# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email mehr@chem.ubc.ca _publ_contact_author_name 'Mehrkhodavandi, Parisa' _publ_author_name 'Parisa Mehrkhodavandi' data_pm075 _database_code_depnum_ccdc_archive 'CCDC 882421' #TrackingRef '- cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H52 Cl In N2 O2' _chemical_formula_weight 695.07 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.805(3) _cell_length_b 26.307(6) _cell_length_c 10.923(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.242(4) _cell_angle_gamma 90.00 _cell_volume 3494.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(1) _cell_measurement_reflns_used 5978 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 22.50 _exptl_crystal_description blade _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.785 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.498 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX DUO' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4571 _diffrn_reflns_av_R_equivalents 0.102 _diffrn_reflns_av_sigmaI/netI 0.0980 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 22.53 _reflns_number_total 4571 _reflns_number_gt 3314 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+9.7000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4571 _refine_ls_number_parameters 392 _refine_ls_number_restraints 504 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1614 _refine_ls_wR_factor_gt 0.1408 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 0.976 _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 0.3979(8) 0.4882(3) 0.8211(8) 0.031(2) Uani 1 1 d U . . H1 H 0.3683 0.5184 0.8446 0.037 Uiso 1 1 calc R . . C2 C 0.6908(7) 0.4864(3) 0.5780(8) 0.024(2) Uani 1 1 d U . . H2 H 0.7069 0.5161 0.5380 0.029 Uiso 1 1 calc R . . C3 C 0.5452(7) 0.5411(3) 0.7880(8) 0.026(2) Uani 1 1 d U . . H3 H 0.6152 0.5404 0.8616 0.031 Uiso 1 1 calc R . . C4 C 0.5767(8) 0.5415(3) 0.6645(9) 0.031(2) Uani 1 1 d U . . H4 H 0.5060 0.5429 0.5920 0.038 Uiso 1 1 calc R . . C5 C 0.6394(7) 0.5884(3) 0.6518(8) 0.026(2) Uani 1 1 d U . . H5A H 0.6487 0.5890 0.5652 0.031 Uiso 1 1 calc R . . H5B H 0.7135 0.5872 0.7165 0.031 Uiso 1 1 calc R . . C6 C 0.5818(8) 0.6367(3) 0.6709(9) 0.035(2) Uani 1 1 d U . . H6A H 0.6307 0.6661 0.6739 0.042 Uiso 1 1 calc R . . H6B H 0.5144 0.6415 0.5966 0.042 Uiso 1 1 calc R . . C7 C 0.5514(8) 0.6349(3) 0.7936(9) 0.037(2) Uani 1 1 d U . . H7A H 0.6195 0.6350 0.8682 0.044 Uiso 1 1 calc R . . H7B H 0.5091 0.6659 0.7990 0.044 Uiso 1 1 calc R . . C8 C 0.4849(7) 0.5894(3) 0.8016(8) 0.025(2) Uani 1 1 d U . . H8A H 0.4133 0.5908 0.7324 0.030 Uiso 1 1 calc R . . H8B H 0.4705 0.5892 0.8856 0.030 Uiso 1 1 calc R . . C9 C 0.7157(7) 0.3911(3) 0.5896(8) 0.026(2) Uani 1 1 d U . . C10 C 0.7372(7) 0.4404(3) 0.5516(8) 0.023(2) Uani 1 1 d U . . C11 C 0.8164(7) 0.4460(3) 0.4838(8) 0.028(2) Uani 1 1 d U . . H11 H 0.8304 0.4790 0.4568 0.033 Uiso 1 1 calc R . . C12 C 0.8720(7) 0.4054(3) 0.4572(8) 0.024(2) Uani 1 1 d U . . C13 C 0.8521(7) 0.3583(3) 0.5042(8) 0.028(2) Uani 1 1 d U . . H13 H 0.8936 0.3302 0.4901 0.033 Uiso 1 1 calc R . . C14 C 0.7790(7) 0.3488(3) 0.5683(8) 0.023(2) Uani 1 1 d U . . C15 C 0.3613(7) 0.3949(3) 0.7708(8) 0.025(2) Uani 1 1 d U . . C16 C 0.3390(7) 0.4422(3) 0.8218(8) 0.022(2) Uani 1 1 d U . . C17 C 0.2516(7) 0.4452(3) 0.8771(8) 0.027(2) Uani 1 1 d U . . H17 H 0.2378 0.4767 0.9119 0.032 Uiso 1 1 calc R . . C18 C 0.1879(7) 0.4045(3) 0.8814(8) 0.026(2) Uani 1 1 d U . . C19 C 0.2089(7) 0.3588(3) 0.8250(8) 0.025(2) Uani 1 1 d U . . H19 H 0.1628 0.3304 0.8241 0.030 Uiso 1 1 calc R . . C20 C 0.2920(7) 0.3531(3) 0.7715(8) 0.0211(19) Uani 1 1 d U . . C21 C 0.9605(7) 0.4100(3) 0.3899(9) 0.030(2) Uani 1 1 d U . . C22 C 0.9573(8) 0.4612(3) 0.3259(9) 0.037(2) Uani 1 1 d U . . H22A H 1.0139 0.4624 0.2828 0.055 Uiso 1 1 calc R . . H22B H 0.9713 0.4881 0.3912 0.055 Uiso 1 1 calc R . . H22C H 0.8848 0.4664 0.2622 0.055 Uiso 1 1 calc R . . C23 C 1.0752(8) 0.4022(4) 0.4910(10) 0.039(3) Uani 1 1 d U . . H23A H 1.1315 0.4017 0.4474 0.058 Uiso 1 1 calc R . . H23B H 1.0763 0.3698 0.5358 0.058 Uiso 1 1 calc R . . H23C H 1.0903 0.4301 0.5535 0.058 Uiso 1 1 calc R . . C24 C 0.9407(9) 0.3690(4) 0.2859(9) 0.042(3) Uani 1 1 d U . . H24A H 0.8675 0.3736 0.2230 0.063 Uiso 1 1 calc R . . H24B H 0.9453 0.3354 0.3258 0.063 Uiso 1 1 calc R . . H24C H 0.9966 0.3718 0.2421 0.063 Uiso 1 1 calc R . . C25 C 0.7618(7) 0.2952(3) 0.6165(9) 0.029(2) Uani 1 1 d U . . C26 C 0.8472(7) 0.2582(3) 0.5970(9) 0.034(2) Uani 1 1 d U . . H26A H 0.8330 0.2240 0.6240 0.051 Uiso 1 1 calc R . . H26B H 0.9209 0.2692 0.6488 0.051 Uiso 1 1 calc R . . H26C H 0.8425 0.2576 0.5058 0.051 Uiso 1 1 calc R . . C27 C 0.6481(7) 0.2753(3) 0.5398(9) 0.034(2) Uani 1 1 d U . . H27A H 0.5916 0.2972 0.5553 0.052 Uiso 1 1 calc R . . H27B H 0.6393 0.2406 0.5673 0.052 Uiso 1 1 calc R . . H27C H 0.6405 0.2755 0.4477 0.052 Uiso 1 1 calc R . . C29 C 0.3138(7) 0.3009(3) 0.7179(9) 0.028(2) Uani 1 1 d U . . C30 C 0.2267(7) 0.2623(3) 0.7202(8) 0.028(2) Uani 1 1 d U . . H30A H 0.2418 0.2301 0.6837 0.043 Uiso 1 1 calc R . . H30B H 0.1542 0.2749 0.6690 0.043 Uiso 1 1 calc R . . H30C H 0.2278 0.2568 0.8093 0.043 Uiso 1 1 calc R . . C32 C 0.4260(7) 0.2812(3) 0.8027(9) 0.031(2) Uani 1 1 d U . . H32A H 0.4263 0.2789 0.8923 0.047 Uiso 1 1 calc R . . H32B H 0.4839 0.3046 0.7972 0.047 Uiso 1 1 calc R . . H32C H 0.4394 0.2475 0.7726 0.047 Uiso 1 1 calc R . . C28 C 0.7744(9) 0.2953(4) 0.7604(9) 0.038(3) Uani 1 1 d U . . H28A H 0.7191 0.3179 0.7762 0.058 Uiso 1 1 calc R . . H28B H 0.8481 0.3074 0.8092 0.058 Uiso 1 1 calc R . . H28C H 0.7641 0.2608 0.7880 0.058 Uiso 1 1 calc R . . C31 C 0.3150(8) 0.3052(3) 0.5788(9) 0.031(2) Uani 1 1 d U . . H31A H 0.3713 0.3298 0.5744 0.046 Uiso 1 1 calc R . . H31B H 0.2428 0.3167 0.5235 0.046 Uiso 1 1 calc R . . H31C H 0.3317 0.2719 0.5492 0.046 Uiso 1 1 calc R . . C33 C 0.0921(7) 0.4075(4) 0.9372(9) 0.029(2) Uani 1 1 d U . . C35 C -0.0162(7) 0.4122(4) 0.8262(10) 0.042(3) Uani 1 1 d U . . H35A H -0.0782 0.4104 0.8605 0.062 Uiso 1 1 calc R . . H35B H -0.0216 0.3844 0.7647 0.062 Uiso 1 1 calc R . . H35C H -0.0180 0.4449 0.7823 0.062 Uiso 1 1 calc R . . C34 C 0.1045(8) 0.4521(4) 1.0268(10) 0.039(3) Uani 1 1 d U . . H34A H 0.1017 0.4837 0.9786 0.059 Uiso 1 1 calc R . . H34B H 0.1752 0.4498 1.0954 0.059 Uiso 1 1 calc R . . H34C H 0.0446 0.4518 1.0649 0.059 Uiso 1 1 calc R . . C36 C 0.0889(9) 0.3594(4) 1.0153(10) 0.042(3) Uani 1 1 d U . . H36A H 0.1592 0.3555 1.0840 0.062 Uiso 1 1 calc R . . H36B H 0.0762 0.3297 0.9584 0.062 Uiso 1 1 calc R . . H36C H 0.0294 0.3622 1.0535 0.062 Uiso 1 1 calc R . . N1 N 0.4887(6) 0.4929(3) 0.7911(7) 0.0283(18) Uani 1 1 d U . . N2 N 0.6283(6) 0.4923(3) 0.6515(7) 0.0251(17) Uani 1 1 d U . . O1 O 0.4414(5) 0.3897(2) 0.7207(6) 0.0309(15) Uani 1 1 d U . . O2 O 0.6363(5) 0.3824(2) 0.6410(6) 0.0294(15) Uani 1 1 d U . . Cl1 Cl 0.71311(19) 0.41907(9) 0.9702(2) 0.0360(6) Uani 1 1 d U . . In1 In 0.58604(5) 0.42935(2) 0.76081(6) 0.0248(2) Uani 1 1 d U . . 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 0.045(6) 0.025(5) 0.028(5) -0.004(4) 0.019(5) 0.001(4) C2 0.037(5) 0.023(5) 0.012(4) -0.004(4) 0.006(4) -0.001(4) C3 0.040(5) 0.025(5) 0.013(4) 0.002(4) 0.009(4) 0.000(4) C4 0.046(6) 0.017(5) 0.030(5) -0.004(4) 0.011(5) -0.004(4) C5 0.036(5) 0.024(5) 0.015(5) -0.005(4) 0.006(4) -0.001(4) C6 0.047(6) 0.020(5) 0.036(6) -0.004(4) 0.007(5) 0.002(5) C7 0.057(6) 0.026(5) 0.033(5) -0.002(4) 0.024(5) 0.006(5) C8 0.034(5) 0.022(5) 0.022(5) -0.015(4) 0.014(4) -0.017(4) C9 0.028(5) 0.031(5) 0.017(5) -0.008(4) 0.005(4) -0.010(4) C10 0.031(5) 0.022(5) 0.018(5) 0.001(4) 0.012(4) 0.005(4) C11 0.032(5) 0.024(5) 0.023(5) 0.008(4) 0.002(4) -0.004(4) C12 0.035(5) 0.026(5) 0.012(4) 0.001(4) 0.007(4) 0.001(4) C13 0.036(5) 0.031(5) 0.016(5) -0.004(4) 0.008(4) 0.006(4) C14 0.032(5) 0.020(5) 0.016(4) -0.002(4) 0.004(4) 0.005(4) C15 0.026(5) 0.026(5) 0.021(5) -0.009(4) 0.005(4) -0.003(4) C16 0.022(4) 0.025(5) 0.015(5) 0.000(4) 0.000(4) 0.000(4) C17 0.033(5) 0.029(5) 0.019(5) -0.002(4) 0.010(4) 0.005(4) C18 0.034(5) 0.028(5) 0.013(4) 0.002(4) 0.004(4) -0.003(4) C19 0.040(5) 0.025(5) 0.015(5) 0.002(4) 0.013(4) 0.000(4) C20 0.034(5) 0.015(4) 0.014(4) 0.000(4) 0.006(4) 0.001(4) C21 0.037(5) 0.033(5) 0.023(5) 0.001(4) 0.016(4) -0.001(4) C22 0.051(6) 0.034(6) 0.034(6) 0.002(5) 0.026(5) 0.005(5) C23 0.050(6) 0.033(6) 0.046(6) 0.006(5) 0.031(5) 0.015(5) C24 0.066(7) 0.041(6) 0.024(5) -0.009(5) 0.022(5) -0.004(5) C25 0.036(5) 0.027(5) 0.025(5) 0.000(4) 0.012(4) -0.007(4) C26 0.052(6) 0.019(5) 0.035(6) 0.002(4) 0.019(5) 0.008(5) C27 0.049(6) 0.031(5) 0.026(5) 0.004(5) 0.016(5) 0.005(5) C29 0.034(5) 0.028(5) 0.028(5) -0.001(4) 0.016(4) -0.005(4) C30 0.035(5) 0.028(5) 0.023(5) -0.001(4) 0.011(4) -0.007(4) C32 0.040(6) 0.026(5) 0.032(5) -0.004(4) 0.018(5) 0.002(5) C28 0.063(7) 0.027(5) 0.033(6) 0.005(5) 0.026(5) -0.006(5) C31 0.034(5) 0.026(5) 0.030(5) -0.010(4) 0.008(4) -0.001(4) C33 0.036(5) 0.028(5) 0.031(5) 0.002(4) 0.020(5) 0.000(4) C35 0.017(5) 0.075(8) 0.034(6) -0.003(6) 0.009(4) 0.003(5) C34 0.033(6) 0.054(6) 0.034(6) -0.006(5) 0.016(5) 0.005(5) C36 0.057(7) 0.043(6) 0.037(6) 0.005(5) 0.033(5) 0.008(5) N1 0.040(5) 0.018(4) 0.029(4) -0.003(3) 0.014(4) -0.004(3) N2 0.030(4) 0.023(4) 0.022(4) 0.001(3) 0.009(4) 0.002(3) O1 0.038(4) 0.021(3) 0.043(4) -0.009(3) 0.027(3) -0.006(3) O2 0.044(4) 0.021(3) 0.029(3) -0.006(3) 0.019(3) -0.009(3) Cl1 0.0458(14) 0.0351(13) 0.0278(13) -0.0001(11) 0.0125(11) 0.0078(11) In1 0.0317(4) 0.0198(3) 0.0266(4) -0.0005(3) 0.0143(3) -0.0001(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.308(11) . ? C1 C16 1.428(12) . ? C1 H1 0.9500 . ? C2 N2 1.308(11) . ? C2 C10 1.416(11) . ? C2 H2 0.9500 . ? C3 N1 1.466(11) . ? C3 C8 1.518(12) . ? C3 C4 1.525(12) . ? C3 H3 1.0000 . ? C4 N2 1.480(11) . ? C4 C5 1.501(12) . ? C4 H4 1.0000 . ? C5 C6 1.516(12) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.509(13) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.489(12) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O2 1.326(10) . ? C9 C10 1.416(12) . ? C9 C14 1.436(12) . ? C10 C11 1.438(12) . ? C11 C12 1.366(12) . ? C11 H11 0.9500 . ? C12 C13 1.395(12) . ? C12 C21 1.537(12) . ? C13 C14 1.356(12) . ? C13 H13 0.9500 . ? C14 C25 1.546(12) . ? C15 O1 1.312(10) . ? C15 C20 1.416(12) . ? C15 C16 1.428(12) . ? C16 C17 1.429(12) . ? C17 C18 1.356(12) . ? C17 H17 0.9500 . ? C18 C19 1.415(12) . ? C18 C33 1.533(12) . ? C19 C20 1.373(12) . ? C19 H19 0.9500 . ? C20 C29 1.551(12) . ? C21 C22 1.514(12) . ? C21 C24 1.529(13) . ? C21 C23 1.550(13) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C27 1.527(12) . ? C25 C28 1.528(12) . ? C25 C26 1.529(12) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C29 C30 1.515(11) . ? C29 C31 1.529(12) . ? C29 C32 1.536(12) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C33 C34 1.503(13) . ? C33 C36 1.535(13) . ? C33 C35 1.535(13) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? N1 In1 2.171(7) . ? N2 In1 2.207(7) . ? O1 In1 2.050(6) . ? O2 In1 2.044(6) . ? Cl1 In1 2.371(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 N1 C1 C16 126.5(8) . . ? N1 C1 H1 116.8 . . ? C16 C1 H1 116.8 . . ? N2 C2 C10 127.1(8) . . ? N2 C2 H2 116.4 . . ? C10 C2 H2 116.4 . . ? N1 C3 C8 116.9(7) . . ? N1 C3 C4 107.2(7) . . ? C8 C3 C4 111.4(7) . . ? N1 C3 H3 107.0 . . ? C8 C3 H3 107.0 . . ? C4 C3 H3 107.0 . . ? N2 C4 C5 116.2(7) . . ? N2 C4 C3 109.2(7) . . ? C5 C4 C3 112.7(7) . . ? N2 C4 H4 106.0 . . ? C5 C4 H4 106.0 . . ? C3 C4 H4 106.0 . . ? C4 C5 C6 112.2(7) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 111.6(8) . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 112.9(8) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C3 110.5(7) . . ? C7 C8 H8A 109.5 . . ? C3 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O2 C9 C10 121.8(8) . . ? O2 C9 C14 118.8(8) . . ? C10 C9 C14 119.4(8) . . ? C9 C10 C2 126.2(8) . . ? C9 C10 C11 118.6(7) . . ? C2 C10 C11 115.2(8) . . ? C12 C11 C10 121.8(8) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 116.8(8) . . ? C11 C12 C21 123.5(8) . . ? C13 C12 C21 119.5(8) . . ? C14 C13 C12 126.0(8) . . ? C14 C13 H13 117.0 . . ? C12 C13 H13 117.0 . . ? C13 C14 C9 117.3(8) . . ? C13 C14 C25 122.5(8) . . ? C9 C14 C25 120.2(7) . . ? O1 C15 C20 119.6(8) . . ? O1 C15 C16 122.2(8) . . ? C20 C15 C16 118.1(7) . . ? C1 C16 C15 124.3(8) . . ? C1 C16 C17 116.1(8) . . ? C15 C16 C17 119.5(8) . . ? C18 C17 C16 122.0(8) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C17 C18 C19 117.3(8) . . ? C17 C18 C33 122.6(8) . . ? C19 C18 C33 120.1(8) . . ? C20 C19 C18 123.8(8) . . ? C20 C19 H19 118.1 . . ? C18 C19 H19 118.1 . . ? C19 C20 C15 119.2(8) . . ? C19 C20 C29 120.8(7) . . ? C15 C20 C29 119.9(7) . . ? C22 C21 C24 108.1(8) . . ? C22 C21 C12 112.0(7) . . ? C24 C21 C12 108.9(8) . . ? C22 C21 C23 109.2(8) . . ? C24 C21 C23 109.6(8) . . ? C12 C21 C23 109.0(8) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 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 . . ? C27 C25 C28 109.9(8) . . ? C27 C25 C26 107.8(7) . . ? C28 C25 C26 107.1(8) . . ? C27 C25 C14 109.8(7) . . ? C28 C25 C14 111.6(7) . . ? C26 C25 C14 110.5(7) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C30 C29 C31 107.6(7) . . ? C30 C29 C32 108.5(7) . . ? C31 C29 C32 109.0(7) . . ? C30 C29 C20 111.5(7) . . ? C31 C29 C20 111.7(7) . . ? C32 C29 C20 108.5(7) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C34 C33 C18 111.4(8) . . ? C34 C33 C36 107.3(8) . . ? C18 C33 C36 110.0(7) . . ? C34 C33 C35 109.7(8) . . ? C18 C33 C35 109.1(7) . . ? C36 C33 C35 109.3(8) . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C1 N1 C3 124.8(7) . . ? C1 N1 In1 124.3(6) . . ? C3 N1 In1 110.6(5) . . ? C2 N2 C4 122.8(7) . . ? C2 N2 In1 122.9(6) . . ? C4 N2 In1 114.3(5) . . ? C15 O1 In1 129.0(5) . . ? C9 O2 In1 127.2(5) . . ? O2 In1 O1 90.0(2) . . ? O2 In1 N1 150.9(3) . . ? O1 In1 N1 84.3(3) . . ? O2 In1 N2 85.8(2) . . ? O1 In1 N2 128.6(3) . . ? N1 In1 N2 75.8(3) . . ? O2 In1 Cl1 106.86(19) . . ? O1 In1 Cl1 116.72(19) . . ? N1 In1 Cl1 101.2(2) . . ? N2 In1 Cl1 113.40(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C3 C4 N2 -47.2(10) . . . . ? C8 C3 C4 N2 -176.2(7) . . . . ? N1 C3 C4 C5 -177.8(7) . . . . ? C8 C3 C4 C5 53.1(10) . . . . ? N2 C4 C5 C6 -178.2(8) . . . . ? C3 C4 C5 C6 -51.1(10) . . . . ? C4 C5 C6 C7 51.1(11) . . . . ? C5 C6 C7 C8 -54.5(11) . . . . ? C6 C7 C8 C3 56.3(11) . . . . ? N1 C3 C8 C7 -178.7(8) . . . . ? C4 C3 C8 C7 -54.9(10) . . . . ? O2 C9 C10 C2 9.2(14) . . . . ? C14 C9 C10 C2 -172.8(8) . . . . ? O2 C9 C10 C11 -173.3(8) . . . . ? C14 C9 C10 C11 4.7(12) . . . . ? N2 C2 C10 C9 6.8(15) . . . . ? N2 C2 C10 C11 -170.7(8) . . . . ? C9 C10 C11 C12 -1.0(13) . . . . ? C2 C10 C11 C12 176.7(8) . . . . ? C10 C11 C12 C13 -2.9(13) . . . . ? C10 C11 C12 C21 -177.5(8) . . . . ? C11 C12 C13 C14 3.4(14) . . . . ? C21 C12 C13 C14 178.2(8) . . . . ? C12 C13 C14 C9 0.2(13) . . . . ? C12 C13 C14 C25 179.7(8) . . . . ? O2 C9 C14 C13 173.8(8) . . . . ? C10 C9 C14 C13 -4.3(12) . . . . ? O2 C9 C14 C25 -5.7(12) . . . . ? C10 C9 C14 C25 176.2(8) . . . . ? N1 C1 C16 C15 -10.0(15) . . . . ? N1 C1 C16 C17 170.6(9) . . . . ? O1 C15 C16 C1 1.6(14) . . . . ? C20 C15 C16 C1 -176.4(8) . . . . ? O1 C15 C16 C17 -179.0(8) . . . . ? C20 C15 C16 C17 3.0(12) . . . . ? C1 C16 C17 C18 178.7(8) . . . . ? C15 C16 C17 C18 -0.8(13) . . . . ? C16 C17 C18 C19 -2.0(13) . . . . ? C16 C17 C18 C33 -178.4(8) . . . . ? C17 C18 C19 C20 2.6(13) . . . . ? C33 C18 C19 C20 179.2(8) . . . . ? C18 C19 C20 C15 -0.4(13) . . . . ? C18 C19 C20 C29 176.7(8) . . . . ? O1 C15 C20 C19 179.5(8) . . . . ? C16 C15 C20 C19 -2.4(12) . . . . ? O1 C15 C20 C29 2.4(12) . . . . ? C16 C15 C20 C29 -179.5(8) . . . . ? C11 C12 C21 C22 -15.2(13) . . . . ? C13 C12 C21 C22 170.4(8) . . . . ? C11 C12 C21 C24 -134.8(9) . . . . ? C13 C12 C21 C24 50.8(11) . . . . ? C11 C12 C21 C23 105.7(10) . . . . ? C13 C12 C21 C23 -68.7(10) . . . . ? C13 C14 C25 C27 -111.6(9) . . . . ? C9 C14 C25 C27 67.9(10) . . . . ? C13 C14 C25 C28 126.3(9) . . . . ? C9 C14 C25 C28 -54.2(11) . . . . ? C13 C14 C25 C26 7.2(12) . . . . ? C9 C14 C25 C26 -173.3(8) . . . . ? C19 C20 C29 C30 6.2(11) . . . . ? C15 C20 C29 C30 -176.6(7) . . . . ? C19 C20 C29 C31 