# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ales Ruzicka' _publ_contact_author_email ales.ruzicka@upce.cz loop_ _publ_author_name L.Dostal R.Jambor A.Ruzicka R.Jirasko J.Holecek #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 801796' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H25 Cl O2 Sb, C F3 O3 S' _chemical_formula_sum 'C17 H25 Cl F3 O5 S Sb' _chemical_formula_weight 555.63 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 '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 9.3050(10) _cell_length_b 12.4460(12) _cell_length_c 19.4031(14) _cell_angle_alpha 90 _cell_angle_beta 104.615(6) _cell_angle_gamma 90 _cell_volume 2174.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 17629 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.697 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 1.538 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.078 0 1 -1 0.100 0 -1 -1 0.139 1 0 0 0.040 -1 0 0 0.057 0 0 -1 0.170 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_T_max 0.854 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17557 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4950 _reflns_number_gt 3668 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0286P)^2^+1.6163P] 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 4950 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0691 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.29742(2) 0.358721(18) 0.344472(11) 0.03058(8) Uani 1 1 d . . . S1 S 0.30741(10) 0.35687(9) 0.16336(5) 0.0450(2) Uani 1 1 d . . . Cl1 Cl 0.28437(10) 0.36552(8) 0.46610(5) 0.0488(2) Uani 1 1 d . . . F1 F 0.0218(3) 0.3604(2) 0.14455(17) 0.0843(9) Uani 1 1 d . . . O1 O 0.3662(2) 0.18078(18) 0.36523(13) 0.0375(5) Uani 1 1 d . . . O2 O 0.3636(2) 0.53507(17) 0.35513(12) 0.0344(5) Uani 1 1 d . . . C17 C 0.1229(5) 0.3588(4) 0.1066(2) 0.0621(12) Uani 1 1 d . . . C1 C 0.5296(3) 0.3575(3) 0.36742(16) 0.0329(7) Uani 1 1 d . . . C13 C 0.2644(4) 0.6297(3) 0.35292(19) 0.0391(8) Uani 1 1 d . . . C6 C 0.6027(3) 0.4549(3) 0.37181(17) 0.0348(8) Uani 1 1 d . . . F3 F 0.0960(3) 0.2728(3) 0.06592(19) 0.1276(15) Uani 1 1 d . . . O3 O 0.3126(4) 0.4516(3) 0.20542(17) 0.0803(10) Uani 1 1 d . . . C12 C 0.5164(3) 0.5570(3) 0.3564(2) 0.0411(8) Uani 1 1 d . . . H12A H 0.5572 0.6098 0.3928 0.049 Uiso 1 1 d R . . H12B H 0.5228 0.5855 0.3107 0.049 Uiso 1 1 d R . . C14 C 0.2698(5) 0.6978(3) 0.2890(2) 0.0582(11) Uani 1 1 d . . . H14A H 0.3639 0.7339 0.2976 0.070 Uiso 1 1 d R . . H14B H 0.1914 0.7501 0.2806 0.070 Uiso 1 1 d R . . H14C H 0.2575 0.6522 0.2480 0.070 Uiso 1 1 d R . . C9 C 0.2702(5) 0.0205(3) 0.2973(2) 0.0550(10) Uani 1 1 d . . . H9A H 0.2506 0.0653 0.2556 0.066 Uiso 1 1 d R . . H9B H 0.1962 -0.0349 0.2911 0.066 Uiso 1 1 d R . . H9C H 0.3666 -0.0116 0.3042 0.066 Uiso 1 1 d R . . C8 C 0.2655(4) 0.0869(3) 0.36179(18) 0.0377(8) Uani 1 1 d . . . O4 O 0.3998(3) 0.3567(3) 0.11490(16) 0.0686(9) Uani 1 1 d . . . C4 C 0.8331(4) 0.3595(4) 0.4037(2) 0.0498(9) Uani 1 1 d . . . H4 H 0.9364 0.3601 0.4159 0.060 Uiso 1 1 d R . . O5 O 0.3093(4) 0.2615(3) 0.20468(18) 0.0830(11) Uani 1 1 d . . . C5 C 0.7577(4) 0.4552(3) 0.39015(19) 0.0451(9) Uani 1 1 d . . . H5 H 0.8092 0.5198 0.3932 0.054 Uiso 1 1 d R . . C2 C 0.6049(4) 0.2617(3) 0.38107(18) 0.0375(8) Uani 1 1 d . . . C10 C 0.1125(4) 0.1346(3) 0.3539(3) 0.0559(11) Uani 1 1 d . . . H10A H 0.1121 0.1778 0.3948 0.067 Uiso 1 1 d R . . H10B H 0.0415 0.0775 0.3500 0.067 Uiso 1 1 d R . . H10C H 0.0868 0.1783 0.3118 0.067 Uiso 1 1 d R . . C15 C 0.1099(4) 0.5818(3) 0.3436(3) 0.0573(11) Uani 1 1 d . . . H15A H 0.0397 0.6384 0.3435 0.069 Uiso 1 1 d R . . H15B H 0.1106 0.5334 0.3822 0.069 Uiso 1 1 d R . . H15C H 0.0821 0.5434 0.2993 0.069 Uiso 1 1 d R . . C3 C 0.7600(4) 0.2627(3) 0.3994(2) 0.0465(9) Uani 1 1 d . . . H3 H 0.8129 0.1987 0.4088 0.056 Uiso 1 1 d R . . C16 C 0.3135(5) 0.6894(4) 0.4223(2) 0.0563(11) Uani 1 1 d . . . H16A H 0.4031 0.7281 0.4230 0.068 Uiso 1 1 d R . . H16B H 0.3317 0.6392 0.4611 0.068 Uiso 1 1 d R . . H16C H 0.2376 0.7391 0.4270 0.068 Uiso 1 1 d R . . F2 F 0.1008(4) 0.4442(3) 0.06536(19) 0.1260(15) Uani 1 1 d . . . C7 C 0.5220(4) 0.1579(3) 0.3773(3) 0.0537(11) Uani 1 1 d . . . H7A H 0.5392 0.1141 0.3388 0.064 Uiso 1 1 d R . . H7B H 0.5569 0.1186 0.4215 0.064 Uiso 1 1 d R . . C11 C 0.3135(4) 0.0232(4) 0.4302(2) 0.0568(11) Uani 1 1 d . . . H11A H 0.4024 -0.0161 0.4303 0.068 Uiso 1 1 d R . . H11B H 0.2362 -0.0262 0.4333 0.068 Uiso 1 1 d R . . H11C H 0.3324 0.0711 0.4703 0.068 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 Sb1 0.02444(11) 0.03353(13) 0.03208(12) -0.00047(10) 0.00403(8) -0.00022(10) S1 0.0400(5) 0.0565(6) 0.0392(5) -0.0003(5) 0.0111(4) 0.0006(5) Cl1 0.0490(5) 0.0637(6) 0.0361(4) 0.0004(4) 0.0154(4) 0.0015(5) F1 0.0462(14) 0.104(2) 0.112(2) -0.0110(18) 0.0364(15) 0.0030(15) O1 0.0292(12) 0.0333(13) 0.0484(14) 0.0021(10) 0.0065(10) 0.0024(10) O2 0.0299(11) 0.0296(12) 0.0437(13) -0.0013(10) 0.0093(10) -0.0011(10) C17 0.048(2) 0.080(3) 0.058(3) -0.008(3) 0.013(2) 0.004(2) C1 0.0259(15) 0.0400(18) 0.0327(16) -0.0057(15) 0.0074(13) -0.0030(16) C13 0.0355(18) 0.0324(19) 0.047(2) 0.0008(16) 0.0059(15) 0.0032(15) C6 0.0316(17) 0.044(2) 0.0288(16) -0.0041(14) 0.0073(14) -0.0022(15) F3 0.080(2) 0.185(4) 0.114(3) -0.099(3) 0.0171(19) -0.039(2) O3 0.100(3) 0.076(2) 0.071(2) -0.0339(17) 0.0323(19) -0.0330(19) C12 0.0316(17) 0.043(2) 0.050(2) -0.0026(17) 0.0126(15) -0.0099(16) C14 0.060(3) 0.047(2) 0.063(3) 0.016(2) 0.008(2) 0.004(2) C9 0.056(2) 0.052(3) 0.053(2) -0.0124(19) 0.0057(19) -0.005(2) C8 0.0332(17) 0.0307(18) 0.046(2) 0.0011(16) 0.0047(15) -0.0036(15) O4 0.0468(16) 0.106(3) 0.0604(18) 0.0013(17) 0.0269(14) 0.0011(17) C4 0.0243(16) 0.066(3) 0.059(2) -0.008(2) 0.0105(16) -0.002(2) O5 0.103(3) 0.079(2) 0.077(2) 0.0372(18) 0.039(2) 0.037(2) C5 0.0281(17) 0.059(3) 0.049(2) -0.0060(18) 0.0111(16) -0.0089(17) C2 0.0290(17) 0.045(2) 0.0405(19) -0.0031(15) 0.0119(15) 0.0014(16) C10 0.0340(19) 0.043(2) 0.089(3) -0.002(2) 0.012(2) -0.0042(19) C15 0.0323(19) 0.041(2) 0.094(3) 0.005(2) 0.009(2) 0.0095(19) C3 0.0342(18) 0.050(2) 0.055(2) -0.0003(18) 0.0107(17) 0.0118(17) C16 0.055(2) 0.055(3) 0.058(2) -0.012(2) 0.012(2) 0.010(2) F2 0.101(2) 0.180(4) 0.097(2) 0.075(3) 0.025(2) 0.064(3) C7 0.0323(19) 0.042(2) 0.086(3) -0.001(2) 0.012(2) 0.0061(17) C11 0.051(2) 0.062(3) 0.055(2) 0.019(2) 0.0077(19) -0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 C1 2.093(3) . ? Sb1 O2 2.275(2) . ? Sb1 O1 2.312(2) . ? Sb1 Cl1 2.3950(9) . ? S1 O4 1.425(3) . ? S1 O3 1.428(3) . ? S1 O5 1.430(3) . ? S1 C17 1.791(4) . ? F1 C17 1.333(5) . ? O1 C7 1.438(4) . ? O1 C8 1.488(4) . ? O2 C12 1.442(4) . ? O2 C13 1.490(4) . ? C17 F2 1.314(6) . ? C17 F3 1.315(5) . ? C1 C2 1.374(5) . ? C1 C6 1.383(5) . ? C13 C16 1.504(5) . ? C13 C14 1.514(5) . ? C13 C15 1.524(5) . ? C6 C5 1.396(4) . ? C6 C12 1.492(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 H14A 0.9599 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C9 C8 1.510(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9599 . ? C8 C10 1.514(5) . ? C8 C11 1.514(5) . ? C4 C5 1.374(5) . ? C4 C3 1.376(5) . ? C4 H4 0.9300 . ? C5 H5 0.9301 . ? C2 C3 1.396(5) . ? C2 C7 1.497(5) . ? C10 H10A 0.9599 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C3 H3 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9601 . ? C7 H7A 0.9701 . ? C7 H7B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9598 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Sb1 O2 75.32(11) . . ? C1 Sb1 O1 74.37(11) . . ? O2 Sb1 O1 148.40(8) . . ? C1 Sb1 Cl1 95.56(9) . . ? O2 Sb1 Cl1 87.49(6) . . ? O1 Sb1 Cl1 86.72(6) . . ? O4 S1 O3 116.0(2) . . ? O4 S1 O5 116.4(2) . . ? O3 S1 O5 111.8(2) . . ? O4 S1 C17 103.79(19) . . ? O3 S1 C17 103.3(2) . . ? O5 S1 C17 103.3(2) . . ? C7 O1 C8 116.7(3) . . ? C7 O1 Sb1 116.2(2) . . ? C8 O1 Sb1 126.91(18) . . ? C12 O2 C13 116.9(2) . . ? C12 O2 Sb1 115.28(19) . . ? C13 O2 Sb1 127.47(18) . . ? F2 C17 F3 108.5(4) . . ? F2 C17 F1 107.5(4) . . ? F3 C17 F1 106.8(4) . . ? F2 C17 S1 111.3(4) . . ? F3 C17 S1 111.5(3) . . ? F1 C17 S1 111.1(3) . . ? C2 C1 C6 122.0(3) . . ? C2 C1 Sb1 119.8(2) . . ? C6 C1 Sb1 118.2(2) . . ? O2 C13 C16 108.6(3) . . ? O2 C13 C14 108.5(3) . . ? C16 C13 C14 113.0(3) . . ? O2 C13 C15 104.7(3) . . ? C16 C13 C15 111.3(3) . . ? C14 C13 C15 110.3(3) . . ? C1 C6 C5 118.6(3) . . ? C1 C6 C12 120.2(3) . . ? C5 C6 C12 121.2(3) . . ? O2 C12 C6 108.7(3) . . ? O2 C12 H12A 110.1 . . ? C6 C12 H12A 109.8 . . ? O2 C12 H12B 109.9 . . ? C6 C12 H12B 110.0 . . ? H12A C12 H12B 108.3 . . ? C13 C14 H14A 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.0 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C9 H9A 109.9 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.4 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C8 C9 108.5(3) . . ? O1 C8 C10 105.2(3) . . ? C9 C8 C10 110.7(3) . . ? O1 C8 C11 109.2(3) . . ? C9 C8 C11 112.1(3) . . ? C10 C8 C11 110.9(3) . . ? C5 C4 C3 121.8(3) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 119.5(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.1 . . ? C1 C2 C3 119.1(3) . . ? C1 C2 C7 120.5(3) . . ? C3 C2 C7 120.4(3) . . ? C8 C10 H10A 109.6 . . ? C8 C10 H10B 109.2 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.6 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.4 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C4 C3 C2 119.1(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.3 . . ? C13 C16 H16A 109.1 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.8 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C7 C2 108.9(3) . . ? O1 C7 H7A 109.9 . . ? C2 C7 H7A 109.9 . . ? O1 C7 H7B 110.0 . . ? C2 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C8 C11 H11A 109.4 . . ? C8 C11 H11B 109.3 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.7 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.440 _refine_diff_density_min -0.966 _refine_diff_density_rms 0.093 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 801797' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 As Cl O2' _chemical_formula_sum 'C12 H16 As Cl O2' _chemical_formula_weight 302.62 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' 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' As As 0.0499 2.0058 '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 25.3962(7) _cell_length_b 8.1221(9) _cell_length_c 14.6069(12) _cell_angle_alpha 90 _cell_angle_beta 116.012(7) _cell_angle_gamma 90 _cell_volume 2707.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 3091 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 2.692 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 1 0 0.089 -1 0 0 0.101 0 -1 0 0.205 1 0 0 0.112 1 0 -1 0.135 -1 0 2 0.175 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.460 _exptl_absorpt_correction_T_max 0.607 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10758 _diffrn_reflns_av_R_equivalents 0.1349 _diffrn_reflns_av_sigmaI/netI 0.1533 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3091 _reflns_number_gt 1339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0255P)^2^+8.1367P] 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 3091 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2093 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group As1 As 0.10424(3) 0.15882(7) -0.26403(5) 0.0569(2) Uani 1 1 d . . . Cl1 Cl 0.13054(7) 0.1581(2) -0.39329(13) 0.0795(5) Uani 1 1 d . . . O2 O 0.12657(16) 0.4749(4) -0.2313(3) 0.0515(10) Uani 1 1 d . . . O1 O 0.06117(18) -0.0247(4) -0.2954(3) 0.0697(12) Uani 1 1 d . . . C1 C 0.0341(2) 0.2809(6) -0.3364(4) 0.0388(14) Uani 1 1 d . . . C2 C -0.0132(2) 0.1729(7) -0.3849(4) 0.0445(13) Uani 1 1 d . . . C3 C -0.0682(3) 0.2355(8) -0.4426(4) 0.0566(17) Uani 1 1 d . . . H3 H -0.0998 0.1648 -0.4752 0.068 Uiso 1 1 d R . . C4 C -0.0762(3) 0.4039(8) -0.4517(4) 0.0578(18) Uani 1 1 d . . . H4 H -0.1133 0.4469 -0.4903 0.069 Uiso 1 1 d R . . C6 C 0.0258(2) 0.4489(6) -0.3453(4) 0.0394(13) Uani 1 1 d . . . C8 C 0.0759(2) 0.5662(6) -0.2955(4) 0.0516(16) Uani 1 1 d . . . H8A H 0.0833 0.6240 -0.3467 0.062 Uiso 1 1 d R . . H8B H 0.0668 0.6469 -0.2555 0.062 Uiso 1 1 d R . . C7 C 0.0021(3) -0.0062(7) -0.3685(5) 0.0599(17) Uani 1 1 d . . . H7A H -0.0236 -0.0620 -0.3453 0.072 Uiso 1 1 d R . . H7B H -0.0030 -0.0561 -0.4322 0.072 Uiso 1 1 d R . . C5 C -0.0297(3) 0.5092(7) -0.4043(4) 0.0539(16) Uani 1 1 d . . . H5 H -0.0356 0.6224 -0.4119 0.065 Uiso 1 1 d R . . C11 C 0.1781(3) 0.7144(8) -0.1307(6) 0.109(3) Uani 1 1 d . . . H11A H 0.1492 0.7881 -0.1774 0.130 Uiso 1 1 d R . . H11B H 0.2155 0.7685 -0.1008 0.130 Uiso 1 1 d R . . H11C H 0.1671 0.6830 -0.0781 0.130 Uiso 1 1 d R . . C9 C 0.1818(3) 0.5628(8) -0.1881(5) 0.070(2) Uani 1 1 d . . . C10 C 0.2242(3) 0.4411(8) -0.1139(5) 0.087(2) Uani 1 1 d . . . H10A H 0.2104 0.4074 -0.0652 0.104 Uiso 1 1 d R . . H10B H 0.2619 0.4923 -0.0789 0.104 Uiso 1 1 d R . . H10C H 0.2274 0.3466 -0.1505 0.104 Uiso 1 1 d R . . C12 C 0.1995(3) 0.6063(12) -0.2707(6) 0.140(4) Uani 1 1 d . . . H12A H 0.1933 0.5131 -0.3147 0.167 Uiso 1 1 d R . . H12B H 0.2402 0.6365 -0.2411 0.167 Uiso 1 1 d R . . H12C H 0.1762 0.6972 -0.3095 0.167 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 As1 0.0557(4) 0.0419(3) 0.0571(4) 0.0016(4) 0.0102(3) 0.0072(4) Cl1 0.0575(10) 0.0928(13) 0.0884(13) -0.0240(12) 0.0321(10) 0.0079(10) O2 0.049(2) 0.042(2) 0.053(3) -0.001(2) 0.013(2) -0.006(2) O1 0.076(3) 0.036(2) 0.081(3) 0.007(2) 0.020(3) 0.005(2) C1 0.041(3) 0.042(3) 0.030(3) -0.003(3) 0.012(3) 0.001(3) C2 0.050(3) 0.044(3) 0.037(3) -0.004(3) 0.017(3) 0.000(3) C3 0.058(4) 0.068(4) 0.039(4) -0.014(3) 0.017(3) -0.015(4) C4 0.045(4) 0.075(5) 0.047(4) -0.004(3) 0.014(3) 0.012(3) C6 0.044(3) 0.041(3) 0.029(3) -0.002(3) 0.012(3) 0.004(3) C8 0.055(4) 0.036(3) 0.055(4) 0.002(3) 0.017(3) 0.001(3) C7 0.078(5) 0.042(4) 0.058(4) -0.008(3) 0.029(4) -0.010(3) C5 0.061(4) 0.042(4) 0.048(4) 0.005(3) 0.014(3) 0.011(3) C11 0.102(6) 0.064(5) 0.096(6) -0.014(5) -0.016(5) -0.012(4) C9 0.052(4) 0.068(5) 0.064(5) 0.004(4) 0.003(4) -0.015(4) C10 0.049(4) 0.088(5) 0.097(6) -0.005(5) 0.007(4) -0.005(4) C12 0.076(6) 0.235(12) 0.087(6) 0.022(7) 0.016(5) -0.076(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag As1 O1 1.785(4) . ? As1 C1 1.903(5) . ? As1 Cl1 2.2621(18) . ? O2 C8 1.424(6) . ? O2 C9 1.449(6) . ? O1 C7 1.417(6) . ? C1 C6 1.379(7) . ? C1 C2 1.403(7) . ? C2 C3 1.375(7) . ? C2 C7 1.497(7) . ? C3 C4 1.380(8) . ? C3 H3 0.9299 . ? C4 C5 1.374(7) . ? C4 H4 0.9300 . ? C6 C5 1.379(7) . ? C6 C8 1.497(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9699 . ? C5 H5 0.9299 . ? C11 C9 1.516(9) . ? C11 H11A 0.9600 . ? C11 H11B 0.9601 . ? C11 H11C 0.9599 . ? C9 C12 1.503(9) . ? C9 C10 1.513(8) . ? C10 H10A 0.9601 . ? C10 H10B 0.9599 . ? C10 H10C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 As1 C1 88.5(2) . . ? O1 As1 Cl1 98.93(15) . . ? C1 As1 Cl1 94.88(17) . . ? C8 O2 C9 117.0(4) . . ? C7 O1 As1 115.6(3) . . ? C6 C1 C2 120.7(5) . . ? C6 C1 As1 129.4(4) . . ? C2 C1 As1 109.9(4) . . ? C3 C2 C1 119.6(5) . . ? C3 C2 C7 125.5(5) . . ? C1 C2 C7 115.0(5) . . ? C2 C3 C4 119.5(6) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.8(6) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.8 . . ? C1 C6 C5 118.8(5) . . ? C1 C6 C8 121.5(5) . . ? C5 C6 C8 119.7(5) . . ? O2 C8 C6 108.6(4) . . ? O2 C8 H8A 109.5 . . ? C6 C8 H8A 110.1 . . ? O2 C8 H8B 109.9 . . ? C6 C8 H8B 110.3 . . ? H8A C8 H8B 108.4 . . ? O1 C7 C2 109.7(4) . . ? O1 C7 H7A 109.9 . . ? C2 C7 H7A 110.1 . . ? O1 C7 H7B 109.3 . . ? C2 C7 H7B 109.6 . . ? H7A C7 H7B 108.2 . . ? C4 C5 C6 120.7(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.5 . . ? C9 C11 H11A 109.1 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.7 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C9 C12 109.9(5) . . ? O2 C9 C10 103.9(5) . . ? C12 C9 C10 111.1(6) . . ? O2 C9 C11 110.9(6) . . ? C12 C9 C11 111.5(7) . . ? C10 C9 C11 109.4(6) . . ? C9 C10 H10A 109.9 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.3 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C12 H12A 109.3 . . ? C9 C12 H12B 109.8 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.3 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.368 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.088 data_2 _database_code_depnum_ccdc_archive 'CCDC 801798' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C20 H26 As Cl O4)' _chemical_formula_sum 'C40 H52 As2 Cl2 O8' _chemical_formula_weight 881.56 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' 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' As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 17.0370(5) _cell_length_b 7.618(2) _cell_length_c 31.5390(14) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4093.4(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 