ? N3 Zn1 N1 83.31(6) . . ? N5 Zn1 N1 83.91(6) 5 . ? N5 Zn1 N1 167.49(5) . . ? N3 Zn1 N1 83.31(6) 5 5 ? N3 Zn1 N1 94.92(6) . 5 ? N5 Zn1 N1 167.49(5) 5 5 ? N5 Zn1 N1 83.91(6) . 5 ? N1 Zn1 N1 99.12(10) . 5 ? C3 N1 C1 111.4(5) . . ? C3 N1 C1B 101.8(8) . . ? C1 N1 C1B 14.4(10) . . ? C3 N1 Zn1 123.61(13) . . ? C1 N1 Zn1 122.1(6) . . ? C1B N1 Zn1 126.3(9) . . ? C4 N2 C3 120.52(16) . . ? C4 N3 C11 107.06(14) . . ? C4 N3 Zn1 126.76(11) . . ? C11 N3 Zn1 126.08(11) . . ? C11 N4 C12 121.92(15) . . ? C12 N5 C14 107.85(15) . . ? C12 N5 Zn1 124.67(13) . . ? C14 N5 Zn1 123.45(11) . . ? C3 O1 C2 105.62(15) . . ? C12 O2 C13 107.02(14) . . ? N1 C1 C15 115.1(7) . . ? N1 C1 C2 98.7(8) . . ? C15 C1 C2 111.7(9) . . ? N1 C1 H1 110.3 . . ? C15 C1 H1 110.3 . . ? C2 C1 H1 110.3 . . ? C2 C1B C15B 116.7(18) . . ? C2 C1B N1 107.8(15) . . ? C15B C1B N1 106.1(9) . . ? C2 C1B H1B 108.6 . . ? C15B C1B H1B 108.6 . . ? N1 C1B H1B 108.6 . . ? C1B C2 O1 106.8(10) . . ? C1B C2 C1 9.1(14) . . ? O1 C2 C1 102.6(5) . . ? C1B C2 H2A 116.0 . . ? O1 C2 H2A 111.3 . . ? C1 C2 H2A 111.3 . . ? C1B C2 H2B 102.1 . . ? O1 C2 H2B 111.3 . . ? C1 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? C1B C2 H2C 114.1 . . ? O1 C2 H2C 110.2 . . ? C1 C2 H2C 123.2 . . ? H2A C2 H2C 98.4 . . ? H2B C2 H2C 13.0 . . ? C1B C2 H2D 106.8 . . ? O1 C2 H2D 110.4 . . ? C1 C2 H2D 101.3 . . ? H2A C2 H2D 11.0 . . ? H2B C2 H2D 118.5 . . ? H2C C2 H2D 108.5 . . ? N1 C3 O1 117.22(16) . . ? N1 C3 N2 131.46(19) . . ? O1 C3 N2 111.27(17) . . ? N2 C4 N3 129.80(16) . . ? N2 C4 C5 120.01(16) . . ? N3 C4 C5 110.15(15) . . ? C10 C5 C6 122.27(17) . . ? C10 C5 C4 106.43(16) . . ? C6 C5 C4 131.30(18) . . ? C5 C6 C7 116.96(19) . . ? C5 C6 H6 121.5 . . ? C7 C6 H6 121.5 . . ? C8 C7 C6 120.65(18) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 121.97(17) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 116.60(18) . . ? C8 C9 H9 121.7 . . ? C10 C9 H9 121.7 . . ? C5 C10 C9 121.55(17) . . ? C5 C10 C11 106.71(15) . . ? C9 C10 C11 131.72(17) . . ? N4 C11 N3 129.50(16) . . ? N4 C11 C10 120.89(15) . . ? N3 C11 C10 109.57(14) . . ? N5 C12 O2 116.75(17) . . ? N5 C12 N4 131.34(17) . . ? O2 C12 N4 111.91(15) . . ? O2 C13 C14 104.64(15) . . ? O2 C13 H13A 110.8 . . ? C14 C13 H13A 110.8 . . ? O2 C13 H13B 110.8 . . ? C14 C13 H13B 110.8 . . ? H13A C13 H13B 108.9 . . ? N5 C14 C21 112.77(15) . . ? N5 C14 C13 103.69(15) . . ? C21 C14 C13 113.90(17) . . ? N5 C14 H14 108.8 . . ? C21 C14 H14 108.8 . . ? C13 C14 H14 108.8 . . ? C22 C21 C26 119.1(2) . . ? C22 C21 C14 119.83(19) . . ? C26 C21 C14 121.0(2) . . ? C21 C22 C23 121.0(2) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C22 C23 C24 118.7(3) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C25 C24 C23 120.4(3) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 120.7(2) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 120.1(2) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? C16 C15 C20 120.0 . . ? C16 C15 C1 118.6(6) . . ? C20 C15 C1 121.3(6) . