# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_to3znns10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H66 N4 O3 Si2 Zn' _chemical_formula_weight 844.58 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' Si Si 0.0817 0.0704 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.8655(11) _cell_length_b 15.0021(12) _cell_length_c 22.8550(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4754.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9728 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 30.38 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 0.608 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7757 _exptl_absorpt_correction_T_max 0.9417 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 76604 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 30.55 _reflns_number_total 14503 _reflns_number_gt 11909 _reflns_threshold_expression >2sigma(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 ; 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^)+(0.0461P)^2^+0.5140P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.012(6) _refine_ls_number_reflns 14503 _refine_ls_number_parameters 520 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0877 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 Zn Zn -0.413799(14) -0.745622(13) -0.089528(8) 0.02253(5) Uani 1 1 d . . . O1 O -0.41615(9) -0.88456(8) -0.08024(6) 0.0275(3) Uani 1 1 d . . . O2 O -0.56470(11) -0.72364(11) -0.13898(6) 0.0391(4) Uani 1 1 d . . . O3 O -0.35204(10) -0.68755(11) -0.01060(6) 0.0354(3) Uani 1 1 d . . . N1 N -0.56025(10) -0.85135(9) -0.03672(6) 0.0189(3) Uani 1 1 d . . . N2 N -0.60400(10) -0.69727(9) -0.04404(6) 0.0206(3) Uani 1 1 d . . . N3 N -0.48918(9) -0.74601(11) 0.02968(6) 0.0197(3) Uani 1 1 d . . . N4 N -0.32916(12) -0.70611(10) -0.15002(7) 0.0253(3) Uani 1 1 d . . . Si1 Si -0.29311(4) -0.78644(4) -0.19809(2) 0.02577(11) Uani 1 1 d . . . Si2 Si -0.32949(4) -0.59417(3) -0.16173(2) 0.02709(11) Uani 1 1 d . . . C1 C -0.52586(11) -0.75967(12) -0.02976(7) 0.0195(3) Uani 1 1 d . . . C11 C -0.49838(12) -0.91014(12) -0.06448(8) 0.0221(3) Uani 1 1 d . . . C12 C -0.53301(13) -0.99832(12) -0.07383(8) 0.0240(4) Uani 1 1 d . . . H12A H -0.4921 -1.0401 -0.0928 0.029 Uiso 1 1 calc R . . C13 C -0.62231(13) -1.02514(11) -0.05668(8) 0.0220(3) Uani 1 1 d . . . C14 C -0.66157(15) -1.11802(12) -0.06717(9) 0.0291(4) Uani 1 1 d . . . C15 C -0.75287(17) -1.11023(16) -0.10433(10) 0.0410(5) Uani 1 1 d . . . H15A H -0.7370 -1.0823 -0.1419 0.061 Uiso 1 1 calc R . . H15B H -0.8005 -1.0736 -0.0837 0.061 Uiso 1 1 calc R . . H15C H -0.7796 -1.1698 -0.1112 0.061 Uiso 1 1 calc R . . C16 C -0.6883(2) -1.15993(15) -0.00803(10) 0.0435(6) Uani 1 1 d . . . H16A H -0.6305 -1.1646 0.0164 0.065 Uiso 1 1 calc R . . H16B H -0.7153 -1.2195 -0.0145 0.065 Uiso 1 1 calc R . . H16C H -0.7362 -1.1224 0.0117 0.065 Uiso 1 1 calc R . . C17 C -0.58931(18) -1.17784(13) -0.09853(10) 0.0401(5) Uani 1 1 d . . . H17A H -0.5722 -1.1512 -0.1363 0.060 Uiso 1 1 calc R . . H17B H -0.6181 -1.2367 -0.1050 0.060 Uiso 1 1 calc R . . H17C H -0.5312 -1.1841 -0.0745 0.060 Uiso 1 1 calc R . . C18 C -0.68226(12) -0.96134(12) -0.02873(7) 0.0217(3) Uani 1 1 d . . . H18A H -0.7450 -0.9780 -0.0160 0.026 Uiso 1 1 calc R . . C19 C -0.65098(12) -0.87738(12) -0.02007(8) 0.0209(3) Uani 1 1 d . . . H19A H -0.6927 -0.8353 -0.0020 0.025 Uiso 1 1 calc R . . C21 C -0.61525(13) -0.68155(13) -0.10387(8) 0.0261(4) Uani 1 1 d . . . C22 C -0.68423(14) -0.61512(13) -0.11980(8) 0.0298(4) Uani 1 1 d . . . H22A H -0.6934 -0.6027 -0.1602 0.036 Uiso 1 1 calc R . . C23 C -0.73733(13) -0.56887(11) -0.08025(9) 0.0259(4) Uani 1 1 d . . . C24 C -0.80534(14) -0.49333(12) -0.09770(10) 0.0325(4) Uani 1 1 d . . . C25 C -0.8249(2) -0.4909(2) -0.16316(12) 0.0625(8) Uani 1 1 d . . . H25A H -0.8670 -0.4404 -0.1723 0.094 Uiso 1 1 calc R . . H25B H -0.8565 -0.5465 -0.1751 0.094 Uiso 1 1 calc R . . H25C H -0.7638 -0.4845 -0.1843 0.094 Uiso 1 1 calc R . . C26 C -0.7568(2) -0.40634(15) -0.08150(16) 0.0663(9) Uani 1 1 d . . . H26A H -0.7965 -0.3563 -0.0949 0.099 Uiso 1 1 calc R . . H26B H -0.6932 -0.4033 -0.1002 0.099 Uiso 1 1 calc R . . H26C H -0.7492 -0.4031 -0.0389 0.099 Uiso 1 1 calc R . . C27 C -0.90065(18) -0.5026(2) -0.06614(15) 0.0670(9) Uani 1 1 d . . . H27A H -0.9445 -0.4552 -0.0789 0.101 Uiso 1 1 calc R . . H27B H -0.8901 -0.4979 -0.0239 0.101 Uiso 1 1 calc R . . H27C H -0.9291 -0.5608 -0.0752 0.101 Uiso 1 1 calc R . . C28 C -0.72462(15) -0.59056(13) -0.02026(9) 0.0304(4) Uani 1 1 d . . . H28A H -0.7621 -0.5611 0.0087 0.037 Uiso 1 1 calc R . . C29 C -0.65958(14) -0.65272(13) -0.00411(8) 0.0266(4) Uani 1 1 d . . . H29A H -0.6521 -0.6660 0.0363 0.032 Uiso 1 1 calc R . . C31 C -0.39883(13) -0.70617(13) 0.03414(8) 0.0254(4) Uani 1 1 d . . . C32 C -0.36532(13) -0.68659(12) 0.09198(9) 0.0269(4) Uani 1 1 d . . . H32A H -0.3058 -0.6559 0.0961 0.032 Uiso 1 1 calc R . . C33 C -0.41386(14) -0.70943(12) 0.14092(7) 0.0238(3) Uani 1 1 d . . . C34 C -0.38024(14) -0.68409(14) 0.20245(9) 0.0290(4) Uani 1 1 d . . . C35 C -0.45474(18) -0.62164(19) 0.22893(11) 0.0504(6) Uani 1 1 d . . . H35A H -0.4590 -0.5673 0.2052 0.076 Uiso 1 1 calc R . . H35B H -0.4355 -0.6061 0.2689 0.076 Uiso 1 1 calc R . . H35C H -0.5177 -0.6513 0.2297 0.076 Uiso 1 1 calc R . . C36 C -0.28239(16) -0.63770(16) 0.20116(9) 0.0395(5) Uani 1 1 d . . . H36A H -0.2868 -0.5835 0.1774 0.059 Uiso 1 1 calc R . . H36B H -0.2342 -0.6779 0.1842 0.059 Uiso 1 1 calc R . . H36C H -0.2632 -0.6219 0.2411 0.059 Uiso 1 1 calc R . . C37 C -0.37150(18) -0.76836(17) 0.23994(10) 0.0466(6) Uani 1 1 d . . . H37A H -0.4344 -0.7979 0.2423 0.070 Uiso 1 1 calc R . . H37B H -0.3500 -0.7521 0.2794 0.070 Uiso 1 1 calc R . . H37C H -0.3245 -0.8089 0.2222 0.070 Uiso 1 1 calc R . . C38 C -0.50162(12) -0.75760(14) 0.13359(7) 0.0252(3) Uani 1 1 d . . . H38A H -0.5359 -0.7784 0.1669 0.030 Uiso 1 1 calc R . . C39 C -0.53615(12) -0.77375(11) 0.07941(8) 0.0233(4) Uani 1 1 d . . . H39A H -0.5951 -0.8055 0.0755 0.028 Uiso 1 1 calc R . . C41 C -0.21296(16) -0.74192(17) -0.25745(9) 0.0396(5) Uani 1 1 d . . . H41A H -0.1597 -0.7083 -0.2399 0.059 Uiso 1 1 calc R . . H41B H -0.2503 -0.7026 -0.2831 0.059 Uiso 1 1 calc R . . H41C H -0.1870 -0.7916 -0.2804 0.059 Uiso 1 1 calc R . . C42 C -0.39715(16) -0.84138(17) -0.23525(11) 0.0450(6) Uani 1 1 d . . . H42A H -0.4419 -0.8646 -0.2058 0.068 Uiso 1 1 calc R . . H42B H -0.3736 -0.8905 -0.2596 0.068 Uiso 1 1 calc R . . H42C H -0.4306 -0.7978 -0.2599 0.068 Uiso 1 1 calc R . . C43 C -0.22283(14) -0.87629(13) -0.16100(9) 0.0294(4) Uani 1 1 d . . . H43A H -0.2613 -0.9016 -0.1291 0.044 Uiso 1 1 calc R . . H43B H -0.1630 -0.8513 -0.1451 0.044 Uiso 1 1 calc R . . H43C H -0.2073 -0.9232 -0.1893 0.044 Uiso 1 1 calc R . . C51 C -0.20590(18) -0.54377(15) -0.15709(13) 0.0484(6) Uani 1 1 d . . . H51A H -0.1649 -0.5691 -0.1878 0.073 Uiso 1 1 calc R . . H51B H -0.1778 -0.5568 -0.1187 0.073 Uiso 1 1 calc R . . H51C H -0.2105 -0.4791 -0.1624 0.073 Uiso 1 1 calc R . . C52 C -0.40301(19) -0.53481(14) -0.10544(10) 0.0444(6) Uani 1 1 d . . . H52A H -0.4704 -0.5541 -0.1083 0.067 Uiso 1 1 calc R . . H52B H -0.3992 -0.4704 -0.1121 0.067 Uiso 1 1 calc R . . H52C H -0.3781 -0.5488 -0.0664 0.067 Uiso 1 1 calc R . . C53 C -0.3830(2) -0.56052(16) -0.23344(10) 0.0456(6) Uani 1 1 d . . . H53A H -0.4483 -0.5850 -0.2367 0.068 Uiso 1 1 calc R . . H53B H -0.3430 -0.5836 -0.2654 0.068 Uiso 1 1 calc R . . H53C H -0.3858 -0.4953 -0.2358 0.068 Uiso 1 1 calc R . . C61 C -0.11330(16) -0.80417(17) 0.28924(10) 0.0417(5) Uani 1 1 d . . . H61A H -0.0795 -0.8025 0.2531 0.050 Uiso 1 1 calc R . . C62 C -0.12940(16) -0.72706(15) 0.32015(10) 0.0383(5) Uani 1 1 d . . . H62A H -0.1052 -0.6720 0.3058 0.046 Uiso 1 1 calc R . . C63 C -0.18032(18) -0.72932(15) 0.37164(10) 0.0438(5) Uani 1 1 d . . . H63A H -0.1915 -0.6757 0.3927 0.053 Uiso 1 1 calc R . . C64 C -0.2151(2) -0.80827(18) 0.39281(11) 0.0523(6) Uani 1 1 d . . . H64A H -0.2512 -0.8094 0.4281 0.063 Uiso 1 1 calc R . . C65 C -0.1975(2) -0.88598(17) 0.36287(12) 0.0518(6) Uani 1 1 d . . . H65A H -0.2205 -0.9411 0.3779 0.062 Uiso 1 1 calc R . . C66 C -0.14673(17) -0.88423(16) 0.31124(11) 0.0456(6) Uani 1 1 d . . . H66A H -0.1346 -0.9381 0.2907 0.055 Uiso 1 1 calc R . . C71 C -0.4848(2) -1.3597(2) 0.00938(14) 0.0620(8) Uani 1 1 d . . . H71A H -0.4695 -1.3503 -0.0307 0.074 Uiso 1 1 calc R . . C72 C -0.4750(2) -1.2918(2) 0.04848(16) 0.0667(8) Uani 1 1 d . . . H72A H -0.4527 -1.2352 0.0357 0.080 Uiso 1 1 calc R . . C73 C -0.4972(2) -1.3052(2) 0.10672(15) 0.0705(9) Uani 1 1 d . . . H73A H -0.4905 -1.2580 0.1341 0.085 Uiso 1 1 calc R . . C74 C -0.5287(2) -1.3866(3) 0.12439(14) 0.0747(10) Uani 1 1 d . . . H74A H -0.5444 -1.3959 0.1644 0.090 Uiso 1 1 calc R . . C75 C -0.5383(2) -1.4553(2) 0.08553(15) 0.0730(9) Uani 1 1 d . . . H75A H -0.5597 -1.5121 0.0985 0.088 Uiso 1 1 calc R . . C76 C -0.5169(2) -1.4413(2) 0.02769(13) 0.0637(8) Uani 1 1 d . . . H76A H -0.5243 -1.4884 0.0003 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 Zn 0.02163(9) 0.02390(9) 0.02206(9) -0.00010(8) 0.00416(8) -0.00330(9) O1 0.0203(5) 0.0241(6) 0.0380(7) 0.0001(5) 0.0086(6) -0.0017(5) O2 0.0408(8) 0.0566(10) 0.0200(6) -0.0036(6) 0.0007(6) 0.0204(7) O3 0.0280(7) 0.0566(9) 0.0216(7) -0.0009(6) 0.0010(5) -0.0190(7) N1 0.0169(6) 