17743 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 1.813 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.036 -1 0 0 0.147 1 0 0 0.178 0 0 1 0.124 0 1 0 0.052 0 -1 1 0.079 0 1 1 0.055 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.703 _exptl_absorpt_correction_T_max 0.842 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17720 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 27.49 _reflns_number_total 8315 _reflns_number_gt 6532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0331P)^2^+12.5318P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(2) _refine_ls_number_reflns 8315 _refine_ls_number_parameters 469 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.158 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group As2 As 0.90559(4) -0.02379(9) 0.21898(2) 0.03681(18) Uani 1 1 d . . . As1 As 0.85169(4) 0.03266(9) 0.52519(2) 0.03447(16) Uani 1 1 d . . . Cl2 Cl 0.98577(14) -0.2622(2) 0.21847(11) 0.0519(6) Uani 1 1 d . . . Cl1 Cl 0.77264(13) 0.2706(2) 0.52678(11) 0.0491(5) Uani 1 1 d . . . O24 O 0.8172(3) 0.2361(7) 0.2423(3) 0.0466(17) Uani 1 1 d . . . C16 C 0.8875(5) 0.1864(10) 0.4384(2) 0.0354(17) Uani 1 1 d . . . C1 C 0.7806(4) -0.1331(9) 0.4964(2) 0.0332(16) Uani 1 1 d . . . O21 O 0.9670(4) -0.2336(8) 0.3582(3) 0.0544(19) Uani 1 1 d . . . C12 C 0.9935(4) 0.1723(9) 0.4895(2) 0.0344(17) Uani 1 1 d . . . C11 C 0.9150(4) 0.1370(9) 0.4784(2) 0.0301(16) Uani 1 1 d . . . O22 O 0.7526(6) -0.2527(8) 0.1838(3) 0.065(2) Uani 1 1 d . . . C6 C 0.7011(4) -0.1519(10) 0.5078(3) 0.0400(18) Uani 1 1 d . . . C2 C 0.8124(5) -0.2541(9) 0.4677(3) 0.035(2) Uani 1 1 d . . . O3 O 1.0037(5) 0.2619(8) 0.5610(3) 0.062(2) Uani 1 1 d . . . C207 C 0.9495(5) -0.1348(12) 0.3211(3) 0.044(2) Uani 1 1 d . . . H207A H 0.9867 -0.1666 0.2991 0.052 Uiso 1 1 d R . . H207B H 0.9551 -0.0102 0.3267 0.052 Uiso 1 1 d R . . C208 C 1.0403(6) -0.1960(15) 0.3742(3) 0.064(3) Uani 1 1 d . . . H208A H 1.0795 -0.2379 0.3548 0.077 Uiso 1 1 d R . . H208B H 1.0464 -0.2533 0.4011 0.077 Uiso 1 1 d R . . H208C H 1.0460 -0.0715 0.3778 0.077 Uiso 1 1 d R . . C17 C 1.0268(4) 0.1313(10) 0.5322(3) 0.0446(19) Uani 1 1 d . . . H17A H 1.0086 0.0176 0.5419 0.053 Uiso 1 1 d R . . H17B H 1.0836 0.1278 0.5304 0.053 Uiso 1 1 d R . . C211 C 0.9756(4) 0.1460(9) 0.2482(2) 0.0344(16) Uani 1 1 d . . . O4 O 0.7901(4) 0.2462(8) 0.3869(3) 0.057(2) Uani 1 1 d . . . O1 O 0.9398(3) -0.2253(7) 0.4987(3) 0.0452(16) Uani 1 1 d . . . C219 C 1.0954(5) 0.0719(12) 0.2011(3) 0.052(2) Uani 1 1 d . . . C13 C 1.0429(6) 0.2557(10) 0.4616(4) 0.042(2) Uani 1 1 d . . . H13 H 1.0950 0.2777 0.4687 0.051 Uiso 1 1 d R . . C217 C 0.8578(6) 0.2713(13) 0.2828(4) 0.053(3) Uani 1 1 d . . . H217A H 0.8425 0.3861 0.2933 0.064 Uiso 1 1 d R . . H217B H 0.8419 0.1846 0.3036 0.064 Uiso 1 1 d R . . C3 C 0.7655(5) -0.3708(10) 0.4462(2) 0.0431(19) Uani 1 1 d . . . H3 H 0.7874 -0.4485 0.4268 0.052 Uiso 1 1 d R . . C4 C 0.6844(5) -0.3741(12) 0.4543(3) 0.056(3) Uani 1 1 d . . . H4 H 0.6516 -0.4495 0.4393 0.067 Uiso 1 1 d R . . C209 C 0.7293(5) -0.1193(11) 0.2114(3) 0.048(2) Uani 1 1 d . . . H209A H 0.6725 -0.1127 0.2125 0.057 Uiso 1 1 d R . . H209B H 0.7495 -0.0068 0.2020 0.057 Uiso 1 1 d R . . C212 C 0.9429(5) 0.2661(10) 0.2773(4) 0.037(2) Uani 1 1 d . . . C201 C 0.8419(4) -0.1251(11) 0.2653(3) 0.0386(18) Uani 1 1 d . . . C213 C 0.9890(6) 0.3833(11) 0.2987(3) 0.050(2) Uani 1 1 d . . . H213 H 0.9673 0.4646 0.3174 0.060 Uiso 1 1 d R . . C5 C 0.6542(5) -0.2678(12) 0.4842(4) 0.051(3) Uani 1 1 d . . . H5 H 0.6003 -0.2689 0.4889 0.061 Uiso 1 1 d R . . C216 C 1.0559(5) 0.1589(11) 0.2386(3) 0.0435(19) Uani 1 1 d . . . C8 C 0.9361(5) -0.3689(11) 0.5277(4) 0.060(2) Uani 1 1 d . . . H8A H 0.8824 -0.3859 0.5361 0.072 Uiso 1 1 d R . . H8B H 0.9674 -0.3440 0.5523 0.072 Uiso 1 1 d R . . H8C H 0.9552 -0.4735 0.5143 0.072 Uiso 1 1 d R . . C206 C 0.7636(5) -0.1645(10) 0.2541(3) 0.0422(19) Uani 1 1 d . . . C15 C 0.9379(6) 0.2717(12) 0.4099(4) 0.053(3) Uani 1 1 d . . . H15 H 0.9207 0.3017 0.3828 0.063 Uiso 1 1 d R . . C218 C 0.8224(6) 0.3799(12) 0.2135(4) 0.070(3) Uani 1 1 d . . . H218A H 0.7974 0.4809 0.2257 0.083 Uiso 1 1 d R . . H218B H 0.7960 0.3481 0.1877 0.083 Uiso 1 1 d R . . H218C H 0.8763 0.4067 0.2074 0.083 Uiso 1 1 d R . . C210 C 0.7218(12) -0.2298(19) 0.1413(6) 0.112(6) Uani 1 1 d . . . H210A H 0.6658 -0.2438 0.1417 0.134 Uiso 1 1 d R . . H210B H 0.7446 -0.3159 0.1228 0.134 Uiso 1 1 d R . . H210C H 0.7347 -0.1143 0.1313 0.134 Uiso 1 1 d R . . O23 O 1.1069(12) 0.239(2) 0.1639(5) 0.312(15) Uani 1 1 d . . . C19 C 0.8048(5) 0.1468(12) 0.4231(3) 0.048(2) Uani 1 1 d . . . H19A H 0.8006 0.0229 0.4163 0.058 Uiso 1 1 d R . . H19B H 0.7667 0.1741 0.4449 0.058 Uiso 1 1 d R . . C7 C 0.9013(5) -0.2612(10) 0.4613(4) 0.041(2) Uani 1 1 d . . . H7A H 0.9159 -0.3770 0.4512 0.049 Uiso 1 1 d R . . H7B H 0.9164 -0.1762 0.4399 0.049 Uiso 1 1 d R . . C202 C 0.8692(5) -0.1740(10) 0.3063(3) 0.0400(18) Uani 1 1 d . . . O2 O 0.6236(5) -0.1864(13) 0.5735(3) 0.096(3) Uani 1 1 d . . . C9 C 0.6699(6) -0.0644(12) 0.5498(4) 0.084(4) Uani 1 1 d . . . H9A H 0.7114 -0.0064 0.5655 0.101 Uiso 1 1 d R . . H9B H 0.6330 0.0246 0.5405 0.101 Uiso 1 1 d R . . C14 C 1.0137(5) 0.3078(13) 0.4219(3) 0.053(2) Uani 1 1 d . . . H14 H 1.0458 0.3701 0.4034 0.064 Uiso 1 1 d R . . C20 C 0.7164(6) 0.2037(17) 0.3681(4) 0.068(3) Uani 1 1 d . . . H20A H 0.7210 0.0962 0.3524 0.081 Uiso 1 1 d R . . H20B H 0.6999 0.2961 0.3494 0.081 Uiso 1 1 d R . . H20C H 0.6784 0.1893 0.3903 0.081 Uiso 1 1 d R . . C10 C 0.6891(9) -0.2854(19) 0.5952(4) 0.116(6) Uani 1 1 d . . . H10A H 0.6992 -0.3908 0.5794 0.139 Uiso 1 1 d R . . H10B H 0.6733 -0.3153 0.6235 0.139 Uiso 1 1 d R . . H10C H 0.7359 -0.2154 0.5962 0.139 Uiso 1 1 d R . . C215 C 1.1044(6) 0.2733(14) 0.2604(4) 0.061(3) Uani 1 1 d . . . H215 H 1.1575 0.2815 0.2539 0.073 Uiso 1 1 d R . . C214 C 1.0713(6) 0.3787(13) 0.2919(3) 0.057(2) Uani 1 1 d . . . H214 H 1.1042 0.4470 0.3087 0.069 Uiso 1 1 d R . . C203 C 0.8183(5) -0.2572(11) 0.3328(4) 0.045(2) Uani 1 1 d . . . H203 H 0.8369 -0.2924 0.3592 0.054 Uiso 1 1 d R . . C204 C 0.7426(6) -0.2959(15) 0.3230(3) 0.060(3) Uani 1 1 d . . . H204 H 0.7093 -0.3507 0.3423 0.072 Uiso 1 1 d R . . C220 C 1.0492(8) 0.094(3) 0.1658(5) 0.153(8) Uani 1 1 d . . . C205 C 0.7158(6) -0.2487(12) 0.2832(5) 0.058(3) Uani 1 1 d . . . H205 H 0.6641 -0.2732 0.2757 0.069 Uiso 1 1 d R . . C18 C 1.0329(11) 0.2332(17) 0.6020(5) 0.089(5) Uani 1 1 d . . . H18A H 1.0186 0.1170 0.6110 0.107 Uiso 1 1 d R . . H18B H 1.0105 0.3176 0.6211 0.107 Uiso 1 1 d R . . H18C H 1.0890 0.2445 0.6021 0.107 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 As2 0.0427(4) 0.0364(4) 0.0313(4) -0.0006(5) -0.0017(3) -0.0017(3) As1 0.0397(4) 0.0330(3) 0.0307(3) 0.0005(5) 0.0006(3) -0.0029(3) Cl2 0.0635(13) 0.0388(10) 0.0534(15) -0.0035(11) 0.0106(14) 0.0126(8) Cl1 0.0568(12) 0.0379(9) 0.0526(15) -0.0021(11) 0.0119(13) 0.0041(8) O24 0.038(3) 0.034(3) 0.067(5) -0.010(3) -0.006(3) -0.001(2) C16 0.042(4) 0.038(4) 0.026(4) -0.004(3) 0.003(3) -0.007(4) C1 0.040(4) 0.029(4) 0.030(4) 0.003(3) 0.000(3) 0.003(3) O21 0.061(4) 0.070(5) 0.031(4) 0.008(3) 0.003(3) -0.009(3) C12 0.037(4) 0.022(3) 0.044(5) -0.012(3) 0.001(3) 0.001(3) C11 0.037(4) 0.022(3) 0.031(4) -0.005(3) 0.001(3) -0.001(3) O22 0.101(6) 0.052(5) 0.043(5) -0.007(3) -0.023(5) 0.008(4) C6 0.034(4) 0.036(4) 0.050(5) 0.008(3) -0.001(3) 0.000(3) C2 0.042(5) 0.034(5) 0.030(5) 0.006(3) -0.002(4) -0.001(3) O3 0.093(6) 0.049(4) 0.046(6) -0.001(3) -0.003(4) 0.008(3) C207 0.049(5) 0.050(5) 0.033(5) 0.004(4) -0.004(4) -0.007(4) C208 0.050(5) 0.089(7) 0.053(7) 0.027(6) -0.014(4) -0.005(5) C17 0.043(4) 0.038(4) 0.053(6) -0.001(4) -0.007(4) 0.000(3) C211 0.035(4) 0.032(4) 0.037(4) 0.007(3) -0.003(3) -0.006(3) O4 0.049(4) 0.068(5) 0.053(5) 0.016(3) -0.023(4) -0.009(3) O1 0.041(3) 0.037(3) 0.058(5) 0.006(3) 0.005(3) 0.000(3) C219 0.036(4) 0.067(6) 0.054(5) 0.008(4) 0.006(4) 0.002(4) C13 0.037(4) 0.040(5) 0.051(7) -0.008(4) 0.011(4) -0.002(3) C217 0.067(7) 0.043(5) 0.049(7) -0.014(4) 0.007(5) -0.013(4) C3 0.063(5) 0.040(4) 0.026(4) 0.001(3) -0.001(4) -0.006(4) C4 0.050(5) 0.044(5) 0.074(7) 0.016(5) -0.022(5) -0.019(4) C209 0.042(4) 0.045(4) 0.056(6) -0.007(4) -0.008(4) 0.000(4) C212 0.036(4) 0.031(4) 0.042(6) 0.000(3) 0.002(4) -0.006(3) C201 0.035(4) 0.036(4) 0.044(5) -0.001(3) 0.002(3) 0.001(3) C213 0.069(6) 0.037(4) 0.046(5) 0.001(4) -0.008(4) -0.009(4) C5 0.023(4) 0.048(5) 0.081(9) 0.001(5) 0.007(4) 0.000(4) C216 0.037(4) 0.051(5) 0.043(5) 0.012(4) 0.001(4) 0.001(4) C8 0.063(5) 0.043(5) 0.073(6) 0.003(5) -0.018(6) 0.004(4) C206 0.048(5) 0.038(4) 0.041(5) -0.004(4) -0.005(4) -0.001(4) C15 0.056(6) 0.055(6) 0.047(7) 0.017(4) 0.018(5) 0.000(4) C218 0.069(6) 0.046(5) 0.093(8) 0.019(6) -0.025(6) 0.003(5) C210 0.185(18) 0.105(12) 0.046(10) -0.002(7) -0.017(11) 0.003(11) O23 0.42(2) 0.32(2) 0.195(14) -0.190(14) 0.235(16) -0.33(2) C19 0.046(5) 0.053(5) 0.045(5) 0.013(4) -0.007(4) -0.005(4) C7 0.034(4) 0.034(5) 0.055(7) -0.006(4) 0.011(4) -0.003(3) C202 0.037(4) 0.039(4) 0.044(5) -0.007(4) 0.001(4) 0.005(4) O2 0.074(5) 0.108(6) 0.107(7) 0.031(5) 0.029(5) 0.025(5) C9 0.073(7) 0.038(5) 0.141(10) -0.009(5) 0.084(7) -0.009(5) C14 0.054(5) 0.056(5) 0.050(6) 0.006(5) 0.014(4) -0.017(5) C20 0.044(5) 0.108(8) 0.051(7) -0.011(6) -0.005(4) 0.010(6) C10 0.178(15) 0.111(11) 0.058(7) 0.030(7) -0.016(8) 0.075(11) C215 0.049(6) 0.073(7) 0.060(8) 0.021(5) -0.011(5) -0.030(5) C214 0.065(6) 0.059(6) 0.049(5) 0.010(4) -0.017(4) -0.022(5) C203 0.043(5) 0.057(6) 0.034(6) 0.004(4) 0.007(4) 0.006(4) C204 0.054(6) 0.068(6) 0.058(7) 0.002(5) 0.016(5) -0.004(5) C220 0.076(8) 0.29(2) 0.091(10) -0.098(14) 0.010(8) -0.002(12) C205 0.025(4) 0.055(7) 0.093(11) -0.005(5) 0.006(5) -0.008(4) C18 0.135(13) 0.079(9) 0.052(10) -0.006(6) -0.018(9) 0.018(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag As2 C201 1.976(8) . ? As2 C211 1.986(7) . ? As2 Cl2 2.273(2) . ? As1 C1 1.971(7) . ? As1 C11 1.992(7) . ? As1 Cl1 2.259(2) . ? O24 C218 1.427(11) . ? O24 C217 1.478(13) . ? C16 C11 1.398(11) . ? C16 C15 1.403(12) . ? C16 C19 1.521(11) . ? C1 C2 1.400(12) . ? C1 C6 1.408(10) . ? O21 C208 1.376(12) . ? O21 C207 1.424(11) . ? C12 C13 1.374(13) . ? C12 C11 1.408(10) . ? C12 C17 1.492(11) . ? O22 C209 1.396(11) . ? O22 C210 1.448(18) . ? C6 C5 1.405(13) . ? C6 C9 1.577(12) . ? C2 C3 1.376(12) . ? C2 C7 1.528(12) . ? O3 C18 1.403(18) . ? O3 C17 1.405(11) . ? C207 C202 1.475(11) . ? C207 H207A 0.9698 . ? C207 H207B 0.9700 . ? C208 H208A 0.9599 . ? C208 H208B 0.9600 . ? C208 H208C 0.9600 . ? C17 H17A 0.9699 . ? C17 H17B 0.9700 . ? C211 C216 1.404(11) . ? C211 C212 1.412(12) . ? O4 C19 1.392(11) . ? O4 C20 1.426(12) . ? O1 C7 1.377(13) . ? O1 C8 1.428(11) . ? C219 C220 1.373(17) . ? C219 C216 1.513(12) . ? C219 O23 1.74(2) . ? C13 C14 1.405(16) . ? C13 H13 0.9309 . ? C217 C212 1.459(14) . ? C217 H217A 0.9702 . ? C217 H217B 0.9701 . ? C3 C4 1.406(12) . ? C3 H3 0.9295 . ? C4 C5 1.345(14) . ? C4 H4 0.9304 . ? C209 C206 1.511(11) . ? C209 H209A 0.9700 . ? C209 H209B 0.9701 . ? C212 C213 1.366(12) . ? C201 C206 1.411(11) . ? C201 C202 1.424(12) . ? C213 C214 1.418(13) . ? C213 H213 0.9317 . ? C5 H5 0.9302 . ? C216 C215 1.384(14) . ? C8 H8A 0.9601 . ? C8 H8B 0.9599 . ? C8 H8C 0.9600 . ? C206 C205 1.383(14) . ? C15 C14 1.374(14) . ? C15 H15 0.9320 . ? C218 H218A 0.9599 . ? C218 H218B 0.9601 . ? C218 H218C 0.9601 . ? C210 H210A 0.9599 . ? C210 H210B 0.9599 . ? C210 H210C 0.9599 . ? O23 C220 1.48(2) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C7 H7A 0.9704 . ? C7 H7B 0.9701 . ? C202 C203 1.362(13) . ? O2 C9 1.429(12) . ? O2 C10 1.511(14) . ? C9 H9A 0.9697 . ? C9 H9B 0.9700 . ? C14 H14 0.9299 . ? C20 H20A 0.9601 . ? C20 H20B 0.9601 . ? C20 H20C 0.9599 . ? C10 H10A 0.9600 . ? C10 H10B 0.9598 . ? C10 H10C 0.9599 . ? C215 C214 1.396(16) . ? C215 H215 0.9296 . ? C214 H214 0.9302 . ? C203 C204 1.360(14) . ? C203 H203 0.9304 . ? C204 C205 1.385(17) . ? C204 H204 0.9309 . ? C205 H205 0.9309 . ? C18 H18A 0.9599 . ? C18 H18B 0.9598 . ? C18 H18C 0.9599 . ? 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 C201 As2 C211 104.0(3) . . ? C201 As2 Cl2 91.3(2) . . ? C211 As2 Cl2 99.4(2) . . ? C1 As1 C11 104.3(3) . . ? C1 As1 Cl1 99.1(2) . . ? C11 As1 Cl1 91.1(2) . . ? C218 O24 C217 112.5(7) . . ? C11 C16 C15 119.9(8) . . ? C11 C16 C19 123.0(7) . . ? C15 C16 C19 117.1(8) . . ? C2 C1 C6 118.0(7) . . ? C2 C1 As1 118.8(6) . . ? C6 C1 As1 122.6(6) . . ? C208 O21 C207 112.3(7) . . ? C13 C12 C11 120.7(8) . . ? C13 C12 C17 116.2(8) . . ? C11 C12 C17 123.0(7) . . ? C16 C11 C12 119.4(7) . . ? C16 C11 As1 126.5(5) . . ? C12 C11 As1 114.0(5) . . ? C209 O22 C210 112.7(9) . . ? C5 C6 C1 118.4(8) . . ? C5 C6 C9 121.3(8) . . ? C1 C6 C9 119.7(8) . . ? C3 C2 C1 121.3(8) . . ? C3 C2 C7 119.1(8) . . ? C1 C2 C7 119.5(8) . . ? C18 O3 C17 112.8(8) . . ? O21 C207 C202 110.3(7) . . ? O21 C207 H207A 108.6 . . ? C202 C207 H207A 109.2 . . ? O21 C207 H207B 110.3 . . ? C202 C207 H207B 110.3 . . ? H207A C207 H207B 108.0 . . ? O21 C208 H208A 109.4 . . ? O21 C208 H208B 109.1 . . ? H208A C208 H208B 109.5 . . ? O21 C208 H208C 109.9 . . ? H208A C208 H208C 109.5 . . ? H208B C208 H208C 109.5 . . ? O3 C17 C12 109.1(6) . . ? O3 C17 H17A 109.7 . . ? C12 C17 H17A 110.5 . . ? O3 C17 H17B 109.7 . . ? C12 C17 H17B 109.4 . . ? H17A C17 H17B 108.3 . . ? C216 C211 C212 118.7(7) . . ? C216 C211 As2 122.0(6) . . ? C212 C211 As2 119.1(5) . . ? C19 O4 C20 112.0(8) . . ? C7 O1 C8 112.1(7) . . ? C220 C219 C216 108.9(8) . . ? C220 C219 O23 55.2(11) . . ? C216 C219 O23 104.8(8) . . ? C12 C13 C14 119.1(9) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.1 . . ? C212 C217 O24 110.9(9) . . ? C212 C217 H217A 109.4 . . ? O24 C217 H217A 109.4 . . ? C212 C217 H217B 109.9 . . ? O24 C217 H217B 109.2 . . ? H217A C217 H217B 107.9 . . ? C2 C3 C4 119.5(8) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 119.5(8) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 120.6 . . ? O22 C209 C206 106.3(7) . . ? O22 C209 H209A 110.2 . . ? C206 C209 H209A 111.4 . . ? O22 C209 H209B 110.6 . . ? C206 C209 H209B 109.7 . . ? H209A C209 H209B 108.7 . . ? C213 C212 C211 121.1(8) . . ? C213 C212 C217 119.6(9) . . ? C211 C212 C217 119.2(8) . . ? C206 C201 C202 118.6(7) . . ? C206 C201 As2 114.7(6) . . ? C202 C201 As2 126.4(6) . . ? C212 C213 C214 118.5(9) . . ? C212 C213 H213 121.2 . . ? C214 C213 H213 120.3 . . ? C4 C5 C6 122.2(8) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C215 C216 C211 121.2(9) . . ? C215 C216 C219 113.5(8) . . ? C211 C216 C219 124.8(8) . . ? O1 C8 H8A 108.7 . . ? O1 C8 H8B 110.0 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.7 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C205 C206 C201 119.4(9) . . ? C205 C206 C209 118.0(8) . . ? C201 C206 C209 122.6(8) . . ? C14 C15 C16 119.5(10) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 120.6 . . ? O24 C218 H218A 109.4 . . ? O24 C218 H218B 108.5 . . ? H218A C218 H218B 109.5 . . ? O24 C218 H218C 110.5 . . ? H218A C218 H218C 109.5 . . ? H218B C218 H218C 109.5 . . ? O22 C210 H210A 109.6 . . ? O22 C210 H210B 109.4 . . ? H210A C210 H210B 109.5 . . ? O22 C210 H210C 109.4 . . ? H210A C210 H210C 109.5 . . ? H210B C210 H210C 109.5 . . ? C220 O23 C219 49.7(9) . . ? O4 C19 C16 108.7(7) . . ? O4 C19 H19A 109.6 . . ? C16 C19 H19A 109.3 . . ? O4 C19 H19B 110.2 . . ? C16 C19 H19B 110.6 . . ? H19A C19 H19B 108.4 . . ? O1 C7 C2 110.6(9) . . ? O1 C7 H7A 109.9 . . ? C2 C7 H7A 109.2 . . ? O1 C7 H7B 109.7 . . ? C2 C7 H7B 109.3 . . ? H7A C7 H7B 108.1 . . ? C203 C202 C201 118.2(8) . . ? C203 C202 C207 119.3(8) . . ? C201 C202 C207 122.5(7) . . ? C9 O2 C10 98.8(9) . . ? O2 C9 C6 110.5(8) . . ? O2 C9 H9A 115.6 . . ? C6 C9 H9A 112.1 . . ? O2 C9 H9B 104.8 . . ? C6 C9 H9B 105.1 . . ? H9A C9 H9B 108.0 . . ? C15 C14 C13 121.4(9) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 119.7 . . ? O4 C20 H20A 109.6 . . ? O4 C20 H20B 110.3 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 108.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 C10 H10A 108.4 . . ? O2 C10 H10B 109.4 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 110.6 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C216 C215 C214 118.3(9) . . ? C216 C215 H215 120.9 . . ? C214 C215 H215 120.8 . . ? C215 C214 C213 121.4(9) . . ? C215 C214 H214 118.9 . . ? C213 C214 H214 119.7 . . ? C204 C203 C202 124.4(10) . . ? C204 C203 H203 117.7 . . ? C202 C203 H203 117.9 . . ? C203 C204 C205 117.5(9) . . ? C203 C204 H204 121.8 . . ? C205 C204 H204 120.7 . . ? C219 C220 O23 75.2(12) . . ? C206 C205 C204 121.9(9) . . ? C206 C205 H205 118.8 . . ? C204 C205 H205 119.3 . . ? O3 C18 H18A 109.0 . . ? O3 C18 H18B 109.4 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 110.0 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.013 _refine_diff_density_min -0.831 _refine_diff_density_rms 0.096 #===END data_8 _database_code_depnum_ccdc_archive 'CCDC 801799' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 Cl2 N O Sb' _chemical_formula_sum 'C14 H22 Cl2 N O Sb' _chemical_formula_weight 412.