# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email mehr@chem.ubc.ca _publ_contact_author_name 'Parisa Mehrkhodavandi' loop_ _publ_author_name 'Parisa Mehrkhodavandi' 'Kimberley Osten' 'Insun Yu' 'Paraskevi Lagaditis' 'Ian Duffy' 'Joey Yu' 'Christopher Wallis' data_pm070 _database_code_depnum_ccdc_archive 'CCDC 864181' #TrackingRef '- Mehr_DaltonJan192012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H35 Cl2 In N2 O' _chemical_formula_sum 'C20 H35 Cl2 In N2 O' _chemical_formula_weight 505.22 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/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5289(15) _cell_length_b 15.574(3) _cell_length_c 17.297(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.964(5) _cell_angle_gamma 90.00 _cell_volume 2269.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9935 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 25.36 _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 1.288 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.696 _exptl_absorpt_correction_T_max 0.938 _exptl_absorpt_process_details ? _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 '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 4168 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.42 _reflns_number_total 4168 _reflns_number_gt 3099 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0690P)^2^+0.1391P] 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 4168 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 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 C5 C 0.8323(5) 0.3597(3) 0.4650(2) 0.0208(9) Uani 1 1 d . . . C7 C 0.8304(5) 0.2111(3) 0.5077(2) 0.0234(9) Uani 1 1 d . . . C6 C 0.7663(5) 0.2928(3) 0.5026(2) 0.0226(9) Uani 1 1 d . . . H6 H 0.6741 0.3037 0.5256 0.027 Uiso 1 1 calc R . . C010 C 1.1842(5) 0.2433(3) 0.3955(2) 0.0233(9) Uani 1 1 d . . . C17 C 1.1648(5) 0.2735(3) 0.3096(2) 0.0283(10) Uani 1 1 d . . . H17A H 1.2616 0.2603 0.2879 0.042 Uiso 1 1 calc R . . H17B H 1.1461 0.3356 0.3072 0.042 Uiso 1 1 calc R . . H17C H 1.0744 0.2439 0.2790 0.042 Uiso 1 1 calc R . . C8 C 0.9628(5) 0.1978(3) 0.4703(2) 0.0232(9) Uani 1 1 d . . . H8 H 1.0062 0.1416 0.4712 0.028 Uiso 1 1 calc R . . C3 C 0.7623(5) 0.4486(3) 0.4634(2) 0.0235(9) Uani 1 1 d . . . H3A H 0.6701 0.4480 0.4918 0.028 Uiso 1 1 calc R . . H3B H 0.8424 0.4884 0.4913 0.028 Uiso 1 1 calc R . . C16 C 1.2215(6) 0.1473(3) 0.3961(3) 0.0320(11) Uani 1 1 d . . . H16A H 1.3172 0.1376 0.3725 0.048 Uiso 1 1 calc R . . H16B H 1.1320 0.1164 0.3661 0.048 Uiso 1 1 calc R . . H16C H 1.2391 0.1263 0.4502 0.048 Uiso 1 1 calc R . . C10 C 0.8110(6) 0.6535(3) 0.2141(2) 0.0331(11) Uani 1 1 d . . . H10A H 0.9202 0.6594 0.2038 0.050 Uiso 1 1 calc R . . H10B H 0.7557 0.7085 0.2046 0.050 Uiso 1 1 calc R . . H10C H 0.7558 0.6097 0.1794 0.050 Uiso 1 1 calc R . . C12 C 0.5857(5) 0.4240(3) 0.3387(2) 0.0261(10) Uani 1 1 d . . . H12A H 0.6293 0.3662 0.3352 0.039 Uiso 1 1 calc R . . H12B H 0.5518 0.4467 0.2859 0.039 Uiso 1 1 calc R . . H12C H 0.4943 0.4215 0.3667 0.039 Uiso 1 1 calc R . . C017 C 0.7644(5) 0.1366(3) 0.5504(2) 0.0255(10) Uani 1 1 d . . . C2 C 0.6434(6) 0.5692(3) 0.3867(2) 0.0282(10) Uani 1 1 d . . . H2A H 0.7053 0.6004 0.4312 0.034 Uiso 1 1 calc R . . H2B H 0.5323 0.5650 0.3965 0.034 Uiso 1 1 calc R . . C18 C 1.3262(5) 0.2898(3) 0.4431(2) 0.0274(10) Uani 1 1 d . . . H18A H 1.4222 0.2778 0.4204 0.041 Uiso 1 1 calc R . . H18B H 1.3408 0.2695 0.4974 0.041 Uiso 1 1 calc R . . H18C H 1.3062 0.3518 0.4420 0.041 Uiso 1 1 calc R . . C9 C 1.0352(5) 0.2621(2) 0.4317(2) 0.0195(9) Uani 1 1 d . . . C15 C 0.8968(5) 0.0941(3) 0.6080(3) 0.0323(11) Uani 1 1 d . . . H15A H 0.8523 0.0467 0.6350 0.048 Uiso 1 1 calc R . . H15B H 0.9440 0.1365 0.6466 0.048 Uiso 1 1 calc R . . H15C H 0.9786 0.0718 0.5794 0.048 Uiso 1 1 calc R . . C4 C 0.9696(5) 0.3457(3) 0.4311(2) 0.0198(9) Uani 1 1 d . . . C1 C 0.6478(5) 0.6190(3) 0.3117(2) 0.0269(10) Uani 1 1 d . . . H1A H 0.5832 0.5888 0.2674 0.032 Uiso 1 1 calc R . . H1B H 0.6013 0.6767 0.3162 0.032 Uiso 1 1 calc R . . C14 C 0.6366(6) 0.1664(3) 0.5975(3) 0.0445(14) Uani 1 1 d . . . H14A H 0.5975 0.1170 0.6239 0.067 Uiso 1 1 calc R . . H14B H 0.5486 0.1924 0.5621 0.067 Uiso 1 1 calc R . . H14C H 0.6820 0.2088 0.6365 0.067 Uiso 1 1 calc R . . C11 C 0.9002(6) 0.6951(3) 0.3479(3) 0.0344(11) Uani 1 1 d . . . H11A H 1.0093 0.6994 0.3371 0.052 Uiso 1 1 calc R . . H11B H 0.9017 0.6793 0.4029 0.052 Uiso 1 1 calc R . . H11C H 0.8467 0.7505 0.3375 0.052 Uiso 1 1 calc R . . C13 C 0.6924(6) 0.0687(3) 0.4906(3) 0.0383(12) Uani 1 1 d . . . H13A H 0.6499 0.0211 0.5180 0.057 Uiso 1 1 calc R . . H13B H 0.7747 0.0471 0.4619 0.057 Uiso 1 1 calc R . . H13C H 0.6066 0.0947 0.4537 0.057 Uiso 1 1 calc R . . N2 N 0.7101(4) 0.4814(2) 0.38198(19) 0.0220(8) Uani 1 1 d . . . N1 N 0.8129(4) 0.6277(2) 0.29626(19) 0.0233(8) Uani 1 1 d . . . O1 O 1.0415(3) 0.41279(17) 0.40154(15) 0.0205(6) Uani 1 1 d . . . Cl1 Cl 0.82316(14) 0.42257(7) 0.20012(6) 0.0310(3) Uani 1 1 d . . . Cl2 Cl 1.18379(14) 0.55608(7) 0.30234(7) 0.0348(3) Uani 1 1 d . . . In1 In 0.93078(3) 0.494847(17) 0.317192(15) 0.02019(12) 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 C5 0.022(2) 0.022(2) 0.017(2) 0.0013(16) -0.0021(17) -0.0007(17) C7 0.023(2) 0.026(2) 0.020(2) 0.0051(17) 0.0016(18) -0.0047(19) C6 0.018(2) 0.027(2) 0.022(2) 0.0020(17) 0.0030(17) -0.0045(18) C010 0.023(2) 0.023(2) 0.025(2) -0.0005(17) 0.0064(19) -0.0014(18) C17 0.032(3) 0.032(2) 0.023(2) 0.0018(19) 0.0108(19) -0.002(2) C8 0.022(2) 0.022(2) 0.024(2) 0.0024(18) -0.0014(17) 0.0011(18) C3 0.028(2) 0.025(2) 0.018(2) 0.0035(17) 0.0066(18) 0.0004(19) C16 0.032(3) 0.027(2) 0.039(3) -0.001(2) 0.011(2) 0.003(2) C10 0.042(3) 0.033(3) 0.025(2) 0.011(2) 0.008(2) 0.005(2) C12 0.023(2) 0.029(2) 0.024(2) 0.0028(18) 0.0000(19) -0.0010(19) C017 0.022(2) 0.030(2) 0.024(2) 0.0087(18) 0.0010(19) -0.0032(19) C2 0.035(3) 0.022(2) 0.028(2) 0.0065(18) 0.008(2) 0.008(2) C18 0.021(2) 0.033(2) 0.027(2) 0.0001(19) 0.0033(19) -0.0014(19) C9 0.019(2) 0.019(2) 0.021(2) 0.0004(16) 0.0043(17) -0.0041(17) C15 0.033(3) 0.028(2) 0.032(2) 0.012(2) -0.007(2) -0.004(2) C4 0.021(2) 0.022(2) 0.0158(19) 0.0004(16) -0.0008(17) -0.0025(17) C1 0.031(3) 0.024(2) 0.025(2) 0.0049(18) 0.0033(19) 0.007(2) C14 0.042(3) 0.048(3) 0.050(3) 0.025(3) 0.028(3) 0.005(3) C11 0.040(3) 0.024(2) 0.037(3) -0.002(2) -0.002(2) -0.005(2) C13 0.039(3) 0.036(3) 0.037(3) 0.015(2) -0.003(2) -0.016(2) N2 0.026(2) 0.0184(17) 0.0213(18) -0.0027(14) 0.0016(15) 0.0001(15) N1 0.026(2) 0.0208(18) 0.0217(18) 0.0025(14) -0.0004(15) 0.0001(15) O1 0.0223(16) 0.0188(14) 0.0205(14) 0.0052(11) 0.0035(12) 0.0003(12) Cl1 0.0321(6) 0.0371(6) 0.0236(5) -0.0070(5) 0.0037(5) 0.0012(5) Cl2 0.0252(6) 0.0343(6) 0.0458(7) 0.0146(5) 0.0085(5) -0.0022(5) In1 0.02111(19) 0.02006(17) 0.01943(17) 0.00210(12) 0.00324(12) -0.00038(13) _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 C5 C6 1.393(6) . ? C5 C4 1.406(6) . ? C5 C3 1.506(6) . ? C7 C6 1.382(6) . ? C7 C8 1.401(6) . ? C7 C017 1.529(6) . ? C6 H6 0.9500 . ? C010 C16 1.528(6) . ? C010 C9 1.530(6) . ? C010 C18 1.536(6) . ? C010 C17 1.544(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C8 C9 1.399(6) . ? C8 H8 0.9500 . ? C3 N2 1.499(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C10 N1 1.474(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 N2 1.495(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C017 C14 1.531(6) . ? C017 C13 1.539(6) . ? C017 C15 1.535(6) . ? C2 N2 1.488(5) . ? C2 C1 1.516(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C9 C4 1.416(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C4 O1 1.352(5) . ? C1 N1 1.480(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C11 N1 1.499(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N2 In1 2.345(4) . ? N1 In1 2.305(3) . ? O1 In1 2.055(3) . ? Cl1 In1 2.3729(11) . ? Cl2 In1 2.4093(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C5 C4 120.1(4) . . ? C6 C5 C3 120.6(4) . . ? C4 C5 C3 119.3(4) . . ? C6 C7 C8 116.5(4) . . ? C6 C7 C017 123.9(4) . . ? C8 C7 C017 119.7(4) . . ? C7 C6 C5 122.2(4) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C16 C010 C9 111.7(4) . . ? C16 C010 C18 108.2(4) . . ? C9 C010 C18 109.0(3) . . ? C16 C010 C17 107.2(3) . . ? C9 C010 C17 111.4(3) . . ? C18 C010 C17 109.2(3) . . ? C010 C17 H17A 109.5 . . ? C010 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C010 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C7 C8 C9 124.2(4) . . ? C7 C8 H8 117.9 . . ? C9 C8 H8 117.9 . . ? N2 C3 C5 112.9(3) . . ? N2 C3 H3A 109.0 . . ? C5 C3 H3A 109.0 . . ? N2 C3 H3B 109.0 . . ? C5 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C010 C16 H16A 109.5 . . ? C010 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C010 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C017 C7 111.9(4) . . ? C14 C017 C13 108.8(4) . . ? C7 C017 C13 109.5(3) . . ? C14 C017 C15 107.3(4) . . ? C7 C017 C15 110.6(4) . . ? C13 C017 C15 108.4(4) . . ? N2 C2 C1 111.2(3) . . ? N2 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? N2 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C010 C18 H18A 109.5 . . ? C010 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C010 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 C9 C4 117.3(4) . . ? C8 C9 C010 120.9(4) . . ? C4 C9 C010 121.7(3) . . ? C017 C15 H15A 109.5 . . ? C017 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C017 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O1 C4 C5 119.6(4) . . ? O1 C4 C9 120.7(4) . . ? C5 C4 C9 119.6(4) . . ? N1 C1 C2 110.7(3) . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C017 C14 H14A 109.5 . . ? C017 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C017 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C017 C13 H13A 109.5 . . ? C017 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C017 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 N2 C2 109.2(3) . . ? C12 N2 C3 110.5(3) . . ? C2 N2 C3 108.8(3) . . ? C12 N2 In1 112.0(2) . . ? C2 N2 In1 106.6(3) . . ? C3 N2 In1 109.6(2) . . ? C10 N1 C1 109.4(3) . . ? C10 N1 C11 108.3(4) . . ? C1 N1 C11 110.8(4) . . ? C10 N1 In1 109.6(3) . . ? C1 N1 In1 107.1(2) . . ? C11 N1 In1 111.8(3) . . ? C4 O1 In1 124.3(2) . . ? O1 In1 N1 144.18(11) . . ? O1 In1 N2 85.38(11) . . ? N1 In1 N2 78.00(12) . . ? O1 In1 Cl1 112.62(8) . . ? N1 In1 Cl1 100.99(9) . . ? N2 In1 Cl1 97.63(9) . . ? O1 In1 Cl2 90.10(8) . . ? N1 In1 Cl2 90.23(9) . . ? N2 In1 Cl2 152.27(9) . . ? Cl1 In1 Cl2 109.31(4) . . ? 