# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name 'Paul J. Ragogna' _publ_contact_author_address ;Department of Chemistry The University of Western Ontario 1151 Richmond St. London, ON N6A 5B7 ; _publ_contact_author_email pragogna@uwo.ca _publ_contact_author_phone +15196612111 _publ_contact_author_fax +15196613022 loop_ _publ_author_name _publ_author_address A.L.Brazeau ;Department of Chemistry The University of Western Ontario 1151 Richmond St. London, ON N6A 5B7 ; N.D.Jones ;Department of Chemistry The University of Western Ontario 1151 Richmond St. London, ON N6A 5B7 ; P.J.Ragogna ;Department of Chemistry The University of Western Ontario 1151 Richmond St. London, ON N6A 5B7 ; data_2Sn _database_code_depnum_ccdc_archive 'CCDC 864988' #TrackingRef '- CIF_Ragogna_clamshell.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 Cl4 N3 Sn, C H2 Cl2' _chemical_formula_sum 'C34 H27 Cl6 N3 Sn' _chemical_formula_weight 808.98 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' Cl Cl 0.1484 0.1585 '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' Sn Sn -0.6537 1.4246 '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 _symmetry_space_group_name_Hall -P2ybc 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 11.498(2) _cell_length_b 17.844(4) _cell_length_c 18.107(6) _cell_angle_alpha 90.00 _cell_angle_beta 113.49(2) _cell_angle_gamma 90.00 _cell_volume 3407.2(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7984 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 1.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7452 _exptl_absorpt_correction_T_max 0.8347 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15195 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.46 _reflns_number_total 7779 _reflns_number_gt 6383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.1166P)^2^+5.8006P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0119(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7779 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1808 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 Sn1 Sn 0.11389(3) -0.132235(16) 0.868595(16) 0.02288(15) Uani 1 1 d . . . Cl1 Cl 0.05262(12) -0.05401(7) 0.95019(7) 0.0360(3) Uani 1 1 d . . . Cl2 Cl -0.05233(10) -0.09112(6) 0.74514(6) 0.0282(2) Uani 1 1 d . . . Cl3 Cl -0.00306(11) -0.24074(6) 0.87248(7) 0.0319(3) Uani 1 1 d . . . Cl4 Cl 0.30314(11) -0.17210(7) 0.98185(7) 0.0342(3) Uani 1 1 d . . . N1 N 0.2445(3) -0.0438(2) 0.8503(2) 0.0238(7) Uani 1 1 d . . . N2 N 0.2082(3) -0.1874(2) 0.7945(2) 0.0234(7) Uani 1 1 d . . . N3 N 0.2032(4) -0.0469(2) 0.6215(2) 0.0289(8) Uani 1 1 d . . . C1 C 0.3278(4) -0.0737(2) 0.8290(2) 0.0237(8) Uani 1 1 d . . . C2 C 0.3075(4) -0.1531(3) 0.7990(3) 0.0249(8) Uani 1 1 d . . . C3 C 0.4161(4) -0.1739(3) 0.7795(3) 0.0271(9) Uani 1 1 d . . . C4 C 0.4544(5) -0.2382(3) 0.7542(3) 0.0341(10) Uani 1 1 d . . . H4A H 0.4029 -0.2819 0.7413 0.041 Uiso 1 1 calc R . . C5 C 0.5724(5) -0.2373(3) 0.7480(3) 0.0421(12) Uani 1 1 d . . . H5A H 0.5989 -0.2811 0.7291 0.050 Uiso 1 1 calc R . . C6 C 0.6518(5) -0.1755(3) 0.7682(4) 0.0433(13) Uani 1 1 d . . . H6A H 0.7313 -0.1780 0.7638 0.052 Uiso 1 1 calc R . . C7 C 0.6156(4) -0.1090(3) 0.7951(3) 0.0341(10) Uani 1 1 d . . . C8 C 0.4963(4) -0.1095(3) 0.7992(3) 0.0278(9) Uani 1 1 d . . . C9 C 0.6863(5) -0.0415(3) 0.8197(3) 0.0406(12) Uani 1 1 d . . . H9A H 0.7677 -0.0382 0.8181 0.049 Uiso 1 1 calc R . . C10 C 0.6395(5) 0.0185(3) 0.8456(3) 0.0394(12) Uani 1 1 d . . . H10A H 0.6889 0.0630 0.8604 0.047 Uiso 1 1 calc R . . C11 C 0.5187(4) 0.0173(3) 0.8514(3) 0.0319(10) Uani 1 1 d . . . H11A H 0.4886 0.0594 0.8708 0.038 Uiso 1 1 calc R . . C12 C 0.4481(4) -0.0475(3) 0.8276(3) 0.0266(9) Uani 1 1 d . . . C13 C 0.1744(4) -0.2596(2) 0.7562(3) 0.0262(9) Uani 1 1 d . . . C14 C 0.2018(5) -0.3232(3) 0.8036(3) 0.0339(10) Uani 1 1 d . . . H14A H 0.2444 -0.3192 0.8605 0.041 Uiso 1 1 calc R . . C15 C 0.1665(5) -0.3932(3) 0.7675(4) 0.0403(12) Uani 1 1 d . . . H15A H 0.1859 -0.4373 0.7995 0.048 Uiso 1 1 calc R . . C16 C 0.1039(5) -0.3980(3) 0.6860(4) 0.0420(13) Uani 1 1 d . . . H16A H 0.0791 -0.4457 0.6615 0.050 Uiso 1 1 calc R . . C17 C 0.0758(5) -0.3342(3) 0.6385(3) 0.0377(11) Uani 1 1 d . . . H17A H 0.0328 -0.3391 0.5817 0.045 Uiso 1 1 calc R . . C18 C 0.1092(4) -0.2631(3) 0.6720(3) 0.0293(9) Uani 1 1 d . . . C19 C 0.0788(5) -0.1943(3) 0.6199(3) 0.0323(10) Uani 1 1 d . . . H19A H 0.0742 -0.1507 0.6525 0.039 Uiso 1 1 calc R . . H19B H -0.0060 -0.2007 0.5758 0.039 Uiso 1 1 calc R . . C20 C 0.1765(5) -0.1768(3) 0.5823(3) 0.0354(11) Uani 1 1 d . . . H20A H 0.2627 -0.1898 0.6215 0.042 Uiso 1 1 calc R . . H20B H 0.1573 -0.2080 0.5337 0.042 Uiso 1 1 calc R . . C21 C 0.1732(4) -0.0958(3) 0.5600(3) 0.0298(10) Uani 1 1 d . . . C22 C 0.1421(5) -0.0731(3) 0.4813(3) 0.0368(11) Uani 1 1 d . . . H22A H 0.1234 -0.1089 0.4394 0.044 Uiso 1 1 calc R . . C23 C 0.1386(5) 0.0034(3) 0.4646(3) 0.0397(12) Uani 1 1 d . . . H23A H 0.1163 0.0205 0.4110 0.048 Uiso 1 1 calc R . . C24 C 0.1685(5) 0.0538(3) 0.5278(3) 0.0350(10) Uani 1 1 d . . . H24A H 0.1677 0.1061 0.5181 0.042 Uiso 1 1 calc R . . C25 C 0.1995(4) 0.0269(3) 0.6049(3) 0.0292(9) Uani 1 1 d . . . C26 C 0.2322(5) 0.0782(3) 0.6770(3) 0.0297(9) Uani 1 1 d . . . H26A H 0.2266 0.1309 0.6589 0.036 Uiso 1 1 calc R . . H26B H 0.3208 0.0686 0.7150 0.036 Uiso 1 1 calc R . . C27 C 0.1428(4) 0.0666(3) 0.7211(3) 0.0294(9) Uani 1 1 d . . . H27A H 0.0651 0.0967 0.6937 0.035 Uiso 1 1 calc R . . H27B H 0.1175 0.0132 0.7167 0.035 Uiso 1 1 calc R . . C28 C 0.2010(4) 0.0880(2) 0.8086(3) 0.0258(9) Uani 1 1 d . . . C29 C 0.2081(5) 0.1634(3) 0.8311(3) 0.0321(10) Uani 1 1 d . . . H29A H 0.1739 0.2006 0.7906 0.039 Uiso 1 1 calc R . . C30 C 0.2641(5) 0.1849(3) 0.9111(3) 0.0412(12) Uani 1 1 d . . . H30A H 0.2696 0.2365 0.9250 0.049 Uiso 1 1 calc R . . C31 C 0.3123(6) 0.1310(3) 0.9712(3) 0.0457(14) Uani 1 1 d . . . H31A H 0.3510 0.1456 1.0261 0.055 Uiso 1 1 calc R . . C32 C 0.3036(5) 0.0563(3) 0.9507(3) 0.0362(11) Uani 1 1 d . . . H32A H 0.3342 0.0192 0.9915 0.043 Uiso 1 1 calc R . . C33 C 0.2501(4) 0.0354(3) 0.8703(3) 0.0265(9) Uani 1 1 d . . . Cl5 Cl -0.4646(5) -0.3370(4) -0.0552(4) 0.245(3) Uani 1 1 d . . . Cl6 Cl -0.4011(8) -0.4221(7) 0.0901(3) 0.373(6) Uani 1 1 d . . . C100 C -0.5225(9) -0.3447(5) 0.0289(5) 0.085(3) Uani 1 1 d . . . H10B H -0.6116 -0.3619 0.0095 0.102 Uiso 1 1 calc R . . H10C H -0.5119 -0.2973 0.0594 0.102 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.0241(2) 0.0228(2) 0.0235(2) 0.00048(10) 0.01131(14) 0.00150(10) Cl1 0.0466(7) 0.0362(6) 0.0321(6) -0.0020(5) 0.0231(5) 0.0079(5) Cl2 0.0262(5) 0.0325(6) 0.0261(5) 0.0039(4) 0.0108(4) 0.0037(4) Cl3 0.0316(6) 0.0280(6) 0.0382(6) 0.0041(4) 0.0161(5) -0.0022(4) Cl4 0.0315(6) 0.0381(6) 0.0291(6) 0.0057(5) 0.0080(5) 0.0031(5) N1 0.0245(17) 0.0245(18) 0.0228(17) 0.0005(14) 0.0099(14) -0.0004(14) N2 0.0234(17) 0.0256(18) 0.0229(17) -0.0014(14) 0.0109(14) 0.0031(14) N3 0.0310(19) 0.032(2) 0.0231(18) -0.0013(15) 0.0105(15) 0.0023(16) C1 0.025(2) 0.027(2) 0.0201(19) 0.0000(16) 0.0095(16) -0.0003(16) C2 0.026(2) 0.025(2) 0.023(2) 0.0031(17) 0.0097(17) -0.0005(17) C3 0.024(2) 0.029(2) 0.029(2) 0.0041(18) 0.0111(18) 0.0029(17) C4 0.034(2) 0.030(2) 0.042(3) 0.002(2) 0.018(2) 0.0046(19) C5 0.038(3) 0.042(3) 0.053(3) 0.004(2) 0.025(2) 0.011(2) C6 0.033(3) 0.046(3) 0.059(3) 0.011(3) 0.027(3) 0.010(2) C7 0.024(2) 0.044(3) 0.037(3) 0.007(2) 0.0152(19) 0.003(2) C8 0.024(2) 0.033(2) 0.025(2) 0.0057(18) 0.0077(17) 0.0022(18) C9 0.026(2) 0.050(3) 0.047(3) 0.001(2) 0.016(2) -0.006(2) C10 0.030(2) 0.048(3) 0.037(3) -0.001(2) 0.010(2) -0.010(2) C11 0.028(2) 0.036(3) 0.028(2) 0.0004(19) 0.0075(18) -0.0062(19) C12 0.023(2) 0.033(2) 0.024(2) 0.0017(17) 0.0089(17) -0.0020(17) C13 0.024(2) 0.024(2) 0.035(2) -0.0015(17) 0.0151(18) 0.0008(16) C14 0.040(3) 0.028(2) 0.041(3) -0.001(2) 0.024(2) 0.002(2) C15 0.045(3) 0.024(2) 0.063(4) 0.002(2) 0.033(3) -0.002(2) C16 0.039(3) 0.028(2) 0.067(4) -0.013(2) 0.031(3) -0.004(2) C17 0.032(2) 0.039(3) 0.042(3) -0.014(2) 0.015(2) -0.003(2) C18 0.027(2) 0.026(2) 0.036(2) -0.0042(18) 0.0140(19) 0.0004(17) C19 0.033(2) 0.039(3) 0.024(2) -0.0042(19) 0.0101(18) 0.006(2) C20 0.039(3) 0.039(3) 0.028(2) -0.007(2) 0.013(2) 0.006(2) C21 0.025(2) 0.039(3) 0.024(2) -0.0001(19) 0.0084(18) 0.0050(19) C22 0.039(3) 0.049(3) 0.021(2) -0.004(2) 0.012(2) -0.001(2) C23 0.040(3) 0.055(3) 0.022(2) 0.005(2) 0.011(2) 0.000(2) C24 0.037(3) 0.040(3) 0.027(2) 0.007(2) 0.011(2) 0.001(2) C25 0.030(2) 0.033(2) 0.026(2) 0.0030(18) 0.0128(18) 0.0003(18) C26 0.036(2) 0.029(2) 0.025(2) 0.0015(18) 0.0137(19) -0.0046(19) C27 0.033(2) 0.029(2) 0.027(2) 0.0010(18) 0.0125(18) -0.0030(18) C28 0.024(2) 0.026(2) 0.029(2) -0.0006(17) 0.0123(17) -0.0005(16) C29 0.035(2) 0.025(2) 0.039(3) -0.0018(19) 0.018(2) -0.0012(19) C30 0.055(3) 0.027(2) 0.044(3) -0.009(2) 0.022(3) -0.002(2) C31 0.060(4) 0.046(3) 0.029(3) -0.010(2) 0.016(3) -0.006(3) C32 0.047(3) 0.035(3) 0.025(2) -0.0033(19) 0.012(2) -0.003(2) C33 0.028(2) 0.028(2) 0.025(2) -0.0023(17) 0.0108(17) 0.0001(17) Cl5 0.112(3) 0.330(8) 0.241(6) -0.088(6) 0.016(4) 0.033(4) Cl6 0.342(10) 0.613(17) 0.113(4) -0.117(7) 0.038(5) 0.165(11) C100 0.090(6) 0.071(5) 0.058(5) 0.016(4) -0.009(4) -0.020(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 Sn1 N2 2.259(3) . ? Sn1 N1 2.291(4) . ? Sn1 Cl1 2.3360(12) . ? Sn1 Cl3 2.3742(12) . ? Sn1 Cl2 2.4045(13) . ? Sn1 Cl4 2.4268(13) . ? N1 C1 1.283(5) . ? N1 C33 1.454(6) . ? N2 C2 1.269(6) . ? N2 C13 1.442(6) . ? N3 C21 1.347(6) . ? N3 C25 1.347(6) . ? C1 C12 1.470(6) . ? C1 C2 1.502(6) . ? C2 C3 1.475(6) . ? C3 C4 1.371(7) . ? C3 C8 1.426(7) . ? C4 C5 1.406(7) . ? C4 H4A 0.9500 . ? C5 C6 1.385(8) . ? C5 H5A 0.9500 . ? C6 C7 1.408(8) . ? C6 H6A 0.9500 . ? C7 C8 1.403(6) . ? C7 C9 1.421(8) . ? C8 C12 1.423(7) . ? C9 C10 1.363(8) . ? C9 H9A 0.9500 . ? C10 C11 1.435(7) . ? C10 H10A 0.9500 . ? C11 C12 1.380(6) . ? C11 H11A 0.9500 . ? C13 C14 1.382(7) . ? C13 C18 1.406(7) . ? C14 C15 1.393(7) . ? C14 H14A 0.9500 . ? C15 C16 1.362(8) . ? C15 H15A 0.9500 . ? C16 C17 1.386(8) . ? C16 H16A 0.9500 . ? C17 C18 1.393(7) . ? C17 H17A 0.9500 . ? C18 C19 1.502(7) . ? C19 C20 1.559(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.496(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.385(7) . ? C22 C23 1.394(8) . ? C22 H22A 0.9500 . ? C23 C24 1.386(7) . ? C23 H23A 0.9500 . ? C24 C25 1.383(6) . ? C24 H24A 0.9500 . ? C25 C26 1.513(6) . ? C26 C27 1.547(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.504(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C33 1.395(6) . ? C28 C29 1.398(6) . ? C29 C30 1.385(7) . ? C29 H29A 0.9500 . ? C30 C31 1.392(8) . ? C30 H30A 0.9500 . ? C31 C32 1.375(7) . ? C31 H31A 0.9500 . ? C32 C33 1.387(6) . ? C32 H32A 0.9500 . ? Cl5 C100 1.895(11) . ? Cl6 C100 1.963(13) . ? C100 H10B 0.9900 . ? C100 H10C 0.9900 . ? 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 N2 Sn1 N1 73.55(13) . . ? N2 Sn1 Cl1 166.65(10) . . ? N1 Sn1 Cl1 93.45(10) . . ? N2 Sn1 Cl3 94.23(10) . . ? N1 Sn1 Cl3 167.77(9) . . ? Cl1 Sn1 Cl3 98.71(5) . . ? N2 Sn1 Cl2 88.44(10) . . ? N1 Sn1 Cl2 88.82(9) . . ? Cl1 Sn1 Cl2 94.44(5) . . ? Cl3 Sn1 Cl2 91.53(4) . . ? N2 Sn1 Cl4 83.86(10) . . ? N1 Sn1 Cl4 84.57(10) . . ? Cl1 Sn1 Cl4 92.04(5) . . ? Cl3 Sn1 Cl4 93.65(4) . . ? Cl2 Sn1 Cl4 171.01(4) . . ? C1 N1 C33 120.9(4) . . ? C1 N1 Sn1 111.6(3) . . ? C33 N1 Sn1 126.9(3) . . ? C2 N2 C13 121.6(4) . . ? C2 N2 Sn1 112.6(3) . . ? C13 N2 Sn1 125.1(3) . . ? C21 N3 C25 118.4(4) . . ? N1 C1 C12 133.9(4) . . ? N1 C1 C2 118.3(4) . . ? C12 C1 C2 107.8(4) . . ? N2 C2 C3 133.6(4) . . ? N2 C2 C1 119.0(4) . . ? C3 C2 C1 107.4(4) . . ? C4 C3 C8 119.7(4) . . ? C4 C3 C2 134.9(4) . . ? C8 C3 C2 105.2(4) . . ? C3 C4 C5 117.8(5) . . ? C3 C4 H4A 121.1 . . ? C5 C4 H4A 121.1 . . ? C6 C5 C4 122.9(5) . . ? C6 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? C5 C6 C7 120.6(5) . . ? C5 C6 H6A 119.7 . . ? C7 C6 H6A 119.7 . . ? C8 C7 C6 116.3(5) . . ? C8 C7 C9 116.0(5) . . ? C6 C7 C9 127.7(5) . . ? C7 C8 C12 122.9(4) . . ? C7 C8 C3 122.7(4) . . ? C12 C8 C3 114.3(4) . . ? C10 C9 C7 121.3(5) . . ? C10 C9 H9A 119.4 . . ? C7 C9 H9A 119.4 . . ? C9 C10 C11 122.7(5) . . ? C9 C10 H10A 118.7 . . ? C11 C10 H10A 118.7 . . ? C12 C11 C10 117.1(5) . . ? C12 C11 H11A 121.4 . . ? C10 C11 H11A 121.4 . . ? C11 C12 C8 120.0(4) . . ? C11 C12 C1 134.6(4) . . ? C8 C12 C1 105.3(4) . . ? C14 C13 C18 121.9(4) . . ? C14 C13 N2 118.9(4) . . ? C18 C13 N2 119.1(4) . . ? C13 C14 C15 119.5(5) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C16 C15 C14 119.7(5) . . ? C16 C15 H15A 120.2 . . ? C14 C15 H15A 120.2 . . ? C15 C16 C17 120.8(5) . . ? C15 C16 H16A 119.6 . . ? C17 C16 H16A 119.6 . . ? C16 C17 C18 121.5(5) . . ? C16 C17 H17A 119.3 . . ? C18 C17 H17A 119.3 . . ? C17 C18 C13 116.6(5) . . ? C17 C18 C19 121.0(4) . . ? C13 C18 C19 122.4(4) . . ? C18 C19 C20 114.2(4) . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C21 C20 C19 111.5(4) . . ? C21 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? C21 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? N3 C21 C22 122.4(5) . . ? N3 C21 C20 115.7(4) . . ? C22 C21 C20 122.0(4) . . ? C21 C22 C23 118.9(5) . . ? C21 C22 H22A 120.5 . . ? C23 C22 H22A 120.5 . . ? C24 C23 C22 118.7(4) . . ? C24 C23 H23A 120.7 . . ? C22 C23 H23A 120.7 . . ? C25 C24 C23 119.2(5) . . ? C25 C24 H24A 120.4 . . ? C23 C24 H24A 120.4 . . ? N3 C25 C24 122.4(4) . . ? N3 C25 C26 115.1(4) . . ? C24 C25 C26 122.5(4) . . ? C25 C26 C27 112.1(4) . . ? C25 C26 H26A 109.2 . . ? C27 C26 H26A 109.2 . . ? C25 C26 H26B 109.2 . . ? C27 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C28 C27 C26 113.8(4) . . ? C28 C27 H27A 108.8 . . ? C26 C27 H27A 108.8 . . ? C28 C27 H27B 108.8 . . ? C26 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C33 C28 C29 117.2(4) . . ? C33 C28 C27 122.7(4) . . ? C29 C28 C27 120.1(4) . . ? C30 C29 C28 121.3(5) . . ? C30 C29 H29A 119.3 . . ? C28 C29 H29A 119.3 . . ? C29 C30 C31 120.0(5) . . ? C29 C30 H30A 120.0 . . ? C31 C30 H30A 120.0 . . ? C32 C31 C30 119.7(5) . . ? C32 C31 H31A 120.1 . . ? C30 C31 H31A 120.1 . . ? C31 C32 C33 119.9(5) . . ? C31 C32 H32A 120.1 . . ? C33 C32 H32A 120.1 . . ? C32 C33 C28 121.8(4) . . ? C32 C33 N1 118.7(4) . . ? C28 C33 N1 119.5(4) . . ? Cl5 C100 Cl6 96.1(6) . . ? Cl5 C100 H10B 112.5 . . ? Cl6 C100 H10B 112.5 . . ? Cl5 C100 H10C 112.5 . . ? Cl6 C100 H10C 112.5 . . ? H10B C100 H10C 110.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Sn1 N1 C1 -18.0(3) . . . . ? Cl1 Sn1 N1 C1 158.9(3) . . . . ? Cl3 Sn1 N1 C1 -14.9(7) . . . . ? Cl2 Sn1 N1 C1 -106.7(3) . . . . ? Cl4 Sn1 N1 C1 67.2(3) . . . . ? N2 Sn1 N1 C33 170.6(4) . . . . ? Cl1 Sn1 N1 C33 -12.5(3) . . . . ? Cl3 Sn1 N1 C33 173.7(3) . . . . ? Cl2 Sn1 N1 C33 81.9(3) . . . . ? Cl4 Sn1 N1 C33 -104.2(3) . . . . ? N1 Sn1 N2 C2 18.7(3) . . . . ? Cl1 Sn1 N2 C2 5.2(6) . . . . ? Cl3 Sn1 N2 C2 -160.6(3) . . . . ? Cl2 Sn1 N2 C2 108.0(3) . . . . ? Cl4 Sn1 N2 C2 -67.4(3) . . . . ? N1 Sn1 N2 C13 -170.7(4) . . . . ? Cl1 Sn1 N2 C13 175.8(3) . . . . ? Cl3 Sn1 N2 C13 10.0(3) . . . . ? Cl2 Sn1 N2 C13 -81.5(3) . . . . ? Cl4 Sn1 N2 C13 103.2(3) . . . . ? C33 N1 C1 C12 8.6(7) . . . . ? Sn1 N1 C1 C12 -163.4(4) . . . . ? C33 N1 C1 C2 -172.3(4) . . . . ? Sn1 N1 C1 C2 15.7(5) . . . . ? C13 N2 C2 C3 -7.8(7) . . . . ? Sn1 N2 C2 C3 163.2(4) . . . . ? C13 N2 C2 C1 171.4(4) . . . . ? Sn1 N2 C2 C1 -17.7(5) . . . . ? N1 C1 C2 N2 1.1(6) . . . . ? C12 C1 C2 N2 -179.6(4) . . . . ? N1 C1 C2 C3 -179.5(4) . . . . ? C12 C1 C2 C3 -0.2(5) . . . . ? N2 C2 C3 C4 -4.8(9) . . . . ? C1 C2 C3 C4 176.0(5) . . . . ? N2 C2 C3 C8 -179.6(5) . . . . ? C1 C2 C3 C8 1.2(5) . . . . ? C8 C3 C4 C5 -0.7(7) . . . . ? C2 C3 C4 C5 -174.9(5) . . . . ? C3 C4 C5 C6 1.8(8) . . . . ? C4 C5 C6 C7 -1.1(9) . . . . ? C5 C6 C7 C8 -0.6(8) . . . . ? C5 C6 C7 C9 178.5(5) . . . . ? C6 C7 C8 C12 178.0(5) . . . . ? C9 C7 C8 C12 -1.2(7) . . . . ? C6 C7 C8 C3 1.6(7) . . . . ? C9 C7 C8 C3 -177.6(4) . . . . ? C4 C3 C8 C7 -1.0(7) . . . . ? C2 C3 C8 C7 174.8(4) . . . . ? C4 C3 C8 C12 -177.6(4) . . . . ? C2 C3 C8 C12 -1.9(5) . . . . ? C8 C7 C9 C10 0.0(8) . . . . ? C6 C7 C9 C10 -179.1(5) . . . . ? C7 C9 C10 C11 1.4(8) . . . . ? C9 C10 C11 C12 -1.5(7) . . . . ? C10 C11 C12 C8 0.3(6) . . . . ? C10 C11 C12 C1 174.9(5) . . . . ? C7 C8 C12 C11 1.1(7) . . . . ? C3 C8 C12 C11 177.8(4) . . . . ? C7 C8 C12 C1 -174.9(4) . . . . ? C3 C8 C12 C1 1.8(5) . . . . ? N1 C1 C12 C11 3.2(9) . . . . ? C2 C1 C12 C11 -176.0(5) . . . . ? N1 C1 C12 C8 178.3(5) . . . . ? C2 C1 C12 C8 -0.9(5) . . . . ? C2 N2 C13 C14 99.7(5) . . . . ? Sn1 N2 C13 C14 -70.0(5) . . . . ? C2 N2 C13 C18 -83.3(5) . . . . ? Sn1 N2 C13 C18 106.9(4) . . . . ? C18 C13 C14 C15 1.3(7) . . . . ? N2 C13 C14 C15 178.2(4) . . . . ? C13 C14 C15 C16 -0.9(7) . . . . ? C14 C15 C16 C17 0.6(8) . . . . ? C15 C16 C17 C18 -0.7(8) . . . . ? C16 C17 C18 C13 1.0(7) . . . . ? C16 C17 C18 C19 179.8(4) . . . . ? C14 C13 C18 C17 -1.3(7) . . . . ? N2 C13 C18 C17 -178.2(4) . . . . ? C14 C13 C18 C19 179.9(4) . . . . ? N2 C13 C18 C19 3.0(6) . . . . ? C17 C18 C19 C20 -82.9(6) . . . . ? C13 C18 C19 C20 95.8(5) . . . . ? C18 C19 C20 C21 -157.2(4) . . . . ? C25 N3 C21 C22 1.6(7) . . . . ? C25 N3 C21 C20 -178.7(4) . . . . ? C19 C20 C21 N3 61.8(5) . . . . ? C19 C20 C21 C22 -118.6(5) . . . . ? N3 C21 C22 C23 -1.6(8) . . . . ? C20 C21 C22 C23 178.8(5) . . . . ? C21 C22 C23 C24 1.0(8) . . . . ? C22 C23 C24 C25 -0.6(8) . . . . ? C21 N3 C25 C24 -1.2(7) . . . . ? C21 N3 C25 C26 179.0(4) . . . . ? C23 C24 C25 N3 0.8(7) . . . . ? C23 C24 C25 C26 -179.5(5) . . . . ? N3 C25 C26 C27 -58.6(5) . . . . ? C24 C25 C26 C27 121.6(5) . . . . ? C25 C26 C27 C28 154.4(4) . . . . ? C26 C27 C28 C33 -100.9(5) . . . . ? C26 C27 C28 C29 78.7(5) . . . . ? C33 C28 C29 C30 1.3(7) . . . . ? C27 C28 C29 C30 -178.3(5) . . . . ? C28 C29 C30 C31 -1.3(8) . . . . ? C29 C30 C31 C32 -0.2(9) . . . . ? C30 C31 C32 C33 1.8(9) . . . . ? C31 C32 C33 C28 -1.8(8) . . . . ? C31 C32 C33 N1 178.8(5) . . . . ? C29 C28 C33 C32 0.3(7) . . . . ? C27 C28 C33 C32 179.9(4) . . . . ? C29 C28 C33 N1 179.6(4) . . . . ? C27 C28 C33 N1 -0.8(6) . . . . ? C1 N1 C33 C32 -98.3(5) . . . . ? Sn1 N1 C33 C32 72.3(5) . . . . ? C1 N1 C33 C28 82.3(5) . . . . ? Sn1 N1 C33 C28 -107.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.546 _refine_diff_density_min -1.191 _refine_diff_density_rms 0.266 data_3As _database_code_depnum_ccdc_archive 'CCDC 864989' #TrackingRef '- CIF_Ragogna_clamshell.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 As Cl N3' _chemical_formula_sum 'C33 H25 As Cl N3' _chemical_formula_weight 573.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.106(2) _cell_length_b 14.813(3) _cell_length_c 16.560(3) _cell_angle_alpha 103.03(3) _cell_angle_beta 99.79(3) _cell_angle_gamma 94.54(3) _cell_volume 2595.