0.0203(7) 0.0195(7) -0.0016(5) 0.0008(5) -0.0017(5) N2 0.0207(7) 0.0203(7) 0.0208(7) -0.0002(5) 0.0001(5) 0.0001(5) N3 0.0187(6) 0.0213(7) 0.0192(6) -0.0018(6) -0.0011(5) -0.0021(6) N4 0.0289(8) 0.0227(7) 0.0243(7) 0.0002(6) 0.0073(6) -0.0013(6) Si1 0.0260(2) 0.0286(2) 0.0227(2) -0.0028(2) 0.0018(2) 0.0023(2) Si2 0.0322(3) 0.0231(2) 0.0259(2) 0.0018(2) 0.0024(2) -0.0046(2) C1 0.0201(7) 0.0186(8) 0.0197(7) -0.0006(6) -0.0018(6) -0.0019(7) C11 0.0201(8) 0.0215(8) 0.0246(8) 0.0001(7) 0.0018(7) 0.0025(7) C12 0.0236(8) 0.0215(8) 0.0268(9) -0.0003(7) 0.0051(7) 0.0021(7) C13 0.0261(8) 0.0202(8) 0.0196(8) 0.0011(6) -0.0008(7) -0.0021(7) C14 0.0363(10) 0.0206(8) 0.0305(9) -0.0024(7) 0.0083(8) -0.0084(8) C15 0.0408(12) 0.0394(12) 0.0428(13) -0.0122(10) 0.0019(10) -0.0152(10) C16 0.0600(15) 0.0295(11) 0.0409(12) 0.0072(9) 0.0156(11) -0.0068(10) C17 0.0487(12) 0.0230(9) 0.0486(13) -0.0067(8) 0.0114(11) -0.0049(9) C18 0.0189(8) 0.0244(8) 0.0217(8) -0.0015(6) 0.0018(6) -0.0035(7) C19 0.0170(8) 0.0247(9) 0.0211(8) -0.0027(7) -0.0010(6) 0.0019(6) C21 0.0266(9) 0.0305(9) 0.0213(9) 0.0005(7) -0.0006(7) 0.0034(7) C22 0.0312(10) 0.0343(10) 0.0239(9) 0.0063(8) -0.0020(7) 0.0023(8) C23 0.0237(9) 0.0179(8) 0.0360(10) 0.0034(7) -0.0004(7) -0.0026(6) C24 0.0296(10) 0.0219(8) 0.0460(12) 0.0079(8) 0.0008(9) 0.0028(7) C25 0.080(2) 0.0590(17) 0.0481(15) 0.0086(13) -0.0100(15) 0.0355(15) C26 0.0661(17) 0.0243(11) 0.108(3) 0.0043(14) -0.0285(18) 0.0026(11) C27 0.0347(13) 0.0702(18) 0.096(2) 0.0443(16) 0.0159(14) 0.0199(12) C28 0.0363(11) 0.0251(9) 0.0299(10) -0.0040(8) 0.0023(8) 0.0081(8) C29 0.0322(10) 0.0271(9) 0.0206(9) -0.0028(7) 0.0031(7) 0.0043(8) C31 0.0231(9) 0.0296(9) 0.0235(8) 0.0008(7) -0.0007(7) -0.0073(7) C32 0.0223(8) 0.0331(9) 0.0254(9) 0.0004(8) -0.0031(7) -0.0069(7) C33 0.0245(8) 0.0252(8) 0.0218(8) 0.0005(6) -0.0034(7) 0.0012(8) C34 0.0265(9) 0.0378(10) 0.0229(9) -0.0017(8) -0.0050(7) -0.0034(8) C35 0.0432(13) 0.0684(17) 0.0396(13) -0.0242(12) -0.0082(10) 0.0054(12) C36 0.0389(11) 0.0522(13) 0.0273(10) 0.0005(9) -0.0098(9) -0.0144(10) C37 0.0495(13) 0.0586(16) 0.0315(11) 0.0130(10) -0.0145(10) -0.0122(11) C38 0.0233(8) 0.0325(10) 0.0199(7) 0.0026(8) 0.0022(6) -0.0025(8) C39 0.0202(8) 0.0252(8) 0.0245(9) 0.0011(6) 0.0018(6) -0.0042(6) C41 0.0484(12) 0.0428(12) 0.0276(9) 0.0047(9) 0.0115(8) 0.0092(11) C42 0.0367(12) 0.0499(14) 0.0485(14) -0.0170(11) -0.0086(10) 0.0051(10) C43 0.0277(9) 0.0276(9) 0.0328(10) -0.0004(8) 0.0040(8) 0.0017(7) C51 0.0422(13) 0.0349(12) 0.0680(17) 0.0091(12) -0.0051(12) -0.0115(10) C52 0.0624(15) 0.0253(10) 0.0454(13) -0.0050(9) 0.0114(12) 0.0023(10) C53 0.0603(15) 0.0379(12) 0.0385(12) 0.0037(10) -0.0111(11) 0.0065(11) C61 0.0310(11) 0.0606(15) 0.0335(11) -0.0039(10) -0.0019(9) 0.0054(10) C62 0.0344(11) 0.0382(12) 0.0423(12) 0.0048(9) -0.0045(9) -0.0013(9) C63 0.0530(14) 0.0351(12) 0.0433(12) -0.0101(9) 0.0032(10) -0.0017(10) C64 0.0692(17) 0.0477(14) 0.0400(13) -0.0035(11) 0.0131(12) -0.0074(13) C65 0.0627(17) 0.0364(13) 0.0565(16) 0.0032(11) 0.0010(13) -0.0089(12) C66 0.0466(13) 0.0398(12) 0.0504(14) -0.0167(11) -0.0060(11) 0.0064(10) C71 0.0537(17) 0.077(2) 0.0555(17) 0.0009(15) -0.0027(14) 0.0006(15) C72 0.0516(16) 0.0597(18) 0.089(2) -0.0038(17) -0.0127(16) 0.0110(14) C73 0.0562(17) 0.077(2) 0.079(2) -0.0339(18) -0.0090(16) 0.0196(16) C74 0.072(2) 0.095(3) 0.0567(18) -0.0153(18) 0.0190(16) 0.007(2) C75 0.073(2) 0.075(2) 0.071(2) -0.0106(18) 0.0303(18) -0.0157(16) C76 0.0578(17) 0.076(2) 0.0570(17) -0.0197(15) 0.0083(14) -0.0113(15) _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 Zn N4 1.9078(15) . ? Zn C1 2.0796(16) . ? Zn O1 2.0955(12) . ? Zn O3 2.1786(14) . ? Zn O2 2.4008(14) . ? O1 C11 1.256(2) . ? O2 C21 1.239(2) . ? O3 C31 1.243(2) . ? N1 C19 1.371(2) . ? N1 C11 1.384(2) . ? N1 C1 1.464(2) . ? N2 C29 1.369(2) . ? N2 C21 1.396(2) . ? N2 C1 1.469(2) . ? N3 C39 1.374(2) . ? N3 C31 1.392(2) . ? N3 C1 1.4650(19) . ? N4 Si2 1.7005(16) . ? N4 Si1 1.7058(16) . ? Si1 C42 1.866(2) . ? Si1 C43 1.867(2) . ? Si1 C41 1.877(2) . ? Si2 C52 1.868(2) . ? Si2 C53 1.869(2) . ? Si2 C51 1.876(2) . ? C11 C12 1.423(2) . ? C12 C13 1.360(2) . ? C13 C18 1.420(2) . ? C13 C14 1.515(2) . ? C14 C17 1.524(3) . ? C14 C15 1.529(3) . ? C14 C16 1.536(3) . ? C18 C19 1.347(2) . ? C21 C22 1.428(3) . ? C22 C23 1.357(3) . ? C23 C28 1.420(3) . ? C23 C24 1.527(3) . ? C24 C27 1.512(3) . ? C24 C26 1.514(3) . ? C24 C25 1.521(3) . ? C28 C29 1.349(3) . ? C31 C32 1.432(2) . ? C32 C33 1.350(3) . ? C33 C38 1.425(3) . ? C33 C34 1.529(2) . ? C34 C35 1.520(3) . ? C34 C36 1.525(3) . ? C34 C37 1.532(3) . ? C38 C39 1.350(2) . ? C61 C62 1.374(3) . ? C61 C66 1.382(4) . ? C62 C63 1.373(3) . ? C63 C64 1.367(3) . ? C64 C65 1.373(4) . ? C65 C66 1.374(4) . ? C71 C72 1.361(4) . ? C71 C76 1.368(4) . ? C72 C73 1.381(5) . ? C73 C74 1.358(5) . ? C74 C75 1.367(5) . ? C75 C76 1.371(4) . ? 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 N4 Zn C1 165.26(7) . . ? N4 Zn O1 113.08(6) . . ? C1 Zn O1 79.69(6) . . ? N4 Zn O3 103.53(6) . . ? C1 Zn O3 77.90(6) . . ? O1 Zn O3 108.66(6) . . ? N4 Zn O2 98.76(6) . . ? C1 Zn O2 70.85(5) . . ? O1 Zn O2 99.83(5) . . ? O3 Zn O2 132.64(5) . . ? C11 O1 Zn 110.31(11) . . ? C21 O2 Zn 104.96(12) . . ? C31 O3 Zn 112.71(12) . . ? C19 N1 C11 120.95(14) . . ? C19 N1 C1 122.42(14) . . ? C11 N1 C1 116.51(13) . . ? C29 N2 C21 120.50(15) . . ? C29 N2 C1 125.35(14) . . ? C21 N2 C1 114.06(14) . . ? C39 N3 C31 119.73(14) . . ? C39 N3 C1 124.06(14) . . ? C31 N3 C1 116.13(13) . . ? Si2 N4 Si1 126.66(9) . . ? Si2 N4 Zn 114.79(8) . . ? Si1 N4 Zn 115.31(8) . . ? N4 Si1 C42 112.25(9) . . ? N4 Si1 C43 111.75(9) . . ? C42 Si1 C43 106.94(11) . . ? N4 Si1 C41 112.82(10) . . ? C42 Si1 C41 106.62(11) . . ? C43 Si1 C41 106.03(10) . . ? N4 Si2 C52 111.34(9) . . ? N4 Si2 C53 113.95(10) . . ? C52 Si2 C53 104.98(12) . . ? N4 Si2 C51 112.75(10) . . ? C52 Si2 C51 105.51(12) . . ? C53 Si2 C51 107.67(12) . . ? N1 C1 N3 110.19(13) . . ? N1 C1 N2 109.53(12) . . ? N3 C1 N2 111.90(13) . . ? N1 C1 Zn 105.49(10) . . ? N3 C1 Zn 109.61(10) . . ? N2 C1 Zn 109.92(10) . . ? O1 C11 N1 119.96(16) . . ? O1 C11 C12 123.17(16) . . ? N1 C11 C12 116.87(15) . . ? C13 C12 C11 122.61(16) . . ? C12 C13 C18 117.61(16) . . ? C12 C13 C14 123.63(17) . . ? C18 C13 C14 118.74(16) . . ? C13 C14 C17 112.32(16) . . ? C13 C14 C15 108.37(17) . . ? C17 C14 C15 109.15(17) . . ? C13 C14 C16 108.90(16) . . ? C17 C14 C16 109.35(18) . . ? C15 C14 C16 108.68(18) . . ? C19 C18 C13 120.54(16) . . ? C18 C19 N1 121.40(16) . . ? O2 C21 N2 119.03(16) . . ? O2 C21 C22 124.71(17) . . ? N2 C21 C22 116.24(16) . . ? C23 C22 C21 123.39(17) . . ? C22 C23 C28 117.31(17) . . ? C22 C23 C24 122.72(18) . . ? C28 C23 C24 119.92(17) . . ? C27 C24 C26 110.6(2) . . ? C27 C24 C25 108.4(2) . . ? C26 C24 C25 107.4(2) . . ? C27 C24 C23 110.27(17) . . ? C26 C24 C23 107.52(17) . . ? C25 C24 C23 112.61(18) . . ? C29 C28 C23 120.37(18) . . ? C28 C29 N2 122.11(17) . . ? O3 C31 N3 120.41(16) . . ? O3 C31 C32 122.96(16) . . ? N3 C31 C32 116.61(15) . . ? C33 C32 C31 123.46(16) . . ? C32 C33 C38 117.19(15) . . ? C32 C33 C34 123.16(17) . . ? C38 C33 C34 119.63(16) . . ? C35 C34 C36 109.33(18) . . ? C35 C34 C33 108.19(17) . . ? C36 C34 C33 111.51(17) . . ? C35 C34 C37 109.9(2) . . ? C36 C34 C37 108.48(17) . . ? C33 C34 C37 109.47(17) . . ? C39 C38 C33 120.12(15) . . ? C38 C39 N3 122.44(15) . . ? C62 C61 C66 119.4(2) . . ? C63 C62 C61 120.2(2) . . ? C64 C63 C62 120.4(2) . . ? C63 C64 C65 119.8(2) . . ? C64 C65 C66 120.2(2) . . ? C65 C66 C61 120.0(2) . . ? C72 C71 C76 120.1(3) . . ? C71 C72 C73 120.1(3) . . ? C74 C73 C72 119.3(3) . . ? C73 C74 C75 121.1(3) . . ? C74 C75 C76 119.3(3) . . ? C71 C76 C75 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.410 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 951232' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_t-o3tls10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C56 H72 N6 O6 Tl2' _chemical_formula_weight 1333.94 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' Tl Tl -2.8358 9.6688 '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 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 11.9498(15) _cell_length_b 10.7516(13) _cell_length_c 21.365(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.803(2) _cell_angle_gamma 90.00 _cell_volume 2741.