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 120.0 . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 120.0 . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C15 120.0 . . ? C19 C20 H20 120.0 . . ? C15 C20 H20 120.0 . . ? C16B C15B C20B 120.0 . . ? C16B C15B C1B 120.1(10) . . ? C20B C15B C1B 119.4(10) . . ? C15B C16B C17B 120.0 . . ? C15B C16B H16B 120.0 . . ? C17B C16B H16B 120.0 . . ? C16B C17B C18B 120.0 . . ? C16B C17B H17B 120.0 . . ? C18B C17B H17B 120.0 . . ? C19B C18B C17B 120.0 . . ? C19B C18B H18B 120.0 . . ? C17B C18B H18B 120.0 . . ? C20B C19B C18B 120.0 . . ? C20B C19B H19B 120.0 . . ? C18B C19B H19B 120.0 . . ? C19B C20B C15B 120.0 . . ? C19B C20B H20B 120.0 . . ? C15B C20B H20B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 65.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.191 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.032 ###END data_daley07/Zn((S,S)-6)2 _database_code_depnum_ccdc_archive 'CCDC 783917' #TrackingRef '1723_web_deposit_cif_file_0_ChristopherJ.A.Daley_1278646485.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H62 N10 O6.33 Zn' _chemical_formula_weight 933.77 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 Trigonal _symmetry_space_group_name_H-M P3(2)21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'y, x, -z' 'x-y, -y, -z+1/3' '-x, -x+y, -z+2/3' _cell_length_a 18.788(5) _cell_length_b 18.788(5) _cell_length_c 11.730(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3586(2) _cell_formula_units_Z 3 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4506 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 25.41 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1484 _exptl_absorpt_coefficient_mu 0.572 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7992 _exptl_absorpt_correction_T_max 0.9450 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 31203 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.24 _reflns_number_total 4261 _reflns_number_gt 3951 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; SQUEEZE found one void containing 7 disordered acetone molecules. Their formula was added to the formula for the unit-cell and the electron density removed. 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^)+(0.0383P)^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 _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.006(9) _refine_ls_number_reflns 4261 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.013 798 228 ' ' _platon_squeeze_details ; SQUEEZE found one void containing 7 disordered acetone molecules. Their formula was added to the formula for the unit-cell and the electron density removed. ; 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 0.574877(17) 0.574877(17) 0.0000 0.02492(9) Uani 1 2 d S . . O1 O 0.62558(11) 0.76511(10) -0.24668(14) 0.0491(5) Uani 1 1 d . . . O2 O 0.57076(10) 0.34646(10) 0.06932(12) 0.0373(4) Uani 1 1 d . . . N1 N 0.61595(11) 0.68823(11) -0.09240(14) 0.0306(4) Uani 1 1 d . . . N3 N 0.60829(10) 