# Electronic Supplementary Material (ESI) for Chemical Communications # 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_e2479b _database_code_depnum_ccdc_archive 'CCDC 923939' #TrackingRef 'web_deposit_cif_file_0_Gruber_1360327886.s2479.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H32 N2 O2' _chemical_formula_sum 'C26 H32 N2 O2' _chemical_formula_weight 404.54 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 Triclinic _symmetry_space_group_name_H-M P1 _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.4044(5) _cell_length_b 9.3965(6) _cell_length_c 10.5878(7) _cell_angle_alpha 65.760(3) _cell_angle_beta 86.256(3) _cell_angle_gamma 84.669(3) _cell_volume 578.21(7) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2654 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 29.67 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 218 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9942 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details sadabs _exptl_special_details ; there is not a symetry center because it is a chiral molecule' ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8369 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 29.10 _reflns_number_total 5084 _reflns_number_gt 3750 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1274P)^2^+0.3002P] 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' _chemical_absolute_configuration rm _refine_ls_number_reflns 5084 _refine_ls_number_parameters 275 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0979 _refine_ls_R_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.2271 _refine_ls_wR_factor_gt 0.2050 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.031 _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 C1 C 0.7597(6) 0.6277(4) 0.6629(4) 0.0264(8) Uani 1 1 d . . . C2 C 0.9105(7) 0.6969(5) 0.7033(4) 0.0360(10) Uani 1 1 d . . . H2 H 1.0545 0.6627 0.7013 0.043 Uiso 1 1 calc R . . C3 C 0.8502(8) 0.8164(5) 0.7467(5) 0.0436(11) Uani 1 1 d . . . H3 H 0.9574 0.8642 0.7698 0.052 Uiso 1 1 calc R . . N1 N 0.6517(7) 0.8679(4) 0.7579(4) 0.0469(10) Uani 1 1 d . . . C4 C 0.5088(7) 0.7990(5) 0.7207(5) 0.0413(11) Uani 1 1 d . . . H4 H 0.3656 0.8339 0.7254 0.050 Uiso 1 1 calc R . . C5 C 0.5546(7) 0.6803(5) 0.6757(5) 0.0382(10) Uani 1 1 d . . . H5 H 0.4439 0.6348 0.6534 0.046 Uiso 1 1 calc R . . C6 C 0.8232(5) 0.5096(4) 0.6089(3) 0.0247(8) Uani 1 1 d . . . C7 C 0.7100(6) 0.3731(4) 0.6451(4) 0.0290(9) Uani 1 1 d . . . C8 C 0.7853(6) 0.2636(4) 0.5888(4) 0.0308(9) Uani 1 1 d . . . H8 H 0.7115 0.1728 0.6111 0.037 Uiso 1 1 calc R . . C9 C 0.9592(6) 0.2843(4) 0.5040(4) 0.0288(9) Uani 1 1 d . . . C10 C 1.0690(6) 0.4150(4) 0.4714(4) 0.0280(9) Uani 1 1 d . . . C11 C 1.0022(6) 0.5256(4) 0.5207(4) 0.0282(9) Uani 1 1 d . . . H11 H 1.0786 0.6159 0.4947 0.034 Uiso 1 1 calc R . . O1 O 0.5392(4) 0.3599(3) 0.7278(3) 0.0406(8) Uani 1 1 d . . . C12 C 0.4371(8) 0.2164(6) 0.7795(5) 0.0448(12) Uani 1 1 d . . . H12A H 0.5326 0.1292 0.8397 0.054 Uiso 1 1 calc R . . H12B H 0.3998 0.1925 0.7013 0.054 Uiso 1 1 calc R . . C13 C 0.2431(7) 0.2332(6) 0.8604(5) 0.0427(11) Uani 1 1 d D . . H13 H 0.1480 0.3203 0.7971 0.051 Uiso 1 1 calc R . . C16 C 0.1316(11) 0.0825(8) 0.9116(8) 0.076(2) Uani 1 1 d D . . H16A H 0.2148 -0.0014 0.9829 0.114 Uiso 1 1 calc R . . H16B H 0.1152 0.0537 0.8340 0.114 Uiso 1 1 calc R . . H16C H -0.0069 0.0982 0.9510 0.114 Uiso 1 1 calc R . . C14 C 0.2966(10) 0.2741(9) 0.9794(6) 0.0768(19) Uani 1 1 d D . . H14A H 0.3858 0.3639 0.9460 0.092 Uiso 1 1 calc R . . H14B H 0.3706 0.1837 1.0526 0.092 Uiso 1 1 calc R . . C15 C 0.0729(14) 0.3183(10) 1.0359(8) 0.0768(19) Uani 1 1 d D . . H15A H -0.0191 0.2333 1.0564 0.092 Uiso 1 1 calc R . . H15B H 0.0097 0.4150 0.9653 0.092 Uiso 1 1 calc R . . H15C H 0.0911 0.3338 1.1205 0.092 Uiso 1 1 calc R . . O2 O 1.2420(4) 0.4327(3) 0.3801(3) 0.0375(8) Uani 1 1 d . . . C17 C 1.3530(6) 0.5705(5) 0.3438(4) 0.0313(9) Uani 1 1 d . . . H17A H 1.4078 0.5732 0.4280 0.038 Uiso 1 1 calc R . . H17B H 1.2574 0.6652 0.2994 0.038 Uiso 1 1 calc R . . C18 C 1.5328(8) 0.5669(6) 0.2444(5) 0.0459(12) Uani 1 1 d . . . H18 H 1.6258 0.4702 0.2929 0.055 Uiso 1 1 calc R . . C19 C 1.6588(7) 0.7090(5) 0.2179(5) 0.0456(11) Uani 1 1 d . . . H19A H 1.5692 0.8059 0.1693 0.055 Uiso 1 1 calc R . . H19B H 1.6939 0.7073 0.3082 0.055 Uiso 1 1 calc R . . C20 C 1.8596(8) 0.7138(7) 0.1328(6) 0.0739(15) Uani 1 1 d . . . H20A H 1.8257 0.7271 0.0395 0.111 Uiso 1 1 calc R . . H20B H 1.9461 0.6157 0.1773 0.111 Uiso 1 1 calc R . . H20C H 1.9371 0.8017 0.1266 0.111 Uiso 1 1 calc R . . C21 C 1.4674(11) 0.5623(10) 0.1161(7) 0.088(2) Uani 1 1 d . . . H21A H 1.5917 0.5505 0.0613 0.132 Uiso 1 1 calc R . . H21B H 1.3853 0.6598 0.0626 0.132 Uiso 1 1 calc R . . H21C H 1.3814 0.4736 0.1388 0.132 Uiso 1 1 calc R . . C22 C 1.0201(6) 0.1633(4) 0.4455(4) 0.0312(9) Uani 1 1 d . . . C23 C 1.2263(7) 0.1035(5) 0.4424(5) 0.0384(10) Uani 1 1 d . . . H23 H 1.3367 0.1411 0.4733 0.046 Uiso 1 1 calc R . . C24 C 1.2669(9) -0.0132(5) 0.3928(5) 0.0456(12) Uani 1 1 d . . . H24 H 1.4081 -0.0537 0.3907 0.055 Uiso 1 1 calc R . . N2 N 1.1204(7) -0.0712(4) 0.3483(4) 0.0447(10) Uani 1 1 d . . . C25 C 0.9257(8) -0.0117(6) 0.3522(5) 0.0513(13) Uani 1 1 d . . . H25 H 0.8191 -0.0506 0.3193 0.062 Uiso 1 1 calc R . . C26 C 0.8652(7) 0.1024(5) 0.4002(5) 0.0416(11) Uani 1 1 d . . . H26 H 0.7220 0.1383 0.4023 0.050 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 C1 0.044(2) 0.0161(17) 0.0196(18) -0.0081(15) 0.0042(17) -0.0067(16) C2 0.040(2) 0.033(2) 0.040(2) -0.021(2) 0.012(2) -0.0108(18) C3 0.055(3) 0.039(2) 0.051(3) -0.034(2) 0.024(2) -0.018(2) N1 0.065(3) 0.028(2) 0.053(2) -0.0229(19) 0.013(2) -0.0080(19) C4 0.039(2) 0.034(2) 0.055(3) -0.025(2) 0.011(2) 0.0019(19) C5 0.040(2) 0.032(2) 0.047(3) -0.021(2) -0.001(2) -0.0040(19) C6 0.031(2) 0.0197(18) 0.0190(18) -0.0031(16) 0.0009(16) -0.0057(16) C7 0.039(2) 0.023(2) 0.028(2) -0.0144(18) 0.0055(18) -0.0079(17) C8 0.036(2) 0.0224(19) 0.044(2) -0.0231(18) 0.0031(18) -0.0062(16) C9 0.037(2) 0.0205(19) 0.036(2) -0.0199(17) 0.0020(18) 0.0004(16) C10 0.029(2) 0.025(2) 0.032(2) -0.0135(18) 0.0067(17) -0.0052(16) C11 0.037(2) 0.0216(19) 0.025(2) -0.0078(17) 0.0089(17) -0.0111(16) O1 0.0432(18) 0.0349(17) 0.054(2) -0.0288(16) 0.0247(16) -0.0172(14) C12 0.058(3) 0.038(2) 0.051(3) -0.029(2) 0.022(2) -0.028(2) C13 0.044(3) 0.043(3) 0.042(3) -0.017(2) 0.005(2) -0.010(2) C16 0.088(5) 0.069(4) 0.083(4) -0.039(4) 0.022(4) -0.037(3) C14 0.103(5) 0.096(4) 0.046(3) -0.042(3) 0.035(3) -0.042(4) C15 0.103(5) 0.096(4) 0.046(3) -0.042(3) 0.035(3) -0.042(4) O2 0.0449(18) 0.0253(15) 0.0491(19) -0.0225(14) 0.0191(15) -0.0145(13) C17 0.033(2) 0.0257(19) 0.037(2) -0.0152(18) 0.0078(17) -0.0070(16) C18 0.054(3) 0.035(2) 0.053(3) -0.022(2) 0.020(2) -0.018(2) C19 0.040(2) 0.042(2) 0.050(3) -0.011(2) 0.010(2) -0.0167(19) C20 0.067(3) 0.089(4) 0.062(3) -0.022(3) 0.009(2) -0.035(3) C21 0.090(4) 0.128(6) 0.067(4) -0.052(4) 0.023(3) -0.067(4) C22 0.037(2) 0.0211(19) 0.037(2) -0.0136(18) 0.0110(19) -0.0059(17) C23 0.043(2) 0.031(2) 0.045(3) -0.021(2) 0.003(2) 0.0024(19) C24 0.063(3) 0.029(2) 0.047(3) -0.019(2) 0.003(2) 0.003(2) N2 0.064(3) 0.032(2) 0.047(2) -0.0271(19) 0.019(2) -0.0119(18) C25 0.066(3) 0.041(3) 0.062(3) -0.033(2) 0.006(3) -0.025(2) C26 0.043(2) 0.034(2) 0.058(3) -0.030(2) 0.010(2) -0.0125(19) _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 C1 C5 1.378(6) . ? C1 C2 1.392(5) . ? C1 C6 1.460(5) . ? C2 C3 1.392(5) . ? C2 H2 0.9500 . ? C3 N1 1.333(6) . ? C3 H3 0.9500 . ? N1 C4 1.334(6) . ? C4 C5 1.383(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C11 1.409(5) . ? C6 C7 1.432(5) . ? C7 O1 1.337(5) . ? C7 C8 1.421(5) . ? C8 C9 1.360(5) . ? C8 H8 0.9500 . ? C9 C10 1.379(5) . ? C9 C22 1.514(5) . ? C10 C11 1.367(5) . ? C10 O2 1.397(5) . ? C11 H11 0.9500 . ? O1 C12 1.435(5) . ? C12 C13 1.496(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C16 1.522(7) . ? C13 C14 1.526(6) . ? C13 H13 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C14 C15 1.602(8) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? O2 C17 1.434(4) . ? C17 C18 1.517(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C21 1.465(7) . ? C18 C19 1.541(6) . ? C18 H18 1.0000 . ? C19 C20 1.515(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C26 1.390(6) . ? C22 C23 1.390(6) . ? C23 C24 1.397(6) . ? C23 H23 0.9500 . ? C24 N2 1.328(6) . ? C24 H24 0.9500 . ? N2 C25 1.324(6) . ? C25 C26 1.379(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C1 C2 115.6(3) . . ? C5 C1 C6 124.2(3) . . ? C2 C1 C6 120.2(4) . . ? C3 C2 C1 120.0(4) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? N1 C3 C2 124.2(4) . . ? N1 C3 H3 117.9 . . ? C2 C3 H3 117.9 . . ? C4 N1 C3 115.1(4) . . ? N1 C4 C5 124.5(4) . . ? N1 C4 H4 117.7 . . ? C5 C4 H4 117.7 . . ? C1 C5 C4 120.5(4) . . ? C1 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C11 C6 C7 117.8(3) . . ? C11 C6 C1 120.5(3) . . ? C7 C6 C1 121.7(3) . . ? O1 C7 C8 125.1(3) . . ? O1 C7 C6 117.2(3) . . ? C8 C7 C6 117.7(4) . . ? C9 C8 C7 122.4(4) . . ? C9 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? C8 C9 C10 119.5(3) . . ? C8 C9 C22 117.8(3) . . ? C10 C9 C22 122.7(4) . . ? C11 C10 C9 120.8(3) . . ? C11 C10 O2 122.2(3) . . ? C9 C10 O2 116.9(3) . . ? C10 C11 C6 121.9(3) . . ? C10 C11 H11 119.1 . . ? C6 C11 H11 119.1 . . ? C7 O1 C12 118.6(3) . . ? O1 C12 C13 108.9(3) . . ? O1 C12 H12A 109.9 . . ? C13 C12 H12A 109.9 . . ? O1 C12 H12B 109.9 . . ? C13 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? C12 C13 C16 108.8(4) . . ? C12 C13 C14 110.7(4) . . ? C16 C13 C14 112.0(5) . . ? C12 C13 H13 108.4 . . ? C16 C13 H13 108.4 . . ? C14 C13 H13 108.4 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C14 C15 103.9(5) . . ? C13 C14 H14A 111.0 . . ? C15 C14 H14A 111.0 . . ? C13 C14 H14B 111.0 . . ? C15 C14 H14B 111.0 . . ? H14A C14 H14B 109.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 O2 C17 116.9(3) . . ? O2 C17 C18 108.3(3) . . ? O2 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? O2 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? C21 C18 C17 114.2(5) . . ? C21 C18 C19 112.7(5) . . ? C17 C18 C19 106.7(3) . . ? C21 C18 H18 107.7 . . ? C17 C18 H18 107.7 . . ? C19 C18 H18 107.7 . . ? C20 C19 C18 113.9(4) . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C26 C22 C23 118.2(4) . . ? C26 C22 C9 119.7(4) . . ? C23 C22 C9 122.0(4) . . ? C22 C23 C24 118.2(4) . . ? C22 C23 H23 120.9 . . ? C24 C23 H23 120.9 . . ? N2 C24 C23 124.0(5) . . ? N2 C24 H24 118.0 . . ? C23 C24 H24 118.0 . . ? C25 N2 C24 116.3(4) . . ? N2 C25 C26 125.2(4) . . ? N2 C25 H25 117.4 . . ? C26 C25 H25 117.4 . . ? C25 C26 C22 118.1(4) . . ? C25 C26 H26 121.0 . . ? C22 C26 H26 121.0 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.446 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.064 data_e2502b _database_code_depnum_ccdc_archive 'CCDC 923940' #TrackingRef 'web_deposit_cif_file_1_Gruber_1360327886.s2502.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H56 F6 N4 O4 Si Zn, 3(C H Cl3)' _chemical_formula_sum 'C51 H59 Cl9 F6 N4 O4 Si Zn' _chemical_formula_weight 1318.53 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4 _symmetry_space_group_name_Hall 'P 4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z' 'y, -x, z' _cell_length_a 22.0656(6) _cell_length_b 22.0656(6) _cell_length_c 15.2730(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7436.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9884 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.75 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2704 _exptl_absorpt_coefficient_mu 0.721 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9445 _exptl_absorpt_correction_T_max 0.9717 _exptl_absorpt_process_details sadabs _exptl_special_details ; Owing to large disorder of the solvent present in the cavities of this structure, the SQUEEZE command has been applied. Because of the flopiness of the four chain we let theses atoms isotrop and we didn't introduce the hydrogenes on theses atoms. Note however that the hydrogen atoms have been introduced in the formula and the moiety of the compound. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 78262 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 30.10 _reflns_number_total 21762 _reflns_number_gt 11626 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0200P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(3) _refine_ls_number_reflns 21762 _refine_ls_number_parameters 533 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1980 _refine_ls_R_factor_gt 0.1136 _refine_ls_wR_factor_ref 0.4329 _refine_ls_wR_factor_gt 0.4063 _refine_ls_goodness_of_fit_ref 1.270 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.038 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.5000 0.02092(9) 0.0154(3) Uani 1 4 d S . . Zn2 Zn 0.5000 0.5000 0.51983(9) 0.0149(3) Uani 1 4 d S . . Zn3 Zn 0.0000 0.0000 -0.00895(15) 0.0369(5) Uani 1 4 d S . . Zn4 Zn 0.0000 0.0000 0.48979(15) 0.0369(5) Uani 1 4 d S . . Si1 Si 0.5000 0.5000 0.2697(3) 0.0250(12) Uani 1 4 d S . . F1 F 0.5000 0.5000 0.1585(5) 0.0250(12) Uani 1 4 d S . . F2 F 0.5103(2) 0.4260(2) 0.2687(5) 0.0250(12) Uani 1 4 d S . . F3 F 0.5000 0.5000 0.3806(7) 0.0250(12) Uani 1 4 d S . . Si2 Si 0.5000 0.5000 0.7686(3) 0.0257(12) Uani 1 4 d S . . F4 F 0.5000 0.5000 0.6605(7) 0.0257(12) Uani 1 4 d S . . F5 F 0.5753(4) 0.5006(4) 0.7718(8) 0.0257(12) Uani 1 4 d S . . F6 F 0.5000 0.5000 -0.1181(6) 0.0257(12) Uani 1 4 d S . . Si3 Si 0.0000 0.0000 0.2405(4) 0.0257(12) Uani 1 4 d S . . F7 F 0.0000 0.0000 0.3552(6) 0.0257(12) Uani 1 4 d S . . F8 F 0.0738(3) -0.0120(3) 0.2402(5) 0.0257(12) Uani 1 4 d S . . F9 F 0.0000 0.0000 0.1257(7) 0.0257(12) Uani 1 4 d S . . Si4 Si 0.0000 0.0000 0.7421(4) 0.0278(12) Uani 1 4 d S . . F10 F 0.0000 0.0000 0.6277(7) 0.0278(12) Uani 1 4 d S . . F11 F 0.0728(5) 0.0087(5) 0.7401(10) 0.0278(12) Uani 1 4 d S . . F12 F 0.0000 0.0000 0.8558(8) 0.0278(12) Uani 1 4 d S . . N1 N 0.4319(2) 0.4342(2) 0.0189(5) 0.0208(11) Uani 1 1 d . . . C1 C 0.4241(4) 0.3909(4) 0.0840(5) 0.0354(19) Uani 1 1 d . . . H1 H 0.4495 0.3926 0.1342 0.043 Uiso 1 1 calc R . . C2 C 0.3821(4) 0.3467(4) 0.0792(6) 0.039(2) Uani 1 1 d . . . H2 H 0.3837 0.3145 0.1206 0.047 Uiso 1 1 calc R . . C3 C 0.3362(3) 0.3460(4) 0.0157(6) 0.0337(17) Uani 1 1 d . . . C4 C 0.3401(4) 0.3942(4) -0.0448(6) 0.042(2) Uani 1 1 d . . . H4 H 0.3100 0.3978 -0.0890 0.051 Uiso 1 1 calc R . . C5 C 0.3868(4) 0.4365(3) -0.0415(5) 0.0301(17) Uani 1 1 d . . . H5 H 0.3872 0.4684 -0.0833 0.036 Uiso 1 1 calc R . . C6 C 0.2917(4) 0.3011(4) 0.0107(6) 0.045(2) Uani 1 1 d . . . C7 C 0.3084(4) 0.2376(4) 0.0188(7) 0.0421(19) Uani 1 1 d . . . H7 H 0.3498 0.2271 0.0273 0.051 Uiso 1 1 calc R . . C8 C 0.2658(4) 0.1928(4) 0.0143(6) 0.0393(18) Uani 1 1 d . . . C9 C 0.2055(4) 0.2071(4) 0.0037(5) 0.042(2) Uani 1 1 d . . . C10 C 0.1872(4) 0.2661(6) 0.0046(6) 0.055(3) Uani 1 1 d . . . H10 H 0.1450 0.2745 0.0032 0.066 Uiso 1 1 calc R . . C11 C 0.2274(4) 0.3145(4) 0.0073(6) 0.046(2) Uiso 1 1 d . . . O1 O 0.2861(4) 0.1337(4) 0.0168(7) 0.096(3) Uani 1 1 d D . . C12 C 0.3494(5) 0.1127(4) -0.0129(9) 0.089 Uiso 1 1 d D . . C13 C 0.3754(16) 0.1462(10) -0.0936(16) 0.089 Uiso 0.467(16) 1 d PD . . C14 C 0.3499(13) 0.0493(7) 0.0274(16) 0.089 Uiso 0.467(16) 1 d PD . . C15 C 0.3183(13) 0.0030(7) -0.033(2) 0.089 Uiso 0.467(16) 1 d PD . . O2 O 0.2139(3) 0.3712(4) -0.0005(7) 0.079(3) Uani 1 1 d D . . C16 C 0.1460(4) 0.3853(6) 0.0078(8) 0.096(4) Uiso 1 1 d D . . C17 C 0.1300(13) 0.4476(11) -0.032(3) 0.107 Uiso 0.44(2) 1 d PD . . C18 C 0.1274(7) 0.3864(7) 0.1061(9) 0.107 Uiso 1 1 d D . . C19 C 0.1745(13) 0.4237(15) 0.1585(14) 0.102 Uiso 0.44(2) 1 d PD . . C20 C 0.1563(5) 0.1572(5) 0.0012(7) 0.053(3) Uani 1 1 d . . . C21 C 0.1132(5) 0.1583(5) -0.0647(7) 0.061(3) Uani 1 1 d . . . H21 H 0.1133 0.1890 -0.1083 0.073 Uiso 1 1 calc R . . C22 C 0.0687(5) 0.1116(5) -0.0646(6) 0.053(3) Uani 1 1 d . . . H22 H 0.0363 0.1133 -0.1056 0.063 Uiso 1 1 calc R K . N2 N 0.0714(3) 0.0684(3) -0.0117(6) 0.0423(17) Uani 1 1 d . . . C23 C 0.1133(4) 0.0657(4) 0.0551(7) 0.051(2) Uani 1 1 d . . . H23 H 0.1113 0.0339 0.0969 0.061 Uiso 1 1 calc R . . C24 C 0.1604(5) 0.1110(5) 0.0617(8) 0.056(3) Uiso 1 1 d . . . H24 H 0.1917 0.1091 0.1043 0.067 Uiso 1 1 calc R . . N3 N 0.4330(3) 0.4293(2) 0.5148(4) 0.0236(12) Uani 1 1 d . . . C27 C 0.3890(3) 0.4285(4) 0.5794(6) 0.038(2) Uani 1 1 d . . . H27 H 0.3895 0.4576 0.6253 0.046 Uiso 1 1 calc R . . C28 C 0.3430(4) 0.3836(5) 0.5760(6) 0.053(3) Uani 1 1 d . . . H28 H 0.3114 0.3830 0.6182 0.064 Uiso 1 1 calc R . . C29 C 0.3449(4) 0.3399(4) 0.5089(6) 0.043(2) Uani 1 1 d . . . C30 C 0.3910(4) 0.3438(4) 0.4509(6) 0.044(2) Uani 1 1 d . . . H30 H 0.3933 0.3148 0.4050 0.053 Uiso 1 1 calc R . . C31 C 0.4332(3) 0.3865(3) 0.4555(5) 0.0307(16) Uani 1 1 d . . . H31 H 0.4651 0.3861 0.4138 0.037 Uiso 1 1 calc R . . C32 C 0.2957(2) 0.2943(2) 0.5066(5) 0.0546(11) Uani 1 1 d G . . C33 C 0.30882(19) 0.2331(2) 0.4958(5) 0.0546(11) Uani 1 1 d G . . C34 C 0.2621(2) 0.1911(2) 0.4898(5) 0.0546(11) Uani 1 1 d G . . H34 H 0.2710 0.1493 0.4824 0.066 Uiso 1 1 calc R . . C35 C 0.2021(2) 0.2103(2) 0.4946(5) 0.0546(11) Uani 1 1 d G . . C36 C 0.18899(19) 0.2714(2) 0.5055(5) 0.0546(11) Uani 1 1 d G . . C37 C 0.2358(2) 0.3134(2) 0.5115(5) 0.0546(11) Uani 1 1 d G . . H37 H 0.2268 0.3552 0.5189 0.066 Uiso 1 1 calc R . . O3 O 0.3663(3) 0.2164(3) 0.4880(6) 0.067(2) Uani 1 1 d D . . C38 C 0.3861(7) 0.1524(6) 0.5186(11) 0.129(6) Uiso 1 1 d D . . H38 H 0.3621 0.1260 0.4781 0.154 Uiso 1 1 calc R . . C39 C 0.3773(8) 0.1193(8) 0.6062(10) 0.111(5) Uiso 1 1 d D . . H39A H 0.4157 0.1010 0.6244 0.166 Uiso 1 1 calc R . . H39B H 0.3467 0.0874 0.5992 0.166 Uiso 1 1 calc R . . H39C H 0.3637 0.1482 0.6508 0.166 Uiso 1 1 calc R . . C40 C 0.4508(7) 0.1421(8) 0.4843(11) 0.126 Uiso 1 1 d D . . H40A H 0.4671 0.1020 0.5014 0.151 Uiso 1 1 calc R . . H40B H 0.4537 0.1473 0.4200 0.151 Uiso 1 1 calc R . . C41 C 0.4810(9) 0.1944(8) 0.5346(14) 0.126 Uiso 1 1 d D . . H41A H 0.4554 0.2305 0.5311 0.189 Uiso 1 1 calc R . . H41B H 0.5207 0.2031 0.5086 0.189 Uiso 1 1 calc R . . H41C H 0.4863 0.1827 0.5960 0.189 Uiso 1 1 calc R . . O4 O 0.1284(4) 0.2903(4) 0.5024(9) 0.101(4) Uani 1 1 d D . . C42 C 0.1094(6) 0.3551(5) 0.4857(9) 0.099(4) Uiso 1 1 d D . . H42 H 0.1335 0.3866 0.5175 0.118 Uiso 1 1 calc R . . C43 C 0.1221(7) 0.3503(8) 0.3878(8) 0.097(5) Uiso 1 1 d D . . H43A H 0.1280 0.3061 0.3812 0.117 Uiso 1 1 calc R . . H43B H 0.1635 0.3675 0.3846 0.117 Uiso 1 1 calc R . . C44 C 0.0972(8) 0.3671(8) 0.2972(9) 0.109 Uiso 1 1 d D . . H44A H 0.0529 0.3681 0.2993 0.164 Uiso 1 1 calc R . . H44B H 0.1104 0.3369 0.2542 0.164 Uiso 1 1 calc R . . H44C H 0.1125 0.4071 0.2802 0.164 Uiso 1 1 calc R . . C45 C 0.0438(6) 0.3473(7) 0.5170(11) 0.098(4) Uiso 1 1 d D . . H45A H 0.0283 0.3079 0.4976 0.146 Uiso 1 1 calc R . . H45B H 0.0186 0.3797 0.4924 0.146 Uiso 1 1 calc R . . H45C H 0.0425 0.3494 0.5811 0.146 Uiso 1 1 calc R . . C46 C 0.1516(2) 0.1624(2) 0.4895(4) 0.049(2) Uani 1 1 d G . . C47 C 0.1041(3) 0.1620(2) 0.5492(4) 0.053(3) Uani 1 1 d G . . H47 H 0.1011 0.1931 0.5921 0.063 Uiso 1 1 calc R . . C48 C 0.0609(2) 0.1162(3) 0.5461(4) 0.056(3) Uani 1 1 d G . . H48 H 0.0284 0.1160 0.5869 0.067 Uiso 1 1 calc R . . N4 N 0.0653(2) 0.0708(2) 0.4834(4) 0.050(2) Uani 1 1 d G . . C49 C 0.1128(3) 0.0712(3) 0.4237(4) 0.066(3) Uani 1 1 d G . . H49 H 0.1158 0.0402 0.3808 0.080 Uiso 1 1 calc R . . C50 C 0.1560(3) 0.1170(3) 0.4267(4) 0.053(2) Uani 1 1 d G . . H50 H 0.1885 0.1173 0.3859 0.064 Uiso 1 1 calc R . . C51 C 0.5755(6) 0.3051(6) 0.2672(10) 0.081(3) Uani 1 1 d . . . H51 H 0.5759 0.3504 0.2704 0.097 Uiso 1 1 calc R . . Cl1 Cl 0.54038(16) 0.27700(18) 0.3658(3) 0.0914(12) Uani 1 1 d . . . Cl2 Cl 0.53162(19) 0.28395(17) 0.1754(3) 0.0952(11) Uani 1 1 d . . . Cl3 Cl 0.64718(14) 0.28152(15) 0.2636(3) 0.0813(9) Uani 1 1 d . . . C52 C 0.6960(8) 0.4303(7) 0.7867(12) 0.103(6) Uani 1 1 d . . . H52 H 0.6510 0.4330 0.7934 0.123 Uiso 1 1 calc R . . Cl4 Cl 0.7215(2) 0.4589(2) 0.8741(4) 0.1236(17) Uani 1 1 d . . . Cl5 Cl 0.7100(3) 0.3514(2) 0.7708(4) 0.1299(17) Uani 1 1 d . . . Cl6 Cl 0.7105(3) 0.4664(3) 0.6854(4) 0.156(3) Uani 1 1 d . . . C54 C 0.0768(7) 0.1907(8) 0.2394(10) 0.100(5) Uani 1 1 d . . . H54 H 0.0783 0.1454 0.2358 0.119 Uiso 1 1 calc R . . Cl7 Cl 0.0412(2) 0.2247(2) 0.1403(4) 0.1196(16) Uani 1 1 d . . . Cl8 Cl 0.0311(2) 0.2170(2) 0.3340(4) 0.1205(16) Uani 1 1 d . . . Cl9 Cl 0.14637(19) 0.2210(2) 0.2442(3) 0.1037(12) Uani 1 1 d . . . C13A C 0.3552(14) 0.1297(14) -0.114(2) 0.089 Uiso 0.533(16) 1 d P K 2 C14A C 0.3482(7) 0.0434(5) -0.0315(14) 0.089 Uiso 0.533(16) 1 d PD K 2 C15A C 0.4055(10) 0.0133(8) 0.0063(18) 0.089 Uiso 0.533(16) 1 d PD K 2 C17A C 0.1567(16) 0.4519(8) -0.021(2) 0.107 Uiso 0.56(2) 1 d PD K 2 C19A C 0.1068(14) 0.4533(9) 0.098(2) 0.107 Uiso 0.56(2) 1 d PD K 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0231(5) 0.0231(5) 0.0027(5) 0.000 0.000 0.000 Zn2 0.0211(4) 0.0211(4) 0.0025(6) 0.000 0.000 0.000 Zn3 0.0211(5) 0.0211(5) 0.0684(14) 0.000 0.000 0.000 Zn4 0.0222(5) 0.0222(5) 0.0663(13) 0.000 0.000 0.000 Si1 0.0215(17) 0.0215(17) 0.032(3) 0.000 0.000 0.000 F1 0.0215(17) 0.0215(17) 0.032(3) 0.000 0.000 0.000 F2 0.0215(17) 0.0215(17) 0.032(3) 0.000 0.000 0.000 F3 0.0215(17) 0.0215(17) 0.032(3) 0.000 0.000 0.000 Si2 0.0278(19) 0.0278(19) 0.022(3) 0.000 0.000 0.000 F4 0.0278(19) 0.0278(19) 0.022(3) 0.000 0.000 0.000 F5 0.0278(19) 0.0278(19) 0.022(3) 0.000 0.000 0.000 F6 0.0278(19) 0.0278(19) 0.022(3) 0.000 0.000 0.000 Si3 0.0251(18) 0.0251(18) 0.025(2) 0.000 0.000 0.000 F7 0.0251(18) 0.0251(18) 0.025(2) 0.000 0.000 0.000 F8 0.0251(18) 0.0251(18) 0.025(2) 0.000 0.000 0.000 F9 0.0251(18) 0.0251(18) 0.025(2) 0.000 0.000 0.000 Si4 0.0310(19) 0.0310(19) 0.020(2) 0.000 0.000 0.000 F10 0.0310(19) 0.0310(19) 0.020(2) 0.000 0.000 0.000 F11 0.0310(19) 0.0310(19) 0.020(2) 0.000 0.000 0.000 F12 0.0310(19) 0.0310(19) 0.020(2) 0.000 0.000 0.000 N1 0.024(3) 0.016(3) 0.022(3) 0.006(3) -0.003(3) 0.005(2) C1 0.041(4) 0.033(4) 0.032(4) 0.005(3) 0.006(3) -0.024(3) C2 0.037(4) 0.045(5) 0.035(5) 0.001(4) 0.003(3) 0.013(4) C3 0.032(4) 0.042(4) 0.027(4) 0.015(4) 0.002(3) -0.010(3) C4 0.038(4) 0.057(5) 0.032(4) 0.012(4) -0.011(3) -0.025(4) C5 0.045(5) 0.032(4) 0.013(3) 0.006(3) 0.004(3) -0.012(3) C6 0.047(5) 0.049(5) 0.039(5) 0.004(4) -0.006(4) -0.027(4) C7 0.037(4) 0.033(4) 0.056(5) 0.005(4) 0.000(4) -0.008(3) C8 0.045(4) 0.042(4) 0.031(4) 0.008(3) 0.002(4) -0.012(3) C9 0.055(5) 0.045(5) 0.026(5) 0.015(3) -0.009(3) -0.018(4) C10 0.036(5) 0.097(8) 0.032(5) 0.020(4) -0.007(3) -0.030(5) O1 0.118(7) 0.069(5) 0.100(8) 0.000(5) -0.025(6) 0.017(5) O2 0.036(3) 0.073(5) 0.129(8) 0.034(5) 0.012(4) -0.029(3) C20 0.059(6) 0.048(5) 0.052(7) 0.011(4) -0.010(5) -0.015(4) C21 0.073(7) 0.057(6) 0.052(6) 0.024(5) -0.021(5) -0.032(5) C22 0.054(6) 0.068(7) 0.036(5) 0.012(4) -0.018(4) 0.028(5) N2 0.028(3) 0.040(4) 0.058(5) -0.003(4) -0.010(4) -0.018(3) C23 0.042(5) 0.037(5) 0.073(7) 0.015(5) -0.025(5) -0.018(4) N3 0.031(3) 0.026(3) 0.013(3) -0.004(2) 0.014(2) -0.019(2) C27 0.023(4) 0.037(4) 0.055(6) -0.009(4) 0.021(4) -0.012(3) C28 0.047(5) 0.064(6) 0.049(6) 0.010(5) 0.020(4) -0.039(5) C29 0.027(4) 0.063(6) 0.039(5) -0.011(4) 0.012(3) -0.027(4) C30 0.060(5) 0.047(5) 0.026(4) -0.017(4) 0.015(4) -0.009(4) C31 0.024(3) 0.035(4) 0.032(4) 0.001(3) 0.010(3) 0.010(3) C32 0.0465(18) 0.0436(18) 0.074(3) -0.0154(16) 0.0202(17) -0.0180(15) C33 0.0465(18) 0.0436(18) 0.074(3) -0.0154(16) 0.0202(17) -0.0180(15) C34 0.0465(18) 0.0436(18) 0.074(3) -0.0154(16) 0.0202(17) -0.0180(15) C35 0.0465(18) 0.0436(18) 0.074(3) -0.0154(16) 0.0202(17) -0.0180(15) C36 0.0465(18) 0.0436(18) 0.074(3) -0.0154(16) 0.0202(17) -0.0180(15) C37 0.0465(18) 0.0436(18) 0.074(3) -0.0154(16) 0.0202(17) -0.0180(15) O3 0.058(4) 0.043(4) 0.100(6) 0.011(4) 0.024(4) 0.000(3) O4 0.066(5) 0.065(5) 0.172(12) 0.011(6) 0.043(6) 0.010(4) C46 0.056(6) 0.028(4) 0.064(6) -0.012(4) -0.003(5) -0.010(4) C47 0.048(5) 0.034(5) 0.075(7) -0.005(4) 0.030(5) -0.009(4) C48 0.066(6) 0.059(6) 0.043(5) -0.024(4) 0.019(5) -0.037(5) N4 0.039(4) 0.036(4) 0.076(6) -0.014(4) -0.001(4) 0.006(3) C49 0.082(8) 0.054(6) 0.063(7) -0.012(5) -0.011(6) -0.017(6) C50 0.067(6) 0.040(5) 0.052(6) -0.008(4) 0.015(5) 