# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'William B. Tolman' _publ_contact_author_address ; Department of Chemistry University of Minnesota 207 Pleasant Street SE Minneapolis MN 55455 USA ; _publ_contact_author_email tolman@chem.umn.edu _publ_contact_author_fax 1-612-624-7029 _publ_contact_author_phone 1-612-625-4061 _publ_section_title ; Stereoelective Polymerization of D,L-Lactide Using N-Heterocyclic Carbene Based Compounds ; loop_ _publ_author_name _publ_author_address T.R.Jensen ; Department of Chemistry University of Minnesota 207 Pleasant Street SE Minneapolis MN 55455 USA ; L.E.Breyfogle ; Department of Chemistry University of Minnesota 207 Pleasant Street SE Minneapolis MN 55455 USA ; W.B.Tolman ; Department of Chemistry University of Minnesota 207 Pleasant Street SE Minneapolis MN 55455 USA ; M.A.Hillmyer ; Department of Chemistry University of Minnesota 207 Pleasant Street SE Minneapolis MN 55455 USA ; data_04009 _database_code_depnum_ccdc_archive 'CCDC 237615' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common "Tryg's Zn Carbene with Benzyl Alchohol" _chemical_melting_point ? _chemical_formula_moiety 'C70 H76 N4 O4 Zn2' _chemical_formula_sum 'C70 H76 N4 O4 Zn2' _chemical_formula_weight 1168.09 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.0338(17) _cell_length_b 19.045(3) _cell_length_c 13.3803(17) _cell_angle_alpha 90.00 _cell_angle_beta 113.930(2) _cell_angle_gamma 90.00 _cell_volume 3035.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.920514 _cell_measurement_theta_max 1.000000 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.920514 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23289 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6883 _reflns_number_gt 5987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _computing_publication_material ? _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^)+(0.0394P)^2^+1.3957P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6883 _refine_ls_number_parameters 366 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.480243(17) 0.421810(9) 0.985310(15) 0.02807(7) Uani 1 1 d . . . O1 O 0.39135(10) 0.51171(6) 0.95464(10) 0.0311(3) Uani 1 1 d . . . O2 O 0.47290(11) 0.37710(6) 0.85397(10) 0.0390(3) Uani 1 1 d . . . N1 N 0.50501(13) 0.30799(7) 1.16249(12) 0.0334(3) Uani 1 1 d . . . N2 N 0.33545(13) 0.32202(7) 1.04844(12) 0.0340(3) Uani 1 1 d . . . C1 C 0.62490(16) 0.31248(8) 1.22331(14) 0.0336(4) Uani 1 1 d . . . C2 C 0.66579(18) 0.35003(9) 1.32132(15) 0.0414(4) Uani 1 1 d . . . C3 C 0.7813(2) 0.34812(11) 1.38380(16) 0.0494(5) Uani 1 1 d . . . H3A H 0.8115 0.3737 1.4504 0.059 Uiso 1 