0.53736(11) -0.15706(13) 0.0261(4) Uani 1 1 d . . . N5 N 0.54398(11) 0.45191(11) 0.05548(14) 0.0294(4) Uani 1 1 d . . . N2 N 0.64051(12) 0.65368(12) -0.28273(14) 0.0355(5) Uani 1 1 d . . . N4 N 0.58105(11) 0.39874(11) -0.10879(14) 0.0293(4) Uani 1 1 d . . . C1 C 0.60533(16) 0.75655(15) -0.0462(2) 0.0414(6) Uani 1 1 d . . . H1 H 0.5519 0.7320 -0.0042 0.050 Uiso 1 1 calc R . . C2 C 0.59814(19) 0.79959(17) -0.1549(2) 0.0518(7) Uani 1 1 d . . . H2A H 0.5407 0.7865 -0.1673 0.062 Uiso 1 1 calc R . . H2B H 0.6340 0.8600 -0.1497 0.062 Uiso 1 1 calc R . . C3 C 0.62705(14) 0.69864(14) -0.20098(18) 0.0348(5) Uani 1 1 d . . . C4 C 0.63005(13) 0.58055(14) -0.25876(16) 0.0306(5) Uani 1 1 d . . . C5 C 0.63259(14) 0.52704(15) -0.35084(16) 0.0322(5) Uani 1 1 d . . . C6 C 0.64897(15) 0.54005(17) -0.46734(18) 0.0416(6) Uani 1 1 d . . . H6 H 0.6659 0.5919 -0.5016 0.050 Uiso 1 1 calc R . . C7 C 0.63917(15) 0.47249(18) -0.53153(17) 0.0452(7) Uani 1 1 d . . . H7 H 0.6499 0.4792 -0.6111 0.054 Uiso 1 1 calc R . . C8 C 0.61417(14) 0.39557(16) -0.48226(19) 0.0393(6) Uani 1 1 d . . . H8 H 0.6067 0.3512 -0.5292 0.047 Uiso 1 1 calc R . . C9 C 0.60005(13) 0.38326(14) -0.36537(18) 0.0330(5) Uani 1 1 d . . . H9 H 0.5847 0.3319 -0.3305 0.040 Uiso 1 1 calc R . . C10 C 0.60986(13) 0.45090(14) -0.30225(17) 0.0288(5) Uani 1 1 d . . . C11 C 0.59711(12) 0.45910(13) -0.17838(16) 0.0250(5) Uani 1 1 d . . . C12 C 0.56532(13) 0.40490(13) 0.00480(17) 0.0281(5) Uani 1 1 d . . . C13 C 0.56086(18) 0.36567(16) 0.18646(19) 0.0425(6) Uani 1 1 d . . . H13B H 0.6145 0.3937 0.2264 0.051 Uiso 1 1 calc R . . H13A H 0.5231 0.3151 0.2289 0.051 Uiso 1 1 calc R . . C14 C 0.52432(15) 0.42316(15) 0.17549(18) 0.0368(6) Uani 1 1 d . . . H14 H 0.5544 0.4711 0.2279 0.044 Uiso 1 1 calc R . . C15 C 0.67429(19) 0.80994(16) 0.0369(2) 0.0591(8) Uani 1 1 d . . . H15 H 0.6830 0.7718 0.0869 0.071 Uiso 1 1 calc R . . C16\ C 0.6443(3) 0.8568(2) 0.1153(4) 0.1053(14) Uani 1 1 d . . . H16A H 0.5912 0.8176 0.1491 0.158 Uiso 1 1 calc R . . H16B H 0.6382 0.8973 0.0700 0.158 Uiso 1 1 calc R . . H16C H 0.6846 0.8850 0.1760 0.158 Uiso 1 1 calc R . . C17 C 0.7576(2) 0.8673(2) -0.0227(4) 0.0901(12) Uani 1 1 d . . . H17A H 0.7735 0.8343 -0.0694 0.135 Uiso 1 1 calc R . . H17C H 0.7999 0.8972 0.0350 0.135 Uiso 1 1 calc R . . H17B H 0.7519 0.9066 -0.0714 0.135 Uiso 1 1 calc R . . C18 C 0.43126(17) 0.38277(17) 0.1980(2) 0.0502(7) Uani 1 1 d . . . H18 H 0.4136 0.4229 0.1748 0.060 Uiso 1 1 calc R . . C19 C 0.37981(18) 0.30295(19) 0.1282(3) 0.0724(9) Uani 1 1 d . . . H19A H 0.3215 0.2792 0.1473 0.109 Uiso 1 1 calc R . . H19C H 0.3976 0.2634 0.1465 0.109 Uiso 1 1 calc R . . H19B H 0.3878 0.3158 0.0466 0.109 Uiso 1 1 calc R . . C20 C 0.4138(2) 0.3659(2) 0.3260(3) 0.0860(12) Uani 1 1 d . . . H20C H 0.4469 0.4170 0.3687 0.129 Uiso 1 1 calc R . . H20B H 0.4281 0.3247 0.3503 0.129 Uiso 1 1 calc R . . H20A H 0.3554 0.3454 0.3406 0.129 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 0.03304(15) 0.03304(15) 0.01580(14) 0.00013(7) -0.00013(7) 