0.005(4) C51 0.094(8) 0.083(8) 0.066(7) 0.017(7) -0.005(7) 0.006(7) Cl1 0.085(2) 0.102(3) 0.088(3) 0.0190(19) 0.0284(18) 0.0276(18) Cl2 0.104(3) 0.090(2) 0.091(3) 0.0041(19) -0.023(2) 0.0167(19) Cl3 0.0790(19) 0.103(2) 0.0622(18) 0.0205(18) 0.0040(16) 0.0245(16) C52 0.113(12) 0.080(9) 0.115(14) 0.032(9) 0.038(10) 0.019(8) Cl4 0.121(4) 0.129(4) 0.120(4) -0.044(3) -0.010(3) 0.031(3) Cl5 0.193(5) 0.113(3) 0.084(3) 0.005(3) -0.033(3) 0.021(3) Cl6 0.153(5) 0.182(6) 0.134(5) 0.078(4) 0.023(4) 0.005(4) C54 0.106(10) 0.119(12) 0.073(9) 0.050(9) 0.001(8) -0.033(9) Cl7 0.125(3) 0.108(3) 0.126(4) 0.022(3) -0.021(3) -0.020(3) Cl8 0.137(4) 0.107(3) 0.117(4) 0.002(3) 0.020(3) -0.042(3) Cl9 0.104(3) 0.125(3) 0.082(3) 0.010(2) 0.002(2) -0.026(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N1 2.090(5) . ? Zn1 N1 2.090(5) 2_665 ? Zn1 N1 2.090(5) 4_565 ? Zn1 N1 2.090(5) 3_655 ? Zn1 F1 2.101(8) . ? Zn1 F6 2.123(9) . ? Zn2 F3 2.126(10) . ? Zn2 F4 2.148(10) . ? Zn2 N3 2.151(5) 2_665 ? Zn2 N3 2.151(5) 4_565 ? Zn2 N3 2.151(5) 3_655 ? Zn2 N3 2.151(5) . ? Zn3 F9 2.056(11) . ? Zn3 F12 2.065(12) 1_554 ? Zn3 N2 2.182(6) 3 ? Zn3 N2 2.182(6) . ? Zn3 N2 2.182(6) 2 ? Zn3 N2 2.182(6) 4 ? Zn4 F7 2.056(10) . ? Zn4 F10 2.107(10) . ? Zn4 N4 2.128(4) 3 ? Zn4 N4 2.128(4) 4 ? Zn4 N4 2.128(4) 2 ? Zn4 N4 2.128(4) . ? Si1 F2 1.648(5) 2_665 ? Si1 F2 1.648(5) . ? Si1 F2 1.648(5) 3_655 ? Si1 F2 1.648(5) 4_565 ? Si1 F3 1.693(11) . ? Si1 F1 1.699(9) . ? Si2 F4 1.651(11) . ? Si2 F5 1.663(8) 3_655 ? Si2 F5 1.663(8) 4_565 ? Si2 F5 1.663(8) . ? Si2 F5 1.663(8) 2_665 ? Si2 F6 1.731(10) 1_556 ? F6 Si2 1.731(10) 1_554 ? Si3 F8 1.649(6) 3 ? Si3 F8 1.649(6) 2 ? Si3 F8 1.649(6) . ? Si3 F8 1.649(6) 4 ? Si3 F7 1.751(12) . ? Si3 F9 1.754(12) . ? Si4 F11 1.619(11) . ? Si4 F11 1.619(11) 3 ? Si4 F11 1.619(11) 2 ? Si4 F11 1.619(11) 4 ? Si4 F12 1.737(14) . ? Si4 F10 1.746(12) . ? F12 Zn3 2.066(12) 1_556 ? N1 C5 1.358(10) . ? N1 C1 1.390(10) . ? C1 C2 1.347(12) . ? C1 H1 0.9500 . ? C2 C3 1.404(12) . ? C2 H2 0.9500 . ? C3 C6 1.397(11) . ? C3 C4 1.410(11) . ? C4 C5 1.392(11) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.455(13) . ? C6 C11 1.450(13) . ? C7 C8 1.367(11) . ? C7 H7 0.9500 . ? C8 C9 1.376(13) . ? C8 O1 1.380(12) . ? C9 C10 1.362(15) . ? C9 C20 1.546(12) . ? C10 C11 1.389(13) . ? C10 H10 0.9500 . ? C11 O2 1.291(12) . ? O1 C12 1.540(9) . ? C12 C14 1.528(10) . ? C12 C13 1.548(10) . ? C12 C14A 1.554(9) . ? C12 C13A 1.59(4) . ? C14 C15 1.543(10) . ? O2 C16 1.536(9) . ? C16 C17 1.547(10) . ? C16 C17A 1.551(10) . ? C16 C18 1.556(9) . ? C18 C19 1.548(10) . ? C18 C19A 1.550(10) . ? C20 C24 1.379(14) . ? C20 C21 1.387(14) . ? C21 C22 1.423(15) . ? C21 H21 0.9500 . ? C22 N2 1.251(12) . ? C22 H22 0.9500 . ? N2 C23 1.378(11) . ? C23 C24 1.446(14) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? N3 C31 1.307(10) . ? N3 C27 1.384(9) . ? C27 C28 1.420(11) . ? C27 H27 0.9500 . ? C28 C29 1.406(13) . ? C28 H28 0.9500 . ? C29 C30 1.352(11) . ? C29 C32 1.483(8) . ? C30 C31 1.328(12) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 C33 1.3900 . ? C32 C37 1.3900 . ? C33 O3 1.326(8) . ? C33 C34 1.3900 . ? C34 C35 1.3900 . ? C34 H34 0.9500 . ? C35 C36 1.3900 . ? C35 C46 1.537(5) . ? C36 C37 1.3900 . ? C36 O4 1.401(10) . ? C37 H37 0.9500 . ? O3 C38 1.550(9) . ? C38 C39 1.536(9) . ? C38 C40 1.538(9) . ? C38 H38 1.0000 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 C41 1.538(9) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 H41A 0.9805 . ? C41 H41B 0.9805 . ? C41 H41C 0.9805 . ? O4 C42 1.512(9) . ? C42 C43 1.524(9) . ? C42 C45 1.535(9) . ? C42 H42 1.0000 . ? C43 C44 1.535(9) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9802 . ? C45 H45B 0.9802 . ? C45 H45C 0.9802 . ? C46 C47 1.3900 . ? C46 C50 1.3900 . ? C47 C48 1.3900 . ? C47 H47 0.9500 . ? C48 N4 1.3900 . ? C48 H48 0.9500 . ? N4 C49 1.3900 . ? C49 C50 1.3900 . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? C51 Cl3 1.666(13) . ? C51 Cl2 1.767(15) . ? C51 Cl1 1.803(14) . ? C51 H51 1.0000 . ? C52 Cl4 1.58(2) . ? C52 Cl6 1.770(16) . ? C52 Cl5 1.785(16) . ? C52 H52 1.0000 . ? C54 Cl9 1.676(14) . ? C54 Cl8 1.856(18) . ? C54 Cl7 1.863(15) . ? C54 H54 1.0000 . ? C14A C15A 1.541(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N1 178.3(4) . 2_665 ? N1 Zn1 N1 89.988(6) . 4_565 ? N1 Zn1 N1 89.989(6) 2_665 4_565 ? N1 Zn1 N1 89.986(6) . 3_655 ? N1 Zn1 N1 89.987(7) 2_665 3_655 ? N1 Zn1 N1 178.3(4) 4_565 3_655 ? N1 Zn1 F1 90.85(19) . . ? N1 Zn1 F1 90.84(19) 2_665 . ? N1 Zn1 F1 90.84(19) 4_565 . ? N1 Zn1 F1 90.84(19) 3_655 . ? N1 Zn1 F6 89.15(19) . . ? N1 Zn1 F6 89.16(19) 2_665 . ? N1 Zn1 F6 89.16(19) 4_565 . ? N1 Zn1 F6 89.16(19) 3_655 . ? F1 Zn1 F6 180.000(1) . . ? F3 Zn2 F4 180.000(3) . . ? F3 Zn2 N3 87.95(18) . 2_665 ? F4 Zn2 N3 92.05(18) . 2_665 ? F3 Zn2 N3 87.95(17) . 4_565 ? F4 Zn2 N3 92.05(17) . 4_565 ? N3 Zn2 N3 89.929(13) 2_665 4_565 ? F3 Zn2 N3 87.95(17) . 3_655 ? F4 Zn2 N3 92.05(17) . 3_655 ? N3 Zn2 N3 89.927(14) 2_665 3_655 ? N3 Zn2 N3 175.9(3) 4_565 3_655 ? F3 Zn2 N3 87.95(18) . . ? F4 Zn2 N3 92.05(18) . . ? N3 Zn2 N3 175.9(3) 2_665 . ? N3 Zn2 N3 89.927(14) 4_565 . ? N3 Zn2 N3 89.925(14) 3_655 . ? F9 Zn3 F12 180.0 . 1_554 ? F9 Zn3 N2 91.1(2) . 3 ? F12 Zn3 N2 88.9(2) 1_554 3 ? F9 Zn3 N2 91.1(2) . . ? F12 Zn3 N2 88.9(2) 1_554 . ? N2 Zn3 N2 89.983(9) 3 . ? F9 Zn3 N2 91.1(2) . 2 ? F12 Zn3 N2 88.9(2) 1_554 2 ? N2 Zn3 N2 89.979(9) 3 2 ? N2 Zn3 N2 177.8(5) . 2 ? F9 Zn3 N2 91.1(2) . 4 ? F12 Zn3 N2 88.9(2) 1_554 4 ? N2 Zn3 N2 177.8(5) 3 4 ? N2 Zn3 N2 89.977(9) . 4 ? N2 Zn3 N2 89.978(9) 2 4 ? F7 Zn4 F10 180.000(2) . . ? F7 Zn4 N4 87.4(4) . 3 ? F10 Zn4 N4 92.6(4) . 3 ? F7 Zn4 N4 87.4(5) . 4 ? F10 Zn4 N4 92.6(5) . 4 ? N4 Zn4 N4 174.7(7) 3 4 ? F7 Zn4 N4 87.4(6) . 2 ? F10 Zn4 N4 92.6(6) . 2 ? N4 Zn4 N4 89.88(18) 3 2 ? N4 Zn4 N4 89.9(2) 4 2 ? F7 Zn4 N4 87.35(19) . . ? F10 Zn4 N4 92.65(19) . . ? N4 Zn4 N4 89.88(19) 3 . ? N4 Zn4 N4 89.9(2) 4 . ? N4 Zn4 N4 174.7(7) 2 . ? F2 Si1 F2 178.9(7) 2_665 . ? F2 Si1 F2 89.997(8) 2_665 3_655 ? F2 Si1 F2 89.992(8) . 3_655 ? F2 Si1 F2 89.995(8) 2_665 4_565 ? F2 Si1 F2 89.995(9) . 4_565 ? F2 Si1 F2 178.9(7) 3_655 4_565 ? F2 Si1 F3 90.6(3) 2_665 . ? F2 Si1 F3 90.6(3) . . ? F2 Si1 F3 90.6(3) 3_655 . ? F2 Si1 F3 90.6(3) 4_565 . ? F2 Si1 F1 89.4(3) 2_665 . ? F2 Si1 F1 89.4(3) . . ? F2 Si1 F1 89.4(3) 3_655 . ? F2 Si1 F1 89.4(3) 4_565 . ? F3 Si1 F1 180.000(3) . . ? Si1 F1 Zn1 180.000(1) . . ? Si1 F3 Zn2 180.000(1) . . ? F4 Si2 F5 91.7(5) . 3_655 ? F4 Si2 F5 91.7(5) . 4_565 ? F5 Si2 F5 176.6(9) 3_655 4_565 ? F4 Si2 F5 91.7(5) . . ? F5 Si2 F5 89.95(3) 3_655 . ? F5 Si2 F5 89.95(3) 4_565 . ? F4 Si2 F5 91.7(5) . 2_665 ? F5 Si2 F5 89.95(3) 3_655 2_665 ? F5 Si2 F5 89.95(3) 4_565 2_665 ? F5 Si2 F5 176.6(9) . 2_665 ? F4 Si2 F6 180.0 . 1_556 ? F5 Si2 F6 88.3(4) 3_655 1_556 ? F5 Si2 F6 88.3(4) 4_565 1_556 ? F5 Si2 F6 88.3(4) . 1_556 ? F5 Si2 F6 88.3(4) 2_665 1_556 ? Si2 F4 Zn2 180.000(1) . . ? Si2 F6 Zn1 180.0 1_554 . ? F8 Si3 F8 90.001(2) 3 2 ? F8 Si3 F8 90.001(2) 3 . ? F8 Si3 F8 179.7(7) 2 . ? F8 Si3 F8 179.7(7) 3 4 ? F8 Si3 F8 89.998(3) 2 4 ? F8 Si3 F8 89.998(2) . 4 ? F8 Si3 F7 90.1(4) 3 . ? F8 Si3 F7 90.1(4) 2 . ? F8 Si3 F7 90.1(4) . . ? F8 Si3 F7 90.1(4) 4 . ? F8 Si3 F9 89.9(4) 3 . ? F8 Si3 F9 89.9(4) 2 . ? F8 Si3 F9 89.9(4) . . ? F8 Si3 F9 89.9(4) 4 . ? F7 Si3 F9 180.000(1) . . ? Si3 F7 Zn4 180.0 . . ? Si3 F9 Zn3 180.0 . . ? F11 Si4 F11 89.98(3) . 3 ? F11 Si4 F11 177.9(12) . 2 ? F11 Si4 F11 89.98(2) 3 2 ? F11 Si4 F11 89.98(2) . 4 ? F11 Si4 F11 177.9(12) 3 4 ? F11 Si4 F11 89.98(3) 2 4 ? F11 Si4 F12 91.1(6) . . ? F11 Si4 F12 91.1(6) 3 . ? F11 Si4 F12 91.1(6) 2 . ? F11 Si4 F12 91.1(6) 4 . ? F11 Si4 F10 88.9(6) . . ? F11 Si4 F10 88.9(6) 3 . ? F11 Si4 F10 88.9(6) 2 . ? F11 Si4 F10 88.9(6) 4 . ? F12 Si4 F10 180.000(3) . . ? Si4 F10 Zn4 180.000(1) . . ? Si4 F12 Zn3 180.0 . 1_556 ? C5 N1 C1 114.9(6) . . ? C5 N1 Zn1 120.7(5) . . ? C1 N1 Zn1 123.8(5) . . ? C2 C1 N1 123.0(8) . . ? C2 C1 H1 118.4 . . ? N1 C1 H1 118.6 . . ? C1 C2 C3 122.8(8) . . ? C1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C6 C3 C2 123.6(8) . . ? C6 C3 C4 122.7(8) . . ? C2 C3 C4 113.7(7) . . ? C5 C4 C3 121.8(7) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? N1 C5 C4 122.8(7) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.5 . . ? C3 C6 C7 120.0(8) . . ? C3 C6 C11 123.1(9) . . ? C7 C6 C11 116.6(7) . . ? C8 C7 C6 121.2(8) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 120.3(8) . . ? C7 C8 O1 117.3(8) . . ? C9 C8 O1 122.3(8) . . ? C10 C9 C8 120.3(8) . . ? C10 C9 C20 118.2(9) . . ? C8 C9 C20 121.2(8) . . ? C9 C10 C11 123.1(9) . . ? C9 C10 H10 118.4 . . ? C11 C10 H10 118.5 . . ? O2 C11 C10 126.5(9) . . ? O2 C11 C6 115.2(8) . . ? C10 C11 C6 118.0(9) . . ? C8 O1 C12 124.9(9) . . ? C14 C12 O1 99.5(14) . . ? C14 C12 C13 139.1(16) . . ? O1 C12 C13 115.2(15) . . ? C14 C12 C14A 34.3(11) . . ? O1 C12 C14A 109.5(7) . . ? C13 C12 C14A 109.3(8) . . ? C14 C12 C13A 127.3(17) . . ? O1 C12 C13A 106.6(13) . . ? C14A C12 C13A 93.2(15) . . ? C12 C14 C15 111.1(10) . . ? C11 O2 C16 114.4(7) . . ? O2 C16 C17 111.7(12) . . ? O2 C16 C17A 91.1(14) . . ? O2 C16 C18 109.9(10) . . ? C17 C16 C18 108(2) . . ? C17A C16 C18 107.1(17) . . ? C19 C18 C16 109.3(9) . . ? C19A C18 C16 91.0(15) . . ? C24 C20 C21 122.9(9) . . ? C24 C20 C9 117.7(9) . . ? C21 C20 C9 119.2(8) . . ? C20 C21 C22 117.5(8) . . ? C20 C21 H21 121.4 . . ? C22 C21 H21 121.2 . . ? N2 C22 C21 121.3(8) . . ? N2 C22 H22 119.3 . . ? C21 C22 H22 119.5 . . ? C22 N2 C23 122.9(8) . . ? C22 N2 Zn3 120.3(7) . . ? C23 N2 Zn3 116.1(6) . . ? N2 C23 C24 120.3(9) . . ? N2 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C20 C24 C23 114.7(10) . . ? C20 C24 H24 122.7 . . ? C23 C24 H24 122.6 . . ? C31 N3 C27 119.1(6) . . ? C31 N3 Zn2 123.0(5) . . ? C27 N3 Zn2 117.8(5) . . ? N3 C27 C28 119.0(8) . . ? N3 C27 H27 120.5 . . ? C28 C27 H27 120.6 . . ? C29 C28 C27 118.9(7) . . ? C29 C28 H28 120.7 . . ? C27 C28 H28 120.4 . . ? C30 C29 C28 117.2(7) . . ? C30 C29 C32 125.4(8) . . ? C28 C29 C32 117.4(6) . . ? C31 C30 C29 122.5(8) . . ? C31 C30 H30 118.7 . . ? C29 C30 H30 118.8 . . ? N3 C31 C30 123.2(7) . . ? N3 C31 H31 118.3 . . ? C30 C31 H31 118.5 . . ? C33 C32 C37 120.0 . . ? C33 C32 C29 120.6(5) . . ? C37 C32 C29 119.3(5) . . ? O3 C33 C34 121.2(4) . . ? O3 C33 C32 118.7(4) . . ? C34 C33 C32 120.0 . . ? C33 C34 C35 120.0 . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C36 C35 C34 120.0 . . ? C36 C35 C46 121.4(4) . . ? C34 C35 C46 118.6(4) . . ? C37 C36 C35 120.0 . . ? C37 C36 O4 120.8(5) . . ? C35 C36 O4 119.0(5) . . ? C36 C37 C32 120.0 . . ? C36 C37 H37 120.0 . . ? C32 C37 H37 120.0 . . ? C33 O3 C38 119.7(8) . . ? C39 C38 C40 110.1(8) . . ? C39 C38 O3 131.3(13) . . ? C40 C38 O3 107.1(12) . . ? C39 C38 H38 101.3 . . ? C40 C38 H38 100.9 . . ? O3 C38 H38 101.3 . . ? C38 C39 H39A 109.6 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.3 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C41 C40 C38 97.0(14) . . ? C41 C40 H40A 111.9 . . ? C38 C40 H40A 112.1 . . ? C41 C40 H40B 112.7 . . ? C38 C40 H40B 112.9 . . ? H40A C40 H40B 109.9 . . ? C40 C41 H41A 109.2 . . ? C40 C41 H41B 109.3 . . ? H41A C41 H41B 109.4 . . ? C40 C41 H41C 110.0 . . ? H41A C41 H41C 109.4 . . ? H41B C41 H41C 109.4 . . ? C36 O4 C42 123.5(8) . . ? O4 C42 C43 92.8(10) . . ? O4 C42 C45 95.9(10) . . ? C43 C42 C45 118.2(14) . . ? O4 C42 H42 115.3 . . ? C43 C42 H42 115.2 . . ? C45 C42 H42 115.3 . . ? C42 C43 C44 143.3(14) . . ? C42 C43 H43A 100.9 . . ? C44 C43 H43A 101.3 . . ? C42 C43 H43B 101.1 . . ? C44 C43 H43B 101.2 . . ? H43A C43 H43B 104.4 . . ? C43 C44 H44A 109.8 . . ? C43 C44 H44B 109.0 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C42 C45 H45A 109.5 . . ? C42 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C42 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C47 C46 C50 120.0 . . ? C47 C46 C35 121.2(4) . . ? C50 C46 C35 118.7(4) . . ? C46 C47 C48 120.0 . . ? C46 C47 H47 120.0 . . ? C48 C47 H47 120.0 . . ? N4 C48 C47 120.0 . . ? N4 C48 H48 120.0 . . ? C47 C48 H48 120.0 . . ? C48 N4 C49 120.0 . . ? C48 N4 Zn4 116.8(3) . . ? C49 N4 Zn4 123.1(3) . . ? C50 C49 N4 120.0 . . ? C50 C49 H49 120.0 . . ? N4 C49 H49 120.0 . . ? C49 C50 C46 120.0 . . ? C49 C50 H50 120.0 . . ? C46 C50 H50 120.0 . . ? Cl3 C51 Cl2 114.3(9) . . ? Cl3 C51 Cl1 109.2(7) . . ? Cl2 C51 Cl1 109.6(7) . . ? Cl3 C51 H51 107.9 . . ? Cl2 C51 H51 107.9 . . ? Cl1 C51 H51 107.9 . . ? Cl4 C52 Cl6 119.6(10) . . ? Cl4 C52 Cl5 116.3(10) . . ? Cl6 C52 Cl5 106.8(9) . . ? Cl4 C52 H52 104.1 . . ? Cl6 C52 H52 104.1 . . ? Cl5 C52 H52 104.1 . . ? Cl9 C54 Cl8 109.8(10) . . ? Cl9 C54 Cl7 105.1(7) . . ? Cl8 C54 Cl7 106.1(9) . . ? Cl9 C54 H54 111.8 . . ? Cl8 C54 H54 111.8 . . ? Cl7 C54 H54 111.9 . . ? C15A C14A C12 109.9(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.10 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.539 _refine_diff_density_min -1.451 _refine_diff_density_rms 0.202 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 -0.011 0.496 -0.001 3524.3 364.8 _platon_squeeze_details ; ; data_e2503a _database_code_depnum_ccdc_archive 'CCDC 923941' #TrackingRef 'web_deposit_cif_file_2_Gruber_1360327886.s2503.