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 79727 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 26.730 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 1.441 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8129 _exptl_absorpt_correction_T_max 0.8812 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 75290 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.73 _reflns_number_total 11003 _reflns_number_gt 8468 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+2.6425P] 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 11003 _refine_ls_number_parameters 685 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.005 _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 1.03421(3) 1.197419(18) 0.623726(17) 0.02641(8) Uani 1 1 d . . . As2 As 0.72864(3) 0.791849(19) 0.773897(17) 0.02539(8) Uani 1 1 d . . . Cl2 Cl 0.94684(7) 0.82207(6) 0.80448(5) 0.04056(18) Uani 1 1 d . . . Cl1 Cl 0.88297(8) 1.28335(5) 0.56610(5) 0.04307(19) Uani 1 1 d . . . N5 N 0.70342(19) 0.75324(15) 0.86728(13) 0.0220(4) Uani 1 1 d . . . N1 N 1.07653(19) 1.27484(14) 0.73057(13) 0.0224(5) Uani 1 1 d . . . N2 N 0.93793(19) 1.12268(14) 0.66741(13) 0.0225(5) Uani 1 1 d . . . C18 C 0.9095(2) 0.95223(17) 0.61812(15) 0.0205(5) Uani 1 1 d . . . N3 N 1.26170(19) 1.08931(15) 0.68677(14) 0.0258(5) Uani 1 1 d . . . C45 C 0.7010(2) 0.51113(19) 0.76696(18) 0.0278(6) Uani 1 1 d . . . N4 N 0.7116(2) 0.66843(15) 0.71760(13) 0.0245(5) Uani 1 1 d . . . C54 C 0.3630(2) 0.78986(17) 0.77544(17) 0.0232(5) Uani 1 1 d . . . C35 C 0.6988(2) 0.65737(18) 0.85347(16) 0.0238(5) Uani 1 1 d . . . C22 C 1.3604(2) 0.95206(19) 0.65309(17) 0.0279(6) Uani 1 1 d . . . H22A H 1.3548 0.8879 0.6253 0.033 Uiso 1 1 calc R . . N6 N 0.42822(19) 0.73890(15) 0.72447(14) 0.0240(5) Uani 1 1 d . . . C4 C 0.7967(2) 1.06089(18) 0.81910(18) 0.0264(6) Uani 1 1 d . . . H4A H 0.7691 1.0098 0.7714 0.032 Uiso 1 1 calc R . . C11 C 1.0333(2) 1.36098(18) 0.93668(17) 0.0267(6) Uani 1 1 d . . . H11A H 1.0856 1.4111 0.9291 0.032 Uiso 1 1 calc R . . C13 C 0.8621(2) 1.03744(16) 0.62055(15) 0.0198(5) Uani 1 1 d . . . C17 C 0.8335(2) 0.87137(18) 0.57243(16) 0.0250(6) Uani 1 1 d . . . H17A H 0.8629 0.8125 0.5704 0.030 Uiso 1 1 calc R . . C51 C 0.6000(2) 0.83178(18) 0.97754(16) 0.0227(5) Uani 1 1 d . . . C41 C 0.6861(2) 0.50165(19) 0.84899(18) 0.0277(6) Uani 1 1 d . . . C10 C 0.9974(3) 1.3645(2) 1.01601(17) 0.0325(7) Uani 1 1 d . . . H10A H 1.0270 1.4181 1.0611 0.039 Uiso 1 1 calc R . . C12 C 0.9908(2) 1.28388(17) 0.87176(16) 0.0214(5) Uani 1 1 d . . . C53 C 0.4373(2) 0.84839(18) 0.85750(17) 0.0253(6) Uani 1 1 d . . . H53A H 0.3876 0.8958 0.8827 0.030 Uiso 1 1 calc R . . H53B H 0.5111 0.8818 0.8463 0.030 Uiso 1 1 calc R . . C61 C 0.6627(2) 0.64767(18) 0.56438(16) 0.0250(6) Uani 1 1 d . . . C32 C 1.0795(3) 1.44346(18) 0.76623(17) 0.0294(6) Uani 1 1 d . . . H32A H 0.9948 1.4350 0.7691 0.035 Uiso 1 1 calc R . . C33 C 1.1421(2) 1.36691(17) 0.74642(16) 0.0235(5) Uani 1 1 d . . . C19 C 1.0398(2) 0.94994(18) 0.66017(17) 0.0245(6) Uani 1 1 d . . . H19A H 1.0449 0.8919 0.6802 0.029 Uiso 1 1 calc R . . H19B H 1.0637 1.0035 0.7101 0.029 Uiso 1 1 calc R . . C1 C 1.0027(2) 1.24891(17) 0.78368(16) 0.0214(5) Uani 1 1 d . . . C25 C 1.3690(2) 1.13586(19) 0.73398(17) 0.0266(6) Uani 1 1 d . . . C49 C 0.7229(3) 0.9353(2) 1.10492(17) 0.0323(6) Uani 1 1 d . . . H49A H 0.7268 0.9765 1.1586 0.039 Uiso 1 1 calc R . . C8 C 0.9099(2) 1.21206(17) 0.88680(16) 0.0216(5) Uani 1 1 d . . . C52 C 0.4783(2) 0.78978(19) 0.92141(16) 0.0255(6) Uani 1 1 d . . . H52A H 0.4152 0.7861 0.9566 0.031 Uiso 1 1 calc R . . H52B H 0.4850 0.7255 0.8903 0.031 Uiso 1 1 calc R . . C46 C 0.7095(2) 0.81493(17) 0.94905(15) 0.0220(5) Uani 1 1 d . . . C24 C 1.4759(3) 1.0927(2) 0.74083(19) 0.0334(7) Uani 1 1 d . . . H24A H 1.5513 1.1266 0.7734 0.040 Uiso 1 1 calc R . . C14 C 0.7435(2) 1.04125(19) 0.57960(17) 0.0275(6) Uani 1 1 d . . . H14A H 0.7122 1.0996 0.5830 0.033 Uiso 1 1 calc R . . C2 C 0.9310(2) 1.16475(17) 0.75001(16) 0.0207(5) Uani 1 1 d . . . C62 C 0.6984(3) 0.61895(19) 0.48624(18) 0.0319(6) Uani 1 1 d . . . H62A H 0.6455 0.6241 0.4364 0.038 Uiso 1 1 calc R . . C21 C 1.2567(2) 0.99922(18) 0.64739(16) 0.0232(5) Uani 1 1 d . . . C23 C 1.4707(3) 0.9995(2) 0.69932(19) 0.0334(7) Uani 1 1 d . . . H23A H 1.5427 0.9688 0.7029 0.040 Uiso 1 1 calc R . . C5 C 0.7615(3) 1.0605(2) 0.89824(18) 0.0318(6) Uani 1 1 d . . . H5A H 0.7107 1.0079 0.9026 0.038 Uiso 1 1 calc R . . C34 C 0.7066(2) 0.61146(18) 0.77324(17) 0.0251(6) Uani 1 1 d . . . C57 C 0.2415(2) 0.67597(19) 0.62567(18) 0.0279(6) Uani 1 1 d . . . H57A H 0.2010 0.6359 0.5732 0.033 Uiso 1 1 calc R . . C36 C 0.6826(2) 0.59012(19) 0.90442(17) 0.0252(6) Uani 1 1 d . . . C28 C 1.2668(3) 1.37716(18) 0.73938(16) 0.0269(6) Uani 1 1 d . . . C20 C 1.1309(2) 0.95408(18) 0.60000(16) 0.0250(6) Uani 1 1 d . . . H20A H 1.1368 0.8900 0.5682 0.030 Uiso 1 1 calc R . . H20B H 1.0995 0.9898 0.5588 0.030 Uiso 1 1 calc R . . C6 C 0.7986(3) 1.1335(2) 0.96781(18) 0.0316(6) Uani 1 1 d . . . H6B H 0.7735 1.1306 1.0193 0.038 Uiso 1 1 calc R . . C59 C 0.4477(2) 0.62549(19) 0.59913(17) 0.0278(6) Uani 1 1 d . . . H59A H 0.3947 0.5831 0.5485 0.033 Uiso 1 1 calc R . . H59B H 0.4915 0.5865 0.6329 0.033 Uiso 1 1 calc R . . C50 C 0.6091(3) 0.89288(19) 1.05631(17) 0.0299(6) Uani 1 1 d . . . H50A H 0.5363 0.9059 1.0773 0.036 Uiso 1 1 calc R . . C3 C 0.8711(2) 1.13664(17) 0.81382(16) 0.0206(5) Uani 1 1 d . . . C63 C 0.8089(3) 0.5832(2) 0.47979(19) 0.0375(7) Uani 1 1 d . . . H63A H 0.8317 0.5650 0.4262 0.045 Uiso 1 1 calc R . . C58 C 0.3678(2) 0.68212(17) 0.65089(16) 0.0239(5) Uani 1 1 d . . . C9 C 0.9225(3) 1.2946(2) 1.02997(17) 0.0318(6) Uani 1 1 d . . . H9A H 0.9021 1.2998 1.0841 0.038 Uiso 1 1 calc R . . C40 C 0.6792(2) 0.4180(2) 0.8727(2) 0.0355(7) Uani 1 1 d . . . C48 C 0.8290(3) 0.9180(2) 1.07586(18) 0.0334(7) Uani 1 1 d . . . H48A H 0.9065 0.9474 1.1090 0.040 Uiso 1 1 calc R . . C37 C 0.6659(3) 0.5925(2) 0.98523(18) 0.0331(7) Uani 1 1 d . . . H37A H 0.6609 0.6498 1.0235 0.040 Uiso 1 1 calc R . . C26 C 1.3607(3) 1.23583(19) 0.77779(17) 0.0296(6) Uani 1 1 d . . . H26A H 1.4389 1.2624 0.8177 0.036 Uiso 1 1 calc R . . H26B H 1.2937 1.2376 0.8104 0.036 Uiso 1 1 calc R . . C15 C 0.6708(2) 0.9591(2) 0.53352(18) 0.0298(6) Uani 1 1 d . . . H15A H 0.5899 0.9611 0.5045 0.036 Uiso 1 1 calc R . . C66 C 0.7425(2) 0.63829(18) 0.63600(16) 0.0256(6) Uani 1 1 d . . . C47 C 0.8229(3) 0.8571(2) 0.99725(17) 0.0294(6) Uani 1 1 d . . . H47A H 0.8962 0.8445 0.9768 0.035 Uiso 1 1 calc R . . C60 C 0.5428(2) 0.68736(19) 0.57104(17) 0.0273(6) Uani 1 1 d . . . H60A H 0.5061 0.6972 0.5154 0.033 Uiso 1 1 calc R . . H60B H 0.5603 0.7491 0.6119 0.033 Uiso 1 1 calc R . . C27 C 1.3353(3) 1.29454(19) 0.71237(18) 0.0296(6) Uani 1 1 d . . . H27A H 1.4148 1.3177 0.7003 0.036 Uiso 1 1 calc R . . H27B H 1.2867 1.2536 0.6592 0.036 Uiso 1 1 calc R . . C44 C 0.7076(3) 0.4304(2) 0.7075(2) 0.0362(7) Uani 1 1 d . . . H44A H 0.7166 0.4328 0.6520 0.043 Uiso 1 1 calc R . . C29 C 1.3257(3) 1.46851(19) 0.75635(17) 0.0306(6) Uani 1 1 d . . . H29A H 1.4101 1.4780 0.7530 0.037 Uiso 1 1 calc R . . C30 C 1.2641(3) 1.54490(19) 0.77781(17) 0.0335(7) Uani 1 1 d . . . H30A H 1.3064 1.6061 0.7898 0.040 Uiso 1 1 calc R . . C64 C 0.8857(3) 0.5742(2) 0.5517(2) 0.0409(8) Uani 1 1 d . . . H64A H 0.9610 0.5489 0.5476 0.049 Uiso 1 1 calc R . . C31 C 1.1409(3) 1.53265(19) 0.78186(17) 0.0322(6) Uani 1 1 d . . . H31A H 1.0982 1.5854 0.7954 0.039 Uiso 1 1 calc R . . C16 C 0.7165(2) 0.87479(19) 0.53005(17) 0.0276(6) Uani 1 1 d . . . H16A H 0.6670 0.8186 0.4982 0.033 Uiso 1 1 calc R . . C56 C 0.1751(2) 0.72879(19) 0.67769(19) 0.0311(6) Uani 1 1 d . . . H56A H 0.0884 0.7260 0.6612 0.037 Uiso 1 1 calc R . . C65 C 0.8530(3) 0.6022(2) 0.63001(19) 0.0353(7) Uani 1 1 d . . . H65A H 0.9064 0.5967 0.6795 0.042 Uiso 1 1 calc R . . C43 C 0.7008(3) 0.3439(2) 0.7308(2) 0.0424(8) Uani 1 1 d . . . H43A H 0.7057 0.2887 0.6898 0.051 Uiso 1 1 calc R . . C7 C 0.8747(2) 1.21394(19) 0.96384(17) 0.0261(6) Uani 1 1 d . . . C42 C 0.6875(3) 0.3367(2) 0.8099(2) 0.0427(8) Uani 1 1 d . . . H42A H 0.6838 0.2774 0.8229 0.051 Uiso 1 1 calc R . . C55 C 0.2361(2) 0.78584(18) 0.75422(18) 0.0285(6) Uani 1 1 d . . . H55A H 0.1918 0.8216 0.7916 0.034 Uiso 1 1 calc R . . C38 C 0.6564(3) 0.5070(2) 1.0099(2) 0.0417(8) Uani 1 1 d . . . H38A H 0.6446 0.5083 1.0656 0.050 Uiso 1 1 calc R . . C39 C 0.6634(3) 0.4229(2) 0.9572(2) 0.0430(8) Uani 1 1 d . . . H39A H 0.6577 0.3675 0.9769 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 As1 0.03467(16) 0.02063(14) 0.02373(15) 0.00149(11) 0.01235(12) -0.00106(11) As2 0.03159(15) 0.02443(15) 0.02271(15) 0.00688(11) 0.00816(11) 0.00914(11) Cl2 0.0340(4) 0.0519(5) 0.0393(4) 0.0154(4) 0.0128(3) 0.0017(3) Cl1 0.0649(5) 0.0363(4) 0.0294(4) 0.0108(3) 0.0069(4) 0.0117(4) N5 0.0245(11) 0.0227(11) 0.0194(11) 0.0039(9) 0.0060(9) 0.0065(9) N1 0.0273(11) 0.0166(10) 0.0223(11) 0.0015(9) 0.0075(9) -0.0007(9) N2 0.0267(11) 0.0172(10) 0.0228(11) 0.0019(9) 0.0073(9) 0.0001(9) C18 0.0223(13) 0.0222(13) 0.0180(12) 0.0051(10) 0.0065(10) 0.0026(10) N3 0.0231(11) 0.0272(12) 0.0285(12) 0.0084(10) 0.0056(9) 0.0049(9) C45 0.0193(13) 0.0258(14) 0.0377(16) 0.0054(12) 0.0058(11) 0.0043(11) N4 0.0284(12) 0.0246(11) 0.0215(11) 0.0036(9) 0.0085(9) 0.0077(9) C54 0.0218(13) 0.0197(13) 0.0292(14) 0.0098(11) 0.0024(11) 0.0032(10) C35 0.0203(13) 0.0274(14) 0.0247(14) 0.0068(11) 0.0048(10) 0.0066(11) C22 0.0306(15) 0.0260(14) 0.0311(15) 0.0097(12) 0.0101(12) 0.0101(12) N6 0.0235(11) 0.0229(11) 0.0259(12) 0.0078(9) 0.0038(9) 0.0006(9) C4 0.0220(13) 0.0243(14) 0.0326(15) 0.0069(11) 0.0049(11) 0.0026(11) C11 0.0246(14) 0.0242(14) 0.0281(15) 0.0034(11) 0.0004(11) 0.0028(11) C13 0.0253(13) 0.0162(12) 0.0180(12) 0.0029(10) 0.0069(10) 0.0008(10) C17 0.0293(14) 0.0178(13) 0.0277(14) 0.0041(11) 0.0074(11) 0.0024(11) C51 0.0252(13) 0.0235(13) 0.0205(13) 0.0066(10) 0.0046(10) 0.0055(11) C41 0.0163(12) 0.0290(14) 0.0385(16) 0.0117(12) 0.0030(11) 0.0027(11) C10 0.0365(16) 0.0334(16) 0.0215(14) -0.0042(12) 0.0005(12) 0.0105(13) C12 0.0208(13) 0.0215(13) 0.0220(13) 0.0055(10) 0.0018(10) 0.0074(10) C53 0.0208(13) 0.0232(13) 0.0313(15) 0.0047(11) 0.0047(11) 0.0057(10) C61 0.0312(14) 0.0203(13) 0.0233(14) 0.0034(10) 0.0100(11) -0.0024(11) C32 0.0346(15) 0.0232(14) 0.0290(15) 0.0040(11) 0.0057(12) 0.0024(12) C33 0.0327(14) 0.0180(12) 0.0189(13) 0.0040(10) 0.0057(11) -0.0015(11) C19 0.0238(13) 0.0225(13) 0.0279(14) 0.0094(11) 0.0021(11) 0.0029(10) C1 0.0231(13) 0.0190(12) 0.0227(13) 0.0058(10) 0.0041(10) 0.0049(10) C25 0.0247(14) 0.0287(14) 0.0285(15) 0.0122(12) 0.0054(11) 0.0007(11) C49 0.0437(17) 0.0323(15) 0.0181(14) 0.0017(11) 0.0006(12) 0.0122(13) C8 0.0194(12) 0.0226(13) 0.0238(13) 0.0075(10) 0.0029(10) 0.0064(10) C52 0.0228(13) 0.0289(14) 0.0249(14) 0.0039(11) 0.0080(11) 0.0039(11) C46 0.0258(13) 0.0234(13) 0.0179(13) 0.0057(10) 0.0040(10) 0.0078(11) C24 0.0222(14) 0.0359(16) 0.0424(18) 0.0132(14) 0.0034(12) 0.0013(12) C14 0.0265(14) 0.0243(14) 0.0340(16) 0.0085(12) 0.0080(12) 0.0071(11) C2 0.0212(12) 0.0196(12) 0.0219(13) 0.0059(10) 0.0039(10) 0.0044(10) C62 0.0425(17) 0.0276(15) 0.0236(14) 0.0028(11) 0.0105(12) -0.0056(13) C21 0.0244(13) 0.0265(14) 0.0211(13) 0.0088(11) 0.0068(10) 0.0040(11) C23 0.0227(14) 0.0392(17) 0.0429(18) 0.0167(14) 0.0077(12) 0.0094(12) C5 0.0283(15) 0.0342(16) 0.0379(17) 0.0153(13) 0.0117(12) 0.0035(12) C34 0.0209(13) 0.0276(14) 0.0270(14) 0.0051(11) 0.0063(11) 0.0045(11) C57 0.0268(14) 0.0251(14) 0.0292(15) 0.0100(11) -0.0038(11) -0.0009(11) C36 0.0183(13) 0.0287(14) 0.0307(15) 0.0122(12) 0.0033(11) 0.0033(11) C28 0.0322(15) 0.0243(14) 0.0235(14) 0.0074(11) 0.0038(11) -0.0012(11) C20 0.0267(14) 0.0248(13) 0.0218(13) 0.0027(11) 0.0030(11) 0.0057(11) C6 0.0324(15) 0.0378(16) 0.0319(16) 0.0146(13) 0.0157(12) 0.0098(13) C59 0.0266(14) 0.0263(14) 0.0277(15) 0.0046(11) 0.0031(11) -0.0030(11) C50 0.0332(15) 0.0340(16) 0.0235(14) 0.0054(12) 0.0075(12) 0.0107(12) C3 0.0183(12) 0.0216(13) 0.0237(13) 0.0081(10) 0.0029(10) 0.0077(10) C63 0.0484(18) 0.0311(16) 0.0306(16) -0.0048(12) 0.0212(14) -0.0030(14) C58 0.0256(13) 0.0205(13) 0.0260(14) 0.0099(11) 0.0021(11) -0.0009(10) C9 0.0377(16) 0.0382(16) 0.0226(14) 0.0075(12) 0.0098(12) 0.0147(13) C40 0.0198(14) 0.0317(16) 0.056(2) 0.0179(14) 0.0015(13) 0.0028(12) C48 0.0294(15) 0.0369(16) 0.0282(15) 0.0059(13) -0.0075(12) 0.0032(13) C37 0.0284(15) 0.0413(17) 0.0320(16) 0.0149(13) 0.0047(12) 0.0041(13) C26 0.0257(14) 0.0321(15) 0.0290(15) 0.0076(12) 0.0025(11) -0.0024(11) C15 0.0196(13) 0.0351(16) 0.0340(16) 0.0091(12) 0.0032(11) 0.0016(11) C66 0.0283(14) 0.0241(14) 0.0237(14) 0.0011(11) 0.0095(11) 0.0033(11) C47 0.0252(14) 0.0354(16) 0.0268(15) 0.0058(12) 0.0032(11) 0.0086(12) C60 0.0303(15) 0.0283(14) 0.0239(14) 0.0085(11) 0.0051(11) 0.0012(11) C27 0.0271(14) 0.0299(15) 0.0342(16) 0.0107(12) 0.0101(12) -0.0007(11) C44 0.0300(15) 0.0312(16) 0.0454(18) 0.0015(13) 0.0116(13) 0.0050(12) C29 0.0334(15) 0.0317(15) 0.0256(15) 0.0098(12) 0.0031(12) -0.0050(12) C30 0.0537(19) 0.0198(14) 0.0236(15) 0.0070(11) 0.0015(13) -0.0075(13) C64 0.0341(16) 0.0420(18) 0.0411(18) -0.0076(14) 0.0154(14) 0.0069(14) C31 0.0483(18) 0.0227(14) 0.0248(15) 0.0042(11) 0.0057(13) 0.0066(13) C16 0.0286(14) 0.0266(14) 0.0246(14) 0.0021(11) 0.0063(11) -0.0055(11) C56 0.0200(13) 0.0275(14) 0.0444(18) 0.0140(13) -0.0047(12) 0.0032(11) C65 0.0281(15) 0.0427(17) 0.0316(16) -0.0014(13) 0.0090(12) 0.0078(13) C43 0.0277(16) 0.0251(15) 0.069(2) -0.0013(15) 0.0118(15) 0.0046(12) C7 0.0253(14) 0.0311(15) 0.0245(14) 0.0083(11) 0.0061(11) 0.0119(11) C42 0.0247(15) 0.0283(16) 0.077(3) 0.0186(16) 0.0075(15) 0.0038(12) C55 0.0236(14) 0.0232(14) 0.0407(17) 0.0113(12) 0.0058(12) 0.0052(11) C38 0.0329(16) 0.057(2) 0.0424(19) 0.0300(17) 0.0038(14) 0.0014(15) C39 0.0290(16) 0.047(2) 0.061(2) 0.0340(18) 0.0024(15) 0.0027(14) _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 N2 1.825(2) . ? As1 N1 1.839(2) . ? As1 Cl1 2.3859(11) . ? As2 N5 1.822(2) . ? As2 N4 1.834(2) . ? As2 Cl2 2.3745(10) . ? N5 C35 1.382(3) . ? N5 C46 1.440(3) . ? N1 C1 1.393(3) . ? N1 C33 1.441(3) . ? N2 C2 1.387(3) . ? N2 C13 1.440(3) . ? C18 C17 1.390(3) . ? C18 C13 1.400(3) . ? C18 C19 1.503(4) . ? N3 C21 1.339(3) . ? N3 C25 1.348(3) . ? C45 C44 1.382(4) . ? C45 C41 1.432(4) . ? C45 C34 1.462(4) . ? N4 C34 1.387(3) . ? N4 C66 1.433(3) . ? C54 N6 1.347(3) . ? C54 C55 1.387(4) . ? C54 C53 1.501(4) . ? C35 C34 1.370(4) . ? C35 C36 1.463(4) . ? C22 C23 1.372(4) . ? C22 C21 1.394(4) . ? C22 H22A 0.9500 . ? N6 C58 1.346(3) . ? C4 C3 1.368(4) . ? C4 C5 1.431(4) . ? C4 H4A 0.9500 . ? C11 C12 1.368(4) . ? C11 C10 1.428(4) . ? C11 H11A 0.9500 . ? C13 C14 1.387(4) . ? C17 C16 1.379(4) . ? C17 H17A 0.9500 . ? C51 C50 1.392(4) . ? C51 C46 1.397(4) . ? C51 C52 1.503(4) . ? C41 C40 1.381(4) . ? C41 C36 1.428(4) . ? C10 C9 1.362(4) . ? C10 H10A 0.9500 . ? C12 C8 1.430(4) . ? C12 C1 1.466(3) . ? C53 C52 1.547(4) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C61 C66 1.396(4) . ? C61 C62 1.402(4) . ? C61 C60 1.509(4) . ? C32 C33 1.383(4) . ? C32 C31 1.386(4) . ? C32 H32A 0.9500 . ? C33 C28 1.409(4) . ? C19 C20 1.543(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C1 C2 1.370(3) . ? C25 C24 1.392(4) . ? C25 C26 1.512(4) . ? C49 C48 1.368(4) . ? C49 C50 1.393(4) . ? C49 H49A 0.9500 . ? C8 C7 1.392(4) . ? C8 C3 1.426(4) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C46 C47 1.386(4) . ? C24 C23 1.390(4) . ? C24 H24A 0.9500 . ? C14 C15 1.390(4) . ? C14 H14A 0.9500 . ? C2 C3 1.458(3) . ? C62 C63 1.385(4) . ? C62 H62A 0.9500 . ? C21 C20 1.502(4) . ? C23 H23A 0.9500 . ? C5 C6 1.369(4) . ? C5 H5A 0.9500 . ? C57 C56 1.379(4) . ? C57 C58 1.383(4) . ? C57 H57A 0.9500 . ? C36 C37 1.375(4) . ? C28 C29 1.401(4) . ? C28 C27 1.514(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C6 C7 1.425(4) . ? C6 H6B 0.9500 . ? C59 C58 1.509(4) . ? C59 C60 1.542(4) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C50 H50A 0.9500 . ? C63 C64 1.381(5) . ? C63 H63A 0.9500 . ? C9 C7 1.422(4) . ? C9 H9A 0.9500 . ? C40 C42 1.423(5) . ? C40 C39 1.427(5) . ? C48 C47 1.394(4) . ? C48 H48A 0.9500 . ? C37 C38 1.416(4) . ? C37 H37A 0.9500 . ? C26 C27 1.539(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C15 C16 1.378(4) . ? C15 H15A 0.9500 . ? C66 C65 1.386(4) . ? C47 H47A 0.9500 . ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C44 C43 1.419(4) . ? C44 H44A 0.9500 . ? C29 C30 1.378(4) . ? C29 H29A 0.9500 . ? C30 C31 1.380(4) . ? C30 H30A 0.9500 . ? C64 C65 1.388(4) . ? C64 H64A 0.9500 . ? C31 H31A 0.9500 . ? C16 H16A 0.9500 . ? C56 C55 1.383(4) . ? C56 H56A 0.9500 . ? C65 H65A 0.9500 . ? C43 C42 1.369(5) . ? C43 H43A 0.9500 . ? C42 H42A 0.9500 . ? C55 H55A 0.9500 . ? C38 C39 1.367(5) . ? C38 H38A 0.9500 . ? C39 H39A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 As1 N1 87.19(9) . . ? N2 As1 Cl1 99.99(7) . . ? N1 As1 Cl1 97.76(8) . . ? N5 As2 N4 87.76(10) . . ? N5 As2 Cl2 99.80(7) . . ? N4 As2 Cl2 99.10(8) . . ? C35 N5 C46 123.7(2) . . ? C35 N5 As2 111.12(16) . . ? C46 N5 As2 124.30(17) . . ? C1 N1 C33 123.2(2) . . ? C1 N1 As1 111.07(16) . . ? C33 N1 As1 121.93(16) . . ? C2 N2 C13 122.2(2) . . ? C2 N2 As1 111.46(16) . . ? C13 N2 As1 125.65(16) . . ? C17 C18 C13 117.5(2) . . ? C17 C18 C19 121.9(2) . . ? C13 C18 C19 120.5(2) . . ? C21 N3 C25 119.6(2) . . ? C44 C45 C41 117.2(3) . . ? C44 C45 C34 138.4(3) . . ? C41 C45 C34 104.4(2) . . ? C34 N4 C66 123.5(2) . . ? C34 N4 As2 110.64(16) . . ? C66 N4 As2 122.54(17) . . ? N6 C54 C55 122.0(2) . . ? N6 C54 C53 115.1(2) . . ? C55 C54 C53 122.8(2) . . ? C34 C35 N5 115.1(2) . . ? C34 C35 C36 110.0(2) . . ? N5 C35 C36 134.9(2) . . ? C23 C22 C21 119.2(3) . . ? C23 C22 H22A 120.4 . . ? C21 C22 H22A 120.4 . . ? C54 N6 C58 118.7(2) . . ? C3 C4 C5 118.4(3) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? C12 C11 C10 118.6(3) . . ? C12 C11 H11A 120.7 . . ? C10 C11 H11A 120.7 . . ? C14 C13 C18 121.4(2) . . ? C14 C13 N2 119.5(2) . . ? C18 C13 N2 119.1(2) . . ? C16 C17 C18 121.4(2) . . ? C16 C17 H17A 119.3 . . ? C18 C17 H17A 119.3 . . ? C50 C51 C46 117.4(2) . . ? C50 C51 C52 122.4(2) . . ? C46 C51 C52 120.1(2) . . ? C40 C41 C36 123.9(3) . . ? C40 C41 C45 124.6(3) . . ? C36 C41 C45 111.5(2) . . ? C9 C10 C11 122.9(3) . . ? C9 C10 H10A 118.5 . . ? C11 C10 H10A 118.5 . . ? C11 C12 C8 117.8(2) . . ? C11 C12 C1 138.2(2) . . ? C8 C12 C1 104.0(2) . . ? C54 C53 C52 112.6(2) . . ? C54 C53 H53A 109.1 . . ? C52 C53 H53A 109.1 . . ? C54 C53 H53B 109.1 . . ? C52 C53 H53B 109.1 . . ? H53A C53 H53B 107.8 . . ? C66 C61 C62 117.4(3) . . ? C66 C61 C60 121.2(2) . . ? C62 C61 C60 121.4(3) . . ? C33 C32 C31 119.6(3) . . ? C33 C32 H32A 120.2 . . ? C31 C32 H32A 120.2 . . ? C32 C33 C28 121.5(2) . . ? C32 C33 N1 118.7(2) . . ? C28 C33 N1 119.7(2) . . ? C18 C19 C20 112.1(2) . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C2 C1 N1 114.0(2) . . ? C2 C1 C12 109.6(2) . . ? N1 C1 C12 136.0(2) . . ? N3 C25 C24 121.2(3) . . ? N3 C25 C26 114.2(2) . . ? C24 C25 C26 124.6(2) . . ? C48 C49 C50 120.4(3) . . ? C48 C49 H49A 119.8 . . ? C50 C49 H49A 119.8 . . ? C7 C8 C3 123.5(2) . . ? C7 C8 C12 124.4(2) . . ? C3 C8 C12 112.1(2) . . ? C51 C52 C53 111.4(2) . . ? C51 C52 H52A 109.4 . . ? C53 C52 H52A 109.4 . . ? C51 C52 H52B 109.4 . . ? C53 C52 H52B 109.4 . . ? H52A C52 H52B 108.0 . . ? C47 C46 C51 121.4(2) . . ? C47 C46 N5 119.7(2) . . ? C51 C46 N5 118.9(2) . . ? C23 C24 C25 119.1(3) . . ? C23 C24 H24A 120.5 . . ? C25 C24 H24A 120.5 . . ? C13 C14 C15 119.5(2) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C1 C2 N2 115.1(2) . . ? C1 C2 C3 110.3(2) . . ? N2 C2 C3 134.4(2) . . ? C63 C62 C61 121.7(3) . . ? C63 C62 H62A 119.1 . . ? C61 C62 H62A 119.1 . . ? N3 C21 C22 121.7(2) . . ? N3 C21 C20 114.5(2) . . ? C22 C21 C20 123.8(2) . . ? C22 C23 C24 119.3(3) . . ? C22 C23 H23A 120.4 . . ? C24 C23 H23A 120.4 . . ? C6 C5 C4 122.2(3) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C35 C34 N4 114.6(2) . . ? C35 C34 C45 109.8(2) . . ? N4 C34 C45 135.6(2) . . ? C56 C57 C58 119.1(3) . . ? C56 C57 H57A 120.4 . . ? C58 C57 H57A 120.4 . . ? C37 C36 C41 118.5(3) . . ? C37 C36 C35 137.2(3) . . ? C41 C36 C35 104.3(2) . . ? C29 C28 C33 116.9(3) . . ? C29 C28 C27 120.5(3) . . ? C33 C28 C27 122.6(2) . . ? C21 C20 C19 111.6(2) . . ? C21 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? C21 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? C5 C6 C7 120.7(3) . . ? C5 C6 H6B 119.7 . . ? C7 C6 H6B 119.7 . . ? C58 C59 C60 112.4(2) . . ? C58 C59 H59A 109.1 . . ? C60 C59 H59A 109.1 . . ? C58 C59 H59B 109.1 . . ? C60 C59 H59B 109.1 . . ? H59A C59 H59B 107.9 . . ? C51 C50 C49 121.3(3) . . ? C51 C50 H50A 119.3 . . ? C49 C50 H50A 119.3 . . ? C4 C3 C8 119.0(2) . . ? C4 C3 C2 136.9(2) . . ? C8 C3 C2 104.0(2) . . ? C64 C63 C62 119.6(3) . . ? C64 C63 H63A 120.2 . . ? C62 C63 H63A 120.2 . . ? N6 C58 C57 122.0(3) . . ? N6 C58 C59 115.1(2) . . ? C57 C58 C59 122.9(2) . . ? C10 C9 C7 120.3(3) . . ? C10 C9 H9A 119.9 . . ? C7 C9 H9A 119.9 . . ? C41 C40 C42 116.5(3) . . ? C41 C40 C39 116.2(3) . . ? C42 C40 C39 127.3(3) . . ? C49 C48 C47 119.6(3) . . ? C49 C48 H48A 120.2 . . ? C47 C48 H48A 120.2 . . ? C36 C37 C38 118.1(3) . . ? C36 C37 H37A 120.9 . . ? C38 C37 H37A 120.9 . . ? C25 C26 C27 110.2(2) . . ? C25 C26 H26A 109.6 . . ? C27 C26 H26A 109.6 . . ? C25 C26 H26B 109.6 . . ? C27 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? C16 C15 C14 119.8(3) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C65 C66 C61 121.2(2) . . ? C65 C66 N4 119.1(2) . . ? C61 C66 N4 119.6(2) . . ? C46 C47 C48 119.8(3) . . ? C46 C47 H47A 120.1 . . ? C48 C47 H47A 120.1 . . ? C61 C60 C59 114.3(2) . . ? C61 C60 H60A 108.7 . . ? C59 C60 H60A 108.7 . . ? C61 C60 H60B 108.7 . . ? C59 C60 H60B 108.7 . . ? H60A C60 H60B 107.6 . . ? C28 C27 C26 114.5(2) . . ? C28 C27 H27A 108.6 . . ? C26 C27 H27A 108.6 . . ? C28 C27 H27B 108.6 . . ? C26 C27 H27B 108.6 . . ? H27A C27 H27B 107.6 . . ? C45 C44 C43 118.9(3) . . ? C45 C44 H44A 120.5 . . ? C43 C44 H44A 120.5 . . ? C30 C29 C28 121.6(3) . . ? C30 C29 H29A 119.2 . . ? C28 C29 H29A 119.2 . . ? C29 C30 C31 120.1(3) . . ? C29 C30 H30A 119.9 . . ? C31 C30 H30A 119.9 . . ? C63 C64 C65 120.1(3) . . ? C63 C64 H64A 120.0 . . ? C65 C64 H64A 120.0 . . ? C30 C31 C32 120.1(3) . . ? C30 C31 H31A 119.9 . . ? C32 C31 H31A 119.9 . . ? C15 C16 C17 120.4(2) . . ? C15 C16 H16A 119.8 . . ? C17 C16 H16A 119.8 . . ? C57 C56 C55 119.3(3) . . ? C57 C56 H56A 120.4 . . ? C55 C56 H56A 120.4 . . ? C66 C65 C64 120.0(3) . . ? C66 C65 H65A 120.0 . . ? C64 C65 H65A 120.0 . . ? C42 C43 C44 122.8(3) . . ? C42 C43 H43A 118.6 . . ? C44 C43 H43A 118.6 . . ? C8 C7 C9 115.9(3) . . ? C8 C7 C6 116.2(2) . . ? C9 C7 C6 127.8(3) . . ? C43 C42 C40 120.0(3) . . ? C43 C42 H42A 120.0 . . ? C40 C42 H42A 120.0 . . ? C56 C55 C54 118.8(3) . . ? C56 C55 H55A 120.6 . . ? C54 C55 H55A 120.6 . . ? C39 C38 C37 123.0(3) . . ? C39 C38 H38A 118.5 . . ? C37 C38 H38A 118.5 . . ? C38 C39 C40 120.1(3) . . ? C38 C39 H39A 119.9 . . ? C40 C39 H39A 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 As2 N5 C35 6.65(17) . . . . ? Cl2 As2 N5 C35 -92.20(17) . . . . ? N4 As2 N5 C46 176.3(2) . . . . ? Cl2 As2 N5 C46 77.47(19) . . . . ? N2 As1 N1 C1 -10.17(17) . . . . ? Cl1 As1 N1 C1 89.54(16) . . . . ? N2 As1 N1 C33 -168.9(2) . . . . ? Cl1 As1 N1 C33 -69.2(2) . . . . ? N1 As1 N2 C2 8.10(17) . . . . ? Cl1 As1 N2 C2 -89.28(17) . . . . ? N1 As1 N2 C13 178.9(2) . . . . ? Cl1 As1 N2 C13 81.5(2) . . . . ? N5 As2 N4 C34 -8.24(17) . . . . ? Cl2 As2 N4 C34 91.34(17) . . . . ? N5 As2 N4 C66 -168.3(2) . . . . ? Cl2 As2 N4 C66 -68.7(2) . . . . ? C46 N5 C35 C34 -173.4(2) . . . . ? As2 N5 C35 C34 -3.6(3) . . . . ? C46 N5 C35 C36 9.5(4) . . . . ? As2 N5 C35 C36 179.2(2) . . . . ? C55 C54 N6 C58 -0.3(4) . . . . ? C53 C54 N6 C58 177.8(2) . . . . ? C17 C18 C13 C14 0.6(4) . . . . ? C19 C18 C13 C14 177.7(2) . . . . ? C17 C18 C13 N2 179.9(2) . . . . ? C19 C18 C13 N2 -3.0(3) . . . . ? C2 N2 C13 C14 83.7(3) . . . . ? As1 N2 C13 C14 -86.1(3) . . . . ? C2 N2 C13 C18 -95.6(3) . . . . ? As1 N2 C13 C18 94.6(3) . . . . ? C13 C18 C17 C16 0.9(4) . . . . ? C19 C18 C17 C16 -176.2(2) . . . . ? C44 C45 C41 C40 0.6(4) . . . . ? C34 C45 C41 C40 -178.6(2) . . . . ? C44 C45 C41 C36 179.1(2) . . . . ? C34 C45 C41 C36 -0.1(3) . . . . ? C12 C11 C10 C9 -0.1(4) . . . . ? C10 C11 C12 C8 1.6(4) . . . . ? C10 C11 C12 C1 -178.9(3) . . . . ? N6 C54 C53 C52 -74.8(3) . . . . ? C55 C54 C53 C52 103.3(3) . . . . ? C31 C32 C33 C28 -1.8(4) . . . . ? C31 C32 C33 N1 179.9(2) . . . . ? C1 N1 C33 C32 -48.5(4) . . . . ? As1 N1 C33 C32 107.7(2) . . . . ? C1 N1 C33 C28 133.1(3) . . . . ? As1 N1 C33 C28 -70.7(3) . . . . ? C17 C18 C19 C20 87.2(3) . . . . ? C13 C18 C19 C20 -89.8(3) . . . . ? C33 N1 C1 C2 168.6(2) . . . . ? As1 N1 C1 C2 10.2(3) . . . . ? C33 N1 C1 C12 -19.7(4) . . . . ? As1 N1 C1 C12 -178.2(2) . . . . ? C11 C12 C1 C2 -177.8(3) . . . . ? C8 C12 C1 C2 1.8(3) . . . . ? C11 C12 C1 N1 10.3(5) . . . . ? C8 C12 C1 N1 -170.1(3) . . . . ? C21 N3 C25 C24 1.8(4) . . . . ? C21 N3 C25 C26 -177.6(2) . . . . ? C11 C12 C8 C7 -2.2(4) . . . . ? C1 C12 C8 C7 178.1(2) . . . . ? C11 C12 C8 C3 179.1(2) . . . . ? C1 C12 C8 C3 -0.6(3) . . . . ? C50 C51 C52 C53 93.9(3) . . . . ? C46 C51 C52 C53 -81.9(3) . . . . ? C54 C53 C52 C51 148.5(2) . . . . ? C50 C51 C46 C47 0.1(4) . . . . ? C52 C51 C46 C47 176.1(2) . . . . ? C50 C51 C46 N5 -179.0(2) . . . . ? C52 C51 C46 N5 -3.1(4) . . . . ? C35 N5 C46 C47 95.0(3) . . . . ? As2 N5 C46 C47 -73.4(3) . . . . ? C35 N5 C46 C51 -85.8(3) . . . . ? As2 N5 C46 C51 105.8(2) . . . . ? N3 C25 C24 C23 -1.2(4) . . . . ? C26 C25 C24 C23 178.1(3) . . . . ? C18 C13 C14 C15 -1.5(4) . . . . ? N2 C13 C14 C15 179.2(2) . . . . ? N1 C1 C2 N2 -3.9(3) . . . . ? C12 C1 C2 N2 -177.8(2) . . . . ? N1 C1 C2 C3 171.6(2) . . . . ? C12 C1 C2 C3 -2.3(3) . . . . ? C13 N2 C2 C1 -175.5(2) . . . . ? As1 N2 C2 C1 -4.3(3) . . . . ? C13 N2 C2 C3 10.4(4) . . . . ? As1 N2 C2 C3 -178.4(2) . . . . ? C66 C61 C62 C63 -0.5(4) . . . . ? C60 C61 C62 C63 179.4(3) . . . . ? C25 N3 C21 C22 -0.7(4) . . . . ? C25 N3 C21 C20 177.4(2) . . . . ? C23 C22 C21 N3 -0.8(4) . . . . ? C23 C22 C21 C20 -178.8(2) . . . . ? C21 C22 C23 C24 1.4(4) . . . . ? C25 C24 C23 C22 -0.4(4) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? N5 C35 C34 N4 -3.1(3) . . . . ? C36 C35 C34 N4 174.8(2) . . . . ? N5 C35 C34 C45 179.8(2) . . . . ? C36 C35 C34 C45 -2.3(3) . . . . ? C66 N4 C34 C35 168.0(2) . . . . ? As2 N4 C34 C35 8.2(3) . . . . ? C66 N4 C34 C45 -15.9(5) . . . . ? As2 N4 C34 C45 -175.7(3) . . . . ? C44 C45 C34 C35 -177.4(3) . . . . ? C41 C45 C34 C35 1.5(3) . . . . ? C44 C45 C34 N4 6.3(6) . . . . ? C41 C45 C34 N4 -174.7(3) . . . . ? C40 C41 C36 C37 -2.9(4) . . . . ? C45 C41 C36 C37 178.6(2) . . . . ? C40 C41 C36 C35 177.3(2) . . . . ? C45 C41 C36 C35 -1.2(3) . . . . ? C34 C35 C36 C37 -177.6(3) . . . . ? N5 C35 C36 C37 -0.3(5) . . . . ? C34 C35 C36 C41 2.2(3) . . . . ? N5 C35 C36 C41 179.4(3) . . . . ? C32 C33 C28 C29 2.2(4) . . . . ? N1 C33 C28 C29 -179.4(2) . . . . ? C32 C33 C28 C27 -176.0(3) . . . . ? N1 C33 C28 C27 2.3(4) . . . . ? N3 C21 C20 C19 -64.7(3) . . . . ? C22 C21 C20 C19 113.4(3) . . . . ? C18 C19 C20 C21 151.1(2) . . . . ? C4 C5 C6 C7 0.2(4) . . . . ? C46 C51 C50 C49 -0.2(4) . . . . ? C52 C51 C50 C49 -176.1(3) . . . . ? C48 C49 C50 C51 0.4(4) . . . . ? C5 C4 C3 C8 -0.3(4) . . . . ? C5 C4 C3 C2 177.4(3) . . . . ? C7 C8 C3 C4 -1.1(4) . . . . ? C12 C8 C3 C4 177.7(2) . . . . ? C7 C8 C3 C2 -179.4(2) . . . . ? C12 C8 C3 C2 -0.6(3) . . . . ? C1 C2 C3 C4 -176.1(3) . . . . ? N2 C2 C3 C4 -1.8(5) . . . . ? C1 C2 C3 C8 1.8(3) . . . . ? N2 C2 C3 C8 176.1(3) . . . . ? C61 C62 C63 C64 0.9(4) . . . . ? C54 N6 C58 C57 1.2(4) . . . . ? C54 N6 C58 C59 -178.2(2) . . . . ? C56 C57 C58 N6 -0.6(4) . . . . ? C56 C57 C58 C59 178.6(2) . . . . ? C60 C59 C58 N6 -62.6(3) . . . . ? C60 C59 C58 C57 118.1(3) . . . . ? C11 C10 C9 C7 -0.9(4) . . . . ? C36 C41 C40 C42 -178.3(2) . . . . ? C45 C41 C40 C42 -0.1(4) . . . . ? C36 C41 C40 C39 2.2(4) . . . . ? C45 C41 C40 C39 -179.6(3) . . . . ? C50 C49 C48 C47 -0.4(4) . . . . ? C41 C36 C37 C38 1.6(4) . . . . ? C35 C36 C37 C38 -178.7(3) . . . . ? N3 C25 C26 C27 -67.7(3) . . . . ? C24 C25 C26 C27 112.9(3) . . . . ? C13 C14 C15 C16 1.0(4) . . . . ? C62 C61 C66 C65 0.2(4) . . . . ? C60 C61 C66 C65 -179.7(3) . . . . ? C62 C61 C66 N4 178.7(2) . . . . ? C60 C61 C66 N4 -1.2(4) . . . . ? C34 N4 C66 C65 -55.9(4) . . . . ? As2 N4 C66 C65 101.7(3) . . . . ? C34 N4 C66 C61 125.6(3) . . . . ? As2 N4 C66 C61 -76.9(3) . . . . ? C51 C46 C47 C48 -0.2(4) . . . . ? N5 C46 C47 C48 179.0(2) . . . . ? C49 C48 C47 C46 0.3(4) . . . . ? C66 C61 C60 C59 -67.0(3) . . . . ? C62 C61 C60 C59 113.1(3) . . . . ? C58 C59 C60 C61 147.5(2) . . . . ? C29 C28 C27 C26 111.8(3) . . . . ? C33 C28 C27 C26 -70.0(3) . . . . ? C25 C26 C27 C28 152.1(2) . . . . ? C41 C45 C44 C43 -0.7(4) . . . . ? C34 C45 C44 C43 178.2(3) . . . . ? C33 C28 C29 C30 -0.9(4) . . . . ? C27 C28 C29 C30 177.4(3) . . . . ? C28 C29 C30 C31 -1.0(4) . . . . ? C62 C63 C64 C65 -1.0(5) . . . . ? C29 C30 C31 C32 1.5(4) . . . . ? C33 C32 C31 C30 -0.1(4) . . . . ? C14 C15 C16 C17 0.4(4) . . . . ? C18 C17 C16 C15 -1.4(4) . . . . ? C58 C57 C56 C55 -0.7(4) . . . . ? C61 C66 C65 C64 -0.3(4) . . . . ? N4 C66 C65 C64 -178.8(3) . . . . ? C63 C64 C65 C66 0.7(5) . . . . ? C45 C44 C43 C42 0.2(4) . . . . ? C3 C8 C7 C9 179.8(2) . . . . ? C12 C8 C7 C9 1.2(4) . . . . ? C3 C8 C7 C6 1.9(4) . . . . ? C12 C8 C7 C6 -176.7(2) . . . . ? C10 C9 C7 C8 0.4(4) . . . . ? C10 C9 C7 C6 178.0(3) . . . . ? C5 C6 C7 C8 -1.4(4) . . . . ? C5 C6 C7 C9 -179.0(3) . . . . ? C44 C43 C42 C40 0.4(5) . . . . ? C41 C40 C42 C43 -0.4(4) . . . . ? C39 C40 C42 C43 179.0(3) . . . . ? C57 C56 C55 C54 1.5(4) . . . . ? N6 C54 C55 C56 -1.0(4) . . . . ? C53 C54 C55 C56 -179.0(2) . . . . ? C36 C37 C38 C39 0.2(4) . . . . ? C37 C38 C39 C40 -1.0(5) . . . . ? C41 C40 C39 C38 -0.2(4) . . . . ? C42 C40 C39 C38 -179.6(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.439 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.065 data_3P _database_code_depnum_ccdc_archive 'CCDC 864990' #TrackingRef '- CIF_Ragogna_clamshell.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 Cl N3 P' _chemical_formula_sum 'C33 H25 Cl N3 P' _chemical_formula_weight 529.98 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' Cl Cl 0.1484 0.1585 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 _symmetry_space_group_name_Hall P2c-2n 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 20.871(4) _cell_length_b 13.861(3) _cell_length_c 22.172(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6414(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9973 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 21.54 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2208 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9904 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details ? _exptl_special_details ; Disordered solvates could not be modelled, squeeze function was employed ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 109414 _diffrn_reflns_av_R_equivalents 0.0817 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 26.86 _reflns_number_total 13749 _reflns_number_gt 10016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0935P)^2^+2.5184P] 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 0.20(8) _refine_ls_number_reflns 13749 _refine_ls_number_parameters 686 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1653 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Cl1 Cl -0.48574(5) 0.32009(8) -0.47480(5) 0.0302(2) Uani 1 1 d . . . P1 P -0.53265(5) 0.27680(9) -0.37912(5) 0.0240(2) Uani 1 1 d . . . N2 N -0.46420(17) 0.2468(2) -0.3386(2) 0.0213(10) Uani 1 1 d . . . N1 N -0.55034(16) 0.1593(2) -0.38853(16) 0.0248(8) Uani 1 1 d . . . N3 N -0.60075(18) 0.2063(3) -0.22987(18) 0.0297(9) Uani 1 1 d . . . C2 C -0.45332(19) 0.1506(3) -0.3417(2) 0.0266(10) Uani 1 1 d . . . C1 C -0.5020(2) 0.0984(3) -0.37018(19) 0.0277(10) Uani 1 1 d . . . C12 C -0.4870(2) -0.0026(3) -0.3667(2) 0.0332(11) Uani 1 1 d . . . C11 C -0.5173(2) -0.0904(3) -0.3856(2) 0.0290(10) Uani 1 1 d . . . H11A H -0.5575 -0.0902 -0.4057 0.035 Uiso 1 1 calc R . . C10 C -0.4852(3) -0.1751(3) -0.3731(2) 0.0406(13) Uani 1 1 d . . . H10A H -0.5057 -0.2337 -0.3842 0.049 Uiso 1 1 calc R . . C9 C -0.4264(3) -0.1820(3) -0.3462(2) 0.0387(13) Uani 1 1 d . . . H9A H -0.4073 -0.2432 -0.3394 0.046 Uiso 1 1 calc R . . C7 C -0.3930(3) -0.0918(3) -0.3278(3) 0.0415(12) Uani 1 1 d . . . C8 C -0.4276(2) -0.0092(3) -0.3396(2) 0.0278(10) Uani 1 1 d . . . C6 C -0.3356(2) -0.0864(3) -0.2961(3) 0.0393(13) Uani 1 1 d . . . H6A H -0.3128 -0.1431 -0.2853 0.047 Uiso 1 1 calc R . . C5 C -0.3128(3) 0.0034(4) -0.2811(3) 0.0414(12) Uani 1 1 d . . . H5A H -0.2719 0.0085 -0.2624 0.050 Uiso 1 1 calc R . . C4 C -0.3469(2) 0.0860(4) -0.2921(2) 0.0372(12) Uani 1 1 d . . . H4A H -0.3304 0.1455 -0.2775 0.045 Uiso 1 1 calc R . . C3 C -0.4014(2) 0.0868(3) -0.3219(2) 0.0287(11) Uani 1 1 d . . . C33 C -0.6087(2) 0.1302(3) -0.4189(2) 0.0290(10) Uani 1 1 d . . . C32 C -0.6170(2) 0.1554(3) -0.4802(2) 0.0347(11) Uani 1 1 d . . . H32A H -0.5849 0.1922 -0.5001 0.042 Uiso 1 1 calc R . . C31 C -0.6706(3) 0.1277(4) -0.5115(2) 0.0425(12) Uani 1 1 d . . . H31A H -0.6758 0.1430 -0.5530 0.051 Uiso 1 1 calc R . . C30 C -0.7179(2) 0.0752(3) -0.4794(3) 0.0359(12) Uani 1 1 d . . . H30A H -0.7562 0.0569 -0.4996 0.043 Uiso 1 1 calc R . . C29 C -0.7099(2) 0.0507(3) -0.4215(3) 0.0326(11) Uani 1 1 d . . . H29A H -0.7422 0.0134 -0.4024 0.039 Uiso 1 1 calc R . . C28 C -0.6558(2) 0.0778(3) -0.3876(2) 0.0314(10) Uani 1 1 d . . . C27 C -0.6503(2) 0.0510(4) -0.3248(3) 0.0454(13) Uani 1 1 d . . . H27A H -0.6043 0.0503 -0.3137 0.054 Uiso 1 1 calc R . . H27B H -0.6668 -0.0155 -0.3199 0.054 Uiso 1 1 calc R . . C26 C -0.6871(2) 0.1194(4) -0.2789(2) 0.0412(12) Uani 1 1 d . . . H26A H -0.7305 0.1328 -0.2950 0.049 Uiso 1 1 calc R . . H26B H -0.6923 0.0851 -0.2400 0.049 Uiso 1 1 calc R . . C25 C -0.6536(2) 0.2129(5) -0.2679(2) 0.0435(14) Uani 1 1 d . . . C24 C -0.6737(2) 0.3011(5) -0.2867(2) 0.0424(14) Uani 1 1 d . . . H24A H -0.7115 0.3049 -0.3103 0.051 Uiso 1 1 calc R . . C23 C -0.6426(2) 0.3835(4) -0.2735(2) 0.0357(11) Uani 1 1 d . . . H23A H -0.6573 0.4441 -0.2880 0.043 Uiso 1 1 calc R . . C22 C -0.5877(2) 0.3760(4) -0.2375(2) 0.0352(11) Uani 1 1 d . . . H22A H -0.5628 0.4311 -0.2275 0.042 Uiso 1 1 calc R . . C21 C -0.5713(2) 0.2848(3) -0.21720(19) 0.0241(9) Uani 1 1 d . . . C20 C -0.5118(2) 0.2700(4) -0.1745(2) 0.0262(10) Uani 1 1 d . . . H20A H -0.5021 0.3311 -0.1533 0.031 Uiso 1 1 calc R . . H20B H -0.5219 0.2204 -0.1438 0.031 Uiso 1 1 calc R . . C19 C -0.4539(2) 0.2385(3) -0.2105(2) 0.0248(11) Uani 1 1 d . . . H19A H -0.4225 0.2097 -0.1824 0.030 Uiso 1 1 calc R . . H19B H -0.4675 0.1872 -0.2388 0.030 Uiso 1 1 calc R . . C18 C -0.4216(2) 0.3136(3) -0.24505(19) 0.0227(9) Uani 1 1 d . . . C17 C -0.38457(19) 0.3840(3) -0.2180(2) 0.0258(9) Uani 1 1 d . . . H17A H -0.3788 0.3832 -0.1755 0.031 Uiso 1 1 calc R . . C16 C -0.3548(2) 0.4578(3) -0.2530(2) 0.0315(10) Uani 1 1 d . . . H16A H -0.3317 0.5078 -0.2334 0.038 Uiso 1 1 calc R . . C15 C -0.3594(2) 0.4570(4) -0.3125(2) 0.0321(11) Uani 1 1 d . . . H15A H -0.3378 0.5044 -0.3358 0.039 Uiso 1 1 calc R . . C14 C -0.39538(19) 0.3873(3) -0.3405(2) 0.0222(9) Uani 1 1 d . . . H14A H -0.3982 0.3868 -0.3832 0.027 Uiso 1 1 calc R . . C13 C -0.42793(19) 0.3172(3) -0.30737(19) 0.0206(9) Uani 1 1 d . . . Cl2 Cl -0.25961(5) -0.32056(8) -0.32898(5) 0.0304(2) Uani 1 1 d . . . P2 P -0.21361(5) -0.28016(8) -0.42406(6) 0.0250(2) Uani 1 1 d . . . N5 N -0.19394(17) -0.1620(3) -0.41436(17) 0.0274(8) Uani 1 1 d . . . N4 N -0.27752(18) -0.2483(2) -0.4628(2) 0.0182(9) Uani 1 1 d . . . N6 N -0.14634(18) -0.2029(3) -0.57287(17) 0.0284(9) Uani 1 1 d . . . C35 C -0.2440(2) -0.1006(3) -0.43437(19) 0.0246(9) Uani 1 1 d . . . C34 C -0.29210(19) -0.1469(3) -0.46013(19) 0.0233(9) Uani 1 1 d . . . C45 C -0.3413(2) -0.0811(3) -0.4798(2) 0.0281(11) Uani 1 1 d . . . C44 C -0.4006(2) -0.0920(3) -0.5113(2) 0.0348(12) Uani 1 1 d . . . H44 H -0.4173 -0.1528 -0.5232 0.042 Uiso 1 1 calc R . . C43 C -0.4332(2) -0.0005(4) -0.5237(3) 0.0469(14) Uani 1 1 d . . . H43A H -0.4726 -0.0023 -0.5450 0.056 Uiso 1 1 calc R . . C42 C -0.4104(3) 0.0860(4) -0.5064(2) 0.0428(13) Uani 1 1 d . . . H42A H -0.4350 0.1422 -0.5146 0.051 Uiso 1 1 calc R . . C40 C -0.3496(2) 0.0961(3) -0.4759(2) 0.0299(10) Uani 1 1 d . . . C41 C -0.3196(2) 0.0085(3) -0.4625(2) 0.0261(10) Uani 1 1 d . . . C39 C -0.3191(3) 0.1806(4) -0.4577(2) 0.0392(12) Uani 1 1 d . . . H39A H -0.3402 0.2407 -0.4629 0.047 Uiso 1 1 calc R . . C38 C -0.2587(2) 0.1784(4) -0.4321(2) 0.0373(12) Uani 1 1 d . . . H38A H -0.2382 0.2369 -0.4210 0.045 Uiso 1 1 calc R . . C37 C -0.2253(3) 0.0830(4) -0.4217(2) 0.0406(13) Uani 1 1 d . . . H37A H -0.1827 0.0806 -0.4067 0.049 Uiso 1 1 calc R . . C36 C -0.25660(19) 0.0046(3) -0.43372(19) 0.0224(9) Uani 1 1 d . . . C66 C -0.31897(19) -0.3169(3) -0.4942(2) 0.0273(10) Uani 1 1 d . . . C65 C -0.3480(2) -0.3883(4) -0.4587(2) 0.0329(12) Uani 1 1 d . . . H65A H -0.3442 -0.3876 -0.4160 0.039 Uiso 1 1 calc R . . C64 C -0.3828(2) -0.4607(3) -0.4881(2) 0.0320(11) Uani 1 1 d . . . H64A H -0.4034 -0.5095 -0.4650 0.038 Uiso 1 1 calc R . . C63 C -0.3878(2) -0.4618(4) -0.5530(2) 0.0364(12) Uani 1 1 d . . . H63A H -0.4112 -0.5108 -0.5733 0.044 Uiso 1 1 calc R . . C62 C -0.3575(2) -0.3893(4) -0.5846(2) 0.0340(11) Uani 1 1 d . . . H62A H -0.3597 -0.3901 -0.6274 0.041 Uiso 1 1 calc R . . C61 C -0.32411(19) -0.3156(3) -0.5568(2) 0.0255(10) Uani 1 1 d . . . C60 C -0.2947(2) -0.2408(3) -0.6017(2) 0.0292(12) Uani 1 1 d . . . H60A H -0.2852 -0.1803 -0.5797 0.035 Uiso 1 1 calc R . . H60B H -0.3267 -0.2257 -0.6333 0.035 Uiso 1 1 calc R . . C59 C -0.2319(2) -0.2782(4) -0.6324(2) 0.0357(11) Uani 1 1 d . . . H59A H -0.2406 -0.3413 -0.6516 0.043 Uiso 1 1 calc R . . H59B H -0.2190 -0.2325 -0.6645 0.043 Uiso 1 1 calc R . . C58 C -0.1777(2) -0.2894(4) -0.5888(2) 0.0361(13) Uani 1 1 d . . . C57 C -0.1560(2) -0.3772(3) -0.5695(2) 0.0340(11) Uani 1 1 d . . . H57A H -0.1784 -0.4345 -0.5801 0.041 Uiso 1 1 calc R . . C56 C -0.1021(3) -0.3822(4) -0.5352(3) 0.0456(14) Uani 1 1 d . . . H56A H -0.0867 -0.4434 -0.5224 0.055 Uiso 1 1 calc R . . C55 C -0.0691(2) -0.2987(3) -0.5182(3) 0.0363(12) Uani 1 1 d . . . H55A H -0.0320 -0.3016 -0.4935 0.044 Uiso 1 1 calc R . . C54 C -0.0934(2) -0.2103(4) -0.53950(18) 0.0245(10) Uani 1 1 d . . . C53 C -0.0600(3) -0.1152(4) -0.5257(2) 0.0415(13) Uani 1 1 d . . . H53A H -0.0180 -0.1290 -0.5067 0.050 Uiso 1 1 calc R . . H53B H -0.0518 -0.0808 -0.5640 0.050 Uiso 1 1 calc R . . C52 C -0.0983(2) -0.0498(3) -0.4841(2) 0.0317(10) Uani 1 1 d . . . H52A H -0.1441 -0.0527 -0.4956 0.038 Uiso 1 1 calc R . . H52B H -0.0837 0.0176 -0.4895 0.038 Uiso 1 1 calc R . . C51 C -0.0916(2) -0.0779(3) -0.4168(2) 0.0293(10) Uani 1 1 d . . . C50 C -0.0355(2) -0.0508(4) -0.3863(3) 0.0400(13) Uani 1 1 d . . . H50A H -0.0033 -0.0149 -0.4067 0.048 Uiso 1 1 calc R . . C49 C -0.0267(2) -0.0767(4) -0.3255(2) 0.0368(11) Uani 1 1 d . . . H49A H 0.0109 -0.0566 -0.3050 0.044 Uiso 1 1 calc R . . C48 C -0.0712(2) -0.1299(3) -0.2958(2) 0.0366(12) Uani 1 1 d . . . H48A H -0.0638 -0.1499 -0.2554 0.044 Uiso 1 1 calc R . . C47 C -0.1294(2) -0.1557(3) -0.3259(2) 0.0335(11) Uani 1 1 d . . . H47A H -0.1618 -0.1901 -0.3049 0.040 Uiso 1 1 calc R . . C46 C -0.1380(2) -0.1310(3) -0.3842(2) 0.0261(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 Cl1 0.0325(6) 0.0234(5) 0.0347(6) 0.0023(5) 0.0009(5) -0.0031(4) P1 0.0203(5) 0.0277(6) 0.0241(6) -0.0014(6) -0.0014(5) -0.0001(5) N2 0.0134(18) 0.016(2) 0.035(3) -0.0032(14) -0.0068(18) -0.0054(12) N1 0.0283(19) 0.0157(17) 0.030(2) 0.0086(15) -0.0080(17) 0.0016(15) N3 0.026(2) 0.033(2) 0.030(2) 0.0058(18) 0.0098(17) 0.0026(16) C2 0.018(2) 0.022(2) 0.040(3) -0.0006(19) 0.0036(19) -0.0043(17) C1 0.037(2) 0.026(2) 0.021(2) -0.0073(18) -0.004(2) 0.0022(19) C12 0.047(3) 0.020(2) 0.033(3) 0.002(2) -0.005(2) -0.0048(19) C11 0.042(3) 0.0075(18) 0.038(3) -0.0099(18) 0.007(2) -0.0069(17) C10 0.066(4) 0.013(2) 0.043(3) -0.002(2) -0.004(3) -0.019(2) C9 0.056(3) 0.0071(19) 0.053(3) -0.007(2) 0.009(3) -0.002(2) C7 0.045(3) 0.031(3) 0.049(3) -0.005(2) 0.011(3) 0.004(2) C8 0.046(3) 0.0107(19) 0.027(2) -0.0002(17) 0.006(2) -0.0032(18) C6 0.034(3) 0.026(2) 0.058(3) 0.009(2) 0.008(2) 0.003(2) C5 0.038(3) 0.036(3) 0.050(3) -0.008(2) 0.008(2) 0.017(2) C4 0.031(3) 0.032(3) 0.049(3) 0.007(2) 0.019(2) -0.005(2) C3 0.031(2) 0.027(2) 0.028(3) -0.007(2) 0.000(2) 0.0023(19) C33 0.029(2) 0.012(2) 0.046(3) -0.002(2) -0.006(2) -0.0008(16) C32 0.037(3) 0.034(3) 0.034(3) -0.001(2) -0.003(2) -0.011(2) C31 0.046(3) 0.040(3) 0.041(3) 0.000(2) -0.011(2) -0.003(2) C30 0.028(2) 0.026(2) 0.054(3) -0.018(2) -0.004(2) -0.0051(19) C29 0.038(3) 0.017(2) 0.042(3) -0.008(2) 0.011(2) -0.0019(19) C28 0.031(2) 0.021(2) 0.042(3) -0.002(2) -0.001(2) -0.0045(18) C27 0.041(3) 0.044(3) 0.052(3) 0.013(3) -0.001(3) -0.028(2) C26 0.035(3) 0.056(3) 0.032(3) -0.007(3) 0.012(2) -0.014(3) C25 0.028(3) 0.062(4) 0.040(3) -0.003(3) 0.013(2) 0.005(3) C24 0.027(3) 0.080(4) 0.020(2) 0.012(3) 0.006(2) 0.012(3) C23 0.025(3) 0.053(3) 0.029(2) 0.000(2) 0.001(2) 0.009(2) C22 0.045(3) 0.032(3) 0.028(2) -0.001(2) -0.005(2) 0.002(2) C21 0.033(2) 0.024(2) 0.016(2) 0.0023(18) 0.0032(18) 0.005(2) C20 0.025(2) 0.039(2) 0.015(2) 0.003(2) -0.0009(18) -0.013(2) C19 0.022(2) 0.038(3) 0.013(2) -0.0174(18) -0.0057(18) -0.0011(18) C18 0.025(2) 0.018(2) 0.025(2) -0.0025(17) -0.0042(18) 0.0010(17) C17 0.016(2) 0.026(2) 0.035(2) -0.0034(19) -0.0061(18) -0.0031(17) C16 0.027(2) 0.027(2) 0.040(3) -0.004(2) -0.001(2) -0.0028(19) C15 0.013(2) 0.036(3) 0.047(3) -0.004(2) 