0.02185(17) O1 0.0755(14) 0.0539(11) 0.0424(9) 0.0200(8) 0.0186(9) 0.0508(11) O2 0.0613(11) 0.0425(9) 0.0226(7) 0.0069(7) 0.0088(7) 0.0369(9) N1 0.0398(11) 0.0353(10) 0.0257(9) 0.0024(8) 0.0030(8) 0.0255(9) N3 0.0318(10) 0.0372(10) 0.0173(8) 0.0028(8) 0.0015(7) 0.0231(8) N5 0.0420(11) 0.0373(10) 0.0166(8) 0.0033(8) 0.0044(8) 0.0257(9) N2 0.0503(12) 0.0480(12) 0.0229(9) 0.0095(8) 0.0075(8) 0.0354(10) N4 0.0379(11) 0.0314(10) 0.0212(9) 0.0010(8) 0.0038(8) 0.0192(9) C1 0.0574(16) 0.0424(14) 0.0398(13) 0.0101(11) 0.0143(12) 0.0365(12) C2 0.079(2) 0.0547(17) 0.0472(14) 0.0146(13) 0.0186(14) 0.0524(17) C3 0.0390(14) 0.0399(13) 0.0348(11) 0.0122(10) 0.0071(10) 0.0268(11) C4 0.0392(12) 0.0437(13) 0.0215(10) 0.0044(9) 0.0034(9) 0.0302(11) C5 0.0357(12) 0.0560(15) 0.0189(9) 0.0013(11) 0.0015(9) 0.0335(12) C6 0.0520(15) 0.0729(18) 0.0220(10) 0.0105(11) 0.0062(10) 0.0478(15) C7 0.0551(16) 0.090(2) 0.0157(10) -0.0033(12) 0.0011(10) 0.0552(16) C8 0.0379(13) 0.0626(16) 0.0264(11) -0.0152(11) -0.0062(10) 0.0320(13) C9 0.0288(12) 0.0478(14) 0.0243(11) -0.0096(10) -0.0031(9) 0.0208(11) C10 0.0295(11) 0.0436(13) 0.0204(10) -0.0024(10) -0.0009(9) 0.0237(11) C11 0.0281(11) 0.0335(12) 0.0173(9) -0.0043(9) -0.0022(8) 0.0183(10) C12 0.0370(13) 0.0250(11) 0.0235(11) 0.0037(9) 0.0020(9) 0.0164(10) C13 0.0739(18) 0.0519(15) 0.0191(11) 0.0104(10) 0.0127(11) 0.0444(14) C14 0.0591(15) 0.0438(14) 0.0209(10) 0.0102(10) 0.0098(10) 0.0359(12) C15 0.082(2) 0.0465(15) 0.0573(16) -0.0146(13) -0.0065(15) 0.0381(15) C16\ 0.135(4) 0.086(3) 0.111(3) -0.052(2) -0.009(3) 0.068(3) C17 0.081(2) 0.060(2) 0.110(3) 0.001(2) -0.001(2) 0.021(2) C18 0.0614(18) 0.0526(17) 0.0486(15) 0.0198(13) 0.0271(13) 0.0376(15) C19 0.0525(18) 0.0548(19) 0.100(3) 0.0066(18) 0.0226(18) 0.0197(15) C20 0.115(3) 0.116(3) 0.062(2) 0.051(2) 0.062(2) 0.085(3) _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 Zn1 N1 2.1592(18) 4 ? Zn1 N1 2.1592(18) . ? Zn1 N3 2.1743(18) 4 ? Zn1 N3 2.1743(18) . ? Zn1 N5 2.1811(18) 4 ? Zn1 N5 2.1811(18) . ? O1 C3 1.372(3) . ? O1 C2 1.476(3) . ? O2 C12 1.379(2) . ? O2 C13 1.456(3) . ? N1 C3 1.290(3) . ? N1 C1 1.496(3) . ? N3 C4 1.384(3) . ? N3 C11 1.400(3) . ? N5 C12 1.284(3) . ? N5 C14 1.487(3) . ? N2 C4 1.317(3) . ? N2 C3 1.382(3) . ? N4 C11 1.304(3) . ? N4 C12 1.382(3) . ? C1 C15 1.528(4) . ? C1 C2 1.552(3) . ? C1 H1 1.0000 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C4 C5 1.492(3) . ? C5 C10 1.394(3) . ? C5 C6 1.395(3) . ? C6 C7 1.407(4) . ? C6 H6 0.9500 . ? C7 C8 1.402(4) . ? C7 H7 0.9500 . ? C8 C9 1.394(3) . ? C8 H8 0.9500 . ? C9 C10 1.401(3) . ? C9 H9 0.9500 . ? C10 C11 1.493(3) . ? C13 C14 1.548(3) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 C18 1.541(4) . ? C14 H14 1.0000 . ? C15 C17 1.554(5) . ? C15 C16\ 1.560(4) . ? C15 H15 1.0000 . ? C16\ H16A 0.9800 . ? C16\ H16B 0.9800 . ? C16\ H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17C 0.9800 . ? C17 H17B 0.9800 . ? C18 C20 1.535(4) . ? C18 C19 1.551(4) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19C 0.9800 . ? C19 H19B 0.9800 . ? C20 H20C 0.9800 . ? C20 H20B 0.9800 . ? C20 H20A 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 N1 Zn1 N1 95.58(9) 4 . ? N1 Zn1 N3 82.85(7) 4 4 ? N1 Zn1 N3 98.52(7) . 