126.6(9) . . . . ? C15 C20 C29 C31 -56.2(11) . . . . ? C19 C20 C29 C32 -113.2(9) . . . . ? C15 C20 C29 C32 63.9(10) . . . . ? C17 C18 C33 C34 -21.3(12) . . . . ? C19 C18 C33 C34 162.4(8) . . . . ? C17 C18 C33 C36 -140.1(9) . . . . ? C19 C18 C33 C36 43.5(11) . . . . ? C17 C18 C33 C35 99.9(10) . . . . ? C19 C18 C33 C35 -76.4(11) . . . . ? C16 C1 N1 C3 178.2(8) . . . . ? C16 C1 N1 In1 -9.2(13) . . . . ? C8 C3 N1 C1 -9.3(13) . . . . ? C4 C3 N1 C1 -135.1(9) . . . . ? C8 C3 N1 In1 177.3(6) . . . . ? C4 C3 N1 In1 51.5(8) . . . . ? C10 C2 N2 C4 -175.0(9) . . . . ? C10 C2 N2 In1 2.7(12) . . . . ? C5 C4 N2 C2 -31.3(12) . . . . ? C3 C4 N2 C2 -160.0(8) . . . . ? C5 C4 N2 In1 150.8(6) . . . . ? C3 C4 N2 In1 22.1(9) . . . . ? C20 C15 O1 In1 -154.5(6) . . . . ? C16 C15 O1 In1 27.5(12) . . . . ? C10 C9 O2 In1 -34.8(11) . . . . ? C14 C9 O2 In1 147.1(6) . . . . ? C9 O2 In1 O1 162.0(7) . . . . ? C9 O2 In1 N1 83.7(9) . . . . ? C9 O2 In1 N2 33.2(7) . . . . ? C9 O2 In1 Cl1 -80.0(7) . . . . ? C15 O1 In1 O2 174.8(7) . . . . ? C15 O1 In1 N1 -33.8(7) . . . . ? C15 O1 In1 N2 -100.5(8) . . . . ? C15 O1 In1 Cl1 65.9(7) . . . . ? C1 N1 In1 O2 103.5(8) . . . . ? C3 N1 In1 O2 -83.0(7) . . . . ? C1 N1 In1 O1 23.8(7) . . . . ? C3 N1 In1 O1 -162.7(6) . . . . ? C1 N1 In1 N2 156.1(8) . . . . ? C3 N1 In1 N2 -30.4(5) . . . . ? C1 N1 In1 Cl1 -92.4(7) . . . . ? C3 N1 In1 Cl1 81.1(6) . . . . ? C2 N2 In1 O2 -16.9(6) . . . . ? C4 N2 In1 O2 161.0(6) . . . . ? C2 N2 In1 O1 -103.6(7) . . . . ? C4 N2 In1 O1 74.3(6) . . . . ? C2 N2 In1 N1 -174.1(7) . . . . ? C4 N2 In1 N1 3.8(6) . . . . ? C2 N2 In1 Cl1 89.7(6) . . . . ? C4 N2 In1 Cl1 -92.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 22.53 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.307 _refine_diff_density_min -1.177 _refine_diff_density_rms 0.144 #===END data_pm079 _database_code_depnum_ccdc_archive 'CCDC 882422' #TrackingRef '- cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C100 H162 In2 N4 O6' _chemical_formula_weight 1745.98 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' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.0584(14) _cell_length_b 17.6316(9) _cell_length_c 20.2917(11) _cell_angle_alpha 90.00 _cell_angle_beta 110.009(3) _cell_angle_gamma 90.00 _cell_volume 9768.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 9614 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 22.47 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3744 _exptl_absorpt_coefficient_mu 0.523 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.374 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6331 _diffrn_reflns_av_R_equivalents 0.141 _diffrn_reflns_av_sigmaI/netI 0.0830 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 22.51 _reflns_number_total 6435 _reflns_number_gt 4925 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0974P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0033(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6435 _refine_ls_number_parameters 520 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1798 _refine_ls_wR_factor_gt 0.1460 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 0.4983(3) 0.7948(4) 0.4187(4) 0.0220(17) Uani 1 1 d . . . C2 C 0.5353(3) 0.8344(4) 0.4730(4) 0.0239(19) Uani 1 1 d . . . C3 C 0.5662(3) 0.7947(4) 0.5314(4) 0.0241(18) Uani 1 1 d . . . H3 H 0.5906 0.8221 0.5668 0.029 Uiso 1 1 calc R . . C4 C 0.5628(3) 0.7177(4) 0.5395(4) 0.028(2) Uani 1 1 d . . . C5 C 0.5244(3) 0.6811(4) 0.4878(4) 0.0241(18) Uani 1 1 d . . . H5 H 0.5201 0.6285 0.4940 0.029 Uiso 1 1 calc R . . C6 C 0.4926(3) 0.7148(4) 0.4290(4) 0.0252(19) Uani 1 1 d . . . C7 C 0.5438(3) 0.9152(4) 0.4737(4) 0.0207(19) Uani 1 1 d . . . H7 H 0.5680 0.9344 0.5148 0.025 Uiso 1 1 calc R . . C8 C 0.5362(3) 1.0463(4) 0.4379(4) 0.0251(19) Uani 1 1 d . . . H8 H 0.5121 1.0700 0.4569 0.030 Uiso 1 1 calc R . . C9 C 0.5868(3) 1.0639(4) 0.4893(4) 0.0254(19) Uani 1 1 d . . . H9A H 0.6119 1.0390 0.4736 0.030 Uiso 1 1 calc R . . H9B H 0.5900 1.0434 0.5360 0.030 Uiso 1 1 calc R . . C10 C 0.5958(3) 1.1503(4) 0.4945(4) 0.030(2) Uani 1 1 d . . . H10A H 0.5730 1.1744 0.5150 0.036 Uiso 1 1 calc R . . H10B H 0.6296 1.1606 0.5260 0.036 Uiso 1 1 calc R . . C11 C 0.5882(3) 1.1838(4) 0.4236(4) 0.027(2) Uani 1 1 d . . . H11A H 0.6123 1.1618 0.4045 0.032 Uiso 1 1 calc R . . H11B H 0.5938 1.2392 0.4283 0.032 Uiso 1 1 calc R . . C12 C 0.5372(3) 1.1688(4) 0.3733(4) 0.027(2) Uani 1 1 d . . . H12A H 0.5333 1.1916 0.3271 0.032 Uiso 1 1 calc R . . H12B H 0.5129 1.1924 0.3912 0.032 Uiso 1 1 calc R . . C13 C 0.5281(3) 1.0834(4) 0.3649(4) 0.0251(19) Uani 1 1 d . . . H13 H 0.5528 1.0614 0.3461 0.030 Uiso 1 1 calc R . . C14 C 0.4434(3) 1.1034(4) 0.2928(4) 0.0222(18) Uani 1 1 d . . . H14 H 0.4507 1.1561 0.2953 0.027 Uiso 1 1 calc R . . C15 C 0.3931(3) 1.0814(4) 0.2593(4) 0.0207(18) Uani 1 1 d . . . C16 C 0.3608(3) 1.1374(4) 0.2178(4) 0.0252(19) Uani 1 1 d . . . H16 H 0.3740 1.1851 0.2117 0.030 Uiso 1 1 calc R . . C17 C 0.3120(3) 1.1255(4) 0.1866(4) 0.0229(19) Uani 1 1 d . . . C18 C 0.2941(3) 1.0559(4) 0.2025(4) 0.027(2) Uani 1 1 d . . . H18 H 0.2599 1.0471 0.1826 0.032 Uiso 1 1 calc R . . C19 C 0.3222(3) 0.9997(4) 0.2445(5) 0.0215(19) Uani 1 1 d . . . C20 C 0.3737(3) 1.0108(4) 0.2711(5) 0.0227(19) Uani 1 1 d . . . C21 C 0.5978(3) 0.6735(4) 0.6010(4) 0.032(2) Uani 1 1 d . . . C22 C 0.6408(3) 0.7210(5) 0.6445(5) 0.047(3) Uani 1 1 d . . . H22A H 0.6288 0.7651 0.6632 0.071 