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 '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 11.525(4) _cell_length_b 10.5691(13) _cell_length_c 16.038(3) _cell_angle_alpha 90 _cell_angle_beta 122.680(18) _cell_angle_gamma 90 _cell_volume 1644.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.995 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 -1 0.113 -1 0 1 0.090 1 0 1 0.076 1 0 -1 0.140 0 -1 0 0.057 0 1 0 0.072 0 0 -1 0.109 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.647 _exptl_absorpt_correction_T_max 0.793 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12117 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3748 _reflns_number_gt 3172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0313P)^2^+3.7537P] 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 3748 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.75434(2) 0.26497(2) 0.271251(16) 0.01713(8) Uani 1 1 d . . . Cl2 Cl 0.49114(9) 0.28362(8) 0.13538(6) 0.02497(18) Uani 1 1 d . . . Cl1 Cl 1.00855(9) 0.25469(9) 0.41767(7) 0.0284(2) Uani 1 1 d . . . O1 O 0.7794(3) 0.4990(2) 0.28163(19) 0.0282(6) Uani 1 1 d . . . C2 C 0.6417(3) 0.2491(3) 0.4010(3) 0.0206(7) Uani 1 1 d . . . C6 C 0.7386(4) 0.4555(3) 0.4090(2) 0.0215(7) Uani 1 1 d . . . N1 N 0.6990(3) 0.0807(3) 0.3229(2) 0.0196(6) Uani 1 1 d . . . C4 C 0.6459(4) 0.4091(4) 0.5087(3) 0.0272(8) Uani 1 1 d . . . H4 H 0.6267 0.4342 0.5556 0.033 Uiso 1 1 d R . . C1 C 0.7064(3) 0.3341(3) 0.3722(2) 0.0182(7) Uani 1 1 d . . . C7 C 0.5990(4) 0.1226(3) 0.3502(3) 0.0236(7) Uani 1 1 d . . . H7A H 0.5071 0.1289 0.2911 0.028 Uiso 1 1 d R . . H7B H 0.5969 0.0607 0.3940 0.028 Uiso 1 1 d R . . C5 C 0.7074(4) 0.4930(4) 0.4788(3) 0.0251(8) Uani 1 1 d . . . H5 H 0.7284 0.5744 0.5050 0.030 Uiso 1 1 d R . . C3 C 0.6117(4) 0.2874(4) 0.4707(3) 0.0248(7) Uani 1 1 d . . . H3 H 0.5692 0.2322 0.4913 0.030 Uiso 1 1 d R . . C11 C 0.8356(4) 0.5736(4) 0.2332(3) 0.0277(8) Uani 1 1 d . . . C12 C 0.7674(8) 0.5168(6) 0.1304(5) 0.079(2) Uani 1 1 d . . . H12A H 0.7829 0.5716 0.0895 0.095 Uiso 1 1 d R . . H12B H 0.6702 0.5092 0.1025 0.095 Uiso 1 1 d R . . H12C H 0.8055 0.4348 0.1336 0.095 Uiso 1 1 d R . . C13 C 0.9859(6) 0.5596(7) 0.2893(5) 0.082(2) Uani 1 1 d . . . H13A H 1.0275 0.6163 0.3449 0.099 Uiso 1 1 d R . . H13B H 1.0186 0.5790 0.2469 0.099 Uiso 1 1 d R . . H13C H 1.0100 0.4740 0.3125 0.099 Uiso 1 1 d R . . C10 C 0.8042(4) 0.5456(3) 0.3737(3) 0.0253(8) Uani 1 1 d . . . H10A H 0.7646 0.6293 0.3645 0.030 Uiso 1 1 d R . . H10B H 0.9026 0.5512 0.4222 0.030 Uiso 1 1 d R . . C8 C 0.8197(4) 0.0210(4) 0.4100(3) 0.0283(8) Uani 1 1 d . . . H8A H 0.7914 -0.0545 0.4275 0.034 Uiso 1 1 d R . . H8B H 0.8595 0.0789 0.4647 0.034 Uiso 1 1 d R . . H8C H 0.8867 -0.0001 0.3942 0.034 Uiso 1 1 d R . . C9 C 0.6346(4) -0.0119(3) 0.2407(3) 0.0246(7) Uani 1 1 d . . . H9A H 0.6968 -0.0307 0.2201 0.030 Uiso 1 1 d R . . H9B H 0.5508 0.0229 0.1860 0.030 Uiso 1 1 d R . . H9C H 0.6141 -0.0880 0.2630 0.030 Uiso 1 1 d R . . C14 C 0.7894(7) 0.7090(5) 0.2221(5) 0.0573(14) Uani 1 1 d . . . H14A H 0.7983 0.7365 0.2824 0.069 Uiso 1 1 d R . . H14B H 0.6947 0.7157 0.1684 0.069 Uiso 1 1 d R . . H14C H 0.8455 0.7614 0.2086 0.069 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 Sb1 0.02103(12) 0.01622(12) 0.01763(12) -0.00103(9) 0.01272(9) 0.00032(9) Cl2 0.0253(4) 0.0269(4) 0.0204(4) -0.0009(3) 0.0108(3) 0.0037(3) Cl1 0.0223(4) 0.0290(5) 0.0295(5) -0.0047(4) 0.0111(4) -0.0003(3) O1 0.0471(17) 0.0200(12) 0.0303(14) -0.0028(11) 0.0293(13) -0.0054(11) C2 0.0201(16) 0.0248(18) 0.0188(16) 0.0026(14) 0.0118(13) 0.0051(13) C6 0.0217(17) 0.0248(18) 0.0150(15) 0.0007(13) 0.0079(14) 0.0058(14) N1 0.0218(15) 0.0180(14) 0.0208(14) -0.0001(12) 0.0127(12) 0.0000(11) C4 0.030(2) 0.037(2) 0.0164(16) 0.0005(16) 0.0140(15) 0.0107(16) C1 0.0180(16) 0.0209(16) 0.0157(15) 0.0008(13) 0.0091(13) 0.0032(13) C7 0.0277(19) 0.0231(18) 0.0273(18) 0.0019(15) 0.0196(16) -0.0017(14) C5 0.0298(19) 0.0251(18) 0.0177(16) -0.0039(14) 0.0109(15) 0.0061(15) C3 0.0266(18) 0.032(2) 0.0206(16) 0.0043(15) 0.0158(15) 0.0034(15) C11 0.037(2) 0.0228(18) 0.031(2) 0.0034(16) 0.0234(18) -0.0025(16) C12 0.148(7) 0.056(4) 0.067(4) -0.017(3) 0.080(5) -0.041(4) C13 0.044(3) 0.104(5) 0.108(5) 0.059(5) 0.048(4) 0.013(3) C10 0.034(2) 0.0194(17) 0.0231(18) -0.0055(14) 0.0156(16) -0.0042(15) C8 0.0264(19) 0.0267(19) 0.0288(19) 0.0097(16) 0.0130(16) 0.0069(15) C9 0.0292(19) 0.0190(17) 0.0266(18) -0.0019(15) 0.0157(16) -0.0013(14) C14 0.075(4) 0.039(3) 0.075(4) 0.015(3) 0.052(3) 0.005(3) _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 Sb1 C1 2.103(3) . ? Sb1 N1 2.335(3) . ? Sb1 O1 2.486(3) . ? Sb1 Cl1 2.5847(13) . ? Sb1 Cl2 2.6174(13) . ? O1 C10 1.431(4) . ? O1 C11 1.479(4) . ? C2 C3 1.396(5) . ? C2 C1 1.396(5) . ? C2 C7 1.503(5) . ? C6 C1 1.378(5) . ? C6 C5 1.406(5) . ? C6 C10 1.503(5) . ? N1 C8 1.478(5) . ? N1 C9 1.479(4) . ? N1 C7 1.504(4) . ? C4 C5 1.374(6) . ? C4 C3 1.386(6) . ? C4 H4 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9699 . ? C5 H5 0.9300 . ? C3 H3 0.9300 . ? C11 C13 1.466(7) . ? C11 C14 1.504(6) . ? C11 C12 1.516(7) . ? C12 H12A 0.9601 . ? C12 H12B 0.9600 . ? C12 H12C 0.9599 . ? C13 H13A 0.9600 . ? C13 H13B 0.9601 . ? C13 H13C 0.9600 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9601 . ? C9 H9C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9599 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Sb1 N1 77.36(12) . . ? C1 Sb1 O1 70.88(11) . . ? N1 Sb1 O1 148.24(9) . . ? C1 Sb1 Cl1 87.44(9) . . ? N1 Sb1 Cl1 92.02(8) . . ? O1 Sb1 Cl1 86.97(7) . . ? C1 Sb1 Cl2 86.94(9) . . ? N1 Sb1 Cl2 86.71(8) . . ? O1 Sb1 Cl2 91.23(7) . . ? Cl1 Sb1 Cl2 174.38(3) . . ? C10 O1 C11 117.3(3) . . ? C10 O1 Sb1 111.2(2) . . ? C11 O1 Sb1 124.3(2) . . ? C3 C2 C1 119.1(3) . . ? C3 C2 C7 122.8(3) . . ? C1 C2 C7 118.0(3) . . ? C1 C6 C5 118.6(3) . . ? C1 C6 C10 120.1(3) . . ? C5 C6 C10 121.3(3) . . ? C8 N1 C9 108.8(3) . . ? C8 N1 C7 109.2(3) . . ? C9 N1 C7 111.0(3) . . ? C8 N1 Sb1 113.2(2) . . ? C9 N1 Sb1 109.7(2) . . ? C7 N1 Sb1 104.9(2) . . ? C5 C4 C3 121.6(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.1 . . ? C6 C1 C2 121.7(3) . . ? C6 C1 Sb1 122.1(3) . . ? C2 C1 Sb1 116.2(2) . . ? C2 C7 N1 110.0(3) . . ? C2 C7 H7A 109.5 . . ? N1 C7 H7A 109.9 . . ? C2 C7 H7B 109.7 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 108.2 . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 120.2 . . ? C4 C3 C2 119.1(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.5 . . ? C13 C11 O1 109.3(4) . . ? C13 C11 C14 113.2(5) . . ? O1 C11 C14 110.0(3) . . ? C13 C11 C12 112.0(5) . . ? O1 C11 C12 104.1(3) . . ? C14 C11 C12 107.8(5) . . ? C11 C12 H12A 109.0 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 110.2 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.8 . . ? C11 C13 H13B 109.2 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.4 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C10 C6 108.1(3) . . ? O1 C10 H10A 109.9 . . ? C6 C10 H10A 110.1 . . ? O1 C10 H10B 110.1 . . ? C6 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? N1 C8 H8A 109.7 . . ? N1 C8 H8B 109.4 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.3 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.6 . . ? N1 C9 H9B 109.6 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.3 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C14 H14A 109.2 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.7 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.391 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.125 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 801800' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H29 As Cl2 O2' _chemical_formula_sum 'C26 H29 As Cl2 O2' _chemical_formula_weight 519.31 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' 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' As As 0.0499 2.0058 '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 8.0719(6) _cell_length_b 11.9821(9) _cell_length_c 13.1989(6) _cell_angle_alpha 80.579(5) _cell_angle_beta 79.169(4) _cell_angle_gamma 79.737(7) _cell_volume 1222.53(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 22807 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 1.629 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.103 0 0 -1 0.104 -1 0 0 0.165 1 0 0 0.099 0 1 0 0.069 0 -1 0 0.067 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.654 _exptl_absorpt_correction_T_max 0.805 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22718 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5590 _reflns_number_gt 4584 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0290P)^2^+1.0459P] 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 5590 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group As1 As 0.89854(3) 0.25151(2) 0.763156(19) 0.02522(8) Uani 1 1 d . . . Cl1 Cl 0.75909(8) 0.27757(5) 0.62877(5) 0.03100(14) Uani 1 1 d . . . Cl2 Cl 0.68978(8) 0.32263(6) 0.87914(5) 0.03311(15) Uani 1 1 d . . . O1 O 0.7474(2) 0.64760(14) 0.68071(13) 0.0259(4) Uani 1 1 d . . . O2 O 1.1218(2) 0.22274(17) 0.88645(14) 0.0335(4) Uani 1 1 d . . . C7 C 0.7805(3) 0.53236(19) 0.65579(19) 0.0232(5) Uani 1 1 d . . . H7A H 0.7613 0.5315 0.5856 0.028 Uiso 1 1 d R . . H7B H 0.7065 0.4851 0.7039 0.028 Uiso 1 1 d R . . C13 C 0.5766(3) 0.7779(2) 0.57100(19) 0.0277(5) Uani 1 1 d . . . C18 C 1.1754(3) 0.1680(2) 0.97948(19) 0.0273(5) Uani 1 1 d . . . C3 C 1.0829(3) 0.5614(2) 0.62047(19) 0.0284(5) Uani 1 1 d . . . H3 H 1.0467 0.6308 0.5820 0.034 Uiso 1 1 d R . . C8 C 0.5882(3) 0.7073(2) 0.66486(18) 0.0237(5) Uani 1 1 d . . . C10 C 0.2955(3) 0.7717(2) 0.7283(2) 0.0316(6) Uani 1 1 d . . . H10 H 0.2012 0.7700 0.7810 0.038 Uiso 1 1 d R . . C2 C 0.9650(3) 0.4889(2) 0.66537(17) 0.0223(5) Uani 1 1 d . . . C1 C 1.0225(3) 0.3823(2) 0.71984(17) 0.0226(5) Uani 1 1 d . . . C9 C 0.4495(3) 0.7040(2) 0.74561(19) 0.0277(5) Uani 1 1 d . . . C22 C 1.2892(3) 0.0028(2) 1.0853(2) 0.0293(5) Uani 1 1 d . . . H22 H 1.3320 -0.0749 1.0944 0.035 Uiso 1 1 d R . . C12 C 0.4201(3) 0.8436(2) 0.5572(2) 0.0328(6) Uani 1 1 d . . . H12 H 0.4104 0.8902 0.4942 0.039 Uiso 1 1 d R . . C14 C 0.4638(4) 0.6301(3) 0.8480(2) 0.0380(6) Uani 1 1 d . . . H14A H 0.4074 0.5649 0.8529 0.046 Uiso 1 1 d R . . H14B H 0.4115 0.6735 0.9038 0.046 Uiso 1 1 d R . . H14C H 0.5821 0.6048 0.8528 0.046 Uiso 1 1 d R . . C6 C 1.1936(3) 0.3567(2) 0.73658(19) 0.0282(5) Uani 1 1 d . . . C4 C 1.2529(3) 0.5326(2) 0.6311(2) 0.0331(6) Uani 1 1 d . . . H4 H 1.3307 0.5809 0.5979 0.040 Uiso 1 1 d R . . C17 C 1.2569(3) 0.2494(3) 0.8031(2) 0.0387(7) Uani 1 1 d . . . H17A H 1.2924 0.1868 0.7618 0.046 Uiso 1 1 d R . . H17B H 1.3544 0.2607 0.8313 0.046 Uiso 1 1 d R . . C19 C 1.1648(3) 0.2348(2) 1.0574(2) 0.0310(5) Uani 1 1 d . . . C11 C 0.2786(3) 0.8415(2) 0.6350(2) 0.0340(6) Uani 1 1 d . . . C21 C 1.2839(3) 0.0663(2) 1.1644(2) 0.0291(5) Uani 1 1 d . . . C23 C 1.2323(3) 0.0510(2) 0.9918(2) 0.0286(5) Uani 1 1 d . . . C20 C 1.2187(3) 0.1823(2) 1.1497(2) 0.0308(5) Uani 1 1 d . . . H20 H 1.2112 0.2258 1.2031 0.037 Uiso 1 1 d R . . C24 C 1.0970(4) 0.3618(2) 1.0417(3) 0.0468(8) Uani 1 1 d . . . H24A H 1.1728 0.4002 0.9879 0.056 Uiso 1 1 d R . . H24B H 1.0889 0.3926 1.1055 0.056 Uiso 1 1 d R . . H24C H 0.9860 0.3729 1.0221 0.056 Uiso 1 1 d R . . C26 C 1.2303(4) -0.0233(3) 0.9104(2) 0.0399(6) Uani 1 1 d . . . H26A H 1.1363 0.0073 0.8740 0.048 Uiso 1 1 d R . . H26B H 1.2178 -0.0995 0.9437 0.048 Uiso 1 1 d R . . H26C H 1.3352 -0.0252 0.8619 0.048 Uiso 1 1 d R . . C16 C 0.7314(4) 0.7864(3) 0.4880(2) 0.0392(6) Uani 1 1 d . . . H16A H 0.8165 0.8148 0.5144 0.047 Uiso 1 1 d R . . H16B H 0.6995 0.8378 0.4286 0.047 Uiso 1 1 d R . . H16C H 0.7767 0.7121 0.4678 0.047 Uiso 1 1 d R . . C5 C 1.3064(3) 0.4328(2) 0.6916(2) 0.0335(6) Uani 1 1 d . . . H5 H 1.4195 0.4158 0.7021 0.040 Uiso 1 1 d R . . C25 C 1.3466(4) 0.0131(3) 1.2645(2) 0.0381(6) Uani 1 1 d . . . H25A H 1.2515 0.0091 1.3202 0.046 Uiso 1 1 d R . . H25B H 1.4226 0.0588 1.2800 0.046 Uiso 1 1 d R . . H25C H 1.4062 -0.0627 1.2569 0.046 Uiso 1 1 d R . . C15 C 0.1092(4) 0.9123(3) 0.6187(3) 0.0516(8) Uani 1 1 d . . . H15A H 0.0248 0.8631 0.6261 0.062 Uiso 1 1 d R . . H15B H 0.1206 0.9546 0.5500 0.062 Uiso 1 1 d R . . H15C H 0.0747 0.9646 0.6693 0.062 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 As1 0.02552(13) 0.02375(13) 0.02590(13) -0.00279(9) -0.00412(10) -0.00301(9) Cl1 0.0342(3) 0.0321(3) 0.0305(3) -0.0043(2) -0.0105(3) -0.0095(2) Cl2 0.0333(3) 0.0345(3) 0.0272(3) -0.0028(3) 0.0044(3) -0.0049(3) O1 0.0235(8) 0.0257(9) 0.0309(9) -0.0106(7) -0.0090(7) 0.0014(7) O2 0.0252(9) 0.0442(11) 0.0292(9) 0.0023(8) -0.0091(7) -0.0021(8) C7 0.0249(11) 0.0204(11) 0.0252(11) -0.0059(9) -0.0056(9) -0.0018(9) C13 0.0320(13) 0.0281(13) 0.0249(12) -0.0077(10) -0.0061(10) -0.0045(10) C18 0.0223(12) 0.0308(13) 0.0294(12) -0.0010(10) -0.0080(10) -0.0041(10) C3 0.0293(13) 0.0282(13) 0.0281(12) -0.0044(10) -0.0036(10) -0.0060(10) C8 0.0241(11) 0.0254(12) 0.0236(11) -0.0088(9) -0.0070(9) -0.0007(9) C10 0.0279(13) 0.0317(14) 0.0358(14) -0.0126(11) -0.0025(11) -0.0017(10) C2 0.0223(11) 0.0259(12) 0.0202(11) -0.0076(9) -0.0033(9) -0.0040(9) C1 0.0206(11) 0.0282(12) 0.0199(11) -0.0071(9) -0.0029(9) -0.0031(9) C9 0.0305(13) 0.0255(12) 0.0275(12) -0.0071(10) -0.0053(10) -0.0016(10) C22 0.0261(12) 0.0210(12) 0.0383(14) -0.0013(10) -0.0026(11) -0.0018(9) C12 0.0400(15) 0.0302(14) 0.0301(13) -0.0019(11) -0.0155(12) -0.0024(11) C14 0.0421(16) 0.0405(16) 0.0259(13) -0.0022(12) 0.0009(12) -0.0011(12) C6 0.0242(12) 0.0361(14) 0.0241(12) -0.0074(10) -0.0054(10) 0.0008(10) C4 0.0272(13) 0.0359(15) 0.0378(14) -0.0097(12) 0.0012(11) -0.0117(11) C17 0.0268(13) 0.0499(18) 0.0335(14) 0.0006(13) -0.0055(11) 0.0042(12) C19 0.0334(13) 0.0220(12) 0.0377(14) -0.0027(10) -0.0115(11) 0.0002(10) C11 0.0318(14) 0.0292(14) 0.0449(15) -0.0101(12) -0.0161(12) 0.0005(11) C21 0.0260(12) 0.0272(13) 0.0323(13) 0.0011(10) -0.0047(10) -0.0038(10) C23 0.0228(12) 0.0304(13) 0.0329(13) -0.0094(11) -0.0006(10) -0.0048(10) C20 0.0358(14) 0.0257(13) 0.0338(13) -0.0072(11) -0.0125(11) -0.0018(10) C24 0.062(2) 0.0254(14) 0.0540(18) -0.0046(13) -0.0241(16) 0.0040(13) C26 0.0418(16) 0.0375(16) 0.0425(16) -0.0155(13) -0.0017(13) -0.0078(12) C16 0.0447(16) 0.0420(16) 0.0276(13) -0.0021(12) -0.0013(12) -0.0052(13) C5 0.0200(12) 0.0451(16) 0.0384(14) -0.0114(12) -0.0074(11) -0.0049(11) C25 0.0377(15) 0.0367(15) 0.0354(14) 0.0050(12) -0.0087(12) 0.0000(12) C15 0.0353(16) 0.0446(18) 0.073(2) -0.0032(16) -0.0193(16) 0.0061(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 As1 C1 1.958(2) . ? As1 Cl2 2.2035(7) . ? As1 Cl1 2.2258(6) . ? O1 C8 1.390(3) . ? O1 C7 1.439(3) . ? O2 C18 1.400(3) . ? O2 C17 1.436(3) . ? C7 C2 1.509(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9699 . ? C13 C8 1.390(3) . ? C13 C12 1.391(4) . ? C13 C16 1.506(4) . ? C18 C19 1.385(4) . ? C18 C23 1.388(4) . ? C3 C4 1.383(4) . ? C3 C2 1.387(3) . ? C3 H3 0.9299 . ? C8 C9 1.394(3) . ? C10 C11 1.385(4) . ? C10 C9 1.394(3) . ? C10 H10 0.9300 . ? C2 C1 1.407(3) . ? C1 C6 1.411(3) . ? C9 C14 1.501(4) . ? C22 C21 1.380(4) . ? C22 C23 1.397(4) . ? C22 H22 0.9300 . ? C12 C11 1.386(4) . ? C12 H12 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C6 C5 1.389(4) . ? C6 C17 1.499(4) . ? C4 C5 1.373(4) . ? C4 H4 0.9300 . ? C17 H17A 0.9701 . ? C17 H17B 0.9699 . ? C19 C20 1.386(4) . ? C19 C24 1.517(4) . ? C11 C15 1.508(4) . ? C21 C20 1.391(4) . ? C21 C25 1.506(4) . ? C23 C26 1.507(4) . ? C20 H20 0.9299 . ? C24 H24A 0.9600 . ? C24 H24B 0.9599 . ? C24 H24C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9599 . ? C16 H16C 0.9600 . ? C5 H5 0.9301 . ? C25 H25A 0.9599 . ? C25 H25B 0.9600 . ? C25 H25C 0.9601 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9599 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 As1 Cl2 100.19(7) . . ? C1 As1 Cl1 97.63(7) . . ? Cl2 As1 Cl1 98.78(3) . . ? C8 O1 C7 114.70(17) . . ? C18 O2 C17 114.93(18) . . ? O1 C7 C2 106.00(18) . . ? O1 C7 H7A 110.5 . . ? C2 C7 H7A 110.6 . . ? O1 C7 H7B 110.5 . . ? C2 C7 H7B 110.5 . . ? H7A C7 H7B 108.7 . . ? C8 C13 C12 118.4(2) . . ? C8 C13 C16 120.7(2) . . ? C12 C13 C16 120.8(2) . . ? C19 C18 C23 122.6(2) . . ? C19 C18 O2 117.2(2) . . ? C23 C18 O2 120.2(2) . . ? C4 C3 C2 121.5(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.2 . . ? C13 C8 O1 118.0(2) . . ? C13 C8 C9 121.8(2) . . ? O1 C8 C9 119.9(2) . . ? C11 C10 C9 122.0(2) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C3 C2 C1 118.7(2) . . ? C3 C2 C7 117.2(2) . . ? C1 C2 C7 124.1(2) . . ? C2 