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 C8 C7 C6 C5 -2.3(6) . . . . ? C017 C7 C6 C5 178.2(4) . . . . ? C4 C5 C6 C7 -0.6(6) . . . . ? C3 C5 C6 C7 -177.7(4) . . . . ? C6 C7 C8 C9 2.5(6) . . . . ? C017 C7 C8 C9 -178.0(4) . . . . ? C6 C5 C3 N2 -121.4(4) . . . . ? C4 C5 C3 N2 61.5(5) . . . . ? C6 C7 C017 C14 -9.0(6) . . . . ? C8 C7 C017 C14 171.5(4) . . . . ? C6 C7 C017 C13 111.8(5) . . . . ? C8 C7 C017 C13 -67.7(5) . . . . ? C6 C7 C017 C15 -128.7(4) . . . . ? C8 C7 C017 C15 51.8(5) . . . . ? C7 C8 C9 C4 0.2(6) . . . . ? C7 C8 C9 C010 177.2(4) . . . . ? C16 C010 C9 C8 9.0(5) . . . . ? C18 C010 C9 C8 -110.5(4) . . . . ? C17 C010 C9 C8 128.9(4) . . . . ? C16 C010 C9 C4 -174.2(4) . . . . ? C18 C010 C9 C4 66.3(5) . . . . ? C17 C010 C9 C4 -54.3(5) . . . . ? C6 C5 C4 O1 -173.5(4) . . . . ? C3 C5 C4 O1 3.6(5) . . . . ? C6 C5 C4 C9 3.5(6) . . . . ? C3 C5 C4 C9 -179.4(4) . . . . ? C8 C9 C4 O1 173.7(3) . . . . ? C010 C9 C4 O1 -3.1(6) . . . . ? C8 C9 C4 C5 -3.2(6) . . . . ? C010 C9 C4 C5 179.9(3) . . . . ? N2 C2 C1 N1 -60.0(5) . . . . ? C1 C2 N2 C12 -81.4(4) . . . . ? C1 C2 N2 C3 157.9(4) . . . . ? C1 C2 N2 In1 39.7(4) . . . . ? C5 C3 N2 C12 60.3(4) . . . . ? C5 C3 N2 C2 -179.9(4) . . . . ? C5 C3 N2 In1 -63.6(4) . . . . ? C2 C1 N1 C10 164.0(4) . . . . ? C2 C1 N1 C11 -76.7(4) . . . . ? C2 C1 N1 In1 45.4(4) . . . . ? C5 C4 O1 In1 -56.2(4) . . . . ? C9 C4 O1 In1 126.9(3) . . . . ? C4 O1 In1 N1 100.0(3) . . . . ? C4 O1 In1 N2 37.9(3) . . . . ? C4 O1 In1 Cl1 -58.5(3) . . . . ? C4 O1 In1 Cl2 -169.5(3) . . . . ? C10 N1 In1 O1 159.6(3) . . . . ? C1 N1 In1 O1 -81.9(3) . . . . ? C11 N1 In1 O1 39.5(4) . . . . ? C10 N1 In1 N2 -136.2(3) . . . . ? C1 N1 In1 N2 -17.7(2) . . . . ? C11 N1 In1 N2 103.8(3) . . . . ? C10 N1 In1 Cl1 -40.7(3) . . . . ? C1 N1 In1 Cl1 77.8(2) . . . . ? C11 N1 In1 Cl1 -160.7(3) . . . . ? C10 N1 In1 Cl2 69.1(3) . . . . ? C1 N1 In1 Cl2 -172.4(2) . . . . ? C11 N1 In1 Cl2 -50.9(3) . . . . ? C12 N2 In1 O1 -104.1(3) . . . . ? C2 N2 In1 O1 136.5(3) . . . . ? C3 N2 In1 O1 18.9(2) . . . . ? C12 N2 In1 N1 107.8(3) . . . . ? C2 N2 In1 N1 -11.6(2) . . . . ? C3 N2 In1 N1 -129.2(3) . . . . ? C12 N2 In1 Cl1 8.1(3) . . . . ? C2 N2 In1 Cl1 -111.3(2) . . . . ? C3 N2 In1 Cl1 131.2(2) . . . . ? C12 N2 In1 Cl2 174.51(19) . . . . ? C2 N2 In1 Cl2 55.1(3) . . . . ? C3 N2 In1 Cl2 -62.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.063 _refine_diff_density_min -1.043 _refine_diff_density_rms 0.149 #===END data_pm068_0m _database_code_depnum_ccdc_archive 'CCDC 864182' #TrackingRef '- Mehr_DaltonJan192012.cif' _audit_creation_method shelxl-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'c27 h47 cl2 in n2 o' _chemical_formula_sum 'c27 h47 cl2 in n2 o' _chemical_formula_weight 601.39 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 triclinic _symmetry_space_group_name_h-m 'p -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6106(10) _cell_length_b 18.028(2) _cell_length_c 20.770(2) _cell_angle_alpha 112.588(5) _cell_angle_beta 99.361(6) _cell_angle_gamma 90.583(6) _cell_volume 2927.9(6) _cell_formula_units_z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9731 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.52 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_f_000 1256 _exptl_absorpt_coefficient_mu 1.011 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_t_min 0.7448 _exptl_absorpt_correction_t_max 0.8593 _exptl_absorpt_process_details ? _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 '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 59526 _diffrn_reflns_av_r_equivalents 0.0273 _diffrn_reflns_av_sigmai/neti 0.0225 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 27.55 _reflns_number_total 13413 _reflns_number_gt 12039 _reflns_threshold_expression >2sigma(i) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'shelxl-97 (sheldrick, 1997)' _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^ > 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^)+(0.0327p)^2^+2.6420p] where p=(fo^2^+2fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13413 _refine_ls_number_parameters 603 _refine_ls_number_restraints 0 _refine_ls_r_factor_all 0.0318 _refine_ls_r_factor_gt 0.0267 _refine_ls_wr_factor_ref 0.0742 _refine_ls_wr_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_s_all 1.146 _refine_ls_shift/su_max 0.003 _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 0.4931(2) 0.81876(12) 0.33516(11) 0.0152(4) uani 1 1 d . . . h1 h 0.4494 0.7926 0.2833 0.018 uiso 1 1 calc r . . c1a c 0.7304(3) 0.68574(13) 0.65826(11) 0.0169(4) uani 1 1 d . . . h1a h 0.7190 0.7202 0.7079 0.020 uiso 1 1 calc r . . c2 c 0.6611(2) 0.85583(13) 0.34494(11) 0.0161(4) uani 1 1 d . . . h2 h 0.7018 0.8799 0.3972 0.019 uiso 1 1 calc r . . c2a c 0.8956(3) 0.65472(13) 0.65938(12) 0.0179(4) uani 1 1 d . . . h2a h 0.9056 0.6256 0.6086 0.021 uiso 1 1 calc r . . c3 c 0.7707(3) 0.79057(14) 0.31305(13) 0.0230(5) uani 1 1 d . . . h3a h 0.8792 0.8156 0.3222 0.028 uiso 1 1 calc r . . h3b h 0.7350 0.7644 0.2611 0.028 uiso 1 1 calc r . . c3a c 1.0224(3) 0.72519(15) 0.69016(14) 0.0245(5) uani 1 1 d . . . h3a1 h 1.0143 0.7580 0.7400 0.029 uiso 1 1 calc r . . h3a2 h 1.1282 0.7042 0.6897 0.029 uiso 1 1 calc r . . c4 c 0.7717(3) 0.72690(14) 0.34515(14) 0.0244(5) uani 1 1 d . . . h4a h 0.8400 0.6842 0.3225 0.029 uiso 1 1 calc r . . h4b h 0.8157 0.7521 0.3965 0.029 uiso 1 1 calc r . . c4a c 1.0034(3) 0.77794(16) 0.64722(15) 0.0294(5) uani 1 1 d . . . h4a1 h 1.0831 0.8247 0.6694 0.035 uiso 1 1 calc r . . h4a2 h 1.0220 0.7465 0.5986 0.035 uiso 1 1 calc r . . c5 c 0.6042(3) 0.68955(14) 0.33415(14) 0.0247(5) uani 1 1 d . . . h5a h 0.5631 0.6609 0.2828 0.030 uiso 1 1 calc r . . h5b h 0.6062 0.6498 0.3565 0.030 uiso 1 1 calc r . . c5a c 0.8388(3) 0.80779(15) 0.64350(15) 0.0283(5) uani 1 1 d . . . h5a1 h 0.8270 0.8387 0.6128 0.034 uiso 1 1 calc r . . h5a2 h 0.8246 0.8442 0.6915 0.034 uiso 1 1 calc r . . c6 c 0.4959(3) 0.75451(13) 0.36657(12) 0.0190(4) uani 1 1 d . . . h6a h 0.5327 0.7803 0.4185 0.023 uiso 1 1 calc r . . h6b h 0.3876 0.7295 0.3578 0.023 uiso 1 1 calc r . . c6a c 0.7123(3) 0.73712(13) 0.61381(13) 0.0206(4) uani 1 1 d . . . h6a1 h 0.7210 0.7032 0.5643 0.025 uiso 1 1 calc r . . h6a2 h 0.6064 0.7580 0.6135 0.025 uiso 1 1 calc r . . c7 c 0.2203(2) 0.86128(13) 0.34785(11) 0.0149(4) uani 1 1 d . . . h7a h 0.1634 0.9066 0.3758 0.018 uiso 1 1 calc r . . h7b h 0.1969 0.8146 0.3596 0.018 uiso 1 1 calc r . . c7a c 0.4514(2) 0.63860(13) 0.64919(11) 0.0158(4) uani 1 1 d . . . h7a1 h 0.3719 0.5927 0.6212 0.019 uiso 1 1 calc r . . h7a2 h 0.4198 0.6848 0.6368 0.019 uiso 1 1 calc r . . c8 c 0.1577(2) 0.90051(12) 0.24302(11) 0.0142(4) uani 1 1 d . . . c8a c 0.4682(2) 0.60025(13) 0.75440(11) 0.0152(4) uani 1 1 d . . . c9 c 0.0873(2) 0.88208(13) 0.17131(11) 0.0152(4) uani 1 1 d . . . c9a c 0.4501(2) 0.61888(13) 0.82578(11) 0.0161(4) uani 1 1 d . . . c10 c 0.0363(3) 0.80173(13) 0.12951(11) 0.0166(4) uani 1 1 d . . . h10 h -0.0103 0.7884 0.0813 0.020 uiso 1 1 calc r . . c10a c 0.4326(2) 0.69908(13) 0.86685(11) 0.0163(4) uani 1 1 d . . . h10a h 0.4231 0.7125 0.9149 0.020 uiso 1 1 calc r . . c11 c 0.0495(2) 0.73923(13) 0.15404(11) 0.0159(4) uani 1 1 d . . . c11a c 0.4279(2) 0.76154(13) 0.84201(11) 0.0155(4) uani 1 1 d . . . c12 c 0.1092(2) 0.76024(12) 0.22553(11) 0.0143(4) uani 1 1 d . . . h12 h 0.1148 0.7198 0.2445 0.017 uiso 1 1 calc r . . c12a c 0.4343(2) 0.74025(13) 0.77072(11) 0.0155(4) uani 1 1 d . . . h12a h 0.4264 0.7804 0.7515 0.019 uiso 1 1 calc r . . c13 c 0.1610(2) 0.83974(13) 0.26984(11) 0.0145(4) uani 1 1 d . . . c13a c 0.4523(2) 0.66083(13) 0.72701(11) 0.0147(4) uani 1 1 d . . . c14 c 0.0669(3) 0.94823(13) 0.14153(11) 0.0174(4) uani 1 1 d . . . c14a c 0.4471(3) 0.55321(13) 0.85584(11) 0.0182(4) uani 1 1 d . . . c15 c 0.2282(3) 0.98577(15) 0.14211(13) 0.0232(5) uani 1 1 d . . . h15a h 0.2886 0.9438 0.1134 0.035 uiso 1 1 calc r . . h15b h 0.2863 1.0104 0.1909 0.035 uiso 1 1 calc r . . h15c h 0.2128 1.0271 0.1224 0.035 uiso 1 1 calc r . . c15a c 0.6050(3) 0.51434(15) 0.85623(13) 0.0240(5) uani 1 1 d . . . h15d h 0.6000 0.4728 0.8756 0.036 uiso 1 1 calc r . . h15e h 0.6902 0.5557 0.8857 0.036 uiso 1 1 calc r . . h15f h 0.6254 0.4898 0.8077 0.036 uiso 1 1 calc r . . c16 c -0.0283(3) 1.01382(14) 0.18639(13) 0.0231(5) uani 1 1 d . . . h16a h 0.0259 1.0359 0.2359 0.035 uiso 1 1 calc r . . h16b h -0.1339 0.9904 0.1832 0.035 uiso 1 1 calc r . . h16c h -0.0377 1.0570 0.1686 0.035 uiso 1 1 calc r . . c16a c 0.3131(3) 0.48847(14) 0.81008(13) 0.0217(5) uani 1 1 d . . . h16d h 0.3103 0.4463 0.8289 0.033 uiso 1 1 calc r . . h16e h 0.3314 0.4647 0.7611 0.033 uiso 1 1 calc r . . h16f h 0.2121 0.5131 0.8111 0.033 uiso 1 1 calc r . . c17 c -0.0226(3) 0.91550(15) 0.06467(13) 0.0261(5) uani 1 1 d . . . h17a h 0.0352 0.8733 0.0346 0.039 uiso 1 1 calc r . . h17b h -0.0318 0.9594 0.0478 0.039 uiso 1 1 calc r . . h17c h -0.1283 0.8930 0.0625 0.039 uiso 1 1 calc r . . c17a c 0.4161(3) 0.58647(15) 0.93219(12) 0.0261(5) uani 1 1 d . . . h17d h 0.4153 0.5427 0.9491 0.039 uiso 1 1 calc r . . h17e h 0.3137 0.6097 0.9334 0.039 uiso 1 1 calc r . . h17f h 0.4996 0.6283 0.9628 0.039 uiso 1 1 calc r . . c18 c 0.0022(3) 0.65207(13) 0.10179(11) 0.0192(4) uani 1 1 d . . . c18a c 0.4211(3) 0.84868(13) 0.89355(11) 0.0178(4) uani 1 1 d . . . c19 c -0.1705(3) 0.64324(15) 0.06490(14) 0.0288(5) uani 1 1 d . . . h19a h -0.1989 0.5873 0.0316 0.043 uiso 1 1 calc r . . h19b h -0.1838 0.6788 0.0390 0.043 uiso 1 1 calc r . . h19c h -0.2391 0.6580 0.1005 0.043 uiso 1 1 calc r . . c19a c 0.4064(3) 0.90644(13) 0.85531(12) 0.0214(5) uani 1 1 d . . . h19d h 0.4024 0.9615 0.8897 0.032 uiso 1 1 calc r . . h19e h 0.3095 0.8908 0.8195 0.032 uiso 1 1 calc r . . h19f h 0.4978 0.9041 0.8322 0.032 uiso 1 1 calc r . . c20 c 0.1104(3) 0.62975(15) 0.04616(13) 0.0281(5) uani 1 1 d . . . h20a h 0.0816 0.5741 0.0122 0.042 uiso 1 1 calc r . . h20b h 0.2205 0.6348 0.0698 0.042 uiso 1 1 calc r . . h20c h 0.0979 0.6661 0.0210 0.042 uiso 1 1 calc r . . c20a c 0.5742(3) 0.87372(14) 0.94877(12) 0.0252(5) uani 1 1 d . . . h20d h 0.5850 0.8372 0.9738 0.038 uiso 1 1 calc r . . h20e h 0.5708 0.9290 0.9828 0.038 uiso 1 1 calc r . . h20f h 0.6646 0.8709 0.9249 0.038 uiso 1 1 calc r . . c21 c 0.0216(3) 0.59295(14) 0.13890(12) 0.0236(5) uani 1 1 d . . . h21a h -0.0095 0.5380 0.1039 0.035 uiso 1 1 calc r . . h21b h -0.0455 0.6066 0.1751 0.035 uiso 1 1 calc r . . h21c h 0.1322 0.5966 0.1614 0.035 uiso 1 1 calc r . . c21a c 0.2791(3) 0.85525(15) 0.93116(13) 0.0264(5) uani 1 1 d . . . h21d h 0.2871 0.8186 0.9561 0.040 uiso 1 1 calc r . . h21e h 0.1812 0.8406 0.8960 0.040 uiso 1 