Uiso 1 1 calc R . . H22B H 0.6594 0.7381 0.6151 0.071 Uiso 1 1 calc R . . H22C H 0.6620 0.6904 0.6834 0.071 Uiso 1 1 calc R . . C23 C 0.5709(4) 0.6433(6) 0.6485(6) 0.063(3) Uani 1 1 d . . . H23A H 0.5411 0.6169 0.6200 0.095 Uiso 1 1 calc R . . H23B H 0.5622 0.6857 0.6732 0.095 Uiso 1 1 calc R . . H23C H 0.5922 0.6080 0.6828 0.095 Uiso 1 1 calc R . . C24 C 0.6183(4) 0.6049(5) 0.5723(5) 0.050(3) Uani 1 1 d . . . H24A H 0.6348 0.6229 0.5405 0.075 Uiso 1 1 calc R . . H24B H 0.5913 0.5710 0.5469 0.075 Uiso 1 1 calc R . . H24C H 0.6418 0.5774 0.6115 0.075 Uiso 1 1 calc R . . C25 C 0.4528(3) 0.6700(4) 0.3725(4) 0.027(2) Uani 1 1 d . . . C26 C 0.4637(3) 0.6693(5) 0.3043(4) 0.036(2) Uani 1 1 d . . . H26A H 0.4949 0.6435 0.3118 0.053 Uiso 1 1 calc R . . H26B H 0.4657 0.7216 0.2890 0.053 Uiso 1 1 calc R . . H26C H 0.4374 0.6425 0.2681 0.053 Uiso 1 1 calc R . . C27 C 0.4021(3) 0.7036(4) 0.3609(4) 0.029(2) Uani 1 1 d . . . H27A H 0.4012 0.7562 0.3451 0.044 Uiso 1 1 calc R . . H27B H 0.3953 0.7021 0.4050 0.044 Uiso 1 1 calc R . . H27C H 0.3773 0.6739 0.3253 0.044 Uiso 1 1 calc R . . C28 C 0.4501(3) 0.5863(4) 0.3943(5) 0.035(2) Uani 1 1 d . . . H28A H 0.4423 0.5846 0.4376 0.053 Uiso 1 1 calc R . . H28B H 0.4818 0.5617 0.4021 0.053 Uiso 1 1 calc R . . H28C H 0.4246 0.5597 0.3569 0.053 Uiso 1 1 calc R . . C29 C 0.2762(3) 1.1820(4) 0.1378(4) 0.028(2) Uani 1 1 d . . . C30 C 0.3007(3) 1.2600(5) 0.1369(5) 0.037(2) Uani 1 1 d . . . H30A H 0.2762 1.2957 0.1081 0.056 Uiso 1 1 calc R . . H30B H 0.3270 1.2540 0.1173 0.056 Uiso 1 1 calc R . . H30C H 0.3145 1.2795 0.1849 0.056 Uiso 1 1 calc R . . C31 C 0.2326(3) 1.1967(5) 0.1630(5) 0.047(3) Uani 1 1 d . . . H31A H 0.2140 1.1497 0.1600 0.070 Uiso 1 1 calc R . . H31B H 0.2112 1.2355 0.1332 0.070 Uiso 1 1 calc R . . H31C H 0.2448 1.2144 0.2117 0.070 Uiso 1 1 calc R . . C32 C 0.2573(3) 1.1497(5) 0.0638(5) 0.046(3) Uani 1 1 d . . . H32A H 0.2392 1.1028 0.0635 0.069 Uiso 1 1 calc R . . H32B H 0.2850 1.1389 0.0481 0.069 Uiso 1 1 calc R . . H32C H 0.2355 1.1867 0.0321 0.069 Uiso 1 1 calc R . . C33 C 0.2975(3) 0.9284(4) 0.2607(4) 0.0246(19) Uani 1 1 d . . . C34 C 0.2418(3) 0.9322(5) 0.2321(5) 0.041(2) Uani 1 1 d . . . H34A H 0.2309 0.9790 0.2484 0.061 Uiso 1 1 calc R . . H34B H 0.2283 0.8884 0.2490 0.061 Uiso 1 1 calc R . . H34C H 0.2303 0.9318 0.1808 0.061 Uiso 1 1 calc R . . C35 C 0.3131(3) 0.9176(5) 0.3403(4) 0.033(2) Uani 1 1 d . . . H35A H 0.2959 0.8738 0.3505 0.049 Uiso 1 1 calc R . . H35B H 0.3049 0.9632 0.3615 0.049 Uiso 1 1 calc R . . H35C H 0.3485 0.9089 0.3597 0.049 Uiso 1 1 calc R . . C36 C 0.3132(3) 0.8578(4) 0.2296(5) 0.034(2) Uani 1 1 d . . . H36A H 0.3046 0.8643 0.1788 0.051 Uiso 1 1 calc R . . H36B H 0.2964 0.8131 0.2390 0.051 Uiso 1 1 calc R . . H36C H 0.3487 0.8509 0.2511 0.051 Uiso 1 1 calc R . . C37 C 0.4096(3) 0.8976(4) 0.1589(4) 0.0248(19) Uani 1 1 d . . . H37A H 0.4056 0.9166 0.1113 0.030 Uiso 1 1 calc R . . H37B H 0.3837 0.9208 0.1737 0.030 Uiso 1 1 calc R . . C38 C 0.4033(3) 0.8112(4) 0.1562(5) 0.034(2) Uani 1 1 d . . . H38A H 0.4049 0.7925 0.2024 0.051 Uiso 1 1 calc R . . H38B H 0.4295 0.7878 0.1430 0.051 Uiso 1 1 calc R . . H38C H 0.3715 0.7980 0.1214 0.051 Uiso 1 1 calc R . . C39 C 0.3780(4) 0.5920(5) 0.5462(5) 0.049(3) Uani 1 1 d . . . H39A H 0.3643 0.6412 0.5540 0.059 Uiso 1 1 calc R . . H39B H 0.3702 0.5855 0.4950 0.059 Uiso 1 1 calc R . . C40 C 0.4330(4) 0.5924(6) 0.5823(5) 0.056(3) Uani 1 1 d . . . H40A H 0.4470 0.5467 0.5682 0.067 Uiso 1 1 calc R . . H40B H 0.4468 0.6374 0.5667 0.067 Uiso 1 1 calc R . . C41 C 0.4475(5) 0.5940(8) 0.6612(6) 0.080(4) Uani 1 1 d . . . H41A H 0.4836 0.5908 0.6825 0.096 Uiso 1 1 calc R . . H41B H 0.4369 0.6425 0.6759 0.096 Uiso 1 1 calc R . . C42 C 0.4246(5) 0.5290(7) 0.6871(6) 0.069(3) Uani 1 1 d . . . H42A H 0.4338 0.5322 0.7387 0.083 Uiso 1 1 calc R . . H42B H 0.4372 0.4803 0.6756 0.083 Uiso 1 1 calc R . . C43 C 0.3692(5) 0.5312(7) 0.6534(6) 0.065(3) Uani 1 1 d . . . H43A H 0.3563 0.5780 0.6678 0.078 Uiso 1 1 calc R . . H43B H 0.3547 0.4871 0.6694 0.078 Uiso 1 1 calc R . . C44 C 0.3545(5) 0.5292(8) 0.5733(6) 0.073(4) Uani 1 1 d . . . H44A H 0.3643 0.4798 0.5589 0.088 Uiso 1 1 calc R . . H44B H 0.3185 0.5336 0.5520 0.088 Uiso 1 1 calc R . . C45 C 0.2133(4) 0.4340(6) 0.5046(6) 0.053(3) Uani 1 1 d . . . H45A H 0.2316 0.4802 0.5261 0.064 Uiso 1 1 calc R . . H45B H 0.1878 0.4488 0.4599 0.064 Uiso 1 1 calc R . . C46 C 0.2484(4) 0.3774(6) 0.4896(5) 0.052(3) Uani 1 1 d . . . H46A H 0.2659 0.4024 0.4614 0.063 Uiso 1 1 calc R . . H46B H 0.2295 0.3344 0.4621 0.063 Uiso 1 1 calc R . . C47 C 0.2855(3) 0.3479(5) 0.5582(6) 0.051(3) Uani 1 1 d . . . H47A H 0.3054 0.3072 0.5476 0.062 Uiso 1 1 calc R . . H47B H 0.3079 0.3896 0.5818 0.062 Uiso 1 1 calc R . . C48 C 0.2604(4) 0.3171(5) 0.6075(6) 0.054(3) Uani 1 1 d . . . H48A H 0.2411 0.2715 0.5864 0.064 Uiso 1 1 calc R . . H48B H 0.2855 0.3020 0.6525 0.064 Uiso 1 1 calc R . . C49 C 0.2272(4) 0.3754(5) 0.6213(5) 0.052(3) Uani 1 1 d . . . H49A H 0.2468 0.4195 0.6458 0.062 Uiso 1 1 calc R . . H49B H 0.2105 0.3535 0.6520 0.062 Uiso 1 1 calc R . . C50 C 0.1892(3) 0.4015(6) 0.5528(5) 0.049(3) Uani 1 1 d . . . H50A H 0.1684 0.3580 0.5297 0.059 Uiso 1 1 calc R . . H50B H 0.1679 0.4404 0.5627 0.059 Uiso 1 1 calc R . . N1 N 0.5232(2) 0.9646(3) 0.4262(3) 0.0201(14) Uani 1 1 d . . . N2 N 0.4792(2) 1.0570(3) 0.3196(4) 0.0238(16) Uani 1 1 d . . . O1 O 0.46971(18) 0.8278(3) 