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9581 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 32.56 _exptl_crystal_description Block _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 5.924 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3190 _exptl_absorpt_correction_T_max 0.7176 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 46294 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 32.03 _reflns_number_total 9456 _reflns_number_gt 7171 _reflns_threshold_expression >2sigma(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 ; 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^)+(0.0388P)^2^+0.9968P] 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 9456 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Tl Tl 0.884542(10) 0.965779(10) 0.084187(5) 0.02845(4) Uani 1 1 d . . . O1 O 1.07173(17) 0.8498(2) 0.13235(9) 0.0260(4) Uani 1 1 d . . . O2 O 0.9203(2) 0.9350(2) -0.03781(11) 0.0335(5) Uani 1 1 d . . . O3 O 0.72992(17) 0.7433(2) 0.08728(10) 0.0281(5) Uani 1 1 d . . . N1 N 1.05480(18) 0.7518(2) 0.03735(10) 0.0165(4) Uani 1 1 d . . . N2 N 0.87623(18) 0.7346(2) -0.01733(10) 0.0168(4) Uani 1 1 d . . . N3 N 0.90259(18) 0.6545(2) 0.08723(10) 0.0172(4) Uani 1 1 d . . . C1 C 0.9336(2) 0.7527(2) 0.04375(12) 0.0170(5) Uani 1 1 d . . . C11 C 1.1184(2) 0.8098(3) 0.08569(12) 0.0211(5) Uani 1 1 d . . . C12 C 1.2361(2) 0.8145(3) 0.07735(14) 0.0271(6) Uani 1 1 d . . . H12A H 1.2818 0.8571 0.1080 0.032 Uiso 1 1 calc R . . C13 C 1.2868(2) 0.7624(3) 0.02865(14) 0.0253(6) Uani 1 1 d . . . C14 C 1.4140(3) 0.7631(4) 0.02387(18) 0.0376(8) Uani 1 1 d . . . C15 C 1.4580(4) 0.6419(5) 0.0514(4) 0.112(3) Uani 1 1 d . . . H15A H 1.5379 0.6338 0.0437 0.168 Uiso 1 1 calc R . . H15B H 1.4168 0.5722 0.0317 0.168 Uiso 1 1 calc R . . H15C H 1.4478 0.6411 0.0967 0.168 Uiso 1 1 calc R . . C16 C 1.4447(4) 0.7788(9) -0.0433(3) 0.116(3) Uani 1 1 d . . . H16A H 1.4067 0.8523 -0.0612 0.174 Uiso 1 1 calc R . . H16B H 1.4213 0.7049 -0.0674 0.174 Uiso 1 1 calc R . . H16C H 1.5259 0.7894 -0.0449 0.174 Uiso 1 1 calc R . . C17 C 1.4675(3) 0.8687(4) 0.0605(2) 0.0552(11) Uani 1 1 d . . . H17A H 1.4339 0.9475 0.0462 0.083 Uiso 1 1 calc R . . H17B H 1.5481 0.8701 0.0539 0.083 Uiso 1 1 calc R . . H17C H 1.4554 0.8574 0.1052 0.083 Uiso 1 1 calc R . . C18 C 1.2160(2) 0.7024(3) -0.01809(14) 0.0243(6) Uani 1 1 d . . . H18A H 1.2478 0.6640 -0.0531 0.029 Uiso 1 1 calc R . . C19 C 1.1050(2) 0.7004(3) -0.01230(13) 0.0208(5) Uani 1 1 d . . . H19A H 1.0593 0.6614 -0.0442 0.025 Uiso 1 1 calc R . . C21 C 0.8714(3) 0.8384(3) -0.05620(13) 0.0236(6) Uani 1 1 d . . . C22 C 0.8130(3) 0.8244(3) -0.11516(13) 0.0275(6) Uani 1 1 d . . . H22A H 0.8116 0.8926 -0.1434 0.033 Uiso 1 1 calc R . . C23 C 0.7587(2) 0.7182(3) -0.13332(13) 0.0240(6) Uani 1 1 d . . . C24 C 0.6962(3) 0.7088(3) -0.19746(14) 0.0315(7) Uani 1 1 d . . . C25 C 0.7812(4) 0.7206(6) -0.24765(18) 0.0708(17) Uani 1 1 d . . . H25A H 0.7424 0.7190 -0.2891 0.106 Uiso 1 1 calc R . . H25B H 0.8342 0.6511 -0.2440 0.106 Uiso 1 1 calc R . . H25C H 0.8219 0.7993 -0.2422 0.106 Uiso 1 1 calc R . . C26 C 0.6331(5) 0.5879(5) -0.2062(2) 0.0737(16) Uani 1 1 d . . . H26A H 0.5779 0.5804 -0.1739 0.110 Uiso 1 1 calc R . . H26B H 0.6858 0.5182 -0.2026 0.110 Uiso 1 1 calc R . . H26C H 0.5945 0.5867 -0.2477 0.110 Uiso 1 1 calc R . . C27 C 0.6118(4) 0.8150(5) -0.2053(2) 0.0580(12) Uani 1 1 d . . . H27A H 0.5563 0.8082 -0.1732 0.087 Uiso 1 1 calc R . . H27B H 0.5739 0.8102 -0.2469 0.087 Uiso 1 1 calc R . . H27C H 0.6511 0.8948 -0.2008 0.087 Uiso 1 1 calc R . . C28 C 0.7640(2) 0.6173(3) -0.09099(13) 0.0229(6) Uani 1 1 d . . . H28A H 0.7264 0.5418 -0.1016 0.027 Uiso 1 1 calc R . . C29 C 0.8223(2) 0.6277(2) -0.03528(13) 0.0198(5) Uani 1 1 d . . . H29A H 0.8258 0.5583 -0.0078 0.024 Uiso 1 1 calc R . . C31 C 0.7936(2) 0.6609(3) 0.10823(12) 0.0206(5) Uani 1 1 d . . . C32 C 0.7647(2) 0.5670(3) 0.15188(13) 0.0230(6) Uani 1 1 d . . . H32A H 0.6897 0.5644 0.1647 0.028 Uiso 1 1 calc R . . C33 C 0.8384(3) 0.4810(3) 0.17628(13) 0.0216(5) Uani 1 1 d . . . C34 C 0.8096(3) 0.3859(3) 0.22544(14) 0.0290(6) Uani 1 1 d . . . C35 C 0.8706(3) 0.4217(4) 0.28691(16) 0.0414(9) Uani 1 1 d . . . H35A H 0.8499 0.5067 0.2983 0.062 Uiso 1 1 calc R . . H35B H 0.9517 0.4173 0.2822 0.062 Uiso 1 1 calc R . . H35C H 0.8496 0.3642 0.3199 0.062 Uiso 1 1 calc R . . C36 C 0.8473(4) 0.2559(3) 0.2046(2) 0.0519(11) Uani 1 1 d . . . H36A H 0.9283 0.2563 0.1993 0.078 Uiso 1 1 calc R . . H36B H 0.8081 0.2341 0.1647 0.078 Uiso 1 1 calc R . . H36C H 0.8294 0.1945 0.2365 0.078 Uiso 1 1 calc R . . C37 C 0.6845(3) 0.3810(4) 0.23563(17) 0.0406(8) Uani 1 1 d . . . H37A H 0.6600 0.4613 0.2518 0.061 Uiso 1 1 calc R . . H37B H 0.6694 0.3154 0.2659 0.061 Uiso 1 1 calc R . . H37C H 0.6437 0.3633 0.1957 0.061 Uiso 1 1 calc R . . C38 C 0.9490(3) 0.4841(3) 0.15486(14) 0.0236(6) Uani 1 1 d . . . H38A H 1.0035 0.4266 0.1710 0.028 Uiso 1 1 calc R . . C39 C 0.9768(2) 0.5688(3) 0.11140(13) 0.0206(5) Uani 1 1 d . . . H39A H 1.0509 0.5686 0.0972 0.025 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 Tl 0.03879(7) 0.02049(6) 0.02645(6) -0.00307(5) 0.00527(5) 0.00284(5) O1 0.0305(11) 0.0331(11) 0.0139(9) -0.0023(8) -0.0026(8) -0.0026(9) O2 0.0507(15) 0.0247(10) 0.0244(11) 0.0032(9) -0.0063(10) -0.0113(10) O3 0.0213(10) 0.0336(11) 0.0297(11) 0.0068(9) 0.0034(8) 0.0061(9) N1 0.0182(10) 0.0176(10) 0.0134(10) -0.0012(8) -0.0017(8) -0.0014(8) N2 0.0173(10) 0.0187(10) 0.0142(10) 0.0004(8) -0.0026(8) -0.0001(8) N3 0.0193(11) 0.0194(10) 0.0127(10) -0.0004(8) -0.0008(8) 0.0011(8) C1 0.0166(12) 0.0203(12) 0.0138(11) 0.0015(9) -0.0020(9) -0.0005(10) C11 0.0249(14) 0.0230(13) 0.0148(12) 0.0002(10) -0.0040(10) -0.0048(11) C12 0.0244(14) 0.0346(16) 0.0215(14) 0.0001(12) -0.0053(11) -0.0073(12) C13 0.0201(13) 0.0283(14) 0.0274(15) 0.0041(12) 0.0007(11) -0.0027(11) C14 0.0192(15) 0.0439(19) 0.050(2) -0.0006(17) 0.0033(14) -0.0060(14) C15 0.022(2) 0.047(3) 0.266(10) 0.032(4) 0.001(4) 0.0021(19) C16 0.044(3) 0.236(10) 0.072(4) -0.038(5) 0.028(3) -0.059(4) C17 0.0254(18) 0.063(3) 0.077(3) -0.007(2) -0.0030(19) -0.0116(18) C18 0.0258(14) 0.0255(14) 0.0220(13) -0.0019(11) 0.0054(11) -0.0013(11) C19 0.0261(14) 0.0198(12) 0.0162(12) -0.0025(10) -0.0004(10) 0.0003(10) C21 0.0308(15) 0.0218(13) 0.0177(13) 0.0030(10) -0.0038(11) -0.0017(11) C22 0.0364(17) 0.0279(15) 0.0175(13) 0.0048(11) -0.0058(12) -0.0014(13) C23 0.0216(13) 0.0327(15) 0.0169(13) -0.0012(11) -0.0058(10) 0.0050(11) C24 0.0305(16) 0.0434(19) 0.0197(14) -0.0014(13) -0.0086(12) 0.0020(14) C25 0.055(3) 0.134(5) 0.0228(19) -0.010(3) -0.0028(18) 0.004(3) C26 0.095(4) 0.070(3) 0.051(3) 0.003(2) -0.046(3) -0.030(3) C27 0.056(3) 0.073(3) 0.043(2) 0.004(2) -0.022(2) 0.018(2) C28 0.0250(14) 0.0229(13) 0.0203(13) -0.0035(10) -0.0028(11) -0.0021(11) C29 0.0210(13) 0.0180(12) 0.0200(13) 0.0000(10) -0.0014(10) -0.0017(10) C31 0.0217(13) 0.0237(13) 0.0166(12) -0.0018(10) 0.0016(10) -0.0010(11) C32 0.0244(14) 0.0257(13) 0.0191(13) -0.0014(10) 0.0044(11) -0.0011(11) C33 0.0288(14) 0.0203(13) 0.0158(12) -0.0009(10) 0.0019(10) -0.0046(11) C34 0.0409(18) 0.0256(14) 0.0211(14) 0.0054(11) 0.0065(12) -0.0046(13) C35 0.050(2) 0.049(2) 0.0250(17) 0.0105(15) -0.0009(15) -0.0117(18) C36 0.080(3) 0.0249(17) 0.053(2) 0.0112(17) 0.020(2) -0.0017(19) C37 0.045(2) 0.042(2) 0.0348(18) 0.0104(15) 0.0059(15) -0.0153(16) C38 0.0285(14) 0.0221(14) 0.0200(13) 0.0023(10) -0.0018(11) 0.0021(11) C39 0.0198(13) 0.0231(13) 0.0189(13) 0.0007(10) 0.0006(10) 0.0024(10) _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 Tl C1 2.527(3) . ? Tl O2 2.682(2) . ? Tl O1 2.719(2) . ? Tl O2 2.790(2) 3_775 ? O1 C11 1.243(3) . ? O2 C21 1.246(4) . ? O2 Tl 2.790(2) 3_775 ? O3 C31 1.237(3) . ? N1 C19 1.362(3) . ? N1 C11 1.399(3) . ? N1 C1 1.461(3) . ? N2 C29 1.363(3) . ? N2 C21 1.391(3) . ? N2 C1 1.457(3) . ? N3 C39 1.363(3) . ? N3 C31 1.399(3) . ? N3 C1 1.466(3) . ? C11 C12 1.427(4) . ? C12 C13 1.351(4) . ? C13 C18 1.430(4) . ? C13 C14 1.529(4) . ? C14 C17 1.504(5) . ? C14 C16 1.508(7) . ? C14 C15 1.514(6) . ? C18 C19 1.339(4) . ? C21 C22 1.418(4) . ? C22 C23 1.359(4) . ? C23 C28 1.412(4) . ? C23 C24 1.532(4) . ? C24 C26 1.510(6) . ? C24 C25 1.518(5) . ? C24 C27 1.527(5) . ? C28 C29 1.354(4) . ? C31 C32 1.428(4) . ? C32 C33 1.363(4) . ? C33 C38 1.420(4) . ? C33 C34 1.517(4) . ? C34 C35 1.520(5) . ? C34 C37 1.521(5) . ? C34 C36 1.542(5) . ? C38 C39 1.354(4) . ? 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 C1 Tl O2 60.36(7) . . ? C1 Tl O1 60.87(7) . . ? O2 Tl O1 98.28(7) . . ? C1 Tl O2 90.75(8) . 3_775 ? O2 Tl O2 61.73(8) . 3_775 ? O1 Tl O2 67.87(7) . 3_775 ? C11 O1 Tl 104.37(17) . . ? C21 O2 Tl 108.34(19) . . ? C21 O2 Tl 126.4(2) . 3_775 ? Tl O2 Tl 118.27(8) . 3_775 ? C19 N1 C11 120.8(2) . . ? C19 N1 C1 123.5(2) . . ? C11 N1 C1 115.7(2) . . ? C29 N2 C21 120.2(2) . . ? C29 N2 C1 124.0(2) . . ? C21 N2 C1 115.6(2) . . ? C39 N3 C31 120.7(2) . . ? C39 N3 C1 123.2(2) . . ? C31 N3 C1 115.8(2) . . ? N2 C1 N1 109.9(2) . . ? N2 C1 N3 110.4(2) . . ? N1 C1 N3 109.7(2) . . ? N2 C1 Tl 108.69(16) . . ? N1 C1 Tl 106.59(16) . . ? N3 C1 Tl 111.47(16) . . ? O1 C11 N1 119.8(3) . . ? O1 C11 C12 124.9(3) . . ? N1 C11 C12 115.3(2) . . ? C13 C12 C11 124.3(3) . . ? C12 C13 C18 116.9(3) . . ? C12 C13 C14 122.3(3) . . ? C18 C13 C14 120.7(3) . . ? C17 C14 C16 107.0(4) . . ? C17 C14 C15 108.5(4) . . ? C16 C14 C15 111.8(5) . . ? C17 C14 C13 111.6(3) . . ? C16 C14 C13 110.7(3) . . ? C15 C14 C13 107.3(3) . . ? C19 C18 C13 119.8(3) . . ? C18 C19 N1 122.8(3) . . ? O2 C21 N2 118.4(2) . . ? O2 C21 C22 124.9(3) . . ? N2 C21 C22 116.7(3) . . ? C23 C22 C21 123.4(3) . . ? C22 C23 C28 117.2(3) . . ? C22 C23 C24 121.1(3) . . ? C28 C23 C24 121.8(3) . . ? C26 C24 C25 109.4(4) . . ? C26 C24 C27 107.9(3) . . ? C25 C24 C27 108.7(4) . . ? C26 C24 C23 112.7(3) . . ? C25 C24 C23 108.2(3) . . ? C27 C24 C23 109.8(3) . . ? C29 C28 C23 120.3(3) . . ? C28 C29 N2 122.2(3) . . ? O3 C31 N3 119.0(2) . . ? O3 C31 C32 125.3(3) . . ? N3 C31 C32 115.7(2) . . ? C33 C32 C31 123.9(3) . . ? C32 C33 C38 117.1(3) . . ? C32 C33 C34 123.9(3) . . ? C38 C33 C34 119.0(3) . . ? C33 C34 C35 108.2(3) . . ? C33 C34 C37 112.4(3) . . ? C35 C34 C37 108.6(3) . . ? C33 C34 C36 109.4(3) . . ? C35 C34 C36 110.1(3) . . ? C37 C34 C36 108.2(3) . . ? C39 C38 C33 120.0(3) . . ? C38 C39 N3 122.6(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 32.03 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.326 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.124 _database_code_depnum_ccdc_archive 'CCDC 951233' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_t-o3s10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H37 N3 O3' _chemical_formula_weight 463.61 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' _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 11.8366(15) _cell_length_b 18.801(2) _cell_length_c 12.2176(16) _cell_angle_alpha 90.00 _cell_angle_beta 106.441(2) _cell_angle_gamma 90.00 _cell_volume 2607.