1 calc r . . h21f h 0.2785 0.9107 0.9654 0.040 uiso 1 1 calc r . . c22 c 0.8083(3) 0.98174(14) 0.35856(12) 0.0197(4) uani 1 1 d . . . h22a h 0.8113 1.0228 0.3379 0.024 uiso 1 1 calc r . . h22b h 0.9026 0.9511 0.3495 0.024 uiso 1 1 calc r . . c22a c 1.0499(2) 0.54046(15) 0.66568(12) 0.0207(5) uani 1 1 d . . . h22c h 1.1510 0.5744 0.6837 0.025 uiso 1 1 calc r . . h22d h 1.0571 0.4991 0.6862 0.025 uiso 1 1 calc r . . c23 c 0.8200(3) 1.02483(15) 0.43799(12) 0.0225(5) uani 1 1 d . . . h23a h 0.8522 0.9873 0.4613 0.027 uiso 1 1 calc r . . h23b h 0.7154 1.0425 0.4488 0.027 uiso 1 1 calc r . . c23a c 1.0317(3) 0.49882(15) 0.58695(13) 0.0255(5) uani 1 1 d . . . h23c h 1.0618 0.5373 0.5667 0.031 uiso 1 1 calc r . . h23d h 0.9201 0.4785 0.5662 0.031 uiso 1 1 calc r . . c24 c 0.9401(3) 1.09780(16) 0.46697(14) 0.0300(5) uani 1 1 d . . . h24a h 0.9462 1.1250 0.5183 0.045 uiso 1 1 calc r . . h24b h 0.9074 1.1352 0.4443 0.045 uiso 1 1 calc r . . h24c h 1.0440 1.0801 0.4569 0.045 uiso 1 1 calc r . . c24a c 1.1369(4) 0.42878(17) 0.56883(16) 0.0353(6) uani 1 1 d . . . h24d h 1.1249 0.4013 0.5172 0.053 uiso 1 1 calc r . . h24e h 1.1061 0.3907 0.5887 0.053 uiso 1 1 calc r . . h24f h 1.2473 0.4493 0.5890 0.053 uiso 1 1 calc r . . c25 c 0.6679(3) 0.89951(14) 0.24251(11) 0.0207(5) uani 1 1 d . . . h25a h 0.7667 0.8730 0.2332 0.025 uiso 1 1 calc r . . h25b h 0.6740 0.9489 0.2327 0.025 uiso 1 1 calc r . . c25a c 0.9660(3) 0.62688(15) 0.77216(12) 0.0237(5) uani 1 1 d . . . h25c h 0.9804 0.5808 0.7867 0.028 uiso 1 1 calc r . . h25d h 1.0704 0.6572 0.7846 0.028 uiso 1 1 calc r . . c26 c 0.5315(3) 0.84341(15) 0.18989(12) 0.0239(5) uani 1 1 d . . . h26a h 0.4301 0.8661 0.2006 0.029 uiso 1 1 calc r . . h26b h 0.5320 0.7903 0.1937 0.029 uiso 1 1 calc r . . c26a c 0.8578(3) 0.68097(16) 0.81605(12) 0.0262(5) uani 1 1 d . . . h26c h 0.7485 0.6554 0.8002 0.031 uiso 1 1 calc r . . h26d h 0.8582 0.7329 0.8101 0.031 uiso 1 1 calc r . . c27 c 0.5481(3) 0.83318(17) 0.11450(13) 0.0313(6) uani 1 1 d . . . h27a h 0.4604 0.7969 0.0804 0.047 uiso 1 1 calc r . . h27b h 0.6483 0.8103 0.1041 0.047 uiso 1 1 calc r . . h27c h 0.5464 0.8858 0.1109 0.047 uiso 1 1 calc r . . c27a c 0.9145(3) 0.69573(17) 0.89434(12) 0.0315(6) uani 1 1 d . . . h27d h 0.8443 0.7309 0.9232 0.047 uiso 1 1 calc r . . h27e h 1.0222 0.7216 0.9099 0.047 uiso 1 1 calc r . . h27f h 0.9131 0.6442 0.8999 0.047 uiso 1 1 calc r . . n1 n 0.3940(2) 0.88464(11) 0.36834(9) 0.0134(3) uani 1 1 d . . . n1a n 0.6087(2) 0.61613(11) 0.62950(9) 0.0149(3) uani 1 1 d . . . n2 n 0.6634(2) 0.92459(11) 0.32014(9) 0.0161(4) uani 1 1 d . . . n2a n 0.9178(2) 0.59346(11) 0.69258(9) 0.0173(4) uani 1 1 d . . . o1 o 0.22161(17) 0.97584(9) 0.28532(8) 0.0165(3) uani 1 1 d . . . o1a o 0.49923(18) 0.52565(9) 0.71269(8) 0.0171(3) uani 1 1 d . . . cl1 cl 0.54722(6) 1.10106(3) 0.31768(3) 0.02048(11) uani 1 1 d . . . cl1a cl 0.59214(8) 0.42084(4) 0.53615(3) 0.02749(13) uani 1 1 d . . . cl2 cl 0.39639(6) 1.07573(3) 0.46470(3) 0.01894(10) uani 1 1 d . . . cl2a cl 0.81579(7) 0.41427(3) 0.69731(3) 0.02318(11) uani 1 1 d . . . in1 in 0.442316(16) 0.996291(8) 0.347023(7) 0.01261(4) uani 1 1 d . . . in1a in 0.683888(17) 0.510084(9) 0.657608(7) 0.01455(4) uani 1 1 d . . . h1n h 0.423(3) 0.8978(17) 0.4107(16) 0.024(7) uiso 1 1 d . . . h1na h 0.595(3) 0.5979(15) 0.5846(14) 0.014(6) uiso 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 0.0163(10) 0.0146(10) 0.0131(9) 0.0030(8) 0.0036(8) 0.0029(8) c1a 0.0167(10) 0.0154(10) 0.0158(10) 0.0030(8) 0.0034(8) 0.0000(8) c2 0.0168(10) 0.0172(10) 0.0153(10) 0.0070(8) 0.0040(8) 0.0028(8) c2a 0.0170(10) 0.0175(10) 0.0207(11) 0.0088(9) 0.0043(8) 0.0011(8) c3 0.0218(11) 0.0235(12) 0.0265(12) 0.0109(10) 0.0087(9) 0.0084(9) c3a 0.0177(11) 0.0239(12) 0.0320(13) 0.0119(10) 0.0025(9) -0.0018(9) c4 0.0236(12) 0.0194(11) 0.0318(13) 0.0111(10) 0.0066(10) 0.0081(9) c4a 0.0219(12) 0.0262(13) 0.0445(15) 0.0185(12) 0.0067(11) -0.0002(10) c5 0.0269(12) 0.0149(10) 0.0310(13) 0.0079(10) 0.0044(10) 0.0045(9) c5a 0.0255(12) 0.0197(11) 0.0423(15) 0.0146(11) 0.0070(11) 0.0008(10) c6 0.0200(11) 0.0158(10) 0.0199(11) 0.0058(9) 0.0035(8) 0.0006(8) c6a 0.0184(11) 0.0176(11) 0.0270(12) 0.0095(9) 0.0053(9) 0.0026(8) c7 0.0142(10) 0.0178(10) 0.0124(9) 0.0055(8) 0.0028(8) 0.0007(8) c7a 0.0143(10) 0.0205(10) 0.0124(9) 0.0065(8) 0.0021(8) 0.0009(8) c8 0.0115(9) 0.0153(10) 0.0140(9) 0.0040(8) 0.0021(7) 0.0001(7) c8a 0.0127(9) 0.0156(10) 0.0156(10) 0.0046(8) 0.0017(8) 0.0002(8) c9 0.0140(10) 0.0171(10) 0.0156(10) 0.0080(8) 0.0015(8) 0.0004(8) c9a 0.0159(10) 0.0169(10) 0.0160(10) 0.0071(8) 0.0026(8) -0.0002(8) c10 0.0169(10) 0.0188(10) 0.0129(9) 0.0055(8) 0.0009(8) 0.0001(8) c10a 0.0181(10) 0.0190(10) 0.0122(9) 0.0064(8) 0.0034(8) 0.0006(8) c11 0.0158(10) 0.0162(10) 0.0139(10) 0.0041(8) 0.0019(8) -0.0001(8) c11a 0.0152(10) 0.0149(10) 0.0152(10) 0.0043(8) 0.0031(8) 0.0002(8) c12 0.0136(9) 0.0154(10) 0.0143(9) 0.0062(8) 0.0029(8) -0.0003(8) c12a 0.0141(10) 0.0173(10) 0.0160(10) 0.0077(8) 0.0020(8) -0.0006(8) c13 0.0125(9) 0.0180(10) 0.0123(9) 0.0054(8) 0.0019(7) 0.0008(8) c13a 0.0123(9) 0.0187(10) 0.0125(9) 0.0053(8) 0.0022(7) 0.0010(8) c14 0.0176(10) 0.0190(10) 0.0169(10) 0.0098(9) -0.0006(8) -0.0013(8) c14a 0.0215(11) 0.0192(10) 0.0177(10) 0.0101(9) 0.0069(8) 0.0032(8) c15 0.0221(11) 0.0282(12) 0.0236(11) 0.0159(10) 0.0018(9) -0.0024(9) c15a 0.0241(12) 0.0287(12) 0.0247(12) 0.0162(10) 0.0049(9) 0.0049(10) c16 0.0225(11) 0.0225(11) 0.0270(12) 0.0132(10) 0.0028(9) 0.0046(9) c16a 0.0219(11) 0.0196(11) 0.0277(12) 0.0128(10) 0.0070(9) 0.0010(9) c17 0.0318(13) 0.0267(12) 0.0205(11) 0.0144(10) -0.0063(10) -0.0034(10) c17a 0.0401(14) 0.0249(12) 0.0200(11) 0.0130(10) 0.0129(10) 0.0067(10) c18 0.0237(11) 0.0164(10) 0.0147(10) 0.0045(8) -0.0003(8) -0.0012(8) c18a 0.0239(11) 0.0149(10) 0.0146(10) 0.0044(8) 0.0064(8) 0.0019(8) c19 0.0286(13) 0.0236(12) 0.0271(13) 0.0074(10) -0.0078(10) -0.0054(10) c19a 0.0285(12) 0.0165(10) 0.0195(11) 0.0063(9) 0.0067(9) 0.0036(9) c20 0.0415(15) 0.0217(12) 0.0189(11) 0.0037(10) 0.0094(10) 0.0027(10) c20a 0.0329(13) 0.0203(11) 0.0177(11) 0.0043(9) -0.0005(10) -0.0012(10) c21 0.0322(13) 0.0164(11) 0.0201(11) 0.0067(9) 0.0004(9) -0.0010(9) c21a 0.0324(13) 0.0224(12) 0.0269(12) 0.0080(10) 0.0166(10) 0.0064(10) c22 0.0155(10) 0.0251(11) 0.0230(11) 0.0139(10) 0.0049(8) -0.0003(9) c22a 0.0094(9) 0.0381(13) 0.0226(11) 0.0213(10) 0.0008(8) 0.0006(9) c23 0.0174(11) 0.0279(12) 0.0232(11) 0.0125(10) 0.0003(9) -0.0051(9) c23a 0.0251(12) 0.0299(13) 0.0254(12) 0.0131(10) 0.0087(10) 0.0110(10) c24 0.0275(13) 0.0297(13) 0.0319(14) 0.0133(11) 0.0001(10) -0.0083(10) c24a 0.0400(16) 0.0333(14) 0.0378(15) 0.0157(12) 0.0162(12) 0.0183(12) c25 0.0213(11) 0.0279(12) 0.0170(10) 0.0109(9) 0.0097(9) 0.0060(9) c25a 0.0212(11) 0.0303(13) 0.0169(11) 0.0084(10) -0.0012(9) -0.0038(9) c26 0.0271(12) 0.0307(13) 0.0147(10) 0.0082(10) 0.0075(9) 0.0062(10) c26a 0.0240(12) 0.0325(13) 0.0183(11) 0.0069(10) 0.0015(9) -0.0017(10) c27 0.0410(15) 0.0393(15) 0.0168(11) 0.0121(11) 0.0109(10) 0.0126(12) c27a 0.0325(14) 0.0423(15) 0.0149(11) 0.0077(11) 0.0003(10) -0.0073(12) n1 0.0137(8) 0.0155(8) 0.0094(8) 0.0033(7) 0.0019(7) 0.0013(7) n1a 0.0148(9) 0.0179(9) 0.0098(8) 0.0029(7) 0.0024(7) 0.0009(7) n2 0.0163(9) 0.0188(9) 0.0150(8) 0.0080(7) 0.0042(7) 0.0014(7) n2a 0.0174(9) 0.0207(9) 0.0142(9) 0.0076(7) 0.0020(7) 0.0014(7) o1 0.0161(7) 0.0144(7) 0.0166(7) 0.0050(6) -0.0012(6) 0.0004(6) o1a 0.0201(8) 0.0149(7) 0.0155(7) 0.0040(6) 0.0064(6) 0.0009(6) cl1 0.0227(3) 0.0187(2) 0.0242(3) 0.0123(2) 0.0058(2) 0.0010(2) cl1a 0.0353(3) 0.0240(3) 0.0144(2) 0.0005(2) -0.0024(2) 0.0045(2) cl2 0.0238(3) 0.0182(2) 0.0118(2) 0.00260(19) 0.00333(19) 0.0033(2) cl2a 0.0241(3) 0.0202(3) 0.0278(3) 0.0130(2) 0.0026(2) 0.0033(2) in1 0.01359(7) 0.01279(7) 0.01085(7) 0.00409(5) 0.00192(5) 0.00058(5) in1a 0.01593(8) 0.01439(8) 0.01205(7) 0.00396(6) 0.00203(5) 0.00143(5) _geom_special_details ; all esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. the cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. an approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag c1 n1 1.482(3) . ? c1 c6 1.531(3) . ? c1 c2 1.536(3) . ? c1 h1 1.0000 . ? c1a n1a 1.491(3) . ? c1a c6a 1.532(3) . ? c1a c2a 1.534(3) . ? c1a h1a 1.0000 . ? c2 n2 1.515(3) . ? c2 c3 1.530(3) . ? c2 h2 1.0000 . ? c2a n2a 1.509(3) . ? c2a c3a 1.528(3) . ? c2a h2a 1.0000 . ? c3 c4 1.533(3) . ? c3 h3a 0.9900 . ? c3 h3b 0.9900 . ? c3a c4a 1.528(3) . ? c3a h3a1 0.9900 . ? c3a h3a2 0.9900 . ? c4 c5 1.530(3) . ? c4 h4a 0.9900 . ? c4 h4b 0.9900 . ? c4a c5a 1.522(3) . ? c4a h4a1 0.9900 . ? c4a h4a2 0.9900 . ? c5 c6 1.521(3) . ? c5 h5a 0.9900 . ? c5 h5b 0.9900 . ? c5a c6a 1.529(3) . ? c5a h5a1 0.9900 . ? c5a h5a2 0.9900 . ? c6 h6a 0.9900 . ? c6 h6b 0.9900 . ? c6a h6a1 0.9900 . ? c6a h6a2 0.9900 . ? c7 n1 1.496(3) . ? c7 c13 1.510(3) . ? c7 h7a 0.9900 . ? c7 h7b 0.9900 . ? c7a n1a 1.494(3) . ? c7a c13a 1.507(3) . ? c7a h7a1 0.9900 . ? c7a h7a2 0.9900 . ? c8 o1 1.353(2) . ? c8 c13 1.406(3) . ? c8 c9 1.421(3) . ? c8a o1a 1.349(3) . ? c8a c13a 1.411(3) . ? c8a c9a 1.424(3) . ? c9 c10 1.394(3) . ? c9 c14 1.540(3) . ? c9a c10a 1.393(3) . ? c9a c14a 1.538(3) . ? c10 c11 1.403(3) . ? c10 h10 0.9500 . ? c10a c11a 1.406(3) . ? c10a h10a 0.9500 . ? c11 c12 1.388(3) . ? c11 c18 1.532(3) . ? c11a c12a 1.391(3) . ? c11a c18a 1.532(3) . ? c12 c13 1.393(3) . ? c12 h12 0.9500 . ? c12a c13a 1.396(3) . ? c12a h12a 0.9500 . ? c14 c17 1.535(3) . ? c14 c15 1.536(3) . ? c14 c16 1.536(3) . ? c14a c17a 1.535(3) . ? c14a c15a 1.536(3) . ? c14a c16a 1.537(3) . ? c15 h15a 0.9800 . ? c15 h15b 0.9800 . ? c15 h15c 0.9800 . ? c15a h15d 0.9800 . ? c15a h15e 0.9800 . ? c15a h15f 0.9800 . ? c16 h16a 0.9800 . ? c16 h16b 0.9800 . ? c16 h16c 0.9800 . ? c16a h16d 0.9800 . ? c16a h16e 0.9800 . ? c16a h16f 0.9800 . ? c17 h17a 0.9800 . ? c17 h17b 0.9800 . ? c17 h17c 0.9800 . ? c17a h17d 0.9800 . ? c17a h17e 0.9800 . ? c17a h17f 0.9800 . ? c18 c21 1.533(3) . ? c18 c19 1.534(3) . ? c18 c20 1.538(3) . ? c18a c19a 1.529(3) . ? c18a c20a 1.535(3) . ? c18a c21a 1.536(3) . ? c19 h19a 0.9800 . ? c19 h19b 0.9800 . ? c19 h19c 0.9800 . ? c19a h19d 0.9800 . ? c19a h19e 0.9800 . ? c19a h19f 0.9800 . ? c20 h20a 0.9800 . ? c20 h20b 0.9800 . ? c20 h20c 0.9800 . ? c20a h20d 0.9800 . ? c20a h20e 0.9800 . ? c20a h20f 0.9800 . ? c21 h21a 0.9800 . ? c21 h21b 0.9800 . ? c21 h21c 0.9800 . ? c21a h21d 0.9800 . ? c21a h21e 0.9800 . ? c21a h21f 0.9800 . ? c22 n2 1.508(3) . ? c22 c23 1.515(3) . ? c22 h22a 0.9900 . ? c22 h22b 0.9900 . ? c22a c23a 1.494(3) . ? c22a n2a 