0.3608(3) 0.0256(13) Uani 1 1 d . . . O2 O 0.40223(17) 0.9559(3) 0.3093(3) 0.0222(12) Uani 1 1 d . . . O3 O 0.45645(17) 0.9202(3) 0.2062(3) 0.0188(12) Uani 1 1 d . . . In1 In 0.47555(2) 0.93206(3) 0.31633(3) 0.0197(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.017(4) 0.020(4) 0.030(5) -0.003(4) 0.009(4) 0.001(3) C2 0.026(5) 0.015(4) 0.033(5) 0.005(4) 0.012(4) -0.002(3) C3 0.028(4) 0.014(4) 0.025(4) -0.001(4) 0.002(4) 0.000(4) C4 0.031(5) 0.022(5) 0.032(5) 0.006(4) 0.012(4) 0.006(4) C5 0.032(5) 0.010(4) 0.031(5) -0.001(4) 0.011(4) 0.001(4) C6 0.028(5) 0.012(4) 0.038(5) 0.003(4) 0.013(4) 0.005(3) C7 0.015(4) 0.024(5) 0.022(4) -0.003(4) 0.005(3) -0.005(3) C8 0.026(5) 0.013(4) 0.036(5) 0.000(4) 0.011(4) 0.009(3) C9 0.027(5) 0.019(5) 0.029(5) -0.003(4) 0.008(4) -0.002(4) C10 0.038(5) 0.016(4) 0.035(5) -0.001(4) 0.010(4) -0.007(4) C11 0.023(5) 0.013(4) 0.040(5) -0.003(4) 0.005(4) -0.010(3) C12 0.038(5) 0.008(4) 0.038(5) -0.001(4) 0.017(4) -0.004(3) C13 0.030(5) 0.013(4) 0.034(5) 0.004(3) 0.013(4) 0.001(4) C14 0.027(5) 0.016(4) 0.024(4) 0.004(4) 0.010(4) 0.011(4) C15 0.023(5) 0.012(4) 0.031(5) -0.001(3) 0.014(4) -0.002(3) C16 0.035(5) 0.012(4) 0.034(5) -0.006(4) 0.018(4) 0.001(4) C17 0.030(5) 0.010(4) 0.026(5) 0.000(3) 0.006(4) 0.011(4) C18 0.023(4) 0.022(5) 0.036(5) -0.008(4) 0.011(4) -0.001(4) C19 0.020(5) 0.017(4) 0.027(5) -0.001(3) 0.007(4) 0.004(3) C20 0.024(5) 0.011(4) 0.031(5) -0.001(4) 0.007(4) 0.003(3) C21 0.040(5) 0.016(4) 0.033(5) 0.005(4) 0.006(4) 0.004(4) C22 0.050(6) 0.026(5) 0.046(6) 0.005(5) -0.009(5) 0.009(4) C23 0.084(8) 0.040(7) 0.062(7) 0.031(6) 0.020(6) 0.016(6) C24 0.051(6) 0.020(5) 0.059(7) -0.004(5) -0.005(5) 0.018(5) C25 0.029(5) 0.013(4) 0.040(5) 0.000(4) 0.012(4) -0.005(4) C26 0.039(5) 0.020(4) 0.042(5) -0.006(4) 0.005(4) 0.004(4) C27 0.029(5) 0.017(4) 0.034(5) -0.003(4) 0.001(4) -0.006(4) C28 0.051(6) 0.012(4) 0.036(5) -0.002(4) 0.008(4) -0.005(4) C29 0.024(4) 0.019(5) 0.038(5) 0.007(4) 0.008(4) 0.005(4) C30 0.036(5) 0.025(5) 0.047(6) 0.009(4) 0.008(4) 0.010(4) C31 0.030(5) 0.030(5) 0.078(7) 0.014(5) 0.017(5) 0.010(4) C32 0.054(6) 0.029(5) 0.042(6) 0.001(5) 0.001(5) 0.006(5) C33 0.027(5) 0.019(5) 0.029(5) 0.001(4) 0.011(4) -0.008(4) C34 0.034(5) 0.040(6) 0.045(6) 0.006(5) 0.009(4) -0.007(4) C35 0.032(5) 0.023(5) 0.046(6) -0.002(4) 0.017(4) -0.007(4) C36 0.048(6) 0.016(4) 0.044(5) -0.002(4) 0.022(5) -0.010(4) C37 0.026(5) 0.015(4) 0.033(5) 0.002(4) 0.009(4) -0.002(4) C38 0.035(5) 0.026(5) 0.043(5) -0.009(4) 0.016(4) -0.008(4) C39 0.058(7) 0.028(6) 0.058(7) -0.001(5) 0.014(5) -0.001(5) C40 0.045(6) 0.066(8) 0.060(7) 0.020(6) 0.024(5) 0.017(5) C41 0.071(8) 0.106(11) 0.065(8) -0.001(8) 0.024(7) -0.011(8) C42 0.095(10) 0.066(8) 0.045(7) 0.008(6) 0.023(7) 0.025(7) C43 0.090(10) 0.052(7) 0.057(7) 0.006(6) 0.033(7) -0.020(7) C44 0.070(8) 0.075(9) 0.063(8) 0.019(7) 0.008(6) -0.022(7) C45 0.042(6) 0.048(7) 0.056(7) 0.007(5) -0.001(5) 0.002(5) C46 0.058(7) 0.043(7) 0.055(7) 0.000(5) 0.018(6) -0.007(5) C47 0.045(6) 0.029(6) 0.082(8) -0.005(5) 0.025(6) 0.001(4) C48 0.070(7) 0.026(6) 0.061(7) 0.006(5) 0.019(6) 0.001(5) C49 0.064(7) 0.027(6) 0.063(7) -0.001(5) 0.021(6) -0.003(5) C50 0.040(6) 0.038(6) 0.066(7) -0.009(5) 0.014(5) -0.010(5) N1 0.024(3) 0.008(3) 0.029(4) 0.003(3) 0.011(3) 0.000(3) N2 0.003(3) 0.020(4) 0.041(4) 0.001(3) -0.002(3) -0.003(3) O1 0.019(3) 0.018(3) 0.032(3) 0.006(2) -0.002(3) -0.006(2) O2 0.018(3) 0.012(3) 0.036(3) -0.003(2) 0.007(2) -0.001(2) O3 0.011(3) 0.014(3) 0.027(3) 0.000(2) 0.001(2) -0.001(2) In1 0.0218(4) 0.0076(3) 0.0278(4) 0.0008(3) 0.0061(3) -0.0002(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.320(9) . ? C1 C2 1.431(10) . ? C1 C6 1.443(10) . ? C2 C3 1.406(10) . ? C2 C7 1.445(10) . ? C3 C4 1.375(11) . ? C3 H3 0.9500 . ? C4 C5 1.400(11) . ? C4 C21 1.528(11) . ? C5 C6 1.370(11) . ? C5 H5 0.9500 . ? C6 C25 1.540(11) . ? C7 N1 1.286(9) . ? C7 H7 0.9500 . ? C8 N1 1.487(9) . ? C8 C9 1.516(11) . ? C8 C13 1.560(11) . ? C8 H8 1.0000 . ? C9 C10 1.543(10) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.500(11) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.507(10) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.528(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N2 1.477(10) . ? C13 H13 1.0000 . ? C14 N2 1.290(9) . ? C14 C15 1.439(10) . ? C14 H14 0.9500 . ? C15 C20 1.419(10) . ? C15 C16 1.422(11) . ? C16 C17 1.357(11) . ? C16 H16 0.9500 . ? C17 C18 1.413(11) . ? C17 C29 1.533(10) . ? C18 C19 1.377(11) . ? C18 H18 0.9500 . ? C19 C20 1.420(11) . ? C19 C33 1.538(10) . ? C20 O2 1.335(9) . ? C21 C22 1.512(12) . ? C21 C23 1.529(13) . ? C21 C24 1.547(12) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.523(12) . ? C25 C27 1.529(11) . ? C25 C28 1.550(11) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C32 1.521(12) . ? C29 C31 1.543(12) . ? C29 C30 1.552(11) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.524(11) . ? C33 C35 1.533(11) . ? C33 C36 1.534(11) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 O3 1.428(9) . ? C37 C38 1.533(11) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C44 1.499(14) . ? C39 C40 1.513(14) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.510(15) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.507(16) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.520(16) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.533(15) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C50 1.497(14) . ? C45 C46 1.529(14) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 C47 1.531(13) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C48 1.526(14) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 C49 1.500(13) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 C50 1.521(13) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? N1 In1 2.259(6) . ? N2 In1 2.206(6) . ? O1 In1 2.080(5) . ? O2 In1 2.128(5) . ? O3 In1 2.121(5) . ? O3 In1 2.185(5) 2_655 ? In1 O3 2.185(5) 2_655 ? 