1 calc R . . C4 C 0.85340(18) 0.31013(11) 1.35170(17) 0.0481(5) Uani 1 1 d . . . C5 C 0.80904(17) 0.27453(10) 1.25321(16) 0.0430(4) Uani 1 1 d . . . H5A H 0.8581 0.2490 1.2301 0.052 Uiso 1 1 calc R . . C6 C 0.69482(16) 0.27499(9) 1.18709(15) 0.0367(4) Uani 1 1 d . . . C7 C 0.9781(2) 0.30761(16) 1.4222(2) 0.0685(7) Uani 1 1 d . . . H7A H 0.9920 0.3226 1.4967 0.103 Uiso 1 1 calc R . . H7B H 1.0176 0.3391 1.3917 0.103 Uiso 1 1 calc R . . H7C H 1.0055 0.2595 1.4239 0.103 Uiso 1 1 calc R . . C8 C 0.5877(2) 0.39008(12) 1.35814(18) 0.0568(6) Uani 1 1 d . . . H8A H 0.5435 0.4234 1.3010 0.085 Uiso 1 1 calc R . . H8B H 0.6316 0.4158 1.4255 0.085 Uiso 1 1 calc R . . H8C H 0.5371 0.3572 1.3719 0.085 Uiso 1 1 calc R . . C9 C 0.64793(18) 0.23559(11) 1.08012(17) 0.0468(5) Uani 1 1 d . . . H9A H 0.6089 0.2685 1.0203 0.070 Uiso 1 1 calc R . . H9B H 0.5951 0.1998 1.0827 0.070 Uiso 1 1 calc R . . H9C H 0.7094 0.2130 1.0679 0.070 Uiso 1 1 calc R . . C10 C 0.23241(15) 0.34772(9) 0.96456(15) 0.0340(4) Uani 1 1 d . . . C11 C 0.17456(16) 0.40057(9) 0.99192(16) 0.0368(4) Uani 1 1 d . . . C12 C 0.07033(17) 0.42015(10) 0.91313(19) 0.0455(5) Uani 1 1 d . . . H12A H 0.0290 0.4558 0.9301 0.055 Uiso 1 1 calc R . . C13 C 0.02521(18) 0.38939(11) 0.81114(19) 0.0518(5) Uani 1 1 d . . . C14 C 0.08621(19) 0.33746(12) 0.78715(17) 0.0515(5) Uani 1 1 d . . . H14A H 0.0559 0.3165 0.7166 0.062 Uiso 1 1 calc R . . C15 C 0.19054(17) 0.31487(10) 0.86291(16) 0.0423(4) Uani 1 1 d . . . C16 C -0.0892(2) 0.41180(14) 0.7281(3) 0.0796(9) Uani 1 1 d . . . H16A H -0.0914 0.4631 0.7211 0.119 Uiso 0.50 1 calc PR . . H16B H -0.1470 0.3964 0.7525 0.119 Uiso 0.50 1 calc PR . . H16C H -0.1030 0.3904 0.6572 0.119 Uiso 0.50 1 calc PR . . H16D H -0.1363 0.3702 0.6994 0.119 Uiso 0.50 1 calc PR . . H16E H -0.0806 0.4369 0.6680 0.119 Uiso 0.50 1 calc PR . . H16F H -0.1246 0.4428 0.7633 0.119 Uiso 0.50 1 calc PR . . C17 C 0.22356(19) 0.43582(11) 1.10213(18) 0.0481(5) Uani 1 1 d . . . H17A H 0.2478 0.4000 1.1597 0.072 Uiso 1 1 calc R . . H17B H 0.1666 0.4659 1.1106 0.072 Uiso 1 1 calc R . . H17C H 0.2882 0.4644 1.1078 0.072 Uiso 1 1 calc R . . C18 C 0.2556(2) 0.25759(12) 0.8378(2) 0.0591(6) Uani 1 1 d . . . H18A H 0.2104 0.2376 0.7658 0.089 Uiso 1 1 calc R . . H18B H 0.2737 0.2208 0.8935 0.089 Uiso 1 1 calc R . . H18C H 0.3252 0.2770 0.8378 0.089 Uiso 1 1 calc R . . C19 C 0.44032(15) 0.34806(8) 1.07558(14) 0.0303(3) Uani 1 1 d . . . C20 C 0.44178(17) 0.25844(10) 1.18845(17) 0.0419(4) Uani 1 1 d . . . H20A H 0.4686 0.2250 1.2460 0.050 Uiso 1 1 calc R . . C21 C 0.33581(17) 0.26710(10) 1.11660(17) 0.0436(4) Uani 1 1 d . . . H21A H 0.2726 0.2406 1.1129 