C1 C6 119.4(2) . . ? C2 C1 As1 127.01(17) . . ? C6 C1 As1 113.13(18) . . ? C10 C9 C8 117.7(2) . . ? C10 C9 C14 120.6(2) . . ? C8 C9 C14 121.6(2) . . ? C21 C22 C23 122.3(2) . . ? C21 C22 H22 118.9 . . ? C23 C22 H22 118.8 . . ? C11 C12 C13 121.6(2) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.1 . . ? C9 C14 H14A 109.7 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.3 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C5 C6 C1 119.6(2) . . ? C5 C6 C17 118.8(2) . . ? C1 C6 C17 121.6(2) . . ? C5 C4 C3 119.8(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? O2 C17 C6 108.6(2) . . ? O2 C17 H17A 110.1 . . ? C6 C17 H17A 110.1 . . ? O2 C17 H17B 109.8 . . ? C6 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? C18 C19 C20 118.0(2) . . ? C18 C19 C24 120.9(2) . . ? C20 C19 C24 121.1(2) . . ? C10 C11 C12 118.5(2) . . ? C10 C11 C15 120.4(3) . . ? C12 C11 C15 121.1(3) . . ? C22 C21 C20 118.2(2) . . ? C22 C21 C25 121.6(2) . . ? C20 C21 C25 120.2(2) . . ? C18 C23 C22 117.0(2) . . ? C18 C23 C26 122.6(2) . . ? C22 C23 C26 120.4(2) . . ? C19 C20 C21 121.7(2) . . ? C19 C20 H20 119.1 . . ? C21 C20 H20 119.2 . . ? C19 C24 H24A 109.7 . . ? C19 C24 H24B 109.4 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.4 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.2 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.7 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C13 C16 H16A 109.6 . . ? C13 C16 H16B 109.3 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.6 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C21 C25 H25A 109.7 . . ? C21 C25 H25B 109.4 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.3 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C11 C15 H15A 109.7 . . ? C11 C15 H15B 109.2 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.453 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.070 #===END data_11 _database_code_depnum_ccdc_archive 'CCDC 801801' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 Bi Cl F3 N O4 S' _chemical_formula_sum 'C15 H22 Bi Cl F3 N O4 S' _chemical_formula_weight 613.83 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' O O 0.0106 0.0060 '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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' F F 0.0171 0.0103 '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 7.7441(5) _cell_length_b 11.0320(8) _cell_length_c 12.5790(8) _cell_angle_alpha 74.564(5) _cell_angle_beta 85.146(5) _cell_angle_gamma 74.351(5) _cell_volume 997.39(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 18731 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 9.124 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.054 0 0 -1 0.084 -1 0 0 0.189 1 0 0 0.157 0 -1 0 0.069 0 1 0 0.095 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.138 _exptl_absorpt_correction_T_max 0.356 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18498 _diffrn_reflns_av_R_equivalents 0.1537 _diffrn_reflns_av_sigmaI/netI 0.0871 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4494 _reflns_number_gt 4155 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1292P)^2^+13.6908P] 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 4494 _refine_ls_number_parameters 229 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0785 _refine_ls_wR_factor_ref 0.1994 _refine_ls_wR_factor_gt 0.1921 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.46192(5) 0.15626(3) 0.25765(3) 0.01853(18) Uani 1 1 d . . . S1 S 0.6214(4) 0.1325(3) 0.5365(2) 0.0229(6) Uani 1 1 d . . . Cl1 Cl 0.3215(5) 0.1462(3) 0.0857(3) 0.0334(7) Uani 1 1 d . . . O1 O 0.2677(10) 0.3859(8) 0.2513(6) 0.0212(15) Uani 1 1 d . . . O2 O 0.6140(14) 0.2021(9) 0.4202(7) 0.031(2) Uani 1 1 d . . . F1 F 0.7963(15) 0.2882(12) 0.5759(9) 0.060(3) Uani 1 1 d . . . C10 C 0.3828(16) 0.4729(12) 0.2391(10) 0.026(2) Uani 1 1 d . . . H10A H 0.4266 0.4674 0.3107 0.031 Uiso 1 1 d R . . H10B H 0.3166 0.5621 0.2079 0.031 Uiso 1 1 d R . . C11 C 0.1042(15) 0.4082(11) 0.3218(9) 0.022(2) Uani 1 1 d . . . F2 F 0.5098(16) 0.3589(9) 0.5822(10) 0.061(3) Uani 1 1 d . . . F3 F 0.6472(15) 0.2101(10) 0.7125(7) 0.047(2) Uani 1 1 d . . . O3 O 0.4530(12) 0.1071(8) 0.5808(7) 0.0297(18) Uani 1 1 d . . . O4 O 0.7788(12) 0.0281(9) 0.5688(8) 0.0318(19) Uani 1 1 d . . . C1 C 0.5975(15) 0.3036(10) 0.1613(8) 0.0192(14) Uani 1 1 d U . . C5 C 0.6247(17) 0.5237(11) 0.1003(10) 0.025(2) Uani 1 1 d . . . H5 H 0.5882 0.6101 0.1036 0.030 Uiso 1 1 d R . . N1 N 0.7465(14) 0.0355(10) 0.1961(8) 0.0245(19) Uani 1 1 d . . . C6 C 0.5374(15) 0.4318(10) 0.1650(8) 0.0192(14) Uani 1 1 d . . . C8 C 0.742(2) -0.0929(14) 0.1799(11) 0.033(3) Uani 1 1 d . . . H8A H 0.8516 -0.1290 0.1447 0.040 Uiso 1 1 d R . . H8B H 0.6424 -0.0810 0.1343 0.040 Uiso 1 1 d R . . H8C H 0.7291 -0.1512 0.2501 0.040 Uiso 1 1 d R . . C14 C 0.0121(18) 0.3083(13) 0.3099(11) 0.032(3) Uani 1 1 d . . . H14A H -0.0009 0.3152 0.2331 0.039 Uiso 1 1 d R . . H14B H -0.1043 0.3244 0.3445 0.039 Uiso 1 1 d R . . H14C H 0.0812 0.2224 0.3447 0.039 Uiso 1 1 d R . . C15 C 0.645(2) 0.2539(12) 0.6050(11) 0.034(3) Uani 1 1 d . . . C7 C 0.7903(17) 0.1228(12) 0.0890(9) 0.028(2) Uani 1 1 d . . . H7A H 0.9181 0.0969 0.0742 0.033 Uiso 1 1 d R . . H7B H 0.7280 0.1133 0.0292 0.033 Uiso 1 1 d R . . C9 C 0.8819(18) 0.0113(14) 0.2811(11) 0.033(3) Uani 1 1 d . . . H9A H 0.9963 -0.0342 0.2572 0.039 Uiso 1 1 d R . . H9B H 0.8473 -0.0405 0.3495 0.039 Uiso 1 1 d R . . H9C H 0.8902 0.0928 0.2912 0.039 Uiso 1 1 d R . . C12 C -0.0111(17) 0.5448(11) 0.2773(10) 0.027(2) Uani 1 1 d . . . H12A H 0.0526 0.6070 0.2812 0.033 Uiso 1 1 d R . . H12B H -0.1192 0.5572 0.3211 0.033 Uiso 1 1 d R . . H12C H -0.0409 0.5566 0.2021 0.033 Uiso 1 1 d R . . C3 C 0.8262(17) 0.3522(13) 0.0304(10) 0.029(3) Uani 1 1 d . . . H3 H 0.9245 0.3255 -0.0134 0.035 Uiso 1 1 d R . . C2 C 0.7395(15) 0.2606(12) 0.0950(8) 0.024(2) Uani 1 1 d . . . C13 C 0.1588(17) 0.3844(12) 0.4393(10) 0.028(2) Uani 1 1 d . . . H13A H 0.2243 0.2952 0.4662 0.034 Uiso 1 1 d R . . H13B H 0.0527 0.4026 0.4838 0.034 Uiso 1 1 d R . . H13C H 0.2326 0.4404 0.4430 0.034 Uiso 1 1 d R . . C4 C 0.7665(16) 0.4839(12) 0.0328(9) 0.028(3) Uani 1 1 d . . . H4 H 0.8220 0.5446 -0.0123 0.034 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 Bi1 0.0266(3) 0.0140(2) 0.0140(2) 0.00311(15) -0.00093(16) -0.00993(18) S1 0.0339(14) 0.0171(12) 0.0163(12) 0.0051(9) -0.0029(10) -0.0129(11) Cl1 0.0393(16) 0.0349(16) 0.0291(14) -0.0074(12) -0.0082(12) -0.0131(14) O1 0.024(4) 0.022(4) 0.020(4) 0.000(3) 0.001(3) -0.014(3) O2 0.049(5) 0.026(4) 0.019(4) 0.006(3) 0.003(4) -0.022(4) F1 0.068(6) 0.080(7) 0.058(6) -0.026(5) 0.010(5) -0.059(6) C10 0.030(6) 0.025(6) 0.024(5) -0.004(4) 0.004(4) -0.011(5) C11 0.022(5) 0.020(5) 0.023(5) -0.002(4) 0.000(4) -0.006(4) F2 0.081(7) 0.028(4) 0.077(7) -0.019(5) -0.032(6) -0.005(5) F3 0.071(6) 0.053(6) 0.025(4) -0.008(4) -0.008(4) -0.029(5) O3 0.035(5) 0.021(4) 0.030(4) 0.005(3) 0.003(4) -0.015(4) O4 0.034(5) 0.024(4) 0.032(4) 0.002(4) -0.009(4) -0.005(4) C1 0.027(4) 0.018(3) 0.013(3) 0.006(2) -0.002(3) -0.015(3) C5 0.033(6) 0.011(5) 0.029(6) 0.005(4) -0.004(5) -0.012(4) N1 0.030(5) 0.025(5) 0.018(4) -0.001(4) -0.001(4) -0.011(4) C6 0.027(4) 0.018(3) 0.013(3) 0.006(2) -0.002(3) -0.015(3) C8 0.040(7) 0.028(6) 0.028(6) -0.006(5) 0.006(5) -0.007(6) C14 0.035(6) 0.032(6) 0.028(6) -0.001(5) 0.009(5) -0.014(5) C15 0.052(8) 0.021(6) 0.034(7) -0.003(5) -0.001(6) -0.022(6) C7 0.030(6) 0.027(6) 0.020(5) 0.002(4) 0.005(4) -0.005(5) C9 0.031(6) 0.031(6) 0.035(7) -0.005(5) -0.007(5) -0.008(5) C12 0.032(6) 0.021(5) 0.026(6) 0.001(4) -0.005(5) -0.008(5) C3 0.029(6) 0.032(6) 0.023(6) 0.001(5) 0.001(5) -0.009(5) C2 0.025(5) 0.035(6) 0.012(4) 0.006(4) -0.004(4) -0.018(5) C13 0.031(6) 0.026(6) 0.026(6) -0.002(5) -0.001(5) -0.009(5) C4 0.030(6) 0.031(6) 0.019(5) 0.013(4) -0.005(4) -0.018(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 Bi1 C1 2.207(10) . ? Bi1 N1 2.431(10) . ? Bi1 Cl1 2.542(3) . ? Bi1 O1 2.558(8) . ? Bi1 O2 2.666(10) . ? S1 O4 1.433(9) . ? S1 O3 1.442(9) . ? S1 O2 1.457(8) . ? S1 C15 1.830(13) . ? O1 C10 1.449(14) . ? O1 C11 1.486(13) . ? F1 C15 1.318(17) . ? C10 C6 1.501(15) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C13 1.507(16) . ? C11 C14 1.509(17) . ? C11 C12 1.513(16) . ? F2 C15 1.321(18) . ? F3 C15 1.309(16) . ? C1 C6 1.376(15) . ? C1 C2 1.380(16) . ? C5 C4 1.378(18) . ? C5 C6 1.409(14) . ? C5 H5 0.9300 . ? N1 C8 1.494(17) . ? N1 C9 1.483(16) . ? N1 C7 1.505(14) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C7 C2 1.485(18) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9601 . ? C12 H12C 0.9600 . ? C3 C4 1.409(19) . ? C3 C2 1.403(16) . ? C3 H3 0.9301 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C4 H4 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Bi1 N1 74.0(4) . . ? C1 Bi1 Cl1 91.9(3) . . ? N1 Bi1 Cl1 88.1(2) . . ? C1 Bi1 O1 69.4(3) . . ? N1 Bi1 O1 143.4(3) . . ? Cl1 Bi1 O1 93.02(19) . . ? C1 Bi1 O2 80.0(3) . . ? N1 Bi1 O2 92.7(3) . . ? Cl1 Bi1 O2 171.3(2) . . ? O1 Bi1 O2 81.2(3) . . ? O4 S1 O3 116.3(5) . . ? O4 S1 O2 115.5(6) . . ? O3 S1 O2 113.6(6) . . ? O4 S1 C15 103.4(6) . . ? O3 S1 C15 102.5(6) . . ? O2 S1 C15 102.9(6) . . ? C10 O1 C11 117.6(8) . . ? C10 O1 Bi1 109.1(6) . . ? C11 O1 Bi1 121.4(6) . . ? S1 O2 Bi1 127.5(5) . . ? O1 C10 C6 107.9(9) . . ? O1 C10 H10A 109.8 . . ? C6 C10 H10A 109.9 . . ? O1 C10 H10B 110.3 . . ? C6 C10 H10B 110.5 . . ? H10A C10 H10B 108.4 . . ? O1 C11 C13 109.2(9) . . ? O1 C11 C14 103.4(9) . . ? C13 C11 C14 111.3(10) . . ? O1 C11 C12 109.3(9) . . ? C13 C11 C12 112.3(10) . . ? C14 C11 C12 110.9(10) . . ? C6 C1 C2 122.7(10) . . ? C6 C1 Bi1 121.0(8) . . ? C2 C1 Bi1 116.2(8) . . ? C4 C5 C6 119.3(11) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.5 . . ? C8 N1 C9 108.0(10) . . ? C8 N1 C7 110.5(9) . . ? C9 N1 C7 111.4(10) . . ? C8 N1 Bi1 113.8(8) . . ? C9 N1 Bi1 107.9(7) . . ? C7 N1 Bi1 105.3(7) . . ? C1 C6 C5 119.4(10) . . ? C1 C6 C10 120.3(9) . . ? C5 C6 C10 120.2(10) . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.3 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.6 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C14 H14A 109.6 . . ? C11 C14 H14B 108.7 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 110.0 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? F3 C15 F1 106.7(13) . . ? F3 C15 F2 106.4(12) . . ? F1 C15 F2 108.9(12) . . ? F3 C15 S1 112.0(9) . . ? F1 C15 S1 111.6(10) . . ? F2 C15 S1 111.1(10) . . ? C2 C7 N1 110.6(9) . . ? C2 C7 H7A 109.1 . . ? N1 C7 H7A 109.1 . . ? C2 C7 H7B 110.3 . . ? N1 C7 H7B 109.7 . . ? H7A C7 H7B 108.0 . . ? N1 C9 H9A 109.2 . . ? N1 C9 H9B 109.6 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C12 H12A 109.8 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.7 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C4 C3 C2 120.4(11) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C1 C2 C3 117.9(11) . . ? C1 C2 C7 120.2(10) . . ? C3 C2 C7 121.9(11) . . ? C11 C13 H13A 109.8 . . ? C11 C13 H13B 108.8 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.8 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C5 C4 C3 120.3(10) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.8 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 7.820 _refine_diff_density_min -7.918 _refine_diff_density_rms 0.470 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 801802' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 As Cl2 N O' _chemical_formula_sum 'C14 H22 As Cl2 N O' _chemical_formula_weight 366.15 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.0499 2.0058 '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 11.2757(8) _cell_length_b 10.3700(4) _cell_length_c 16.1121(16) _cell_angle_alpha 90 _cell_angle_beta 121.939(6) _cell_angle_gamma 90 _cell_volume 1598.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 14262 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 2.453 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 -1 0 0.046 1 1 0 0.056 1 -1 0 0.090 -1 1 0 0.082 1 0 1 0.052 -1 0 -1 0.075 -1 0 1 0.129 1 0 -1 0.102 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.578 _exptl_absorpt_correction_T_max 0.813 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14207 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3642 _reflns_number_gt 2839 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0300P)^2^+2.9508P] 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 3642 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group As1 As 0.75218(3) 0.24164(3) 0.28250(2) 0.01741(10) Uani 1 1 d . . . Cl2 Cl 0.99794(8) 0.24759(8) 0.41530(6) 0.02655(18) Uani 1 1 d . . . Cl1 Cl 0.50086(9) 0.21812(8) 0.14649(6) 0.02439(18) Uani 1 1 d . . . N1 N 0.6984(3) 0.4178(2) 0.32277(19) 0.0183(5) Uani 1 1 d . . . O1 O 0.7796(3) 0.0039(2) 0.28025(16) 0.0244(5) Uani 1 1 d . . . C6 C 0.7405(3) 0.0441(3) 0.4076(2) 0.0215(7) Uani 1 1 d . . . C10 C 0.8102(4) -0.0445(3) 0.3727(2) 0.0241(7) Uani 1 1 d . . . H10A H 0.9103 -0.0463 0.4191 0.029 Uiso 1 1 d R . . H10B H 0.7741 -0.1314 0.3654 0.029 Uiso 1 1 d R . . C8 C 0.6375(4) 0.5083(3) 0.2384(2) 0.0236(7) Uani 1 1 d . . . H8A H 0.6092 0.5863 0.2551 0.028 Uiso 1 1 d R . . H8B H 0.5578 0.4688 0.1830 0.028 Uiso 1 1 d R . . H8C H 0.7063 0.5279 0.2223 0.028 Uiso 1 1 d R . . C5 C 0.7082(3) 0.0039(3) 0.4762(2) 0.0246(7) Uani 1 1 d . . . H5 H 0.7296 -0.0796 0.5010 0.030 Uiso 1 1 d R . . C11 C 0.8387(4) -0.0663(3) 0.2317(2) 0.0257(7) Uani 1 1 d . . . C12 C 0.7925(5) -0.2058(4) 0.2162(4) 0.0445(10) Uani 1 1 d . . . H12A H 0.8299 -0.2476 0.2784 0.053 Uiso 1 1 d R . . H12B H 0.8257 -0.2488 0.1796 0.053 Uiso 1 1 d R . . H12C H 0.6923 -0.2096 0.1806 0.053 Uiso 1 1 d R . . C13 C 0.9943(5) -0.0556(5) 0.2893(4) 0.0576(14) Uani 1 1 d . . . H13A H 1.0210 0.0333 0.3042 0.069 Uiso 1 1 d R . . H13B H 1.0303 -0.0900 0.2516 0.069 Uiso 1 1 d R . . H13C H 1.0317 -0.1035 0.3490 0.069 Uiso 1 1 d R . . C14 C 0.7752(7) 0.0001(5) 0.1336(4) 0.0643(16) Uani 1 1 d . . . H14A H 0.6752 -0.0012 0.1011 0.077 Uiso 1 1 d R . . H14B H 0.8031 -0.0449 0.0945 0.077 Uiso 1 1 d R . . H14C H 0.8071 0.0878 0.1426 0.077 Uiso 1 1 d R . . C2 C 0.6373(3) 0.2527(3) 0.4006(2) 0.0210(6) Uani 1 1 d . . . C1 C 0.7058(3) 0.1690(3) 0.3720(2) 0.0192(6) Uani 1 1 d . . . C9 C 0.8194(4) 0.4825(3) 0.4082(2) 0.0261(7) Uani 1 1 d . . . H9A H 0.7894 0.5621 0.4216 0.031 Uiso 1 1 d R . . H9B H 0.8900 0.4997 0.3934 0.031 Uiso 1 1 d R . . H9C H 0.8571 0.4272 0.4643 0.031 Uiso 1 1 d R . . C7 C 0.5948(3) 0.3813(3) 0.3497(2) 0.0219(7) Uani 1 1 d . . . H7A H 0.5935 0.4459 0.3928 0.026 Uiso 1 1 d R . . H7B H 0.5018 0.3757 0.2916 0.026 Uiso 1 1 d R . . C3 C 0.6070(4) 0.2119(3) 0.4698(2) 0.0245(7) Uani 1 1 d . . . H3 H 0.5625 0.2670 0.4905 0.029 Uiso 1 1 d R . . C4 C 0.6441(4) 0.0883(3) 0.5071(2) 0.0256(7) Uani 1 1 d . . . H4 H 0.6254 0.0611 0.5540 0.031 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 As1 0.01927(16) 0.01849(16) 0.01626(16) 0.00082(12) 0.01060(12) -0.00048(13) Cl2 0.0205(4) 0.0281(4) 0.0277(4) 0.0031(3) 0.0105(3) -0.0004(3) Cl1 0.0258(4) 0.0253(4) 0.0194(4) 0.0013(3) 0.0101(3) -0.0021(3) N1 0.0192(13) 0.0172(12) 0.0184(13) -0.0009(10) 0.0099(11) -0.0015(10) O1 0.0363(14) 0.0210(11) 0.0222(12) 0.0050(9) 0.0197(11) 0.0074(10) C6 0.0211(16) 0.0235(16) 0.0141(14) 0.0000(12) 0.0054(12) -0.0020(13) C10 0.0296(18) 0.0214(16) 0.0218(16) 0.0068(12) 0.0141(14) 0.0043(13) C8 0.0261(17) 0.0211(15) 0.0239(16) 0.0033(12) 0.0134(14) 0.0035(13) C5 0.0240(17) 0.0259(17) 0.0172(16) 0.0043(12) 0.0063(13) -0.0038(14) C11 0.0312(19) 0.0243(17) 0.0240(17) -0.0022(13) 0.0161(15) 0.0031(14) C12 0.051(3) 0.033(2) 0.059(3) -0.0153(19) 0.036(2) -0.0097(19) C13 0.040(3) 0.075(3) 0.067(3) -0.034(3) 0.034(2) -0.014(2) C14 0.112(5) 0.059(3) 0.050(3) 0.019(2) 0.062(3) 0.039(3) C2 0.0214(15) 0.0239(15) 0.0178(15) -0.0035(13) 0.0105(12) -0.0045(14) C1 0.0208(16) 0.0205(15) 0.0165(15) 0.0011(12) 0.0100(13) -0.0023(12) C9 0.0261(17) 0.0248(17) 0.0221(17) -0.0078(13) 0.0093(14) -0.0072(14) C7 0.0226(17) 0.0246(16) 0.0225(16) -0.0013(13) 0.0147(14) 0.0007(13) C3 0.0237(16) 0.0335(18) 0.0158(15) -0.0047(13) 0.0101(13) -0.0050(14) C4 0.0247(17) 0.040(2) 0.0116(15) 0.0020(13) 0.0094(13) -0.0074(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag As1 C1 1.928(3) . ? As1 N1 2.131(3) . ? As1 Cl2 2.4470(9) . ? As1 Cl1 2.5144(9) . ? N1 C8 1.488(4) . ? N1 C9 1.489(4) . ? N1 C7 1.495(4) . ? O1 C10 1.430(4) . ? O1 C11 1.462(4) . ? C6 C1 1.386(4) . ? C6 C5 1.399(5) . ? C6 C10 1.498(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9601 . ? C5 C4 1.384(5) . ? C5 H5 0.9300 . ? C11 C13 1.493(6) . ? C11 C14 1.513(5) . ? C11 C12 1.513(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9599 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9599 . ? C13 H13C 0.9599 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C2 