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 O1 C1 C2 123.3(7) . . ? O1 C1 C6 119.4(7) . . ? C2 C1 C6 117.3(7) . . ? C3 C2 C1 120.1(7) . . ? C3 C2 C7 115.1(7) . . ? C1 C2 C7 124.8(7) . . ? C4 C3 C2 122.7(7) . . ? C4 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C3 C4 C5 116.0(7) . . ? C3 C4 C21 123.1(7) . . ? C5 C4 C21 120.9(7) . . ? C6 C5 C4 125.4(7) . . ? C6 C5 H5 117.3 . . ? C4 C5 H5 117.3 . . ? C5 C6 C1 118.3(7) . . ? C5 C6 C25 122.5(7) . . ? C1 C6 C25 119.2(7) . . ? N1 C7 C2 128.8(7) . . ? N1 C7 H7 115.6 . . ? C2 C7 H7 115.6 . . ? N1 C8 C9 116.2(6) . . ? N1 C8 C13 107.9(6) . . ? C9 C8 C13 111.3(7) . . ? N1 C8 H8 107.0 . . ? C9 C8 H8 107.0 . . ? C13 C8 H8 107.0 . . ? C8 C9 C10 110.5(6) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 110.9(7) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C10 C11 C12 111.6(7) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 109.9(6) . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N2 C13 C12 118.2(6) . . ? N2 C13 C8 105.1(6) . . ? C12 C13 C8 110.1(7) . . ? N2 C13 H13 107.7 . . ? C12 C13 H13 107.7 . . ? C8 C13 H13 107.7 . . ? N2 C14 C15 124.9(7) . . ? N2 C14 H14 117.6 . . ? C15 C14 H14 117.6 . . ? C20 C15 C16 119.4(7) . . ? C20 C15 C14 123.7(7) . . ? C16 C15 C14 116.6(7) . . ? C17 C16 C15 122.7(7) . . ? C17 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? C16 C17 C18 115.8(7) . . ? C16 C17 C29 124.8(7) . . ? C18 C17 C29 119.3(7) . . ? C19 C18 C17 125.4(7) . . ? C19 C18 H18 117.3 . . ? C17 C18 H18 117.3 . . ? C18 C19 C20 117.4(7) . . ? C18 C19 C33 120.0(7) . . ? C20 C19 C33 122.6(7) . . ? O2 C20 C15 122.0(7) . . ? O2 C20 C19 119.0(7) . . ? C15 C20 C19 118.9(7) . . ? C22 C21 C4 112.4(7) . . ? C22 C21 C23 108.9(8) . . ? C4 C21 C23 110.6(7) . . ? C22 C21 C24 107.7(7) . . ? C4 C21 C24 109.0(7) . . ? C23 C21 C24 108.1(7) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 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 . . ? C26 C25 C27 110.7(7) . . ? C26 C25 C6 110.1(6) . . ? C27 C25 C6 110.8(6) . . ? C26 C25 C28 107.3(7) . . ? C27 C25 C28 105.9(6) . . ? C6 C25 C28 112.0(7) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C32 C29 C17 109.4(7) . . ? C32 C29 C31 109.3(7) . . ? C17 C29 C31 110.4(7) . . ? C32 C29 C30 109.4(7) . . ? C17 C29 C30 111.7(7) . . ? C31 C29 C30 106.6(7) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C35 107.3(7) . . ? C34 C33 C36 107.9(7) . . ? C35 C33 C36 108.1(7) . . ? C34 C33 C19 113.3(7) . . ? C35 C33 C19 109.6(6) . . ? C36 C33 C19 110.5(6) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O3 C37 C38 112.1(6) . . ? O3 C37 H37A 109.2 . . ? C38 C37 H37A 109.2 . . ? O3 C37 H37B 109.2 . . ? C38 C37 H37B 109.2 . . ? H37A C37 H37B 107.9 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C44 C39 C40 111.3(9) . . ? C44 C39 H39A 109.4 . . ? C40 C39 H39A 109.4 . . ? C44 C39 H39B 109.4 . . ? C40 C39 H39B 109.4 . . ? H39A C39 H39B 108.0 . . ? C41 C40 C39 112.3(9) . . ? C41 C40 H40A 109.1 . . ? C39 C40 H40A 109.1 . . ? C41 C40 H40B 109.1 . . ? C39 C40 H40B 109.1 . . ? H40A C40 H40B 107.9 . . ? C42 C41 C40 111.1(10) . . ? C42 C41 H41A 109.4 . . ? C40 C41 H41A 109.4 . . ? C42 C41 H41B 109.4 . . ? C40 C41 H41B 109.4 . . ? H41A C41 H41B 108.0 . . ? C41 C42 C43 110.4(10) . . ? C41 C42 H42A 109.6 . . ? C43 C42 H42A 109.6 . . ? C41 C42 H42B 109.6 . . ? C43 C42 H42B 109.6 . . ? H42A C42 H42B 108.1 . . ? C42 C43 C44 110.1(10) . . ? C42 C43 H43A 109.6 . . ? C44 C43 H43A 109.6 . . ? C42 C43 H43B 109.6 . . ? C44 C43 H43B 109.6 . . ? H43A C43 H43B 108.2 . . ? C39 C44 C43 112.1(10) . . ? C39 C44 H44A 109.2 . . ? C43 C44 H44A 109.2 . . ? C39 C44 H44B 109.2 . . ? C43 C44 H44B 109.2 . . ? H44A C44 H44B 107.9 . . ? C50 C45 C46 111.9(9) . . ? C50 C45 H45A 109.2 . . ? C46 C45 H45A 109.2 . . ? C50 C45 H45B 109.2 . . ? C46 C45 H45B 109.2 . . ? H45A C45 H45B 107.9 . . ? C45 C46 C47 110.6(8) . . ? C45 C46 H46A 109.5 . . ? C47 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? C47 C46 H46B 109.5 . . ? H46A C46 H46B 108.1 . . ? C48 C47 C46 111.7(8) . . ? C48 C47 H47A 109.3 . . ? C46 C47 H47A 109.3 . . ? C48 C47 H47B 109.3 . . ? C46 C47 H47B 109.3 . . ? H47A C47 H47B 107.9 . . ? C49 C48 C47 111.1(8) . . ? C49 C48 H48A 109.4 . . ? C47 C48 H48A 109.4 . . ? C49 C48 H48B 109.4 . . ? C47 C48 H48B 109.4 . . ? H48A C48 H48B 108.0 . . ? C48 C49 C50 110.4(9) . . ? C48 C49 H49A 109.6 . . ? C50 C49 H49A 109.6 . . ? C48 C49 H49B 109.6 . . ? C50 C49 H49B 109.6 . . ? H49A C49 H49B 108.1 . . ? C45 C50 C49 110.9(8) . . ? C45 C50 H50A 109.5 . . ? C49 C50 H50A 109.5 . . ? C45 C50 H50B 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 108.0 . . ? C7 N1 C8 120.6(7) . . ? C7 N1 In1 122.6(5) . . ? C8 N1 In1 116.1(5) . . ? C14 N2 C13 121.9(6) . . ? C14 N2 In1 126.6(5) . . ? C13 N2 In1 111.1(4) . . ? C1 O1 In1 131.0(5) . . ? C20 O2 In1 126.2(5) . . ? C37 O3 In1 125.6(4) . . ? C37 O3 In1 127.5(5) . 