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H64 F6 N4 O4 Si Zn, 2(C H Cl3)' _chemical_formula_sum 'C54 H66 Cl6 F6 N4 O4 Si Zn' _chemical_formula_weight 1255.27 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4 _symmetry_space_group_name_Hall 'I 4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z' 'y, -x, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' 'y+1/2, -x+1/2, z+1/2' _cell_length_a 22.0927(4) _cell_length_b 22.0927(4) _cell_length_c 15.2503(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7443.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9673 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 30.03 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.120 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2600 _exptl_absorpt_coefficient_mu 0.614 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9412 _exptl_absorpt_correction_T_max 0.9468 _exptl_absorpt_process_details sadabs _exptl_special_details ; Owing to large disorder of the solvent present in the cavities of this structure, the SQUEEZE command has been applied. The two chains are disordered over two positions. This disorder has been refined isotropicaly accordingly. Note however that the H atoms have not been introduced on the corresponding carbons although they are taken into account in the formula of the title compound ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61327 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0822 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 30.03 _reflns_number_total 9864 _reflns_number_gt 5517 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0998P)^2^+1.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.16(2) _refine_ls_number_reflns 9864 _refine_ls_number_parameters 322 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1964 _refine_ls_wR_factor_gt 0.1842 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.028 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 1.0000 1.0000 0.41515(6) 0.0147(2) Uani 1 4 d S . 1 Zn2 Zn 1.0000 1.0000 -0.08264(6) 0.0133(2) Uani 1 4 d S . 1 Si1 Si 1.0000 1.0000 -0.3350(3) 0.0191(3) Uani 1 4 d S . 1 Si2 Si 1.0000 1.0000 0.1651(3) 0.0162(3) Uani 1 4 d S . 1 F1 F 1.0000 1.0000 -0.2180(5) 0.0276(16) Uani 1 4 d S A 1 F2 F 0.9932(2) 0.92552(11) -0.3380(4) 0.0881(13) Uani 1 1 d . B 1 F3 F 1.0000 1.0000 0.5580(4) 0.0270(17) Uani 1 4 d S . 1 F4 F 1.0000 1.0000 0.0527(5) 0.0288(17) Uani 1 4 d S C 1 F5 F 0.92592(9) 1.01508(12) 0.1665(3) 0.0454(6) Uani 1 1 d . D 1 F6 F 1.0000 1.0000 0.2765(4) 0.0263(16) Uani 1 4 d S E 1 N1 N 0.9320(2) 0.93261(18) 0.4115(3) 0.0232(10) Uani 1 1 d . F 1 C1 C 0.8870(3) 0.9331(2) 0.3557(4) 0.0271(13) Uani 1 1 d . F 1 H1 H 0.8866 0.9646 0.3132 0.032 Uiso 1 1 calc R F 1 C2 C 0.8399(2) 0.8916(3) 0.3531(4) 0.0297(14) Uani 1 1 d . F 1 H2 H 0.8086 0.8952 0.3108 0.036 Uiso 1 1 calc R F 1 C3 C 0.8396(2) 0.8443(3) 0.4143(5) 0.0311(13) Uani 1 1 d . F 1 C4 C 0.8902(2) 0.8424(2) 0.4767(5) 0.0297(13) Uani 1 1 d . F 1 H4 H 0.8934 0.8117 0.5201 0.036 Uiso 1 1 calc R F 1 C5 C 0.9313(3) 0.8861(3) 0.4688(4) 0.0315(14) Uani 1 1 d . F 1 H5 H 0.9643 0.8844 0.5087 0.038 Uiso 1 1 calc R F 1 C6 C 0.7933(3) 0.7969(2) 0.4173(5) 0.0306(13) Uani 1 1 d . F 1 C7 C 0.7320(3) 0.8077(3) 0.4266(8) 0.071(3) Uani 1 1 d . F 1 C8 C 0.6915(3) 0.7637(3) 0.4231(7) 0.061(2) Uani 1 1 d . F 1 H8 H 0.6498 0.7744 0.4230 0.073 Uiso 1 1 calc R F 1 C9 C 0.7063(2) 0.7042(2) 0.4195(5) 0.0298(12) Uani 1 1 d . F 1 C10 C 0.7679(3) 0.6883(3) 0.4189(7) 0.0475(17) Uani 1 1 d . F 1 C11 C 0.8115(3) 0.7368(3) 0.4175(7) 0.0482(18) Uani 1 1 d . F 1 H11 H 0.8535 0.7275 0.4168 0.058 Uiso 1 1 calc R F 1 C12 C 0.6586(2) 0.6560(2) 0.4185(5) 0.0273(11) Uani 1 1 d . F 1 C13 C 1.1100(3) 0.8429(3) -0.0220(5) 0.0413(17) Uani 1 1 d . G 1 H13 H 1.1072 0.8112 0.0199 0.050 Uiso 1 1 calc R G 1 C14 C 1.0680(3) 0.8879(3) -0.0201(4) 0.0314(14) Uani 1 1 d . G 1 H14 H 1.0382 0.8888 0.0249 0.038 Uiso 1 1 calc R G 1 N2 N 1.06896(17) 0.93241(16) -0.0841(3) 0.0177(8) Uani 1 1 d . G 1 C15 C 1.1118(3) 0.9322(3) -0.1457(4) 0.0296(12) Uani 1 1 d . G 1 H15 H 1.1138 0.9627 -0.1894 0.035 Uiso 1 1 calc R G 1 C16 C 1.1550(3) 0.8834(3) -0.1428(5) 0.0414(18) Uani 1 1 d . G 1 H16 H 1.1846 0.8813 -0.1880 0.050 Uiso 1 1 calc R G 1 O1 O 0.7189(2) 0.8696(2) 0.4401(5) 0.099(3) Uani 1 1 d . F 1 C17 C 0.6591(4) 0.8846(3) 0.4704(5) 0.074(2) Uiso 1 1 d D F 1 H17A H 0.6489 0.8606 0.5232 0.089 Uiso 1 1 calc R F 1 H17B H 0.6288 0.8755 0.4243 0.089 Uiso 1 1 calc R F 1 C18 C 0.6584(5) 0.9532(4) 0.4925(6) 0.104(3) Uiso 1 1 d D F 1 C19 C 0.5903(8) 0.9683(10) 0.5161(15) 0.161(7) Uiso 0.826(13) 1 d PD F 1 C20 C 0.5960(15) 0.9580(16) 0.6194(18) 0.250(13) Uiso 0.826(13) 1 d PD F 1 C21 C 0.6551(8) 0.9857(8) 0.3993(9) 0.134(6) Uiso 0.826(13) 1 d PD F 1 C24A C 0.8168(5) 0.5094(4) 0.4068(6) 0.054(2) Uiso 0.826(13) 1 d PD F 1 C26A C 0.9243(10) 0.5486(15) 0.393(2) 2.0(6) Uiso 0.826(13) 1 d PD F 1 C25A C 0.9107(7) 0.5347(12) 0.4906(16) 0.198(12) Uiso 0.826(13) 1 d PD F 1 O2 O 0.7834(2) 0.6324(2) 0.4405(5) 0.092(2) Uani 1 1 d . . . C22 C 0.8447(4) 0.6166(4) 0.4623(6) 0.080(2) Uiso 1 1 d D F . H22A H 0.8597 0.6419 0.5113 0.096 Uiso 1 1 calc R . . H22B H 0.8716 0.6223 0.4111 0.096 Uiso 1 1 calc R . . C23 C 0.8421(4) 0.5463(4) 0.4904(6) 0.094(3) Uiso 1 1 d D . . C27 C 0.6949(3) 0.4219(3) 0.6720(7) 0.0737(17) Uani 1 1 d . . . H27 H 0.6497 0.4250 0.6745 0.088 Uiso 1 1 calc R . . Cl1 Cl 0.72031(14) 0.45789(14) 0.5682(2) 0.1017(10) Uani 1 1 d . . . Cl2 Cl 0.72146(13) 0.45280(13) 0.7592(2) 0.0904(8) Uani 1 1 d . . . Cl3 Cl 0.71370(9) 0.34383(8) 0.6639(3) 0.0933(5) Uani 1 1 d . . . C21A C 0.7124(14) 0.9929(16) 0.468(3) 0.067(12) Uiso 0.174(13) 1 d PD F 2 C19A C 0.6078(13) 0.9696(14) 0.5578(19) 0.044(8) Uiso 0.174(13) 1 d PD F 2 C20A C 0.602(3) 0.938(3) 0.648(3) 0.103(18) Uiso 0.174(13) 1 d PD F 2 C24 C 0.799(3) 0.515(4) 0.423(4) 0.11(3) Uiso 0.174(13) 1 d PD F 2 C25 C 0.9063(15) 0.526(2) 0.517(5) 0.095 Uiso 0.174(13) 1 d PD F 2 C26 C 0.888(2) 0.461(2) 0.492(3) 0.095 Uiso 0.174(13) 1 d PD F 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0096(3) 0.0096(3) 0.0250(7) 0.000 0.000 0.000 Zn2 0.0093(3) 0.0093(3) 0.0215(6) 0.000 0.000 0.000 Si1 0.0199(5) 0.0199(5) 0.0176(9) 0.000 0.000 0.000 Si2 0.0134(4) 0.0134(4) 0.0218(9) 0.000 0.000 0.000 F1 0.036(2) 0.036(2) 0.011(3) 0.000 0.000 0.000 F2 0.207(4) 0.0229(12) 0.0339(17) 0.011(2) 0.004(4) -0.0147(16) F3 0.026(2) 0.026(2) 0.028(5) 0.000 0.000 0.000 F4 0.0211(19) 0.0211(19) 0.044(5) 0.000 0.000 0.000 F5 0.0205(9) 0.0771(17) 0.0385(13) 0.019(3) -0.004(2) 0.0110(9) F6 0.037(2) 0.037(2) 0.005(4) 0.000 0.000 0.000 N1 0.024(2) 0.015(2) 0.030(3) 0.010(2) -0.007(2) -0.0014(17) C1 0.021(3) 0.020(3) 0.041(3) 0.009(3) -0.005(3) -0.012(2) C2 0.019(3) 0.032(3) 0.038(3) 0.020(3) -0.012(2) -0.017(2) C3 0.020(3) 0.023(3) 0.050(4) 0.003(3) -0.004(3) -0.015(2) C4 0.020(2) 0.021(2) 0.048(4) 0.007(2) -0.011(2) -0.0030(18) C5 0.022(3) 0.025(3) 0.048(4) 0.023(3) -0.016(3) -0.009(2) C6 0.027(3) 0.023(3) 0.042(3) -0.006(3) -0.002(3) -0.017(2) C7 0.038(4) 0.014(3) 0.160(8) -0.009(4) 0.020(5) -0.002(2) C8 0.024(3) 0.040(4) 0.118(7) 0.001(5) 0.023(4) -0.001(3) C9 0.022(3) 0.024(3) 0.044(3) 0.005(3) 0.004(3) -0.009(2) C10 0.021(3) 0.028(3) 0.093(5) 0.013(3) 0.001(3) -0.012(2) C11 0.022(3) 0.021(3) 0.102(5) 0.014(4) -0.007(4) -0.012(2) C12 0.021(3) 0.024(3) 0.036(3) -0.002(3) 0.006(3) -0.007(2) C13 0.041(4) 0.027(3) 0.057(5) 0.015(3) -0.005(3) 0.009(3) C14 0.030(3) 0.022(3) 0.043(4) 0.011(3) 0.013(3) 0.006(2) N2 0.0136(19) 0.0090(17) 0.030(2) -0.0021(19) 0.000(2) 0.0066(14) C15 0.029(3) 0.032(3) 0.027(3) 0.006(2) 0.003(2) 0.013(2) C16 0.038(3) 0.048(4) 0.038(4) 0.012(3) 0.026(3) 0.031(3) O1 0.039(2) 0.023(2) 0.235(8) -0.025(3) 0.040(4) -0.0148(17) O2 0.044(3) 0.023(2) 0.208(7) 0.005(3) -0.020(3) 0.0009(17) C27 0.065(3) 0.099(4) 0.057(4) 0.006(6) 0.023(5) 0.023(3) Cl1 0.103(2) 0.101(2) 0.101(2) 0.0244(16) 0.0004(16) 0.0335(16) Cl2 0.0980(19) 0.0943(18) 0.0790(17) -0.0177(14) -0.0177(14) -0.0036(14) Cl3 0.1050(12) 0.0836(10) 0.0912(11) 0.0016(19) -0.008(2) 0.0342(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 F6 2.115(6) . ? Zn1 N1 2.116(4) 2_775 ? Zn1 N1 2.116(4) 3_755 ? Zn1 N1 2.116(4) . ? Zn1 N1 2.116(4) 4_575 ? Zn1 F3 2.178(7) . ? Zn2 F1 2.065(7) . ? Zn2 F4 2.064(8) . ? Zn2 N2 2.133(3) 3_755 ? Zn2 N2 2.133(3) 2_775 ? Zn2 N2 2.133(3) 4_575 ? Zn2 N2 2.133(3) . ? Si1 F3 1.631(8) 1_554 ? Si1 F2 1.653(2) 3_755 ? Si1 F2 1.653(2) 2_775 ? Si1 F2 1.653(2) . ? Si1 F2 1.653(2) 4_575 ? Si1 F1 1.784(9) . ? Si2 F5 1.6703(19) 2_775 ? Si2 F5 1.6703(19) 4_575 ? Si2 F5 1.6704(19) . ? Si2 F5 1.6704(19) 3_755 ? Si2 F6 1.699(8) . ? Si2 F4 1.714(9) . ? F3 Si1 1.631(8) 1_556 ? N1 C1 1.308(7) . ? N1 C5 1.349(7) . ? C1 C2 1.387(7) . ? C1 H1 0.9500 . ? C2 C3 1.402(8) . ? C2 H2 0.9500 . ? C3 C6 1.463(6) . ? C3 C4 1.469(9) . ? C4 C5 1.331(8) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.382(9) . ? C6 C11 1.388(8) . ? C7 C8 1.322(9) . ? C7 O1 1.414(8) . ? C8 C9 1.356(9) . ? C8 H8 0.9500 . ? C9 C10 1.406(8) . ? C9 C12 1.501(7) . ? C10 O2 1.324(8) . ? C10 C11 1.442(7) . ? C11 H11 0.9500 . ? C12 C16 1.316(9) 7_645 ? C12 C13 1.362(9) 7_645 ? C13 C12 1.362(9) 8_564 ? C13 C14 1.360(8) . ? C13 H13 0.9500 . ? C14 N2 1.386(7) . ? C14 H14 0.9500 . ? N2 C15 1.334(7) . ? C15 C16 1.440(8) . ? C15 H15 0.9500 . ? C16 C12 1.316(9) 8_564 ? C16 H16 0.9500 . ? O1 C17 1.440(9) . ? C17 C18 1.552(11) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C21A 1.531(19) . ? C18 C19A 1.539(17) . ? C18 C19 1.583(15) . ? C18 C21 1.593(13) . ? C19 C20 1.596(17) . ? C24A C23 1.612(11) . ? C26A C25A 1.55(2) . ? C25A C23 1.537(15) . ? O2 C22 1.436(9) . ? C22 C23 1.613(11) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C25 1.54(2) . ? C23 C24 1.56(2) . ? C27 Cl2 1.606(10) . ? C27 Cl3 1.778(7) . ? C27 Cl1 1.860(9) . ? C27 H27 1.0000 . ? C19A C20A 1.56(2) . ? C25 C26 1.54(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 F6 Zn1 N1 88.47(14) . 2_775 ? F6 Zn1 N1 88.47(14) . 3_755 ? N1 Zn1 N1 89.961(9) 2_775 3_755 ? F6 Zn1 N1 88.47(14) . . ? N1 Zn1 N1 176.9(3) 2_775 . ? N1 Zn1 N1 89.956(9) 3_755 . ? F6 Zn1 N1 88.47(14) . 4_575 ? N1 Zn1 N1 89.960(8) 2_775 4_575 ? N1 Zn1 N1 176.9(3) 3_755 4_575 ? N1 Zn1 N1 89.960(9) . 4_575 ? F6 Zn1 F3 180.000(2) . . ? N1 Zn1 F3 91.53(14) 2_775 . ? N1 Zn1 F3 91.53(14) 3_755 . ? N1 Zn1 F3 91.53(14) . . ? N1 Zn1 F3 91.53(14) 4_575 . ? F1 Zn2 F4 180.000(3) . . ? F1 Zn2 N2 89.41(14) . 3_755 ? F4 Zn2 N2 90.59(14) . 3_755 ? F1 Zn2 N2 89.41(14) . 2_775 ? F4 Zn2 N2 90.59(14) . 2_775 ? N2 Zn2 N2 89.995(3) 3_755 2_775 ? F1 Zn2 N2 89.41(14) . 4_575 ? F4 Zn2 N2 90.59(14) . 4_575 ? N2 Zn2 N2 178.8(3) 3_755 4_575 ? N2 Zn2 N2 89.992(4) 2_775 4_575 ? F1 Zn2 N2 89.41(14) . . ? F4 Zn2 N2 90.59(14) . . ? N2 Zn2 N2 89.994(4) 3_755 . ? N2 Zn2 N2 178.8(3) 2_775 . ? N2 Zn2 N2 89.995(3) 4_575 . ? F3 Si1 F2 88.4(3) 1_554 3_755 ? F3 Si1 F2 88.4(3) 1_554 2_775 ? F2 Si1 F2 89.959(16) 3_755 2_775 ? F3 Si1 F2 88.4(3) 1_554 . ? F2 Si1 F2 89.953(17) 3_755 . ? F2 Si1 F2 176.8(6) 2_775 . ? F3 Si1 F2 88.4(3) 1_554 4_575 ? F2 Si1 F2 176.8(6) 3_755 4_575 ? F2 Si1 F2 89.956(17) 2_775 4_575 ? F2 Si1 F2 89.958(16) . 