0.052 Uiso 1 1 calc R . . C22 C 0.28806(15) 0.51959(9) 0.86445(14) 0.0325(4) Uani 1 1 d . . . H22A H 0.2535 0.4727 0.8428 0.039 Uiso 1 1 calc R . . H22B H 0.3023 0.5386 0.8024 0.039 Uiso 1 1 calc R . . C23 C 0.20513(15) 0.56719(8) 0.88433(15) 0.0334(4) Uani 1 1 d . . . C24 C 0.09539(16) 0.57125(10) 0.80525(17) 0.0418(4) Uani 1 1 d . . . H24A H 0.0744 0.5443 0.7402 0.050 Uiso 1 1 calc R . . C25 C 0.01651(17) 0.61375(11) 0.8198(2) 0.0500(5) Uani 1 1 d . . . H25A H -0.0578 0.6160 0.7650 0.060 Uiso 1 1 calc R . . C26 C 0.04594(19) 0.65294(12) 0.9141(2) 0.0545(6) Uani 1 1 d . . . H26A H -0.0081 0.6819 0.9247 0.065 Uiso 1 1 calc R . . C27 C 0.1541(2) 0.64978(12) 0.99283(19) 0.0526(5) Uani 1 1 d . . . H27A H 0.1747 0.6771 1.0575 0.063 Uiso 1 1 calc R . . C28 C 0.23374(17) 0.60687(10) 0.97842(16) 0.0405(4) Uani 1 1 d . . . H28A H 0.3080 0.6049 1.0335 0.049 Uiso 1 1 calc R . . C29 C 0.50732(18) 0.41291(11) 0.78234(15) 0.0442(4) Uani 1 1 d U . . H29A H 0.5731 0.3884 0.7796 0.053 Uiso 1 1 calc R . . H29B H 0.5317 0.4607 0.8115 0.053 Uiso 1 1 calc R . . C30 C 0.41797(18) 0.41918(9) 0.66723(16) 0.0409(4) Uani 1 1 d U . . C31 C 0.4487(2) 0.42833(10) 0.57954(17) 0.0522(5) Uani 1 1 d U . . H31A H 0.5260 0.4287 0.5925 0.063 Uiso 1 1 calc R . . C32 C 0.3688(3) 0.43690(13) 0.4745(2) 0.0746(7) Uani 1 1 d U . . H32A H 0.3910 0.4420 0.4154 0.090 Uiso 1 1 calc R . . C33 C 0.2583(3) 0.43805(14) 0.4554(2) 0.0875(9) Uani 1 1 d U . . H33A H 0.2034 0.4453 0.3833 0.105 Uiso 1 1 calc R . . C34 C 0.2250(2) 0.42866(13) 0.5410(3) 0.0795(8) Uani 1 1 d U . . H34A H 0.1475 0.4293 0.5272 0.095 Uiso 1 1 calc R . . C35 C 0.3054(2) 0.41822(11) 0.6473(2) 0.0549(5) Uani 1 1 d U . . H35A H 0.2828 0.4105 0.7056 0.066 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 0.03505(11) 0.01994(10) 0.03289(11) 0.00159(7) 0.01756(8) -0.00153(7) O1 0.0315(6) 0.0219(5) 0.0397(6) 0.0021(5) 0.0143(5) -0.0007(4) O2 0.0547(8) 0.0320(6) 0.0360(6) -0.0050(5) 0.0242(6) -0.0098(6) N1 0.0426(8) 0.0239(6) 0.0395(8) 0.0052(6) 0.0226(7) 0.0018(6) N2 0.0412(8) 0.0261(7) 0.0426(8) 0.0055(6) 0.0251(7) -0.0008(6) C1 0.0445(10) 0.0221(7) 0.0359(9) 0.0059(6) 0.0179(8) 0.0000(7) C2 0.0646(13) 0.0250(8) 0.0375(9) 0.0047(7) 0.0239(9) 0.0003(8) C3 0.0695(14) 0.0386(10) 0.0332(9) 0.0014(8) 0.0138(10) -0.0129(10) C4 0.0516(12) 0.0434(11) 0.0453(11) 0.0102(9) 0.0155(10) -0.0095(9) C5 0.0439(11) 0.0369(10) 0.0514(11) 0.0057(8) 0.0224(9) -0.0016(8) C6 0.0447(10) 0.0257(8) 0.0424(10) 0.0018(7) 0.0205(8) -0.0016(7) C7 0.0539(14) 0.0832(18) 0.0557(14) 0.0129(13) 0.0090(11) -0.0155(13) C8 0.0874(18) 0.0410(11) 0.0470(12) -0.0016(9) 0.0326(12) 0.0124(11) C9 0.0491(12) 