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9991 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 30.51 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 41441 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 30.75 _reflns_number_total 8080 _reflns_number_gt 5146 _reflns_threshold_expression >2sigma(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 ; 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^)+(0.0802P)^2^+0.3393P] 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 8080 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1628 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 O1 O 0.47676(10) 0.60448(6) 0.01968(9) 0.0314(3) Uani 1 1 d . . . O2 O 0.54539(10) 0.78323(7) 0.12873(10) 0.0358(3) Uani 1 1 d . . . O3 O 0.24408(9) 0.78353(6) -0.04063(10) 0.0315(3) Uani 1 1 d . . . N1 N 0.40606(10) 0.66593(6) -0.14579(10) 0.0219(2) Uani 1 1 d . . . N2 N 0.56914(10) 0.73759(6) -0.03615(10) 0.0224(3) Uani 1 1 d . . . N3 N 0.38516(10) 0.79360(6) -0.13445(10) 0.0227(3) Uani 1 1 d . . . C1 C 0.44070(12) 0.73003(7) -0.07663(12) 0.0217(3) Uani 1 1 d . . . H1A H 0.4123 0.7241 -0.0075 0.026 Uiso 1 1 calc R . . C11 C 0.42453(12) 0.60224(8) -0.08300(12) 0.0242(3) Uani 1 1 d . . . C12 C 0.37729(13) 0.53950(8) -0.14584(13) 0.0257(3) Uani 1 1 d . . . H12A H 0.3872 0.4952 -0.1067 0.031 Uiso 1 1 calc R . . C13 C 0.31897(12) 0.54045(8) -0.25898(13) 0.0240(3) Uani 1 1 d . . . C14 C 0.26236(13) 0.47453(8) -0.32478(14) 0.0298(3) Uani 1 1 d . . . C15 C 0.13125(15) 0.49069(11) -0.37848(19) 0.0471(5) Uani 1 1 d . . . H15A H 0.0958 0.5057 -0.3188 0.071 Uiso 1 1 calc R . . H15B H 0.0913 0.4478 -0.4160 0.071 Uiso 1 1 calc R . . H15C H 0.1230 0.5288 -0.4349 0.071 Uiso 1 1 calc R . . C16 C 0.27363(17) 0.40898(9) -0.24858(16) 0.0396(4) Uani 1 1 d . . . H16A H 0.3571 0.3992 -0.2120 0.059 Uiso 1 1 calc R . . H16B H 0.2376 0.3680 -0.2950 0.059 Uiso 1 1 calc R . . H16C H 0.2334 0.4178 -0.1899 0.059 Uiso 1 1 calc R . . C17 C 0.32044(17) 0.45896(10) -0.41951(16) 0.0415(4) Uani 1 1 d . . . H17A H 0.4046 0.4498 -0.3856 0.062 Uiso 1 1 calc R . . H17B H 0.3104 0.5000 -0.4708 0.062 Uiso 1 1 calc R . . H17C H 0.2834 0.4171 -0.4628 0.062 Uiso 1 1 calc R . . C18 C 0.30832(13) 0.60678(8) -0.31721(12) 0.0255(3) Uani 1 1 d . . . H18A H 0.2710 0.6086 -0.3970 0.031 Uiso 1 1 calc R . . C19 C 0.35040(12) 0.66687(8) -0.26083(12) 0.0243(3) Uani 1 1 d . . . H19A H 0.3415 0.7107 -0.3012 0.029 Uiso 1 1 calc R . . C21 C 0.61324(13) 0.76426(8) 0.07436(13) 0.0258(3) Uani 1 1 d . . . C22 C 0.73996(13) 0.76691(9) 0.11610(13) 0.0279(3) Uani 1 1 d . . . H22A H 0.7743 0.7843 0.1912 0.033 Uiso 1 1 calc R . . C23 C 0.81277(12) 0.74614(8) 0.05461(13) 0.0248(3) Uani 1 1 d . . . C24 C 0.94671(13) 0.75112(9) 0.09893(14) 0.0302(3) Uani 1 1 d . . . C25 C 1.00404(17) 0.68343(12) 0.0704(2) 0.0537(5) Uani 1 1 d . . . H25A H 0.9752 0.6423 0.1037 0.081 Uiso 1 1 calc R . . H25B H 1.0898 0.6869 0.1017 0.081 Uiso 1 1 calc R . . H25C H 0.9839 0.6778 -0.0127 0.081 Uiso 1 1 calc R . . C26 C 0.98869(16) 0.76295(14) 0.22704(16) 0.0513(5) Uani 1 1 d . . . H26A H 0.9591 0.7246 0.2658 0.077 Uiso 1 1 calc R . . H26B H 0.9590 0.8087 0.2456 0.077 Uiso 1 1 calc R . . H26C H 1.0750 0.7631 0.2523 0.077 Uiso 1 1 calc R . . C27 C 0.98641(16) 0.81430(12) 0.03982(18) 0.0468(5) Uani 1 1 d . . . H27A H 0.9542 0.8584 0.0616 0.070 Uiso 1 1 calc R . . H27B H 0.9578 0.8081 -0.0431 0.070 Uiso 1 1 calc R . . H27C H 1.0726 0.8168 0.0632 0.070 Uiso 1 1 calc R . . C28 C 0.75948(13) 0.72036(9) -0.05793(13) 0.0294(3) Uani 1 1 d . . . H28A H 0.8078 0.7062 -0.1043 0.035 Uiso 1 1 calc R . . C29 C 0.64133(13) 0.71589(8) -0.09937(13) 0.0264(3) Uani 1 1 d . . . H29A H 0.6077 0.6973 -0.1738 0.032 Uiso 1 1 calc R . . C31 C 0.28447(12) 0.81786(8) -0.10637(13) 0.0241(3) Uani 1 1 d . . . C32 C 0.23654(13) 0.88373(8) -0.16012(13) 0.0270(3) Uani 1 1 d . . . H32A H 0.1701 0.9034 -0.1420 0.032 Uiso 1 1 calc R . . C33 C 0.28121(13) 0.91924(8) -0.23542(13) 0.0268(3) Uani 1 1 d . . . C34 C 0.23283(15) 0.98994(9) -0.29074(15) 0.0350(4) Uani 1 1 d . . . C35 C 0.12151(17) 1.01259(10) -0.26066(19) 0.0453(5) Uani 1 1 d . . . H35A H 0.0607 0.9761 -0.2864 0.068 Uiso 1 1 calc R . . H35B H 0.0931 1.0578 -0.2985 0.068 Uiso 1 1 calc R . . H35C H 0.1392 1.0185 -0.1778 0.068 Uiso 1 1 calc R . . C36 C 0.20469(19) 0.98381(12) -0.42040(17) 0.0505(5) Uani 1 1 d . . . H36A H 0.1457 0.9465 -0.4478 0.076 Uiso 1 1 calc R . . H36B H 0.2766 0.9718 -0.4410 0.076 Uiso 1 1 calc R . . H36C H 0.1737 1.0293 -0.4556 0.076 Uiso 1 1 calc R . . C37 C 0.32837(18) 1.04652(10) -0.2457(2) 0.0477(5) Uani 1 1 d . . . H37A H 0.3497 1.0476 -0.1621 0.072 Uiso 1 1 calc R . . H37B H 0.2983 1.0932 -0.2759 0.072 Uiso 1 1 calc R . . H37C H 0.3981 1.0348 -0.2703 0.072 Uiso 1 1 calc R . . C38 C 0.38042(14) 0.88899(8) -0.26277(14) 0.0286(3) Uani 1 1 d . . . H38A H 0.4120 0.9116 -0.3171 0.034 Uiso 1 1 calc R . . C39 C 0.42934(13) 0.82869(8) -0.21206(13) 0.0267(3) Uani 1 1 d . . . H39A H 0.4962 0.8098 -0.2303 0.032 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 O1 0.0372(6) 0.0308(6) 0.0223(5) 0.0024(4) 0.0022(5) 0.0003(5) O2 0.0274(6) 0.0544(8) 0.0277(6) -0.0116(5) 0.0114(5) -0.0025(5) O3 0.0262(5) 0.0372(6) 0.0352(6) 0.0036(5) 0.0153(5) 0.0000(4) N1 0.0211(6) 0.0216(6) 0.0219(6) 0.0004(5) 0.0044(5) -0.0001(4) N2 0.0190(5) 0.0268(6) 0.0214(6) -0.0011(5) 0.0057(4) 0.0002(5) N3 0.0204(6) 0.0244(6) 0.0242(6) 0.0004(5) 0.0080(5) 0.0001(4) C1 0.0189(6) 0.0247(7) 0.0218(7) -0.0007(5) 0.0059(5) 0.0000(5) C11 0.0222(7) 0.0265(7) 0.0241(7) 0.0022(6) 0.0071(6) 0.0007(5) C12 0.0267(7) 0.0234(7) 0.0263(7) 0.0029(6) 0.0065(6) 0.0003(6) C13 0.0170(6) 0.0269(7) 0.0280(7) -0.0013(6) 0.0062(5) 0.0000(5) C14 0.0245(7) 0.0266(8) 0.0334(8) -0.0039(6) 0.0003(6) -0.0012(6) C15 0.0253(8) 0.0415(10) 0.0645(13) -0.0093(9) -0.0037(8) -0.0043(7) C16 0.0422(10) 0.0279(9) 0.0430(10) -0.0027(7) 0.0029(8) -0.0080(7) C17 0.0460(10) 0.0376(10) 0.0372(9) -0.0083(8) 0.0056(8) 0.0050(8) C18 0.0239(7) 0.0297(8) 0.0210(7) 0.0012(6) 0.0036(5) 0.0001(6) C19 0.0218(6) 0.0271(7) 0.0232(7) 0.0034(6) 0.0049(5) 0.0000(5) C21 0.0239(7) 0.0311(8) 0.0230(7) -0.0026(6) 0.0075(6) -0.0019(6) C22 0.0229(7) 0.0377(9) 0.0217(7) -0.0044(6) 0.0042(6) -0.0032(6) C23 0.0216(7) 0.0261(7) 0.0260(8) 0.0032(6) 0.0054(6) 0.0005(5) C24 0.0198(7) 0.0397(9) 0.0291(8) 0.0009(7) 0.0036(6) 0.0021(6) C25 0.0337(10) 0.0527(12) 0.0654(14) -0.0064(10) -0.0014(9) 0.0162(9) C26 0.0280(9) 0.0858(16) 0.0329(10) -0.0026(10) -0.0028(7) 0.0019(9) C27 0.0262(8) 0.0595(12) 0.0530(12) 0.0072(10) 0.0083(8) -0.0076(8) C28 0.0229(7) 0.0401(9) 0.0257(8) -0.0034(6) 0.0076(6) 0.0030(6) C29 0.0233(7) 0.0344(8) 0.0218(7) -0.0047(6) 0.0071(6) 0.0015(6) C31 0.0194(6) 0.0284(7) 0.0249(7) -0.0045(6) 0.0071(5) -0.0030(5) C32 0.0215(7) 0.0287(8) 0.0321(8) -0.0022(6) 0.0098(6) 0.0026(6) C33 0.0240(7) 0.0267(8) 0.0296(8) -0.0011(6) 0.0073(6) -0.0003(6) C34 0.0333(8) 0.0309(9) 0.0429(10) 0.0067(7) 0.0141(7) 0.0064(7) C35 0.0406(10) 0.0378(10) 0.0604(12) 0.0110(9) 0.0188(9) 0.0155(8) C36 0.0553(12) 0.0533(12) 0.0436(11) 0.0173(9) 0.0153(9) 0.0192(10) C37 0.0481(11) 0.0290(9) 0.0699(14) 0.0078(9) 0.0229(10) 0.0005(8) C38 0.0274(7) 0.0298(8) 0.0314(8) 0.0028(6) 0.0127(6) -0.0011(6) C39 0.0232(7) 0.0301(8) 0.0298(8) -0.0004(6) 0.0124(6) -0.0009(6) _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 O1 C11 1.2324(18) . ? O2 C21 1.2310(18) . ? O3 C31 1.2280(18) . ? N1 C19 1.3733(18) . ? N1 C11 1.4054(18) . ? N1 C1 1.4622(18) . ? N2 C29 1.3663(18) . ? N2 C21 1.3957(19) . ? N2 C1 1.4665(18) . ? N3 C39 1.3742(18) . ? N3 C31 1.4064(18) . ? N3 C1 1.4480(18) . ? C11 C12 1.432(2) . ? C12 C13 1.359(2) . ? C13 C18 1.423(2) . ? C13 C14 1.525(2) . ? C14 C16 1.527(2) . ? C14 C17 1.532(2) . ? C14 C15 1.535(2) . ? C18 C19 1.343(2) . ? C21 C22 1.442(2) . ? C22 C23 1.351(2) . ? C23 C28 1.426(2) . ? C23 C24 1.526(2) . ? C24 C26 1.519(2) . ? C24 C25 1.528(3) . ? C24 C27 1.531(3) . ? C28 C29 1.348(2) . ? C31 C32 1.441(2) . ? C32 C33 1.359(2) . ? C33 C38 1.427(2) . ? C33 C34 1.527(2) . ? C34 C35 1.525(2) . ? C34 C36 1.528(3) . ? C34 C37 1.537(3) . ? C38 C39 1.342(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 N1 C11 121.67(12) . . ? C19 N1 C1 123.76(12) . . ? C11 N1 C1 114.32(11) . . ? C29 N2 C21 122.11(12) . . ? C29 N2 C1 122.34(12) . . ? C21 N2 C1 115.42(12) . . ? C39 N3 C31 121.79(12) . . ? C39 N3 C1 121.60(12) . . ? C31 N3 C1 116.60(12) . . ? N3 C1 N1 112.58(11) . . ? N3 C1 N2 111.63(11) . . ? N1 C1 N2 111.67(11) . . ? O1 C11 N1 118.83(13) . . ? O1 C11 C12 125.53(14) . . ? N1 C11 C12 115.62(12) . . ? C13 C12 C11 122.90(14) . . ? C12 C13 