0.003(2) -0.0053(18) C14 0.023(2) 0.0132(19) 0.030(2) 0.0095(18) -0.0085(18) 0.0037(16) C13 0.023(2) 0.0062(17) 0.033(2) -0.0028(16) -0.0037(18) 0.0018(15) Cl2 0.0336(6) 0.0252(5) 0.0323(6) 0.0034(5) 0.0012(5) 0.0003(4) P2 0.0251(6) 0.0146(5) 0.0352(6) 0.0006(6) -0.0024(5) -0.0021(5) N5 0.0247(19) 0.0250(19) 0.033(2) -0.0023(16) 0.0033(17) -0.0039(15) N4 0.0181(19) 0.020(2) 0.017(2) 0.0009(13) -0.0035(16) -0.0011(13) N6 0.027(2) 0.030(2) 0.028(2) -0.0013(17) 0.0046(17) -0.0128(16) C35 0.029(2) 0.021(2) 0.024(2) 0.0055(18) -0.0013(19) 0.0024(17) C34 0.020(2) 0.025(2) 0.025(2) 0.0006(18) -0.0014(18) 0.0038(17) C45 0.020(2) 0.013(2) 0.052(3) -0.003(2) 0.006(2) -0.0100(16) C44 0.029(2) 0.025(2) 0.051(3) -0.008(2) -0.009(2) 0.015(2) C43 0.019(2) 0.057(4) 0.065(4) 0.008(3) -0.008(2) 0.002(2) C42 0.045(3) 0.040(3) 0.043(3) 0.003(2) 0.000(2) 0.025(2) C40 0.038(3) 0.015(2) 0.037(3) 0.0037(19) 0.007(2) 0.0072(18) C41 0.028(2) 0.022(2) 0.029(2) 0.0045(18) 0.0016(19) 0.0037(18) C39 0.050(3) 0.037(3) 0.030(3) 0.013(2) 0.002(2) 0.009(2) C38 0.052(3) 0.034(3) 0.026(2) 0.004(2) 0.005(2) 0.008(2) C37 0.056(3) 0.041(3) 0.025(3) 0.004(2) -0.002(2) -0.003(2) C36 0.023(2) 0.022(2) 0.022(2) -0.0045(18) 0.0051(17) 0.0039(16) C66 0.011(2) 0.033(2) 0.038(3) 0.000(2) -0.0006(18) 0.0021(17) C65 0.022(2) 0.042(3) 0.034(3) 0.014(2) -0.002(2) -0.006(2) C64 0.036(3) 0.018(2) 0.042(3) 0.010(2) -0.005(2) -0.0043(19) C63 0.022(2) 0.030(3) 0.057(3) 0.002(2) -0.008(2) -0.0110(19) C62 0.035(3) 0.046(3) 0.021(2) 0.000(2) -0.0039(19) 0.004(2) C61 0.014(2) 0.032(2) 0.030(2) 0.011(2) 0.0003(18) 0.0020(18) C60 0.035(3) 0.027(2) 0.026(3) 0.0202(19) 0.003(2) 0.0029(19) C59 0.034(3) 0.044(3) 0.029(3) -0.015(3) 0.004(2) 0.002(2) C58 0.026(3) 0.058(4) 0.025(2) -0.012(2) 0.008(2) -0.017(2) C57 0.042(3) 0.025(2) 0.034(3) -0.007(2) 0.014(2) -0.002(2) C56 0.053(4) 0.035(3) 0.049(3) 0.003(3) 0.015(3) 0.006(3) C55 0.023(2) 0.034(3) 0.051(3) -0.008(2) 0.007(2) -0.008(2) C54 0.024(2) 0.036(3) 0.013(2) 0.0042(19) 0.0038(17) -0.0109(19) C53 0.044(3) 0.041(3) 0.039(3) 0.010(2) 0.001(2) -0.017(2) C52 0.036(3) 0.027(2) 0.032(3) 0.007(2) -0.001(2) -0.009(2) C51 0.033(2) 0.023(2) 0.032(2) 0.001(2) -0.001(2) -0.0066(18) C50 0.021(2) 0.038(3) 0.061(4) 0.002(3) -0.004(2) -0.017(2) C49 0.026(2) 0.043(3) 0.041(3) 0.001(2) -0.014(2) 0.001(2) C48 0.035(3) 0.027(2) 0.047(3) -0.004(2) -0.010(2) -0.010(2) C47 0.028(2) 0.031(2) 0.042(3) 0.002(2) 0.000(2) -0.0043(19) C46 0.026(2) 0.022(2) 0.030(2) -0.0042(19) -0.002(2) -0.0034(17) _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 Cl1 P1 2.4122(17) . ? P1 N1 1.683(4) . ? P1 N2 1.738(4) . ? N2 C2 1.355(5) . ? N2 C13 1.415(5) . ? N1 C1 1.376(5) . ? N1 C33 1.449(6) . ? N3 C21 1.280(6) . ? N3 C25 1.392(7) . ? C2 C1 1.398(6) . ? C2 C3 1.465(6) . ? C1 C12 1.438(6) . ? C12 C8 1.380(7) . ? C12 C11 1.434(6) . ? C11 C10 1.380(7) . ? C11 H11A 0.9500 . ? C10 C9 1.367(7) . ? C10 H10A 0.9500 . ? C9 C7 1.489(7) . ? C9 H9A 0.9500 . ? C7 C8 1.379(6) . ? C7 C6 1.391(8) . ? C8 C3 1.492(6) . ? C6 C5 1.374(7) . ? C6 H6A 0.9500 . ? C5 C4 1.370(7) . ? C5 H5A 0.9500 . ? C4 C3 1.316(7) . ? C4 H4A 0.9500 . ? C33 C28 1.405(6) . ? C33 C32 1.415(7) . ? C32 C31 1.370(7) . ? C32 H32A 0.9500 . ? C31 C30 1.418(7) . ? C31 H31A 0.9500 . ? C30 C29 1.338(8) . ? C30 H30A 0.9500 . ? C29 C28 1.409(7) . ? C29 H29A 0.9500 . ? C28 C27 1.447(7) . ? C27 C26 1.588(8) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C26 C25 1.493(8) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C25 C24 1.358(8) . ? C24 C23 1.344(8) . ? C24 H24A 0.9500 . ? C23 C22 1.400(7) . ? C23 H23A 0.9500 . ? C22 C21 1.385(6) . ? C22 H22A 0.9500 . ? C21 C20 1.576(6) . ? C20 C19 1.512(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C19 C18 1.458(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C18 C17 1.380(6) . ? C18 C13 1.389(6) . ? C17 C16 1.426(7) . ? C17 H17A 0.9500 . ? C16 C15 1.323(7) . ? C16 H16A 0.9500 . ? C15 C14 1.371(6) . ? C15 H15A 0.9500 . ? C14 C13 1.395(6) . ? C14 H14A 0.9500 . ? Cl2 P2 2.3832(17) . ? P2 N4 1.646(4) . ? P2 N5 1.703(4) . ? N5 C46 1.412(5) . ? N5 C35 1.418(5) . ? N4 C34 1.439(5) . ? N4 C66 1.462(6) . ? N6 C54 1.334(6) . ? N6 C58 1.410(6) . ? C35 C34 1.322(6) . ? C35 C36 1.482(6) . ? C34 C45 1.441(6) . ? C45 C41 1.377(6) . ? C45 C44 1.430(6) . ? C44 C43 1.464(7) . ? C44 H44 0.9500 . ? C43 C42 1.345(8) . ? C43 H43A 0.9500 . ? C42 C40 1.444(7) . ? C42 H42A 0.9500 . ? C40 C39 1.393(7) . ? C40 C41 1.398(6) . ? C41 C36 1.462(6) . ? C39 C38 1.382(7) . ? C39 H39A 0.9500 . ? C38 C37 1.513(7) . ? C38 H38A 0.9500 . ? C37 C36 1.295(7) . ? C37 H37A 0.9500 . ? C66 C61 1.393(6) . ? C66 C65 1.402(6) . ? C65 C64 1.399(7) . ? C65 H65A 0.9500 . ? C64 C63 1.444(7) . ? C64 H64A 0.9500 . ? C63 C62 1.378(7) . ? C63 H63A 0.9500 . ? C62 C61 1.382(7) . ? C62 H62A 0.9500 . ? C61 C60 1.562(6) . ? C60 C59 1.567(7) . ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? C59 C58 1.496(7) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C58 C57 1.368(8) . ? C57 C56 1.359(8) . ? C57 H57A 0.9500 . ? C56 C55 1.398(7) . ? C56 H56A 0.9500 . ? C55 C54 1.407(7) . ? C55 H55A 0.9500 . ? C54 C53 1.522(7) . ? C53 C52 1.521(7) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C52 C51 1.550(6) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C51 C50 1.403(7) . ? C51 C46 1.414(6) . ? C50 C49 1.406(8) . ? C50 H50A 0.9500 . ? C49 C48 1.356(7) . ? C49 H49A 0.9500 . ? C48 C47 1.431(6) . ? C48 H48A 0.9500 . ? C47 C46 1.350(7) . ? C47 H47A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 N2 90.73(16) . . ? N1 P1 Cl1 102.75(14) . . ? N2 P1 Cl1 100.41(16) . . ? C2 N2 C13 127.9(4) . . ? C2 N2 P1 110.3(3) . . ? C13 N2 P1 121.8(3) . . ? C1 N1 C33 125.6(3) . . ? C1 N1 P1 113.3(3) . . ? C33 N1 P1 120.8(3) . . ? C21 N3 C25 117.2(4) . . ? N2 C2 C1 114.2(4) . . ? N2 C2 C3 134.6(4) . . ? C1 C2 C3 111.2(4) . . ? N1 C1 C2 110.5(4) . . ? N1 C1 C12 140.6(4) . . ? C2 C1 C12 108.7(4) . . ? C8 C12 C11 117.8(4) . . ? C8 C12 C1 106.5(4) . . ? C11 C12 C1 135.6(5) . . ? C10 C11 C12 116.7(4) . . ? C10 C11 H11A 121.6 . . ? C12 C11 H11A 121.6 . . ? C9 C10 C11 125.6(4) . . ? C9 C10 H10A 117.2 . . ? C11 C10 H10A 117.2 . . ? C10 C9 C7 118.8(4) . . ? C10 C9 H9A 120.6 . . ? C7 C9 H9A 120.6 . . ? C8 C7 C6 120.2(4) . . ? C8 C7 C9 113.5(5) . . ? C6 C7 C9 126.0(5) . . ? C7 C8 C12 127.5(4) . . ? C7 C8 C3 119.9(4) . . ? C12 C8 C3 112.6(4) . . ? C5 C6 C7 118.1(5) . . ? C5 C6 H6A 121.0 . . ? C7 C6 H6A 121.0 . . ? C4 C5 C6 122.3(5) . . ? C4 C5 H5A 118.9 . . ? C6 C5 H5A 118.9 . . ? C3 C4 C5 123.1(5) . . ? C3 C4 H4A 118.5 . . ? C5 C4 H4A 118.5 . . ? C4 C3 C2 142.6(4) . . ? C4 C3 C8 116.2(4) . . ? C2 C3 C8 100.9(4) . . ? C28 C33 C32 121.1(4) . . ? C28 C33 N1 120.1(4) . . ? C32 C33 N1 118.8(4) . . ? C31 C32 C33 121.2(5) . . ? C31 C32 H32A 119.4 . . ? C33 C32 H32A 119.4 . . ? C32 C31 C30 117.3(5) . . ? C32 C31 H31A 121.4 . . ? C30 C31 H31A 121.4 . . ? C29 C30 C31 121.6(4) . . ? C29 C30 H30A 119.2 . . ? C31 C30 H30A 119.2 . . ? C30 C29 C28 123.1(4) . . ? C30 C29 H29A 118.5 . . ? C28 C29 H29A 118.5 . . ? C33 C28 C29 115.7(4) . . ? C33 C28 C27 123.6(4) . . ? C29 C28 C27 120.7(4) . . ? C28 C27 C26 115.1(5) . . ? C28 C27 H27A 108.5 . . ? C26 C27 H27A 108.5 . . ? C28 C27 H27B 108.5 . . ? C26 C27 H27B 108.5 . . ? H27A C27 H27B 107.5 . . ? C25 C26 C27 113.3(4) . . ? C25 C26 H26A 108.9 . . ? C27 C26 H26A 108.9 . . ? C25 C26 H26B 108.9 . . ? C27 C26 H26B 108.9 . . ? H26A C26 H26B 107.7 . . ? C24 C25 N3 119.3(6) . . ? C24 C25 C26 126.0(5) . . ? N3 C25 C26 114.4(5) . . ? C23 C24 C25 123.3(5) . . ? C23 C24 H24A 118.3 . . ? C25 C24 H24A 118.3 . . ? C24 C23 C22 117.1(5) . . ? C24 C23 H23A 121.4 . . ? C22 C23 H23A 121.4 . . ? C21 C22 C23 117.0(5) . . ? C21 C22 H22A 121.5 . . ? C23 C22 H22A 121.5 . . ? N3 C21 C22 125.9(5) . . ? N3 C21 C20 113.5(4) . . ? C22 C21 C20 120.6(4) . . ? C19 C20 C21 110.6(4) . . ? C19 C20 H20A 109.5 . . ? C21 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? C18 C19 C20 116.2(4) . . ? C18 C19 H19A 108.2 . . ? C20 C19 H19A 108.2 . . ? C18 C19 H19B 108.2 . . ? C20 C19 H19B 108.2 . . ? H19A C19 H19B 107.4 . . ? C17 C18 C13 117.4(4) . . ? C17 C18 C19 122.4(4) . . ? C13 C18 C19 120.2(4) . . ? C18 C17 C16 121.0(4) . . ? C18 C17 H17A 119.5 . . ? C16 C17 H17A 119.5 . . ? C15 C16 C17 120.3(5) . . ? C15 C16 H16A 119.8 . . ? C17 C16 H16A 119.8 . . ? C16 C15 C14 119.7(5) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C15 C14 C13 121.3(4) . . ? C15 C14 H14A 119.3 . . ? C13 C14 H14A 119.3 . . ? C18 C13 C14 120.1(4) . . ? C18 C13 N2 120.9(4) . . ? C14 C13 N2 118.9(4) . . ? N4 P2 N5 90.17(17) . . ? N4 P2 Cl2 101.42(16) . . ? N5 P2 Cl2 102.21(14) . . ? C46 N5 C35 125.1(3) . . ? C46 N5 P2 123.5(3) . . ? C35 N5 P2 111.1(3) . . ? C34 N4 C66 122.0(4) . . ? C34 N4 P2 114.3(3) . . ? C66 N4 P2 123.6(3) . . ? C54 N6 C58 117.2(4) . . ? C34 C35 N5 113.8(4) . . ? C34 C35 C36 110.3(4) . . ? N5 C35 C36 135.9(4) . . ? C35 C34 N4 109.3(4) . . ? C35 C34 C45 111.4(4) . . ? N4 C34 C45 139.2(4) . . ? C41 C45 C44 121.1(4) . . ? C41 C45 C34 104.6(4) . . ? C44 C45 C34 134.3(4) . . ? C45 C44 C43 113.7(4) . . ? C45 C44 H44 123.2 . . ? C43 C44 H44 123.2 . . ? C42 C43 C44 123.7(5) . . ? C42 C43 H43A 118.2 . . ? C44 C43 H43A 118.2 . . ? C43 C42 C40 122.0(4) . . ? C43 C42 H42A 119.0 . . ? C40 C42 H42A 119.0 . . ? C39 C40 C41 117.6(4) . . ? C39 C40 C42 128.2(4) . . ? C41 C40 C42 114.2(4) . . ? C45 C41 C40 125.2(4) . . ? C45 C41 C36 112.6(4) . . ? C40 C41 C36 121.8(4) . . ? C38 C39 C40 121.1(5) . . ? C38 C39 H39A 119.4 . . ? C40 C39 H39A 119.4 . . ? C39 C38 C37 120.2(5) . . ? C39 C38 H38A 119.9 . . ? C37 C38 H38A 119.9 . . ? C36 C37 C38 117.9(5) . . ? C36 C37 H37A 121.0 . . ? C38 C37 H37A 121.0 . . ? C37 C36 C41 120.9(4) . . ? C37 C36 C35 137.5(4) . . ? C41 C36 C35 101.0(3) . . ? C61 C66 C65 122.3(4) . . ? C61 C66 N4 120.8(4) . . ? C65 C66 N4 116.6(4) . . ? C64 C65 C66 118.0(5) . . ? C64 C65 H65A 121.0 . . ? C66 C65 H65A 121.0 . . ? C65 C64 C63 120.5(4) . . ? C65 C64 H64A 119.7 . . ? C63 C64 H64A 119.7 . . ? C62 C63 C64 117.9(4) . . ? C62 C63 H63A 121.1 . . ? C64 C63 H63A 121.1 . . ? C63 C62 C61 122.9(4) . . ? C63 C62 H62A 118.5 . . ? C61 C62 H62A 118.5 . . ? C62 C61 C66 118.3(4) . . ? C62 C61 C60 113.9(4) . . ? C66 C61 C60 127.8(4) . . ? C61 C60 C59 112.7(4) . . ? C61 C60 H60A 109.1 . . ? C59 C60 H60A 109.1 . . ? C61 C60 H60B 109.1 . . ? C59 C60 H60B 109.1 . . ? H60A C60 H60B 107.8 . . ? C58 C59 C60 112.8(4) . . ? C58 C59 H59A 109.0 . . ? C60 C59 H59A 109.0 . . ? C58 C59 H59B 109.0 . . ? C60 C59 H59B 109.0 . . ? H59A C59 H59B 107.8 . . ? C57 C58 N6 121.7(5) . . ? C57 C58 C59 123.0(5) . . ? N6 C58 C59 115.1(5) . . ? C56 C57 C58 119.6(5) . . ? C56 C57 H57A 120.2 . . ? C58 C57 H57A 120.2 . . ? C57 C56 C55 121.1(5) . . ? C57 C56 H56A 119.4 . . ? C55 C56 H56A 119.4 . . ? C56 C55 C54 116.9(5) . . ? C56 C55 H55A 121.5 . . ? C54 C55 H55A 121.5 . . ? N6 C54 C55 123.5(4) . . ? N6 C54 C53 115.1(4) . . ? C55 C54 C53 121.4(4) . . ? C52 C53 C54 113.4(4) . . ? C52 C53 H53A 108.9 . . ? C54 C53 H53A 108.9 . . ? C52 C53 H53B 108.9 . . ? C54 C53 H53B 108.9 . . ? H53A C53 H53B 107.7 . . ? C53 C52 C51 112.7(4) . . ? C53 C52 H52A 109.1 . . ? C51 C52 H52A 109.1 . . ? C53 C52 H52B 109.1 . . ? C51 C52 H52B 109.1 . . ? H52A C52 H52B 107.8 . . ? C50 C51 C46 117.7(4) . . ? C50 C51 C52 118.2(4) . . ? C46 C51 C52 124.1(4) . . ? C51 C50 C49 120.1(4) . . ? C51 C50 H50A 120.0 . . ? C49 C50 H50A 120.0 . . ? C48 C49 C50 121.0(4) . . ? C48 C49 H49A 119.5 . . ? C50 C49 H49A 119.5 . . ? C49 C48 C47 119.3(5) . . ? C49 C48 H48A 120.3 . . ? C47 C48 H48A 120.3 . . ? C46 C47 C48 119.7(4) . . ? C46 C47 H47A 120.1 . . ? C48 C47 H47A 120.1 . . ? C47 C46 N5 119.1(4) . . ? C47 C46 C51 122.0(4) . . ? N5 C46 C51 118.9(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 P1 N2 C2 8.8(4) . . . . ? Cl1 P1 N2 C2 -94.3(3) . . . . ? N1 P1 N2 C13 -170.6(4) . . . . ? Cl1 P1 N2 C13 86.3(4) . . . . ? N2 P1 N1 C1 -9.1(3) . . . . ? Cl1 P1 N1 C1 91.8(3) . . . . ? N2 P1 N1 C33 176.8(4) . . . . ? Cl1 P1 N1 C33 -82.4(3) . . . . ? C13 N2 C2 C1 172.8(5) . . . . ? P1 N2 C2 C1 -6.6(5) . . . . ? C13 N2 C2 C3 -7.3(9) . . . . ? P1 N2 C2 C3 173.4(4) . . . . ? C33 N1 C1 C2 -179.2(4) . . . . ? P1 N1 C1 C2 7.0(5) . . . . ? C33 N1 C1 C12 -5.3(9) . . . . ? P1 N1 C1 C12 -179.1(5) . . . . ? N2 C2 C1 N1 0.0(6) . . . . ? C3 C2 C1 N1 -180.0(4) . . . . ? N2 C2 C1 C12 -175.9(4) . . . . ? C3 C2 C1 C12 4.1(5) . . . . ? N1 C1 C12 C8 -177.7(5) . . . . ? C2 C1 C12 C8 -3.7(5) . . . . ? N1 C1 C12 C11 4.5(11) . . . . ? C2 C1 C12 C11 178.5(5) . . . . ? C8 C12 C11 C10 2.1(7) . . . . ? C1 C12 C11 C10 179.8(5) . . . . ? C12 C11 C10 C9 -2.2(8) . . . . ? C11 C10 C9 C7 0.5(8) . . . . ? C10 C9 C7 C8 1.2(7) . . . . ? C10 C9 C7 C6 175.0(5) . . . . ? C6 C7 C8 C12 -175.4(5) . . . . ? C9 C7 C8 C12 -1.2(8) . . . . ? C6 C7 C8 C3 3.8(7) . . . . ? C9 C7 C8 C3 178.0(4) . . . . ? C11 C12 C8 C7 -0.5(7) . . . . ? C1 C12 C8 C7 -178.7(5) . . . . ? C11 C12 C8 C3 -179.7(4) . . . . ? C1 C12 C8 C3 2.0(5) . . . . ? C8 C7 C6 C5 -4.3(8) . . . . ? C9 C7 C6 C5 -177.8(5) . . . . ? C7 C6 C5 C4 5.1(8) . . . . ? C6 C5 C4 C3 -5.5(8) . . . . ? C5 C4 C3 C2 176.8(6) . . . . ? C5 C4 C3 C8 4.5(7) . . . . ? N2 C2 C3 C4 4.4(11) . . . . ? C1 C2 C3 C4 -175.6(6) . . . . ? N2 C2 C3 C8 177.3(5) . . . . ? C1 C2 C3 C8 -2.7(5) . . . . ? C7 C8 C3 C4 -3.7(7) . . . . ? C12 C8 C3 C4 175.6(4) . . . . ? C7 C8 C3 C2 -179.0(4) . . . . ? C12 C8 C3 C2 0.3(5) . . . . ? C1 N1 C33 C28 69.8(6) . . . . ? P1 N1 C33 C28 -116.8(4) . . . . ? C1 N1 C33 C32 -110.1(5) . . . . ? P1 N1 C33 C32 63.2(5) . . . . ? C28 C33 C32 C31 -1.5(7) . . . . ? N1 C33 C32 C31 178.4(4) . . . . ? C33 C32 C31 C30 1.7(7) . . . . ? C32 C31 C30 C29 -2.2(7) . . . . ? C31 C30 C29 C28 2.4(7) . . . . ? C32 C33 C28 C29 1.5(6) . . . . ? N1 C33 C28 C29 -178.4(4) . . . . ? C32 C33 C28 C27 -179.2(5) . . . . ? N1 C33 C28 C27 0.9(7) . . . . ? C30 C29 C28 C33 -2.0(7) . . . . ? C30 C29 C28 C27 178.7(5) . . . . ? C33 C28 C27 C26 98.5(5) . . . . ? C29 C28 C27 C26 -82.3(5) . . . . ? C28 C27 C26 C25 -76.4(6) . . . . ? C21 N3 C25 C24 -3.8(6) . . . . ? C21 N3 C25 C26 -177.8(4) . . . . ? C27 C26 C25 C24 110.3(6) . . . . ? C27 C26 C25 N3 -76.2(6) . . . . ? N3 C25 C24 C23 4.3(7) . . . . ? C26 C25 C24 C23 177.5(5) . . . . ? C25 C24 C23 C22 -1.3(7) . . . . ? C24 C23 C22 C21 -1.9(7) . . . . ? C25 N3 C21 C22 0.6(7) . . . . ? C25 N3 C21 C20 -179.3(4) . . . . ? C23 C22 C21 N3 2.3(7) . . . . ? C23 C22 C21 C20 -177.8(4) . . . . ? N3 C21 C20 C19 82.1(5) . . . . ? C22 C21 C20 C19 -97.8(5) . . . . ? C21 C20 C19 C18 76.4(5) . . . . ? C20 C19 C18 C17 73.0(6) . . . . ? C20 C19 C18 C13 -106.2(5) . . . . ? C13 C18 C17 C16 0.8(6) . . . . ? C19 C18 C17 C16 -178.5(4) . . . . ? C18 C17 C16 C15 -3.8(7) . . . . ? C17 C16 C15 C14 3.1(7) . . . . ? C16 C15 C14 C13 0.4(7) . . . . ? C17 C18 C13 C14 2.7(6) . . . . ? C19 C18 C13 C14 -178.1(4) . . . . ? C17 C18 C13 N2 179.0(4) . . . . ? C19 C18 C13 N2 -1.8(6) . . . . ? C15 C14 C13 C18 -3.4(6) . . . . ? C15 C14 C13 N2 -179.8(4) . . . . ? C2 N2 C13 C18 -62.3(7) . . . . ? P1 N2 C13 C18 117.0(4) . . . . ? C2 N2 C13 C14 114.0(5) . . . . ? P1 N2 C13 C14 -66.7(5) . . . . ? N4 P2 N5 C46 -177.5(4) . . . . ? Cl2 P2 N5 C46 80.8(3) . . . . ? N4 P2 N5 C35 8.9(3) . . . . ? Cl2 P2 N5 C35 -92.8(3) . . . . ? N5 P2 N4 C34 -10.8(3) . . . . ? Cl2 P2 N4 C34 91.7(3) . . . . ? N5 P2 N4 C66 173.1(4) . . . . ? Cl2 P2 N4 C66 -84.4(4) . . . . ? C46 N5 C35 C34 -178.4(4) . . . . ? P2 N5 C35 C34 -5.0(5) . . . . ? C46 N5 C35 C36 1.4(8) . . . . ? P2 N5 C35 C36 174.9(4) . . . . ? N5 C35 C34 N4 -2.8(5) . . . . ? C36 C35 C34 N4 177.4(3) . . . . ? N5 C35 C34 C45 -179.7(4) . . . . ? C36 C35 C34 C45 0.4(5) . . . . ? C66 N4 C34 C35 -173.9(4) . . . . ? P2 N4 C34 C35 9.9(5) . . . . ? C66 N4 C34 C45 1.7(8) . . . . ? P2 N4 C34 C45 -174.5(5) . . . . ? C35 C34 C45 C41 -1.4(5) . . . . ? N4 C34 C45 C41 -177.0(5) . . . . ? C35 C34 C45 C44 177.3(5) . . . . ? N4 C34 C45 C44 1.7(10) . . . . ? C41 C45 C44 C43 1.3(7) . . . . ? C34 C45 C44 C43 -177.2(5) . . . . ? C45 C44 C43 C42 -0.9(8) . . . . ? C44 C43 C42 C40 2.6(9) . . . . ? C43 C42 C40 C39 177.4(6) . . . . ? C43 C42 C40 C41 -4.3(7) . . . . ? C44 C45 C41 C40 -3.7(7) . . . . ? C34 C45 C41 C40 175.2(4) . . . . ? C44 C45 C41 C36 -177.0(4) . . . . ? C34 C45 C41 C36 1.9(5) . . . . ? C39 C40 C41 C45 -176.5(5) . . . . ? C42 C40 C41 C45 5.0(7) . . . . ? C39 C40 C41 C36 -3.9(7) . . . . ? C42 C40 C41 C36 177.7(4) . . . . ? C41 C40 C39 C38 5.8(7) . . . . ? C42 C40 C39 C38 -176.0(5) . . . . ? C40 C39 C38 C37 -1.9(7) . . . . ? C39 C38 C37 C36 -4.4(7) . . . . ? C38 C37 C36 C41 6.4(7) . . . . ? C38 C37 C36 C35 175.7(5) . . . . ? C45 C41 C36 C37 171.0(5) . . . . ? C40 C41 C36 C37 -2.5(7) . . . . ? C45 C41 C36 C35 -1.7(5) . . . . ? C40 C41 C36 C35 -175.2(4) . . . . ? C34 C35 C36 C37 -169.9(6) . . . . ? N5 C35 C36 C37 10.2(9) . . . . ? C34 C35 C36 C41 0.7(5) . . . . ? N5 C35 C36 C41 -179.1(5) . . . . ? C34 N4 C66 C61 69.1(6) . . . . ? P2 N4 C66 C61 -115.0(4) . . . . ? C34 N4 C66 C65 -116.5(5) . . . . ? P2 N4 C66 C65 59.4(5) . . . . ? C61 C66 C65 C64 0.5(7) . . . . ? N4 C66 C65 C64 -173.8(4) . . . . ? C66 C65 C64 C63 0.7(7) . . . . ? C65 C64 C63 C62 -0.3(7) . . . . ? C64 C63 C62 C61 -1.3(7) . . . . ? C63 C62 C61 C66 2.4(7) . . . . ? C63 C62 C61 C60 -179.1(4) . . . . ? C65 C66 C61 C62 -2.0(7) . . . . ? N4 C66 C61 C62 172.1(4) . . . . ? C65 C66 C61 C60 179.7(4) . . . . ? N4 C66 C61 C60 -6.2(7) . . . . ? C62 C61 C60 C59 -78.2(5) . . . . ? C66 C61 C60 C59 100.1(6) . . . . ? C61 C60 C59 C58 -67.0(6) . . . . ? C54 N6 C58 C57 1.9(6) . . . . ? C54 N6 C58 C59 -172.7(4) . . . . ? C60 C59 C58 C57 107.0(5) . . . . ? C60 C59 C58 N6 -78.5(5) . . . . ? N6 C58 C57 C56 -1.4(7) . . . . ? C59 C58 C57 C56 172.8(5) . . . . ? C58 C57 C56 C55 1.1(7) . . . . ? C57 C56 C55 C54 -1.4(7) . . . . ? C58 N6 C54 C55 -2.2(6) . . . . ? C58 N6 C54 C53 177.7(4) . . . . ? C56 C55 C54 N6 2.0(7) . . . . ? C56 C55 C54 C53 -177.9(5) . . . . ? N6 C54 C53 C52 67.7(5) . . . . ? C55 C54 C53 C52 -112.4(5) . . . . ? C54 C53 C52 C51 80.8(5) . . . . ? C53 C52 C51 C50 77.9(5) . . . . ? C53 C52 C51 C46 -100.8(5) . . . . ? C46 C51 C50 C49 0.2(7) . . . . ? C52 C51 C50 C49 -178.6(4) . . . . ? C51 C50 C49 C48 1.6(8) . . . . ? C50 C49 C48 C47 -3.3(8) . . . . ? C49 C48 C47 C46 3.2(7) . . . . ? C48 C47 C46 N5 176.2(4) . . . . ? C48 C47 C46 C51 -1.4(7) . . . . ? C35 N5 C46 C47 112.3(5) . . . . ? P2 N5 C46 C47 -60.4(5) . . . . ? C35 N5 C46 C51 -70.0(6) . . . . ? P2 N5 C46 C51 117.2(4) . . . . ? C50 C51 C46 C47 -0.3(7) . . . . ? C52 C51 C46 C47 178.5(4) . . . . ? C50 C51 C46 N5 -177.9(4) . . . . ? C52 C51 C46 N5 0.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.86 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.798 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.069 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 -0.016 0.250 -0.049 831 294 ' ' 2 0.007 -0.250 0.451 831 294 ' ' _platon_squeeze_details ; ; data_4Sb _database_code_depnum_ccdc_archive 'CCDC 864991' #TrackingRef '- CIF_Ragogna_clamshell.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 Cl3 N3 Sb, C H2 Cl2' _chemical_formula_sum 'C34 H27 Cl5 N3 Sb' _chemical_formula_weight 776.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.222(2) _cell_length_b 11.568(2) _cell_length_c 14.686(3) _cell_angle_alpha 101.08(3) _cell_angle_beta 91.95(3) _cell_angle_gamma 108.62(3) _cell_volume 1606.