1.529(3) . ? c22a h22c 0.9900 . ? c22a h22d 0.9900 . ? c23 c24 1.525(3) . ? c23 h23a 0.9900 . ? c23 h23b 0.9900 . ? c23a c24a 1.525(3) . ? c23a h23c 0.9900 . ? c23a h23d 0.9900 . ? c24 h24a 0.9800 . ? c24 h24b 0.9800 . ? c24 h24c 0.9800 . ? c24a h24d 0.9800 . ? c24a h24e 0.9800 . ? c24a h24f 0.9800 . ? c25 n2 1.506(3) . ? c25 c26 1.519(3) . ? c25 h25a 0.9900 . ? c25 h25b 0.9900 . ? c25a c26a 1.504(3) . ? c25a n2a 1.508(3) . ? c25a h25c 0.9900 . ? c25a h25d 0.9900 . ? c26 c27 1.536(3) . ? c26 h26a 0.9900 . ? c26 h26b 0.9900 . ? c26a c27a 1.536(3) . ? c26a h26c 0.9900 . ? c26a h26d 0.9900 . ? c27 h27a 0.9800 . ? c27 h27b 0.9800 . ? c27 h27c 0.9800 . ? c27a h27d 0.9800 . ? c27a h27e 0.9800 . ? c27a h27f 0.9800 . ? n1 in1 2.2690(18) . ? n1 h1n 0.81(3) . ? n1a in1a 2.2748(18) . ? n1a h1na 0.85(3) . ? n2 in1 2.3339(18) . ? n2a in1a 2.3382(18) . ? o1 in1 2.0543(15) . ? o1a in1a 2.0664(15) . ? cl1 in1 2.4049(6) . ? cl1a in1a 2.4050(6) . ? cl2 in1 2.4121(6) . ? cl2a in1a 2.4048(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag n1 c1 c6 112.28(17) . . ? n1 c1 c2 108.33(17) . . ? c6 c1 c2 110.43(17) . . ? n1 c1 h1 108.6 . . ? c6 c1 h1 108.6 . . ? c2 c1 h1 108.6 . . ? n1a c1a c6a 111.70(18) . . ? n1a c1a c2a 109.55(17) . . ? c6a c1a c2a 109.07(18) . . ? n1a c1a h1a 108.8 . . ? c6a c1a h1a 108.8 . . ? c2a c1a h1a 108.8 . . ? n2 c2 c3 114.11(17) . . ? n2 c2 c1 112.47(17) . . ? c3 c2 c1 110.98(18) . . ? n2 c2 h2 106.2 . . ? c3 c2 h2 106.2 . . ? c1 c2 h2 106.2 . . ? n2a c2a c3a 114.36(18) . . ? n2a c2a c1a 113.42(17) . . ? c3a c2a c1a 110.46(18) . . ? n2a c2a h2a 105.9 . . ? c3a c2a h2a 105.9 . . ? c1a c2a h2a 105.9 . . ? c2 c3 c4 110.88(19) . . ? c2 c3 h3a 109.5 . . ? c4 c3 h3a 109.5 . . ? c2 c3 h3b 109.5 . . ? c4 c3 h3b 109.5 . . ? h3a c3 h3b 108.1 . . ? c4a c3a c2a 110.8(2) . . ? c4a c3a h3a1 109.5 . . ? c2a c3a h3a1 109.5 . . ? c4a c3a h3a2 109.5 . . ? c2a c3a h3a2 109.5 . . ? h3a1 c3a h3a2 108.1 . . ? c5 c4 c3 110.5(2) . . ? c5 c4 h4a 109.6 . . ? c3 c4 h4a 109.6 . . ? c5 c4 h4b 109.6 . . ? c3 c4 h4b 109.6 . . ? h4a c4 h4b 108.1 . . ? c5a c4a c3a 111.0(2) . . ? c5a c4a h4a1 109.4 . . ? c3a c4a h4a1 109.4 . . ? c5a c4a h4a2 109.4 . . ? c3a c4a h4a2 109.4 . . ? h4a1 c4a h4a2 108.0 . . ? c6 c5 c4 110.44(19) . . ? c6 c5 h5a 109.6 . . ? c4 c5 h5a 109.6 . . ? c6 c5 h5b 109.6 . . ? c4 c5 h5b 109.6 . . ? h5a c5 h5b 108.1 . . ? c4a c5a c6a 110.8(2) . . ? c4a c5a h5a1 109.5 . . ? c6a c5a h5a1 109.5 . . ? c4a c5a h5a2 109.5 . . ? c6a c5a h5a2 109.5 . . ? h5a1 c5a h5a2 108.1 . . ? c5 c6 c1 111.37(18) . . ? c5 c6 h6a 109.4 . . ? c1 c6 h6a 109.4 . . ? c5 c6 h6b 109.4 . . ? c1 c6 h6b 109.4 . . ? h6a c6 h6b 108.0 . . ? c5a c6a c1a 111.12(19) . . ? c5a c6a h6a1 109.4 . . ? c1a c6a h6a1 109.4 . . ? c5a c6a h6a2 109.4 . . ? c1a c6a h6a2 109.4 . . ? h6a1 c6a h6a2 108.0 . . ? n1 c7 c13 112.21(16) . . ? n1 c7 h7a 109.2 . . ? c13 c7 h7a 109.2 . . ? n1 c7 h7b 109.2 . . ? c13 c7 h7b 109.2 . . ? h7a c7 h7b 107.9 . . ? n1a c7a c13a 112.44(17) . . ? n1a c7a h7a1 109.1 . . ? c13a c7a h7a1 109.1 . . ? n1a c7a h7a2 109.1 . . ? c13a c7a h7a2 109.1 . . ? h7a1 c7a h7a2 107.8 . . ? o1 c8 c13 120.05(18) . . ? o1 c8 c9 120.46(19) . . ? c13 c8 c9 119.49(19) . . ? o1a c8a c13a 119.69(18) . . ? o1a c8a c9a 121.02(19) . . ? c13a c8a c9a 119.29(19) . . ? c10 c9 c8 117.00(19) . . ? c10 c9 c14 121.65(19) . . ? c8 c9 c14 121.35(19) . . ? c10a c9a c8a 117.02(19) . . ? c10a c9a c14a 121.44(19) . . ? c8a c9a c14a 121.53(19) . . ? c9 c10 c11 124.1(2) . . ? c9 c10 h10 117.9 . . ? c11 c10 h10 117.9 . . ? c9a c10a c11a 124.43(19) . . ? c9a c10a h10a 117.8 . . ? c11a c10a h10a 117.8 . . ? c12 c11 c10 117.26(19) . . ? c12 c11 c18 123.16(19) . . ? c10 c11 c18 119.57(19) . . ? c12a c11a c10a 117.01(19) . . ? c12a c11a c18a 123.14(19) . . ? c10a c11a c18a 119.82(18) . . ? c11 c12 c13 120.92(19) . . ? c11 c12 h12 119.5 . . ? c13 c12 h12 119.5 . . ? c11a c12a c13a 121.05(19) . . ? c11a c12a h12a 119.5 . . ? c13a c12a h12a 119.5 . . ? c12 c13 c8 120.86(19) . . ? c12 c13 c7 119.74(19) . . ? c8 c13 c7 119.40(18) . . ? c12a c13a c8a 120.84(19) . . ? c12a c13a c7a 119.98(19) . . ? c8a c13a c7a 119.17(19) . . ? c17 c14 c15 107.15(18) . . ? c17 c14 c16 107.50(19) . . ? c15 c14 c16 109.70(19) . . ? c17 c14 c9 112.26(18) . . ? c15 c14 c9 110.68(18) . . ? c16 c14 c9 109.47(18) . . ? c17a c14a c15a 107.41(19) . . ? c17a c14a c16a 107.49(19) . . ? c15a c14a c16a 109.59(19) . . ? c17a c14a c9a 112.27(18) . . ? c15a c14a c9a 111.11(18) . . ? c16a c14a c9a 108.87(18) . . ? 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 . . ? c14a c15a h15d 109.5 . . ? c14a c15a h15e 109.5 . . ? h15d c15a h15e 109.5 . . ? c14a c15a h15f 109.5 . . ? h15d c15a h15f 109.5 . . ? h15e c15a h15f 109.5 . . ? c14 c16 h16a 109.5 . . ? c14 c16 h16b 109.5 . . ? h16a c16 h16b 109.5 . . ? c14 c16 h16c 109.5 . . ? h16a c16 h16c 109.5 . . ? h16b c16 h16c 109.5 . . ? c14a c16a h16d 109.5 . . ? c14a c16a h16e 109.5 . . ? h16d c16a h16e 109.5 . . ? c14a c16a h16f 109.5 . . ? h16d c16a h16f 109.5 . . ? h16e c16a h16f 109.5 . . ? c14 c17 h17a 109.5 . . ? c14 c17 h17b 109.5 . . ? h17a c17 h17b 109.5 . . ? c14 c17 h17c 109.5 . . ? h17a c17 h17c 109.5 . . ? h17b c17 h17c 109.5 . . ? c14a c17a h17d 109.5 . . ? c14a c17a h17e 109.5 . . ? h17d c17a h17e 109.5 . . ? c14a c17a h17f 109.5 . . ? h17d c17a h17f 109.5 . . ? h17e c17a h17f 109.5 . . ? c11 c18 c21 111.74(18) . . ? c11 c18 c19 110.46(19) . . ? c21 c18 c19 108.45(19) . . ? c11 c18 c20 108.37(18) . . ? c21 c18 c20 108.14(19) . . ? c19 c18 c20 109.6(2) . . ? c19a c18a c11a 111.58(18) . . ? c19a c18a c20a 108.60(19) . . ? c11a c18a c20a 108.42(18) . . ? c19a c18a c21a 108.54(19) . . ? c11a c18a c21a 110.21(18) . . ? c20a c18a c21a 109.45(19) . . ? 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 . . ? c18a c19a h19d 109.5 . . ? c18a c19a h19e 109.5 . . ? h19d c19a h19e 109.5 . . ? c18a c19a h19f 109.5 . . ? h19d c19a h19f 109.5 . . ? h19e c19a h19f 109.5 . . ? c18 c20 h20a 109.5 . . ? c18 c20 h20b 109.5 . . ? h20a c20 h20b 109.5 . . ? c18 c20 h20c 109.5 . . ? h20a c20 h20c 109.5 . . ? h20b c20 h20c 109.5 . . ? c18a c20a h20d 109.5 . . ? c18a c20a h20e 109.5 . . ? h20d c20a h20e 109.5 . . ? c18a c20a h20f 109.5 . . ? h20d c20a h20f 109.5 . . ? h20e c20a h20f 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 . . ? c18a c21a h21d 109.5 . . ? c18a c21a h21e 109.5 . . ? h21d c21a h21e 109.5 . . ? c18a c21a h21f 109.5 . . ? h21d c21a h21f 109.5 . . ? h21e c21a h21f 109.5 . . ? n2 c22 c23 115.78(17) . . ? n2 c22 h22a 108.3 . . ? c23 c22 h22a 108.3 . . ? n2 c22 h22b 108.3 . . ? c23 c22 h22b 108.3 . . ? h22a c22 h22b 107.4 . . ? c23a c22a n2a 115.60(18) . . ? c23a c22a h22c 108.4 . . ? n2a c22a h22c 108.4 . . ? c23a c22a h22d 108.4 . . ? n2a c22a h22d 108.4 . . ? h22c c22a h22d 107.4 . . ? c22 c23 c24 110.52(19) . . ? c22 c23 h23a 109.5 . . ? c24 c23 h23a 109.5 . . ? c22 c23 h23b 109.5 . . ? c24 c23 h23b 109.5 . . ? h23a c23 h23b 108.1 . . ? c22a c23a c24a 109.4(2) . . ? c22a c23a h23c 109.8 . . ? c24a c23a h23c 109.8 . . ? c22a c23a h23d 109.8 . . ? c24a c23a h23d 109.8 . . ? h23c c23a h23d 108.2 . . ? c23 c24 h24a 109.5 . . ? c23 c24 h24b 109.5 . . ? h24a c24 h24b 109.5 . . ? c23 c24 h24c 109.5 . . ? h24a c24 h24c 109.5 . . ? h24b c24 h24c 109.5 . . ? c23a c24a h24d 109.5 . . ? c23a c24a h24e 109.5 . . ? h24d c24a h24e 109.5 . . ? c23a c24a h24f 109.5 . . ? h24d c24a h24f 109.5 . . ? h24e c24a h24f 109.5 . . ? n2 c25 c26 117.37(18) . . ? n2 c25 h25a 108.0 . . ? c26 c25 h25a 108.0 . . ? n2 c25 h25b 108.0 . . ? c26 c25 h25b 108.0 . . ? h25a c25 h25b 107.2 . . ? c26a c25a n2a 118.07(19) . . ? c26a c25a h25c 107.8 . . ? n2a c25a h25c 107.8 . . ? c26a c25a h25d 107.8 . . ? n2a c25a h25d 107.8 . . ? h25c c25a h25d 107.1 . . ? c25 c26 c27 109.3(2) . . ? c25 c26 h26a 109.8 . . ? c27 c26 h26a 109.8 . . ? c25 c26 h26b 109.8 . . ? c27 c26 h26b 109.8 . . ? h26a c26 h26b 108.3 . . ? c25a c26a c27a 109.1(2) . . ? c25a c26a h26c 109.9 . . ? c27a c26a h26c 109.9 . . ? c25a c26a h26d 109.9 . . ? c27a c26a h26d 109.9 . . ? h26c c26a h26d 108.3 . . ? c26 c27 h27a 109.5 . . ? c26 c27 h27b 109.5 . . ? h27a c27 h27b 109.5 . . ? c26 c27 h27c 109.5 . . ? h27a c27 h27c 109.5 . . ? h27b c27 h27c 109.5 . . ? c26a c27a h27d 109.5 . . ? c26a c27a h27e 109.5 . . ? h27d c27a h27e 109.5 . . ? c26a c27a h27f 109.5 . . ? h27d c27a h27f 109.5 . . ? h27e c27a h27f 109.5 . . ? c1 n1 c7 114.28(16) . . ? c1 n1 in1 112.81(12) . . ? c7 n1 in1 108.39(12) . . ? c1 n1 h1n 105(2) . . ? c7 n1 h1n 111(2) . . ? in1 n1 h1n 106(2) . . ? c1a n1a c7a 113.33(16) . . ? c1a n1a in1a 113.73(13) . . ? c7a n1a in1a 109.72(13) . . ? c1a n1a h1na 108.1(17) . . ? c7a n1a h1na 106.6(17) . . ? in1a n1a h1na 104.8(17) . . ? c25 n2 c22 105.32(16) . . ? c25 n2 c2 114.81(17) . . ? c22 n2 c2 110.51(16) . . ? c25 n2 in1 109.51(13) . . ? c22 n2 in1 107.83(13) . . ? c2 n2 in1 108.64(12) . . ? c25a n2a c2a 116.08(18) . . ? c25a n2a c22a 104.10(17) . . ? c2a n2a c22a 110.49(16) . . ? c25a n2a in1a 110.09(13) . . ? c2a n2a in1a 108.05(12) . . ? c22a n2a in1a 107.73(13) . . ? c8 o1 in1 121.80(13) . . ? c8a o1a in1a 120.30(13) . . ? o1 in1 n1 89.42(6) . . ? o1 in1 n2 127.73(6) . . ? n1 in1 n2 76.80(6) . . ? o1 in1 cl1 98.72(4) . . ? n1 in1 cl1 167.14(5) . . ? n2 in1 cl1 90.34(5) . . ? o1 in1 cl2 103.52(4) . . ? n1 in1 cl2 87.89(5) . . ? n2 in1 cl2 125.56(5) . . ? cl1 in1 cl2 99.76(2) . . ? o1a in1a n1a 88.50(6) . . ? o1a in1a n2a 126.25(6) . . ? n1a in1a n2a 77.09(6) . . ? o1a in1a cl2a 98.17(5) . . ? n1a in1a cl2a 167.99(5) . . ? n2a in1a cl2a 90.92(5) . . ? o1a in1a cl1a 109.16(5) . . ? n1a in1a cl1a 89.33(5) . . ? n2a in1a cl1a 121.90(5) . . ? cl2a in1a cl1a 97.80(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 n1 c1 c2 n2 -51.9(2) . . . . ? c6 c1 c2 n2 -175.29(16) . . . . ? n1 c1 c2 c3 178.86(17) . . . . ? c6 c1 c2 c3 55.5(2) . . . . ? n1a c1a c2a n2a -48.9(2) . . . . ? c6a c1a c2a n2a -171.45(17) . . . . ? n1a c1a c2a c3a -178.81(17) . . . . ? c6a c1a c2a c3a 58.6(2) . . . . ? n2 c2 c3 c4 175.45(19) . . . . ? c1 c2 c3 c4 -56.2(2) . . . . ? n2a c2a c3a c4a 172.48(19) . . . . ? c1a c2a c3a c4a -58.1(3) . . . . ? c2 c3 c4 c5 57.0(3) . . . . ? c2a c3a c4a c5a 56.2(3) . . . . ? c3 c4 c5 c6 -57.4(3) . . . . ? c3a c4a c5a c6a -55.4(3) . . . . ? c4 c5 c6 c1 57.5(3) . . . . ? n1 c1 c6 c5 -177.42(18) . . . . ? c2 c1 c6 c5 -56.4(2) . . . . ? c4a c5a c6a c1a 57.0(3) . . . . ? n1a c1a c6a c5a -179.46(18) . . . . ? c2a c1a c6a c5a -58.2(2) . . . . ? o1 c8 c9 c10 174.65(19) . . . . ? c13 c8 c9 c10 -5.2(3) . . . . ? o1 c8 c9 c14 -6.0(3) . . . . ? c13 c8 c9 c14 174.15(19) . . . . ? o1a c8a c9a c10a 174.30(19) . . . . ? c13a c8a c9a c10a -6.1(3) . . . . ? o1a c8a c9a c14a -6.7(3) . . . . ? c13a c8a c9a c14a 172.89(19) . . . . ? c8 c9 c10 c11 0.5(3) . . . . ? c14 c9 c10 c11 -178.9(2) . . . . ? c8a c9a c10a c11a 1.6(3) . . . . ? c14a c9a c10a c11a -177.4(2) . . . . ? c9 c10 c11 c12 3.8(3) . . . . ? c9 c10 c11 c18 -174.9(2) . . . . ? c9a c10a c11a c12a 2.9(3) . . . . ? c9a c10a c11a c18a -175.2(2) . . . . ? c10 c11 c12 c13 -3.2(3) . . . . ? c18 c11 c12 c13 175.4(2) . . . . ? c10a c11a c12a c13a -3.0(3) . . . . ? c18a c11a c12a c13a 175.1(2) . . . . ? c11 c12 c13 c8 -1.6(3) . . . . ? c11 c12 c13 c7 177.99(19) . . . . ? o1 c8 c13 c12 -173.99(19) . . . . ? c9 c8 c13 c12 5.9(3) . . . . ? o1 c8 c13 c7 6.5(3) . . . . ? c9 c8 c13 c7 -173.65(19) . . . . ? n1 c7 c13 c12 111.3(2) . . . . ? n1 c7 c13 c8 -69.1(2) . . . . ? c11a c12a c13a c8a -1.5(3) . . . . ? c11a c12a c13a c7a 177.15(19) . . . . ? o1a c8a c13a c12a -174.18(19) . . . . ? c9a c8a c13a c12a 6.2(3) . . . . ? o1a c8a c13a c7a 7.1(3) . . . . ? c9a c8a c13a c7a -172.48(19) . . . . ? n1a c7a c13a c12a 112.1(2) . . . . ? n1a c7a c13a c8a -69.2(2) . . . . ? c10 c9 c14 c17 3.5(3) . . . . ? c8 c9 c14 c17 -175.8(2) . . . . ? c10 c9 c14 c15 -116.2(2) . . . . ? c8 c9 c14 c15 64.5(3) . . . . ? c10 c9 c14 c16 122.8(2) . . . . ? c8 c9 c14 c16 -56.6(3) . . . . ? c10a c9a c14a c17a 2.5(3) . . . . ? c8a c9a c14a c17a -176.4(2) . . . . ? c10a c9a c14a c15a -117.8(2) . . . . ? c8a c9a c14a c15a 63.3(3) . . . . ? c10a c9a c14a c16a 121.4(2) . . . . ? c8a c9a c14a c16a -57.5(3) . . . . ? c12 c11 c18 c21 2.7(3) . . . . ? c10 c11 c18 c21 -178.8(2) . . . . ? c12 c11 c18 c19 123.5(2) . . . . ? c10 c11 c18 c19 -57.9(3) . . . . ? c12 c11 c18 c20 -116.4(2) . . . . ? c10 c11 c18 c20 62.2(3) . . . . ? c12a c11a c18a c19a 5.5(3) . . . . ? c10a c11a c18a c19a -176.46(19) . . . . ? c12a c11a c18a c20a -114.1(2) . . . . ? c10a c11a c18a c20a 64.0(3) . . . . ? c12a c11a c18a c21a 126.2(2) . . . . ? c10a c11a c18a c21a -55.8(3) . . . . ? n2 c22 c23 c24 -162.7(2) . . . . ? n2a c22a c23a c24a -161.3(2) . . . . ? n2 c25 c26 c27 173.4(2) . . . . ? n2a c25a c26a c27a 170.2(2) . . . . ? c6 c1 n1 c7 -72.2(2) . . . . ? c2 c1 n1 c7 165.57(16) . . . . ? c6 c1 n1 in1 163.38(14) . . . . ? c2 c1 n1 in1 41.16(19) . . . . ? c13 c7 n1 c1 -64.5(2) . . . . ? c13 c7 n1 in1 62.22(18) . . . . ? c6a c1a n1a c7a -79.3(2) . . . . ? c2a c1a n1a c7a 159.73(17) . . . . ? c6a c1a n1a in1a 154.46(14) . . . . ? c2a c1a n1a in1a 33.5(2) . . . . ? c13a c7a n1a c1a -69.6(2) . . . . ? c13a c7a n1a in1a 58.74(19) . . . . ? c26 c25 n2 c22 -177.86(19) . . . . ? c26 c25 n2 c2 60.4(3) . . . . ? c26 c25 n2 in1 -62.1(2) . . . . ? c23 c22 n2 c25 171.99(19) . . . . ? c23 c22 n2 c2 -63.5(2) . . . . ? c23 c22 n2 in1 55.1(2) . . . . ? c3 c2 n2 c25 40.8(2) . . . . ? c1 c2 n2 c25 -86.7(2) . . . . ? c3 c2 n2 c22 -78.1(2) . . . . ? c1 c2 n2 c22 154.34(17) . . . . ? c3 c2 n2 in1 163.78(15) . . . . ? c1 c2 n2 in1 36.23(19) . . . . ? c26a c25a n2a c2a 59.8(3) . . . . ? c26a c25a n2a c22a -178.5(2) . . . . ? c26a c25a n2a in1a -63.3(2) . . . . ? c3a c2a n2a c25a 42.5(3) . . . . ? c1a c2a n2a c25a -85.4(2) . . . . ? c3a c2a n2a c22a -75.7(2) . . . . ? c1a c2a n2a c22a 156.39(18) . . . . ? c3a c2a n2a in1a 166.68(15) . . . . ? c1a c2a n2a in1a 38.8(2) . . . . ? c23a c22a n2a c25a 179.8(2) . . . . ? c23a c22a n2a c2a -54.9(3) . . . . ? c23a c22a n2a in1a 62.9(2) . . . . ? c13 c8 o1 in1 47.8(2) . . . . ? c9 c8 o1 in1 -132.13(17) . . . . ? c13a c8a o1a in1a 50.9(2) . . . . ? c9a c8a o1a in1a -129.46(17) . . . . ? c8 o1 in1 n1 -37.41(15) . . . . ? c8 o1 in1 n2 35.34(17) . . . . ? c8 o1 in1 cl1 132.59(14) . . . . ? c8 o1 in1 cl2 -125.10(14) . . . . ? c1 n1 in1 o1 111.97(14) . . . . ? c7 n1 in1 o1 -15.61(13) . . . . ? c1 n1 in1 n2 -17.15(13) . . . . ? c7 n1 in1 n2 -144.73(13) . . . . ? c1 n1 in1 cl1 -17.6(3) . . . . ? c7 n1 in1 cl1 -145.15(17) . . . . ? c1 n1 in1 cl2 -144.48(13) . . . . ? c7 n1 in1 cl2 87.94(12) . . . . ? c25 n2 in1 o1 37.00(16) . . . . ? c22 n2 in1 o1 151.10(12) . . . . ? c2 n2 in1 o1 -89.10(14) . . . . ? c25 n2 in1 n1 115.78(14) . . . . ? c22 n2 in1 n1 -130.12(13) . . . . ? c2 n2 in1 n1 -10.32(13) . . . . ? c25 n2 in1 cl1 -64.31(13) . . . . ? c22 n2 in1 cl1 49.79(12) . . . . ? c2 n2 in1 cl1 169.58(12) . . . . ? c25 n2 in1 cl2 -166.59(11) . . . . ? c22 n2 in1 cl2 -52.49(14) . . . . ? c2 n2 in1 cl2 67.31(14) . . . . ? c8a o1a in1a n1a -42.78(15) . . . . ? c8a o1a in1a n2a 29.99(17) . . . . ? c8a o1a in1a cl2a 127.19(14) . . . . ? c8a o1a in1a cl1a -131.55(14) . . . . ? c1a n1a in1a o1a 117.50(14) . . . . ? c7a n1a in1a o1a -10.61(13) . . . . ? c1a n1a in1a n2a -10.29(13) . . . . ? c7a n1a in1a n2a -138.40(14) . . . . ? c1a n1a in1a cl2a -6.6(3) . . . . ? c7a n1a in1a cl2a -134.72(19) . . . . ? c1a n1a in1a cl1a -133.31(13) . . . . ? c7a n1a in1a cl1a 98.58(12) . . . . ? c25a n2a in1a o1a 34.37(17) . . . . ? c2a n2a in1a o1a -93.34(14) . . . . ? c22a n2a in1a o1a 147.28(12) . . . . ? c25a n2a in1a n1a 112.75(15) . . . . ? c2a n2a in1a n1a -14.95(13) . . . . ? c22a n2a in1a n1a -134.33(13) . . . . ? c25a n2a in1a cl2a -66.48(14) . . . . ? c2a n2a in1a cl2a 165.82(12) . . . . ? c22a n2a in1a cl2a 46.43(12) . . . . ? c25a n2a in1a cl1a -166.27(12) . . . . ? c2a n2a in1a cl1a 66.03(14) . . . . ? c22a n2a in1a cl1a -53.35(13) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.030 _refine_diff_density_min -0.741 _refine_diff_density_rms 0.106 #===END data_pm066_0m _database_code_depnum_ccdc_archive 'CCDC 864183' #TrackingRef '- Mehr_DaltonJan192012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H45 Cl2 In N2 O, C4 H8 O' _chemical_formula_sum 'C34 H53 Cl2 In N2 O2' _chemical_formula_weight 707.50 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 11.4157(3) _cell_length_b 17.5129(4) _cell_length_c 17.1967(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.3240(10) _cell_angle_gamma 90.00 _cell_volume 3331.12(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9750 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 29.19 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7806 _exptl_absorpt_correction_T_max 0.8734 _exptl_absorpt_process_details ? _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 '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 52518 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 29.20 _reflns_number_total 9024 _reflns_number_gt 7927 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0373P)^2^+4.6915P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9024 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 1.683 _refine_ls_shift/su_mean 0.006 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 0.70963(17) 0.26636(11) 0.73180(11) 0.0124(3) Uani 1 1 d . . . H1 H 0.6466 0.2255 0.7244 0.015 Uiso 1 1 calc R . . C2 C 0.70404(19) 0.30301(12) 0.65027(12) 0.0164(4) Uani 1 1 d . . . H2A H 0.7715 0.3398 0.6560 0.020 Uiso 1 1 calc R . . H2B H 0.7147 0.2629 0.6120 0.020 Uiso 1 1 calc R . . C3 C 0.58474(19) 0.34437(12) 0.61638(12) 0.0177(4) Uani 1 1 d . . . H3A H 0.5180 0.3067 0.6038 0.021 Uiso 1 1 calc R . . H3B H 0.5878 0.3705 0.5659 0.021 Uiso 1 1 calc R . . C4 C 0.5598(2) 0.40289(12) 0.67620(12) 0.0192(4) Uani 1 1 d . . . H4A H 0.6220 0.4435 0.6846 0.023 Uiso 1 1 calc R . . H4B H 0.4799 0.4268 0.6542 0.023 Uiso 1 1 calc R . . C5 C 0.56157(18) 0.36471(11) 0.75610(12) 0.0145(4) Uani 1 1 d . . . H5A H 0.5470 0.4035 0.7946 0.017 Uiso 1 1 calc R . . H5B H 0.4961 0.3263 0.7483 0.017 Uiso 1 1 calc R . . C6 C 0.68306(17) 0.32599(11) 0.79022(11) 0.0123(3) Uani 1 1 d . . . H6 H 0.7476 0.3659 0.7984 0.015 Uiso 1 1 calc R . . C7 C 0.86100(17) 0.16470(12) 0.72221(12) 0.0146(4) Uani 1 1 d . . . H7A H 0.8426 0.1776 0.6644 0.018 Uiso 1 1 calc R . . H7B H 0.8106 0.1203 0.7288 0.018 Uiso 1 1 calc R . . C8 C 1.04008(17) 0.12133(11) 0.83099(11) 0.0124(3) Uani 1 1 d . . . C9 C 1.16484(17) 0.10269(11) 0.85740(11) 0.0125(3) Uani 1 1 d . . . C10 C 1.23356(17) 0.10637(11) 0.80072(12) 0.0138(4) Uani 1 1 d . . . H10 H 1.3171 0.0942 0.8179 0.017 Uiso 1 1 calc R . . C11 C 1.18745(17) 0.12681(11) 0.72034(12) 0.0130(3) Uani 1 1 d . . . C12 C 1.06600(18) 0.14607(11) 0.69677(11) 0.0136(4) Uani 1 1 d . . . H12 H 1.0320 0.1612 0.6428 0.016 Uiso 1 1 calc R . . C13 C 0.99267(17) 0.14370(11) 0.75091(12) 0.0137(3) Uani 1 1 d . . . C14 C 1.27179(18) 0.12744(11) 0.66350(12) 0.0141(4) Uani 1 1 d . . . C15 C 1.2025(2) 0.13850(15) 0.57590(13) 0.0232(4) Uani 1 1 d . . . H15A H 1.2595 0.1386 0.5416 0.035 Uiso 1 1 calc R . . H15B H 1.1591 0.1873 0.5702 0.035 Uiso 1 1 calc R . . H15C H 1.1445 0.0967 0.5597 0.035 Uiso 1 1 calc R . . C16 C 1.3647(2) 0.19209(12) 0.68717(14) 0.0209(4) Uani 1 1 d . . . H16A H 1.4183 0.1923 0.6506 0.031 Uiso 1 1 calc R . . H16B H 1.4125 0.1840 0.7423 0.031 Uiso 1 1 calc R . . H16C H 1.3224 0.2412 0.6837 0.031 Uiso 1 1 calc R . . C17 C 1.34091(19) 0.05151(12) 0.67016(13) 0.0191(4) Uani 1 1 d . . . H17A H 1.3946 0.0522 0.6337 0.029 Uiso 1 1 calc R . . H17B H 1.2832 0.0093 0.6556 0.029 Uiso 1 1 calc R . . H17C H 1.3890 0.0446 0.7254 0.029 Uiso 1 1 calc R . . C18 C 1.22144(17) 0.07993(12) 0.94458(11) 0.0143(4) Uani 1 1 d . . . C19 C 1.1579(2) 0.00965(13) 0.96844(13) 0.0221(4) Uani 1 1 d . . . H19A H 1.1956 -0.0038 1.0243 0.033 Uiso 1 1 calc R . . H19B H 1.1654 -0.0333 0.9335 0.033 Uiso 1 1 calc R . . H19C H 1.0722 0.0212 0.9627 0.033 Uiso 1 1 calc R . . C20 C 1.2125(2) 0.14717(14) 1.00038(13) 0.0227(4) Uani 1 1 d . . . H20A H 1.2488 0.1326 1.0561 0.034 Uiso 1 1 calc R . . H20B H 1.1273 0.1604 0.9944 0.034 Uiso 1 1 calc R . . H20C H 1.2556 0.1913 0.9862 0.034 Uiso 1 1 calc R . . C21 C 1.35588(18) 0.05941(13) 0.95861(12) 0.0189(4) Uani 1 1 d . . . H21A H 1.3884 0.0453 1.0150 0.028 Uiso 1 1 calc R . . H21B H 1.4003 0.1035 0.9457 0.028 Uiso 1 1 calc R . . H21C H 1.3647 0.0163 0.9241 0.028 Uiso 1 1 calc R . . C22 C 0.68064(17) 0.34086(11) 0.93375(11) 0.0131(3) Uani 1 1 d . . . C23 C 0.77472(18) 0.39146(12) 0.96602(12) 0.0156(4) Uani 1 1 d . . . C24 C 0.76217(19) 0.43960(12) 1.02787(12) 0.0185(4) Uani 1 1 d . . . H24 H 0.8254 0.4746 1.0496 0.022 Uiso 1 1 calc R . . C25 C 0.6610(2) 0.43860(13) 1.05921(13) 0.0199(4) Uani 1 1 d . . . C26 C 0.5703(2) 0.38638(13) 1.02659(13) 0.0193(4) Uani 1 1 d . . . H26 H 0.5008 0.3842 1.0476 0.023 Uiso 1 1 calc R . . C27 C 0.57762(18) 0.33738(12) 0.96454(12) 0.0156(4) Uani 1 1 d . . . C28 C 0.88954(19) 0.39630(13) 0.93795(13) 0.0201(4) Uani 1 1 d . . . H28A H 0.8798 0.4343 0.8950 0.030 Uiso 1 1 calc R . . H28B H 0.9070 0.3464 0.9176 0.030 Uiso 1 1 calc R . . H28C H 0.9566 0.4113 0.9829 0.030 Uiso 1 1 calc R . . C29 C 0.6496(2) 0.49191(15) 1.12551(14) 0.0276(5) Uani 1 1 d . . . H29A H 0.7218 0.5242 1.1406 0.041 Uiso 1 1 calc R . . H29B H 0.6415 0.4621 1.1721 0.041 Uiso 1 1 calc R . . H29C H 0.5779 0.5242 1.1070 0.041 Uiso 1 1 calc R . . C30 C 0.4756(2) 0.28255(13) 0.93211(14) 0.0212(4) Uani 1 1 d . . . H30A H 0.4157 0.2862 0.9641 0.032 Uiso 1 1 calc R . . H30B H 0.5074 0.2304 0.9351 0.032 Uiso 1 1 calc R . . H30C H 0.4374 0.2954 0.8761 0.032 Uiso 1 1 calc R . . O2 O 1.00727(17) 0.35411(11) 0.78442(13) 0.0357(4) Uani 1 1 d . . . C31 C 1.13205(4) 0.331054(18) 0.798726(13) 0.0339(6) Uani 1 1 d . . . H31A H 1.13882(4) 0.274788(13) 0.802487(13) 0.041 Uiso 1 1 calc R . . H31B H 1.18005(4) 0.35339(2) 0.849491(9) 0.041 Uiso 1 1 calc R . . C32 C 1.17972(4) 0.36138(2) 0.72490(2) 0.0363(6) Uani 1 1 d R . . H32A H 1.26402(5) 0.37988(2) 0.742155(19) 0.044 Uiso 1 1 calc R . . H32B H 1.17397(4) 0.321702(17) 0.68321(3) 0.044 Uiso 1 1 calc R . . C33 C 1.08837(3) 0.42873(3) 0.69493(2) 0.0314(5) Uani 1 1 d R . . H33A H 1.04295(3) 0.42044(3) 0.63871(3) 0.038 Uiso 1 1 calc R . . H33B H 1.13147(4) 0.47805(3) 0.69859(2) 0.038 Uiso 1 1 calc R . . C34 C 1.00022(2) 0.42755(3) 0.753203(18) 0.0173(4) Uani 1 1 d R . . H34A H 1.02607(3) 0.46547(3) 0.796689(13) 0.021 Uiso 1 1 calc R . . H34B H 0.916482(15) 0.43942(3) 0.72332(2) 0.021 Uiso 1 1 calc R . . N1 N 0.829995(11) 0.231441(9) 0.768148(16) 0.0123(3) Uani 1 1 d R . . N2 N 0.688432(19) 0.288982(14) 0.869391(8) 0.0122(3) Uani 1 1 d R . . O1 O 0.96812(2) 0.115763(11) 0.882086(7) 0.0158(3) Uani 1 1 d R . . Cl1 Cl 0.902879(14) 0.214483(8) 1.027666(17) 0.01934(10) Uani 1 1 d R . . Cl2 Cl 0.65175(2) 0.105633(12) 0.855629(9) 0.02082(10) Uani 1 1 d R . . In1 In 0.827979(11) 0.185597(7) 0.889925(7) 0.01193(4) Uani 1 1 d R . . H2N H 0.6273 0.2584 0.8600 0.017(6) Uiso 1 1 d R . . H1N H 0.8827 0.2653 0.7698 0.023(7) Uiso 1 1 d 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 0.0099(8) 0.0140(8) 0.0125(8) 0.0004(7) 0.0017(6) 0.0014(6) C2 0.0169(9) 0.0201(10) 0.0121(9) 0.0027(7) 0.0036(7) 0.0034(7) C3 0.0201(10) 0.0187(9) 0.0128(9) 0.0020(7) 0.0015(7) 0.0036(8) C4 0.0238(10) 0.0177(10) 0.0153(9) 0.0037(7) 0.0031(8) 0.0061(8) C5 0.0146(9) 0.0144(9) 0.0139(9) 0.0015(7) 0.0023(7) 0.0031(7) C6 0.0128(8) 0.0128(8) 0.0110(8) 0.0016(6) 0.0023(7) 0.0013(7) C7 0.0133(8) 0.0165(9) 0.0135(8) -0.0024(7) 0.0025(7) 0.0025(7) C8 0.0131(8) 0.0116(8) 0.0129(8) -0.0010(7) 0.0039(7) 0.0003(6) C9 0.0136(8) 0.0109(8) 0.0122(8) -0.0006(6) 0.0019(7) 0.0010(6) C10 0.0112(8) 0.0135(9) 0.0160(9) -0.0009(7) 0.0020(7) 0.0010(7) C11 0.0142(8) 0.0118(8) 0.0137(8) -0.0003(7) 0.0047(7) -0.0001(7) C12 0.0152(9) 0.0132(8) 0.0119(8) 0.0003(7) 0.0025(7) 0.0018(7) C13 0.0119(8) 0.0140(9) 0.0146(9) 0.0000(7) 0.0026(7) 0.0018(7) C14 0.0135(8) 0.0154(9) 0.0142(9) 0.0008(7) 0.0049(7) 0.0017(7) C15 0.0181(10) 0.0371(13) 0.0153(10) 0.0041(9) 0.0060(8) 0.0027(9) C16 0.0194(10) 0.0179(10) 0.0276(11) -0.0017(8) 0.0104(9) -0.0040(8) C17 0.0204(10) 0.0190(10) 0.0200(10) -0.0002(8) 0.0092(8) 0.0028(8) C18 0.0127(8) 0.0173(9) 0.0117(8) -0.0006(7) 0.0008(7) 0.0011(7) C19 0.0206(10) 0.0230(11) 0.0208(10) 0.0095(8) 0.0017(8) 0.0004(8) C20 0.0207(10) 0.0288(12) 0.0173(10) -0.0077(8) 0.0019(8) 0.0040(9) C21 0.0149(9) 0.0262(11) 0.0140(9) -0.0023(8) 0.0002(7) 0.0048(8) C22 0.0145(8) 0.0133(8) 0.0112(8) 0.0014(7) 0.0027(7) 0.0027(7) C23 0.0145(9) 0.0177(9) 0.0138(9) 0.0029(7) 0.0023(7) 0.0017(7) C24 0.0199(10) 0.0173(9) 0.0163(9) -0.0004(7) 0.0006(8) -0.0004(8) C25 0.0256(11) 0.0189(10) 0.0148(9) -0.0005(8) 0.0044(8) 0.0050(8) C26 0.0211(10) 0.0214(10) 0.0175(9) 0.0003(8) 0.0086(8) 0.0034(8) C27 0.0144(9) 0.0173(9) 0.0155(9) 0.0023(7) 0.0044(7) 0.0015(7) C28 0.0135(9) 0.0254(11) 0.0201(10) -0.0005(8) 0.0017(8) -0.0026(8) C29 0.0329(12) 0.0280(12) 0.0219(11) -0.0070(9) 0.0069(9) 0.0045(10) C30 0.0189(10) 0.0238(11) 0.0241(11) -0.0035(9) 0.0111(8) -0.0049(8) O2 0.0315(10) 0.0309(10) 0.0469(11) 0.0023(8) 0.0136(9) -0.0034(8) C31 0.0298(13) 0.0271(12) 0.0411(15) 0.0024(11) 0.0018(11) -0.0021(10) C32 0.0541(17) 0.0266(12) 0.0220(11) -0.0064(10) -0.0024(11) 0.0194(12) C33 0.0300(13) 0.0274(12) 0.0379(14) 0.0094(10) 0.0105(11) 0.0042(10) C34 0.0141(9) 0.0151(9) 0.0243(10) -0.0012(8) 0.0082(8) -0.0029(7) N1 0.0103(7) 0.0137(7) 0.0127(7) 0.0000(6) 0.0023(6) 0.0017(6) N2 0.0125(7) 0.0127(7) 0.0119(7) 0.0015(6) 0.0037(6) 0.0008(6) O1 0.0150(7) 0.0183(7) 0.0154(7) 0.0033(5) 0.0064(5) 0.0048(5) Cl1 0.0214(2) 0.0247(2) 0.0117(2) 0.00044(18) 0.00373(17) 0.00623(19) Cl2 0.0152(2) 0.0180(2) 0.0280(3) 0.00461(19) 0.00287(19) -0.00178(17) In1 0.01146(7) 0.01331(7) 0.01142(7) 0.00170(5) 0.00356(5) 0.00171(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.4925(18) . ? C1 C2 1.529(3) . ? C1 C6 1.531(3) . ? C1 H1 1.0000 . ? C2 C3 1.525(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.528(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.524(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.525(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N2 1.4954(19) . ? C6 H6 1.0000 . ? C7 N1 1.5013(19) . ? C7 C13 1.507(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.3467(19) . ? C8 C13 1.405(3) . ? C8 C9 1.422(3) . ? C9 C10 1.396(3) . ? C9 C18 1.531(3) . ? C10 C11 1.399(3) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 C14 1.532(3) . ? C12 C13 1.398(3) . ? C12 H12 0.9500 . ? C14 C15 1.531(3) . ? C14 C16 1.536(3) . ? C14 C17 1.536(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.535(3) . ? C18 C21 1.536(3) . ? C18 C20 1.538(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 C23 1.397(3) . ? C22 C27 1.405(3) . ? C22 N2 1.4515(19) . ? C23 C24 1.392(3) . ? C23 C28 1.507(3) . ? C24 C25 1.390(3) . ? C24 H24 0.9500 . ? C25 C26 1.392(3) . ? C25 C29 1.504(3) . ? C26 C27 1.388(3) . ? C26 H26 0.9500 . ? C27 C30 1.506(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? O2 C34 1.388(2) . ? O2 C31 1.442(2) . ? C31 C32 1.5913 . ? C31 H31A 0.9893 . ? C31 H31B 0.9893 . ? C32 C33 1.5743 . ? C32 H32A 0.9889 . ? C32 H32B 0.9889 . ? C33 C34 1.5862 . ? C33 H33A 0.9883 . ? C33 H33B 0.9883 . ? C34 H34A 0.9890 . ? C34 H34B 0.9887 . ? N1 In1 2.2482 . ? N1 H1N 0.8399 . ? N2 In1 2.3795 . ? N2 H2N 0.8627 . ? O1 In1 2.0445 . ? Cl1 In1 2.3655 . ? Cl2 In1 2.4019 . ? 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 C2 112.41(14) . . ? N1 C1 C6 108.43(13) . . ? C2 C1 C6 110.20(16) . . ? N1 C1 H1 108.6 . . ? C2 C1 H1 108.6 . . ? C6 C1 H1 108.6 . . ? C3 C2 C1 112.36(16) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 111.02(17) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 110.47(17) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 110.47(16) . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? N2 C6 C5 111.82(14) . . ? N2 C6 C1 109.37(14) . . ? C5 C6 C1 111.10(16) . . ? N2 C6 H6 108.1 . . ? C5 C6 H6 108.1 . . ? C1 C6 H6 108.1 . . ? N1 C7 C13 111.32(14) . . ? N1 C7 H7A 109.4 . . ? C13 C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? C13 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O1 C8 C13 120.70(16) . . ? O1 C8 C9 119.97(16) . . ? C13 C8 C9 119.32(17) . . ? C10 C9 C8 117.26(17) . . ? C10 C9 C18 121.46(17) . . ? C8 C9 C18 121.28(17) . . ? C9 C10 C11 124.26(18) . . ? C9 C10 H10 117.9 . . ? C11 C10 H10 117.9 . . ? C12 C11 C10 117.13(17) . . ? C12 C11 C14 123.53(17) . . ? C10 C11 C14 119.34(17) . . ? C11 C12 C13 121.21(18) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 120.80(18) . . ? C12 C13 C7 119.19(17) . . ? C8 C13 C7 120.01(17) . . ? C15 C14 C11 112.05(16) . . ? C15 C14 C16 108.80(18) . . ? C11 C14 C16 109.74(16) . . ? C15 C14 C17 108.29(17) . . ? C11 C14 C17 109.79(16) . . ? C16 C14 C17 108.08(17) . . ? 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 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C9 C18 C19 110.95(16) . . ? C9 C18 C21 112.20(16) . . ? C19 C18 C21 106.87(17) . . ? C9 C18 C20 109.54(17) . . ? C19 C18 C20 109.77(18) . . ? C21 C18 C20 107.42(16) . . ? 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 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 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 . . ? C23 C22 C27 120.70(18) . . ? C23 C22 N2 120.91(16) . . ? C27 C22 N2 118.36(16) . . ? C24 C23 C22 118.25(19) . . ? C24 C23 C28 118.21(19) . . ? C22 C23 C28 123.54(18) . . ? C25 C24 C23 122.8(2) . . ? C25 C24 H24 118.6 . . ? C23 C24 H24 118.6 . . ? C24 C25 C26 117.33(19) . . ? C24 C25 C29 121.5(2) . . ? C26 C25 C29 121.2(2) . . ? C27 C26 C25 122.4(2) . . ? C27 C26 H26 118.8 . . ? C25 C26 H26 118.8 . . ? C26 C27 C22 118.57(19) . . ? C26 C27 C30 119.38(19) . . ? C22 C27 C30 122.05(18) . . ? C23 C28 H28A 109.5 . . ? C23 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C23 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 H29A 109.5 . . ? C25 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C25 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C34 O2 C31 106.60(13) . . ? O2 C31 C32 106.79(8) . . ? O2 C31 H31A 110.4 . . ? C32 C31 H31A 110.4 . . ? O2 C31 H31B 110.4 . . ? C32 C31 H31B 110.4 . . ? H31A C31 H31B 108.6 . . ? C33 C32 C31 100.5 . . ? C33 C32 H32A 111.7 . . ? C31 C32 H32A 111.7 . . ? C33 C32 H32B 111.7 . . ? C31 C32 H32B 111.7 . . ? H32A C32 H32B 109.5 . . ? C32 C33 C34 104.8 . . ? C32 C33 H33A 110.8 . . ? C34 C33 H33A 110.8 . . ? C32 C33 H33B 110.8 . . ? C34 C33 H33B 110.8 . . ? H33A C33 H33B 108.9 . . ? O2 C34 C33 105.74(8) . . ? O2 C34 H34A 110.6 . . ? C33 C34 H34A 110.6 . . ? O2 C34 H34B 110.6 . . ? C33 C34 H34B 110.6 . . ? H34A C34 H34B 108.8 . . ? C1 N1 C7 114.28(10) . . ? C1 N1 In1 108.41(7) . . ? C7 N1 In1 105.67(8) . . ? C1 N1 H1N 107.6 . . ? C7 N1 H1N 108.0 . . ? In1 N1 H1N 113.1 . . ? C22 N2 C6 115.24(11) . . ? C22 N2 In1 121.88(7) . . ? C6 N2 In1 109.88(7) . . ? C22 N2 H2N 109.4 . . ? C6 N2 H2N 104.4 . . ? In1 N2 H2N 92.1 . . ? C8 O1 In1 127.83(8) . . ? O1 In1 N1 87.9 . . ? O1 In1 Cl1 95.7 . . ? N1 In1 Cl1 140.5 . . ? O1 In1 N2 162.1 . . ? N1 In1 N2 75.6 . . ? Cl1 In1 N2 92.8 . . ? O1 In1 Cl2 104.9 . . ? N1 In1 Cl2 100.4 . . ? Cl1 In1 Cl2 116.4 . . ? N2 In1 Cl2 85.3 . . ? 