4 ? N1 Zn1 N3 98.52(7) 4 . ? N1 Zn1 N3 82.85(7) . . ? N3 Zn1 N3 177.97(10) 4 . ? N1 Zn1 N5 165.72(6) 4 4 ? N1 Zn1 N5 85.49(7) . 4 ? N3 Zn1 N5 82.91(6) 4 4 ? N3 Zn1 N5 95.74(7) . 4 ? N1 Zn1 N5 85.49(7) 4 . ? N1 Zn1 N5 165.72(6) . . ? N3 Zn1 N5 95.74(7) 4 . ? N3 Zn1 N5 82.91(6) . . ? N5 Zn1 N5 96.99(10) 4 . ? C3 O1 C2 106.55(17) . . ? C12 O2 C13 104.54(16) . . ? C3 N1 C1 107.99(18) . . ? C3 N1 Zn1 126.61(15) . . ? C1 N1 Zn1 121.94(13) . . ? C4 N3 C11 107.87(16) . . ? C4 N3 Zn1 126.06(13) . . ? C11 N3 Zn1 125.15(13) . . ? C12 N5 C14 107.15(17) . . ? C12 N5 Zn1 125.54(14) . . ? C14 N5 Zn1 123.61(13) . . ? C4 N2 C3 120.78(18) . . ? C11 N4 C12 119.79(18) . . ? N1 C1 C15 111.19(19) . . ? N1 C1 C2 103.47(18) . . ? C15 C1 C2 116.6(2) . . ? N1 C1 H1 108.4 . . ? C15 C1 H1 108.4 . . ? C2 C1 H1 108.4 . . ? O1 C2 C1 103.31(17) . . ? O1 C2 H2A 111.1 . . ? C1 C2 H2A 111.1 . . ? O1 C2 H2B 111.1 . . ? C1 C2 H2B 111.1 . . ? H2A C2 H2B 109.1 . . ? N1 C3 O1 116.65(19) . . ? N1 C3 N2 131.1(2) . . ? O1 C3 N2 112.23(18) . . ? N2 C4 N3 129.90(19) . . ? N2 C4 C5 120.64(18) . . ? N3 C4 C5 109.17(18) . . ? C10 C5 C6 120.5(2) . . ? C10 C5 C4 107.39(17) . . ? C6 C5 C4 132.0(2) . . ? C5 C6 C7 116.6(2) . . ? C5 C6 H6 121.7 . . ? C7 C6 H6 121.7 . . ? C8 C7 C6 122.34(19) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 116.2(2) . . ? C8 C9 H9 121.9 . . ? C10 C9 H9 121.9 . . ? C5 C10 C9 123.28(19) . . ? C5 C10 C11 105.95(18) . . ? C9 C10 C11 130.7(2) . . ? N4 C11 N3 130.49(18) . . ? N4 C11 C10 119.92(19) . . ? N3 C11 C10 109.54(17) . . ? N5 C12 O2 117.82(18) . . ? N5 C12 N4 131.11(19) . . ? O2 C12 N4 111.00(18) . . ? O2 C13 C14 104.52(17) . . ? O2 C13 H13B 110.8 . . ? C14 C13 H13B 110.8 . . ? O2 C13 H13A 110.8 . . ? C14 C13 H13A 110.8 . . ? H13B C13 H13A 108.9 . . ? N5 C14 C18 110.83(19) . . ? N5 C14 C13 102.47(17) . . ? C18 C14 C13 115.6(2) . . ? N5 C14 H14 109.2 . . ? C18 C14 H14 109.2 . . ? C13 C14 H14 109.2 . . ? C1 C15 C17 113.4(2) . . ? C1 C15 C16\ 108.6(2) . . ? C17 C15 C16\ 113.4(3) . . ? C1 C15 H15 107.0 . . ? C17 C15 H15 107.0 . . ? C16\ C15 H15 107.0 . . ? C15 C16\ H16A 109.5 . . ? C15 C16\ H16B 109.5 . . ? H16A C16\ H16B 109.5 . . ? C15 C16\ H16C 109.5 . . ? H16A C16\ H16C 109.5 . . ? H16B C16\ H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? C20 C18 C14 110.0(2) . . ? C20 C18 C19 110.6(3) . . ? C14 C18 C19 113.0(2) . . ? C20 C18 H18 107.7 . . ? C14 C18 H18 107.7 . . ? C19 C18 H18 107.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? H19C C19 H19B 109.5 . . ? C18 C20 H20C 109.5 . . ? C18 C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? C18 C20 H20A 109.5 . . ? H20C C20 H20A 109.5 . . ? H20B C20 H20A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.179 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.032