C1 1.392(5) . ? C2 C3 1.393(5) . ? C2 C7 1.505(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C3 C4 1.384(5) . ? C3 H3 0.9301 . ? C4 H4 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 As1 N1 82.75(12) . . ? C1 As1 Cl2 89.19(9) . . ? N1 As1 Cl2 94.89(7) . . ? C1 As1 Cl1 89.27(9) . . ? N1 As1 Cl1 88.71(7) . . ? Cl2 As1 Cl1 175.88(3) . . ? C8 N1 C9 108.4(2) . . ? C8 N1 C7 111.8(3) . . ? C9 N1 C7 108.7(3) . . ? C8 N1 As1 109.29(19) . . ? C9 N1 As1 113.4(2) . . ? C7 N1 As1 105.29(18) . . ? C10 O1 C11 117.1(2) . . ? C1 C6 C5 118.1(3) . . ? C1 C6 C10 120.5(3) . . ? C5 C6 C10 121.4(3) . . ? O1 C10 C6 106.9(2) . . ? O1 C10 H10A 110.5 . . ? C6 C10 H10A 110.5 . . ? O1 C10 H10B 110.2 . . ? C6 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N1 C8 H8A 109.6 . . ? N1 C8 H8B 109.4 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.4 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? O1 C11 C13 110.4(3) . . ? O1 C11 C14 103.6(3) . . ? C13 C11 C14 111.5(4) . . ? O1 C11 C12 110.4(3) . . ? C13 C11 C12 111.2(4) . . ? C14 C11 C12 109.4(4) . . ? C11 C12 H12A 109.6 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.3 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.7 . . ? C11 C13 H13B 109.3 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.0 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.9 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 C2 C3 119.3(3) . . ? C1 C2 C7 116.4(3) . . ? C3 C2 C7 124.2(3) . . ? C6 C1 C2 122.0(3) . . ? C6 C1 As1 123.0(3) . . ? C2 C1 As1 114.9(2) . . ? N1 C9 H9A 109.6 . . ? N1 C9 H9B 109.3 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C7 C2 108.0(3) . . ? N1 C7 H7A 110.1 . . ? C2 C7 H7A 110.1 . . ? N1 C7 H7B 110.2 . . ? C2 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 121.7(3) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.1 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.744 _refine_diff_density_min -0.849 _refine_diff_density_rms 0.112 #===END data_12 _database_code_depnum_ccdc_archive 'CCDC 801803' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 Bi Cl N O, C H12 B11, 2(C H2 Cl2)' _chemical_formula_sum 'C17 H38 B11 Bi Cl5 N O' _chemical_formula_weight 777.62 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' O O 0.0106 0.0060 '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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1429(7) _cell_length_b 11.9780(4) _cell_length_c 15.2951(9) _cell_angle_alpha 71.583(6) _cell_angle_beta 81.044(6) _cell_angle_gamma 87.254(7) _cell_volume 1569.86(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 27477 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 6.056 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.075 0 0 -1 0.062 0 -1 0 0.147 0 1 0 0.201 9 0 0 0.108 -1 0 0 0.070 0 1 -1 0.107 0 -1 -1 0.148 1 1 0 0.150 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.223 _exptl_absorpt_correction_T_max 0.490 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27420 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7142 _reflns_number_gt 6508 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0285P)^2^+5.8275P] 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 7142 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.750236(16) 0.386336(13) 0.318792(10) 0.01972(5) Uani 1 1 d . . . Cl1 Cl 0.60374(12) 0.54213(10) 0.36751(8) 0.0324(2) Uani 1 1 d . . . Cl3 Cl 0.3210(2) 0.29342(19) 0.29179(13) 0.0734(5) Uani 1 1 d . . . Cl5 Cl 0.59445(16) 0.85829(14) 0.00911(13) 0.0597(4) Uani 1 1 d . . . Cl2 Cl 0.4342(3) 0.4014(2) 0.0971(2) 0.1148(10) Uani 1 1 d . . . N1 N 0.8827(4) 0.5405(3) 0.1921(2) 0.0241(7) Uani 1 1 d . . . C28 C 0.4168(8) 0.8343(7) 0.0852(10) 0.130(5) Uani 1 1 d . . . H28A H 0.4152 0.8719 0.1329 0.157 Uiso 1 1 d R . . H28B H 0.3433 0.8723 0.0460 0.157 Uiso 1 1 d R . . C3 C 1.1493(5) 0.5508(4) 0.3506(3) 0.0303(10) Uani 1 1 d . . . H3 H 1.2027 0.6194 0.3181 0.036 Uiso 1 1 d R . . B22 B 1.0487(6) 0.0377(4) 0.1243(4) 0.0272(10) Uani 1 1 d . . . H22 H 1.1449 0.0226 0.0764 0.033 Uiso 1 1 d R . . C10 C 0.9054(5) 0.2348(4) 0.5042(3) 0.0287(9) Uani 1 1 d . . . H10A H 0.9503 0.1686 0.4865 0.034 Uiso 1 1 d R . . H10B H 0.9054 0.2185 0.5704 0.034 Uiso 1 1 d R . . B26 B 0.8835(5) -0.0290(5) 0.1416(4) 0.0262(10) Uani 1 1 d . . . H26 H 0.8690 -0.0906 0.1033 0.031 Uiso 1 1 d R . . C11 C 0.6442(5) 0.1664(4) 0.5469(3) 0.0241(9) Uani 1 1 d . . . C4 C 1.1945(5) 0.4749(5) 0.4298(3) 0.0321(10) Uani 1 1 d . . . H4 H 1.2788 0.4930 0.4498 0.039 Uiso 1 1 d R . . C13 C 0.6271(5) 0.1809(4) 0.6433(3) 0.0307(10) Uani 1 1 d . . . H13A H 0.7193 0.1633 0.6674 0.037 Uiso 1 1 d R . . H13B H 0.5519 0.1280 0.6841 0.037 Uiso 1 1 d R . . H13C H 0.5990 0.2604 0.6392 0.037 Uiso 1 1 d R . . C5 C 1.1174(5) 0.3728(4) 0.4805(3) 0.0303(10) Uani 1 1 d . . . H5 H 1.1502 0.3229 0.5339 0.036 Uiso 1 1 d R . . C15 C 0.9276(6) 0.1537(4) 0.2533(4) 0.0344(11) Uani 1 1 d . . . H15 H 0.9435 0.2155 0.2911 0.041 Uiso 1 1 d R . . C12 C 0.6892(6) 0.0428(4) 0.5482(4) 0.0347(11) Uani 1 1 d . . . H12A H 0.7064 0.0398 0.4855 0.042 Uiso 1 1 d R . . H12B H 0.6113 -0.0110 0.5839 0.042 Uiso 1 1 d R . . H12C H 0.7781 0.0213 0.5757 0.042 Uiso 1 1 d R . . B25 B 0.7373(6) 0.0588(5) 0.1624(4) 0.0292(11) Uani 1 1 d . . . H25 H 0.6283 0.0576 0.1408 0.035 Uiso 1 1 d R . . C6 C 0.9918(4) 0.3443(4) 0.4511(3) 0.0234(8) Uani 1 1 d . . . C14 C 0.5035(5) 0.2038(4) 0.5044(4) 0.0336(10) Uani 1 1 d . . . H14A H 0.4812 0.2841 0.5009 0.040 Uiso 1 1 d R . . H14B H 0.4228 0.1543 0.5420 0.040 Uiso 1 1 d R . . H14C H 0.5180 0.1967 0.4429 0.040 Uiso 1 1 d R . . B20 B 0.8188(6) 0.1910(5) 0.1613(4) 0.0268(10) Uani 1 1 d . . . H20 H 0.7625 0.2764 0.1390 0.032 Uiso 1 1 d R . . B17 B 1.0727(5) 0.0594(5) 0.2286(4) 0.0276(10) Uani 1 1 d . . . H17 H 1.1821 0.0597 0.2500 0.033 Uiso 1 1 d R . . C2 C 1.0227(5) 0.5248(4) 0.3203(3) 0.0232(8) Uani 1 1 d . . . B23 B 0.9899(6) -0.0718(5) 0.2296(4) 0.0281(10) Uani 1 1 d . . . H23 H 1.0455 -0.1576 0.2506 0.034 Uiso 1 1 d R . . B24 B 0.7953(6) -0.0588(5) 0.2539(4) 0.0314(11) Uani 1 1 d . . . H24 H 0.7250 -0.1364 0.2914 0.038 Uiso 1 1 d R . . C1 C 0.9467(4) 0.4206(4) 0.3709(3) 0.0202(8) Uani 1 1 d . . . B21 B 0.8969(6) 0.1179(5) 0.0806(4) 0.0293(11) Uani 1 1 d . . . H21 H 0.8926 0.1550 0.0054 0.035 Uiso 1 1 d R . . B18 B 0.9128(6) 0.0003(5) 0.3109(4) 0.0301(11) Uani 1 1 d . . . H18 H 0.9175 -0.0378 0.3860 0.036 Uiso 1 1 d R . . C7 C 0.9614(5) 0.6073(4) 0.2382(3) 0.0256(9) Uani 1 1 d . . . H7A H 0.8925 0.6610 0.2591 0.031 Uiso 1 1 d R . . H7B H 1.0408 0.6534 0.1939 0.031 Uiso 1 1 d R . . C9 C 0.7849(6) 0.6196(5) 0.1309(4) 0.0386(11) Uani 1 1 d . . . H9A H 0.7133 0.6535 0.1681 0.046 Uiso 1 1 d R . . H9B H 0.7347 0.5755 0.1018 0.046 Uiso 1 1 d R . . H9C H 0.8423 0.6811 0.0838 0.046 Uiso 1 1 d R . . C8 C 0.9931(6) 0.4849(4) 0.1369(3) 0.0332(10) Uani 1 1 d . . . H8A H 1.0611 0.5438 0.0956 0.040 Uiso 1 1 d R . . H8B H 0.9437 0.4497 0.1012 0.040 Uiso 1 1 d R . . H8C H 1.0464 0.4255 0.1782 0.040 Uiso 1 1 d R . . O1 O 0.7559(3) 0.2515(3) 0.4835(2) 0.0261(6) Uani 1 1 d . . . B16 B 1.0143(6) 0.1776(5) 0.1366(4) 0.0272(10) Uani 1 1 d . . . H16 H 1.0852 0.2546 0.0984 0.033 Uiso 1 1 d R . . B19 B 0.7566(6) 0.0813(5) 0.2691(4) 0.0279(10) Uani 1 1 d . . . H19 H 0.6600 0.0960 0.3169 0.034 Uiso 1 1 d R . . C27 C 0.3950(6) 0.2709(5) 0.1869(4) 0.0451(13) Uani 1 1 d . . . H27A H 0.4850 0.2249 0.1950 0.054 Uiso 1 1 d R . . H27B H 0.3249 0.2256 0.1702 0.054 Uiso 1 1 d R . . Cl4 Cl 0.3744(2) 0.6904(2) 0.1298(2) 0.1058(9) 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 Bi1 0.01919(8) 0.01827(8) 0.02158(8) -0.00536(6) -0.00444(5) -0.00017(5) Cl1 0.0275(5) 0.0305(6) 0.0387(6) -0.0129(5) -0.0017(4) 0.0089(4) Cl3 0.0815(12) 0.0917(14) 0.0626(10) -0.0427(10) -0.0282(9) 0.0354(11) Cl5 0.0323(7) 0.0537(9) 0.0748(11) 0.0059(8) -0.0078(7) -0.0008(6) Cl2 0.118(2) 0.0689(14) 0.110(2) 0.0261(13) 0.0160(16) -0.0159(13) N1 0.0299(19) 0.0196(17) 0.0208(17) -0.0034(14) -0.0043(14) -0.0001(14) C28 0.032(4) 0.050(4) 0.258(15) 0.018(6) -0.009(6) 0.003(3) C3 0.025(2) 0.034(2) 0.036(2) -0.020(2) 0.0034(19) -0.0075(18) B22 0.026(2) 0.027(2) 0.035(3) -0.018(2) -0.005(2) 0.0046(19) C10 0.020(2) 0.032(2) 0.026(2) 0.0017(18) -0.0051(17) 0.0040(17) B26 0.022(2) 0.033(3) 0.028(2) -0.015(2) -0.0027(19) 0.0023(19) C11 0.024(2) 0.020(2) 0.025(2) -0.0017(17) -0.0008(16) -0.0040(16) C4 0.020(2) 0.050(3) 0.034(2) -0.024(2) -0.0013(18) -0.0047(19) C13 0.030(2) 0.034(2) 0.030(2) -0.013(2) -0.0002(19) -0.0013(19) C5 0.021(2) 0.046(3) 0.026(2) -0.014(2) -0.0055(17) 0.0074(19) C15 0.038(3) 0.033(3) 0.037(3) -0.016(2) -0.011(2) 0.009(2) C12 0.044(3) 0.024(2) 0.035(3) -0.008(2) -0.003(2) -0.004(2) B25 0.022(2) 0.035(3) 0.034(3) -0.015(2) -0.006(2) 0.002(2) C6 0.0179(19) 0.030(2) 0.024(2) -0.0127(18) -0.0015(16) 0.0010(16) C14 0.024(2) 0.035(3) 0.037(3) -0.003(2) -0.0044(19) -0.0096(19) B20 0.026(2) 0.030(3) 0.027(2) -0.012(2) -0.0050(19) 0.006(2) B17 0.022(2) 0.027(2) 0.038(3) -0.015(2) -0.009(2) 0.0054(19) C2 0.0208(19) 0.024(2) 0.027(2) -0.0132(17) -0.0009(16) -0.0003(16) B23 0.024(2) 0.025(2) 0.037(3) -0.012(2) -0.004(2) 0.0022(19) B24 0.025(2) 0.029(3) 0.040(3) -0.011(2) 0.000(2) -0.003(2) C1 0.0171(18) 0.024(2) 0.0211(19) -0.0089(16) -0.0024(15) -0.0005(15) B21 0.029(3) 0.040(3) 0.021(2) -0.014(2) -0.0022(19) 0.003(2) B18 0.031(3) 0.029(3) 0.028(3) -0.006(2) -0.004(2) 0.007(2) C7 0.027(2) 0.019(2) 0.031(2) -0.0092(17) 0.0001(17) -0.0026(16) C9 0.043(3) 0.036(3) 0.031(3) 0.000(2) -0.010(2) 0.004(2) C8 0.040(3) 0.031(2) 0.028(2) -0.011(2) 0.004(2) -0.005(2) O1 0.0175(14) 0.0269(15) 0.0273(15) 0.0014(13) -0.0034(12) -0.0034(11) B16 0.026(2) 0.026(2) 0.031(3) -0.011(2) -0.003(2) 0.0016(19) B19 0.024(2) 0.033(3) 0.024(2) -0.008(2) -0.0004(19) 0.006(2) C27 0.041(3) 0.039(3) 0.052(3) -0.011(3) -0.004(3) -0.003(2) Cl4 0.0579(11) 0.0780(14) 0.130(2) 0.0243(14) 0.0202(12) -0.0034(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.180(4) . ? Bi1 N1 2.419(3) . ? Bi1 Cl1 2.4819(11) . ? Bi1 O1 2.534(3) . ? Cl3 C27 1.739(6) . ? Cl5 C28 1.822(9) . ? Cl2 C27 1.732(6) . ? N1 C9 1.481(6) . ? N1 C8 1.484(6) . ? N1 C7 1.491(6) . ? C28 Cl4 1.680(8) . ? C28 H28A 0.9701 . ? C28 H28B 0.9701 . ? C3 C4 1.374(7) . ? C3 C2 1.394(6) . ? C3 H3 0.9300 . ? B22 B26 1.688(7) . ? B22 B17 1.743(7) . ? B22 B21 1.748(7) . ? B22 B23 1.751(8) . ? B22 B16 1.753(7) . ? B22 H22 1.1000 . ? C10 O1 1.440(5) . ? C10 C6 1.493(6) . ? C10 H10A 0.9701 . ? C10 H10B 0.9699 . ? B26 B21 1.712(8) . ? B26 B25 1.714(7) . ? B26 B24 1.715(7) . ? B26 B23 1.716(7) . ? B26 H26 1.0999 . ? C11 O1 1.479(5) . ? C11 C12 1.513(6) . ? C11 C14 1.517(6) . ? C11 C13 1.521(6) . ? C4 C5 1.381(7) . ? C4 H4 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9599 . ? C5 C6 1.391(6) . ? C5 H5 0.9299 . ? C15 B18 1.770(7) . ? C15 B19 1.771(7) . ? C15 B17 1.774(7) . ? C15 B16 1.777(7) . ? C15 B20 1.779(7) . ? C15 H15 1.1000 . ? C12 H12A 0.9601 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? B25 B24 1.772(8) . ? B25 B19 1.772(7) . ? B25 B20 1.777(8) . ? B25 B21 1.779(7) . ? B25 H25 1.1001 . ? C6 C1 1.387(6) . ? C14 H14A 0.9601 . ? C14 H14B 0.9600 . ? C14 H14C 0.9599 . ? B20 B21 1.775(7) . ? B20 B16 1.779(7) . ? B20 B19 1.783(7) . ? B20 H20 1.1000 . ? B17 B23 1.772(7) . ? B17 B16 1.782(7) . ? B17 B18 1.785(8) . ? B17 H17 1.1000 . ? C2 C1 1.395(6) . ? C2 C7 1.500(6) . ? B23 B24 1.770(7) . ? B23 B18 1.771(7) . ? B23 H23 1.1000 . ? B24 B19 1.778(8) . ? B24 B18 1.781(8) . ? B24 H24 1.1000 . ? B21 B16 1.774(7) . ? B21 H21 1.1001 . ? B18 B19 1.775(7) . ? B18 H18 1.1000 . ? C7 H7A 0.9699 . ? C7 H7B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9601 . ? C9 H9C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9599 . ? C8 H8C 0.9600 . ? B16 H16 1.1000 . ? B19 H19 1.1000 . ? C27 H27A 0.9700 . ? C27 H27B 0.9701 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Bi1 N1 74.67(14) . . ? C1 Bi1 Cl1 93.22(11) . . ? N1 Bi1 Cl1 88.02(9) . . ? C1 Bi1 O1 69.55(13) . . ? N1 Bi1 O1 144.20(11) . . ? Cl1 Bi1 O1 94.68(8) . . ? C9 N1 C8 110.0(4) . . ? C9 N1 C7 110.6(4) . . ? C8 N1 C7 109.3(3) . . ? C9 N1 Bi1 113.4(3) . . ? C8 N1 Bi1 108.4(3) . . ? C7 N1 Bi1 105.0(2) . . ? Cl4 C28 Cl5 111.5(5) . . ? Cl4 C28 H28A 112.6 . . ? Cl5 C28 H28A 110.5 . . ? Cl4 C28 H28B 107.7 . . ? Cl5 C28 H28B 106.1 . . ? H28A C28 H28B 108.1 . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 120.6 . . ? B26 B22 B17 107.7(4) . . ? B26 B22 B21 59.8(3) . . ? B17 B22 B21 110.5(3) . . ? B26 B22 B23 59.8(3) . . ? B17 B22 B23 61.0(3) . . ? B21 B22 B23 110.1(4) . . ? B26 B22 B16 107.5(4) . . ? B17 B22 B16 61.3(3) . . ? B21 B22 B16 60.9(3) . . ? B23 B22 B16 110.4(4) . . ? B26 B22 H22 123.3 . . ? B17 B22 H22 120.4 . . ? B21 B22 H22 120.3 . . ? B23 B22 H22 120.3 . . ? B16 B22 H22 120.6 . . ? O1 C10 C6 108.7(3) . . ? O1 C10 H10A 110.1 . . ? C6 C10 H10A 109.9 . . ? O1 C10 H10B 110.1 . . ? C6 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? B22 B26 B21 61.9(3) . . ? B22 B26 B25 112.7(4) . . ? B21 B26 B25 62.6(3) . . ? B22 B26 B24 112.6(4) . . ? B21 B26 B24 113.9(4) . . ? B25 B26 B24 62.2(3) . . ? B22 B26 B23 61.9(3) . . ? B21 B26 B23 113.6(4) . . ? B25 B26 B23 113.3(4) . . ? B24 B26 B23 62.1(3) . . ? B22 B26 H26 119.4 . . ? B21 B26 H26 118.0 . . ? B25 B26 H26 118.4 . . ? B24 B26 H26 118.6 . . ? B23 B26 H26 118.7 . . ? O1 C11 C12 109.8(4) . . ? O1 C11 C14 103.5(3) . . ? C12 C11 C14 111.6(4) . . ? O1 C11 C13 109.0(3) . . ? C12 C11 C13 112.3(4) . . ? C14 C11 C13 110.3(4) . . ? C3 C4 C5 121.5(4) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.3 . . ? C11 C13 H13A 109.6 . . ? C11 C13 H13B 109.3 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 120.2 . . ? B18 C15 B19 60.2(3) . . ? B18 C15 B17 60.5(3) . . ? B19 C15 B17 108.5(4) . . ? B18 C15 B16 108.8(3) . . ? B19 C15 B16 108.5(4) . . ? B17 C15 B16 60.2(3) . . ? B18 C15 B20 108.7(4) . . ? B19 C15 B20 60.3(3) . . ? B17 C15 B20 108.4(3) . . ? B16 C15 B20 60.0(3) . . ? B18 C15 H15 121.2 . . ? B19 C15 H15 121.9 . . ? B17 C15 H15 121.0 . . ? B16 C15 H15 121.1 . . ? B20 C15 H15 121.7 . . ? C11 C12 H12A 109.1 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.8 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? B26 B25 B24 58.9(3) . . ? B26 B25 B19 105.2(4) . . ? B24 B25 B19 60.2(3) . . ? B26 B25 B20 105.1(4) . . ? B24 B25 B20 108.5(4) . . ? B19 B25 B20 60.3(3) . . ? B26 B25 B21 58.7(3) . . ? B24 B25 B21 108.0(4) . . ? B19 B25 B21 108.0(4) . . ? B20 B25 B21 59.9(3) . . ? B26 B25 H25 124.6 . . ? B24 B25 H25 121.1 . . ? B19 B25 H25 121.9 . . ? B20 B25 H25 122.0 . . ? B21 B25 H25 121.9 . . ? C1 C6 C5 118.5(4) . . ? C1 C6 C10 120.0(4) . . ? C5 C6 C10 121.5(4) . . ? C11 C14 H14A 109.7 . . ? C11 C14 H14B 109.8 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 108.9 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? B21 B20 B25 60.1(3) . . ? B21 B20 B16 59.9(3) . . ? B25 B20 B16 108.0(3) . . ? B21 B20 C15 107.4(3) . . ? B25 B20 C15 107.2(4) . . ? B16 B20 C15 59.9(3) . . ? B21 B20 B19 107.7(4) . . ? B25 B20 B19 59.7(3) . . ? B16 B20 B19 107.8(4) . . ? C15 B20 B19 59.6(3) . . ? B21 B20 H20 121.8 . . ? B25 B20 H20 121.7 . . ? B16 B20 H20 121.8 . . ? C15 B20 H20 122.5 . . ? B19 B20 H20 121.9 . . ? B22 B17 B23 59.7(3) . . ? B22 B17 C15 106.6(3) . . ? B23 B17 C15 107.3(4) . . ? B22 B17 B16 59.7(3) . . ? B23 B17 B16 108.1(4) . . ? C15 B17 B16 59.9(3) . . ? B22 B17 B18 106.9(4) . . ? B23 B17 B18 59.7(3) . . ? C15 B17 B18 59.7(3) . . ? B16 B17 B18 108.0(3) . . ? B22 B17 H17 122.9 . . ? B23 B17 H17 122.0 . . ? C15 B17 H17 122.1 . . ? B16 B17 H17 121.5 . . ? B18 B17 H17 121.9 . . ? C3 C2 C1 118.6(4) . . ? C3 C2 C7 122.5(4) . . ? C1 C2 C7 118.8(4) . . ? B26 B23 B22 58.3(3) . . ? B26 B23 B24 58.9(3) . . ? B22 B23 B24 107.1(4) . . ? B26 B23 B18 105.5(4) . . ? B22 B23 B18 107.1(4) . . ? B24 B23 B18 60.4(3) . . ? B26 B23 B17 105.1(4) . . ? B22 B23 B17 59.3(3) . . ? B24 B23 B17 108.7(4) . . ? B18 B23 B17 60.5(3) . . ? B26 B23 H23 124.2 . . ? B22 B23 H23 122.3 . . ? B24 B23 H23 121.6 . . ? B18 B23 H23 122.4 . . ? B17 B23 H23 122.0 . . ? B26 B24 B23 59.0(3) . . ? B26 B24 B25 58.9(3) . . ? B23 B24 B25 108.0(4) . . ? B26 B24 B19 105.0(4) . . ? B23 B24 B19 107.7(4) . . ? B25 B24 B19 59.9(3) . . ? B26 B24 B18 105.1(4) . . ? B23 B24 B18 59.9(3) . . ? B25 B24 B18 107.9(4) . . ? B19 B24 B18 59.9(3) . . ? B26 B24 H24 124.5 . . ? B23 B24 H24 121.2 . . ? B25 B24 H24 121.9 . . ? B19 B24 H24 122.6 . . ? B18 B24 H24 122.0 . . ? C6 C1 C2 121.8(4) . . ? C6 C1 Bi1 121.8(3) . . ? C2 C1 Bi1 116.3(3) . . ? B26 B21 B22 58.4(3) . . ? B26 B21 B16 105.5(4) . . ? B22 B21 B16 59.7(3) . . ? B26 B21 B20 105.3(4) . . ? B22 B21 B20 107.1(4) . . ? B16 B21 B20 60.2(3) . . ? B26 B21 B25 58.8(3) . . ? B22 B21 B25 106.8(4) . . ? B16 B21 B25 108.1(4) . . ? B20 B21 B25 60.0(3) . . ? B26 B21 H21 124.3 . . ? B22 