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6935 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 1.304 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7363 _exptl_absorpt_correction_T_max 0.7713 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13445 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.64 _reflns_number_total 7397 _reflns_number_gt 6485 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0646P)^2^+1.1749P] 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 7397 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.97026(2) 0.150419(17) 0.280348(14) 0.01870(8) Uani 1 1 d . . . Cl2 Cl 0.97483(8) 0.24716(7) 0.43948(5) 0.02419(17) Uani 1 1 d . . . Cl3 Cl 0.90211(9) -0.05468(7) 0.32193(6) 0.02743(18) Uani 1 1 d . . . Cl1 Cl 0.73128(11) 0.16516(11) 0.25638(7) 0.0472(3) Uani 1 1 d . . . N1 N 1.1300(3) 0.3750(2) 0.28756(18) 0.0196(5) Uani 1 1 d . . . C33 C 1.0859(3) 0.4714(3) 0.2624(2) 0.0203(6) Uani 1 1 d . . . C18 C 1.3206(3) 0.0200(3) 0.2968(2) 0.0218(6) Uani 1 1 d . . . N2 N 1.2093(3) 0.1807(2) 0.33731(18) 0.0182(5) Uani 1 1 d . . . C2 C 1.2981(3) 0.2912(3) 0.3460(2) 0.0175(6) Uani 1 1 d . . . C1 C 1.2568(3) 0.3947(3) 0.3160(2) 0.0187(6) Uani 1 1 d . . . C13 C 1.2569(3) 0.0842(3) 0.3615(2) 0.0200(6) Uani 1 1 d . . . C15 C 1.2901(4) -0.0286(3) 0.4766(2) 0.0245(7) Uani 1 1 d . . . H15A H 1.2809 -0.0441 0.5376 0.029 Uiso 1 1 calc R . . C28 C 1.0356(4) 0.4588(3) 0.1698(2) 0.0247(7) Uani 1 1 d . . . C8 C 1.4917(3) 0.4672(3) 0.3640(2) 0.0202(6) Uani 1 1 d . . . C7 C 1.6302(3) 0.5447(3) 0.3824(2) 0.0237(7) Uani 1 1 d . . . C19 C 1.3388(4) 0.0467(3) 0.2005(2) 0.0245(7) Uani 1 1 d . . . H19A H 1.4125 0.0160 0.1744 0.029 Uiso 1 1 calc R . . H19B H 1.3699 0.1382 0.2056 0.029 Uiso 1 1 calc R . . C3 C 1.4462(3) 0.3429(3) 0.3783(2) 0.0194(6) Uani 1 1 d . . . N3 N 1.1908(3) 0.1693(3) 0.0851(2) 0.0279(6) Uani 1 1 d . . . C32 C 1.0853(4) 0.5719(3) 0.3314(2) 0.0239(7) Uani 1 1 d . . . H32A H 1.1162 0.5773 0.3943 0.029 Uiso 1 1 calc R . . C31 C 1.0394(4) 0.6644(3) 0.3083(3) 0.0270(7) Uani 1 1 d . . . H31A H 1.0406 0.7341 0.3551 0.032 Uiso 1 1 calc R . . C11 C 1.4187(4) 0.6180(3) 0.3027(3) 0.0256(7) Uani 1 1 d . . . H11A H 1.3496 0.6442 0.2766 0.031 Uiso 1 1 calc R . . C5 C 1.6802(4) 0.3758(3) 0.4357(2) 0.0256(7) Uani 1 1 d . . . H5A H 1.7456 0.3454 0.4618 0.031 Uiso 1 1 calc R . . C14 C 1.2377(3) 0.0583(3) 0.4494(2) 0.0223(6) Uani 1 1 d . . . H14A H 1.1892 0.0996 0.4908 0.027 Uiso 1 1 calc R . . C22 C 1.2498(4) 0.0230(3) -0.0306(2) 0.0305(8) Uani 1 1 d . . . H22A H 1.2636 -0.0553 -0.0487 0.037 Uiso 1 1 calc R . . C21 C 1.2120(4) 0.0588(3) 0.0575(2) 0.0271(7) Uani 1 1 d . . . C25 C 1.2075(4) 0.2460(3) 0.0256(2) 0.0264(7) Uani 1 1 d . . . C12 C 1.3852(3) 0.5021(3) 0.3255(2) 0.0205(6) Uani 1 1 d . . . C16 C 1.3555(4) -0.0925(3) 0.4145(3) 0.0274(7) Uani 1 1 d . . . H16A H 1.3905 -0.1525 0.4325 0.033 Uiso 1 1 calc R . . C4 C 1.5405(3) 0.2972(3) 0.4144(2) 0.0220(6) Uani 1 1 d . . . H4A H 1.5124 0.2146 0.4248 0.026 Uiso 1 1 calc R . . C9 C 1.6614(4) 0.6621(3) 0.3582(3) 0.0297(8) Uani 1 1 d . . . H9A H 1.7543 0.7180 0.3687 0.036 Uiso 1 1 calc R . . C10 C 1.5596(4) 0.6964(3) 0.3197(3) 0.0323(8) Uani 1 1 d . . . H10A H 1.5842 0.7758 0.3037 0.039 Uiso 1 1 calc R . . C6 C 1.7247(4) 0.4950(3) 0.4199(2) 0.0268(7) Uani 1 1 d . . . H6A H 1.8198 0.5446 0.4343 0.032 Uiso 1 1 calc R . . C30 C 0.9922(4) 0.6548(3) 0.2170(3) 0.0330(8) Uani 1 1 d . . . H30A H 0.9614 0.7182 0.2008 0.040 Uiso 1 1 calc R . . C27 C 1.0387(4) 0.3497(3) 0.0954(2) 0.0271(7) Uani 1 1 d . . . H27A H 0.9734 0.3394 0.0407 0.033 Uiso 1 1 calc R . . H27B H 1.0076 0.2723 0.1198 0.033 Uiso 1 1 calc R . . C20 C 1.2054(4) -0.0140(3) 0.1328(2) 0.0262(7) Uani 1 1 d . . . H20A H 1.1963 -0.1015 0.1046 0.031 Uiso 1 1 calc R . . H20B H 1.1235 -0.0145 0.1670 0.031 Uiso 1 1 calc R . . C26 C 1.1851(4) 0.3689(3) 0.0646(2) 0.0287(8) Uani 1 1 d . . . H26A H 1.1996 0.4197 0.0164 0.034 Uiso 1 1 calc R . . H26B H 1.2547 0.4156 0.1186 0.034 Uiso 1 1 calc R . . C17 C 1.3696(4) -0.0679(3) 0.3255(2) 0.0263(7) Uani 1 1 d . . . H17A H 1.4139 -0.1124 0.2831 0.032 Uiso 1 1 calc R . . C29 C 0.9897(4) 0.5521(4) 0.1488(3) 0.0330(8) Uani 1 1 d . . . H29A H 0.9558 0.5459 0.0864 0.040 Uiso 1 1 calc R . . C24 C 1.2457(4) 0.2170(4) -0.0630(2) 0.0332(8) Uani 1 1 d . . . H24A H 1.2571 0.2736 -0.1036 0.040 Uiso 1 1 calc R . . C23 C 1.2673(4) 0.1028(4) -0.0917(2) 0.0346(9) Uani 1 1 d . . . H23A H 1.2936 0.0803 -0.1522 0.042 Uiso 1 1 calc R . . Cl6 Cl 0.33820(15) 0.71060(12) 0.03314(10) 0.0621(3) Uani 1 1 d . . . Cl5 Cl 0.42501(16) 0.55904(14) -0.11881(11) 0.0716(4) Uani 1 1 d . . . C34 C 0.4066(6) 0.7051(5) -0.0754(4) 0.0593(13) Uani 1 1 d . . . H34A H 0.3443 0.7216 -0.1206 0.071 Uiso 1 1 calc R . . H34B H 0.4983 0.7713 -0.0685 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.01819(12) 0.01622(12) 0.02060(12) 0.00333(8) 0.00046(8) 0.00474(8) Cl2 0.0222(4) 0.0258(4) 0.0206(4) 0.0010(3) 0.0019(3) 0.0049(3) Cl3 0.0319(4) 0.0175(4) 0.0310(4) 0.0079(3) 0.0039(3) 0.0039(3) Cl1 0.0340(5) 0.0688(7) 0.0368(5) -0.0191(5) -0.0124(4) 0.0336(5) N1 0.0211(14) 0.0195(13) 0.0204(13) 0.0052(10) 0.0011(10) 0.0092(11) C33 0.0176(15) 0.0189(14) 0.0262(16) 0.0096(12) 0.0016(12) 0.0060(12) C18 0.0217(16) 0.0175(14) 0.0255(17) 0.0063(12) 0.0004(13) 0.0051(12) N2 0.0175(13) 0.0167(12) 0.0219(13) 0.0068(10) 0.0022(10) 0.0062(10) C2 0.0188(15) 0.0182(14) 0.0174(14) 0.0053(11) 0.0025(11) 0.0078(12) C1 0.0223(16) 0.0168(14) 0.0190(15) 0.0053(11) 0.0037(12) 0.0082(12) C13 0.0186(15) 0.0139(14) 0.0279(17) 0.0078(12) 0.0014(12) 0.0041(12) C15 0.0239(17) 0.0233(16) 0.0276(17) 0.0124(13) 0.0005(13) 0.0057(13) C28 0.0250(17) 0.0264(17) 0.0255(17) 0.0085(13) 0.0017(13) 0.0105(14) C8 0.0192(16) 0.0196(15) 0.0210(15) 0.0021(12) 0.0037(12) 0.0065(12) C7 0.0166(16) 0.0210(15) 0.0290(17) -0.0011(13) 0.0033(13) 0.0038(13) C19 0.0258(17) 0.0265(16) 0.0248(17) 0.0071(13) 0.0055(13) 0.0123(14) C3 0.0164(15) 0.0188(14) 0.0213(15) 0.0027(12) 0.0013(12) 0.0045(12) N3 0.0370(17) 0.0271(15) 0.0240(15) 0.0048(12) 0.0034(12) 0.0169(13) C32 0.0242(17) 0.0242(16) 0.0238(16) 0.0050(13) -0.0005(13) 0.0092(13) C31 0.0275(18) 0.0230(16) 0.0344(19) 0.0062(14) 0.0047(14) 0.0134(14) C11 0.0234(17) 0.0211(16) 0.0348(19) 0.0099(14) 0.0066(14) 0.0083(13) C5 0.0197(16) 0.0282(17) 0.0278(17) 0.0019(13) -0.0045(13) 0.0094(14) C14 0.0220(16) 0.0201(15) 0.0241(16) 0.0065(12) 0.0033(13) 0.0051(13) C22 0.043(2) 0.0260(17) 0.0234(17) -0.0011(13) -0.0012(15) 0.0163(16) C21 0.0317(19) 0.0254(17) 0.0248(17) 0.0020(13) -0.0006(14) 0.0124(15) C25 0.0290(18) 0.0281(17) 0.0231(17) 0.0065(13) 0.0013(14) 0.0103(15) C12 0.0192(16) 0.0170(14) 0.0253(16) 0.0057(12) 0.0039(12) 0.0050(12) C16 0.0264(18) 0.0225(16) 0.037(2) 0.0118(14) -0.0014(15) 0.0101(14) C4 0.0218(16) 0.0215(15) 0.0232(16) 0.0039(12) -0.0006(13) 0.0088(13) C9 0.0203(17) 0.0184(15) 0.045(2) 0.0031(14) 0.0082(15) 0.0010(13) C10 0.031(2) 0.0165(15) 0.049(2) 0.0100(15) 0.0121(17) 0.0056(14) C6 0.0164(16) 0.0270(17) 0.0308(18) -0.0013(14) -0.0004(13) 0.0030(13) C30 0.040(2) 0.0315(19) 0.037(2) 0.0123(16) 0.0054(17) 0.0230(17) C27 0.0316(19) 0.0308(18) 0.0230(17) 0.0083(14) -0.0012(14) 0.0148(15) C20 0.0335(19) 0.0214(16) 0.0248(17) 0.0023(13) 0.0002(14) 0.0124(14) C26 0.040(2) 0.0275(17) 0.0258(18) 0.0099(14) 0.0069(15) 0.0179(16) C17 0.0291(18) 0.0223(16) 0.0302(18) 0.0058(13) 0.0019(14) 0.0122(14) C29 0.041(2) 0.036(2) 0.0296(19) 0.0127(15) -0.0015(16) 0.0201(17) C24 0.044(2) 0.036(2) 0.0215(17) 0.0071(15) 0.0003(16) 0.0155(18) C23 0.047(2) 0.037(2) 0.0179(17) -0.0017(14) -0.0005(15) 0.0170(18) Cl6 0.0591(8) 0.0552(7) 0.0718(9) 0.0007(6) 0.0171(7) 0.0249(6) Cl5 0.0624(9) 0.0726(9) 0.0696(9) -0.0085(7) 0.0194(7) 0.0209(7) C34 0.059(3) 0.062(3) 0.063(3) 0.026(3) 0.006(3) 0.021(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 Cl2 2.3813(10) . ? Sb1 N2 2.449(3) . ? Sb1 Cl3 2.4531(10) . ? Sb1 Cl1 2.5202(11) . ? Sb1 N1 2.570(3) . ? N1 C1 1.282(4) . ? N1 C33 1.432(4) . ? C33 C32 1.390(5) . ? C33 C28 1.401(5) . ? C18 C17 1.392(4) . ? C18 C13 1.399(5) . ? C18 C19 1.509(5) . ? N2 C2 1.290(4) . ? N2 C13 1.448(4) . ? C2 C3 1.463(4) . ? C2 C1 1.522(4) . ? C1 C12 1.472(4) . ? C13 C14 1.387(4) . ? C15 C16 1.387(5) . ? C15 C14 1.393(5) . ? C15 H15A 0.9500 . ? C28 C29 1.386(5) . ? C28 C27 1.513(5) . ? C8 C7 1.398(4) . ? C8 C12 1.412(5) . ? C8 C3 1.422(4) . ? C7 C9 1.411(5) . ? C7 C6 1.416(5) . ? C19 C20 1.539(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C3 C4 1.375(4) . ? N3 C25 1.339(4) . ? N3 C21 1.352(4) . ? C32 C31 1.389(5) . ? C32 H32A 0.9500 . ? C31 C30 1.381(5) . ? C31 H31A 0.9500 . ? C11 C12 1.383(4) . ? C11 C10 1.419(5) . ? C11 H11A 0.9500 . ? C5 C6 1.376(5) . ? C5 C4 1.412(5) . ? C5 H5A 0.9500 . ? C14 H14A 0.9500 . ? C22 C23 1.383(5) . ? C22 C21 1.387(5) . ? C22 H22A 0.9500 . ? C21 C20 1.505(5) . ? C25 C24 1.382(5) . ? C25 C26 1.517(5) . ? C16 C17 1.392(5) . ? C16 H16A 0.9500 . ? C4 H4A 0.9500 . ? C9 C10 1.367(5) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C6 H6A 0.9500 . ? C30 C29 1.391(5) . ? C30 H30A 0.9500 . ? C27 C26 1.539(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C17 H17A 0.9500 . ? C29 H29A 0.9500 . ? C24 C23 1.396(5) . ? C24 H24A 0.9500 . ? C23 H23A 0.9500 . ? Cl6 C34 1.760(6) . ? Cl5 C34 1.759(6) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? 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 Cl2 Sb1 N2 79.63(7) . . ? Cl2 Sb1 Cl3 89.88(4) . . ? N2 Sb1 Cl3 87.94(7) . . ? Cl2 Sb1 Cl1 86.96(4) . . ? N2 Sb1 Cl1 165.31(7) . . ? Cl3 Sb1 Cl1 98.08(5) . . ? Cl2 Sb1 N1 77.83(7) . . ? N2 Sb1 N1 68.57(9) . . ? Cl3 Sb1 N1 154.96(6) . . ? Cl1 Sb1 N1 102.89(7) . . ? C1 N1 C33 121.7(3) . . ? C1 N1 Sb1 113.5(2) . . ? C33 N1 Sb1 124.8(2) . . ? C32 C33 C28 121.0(3) . . ? C32 C33 N1 119.3(3) . . ? C28 C33 N1 119.5(3) . . ? C17 C18 C13 117.2(3) . . ? C17 C18 C19 121.1(3) . . ? C13 C18 C19 121.6(3) . . ? C2 N2 C13 118.4(3) . . ? C2 N2 Sb1 116.8(2) . . ? C13 N2 Sb1 124.81(19) . . ? N2 C2 C3 131.7(3) . . ? N2 C2 C1 121.0(3) . . ? C3 C2 C1 107.2(3) . . ? N1 C1 C12 133.6(3) . . ? N1 C1 C2 120.0(3) . . ? C12 C1 C2 106.4(3) . . ? C14 C13 C18 121.8(3) . . ? C14 C13 N2 118.3(3) . . ? C18 C13 N2 119.9(3) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C29 C28 C33 117.8(3) . . ? C29 C28 C27 121.8(3) . . ? C33 C28 C27 120.3(3) . . ? C7 C8 C12 123.5(3) . . ? C7 C8 C3 122.7(3) . . ? C12 C8 C3 113.7(3) . . ? C8 C7 C9 116.3(3) . . ? C8 C7 C6 116.5(3) . . ? C9 C7 C6 127.1(3) . . ? C18 C19 C20 113.3(3) . . ? C18 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? C18 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C4 C3 C8 119.3(3) . . ? C4 C3 C2 134.6(3) . . ? C8 C3 C2 106.1(3) . . ? C25 N3 C21 118.8(3) . . ? C31 C32 C33 119.9(3) . . ? C31 C32 H32A 120.1 . . ? C33 C32 H32A 120.1 . . ? C30 C31 C32 119.8(3) . . ? C30 C31 H31A 120.1 . . ? C32 C31 H31A 120.1 . . ? C12 C11 C10 117.9(3) . . ? C12 C11 H11A 121.1 . . ? C10 C11 H11A 121.1 . . ? C6 C5 C4 122.2(3) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C13 C14 C15 119.5(3) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C23 C22 C21 119.2(3) . . ? C23 C22 H22A 120.4 . . ? C21 C22 H22A 120.4 . . ? N3 C21 C22 121.8(3) . . ? N3 C21 C20 114.4(3) . . ? C22 C21 C20 123.5(3) . . ? N3 C25 C24 122.6(3) . . ? N3 C25 C26 114.5(3) . . ? C24 C25 C26 122.9(3) . . ? C11 C12 C8 119.0(3) . . ? C11 C12 C1 134.5(3) . . ? C8 C12 C1 106.5(3) . . ? C15 C16 C17 119.4(3) . . ? C15 C16 H16A 120.3 . . ? C17 C16 H16A 120.3 . . ? C3 C4 C5 118.5(3) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? C10 C9 C7 120.8(3) . . ? C10 C9 H9A 119.6 . . ? C7 C9 H9A 119.6 . . ? C9 C10 C11 122.6(3) . . ? C9 C10 H10A 118.7 . . ? C11 C10 H10A 118.7 . . ? C5 C6 C7 120.7(3) . . ? C5 C6 H6A 119.6 . . ? C7 C6 H6A 119.6 . . ? C31 C30 C29 119.9(3) . . ? C31 C30 H30A 120.1 . . ? C29 C30 H30A 120.1 . . ? C28 C27 C26 111.6(3) . . ? C28 C27 H27A 109.3 . . ? C26 C27 H27A 109.3 . . ? C28 C27 H27B 109.3 . . ? C26 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? C21 C20 C19 109.2(3) . . ? C21 C20 H20A 109.8 . . ? C19 C20 H20A 109.8 . . ? C21 C20 H20B 109.8 . . ? C19 C20 H20B 109.8 . . ? H20A C20 H20B 108.3 . . ? C25 C26 C27 112.2(3) . . ? C25 C26 H26A 109.2 . . ? C27 C26 H26A 109.2 . . ? C25 C26 H26B 109.2 . . ? C27 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C18 C17 C16 122.0(3) . . ? C18 C17 H17A 119.0 . . ? C16 C17 H17A 119.0 . . ? C28 C29 C30 121.6(3) . . ? C28 C29 H29A 119.2 . . ? C30 C29 H29A 119.2 . . ? C25 C24 C23 118.6(3) . . ? C25 C24 H24A 120.7 . . ? C23 C24 H24A 120.7 . . ? C22 C23 C24 119.0(3) . . ? C22 C23 H23A 120.5 . . ? C24 C23 H23A 120.5 . . ? Cl5 C34 Cl6 111.5(3) . . ? Cl5 C34 H34A 109.3 . . ? Cl6 C34 H34A 109.3 . . ? Cl5 C34 H34B 109.3 . . ? Cl6 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Sb1 N1 C1 84.3(2) . . . . ? N2 Sb1 N1 C1 0.8(2) . . . . ? Cl3 Sb1 N1 C1 22.1(3) . . . . ? Cl1 Sb1 N1 C1 168.2(2) . . . . ? Cl2 Sb1 N1 C33 -96.0(2) . . . . ? N2 Sb1 N1 C33 -179.5(3) . . . . ? Cl3 Sb1 N1 C33 -158.22(18) . . . . ? Cl1 Sb1 N1 C33 -12.1(2) . . . . ? C1 N1 C33 C32 -68.9(4) . . . . ? Sb1 N1 C33 C32 111.4(3) . . . . ? C1 N1 C33 C28 115.3(4) . . . . ? Sb1 N1 C33 C28 -64.4(4) . . . . ? Cl2 Sb1 N2 C2 -79.2(2) . . . . ? Cl3 Sb1 N2 C2 -169.4(2) . . . . ? Cl1 Sb1 N2 C2 -54.8(4) . . . . ? N1 Sb1 N2 C2 1.7(2) . . . . ? Cl2 Sb1 N2 C13 100.8(2) . . . . ? Cl3 Sb1 N2 C13 10.6(2) . . . . ? Cl1 Sb1 N2 C13 125.2(3) . . . . ? N1 Sb1 N2 C13 -178.3(3) . . . . ? C13 N2 C2 C3 -0.8(5) . . . . ? Sb1 N2 C2 C3 179.2(3) . . . . ? C13 N2 C2 C1 176.1(3) . . . . ? Sb1 N2 C2 C1 -3.9(4) . . . . ? C33 N1 C1 C12 -4.6(6) . . . . ? Sb1 N1 C1 C12 175.1(3) . . . . ? C33 N1 C1 C2 177.4(3) . . . . ? Sb1 N1 C1 C2 -2.9(4) . . . . ? N2 C2 C1 N1 4.8(5) . . . . ? C3 C2 C1 N1 -177.6(3) . . . . ? N2 C2 C1 C12 -173.6(3) . . . . ? C3 C2 C1 C12 3.9(3) . . . . ? C17 C18 C13 C14 -2.7(5) . . . . ? C19 C18 C13 C14 178.8(3) . . . . ? C17 C18 C13 N2 177.2(3) . . . . ? C19 C18 C13 N2 -1.3(5) . . . . ? C2 N2 C13 C14 97.2(4) . . . . ? Sb1 N2 C13 C14 -82.8(3) . . . . ? C2 N2 C13 C18 -82.7(4) . . . . ? Sb1 N2 C13 C18 97.3(3) . . . . ? C32 C33 C28 C29 2.2(5) . . . . ? N1 C33 C28 C29 177.9(3) . . . . ? C32 C33 C28 C27 179.2(3) . . . . ? N1 C33 C28 C27 -5.1(5) . . . . ? C12 C8 C7 C9 -1.5(5) . . . . ? C3 C8 C7 C9 175.4(3) . . . . ? C12 C8 C7 C6 -179.2(3) . . . . ? C3 C8 C7 C6 -2.3(5) . . . . ? C17 C18 C19 C20 103.0(4) . . . . ? C13 C18 C19 C20 -78.5(4) . . . . ? C7 C8 C3 C4 2.1(5) . . . . ? C12 C8 C3 C4 179.2(3) . . . . ? C7 C8 C3 C2 -176.7(3) . . . . ? C12 C8 C3 C2 0.5(4) . . . . ? N2 C2 C3 C4 -4.0(6) . . . . ? C1 C2 C3 C4 178.8(4) . . . . ? N2 C2 C3 C8 174.5(3) . . . . ? C1 C2 C3 C8 -2.7(3) . . . . ? C28 C33 C32 C31 -2.7(5) . . . . ? N1 C33 C32 C31 -178.4(3) . . . . ? C33 C32 C31 C30 1.2(5) . . . . ? C18 C13 C14 C15 3.8(5) . . . . ? N2 C13 C14 C15 -176.1(3) . . . . ? C16 C15 C14 C13 -2.8(5) . . . . ? C25 N3 C21 C22 -0.2(5) . . . . ? C25 N3 C21 C20 173.8(3) . . . . ? C23 C22 C21 N3 0.4(6) . . . . ? C23 C22 C21 C20 -173.1(4) . . . . ? C21 N3 C25 C24 -0.1(5) . . . . ? C21 N3 C25 C26 -178.4(3) . . . . ? C10 C11 C12 C8 -0.2(5) . . . . ? C10 C11 C12 C1 -177.3(3) . . . . ? C7 C8 C12 C11 1.3(5) . . . . ? C3 C8 C12 C11 -175.8(3) . . . . ? C7 C8 C12 C1 179.1(3) . . . . ? C3 C8 C12 C1 2.0(4) . . . . ? N1 C1 C12 C11 -4.4(7) . . . . ? C2 C1 C12 C11 173.7(4) . . . . ? N1 C1 C12 C8 178.2(3) . . . . ? C2 C1 C12 C8 -3.6(3) . . . . ? C14 C15 C16 C17 0.7(5) . . . . ? C8 C3 C4 C5 -0.3(5) . . . . ? C2 C3 C4 C5 178.0(3) . . . . ? C6 C5 C4 C3 -1.2(5) . . . . ? C8 C7 C9 C10 0.5(5) . . . . ? C6 C7 C9 C10 178.0(4) . . . . ? C7 C9 C10 C11 0.5(6) . . . . ? C12 C11 C10 C9 -0.7(6) . . . . ? C4 C5 C6 C7 0.9(5) . . . . ? C8 C7 C6 C5 0.8(5) . . . . ? C9 C7 C6 C5 -176.6(3) . . . . ? C32 C31 C30 C29 0.5(6) . . . . ? C29 C28 C27 C26 99.4(4) . . . . ? C33 C28 C27 C26 -77.4(4) . . . . ? N3 C21 C20 C19 -74.7(4) . . . . ? C22 C21 C20 C19 99.2(4) . . . . ? C18 C19 C20 C21 155.3(3) . . . . ? N3 C25 C26 C27 -59.0(4) . . . . ? C24 C25 C26 C27 122.8(4) . . . . ? C28 C27 C26 C25 154.7(3) . . . . ? C13 C18 C17 C16 0.5(5) . . . . ? C19 C18 C17 C16 179.0(3) . . . . ? C15 C16 C17 C18 0.5(5) . . . . ? C33 C28 C29 C30 -0.5(6) . . . . ? C27 C28 C29 C30 -177.4(4) . . . . ? C31 C30 C29 C28 -0.9(6) . . . . ? N3 C25 C24 C23 0.2(6) . . . . ? C26 C25 C24 C23 178.4(4) . . . . ? C21 C22 C23 C24 -0.3(6) . . . . ? C25 C24 C23 C22 0.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.64 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.752 _refine_diff_density_min -1.103 _refine_diff_density_rms 0.164 data_4Bi _database_code_depnum_ccdc_archive 'CCDC 864992' #TrackingRef '- CIF_Ragogna_clamshell.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 Bi Cl3 N3, C2 H3 N' _chemical_formula_sum 'C35 H28 Bi Cl3 N4' _chemical_formula_weight 819.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall -P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 15.192(3) _cell_length_b 18.558(4) _cell_length_c 22.275(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6280(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7889 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.734 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3200 _exptl_absorpt_coefficient_mu 5.902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3316 _exptl_absorpt_correction_T_max 0.3848 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13718 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7195 _reflns_number_gt 5048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0922P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7195 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1367 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.024 _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 0.403032(13) 0.183289(12) 0.405424(10) 0.02379(10) Uani 1 1 d . . . Cl3 Cl 0.45647(10) 0.22081(9) 0.50835(7) 0.0375(4) Uani 1 1 d . . . Cl2 Cl 0.49273(11) 0.07046(8) 0.41177(8) 0.0406(4) Uani 1 1 d . . . Cl1 Cl 0.52658(10) 0.23771(8) 0.33561(8) 0.0407(4) Uani 1 1 d . . . N2 N 0.2886(3) 0.1031(2) 0.4549(2) 0.0251(10) Uani 1 1 d . . . N1 N 0.3085(3) 0.1052(3) 0.3296(2) 0.0267(11) Uani 1 1 d . . . N3 N 0.2476(3) 0.2859(3) 0.3977(2) 0.0260(11) Uani 1 1 d . . . C2 C 0.2408(4) 0.0624(3) 0.4220(3) 0.0268(13) Uani 1 1 d . . . C1 C 0.2487(3) 0.0659(3) 0.3541(3) 0.0244(12) Uani 1 1 d . . . C12 C 0.1801(3) 0.0187(3) 0.3296(3) 0.0252(12) Uani 1 1 d . . . C11 C 0.1511(4) 0.0022(3) 0.2732(3) 0.0304(13) Uani 1 1 d . . . H11A H 0.1770 0.0241 0.2390 0.036 Uiso 1 1 calc R . . C10 C 0.0822(4) -0.0479(3) 0.2665(3) 0.0322(14) Uani 1 1 d . . . H10A H 0.0616 -0.0589 0.2273 0.039 Uiso 1 1 calc R . . C9 C 0.0438(4) -0.0814(3) 0.3150(3) 0.0354(15) Uani 1 1 d . . . H9A H -0.0018 -0.1156 0.3087 0.042 Uiso 1 1 calc R . . C7 C 0.0713(4) -0.0656(3) 0.3741(3) 0.0289(13) Uani 1 1 d . . . C8 C 0.1397(4) -0.0150(3) 0.3801(3) 0.0259(12) Uani 1 1 d . . . C6 C 0.0377(4) -0.0937(3) 0.4280(3) 0.0327(14) Uani 1 1 d . . . H6A H -0.0077 -0.1288 0.4267 0.039 Uiso 1 1 calc R . . C5 C 0.0697(4) -0.0710(3) 0.4827(3) 0.0337(14) Uani 1 1 d . . . H5A H 0.0457 -0.0911 0.5184 0.040 Uiso 1 1 calc R . . C4 C 0.1367(4) -0.0190(3) 0.4874(3) 0.0284(13) Uani 1 1 d . . . H4A H 0.1571 -0.0036 0.5256 0.034 Uiso 1 1 calc R . . C3 C 0.1721(3) 0.0092(3) 0.4355(3) 0.0258(12) Uani 1 1 d . . . C33 C 0.3135(3) 0.1078(3) 0.2651(2) 0.0246(12) Uani 1 1 d . . . C32 C 0.3688(4) 0.0599(3) 0.2353(3) 0.0293(13) Uani 1 1 d . . . H32A H 0.4042 0.0267 0.2570 0.035 Uiso 1 1 calc R . . C31 C 0.3711(4) 0.0618(3) 0.1732(3) 0.0345(15) Uani 1 1 d . . . H31A H 0.4079 0.0291 0.1521 0.041 Uiso 1 1 calc R . . C30 C 0.3211(4) 0.1101(3) 0.1418(3) 0.0354(15) Uani 1 1 d . . . H30A H 0.3220 0.1097 0.0992 0.042 Uiso 1 1 calc R . . C29 C 0.2685(4) 0.1600(3) 0.1723(3) 0.0303(13) Uani 1 1 d . . . H29A H 0.2351 0.1942 0.1501 0.036 Uiso 1 1 calc R . . C28 C 0.2646(4) 0.1603(3) 0.2348(3) 0.0271(13) Uani 1 1 d . . . C27 C 0.2132(4) 0.2160(3) 0.2689(3) 0.0300(13) Uani 1 1 d . . . H27B H 0.1844 0.1929 0.3039 0.036 Uiso 1 1 calc R . . H27A H 0.1664 0.2357 0.2427 0.036 Uiso 1 1 calc R . . C26 C 0.2720(4) 0.2782(3) 0.2910(3) 0.0282(13) Uani 1 1 d . . . H26B H 0.3303 0.2590 0.3026 0.034 Uiso 1 1 calc R . . H26A H 0.2808 0.3132 0.2580 0.034 Uiso 1 1 calc R . . C25 C 0.2316(4) 0.3156(3) 0.3435(3) 0.0269(13) Uani 1 1 d . . . C24 C 0.1759(4) 0.3742(3) 0.3362(3) 0.0313(13) Uani 1 1 d . . . H24A H 0.1668 0.3946 0.2976 0.038 Uiso 1 1 calc R . . C23 C 0.1343(4) 0.4023(3) 0.3856(3) 0.0345(14) Uani 1 1 d . . . H23A H 0.0958 0.4423 0.3815 0.041 Uiso 1 1 calc R . . C22 C 0.1489(4) 0.3720(3) 0.4416(3) 0.0322(14) Uani 1 1 d . . . H22A H 0.1201 0.3906 0.4761 0.039 Uiso 1 1 calc R . . C21 C 0.2062(4) 0.3139(3) 0.4467(3) 0.0261(13) Uani 1 1 d . . . C20 C 0.2235(4) 0.2772(3) 0.5050(3) 0.0306(13) Uani 1 1 d . . . H20B H 0.2073 0.3101 0.5382 0.037 Uiso 1 1 calc R . . H20A H 0.2874 0.2671 0.5083 0.037 Uiso 1 1 calc R . . C19 C 0.1719(4) 0.2054(3) 