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 C1 C2 C3 -175.26(15) . . . . ? C6 C1 C2 C3 -54.2(2) . . . . ? C1 C2 C3 C4 54.6(2) . . . . ? C2 C3 C4 C5 -56.0(2) . . . . ? C3 C4 C5 C6 58.0(2) . . . . ? C4 C5 C6 N2 179.09(14) . . . . ? C4 C5 C6 C1 -58.4(2) . . . . ? N1 C1 C6 N2 -56.82(17) . . . . ? C2 C1 C6 N2 179.76(14) . . . . ? N1 C1 C6 C5 179.27(14) . . . . ? C2 C1 C6 C5 55.9(2) . . . . ? O1 C8 C9 C10 177.26(16) . . . . ? C13 C8 C9 C10 -1.2(3) . . . . ? O1 C8 C9 C18 -3.1(3) . . . . ? C13 C8 C9 C18 178.46(18) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C18 C9 C10 C11 -179.92(18) . . . . ? C9 C10 C11 C12 1.4(3) . . . . ? C9 C10 C11 C14 -178.96(18) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? C14 C11 C12 C13 179.26(18) . . . . ? C11 C12 C13 C8 -0.3(3) . . . . ? C11 C12 C13 C7 -179.62(18) . . . . ? O1 C8 C13 C12 -176.97(16) . . . . ? C9 C8 C13 C12 1.5(3) . . . . ? O1 C8 C13 C7 2.4(3) . . . . ? C9 C8 C13 C7 -179.17(17) . . . . ? N1 C7 C13 C12 -120.10(18) . . . . ? N1 C7 C13 C8 60.5(2) . . . . ? C12 C11 C14 C15 -9.6(3) . . . . ? C10 C11 C14 C15 170.84(19) . . . . ? C12 C11 C14 C16 111.4(2) . . . . ? C10 C11 C14 C16 -68.2(2) . . . . ? C12 C11 C14 C17 -129.9(2) . . . . ? C10 C11 C14 C17 50.5(2) . . . . ? C10 C9 C18 C19 -121.9(2) . . . . ? C8 C9 C18 C19 58.4(2) . . . . ? C10 C9 C18 C21 -2.5(3) . . . . ? C8 C9 C18 C21 177.85(18) . . . . ? C10 C9 C18 C20 116.7(2) . . . . ? C8 C9 C18 C20 -62.9(2) . . . . ? C27 C22 C23 C24 -1.7(3) . . . . ? N2 C22 C23 C24 -179.75(16) . . . . ? C27 C22 C23 C28 177.79(19) . . . . ? N2 C22 C23 C28 -0.3(3) . . . . ? C22 C23 C24 C25 0.8(3) . . . . ? C28 C23 C24 C25 -178.68(19) . . . . ? C23 C24 C25 C26 0.4(3) . . . . ? C23 C24 C25 C29 -179.4(2) . . . . ? C24 C25 C26 C27 -0.8(3) . . . . ? C29 C25 C26 C27 179.0(2) . . . . ? C25 C26 C27 C22 0.0(3) . . . . ? C25 C26 C27 C30 -179.8(2) . . . . ? C23 C22 C27 C26 1.3(3) . . . . ? N2 C22 C27 C26 179.41(16) . . . . ? C23 C22 C27 C30 -178.91(19) . . . . ? N2 C22 C27 C30 -0.8(3) . . . . ? C34 O2 C31 C32 -40.11(14) . . . . ? O2 C31 C32 C33 23.32(8) . . . . ? C31 C32 C33 C34 -1.0 . . . . ? C31 O2 C34 C33 38.65(13) . . . . ? C32 C33 C34 O2 -22.38(9) . . . . ? C2 C1 N1 C7 -65.41(18) . . . . ? C6 C1 N1 C7 172.50(13) . . . . ? C2 C1 N1 In1 177.04(12) . . . . ? C6 C1 N1 In1 54.96(14) . . . . ? C13 C7 N1 C1 167.15(14) . . . . ? C13 C7 N1 In1 -73.74(15) . . . . ? C23 C22 N2 C6 -69.0(2) . . . . ? C27 C22 N2 C6 112.89(17) . . . . ? C23 C22 N2 In1 68.39(19) . . . . ? C27 C22 N2 In1 -109.72(15) . . . . ? C5 C6 N2 C22 -64.25(17) . . . . ? C1 C6 N2 C22 172.27(13) . . . . ? C5 C6 N2 In1 153.44(12) . . . . ? C1 C6 N2 In1 29.95(15) . . . . ? C13 C8 O1 In1 -38.3(2) . . . . ? C9 C8 O1 In1 143.26(13) . . . . ? C8 O1 In1 N1 15.72(10) . . . . ? C8 O1 In1 Cl1 -124.87(10) . . . . ? C8 O1 In1 N2 -7.05(10) . . . . ? C8 O1 In1 Cl2 115.92(10) . . . . ? C1 N1 In1 O1 158.68(8) . . . . ? C7 N1 In1 O1 35.76(8) . . . . ? C1 N1 In1 Cl1 -104.90(8) . . . . ? C7 N1 In1 Cl1 132.18(8) . . . . ? C1 N1 In1 N2 -28.39(8) . . . . ? C7 N1 In1 N2 -151.31(8) . . . . ? C1 N1 In1 Cl2 53.94(8) . . . . ? C7 N1 In1 Cl2 -68.98(8) . . . . ? C22 N2 In1 O1 -117.01(9) . . . . ? C6 N2 In1 O1 22.36(8) . . . . ? C22 N2 In1 N1 -140.55(9) . . . . ? C6 N2 In1 N1 -1.18(8) . . . . ? C22 N2 In1 Cl1 1.21(9) . . . . ? C6 N2 In1 Cl1 140.58(8) . . . . ? C22 N2 In1 Cl2 117.43(9) . . . . ? C6 N2 In1 Cl2 -103.19(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.20 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.281 _refine_diff_density_min -0.581 _refine_diff_density_rms 0.088 #===END data_pm072_01m _database_code_depnum_ccdc_archive 'CCDC 864184' #TrackingRef '- Mehr_DaltonJan192012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H99 Cl2 In2 N4 O4' _chemical_formula_sum 'C56 H99 Cl2 In2 N4 O4' _chemical_formula_weight 1192.93 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 '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 36.9023(16) _cell_length_b 10.2529(5) _cell_length_c 17.8775(9) _cell_angle_alpha 90.00 _cell_angle_beta 116.647(2) _cell_angle_gamma 90.00 _cell_volume 6045.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9121 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 27.32 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2508 _exptl_absorpt_coefficient_mu 0.895 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8792 _exptl_absorpt_correction_T_max 0.9562 _exptl_absorpt_process_details ? _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 '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 40441 _diffrn_reflns_av_R_equivalents 0.0822 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 27.55 _reflns_number_total 6964 _reflns_number_gt 5023 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0594P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6964 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 In1 In 0.947425(6) 0.97347(3) 0.196446(15) 0.01270(9) Uani 1 1 d . . . Cl1 Cl 0.93357(3) 0.98025(10) 0.31714(6) 0.0221(2) Uani 1 1 d . . . O2 O 1.0000 0.8502(3) 0.2500 0.0196(8) Uani 1 2 d S . 1 O3 O 1.0000 1.0997(3) 0.2500 0.0168(8) Uani 1 2 d S . 1 O1 O 0.90985(7) 0.8166(2) 0.13918(15) 0.0164(5) Uani 1 1 d . . . N1 N 0.90539(8) 1.1624(3) 0.13147(18) 0.0149(6) Uani 1 1 d . . . N2 N 0.95358(8) 1.0038(3) 0.07713(18) 0.0136(7) Uani 1 1 d . . . H2N H 0.9813 1.0100 0.0943 0.016 Uiso 1 1 calc R . . C1 C 0.92654(10) 1.2253(4) 0.0864(2) 0.0176(8) Uani 1 1 d . . . H1 H 0.9533 1.2558 0.1309 0.021 Uiso 1 1 calc R . . C2 C 0.93651(10) 1.1278(4) 0.0330(2) 0.0152(8) Uani 1 1 d . . . H2A H 0.9109 1.1077 -0.0183 0.018 Uiso 1 1 calc R . . C7 C 0.94039(9) 0.8860(4) 0.0224(2) 0.0145(8) Uani 1 1 d . . . H7A H 0.9585 0.8125 0.0522 0.017 Uiso 1 1 calc R . . H7B H 0.9436 0.9034 -0.0287 0.017 Uiso 1 1 calc R . . C13 C 0.89695(9) 0.8449(4) -0.0033(2) 0.0137(7) Uani 1 1 d . . . C12 C 0.86981(10) 0.8434(4) -0.0872(2) 0.0163(8) Uani 1 1 d . . . H12 H 0.8782 0.8747 -0.1269 0.020 Uiso 1 1 calc R . . C11 C 0.83016(10) 0.7970(4) -0.1153(2) 0.0179(8) Uani 1 1 d . . . C15 C 0.80064(10) 0.7923(4) -0.2089(2) 0.0234(9) Uani 1 1 d . . . C19 C 0.80945(13) 0.6696(5) -0.2466(3) 0.0374(11) Uani 1 1 d . . . H19A H 0.7908 0.6654 -0.3065 0.056 Uiso 1 1 calc R . . H19B H 0.8057 0.5923 -0.2185 0.056 Uiso 1 1 calc R . . H19C H 0.8375 0.6724 -0.2389 0.056 Uiso 1 1 calc R . . C21 C 0.80565(12) 0.9104(5) -0.2551(3) 0.0366(11) Uani 1 1 d . . . H21A H 0.7863 0.9048 -0.3144 0.055 Uiso 1 1 calc R . . H21B H 0.8333 0.9122 -0.2494 0.055 Uiso 1 1 calc R . . H21C H 0.8006 0.9902 -0.2310 0.055 Uiso 1 1 calc R . . C20 C 0.75619(11) 0.7886(5) -0.2239(3) 0.0413(13) Uani 1 1 d . . . H20A H 0.7383 0.7867 -0.2842 0.062 Uiso 1 1 calc R . . H20B H 0.7503 0.8664 -0.1994 0.062 Uiso 1 1 calc R . . H20C H 0.7517 0.7103 -0.1977 0.062 Uiso 1 1 calc R . . C10 C 0.82000(10) 0.7482(4) -0.0540(2) 0.0196(8) Uani 1 1 d . . . H10 H 0.7937 0.7126 -0.0719 0.024 Uiso 1 1 calc R . . C9 C 0.84589(10) 0.7485(4) 0.0312(2) 0.0156(8) Uani 1 1 d . . . C14 C 0.83280(10) 0.6920(4) 0.0951(2) 0.0179(8) Uani 1 1 d . . . C18 C 0.79364(12) 0.6120(5) 0.0527(3) 0.0344(11) Uani 1 1 d . . . H18A H 0.7863 0.5779 0.0953 0.052 Uiso 1 1 calc R . . H18B H 0.7979 0.5392 0.0219 0.052 Uiso 1 1 calc R . . H18C H 0.7717 0.6677 0.0137 0.052 Uiso 1 1 calc R . . C16 C 0.86501(12) 0.5990(4) 0.1557(3) 0.0301(10) Uani 1 1 d . . . H16A H 0.8561 0.5644 0.1957 0.045 Uiso 1 1 calc R . . H16B H 0.8906 0.6461 0.1859 0.045 Uiso 1 1 calc R . . H16C H 0.8690 0.5268 0.1241 0.045 Uiso 1 1 calc R . . C17 C 0.82590(11) 0.8016(4) 0.1453(2) 0.0232(9) Uani 1 1 d . . . H17A H 0.8176 0.7642 0.1857 0.035 Uiso 1 1 calc R . . H17B H 0.8046 0.8600 0.1072 0.035 Uiso 1 1 calc R . . H17C H 0.8511 0.8510 0.1753 0.035 Uiso 1 1 calc R . . C8 C 0.88485(10) 0.8044(3) 0.0571(2) 0.0139(7) Uani 1 1 d . . . C3 C 0.96600(11) 1.1928(4) 0.0057(2) 0.0202(8) Uani 1 1 d . . . H3A H 0.9917 1.2119 0.0559 0.024 Uiso 1 1 calc R . . H3B H 0.9721 1.1314 -0.0299 0.024 Uiso 1 1 calc R . . C4 C 0.94932(13) 1.3184(4) -0.0424(3) 0.0288(10) Uani 1 1 d . . . H4A H 0.9704 1.3607 -0.0538 0.035 Uiso 1 1 calc R . . H4B H 0.9259 1.2981 -0.0967 0.035 Uiso 1 1 calc R . . C5 C 0.93599(14) 1.4113(4) 0.0064(3) 0.0331(10) Uani 1 1 d . . . H5A H 0.9226 1.4881 -0.0288 0.040 Uiso 1 1 calc R . . H5B H 0.9600 1.4424 0.0566 0.040 Uiso 1 1 calc R . . C6 C 0.90674(12) 1.3444(4) 0.0332(3) 0.0273(9) Uani 1 1 d . . . H6A H 0.8987 1.4063 0.0656 0.033 Uiso 1 1 calc R . . H6B H 0.8820 1.3178 -0.0170 0.033 Uiso 1 1 calc R . . C25 C 0.90130(10) 1.2501(4) 0.1941(2) 0.0179(8) Uani 1 1 d . . . H25A H 0.8879 1.2003 0.2221 0.022 Uiso 1 1 calc R . . H25B H 0.8830 1.3228 0.1634 0.022 Uiso 1 1 calc R . . C26 C 0.94009(10) 1.3084(4) 0.2615(2) 0.0230(9) Uani 1 1 d . . . H26A H 0.9600 1.2379 0.2888 0.028 Uiso 1 1 calc R . . H26B H 0.9519 1.3694 0.2354 0.028 Uiso 1 1 calc R . . C27 C 0.93229(11) 1.3806(4) 0.3271(2) 0.0241(9) Uani 1 1 d . . . H27A H 0.9578 1.4180 0.3691 0.036 Uiso 1 1 calc R . . H27B H 0.9214 1.3197 0.3543 0.036 Uiso 1 1 calc R . . H27C H 0.9126 1.4507 0.3002 0.036 Uiso 1 1 calc R . . C22 C 0.86424(9) 1.1082(4) 0.0753(2) 0.0166(8) Uani 1 1 d . . . H22A H 0.8585 1.0384 0.1067 0.020 Uiso 1 1 calc R . . H22B H 0.8661 1.0660 0.0274 0.020 Uiso 1 1 calc R . . C23 C 0.82761(10) 1.1980(4) 0.0397(3) 0.0258(9) Uani 1 1 d . . . H23A H 0.8227 1.2336 0.0859 0.031 Uiso 1 1 calc R . . H23B H 0.8329 1.2720 0.0105 0.031 Uiso 1 1 calc R . . C24 C 0.79067(11) 1.1246(5) -0.0205(3) 0.0360(11) Uani 1 1 d . . . H24A H 0.7673 1.1837 -0.0433 0.054 Uiso 1 1 calc R . . H24B H 0.7851 1.0525 0.0089 0.054 Uiso 1 1 calc R . . H24C H 0.7955 1.0898 -0.0663 0.054 Uiso 1 1 calc R . . C28 C 0.9968(2) 0.7128(8) 0.2722(5) 0.0203(17) Uani 0.50 1 d P . . H28A H 0.9722 0.7013 0.2805 0.024 Uiso 0.50 1 calc PR . 1 H28B H 1.0207 0.6891 0.3248 0.024 Uiso 0.50 1 calc PR . 1 C29 C 0.9944(3) 0.6264(9) 0.2015(5) 0.036(2) Uani 0.50 1 d P . . H29A H 0.9684 0.6404 0.1521 0.054 Uiso 0.50 1 calc PR . . H29B H 0.9966 0.5348 0.2186 0.054 Uiso 0.50 1 calc PR . . H29C H 1.0166 0.6482 0.1879 0.054 Uiso 0.50 1 calc PR . . 