4_575 ? F3 Si1 F1 179.998(1) 1_554 . ? F2 Si1 F1 91.6(3) 3_755 . ? F2 Si1 F1 91.6(3) 2_775 . ? F2 Si1 F1 91.6(3) . . ? F2 Si1 F1 91.6(3) 4_575 . ? F5 Si2 F5 89.992(8) 2_775 4_575 ? F5 Si2 F5 178.5(5) 2_775 . ? F5 Si2 F5 89.988(8) 4_575 . ? F5 Si2 F5 89.991(8) 2_775 3_755 ? F5 Si2 F5 178.5(5) 4_575 3_755 ? F5 Si2 F5 89.990(8) . 3_755 ? F5 Si2 F6 89.3(3) 2_775 . ? F5 Si2 F6 89.3(3) 4_575 . ? F5 Si2 F6 89.3(3) . . ? F5 Si2 F6 89.3(3) 3_755 . ? F5 Si2 F4 90.7(3) 2_775 . ? F5 Si2 F4 90.7(3) 4_575 . ? F5 Si2 F4 90.7(3) . . ? F5 Si2 F4 90.7(3) 3_755 . ? F6 Si2 F4 180.000(4) . . ? Si1 F1 Zn2 180.000(1) . . ? Si1 F3 Zn1 179.998(1) 1_556 . ? Si2 F4 Zn2 180.000(1) . . ? Si2 F6 Zn1 180.000(1) . . ? C1 N1 C5 114.8(4) . . ? C1 N1 Zn1 123.4(4) . . ? C5 N1 Zn1 121.8(4) . . ? N1 C1 C2 125.6(5) . . ? N1 C1 H1 117.2 . . ? C2 C1 H1 117.2 . . ? C1 C2 C3 118.6(5) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C6 123.9(6) . . ? C2 C3 C4 116.6(5) . . ? C6 C3 C4 119.4(6) . . ? C5 C4 C3 116.1(5) . . ? C5 C4 H4 121.9 . . ? C3 C4 H4 122.0 . . ? C4 C5 N1 128.2(5) . . ? C4 C5 H5 115.9 . . ? N1 C5 H5 115.9 . . ? C7 C6 C11 116.6(5) . . ? C7 C6 C3 124.5(6) . . ? C11 C6 C3 118.8(5) . . ? C8 C7 C6 122.3(6) . . ? C8 C7 O1 125.3(6) . . ? C6 C7 O1 112.4(6) . . ? C7 C8 C9 123.3(7) . . ? C7 C8 H8 118.3 . . ? C9 C8 H8 118.4 . . ? C8 C9 C10 118.5(6) . . ? C8 C9 C12 121.3(6) . . ? C10 C9 C12 120.2(5) . . ? O2 C10 C9 118.9(5) . . ? O2 C10 C11 121.7(6) . . ? C9 C10 C11 117.4(6) . . ? C6 C11 C10 121.2(6) . . ? C6 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C16 C12 C13 116.4(5) 7_645 7_645 ? C16 C12 C9 120.9(6) 7_645 . ? C13 C12 C9 122.6(6) 7_645 . ? C12 C13 C14 122.7(6) 8_564 . ? C12 C13 H13 118.7 8_564 . ? C14 C13 H13 118.7 . . ? C13 C14 N2 119.5(6) . . ? C13 C14 H14 120.2 . . ? N2 C14 H14 120.2 . . ? C15 N2 C14 120.2(4) . . ? C15 N2 Zn2 121.1(4) . . ? C14 N2 Zn2 118.6(4) . . ? N2 C15 C16 116.9(5) . . ? N2 C15 H15 121.6 . . ? C16 C15 H15 121.5 . . ? C12 C16 C15 123.9(5) 8_564 . ? C12 C16 H16 118.0 8_564 . ? C15 C16 H16 118.0 . . ? C7 O1 C17 117.2(5) . . ? O1 C17 C18 107.6(6) . . ? O1 C17 H17A 110.2 . . ? C18 C17 H17A 110.2 . . ? O1 C17 H17B 110.2 . . ? C18 C17 H17B 110.1 . . ? H17A C17 H17B 108.5 . . ? C21A C18 C19A 126(2) . . ? C21A C18 C17 119.9(17) . . ? C19A C18 C17 112.2(14) . . ? C21A C18 C19 132.6(18) . . ? C17 C18 C19 105.3(10) . . ? C19A C18 C21 115.9(15) . . ? C17 C18 C21 104.3(9) . . ? C19 C18 C21 93.7(12) . . ? C18 C19 C20 96.8(18) . . ? C23 C25A C26A 99.0(12) . . ? C10 O2 C22 121.8(5) . . ? O2 C22 C23 105.1(6) . . ? O2 C22 H22A 110.7 . . ? C23 C22 H22A 110.7 . . ? O2 C22 H22B 110.7 . . ? C23 C22 H22B 110.7 . . ? H22A C22 H22B 108.8 . . ? C25A C23 C24 122(3) . . ? C25 C23 C24 127(4) . . ? C25A C23 C24A 105.0(10) . . ? C25 C23 C24A 112(2) . . ? C25A C23 C22 97.3(12) . . ? C25 C23 C22 108(2) . . ? C24 C23 C22 106(3) . . ? C24A C23 C22 106.8(7) . . ? Cl2 C27 Cl3 112.6(5) . . ? Cl2 C27 Cl1 114.4(4) . . ? Cl3 C27 Cl1 106.5(5) . . ? Cl2 C27 H27 107.7 . . ? Cl3 C27 H27 107.7 . . ? Cl1 C27 H27 107.7 . . ? C18 C19A C20A 122(3) . . ? C26 C25 C23 87(3) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 1.259 _refine_diff_density_min -0.670 _refine_diff_density_rms 0.108 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.498 0.500 0.187 1301.5 336.6 2 0.000 0.998 0.687 1301.5 336.6 _platon_squeeze_details ; ; data_e2505b _database_code_depnum_ccdc_archive 'CCDC 923942' #TrackingRef 'web_deposit_cif_file_3_Gruber_1360327886.s2505.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H48 F6 N4 O8 Si Zn, C H Cl3' _chemical_formula_sum 'C45 H49 Cl3 F6 N4 O8 Si Zn' _chemical_formula_weight 1087.69 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4 _symmetry_space_group_name_Hall 'P 4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z' 'y, -x, z' _cell_length_a 22.0440(15) _cell_length_b 22.0440(15) _cell_length_c 15.1513(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7362.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2951 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.67 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 0.981 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 0.511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9700 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details sadabs _exptl_special_details ; The EADP command was used many times because of the flopiness of many atoms.It's why there is a large Non-solvent H on the chain The disordered solvent molecules could not be refined. The SQUEEZE command was therefore applied. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49262 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.2390 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 30.04 _reflns_number_total 19262 _reflns_number_gt 6772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+0.5000P] 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 0.26(3) _chemical_absolute_configuration rm _refine_ls_number_reflns 19262 _refine_ls_number_parameters 461 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.2082 _refine_ls_R_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.2511 _refine_ls_wR_factor_gt 0.2261 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.093 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.5000 0.01429(9) 0.0119(4) Uani 1 4 d S . . Zn2 Zn 0.5000 0.5000 0.51289(9) 0.0146(4) Uani 1 4 d S . . Zn3 Zn 0.0000 0.0000 -0.00054(12) 0.0219(5) Uani 1 4 d S . . Zn4 Zn 0.0000 0.0000 0.49761(11) 0.0206(5) Uani 1 4 d S . . Si1 Si 0.5000 0.5000 0.2629(3) 0.0151(8) Uani 1 4 d S . . Si2 Si 0.5000 0.5000 0.7630(4) 0.0233(10) Uani 1 4 d S . . Si3 Si 0.0000 0.0000 0.2480(4) 0.0207(11) Uani 1 4 d S . . Si4 Si 0.0000 0.0000 0.7512(4) 0.0291(12) Uani 1 4 d S . . F1 F 0.5000 0.5000 -0.1226(7) 0.046(3) Uani 1 4 d S . . F2 F 0.5000 0.5000 0.1491(5) 0.046(3) Uani 1 4 d S . . F3 F 0.5169(2) 0.42654(16) 0.2595(4) 0.0431(11) Uani 1 1 d . . . F4 F 0.5000 0.5000 0.3760(6) 0.028(3) Uani 1 4 d S . . F5 F 0.5000 0.5000 0.6528(6) 0.032(3) Uani 1 4 d S . . F6 F 0.5727(3) 0.4974(7) 0.7680(5) 0.199(5) Uani 1 1 d . . . F7 F 0.0000 0.0000 0.1389(6) 0.020(2) Uani 1 4 d S . . F9 F -0.07321(17) 0.01903(18) 0.2467(3) 0.0342(11) Uani 1 1 d . . . F10 F 0.0000 0.0000 0.3664(7) 0.031(3) Uani 1 4 d S . . F11 F 0.0000 0.0000 0.6331(7) 0.041(3) Uani 1 4 d S . . F12 F 0.0723(3) 0.0095(5) 0.7485(5) 0.158(4) Uani 1 1 d . . . F13 F 0.0000 0.0000 0.8579(8) 0.049(4) Uani 1 4 d S . . N1 N 0.42979(19) 0.43633(19) 0.0142(3) 0.0276(8) Uani 1 1 d G . . C1 C 0.4312(2) 0.3905(2) 0.0771(3) 0.0276(8) Uani 1 1 d G . . H1 H 0.4631 0.3892 0.1193 0.033 Uiso 1 1 calc R . . C2 C 0.3859(2) 0.3466(2) 0.0785(3) 0.0276(8) Uani 1 1 d G . . H2 H 0.3869 0.3153 0.1215 0.033 Uiso 1 1 calc R . . C3 C 0.3393(2) 0.3485(2) 0.0168(3) 0.0276(8) Uani 1 1 d G . . C4 C 0.3379(2) 0.3944(2) -0.0462(3) 0.0276(8) Uani 1 1 d G . . H4 H 0.3060 0.3957 -0.0883 0.033 Uiso 1 1 calc R . . C5 C 0.3831(2) 0.4383(2) -0.0475(3) 0.0276(8) Uani 1 1 d G . . H5 H 0.3822 0.4696 -0.0905 0.033 Uiso 1 1 calc R . . C6 C 0.2916(4) 0.2974(4) 0.0136(6) 0.0379(9) Uani 1 1 d . . . C7 C 0.2318(4) 0.3112(4) 0.0130(6) 0.0379(9) Uani 1 1 d . . . C8 C 0.1875(4) 0.2633(3) 0.0087(6) 0.0379(9) Uani 1 1 d . . . H8 H 0.1455 0.2725 0.0057 0.045 Uiso 1 1 calc R . . C9 C 0.2080(4) 0.2008(4) 0.0089(6) 0.0379(9) Uani 1 1 d . . . C10 C 0.2711(4) 0.1919(4) 0.0189(6) 0.0379(9) Uani 1 1 d . . . C11 C 0.3107(4) 0.2379(4) 0.0223(6) 0.0379(9) Uani 1 1 d . . . H11 H 0.3526 0.2296 0.0309 0.045 Uiso 1 1 calc R . . O1 O 0.2155(3) 0.3706(3) 0.0018(5) 0.0570(18) Uani 1 1 d D . . C12 C 0.1493(4) 0.3857(4) 0.0021(9) 0.066(3) Uani 1 1 d D . . H12A H 0.1309 0.3753 -0.0555 0.079 Uiso 1 1 calc R . . H12B H 0.1281 0.3625 0.0488 0.079 Uiso 1 1 calc R . . C13 C 0.1435(5) 0.4515(5) 0.0190(12) 0.122(6) Uani 1 1 d D . . H13 H 0.1580 0.4547 0.0814 0.147 Uiso 1 1 calc R . . O2 O 0.0815(4) 0.4719(6) 0.0265(10) 0.122(6) Uani 1 1 d D . . H2A H 0.0649 0.4546 0.0696 0.147 Uiso 1 1 calc R . . C14 C 0.1739(12) 0.5053(10) -0.0233(16) 0.122(6) Uani 1 1 d D . . H14A H 0.1960 0.4920 -0.0760 0.147 Uiso 1 1 calc R . . H14B H 0.2022 0.5237 0.0186 0.147 Uiso 1 1 calc R . . H14C H 0.1431 0.5352 -0.0403 0.147 Uiso 1 1 calc R . . O3 O 0.2870(3) 0.1321(3) 0.0275(7) 0.121(6) Uani 1 1 d D . . C15 C 0.3382(5) 0.1092(5) -0.0215(11) 0.121(6) Uani 1 1 d D . . H15A H 0.3738 0.1364 -0.0166 0.145 Uiso 1 1 calc R . . H15B H 0.3282 0.1031 -0.0845 0.145 Uiso 1 1 calc RD . . C16 C 0.3497(6) 0.0463(5) 0.0275(11) 0.115(6) Uani 1 1 d D . . H16 H 0.3355 0.0392 0.0893 0.138 Uiso 1 1 calc R . . O4 O 0.4132(6) 0.0358(6) 0.001(2) 0.115(6) Uani 1 1 d D . . H4A H 0.4192 -0.0017 -0.0048 0.138 Uiso 1 1 calc R . . C17 C 0.3259(7) 0.0113(8) -0.0468(17) 0.115(6) Uani 1 1 d D . . H17A H 0.3560 0.0105 -0.0944 0.138 Uiso 1 1 calc R . . H17B H 0.2884 0.0302 -0.0683 0.138 Uiso 1 1 calc RD . . H17C H 0.3173 -0.0302 -0.0275 0.432 Uiso 1 1 calc R . . C18 C 0.1616(3) 0.1540(3) 0.0073(5) 0.0285(8) Uani 1 1 d . . . C19 C 0.1161(3) 0.1567(3) -0.0541(5) 0.0285(8) Uani 1 1 d . . . H19 H 0.1150 0.1889 -0.0957 0.034 Uiso 1 1 calc R . . C20 C 0.0709(3) 0.1113(3) -0.0551(5) 0.0285(8) Uani 1 1 d . . . H20 H 0.0403 0.1130 -0.0993 0.034 Uiso 1 1 calc R . . N2 N 0.0696(3) 0.0682(3) 0.0008(4) 0.0285(8) Uani 1 1 d . . . C21 C 0.1118(3) 0.0676(3) 0.0625(5) 0.0285(8) Uani 1 1 d . . . H21 H 0.1105 0.0362 0.1054 0.034 Uiso 1 1 calc R . . C22 C 0.1569(3) 0.1090(3) 0.0680(5) 0.0285(8) Uani 1 1 d . . . H22 H 0.1856 0.1066 0.1147 0.034 Uiso 1 1 calc R . . N3 N 0.4327(2) 0.4315(2) 0.5092(4) 0.0157(10) Uani 1 1 d . . . C23 C 0.4326(3) 0.3868(3) 0.4485(4) 0.0157(10) Uani 1 1 d . . . H23 H 0.4638 0.3873 0.4053 0.019 Uiso 1 1 calc R . . C24 C 0.3927(4) 0.3425(3) 0.4444(5) 0.030(2) Uani 1 1 d . . . H24 H 0.3957 0.3126 0.3995 0.036 Uiso 1 1 calc R . . C25 C 0.3453(3) 0.3396(4) 0.5069(5) 0.0261(18) Uani 1 1 d . . . C26 C 0.3436(3) 0.3862(4) 0.5703(5) 0.029(2) Uani 1 1 d . . . H26 H 0.3117 0.3887 0.6124 0.035 Uiso 1 1 calc R . . C27 C 0.3898(3) 0.4280(3) 0.5689(5) 0.029(2) Uani 1 1 d . . . H27 H 0.3908 0.4570 0.6153 0.035 Uiso 1 1 calc R . . C28 C 0.2950(2) 0.2928(2) 0.5077(4) 0.0352(7) Uani 1 1 d G . . C29 C 0.3078(2) 0.2312(2) 0.5018(5) 0.0352(7) Uani 1 1 d G . . C30 C 0.2608(2) 0.1892(2) 0.4999(4) 0.0352(7) Uani 1 1 d G . . H30 H 0.2695 0.1471 0.4959 0.042 Uiso 1 1 calc R . . C31 C 0.2009(2) 0.2089(2) 0.5039(4) 0.0352(7) Uani 1 1 d G . . C32 C 0.1881(2) 0.2705(2) 0.5098(4) 0.0352(7) Uani 1 1 d G . . C33 C 0.2351(2) 0.3124(2) 0.5117(4) 0.0352(7) Uani 1 1 d G . . H33 H 0.2264 0.3546 0.5157 0.042 Uiso 1 1 calc R . . O5 O 0.3685(2) 0.2131(2) 0.4828(5) 0.058(2) Uani 1 1 d D . . C34 C 0.3897(5) 0.1582(5) 0.5310(9) 0.098(5) Uani 1 1 d DU . . H34A H 0.3879 0.1652 0.5955 0.118 Uiso 1 1 calc R . . H34B H 0.3634 0.1231 0.5166 0.118 Uiso 1 1 calc R . . C35 C 0.4528(5) 0.1459(5) 0.5033(11) 0.102(5) Uani 1 1 d DU . . H35 H 0.4556 0.1573 0.4395 0.122 Uiso 1 1 calc R . . O6 O 0.4698(6) 0.0791(6) 0.5094(16) 0.102(5) Uani 1 1 d D . . H6 H 0.4453 0.0585 0.4793 0.122 Uiso 1 1 calc R . . C36 C 0.4989(8) 0.1870(8) 0.5537(17) 0.102(5) Uani 1 1 d DU . . H36A H 0.4955 0.2288 0.5324 0.122 Uiso 1 1 calc R . . H36B H 0.5402 0.1721 0.5433 0.122 Uiso 1 1 calc R . . H36C H 0.4901 0.1857 0.6171 0.122 Uiso 1 1 calc R . . O7 O 0.1299(3) 0.2855(3) 0.5000(6) 0.068(2) Uani 1 1 d D . . C37 C 0.1150(4) 0.3486(4) 0.4994(7) 0.052(3) Uani 1 1 d D . . H37A H 0.1355 0.3698 0.4502 0.062 Uiso 1 1 calc R . . H37B H 0.1265 0.3681 0.5558 0.062 Uiso 1 1 calc R . . C38 C 0.0451(6) 0.3487(6) 0.4869(14) 0.052(3) Uani 1 1 d DU . . H38 H 0.0353 0.3340 0.4261 0.062 Uiso 1 1 calc R . . O8 O 0.0337(5) 0.4145(4) 0.4914(11) 0.052(3) Uani 1 1 d DU . . H8A H 0.0631 0.4332 0.4689 0.062 Uiso 1 1 calc R . . C39 C 0.0048(11) 0.3179(12) 0.5508(14) 0.052(3) Uani 1 1 d DU . . H39A H 0.0137 0.2744 0.5512 0.062 Uiso 1 1 calc R . . H39B H -0.0376 0.3244 0.5338 0.062 Uiso 1 1 calc R . . H39C H 0.0117 0.3347 0.6099 0.062 Uiso 1 1 calc R . . C40 C 0.1509(2) 0.1638(2) 0.4968(4) 0.029(2) Uani 1 1 d G . . C41 C 0.1540(2) 0.1182(3) 0.4336(3) 0.052(3) Uani 1 1 d G . . H41 H 0.1855 0.1186 0.3908 0.063 Uiso 1 