B21 H21 122.4 . . ? B16 B21 H21 121.7 . . ? B20 B21 H21 122.3 . . ? B25 B21 H21 122.1 . . ? C15 B18 B23 107.5(4) . . ? C15 B18 B19 59.9(3) . . ? B23 B18 B19 107.7(4) . . ? C15 B18 B24 107.7(4) . . ? B23 B18 B24 59.8(3) . . ? B19 B18 B24 60.0(3) . . ? C15 B18 B17 59.9(3) . . ? B23 B18 B17 59.8(3) . . ? B19 B18 B17 107.8(4) . . ? B24 B18 B17 107.6(4) . . ? C15 B18 H18 122.0 . . ? B23 B18 H18 122.2 . . ? B19 B18 H18 121.5 . . ? B24 B18 H18 121.7 . . ? B17 B18 H18 122.2 . . ? N1 C7 C2 110.6(3) . . ? N1 C7 H7A 109.2 . . ? C2 C7 H7A 109.3 . . ? N1 C7 H7B 109.8 . . ? C2 C7 H7B 109.9 . . ? H7A C7 H7B 108.1 . . ? N1 C9 H9A 108.7 . . ? N1 C9 H9B 109.7 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 110.0 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C8 H8A 109.2 . . ? N1 C8 H8B 109.7 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 O1 C11 116.5(3) . . ? C10 O1 Bi1 110.9(2) . . ? C11 O1 Bi1 130.1(2) . . ? B22 B16 B21 59.4(3) . . ? B22 B16 C15 106.1(4) . . ? B21 B16 C15 107.5(4) . . ? B22 B16 B20 106.7(4) . . ? B21 B16 B20 59.9(3) . . ? C15 B16 B20 60.1(3) . . ? B22 B16 B17 59.1(3) . . ? B21 B16 B17 107.6(4) . . ? C15 B16 B17 59.8(3) . . ? B20 B16 B17 108.0(4) . . ? B22 B16 H16 123.5 . . ? B21 B16 H16 121.9 . . ? C15 B16 H16 122.1 . . ? B20 B16 H16 121.6 . . ? B17 B16 H16 121.9 . . ? C15 B19 B25 107.8(4) . . ? C15 B19 B18 59.9(3) . . ? B25 B19 B18 108.1(4) . . ? C15 B19 B24 107.8(3) . . ? B25 B19 B24 59.9(3) . . ? B18 B19 B24 60.2(3) . . ? C15 B19 B20 60.1(3) . . ? B25 B19 B20 60.0(3) . . ? B18 B19 B20 108.3(4) . . ? B24 B19 B20 108.0(4) . . ? C15 B19 H19 121.9 . . ? B25 B19 H19 121.7 . . ? B18 B19 H19 121.6 . . ? B24 B19 H19 121.8 . . ? B20 B19 H19 121.5 . . ? Cl2 C27 Cl3 112.7(3) . . ? Cl2 C27 H27A 109.2 . . ? Cl3 C27 H27A 109.1 . . ? Cl2 C27 H27B 109.2 . . ? Cl3 C27 H27B 108.8 . . ? H27A C27 H27B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.091 _refine_diff_density_min -1.588 _refine_diff_density_rms 0.128 #===END data_10 _database_code_depnum_ccdc_archive 'CCDC 801804' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 Bi Cl2 N O' _chemical_formula_sum 'C14 H22 Bi Cl2 N O' _chemical_formula_weight 500.21 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 '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 9.21985(4) _cell_length_b 11.7940(7) _cell_length_c 17.0903(11) _cell_angle_alpha 90 _cell_angle_beta 112.714(4) _cell_angle_gamma 90 _cell_volume 1714.25(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 12098 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.938 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 10.590 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.069 0 0 -1 0.034 1 0 0 0.063 -1 0 0 0.117 0 1 0 0.090 0 -1 0 0.102 -1 1 0 0.080 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.175 _exptl_absorpt_correction_T_max 0.372 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12032 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3853 _reflns_number_gt 3223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0367P)^2^+14.5008P] 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 3853 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.69317(3) 0.38066(2) 0.107122(16) 0.02560(10) Uani 1 1 d . . . Cl2 Cl 0.9328(3) 0.2530(2) 0.11292(15) 0.0466(6) Uani 1 1 d . . . Cl1 Cl 0.4408(3) 0.5039(2) 0.10524(14) 0.0446(5) Uani 1 1 d . . . N1 N 0.8779(9) 0.5377(6) 0.1454(4) 0.0369(16) Uani 1 1 d . . . C11 C 0.4711(11) 0.1297(7) 0.1246(5) 0.039(2) Uani 1 1 d . . . C2 C 0.9308(9) 0.4470(7) 0.2847(5) 0.0275(16) Uani 1 1 d . . . C6 C 0.7373(10) 0.3167(6) 0.2950(5) 0.0290(16) Uani 1 1 d . . . O1 O 0.5794(7) 0.2221(5) 0.1682(4) 0.0385(14) Uani 1 1 d . . . C4 C 0.9431(11) 0.3859(7) 0.4208(5) 0.0380(19) Uani 1 1 d . . . H4 H 0.9923 0.3876 0.4796 0.046 Uiso 1 1 d R . . C3 C 1.0040(10) 0.4487(7) 0.3734(5) 0.0363(19) Uani 1 1 d . . . H3 H 1.0940 0.4923 0.3996 0.044 Uiso 1 1 d R . . C8 C 0.9483(13) 0.5544(9) 0.0820(6) 0.049(2) Uani 1 1 d . . . H8A H 0.8682 0.5739 0.0281 0.059 Uiso 1 1 d R . . H8B H 0.9997 0.4858 0.0764 0.059 Uiso 1 1 d R . . H8C H 1.0240 0.6146 0.1007 0.059 Uiso 1 1 d R . . C5 C 0.8124(10) 0.3187(7) 0.3837(5) 0.0322(18) Uani 1 1 d . . . H5 H 0.7733 0.2757 0.4168 0.039 Uiso 1 1 d R . . C10 C 0.5918(10) 0.2470(7) 0.2530(5) 0.0349(18) Uani 1 1 d . . . H10A H 0.5971 0.1776 0.2844 0.042 Uiso 1 1 d R . . H10B H 0.4999 0.2895 0.2503 0.042 Uiso 1 1 d R . . C9 C 0.8000(14) 0.6441(8) 0.1533(7) 0.055(3) Uani 1 1 d . . . H9A H 0.8748 0.7051 0.1686 0.065 Uiso 1 1 d R . . H9B H 0.7576 0.6355 0.1962 0.065 Uiso 1 1 d R . . H9C H 0.7164 0.6608 0.1000 0.065 Uiso 1 1 d R . . C1 C 0.7972(9) 0.3831(6) 0.2471(4) 0.0244(14) Uani 1 1 d . . . C7 C 1.0008(10) 0.5079(8) 0.2290(5) 0.0376(19) Uani 1 1 d . . . H7A H 1.0551 0.5758 0.2574 0.045 Uiso 1 1 d R . . H7B H 1.0772 0.4584 0.2202 0.045 Uiso 1 1 d R . . C14 C 0.5459(13) 0.0178(8) 0.1594(6) 0.050(2) Uani 1 1 d . . . H14A H 0.6488 0.0141 0.1578 0.060 Uiso 1 1 d R . . H14B H 0.4823 -0.0429 0.1262 0.060 Uiso 1 1 d R . . H14C H 0.5545 0.0109 0.2170 0.060 Uiso 1 1 d R . . C12 C 0.4542(15) 0.1442(9) 0.0331(6) 0.059(3) Uani 1 1 d . . . H12A H 0.4135 0.2185 0.0139 0.070 Uiso 1 1 d R . . H12B H 0.3817 0.0881 -0.0008 0.070 Uiso 1 1 d R . . H12C H 0.5536 0.1349 0.0280 0.070 Uiso 1 1 d R . . C13 C 0.3167(13) 0.1465(12) 0.1324(10) 0.080(4) Uani 1 1 d . . . H13A H 0.3321 0.1509 0.1912 0.097 Uiso 1 1 d R . . H13B H 0.2500 0.0831 0.1066 0.097 Uiso 1 1 d R . . H13C H 0.2683 0.2151 0.1041 0.097 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 Bi1 0.03196(16) 0.02713(16) 0.01615(14) 0.00236(11) 0.00758(10) 0.00293(12) Cl2 0.0541(13) 0.0507(13) 0.0370(11) 0.0003(10) 0.0196(10) 0.0227(11) Cl1 0.0447(12) 0.0596(14) 0.0304(10) 0.0069(10) 0.0153(9) 0.0178(11) N1 0.051(4) 0.037(4) 0.024(3) 0.002(3) 0.015(3) -0.001(3) C11 0.039(4) 0.039(5) 0.031(4) -0.001(4) 0.004(3) -0.015(4) C2 0.030(4) 0.031(4) 0.017(3) -0.004(3) 0.005(3) 0.002(3) C6 0.039(4) 0.028(4) 0.021(4) -0.001(3) 0.012(3) 0.004(3) O1 0.047(4) 0.042(3) 0.024(3) -0.002(2) 0.011(3) -0.018(3) C4 0.048(5) 0.039(5) 0.018(4) -0.005(3) 0.003(3) 0.005(4) C3 0.031(4) 0.038(5) 0.031(4) -0.009(4) 0.003(3) 0.002(3) C8 0.058(6) 0.057(6) 0.039(5) -0.003(4) 0.026(5) -0.023(5) C5 0.047(5) 0.029(4) 0.023(4) 0.008(3) 0.017(4) 0.011(4) C10 0.046(5) 0.039(4) 0.022(4) 0.004(3) 0.016(4) -0.007(4) C9 0.077(8) 0.039(5) 0.039(5) 0.010(4) 0.013(5) 0.011(5) C1 0.033(4) 0.024(3) 0.014(3) 0.001(3) 0.007(3) 0.009(3) C7 0.033(4) 0.045(5) 0.030(4) 0.000(4) 0.008(3) -0.011(4) C14 0.068(7) 0.041(5) 0.038(5) 0.000(4) 0.018(5) -0.004(5) C12 0.076(8) 0.051(6) 0.030(5) -0.003(4) 0.000(5) -0.021(6) C13 0.033(5) 0.092(9) 0.111(12) -0.025(9) 0.021(6) -0.008(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.208(7) . ? Bi1 N1 2.428(7) . ? Bi1 O1 2.556(6) . ? Bi1 Cl2 2.644(2) . ? Bi1 Cl1 2.733(2) . ? N1 C8 1.475(11) . ? N1 C9 1.479(12) . ? N1 C7 1.483(11) . ? C11 O1 1.470(10) . ? C11 C13 1.493(14) . ? C11 C14 1.502(13) . ? C11 C12 1.520(13) . ? C2 C1 1.373(11) . ? C2 C3 1.401(11) . ? C2 C7 1.522(11) . ? C6 C1 1.392(11) . ? C6 C5 1.401(11) . ? C6 C10 1.500(12) . ? O1 C10 1.440(9) . ? C4 C3 1.368(13) . ? C4 C5 1.376(13) . ? C4 H4 0.9300 . ? C3 H3 0.9299 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C5 H5 0.9300 . ? C10 H10A 0.9699 . ? C10 H10B 0.9699 . ? C9 H9A 0.9600 . ? C9 H9B 0.9599 . ? C9 H9C 0.9600 . ? C7 H7A 0.9700 . ? C7 H7B 0.9699 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9599 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9599 . ? C13 H13A 0.9600 . ? C13 H13B 0.9599 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Bi1 N1 74.5(3) . . ? C1 Bi1 O1 69.0(2) . . ? N1 Bi1 O1 143.5(2) . . ? C1 Bi1 Cl2 87.68(19) . . ? N1 Bi1 Cl2 86.27(19) . . ? O1 Bi1 Cl2 92.11(16) . . ? C1 Bi1 Cl1 91.01(19) . . ? N1 Bi1 Cl1 95.92(19) . . ? O1 Bi1 Cl1 84.96(16) . . ? Cl2 Bi1 Cl1 177.05(8) . . ? C8 N1 C9 108.7(8) . . ? C8 N1 C7 110.5(7) . . ? C9 N1 C7 109.3(7) . . ? C8 N1 Bi1 111.5(5) . . ? C9 N1 Bi1 110.9(6) . . ? C7 N1 Bi1 105.9(5) . . ? O1 C11 C13 110.0(8) . . ? O1 C11 C14 109.4(7) . . ? C13 C11 C14 112.9(9) . . ? O1 C11 C12 102.6(7) . . ? C13 C11 C12 110.7(10) . . ? C14 C11 C12 110.8(9) . . ? C1 C2 C3 119.0(7) . . ? C1 C2 C7 119.1(7) . . ? C3 C2 C7 121.8(7) . . ? C1 C6 C5 119.0(7) . . ? C1 C6 C10 120.8(7) . . ? C5 C6 C10 120.2(7) . . ? C10 O1 C11 115.8(6) . . ? C10 O1 Bi1 112.1(4) . . ? C11 O1 Bi1 129.9(5) . . ? C3 C4 C5 121.7(7) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C4 C3 C2 119.7(8) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 119.8 . . ? N1 C8 H8A 110.0 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 108.9 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C5 C6 119.2(7) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.2 . . ? O1 C10 C6 107.6(6) . . ? O1 C10 H10A 110.6 . . ? C6 C10 H10A 110.7 . . ? O1 C10 H10B 109.2 . . ? C6 C10 H10B 110.1 . . ? H10A C10 H10B 108.6 . . ? N1 C9 H9A 109.7 . . ? N1 C9 H9B 109.6 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.1 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 C1 C6 121.4(7) . . ? C2 C1 Bi1 116.8(5) . . ? C6 C1 Bi1 121.7(5) . . ? N1 C7 C2 111.3(7) . . ? N1 C7 H7A 109.9 . . ? C2 C7 H7A 109.8 . . ? N1 C7 H7B 108.9 . . ? C2 C7 H7B 108.8 . . ? H7A C7 H7B 108.1 . . ? C11 C14 H14A 109.7 . . ? C11 C14 H14B 109.9 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 108.9 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C12 H12A 109.0 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 111.1 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.9 . . ? C11 C13 H13B 108.6 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.9 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 5.265 _refine_diff_density_min -1.786 _refine_diff_density_rms 0.213 #===END data_9 _database_code_depnum_ccdc_archive 'CCDC 801805' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 Cl N O Sb, C H12 B11, C H2 Cl2' _chemical_formula_sum 'C16 H36 B11 Cl3 N O Sb' _chemical_formula_weight 605.47 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' O O 0.0106 0.0060 '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' B B 0.0013 0.0007 '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' Sb Sb -0.5866 1.5461 '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 9.5870(3) _cell_length_b 12.0591(6) _cell_length_c 13.2669(6) _cell_angle_alpha 65.008(5) _cell_angle_beta 88.935(4) _cell_angle_gamma 84.972(3) _cell_volume 1384.54(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 29690 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 1.298 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.088 1 0 0 0.146 0 0 1 0.137 0 0 -1 0.199 0 -1 0 0.098 0 1 0 0.050 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.631 _exptl_absorpt_correction_T_max 0.839 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29624 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.00 _reflns_number_total 6648 _reflns_number_gt 6120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0261P)^2^+1.4124P] 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 6648 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0622 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.293066(13) 0.577614(11) 0.195831(10) 0.01830(4) Uani 1 1 d . . . Cl1 Cl 0.41520(6) 0.43964(5) 0.13366(4) 0.03024(11) Uani 1 1 d . . . Cl2 Cl 0.17817(7) 0.28200(6) 0.73183(6) 0.04471(15) Uani 1 1 d . . . Cl3 Cl 0.35620(7) 0.48448(6) 0.64771(5) 0.03843(13) Uani 1 1 d . . . C6 C 0.0216(2) 0.6385(2) 0.05618(17) 0.0244(4) Uani 1 1 d . . . O1 O 0.23364(15) 0.73701(13) 0.00664(12) 0.0247(3) Uani 1 1 d . . . C1 C 0.0936(2) 0.55254(19) 0.15013(16) 0.0211(4) Uani 1 1 d . . . N1 N 0.22686(18) 0.41619(15) 0.35172(13) 0.0206(3) Uani 1 1 d . . . C5 C -0.1106(2) 0.6151(2) 0.03195(19) 0.0311(5) Uani 1 1 d . . . H5 H -0.1602 0.6714 -0.0311 0.037 Uiso 1 1 d R . . C8 C 0.1505(2) 0.4752(2) 0.41791(17) 0.0269(4) Uani 1 1 d . . . H8A H 0.0755 0.5319 0.3734 0.032 Uiso 1 1 d R . . H8B H 0.2141 0.5185 0.4400 0.032 Uiso 1 1 d R . . H8C H 0.1130 0.4133 0.4829 0.032 Uiso 1 1 d R . . C2 C 0.0376(2) 0.44363(19) 0.21967(16) 0.0226(4) Uani 1 1 d . . . C12 C 0.4634(2) 0.8002(2) -0.01692(19) 0.0307(5) Uani 1 1 d . . . H12A H 0.4636 0.8053 0.0534 0.037 Uiso 1 1 d R . . H12B H 0.5267 0.8551 -0.0660 0.037 Uiso 1 1 d R . . H12C H 0.4926 0.7176 -0.0059 0.037 Uiso 1 1 d R . . C3 C -0.0949(2) 0.4219(2) 0.19585(19) 0.0298(5) Uani 1 1 d . . . H3 H -0.1342 0.3503 0.2421 0.036 Uiso 1 1 d R . . C15 C 0.6725(2) 0.2217(2) 0.6169(2) 0.0321(5) Uani 1 1 d . . . H15 H 0.6049 0.3065 0.5997 0.039 Uiso 1 1 d R . . C11 C 0.3174(2) 0.83615(19) -0.06824(17) 0.0253(4) Uani 1 1 d . . . B20 B 0.6664(3) 0.0892(2) 0.7443(2) 0.0313(5) Uani 1 1 d . . . H20 H 0.5932 0.0880 0.8096 0.038 Uiso 1 1 d R . . B19 B 0.6046(3) 0.0874(2) 0.6205(2) 0.0331(5) Uani 1 1 d . . . H19 H 0.4928 0.0846 0.6052 0.040 Uiso 1 1 d R . . C7 C 0.1283(2) 0.35196(18) 0.31440(17) 0.0239(4) Uani 1 1 d . . . H7A H 0.0701 0.3057 0.3758 0.029 Uiso 1 1 d R . . H7B H 0.1806 0.2947 0.2909 0.029 Uiso 1 1 d R . . C27 C 0.3394(2) 0.3337(2) 0.7465(2) 0.0348(5) Uani 1 1 d . . . H27A H 0.3480 0.3298 0.8207 0.042 Uiso 1 1 d R . . H27B H 0.4149 0.2798 0.7375 0.042 Uiso 1 1 d R . . B22 B 0.8785(3) 0.0927(2) 0.5531(2) 0.0293(5) Uani 1 1 d . . . H22 H 0.9512 0.0939 0.4876 0.035 Uiso 1 1 d R . . C4 C -0.1680(2) 0.5083(2) 0.1017(2) 0.0334(5) Uani 1 1 d . . . H4 H -0.2570 0.4941 0.0856 0.040 Uiso 1 1 d R . . B17 B 0.8460(3) 0.2244(2) 0.5696(3) 0.0345(6) Uani 1 1 d . . . H17 H 0.8915 0.3112 0.5193 0.041 Uiso 1 1 d R . . C9 C 0.3430(2) 0.3280(2) 0.42060(19) 0.0306(5) Uani 1 1 d . . . H9A H 0.3045 0.2608 0.4805 0.037 Uiso 1 1 d R . . H9B H 0.4005 0.3687 0.4504 0.037 Uiso 1 1 d R . . H9C H 0.3987 0.2974 0.3754 0.037 Uiso 1 1 d R . . C14 C 0.2597(3) 0.9581(2) -0.0700(2) 0.0398(6) Uani 1 1 d . . . H14A H 0.1658 0.9780 -0.1000 0.048 Uiso 1 1 d R . . H14B H 0.3174 1.0212 -0.1155 0.048 Uiso 1 1 d R . . H14C H 0.2596 0.9525 0.0044 0.048 Uiso 1 1 d R . . B26 B 0.8818(3) -0.0384(2) 0.6726(2) 0.0332(5) Uani 1 1 d . . . H26 H 0.9509 -0.1224 0.6896 0.040 Uiso 1 1 d R . . B25 B 0.8370(3) 0.0114(3) 0.7774(2) 0.0361(6) Uani 1 1 d . . . H25 H 0.8753 -0.0402 0.8639 0.043 Uiso 1 1 d R . . B16 B 0.8168(3) 0.1741(3) 0.7136(2) 0.0331(6) Uani 1 1 d . . . H16 H 0.8434 0.2283 0.7584 0.040 Uiso 1 1 d R . . C10 C 0.0858(2) 0.7543(2) -0.01707(19) 0.0306(5) Uani 1 1 d . . . H10A H 0.0690 0.7732 -0.0947 0.037 Uiso 1 1 d R . . H10B H 0.0441 0.8224 -0.0027 0.037 Uiso 1 1 d R . . B23 B 0.7399(3) 0.0082(3) 0.5757(2) 0.0363(6) Uani 1 1 d . . . H23 H 0.7178 -0.0459 0.5296 0.044 Uiso 1 1 d R . . B18 B 0.7167(3) 0.1709(2) 0.5123(2) 0.0347(6) Uani 1 1 d . . . H18 H 0.6794 0.2219 0.4256 0.042 Uiso 1 1 d R . . B24 B 0.7075(3) -0.0432(2) 0.7191(2) 0.0344(6) Uani 1 1 d . . . H24 H 0.6622 -0.1306 0.7674 0.041 Uiso 1 1 d R . . B21 B 0.9480(3) 0.0954(3) 0.6684(3) 0.0393(7) Uani 1 1 d . . . H21 H 1.0601 0.0980 0.6825 0.047 Uiso 1 1 d R . . C13 C 0.3164(3) 0.8379(2) -0.18351(18) 0.0351(5) Uani 1 1 d . . . H13A H 0.3420 0.7567 -0.1778 0.042 Uiso 1 1 d R . . H13B H 0.3819 0.8927 -0.2294 0.042 Uiso 1 1 d R . . H13C H 0.2241 0.8655 -0.2160 0.042 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 Sb1 0.01769(7) 0.01759(7) 0.01825(7) -0.00611(5) -0.00006(4) -0.00214(4) Cl1 0.0285(2) 0.0324(3) 0.0307(3) -0.0155(2) 0.0043(2) 0.0042(2) Cl2 0.0458(3) 0.0335(3) 0.0447(3) -0.0046(3) -0.0087(3) -0.0123(3) Cl3 0.0382(3) 0.0325(3) 0.0417(3) -0.0117(2) -0.0020(2) -0.0087(2) C6 0.0207(9) 0.0321(11) 0.0217(9) -0.0133(8) 0.0010(7) 0.0011(8) O1 0.0205(7) 0.0226(7) 0.0219(7) -0.0008(6) -0.0014(5) 0.0004(5) C1 0.0186(9) 0.0260(10) 0.0219(9) -0.0132(8) 0.0020(7) -0.0021(7) N1 0.0243(8) 0.0184(8) 0.0182(7) -0.0064(6) 0.0005(6) -0.0043(6) C5 0.0211(10) 0.0479(14) 0.0271(10) -0.0195(10) -0.0043(8) 0.0035(9) C8 0.0345(11) 0.0272(10) 0.0226(9) -0.0133(8) 0.0033(8) -0.0065(8) C2 0.0233(9) 0.0272(10) 0.0231(9) -0.0159(8) 0.0042(7) -0.0051(8) C12 0.0274(11) 0.0290(11) 0.0269(10) -0.0027(9) -0.0002(8) -0.0064(9) C3 0.0252(10) 0.0401(12) 0.0323(11) -0.0219(10) 0.0065(8) -0.0119(9) C15 0.0306(11) 0.0289(11) 0.0349(12) -0.0122(9) 0.0028(9) 0.0001(9) C11 0.0290(10) 0.0195(9) 0.0208(9) -0.0017(7) -0.0004(8) -0.0027(8) B20 0.0294(12) 0.0280(12) 0.0263(12) -0.0034(10) 0.0042(9) 0.0063(10) B19 0.0299(12) 0.0256(12) 0.0396(14) -0.0088(11) -0.0021(10) -0.0073(10) C7 0.0275(10) 0.0222(9) 0.0253(9) -0.0117(8) 0.0037(8) -0.0099(8) C27 0.0300(11) 0.0323(12) 0.0337(12) -0.0065(10) -0.0062(9) 0.0021(9) B22 0.0336(13) 0.0194(11) 0.0402(13) -0.0180(10) 0.0147(10) -0.0043(9) C4 0.0195(10) 0.0525(15) 0.0382(12) -0.0282(11) 0.0016(9) -0.0077(9) B17 0.0310(13) 0.0228(12) 0.0544(16) -0.0206(12) 0.0185(12) -0.0082(10) C9 0.0319(11) 0.0234(10) 