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 In1 0.01417(12) 0.01631(15) 0.00662(13) 0.00030(11) 0.00378(9) -0.00051(10) Cl1 0.0311(4) 0.0270(5) 0.0111(4) 0.0017(4) 0.0123(4) 0.0008(4) O2 0.0155(16) 0.015(2) 0.018(2) 0.000 -0.0016(15) 0.000 O3 0.0111(14) 0.020(2) 0.0144(19) 0.000 0.0015(14) 0.000 O1 0.0181(11) 0.0215(15) 0.0080(12) 0.0014(11) 0.0044(10) -0.0022(10) N1 0.0211(14) 0.0169(17) 0.0093(15) -0.0025(13) 0.0090(13) -0.0010(12) N2 0.0130(12) 0.0168(18) 0.0094(15) -0.0004(12) 0.0037(12) -0.0017(11) C1 0.0235(17) 0.018(2) 0.0130(19) 0.0013(16) 0.0101(16) -0.0005(15) C2 0.0187(16) 0.018(2) 0.0084(17) 0.0007(15) 0.0057(14) -0.0013(14) C7 0.0159(15) 0.017(2) 0.0119(18) 0.0004(15) 0.0078(14) 0.0011(14) C13 0.0158(15) 0.016(2) 0.0098(17) -0.0028(15) 0.0058(14) 0.0002(14) C12 0.0186(16) 0.021(2) 0.0114(18) -0.0022(16) 0.0081(15) -0.0018(15) C11 0.0181(16) 0.024(2) 0.0124(19) -0.0020(16) 0.0071(15) 0.0002(15) C15 0.0170(16) 0.036(3) 0.0128(19) -0.0043(18) 0.0031(15) -0.0051(16) C19 0.038(2) 0.050(3) 0.017(2) -0.012(2) 0.0056(19) -0.007(2) C21 0.032(2) 0.048(3) 0.019(2) 0.006(2) 0.0021(19) -0.004(2) C20 0.0170(18) 0.082(4) 0.020(2) 0.002(2) 0.0045(17) -0.003(2) C10 0.0154(15) 0.025(2) 0.018(2) -0.0040(17) 0.0074(15) -0.0050(15) C9 0.0182(15) 0.016(2) 0.0138(18) -0.0022(15) 0.0085(15) -0.0001(14) C14 0.0187(16) 0.020(2) 0.0169(19) 0.0023(16) 0.0099(15) -0.0006(15) C18 0.037(2) 0.040(3) 0.029(2) -0.004(2) 0.017(2) -0.021(2) C16 0.037(2) 0.023(2) 0.041(3) 0.016(2) 0.027(2) 0.0083(18) C17 0.0252(18) 0.028(2) 0.023(2) 0.0002(18) 0.0167(17) 0.0006(16) C8 0.0184(16) 0.0128(19) 0.0095(17) -0.0007(15) 0.0054(14) 0.0011(14) C3 0.0269(18) 0.024(2) 0.0127(19) -0.0021(16) 0.0116(16) -0.0033(16) C4 0.046(2) 0.024(2) 0.026(2) 0.0066(19) 0.025(2) 0.0008(19) C5 0.058(3) 0.022(2) 0.033(3) 0.011(2) 0.032(2) 0.005(2) C6 0.042(2) 0.022(2) 0.024(2) 0.0045(18) 0.020(2) 0.0055(18) C25 0.0240(17) 0.018(2) 0.0140(19) -0.0009(16) 0.0105(16) 0.0020(15) C26 0.0248(18) 0.024(2) 0.023(2) -0.0078(18) 0.0133(17) -0.0027(16) C27 0.0275(18) 0.029(2) 0.014(2) -0.0034(17) 0.0075(17) 0.0050(17) C22 0.0185(16) 0.018(2) 0.0120(18) 0.0007(15) 0.0052(15) 0.0004(14) C23 0.0227(18) 0.025(2) 0.023(2) 0.0015(18) 0.0044(17) 0.0063(16) C24 0.0233(19) 0.041(3) 0.032(3) 0.001(2) 0.0023(19) 0.0057(19) C28 0.015(3) 0.023(4) 0.020(5) 0.003(3) 0.005(3) 0.000(3) C29 0.050(5) 0.023(5) 0.030(5) -0.008(4) 0.014(5) -0.001(4) _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 In1 O1 2.070(2) . ? In1 O2 2.147(2) . ? In1 O3 2.165(2) . ? In1 N2 2.266(3) . ? In1 N1 2.427(3) . ? In1 Cl1 2.4314(9) . ? O2 C28 1.483(9) 2_755 ? O2 C28 1.483(9) . ? O2 In1 2.147(2) 2_755 ? O3 In1 2.165(2) 2_755 ? O1 C8 1.344(4) . ? N1 C25 1.496(4) . ? N1 C1 1.496(4) . ? N1 C22 1.502(4) . ? N2 C2 1.480(4) . ? N2 C7 1.492(4) . ? N2 H2N 0.9300 . ? C1 C6 1.519(5) . ? C1 C2 1.537(5) . ? C1 H1 1.0000 . ? C2 C3 1.530(5) . ? C2 H2A 1.0000 . ? C7 C13 1.516(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C13 C12 1.380(5) . ? C13 C8 1.403(5) . ? C12 C11 1.400(4) . ? C12 H12 0.9500 . ? C11 C10 1.399(5) . ? C11 C15 1.535(5) . ? C15 C21 1.522(6) . ? C15 C19 1.529(6) . ? C15 C20 1.539(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C10 C9 1.389(5) . ? C10 H10 0.9500 . ? C9 C8 1.419(4) . ? C9 C14 1.540(5) . ? C14 C16 1.530(5) . ? C14 C17 1.529(5) . ? C14 C18 1.534(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C3 C4 1.517(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.515(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C25 C26 1.520(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.519(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C22 C23 1.519(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.505(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C28 C29 1.514(10) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 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 O1 In1 O2 91.95(10) . . ? O1 In1 O3 162.11(9) . . ? O2 In1 O3 72.74(11) . . ? O1 In1 N2 88.21(10) . . ? O2 In1 N2 92.78(7) . . ? O3 In1 N2 83.46(7) . . ? O1 In1 N1 103.95(10) . . ? O2 In1 N1 159.82(10) . . ? O3 In1 N1 89.32(10) . . ? N2 In1 N1 75.66(10) . . ? O1 In1 Cl1 95.76(7) . . ? O2 In1 Cl1 97.39(2) . . ? O3 In1 Cl1 95.38(3) . . ? N2 In1 Cl1 168.94(8) . . ? N1 In1 Cl1 93.34(7) . . ? C28 O2 C28 36.4(6) 2_755 . ? C28 O2 In1 120.9(3) 2_755 2_755 ? C28 O2 In1 127.2(3) . 2_755 ? C28 O2 In1 127.2(3) 2_755 . ? C28 O2 In1 120.9(3) . . ? In1 O2 In1 107.90(15) 2_755 . ? In1 O3 In1 106.61(15) . 2_755 ? C8 O1 In1 126.3(2) . . ? C25 N1 C1 113.4(3) . . ? C25 N1 C22 108.2(3) . . ? C1 N1 C22 114.5(3) . . ? C25 N1 In1 112.3(2) . . ? C1 N1 In1 103.06(19) . . ? C22 N1 In1 105.2(2) . . ? C2 N2 C7 114.2(3) . . ? C2 N2 In1 114.9(2) . . ? C7 N2 In1 111.4(2) . . ? C2 N2 H2N 105.0 . . ? C7 N2 H2N 105.0 . . ? In1 N2 H2N 105.0 . . ? N1 C1 C6 117.6(3) . . ? N1 C1 C2 112.5(3) . . ? C6 C1 C2 108.4(3) . . ? N1 C1 H1 105.8 . . ? C6 C1 H1 105.8 . . ? C2 C1 H1 105.8 . . ? N2 C2 C3 110.5(3) . . ? N2 C2 C1 113.0(3) . . ? C3 C2 C1 108.5(3) . . ? N2 C2 H2A 108.2 . . ? C3 C2 H2A 108.2 . . ? C1 C2 H2A 108.2 . . ? N2 C7 C13 114.4(3) . . ? N2 C7 H7A 108.7 . . ? C13 C7 H7A 108.7 . . ? N2 C7 H7B 108.7 . . ? C13 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C12 C13 C8 120.4(3) . . ? C12 C13 C7 119.1(3) . . ? C8 C13 C7 120.5(3) . . ? C13 C12 C11 121.8(3) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C10 C11 C12 116.4(3) . . ? C10 C11 C15 122.3(3) . . ? C12 C11 C15 121.2(3) . . ? C21 C15 C19 108.3(4) . . ? C21 C15 C11 111.5(3) . . ? C19 C15 C11 108.6(3) . . ? C21 C15 C20 107.7(3) . . ? C19 C15 C20 108.9(3) . . ? C11 C15 C20 111.7(3) . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C9 C10 C11 124.3(3) . . ? C9 C10 H10 117.8 . . ? C11 C10 H10 117.8 . . ? C10 C9 C8 117.2(3) . . ? C10 C9 C14 121.5(3) . . ? C8 C9 C14 121.3(3) . . ? C16 C14 C17 108.9(3) . . ? C16 C14 C18 106.1(3) . . ? C17 C14 C18 108.4(3) . . ? C16 C14 C9 110.9(3) . . ? C17 C14 C9 110.5(3) . . ? C18 C14 C9 111.9(3) . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C8 C13 120.9(3) . . ? O1 C8 C9 119.5(3) . . ? C13 C8 C9 119.6(3) . . ? C4 C3 C2 112.6(3) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 111.2(3) . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 110.8(4) . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C1 C6 C5 110.4(3) . . ? C1 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? C1 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N1 C25 C26 117.0(3) . . ? N1 C25 H25A 108.0 . . ? C26 C25 H25A 108.0 . . ? N1 C25 H25B 108.0 . . ? C26 C25 H25B 108.0 . . ? H25A C25 H25B 107.3 . . ? C27 C26 C25 111.5(3) . . ? C27 C26 H26A 109.3 . . ? C25 C26 H26A 109.3 . . ? C27 C26 H26B 109.3 . . ? C25 C26 H26B 109.3 . . ? H26A C26 H26B 108.0 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N1 C22 C23 119.9(3) . . ? N1 C22 H22A 107.3 . . ? C23 C22 H22A 107.3 . . ? N1 C22 H22B 107.3 . . ? C23 C22 H22B 107.3 . . ? H22A C22 H22B 106.9 . . ? C24 C23 C22 110.3(3) . . ? C24 C23 H23A 109.6 . . ? C22 C23 H23A 109.6 . . ? C24 C23 H23B 109.6 . . ? C22 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O2 C28 C29 108.3(5) . . ? O2 C28 H28A 110.0 . . ? C29 C28 H28A 110.0 . . ? O2 C28 H28B 110.0 . . ? C29 C28 H28B 110.0 . . ? H28A C28 H28B 108.4 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? 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 In1 O2 C28 13.2(4) . . . 2_755 ? O3 In1 O2 C28 -157.3(4) . . . 2_755 ? N2 In1 O2 C28 -75.1(4) . . . 2_755 ? N1 In1 O2 C28 -129.1(4) . . . 2_755 ? Cl1 In1 O2 C28 109.3(4) . . . 2_755 ? O1 In1 O2 C28 -30.4(4) . . . . ? O3 In1 O2 C28 159.0(3) . . . . ? N2 In1 O2 C28 -118.7(4) . . . . ? N1 In1 O2 C28 -172.8(4) . . . . ? Cl1 In1 O2 C28 65.7(3) . . . . ? O1 In1 O2 In1 170.57(7) . . . 2_755 ? O3 In1 O2 In1 0.000(1) . . . 2_755 ? N2 In1 O2 In1 82.27(7) . . . 2_755 ? N1 In1 O2 In1 28.2(2) . . . 2_755 ? Cl1 In1 O2 In1 -93.37(3) . . . 2_755 ? O1 In1 O3 In1 -32.2(2) . . . 2_755 ? O2 In1 O3 In1 0.000(1) . . . 2_755 ? N2 In1 O3 In1 -94.97(7) . . . 2_755 ? N1 In1 O3 In1 -170.62(7) . . . 2_755 ? Cl1 In1 O3 In1 96.09(3) . . . 2_755 ? O2 In1 O1 C8 -124.2(2) . . . . ? O3 In1 O1 C8 -93.6(3) . . . . ? N2 In1 O1 C8 -31.5(3) . . . . ? N1 In1 O1 C8 43.3(3) . . . . ? Cl1 In1 O1 C8 138.2(2) . . . . ? O1 In1 N1 C25 122.0(2) . . . . ? O2 In1 N1 C25 -97.0(3) . . . . ? O3 In1 N1 C25 -70.1(2) . . . . ? N2 In1 N1 C25 -153.6(2) . . . . ? Cl1 In1 N1 C25 25.2(2) . . . . ? O1 In1 N1 C1 -115.7(2) . . . . ? O2 In1 N1 C1 25.4(4) . . . . ? O3 In1 N1 C1 52.2(2) . . . . ? N2 In1 N1 C1 -31.2(2) . . . . ? Cl1 In1 N1 C1 147.6(2) . . . . ? O1 In1 N1 C22 4.6(2) . . . . ? O2 In1 N1 C22 145.6(2) . . . . ? O3 In1 N1 C22 172.44(19) . . . . ? N2 In1 N1 C22 89.0(2) . . . . ? Cl1 In1 N1 C22 -92.20(19) . . . . ? O1 In1 N2 C2 115.3(2) . . . . ? O2 In1 N2 C2 -152.9(2) . . . . ? O3 In1 N2 C2 -80.6(2) . . . . ? N1 In1 N2 C2 10.4(2) . . . . ? Cl1 In1 N2 C2 4.0(5) . . . . ? O1 In1 N2 C7 -16.7(2) . . . . ? O2 In1 N2 C7 75.2(2) . . . . ? O3 In1 N2 C7 147.4(2) . . . . ? N1 In1 N2 C7 -121.6(2) . . . . ? Cl1 In1 N2 C7 -128.0(3) . . . . ? C25 N1 C1 C6 -62.2(4) . . . . ? C22 N1 C1 C6 62.6(4) . . . . ? In1 N1 C1 C6 176.2(3) . . . . ? C25 N1 C1 C2 170.8(3) . . . . ? C22 N1 C1 C2 -64.4(4) . . . . ? In1 N1 C1 C2 49.2(3) . . . . ? C7 N2 C2 C3 -94.7(3) . . . . ? In1 N2 C2 C3 134.7(2) . . . . ? C7 N2 C2 C1 143.5(3) . . . . ? In1 N2 C2 C1 12.9(3) . . . . ? N1 C1 C2 N2 -44.5(4) . . . . ? C6 C1 C2 N2 -176.3(3) . . . . ? N1 C1 C2 C3 -167.4(3) . . . . ? C6 C1 C2 C3 60.8(4) . . . . ? C2 N2 C7 C13 -73.8(4) . . . . ? In1 N2 C7 C13 58.5(3) . . . . ? N2 C7 C13 C12 118.9(4) . . . . ? N2 C7 C13 C8 -63.4(4) . . . . ? C8 C13 C12 C11 -2.7(6) . . . . ? C7 C13 C12 C11 175.0(3) . . . . ? C13 C12 C11 C10 -2.0(5) . . . . ? C13 C12 C11 C15 -178.3(4) . . . . ? C10 C11 C15 C21 146.1(4) . . . . ? C12 C11 C15 C21 -37.9(5) . . . . ? C10 C11 C15 C19 -94.6(4) . . . . ? C12 C11 C15 C19 81.4(4) . . . . ? C10 C11 C15 C20 25.5(5) . . . . ? C12 C11 C15 C20 -158.5(4) . . . . ? C12 C11 C10 C9 2.8(6) . . . . ? C15 C11 C10 C9 179.0(4) . . . . ? C11 C10 C9 C8 1.2(6) . . . . ? C11 C10 C9 C14 -179.4(4) . . . . ? C10 C9 C14 C16 131.0(4) . . . . ? C8 C9 C14 C16 -49.7(5) . . . . ? C10 C9 C14 C17 -108.2(4) . . . . ? C8 C9 C14 C17 71.2(4) . . . . ? C10 C9 C14 C18 12.7(5) . . . . ? C8 C9 C14 C18 -168.0(3) . . . . ? In1 O1 C8 C13 40.4(4) . . . . ? In1 O1 C8 C9 -140.3(3) . . . . ? C12 C13 C8 O1 -173.9(3) . . . . ? C7 C13 C8 O1 8.4(5) . . . . ? C12 C13 C8 C9 6.8(5) . . . . ? C7 C13 C8 C9 -170.8(3) . . . . ? C10 C9 C8 O1 174.7(3) . . . . ? C14 C9 C8 O1 -4.6(5) . . . . ? C10 C9 C8 C13 -6.0(5) . . . . ? C14 C9 C8 C13 174.6(3) . . . . ? N2 C2 C3 C4 178.1(3) . . . . ? C1 C2 C3 C4 -57.5(4) . . . . ? C2 C3 C4 C5 53.7(4) . . . . ? C3 C4 C5 C6 -53.1(5) . . . . ? N1 C1 C6 C5 168.7(3) . . . . ? C2 C1 C6 C5 -62.3(4) . . . . ? C4 C5 C6 C1 58.4(5) . . . . ? C1 N1 C25 C26 -56.1(4) . . . . ? C22 N1 C25 C26 175.8(3) . . . . ? In1 N1 C25 C26 60.2(4) . . . . ? N1 C25 C26 C27 -172.6(3) . . . . ? C25 N1 C22 C23 45.6(4) . . . . ? C1 N1 C22 C23 -81.9(4) . . . . ? In1 N1 C22 C23 165.7(3) . . . . ? N1 C22 C23 C24 174.9(3) . . . . ? C28 O2 C28 C29 -14.5(6) 2_755 . . . ? In1 O2 C28 C29 -107.6(5) 2_755 . . . ? In1 O2 C28 C29 97.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.712 _refine_diff_density_min -1.582 _refine_diff_density_rms 0.362 #===END