C18 117.87(13) . . ? C12 C13 C14 123.11(14) . . ? C18 C13 C14 119.00(13) . . ? C13 C14 C16 112.63(13) . . ? C13 C14 C17 109.22(13) . . ? C16 C14 C17 109.02(14) . . ? C13 C14 C15 107.74(13) . . ? C16 C14 C15 108.88(15) . . ? C17 C14 C15 109.30(15) . . ? C19 C18 C13 120.86(13) . . ? C18 C19 N1 120.99(13) . . ? O2 C21 N2 120.24(13) . . ? O2 C21 C22 124.84(14) . . ? N2 C21 C22 114.92(13) . . ? C23 C22 C21 123.83(14) . . ? C22 C23 C28 117.17(13) . . ? C22 C23 C24 123.16(14) . . ? C28 C23 C24 119.64(13) . . ? C26 C24 C23 112.25(14) . . ? C26 C24 C25 108.69(16) . . ? C23 C24 C25 110.59(14) . . ? C26 C24 C27 108.54(16) . . ? C23 C24 C27 107.87(13) . . ? C25 C24 C27 108.83(16) . . ? C29 C28 C23 120.80(14) . . ? C28 C29 N2 121.15(14) . . ? O3 C31 N3 120.18(14) . . ? O3 C31 C32 125.03(14) . . ? N3 C31 C32 114.78(13) . . ? C33 C32 C31 123.53(14) . . ? C32 C33 C38 117.80(14) . . ? C32 C33 C34 123.92(14) . . ? C38 C33 C34 118.28(13) . . ? C35 C34 C33 112.19(14) . . ? C35 C34 C36 108.73(16) . . ? C33 C34 C36 109.72(14) . . ? C35 C34 C37 108.60(16) . . ? C33 C34 C37 107.35(14) . . ? C36 C34 C37 110.23(16) . . ? C39 C38 C33 120.32(14) . . ? C38 C39 N3 121.69(14) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.75 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.501 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 951234' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_o3znophs10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H57 Cl8 N3 O4 Zn' _chemical_formula_weight 1016.88 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' Cl Cl 0.1484 0.1585 '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 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 14.5805(16) _cell_length_b 14.0968(15) _cell_length_c 24.168(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.703(2) _cell_angle_gamma 90.00 _cell_volume 4957.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9975 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 30.55 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 0.968 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.5944 _exptl_absorpt_correction_T_max 0.9532 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 43118 _diffrn_reflns_av_R_equivalents 0.1209 _diffrn_reflns_av_sigmaI/netI 0.1037 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 24.71 _reflns_number_total 8462 _reflns_number_gt 5206 _reflns_threshold_expression >2sigma(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 ; 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^)+(0.0719P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8462 _refine_ls_number_parameters 535 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1269 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.1723 _refine_ls_wR_factor_gt 0.1524 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 Zn Zn 0.28572(4) 0.72101(4) 0.18177(2) 0.02136(19) Uani 1 1 d . . . O1 O 0.1399(2) 0.7136(2) 0.15907(14) 0.0246(8) Uani 1 1 d . . . O2 O 0.3929(2) 0.6235(2) 0.16686(14) 0.0268(9) Uani 1 1 d . . . O3 O 0.3044(2) 0.7744(2) 0.26239(14) 0.0259(9) Uani 1 1 d . . . O4 O 0.3129(2) 0.8158(2) 0.12999(14) 0.0262(9) Uani 1 1 d . . . N1 N 0.1625(3) 0.5657(3) 0.19647(16) 0.0191(10) Uani 1 1 d . . . N2 N 0.3198(3) 0.5380(3) 0.23241(16) 0.0167(9) Uani 1 1 d . . . N3 N 0.2206(3) 0.6416(3) 0.28074(16) 0.0182(10) Uani 1 1 d . . . C1 C 0.2443(3) 0.6050(3) 0.22649(19) 0.0172(11) Uani 1 1 d . . . C11 C 0.1122(3) 0.6290(3) 0.1626(2) 0.0210(12) Uani 1 1 d . . . C12 C 0.0320(4) 0.5940(4) 0.1336(2) 0.0231(12) Uani 1 1 d . . . H12A H -0.0045 0.6368 0.1112 0.028 Uiso 1 1 calc R . . C13 C 0.0045(3) 0.5023(4) 0.1363(2) 0.0225(12) Uani 1 1 d . . . C14 C -0.0827(4) 0.4649(4) 0.1054(2) 0.0288(13) Uani 1 1 d . . . C15 C -0.0558(4) 0.3866(4) 0.0660(2) 0.0415(16) Uani 1 1 d . . . H15A H -0.1111 0.3614 0.0460 0.062 Uiso 1 1 calc R . . H15B H -0.0245 0.3355 0.0873 0.062 Uiso 1 1 calc R . . H15C H -0.0144 0.4126 0.0394 0.062 Uiso 1 1 calc R . . C16 C -0.1448(4) 0.4231(5) 0.1474(3) 0.0503(18) Uani 1 1 d . . . H16A H -0.2003 0.3970 0.1280 0.075 Uiso 1 1 calc R . . H16B H -0.1621 0.4728 0.1731 0.075 Uiso 1 1 calc R . . H16C H -0.1120 0.3725 0.1683 0.075 Uiso 1 1 calc R . . C17 C -0.1347(4) 0.5416(4) 0.0725(2) 0.0387(15) Uani 1 1 d . . . H17A H -0.1898 0.5141 0.0534 0.058 Uiso 1 1 calc R . . H17B H -0.0952 0.5684 0.0452 0.058 Uiso 1 1 calc R . . H17C H -0.1527 0.5917 0.0977 0.058 Uiso 1 1 calc R . . C18 C 0.0613(4) 0.4412(4) 0.1700(2) 0.0233(13) Uani 1 1 d . . . H18A H 0.0455 0.3760 0.1724 0.028 Uiso 1 1 calc R . . C19 C 0.1358(3) 0.4727(3) 0.1980(2) 0.0209(12) Uani 1 1 d . . . H19A H 0.1722 0.4293 0.2200 0.025 Uiso 1 1 calc R . . C21 C 0.3936(3) 0.5542(4) 0.1992(2) 0.0200(12) Uani 1 1 d . . . C22 C 0.4676(4) 0.4891(4) 0.2040(2) 0.0230(13) Uani 1 1 d . . . H22A H 0.5163 0.4969 0.1801 0.028 Uiso 1 1 calc R . . C23 C 0.4729(3) 0.4158(3) 0.2409(2) 0.0196(12) Uani 1 1 d . . . C24 C 0.5530(4) 0.3477(4) 0.2466(2) 0.0253(13) Uani 1 1 d . . . C25 C 0.6283(4) 0.3720(4) 0.2082(2) 0.0376(15) Uani 1 1 d . . . H25A H 0.6510 0.4363 0.2163 0.056 Uiso 1 1 calc R . . H25B H 0.6034 0.3689 0.1696 0.056 Uiso 1 1 calc R . . H25C H 0.6789 0.3266 0.2139 0.056 Uiso 1 1 calc R . . C26 C 0.5158(4) 0.2486(4) 0.2317(3) 0.0373(15) Uani 1 1 d . . . H26A H 0.4947 0.2469 0.1924 0.056 Uiso 1 1 calc R . . H26B H 0.4643 0.2339 0.2544 0.056 Uiso 1 1 calc R . . H26C H 0.5646 0.2015 0.2388 0.056 Uiso 1 1 calc R . . C27 C 0.5919(4) 0.3469(4) 0.3065(2) 0.0400(16) Uani 1 1 d . . . H27A H 0.6146 0.4103 0.3168 0.060 Uiso 1 1 calc R . . H27B H 0.6426 0.3013 0.3107 0.060 Uiso 1 1 calc R . . H27C H 0.5436 0.3286 0.3308 0.060 Uiso 1 1 calc R . . C28 C 0.3984(3) 0.4061(3) 0.2754(2) 0.0207(12) Uani 1 1 d . . . H28A H 0.3996 0.3567 0.3022 0.025 Uiso 1 1 calc R . . C29 C 0.3257(4) 0.4661(3) 0.2708(2) 0.0213(12) Uani 1 1 d . . . H29A H 0.2772 0.4580 0.2948 0.026 Uiso 1 1 calc R . . C31 C 0.2560(3) 0.7312(4) 0.2950(2) 0.0213(12) Uani 1 1 d . . . C32 C 0.2339(4) 0.7663(3) 0.3471(2) 0.0226(12) Uani 1 1 d . . . H32A H 0.2579 0.8264 0.3584 0.027 Uiso 1 1 calc R . . C33 C 0.1810(3) 0.7200(4) 0.3821(2) 0.0228(12) Uani 1 1 d . . . C34 C 0.1611(4) 0.7635(4) 0.4382(2) 0.0307(14) Uani 1 1 d . . . C35 C 0.0996(5) 0.7017(5) 0.4706(3) 0.0513(19) Uani 1 1 d . . . H35A H 0.1288 0.6397 0.4772 0.077 Uiso 1 1 calc R . . H35B H 0.0405 0.6931 0.4495 0.077 Uiso 1 1 calc R . . H35C H 0.0895 0.7319 0.5062 0.077 Uiso 1 1 calc R . . C36 C 0.1103(5) 0.8581(4) 0.4274(3) 0.057(2) Uani 1 1 d . . . H36A H 0.0929 0.8848 0.4627 0.085 Uiso 1 1 calc R . . H36B H 0.0549 0.8472 0.4031 0.085 Uiso 1 1 calc R . . H36C H 0.1508 0.9027 0.4096 0.085 Uiso 1 1 calc R . . C37 C 0.2499(5) 0.7798(6) 0.4719(3) 0.064(2) Uani 1 1 d . . . H37A H 0.2834 0.7197 0.4763 0.096 Uiso 1 1 calc R . . H37B H 0.2369 0.8044 0.5085 0.096 Uiso 1 1 calc R . . H37C H 0.2872 0.8258 0.4530 0.096 Uiso 1 1 calc R . . C38 C 0.1456(4) 0.6311(4) 0.3643(2) 0.0241(13) Uani 1 1 d . . . H38A H 0.1077 0.5959 0.3874 0.029 Uiso 1 1 calc R . . C39 C 0.1654(3) 0.5964(3) 0.3150(2) 0.0193(12) Uani 1 1 d . . . H39A H 0.1395 0.5372 0.3035 0.023 Uiso 1 1 calc R . . C40 C 0.3939(4) 0.8593(3) 0.1316(2) 0.0210(12) Uani 1 1 d . . . C41 C 0.4272(4) 0.8969(4) 0.0834(2) 0.0273(13) Uani 1 1 d . . . H41A H 0.3922 0.8889 0.0492 0.033 Uiso 1 1 calc R . . C42 C 0.5095(4) 0.9453(4) 0.0841(2) 0.0258(13) Uani 1 1 d . . . H42A H 0.5292 0.9705 0.0504 0.031 Uiso 1 1 calc R . . C43 C 0.5646(4) 0.9581(4) 0.1328(2) 0.0226(12) Uani 1 1 d . . . C44 C 0.6555(4) 1.0122(4) 0.1318(2) 0.0286(14) Uani 1 1 d . . . C45 C 0.7218(4) 0.9576(4) 0.0962(2) 0.0401(16) Uani 1 1 d . . . H45A H 0.7306 0.8932 0.1109 0.060 Uiso 1 1 calc R . . H45B H 0.7811 0.9905 0.0972 0.060 Uiso 1 1 calc R . . H45C H 0.6957 0.9544 0.0578 0.060 Uiso 1 1 calc R . . C46 C 0.6401(4) 1.1118(4) 0.1072(2) 0.0373(15) Uani 1 1 d . . . H46A H 0.5958 1.1462 0.1286 0.056 Uiso 1 1 calc R . . H46B H 0.6160 1.1065 0.0686 0.056 Uiso 1 1 calc R . . H46C H 0.6985 1.1464 0.1089 0.056 Uiso 1 1 calc R . . C47 C 0.7012(4) 1.0248(4) 0.1896(2) 0.0379(15) Uani 1 1 d . . . H47A H 0.6586 1.0568 0.2133 0.057 Uiso 1 1 calc R . . H47B H 0.7569 1.0632 0.1876 0.057 Uiso 1 1 calc R . . H47C H 0.7175 0.9625 0.2054 0.057 Uiso 1 1 calc R . . C48 C 0.5321(4) 0.9193(4) 0.1801(2) 0.0275(13) Uani 1 1 d . . . H48A H 0.5677 0.9262 0.2142 0.033 Uiso 1 1 calc R . . C49 C 0.4497(4) 0.8705(4) 0.1797(2) 0.0248(13) Uani 1 1 d . . . H49A H 0.4309 0.8440 0.2134 0.030 Uiso 1 1 calc R . . C50 C -0.1551(4) 0.8602(5) 0.5417(2) 0.0449(17) Uani 1 1 d . . . H50A H -0.1026 0.8918 0.5622 0.054 Uiso 1 1 calc R . . H50B H -0.1563 0.7933 0.5540 0.054 Uiso 1 1 calc R . . C60 C 0.4985(6) 0.5809(7) 0.3859(3) 0.093(3) Uani 1 1 d . . . H60A H 0.5159 0.5138 0.3808 0.112 Uiso 1 1 calc R . . H60B H 0.5361 0.6058 0.4183 0.112 Uiso 1 1 calc R . . C70 C 0.9049(4) 1.1950(4) 0.3608(3) 0.0439(17) Uani 1 1 d . . . H70A H 0.8961 1.2555 0.3806 0.053 Uiso 1 1 calc R . . H70B H 0.9682 1.1944 0.3483 0.053 Uiso 1 1 calc R . . C80 C 0.8691(5) 1.1680(6) -0.0516(3) 0.069(2) Uani 1 1 d . . . H80A H 0.8529 1.2323 -0.0655 0.083 Uiso 1 1 calc R . . H80B H 0.8480 1.1218 -0.0805 0.083 Uiso 1 1 calc R . . Cl1 Cl -0.25767(11) 0.91608(12) 0.55786(6) 0.0493(5) Uani 1 1 d . . . Cl2 Cl -0.13915(14) 0.86399(17) 0.47116(7) 