0.5123(3) 0.0297(13) Uani 1 1 d . . . H19B H 0.1154 0.2153 0.5329 0.036 Uiso 1 1 calc R . . H19A H 0.1581 0.1858 0.4721 0.036 Uiso 1 1 calc R . . C18 C 0.2222(3) 0.1494(3) 0.5476(3) 0.0278(13) Uani 1 1 d . . . C17 C 0.2154(4) 0.1438(3) 0.6095(3) 0.0301(13) Uani 1 1 d . . . H17A H 0.1769 0.1754 0.6304 0.036 Uiso 1 1 calc R . . C16 C 0.2635(4) 0.0932(3) 0.6418(3) 0.0368(15) Uani 1 1 d . . . H16A H 0.2564 0.0900 0.6841 0.044 Uiso 1 1 calc R . . C15 C 0.3212(4) 0.0477(3) 0.6131(3) 0.0354(15) Uani 1 1 d . . . H15A H 0.3550 0.0141 0.6354 0.043 Uiso 1 1 calc R . . C14 C 0.3295(4) 0.0513(3) 0.5512(3) 0.0285(13) Uani 1 1 d . . . H14A H 0.3694 0.0204 0.5309 0.034 Uiso 1 1 calc R . . C13 C 0.2792(3) 0.1005(3) 0.5190(2) 0.0249(12) Uani 1 1 d . . . N100 N 0.0587(4) 0.1531(4) 0.3818(3) 0.0478(15) Uani 1 1 d . . . C100 C 0.0203(4) 0.1995(4) 0.3607(3) 0.0385(16) Uani 1 1 d . . . C101 C -0.0287(5) 0.2582(4) 0.3328(3) 0.053(2) Uani 1 1 d . . . H10B H -0.0205 0.2564 0.2892 0.079 Uiso 1 1 calc R . . H10C H -0.0070 0.3044 0.3482 0.079 Uiso 1 1 calc R . . H10D H -0.0914 0.2533 0.3422 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.01977(14) 0.02660(15) 0.02499(15) 0.00080(9) -0.00076(8) -0.00107(8) Cl3 0.0315(8) 0.0486(9) 0.0323(9) -0.0030(7) -0.0041(7) -0.0058(7) Cl2 0.0320(8) 0.0316(8) 0.0580(11) 0.0002(7) -0.0061(7) 0.0052(7) Cl1 0.0346(8) 0.0449(9) 0.0426(10) 0.0043(8) 0.0115(7) -0.0016(7) N2 0.022(2) 0.031(3) 0.022(3) -0.002(2) -0.004(2) -0.002(2) N1 0.022(2) 0.036(3) 0.022(3) 0.005(2) 0.000(2) 0.001(2) N3 0.025(3) 0.027(3) 0.027(3) -0.004(2) 0.001(2) 0.003(2) C2 0.027(3) 0.037(3) 0.017(3) 0.002(2) -0.002(2) 0.005(3) C1 0.023(3) 0.029(3) 0.021(3) 0.002(2) 0.000(2) 0.001(2) C12 0.021(3) 0.029(3) 0.025(3) -0.002(2) 0.000(2) -0.001(2) C11 0.033(3) 0.033(3) 0.025(3) 0.001(3) 0.003(3) 0.000(3) C10 0.036(3) 0.032(3) 0.029(3) -0.010(3) -0.004(3) -0.002(3) C9 0.025(3) 0.038(3) 0.044(4) -0.004(3) 0.001(3) -0.003(3) C7 0.022(3) 0.026(3) 0.038(4) -0.004(3) 0.000(3) -0.002(2) C8 0.024(3) 0.027(3) 0.027(3) 0.002(3) 0.003(3) 0.002(2) C6 0.024(3) 0.037(3) 0.037(4) 0.000(3) 0.005(3) -0.006(3) C5 0.034(3) 0.035(3) 0.033(4) 0.006(3) 0.009(3) -0.001(3) C4 0.033(3) 0.031(3) 0.021(3) 0.001(3) 0.004(3) 0.000(3) C3 0.022(3) 0.028(3) 0.028(3) 0.003(3) 0.001(2) 0.000(2) C33 0.022(3) 0.030(3) 0.021(3) 0.001(2) -0.001(2) -0.005(2) C32 0.029(3) 0.030(3) 0.029(3) 0.003(3) 0.006(3) 0.000(3) C31 0.039(3) 0.033(3) 0.031(4) -0.001(3) 0.010(3) 0.006(3) C30 0.045(4) 0.043(4) 0.018(3) -0.001(3) 0.005(3) 0.000(3) C29 0.037(3) 0.035(3) 0.019(3) 0.001(3) -0.001(3) 0.003(3) C28 0.021(3) 0.034(3) 0.026(3) -0.003(3) 0.002(2) -0.002(2) C27 0.028(3) 0.038(3) 0.025(3) -0.003(3) -0.004(3) 0.002(3) C26 0.029(3) 0.032(3) 0.024(3) 0.005(3) 0.003(2) 0.003(2) C25 0.029(3) 0.024(3) 0.028(3) 0.004(2) -0.001(3) -0.003(2) C24 0.036(3) 0.028(3) 0.030(3) 0.001(3) -0.003(3) -0.001(3) C23 0.034(3) 0.029(3) 0.040(4) -0.002(3) -0.003(3) 0.004(3) C22 0.028(3) 0.033(3) 0.036(4) -0.002(3) 0.003(3) 0.000(3) C21 0.022(3) 0.029(3) 0.027(3) -0.003(3) -0.003(3) -0.003(2) C20 0.035(3) 0.027(3) 0.029(3) -0.005(3) -0.005(3) 0.004(3) C19 0.025(3) 0.034(3) 0.030(3) 0.000(3) -0.002(3) 0.001(3) C18 0.022(3) 0.031(3) 0.031(3) 0.006(3) -0.005(2) -0.003(2) C17 0.031(3) 0.033(3) 0.026(3) -0.005(3) 0.002(3) 0.000(3) C16 0.047(4) 0.036(3) 0.027(3) -0.002(3) -0.006(3) 0.008(3) C15 0.039(4) 0.040(4) 0.026(3) 0.006(3) -0.004(3) 0.004(3) C14 0.027(3) 0.030(3) 0.028(3) 0.002(3) 0.001(3) 0.005(3) C13 0.022(3) 0.032(3) 0.021(3) -0.002(2) -0.003(2) -0.001(2) N100 0.043(4) 0.059(4) 0.041(4) -0.007(3) 0.002(3) 0.002(3) C100 0.034(4) 0.054(4) 0.027(4) 0.000(3) 0.003(3) -0.007(3) C101 0.050(4) 0.068(5) 0.039(4) 0.004(4) -0.009(4) -0.011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 Cl2 2.5023(16) . ? Bi1 Cl3 2.5299(16) . ? Bi1 N2 2.540(5) . ? Bi1 Cl1 2.6385(15) . ? Bi1 N1 2.648(5) . ? N2 C2 1.280(7) . ? N2 C13 1.436(7) . ? N1 C1 1.286(7) . ? N1 C33 1.440(7) . ? N3 C25 1.349(7) . ? N3 C21 1.362(7) . ? C2 C3 1.467(8) . ? C2 C1 1.518(8) . ? C1 C12 1.466(7) . ? C12 C11 1.366(8) . ? C12 C8 1.427(8) . ? C11 C10 1.407(8) . ? C11 H11A 0.9500 . ? C10 C9 1.376(9) . ? C10 H10A 0.9500 . ? C9 C7 1.411(9) . ? C9 H9A 0.9500 . ? C7 C6 1.404(9) . ? C7 C8 1.407(8) . ? C8 C3 1.402(8) . ? C6 C5 1.377(9) . ? C6 H6A 0.9500 . ? C5 C4 1.406(8) . ? C5 H5A 0.9500 . ? C4 C3 1.378(8) . ? C4 H4A 0.9500 . ? C33 C32 1.393(8) . ? C33 C28 1.399(8) . ? C32 C31 1.384(8) . ? C32 H32A 0.9500 . ? C31 C30 1.366(8) . ? C31 H31A 0.9500 . ? C30 C29 1.399(8) . ? C30 H30A 0.9500 . ? C29 C28 1.393(8) . ? C29 H29A 0.9500 . ? C28 C27 1.503(8) . ? C27 C26 1.541(8) . ? C27 H27B 0.9900 . ? C27 H27A 0.9900 . ? C26 C25 1.492(8) . ? C26 H26B 0.9900 . ? C26 H26A 0.9900 . ? C25 C24 1.386(8) . ? C24 C23 1.372(9) . ? C24 H24A 0.9500 . ? C23 C22 1.385(9) . ? C23 H23A 0.9500 . ? C22 C21 1.389(8) . ? C22 H22A 0.9500 . ? C21 C20 1.491(8) . ? C20 C19 1.555(8) . ? C20 H20B 0.9900 . ? C20 H20A 0.9900 . ? C19 C18 1.510(8) . ? C19 H19B 0.9900 . ? C19 H19A 0.9900 . ? C18 C17 1.386(8) . ? C18 C13 1.407(8) . ? C17 C16 1.391(8) . ? C17 H17A 0.9500 . ? C16 C15 1.375(9) . ? C16 H16A 0.9500 . ? C15 C14 1.385(9) . ? C15 H15A 0.9500 . ? C14 C13 1.390(8) . ? C14 H14A 0.9500 . ? N100 C100 1.141(9) . ? C100 C101 1.459(10) . ? C101 H10B 0.9800 . ? C101 H10C 0.9800 . ? C101 H10D 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Bi1 Cl3 90.25(5) . . ? Cl2 Bi1 N2 81.84(11) . . ? Cl3 Bi1 N2 89.29(11) . . ? Cl2 Bi1 Cl1 88.07(5) . . ? Cl3 Bi1 Cl1 101.57(5) . . ? N2 Bi1 Cl1 165.23(11) . . ? Cl2 Bi1 N1 82.72(11) . . ? Cl3 Bi1 N1 154.48(11) . . ? N2 Bi1 N1 65.48(14) . . ? Cl1 Bi1 N1 102.68(11) . . ? C2 N2 C13 119.6(5) . . ? C2 N2 Bi1 119.1(4) . . ? C13 N2 Bi1 121.3(3) . . ? C1 N1 C33 118.6(5) . . ? C1 N1 Bi1 115.1(4) . . ? C33 N1 Bi1 126.1(3) . . ? C25 N3 C21 118.5(5) . . ? N2 C2 C3 133.1(6) . . ? N2 C2 C1 120.0(5) . . ? C3 C2 C1 106.9(5) . . ? N1 C1 C12 133.1(6) . . ? N1 C1 C2 120.1(5) . . ? C12 C1 C2 106.7(5) . . ? C11 C12 C8 119.2(5) . . ? C11 C12 C1 134.9(5) . . ? C8 C12 C1 105.9(5) . . ? C12 C11 C10 119.1(6) . . ? C12 C11 H11A 120.5 . . ? C10 C11 H11A 120.5 . . ? C9 C10 C11 122.0(6) . . ? C9 C10 H10A 119.0 . . ? C11 C10 H10A 119.0 . . ? C10 C9 C7 120.8(6) . . ? C10 C9 H9A 119.6 . . ? C7 C9 H9A 119.6 . . ? C6 C7 C8 115.8(6) . . ? C6 C7 C9 127.7(6) . . ? C8 C7 C9 116.5(6) . . ? C3 C8 C7 123.9(6) . . ? C3 C8 C12 113.7(5) . . ? C7 C8 C12 122.4(6) . . ? C5 C6 C7 121.0(6) . . ? C5 C6 H6A 119.5 . . ? C7 C6 H6A 119.5 . . ? C6 C5 C4 122.0(6) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C3 C4 C5 118.8(6) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C4 C3 C8 118.6(5) . . ? C4 C3 C2 134.9(6) . . ? C8 C3 C2 106.5(5) . . ? C32 C33 C28 122.3(5) . . ? C32 C33 N1 119.1(5) . . ? C28 C33 N1 118.5(5) . . ? C31 C32 C33 118.4(6) . . ? C31 C32 H32A 120.8 . . ? C33 C32 H32A 120.8 . . ? C30 C31 C32 120.9(6) . . ? C30 C31 H31A 119.5 . . ? C32 C31 H31A 119.5 . . ? C31 C30 C29 120.3(6) . . ? C31 C30 H30A 119.9 . . ? C29 C30 H30A 119.9 . . ? C28 C29 C30 120.7(6) . . ? C28 C29 H29A 119.7 . . ? C30 C29 H29A 119.7 . . ? C29 C28 C33 117.3(5) . . ? C29 C28 C27 122.0(5) . . ? C33 C28 C27 120.7(5) . . ? C28 C27 C26 112.1(5) . . ? C28 C27 H27B 109.2 . . ? C26 C27 H27B 109.2 . . ? C28 C27 H27A 109.2 . . ? C26 C27 H27A 109.2 . . ? H27B C27 H27A 107.9 . . ? C25 C26 C27 111.1(5) . . ? C25 C26 H26B 109.4 . . ? C27 C26 H26B 109.4 . . ? C25 C26 H26A 109.4 . . ? C27 C26 H26A 109.4 . . ? H26B C26 H26A 108.0 . . ? N3 C25 C24 122.4(6) . . ? N3 C25 C26 115.9(5) . . ? C24 C25 C26 121.6(5) . . ? C23 C24 C25 119.0(6) . . ? C23 C24 H24A 120.5 . . ? C25 C24 H24A 120.5 . . ? C24 C23 C22 119.6(6) . . ? C24 C23 H23A 120.2 . . ? C22 C23 H23A 120.2 . . ? C23 C22 C21 119.3(6) . . ? C23 C22 H22A 120.4 . . ? C21 C22 H22A 120.4 . . ? N3 C21 C22 121.3(6) . . ? N3 C21 C20 116.2(5) . . ? C22 C21 C20 122.4(6) . . ? C21 C20 C19 113.2(5) . . ? C21 C20 H20B 108.9 . . ? C19 C20 H20B 108.9 . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20A 108.9 . . ? H20B C20 H20A 107.7 . . ? C18 C19 C20 112.9(5) . . ? C18 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? H19B C19 H19A 107.8 . . ? C17 C18 C13 116.6(5) . . ? C17 C18 C19 122.1(5) . . ? C13 C18 C19 121.3(5) . . ? C18 C17 C16 121.8(6) . . ? C18 C17 H17A 119.1 . . ? C16 C17 H17A 119.1 . . ? C15 C16 C17 120.5(6) . . ? C15 C16 H16A 119.7 . . ? C17 C16 H16A 119.7 . . ? C16 C15 C14 119.5(6) . . ? C16 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? C15 C14 C13 119.7(5) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C14 C13 C18 121.9(5) . . ? C14 C13 N2 118.7(5) . . ? C18 C13 N2 119.3(5) . . ? N100 C100 C101 179.1(8) . . ? C100 C101 H10B 109.5 . . ? C100 C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? C100 C101 H10D 109.5 . . ? H10B C101 H10D 109.5 . . ? H10C C101 H10D 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Bi1 N2 C2 -84.5(4) . . . . ? Cl3 Bi1 N2 C2 -174.8(4) . . . . ? Cl1 Bi1 N2 C2 -37.1(7) . . . . ? N1 Bi1 N2 C2 1.2(4) . . . . ? Cl2 Bi1 N2 C13 92.9(4) . . . . ? Cl3 Bi1 N2 C13 2.6(4) . . . . ? Cl1 Bi1 N2 C13 140.3(4) . . . . ? N1 Bi1 N2 C13 178.6(4) . . . . ? Cl2 Bi1 N1 C1 86.2(4) . . . . ? Cl3 Bi1 N1 C1 11.1(5) . . . . ? N2 Bi1 N1 C1 1.8(4) . . . . ? Cl1 Bi1 N1 C1 172.5(4) . . . . ? Cl2 Bi1 N1 C33 -99.4(4) . . . . ? Cl3 Bi1 N1 C33 -174.5(3) . . . . ? N2 Bi1 N1 C33 176.3(5) . . . . ? Cl1 Bi1 N1 C33 -13.0(4) . . . . ? C13 N2 C2 C3 0.4(9) . . . . ? Bi1 N2 C2 C3 177.9(5) . . . . ? C13 N2 C2 C1 178.7(5) . . . . ? Bi1 N2 C2 C1 -3.9(7) . . . . ? C33 N1 C1 C12 1.2(9) . . . . ? Bi1 N1 C1 C12 176.1(5) . . . . ? C33 N1 C1 C2 -179.3(5) . . . . ? Bi1 N1 C1 C2 -4.4(6) . . . . ? N2 C2 C1 N1 5.8(8) . . . . ? C3 C2 C1 N1 -175.5(5) . . . . ? N2 C2 C1 C12 -174.5(5) . . . . ? C3 C2 C1 C12 4.1(6) . . . . ? N1 C1 C12 C11 -4.4(11) . . . . ? C2 C1 C12 C11 176.0(6) . . . . ? N1 C1 C12 C8 174.9(6) . . . . ? C2 C1 C12 C8 -4.6(6) . . . . ? C8 C12 C11 C10 -0.2(8) . . . . ? C1 C12 C11 C10 179.1(6) . . . . ? C12 C11 C10 C9 -0.8(9) . . . . ? C11 C10 C9 C7 1.2(9) . . . . ? C10 C9 C7 C6 178.4(6) . . . . ? C10 C9 C7 C8 -0.6(9) . . . . ? C6 C7 C8 C3 -2.2(9) . . . . ? C9 C7 C8 C3 177.0(5) . . . . ? C6 C7 C8 C12 -179.5(5) . . . . ? C9 C7 C8 C12 -0.4(9) . . . . ? C11 C12 C8 C3 -176.8(5) . . . . ? C1 C12 C8 C3 3.7(6) . . . . ? C11 C12 C8 C7 0.8(9) . . . . ? C1 C12 C8 C7 -178.7(5) . . . . ? C8 C7 C6 C5 1.3(9) . . . . ? C9 C7 C6 C5 -177.7(6) . . . . ? C7 C6 C5 C4 0.1(10) . . . . ? C6 C5 C4 C3 -0.9(9) . . . . ? C5 C4 C3 C8 0.2(8) . . . . ? C5 C4 C3 C2 -179.8(6) . . . . ? C7 C8 C3 C4 1.4(9) . . . . ? C12 C8 C3 C4 179.0(5) . . . . ? C7 C8 C3 C2 -178.6(5) . . . . ? C12 C8 C3 C2 -1.0(6) . . . . ? N2 C2 C3 C4 -3.6(11) . . . . ? C1 C2 C3 C4 178.0(6) . . . . ? N2 C2 C3 C8 176.5(6) . . . . ? C1 C2 C3 C8 -2.0(6) . . . . ? C1 N1 C33 C32 -92.5(6) . . . . ? Bi1 N1 C33 C32 93.2(6) . . . . ? C1 N1 C33 C28 89.7(7) . . . . ? Bi1 N1 C33 C28 -84.6(6) . . . . ? C28 C33 C32 C31 -3.9(9) . . . . ? N1 C33 C32 C31 178.3(5) . . . . ? C33 C32 C31 C30 0.7(9) . . . . ? C32 C31 C30 C29 2.0(10) . . . . ? C31 C30 C29 C28 -1.6(9) . . . . ? C30 C29 C28 C33 -1.4(9) . . . . ? C30 C29 C28 C27 176.2(5) . . . . ? C32 C33 C28 C29 4.2(9) . . . . ? N1 C33 C28 C29 -178.0(5) . . . . ? C32 C33 C28 C27 -173.4(5) . . . . ? N1 C33 C28 C27 4.3(8) . . . . ? C29 C28 C27 C26 -97.2(6) . . . . ? C33 C28 C27 C26 80.4(7) . . . . ? C28 C27 C26 C25 -156.9(5) . . . . ? C21 N3 C25 C24 1.2(8) . . . . ? C21 N3 C25 C26 -174.3(5) . . . . ? C27 C26 C25 N3 85.0(6) . . . . ? C27 C26 C25 C24 -90.5(6) . . . . ? N3 C25 C24 C23 -1.2(9) . . . . ? C26 C25 C24 C23 174.1(5) . . . . ? C25 C24 C23 C22 0.3(9) . . . . ? C24 C23 C22 C21 0.6(9) . . . . ? C25 N3 C21 C22 -0.3(8) . . . . ? C25 N3 C21 C20 177.6(5) . . . . ? C23 C22 C21 N3 -0.6(9) . . . . ? C23 C22 C21 C20 -178.4(5) . . . . ? N3 C21 C20 C19 -77.1(6) . . . . ? C22 C21 C20 C19 100.8(6) . . . . ? C21 C20 C19 C18 146.3(5) . . . . ? C20 C19 C18 C17 90.0(7) . . . . ? C20 C19 C18 C13 -89.5(7) . . . . ? C13 C18 C17 C16 0.9(9) . . . . ? C19 C18 C17 C16 -178.5(6) . . . . ? C18 C17 C16 C15 1.4(10) . . . . ? C17 C16 C15 C14 -1.7(10) . . . . ? C16 C15 C14 C13 -0.4(9) . . . . ? C15 C14 C13 C18 2.8(9) . . . . ? C15 C14 C13 N2 -179.7(5) . . . . ? C17 C18 C13 C14 -3.0(8) . . . . ? C19 C18 C13 C14 176.4(5) . . . . ? C17 C18 C13 N2 179.5(5) . . . . ? C19 C18 C13 N2 -1.1(8) . . . . ? C2 N2 C13 C14 88.7(7) . . . . ? Bi1 N2 C13 C14 -88.6(6) . . . . ? C2 N2 C13 C18 -93.7(7) . . . . ? Bi1 N2 C13 C18 88.9(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.801 _refine_diff_density_min -2.755 _refine_diff_density_rms 0.287 data_5As _database_code_depnum_ccdc_archive 'CCDC 864993' #TrackingRef '- CIF_Ragogna_clamshell.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 As N3, C F3 O3 S, C H2 Cl2' _chemical_formula_sum 'C35 H27 As Cl2 F3 N3 O3 S' _chemical_formula_weight 772.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' As As 0.0499 2.0058 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 _symmetry_space_group_name_Hall -P2ybc 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 11.010(2) _cell_length_b 15.943(3) _cell_length_c 23.006(6) _cell_angle_alpha 90.00 _cell_angle_beta 115.88(2) _cell_angle_gamma 90.00 _cell_volume 3633.3(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15722 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 1.193 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7627 _exptl_absorpt_correction_T_max 0.8507 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; One of the solvates was disordered Disordered solvate could not be modelled, squeeze function was employed ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29821 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.55 _reflns_number_total 8360 _reflns_number_gt 5597 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.1091P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0059(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8360 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1799 _refine_ls_wR_factor_gt 0.1629 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.20072(4) -0.74398(2) -0.048058(18) 0.03286(15) Uani 1 1 d . . . N2 N 0.1879(3) -0.63785(17) -0.08052(14) 0.0286(6) Uani 1 1 d . . . N1 N 0.3195(3) -0.69833(17) 0.02857(14) 0.0305(6) Uani 1 1 d . . . N3 N -0.0327(3) -0.65138(18) 0.00278(15) 0.0349(7) Uani 1 1 d . . . C2 C 0.2662(3) -0.5814(2) -0.03583(16) 0.0283(7) Uani 1 1 d . . . C1 C 0.3399(3) -0.6146(2) 0.02514(16) 0.0285(7) Uani 1 1 d . . . C12 C 0.4181(3) -0.5489(2) 0.06966(17) 0.0283(7) Uani 1 1 d . . . C11 C 0.5044(3) -0.5426(2) 0.13449(17) 0.0341(8) Uani 1 1 d . . . H11A H 0.5274 -0.5904 0.1618 0.041 Uiso 1 1 calc R . . C10 C 0.5574(4) -0.4632(2) 0.15895(18) 0.0394(9) Uani 1 1 d . . . H10A H 0.6192 -0.4588 0.2033 0.047 Uiso 1 1 calc R . . C9 C 0.5244(4) -0.3918(2) 0.12200(19) 0.0395(9) Uani 1 1 d . . . H9A H 0.5609 -0.3393 0.1413 0.047 Uiso 1 1 calc R . . C7 C 0.4357(3) -0.3960(2) 0.05475(17) 0.0322(8) Uani 1 1 d . . . C8 C 0.3865(3) -0.4759(2) 0.03111(17) 0.0284(7) Uani 1 1 d . . . C6 C 0.3904(4) -0.3285(2) 0.00983(19) 0.0380(9) Uani 1 1 d . . . H6A H 0.4204 -0.2730 0.0237 0.046 Uiso 1 1 calc R . . C5 C 0.3031(4) -0.3438(2) -0.0538(2) 0.0386(9) Uani 1 1 d . . . H5A H 0.2754 -0.2982 -0.0834 0.046 Uiso 1 1 calc R . . C4 C 0.2532(4) -0.4251(2) -0.07652(18) 0.0336(8) Uani 1 1 d . . . H4A H 0.1919 -0.4338 -0.1205 0.040 Uiso 1 1 calc R . . C3 C 0.2944(3) -0.4908(2) -0.03428(17) 0.0287(7) Uani 1 1 d . . . C33 C 0.3768(4) -0.74762(19) 0.08724(18) 0.0332(8) Uani 1 1 d . . . C32 C 0.4727(4) -0.8071(2) 0.09219(19) 0.0381(9) Uani 1 1 d . . . H32A H 0.5021 -0.8121 0.0592 0.046 Uiso 1 1 calc R . . C31 C 0.5251(4) -0.8591(2) 0.1454(2) 0.0443(10) Uani 1 1 d . . . H31A H 0.5898 -0.9008 0.1491 0.053 Uiso 1 1 calc R . . C30 C 0.4823(4) -0.8499(2) 0.1929(2) 0.0506(11) Uani 1 1 d . . . H30A H 0.5194 -0.8846 0.2301 0.061 Uiso 1 1 calc R . . C29 C 0.3881(4) -0.7919(2) 0.1873(2) 0.0471(10) Uani 1 1 d . . . H29A H 0.3600 -0.7873 0.2207 0.057 Uiso 1 1 calc R . . C28 C 0.3310(4) -0.7386(2) 0.13403(19) 0.0345(8) Uani 1 1 d . . . C27 C 0.2242(4) -0.6759(2) 0.12974(19) 0.0388(9) Uani 1 1 d . . . H27A H 0.2178 -0.6316 0.0984 0.047 Uiso 1 1 calc R . . H27B H 0.2523 -0.6489 0.1724 0.047 Uiso 1 1 calc R . . C26 C 0.0832(4) -0.7161(3) 0.1088(2) 0.0461(10) Uani 1 1 d . . . H26A H 0.0949 -0.7727 0.1282 0.055 Uiso 1 1 calc R . . H26B H 0.0317 -0.6820 0.1263 0.055 Uiso 1 1 calc R . . C25 C 0.0007(4) -0.7238(3) 0.0360(2) 0.0416(9) Uani 1 1 d . . . C24 C -0.0415(4) -0.8017(2) 0.0067(2) 0.0498(11) Uani 1 1 d . . . H24A H -0.0157 -0.8519 0.0313 0.060 Uiso 1 1 calc R . . C23 C -0.1217(5) -0.8036(3) -0.0589(3) 0.0606(13) Uani 1 1 d . . . H23A H -0.1508 -0.8559 -0.0804 0.073 Uiso 1 1 calc R . . C22 C -0.1601(4) -0.7293(3) -0.0936(2) 0.0511(11) Uani 1 1 d . . . H22A H -0.2169 -0.7299 -0.1387 0.061 Uiso 1 1 calc R . . C21 C -0.1140(4) -0.6544(2) -0.06108(19) 0.0375(9) Uani 1 1 d . . . C20 C -0.1553(4) -0.5712(3) -0.09441(19) 0.0431(9) Uani 1 1 d . . . H20A H -0.1829 -0.5340 -0.0678 0.052 Uiso 1 1 calc R . . H20B H -0.2352 -0.5797 -0.1363 0.052 Uiso 1 1 calc R . . C19 C -0.0451(4) -0.5266(2) -0.10685(18) 0.0359(8) Uani 1 1 d . . . H19A H -0.0730 -0.4679 -0.1197 0.043 Uiso 1 1 calc R . . H19B H 0.0394 -0.5255 -0.0662 0.043 Uiso 1 1 calc R . . C18 C -0.0174(4) -0.5686(2) -0.15908(17) 0.0333(8) Uani 1 1 d . . . C17 C -0.1071(4) -0.5570(3) -0.22338(19) 0.0475(10) Uani 1 1 d . . . H17A H -0.1814 -0.5200 -0.2340 0.057 Uiso 1 1 calc R . . C16 C -0.0904(4) -0.5981(3) -0.2722(2) 0.0572(12) Uani 1 1 d . . . H16A H -0.1537 -0.5894 -0.3158 0.069 Uiso 1 1 calc R . . C15 C 0.0181(4) -0.6522(3) -0.2581(2) 0.0528(11) Uani 1 1 d . . . H15A H 0.0285 -0.6812 -0.2918 0.063 Uiso 1 1 calc R . . C14 C 0.1098(4) -0.6630(2) -0.19490(18) 0.0380(8) Uani 1 1 d . . . H14A H 0.1848 -0.6994 -0.1844 0.046 Uiso 1 1 calc R . . C13 C 0.0927(3) -0.6206(2) -0.14629(17) 0.0302(7) Uani 1 1 d . . . S1 S 0.64904(10) -0.37270(6) -0.34103(5) 0.0369(2) Uani 1 1 d . . . F1 F 0.4580(3) -0.31719(19) -0.31283(17) 0.0867(10) Uani 1 1 d . . . F2 F 0.5425(3) -0.43517(18) -0.26880(12) 0.0662(7) Uani 1 1 d . . . F3 F 0.4065(3) -0.43002(18) -0.36940(13) 0.0700(8) Uani 1 1 d . . . O1 O 0.6000(4) -0.3178(2) -0.39531(17) 0.0755(11) Uani 1 1 d . . . O2 O 0.7489(3) -0.3358(2) -0.28253(16) 0.0719(10) Uani 1 1 d . . . O3 O 0.6807(3) -0.45540(16) -0.35344(15) 0.0547(8) Uani 1 1 d . . . C34 C 0.5065(4) -0.3892(3) -0.3225(2) 0.0463(10) Uani 1 1 d . . . Cl1 Cl -0.19005(13) -0.45410(7) -0.50547(7) 0.0651(3) Uani 1 1 d . . . Cl2 Cl -0.29278(13) -0.59751(7) -0.46243(6) 0.0596(3) Uani 1 1 d . . . C35 C -0.3256(5) -0.4934(3) -0.4924(2) 0.0523(11) Uani 1 1 d . . . H35A H -0.4091 -0.4924 -0.5335 0.063 Uiso 1 1 calc R . . H35B H -0.3399 -0.4571 -0.4610 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 As1 0.0362(2) 0.0242(2) 0.0404(2) -0.00253(15) 0.01876(18) 0.00084(14) N2 0.0250(14) 0.0295(15) 0.0339(16) 0.0005(12) 0.0152(12) 0.0042(11) N1 0.0330(16) 0.0253(15) 0.0378(17) 0.0034(12) 0.0199(14) 0.0050(12) N3 0.0344(17) 0.0338(16) 0.0454(19) 0.0002(14) 0.0257(15) 0.0011(13) C2 0.0260(17) 0.0299(18) 0.0333(19) 0.0004(14) 0.0168(15) 0.0017(14) C1 0.0266(17) 0.0277(17) 0.0341(19) 0.0027(14) 0.0160(15) 0.0020(13) C12 0.0249(17) 0.0287(17) 0.0371(19) -0.0017(14) 0.0190(15) 0.0005(13) C11 0.0313(19) 0.039(2) 0.035(2) 0.0001(16) 0.0176(16) 0.0047(15) C10 0.0273(19) 0.051(2) 0.036(2) -0.0107(18) 0.0097(16) -0.0049(17) C9 0.040(2) 0.039(2) 0.046(2) -0.0092(18) 0.0238(19) -0.0085(17) C7 0.0328(19) 0.0294(18) 0.039(2) -0.0049(15) 0.0203(16) -0.0042(14) C8 0.0236(17) 0.0271(17) 0.040(2) -0.0022(14) 0.0186(16) -0.0007(13) C6 0.040(2) 0.0277(18) 0.055(3) -0.0052(17) 0.029(2) -0.0058(15) C5 0.040(2) 0.0290(19) 0.051(2) 0.0045(17) 0.0248(19) 0.0023(16) C4 0.0346(19) 0.0289(18) 0.039(2) 0.0014(15) 0.0172(17) 0.0005(15) C3 0.0299(18) 0.0259(17) 0.037(2) -0.0009(14) 0.0202(16) 0.0016(14) C33 0.036(2) 0.0238(17) 0.039(2) 0.0043(14) 0.0147(16) 0.0032(14) C32 0.036(2) 0.0316(19) 0.047(2) 0.0029(16) 0.0191(18) 0.0061(15) C31 0.042(2) 0.032(2) 0.055(3) 0.0097(18) 0.018(2) 