0.0274(10) -0.0021(8) -0.0045(9) -0.0008(8) C14 0.0463(14) 0.0240(11) 0.0444(14) -0.0104(10) -0.0044(11) 0.0013(10) B26 0.0317(13) 0.0265(12) 0.0454(15) -0.0197(11) 0.0003(11) 0.0003(10) B25 0.0380(14) 0.0326(13) 0.0372(14) -0.0169(11) -0.0102(11) 0.0131(11) B16 0.0278(12) 0.0332(13) 0.0457(15) -0.0253(12) -0.0060(11) 0.0068(10) C10 0.0217(10) 0.0326(11) 0.0280(10) -0.0047(9) -0.0042(8) 0.0049(8) B23 0.0472(16) 0.0270(13) 0.0384(14) -0.0161(11) -0.0013(12) -0.0101(11) B18 0.0498(16) 0.0268(12) 0.0280(12) -0.0119(10) 0.0049(11) -0.0049(11) B24 0.0315(13) 0.0234(12) 0.0412(14) -0.0067(11) 0.0033(11) -0.0040(10) B21 0.0228(12) 0.0349(14) 0.072(2) -0.0340(15) 0.0008(12) -0.0007(10) C13 0.0339(12) 0.0436(14) 0.0232(10) -0.0093(10) 0.0015(9) -0.0061(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 C1 2.1010(19) . ? Sb1 N1 2.2881(16) . ? Sb1 Cl1 2.3668(5) . ? Sb1 O1 2.4706(14) . ? Cl2 C27 1.760(3) . ? Cl3 C27 1.755(2) . ? C6 C1 1.386(3) . ? C6 C5 1.394(3) . ? C6 C10 1.502(3) . ? O1 C10 1.436(2) . ? O1 C11 1.482(2) . ? C1 C2 1.395(3) . ? N1 C7 1.486(2) . ? N1 C9 1.488(3) . ? N1 C8 1.492(3) . ? C5 C4 1.384(4) . ? C5 H5 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C2 C3 1.388(3) . ? C2 C7 1.502(3) . ? C12 C11 1.513(3) . ? C12 H12A 0.9601 . ? C12 H12B 0.9600 . ? C12 H12C 0.9599 . ? C3 C4 1.394(3) . ? C3 H3 0.9300 . ? C15 B17 1.764(3) . ? C15 B18 1.769(4) . ? C15 B20 1.774(3) . ? C15 B19 1.780(4) . ? C15 B16 1.788(4) . ? C15 H15 1.0999 . ? C11 C14 1.516(3) . ? C11 C13 1.521(3) . ? B20 B19 1.766(4) . ? B20 B24 1.775(4) . ? B20 B25 1.778(4) . ? B20 B16 1.783(4) . ? B20 H20 1.1001 . ? B19 B18 1.772(4) . ? B19 B23 1.784(4) . ? B19 B24 1.789(4) . ? B19 H19 1.1000 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? B22 B23 1.691(4) . ? B22 B21 1.693(4) . ? B22 B17 1.693(3) . ? B22 B26 1.700(4) . ? B22 B18 1.712(4) . ? B22 H22 1.1000 . ? C4 H4 0.9301 . ? B17 B18 1.765(4) . ? B17 B16 1.769(4) . ? B17 B21 1.776(4) . ? B17 H17 1.1000 . ? C9 H9A 0.9600 . ? C9 H9B 0.9599 . ? C9 H9C 0.9601 . ? C14 H14A 0.9601 . ? C14 H14B 0.9599 . ? C14 H14C 0.9600 . ? B26 B21 1.763(4) . ? B26 B25 1.765(4) . ? B26 B24 1.768(4) . ? B26 B23 1.772(4) . ? B26 H26 1.1001 . ? B25 B16 1.772(4) . ? B25 B21 1.773(5) . ? B25 B24 1.783(4) . ? B25 H25 1.0999 . ? B16 B21 1.757(4) . ? B16 H16 1.1000 . ? C10 H10A 0.9702 . ? C10 H10B 0.9700 . ? B23 B24 1.765(4) . ? B23 B18 1.773(4) . ? B23 H23 1.1000 . ? B18 H18 1.1000 . ? B24 H24 1.1000 . ? B21 H21 1.1000 . ? C13 H13A 0.9600 . ? C13 H13B 0.9599 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Sb1 N1 77.27(7) . . ? C1 Sb1 Cl1 95.08(5) . . ? N1 Sb1 Cl1 90.40(4) . . ? C1 Sb1 O1 71.50(6) . . ? N1 Sb1 O1 148.68(5) . . ? Cl1 Sb1 O1 94.57(4) . . ? C1 C6 C5 118.7(2) . . ? C1 C6 C10 120.04(18) . . ? C5 C6 C10 121.27(19) . . ? C10 O1 C11 116.06(15) . . ? C10 O1 Sb1 112.23(11) . . ? C11 O1 Sb1 129.09(11) . . ? C6 C1 C2 121.62(18) . . ? C6 C1 Sb1 122.26(15) . . ? C2 C1 Sb1 116.12(14) . . ? C7 N1 C9 110.40(16) . . ? C7 N1 C8 109.73(16) . . ? C9 N1 C8 109.62(16) . . ? C7 N1 Sb1 106.89(11) . . ? C9 N1 Sb1 115.65(13) . . ? C8 N1 Sb1 104.28(12) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 119.9 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.3 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.6 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C2 C1 119.3(2) . . ? C3 C2 C7 123.00(19) . . ? C1 C2 C7 117.61(17) . . ? C11 C12 H12A 109.7 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.4 . . ? B17 C15 B18 59.96(16) . . ? B17 C15 B20 107.55(18) . . ? B18 C15 B20 107.31(17) . . ? B17 C15 B19 107.87(17) . . ? B18 C15 B19 59.91(15) . . ? B20 C15 B19 59.60(15) . . ? B17 C15 B16 59.75(16) . . ? B18 C15 B16 107.68(18) . . ? B20 C15 B16 60.08(15) . . ? B19 C15 B16 107.89(17) . . ? B17 C15 H15 122.0 . . ? B18 C15 H15 122.3 . . ? B20 C15 H15 121.9 . . ? B19 C15 H15 121.8 . . ? B16 C15 H15 121.6 . . ? O1 C11 C12 104.34(15) . . ? O1 C11 C14 109.91(18) . . ? C12 C11 C14 110.55(19) . . ? O1 C11 C13 109.00(17) . . ? C12 C11 C13 110.73(19) . . ? C14 C11 C13 112.03(19) . . ? B19 B20 C15 60.37(14) . . ? B19 B20 B24 60.67(16) . . ? C15 B20 B24 108.76(18) . . ? B19 B20 B25 109.18(19) . . ? C15 B20 B25 108.58(18) . . ? B24 B20 B25 60.26(15) . . ? B19 B20 B16 108.71(18) . . ? C15 B20 B16 60.34(15) . . ? B24 B20 B16 107.98(18) . . ? B25 B20 B16 59.70(16) . . ? B19 B20 H20 120.6 . . ? C15 B20 H20 121.1 . . ? B24 B20 H20 121.4 . . ? B25 B20 H20 121.6 . . ? B16 B20 H20 121.9 . . ? B20 B19 B18 107.50(19) . . ? B20 B19 C15 60.02(15) . . ? B18 B19 C15 59.72(14) . . ? B20 B19 B23 106.79(19) . . ? B18 B19 B23 59.80(16) . . ? C15 B19 B23 107.19(18) . . ? B20 B19 B24 59.90(15) . . ? B18 B19 B24 107.5(2) . . ? C15 B19 B24 107.86(18) . . ? B23 B19 B24 59.22(16) . . ? B20 B19 H19 122.1 . . ? B18 B19 H19 122.0 . . ? C15 B19 H19 121.9 . . ? B23 B19 H19 122.6 . . ? B24 B19 H19 121.9 . . ? N1 C7 C2 110.05(16) . . ? N1 C7 H7A 109.5 . . ? C2 C7 H7A 109.7 . . ? N1 C7 H7B 109.7 . . ? C2 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? Cl3 C27 Cl2 111.86(13) . . ? Cl3 C27 H27A 109.4 . . ? Cl2 C27 H27A 109.6 . . ? Cl3 C27 H27B 108.9 . . ? Cl2 C27 H27B 109.0 . . ? H27A C27 H27B 107.9 . . ? B23 B22 B21 115.0(2) . . ? B23 B22 B17 114.66(19) . . ? B21 B22 B17 63.25(17) . . ? B23 B22 B26 63.02(16) . . ? B21 B22 B26 62.61(17) . . ? B17 B22 B26 115.0(2) . . ? B23 B22 B18 62.77(17) . . ? B21 B22 B18 115.08(18) . . ? B17 B22 B18 62.44(16) . . ? B26 B22 B18 115.06(19) . . ? B23 B22 H22 117.6 . . ? B21 B22 H22 117.4 . . ? B17 B22 H22 117.6 . . ? B26 B22 H22 117.5 . . ? B18 B22 H22 117.6 . . ? C5 C4 C3 121.1(2) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.5 . . ? B22 B17 C15 105.18(18) . . ? B22 B17 B18 59.31(16) . . ? C15 B17 B18 60.14(15) . . ? B22 B17 B16 104.17(19) . . ? C15 B17 B16 60.78(14) . . ? B18 B17 B16 108.64(18) . . ? B22 B17 B21 58.37(16) . . ? C15 B17 B21 108.40(19) . . ? B18 B17 B21 108.48(18) . . ? B16 B17 B21 59.42(16) . . ? B22 B17 H17 124.9 . . ? C15 B17 H17 121.7 . . ? B18 B17 H17 120.7 . . ? B16 B17 H17 122.5 . . ? B21 B17 H17 121.8 . . ? N1 C9 H9A 109.3 . . ? N1 C9 H9B 109.6 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.4 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? B22 B26 B21 58.51(17) . . ? B22 B26 B25 104.76(18) . . ? B21 B26 B25 60.32(17) . . ? B22 B26 B24 104.40(19) . . ? B21 B26 B24 108.62(19) . . ? B25 B26 B24 60.64(17) . . ? B22 B26 B23 58.24(16) . . ? B21 B26 B23 107.7(2) . . ? B25 B26 B23 108.24(19) . . ? B24 B26 B23 59.82(16) . . ? B22 B26 H26 125.2 . . ? B21 B26 H26 121.4 . . ? B25 B26 H26 122.0 . . ? B24 B26 H26 122.1 . . ? B23 B26 H26 121.7 . . ? B26 B25 B16 107.5(2) . . ? B26 B25 B21 59.79(16) . . ? B16 B25 B21 59.43(16) . . ? B26 B25 B20 107.36(19) . . ? B16 B25 B20 60.30(15) . . ? B21 B25 B20 107.34(19) . . ? B26 B25 B24 59.76(16) . . ? B16 B25 B24 108.09(18) . . ? B21 B25 B24 107.5(2) . . ? B20 B25 B24 59.79(16) . . ? B26 B25 H25 122.1 . . ? B16 B25 H25 121.7 . . ? B21 B25 H25 122.3 . . ? B20 B25 H25 121.9 . . ? B24 B25 H25 121.8 . . ? B21 B16 B17 60.48(17) . . ? B21 B16 B25 60.30(16) . . ? B17 B16 B25 108.43(18) . . ? B21 B16 B20 107.79(19) . . ? B17 B16 B20 106.95(19) . . ? B25 B16 B20 60.00(16) . . ? B21 B16 C15 108.20(19) . . ? B17 B16 C15 59.48(15) . . ? B25 B16 C15 108.22(18) . . ? B20 B16 C15 59.59(14) . . ? B21 B16 H16 121.1 . . ? B17 B16 H16 121.6 . . ? B25 B16 H16 121.4 . . ? B20 B16 H16 122.7 . . ? C15 B16 H16 121.9 . . ? O1 C10 C6 108.57(16) . . ? O1 C10 H10A 110.0 . . ? C6 C10 H10A 110.2 . . ? O1 C10 H10B 109.9 . . ? C6 C10 H10B 109.9 . . ? H10A C10 H10B 108.4 . . ? B22 B23 B24 104.90(19) . . ? B22 B23 B26 58.74(16) . . ? B24 B23 B26 59.96(16) . . ? B22 B23 B18 59.21(16) . . ? B24 B23 B18 108.50(19) . . ? B26 B23 B18 108.62(19) . . ? B22 B23 B19 104.94(18) . . ? B24 B23 B19 60.53(16) . . ? B26 B23 B19 108.42(19) . . ? B18 B23 B19 59.77(15) . . ? B22 B23 H23 124.5 . . ? B24 B23 H23 122.1 . . ? B26 B23 H23 121.0 . . ? B18 B23 H23 121.2 . . ? B19 B23 H23 122.4 . . ? B22 B18 B17 58.25(15) . . ? B22 B18 C15 104.19(19) . . ? B17 B18 C15 59.90(14) . . ? B22 B18 B19 104.53(19) . . ? B17 B18 B19 108.19(19) . . ? C15 B18 B19 60.37(15) . . ? B22 B18 B23 58.02(15) . . ? B17 B18 B23 107.3(2) . . ? C15 B18 B23 108.19(19) . . ? B19 B18 B23 60.43(16) . . ? B22 B18 H18 125.0 . . ? B17 B18 H18 121.7 . . ? C15 B18 H18 122.6 . . ? B19 B18 H18 122.2 . . ? B23 B18 H18 121.5 . . ? B23 B24 B26 60.22(17) . . ? B23 B24 B20 107.23(18) . . ? B26 B24 B20 107.35(19) . . ? B23 B24 B25 107.7(2) . . ? B26 B24 B25 59.60(16) . . ? B20 B24 B25 59.94(15) . . ? B23 B24 B19 60.25(16) . . ? B26 B24 B19 108.40(19) . . ? B20 B24 B19 59.43(15) . . ? B25 B24 B19 107.93(18) . . ? B23 B24 H24 121.9 . . ? B26 B24 H24 121.8 . . ? B20 B24 H24 122.3 . . ? B25 B24 H24 121.8 . . ? B19 B24 H24 121.5 . . ? B22 B21 B16 104.71(19) . . ? B22 B21 B26 58.88(15) . . ? B16 B21 B26 108.2(2) . . ? B22 B21 B25 104.70(19) . . ? B16 B21 B25 60.27(16) . . ? B26 B21 B25 59.88(16) . . ? B22 B21 B17 58.38(16) . . ? B16 B21 B17 60.10(15) . . ? B26 B21 B17 108.0(2) . . ? B25 B21 B17 108.11(18) . . ? B22 B21 H21 124.9 . . ? B16 B21 H21 122.3 . . ? B26 B21 H21 121.2 . . ? B25 B21 H21 122.2 . . ? B17 B21 H21 121.7 . . ? C11 C13 H13A 109.6 . . ? C11 C13 H13B 109.6 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.2 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.208 _refine_diff_density_min -0.752 _refine_diff_density_rms 0.071 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 801806' #TrackingRef '- structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C48 H64 Cl4 O8 Sb4), 4.5(CH2 Cl2)' _chemical_formula_sum 'C52.50 H73 Cl13 O8 Sb4' _chemical_formula_weight 1779.96 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' Cl Cl 0.1484 0.1585 '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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 18.544(2) _cell_length_b 19.350(2) _cell_length_c 26.135(3) _cell_angle_alpha 90 _cell_angle_beta 134.565(12) _cell_angle_gamma 90 _cell_volume 6681.3(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 81384 _cell_measurement_theta_min 1 _cell_measurement_theta_max 26 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.125 _exptl_crystal_size_mid 0.125 _exptl_crystal_size_min 0.123 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.770 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3508 _exptl_absorpt_coefficient_mu 2.167 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.062 0 1 0 0.062 0 0 1 0.062 -1 0 0 0.062 0 -1 0 0.062 0 0 -1 0.062 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_T_max 0.810 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 81089 _diffrn_reflns_av_R_equivalents 0.0759 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 26.00 _reflns_number_total 13081 _reflns_number_gt 8800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0380P)^2^+27.1748P] 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 13081 _refine_ls_number_parameters 631 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.67593(3) 0.26067(2) 0.47203(2) 0.02551(11) Uani 1 1 d . . . Sb3 Sb 0.91850(3) 0.26948(2) 0.77205(2) 0.03212(12) Uani 1 1 d . . . Sb2 Sb 0.62108(3) 0.227433(19) 0.59665(2) 0.02477(11) Uani 1 1 d . . . Sb4 Sb 0.97601(3) 0.22606(2) 0.65009(2) 0.02919(11) Uani 1 1 d . . . Cl1 Cl 0.67659(15) 0.21749(10) 0.38395(10) 0.0499(5) Uani 1 1 d . . . Cl2 Cl 0.44174(13) 0.26463(9) 0.50743(9) 0.0462(4) Uani 1 1 d . . . Cl4 Cl 1.15011(14) 0.27132(11) 0.73214(10) 0.0539(5) Uani 1 1 d . . . O3 O 0.6194(3) 0.2107(2) 0.6947(2) 0.0353(11) Uani 1 1 d . . . Cl3 Cl 0.92716(18) 0.23194(15) 0.86541(11) 0.0783(8) Uani 1 1 d . . . O6 O 0.8004(3) 0.2043(2) 0.6981(2) 0.0306(10) Uani 1 1 d . . . O8 O 0.9400(3) 0.2920(2) 0.6901(2) 0.0319(10) Uani 1 1 d . . . C2 C 0.4918(5) 0.1671(3) 0.4085(3) 0.0332(15) Uani 1 1 d . . . O1 O 0.4817(3) 0.2816(2) 0.3718(2) 0.0342(10) Uani 1 1 d . . . O2 O 0.7936(3) 0.1973(2) 0.5502(2) 0.0314(10) Uani 1 1 d . . . C1 C 0.5956(5) 0.1716(3) 0.4547(3) 0.0273(14) Uani 1 1 d . . . C37 C 0.9258(5) 0.3111(3) 0.5826(3) 0.0334(15) Uani 1 1 d . . . C24 C 0.6536(5) 0.3617(3) 0.5618(3) 0.0286(14) Uani 1 1 d . . . H24A H 0.7043 0.3831 0.5653 0.034 Uiso 1 1 d R . . H24B H 0.5886 0.3819 0.5209 0.034 Uiso 1 1 d R . . C15 C 0.7172(5) 0.3891(3) 0.7523(3) 0.0338(16) Uani 1 1 d . . . H15 H 0.7305 0.3956 0.7935 0.041 Uiso 1 1 d R . . C17 C 0.7140(5) 0.4366(3) 0.6658(3) 0.0373(16) Uani 1 1 d . . . H17 H 0.7229 0.4741 0.6485 0.045 Uiso 1 1 d R . . C48 C 0.9275(5) 0.3626(3) 0.6688(4) 0.0358(16) Uani 1 1 d . . . H48A H 0.8739 0.3836 0.6620 0.043 Uiso 1 1 d R . . H48B H 0.9895 0.3878 0.7065 0.043 Uiso 1 1 d R . . C5 C 0.6156(6) 0.0539(3) 0.4926(4) 0.0399(18) Uani 1 1 d . . . H5 H 0.6566 0.0162 0.5205 0.048 Uiso 1 1 d R . . C31 C 1.1703(6) 0.2353(5) 0.8776(4) 0.059(2) Uani 1 1 d . . . H31A H 1.2032 0.2493 0.8625 0.071 Uiso 1 1 d R . . H31B H 1.2225 0.2222 0.9278 0.071 Uiso 1 1 d R . . C26 C 1.1015(6) 0.1751(4) 0.8330(4) 0.048(2) Uani 1 1 d . . . C12 C 0.7695(5) 0.1258(3) 0.5416(4) 0.0381(17) Uani 1 1 d . . . H12A H 0.7869 0.1033 0.5183 0.046 Uiso 1 1 d R . . H12B H 0.8088 0.1046 0.5883 0.046 Uiso 1 1 d R . . C4 C 0.5123(6) 0.0494(4) 0.4476(4) 0.0449(19) Uani 1 1 d . . . H4 H 0.4842 0.0088 0.4462 0.054 Uiso 1 1 d R . . C6 C 0.6580(5) 0.1158(3) 0.4965(3) 0.0314(15) Uani 1 1 d . . . O4 O 0.6529(3) 0.2893(2) 0.5509(2) 0.0306(10) Uani 1 1 d . . . C25 C 0.9981(5) 0.1802(4) 0.7897(3) 0.0361(16) Uani 1 1 d . . . C16 C 0.7340(5) 0.4434(3) 0.7272(4) 0.0398(17) Uani 1 1 d . . . H16 H 0.7594 0.4850 0.7521 0.048 Uiso 1 1 d R . . C36 C 0.8254(5) 0.1317(3) 0.7105(4) 0.0387(17) Uani 1 1 d . . . H36A H 0.8147 0.1138 0.7395 0.046 Uiso 1 1 d R . . H36B H 0.7817 0.1067 0.6654 0.046 Uiso 1 1 d R . . O5 O 1.1121(4) 0.2914(3) 0.8675(2) 0.0517(13) Uani 1 1 d . . . C19 C 0.6605(5) 0.2676(3) 0.7424(4) 0.0395(17) Uani 1 1 d . . . H19A H 0.6128 0.2820 0.7449 0.047 Uiso 1 1 d R . . H19B H 0.7226 0.2541 0.7903 0.047 Uiso 1 1 d R . . C3 C 0.4497(6) 0.1041(4) 0.4051(4) 0.0443(18) Uani 1 1 d . . . H3 H 0.3798 0.1001 0.3730 0.053 Uiso 1 1 d R . . C29 C 0.9740(6) 0.0607(4) 0.7526(5) 0.060(2) Uani 1 1 d . . . H29 H 0.9313 0.0233 0.7255 0.072 Uiso 1 1 d R . . C9 C 0.5057(6) 0.3932(4) 0.3495(4) 0.054(2) Uani 1 1 d . . . H9A H 0.5439 0.3720 0.3415 0.065 Uiso 1 1 d R . . H9B H 0.4744 0.4346 0.3215 0.065 Uiso 1 1 d R . . H9C H 0.5502 0.4043 0.3995 0.065 Uiso 1 1 d R . . C28 C 1.0768(7) 0.0573(5) 0.7936(5) 0.073(3) Uani 1 1 d . . . H28 H 1.1038 0.0173 0.7929 0.087 Uiso 1 1 d R . . C43 C 0.9369(6) 0.2542(4) 0.5028(4) 0.056(2) Uani 1 1 d . . . H43A H 0.8769 0.2384 0.4550 0.068 Uiso 1 1 d R . . H43B H 0.9867 0.2681 0.5023 0.068 Uiso 1 1 d R . . C14 C 0.6807(5) 0.3265(3) 0.7166(3) 0.0303(14) Uani 1 1 d . . . C22 C 0.4851(7) 0.1831(5) 0.6861(5) 0.078(3) Uani 1 1 d . . . H22A H 0.4339 0.1978 0.6369 0.094 Uiso 1 1 d R . . H22B H 0.4589 0.1465 0.6941 0.094 Uiso 1 1 d R . . H22C H 0.5043 0.2213 0.7170 0.094 Uiso 1 1 d R . . O7 O 0.9785(4) 0.1985(3) 0.5540(2) 0.0462(12) Uani 1 1 d . . . C42 C 0.9029(5) 0.3690(3) 0.6007(4) 0.0368(16) Uani 1 1 d . . . C10 C 0.3523(6) 0.3240(5) 0.2493(4) 0.062(2) Uani 1 1 d . . . H10A H 0.2891 0.3074 0.2312 0.074 Uiso 1 1 d R . . H10B H 0.3405 0.3644 0.2229 0.074 Uiso 1 1 d R . . H10C H 0.3829 0.2887 0.2439 0.074 Uiso 1 1 d R . . C18 C 0.6788(4) 0.3748(3) 0.6298(3) 0.0272(14) Uani 1 1 d . . . C41 C 0.8640(6) 0.4278(4) 0.5595(4) 0.051(2) Uani 1 1 d . . . H41 H 0.8462 0.4661 0.5703 0.061 Uiso 1 1 d R . . C32 C 1.1691(6) 0.3542(5) 0.9088(4) 0.064(2) Uani 1 1 d . . . C20 C 0.5759(6) 0.1561(4) 0.7032(4) 0.0478(19) Uani 1 1 d . . . C13 C 0.6625(4) 0.3197(3) 0.6554(3) 0.0256(14) Uani 1 1 d . . . C39 C 0.8707(6) 0.3724(5) 0.4802(4) 0.059(2) Uani 1 1 d . . . H39 H 0.8608 0.3741 0.4402 0.071 Uiso 1 1 d R . . C30 C 0.9348(5) 0.1234(3) 0.7509(4) 0.0392(17) Uani 1 1 d . . . C44 C 1.0142(6) 0.1364(5) 0.5446(4) 0.061(2) Uani 1 1 d . . . C40 C 0.8462(7) 0.4275(5) 0.4986(4) 0.066(3) Uani 1 1 d . . . H40 H 0.8178 0.4667 0.4697 0.080 Uiso 1 1 d R . . C8 C 0.4246(5) 0.3433(3) 0.3283(3) 0.0375(16) Uani 1 1 d . . . C45 C 1.0535(7) 0.0901(4) 0.6058(5) 0.071(3) Uani 1 1 d . . . H45A H 1.0040 0.0864 0.6079 0.085 Uiso 1 1 d R . . H45B H 1.0663 0.0452 0.5980 0.085 Uiso 1 1 d R . . H45C H 1.1151 0.1086 0.6502 0.085 Uiso 1 1 d R . . C27 C 1.1410(6) 0.1133(5) 0.8339(5) 0.063(3) Uani 1 1 d . . . H27 H 1.2100 0.1095 0.8620 0.076 Uiso 1 1 d R . . C11 C 0.3696(7) 0.3722(4) 0.3466(5) 0.060(2) Uani 1 1 d . . . H11A H 0.4168 0.3798 0.3975 0.072 Uiso 1 1 d R . . H11B H 0.3391 0.4153 0.3219 0.072 Uiso 1 1 d R . . H11C H 0.3179 0.3407 0.3321 0.072 Uiso 1 1 d R . . C47 C 1.0996(7) 0.1559(7) 0.5499(5) 0.103(4) Uani 1 1 d . . . H47A H 1.1566 0.1717 0.5978 0.124 Uiso 1 1 d R . . H47B H 1.1200 