0.0740(6) Uani 1 1 d . . . Cl3 Cl 0.38501(17) 0.5862(2) 0.39965(11) 0.1247(12) Uani 1 1 d . . . Cl4 Cl 0.5237(2) 0.64527(18) 0.32700(11) 0.1253(11) Uani 1 1 d . . . Cl5 Cl 0.89183(13) 1.09994(12) 0.40681(7) 0.0593(5) Uani 1 1 d . . . Cl6 Cl 0.82664(16) 1.18876(17) 0.30315(10) 0.0877(7) Uani 1 1 d . . . Cl7 Cl 0.81294(14) 1.14660(19) 0.00726(8) 0.0891(8) Uani 1 1 d . . . Cl8 Cl 0.98887(13) 1.15985(17) -0.04030(8) 0.0778(7) 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 Zn 0.0254(4) 0.0112(3) 0.0275(4) 0.0014(3) 0.0016(3) -0.0017(3) O1 0.030(2) 0.0091(18) 0.035(2) 0.0011(16) -0.0019(17) -0.0003(17) O2 0.033(2) 0.020(2) 0.028(2) 0.0099(17) 0.0055(17) 0.0071(18) O3 0.031(2) 0.0171(19) 0.030(2) 0.0030(17) 0.0069(17) -0.0083(18) O4 0.024(2) 0.0176(19) 0.036(2) 0.0082(17) -0.0016(17) -0.0043(17) N1 0.022(3) 0.010(2) 0.025(2) 0.0026(19) 0.0009(19) -0.0022(19) N2 0.017(2) 0.009(2) 0.024(2) -0.0019(18) 0.0019(18) -0.0006(19) N3 0.017(2) 0.011(2) 0.026(2) -0.0004(19) 0.0013(19) -0.0033(19) C1 0.020(3) 0.012(3) 0.020(3) -0.003(2) 0.000(2) -0.001(2) C11 0.019(3) 0.016(3) 0.028(3) 0.002(2) 0.002(2) 0.003(2) C12 0.024(3) 0.020(3) 0.025(3) 0.001(2) -0.001(2) 0.004(3) C13 0.020(3) 0.022(3) 0.025(3) -0.003(2) 0.003(2) -0.002(2) C14 0.028(3) 0.028(3) 0.030(3) -0.001(3) -0.004(3) -0.007(3) C15 0.045(4) 0.038(4) 0.040(4) -0.012(3) -0.017(3) 0.003(3) C16 0.033(4) 0.061(5) 0.056(4) 0.009(4) -0.003(3) -0.019(4) C17 0.027(4) 0.041(4) 0.047(4) 0.000(3) -0.009(3) -0.001(3) C18 0.025(3) 0.014(3) 0.030(3) 0.000(2) -0.003(3) -0.001(2) C19 0.023(3) 0.012(3) 0.028(3) 0.000(2) -0.001(2) 0.003(2) C21 0.019(3) 0.017(3) 0.024(3) -0.002(2) 0.000(2) 0.001(2) C22 0.023(3) 0.022(3) 0.024(3) -0.005(2) 0.002(2) -0.003(3) C23 0.019(3) 0.014(3) 0.025(3) -0.003(2) -0.002(2) -0.004(2) C24 0.019(3) 0.019(3) 0.038(3) -0.005(3) 0.001(3) 0.002(2) C25 0.027(4) 0.032(3) 0.055(4) 0.003(3) 0.006(3) 0.007(3) C26 0.035(4) 0.021(3) 0.057(4) -0.004(3) 0.010(3) 0.006(3) C27 0.043(4) 0.038(4) 0.038(4) 0.002(3) -0.004(3) 0.011(3) C28 0.020(3) 0.013(3) 0.029(3) 0.002(2) -0.004(2) -0.003(2) C29 0.027(3) 0.016(3) 0.020(3) -0.001(2) 0.000(2) -0.008(3) C31 0.021(3) 0.015(3) 0.027(3) 0.000(2) -0.002(2) 0.000(3) C32 0.033(3) 0.012(3) 0.022(3) -0.005(2) 0.002(2) -0.006(3) C33 0.020(3) 0.018(3) 0.031(3) 0.000(3) -0.002(2) -0.004(3) C34 0.039(4) 0.030(3) 0.024(3) -0.009(3) 0.002(3) -0.004(3) C35 0.070(5) 0.050(4) 0.035(4) -0.006(3) 0.016(3) -0.017(4) C36 0.093(6) 0.038(4) 0.041(4) -0.004(3) 0.019(4) 0.019(4) C37 0.056(5) 0.096(6) 0.039(4) -0.031(4) 0.000(3) -0.003(5) C38 0.023(3) 0.022(3) 0.027(3) 0.006(2) 0.003(2) -0.004(3) C39 0.016(3) 0.014(3) 0.028(3) 0.001(2) 0.002(2) 0.001(2) C40 0.024(3) 0.009(3) 0.030(3) 0.004(2) 0.002(2) 0.006(2) C41 0.035(4) 0.019(3) 0.028(3) 0.000(2) 0.002(3) -0.001(3) C42 0.035(4) 0.019(3) 0.024(3) 0.003(2) 0.007(3) 0.001(3) C43 0.023(3) 0.019(3) 0.026(3) -0.003(2) 0.002(2) 0.004(2) C44 0.028(3) 0.025(3) 0.033(3) 0.002(3) 0.004(3) 0.002(3) C45 0.029(4) 0.045(4) 0.047(4) -0.005(3) 0.007(3) 0.003(3) C46 0.035(4) 0.027(3) 0.050(4) 0.004(3) 0.003(3) -0.008(3) C47 0.027(4) 0.041(4) 0.046(4) -0.002(3) -0.002(3) -0.006(3) C48 0.032(4) 0.024(3) 0.026(3) 0.001(3) -0.004(3) 0.002(3) C49 0.032(3) 0.021(3) 0.022(3) 0.006(2) 0.007(3) 0.002(3) C50 0.039(4) 0.057(4) 0.038(4) 0.011(3) -0.001(3) -0.003(3) C60 0.095(7) 0.098(7) 0.081(6) -0.013(5) -0.036(5) 0.039(6) C70 0.040(4) 0.035(4) 0.057(4) -0.008(3) 0.004(3) -0.001(3) C80 0.047(5) 0.102(7) 0.057(5) 0.039(5) 0.007(4) 0.014(5) Cl1 0.0477(11) 0.0559(11) 0.0443(10) 0.0076(8) 0.0040(8) 0.0069(9) Cl2 0.0695(14) 0.1113(17) 0.0424(11) 0.0105(11) 0.0122(9) 0.0267(13) Cl3 0.0838(18) 0.186(3) 0.0995(19) -0.0688(19) -0.0325(14) 0.073(2) Cl4 0.198(3) 0.0707(17) 0.103(2) -0.0246(15) -0.024(2) -0.0026(18) Cl5 0.0748(14) 0.0466(11) 0.0600(11) -0.0070(9) 0.0312(10) -0.0129(10) Cl6 0.0755(16) 0.0824(16) 0.1003(17) -0.0088(13) -0.0316(13) 0.0095(13) Cl7 0.0615(14) 0.148(2) 0.0577(13) 0.0388(14) 0.0042(10) -0.0082(14) Cl8 0.0494(13) 0.1144(19) 0.0694(14) 0.0209(13) 0.0025(10) 0.0055(12) _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 Zn O4 1.890(3) . ? Zn C1 2.071(5) . ? Zn O3 2.090(3) . ? Zn O2 2.129(3) . ? Zn O1 2.164(3) . ? O1 C11 1.263(6) . ? O2 C21 1.251(6) . ? O3 C31 1.250(6) . ? O4 C40 1.330(6) . ? N1 C19 1.369(6) . ? N1 C11 1.387(6) . ? N1 C1 1.465(6) . ? N2 C29 1.373(6) . ? N2 C21 1.401(6) . ? N2 C1 1.450(6) . ? N3 C39 1.351(6) . ? N3 C31 1.400(6) . ? N3 C1 1.471(6) . ? C11 C12 1.414(7) . ? C12 C13 1.357(7) . ? C13 C18 1.415(7) . ? C13 C14 1.526(7) . ? C14 C17 1.516(7) . ? C14 C16 1.522(8) . ? C14 C15 1.526(8) . ? C18 C19 1.320(7) . ? C21 C22 1.415(7) . ? C22 C23 1.364(7) . ? C23 C28 1.418(7) . ? C23 C24 1.512(7) . ? C24 C25 1.522(7) . ? C24 C27 1.522(7) . ? C24 C26 1.533(7) . ? C28 C29 1.356(7) . ? C31 C32 1.409(7) . ? C32 C33 1.350(7) . ? C33 C38 1.412(7) . ? C33 C34 1.533(7) . ? C34 C37 1.502(8) . ? C34 C35 1.505(8) . ? C34 C36 1.539(8) . ? C38 C39 1.337(7) . ? C40 C49 1.386(7) . ? C40 C41 1.394(7) . ? C41 C42 1.380(7) . ? C42 C43 1.393(7) . ? C43 C48 1.378(7) . ? C43 C44 1.531(7) . ? C44 C47 1.519(7) . ? C44 C46 1.536(7) . ? C44 C45 1.541(7) . ? C48 C49 1.385(7) . ? C50 Cl2 1.736(6) . ? C50 Cl1 1.756(6) . ? C60 Cl3 1.710(9) . ? C60 Cl4 1.747(10) . ? C70 Cl6 1.746(6) . ? C70 Cl5 1.759(6) . ? C80 Cl7 1.713(7) . ? C80 Cl8 1.754(7) . ? 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 O4 Zn C1 169.78(17) . . ? O4 Zn O3 110.02(14) . . ? C1 Zn O3 79.79(16) . . ? O4 Zn O2 99.03(14) . . ? C1 Zn O2 79.63(16) . . ? O3 Zn O2 109.73(14) . . ? O4 Zn O1 96.36(14) . . ? C1 Zn O1 77.26(16) . . ? O3 Zn O1 108.69(13) . . ? O2 Zn O1 130.20(13) . . ? C11 O1 Zn 109.9(3) . . ? C21 O2 Zn 112.0(3) . . ? C31 O3 Zn 111.6(3) . . ? C40 O4 Zn 122.1(3) . . ? C19 N1 C11 119.5(4) . . ? C19 N1 C1 124.9(4) . . ? C11 N1 C1 115.5(4) . . ? C29 N2 C21 119.3(4) . . ? C29 N2 C1 124.1(4) . . ? C21 N2 C1 116.3(4) . . ? C39 N3 C31 119.9(4) . . ? C39 N3 C1 124.4(4) . . ? C31 N3 C1 115.6(4) . . ? N2 C1 N1 113.1(4) . . ? N2 C1 N3 111.2(4) . . ? N1 C1 N3 110.0(4) . . ? N2 C1 Zn 108.7(3) . . ? N1 C1 Zn 107.2(3) . . ? N3 C1 Zn 106.4(3) . . ? O1 C11 N1 119.2(4) . . ? O1 C11 C12 123.6(5) . . ? N1 C11 C12 117.2(4) . . ? C13 C12 C11 123.1(5) . . ? C12 C13 C18 116.3(5) . . ? C12 C13 C14 123.1(5) . . ? C18 C13 C14 120.6(5) . . ? C17 C14 C16 109.1(5) . . ? C17 C14 C15 109.2(5) . . ? C16 C14 C15 109.0(5) . . ? C17 C14 C13 112.5(4) . . ? C16 C14 C13 108.7(4) . . ? C15 C14 C13 108.4(5) . . ? C19 C18 C13 121.5(5) . . ? C18 C19 N1 122.3(5) . . ? O2 C21 N2 120.6(4) . . ? O2 C21 C22 122.2(5) . . ? N2 C21 C22 117.2(4) . . ? C23 C22 C21 123.8(5) . . ? C22 C23 C28 116.3(5) . . ? C22 C23 C24 123.5(5) . . ? C28 C23 C24 120.1(4) . . ? C23 C24 C25 112.6(4) . . ? C23 C24 C27 109.2(4) . . ? C25 C24 C27 110.1(5) . . ? C23 C24 C26 107.3(4) . . ? C25 C24 C26 108.7(5) . . ? C27 C24 C26 108.7(5) . . ? C29 C28 C23 121.1(5) . . ? C28 C29 N2 122.0(5) . . ? O3 C31 N3 119.9(4) . . ? O3 C31 C32 124.3(5) . . ? N3 C31 C32 115.8(5) . . ? C33 C32 C31 124.3(5) . . ? C32 C33 C38 116.8(5) . . ? C32 C33 C34 120.6(5) . . ? C38 C33 C34 122.6(5) . . ? C37 C34 C35 109.1(5) . . ? C37 C34 C33 109.6(5) . . ? C35 C34 C33 112.4(5) . . ? C37 C34 C36 110.4(5) . . ? C35 C34 C36 107.1(5) . . ? C33 C34 C36 108.3(4) . . ? C39 C38 C33 120.0(5) . . ? C38 C39 N3 123.1(5) . . ? O4 C40 C49 123.2(5) . . ? O4 C40 C41 120.5(5) . . ? C49 C40 C41 116.2(5) . . ? C42 C41 C40 121.8(5) . . ? C41 C42 C43 121.9(5) . . ? C48 C43 C42 116.0(5) . . ? C48 C43 C44 123.7(5) . . ? C42 C43 C44 120.3(5) . . ? C47 C44 C43 111.9(4) . . ? C47 C44 C46 107.1(5) . . ? C43 C44 C46 110.8(4) . . ? C47 C44 C45 108.6(5) . . ? C43 C44 C45 109.6(4) . . ? C46 C44 C45 108.8(5) . . ? C43 C48 C49 122.5(5) . . ? C48 C49 C40 121.5(5) . . ? Cl2 C50 Cl1 112.0(3) . . ? Cl3 C60 Cl4 113.1(5) . . ? Cl6 C70 Cl5 112.0(3) . . ? Cl7 C80 Cl8 112.6(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.003 _refine_diff_density_min -0.820 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 951235' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_o3znntms10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H40 N4 O4 Si2 Zn' _chemical_formula_weight 594.17 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.347(3) _cell_length_b 10.513(3) _cell_length_c 15.117(5) _cell_angle_alpha 102.776(5) _cell_angle_beta 105.658(5) _cell_angle_gamma 97.886(5) _cell_volume 1509.9(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5899 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 28.70 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8888 _exptl_absorpt_correction_T_max 0.9550 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24546 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.1018 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 30.63 _reflns_number_total 9236 _reflns_number_gt 5464 _reflns_threshold_expression >2sigma(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 ; 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^)+(0.0250P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9236 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1087 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.0905 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Zn Zn 0.25409(3) 1.18520(3) 1.25479(2) 