0.0437(11) 0.0525(12) -0.0119(9) 0.0258(10) -0.0023(9) C10 0.0363(9) 0.0299(8) 0.0416(9) 0.0040(7) 0.0219(8) -0.0046(7) C11 0.0393(10) 0.0313(8) 0.0464(10) 0.0027(7) 0.0240(8) -0.0031(7) C12 0.0407(11) 0.0349(9) 0.0642(13) 0.0077(9) 0.0245(10) 0.0004(8) C13 0.0440(12) 0.0433(11) 0.0597(13) 0.0107(10) 0.0123(10) -0.0083(9) C14 0.0568(13) 0.0493(12) 0.0447(11) -0.0027(9) 0.0167(10) -0.0169(10) C15 0.0506(12) 0.0361(9) 0.0481(11) -0.0023(8) 0.0280(9) -0.0115(8) C16 0.0572(16) 0.0603(15) 0.089(2) 0.0139(14) -0.0036(14) -0.0055(12) C17 0.0544(13) 0.0417(10) 0.0555(12) -0.0058(9) 0.0298(10) 0.0016(9) C18 0.0736(16) 0.0513(13) 0.0642(14) -0.0167(11) 0.0402(13) -0.0072(11) C19 0.0405(9) 0.0216(7) 0.0353(8) 0.0002(6) 0.0220(7) 0.0000(6) C20 0.0523(12) 0.0319(9) 0.0511(11) 0.0138(8) 0.0308(10) 0.0020(8) C21 0.0498(11) 0.0334(9) 0.0573(12) 0.0121(8) 0.0318(10) -0.0028(8) C22 0.0373(9) 0.0262(8) 0.0362(9) 0.0013(7) 0.0171(7) -0.0024(7) C23 0.0366(9) 0.0245(8) 0.0418(9) 0.0055(7) 0.0187(8) 0.0000(6) C24 0.0400(10) 0.0343(9) 0.0492(11) 0.0037(8) 0.0161(9) -0.0016(8) C25 0.0347(10) 0.0451(11) 0.0673(14) 0.0120(10) 0.0178(10) 0.0044(9) C26 0.0505(13) 0.0484(12) 0.0751(15) 0.0104(11) 0.0361(12) 0.0154(10) C27 0.0620(14) 0.0467(11) 0.0556(12) -0.0019(10) 0.0304(11) 0.0116(10) C28 0.0429(11) 0.0370(9) 0.0423(10) 0.0022(8) 0.0181(9) 0.0054(8) C29 0.0486(11) 0.0506(11) 0.0368(9) -0.0016(8) 0.0208(8) -0.0109(9) C30 0.0537(11) 0.0299(8) 0.0382(9) -0.0056(7) 0.0177(8) -0.0016(8) C31 0.0813(15) 0.0375(10) 0.0427(10) 0.0003(8) 0.0301(10) 0.0053(10) C32 0.129(2) 0.0450(12) 0.0395(11) 0.0001(9) 0.0236(14) 0.0098(15) C33 0.1157(19) 0.0503(14) 0.0522(13) -0.0061(11) -0.0115(14) 0.0135(16) C34 0.0591(15) 0.0538(14) 0.0936(18) -0.0233(14) -0.0020(12) 0.0014(12) C35 0.0543(12) 0.0431(11) 0.0622(12) -0.0178(10) 0.0185(10) -0.0044(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.9199(12) . ? Zn1 O1 1.9896(12) 3_667 ? Zn1 O1 2.0141(11) . ? Zn1 C19 2.0524(16) . ? Zn1 Zn1 3.0208(5) 3_667 ? O1 C22 1.405(2) . ? O1 Zn1 1.9896(12) 3_667 ? O2 C29 1.391(2) . ? N1 C19 1.360(2) . ? N1 C20 1.387(2) . ? N1 C1 1.442(2) . ? N2 C19 1.358(2) . ? N2 C21 1.386(2) . ? N2 C10 1.442(2) . ? C1 C6 1.390(3) . ? C1 C2 1.396(3) . ? C2 C3 1.395(3) . ? C2 C8 1.506(3) . ? C3 C4 1.385(3) . ? C3 H3A 0.9500 . ? C4 C5 1.383(3) . ? C4 C7 1.513(3) . ? C5 C6 1.389(3) . ? C5 H5A 0.9500 . ? C6 C9 1.509(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.392(3) . ? C10 C11 1.393(3) . ? C11 C12 1.391(3) . ? C11 C17 1.506(3) . ? C12 C13 1.378(3) . ? C12 H12A 0.9500 . ? C13 C14 1.386(3) . ? C13 C16 1.515(3) . ? C14 C15 1.394(3) . ? C14 H14A 0.9500 . ? C15 C18 