0.1183 0.5385 0.124 Uiso 1 1 d R . . H47C H 1.0744 0.1931 0.5166 0.124 Uiso 1 1 d R . . C35 C 1.0880(7) 0.4044(5) 0.8863(5) 0.075(3) Uani 1 1 d . . . H35A H 1.0634 0.3934 0.9076 0.091 Uiso 1 1 d R . . H35B H 1.1171 0.4498 0.9010 0.091 Uiso 1 1 d R . . H35C H 1.0330 0.4029 0.8349 0.091 Uiso 1 1 d R . . C7 C 0.4227(5) 0.2249(3) 0.3621(4) 0.0420(17) Uani 1 1 d . . . H7A H 0.3880 0.2394 0.3758 0.050 Uiso 1 1 d R . . H7B H 0.3725 0.2109 0.3121 0.050 Uiso 1 1 d R . . C38 C 0.9111(5) 0.3131(4) 0.5228(4) 0.0432(18) Uani 1 1 d . . . Cl6 Cl 0.6699(3) -0.0028(2) 0.3670(2) 0.1449(15) Uani 1 1 d . . . Cl5 Cl 0.4920(3) 0.0607(2) 0.2413(2) 0.1559(17) Uani 1 1 d . . . C21 C 0.5453(7) 0.1016(4) 0.6492(4) 0.063(2) Uani 1 1 d . . . H21A H 0.6024 0.0835 0.6594 0.076 Uiso 1 1 d R . . H21B H 0.5112 0.0646 0.6497 0.076 Uiso 1 1 d R . . H21C H 0.4994 0.1231 0.6028 0.076 Uiso 1 1 d R . . C23 C 0.6566(8) 0.1266(4) 0.7793(4) 0.073(3) Uani 1 1 d . . . H23A H 0.6654 0.1572 0.8123 0.087 Uiso 1 1 d R . . H23B H 0.6360 0.0819 0.7811 0.087 Uiso 1 1 d R . . H23C H 0.7194 0.1225 0.7924 0.087 Uiso 1 1 d R . . C33 C 1.2216(8) 0.3821(6) 0.8864(6) 0.095(4) Uani 1 1 d . . . H33A H 1.1807 0.3758 0.8360 0.113 Uiso 1 1 d R . . H33B H 1.2380 0.4301 0.8983 0.113 Uiso 1 1 d R . . H33C H 1.2828 0.3557 0.9135 0.113 Uiso 1 1 d R . . C34 C 1.2415(7) 0.3373(7) 0.9880(5) 0.117(5) Uani 1 1 d . . . H34A H 1.2826 0.2989 0.9979 0.140 Uiso 1 1 d R . . H34B H 1.2838 0.3769 1.0146 0.140 Uiso 1 1 d R . . H34C H 1.2070 0.3258 1.0020 0.140 Uiso 1 1 d R . . C46 C 0.9259(8) 0.1043(5) 0.4724(5) 0.097(4) Uani 1 1 d . . . H46A H 0.9249 0.1205 0.4372 0.117 Uiso 1 1 d R . . H46B H 0.9350 0.0551 0.4773 0.117 Uiso 1 1 d R . . H46C H 0.8630 0.1158 0.4574 0.117 Uiso 1 1 d R . . C49 C 0.5737(12) 0.0577(6) 0.3309(7) 0.137(6) Uani 1 1 d . . . H49A H 0.5395 0.0477 0.3459 0.165 Uiso 1 1 d R . . H49B H 0.6056 0.1026 0.3500 0.165 Uiso 1 1 d R . . Cl7 Cl 0.4207(2) 0.03549(12) 0.00859(13) 0.0839(8) Uani 1 1 d . . . Cl8 Cl 0.3229(3) 0.0887(3) 0.0503(2) 0.176(2) Uani 1 1 d . . . C50 C 0.4343(7) 0.0807(5) 0.0720(5) 0.070(3) Uani 1 1 d . . . H50A H 0.4815 0.0544 0.1161 0.084 Uiso 1 1 d R . . H50B H 0.4639 0.1258 0.0804 0.084 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 Sb1 0.0238(2) 0.0263(2) 0.0267(2) 0.00180(17) 0.0178(2) 0.00026(17) Sb3 0.0244(2) 0.0457(3) 0.0278(2) -0.00703(19) 0.0189(2) -0.00447(19) Sb2 0.0250(2) 0.0265(2) 0.0251(2) -0.00370(17) 0.0184(2) -0.00287(17) Sb4 0.0268(2) 0.0372(2) 0.0261(2) 0.00158(18) 0.0195(2) 0.00482(18) Cl1 0.0619(13) 0.0533(11) 0.0501(11) -0.0029(9) 0.0449(11) -0.0047(9) Cl2 0.0311(10) 0.0544(11) 0.0441(10) -0.0015(8) 0.0230(9) -0.0006(8) Cl4 0.0301(10) 0.0807(14) 0.0430(10) -0.0009(10) 0.0228(9) 0.0000(9) O3 0.040(3) 0.043(3) 0.030(2) -0.004(2) 0.027(2) -0.008(2) Cl3 0.0614(15) 0.142(2) 0.0461(12) -0.0150(13) 0.0432(12) -0.0176(14) O6 0.026(2) 0.030(2) 0.031(2) -0.0006(19) 0.018(2) 0.0013(18) O8 0.037(3) 0.035(2) 0.029(2) -0.0040(19) 0.025(2) -0.0002(19) C2 0.037(4) 0.037(4) 0.034(4) -0.006(3) 0.028(4) -0.004(3) O1 0.027(2) 0.031(2) 0.039(3) 0.0023(19) 0.020(2) -0.0001(19) O2 0.029(3) 0.031(2) 0.032(2) 0.0025(19) 0.020(2) 0.0040(19) C1 0.033(4) 0.022(3) 0.035(4) -0.001(3) 0.027(3) -0.004(3) C37 0.021(4) 0.047(4) 0.027(3) 0.005(3) 0.015(3) 0.002(3) C24 0.027(4) 0.029(3) 0.031(4) 0.004(3) 0.021(3) 0.003(3) C15 0.040(4) 0.037(4) 0.027(3) -0.005(3) 0.025(3) 0.002(3) C17 0.043(4) 0.026(4) 0.037(4) -0.001(3) 0.026(4) -0.001(3) C48 0.037(4) 0.024(3) 0.046(4) -0.002(3) 0.030(4) -0.003(3) C5 0.065(6) 0.024(3) 0.043(4) 0.001(3) 0.043(4) 0.002(3) C31 0.031(4) 0.100(7) 0.038(4) 0.001(4) 0.021(4) -0.006(5) C26 0.036(5) 0.073(5) 0.038(4) 0.029(4) 0.026(4) 0.018(4) C12 0.041(5) 0.032(4) 0.039(4) 0.004(3) 0.027(4) 0.007(3) C4 0.064(6) 0.034(4) 0.060(5) -0.014(4) 0.052(5) -0.020(4) C6 0.041(4) 0.030(4) 0.032(4) 0.000(3) 0.029(4) 0.003(3) O4 0.037(3) 0.027(2) 0.035(2) -0.0035(18) 0.027(2) -0.0022(19) C25 0.022(4) 0.055(4) 0.034(4) 0.017(3) 0.021(3) 0.007(3) C16 0.040(4) 0.026(4) 0.036(4) -0.006(3) 0.020(4) 0.001(3) C36 0.039(4) 0.026(4) 0.056(5) 0.004(3) 0.035(4) 0.001(3) O5 0.034(3) 0.075(4) 0.036(3) -0.003(3) 0.021(3) -0.010(3) C19 0.044(4) 0.042(4) 0.037(4) -0.015(3) 0.031(4) -0.016(3) C3 0.046(5) 0.041(4) 0.054(5) -0.007(4) 0.038(4) -0.014(4) C29 0.045(5) 0.044(5) 0.097(7) 0.022(4) 0.052(5) 0.014(4) C9 0.051(5) 0.039(4) 0.052(5) 0.013(4) 0.029(4) 0.002(4) C28 0.059(6) 0.053(5) 0.120(8) 0.036(5) 0.068(6) 0.025(5) C43 0.063(6) 0.086(6) 0.035(4) -0.002(4) 0.040(4) -0.007(5) C14 0.026(4) 0.037(4) 0.027(3) -0.004(3) 0.018(3) -0.001(3) C22 0.082(7) 0.096(7) 0.102(7) -0.041(6) 0.081(7) -0.049(6) O7 0.044(3) 0.069(3) 0.041(3) -0.002(2) 0.035(3) 0.004(3) C42 0.034(4) 0.040(4) 0.038(4) 0.001(3) 0.026(4) -0.006(3) C10 0.045(5) 0.089(6) 0.041(5) 0.013(4) 0.027(4) 0.001(4) C18 0.022(3) 0.025(3) 0.030(3) 0.001(3) 0.017(3) 0.003(3) C41 0.059(5) 0.037(4) 0.049(5) 0.010(3) 0.035(4) 0.000(4) C32 0.042(5) 0.102(7) 0.046(5) -0.033(5) 0.029(4) -0.024(5) C20 0.061(5) 0.048(4) 0.056(5) -0.008(4) 0.048(5) -0.016(4) C13 0.020(3) 0.024(3) 0.031(3) -0.007(3) 0.018(3) 0.000(2) C39 0.054(6) 0.083(6) 0.037(5) 0.006(4) 0.030(4) -0.007(5) C30 0.041(4) 0.039(4) 0.048(4) 0.020(3) 0.035(4) 0.017(3) C44 0.054(6) 0.088(6) 0.038(5) -0.004(4) 0.031(4) 0.021(5) C40 0.070(6) 0.061(6) 0.051(5) 0.027(4) 0.036(5) -0.001(5) C8 0.032(4) 0.044(4) 0.029(4) 0.011(3) 0.018(3) 0.012(3) C45 0.084(7) 0.067(6) 0.075(6) 0.000(5) 0.061(6) 0.025(5) C27 0.035(5) 0.081(6) 0.075(6) 0.046(5) 0.039(5) 0.033(5) C11 0.071(6) 0.047(5) 0.076(6) 0.021(4) 0.057(5) 0.031(4) C47 0.055(7) 0.203(13) 0.065(6) 0.041(7) 0.047(6) 0.053(7) C35 0.062(6) 0.090(7) 0.069(6) -0.042(5) 0.044(6) -0.032(5) C7 0.021(4) 0.047(4) 0.046(4) 0.000(3) 0.019(3) -0.004(3) C38 0.041(5) 0.058(5) 0.037(4) 0.005(4) 0.030(4) -0.002(4) Cl6 0.187(4) 0.100(3) 0.182(4) -0.035(2) 0.142(4) -0.054(3) Cl5 0.161(4) 0.223(4) 0.123(3) -0.076(3) 0.114(3) -0.064(3) C21 0.090(7) 0.055(5) 0.075(6) -0.023(4) 0.069(6) -0.032(5) C23 0.118(9) 0.046(5) 0.065(6) 0.004(4) 0.068(6) -0.001(5) C33 0.090(8) 0.121(9) 0.115(9) -0.061(7) 0.087(8) -0.062(7) C34 0.045(6) 0.235(15) 0.048(6) -0.048(7) 0.024(5) 0.006(7) C46 0.088(8) 0.090(7) 0.066(6) -0.029(6) 0.037(6) 0.021(6) C49 0.286(19) 0.080(8) 0.151(12) -0.044(8) 0.191(14) -0.063(10) Cl7 0.104(2) 0.0582(14) 0.0679(15) -0.0095(11) 0.0525(16) -0.0105(13) Cl8 0.113(3) 0.319(6) 0.140(3) -0.058(4) 0.104(3) -0.079(4) C50 0.059(6) 0.070(6) 0.063(6) -0.006(5) 0.036(5) -0.026(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 Sb1 O2 2.045(4) . ? Sb1 C1 2.108(6) . ? Sb1 O4 2.444(4) . ? Sb1 Cl1 2.4569(18) . ? Sb3 O6 2.045(4) . ? Sb3 C25 2.102(7) . ? Sb3 Cl3 2.441(2) . ? Sb3 O8 2.476(4) . ? Sb2 O4 2.050(4) . ? Sb2 C13 2.117(5) . ? Sb2 O6 2.432(4) . ? Sb2 Cl2 2.4763(19) . ? Sb4 O8 2.037(4) . ? Sb4 C37 2.093(6) . ? Sb4 Cl4 2.464(2) . ? Sb4 O2 2.485(4) . ? O3 C19 1.419(7) . ? O3 C20 1.438(8) . ? O6 C36 1.443(7) . ? O8 C48 1.432(7) . ? C2 C1 1.382(9) . ? C2 C3 1.416(9) . ? C2 C7 1.477(9) . ? O1 C7 1.441(7) . ? O1 C8 1.465(7) . ? O2 C12 1.421(7) . ? C1 C6 1.387(8) . ? C37 C38 1.384(9) . ? C37 C42 1.396(9) . ? C24 O4 1.429(7) . ? C24 C18 1.510(8) . ? C24 H24A 0.9711 . ? C24 H24B 0.9703 . ? C15 C14 1.382(8) . ? C15 C16 1.387(9) . ? C15 H15 0.9292 . ? C17 C18 1.370(8) . ? C17 C16 1.375(9) . ? C17 H17 0.9289 . ? C48 C42 1.499(9) . ? C48 H48A 0.9678 . ? C48 H48B 0.9699 . ? C5 C4 1.378(10) . ? C5 C6 1.397(9) . ? C5 H5 0.9296 . ? C31 O5 1.419(9) . ? C31 C26 1.501(11) . ? C31 H31A 0.9691 . ? C31 H31B 0.9698 . ? C26 C25 1.388(9) . ? C26 C27 1.394(11) . ? C12 C6 1.510(9) . ? C12 H12A 0.9697 . ? C12 H12B 0.9699 . ? C4 C3 1.376(10) . ? C4 H4 0.9291 . ? C25 C30 1.395(10) . ? C16 H16 0.9291 . ? C36 C30 1.501(9) . ? C36 H36A 0.9716 . ? C36 H36B 0.9694 . ? O5 C32 1.470(9) . ? C19 C14 1.499(9) . ? C19 H19A 0.9707 . ? C19 H19B 0.9691 . ? C3 H3 0.9294 . ? C29 C28 1.385(11) . ? C29 C30 1.399(10) . ? C29 H29 0.9302 . ? C9 C8 1.528(10) . ? C9 H9A 0.9597 . ? C9 H9B 0.9582 . ? C9 H9C 0.9600 . ? C28 C27 1.393(12) . ? C28 H28 0.9289 . ? C43 O7 1.448(9) . ? C43 C38 1.467(10) . ? C43 H43A 0.9704 . ? C43 H43B 0.9707 . ? C14 C13 1.390(8) . ? C22 C20 1.500(11) . ? C22 H22A 0.9604 . ? C22 H22B 0.9612 . ? C22 H22C 0.9601 . ? O7 C44 1.472(9) . ? C42 C41 1.372(9) . ? C10 C8 1.523(9) . ? C10 H10A 0.9605 . ? C10 H10B 0.9610 . ? C10 H10C 0.9599 . ? C18 C13 1.400(8) . ? C41 C40 1.379(11) . ? C41 H41 0.9320 . ? C32 C34 1.514(12) . ? C32 C35 1.520(12) . ? C32 C33 1.542(11) . ? C20 C21 1.518(10) . ? C20 C23 1.530(11) . ? C39 C40 1.372(12) . ? C39 C38 1.396(10) . ? C39 H39 0.9275 . ? C44 C45 1.503(11) . ? C44 C46 1.513(11) . ? C44 C47 1.536(12) . ? C40 H40 0.9302 . ? C8 C11 1.505(9) . ? C45 H45A 0.9598 . ? C45 H45B 0.9595 . ? C45 H45C 0.9589 . ? C27 H27 0.9291 . ? C11 H11A 0.9609 . ? C11 H11B 0.9590 . ? C11 H11C 0.9613 . ? C47 H47A 0.9596 . ? C47 H47B 0.9589 . ? C47 H47C 0.9608 . ? C35 H35A 0.9593 . ? C35 H35B 0.9589 . ? C35 H35C 0.9606 . ? C7 H7A 0.9720 . ? C7 H7B 0.9697 . ? Cl6 C49 1.755(15) . ? Cl5 C49 1.674(13) . ? C21 H21A 0.9600 . ? C21 H21B 0.9603 . ? C21 H21C 0.9591 . ? C23 H23A 0.9607 . ? C23 H23B 0.9597 . ? C23 H23C 0.9595 . ? C33 H33A 0.9608 . ? C33 H33B 0.9587 . ? C33 H33C 0.9604 . ? C34 H34A 0.9608 . ? C34 H34B 0.9595 . ? C34 H34C 0.9598 . ? C46 H46A 0.9596 . ? C46 H46B 0.9594 . ? C46 H46C 0.9601 . ? C49 H49A 0.9709 . ? C49 H49B 0.9695 . ? Cl7 C50 1.728(9) . ? Cl8 C50 1.722(10) . ? C50 H50A 0.9682 . ? C50 H50B 0.9706 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Sb1 C1 79.7(2) . . ? O2 Sb1 O4 89.36(15) . . ? C1 Sb1 O4 81.43(18) . . ? O2 Sb1 Cl1 91.64(12) . . ? C1 Sb1 Cl1 89.32(16) . . ? O4 Sb1 Cl1 170.37(11) . . ? O6 Sb3 C25 79.7(2) . . ? O6 Sb3 Cl3 92.12(13) . . ? C25 Sb3 Cl3 89.55(18) . . ? O6 Sb3 O8 90.38(15) . . ? C25 Sb3 O8 79.65(19) . . ? Cl3 Sb3 O8 168.30(12) . . ? O4 Sb2 C13 79.9(2) . . ? O4 Sb2 O6 90.59(15) . . ? C13 Sb2 O6 80.89(18) . . ? O4 Sb2 Cl2 91.55(13) . . ? C13 Sb2 Cl2 90.11(16) . . ? O6 Sb2 Cl2 170.24(10) . . ? O8 Sb4 C37 80.2(2) . . ? O8 Sb4 Cl4 91.82(13) . . ? C37 Sb4 Cl4 89.44(18) . . ? O8 Sb4 O2 89.14(15) . . ? C37 Sb4 O2 79.53(19) . . ? Cl4 Sb4 O2 168.60(11) . . ? C19 O3 C20 116.6(5) . . ? C36 O6 Sb3 115.2(4) . . ? C36 O6 Sb2 113.7(4) . . ? Sb3 O6 Sb2 130.93(18) . . ? C48 O8 Sb4 114.8(4) . . ? C48 O8 Sb3 115.1(3) . . ? Sb4 O8 Sb3 130.07(19) . . ? C1 C2 C3 118.6(6) . . ? C1 C2 C7 122.8(6) . . ? C3 C2 C7 118.6(6) . . ? C7 O1 C8 116.0(5) . . ? C12 O2 Sb1 115.4(4) . . ? C12 O2 Sb4 115.4(3) . . ? Sb1 O2 Sb4 128.80(19) . . ? C2 C1 C6 121.3(6) . . ? C2 C1 Sb1 125.5(4) . . ? C6 C1 Sb1 113.2(5) . . ? C38 C37 C42 119.7(6) . . ? C38 C37 Sb4 126.3(5) . . ? C42 C37 Sb4 113.9(5) . . ? O4 C24 C18 110.6(5) . . ? O4 C24 H24A 108.1 . . ? C18 C24 H24A 109.8 . . ? O4 C24 H24B 110.2 . . ? C18 C24 H24B 110.3 . . ? H24A C24 H24B 107.8 . . ? C14 C15 C16 120.7(6) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 118.8 . . ? C18 C17 C16 119.6(6) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 119.8 . . ? O8 C48 C42 111.9(5) . . ? O8 C48 H48A 109.7 . . ? C42 C48 H48A 109.2 . . ? O8 C48 H48B 109.4 . . ? C42 C48 H48B 108.7 . . ? H48A C48 H48B 107.9 . . ? C4 C5 C6 119.4(6) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.5 . . ? O5 C31 C26 109.1(6) . . ? O5 C31 H31A 108.9 . . ? C26 C31 H31A 109.6 . . ? O5 C31 H31B 111.1 . . ? C26 C31 H31B 110.2 . . ? H31A C31 H31B 108.0 . . ? C25 C26 C27 118.9(8) . . ? C25 C26 C31 120.9(7) . . ? C27 C26 C31 120.2(7) . . ? O2 C12 C6 110.8(5) . . ? O2 C12 H12A 109.2 . . ? C6 C12 H12A 109.2 . . ? O2 C12 H12B 109.7 . . ? C6 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C3 C4 C5 121.3(6) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.5 . . ? C1 C6 C5 119.6(6) . . ? C1 C6 C12 116.3(5) . . ? C5 C6 C12 124.0(6) . . ? C24 O4 Sb2 115.0(3) . . ? C24 O4 Sb1 114.1(3) . . ? Sb2 O4 Sb1 130.70(18) . . ? C26 C25 C30 120.9(7) . . ? C26 C25 Sb3 126.4(6) . . ? C30 C25 Sb3 112.7(5) . . ? C17 C16 C15 120.9(6) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.8 . . ? O6 C36 C30 108.9(5) . . ? O6 C36 H36A 108.3 . . ? C30 C36 H36A 109.2 . . ? O6 C36 H36B 110.4 . . ? C30 C36 H36B 111.4 . . ? H36A C36 H36B 108.5 . . ? C31 O5 C32 115.8(6) . . ? O3 C19 C14 110.2(5) . . ? O3 C19 H19A 109.2 . . ? C14 C19 H19A 109.7 . . ? O3 C19 H19B 110.1 . . ? C14 C19 H19B 109.8 . . ? H19A C19 H19B 107.7 . . ? C4 C3 C2 119.7(7) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 119.1 . . ? C28 C29 C30 117.9(8) . . ? C28 C29 H29 121.8 . . ? C30 C29 H29 120.3 . . ? C8 C9 H9A 109.9 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 109.6 . . ? C8 C9 H9C 108.8 . . ? H9A C9 H9C 109.3 . . ? H9B C9 H9C 109.5 . . ? C29 C28 C27 122.0(8) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 118.5 . . ? O7 C43 C38 110.2(5) . . ? O7 C43 H43A 109.9 . . ? C38 C43 H43A 109.7 . . ? O7 C43 H43B 108.9 . . ? C38 C43 H43B 109.9 . . ? H43A C43 H43B 108.2 . . ? C15 C14 C13 117.9(6) . . ? C15 C14 C19 121.4(6) . . ? C13 C14 C19 120.6(5) . . ? C20 C22 H22A 110.6 . . ? C20 C22 H22B 108.2 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.9 . . ? H22A C22 H22C 109.4 . . ? H22B C22 H22C 109.3 . . ? C43 O7 C44 117.7(5) . . ? C41 C42 C37 121.0(6) . . ? C41 C42 C48 123.8(6) . . ? C37 C42 C48 115.2(6) . . ? C8 C10 H10A 111.0 . . ? C8 C10 H10B 108.4 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.0 . . ? H10A C10 H10C 109.4 . . ? H10B C10 H10C 109.5 . . ? C17 C18 C13 119.7(6) . . ? C17 C18 C24 124.1(6) . . ? C13 C18 C24 116.3(5) . . ? C42 C41 C40 118.2(7) . . ? C42 C41 H41 121.5 . . ? C40 C41 H41 120.2 . . ? O5 C32 C34 108.4(8) . . ? O5 C32 C35 103.8(6) . . ? C34 C32 C35 110.8(7) . . ? O5 C32 C33 109.2(6) . . ? C34 C32 C33 113.8(8) . . ? C35 C32 C33 110.3(9) . . ? O3 C20 C22 109.4(6) . . ? O3 C20 C21 104.5(5) . . ? C22 C20 C21 110.8(7) . . ? O3 C20 C23 109.4(6) . . ? C22 C20 C23 112.8(7) . . ? C21 C20 C23 109.6(7) . . ? C14 C13 C18 121.2(5) . . ? C14 C13 Sb2 125.9(4) . . ? C18 C13 Sb2 112.7(4) . . ? C40 C39 C38 118.9(7) . . ? C40 C39 H39 121.1 . . ? C38 C39 H39 120.0 . . ? C25 C30 C29 120.5(7) . . ? C25 C30 C36 117.3(6) . . ? C29 C30 C36 122.1(7) . . ? O7 C44 C45 104.4(6) . . ? O7 C44 C46 108.9(7) . . ? C45 C44 C46 112.0(9) . . ? O7 C44 C47 109.9(8) . . ? C45 C44 C47 110.5(7) . . ? C46 C44 C47 111.0(8) . . ? C39 C40 C41 122.5(7) . . ? C39 C40 H40 119.1 . . ? C41 C40 H40 118.3 . . ? O1 C8 C11 109.8(5) . . ? O1 C8 C10 108.7(6) . . ? C11 C8 C10 112.0(6) . . ? O1 C8 C9 104.0(5) . . ? C11 C8 C9 111.3(6) . . ? C10 C8 C9 110.6(6) . . ? C44 C45 H45A 109.7 . . ? C44 C45 H45B 108.8 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 110.0 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C28 C27 C26 119.7(8) . . ? C28 C27 H27 120.5 . . ? C26 C27 H27 119.8 . . ? C8 C11 H11A 109.6 . . ? C8 C11 H11B 108.7 . . ? H11A C11 H11B 109.4 . . ? C8 C11 H11C 110.5 . . ? H11A C11 H11C 109.3 . . ? H11B C11 H11C 109.4 . . ? C44 C47 H47A 108.5 . . ? C44 C47 H47B 113.1 . . ? H47A C47 H47B 109.5 . . ? C44 C47 H47C 106.6 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C32 C35 H35A 112.2 . . ? C32 C35 H35B 107.7 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 108.3 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.6 . . ? O1 C7 C2 108.6(5) . . ? O1 C7 H7A 109.3 . . ? C2 C7 H7A 109.4 . . ? O1 C7 H7B 110.0 . . ? C2 C7 H7B 110.8 . . ? H7A C7 H7B 108.6 . . ? C37 C38 C39 119.6(7) . . ? C37 C38 C43 121.7(6) . . ? C39 C38 C43 118.7(7) . . ? C20 C21 H21A 112.1 . . ? C20 C21 H21B 109.0 . . ? H21A C21 H21B 109.4 . . ? C20 C21 H21C 107.2 . . ? H21A C21 H21C 109.6 . . ? H21B C21 H21C 109.5 . . ? C20 C23 H23A 109.3 . . ? C20 C23 H23B 109.9 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.2 . . ? H23A C23 H23C 109.4 . . ? H23B C23 H23C 109.5 . . ? C32 C33 H33A 112.0 . . ? C32 C33 H33B 110.9 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 105.5 . . ? H33A C33 H33C 109.3 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 108.1 . . ? C32 C34 H34B 107.9 . . ? H34A C34 H34B 109.4 . . ? C32 C34 H34C 112.5 . . ? H34A C34 H34C 109.4 . . ? H34B C34 H34C 109.5 . . ? C44 C46 H46A 109.7 . . ? C44 C46 H46B 107.9 . . ? H46A C46 H46B 109.6 . . ? C44 C46 H46C 110.8 . . ? H46A C46 H46C 109.4 . . ? H46B C46 H46C 109.5 . . ? Cl5 C49 Cl6 110.9(6) . . ? Cl5 C49 H49A 111.4 . . ? Cl6 C49 H49A 110.8 . . ? Cl5 C49 H49B 108.4 . . ? Cl6 C49 H49B 107.3 . . ? H49A C49 H49B 107.8 . . ? Cl8 C50 Cl7 113.3(5) . . ? Cl8 C50 H50A 108.2 . . ? Cl7 C50 H50A 106.1 . . ? Cl8 C50 H50B 110.5 . . ? Cl7 C50 H50B 110.5 . . ? H50A C50 H50B 107.9 . . ? # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 0.000 426.0 217.2 2 0.000 0.500 0.500 426.0 216.3 _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.205 _refine_diff_density_min -0.953 _refine_diff_density_rms 0.128 #===END