0.02233(8) Uani 1 1 d . . . N3 N 0.18557(19) 0.88685(18) 1.18954(13) 0.0190(4) Uani 1 1 d . . . O2 O 0.29686(17) 1.21779(16) 1.40252(11) 0.0282(4) Uani 1 1 d . . . O1 O 0.04646(17) 1.19884(16) 1.21380(13) 0.0318(4) Uani 1 1 d . . . Si1 Si 0.34657(7) 1.23986(7) 1.09071(5) 0.02673(17) Uani 1 1 d . . . Si2 Si 0.47920(7) 1.42643(7) 1.29197(5) 0.02644(17) Uani 1 1 d . . . N1 N 0.02209(18) 0.99735(18) 1.25012(13) 0.0185(4) Uani 1 1 d . . . N2 N 0.23573(18) 0.98913(18) 1.35715(13) 0.0186(4) Uani 1 1 d . . . N4 N 0.35688(19) 1.30148(18) 1.20683(13) 0.0226(4) Uani 1 1 d . . . O3 O 0.41448(16) 0.98358(17) 1.24957(11) 0.0287(4) Uani 1 1 d . . . C31 C 0.3227(2) 0.8925(2) 1.18977(17) 0.0238(5) Uani 1 1 d . . . C15 C -0.0596(2) 0.8994(2) 1.27056(16) 0.0234(5) Uani 1 1 d . . . H15A H -0.0213 0.8286 1.2890 0.028 Uiso 1 1 calc R . . C35 C 0.0795(3) 0.7967(2) 1.11914(17) 0.0260(6) Uani 1 1 d . . . H35A H -0.0119 0.7986 1.1193 0.031 Uiso 1 1 calc R . . C1 C 0.1678(2) 0.9991(2) 1.26006(15) 0.0180(5) Uani 1 1 d . . . C22 C 0.3587(2) 1.1018(3) 1.52021(17) 0.0268(6) Uani 1 1 d . . . H22A H 0.3976 1.1816 1.5704 0.032 Uiso 1 1 calc R . . C11 C -0.0284(2) 1.1063(2) 1.22701(17) 0.0235(5) Uani 1 1 d . . . C25 C 0.2442(2) 0.8698(2) 1.37845(17) 0.0225(5) Uani 1 1 d . . . H25A H 0.2062 0.7893 1.3288 0.027 Uiso 1 1 calc R . . C23 C 0.3627(2) 0.9827(3) 1.54043(18) 0.0298(6) Uani 1 1 d . . . H23A H 0.4046 0.9800 1.6040 0.036 Uiso 1 1 calc R . . C21 C 0.2979(2) 1.1103(2) 1.42566(16) 0.0226(5) Uani 1 1 d . . . C14 C -0.1910(2) 0.9009(2) 1.26525(17) 0.0278(6) Uani 1 1 d . . . H14A H -0.2451 0.8317 1.2789 0.033 Uiso 1 1 calc R . . C12 C -0.1695(2) 1.1051(3) 1.22074(18) 0.0292(6) Uani 1 1 d . . . H12A H -0.2090 1.1758 1.2032 0.035 Uiso 1 1 calc R . . C34 C 0.1011(3) 0.7052(3) 1.04943(19) 0.0365(7) Uani 1 1 d . . . H34A H 0.0260 0.6437 1.0010 0.044 Uiso 1 1 calc R . . C13 C -0.2476(2) 1.0068(3) 1.23905(17) 0.0292(6) Uani 1 1 d . . . H13A H -0.3407 1.0088 1.2343 0.035 Uiso 1 1 calc R . . C50 C 0.5727(3) 1.5448(3) 1.2428(2) 0.0458(8) Uani 1 1 d . . . H50A H 0.5097 1.5961 1.2132 0.069 Uiso 1 1 calc R . . H50B H 0.6076 1.4944 1.1948 0.069 Uiso 1 1 calc R . . H50C H 0.6496 1.6059 1.2946 0.069 Uiso 1 1 calc R . . C10 C 0.1994(3) 1.0946(3) 1.03115(18) 0.0376(7) Uani 1 1 d . . . H10A H 0.2186 1.0196 1.0575 0.056 Uiso 1 1 calc R . . H10B H 0.1861 1.0687 0.9624 0.056 Uiso 1 1 calc R . . H10C H 0.1159 1.1192 1.0422 0.056 Uiso 1 1 calc R . . C60 C 0.6112(3) 1.3564(3) 1.36661(19) 0.0398(7) Uani 1 1 d . . . H60A H 0.5659 1.2928 1.3931 0.060 Uiso 1 1 calc R . . H60B H 0.6758 1.4289 1.4188 0.060 Uiso 1 1 calc R . . H60C H 0.6609 1.3107 1.3271 0.060 Uiso 1 1 calc R . . C32 C 0.3427(3) 0.7911(3) 1.11784(18) 0.0322(6) Uani 1 1 d . . . H32A H 0.4337 0.7859 1.1179 0.039 Uiso 1 1 calc R . . C40 C 0.4003(3) 1.5265(3) 1.3726(2) 0.0465(8) Uani 1 1 d . . . H40A H 0.3479 1.4671 1.3982 0.070 Uiso 1 1 calc R . . H40B H 0.3388 1.5734 1.3368 0.070 Uiso 1 1 calc R . . H40C H 0.4727 1.5916 1.4254 0.070 Uiso 1 1 calc R . . C30 C 0.5036(3) 1.1796(3) 1.0781(2) 0.0497(8) Uani 1 1 d . . . H30A H 0.5219 1.1151 1.1153 0.075 Uiso 1 1 calc R . . H30B H 0.5820 1.2554 1.1015 0.075 Uiso 1 1 calc R . . H30C H 0.4896 1.1368 1.0107 0.075 Uiso 1 1 calc R . . C33 C 0.2371(3) 0.7024(3) 1.04976(19) 0.0374(7) Uani 1 1 d . . . H33A H 0.2542 0.6378 1.0018 0.045 Uiso 1 1 calc R . . C20 C 0.3185(3) 1.3641(3) 1.01916(19) 0.0447(8) Uani 1 1 d . . . H20A H 0.2374 1.3991 1.0252 0.067 Uiso 1 1 calc R . . H20B H 0.3045 1.3205 0.9519 0.067 Uiso 1 1 calc R . . H20C H 0.3991 1.4376 1.0430 0.067 Uiso 1 1 calc R . . C24 C 0.3050(2) 0.8634(3) 1.46774(18) 0.0278(6) Uani 1 1 d . . . H24A H 0.3087 0.7796 1.4812 0.033 Uiso 1 1 calc R . . O4 O 1.02515(19) 1.35608(17) 0.64090(13) 0.0362(5) Uani 1 1 d . . . C42 C 1.0236(3) 1.4882(3) 0.6876(2) 0.0464(8) Uani 1 1 d . . . H42A H 0.9388 1.5136 0.6543 0.056 Uiso 1 1 calc R . . H42B H 1.1033 1.5508 0.6861 0.056 Uiso 1 1 calc R . . C41 C 1.0192(3) 1.3395(3) 0.5444(2) 0.0448(8) Uani 1 1 d . . . H41A H 1.0963 1.4029 0.5406 0.054 Uiso 1 1 calc R . . H41B H 0.9323 1.3591 0.5087 0.054 Uiso 1 1 calc R . . C43 C 1.0272(3) 1.2001(3) 0.5005(2) 0.0526(9) Uani 1 1 d . . . H43A H 1.0207 1.1894 0.4333 0.079 Uiso 1 1 calc R . . H43B H 0.9514 1.1375 0.5050 0.079 Uiso 1 1 calc R . . H43C H 1.1149 1.1821 0.5344 0.079 Uiso 1 1 calc R . . C44 C 1.0296(4) 1.4962(3) 0.7880(2) 0.0600(10) Uani 1 1 d . . . H44A H 1.0347 1.5887 0.8217 0.090 Uiso 1 1 calc R . . H44B H 1.1110 1.4660 0.8195 0.090 Uiso 1 1 calc R . . H44C H 0.9469 1.4392 0.7889 0.090 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 Zn 0.02236(16) 0.02022(15) 0.02384(15) 0.00560(12) 0.00905(12) -0.00068(11) N3 0.0208(10) 0.0187(10) 0.0183(10) 0.0052(8) 0.0068(8) 0.0051(8) O2 0.0362(10) 0.0224(9) 0.0233(9) 0.0016(7) 0.0124(8) -0.0019(8) O1 0.0259(10) 0.0258(10) 0.0495(12) 0.0189(9) 0.0136(9) 0.0061(8) Si1 0.0297(4) 0.0305(4) 0.0220(4) 0.0122(3) 0.0080(3) 0.0047(3) Si2 0.0252(4) 0.0226(4) 0.0289(4) 0.0079(3) 0.0068(3) -0.0019(3) N1 0.0176(10) 0.0178(10) 0.0193(10) 0.0056(8) 0.0052(8) 0.0020(8) N2 0.0174(10) 0.0212(10) 0.0165(10) 0.0042(8) 0.0059(8) 0.0021(8) N4 0.0223(11) 0.0221(11) 0.0239(11) 0.0082(9) 0.0082(9) 0.0006(8) O3 0.0193(9) 0.0395(11) 0.0249(9) 0.0065(8) 0.0064(8) 0.0031(8) C31 0.0233(13) 0.0328(14) 0.0207(13) 0.0131(11) 0.0086(11) 0.0105(11) C15 0.0241(13) 0.0207(12) 0.0249(13) 0.0074(10) 0.0075(11) 0.0008(10) C35 0.0235(13) 0.0264(13) 0.0241(13) 0.0026(11) 0.0069(11) -0.0008(11) C1 0.0147(11) 0.0204(12) 0.0181(12) 0.0044(10) 0.0045(9) 0.0039(9) C22 0.0186(13) 0.0396(16) 0.0174(12) 0.0004(11) 0.0063(10) 0.0009(11) C11 0.0223(13) 0.0223(13) 0.0240(13) 0.0046(10) 0.0049(11) 0.0055(10) C25 0.0202(13) 0.0250(13) 0.0233(13) 0.0085(11) 0.0069(10) 0.0048(10) C23 0.0182(13) 0.0540(18) 0.0212(13) 0.0141(13) 0.0088(11) 0.0089(12) C21 0.0184(12) 0.0282(14) 0.0203(12) 0.0023(11) 0.0103(10) 0.0006(10) C14 0.0228(13) 0.0319(15) 0.0303(14) 0.0111(12) 0.0114(11) 0.0007(11) C12 0.0226(14) 0.0317(15) 0.0338(15) 0.0087(12) 0.0079(12) 0.0093(11) C34 0.0431(18) 0.0310(15) 0.0279(15) -0.0023(12) 0.0121(13) -0.0020(13) C13 0.0186(13) 0.0393(16) 0.0292(14) 0.0075(12) 0.0085(11) 0.0051(11) C50 0.0396(18) 0.0419(18) 0.0476(19) 0.0179(15) 0.0055(15) -0.0114(14) C10 0.0510(18) 0.0337(15) 0.0233(14) 0.0101(12) 0.0042(13) 0.0041(13) C60 0.0311(16) 0.0477(18) 0.0374(16) 0.0162(14) 0.0061(13) -0.0007(13) C32 0.0346(16) 0.0378(16) 0.0318(15) 0.0114(13) 0.0171(13) 0.0158(13) C40 0.054(2) 0.0262(15) 0.052(2) 0.0000(14) 0.0163(16) 0.0022(14) C30 0.054(2) 0.061(2) 0.0482(19) 0.0189(17) 0.0309(17) 0.0232(17) C33 0.0514(19) 0.0326(16) 0.0333(16) 0.0046(13) 0.0213(15) 0.0156(14) C20 0.052(2) 0.0437(18) 0.0348(17) 0.0185(14) 0.0060(15) 0.0001(15) C24 0.0234(13) 0.0357(15) 0.0295(14) 0.0174(12) 0.0092(11) 0.0071(11) O4 0.0452(12) 0.0296(10) 0.0342(11) 0.0133(9) 0.0118(9) 0.0024(9) C42 0.057(2) 0.0310(17) 0.051(2) 0.0165(15) 0.0139(16) 0.0028(14) C41 0.0391(18) 0.060(2) 0.0375(17) 0.0230(16) 0.0120(14) 0.0018(15) C43 0.045(2) 0.082(3) 0.0377(18) 0.0147(18) 0.0226(15) 0.0198(18) C44 0.099(3) 0.0347(18) 0.044(2) 0.0081(15) 0.018(2) 0.0199(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 Zn N4 1.8980(19) . ? Zn C1 2.064(2) . ? Zn O2 2.0946(18) . ? Zn O1 2.1036(18) . ? N3 C35 1.369(3) . ? N3 C31 1.411(3) . ? N3 C1 1.473(3) . ? O2 C21 1.255(3) . ? O1 C11 1.244(3) . ? Si1 N4 1.700(2) . ? Si1 C30 1.864(3) . ? Si1 C10 1.864(3) . ? Si1 C20 1.876(3) . ? Si2 N4 1.703(2) . ? Si2 C40 1.862(3) . ? Si2 C60 1.868(3) . ? Si2 C50 1.872(3) . ? N1 C15 1.383(3) . ? N1 C11 1.397(3) . ? N1 C1 1.472(3) . ? N2 C25 1.371(3) . ? N2 C21 1.393(3) . ? N2 C1 1.480(3) . ? O3 C31 1.241(3) . ? C31 C32 1.425(3) . ? C15 C14 1.343(3) . ? C35 C34 1.350(3) . ? C22 C23 1.356(3) . ? C22 C21 1.426(3) . ? C11 C12 1.435(3) . ? C25 C24 1.348(3) . ? C23 C24 1.403(3) . ? C14 C13 1.410(3) . ? C12 C13 1.348(3) . ? C34 C33 1.410(4) . ? C32 C33 1.346(4) . ? O4 C41 1.413(3) . ? O4 C42 1.416(3) . ? C42 C44 1.485(4) . ? C41 C43 1.493(4) . ? 