1 calc R . . C42 C 0.1111(2) 0.0720(2) 0.4331(3) 0.037(2) Uani 1 1 d G . . H42 H 0.1132 0.0408 0.3899 0.044 Uiso 1 1 calc R . . N4 N 0.0651(2) 0.0714(2) 0.4958(4) 0.0318(18) Uani 1 1 d G . . C43 C 0.0619(2) 0.1170(3) 0.5590(3) 0.054(3) Uani 1 1 d G . . H43 H 0.0305 0.1166 0.6019 0.064 Uiso 1 1 calc R . . C44 C 0.1049(3) 0.1632(2) 0.5595(4) 0.050(3) Uani 1 1 d G . . H44 H 0.1027 0.1944 0.6027 0.060 Uiso 1 1 calc R . . C45 C 0.5758(4) 0.3013(4) 0.2671(7) 0.059(2) Uani 1 1 d . . . H45 H 0.5775 0.3466 0.2712 0.071 Uiso 1 1 calc R . . Cl1 Cl 0.52974(17) 0.28179(15) 0.1773(2) 0.0933(11) Uani 1 1 d . . . Cl2 Cl 0.53916(19) 0.27226(17) 0.3669(2) 0.1055(13) Uani 1 1 d . . . Cl3 Cl 0.64521(14) 0.27544(17) 0.2638(3) 0.1094(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0153(6) 0.0153(6) 0.0052(8) 0.000 0.000 0.000 Zn2 0.0143(6) 0.0143(6) 0.0152(9) 0.000 0.000 0.000 Zn3 0.0136(6) 0.0136(6) 0.0385(13) 0.000 0.000 0.000 Zn4 0.0126(6) 0.0126(6) 0.0364(13) 0.000 0.000 0.000 Si1 0.0176(13) 0.0176(13) 0.0102(18) 0.000 0.000 0.000 Si2 0.0310(16) 0.0310(16) 0.0079(18) 0.000 0.000 0.000 Si3 0.0124(13) 0.0124(13) 0.037(3) 0.000 0.000 0.000 Si4 0.0253(16) 0.0253(16) 0.037(3) 0.000 0.000 0.000 F1 0.060(5) 0.060(5) 0.020(6) 0.000 0.000 0.000 F2 0.060(5) 0.060(5) 0.020(6) 0.000 0.000 0.000 F3 0.077(3) 0.014(2) 0.038(2) -0.005(2) 0.002(3) 0.018(2) F4 0.040(4) 0.040(4) 0.005(5) 0.000 0.000 0.000 F5 0.042(4) 0.042(4) 0.011(5) 0.000 0.000 0.000 F6 0.059(4) 0.512(14) 0.026(3) -0.027(9) 0.007(4) -0.019(8) F7 0.011(3) 0.011(3) 0.037(6) 0.000 0.000 0.000 F9 0.023(2) 0.057(3) 0.023(2) -0.005(2) -0.0050(19) 0.0248(19) F10 0.027(4) 0.027(4) 0.040(6) 0.000 0.000 0.000 F11 0.030(4) 0.030(4) 0.061(8) 0.000 0.000 0.000 F12 0.052(4) 0.362(11) 0.059(5) -0.034(8) 0.006(4) -0.012(7) F13 0.032(4) 0.032(4) 0.083(10) 0.000 0.000 0.000 N1 0.030(2) 0.0262(19) 0.0261(16) 0.0108(15) -0.0006(15) 0.0052(15) C1 0.030(2) 0.0262(19) 0.0261(16) 0.0108(15) -0.0006(15) 0.0052(15) C2 0.030(2) 0.0262(19) 0.0261(16) 0.0108(15) -0.0006(15) 0.0052(15) C3 0.030(2) 0.0262(19) 0.0261(16) 0.0108(15) -0.0006(15) 0.0052(15) C4 0.030(2) 0.0262(19) 0.0261(16) 0.0108(15) -0.0006(15) 0.0052(15) C5 0.030(2) 0.0262(19) 0.0261(16) 0.0108(15) -0.0006(15) 0.0052(15) C6 0.0213(13) 0.0230(14) 0.069(2) 0.0040(16) -0.0082(15) -0.0078(11) C7 0.0213(13) 0.0230(14) 0.069(2) 0.0040(16) -0.0082(15) -0.0078(11) C8 0.0213(13) 0.0230(14) 0.069(2) 0.0040(16) -0.0082(15) -0.0078(11) C9 0.0213(13) 0.0230(14) 0.069(2) 0.0040(16) -0.0082(15) -0.0078(11) C10 0.0213(13) 0.0230(14) 0.069(2) 0.0040(16) -0.0082(15) -0.0078(11) C11 0.0213(13) 0.0230(14) 0.069(2) 0.0040(16) -0.0082(15) -0.0078(11) O1 0.029(4) 0.035(4) 0.106(5) 0.000(4) -0.002(4) -0.010(3) C12 0.031(5) 0.030(5) 0.137(10) -0.020(6) -0.014(6) 0.008(4) C13 0.029(6) 0.088(10) 0.251(19) 0.052(11) 0.027(9) 0.011(6) O2 0.029(6) 0.088(10) 0.251(19) 0.052(11) 0.027(9) 0.011(6) C14 0.029(6) 0.088(10) 0.251(19) 0.052(11) 0.027(9) 0.011(6) O3 0.049(8) 0.079(10) 0.234(18) -0.019(11) 0.038(10) -0.020(7) C15 0.049(8) 0.079(10) 0.234(18) -0.019(11) 0.038(10) -0.020(7) C16 0.068(9) 0.027(6) 0.249(18) 0.008(9) 0.054(11) 0.020(6) O4 0.068(9) 0.027(6) 0.249(18) 0.008(9) 0.054(11) 0.020(6) C17 0.068(9) 0.027(6) 0.249(18) 0.008(9) 0.054(11) 0.020(6) C18 0.0226(18) 0.0216(18) 0.042(2) 0.0025(15) -0.0137(15) -0.0111(15) C19 0.0226(18) 0.0216(18) 0.042(2) 0.0025(15) -0.0137(15) -0.0111(15) C20 0.0226(18) 0.0216(18) 0.042(2) 0.0025(15) -0.0137(15) -0.0111(15) N2 0.0226(18) 0.0216(18) 0.042(2) 0.0025(15) -0.0137(15) -0.0111(15) C21 0.0226(18) 0.0216(18) 0.042(2) 0.0025(15) -0.0137(15) -0.0111(15) C22 0.0226(18) 0.0216(18) 0.042(2) 0.0025(15) -0.0137(15) -0.0111(15) N3 0.017(2) 0.014(2) 0.015(2) 0.0055(18) 0.005(2) -0.002(2) C23 0.017(2) 0.014(2) 0.015(2) 0.0055(18) 0.005(2) -0.002(2) C24 0.039(5) 0.016(4) 0.037(5) -0.010(3) 0.004(4) -0.004(4) C25 0.009(4) 0.035(5) 0.034(4) 0.004(4) -0.007(4) 0.005(3) C26 0.019(4) 0.032(5) 0.037(5) -0.008(4) 0.021(3) -0.008(4) C27 0.019(4) 0.032(5) 0.037(5) -0.008(4) 0.021(3) -0.008(4) C28 0.0246(14) 0.0218(14) 0.0591(17) -0.0064(13) 0.0065(13) -0.0034(11) C29 0.0246(14) 0.0218(14) 0.0591(17) -0.0064(13) 0.0065(13) -0.0034(11) C30 0.0246(14) 0.0218(14) 0.0591(17) -0.0064(13) 0.0065(13) -0.0034(11) C31 0.0246(14) 0.0218(14) 0.0591(17) -0.0064(13) 0.0065(13) -0.0034(11) C32 0.0246(14) 0.0218(14) 0.0591(17) -0.0064(13) 0.0065(13) -0.0034(11) C33 0.0246(14) 0.0218(14) 0.0591(17) -0.0064(13) 0.0065(13) -0.0034(11) O5 0.018(3) 0.018(3) 0.137(6) -0.007(4) 0.027(4) 0.000(2) C34 0.053(8) 0.085(10) 0.157(13) 0.015(9) -0.008(8) 0.025(7) C35 0.046(7) 0.035(6) 0.223(14) -0.004(9) -0.035(9) -0.007(5) O6 0.046(7) 0.035(6) 0.223(14) -0.004(9) -0.035(9) -0.007(5) C36 0.046(7) 0.035(6) 0.223(14) -0.004(9) -0.035(9) -0.007(5) O7 0.016(3) 0.040(4) 0.148(7) -0.008(4) -0.024(4) -0.005(3) C37 0.039(5) 0.032(5) 0.085(7) -0.005(5) -0.010(5) -0.008(4) C38 0.039(5) 0.032(5) 0.085(7) -0.005(5) -0.010(5) -0.008(4) O8 0.039(5) 0.032(5) 0.085(7) -0.005(5) -0.010(5) -0.008(4) C39 0.039(5) 0.032(5) 0.085(7) -0.005(5) -0.010(5) -0.008(4) C40 0.033(5) 0.011(4) 0.045(5) -0.006(4) 0.019(4) -0.014(3) C41 0.041(6) 0.044(7) 0.071(7) -0.031(5) -0.009(5) -0.005(5) C42 0.060(7) 0.041(6) 0.010(4) -0.007(3) 0.006(4) -0.005(5) N4 0.017(3) 0.017(3) 0.062(5) -0.018(3) 0.005(3) 0.000(3) C43 0.018(5) 0.070(7) 0.073(7) -0.025(6) 0.004(5) -0.007(5) C44 0.046(7) 0.016(5) 0.089(8) -0.008(5) 0.009(6) -0.007(4) C45 0.074(6) 0.041(5) 0.063(5) -0.004(5) 0.011(6) 0.019(4) Cl1 0.124(3) 0.078(2) 0.078(2) -0.0188(17) -0.034(2) 0.009(2) Cl2 0.133(3) 0.106(3) 0.077(2) 0.0127(19) 0.008(2) 0.028(3) Cl3 0.078(2) 0.156(3) 0.094(2) -0.018(3) -0.007(2) 0.045(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 F2 2.042(8) . ? Zn1 F1 2.074(11) . ? Zn1 N1 2.089(4) . ? Zn1 N1 2.089(4) 4_565 ? Zn1 N1 2.089(4) 2_665 ? Zn1 N1 2.089(4) 3_655 ? Zn2 F4 2.074(9) . ? Zn2 F5 2.119(8) . ? Zn2 N3 2.118(5) 4_565 ? Zn2 N3 2.118(5) 2_665 ? Zn2 N3 2.118(5) 3_655 ? Zn2 N3 2.118(5) . ? Zn3 F7 2.112(9) . ? Zn3 F13 2.145(12) 1_554 ? Zn3 N2 2.148(6) 2 ? Zn3 N2 2.148(6) . ? Zn3 N2 2.148(6) 3 ? Zn3 N2 2.148(6) 4 ? Zn4 F10 1.988(10) . ? Zn4 F11 2.053(11) . ? Zn4 N4 2.130(4) 2 ? Zn4 N4 2.130(8) 3 ? Zn4 N4 2.130(4) . ? Zn4 N4 2.130(7) 4 ? Si1 F3 1.662(3) 4_565 ? Si1 F3 1.662(3) . ? Si1 F3 1.662(3) 2_665 ? Si1 F3 1.662(3) 3_655 ? Si1 F4 1.714(10) . ? Si1 F2 1.725(9) . ? Si2 F6 1.606(6) . ? Si2 F6 1.606(6) 2_665 ? Si2 F6 1.606(6) 4_565 ? Si2 F6 1.606(6) 3_655 ? Si2 F5 1.670(10) . ? Si2 F1 1.733(11) 1_556 ? Si3 F7 1.654(10) . ? Si3 F9 1.668(4) 3 ? Si3 F9 1.668(4) . ? Si3 F9 1.668(4) 4 ? Si3 F9 1.668(4) 2 ? Si3 F10 1.794(11) . ? Si4 F12 1.607(6) 2 ? Si4 F12 1.607(6) . ? Si4 F12 1.608(6) 3 ? Si4 F12 1.608(6) 4 ? Si4 F13 1.616(13) . ? Si4 F11 1.789(12) . ? F1 Si2 1.733(11) 1_554 ? F13 Zn3 2.145(12) 1_556 ? N1 C1 1.3900 . ? N1 C5 1.3900 . ? C1 C2 1.3900 . ? C1 H1 0.9500 . ? C2 C3 1.3900 . ? C2 H2 0.9500 . ? C3 C4 1.3900 . ? C3 C6 1.541(8) . ? C4 C5 1.3900 . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.354(10) . ? C6 C11 1.383(10) . ? C7 O1 1.369(9) . ? C7 C8 1.438(9) . ? C8 C9 1.450(10) . ? C8 H8 0.9500 . ? C9 C10 1.412(10) . ? C9 C18 1.454(10) . ? C10 C11 1.341(10) . ? C10 O3 1.371(9) . ? C11 H11 0.9500 . ? O1 C12 1.498(9) . ? C12 C13 1.478(12) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O2 1.443(11) . ? C13 C14 1.504(16) . ? C13 H13 1.0000 . ? O2 H2A 0.8475 . ? C14 H14A 0.9824 . ? C14 H14B 0.9823 . ? C14 H14C 0.9823 . ? O3 C15 1.442(11) . ? C15 C16 1.591(14) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.462(16) . ? C16 O4 1.476(14) . ? C16 H16 1.0000 . ? O4 H4A 0.8423 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C22 1.356(10) . ? C18 C19 1.368(9) . ? C19 C20 1.413(9) . ? C19 H19 0.9500 . ? C20 N2 1.273(8) . ? C20 H20 0.9500 . ? N2 C21 1.320(8) . ? C21 C22 1.353(9) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? N3 C27 1.310(8) . ? N3 C23 1.348(7) . ? C23 C24 1.315(9) . ? C23 H23 0.9500 . ? C24 C25 1.411(10) . ? C24 H24 0.9500 . ? C25 C26 1.407(10) . ? C25 C28 1.514(8) . ? C26 C27 1.376(9) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.3900 . ? C28 C33 1.3900 . ? C29 C30 1.3900 . ? C29 O5 1.425(6) . ? C30 C31 1.3900 . ? C30 H30 0.9500 . ? C31 C32 1.3900 . ? C31 C40 1.488(6) . ? C32 O7 1.333(7) . ? C32 C33 1.3900 . ? C33 H33 0.9500 . ? O5 C34 1.489(11) . ? C34 C35 1.479(12) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 O6 1.523(13) . ? C35 C36 1.561(16) . ? C35 H35 1.0000 . ? O6 H6 0.84000 . ? C36 H36A 0.98000 . ? C36 H36B 0.98000 . ? C36 H36C 0.98000 . ? O7 C37 1.429(9) . ? C37 C38 1.553(13) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 O8 1.474(13) . ? C38 C39 1.478(16) . ? C38 H38 1.0000 . ? O8 H8A 0.8439 . ? C39 H39A 0.98000 . ? C39 H39B 0.98000 . ? C39 H39C 0.98000 . ? C40 C41 1.3900 . ? C40 C44 1.3900 . ? C41 C42 1.3900 . ? C41 H41 0.9500 . ? C42 N4 1.3900 . ? C42 H42 0.9500 . ? N4 C43 1.3900 . ? C43 C44 1.3900 . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 Cl3 1.634(8) . ? C45 Cl1 1.751(10) . ? C45 Cl2 1.830(10) . ? C45 H45 1.0000 . ? 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 F2 Zn1 F1 180.000(2) . . ? F2 Zn1 N1 90.05(14) . . ? F1 Zn1 N1 89.95(14) . . ? F2 Zn1 N1 90.06(14) . 4_565 ? F1 Zn1 N1 89.94(14) . 4_565 ? N1 Zn1 N1 90.0 . 4_565 ? F2 Zn1 N1 90.06(14) . 2_665 ? F1 Zn1 N1 89.94(14) . 2_665 ? N1 Zn1 N1 179.9(3) . 2_665 ? N1 Zn1 N1 90.0 4_565 2_665 ? F2 Zn1 N1 90.06(14) . 3_655 ? F1 Zn1 N1 89.94(14) . 3_655 ? N1 Zn1 N1 90.0 . 3_655 ? N1 Zn1 N1 179.9(3) 4_565 3_655 ? N1 Zn1 N1 90.0 2_665 3_655 ? F4 Zn2 F5 180.000(2) . . ? F4 Zn2 N3 88.48(16) . 4_565 ? F5 Zn2 N3 91.52(16) . 4_565 ? F4 Zn2 N3 88.48(16) . 2_665 ? F5 Zn2 N3 91.52(16) . 2_665 ? N3 Zn2 N3 89.960(9) 4_565 2_665 ? F4 Zn2 N3 88.48(16) . 3_655 ? F5 Zn2 N3 91.52(16) . 3_655 ? N3 Zn2 N3 177.0(3) 4_565 3_655 ? N3 Zn2 N3 89.959(10) 2_665 3_655 ? F4 Zn2 N3 88.48(16) . . ? F5 Zn2 N3 91.52(16) . . ? N3 Zn2 N3 89.960(10) 4_565 . ? N3 Zn2 N3 177.0(3) 2_665 . ? N3 Zn2 N3 89.960(9) 3_655 . ? F7 Zn3 F13 180.0 . 1_554 ? F7 Zn3 N2 89.45(19) . 2 ? F13 Zn3 N2 90.55(19) 1_554 2 ? F7 Zn3 N2 89.45(19) . . ? F13 Zn3 N2 90.55(19) 1_554 . ? N2 Zn3 N2 178.9(4) 2 . ? F7 Zn3 N2 89.45(19) . 3 ? F13 Zn3 N2 90.55(19) 1_554 3 ? N2 Zn3 N2 89.995(4) 2 3 ? N2 Zn3 N2 89.995(4) . 3 ? F7 Zn3 N2 89.45(19) . 4 ? F13 Zn3 N2 90.55(19) 1_554 4 ? N2 Zn3 N2 89.995(4) 2 4 ? N2 Zn3 N2 89.994(4) . 4 ? N2 Zn3 N2 178.9(4) 3 4 ? F10 Zn4 F11 180.000(2) . . ? F10 Zn4 N4 89.3(5) . 2 ? F11 Zn4 N4 90.7(5) . 2 ? F10 Zn4 N4 89.3(4) . 3 ? F11 Zn4 N4 90.7(4) . 3 ? N4 Zn4 N4 89.99(17) 2 3 ? F10 Zn4 N4 89.27(15) . . ? F11 Zn4 N4 90.73(15) . . ? N4 Zn4 N4 178.5(6) 2 . ? N4 Zn4 N4 89.99(17) 3 . ? F10 Zn4 N4 89.3(4) . 4 ? F11 Zn4 N4 90.7(4) . 4 ? N4 Zn4 N4 89.99(18) 2 4 ? N4 Zn4 N4 178.5(6) 3 4 ? N4 Zn4 N4 89.99(18) . 4 ? F3 Si1 F3 89.944(18) 4_565 . ? F3 Si1 F3 89.946(18) 4_565 2_665 ? F3 Si1 F3 176.5(5) . 2_665 ? F3 Si1 F3 176.5(5) 4_565 3_655 ? F3 Si1 F3 89.946(18) . 3_655 ? F3 Si1 F3 89.945(18) 2_665 3_655 ? F3 Si1 F4 91.8(3) 4_565 . ? F3 Si1 F4 91.8(3) . . ? F3 Si1 F4 91.8(3) 2_665 . ? F3 Si1 F4 91.8(3) 3_655 . ? F3 Si1 F2 88.2(3) 4_565 . ? F3 Si1 F2 88.2(3) . . ? F3 Si1 F2 88.2(3) 2_665 . ? F3 Si1 F2 88.2(3) 3_655 . ? F4 Si1 F2 180.000(3) . . ? F6 Si2 F6 174.6(7) . 2_665 ? F6 Si2 F6 89.87(3) . 4_565 ? F6 Si2 F6 89.87(3) 2_665 4_565 ? F6 Si2 F6 89.87(3) . 3_655 ? F6 Si2 F6 89.87(3) 2_665 3_655 ? F6 Si2 F6 174.6(7) 4_565 3_655 ? F6 Si2 F5 92.7(3) . . ? F6 Si2 F5 92.7(3) 2_665 . ? F6 Si2 F5 92.7(3) 4_565 . ? F6 Si2 F5 92.7(3) 3_655 . ? F6 Si2 F1 87.3(3) . 1_556 ? F6 Si2 F1 87.3(3) 2_665 1_556 ? F6 Si2 F1 87.3(3) 4_565 1_556 ? F6 Si2 F1 87.3(3) 3_655 1_556 ? F5 Si2 F1 180.000(5) . 1_556 ? F7 Si3 F9 89.3(2) . 3 ? F7 Si3 F9 89.3(2) . . ? F9 Si3 F9 89.993(6) 3 . ? F7 Si3 F9 89.3(2) . 4 ? F9 Si3 F9 178.6(5) 3 4 ? F9 Si3 F9 89.991(6) . 4 ? F7 Si3 F9 89.3(2) . 2 ? F9 Si3 F9 89.991(6) 3 2 ? F9 Si3 F9 178.6(5) . 2 ? F9 Si3 F9 89.991(6) 4 2 ? F7 Si3 F10 180.000(1) . . ? F9 Si3 F10 90.7(2) 3 . ? F9 Si3 F10 90.7(2) . . ? F9 Si3 F10 90.7(2) 4 . ? F9 Si3 F10 90.7(2) 2 . ? F12 Si4 F12 177.1(7) 2 . ? F12 Si4 F12 89.96(2) 2 3 ? F12 Si4 F12 89.96(2) . 