0.0134(16) C30 0.059(3) 0.039(2) 0.049(3) 0.0172(19) 0.020(2) 0.0153(19) C29 0.058(3) 0.042(2) 0.042(2) 0.0089(19) 0.023(2) 0.007(2) C28 0.042(2) 0.0263(18) 0.038(2) 0.0026(15) 0.0195(17) 0.0020(15) C27 0.049(2) 0.0348(19) 0.040(2) 0.0031(16) 0.0262(19) 0.0059(17) C26 0.054(3) 0.046(2) 0.054(3) 0.012(2) 0.038(2) 0.0088(19) C25 0.042(2) 0.041(2) 0.055(3) 0.0033(19) 0.033(2) 0.0017(17) C24 0.056(3) 0.032(2) 0.079(3) -0.003(2) 0.046(3) -0.0039(18) C23 0.058(3) 0.048(3) 0.092(4) -0.026(3) 0.048(3) -0.017(2) C22 0.045(3) 0.055(3) 0.062(3) -0.016(2) 0.032(2) -0.012(2) C21 0.0287(19) 0.044(2) 0.045(2) -0.0028(17) 0.0204(18) -0.0011(16) C20 0.037(2) 0.052(2) 0.043(2) 0.0028(18) 0.0205(19) 0.0098(18) C19 0.0302(19) 0.038(2) 0.043(2) 0.0027(16) 0.0187(17) 0.0128(15) C18 0.0339(19) 0.0345(18) 0.0322(19) 0.0024(15) 0.0150(16) 0.0042(15) C17 0.044(2) 0.059(3) 0.039(2) 0.0054(19) 0.0171(19) 0.0110(19) C16 0.048(3) 0.089(3) 0.030(2) 0.003(2) 0.0136(19) 0.016(2) C15 0.055(3) 0.072(3) 0.037(2) -0.014(2) 0.024(2) 0.003(2) C14 0.037(2) 0.042(2) 0.038(2) -0.0057(17) 0.0205(17) 0.0053(16) C13 0.0313(18) 0.0284(17) 0.0317(18) -0.0028(14) 0.0146(15) -0.0008(14) S1 0.0451(6) 0.0292(5) 0.0427(6) 0.0026(4) 0.0249(5) -0.0006(4) F1 0.078(2) 0.080(2) 0.125(3) -0.0269(19) 0.065(2) 0.0073(16) F2 0.0652(17) 0.091(2) 0.0486(15) -0.0001(14) 0.0305(13) -0.0259(15) F3 0.0471(15) 0.094(2) 0.0612(17) -0.0144(15) 0.0162(13) -0.0204(14) O1 0.080(2) 0.076(2) 0.083(3) 0.052(2) 0.048(2) 0.0323(19) O2 0.072(2) 0.089(2) 0.069(2) -0.0402(19) 0.0441(19) -0.0478(19) O3 0.075(2) 0.0317(15) 0.071(2) -0.0001(14) 0.0443(18) 0.0086(14) C34 0.043(2) 0.054(2) 0.044(2) -0.005(2) 0.020(2) -0.0022(19) Cl1 0.0673(8) 0.0532(7) 0.0841(9) -0.0048(6) 0.0415(7) -0.0178(6) Cl2 0.0802(8) 0.0465(6) 0.0696(8) -0.0030(5) 0.0489(7) -0.0080(6) C35 0.062(3) 0.050(3) 0.055(3) -0.006(2) 0.036(2) -0.002(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 As1 N1 1.826(3) . ? As1 N2 1.830(3) . ? N2 C2 1.355(4) . ? N2 C13 1.442(4) . ? N1 C1 1.361(4) . ? N1 C33 1.447(4) . ? N3 C25 1.344(5) . ? N3 C21 1.347(5) . ? C2 C1 1.383(5) . ? C2 C3 1.474(4) . ? C1 C12 1.455(5) . ? C12 C11 1.379(5) . ? C12 C8 1.411(5) . ? C11 C10 1.403(5) . ? C11 H11A 0.9500 . ? C10 C9 1.372(5) . ? C10 H10A 0.9500 . ? C9 C7 1.426(5) . ? C9 H9A 0.9500 . ? C7 C8 1.399(4) . ? C7 C6 1.422(5) . ? C8 C3 1.420(5) . ? C6 C5 1.378(5) . ? C6 H6A 0.9500 . ? C5 C4 1.417(5) . ? C5 H5A 0.9500 . ? C4 C3 1.364(5) . ? C4 H4A 0.9500 . ? C33 C28 1.382(5) . ? C33 C32 1.387(5) . ? C32 C31 1.379(5) . ? C32 H32A 0.9500 . ? C31 C30 1.373(6) . ? C31 H31A 0.9500 . ? C30 C29 1.352(5) . ? C30 H30A 0.9500 . ? C29 C28 1.394(5) . ? C29 H29A 0.9500 . ? C28 C27 1.514(5) . ? C27 C26 1.549(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C26 C25 1.521(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C25 C24 1.392(6) . ? C24 C23 1.377(7) . ? C24 H24A 0.9500 . ? C23 C22 1.387(7) . ? C23 H23A 0.9500 . ? C22 C21 1.383(5) . ? C22 H22A 0.9500 . ? C21 C20 1.500(5) . ? C20 C19 1.537(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C19 C18 1.518(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C18 C17 1.387(5) . ? C18 C13 1.390(5) . ? C17 C16 1.380(6) . ? C17 H17A 0.9500 . ? C16 C15 1.393(6) . ? C16 H16A 0.9500 . ? C15 C14 1.372(6) . ? C15 H15A 0.9500 . ? C14 C13 1.388(5) . ? C14 H14A 0.9500 . ? S1 O1 1.424(3) . ? S1 O3 1.424(3) . ? S1 O2 1.440(3) . ? S1 C34 1.816(4) . ? F1 C34 1.325(5) . ? F2 C34 1.339(5) . ? F3 C34 1.328(5) . ? Cl1 C35 1.762(4) . ? Cl2 C35 1.773(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 As1 N2 85.44(12) . . ? C2 N2 C13 126.9(3) . . ? C2 N2 As1 113.2(2) . . ? C13 N2 As1 119.7(2) . . ? C1 N1 C33 124.8(3) . . ? C1 N1 As1 113.7(2) . . ? C33 N1 As1 121.4(2) . . ? C25 N3 C21 118.5(3) . . ? N2 C2 C1 114.3(3) . . ? N2 C2 C3 136.6(3) . . ? C1 C2 C3 109.1(3) . . ? N1 C1 C2 113.3(3) . . ? N1 C1 C12 136.6(3) . . ? C2 C1 C12 110.0(3) . . ? C11 C12 C8 118.9(3) . . ? C11 C12 C1 137.0(3) . . ? C8 C12 C1 104.1(3) . . ? C12 C11 C10 118.0(3) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C9 C10 C11 123.3(4) . . ? C9 C10 H10A 118.4 . . ? C11 C10 H10A 118.4 . . ? C10 C9 C7 120.3(3) . . ? C10 C9 H9A 119.9 . . ? C7 C9 H9A 119.9 . . ? C8 C7 C6 116.9(3) . . ? C8 C7 C9 115.5(3) . . ? C6 C7 C9 127.6(3) . . ? C7 C8 C12 124.0(3) . . ? C7 C8 C3 122.7(3) . . ? C12 C8 C3 113.2(3) . . ? C5 C6 C7 120.0(3) . . ? C5 C6 H6A 120.0 . . ? C7 C6 H6A 120.0 . . ? C6 C5 C4 122.1(3) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C3 C4 C5 119.0(3) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C4 C3 C8 119.2(3) . . ? C4 C3 C2 137.2(3) . . ? C8 C3 C2 103.6(3) . . ? C28 C33 C32 122.1(3) . . ? C28 C33 N1 120.8(3) . . ? C32 C33 N1 117.0(3) . . ? C31 C32 C33 119.5(4) . . ? C31 C32 H32A 120.3 . . ? C33 C32 H32A 120.3 . . ? C30 C31 C32 119.1(4) . . ? C30 C31 H31A 120.5 . . ? C32 C31 H31A 120.5 . . ? C29 C30 C31 120.8(4) . . ? C29 C30 H30A 119.6 . . ? C31 C30 H30A 119.6 . . ? C30 C29 C28 122.2(4) . . ? C30 C29 H29A 118.9 . . ? C28 C29 H29A 118.9 . . ? C33 C28 C29 116.3(3) . . ? C33 C28 C27 123.7(3) . . ? C29 C28 C27 120.0(4) . . ? C28 C27 C26 113.0(3) . . ? C28 C27 H27A 109.0 . . ? C26 C27 H27A 109.0 . . ? C28 C27 H27B 109.0 . . ? C26 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C25 C26 C27 114.3(3) . . ? C25 C26 H26A 108.7 . . ? C27 C26 H26A 108.7 . . ? C25 C26 H26B 108.7 . . ? C27 C26 H26B 108.7 . . ? H26A C26 H26B 107.6 . . ? N3 C25 C24 122.7(4) . . ? N3 C25 C26 116.1(4) . . ? C24 C25 C26 121.1(4) . . ? C23 C24 C25 118.0(4) . . ? C23 C24 H24A 121.0 . . ? C25 C24 H24A 121.0 . . ? C24 C23 C22 120.0(4) . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? C21 C22 C23 118.6(4) . . ? C21 C22 H22A 120.7 . . ? C23 C22 H22A 120.7 . . ? N3 C21 C22 122.2(4) . . ? N3 C21 C20 115.8(3) . . ? C22 C21 C20 122.0(4) . . ? C21 C20 C19 114.6(3) . . ? C21 C20 H20A 108.6 . . ? C19 C20 H20A 108.6 . . ? C21 C20 H20B 108.6 . . ? C19 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C18 C19 C20 113.0(3) . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? C18 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C17 C18 C13 117.1(3) . . ? C17 C18 C19 119.3(3) . . ? C13 C18 C19 123.6(3) . . ? C16 C17 C18 121.2(4) . . ? C16 C17 H17A 119.4 . . ? C18 C17 H17A 119.4 . . ? C17 C16 C15 120.7(4) . . ? C17 C16 H16A 119.6 . . ? C15 C16 H16A 119.6 . . ? C14 C15 C16 118.9(4) . . ? C14 C15 H15A 120.5 . . ? C16 C15 H15A 120.5 . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? C14 C13 C18 122.2(3) . . ? C14 C13 N2 117.4(3) . . ? C18 C13 N2 120.2(3) . . ? O1 S1 O3 115.2(2) . . ? O1 S1 O2 114.3(2) . . ? O3 S1 O2 114.3(2) . . ? O1 S1 C34 105.0(2) . . ? O3 S1 C34 103.03(19) . . ? O2 S1 C34 103.01(19) . . ? F1 C34 F3 108.0(3) . . ? F1 C34 F2 107.4(4) . . ? F3 C34 F2 106.7(3) . . ? F1 C34 S1 111.5(3) . . ? F3 C34 S1 112.0(3) . . ? F2 C34 S1 110.9(3) . . ? Cl1 C35 Cl2 110.8(2) . . ? Cl1 C35 H35A 109.5 . . ? Cl2 C35 H35A 109.5 . . ? Cl1 C35 H35B 109.5 . . ? Cl2 C35 H35B 109.5 . . ? H35A C35 H35B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 As1 N2 C2 0.0(2) . . . . ? N1 As1 N2 C13 -175.1(2) . . . . ? N2 As1 N1 C1 0.0(2) . . . . ? N2 As1 N1 C33 175.9(3) . . . . ? C13 N2 C2 C1 174.7(3) . . . . ? As1 N2 C2 C1 0.0(3) . . . . ? C13 N2 C2 C3 -4.7(6) . . . . ? As1 N2 C2 C3 -179.4(3) . . . . ? C33 N1 C1 C2 -175.7(3) . . . . ? As1 N1 C1 C2 0.1(3) . . . . ? C33 N1 C1 C12 2.6(6) . . . . ? As1 N1 C1 C12 178.4(3) . . . . ? N2 C2 C1 N1 -0.1(4) . . . . ? C3 C2 C1 N1 179.5(3) . . . . ? N2 C2 C1 C12 -178.9(3) . . . . ? C3 C2 C1 C12 0.7(4) . . . . ? N1 C1 C12 C11 -0.6(7) . . . . ? C2 C1 C12 C11 177.8(4) . . . . ? N1 C1 C12 C8 -178.8(4) . . . . ? C2 C1 C12 C8 -0.4(3) . . . . ? C8 C12 C11 C10 -0.3(5) . . . . ? C1 C12 C11 C10 -178.4(4) . . . . ? C12 C11 C10 C9 1.9(5) . . . . ? C11 C10 C9 C7 -2.1(5) . . . . ? C10 C9 C7 C8 0.6(5) . . . . ? C10 C9 C7 C6 179.4(3) . . . . ? C6 C7 C8 C12 -178.0(3) . . . . ? C9 C7 C8 C12 1.0(5) . . . . ? C6 C7 C8 C3 -0.7(5) . . . . ? C9 C7 C8 C3 178.3(3) . . . . ? C11 C12 C8 C7 -1.2(5) . . . . ? C1 C12 C8 C7 177.5(3) . . . . ? C11 C12 C8 C3 -178.7(3) . . . . ? C1 C12 C8 C3 0.0(3) . . . . ? C8 C7 C6 C5 -0.6(5) . . . . ? C9 C7 C6 C5 -179.4(3) . . . . ? C7 C6 C5 C4 1.4(5) . . . . ? C6 C5 C4 C3 -1.0(5) . . . . ? C5 C4 C3 C8 -0.3(5) . . . . ? C5 C4 C3 C2 177.2(4) . . . . ? C7 C8 C3 C4 1.1(5) . . . . ? C12 C8 C3 C4 178.7(3) . . . . ? C7 C8 C3 C2 -177.1(3) . . . . ? C12 C8 C3 C2 0.4(3) . . . . ? N2 C2 C3 C4 1.0(7) . . . . ? C1 C2 C3 C4 -178.5(4) . . . . ? N2 C2 C3 C8 178.8(4) . . . . ? C1 C2 C3 C8 -0.7(3) . . . . ? C1 N1 C33 C28 71.6(5) . . . . ? As1 N1 C33 C28 -103.9(3) . . . . ? C1 N1 C33 C32 -112.3(4) . . . . ? As1 N1 C33 C32 72.3(4) . . . . ? C28 C33 C32 C31 -0.3(6) . . . . ? N1 C33 C32 C31 -176.3(3) . . . . ? C33 C32 C31 C30 -1.0(6) . . . . ? C32 C31 C30 C29 1.4(7) . . . . ? C31 C30 C29 C28 -0.6(7) . . . . ? C32 C33 C28 C29 1.0(6) . . . . ? N1 C33 C28 C29 177.0(3) . . . . ? C32 C33 C28 C27 -178.5(4) . . . . ? N1 C33 C28 C27 -2.6(6) . . . . ? C30 C29 C28 C33 -0.6(6) . . . . ? C30 C29 C28 C27 179.0(4) . . . . ? C33 C28 C27 C26 101.7(4) . . . . ? C29 C28 C27 C26 -77.9(5) . . . . ? C28 C27 C26 C25 -85.3(4) . . . . ? C21 N3 C25 C24 2.3(5) . . . . ? C21 N3 C25 C26 -175.1(3) . . . . ? C27 C26 C25 N3 -63.1(4) . . . . ? C27 C26 C25 C24 119.5(4) . . . . ? N3 C25 C24 C23 -0.6(6) . . . . ? C26 C25 C24 C23 176.7(4) . . . . ? C25 C24 C23 C22 -1.2(6) . . . . ? C24 C23 C22 C21 1.2(6) . . . . ? C25 N3 C21 C22 -2.2(5) . . . . ? C25 N3 C21 C20 175.9(3) . . . . ? C23 C22 C21 N3 0.4(6) . . . . ? C23 C22 C21 C20 -177.5(3) . . . . ? N3 C21 C20 C19 76.1(4) . . . . ? C22 C21 C20 C19 -105.9(4) . . . . ? C21 C20 C19 C18 71.2(4) . . . . ? C20 C19 C18 C17 76.8(4) . . . . ? C20 C19 C18 C13 -101.7(4) . . . . ? C13 C18 C17 C16 2.7(6) . . . . ? C19 C18 C17 C16 -175.9(4) . . . . ? C18 C17 C16 C15 -0.5(7) . . . . ? C17 C16 C15 C14 -1.1(7) . . . . ? C16 C15 C14 C13 0.4(6) . . . . ? C15 C14 C13 C18 1.9(6) . . . . ? C15 C14 C13 N2 176.7(3) . . . . ? C17 C18 C13 C14 -3.4(5) . . . . ? C19 C18 C13 C14 175.1(3) . . . . ? C17 C18 C13 N2 -178.0(3) . . . . ? C19 C18 C13 N2 0.4(5) . . . . ? C2 N2 C13 C14 123.7(4) . . . . ? As1 N2 C13 C14 -61.9(4) . . . . ? C2 N2 C13 C18 -61.4(5) . . . . ? As1 N2 C13 C18 113.0(3) . . . . ? O1 S1 C34 F1 -55.7(4) . . . . ? O3 S1 C34 F1 -176.6(3) . . . . ? O2 S1 C34 F1 64.3(4) . . . . ? O1 S1 C34 F3 65.5(4) . . . . ? O3 S1 C34 F3 -55.4(3) . . . . ? O2 S1 C34 F3 -174.5(3) . . . . ? O1 S1 C34 F2 -175.3(3) . . . . ? O3 S1 C34 F2 63.8(3) . . . . ? O2 S1 C34 F2 -55.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.552 _refine_diff_density_min -0.639 _refine_diff_density_rms 0.128 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 -0.081 0.411 0.793 138 58 ' ' 2 0.080 0.589 0.207 138 58 ' ' 3 0.419 0.089 0.293 138 58 ' ' 4 0.580 -0.089 0.707 138 58 ' ' _platon_squeeze_details ; ; data_6Sb _database_code_depnum_ccdc_archive 'CCDC 864994' #TrackingRef '- CIF_Ragogna_clamshell.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 Cl2 N3 Sb, C F3 O3 S, 0.55(C4 O)' _chemical_formula_sum 'C36.20 H25 Cl2 F3 N3 O3.55 S Sb' _chemical_formula_weight 840.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5743(10) _cell_length_b 20.9295(17) _cell_length_c 14.7300(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.609(2) _cell_angle_gamma 90.00 _cell_volume 3868.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6484 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 19.31 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1678 _exptl_absorpt_coefficient_mu 0.958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8540 _exptl_absorpt_correction_T_max 0.9536 _exptl_absorpt_process_details ? _exptl_special_details ; A diethyl ether solvate contained disorder and was left isotropic Hydrogen atoms could not be added to the disordered solvate The resolution was low (theta max 24.04). This compound is prone to decomposition in solution and as a solid at room temperature. This was the best data we could obtain. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 95180 _diffrn_reflns_av_R_equivalents 0.1551 _diffrn_reflns_av_sigmaI/netI 0.0765 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 24.04 _reflns_number_total 6098 _reflns_number_gt 3989 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0995P)^2^+10.3602P] 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 6098 _refine_ls_number_parameters 445 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1905 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.075 _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 0.41071(5) 0.10024(3) -0.46221(4) 0.0324(2) Uani 1 1 d . . . Cl2 Cl 0.2546(2) 0.16145(11) -0.49322(14) 0.0467(6) Uani 1 1 d . . . Cl1 Cl 0.5236(2) 0.18329(11) -0.51438(15) 0.0459(6) Uani 1 1 d . . . N2 N 0.4405(5) 0.1423(3) -0.3199(4) 0.0284(15) Uani 1 1 d . . . N1 N 0.3013(5) 0.0430(3) -0.3501(4) 0.0304(16) Uani 1 1 d . . . N3 N 0.1633(6) 0.1782(4) -0.2289(5) 0.047(2) Uani 1 1 d . . . C2 C 0.4117(6) 0.1093(4) -0.2523(5) 0.0291(18) Uani 1 1 d . . . C1 C 0.3387(6) 0.0530(4) -0.2696(6) 0.0315(19) Uani 1 1 d . . . C12 C 0.3225(7) 0.0226(4) -0.1808(5) 0.033(2) Uani 1 1 d . . . C11 C 0.2685(7) -0.0287(4) -0.1523(5) 0.039(2) Uani 1 1 d . . . H11A H 0.2295 -0.0555 -0.1946 0.047 Uiso 1 1 calc R . . C10 C 0.2717(8) -0.0414(4) -0.0578(6) 0.047(2) Uani 1 1 d . . . H10A H 0.2337 -0.0773 -0.0373 0.056 Uiso 1 1 calc R . . C9 C 0.3274(8) -0.0043(5) 0.0056(6) 0.048(3) Uani 1 1 d . . . H9A H 0.3275 -0.0150 0.0683 0.058 Uiso 1 1 calc R . . C7 C 0.3841(8) 0.0494(4) -0.0219(6) 0.040(2) Uani 1 1 d . . . C8 C 0.3811(7) 0.0618(4) -0.1163(5) 0.032(2) Uani 1 1 d . . . C6 C 0.4433(8) 0.0919(4) 0.0337(6) 0.045(2) Uani 1 1 d . . . H6A H 0.4484 0.0852 0.0977 0.054 Uiso 1 1 calc R . . C5 C 0.4953(8) 0.1441(5) -0.0024(6) 0.045(2) Uani 1 1 d . . . H5A H 0.5340 0.1726 0.0375 0.054 Uiso 1 1 calc R . . C4 C 0.4917(7) 0.1552(4) -0.0954(5) 0.039(2) Uani 1 1 d . . . H4A H 0.5285 0.1906 -0.1189 0.046 Uiso 1 1 calc R . . C3 C 0.4338(6) 0.1141(4) -0.1540(5) 0.0290(19) Uani 1 1 d . . . C33 C 0.2298(7) -0.0086(4) -0.3737(5) 0.035(2) Uani 1 1 d . . . C32 C 0.2704(7) -0.0659(4) -0.3994(6) 0.039(2) Uani 1 1 d . . . H32A H 0.3452 -0.0723 -0.3981 0.047 Uiso 1 1 calc R . . C31 C 0.2007(8) -0.1147(4) -0.4274(6) 0.047(2) Uani 1 1 d . . . H31A H 0.2281 -0.1547 -0.4456 0.057 Uiso 1 1 calc R . . C30 C 0.0935(8) -0.1054(4) -0.4288(7) 0.048(2) Uani 1 1 d . . . H30A H 0.0466 -0.1395 -0.4464 0.058 Uiso 1 1 calc R . . C29 C 0.0519(8) -0.0470(5) -0.4050(7) 0.050(3) Uani 1 1 d . . . H29A H -0.0232 -0.0411 -0.4075 0.060 Uiso 1 1 calc R . . C28 C 0.1186(8) 0.0033(4) -0.3774(6) 0.043(2) Uani 1 1 d . . . C27 C 0.0738(8) 0.0693(5) -0.3561(7) 0.051(2) Uani 1 1 d . . . H27A H 0.1219 0.1024 -0.3785 0.061 Uiso 1 1 calc R . . H27B H 0.0035 0.0744 -0.3895 0.061 Uiso 1 1 calc R . . C26 C 0.0611(8) 0.0806(5) -0.2547(7) 0.051(3) Uani 1 1 d . . . H26A H 0.1189 0.0584 -0.2185 0.061 Uiso 1 1 calc R . . H26B H -0.0078 0.0626 -0.2378 0.061 Uiso 1 1 calc R . . C25 C 0.0649(8) 0.1523(5) -0.2332(7) 0.055(3) Uani 1 1 d . . . C24 C -0.0252(10) 0.1878(7) -0.2224(11) 0.102(5) Uani 1 1 d . . . H24A H -0.0937 0.1684 -0.2258 0.123 Uiso 1 1 calc R . . C23 C -0.0133(9) 0.2526(6) -0.2063(12) 0.112(6) Uani 1 1 d . . . H23A H -0.0744 0.2783 -0.1989 0.134 Uiso 1 1 calc R . . C22 C 0.0862(9) 0.2801(5) -0.2009(9) 0.079(4) Uani 1 1 d . . . H22A H 0.0950 0.3245 -0.1892 0.095 Uiso 1 1 calc R . . C21 C 0.1749(8) 0.2406(5) -0.2133(7) 0.051(3) Uani 1 1 d . . . C20 C 0.2865(8) 0.2648(4) -0.2054(6) 0.047(2) Uani 1 1 d . . . H20A H 0.3297 0.2377 -0.1620 0.057 Uiso 1 1 calc R . . H20B H 0.2872 0.3089 -0.1810 0.057 Uiso 1 1 calc R . . C19 C 0.3374(8) 0.2645(4) -0.2994(6) 0.043(2) Uani 1 1 d . . . H19A H 0.3067 0.2289 -0.3367 0.052 Uiso 1 1 calc R . . H19B H 0.3194 0.3049 -0.3317 0.052 Uiso 1 1 calc R . . C18 C 0.4561(7) 0.2573(4) -0.2895(5) 0.035(2) Uani 1 1 d . . . C17 C 0.5227(9) 0.3094(4) -0.2663(6) 0.044(2) Uani 1 1 d . . . H17A H 0.4919 0.3498 -0.2547 0.052 Uiso 1 1 calc R . . C16 C 0.6314(9) 0.3028(5) -0.2601(6) 0.050(3) Uani 1 1 d . . . H16A H 0.6753 0.3388 -0.2451 0.060 Uiso 1 1 calc R . . C15 C 0.6776(8) 0.2442(5) -0.2758(7) 0.051(3) Uani 1 1 d . . . H15A H 0.7530 0.2401 -0.2725 0.062 Uiso 1 1 calc R . . C14 C 0.6150(7) 0.1923(4) -0.2959(6) 0.040(2) Uani 1 1 d . . . H14A H 0.6464 0.1517 -0.3056 0.048 Uiso 1 1 calc R . . C13 C 0.5064(7) 0.1990(4) -0.3021(5) 0.033(2) Uani 1 1 d . . . S1 S 0.38661(18) 0.01306(10) 0.31861(14) 0.0333(5) Uani 1 1 d . . . F1 F 0.2309(6) -0.0546(4) 0.2455(7) 0.121(3) Uani 1 1 d . . . F2 F 0.2074(6) 0.0449(4) 0.2335(6) 0.108(3) Uani 1 1 d . . . F3 F 0.1924(7) 0.0028(6) 0.3636(8) 0.148(4) Uani 1 1 d . . . O1 O 0.4371(6) 0.0062(3) 0.2350(4) 0.0580(19) Uani 1 1 d . . . O2 O 0.3906(6) 0.0763(3) 0.3551(4) 0.0562(19) Uani 1 1 d . . . O3 O 0.4112(5) -0.0360(3) 0.3844(4) 0.0461(16) Uani 1 1 d . . . C34 C 0.2459(10) 0.0004(6) 0.2904(11) 0.077(4) Uani 1 1 d . . . C103 C 0.114(3) 0.1370(17) 0.032(2) 0.126(11) Uiso 0.55 1 d P . . C102 C 0.054(3) 0.1924(16) 0.036(2) 0.118(10) Uiso 0.55 1 d P . . O4 O -0.041(2) 0.1678(11) 0.0261(16) 0.140(8) Uiso 0.55 1 d P . . C100 C -0.0968(18) 0.2203(11) 0.0415(15) 0.071(6) Uiso 0.55 1 d P . . C101 C -0.220(2) 0.2095(12) -0.0076(17) 0.090(7) Uiso 0.55 1 d P . . 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 0.0449(4) 0.0311(3) 0.0212(3) -0.0010(3) 0.0014(2) 0.0001(3) Cl2 0.0564(15) 0.0549(15) 0.0284(12) 0.0019(10) -0.0002(11) 0.0142(12) Cl1 0.0657(16) 0.0405(13) 0.0319(12) 0.0023(10) 0.0059(11) -0.0111(11) N2 0.032(4) 0.030(4) 0.024(4) 0.001(3) 0.004(3) -0.001(3) N1 0.034(4) 0.031(4) 0.027(4) -0.005(3) 0.004(3) -0.003(3) N3 0.039(5) 0.044(5) 0.057(5) -0.019(4) 0.001(4) 0.002(4) C2 0.032(4) 0.030(5) 0.025(4) 0.001(4) 0.004(4) 0.002(4) C1 0.031(5) 0.028(4) 0.036(5) -0.002(4) 0.003(4) 0.003(4) C12 0.039(5) 0.033(5) 0.027(5) 0.002(4) -0.001(4) 0.009(4) C11 0.049(6) 0.034(5) 0.034(5) 0.001(4) 0.007(4) 0.001(4) C10 0.057(6) 0.039(5) 0.044(6) 0.009(5) 0.012(5) -0.002(5) C9 0.066(7) 0.053(6) 0.027(5) 0.006(5) 0.007(5) 0.005(5) C7 0.056(6) 0.041(5) 0.023(5) 0.000(4) 0.002(4) 0.007(5) C8 0.038(5) 0.035(5) 0.024(5) -0.003(4) 0.005(4) 0.007(4) C6 0.064(6) 0.051(6) 0.019(4) 0.005(4) -0.003(4) 0.015(5) C5 0.059(6) 0.054(6) 0.023(5) -0.012(4) -0.002(4) 0.008(5) C4 0.047(6) 0.039(5) 0.030(5) -0.005(4) 0.004(4) 0.005(4) C3 0.038(5) 0.030(5) 0.019(4) -0.006(3) 0.002(4) 0.004(4) C33 0.045(5) 0.032(5) 0.028(5) -0.005(4) 0.001(4) -0.006(4) C32 0.045(6) 0.033(5) 0.040(5) -0.001(4) 0.007(4) -0.001(4) C31 0.064(7) 0.038(5) 0.040(6) -0.008(4) 0.004(5) -0.002(5) C30 0.060(7) 0.030(5) 0.055(6) 0.005(5) 0.004(5) -0.003(5) C29 0.040(6) 0.056(6) 0.054(6) -0.011(5) 0.001(5) -0.007(5) C28 0.050(6) 0.041(5) 0.040(5) -0.004(4) 0.005(5) -0.002(5) C27 0.036(5) 0.059(6) 0.057(6) -0.004(5) 0.003(5) -0.001(5) C26 0.038(5) 0.065(7) 0.050(6) -0.014(5) 0.002(5) -0.010(5) C25 0.052(7) 0.052(6) 0.060(7) -0.024(5) 0.004(5) 0.011(5) C24 0.042(7) 0.095(10) 0.167(15) -0.069(10) -0.018(8) 0.010(7) C23 0.040(7) 0.076(9) 0.216(18) -0.079(11) -0.015(9) 0.018(7) C22 0.063(8) 0.060(7) 0.112(11) -0.051(7) -0.014(7) 0.026(6) C21 0.049(6) 0.054(6) 0.049(6) -0.023(5) -0.004(5) 0.007(5) C20 0.059(6) 0.040(5) 0.042(5) -0.015(4) 0.000(5) 0.002(5) C19 0.059(6) 0.043(5) 0.027(5) -0.007(4) -0.005(4) 0.010(5) C18 0.049(6) 0.037(5) 0.019(4) -0.001(4) 0.004(4) -0.002(4) C17 0.078(8) 0.031(5) 0.021(5) -0.002(4) -0.001(5) -0.002(5) C16 0.071(8) 0.041(6) 0.036(5) -0.004(4) -0.001(5) -0.022(5) C15 0.037(6) 0.061(7) 0.056(6) -0.007(5) -0.001(5) -0.008(5) C14 0.034(5) 0.041(5) 0.043(5) -0.013(4) -0.003(4) -0.007(4) C13 0.050(6) 0.034(5) 0.015(4) -0.006(3) 0.003(4) 0.000(4) S1 0.0400(13) 0.0351(12) 0.0249(11) -0.0016(9) 0.0010(9) 0.0005(10) F1 0.081(5) 0.081(5) 0.192(9) -0.023(6) -0.061(6) -0.024(4) F2 0.085(5) 0.103(6) 0.129(7) -0.009(5) -0.055(5) 0.035(5) F3 0.061(5) 0.227(12) 0.160(9) 0.037(8) 0.047(6) 0.015(6) O1 0.074(5) 0.072(5) 0.030(4) 0.002(3) 0.018(3) 0.014(4) O2 0.099(6) 0.034(3) 0.035(4) -0.004(3) -0.007(4) -0.002(4) O3 0.064(4) 0.038(3) 0.036(4) 0.005(3) 0.001(3) 0.005(3) C34 0.053(8) 0.067(8) 0.108(11) 0.003(8) -0.024(8) 0.005(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 Sb1 N2 2.283(6) . ? Sb1 Cl2 2.365(2) . ? Sb1 Cl1 2.401(2) . ? Sb1 N1 2.518(6) . ? N2 C2 1.282(10) . ? N2 C13 1.463(10) . ? N1 C1 1.266(10) . ? N1 C33 1.433(10) . ? N3 C21 1.333(12) . ? N3 C25 1.349(12) . ? C2 C3 1.460(11) . ? C2 C1 1.505(11) . ? C1 C12 1.480(12) . ? C12 C11 1.352(12) . ? C12 C8 1.425(11) . ? C11 C10 1.416(12) . ? C11 H11A 0.9500 . ? C10 C9 1.371(13) . ? C10 H10A 0.9500 . ? C9 C7 1.405(13) . ? C9 H9A 0.9500 . ? C7 C6 1.392(13) . ? C7 C8 1.413(11) . ? C8 C3 1.412(11) . ? C6 C5 1.396(13) . ? C6 H6A 0.9500 . ? C5 C4 1.387(11) . ? C5 H5A 0.9500 . ? C4 C3 1.392(11) . ? C4 H4A 0.9500 . ? C33 C32 1.366(12) . ? C33 C28 1.418(13) . ? C32 C31 1.392(13) . ? C32 H32A 0.9500 . ? C31 C30 1.361(13) . ? C31 H31A 0.9500 . ? C30 C29 1.385(13) . ? C30 H30A 0.9500 . ? C29 C28 1.390(13) . ? C29 H29A 0.9500 . ? C28 C27 1.532(13) . ? C27 C26 1.530(13) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C26 C25 1.535(13) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C25 C24 1.372(15) . ? C24 C23 1.383(17) . ? C24 H24A 0.9500 . ? C23 C22 1.375(16) . ? C23 H23A 0.9500 . ? C22 C21 1.408(13) . ? C22 H22A 0.9500 . ? C21 C20 1.490(13) . ? C20 C19 1.562(13) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C19 C18 1.499(13) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C18 C13 1.390(11) . ? C18 C17 1.404(12) . ? C17 C16 1.372(14) . ? C17 H17A 0.9500 . ? C16 C15 1.383(14) . ? C16 H16A 0.9500 . ? C15 C14 1.364(12) . ? C15 H15A 0.9500 . ? C14 C13 1.370(12) . ? C14 H14A 0.9500 . ? S1 O1 1.428(6) . ? S1 O2 1.429(6) . ? S1 O3 1.432(6) . ? S1 C34 1.811(12) . ? F1 C34 1.335(14) . ? F2 C34 1.324(14) . ? F3 C34 1.308(16) . ? C103 C102 1.39(4) . ? C102 O4 1.29(3) . ? C102 C100 1.99(4) . ? O4 C100 1.33(3) . ? C100 C101 1.68(3) . ? 