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 N4 Zn C1 153.20(8) . . ? N4 Zn O2 119.49(8) . . ? C1 Zn O2 79.84(8) . . ? N4 Zn O1 110.11(8) . . ? C1 Zn O1 81.33(8) . . ? O2 Zn O1 101.10(7) . . ? C35 N3 C31 121.2(2) . . ? C35 N3 C1 124.22(19) . . ? C31 N3 C1 113.75(18) . . ? C21 O2 Zn 111.19(14) . . ? C11 O1 Zn 111.90(15) . . ? N4 Si1 C30 112.23(12) . . ? N4 Si1 C10 110.40(11) . . ? C30 Si1 C10 106.76(14) . . ? N4 Si1 C20 113.28(12) . . ? C30 Si1 C20 107.39(14) . . ? C10 Si1 C20 106.39(12) . . ? N4 Si2 C40 110.23(12) . . ? N4 Si2 C60 110.54(12) . . ? C40 Si2 C60 107.69(14) . . ? N4 Si2 C50 113.90(12) . . ? C40 Si2 C50 107.22(14) . . ? C60 Si2 C50 107.00(13) . . ? C15 N1 C11 120.5(2) . . ? C15 N1 C1 122.38(19) . . ? C11 N1 C1 116.86(18) . . ? C25 N2 C21 121.5(2) . . ? C25 N2 C1 123.06(18) . . ? C21 N2 C1 115.39(19) . . ? Si1 N4 Si2 128.00(11) . . ? Si1 N4 Zn 114.41(10) . . ? Si2 N4 Zn 114.80(11) . . ? O3 C31 N3 119.2(2) . . ? O3 C31 C32 125.4(2) . . ? N3 C31 C32 115.4(2) . . ? C14 C15 N1 122.4(2) . . ? C34 C35 N3 121.9(2) . . ? N1 C1 N3 111.89(17) . . ? N1 C1 N2 107.91(17) . . ? N3 C1 N2 108.96(17) . . ? N1 C1 Zn 107.11(14) . . ? N3 C1 Zn 114.55(14) . . ? N2 C1 Zn 106.08(14) . . ? C23 C22 C21 121.8(2) . . ? O1 C11 N1 121.1(2) . . ? O1 C11 C12 122.8(2) . . ? N1 C11 C12 116.1(2) . . ? C24 C25 N2 121.9(2) . . ? C22 C23 C24 120.2(2) . . ? O2 C21 N2 120.1(2) . . ? O2 C21 C22 124.2(2) . . ? N2 C21 C22 115.7(2) . . ? C15 C14 C13 119.0(2) . . ? C13 C12 C11 122.0(2) . . ? C35 C34 C33 118.8(2) . . ? C12 C13 C14 119.9(2) . . ? C33 C32 C31 122.3(2) . . ? C32 C33 C34 120.1(2) . . ? C25 C24 C23 118.7(2) . . ? C41 O4 C42 112.9(2) . . ? O4 C42 C44 109.2(2) . . ? O4 C41 C43 110.3(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.63 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.445 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 951236' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_o3s10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N3 O3' _chemical_formula_weight 295.29 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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' _cell_length_a 15.486(3) _cell_length_b 15.486(3) _cell_length_c 5.0769(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1054.4(4) _cell_formula_units_Z 3 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 4031 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 31.62 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 462 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9429 _exptl_absorpt_correction_T_max 0.9951 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5315 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0407 _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 -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 31.64 _reflns_number_total 1540 _reflns_number_gt 1400 _reflns_threshold_expression >2sigma(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 ; 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^)+(0.0654P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1540 _refine_ls_number_parameters 67 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.06089(8) 0.04286(8) 0.7405(2) 0.0144(2) Uani 1 1 d . . . O1 O 0.01459(8) 0.15596(8) 0.4106(2) 0.0205(2) Uani 1 1 d . . . C1 C 0.0000 0.0000 0.6553(4) 0.0123(4) Uani 1 3 d S . . H1A H 0.0000 0.0000 0.4583 0.015 Uiso 1 3 calc SR . . C2 C -0.04804(10) 0.12438(9) 0.5878(3) 0.0161(2) Uani 1 1 d . . . C3 C -0.11174(11) 0.16359(11) 0.6601(3) 0.0225(3) Uani 1 1 d . . . H3A H -0.1073 0.2184 0.5646 0.027 Uiso 1 1 calc R . . C4 C -0.17807(12) 0.12395(12) 0.8616(3) 0.0235(3) Uani 1 1 d . . . H4A H -0.2186 0.1519 0.9060 0.028 Uiso 1 1 calc R . . C5 C -0.18742(10) 0.04122(11) 1.0067(3) 0.0206(3) Uani 1 1 d . . . H5A H -0.2341 0.0135 1.1467 0.025 Uiso 1 1 calc R . . C6 C -0.12905(10) 0.00248(10) 0.9430(3) 0.0175(3) Uani 1 1 d . . . H6A H -0.1350 -0.0530 1.0384 0.021 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0135(5) 0.0139(4) 0.0171(5) 0.0015(4) 0.0019(4) 0.0078(4) O1 0.0222(5) 0.0174(4) 0.0212(5) 0.0033(3) 0.0046(4) 0.0092(4) C1 0.0103(5) 0.0103(5) 0.0165(10) 0.000 0.000 0.0051(2) C2 0.0183(6) 0.0134(5) 0.0173(6) 0.0002(4) 0.0003(4) 0.0085(5) C3 0.0279(7) 0.0215(6) 0.0253(8) 0.0017(5) 0.0016(6) 0.0178(6) C4 0.0248(7) 0.0270(7) 0.0265(7) -0.0018(5) 0.0017(5) 0.0187(6) C5 0.0175(6) 0.0242(7) 0.0201(7) 0.0004(5) 0.0034(5) 0.0104(5) C6 0.0169(5) 0.0180(5) 0.0158(6) 0.0023(5) 0.0030(4) 0.0073(5) _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 N1 C6 1.3790(17) . ? N1 C2 1.4082(15) . ? N1 C1 1.4639(13) . ? O1 C2 1.2311(16) . ? C1 N1 1.4639(13) 3 ? C1 N1 1.4639(13) 2 ? C2 C3 1.4405(17) . ? C3 C4 1.360(2) . ? C4 C5 1.421(2) . ? C5 C6 1.3505(19) . ? 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 C6 N1 C2 123.36(10) . . ? C6 N1 C1 122.36(11) . . ? C2 N1 C1 114.17(11) . . ? N1 C1 N1 111.65(9) . 3 ? N1 C1 N1 111.64(9) . 2 ? N1 C1 N1 111.65(9) 3 2 ? O1 C2 N1 119.25(11) . . ? O1 C2 C3 126.03(12) . . ? N1 C2 C3 114.72(12) . . ? C4 C3 C2 121.55(14) . . ? C3 C4 C5 120.69(13) . . ? C6 C5 C4 119.17(13) . . ? C5 C6 N1 120.50(12) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 31.64 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.316 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 951237' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mt-o3tls10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H36 N3 O3 Tl' _chemical_formula_weight 666.97 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' Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 15.492(4) _cell_length_b 15.492(4) _cell_length_c 19.782(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4111.6(16) _cell_formula_units_Z 6 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 8372 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 28.97 _exptl_crystal_description Block _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1980 _exptl_absorpt_coefficient_mu 5.925 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.5888 _exptl_absorpt_correction_T_max 0.7560 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21563 _diffrn_reflns_av_R_equivalents 0.0739 _diffrn_reflns_av_sigmaI/netI 0.0433 _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 -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 30.70 _reflns_number_total 2818 _reflns_number_gt 2369 _reflns_threshold_expression >2sigma(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 ; 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^)+(0.0462P)^2^+21.5369P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2818 _refine_ls_number_parameters 109 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.029 _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 Tl Tl 0.0000 0.0000 0.285068(13) 0.02797(10) Uani 1 3 d S . . O O 0.1761(2) 0.0873(2) 0.22104(16) 0.0341(7) Uani 1 1 d . . . N N 0.0823(2) 0.0949(2) 0.13444(15) 0.0211(6) Uani 1 1 d . . . C1 C 0.0000 0.0000 0.1592(4) 0.0255(13) Uani 1 3 d SU . . C11 C 0.1708(3) 0.1340(3) 0.1718(2) 0.0242(7) Uani 1 1 d . . . C12 C 0.2507(3) 0.2280(3) 0.1492(2) 0.0266(8) Uani 1 1 d . . . H12A H 0.3124 0.2560 0.1727 0.032 Uiso 1 1 calc R . . C13 C 0.2431(3) 0.2792(3) 0.0957(2) 0.0253(7) Uani 1 1 d . . . C14 C 0.3277(3) 0.3797(3) 0.0734(2) 0.0339(9) Uani 1 1 d . . . C15 C 0.3603(6) 0.3687(6) 0.0027(3) 0.096(3) Uani 1 1 d . . . H15A H 0.3024 0.3393 -0.0275 0.143 Uiso 1 1 calc R . . H15B H 0.3895 0.3254 0.0045 0.143 Uiso 1 1 calc R . . H15C H 0.4101 0.4344 -0.0145 0.143 Uiso 1 1 calc R . . C16 C 0.2935(4) 0.4555(4) 0.0729(4) 0.069(2) Uani 1 1 d . . . H16A H 0.2669 0.4574 0.1175 0.104 Uiso 1 1 calc R . . H16B H 0.2414 0.4369 0.0387 0.104 Uiso 1 1 calc R . . H16C H 0.3500 0.5215 0.0623 0.104 Uiso 1 1 calc R . . C17 C 0.4177(4) 0.4192(4) 0.1202(3) 0.0429(11) Uani 1 1 d . . . H17A H 0.3973 0.4234 0.1664 0.064 Uiso 1 1 calc R . . H17B H 0.4688 0.4856 0.1051 0.064 Uiso 1 1 calc R . . H17C H 0.4448 0.3740 0.1192 0.064 Uiso 1 1 calc R . . C18 C 0.1504(3) 0.2354(3) 0.06141(19) 0.0274(8) Uani 1 1 d . . . H18A H 0.1417 0.2690 0.0241 0.033 Uiso 1 1 calc R . . C19 C 0.0743(3) 0.1463(3) 0.08132(18) 0.0236(7) Uani 1 1 d . . . H19A H 0.0129 0.1185 0.0574 0.028 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 Tl 0.03092(11) 0.03092(11) 0.02208(13) 0.000 0.000 0.01546(6) O 0.0265(15) 0.0344(16) 0.0383(17) 0.0118(13) -0.0053(12) 0.0128(13) N 0.0232(15) 0.0208(14) 0.0202(14) 0.0017(11) 0.0009(11) 0.0117(12) C1 0.0194(18) 0.0194(18) 0.038(4) 0.000 0.000 0.0097(9) C11 0.0231(17) 0.0252(18) 0.0253(17) -0.0005(14) -0.0023(14) 0.0130(15) C12 0.0202(17) 0.0247(18) 0.032(2) 0.0012(15) -0.0029(15) 0.0089(15) C13 0.0249(18) 0.0237(18) 0.0258(18) 0.0008(14) 0.0043(14) 0.0110(15) C14 0.031(2) 0.026(2) 0.030(2) 0.0060(16) 0.0023(16) 0.0024(17) C15 0.075(5) 0.077(5) 0.040(3) -0.009(3) 0.029(3) -0.033(4) C16 0.044(3) 0.028(3) 0.121(6) 0.024(3) -0.023(3) 0.007(2) C17 0.033(2) 0.028(2) 0.053(3) 0.007(2) -0.004(2) 0.0041(19) C18 0.032(2) 0.029(2) 0.0205(17) 0.0023(14) -0.0011(15) 0.0151(17) C19 0.0262(18) 0.0243(18) 0.0187(16) -0.0006(13) -0.0026(13) 0.0115(15) _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 Tl C1 2.490(7) . ? Tl O 2.681(3) . ? Tl O 2.681(3) 3 ? Tl O 2.681(3) 2 ? O C11 1.241(5) . ? N C19 1.362(5) . ? N C11 1.399(5) . ? N C1 1.467(4) . ? C1 N 1.467(4) 2 ? C1 N 1.467(4) 3 ? C11 C12 1.432(5) . ? C12 C13 1.363(6) . ? C13 C18 1.418(6) . ? C13 C14 1.515(6) . ? C14 C16 1.511(8) . ? C14 C17 1.524(7) . ? C14 C15 1.527(7) . ? C18 C19 1.350(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Tl O 61.81(7) . . ? C1 Tl O 61.81(7) . 3 ? O Tl O 99.51(8) . 3 ? C1 Tl O 61.81(7) . 2 ? O Tl O 99.51(8) . 2 ? O Tl O 99.51(8) 3 2 ? C11 O Tl 108.5(2) . . ? C19 N C11 120.7(3) . . ? C19 N C1 123.8(4) . . ? C11 N C1 115.5(3) . . ? N C1 N 109.4(3) 2 3 ? N C1 N 109.4(3) 2 . ? N C1 N 109.4(3) 3 . ? N C1 Tl 109.5(3) 2 . ? N C1 Tl 109.5(3) 3 . ? N C1 Tl 109.5(3) . . ? O C11 N 119.9(4) . . ? O C11 C12 124.1(4) . . ? N C11 C12 116.0(3) . . ? C13 C12 C11 123.5(4) . . ? C12 C13 C18 117.1(4) . . ? C12 C13 C14 122.9(4) . . ? C18 C13 C14 120.1(4) . . ? C16 C14 C13 109.9(4) . . ? C16 C14 C17 107.3(4) . . ? C13 C14 C17 112.5(4) . . ? C16 C14 C15 110.2(6) . . ? C13 C14 C15 108.5(4) . . ? C17 C14 C15 108.3(5) . . ? C19 C18 C13 120.5(4) . . ? C18 C19 N 122.3(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.70 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 3.122 _refine_diff_density_min -1.514 _refine_diff_density_rms 0.150 _database_code_depnum_ccdc_archive 'CCDC 951238'