1.501(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 H16D 0.9800 . ? C16 H16E 0.9800 . ? C16 H16F 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 C21 1.335(3) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.515(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C28 1.384(3) . ? C23 C24 1.394(3) . ? C24 C25 1.383(3) . ? C24 H24A 0.9500 . ? C25 C26 1.380(3) . ? C25 H25A 0.9500 . ? C26 C27 1.377(3) . ? C26 H26A 0.9500 . ? C27 C28 1.394(3) . ? C27 H27A 0.9500 . ? C28 H28A 0.9500 . ? C29 C30 1.512(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C35 1.381(3) . ? C30 C31 1.396(3) . ? C31 C32 1.379(3) . ? C31 H31A 0.9500 . ? C32 C33 1.357(5) . ? C32 H32A 0.9500 . ? C33 C34 1.391(5) . ? C33 H33A 0.9500 . ? C34 C35 1.397(4) . ? C34 H34A 0.9500 . ? C35 H35A 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 O2 Zn1 O1 111.92(5) . 3_667 ? O2 Zn1 O1 112.31(5) . . ? O1 Zn1 O1 82.04(5) 3_667 . ? O2 Zn1 C19 107.74(6) . . ? O1 Zn1 C19 124.78(6) 3_667 . ? O1 Zn1 C19 116.07(6) . . ? O2 Zn1 Zn1 119.93(4) . 3_667 ? O1 Zn1 Zn1 41.33(3) 3_667 3_667 ? O1 Zn1 Zn1 40.71(3) . 3_667 ? C19 Zn1 Zn1 131.96(5) . 3_667 ? C22 O1 Zn1 129.42(10) . 3_667 ? C22 O1 Zn1 122.51(10) . . ? Zn1 O1 Zn1 97.96(5) 3_667 . ? C29 O2 Zn1 120.21(11) . . ? C19 N1 C20 111.76(15) . . ? C19 N1 C1 127.10(14) . . ? C20 N1 C1 121.14(15) . . ? C19 N2 C21 111.42(15) . . ? C19 N2 C10 127.07(14) . . ? C21 N2 C10 121.44(15) . . ? C6 C1 C2 122.42(18) . . ? C6 C1 N1 119.10(16) . . ? C2 C1 N1 118.29(17) . . ? C3 C2 C1 117.24(19) . . ? C3 C2 C8 121.71(19) . . ? C1 C2 C8 121.05(19) . . ? C4 C3 C2 122.06(19) . . ? C4 C3 H3A 119.0 . . ? C2 C3 H3A 119.0 . . ? C5 C4 C3 118.5(2) . . ? C5 C4 C7 120.4(2) . . ? C3 C4 C7 121.0(2) . . ? C4 C5 C6 122.0(2) . . ? C4 C5 H5A 119.0 . . ? C6 C5 H5A 119.0 . . ? C5 C6 C1 117.76(17) . . ? C5 C6 C9 121.20(18) . . ? C1 C6 C9 121.03(17) . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 122.83(18) . . ? C15 C10 N2 118.70(16) . . ? C11 C10 N2 118.24(16) . . ? C12 C11 C10 117.46(18) . . ? C12 C11 C17 121.23(18) . . ? C10 C11 C17 121.31(18) . . ? C13 C12 C11 122.0(2) . . ? C13 C12 H12A 119.0 . . ? C11 C12 H12A 119.0 . . ? C12 C13 C14 118.6(2) . . ? C12 C13 C16 120.2(2) . . ? C14 C13 C16 121.2(2) . . ? C13 C14 C15 122.3(2) . . ? C13 C14 H14A 118.9 . . ? C15 C14 H14A 118.9 . . ? C10 C15 C14 116.88(19) . . ? C10 C15 C18 120.80(19) . . ? C14 C15 C18 122.3(2) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C16 H16D 109.5 . . ? H16A C16 H16D 141.1 . . ? H16B C16 H16D 56.3 . . ? H16C C16 H16D 56.3 . . ? C13 C16 H16E 109.5 . . ? H16A C16 H16E 56.3 . . ? H16B C16 H16E 141.1 . . ? H16C C16 H16E 56.3 . . ? H16D C16 H16E 109.5 . . ? C13 C16 H16F 109.5 . . ? H16A C16 H16F 56.3 . . ? H16B C16 H16F 56.3 . . ? H16C C16 H16F 141.1 . . ? H16D C16 H16F 109.5 . . ? H16E C16 H16F 109.5 . . ? C11 C17 H17A 109.5 . . ? C11 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C11 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 N1 103.38(14) . . ? N2 C19 Zn1 124.10(12) . . ? N1 C19 Zn1 132.06(13) . . ? C21 C20 N1 106.37(16) . . ? C21 C20 H20A 126.8 . . ? N1 C20 H20A 126.8 . . ? C20 C21 N2 107.07(16) . . ? C20 C21 H21A 126.5 . . ? N2 C21 H21A 126.5 . . ? O1 C22 C23 114.62(14) . . ? O1 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? O1 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C28 C23 C24 118.37(17) . . ? C28 C23 C22 122.59(17) . . ? C24 C23 C22 119.04(17) . . ? C25 C24 C23 121.2(2) . . ? C25 C24 H24A 119.4 . . ? C23 C24 H24A 119.4 . . ? C26 C25 C24 119.9(2) . . ? C26 C25 H25A 120.0 . . ? C24 C25 H25A 120.0 . . ? C27 C26 C25 119.6(2) . . ? C27 C26 H26A 120.2 . . ? C25 C26 H26A 120.2 . . ? C26 C27 C28 120.6(2) . . ? C26 C27 H27A 119.7 . . ? C28 C27 H27A 119.7 . . ? C23 C28 C27 120.33(19) . . ? C23 C28 H28A 119.8 . . ? C27 C28 H28A 119.8 . . ? O2 C29 C30 114.22(17) . . ? O2 C29 H29A 108.7 . . ? C30 C29 H29A 108.7 . . ? O2 C29 H29B 108.7 . . ? C30 C29 H29B 108.7 . . ? H29A C29 H29B 107.6 . . ? C35 C30 C31 119.0(2) . . ? C35 C30 C29 120.94(19) . . ? C31 C30 C29 120.0(2) . . ? C32 C31 C30 121.1(3) . . ? C32 C31 H31A 119.5 . . ? C30 C31 H31A 119.5 . . ? C33 C32 C31 119.9(3) . . ? C33 C32 H32A 120.0 . . ? C31 C32 H32A 120.0 . . ? C32 C33 C34 120.3(3) . . ? C32 C33 H33A 119.8 . . ? C34 C33 H33A 119.8 . . ? C33 C34 C35 120.1(3) . . ? C33 C34 H34A 120.0 . . ? C35 C34 H34A 120.0 . . ? C30 C35 C34 119.6(3) . . ? C30 C35 H35A 120.2 . . ? C34 C35 H35A 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Zn1 O1 C22 37.66(13) . . . . ? O1 Zn1 O1 C22 148.16(14) 3_667 . . . ? C19 Zn1 O1 C22 -86.90(13) . . . . ? Zn1 Zn1 O1 C22 148.16(14) 3_667 . . . ? O2 Zn1 O1 Zn1 -110.49(6) . . . 3_667 ? O1 Zn1 O1 Zn1 0.0 3_667 . . 3_667 ? C19 Zn1 O1 Zn1 124.94(6) . . . 3_667 ? O1 Zn1 O2 C29 -32.63(15) 3_667 . . . ? O1 Zn1 O2 C29 57.59(15) . . . . ? C19 Zn1 O2 C29 -173.37(14) . . . . ? Zn1 Zn1 O2 C29 12.75(16) 3_667 . . . ? C19 N1 C1 C6 -87.0(2) . . . . ? C20 N1 C1 C6 92.0(2) . . . . ? C19 N1 C1 C2 98.0(2) . . . . ? C20 N1 C1 C2 -82.9(2) . . . . ? C6 C1 C2 C3 -0.7(3) . . . . ? N1 C1 C2 C3 174.10(15) . . . . ? C6 C1 C2 C8 -179.99(17) . . . . ? N1 C1 C2 C8 -5.2(2) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? C8 C2 C3 C4 178.52(19) . . . . ? C2 C3 C4 C5 1.6(3) . . . . ? C2 C3 C4 C7 -178.61(19) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C7 C4 C5 C6 179.18(19) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C4 C5 C6 C9 -179.75(18) . . . . ? C2 C1 C6 C5 1.2(3) . . . . ? N1 C1 C6 C5 -173.52(15) . . . . ? C2 C1 C6 C9 -179.35(17) . . . . ? N1 C1 C6 C9 5.9(2) . . . . ? C19 N2 C10 C15 97.3(2) . . . . ? C21 N2 C10 C15 -86.1(2) . . . . ? C19 N2 C10 C11 -87.9(2) . . . . ? C21 N2 C10 C11 88.7(2) . . . . ? C15 C10 C11 C12 0.4(3) . . . . ? N2 C10 C11 C12 -174.15(15) . . . . ? C15 C10 C11 C17 -178.88(17) . . . . ? N2 C10 C11 C17 6.6(2) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C17 C11 C12 C13 178.73(19) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C11 C12 C13 C16 179.4(2) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C16 C13 C14 C15 -178.6(2) . . . . ? C11 C10 C15 C14 0.3(3) . . . . ? N2 C10 C15 C14 174.84(16) . . . . ? C11 C10 C15 C18 -179.32(18) . . . . ? N2 C10 C15 C18 -4.8(3) . . . . ? C13 C14 C15 C10 -0.9(3) . . . . ? C13 C14 C15 C18 178.7(2) . . . . ? C21 N2 C19 N1 -0.31(19) . . . . ? C10 N2 C19 N1 176.58(16) . . . . ? C21 N2 C19 Zn1 172.70(13) . . . . ? C10 N2 C19 Zn1 -10.4(2) . . . . ? C20 N1 C19 N2 0.00(19) . . . . ? C1 N1 C19 N2 179.10(15) . . . . ? C20 N1 C19 Zn1 -172.20(13) . . . . ? C1 N1 C19 Zn1 6.9(3) . . . . ? O2 Zn1 C19 N2 -71.62(14) . . . . ? O1 Zn1 C19 N2 154.00(12) 3_667 . . . ? O1 Zn1 C19 N2 55.26(15) . . . . ? Zn1 Zn1 C19 N2 101.24(13) 3_667 . . . ? O2 Zn1 C19 N1 99.20(16) . . . . ? O1 Zn1 C19 N1 -35.17(18) 3_667 . . . ? O1 Zn1 C19 N1 -133.92(15) . . . . ? Zn1 Zn1 C19 N1 -87.94(16) 3_667 . . . ? C19 N1 C20 C21 0.3(2) . . . . ? C1 N1 C20 C21 -178.85(16) . . . . ? N1 C20 C21 N2 -0.5(2) . . . . ? C19 N2 C21 C20 0.5(2) . . . . ? C10 N2 C21 C20 -176.58(16) . . . . ? Zn1 O1 C22 C23 -75.75(18) 3_667 . . . ? Zn1 O1 C22 C23 146.82(11) . . . . ? O1 C22 C23 C28 8.1(2) . . . . ? O1 C22 C23 C24 -171.67(15) . . . . ? C28 C23 C24 C25 0.0(3) . . . . ? C22 C23 C24 C25 179.75(17) . . . . ? C23 C24 C25 C26 -0.2(3) . . . . ? C24 C25 C26 C27 0.5(3) . . . . ? C25 C26 C27 C28 -0.6(3) . . . . ? C24 C23 C28 C27 -0.1(3) . . . . ? C22 C23 C28 C27 -179.87(18) . . . . ? C26 C27 C28 C23 0.4(3) . . . . ? Zn1 O2 C29 C30 -122.43(15) . . . . ? O2 C29 C30 C35 26.6(3) . . . . ? O2 C29 C30 C31 -155.42(18) . . . . ? C35 C30 C31 C32 0.5(3) . . . . ? C29 C30 C31 C32 -177.46(19) . . . . ? C30 C31 C32 C33 1.4(3) . . . . ? C31 C32 C33 C34 -1.8(4) . . . . ? C32 C33 C34 C35 0.2(4) . . . . ? C31 C30 C35 C34 -2.1(3) . . . . ? C29 C30 C35 C34 175.89(19) . . . . ? C33 C34 C35 C30 1.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.292 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.046