3 ? F12 Si4 F12 89.96(2) 2 4 ? F12 Si4 F12 89.962(19) . 4 ? F12 Si4 F12 177.1(7) 3 4 ? F12 Si4 F13 91.5(4) 2 . ? F12 Si4 F13 91.5(4) . . ? F12 Si4 F13 91.5(4) 3 . ? F12 Si4 F13 91.5(4) 4 . ? F12 Si4 F11 88.5(4) 2 . ? F12 Si4 F11 88.5(4) . . ? F12 Si4 F11 88.5(4) 3 . ? F12 Si4 F11 88.5(4) 4 . ? F13 Si4 F11 180.000(4) . . ? Si2 F1 Zn1 180.0 1_554 . ? Si1 F2 Zn1 180.000(1) . . ? Si1 F4 Zn2 180.000(1) . . ? Si2 F5 Zn2 180.000(1) . . ? Si3 F7 Zn3 180.0 . . ? Si3 F10 Zn4 180.0 . . ? Si4 F11 Zn4 180.000(1) . . ? Si4 F13 Zn3 180.000(1) . 1_556 ? C1 N1 C5 120.0 . . ? C1 N1 Zn1 118.1(2) . . ? C5 N1 Zn1 121.9(2) . . ? C2 C1 N1 120.0 . . ? C2 C1 H1 120.0 . . ? N1 C1 H1 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 C6 119.7(5) . . ? C2 C3 C6 120.2(5) . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 N1 120.0 . . ? C4 C5 H5 120.0 . . ? N1 C5 H5 120.0 . . ? C7 C6 C11 120.6(7) . . ? C7 C6 C3 120.0(7) . . ? C11 C6 C3 118.9(7) . . ? C6 C7 O1 118.1(7) . . ? C6 C7 C8 119.8(7) . . ? O1 C7 C8 121.3(7) . . ? C7 C8 C9 119.1(7) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C10 C9 C8 116.0(7) . . ? C10 C9 C18 126.6(7) . . ? C8 C9 C18 117.1(7) . . ? C11 C10 O3 123.9(7) . . ? C11 C10 C9 122.7(7) . . ? O3 C10 C9 113.4(7) . . ? C10 C11 C6 121.1(8) . . ? C10 C11 H11 119.5 . . ? C6 C11 H11 119.5 . . ? C7 O1 C12 117.9(6) . . ? C13 C12 O1 107.6(8) . . ? C13 C12 H12A 110.5 . . ? O1 C12 H12A 110.2 . . ? C13 C12 H12B 109.9 . . ? O1 C12 H12B 110.1 . . ? H12A C12 H12B 108.5 . . ? O2 C13 C12 113.5(10) . . ? O2 C13 C14 102.1(14) . . ? C12 C13 C14 131.4(15) . . ? O2 C13 H13 101.9 . . ? C12 C13 H13 101.9 . . ? C14 C13 H13 101.8 . . ? C13 O2 H2A 109.8 . . ? C13 C14 H14A 109.9 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.3 . . ? C13 C14 H14C 109.8 . . ? H14A C14 H14C 109.2 . . ? H14B C14 H14C 109.2 . . ? C10 O3 C15 119.3(8) . . ? O3 C15 C16 100.9(9) . . ? O3 C15 H15A 111.5 . . ? C16 C15 H15A 111.4 . . ? O3 C15 H15B 111.7 . . ? C16 C15 H15B 111.8 . . ? H15A C15 H15B 109.4 . . ? C17 C16 O4 92.8(14) . . ? C17 C16 C15 92.5(13) . . ? O4 C16 C15 99.3(10) . . ? C17 C16 H16 121.5 . . ? O4 C16 H16 121.7 . . ? C15 C16 H16 121.8 . . ? C16 O4 H4A 109.7 . . ? C16 C17 H17A 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.6 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C22 C18 C19 116.0(6) . . ? C22 C18 C9 124.1(7) . . ? C19 C18 C9 119.7(7) . . ? C18 C19 C20 119.6(7) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? N2 C20 C19 122.5(6) . . ? N2 C20 H20 118.8 . . ? C19 C20 H20 118.8 . . ? C20 N2 C21 117.6(6) . . ? C20 N2 Zn3 122.2(5) . . ? C21 N2 Zn3 120.2(5) . . ? N2 C21 C22 123.7(7) . . ? N2 C21 H21 118.1 . . ? C22 C21 H21 118.2 . . ? C21 C22 C18 120.5(7) . . ? C21 C22 H22 119.8 . . ? C18 C22 H22 119.7 . . ? C27 N3 C23 115.3(5) . . ? C27 N3 Zn2 121.9(5) . . ? C23 N3 Zn2 122.8(4) . . ? C24 C23 N3 125.2(6) . . ? C24 C23 H23 117.4 . . ? N3 C23 H23 117.4 . . ? C23 C24 C25 119.8(6) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 116.4(6) . . ? C26 C25 C28 118.2(6) . . ? C24 C25 C28 125.4(7) . . ? C27 C26 C25 117.4(6) . . ? C27 C26 H26 121.3 . . ? C25 C26 H26 121.3 . . ? N3 C27 C26 125.7(7) . . ? N3 C27 H27 117.1 . . ? C26 C27 H27 117.1 . . ? C29 C28 C33 120.0 . . ? C29 C28 C25 121.0(4) . . ? C33 C28 C25 118.9(4) . . ? C28 C29 C30 120.0 . . ? C28 C29 O5 118.5(3) . . ? C30 C29 O5 120.7(4) . . ? C31 C30 C29 120.0 . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C32 120.0 . . ? C30 C31 C40 119.5(4) . . ? C32 C31 C40 120.4(4) . . ? O7 C32 C31 115.5(4) . . ? O7 C32 C33 123.7(4) . . ? C31 C32 C33 120.0 . . ? C32 C33 C28 120.0 . . ? C32 C33 H33 120.0 . . ? C28 C33 H33 120.0 . . ? C29 O5 C34 115.0(7) . . ? C35 C34 O5 107.7(9) . . ? C35 C34 H34A 110.1 . . ? O5 C34 H34A 110.2 . . ? C35 C34 H34B 110.1 . . ? O5 C34 H34B 110.2 . . ? H34A C34 H34B 108.5 . . ? C34 C35 O6 113.0(11) . . ? C34 C35 C36 111.6(12) . . ? O6 C35 C36 111.8(12) . . ? C34 C35 H35 106.4 . . ? O6 C35 H35 107.1 . . ? C36 C35 H35 106.5 . . ? C32 O7 C37 117.6(6) . . ? O7 C37 C38 103.3(8) . . ? O7 C37 H37A 111.0 . . ? C38 C37 H37A 111.3 . . ? O7 C37 H37B 111.2 . . ? C38 C37 H37B 110.9 . . ? H37A C37 H37B 109.1 . . ? O8 C38 C39 108.6(16) . . ? O8 C38 C37 99.5(11) . . ? C39 C38 C37 120.9(17) . . ? O8 C38 H38 109.4 . . ? C39 C38 H38 108.7 . . ? C37 C38 H38 109.0 . . ? C38 O8 H8A 109.9 . . ? C41 C40 C44 120.0 . . ? C41 C40 C31 119.7(4) . . ? C44 C40 C31 119.9(4) . . ? C42 C41 C40 120.0 . . ? C42 C41 H41 120.0 . . ? C40 C41 H41 120.0 . . ? N4 C42 C41 120.0 . . ? N4 C42 H42 120.0 . . ? C41 C42 H42 120.0 . . ? C42 N4 C43 120.0 . . ? C42 N4 Zn4 120.5(3) . . ? C43 N4 Zn4 119.5(3) . . ? C44 C43 N4 120.0 . . ? C44 C43 H43 120.0 . . ? N4 C43 H43 120.0 . . ? C43 C44 C40 120.0 . . ? C43 C44 H44 120.0 . . ? C40 C44 H44 120.0 . . ? Cl3 C45 Cl1 115.7(6) . . ? Cl3 C45 Cl2 108.4(5) . . ? Cl1 C45 Cl2 107.4(5) . . ? Cl3 C45 H45 108.4 . . ? Cl1 C45 H45 108.4 . . ? Cl2 C45 H45 108.4 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.480 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.113 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.022 0.242 0.252 1549.5 447.1 2 0.049 0.780 0.757 1898.6 460.4 _platon_squeeze_details ; ; data_e2532a _database_code_depnum_ccdc_archive 'CCDC 923943' #TrackingRef 'web_deposit_cif_file_4_Gruber_1360327886.s2532.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 N2 O4' _chemical_formula_sum 'C22 H24 N2 O4' _chemical_formula_weight 380.43 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) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.9710(7) _cell_length_b 7.7678(4) _cell_length_c 11.9253(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.9420(10) _cell_angle_gamma 90.00 _cell_volume 981.92(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2946 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 30.02 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9938 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8330 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 30.06 _reflns_number_total 4560 _reflns_number_gt 4030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0851P)^2^+0.0078P] 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 -0.3(9) _chemical_absolute_configuration rm _refine_ls_number_reflns 4560 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 C1 C 0.83986(13) 0.5986(2) 0.42641(12) 0.0227(3) Uani 1 1 d . . . C2 C 0.76470(13) 0.5912(2) 0.50474(13) 0.0239(3) Uani 1 1 d . . . H2 H 0.6756 0.5891 0.4754 0.029 Uiso 1 1 calc R . . C3 C 0.81617(13) 0.5869(2) 0.62425(12) 0.0228(3) Uani 1 1 d . . . C4 C 0.94790(13) 0.5883(2) 0.66947(12) 0.0233(3) Uani 1 1 d . . . C5 C 1.02309(13) 0.6013(3) 0.59089(13) 0.0265(3) Uani 1 1 d . . . H5 H 1.1122 0.6063 0.6201 0.032 Uiso 1 1 calc R . . C6 C 0.97136(13) 0.6070(2) 0.47160(12) 0.0249(3) Uani 1 1 d . . . C7 C 0.78026(13) 0.5877(2) 0.29965(12) 0.0228(3) Uani 1 1 d . . . C8 C 0.66447(14) 0.6674(2) 0.25056(13) 0.0264(3) Uani 1 1 d . . . H8 H 0.6259 0.7378 0.2968 0.032 Uiso 1 1 calc R . . C9 C 0.60654(15) 0.6428(3) 0.13376(14) 0.0331(4) Uani 1 1 d . . . H9 H 0.5277 0.6974 0.1022 0.040 Uiso 1 1 calc R . . N1 N 0.65538(14) 0.5465(2) 0.06277(12) 0.0346(4) Uani 1 1 d . . . C10 C 0.76748(15) 0.4741(3) 0.10993(13) 0.0327(4) Uani 1 1 d . . . H10 H 0.8048 0.4073 0.0609 0.039 Uiso 1 1 calc R . . C11 C 0.83270(14) 0.4899(2) 0.22539(13) 0.0268(3) Uani 1 1 d . . . H11 H 0.9121 0.4350 0.2538 0.032 Uiso 1 1 calc R . . C13 C 1.01118(13) 0.5749(2) 0.79495(12) 0.0242(3) Uani 1 1 d . . . C14 C 0.96442(14) 0.6512(3) 0.88178(13) 0.0284(3) Uani 1 1 d . . . H14 H 0.8868 0.7122 0.8619 0.034 Uiso 1 1 calc R . . C15 C 1.03196(16) 0.6373(3) 0.99675(14) 0.0336(4) Uani 1 1 d . . . H15 H 0.9985 0.6906 1.0541 0.040 Uiso 1 1 calc R . . N2 N 1.14136(14) 0.5533(2) 1.03168(12) 0.0349(4) Uani 1 1 d . . . C16 C 1.18634(16) 0.4805(3) 0.94909(15) 0.0376(4) Uani 1 1 d . . . H16 H 1.2644 0.4207 0.9719 0.045 Uiso 1 1 calc R . . C17 C 1.12509(16) 0.4874(3) 0.83165(13) 0.0326(4) Uani 1 1 d . . . H17 H 1.1610 0.4325 0.7765 0.039 Uiso 1 1 calc R . . O1 O 0.74554(9) 0.57062(17) 0.70298(9) 0.0269(3) Uani 1 1 d . . . C18 C 0.61587(13) 0.6182(2) 0.66558(13) 0.0253(3) Uani 1 1 d . . . H18A H 0.5678 0.5291 0.6130 0.030 Uiso 1 1 calc R . . H18B H 0.6071 0.7288 0.6229 0.030 Uiso 1 1 calc R . . C19 C 0.56528(14) 0.6359(3) 0.77196(13) 0.0282(3) Uani 1 1 d . . . H19 H 0.6191 0.7186 0.8276 0.034 Uiso 1 1 calc R . . O2 O 0.56901(12) 0.47276(19) 0.82543(10) 0.0342(3) Uani 1 1 d . . . H2A H 0.5897 0.4847 0.8979 0.051 Uiso 1 1 calc R . . C20 C 0.43044(19) 0.7024(4) 0.73601(18) 0.0482(6) Uani 1 1 d . . . H20A H 0.3987 0.7171 0.8051 0.072 Uiso 1 1 calc R . . H20B H 0.3772 0.6197 0.6833 0.072 Uiso 1 1 calc R . . H20C H 0.4285 0.8134 0.6965 0.072 Uiso 1 1 calc R . . O3 O 1.04197(10) 0.6255(2) 0.39290(9) 0.0317(3) Uani 1 1 d . . . C21 C 1.17581(13) 0.6164(3) 0.43588(12) 0.0256(3) Uani 1 1 d . . . H21A H 1.2004 0.5068 0.4780 0.031 Uiso 1 1 calc R . . H21B H 1.2068 0.7128 0.4900 0.031 Uiso 1 1 calc R . . C22 C 1.23192(13) 0.6272(2) 0.33272(12) 0.0253(3) Uani 1 1 d . . . H22 H 1.1964 0.7292 0.2841 0.030 Uiso 1 1 calc R . . O4 O 1.19912(12) 0.47469(18) 0.26687(10) 0.0334(3) Uani 1 1 d . . . H4 H 1.1890 0.4970 0.1961 0.050 Uiso 1 1 calc R . . C23 C 1.37486(15) 0.6444(3) 0.37490(17) 0.0396(4) Uani 1 1 d . . . H23A H 1.4106 0.6559 0.3080 0.059 Uiso 1 1 calc R . . H23B H 1.4098 0.5418 0.4195 0.059 Uiso 1 1 calc R . . H23C H 1.3960 0.7465 0.4243 0.059 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 C1 0.0229(6) 0.0251(9) 0.0206(6) -0.0005(6) 0.0068(5) -0.0006(6) C2 0.0226(6) 0.0274(9) 0.0224(6) 0.0003(6) 0.0069(5) -0.0007(6) C3 0.0252(6) 0.0238(9) 0.0213(6) -0.0006(6) 0.0098(5) -0.0004(6) C4 0.0257(6) 0.0245(9) 0.0208(6) 0.0000(6) 0.0080(5) 0.0010(6) C5 0.0226(6) 0.0361(10) 0.0212(6) -0.0010(6) 0.0065(5) -0.0001(6) C6 0.0226(6) 0.0329(10) 0.0207(6) -0.0002(6) 0.0086(5) -0.0013(6) C7 0.0231(6) 0.0254(9) 0.0209(6) 0.0009(6) 0.0074(5) -0.0022(6) C8 0.0261(7) 0.0301(9) 0.0247(7) 0.0017(6) 0.0095(5) 0.0026(6) C9 0.0296(7) 0.0419(11) 0.0265(7) 0.0041(8) 0.0045(6) 0.0051(8) N1 0.0342(7) 0.0444(10) 0.0241(6) 0.0004(6) 0.0051(5) 0.0004(6) C10 0.0364(8) 0.0394(11) 0.0245(7) -0.0029(7) 0.0118(6) 0.0017(8) C11 0.0271(7) 0.0296(9) 0.0245(7) -0.0003(6) 0.0082(5) 0.0024(6) C13 0.0257(6) 0.0270(9) 0.0204(6) 0.0005(6) 0.0071(5) -0.0015(6) C14 0.0278(7) 0.0348(10) 0.0240(7) -0.0008(7) 0.0093(5) 0.0027(7) C15 0.0381(8) 0.0400(11) 0.0240(7) -0.0027(7) 0.0105(6) -0.0012(8) N2 0.0399(7) 0.0404(10) 0.0233(6) 0.0043(6) 0.0061(6) 0.0004(7) C16 0.0365(8) 0.0448(12) 0.0284(8) 0.0047(8) 0.0025(6) 0.0105(8) C17 0.0349(8) 0.0377(10) 0.0258(7) 0.0001(7) 0.0090(6) 0.0080(8) O1 0.0235(5) 0.0379(7) 0.0216(5) 0.0036(5) 0.0099(4) 0.0015(5) C18 0.0247(6) 0.0313(9) 0.0217(6) 0.0007(6) 0.0092(5) 0.0016(6) C19 0.0288(7) 0.0331(10) 0.0255(7) -0.0025(7) 0.0123(5) -0.0010(7) O2 0.0414(6) 0.0376(8) 0.0245(5) 0.0020(5) 0.0102(5) -0.0063(6) C20 0.0409(10) 0.0642(16) 0.0453(11) 0.0040(10) 0.0218(8) 0.0158(10) O3 0.0223(5) 0.0544(9) 0.0204(5) 0.0021(5) 0.0091(4) -0.0011(5) C21 0.0221(6) 0.0344(10) 0.0208(6) -0.0010(6) 0.0064(5) -0.0024(6) C22 0.0258(6) 0.0292(9) 0.0226(6) 0.0015(6) 0.0096(5) -0.0013(6) O4 0.0467(7) 0.0312(7) 0.0229(5) -0.0024(5) 0.0101(5) -0.0012(6) C23 0.0278(7) 0.0525(13) 0.0421(9) 0.0032(9) 0.0153(7) -0.0029(8) _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 C1 C2 1.3975(19) . ? C1 C6 1.4054(19) . ? C1 C7 1.4866(19) . ? C2 C3 1.391(2) . ? C2 H2 0.9500 . ? C3 O1 1.3686(16) . ? C3 C4 1.4063(19) . ? C4 C5 1.4026(19) . ? C4 C13 1.4820(19) . ? C5 C6 1.390(2) . ? C5 H5 0.9500 . ? C6 O3 1.3699(16) . ? C7 C11 1.398(2) . ? C7 C8 1.399(2) . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 N1 1.341(2) . ? C9 H9 0.9500 . ? N1 C10 1.337(2) . ? C10 C11 1.384(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C13 C17 1.390(2) . ? C13 C14 1.400(2) . ? C14 C15 1.384(2) . ? C14 H14 0.9500 . ? C15 N2 1.335(2) . ? C15 H15 0.9500 . ? N2 C16 1.336(2) . ? C16 C17 1.389(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? O1 C18 1.4255(17) . ? C18 C19 1.5163(19) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O2 1.414(2) . ? C19 C20 1.521(2) . ? C19 H19 1.0000 . ? O2 H2A 0.8400 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O3 C21 1.4267(17) . ? C21 C22 1.5132(19) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O4 1.415(2) . ? C22 C23 1.524(2) . ? C22 H22 1.0000 . ? O4 H4 0.8400 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.03(13) . . ? C2 C1 C7 119.78(12) . . ? C6 C1 C7 122.10(12) . . ? C3 C2 C1 122.15(12) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? O1 C3 C2 123.56(12) . . ? O1 C3 C4 116.45(12) . . ? C2 C3 C4 119.87(12) . . ? C5 C4 C3 117.89(13) . . ? C5 C4 C13 118.46(12) . . ? C3 C4 C13 123.65(12) . . ? C6 C5 C4 122.06(13) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? O3 C6 C5 123.42(12) . . ? O3 C6 C1 116.62(12) . . ? C5 C6 C1 119.93(12) . . ? C11 C7 C8 116.94(13) . . ? C11 C7 C1 122.00(13) . . ? C8 C7 C1 120.95(13) . . ? C9 C8 C7 119.40(15) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? N1 C9 C8 123.83(15) . . ? N1 C9 H9 118.1 . . ? C8 C9 H9 118.1 . . ? C10 N1 C9 116.30(14) . . ? N1 C10 C11 124.37(15) . . ? N1 C10 H10 117.8 . . ? C11 C10 H10 117.8 . . ? C10 C11 C7 119.13(14) . . ? C10 C11 H11 120.4 . . ? C7 C11 H11 120.4 . . ? C17 C13 C14 116.43(13) . . ? C17 C13 C4 120.09(13) . . ? C14 C13 C4 123.45(13) . . ? C15 C14 C13 119.64(15) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? N2 C15 C14 123.77(15) . . ? N2 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? C15 N2 C16 116.77(14) . . ? N2 C16 C17 123.52(16) . . ? N2 C16 H16 118.2 . . ? C17 C16 H16 118.2 . . ? C16 C17 C13 119.87(15) . . ? C16 C17 H17 120.1 . . ? C13 C17 H17 120.1 . . ? C3 O1 C18 117.22(11) . . ? O1 C18 C19 108.23(12) . . ? O1 C18 H18A 110.1 . . ? C19 C18 H18A 110.1 . . ? O1 C18 H18B 110.1 . . ? C19 C18 H18B 110.1 . . ? H18A C18 H18B 108.4 . . ? O2 C19 C18 108.77(15) . . ? O2 C19 C20 110.16(16) . . ? C18 C19 C20 109.53(13) . . ? O2 C19 H19 109.5 . . ? C18 C19 H19 109.5 . . ? C20 C19 H19 109.5 . . ? C19 O2 H2A 109.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C6 O3 C21 117.39(11) . . ? O3 C21 C22 107.57(11) . . ? O3 C21 H21A 110.2 . . ? C22 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C22 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? O4 C22 C21 107.84(13) . . ? O4 C22 C23 110.44(15) . . ? C21 C22 C23 109.64(12) . . ? O4 C22 H22 109.6 . . ? C21 C22 H22 109.6 . . ? C23 C22 H22 109.6 . . ? C22 O4 H4 109.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.366 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.041 data_e2549a _database_code_depnum_ccdc_archive 'CCDC 923944' #TrackingRef 'web_deposit_cif_file_5_Gruber_1360327886.s2549.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 N2 O2' _chemical_formula_sum 'C24 H28 N2 O2' _chemical_formula_weight 376.48 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 5.9331(5) _cell_length_b 7.4929(7) _cell_length_c 46.754(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2078.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 899 _cell_measurement_theta_min 3.48 _cell_measurement_theta_max 22.79 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9939 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8887 _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_av_sigmaI/netI 0.1557 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -65 _diffrn_reflns_limit_l_max 64 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 30.05 _reflns_number_total 5547 _reflns_number_gt 2993 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.0105P] 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 1(2) _chemical_absolute_configuration rm _refine_ls_number_reflns 5547 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1538 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.1812 _refine_ls_wR_factor_gt 0.1503 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4307(5) 0.2390(4) 0.10050(6) 0.0232(7) Uani 1 1 d . . . C2 C 0.3802(6) 0.1328(5) 0.07681(7) 0.0312(8) Uani 1 1 d . . . H2 H 0.2382 0.1440 0.0676 0.037 Uiso 1 1 calc R . . C3 C 0.5362(6) 0.0119(5) 0.06674(7) 0.0369(8) Uani 1 1 d . . . H3 H 0.4952 -0.0597 0.0508 0.044 Uiso 1 1 calc R . . N1 N 0.7412(5) -0.0113(4) 0.07794(6) 0.0373(7) Uani 1 1 d . . . C4 C 0.7907(6) 0.0913(4) 0.10040(7) 0.0313(8) Uani 1 1 d . . . H4 H 0.9358 0.0788 0.1087 0.038 Uiso 1 1 calc R . . C5 C 0.6450(5) 0.2149(4) 0.11240(7) 0.0254(7) Uani 1 1 d . . . H5 H 0.6902 0.2828 0.1286 0.030 Uiso 1 1 calc R . . C6 C 0.2669(5) 0.3670(4) 0.11359(6) 0.0218(6) Uani 1 1 d . . . C7 C 0.2362(5) 0.3618(4) 0.14308(6) 0.0234(7) Uani 1 1 d . . . H7 H 0.3161 0.2760 0.1541 0.028 Uiso 1 1 calc R . . C8 C 0.0897(5) 0.4807(4) 0.15688(6) 0.0228(6) Uani 1 1 d . . . C9 C -0.0302(5) 0.6052(4) 0.14050(6) 0.0224(7) Uani 1 1 d . . . C10 C -0.0005(5) 0.6080(4) 0.11074(6) 0.0255(7) Uani 1 1 d . . . H10 H -0.0834 0.6910 0.0996 0.031 Uiso 1 1 calc R . . C11 C 0.1492(5) 0.4907(4) 0.09718(6) 0.0235(6) Uani 1 1 d . . . C12 C -0.1939(5) 0.7347(4) 0.15334(7) 0.0249(7) Uani 1 1 d . . . C13 C -0.1384(5) 0.8436(4) 0.17630(7) 0.0296(8) Uani 1 1 d . . . H13 H 0.0043 0.8330 0.1854 0.036 Uiso 1 1 calc R . . C14 C -0.2941(6) 0.9682(4) 0.18585(7) 0.0351(8) Uani 1 1 d . . . H14 H -0.2513 1.0429 0.2013 0.042 Uiso 1 1 calc R . . N2 N -0.5003(5) 0.9907(4) 0.17482(6) 0.0365(7) Uani 1 1 d . . . C15 C -0.5514(6) 0.8834(4) 0.15284(7) 0.0303(8) Uani 1 1 d . . . H15 H -0.6962 0.8959 0.1444 0.036 Uiso 1 1 calc R . . C16 C -0.4082(6) 0.7555(4) 0.14151(7) 0.0284(7) Uani 1 1 d . . . H16 H -0.4552 0.6831 0.1259 0.034 Uiso 1 1 calc R . . O1 O 0.0490(4) 0.4818(3) 0.18587(4) 0.0295(5) Uani 1 1 d . . . C17 C 0.1715(5) 0.3597(4) 0.20410(7) 0.0278(7) Uani 1 1 d . . . H17 H 0.1692 0.2384 0.1952 0.033 Uiso 1 1 calc R . . C18 C 0.4165(6) 0.4179(5) 0.20806(7) 0.0339(8) Uani 1 1 d . . . H18A H 0.4973 0.3233 0.2187 0.041 Uiso 1 1 calc R . . H18B H 0.4875 0.4277 0.1890 0.041 Uiso 1 1 calc R . . C19 C 0.4485(8) 0.5939(6) 0.22377(8) 0.0513(11) Uani 1 1 d . . . H19A H 0.3508 0.6849 0.2153 0.077 Uiso 1 1 calc R . . H19B H 0.6062 0.6317 0.2222 0.077 Uiso 1 1 calc R . . H19C H 0.4093 0.5784 0.2440 0.077 Uiso 1 1 calc R . . C20 C 0.0400(6) 0.3538(5) 0.23186(7) 0.0340(8) Uani 1 1 d . . . H20A H 0.0289 0.4744 0.2398 0.051 Uiso 1 1 calc R . . H20B H 0.1176 0.2759 0.2455 0.051 Uiso 1 1 calc R . . H20C H -0.1116 0.3072 0.2282 0.051 Uiso 1 1 calc R . . O2 O 0.1942(4) 0.4944(3) 0.06845(4) 0.0304(5) Uani 1 1 d . . . C21 C 0.0530(6) 0.5968(5) 0.04934(6) 0.0289(8) Uani 1 1 d . . . H21 H 0.0292 0.7181 0.0577 0.035 Uiso 1 1 calc R . . C22 C 0.1906(6) 0.6154(5) 0.02179(7) 0.0350(8) Uani 1 1 d . . . H22A H 0.1033 0.6885 0.0081 0.042 Uiso 1 1 calc R . . H22B H 0.3310 0.6812 0.0262 0.042 Uiso 1 1 calc R . . C23 C 0.2532(7) 0.4403(6) 0.00739(8) 0.0491(11) Uani 1 1 d . . . H23A H 0.3472 0.3693 0.0203 0.074 Uiso 1 1 calc R . . H23B H 0.3369 0.4649 -0.0102 0.074 Uiso 1 1 calc R . . H23C H 0.1157 0.3737 0.0028 0.074 Uiso 1 1 calc R . . C24 C -0.1721(6) 0.5088(7) 0.04533(8) 0.0501(10) Uani 1 1 d . . . H24A H -0.1501 0.3863 0.0385 0.075 Uiso 1 1 calc R . . H24B H -0.2603 0.5759 0.0313 0.075 Uiso 1 1 calc R . . H24C H -0.2529 0.5067 0.0636 0.075 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 C1 0.0244(17) 0.0154(14) 0.0300(17) 0.0010(13) 0.0026(14) -0.0005(13) C2 0.0296(18) 0.0300(18) 0.0339(18) -0.0031(15) -0.0007(14) 0.0074(15) C3 0.041(2) 0.0290(18) 0.041(2) -0.0112(16) 0.0036(16) 0.0067(17) N1 0.0367(18) 0.0290(15) 0.0462(17) -0.0035(14) 0.0082(14) 0.0100(14) C4 0.0266(18) 0.0256(17) 0.042(2) 0.0037(15) 0.0032(16) 0.0014(15) C5 0.0244(17) 0.0195(15) 0.0321(17) -0.0015(13) 0.0027(14) 0.0007(13) C6 0.0181(16) 0.0175(14) 0.0298(16) -0.0034(13) -0.0010(13) 0.0025(13) C7 0.0226(17) 0.0176(14) 0.0301(17) 0.0000(13) -0.0035(13) 0.0056(13) C8 0.0234(15) 0.0196(15) 0.0253(16) 0.0003(13) -0.0039(12) 0.0003(13) C9 0.0201(16) 0.0183(14) 0.0289(16) -0.0008(13) -0.0018(13) 0.0036(13) C10 0.0269(17) 0.0211(15) 0.0285(17) -0.0011(13) -0.0031(14) 0.0040(13) C11 0.0240(16) 0.0213(15) 0.0252(16) -0.0019(14) -0.0031(13) 0.0031(13) C12 0.0271(17) 0.0171(15) 0.0305(17) 0.0024(13) 0.0034(14) -0.0003(13) C13 0.0255(18) 0.0291(18) 0.0343(19) -0.0017(15) -0.0031(14) 0.0025(14) C14 0.041(2) 0.0235(17) 0.041(2) -0.0085(15) 0.0008(17) 0.0040(16) N2 0.0324(17) 0.0303(16) 0.0468(17) -0.0013(14) 0.0059(13) 0.0081(14) C15 0.0224(17) 0.0280(17) 0.0406(19) 0.0076(15) 0.0051(15) 0.0062(15) C16 0.0256(18) 0.0217(16) 0.0379(18) -0.0007(14) 0.0010(15) 0.0018(14) O1 0.0344(13) 0.0275(12) 0.0265(12) 0.0002(10) -0.0009(10) 0.0108(11) C17 0.0277(18) 0.0228(16) 0.0329(18) -0.0011(14) -0.0033(14) 0.0052(14) C18 0.0279(18) 0.037(2) 0.0372(19) 0.0011(16) -0.0027(16) 0.0005(16) C19 0.050(3) 0.044(2) 0.060(2) -0.007(2) 0.002(2) -0.018(2) C20 0.033(2) 0.0303(18) 0.0388(19) 0.0041(16) 0.0022(16) 0.0039(16) O2 0.0315(12) 0.0334(13) 0.0262(11) 0.0024(10) 0.0010(10) 0.0154(11) C21 0.0310(19) 0.0287(17) 0.0268(17) 0.0025(14) -0.0041(14) 0.0048(15) C22 0.036(2) 0.036(2) 0.0325(18) 0.0039(16) -0.0009(16) 0.0033(17) C23 0.056(3) 0.050(2) 0.041(2) -0.0054(18) 0.004(2) 0.007(2) C24 0.032(2) 0.072(3) 0.046(2) 0.001(2) -0.0023(18) -0.007(2) _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 C1 C2 1.396(4) . ? C1 C5 1.399(4) . ? C1 C6 1.496(4) . ? C2 C3 1.378(4) . ? C2 H2 0.9500 . ? C3 N1 1.336(4) . ? C3 H3 0.9500 . ? N1 C4 1.334(4) . ? C4 C5 1.386(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C11 1.391(4) . ? C6 C7 1.392(4) . ? C7 C8 1.402(4) . ? C7 H7 0.9500 . ? C8 O1 1.377(4) . ? C8 C9 1.401(4) . ? C9 C10 1.403(4) . ? C9 C12 1.498(4) . ? C10 C11 1.401(4) . ? C10 H10 0.9500 . ? C11 O2 1.370(4) . ? C12 C13 1.388(4) . ? C12 C16 1.395(4) . ? C13 C14 1.387(4) . ? C13 H13 0.9500 . ? C14 N2 1.338(4) . ? C14 H14 0.9500 . ? N2 C15 1.340(4) . ? C15 C16 1.386(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? O1 C17 1.446(4) . ? C17 C20 1.515(4) . ? C17 C18 1.529(5) . ? C17 H17 1.0000 . ? C18 C19 1.522(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O2 C21 1.445(4) . ? C21 C24 1.501(5) . ? C21 C22 1.531(5) . ? C21 H21 1.0000 . ? C22 C23 1.521(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C5 115.9(3) . . ? C2 C1 C6 123.4(3) . . ? C5 C1 C6 120.7(3) . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? N1 C3 C2 124.3(3) . . ? N1 C3 H3 117.9 . . ? C2 C3 H3 117.9 . . ? C4 N1 C3 115.7(3) . . ? N1 C4 C5 124.5(3) . . ? N1 C4 H4 117.7 . . ? C5 C4 H4 117.7 . . ? C4 C5 C1 119.5(3) . . ? C4 C5 H5 120.3 . . ? C1 C5 H5 120.3 . . ? C11 C6 C7 119.9(3) . . ? C11 C6 C1 121.8(3) . . ? C7 C6 C1 118.2(3) . . ? C6 C7 C8 121.3(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? O1 C8 C9 116.4(3) . . ? O1 C8 C7 124.4(3) . . ? C9 C8 C7 119.1(3) . . ? C8 C9 C10 119.2(3) . . ? C8 C9 C12 122.8(3) . . ? C10 C9 C12 118.0(3) . . ? C11 C10 C9 121.3(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? O2 C11 C6 117.1(3) . . ? O2 C11 C10 123.7(3) . . ? C6 C11 C10 119.1(3) . . ? C13 C12 C16 117.2(3) . . ? C13 C12 C9 122.5(3) . . ? C16 C12 C9 120.3(3) . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? N2 C14 C13 124.8(3) . . ? N2 C14 H14 117.6 . . ? C13 C14 H14 117.6 . . ? C14 N2 C15 115.2(3) . . ? N2 C15 C16 124.7(3) . . ? N2 C15 H15 117.6 . . ? C16 C15 H15 117.6 . . ? C15 C16 C12 119.0(3) . . ? C15 C16 H16 120.5 . . ? C12 C16 H16 120.5 . . ? C8 O1 C17 119.2(2) . . ? O1 C17 C20 105.3(3) . . ? O1 C17 C18 111.7(3) . . ? C20 C17 C18 113.2(3) . . ? O1 C17 H17 108.8 . . ? C20 C17 H17 108.8 . . ? C18 C17 H17 108.8 . . ? C19 C18 C17 115.1(3) . . ? C19 C18 H18A 108.5 . . ? C17 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C17 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C11 O2 C21 120.3(2) . . ? O2 C21 C24 111.1(3) . . ? O2 C21 C22 105.1(3) . . ? C24 C21 C22 114.2(3) . . ? O2 C21 H21 108.8 . . ? C24 C21 H21 108.8 . . ? C22 C21 H21 108.8 . . ? C23 C22 C21 115.0(3) . . ? C23 C22 H22A 108.5 . . ? C21 C22 H22A 108.5 . . ? C23 C22 H22B 108.5 . . ? C21 C22 H22B 108.5 . . ? H22A C22 H22B 107.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.246 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.061