2_655 ? In1 O3 In1 106.34(19) . 2_655 ? O1 In1 O3 109.79(19) . . ? O1 In1 O2 88.6(2) . . ? O3 In1 O2 93.08(19) . . ? O1 In1 O3 102.68(19) . 2_655 ? O3 In1 O3 72.5(2) . 2_655 ? O2 In1 O3 163.99(19) . 2_655 ? O1 In1 N2 151.6(2) . . ? O3 In1 N2 97.1(2) . . ? O2 In1 N2 80.9(2) . . ? O3 In1 N2 93.7(2) 2_655 . ? O1 In1 N1 84.8(2) . . ? O3 In1 N1 156.4(2) . . ? O2 In1 N1 106.1(2) . . ? O3 In1 N1 86.5(2) 2_655 . ? N2 In1 N1 73.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -176.2(7) . . . . ? C6 C1 C2 C3 3.7(11) . . . . ? O1 C1 C2 C7 4.3(12) . . . . ? C6 C1 C2 C7 -175.7(7) . . . . ? C1 C2 C3 C4 -0.1(12) . . . . ? C7 C2 C3 C4 179.4(7) . . . . ? C2 C3 C4 C5 -3.7(12) . . . . ? C2 C3 C4 C21 177.1(7) . . . . ? C3 C4 C5 C6 4.1(12) . . . . ? C21 C4 C5 C6 -176.7(7) . . . . ? C4 C5 C6 C1 -0.5(12) . . . . ? C4 C5 C6 C25 176.9(7) . . . . ? O1 C1 C6 C5 176.5(7) . . . . ? C2 C1 C6 C5 -3.4(11) . . . . ? O1 C1 C6 C25 -0.9(11) . . . . ? C2 C1 C6 C25 179.1(7) . . . . ? C3 C2 C7 N1 176.0(8) . . . . ? C1 C2 C7 N1 -4.6(13) . . . . ? N1 C8 C9 C10 178.4(6) . . . . ? C13 C8 C9 C10 54.4(9) . . . . ? C8 C9 C10 C11 -55.7(9) . . . . ? C9 C10 C11 C12 58.5(9) . . . . ? C10 C11 C12 C13 -59.5(9) . . . . ? C11 C12 C13 N2 177.7(7) . . . . ? C11 C12 C13 C8 57.0(8) . . . . ? N1 C8 C13 N2 47.4(7) . . . . ? C9 C8 C13 N2 176.0(6) . . . . ? N1 C8 C13 C12 175.7(6) . . . . ? C9 C8 C13 C12 -55.7(8) . . . . ? N2 C14 C15 C20 21.6(12) . . . . ? N2 C14 C15 C16 -164.7(7) . . . . ? C20 C15 C16 C17 -2.3(11) . . . . ? C14 C15 C16 C17 -176.2(7) . . . . ? C15 C16 C17 C18 5.1(11) . . . . ? C15 C16 C17 C29 -176.0(7) . . . . ? C16 C17 C18 C19 -2.1(12) . . . . ? C29 C17 C18 C19 178.9(8) . . . . ? C17 C18 C19 C20 -3.6(12) . . . . ? C17 C18 C19 C33 176.7(7) . . . . ? C16 C15 C20 O2 179.7(7) . . . . ? C14 C15 C20 O2 -6.8(12) . . . . ? C16 C15 C20 C19 -3.8(11) . . . . ? C14 C15 C20 C19 169.7(8) . . . . ? C18 C19 C20 O2 -176.9(7) . . . . ? C33 C19 C20 O2 2.8(12) . . . . ? C18 C19 C20 C15 6.4(12) . . . . ? C33 C19 C20 C15 -173.9(7) . . . . ? C3 C4 C21 C22 -9.4(12) . . . . ? C5 C4 C21 C22 171.4(8) . . . . ? C3 C4 C21 C23 112.5(9) . . . . ? C5 C4 C21 C23 -66.7(10) . . . . ? C3 C4 C21 C24 -128.8(9) . . . . ? C5 C4 C21 C24 52.1(10) . . . . ? C5 C6 C25 C26 -113.5(8) . . . . ? C1 C6 C25 C26 63.9(9) . . . . ? C5 C6 C25 C27 123.8(8) . . . . ? C1 C6 C25 C27 -58.8(9) . . . . ? C5 C6 C25 C28 5.8(11) . . . . ? C1 C6 C25 C28 -176.8(7) . . . . ? C16 C17 C29 C32 112.4(9) . . . . ? C18 C17 C29 C32 -68.7(9) . . . . ? C16 C17 C29 C31 -127.3(8) . . . . ? C18 C17 C29 C31 51.6(10) . . . . ? C16 C17 C29 C30 -8.9(11) . . . . ? C18 C17 C29 C30 170.0(7) . . . . ? C18 C19 C33 C34 -5.6(11) . . . . ? C20 C19 C33 C34 174.7(8) . . . . ? C18 C19 C33 C35 -125.4(8) . . . . ? C20 C19 C33 C35 54.9(10) . . . . ? C18 C19 C33 C36 115.6(8) . . . . ? C20 C19 C33 C36 -64.1(10) . . . . ? C44 C39 C40 C41 -53.2(13) . . . . ? C39 C40 C41 C42 55.4(14) . . . . ? C40 C41 C42 C43 -57.4(14) . . . . ? C41 C42 C43 C44 57.1(13) . . . . ? C40 C39 C44 C43 53.4(14) . . . . ? C42 C43 C44 C39 -55.7(14) . . . . ? C50 C45 C46 C47 -53.9(11) . . . . ? C45 C46 C47 C48 52.5(11) . . . . ? C46 C47 C48 C49 -55.1(11) . . . . ? C47 C48 C49 C50 57.3(11) . . . . ? C46 C45 C50 C49 56.9(11) . . . . ? C48 C49 C50 C45 -58.4(11) . . . . ? C2 C7 N1 C8 178.2(7) . . . . ? C2 C7 N1 In1 -12.0(11) . . . . ? C9 C8 N1 C7 25.6(10) . . . . ? C13 C8 N1 C7 151.4(7) . . . . ? C9 C8 N1 In1 -144.9(6) . . . . ? C13 C8 N1 In1 -19.1(7) . . . . ? C15 C14 N2 C13 -168.0(7) . . . . ? C15 C14 N2 In1 4.3(11) . . . . ? C12 C13 N2 C14 -6.7(11) . . . . ? C8 C13 N2 C14 116.6(8) . . . . ? C12 C13 N2 In1 180.0(5) . . . . ? C8 C13 N2 In1 -56.8(6) . . . . ? C2 C1 O1 In1 15.2(10) . . . . ? C6 C1 O1 In1 -164.8(5) . . . . ? C15 C20 O2 In1 -33.2(10) . . . . ? C19 C20 O2 In1 150.3(6) . . . . ? C38 C37 O3 In1 -82.5(7) . . . . ? C38 C37 O3 In1 87.2(7) . . . 2_655 ? C1 O1 In1 O3 138.4(6) . . . . ? C1 O1 In1 O2 -128.8(6) . . . . ? C1 O1 In1 O3 62.7(6) . . . 2_655 ? C1 O1 In1 N2 -61.1(8) . . . . ? C1 O1 In1 N1 -22.5(6) . . . . ? C37 O3 In1 O1 62.6(5) . . . . ? In1 O3 In1 O1 -109.0(2) 2_655 . . . ? C37 O3 In1 O2 -27.0(5) . . . . ? In1 O3 In1 O2 161.4(2) 2_655 . . . ? C37 O3 In1 O3 160.1(4) . . . 2_655 ? In1 O3 In1 O3 -11.5(3) 2_655 . . 2_655 ? C37 O3 In1 N2 -108.2(5) . . . . ? In1 O3 In1 N2 80.2(2) 2_655 . . . ? C37 O3 In1 N1 -171.7(5) . . . . ? In1 O3 In1 N1 16.8(6) 2_655 . . . ? C20 O2 In1 O1 -165.1(6) . . . . ? C20 O2 In1 O3 -55.3(6) . . . . ? C20 O2 In1 O3 -29.8(10) . . . 2_655 ? C20 O2 In1 N2 41.4(6) . . . . ? C20 O2 In1 N1 110.7(6) . . . . ? C14 N2 In1 O1 -96.6(8) . . . . ? C13 N2 In1 O1 76.3(7) . . . . ? C14 N2 In1 O3 64.9(7) . . . . ? C13 N2 In1 O3 -122.1(5) . . . . ? C14 N2 In1 O2 -27.1(7) . . . . ? C13 N2 In1 O2 145.9(5) . . . . ? C14 N2 In1 O3 137.7(7) . . . 2_655 ? C13 N2 In1 O3 -49.3(5) . . . 2_655 ? C14 N2 In1 N1 -137.1(7) . . . . ? C13 N2 In1 N1 35.9(5) . . . . ? C7 N1 In1 O1 19.8(6) . . . . ? C8 N1 In1 O1 -169.9(5) . . . . ? C7 N1 In1 O3 -110.1(6) . . . . ? C8 N1 In1 O3 60.2(7) . . . . ? C7 N1 In1 O2 106.9(6) . . . . ? C8 N1 In1 O2 -82.8(5) . . . . ? C7 N1 In1 O3 -83.2(6) . . . 2_655 ? C8 N1 In1 O3 87.1(5) . . . 2_655 ? C7 N1 In1 N2 -178.2(6) . . . . ? C8 N1 In1 N2 -7.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 22.64 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.536 _refine_diff_density_min -1.518 _refine_diff_density_rms 0.227 #===END