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 N2 Sb1 Cl2 93.13(17) . . ? N2 Sb1 Cl1 87.08(17) . . ? Cl2 Sb1 Cl1 92.66(9) . . ? N2 Sb1 N1 69.3(2) . . ? Cl2 Sb1 N1 84.44(16) . . ? Cl1 Sb1 N1 155.91(16) . . ? C2 N2 C13 118.9(6) . . ? C2 N2 Sb1 117.9(5) . . ? C13 N2 Sb1 122.4(4) . . ? C1 N1 C33 122.8(7) . . ? C1 N1 Sb1 110.4(5) . . ? C33 N1 Sb1 124.1(5) . . ? C21 N3 C25 119.4(8) . . ? N2 C2 C3 133.4(7) . . ? N2 C2 C1 119.3(7) . . ? C3 C2 C1 107.4(7) . . ? N1 C1 C12 133.9(8) . . ? N1 C1 C2 118.3(7) . . ? C12 C1 C2 107.6(7) . . ? C11 C12 C8 120.0(8) . . ? C11 C12 C1 135.6(8) . . ? C8 C12 C1 104.4(7) . . ? C12 C11 C10 118.1(8) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? C9 C10 C11 123.0(9) . . ? C9 C10 H10A 118.5 . . ? C11 C10 H10A 118.5 . . ? C10 C9 C7 120.3(8) . . ? C10 C9 H9A 119.9 . . ? C7 C9 H9A 119.9 . . ? C6 C7 C9 127.2(8) . . ? C6 C7 C8 116.2(8) . . ? C9 C7 C8 116.6(8) . . ? C3 C8 C7 123.1(8) . . ? C3 C8 C12 114.8(7) . . ? C7 C8 C12 122.1(8) . . ? C7 C6 C5 121.4(8) . . ? C7 C6 H6A 119.3 . . ? C5 C6 H6A 119.3 . . ? C4 C5 C6 121.5(8) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C5 C4 C3 119.4(8) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C3 C8 118.4(7) . . ? C4 C3 C2 135.9(8) . . ? C8 C3 C2 105.8(7) . . ? C32 C33 C28 121.9(8) . . ? C32 C33 N1 119.2(8) . . ? C28 C33 N1 118.6(7) . . ? C33 C32 C31 119.2(9) . . ? C33 C32 H32A 120.4 . . ? C31 C32 H32A 120.4 . . ? C30 C31 C32 120.3(9) . . ? C30 C31 H31A 119.9 . . ? C32 C31 H31A 119.9 . . ? C31 C30 C29 120.8(9) . . ? C31 C30 H30A 119.6 . . ? C29 C30 H30A 119.6 . . ? C30 C29 C28 120.9(9) . . ? C30 C29 H29A 119.6 . . ? C28 C29 H29A 119.6 . . ? C29 C28 C33 117.0(8) . . ? C29 C28 C27 121.4(9) . . ? C33 C28 C27 121.6(8) . . ? C26 C27 C28 113.7(8) . . ? C26 C27 H27A 108.8 . . ? C28 C27 H27A 108.8 . . ? C26 C27 H27B 108.8 . . ? C28 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C27 C26 C25 110.3(9) . . ? C27 C26 H26A 109.6 . . ? C25 C26 H26A 109.6 . . ? C27 C26 H26B 109.6 . . ? C25 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? N3 C25 C24 122.6(10) . . ? N3 C25 C26 114.8(8) . . ? C24 C25 C26 122.5(10) . . ? C25 C24 C23 118.0(12) . . ? C25 C24 H24A 121.0 . . ? C23 C24 H24A 121.0 . . ? C22 C23 C24 120.6(11) . . ? C22 C23 H23A 119.7 . . ? C24 C23 H23A 119.7 . . ? C23 C22 C21 118.2(10) . . ? C23 C22 H22A 120.9 . . ? C21 C22 H22A 120.9 . . ? N3 C21 C22 121.3(10) . . ? N3 C21 C20 116.0(8) . . ? C22 C21 C20 122.7(9) . . ? C21 C20 C19 111.4(8) . . ? C21 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? C21 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? C18 C19 C20 112.0(7) . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C13 C18 C17 116.4(8) . . ? C13 C18 C19 122.2(8) . . ? C17 C18 C19 121.3(8) . . ? C16 C17 C18 121.0(9) . . ? C16 C17 H17A 119.5 . . ? C18 C17 H17A 119.5 . . ? C17 C16 C15 120.3(9) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C14 C15 C16 120.1(9) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C15 C14 C13 119.4(9) . . ? C15 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C14 C13 C18 122.8(8) . . ? C14 C13 N2 118.6(7) . . ? C18 C13 N2 118.6(7) . . ? O1 S1 O2 114.2(4) . . ? O1 S1 O3 115.0(4) . . ? O2 S1 O3 114.1(4) . . ? O1 S1 C34 105.6(6) . . ? O2 S1 C34 103.5(5) . . ? O3 S1 C34 102.5(5) . . ? F3 C34 F2 107.9(11) . . ? F3 C34 F1 112.1(13) . . ? F2 C34 F1 105.0(11) . . ? F3 C34 S1 110.6(10) . . ? F2 C34 S1 110.8(9) . . ? F1 C34 S1 110.2(9) . . ? O4 C102 C103 99(3) . . ? O4 C102 C100 41.7(16) . . ? C103 C102 C100 140(3) . . ? C102 O4 C100 98(3) . . ? O4 C100 C101 107(2) . . ? O4 C100 C102 40.0(15) . . ? C101 C100 C102 142.6(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Sb1 N2 C2 99.4(6) . . . . ? Cl1 Sb1 N2 C2 -168.1(6) . . . . ? N1 Sb1 N2 C2 16.6(6) . . . . ? Cl2 Sb1 N2 C13 -91.3(6) . . . . ? Cl1 Sb1 N2 C13 1.2(6) . . . . ? N1 Sb1 N2 C13 -174.2(6) . . . . ? N2 Sb1 N1 C1 -18.6(5) . . . . ? Cl2 Sb1 N1 C1 -114.1(5) . . . . ? Cl1 Sb1 N1 C1 -30.0(8) . . . . ? N2 Sb1 N1 C33 179.5(7) . . . . ? Cl2 Sb1 N1 C33 84.1(6) . . . . ? Cl1 Sb1 N1 C33 168.1(5) . . . . ? C13 N2 C2 C3 -2.6(13) . . . . ? Sb1 N2 C2 C3 167.0(7) . . . . ? C13 N2 C2 C1 176.5(7) . . . . ? Sb1 N2 C2 C1 -13.8(9) . . . . ? C33 N1 C1 C12 -3.3(14) . . . . ? Sb1 N1 C1 C12 -165.4(8) . . . . ? C33 N1 C1 C2 -178.9(7) . . . . ? Sb1 N1 C1 C2 19.0(9) . . . . ? N2 C2 C1 N1 -5.5(11) . . . . ? C3 C2 C1 N1 173.9(7) . . . . ? N2 C2 C1 C12 177.8(7) . . . . ? C3 C2 C1 C12 -2.8(9) . . . . ? N1 C1 C12 C11 5.4(17) . . . . ? C2 C1 C12 C11 -178.7(9) . . . . ? N1 C1 C12 C8 -174.2(9) . . . . ? C2 C1 C12 C8 1.8(8) . . . . ? C8 C12 C11 C10 0.5(12) . . . . ? C1 C12 C11 C10 -178.9(9) . . . . ? C12 C11 C10 C9 -0.3(14) . . . . ? C11 C10 C9 C7 0.4(15) . . . . ? C10 C9 C7 C6 179.4(9) . . . . ? C10 C9 C7 C8 -0.7(14) . . . . ? C6 C7 C8 C3 -0.4(13) . . . . ? C9 C7 C8 C3 179.7(8) . . . . ? C6 C7 C8 C12 -179.2(8) . . . . ? C9 C7 C8 C12 0.9(13) . . . . ? C11 C12 C8 C3 -179.8(8) . . . . ? C1 C12 C8 C3 -0.2(9) . . . . ? C11 C12 C8 C7 -0.9(13) . . . . ? C1 C12 C8 C7 178.7(8) . . . . ? C9 C7 C6 C5 -179.3(9) . . . . ? C8 C7 C6 C5 0.8(13) . . . . ? C7 C6 C5 C4 -1.1(14) . . . . ? C6 C5 C4 C3 1.0(13) . . . . ? C5 C4 C3 C8 -0.5(12) . . . . ? C5 C4 C3 C2 -179.5(9) . . . . ? C7 C8 C3 C4 0.3(12) . . . . ? C12 C8 C3 C4 179.1(7) . . . . ? C7 C8 C3 C2 179.5(8) . . . . ? C12 C8 C3 C2 -1.6(10) . . . . ? N2 C2 C3 C4 0.9(17) . . . . ? C1 C2 C3 C4 -178.3(9) . . . . ? N2 C2 C3 C8 -178.1(9) . . . . ? C1 C2 C3 C8 2.7(9) . . . . ? C1 N1 C33 C32 -91.3(10) . . . . ? Sb1 N1 C33 C32 68.4(9) . . . . ? C1 N1 C33 C28 94.3(10) . . . . ? Sb1 N1 C33 C28 -106.0(8) . . . . ? C28 C33 C32 C31 -2.0(13) . . . . ? N1 C33 C32 C31 -176.3(8) . . . . ? C33 C32 C31 C30 -0.2(14) . . . . ? C32 C31 C30 C29 1.8(15) . . . . ? C31 C30 C29 C28 -1.2(15) . . . . ? C30 C29 C28 C33 -1.0(14) . . . . ? C30 C29 C28 C27 176.5(9) . . . . ? C32 C33 C28 C29 2.6(13) . . . . ? N1 C33 C28 C29 176.8(8) . . . . ? C32 C33 C28 C27 -174.9(8) . . . . ? N1 C33 C28 C27 -0.6(12) . . . . ? C29 C28 C27 C26 96.9(11) . . . . ? C33 C28 C27 C26 -85.8(11) . . . . ? C28 C27 C26 C25 155.0(8) . . . . ? C21 N3 C25 C24 0.2(17) . . . . ? C21 N3 C25 C26 178.0(9) . . . . ? C27 C26 C25 N3 -77.0(11) . . . . ? C27 C26 C25 C24 100.7(14) . . . . ? N3 C25 C24 C23 0(2) . . . . ? C26 C25 C24 C23 -177.7(14) . . . . ? C25 C24 C23 C22 0(3) . . . . ? C24 C23 C22 C21 1(2) . . . . ? C25 N3 C21 C22 0.2(16) . . . . ? C25 N3 C21 C20 177.3(9) . . . . ? C23 C22 C21 N3 -0.6(19) . . . . ? C23 C22 C21 C20 -177.6(13) . . . . ? N3 C21 C20 C19 71.1(11) . . . . ? C22 C21 C20 C19 -111.8(11) . . . . ? C21 C20 C19 C18 -152.4(8) . . . . ? C20 C19 C18 C13 100.1(9) . . . . ? C20 C19 C18 C17 -79.6(10) . . . . ? C13 C18 C17 C16 2.4(12) . . . . ? C19 C18 C17 C16 -177.9(8) . . . . ? C18 C17 C16 C15 -0.7(14) . . . . ? C17 C16 C15 C14 -1.1(15) . . . . ? C16 C15 C14 C13 1.2(14) . . . . ? C15 C14 C13 C18 0.6(13) . . . . ? C15 C14 C13 N2 -177.4(8) . . . . ? C17 C18 C13 C14 -2.4(12) . . . . ? C19 C18 C13 C14 178.0(8) . . . . ? C17 C18 C13 N2 175.6(7) . . . . ? C19 C18 C13 N2 -4.0(11) . . . . ? C2 N2 C13 C14 89.3(9) . . . . ? Sb1 N2 C13 C14 -79.9(8) . . . . ? C2 N2 C13 C18 -88.8(9) . . . . ? Sb1 N2 C13 C18 102.0(7) . . . . ? O1 S1 C34 F3 177.1(9) . . . . ? O2 S1 C34 F3 -62.6(11) . . . . ? O3 S1 C34 F3 56.4(10) . . . . ? O1 S1 C34 F2 -63.2(11) . . . . ? O2 S1 C34 F2 57.1(11) . . . . ? O3 S1 C34 F2 176.0(9) . . . . ? O1 S1 C34 F1 52.6(11) . . . . ? O2 S1 C34 F1 172.9(9) . . . . ? O3 S1 C34 F1 -68.2(11) . . . . ? C103 C102 O4 C100 172(2) . . . . ? C102 O4 C100 C101 157(2) . . . . ? C103 C102 C100 O4 -12(4) . . . . ? O4 C102 C100 C101 -37(4) . . . . ? C103 C102 C100 C101 -49(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.469 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.144 data_6Bi _database_code_depnum_ccdc_archive 'CCDC 864995' #TrackingRef '- CIF_Ragogna_clamshell.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H25 Bi Cl2 F3 N3 O3 S, 2(C H2 Cl2)' _chemical_formula_sum 'C36 H29 Bi Cl6 F3 N3 O3 S' _chemical_formula_weight 1062.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 C2/c _symmetry_space_group_name_Hall -C2yc 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 42.4663(17) _cell_length_b 9.7165(5) _cell_length_c 20.6524(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.538(2) _cell_angle_gamma 90.00 _cell_volume 7980.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 117141 _cell_measurement_theta_min 1.99 _cell_measurement_theta_max 34.34 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4144 _exptl_absorpt_coefficient_mu 4.927 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2774 _exptl_absorpt_correction_T_max 0.4391 _exptl_absorpt_process_details ? _exptl_special_details ; Triflate anion was disordered and modelled appropriately ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 117141 _diffrn_reflns_av_R_equivalents 0.0817 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -67 _diffrn_reflns_limit_h_max 67 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 34.34 _reflns_number_total 16657 _reflns_number_gt 11763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0262P)^2^+34.3094P] 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 16657 _refine_ls_number_parameters 515 _refine_ls_number_restraints 342 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 0.999 _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 Bi1 Bi 0.138048(3) 0.815881(12) 0.112867(6) 0.01986(3) Uani 1 1 d U . . Cl1 Cl 0.17516(2) 0.60673(9) 0.13888(5) 0.03146(18) Uani 1 1 d U . . Cl2 Cl 0.17457(2) 0.92908(9) 0.22400(4) 0.02709(16) Uani 1 1 d U . . S1 S 0.08936(2) 0.61381(11) 0.16701(6) 0.0359(2) Uani 1 1 d U . . O3 O 0.08801(8) 0.6064(3) 0.09586(16) 0.0449(7) Uani 1 1 d U A . O2 O 0.09272(9) 0.4881(4) 0.2034(2) 0.0698(12) Uani 1 1 d U A . O1 O 0.11162(8) 0.7221(3) 0.20312(15) 0.0440(7) Uani 1 1 d U A . N3 N 0.09304(7) 1.0470(3) 0.04160(14) 0.0247(6) Uani 1 1 d U . . C21 C 0.06130(9) 1.0141(4) 0.00150(19) 0.0283(7) Uani 1 1 d U . . N1 N 0.17959(6) 0.9150(3) 0.06881(13) 0.0202(5) Uani 1 1 d U . . C33 C 0.20368(8) 1.0147(3) 0.10888(16) 0.0209(6) Uani 1 1 d U . . C28 C 0.19438(9) 1.1529(3) 0.10546(17) 0.0233(6) Uani 1 1 d U . . C29 C 0.21825(9) 1.2454(4) 0.14547(18) 0.0290(7) Uani 1 1 d U . . H29A H 0.2127 1.3403 0.1436 0.035 Uiso 1 1 calc R . . C30 C 0.24999(10) 1.2034(4) 0.1880(2) 0.0346(9) Uani 1 1 d U . . H30A H 0.2658 1.2689 0.2148 0.042 Uiso 1 1 calc R . . C31 C 0.25841(8) 1.0645(4) 0.19110(18) 0.0315(8) Uani 1 1 d U . . H31A H 0.2801 1.0348 0.2202 0.038 Uiso 1 1 calc R . . C32 C 0.23518(8) 0.9697(4) 0.15167(17) 0.0269(7) Uani 1 1 d U . . H32A H 0.2407 0.8746 0.1539 0.032 Uiso 1 1 calc R . . C27 C 0.15930(9) 1.1994(4) 0.06263(18) 0.0284(7) Uani 1 1 d U . . H27B H 0.1495 1.1334 0.0243 0.034 Uiso 1 1 calc R . . H27A H 0.1606 1.2902 0.0420 0.034 Uiso 1 1 calc R . . C26 C 0.13576(8) 1.2109(4) 0.10492(17) 0.0263(7) Uani 1 1 d U . . H26B H 0.1436 1.1468 0.1447 0.032 Uiso 1 1 calc R . . H26A H 0.1370 1.3055 0.1234 0.032 Uiso 1 1 calc R . . C25 C 0.09998(9) 1.1781(4) 0.06246(17) 0.0257(6) Uani 1 1 d U . . C22 C 0.03549(10) 1.1108(4) -0.0173(2) 0.0381(9) Uani 1 1 d U . . H22A H 0.0132 1.0846 -0.0444 0.046 Uiso 1 1 calc R . . C23 C 0.04283(10) 1.2454(5) 0.0042(2) 0.0442(10) Uani 1 1 d U . . H23A H 0.0257 1.3134 -0.0084 0.053 Uiso 1 1 calc R . . C24 C 0.07538(10) 1.2800(4) 0.0440(2) 0.0352(8) Uani 1 1 d U . . H24A H 0.0809 1.3723 0.0586 0.042 Uiso 1 1 calc R . . C20 C 0.05525(9) 0.8679(4) -0.0240(2) 0.0305(8) Uani 1 1 d U . . H20B H 0.0310 0.8462 -0.0375 0.037 Uiso 1 1 calc R . . H20A H 0.0678 0.8046 0.0137 0.037 Uiso 1 1 calc R . . C19 C 0.06659(9) 0.8459(4) -0.08668(19) 0.0305(8) Uani 1 1 d U . . H19B H 0.0487 0.8777 -0.1294 0.037 Uiso 1 1 calc R . . H19A H 0.0871 0.9008 -0.0805 0.037 Uiso 1 1 calc R . . C18 C 0.07381(8) 0.6957(4) -0.09366(19) 0.0291(7) Uani 1 1 d U . . C17 C 0.04965(10) 0.6050(5) -0.1344(2) 0.0411(10) Uani 1 1 d U . . H17A H 0.0281 0.6391 -0.1614 0.049 Uiso 1 1 calc R . . C16 C 0.05635(11) 0.4660(5) -0.1364(2) 0.0451(11) Uani 1 1 d U . . H16A H 0.0394 0.4059 -0.1645 0.054 Uiso 1 1 calc R . . C15 C 0.08758(11) 0.4148(4) -0.0977(2) 0.0398(9) Uani 1 1 d U . . H15A H 0.0921 0.3193 -0.0993 0.048 Uiso 1 1 calc R . . C14 C 0.11238(9) 0.5015(4) -0.0567(2) 0.0299(7) Uani 1 1 d U . . H14A H 0.1338 0.4661 -0.0298 0.036 Uiso 1 1 calc R . . C13 C 0.10553(8) 0.6411(4) -0.05522(17) 0.0241(6) Uani 1 1 d U . . N2 N 0.13092(6) 0.7325(3) -0.01242(14) 0.0216(5) Uani 1 1 d U . . C2 C 0.15532(8) 0.7673(3) -0.03177(16) 0.0201(6) Uani 1 1 d U . . C3 C 0.16341(8) 0.7404(3) -0.09423(16) 0.0216(6) Uani 1 1 d U . . C8 C 0.19298(8) 0.8164(4) -0.08633(16) 0.0228(6) Uani 1 1 d U . . C7 C 0.20787(9) 0.8217(4) -0.13728(17) 0.0274(7) Uani 1 1 d U . . C6 C 0.19173(9) 0.7447(4) -0.19828(18) 0.0298(7) Uani 1 1 d U . . H6A H 0.2008 0.7448 -0.2343 0.036 Uiso 1 1 calc R . . C5 C 0.16327(9) 0.6703(4) -0.20591(18) 0.0303(7) Uani 1 1 d U . . H5A H 0.1531 0.6194 -0.2473 0.036 Uiso 1 1 calc R . . C4 C 0.14842(9) 0.6666(4) -0.15420(17) 0.0274(7) Uani 1 1 d U . . H4A H 0.1286 0.6144 -0.1607 0.033 Uiso 1 1 calc R . . C9 C 0.23690(10) 0.9043(5) -0.1226(2) 0.0363(9) Uani 1 1 d U . . H9A H 0.2479 0.9111 -0.1555 0.044 Uiso 1 1 calc R . . C10 C 0.24940(10) 0.9750(5) -0.0613(2) 0.0424(10) Uani 1 1 d U . . H10A H 0.2693 1.0282 -0.0523 0.051 Uiso 1 1 calc R . . C11 C 0.23372(9) 0.9716(4) -0.0105(2) 0.0353(9) Uani 1 1 d U . . H11A H 0.2426 1.0227 0.0312 0.042 Uiso 1 1 calc R . . C12 C 0.20540(8) 0.8921(4) -0.02377(17) 0.0248(7) Uani 1 1 d U . . C1 C 0.18185(8) 0.8662(3) 0.01269(16) 0.0213(6) Uani 1 1 d U . . Cl3 Cl 0.13971(3) 0.88227(14) 0.37376(6) 0.0569(3) Uani 1 1 d U . . Cl4 Cl 0.19242(4) 0.67745(18) 0.42998(7) 0.0697(4) Uani 1 1 d U . . C100 C 0.16045(16) 0.7384(7) 0.3569(3) 0.0667(16) Uani 1 1 d U . . H10B H 0.1439 0.6639 0.3380 0.080 Uiso 1 1 calc R . . H10C H 0.1701 0.7629 0.3213 0.080 Uiso 1 1 calc R . . Cl5 Cl 0.09449(4) 0.0721(2) 0.22842(10) 0.0840(5) Uani 1 1 d U . . Cl6 Cl 0.02444(4) 0.1280(3) 0.19616(15) 0.1346(10) Uani 1 1 d U . . C200 C 0.06430(16) 0.1937(7) 0.2086(4) 0.081(2) Uani 1 1 d U . . H20C H 0.0638 0.2417 0.1660 0.097 Uiso 1 1 calc R . . H20D H 0.0701 0.2624 0.2464 0.097 Uiso 1 1 calc R . . C34 C 0.0493(3) 0.6954(17) 0.1653(8) 0.050(3) Uani 0.66(4) 1 d PU A 1 F1 F 0.0429(3) 0.8080(15) 0.1277(7) 0.063(3) Uani 0.66(4) 1 d PU A 1 F2 F 0.0491(3) 0.7265(19) 0.2268(6) 0.083(4) Uani 0.66(4) 1 d PU A 1 F3 F 0.02431(19) 0.6053(19) 0.1354(10) 0.096(5) Uani 0.66(4) 1 d PU A 1 C35 C 0.0454(5) 0.635(4) 0.1456(16) 0.052(7) Uani 0.34(4) 1 d PU A 2 F6 F 0.0359(7) 0.753(4) 0.1122(15) 0.070(7) Uani 0.34(4) 1 d PU A 2 F4 F 0.0387(6) 0.634(6) 0.2038(16) 0.109(12) Uani 0.34(4) 1 d PU A 2 F5 F 0.0273(4) 0.533(4) 0.1058(16) 0.099(8) Uani 0.34(4) 1 d PU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.01754(5) 0.02069(5) 0.02066(5) 0.00114(5) 0.00586(4) 0.00114(5) Cl1 0.0292(4) 0.0271(4) 0.0344(4) 0.0034(3) 0.0064(3) 0.0095(3) Cl2 0.0299(4) 0.0300(4) 0.0202(3) -0.0018(3) 0.0074(3) -0.0032(3) S1 0.0254(4) 0.0329(5) 0.0441(6) 0.0164(4) 0.0058(4) -0.0025(4) O3 0.0540(18) 0.0292(15) 0.0433(17) -0.0023(13) 0.0069(14) -0.0044(13) O2 0.058(2) 0.054(2) 0.085(3) 0.045(2) 0.010(2) -0.0027(17) O1 0.0521(18) 0.0474(18) 0.0361(16) -0.0038(13) 0.0201(14) -0.0100(14) N3 0.0245(13) 0.0243(14) 0.0241(13) 0.0016(11) 0.0071(11) 0.0057(11) C21 0.0249(16) 0.0296(18) 0.0297(17) -0.0007(14) 0.0087(14) 0.0040(13) N1 0.0165(11) 0.0227(13) 0.0197(12) -0.0019(10) 0.0043(10) -0.0011(10) C33 0.0178(13) 0.0245(15) 0.0214(14) -0.0023(12) 0.0081(11) -0.0017(11) C28 0.0286(16) 0.0248(16) 0.0192(14) 0.0009(11) 0.0118(12) -0.0022(12) C29 0.0365(19) 0.0256(17) 0.0291(17) -0.0054(14) 0.0168(15) -0.0074(14) C30 0.0323(18) 0.042(2) 0.0333(19) -0.0133(17) 0.0158(15) -0.0149(16) C31 0.0183(14) 0.047(2) 0.0265(17) -0.0084(16) 0.0040(13) -0.0049(15) C32 0.0219(15) 0.0297(18) 0.0265(16) -0.0029(14) 0.0054(13) 0.0011(13) C27 0.0331(17) 0.0270(18) 0.0248(16) 0.0047(14) 0.0098(13) 0.0040(14) C26 0.0295(16) 0.0252(17) 0.0241(16) -0.0009(12) 0.0092(13) 0.0027(13) C25 0.0302(16) 0.0248(16) 0.0241(15) 0.0007(14) 0.0121(13) 0.0042(14) C22 0.0256(18) 0.039(2) 0.045(2) -0.0010(18) 0.0064(16) 0.0079(16) C23 0.033(2) 0.039(2) 0.055(3) 0.002(2) 0.0083(19) 0.0163(18) C24 0.038(2) 0.0251(18) 0.040(2) 0.0009(15) 0.0107(17) 0.0082(15) C20 0.0222(16) 0.0315(18) 0.0347(19) -0.0013(15) 0.0062(14) 0.0017(14) C19 0.0248(16) 0.032(2) 0.0281(17) -0.0022(14) 0.0009(13) 0.0044(13) C18 0.0216(14) 0.0331(19) 0.0302(17) -0.0065(15) 0.0063(13) -0.0035(14) C17 0.0259(18) 0.051(3) 0.042(2) -0.016(2) 0.0059(16) -0.0074(17) C16 0.036(2) 0.047(3) 0.053(3) -0.024(2) 0.0168(19) -0.0182(19) C15 0.048(2) 0.030(2) 0.049(2) -0.0125(18) 0.027(2) -0.0115(17) C14 0.0300(17) 0.0273(18) 0.0351(19) -0.0009(15) 0.0147(15) -0.0012(14) C13 0.0221(15) 0.0273(16) 0.0250(16) -0.0041(13) 0.0108(13) -0.0048(12) N2 0.0183(12) 0.0221(13) 0.0226(13) -0.0019(10) 0.0051(10) -0.0018(10) C2 0.0189(13) 0.0208(14) 0.0177(14) 0.0003(11) 0.0029(11) 0.0005(11) C3 0.0233(15) 0.0226(15) 0.0194(14) 0.0039(12) 0.0080(12) 0.0024(12) C8 0.0233(14) 0.0243(15) 0.0214(14) 0.0040(13) 0.0085(11) 0.0046(13) C7 0.0279(16) 0.0320(18) 0.0236(15) 0.0056(14) 0.0105(13) 0.0041(15) C6 0.0345(18) 0.037(2) 0.0193(15) 0.0015(14) 0.0115(14) 0.0054(15) C5 0.0360(18) 0.033(2) 0.0217(15) -0.0025(14) 0.0101(14) 0.0004(15) C4 0.0299(17) 0.0276(18) 0.0238(16) -0.0030(13) 0.0081(13) -0.0029(13) C9 0.038(2) 0.048(2) 0.0292(19) 0.0011(17) 0.0200(16) -0.0075(18) C10 0.037(2) 0.058(3) 0.040(2) -0.003(2) 0.0222(18) -0.0184(19) C11 0.0320(18) 0.049(2) 0.0288(18) -0.0078(17) 0.0150(15) -0.0178(17) C12 0.0234(15) 0.0301(17) 0.0211(15) 0.0015(13) 0.0081(12) -0.0024(13) C1 0.0193(14) 0.0226(15) 0.0206(14) 0.0018(12) 0.0054(11) 0.0009(11) Cl3 0.0665(8) 0.0503(7) 0.0423(6) 0.0066(5) 0.0047(6) -0.0083(6) Cl4 0.0581(8) 0.1048(12) 0.0496(7) 0.0125(8) 0.0232(6) 0.0197(8) C100 0.090(4) 0.073(4) 0.042(3) 0.009(3) 0.030(3) 0.014(3) Cl5 0.0519(8) 0.0937(13) 0.1003(12) 0.0198(10) 0.0189(8) 0.0171(8) Cl6 0.0415(9) 0.160(2) 0.184(3) -0.036(2) 0.0165(12) 0.0100(11) C200 0.072(4) 0.064(4) 0.121(6) 0.026(4) 0.052(4) 0.006(3) C34 0.030(4) 0.061(8) 0.056(7) 0.025(5) 0.010(4) 0.002(5) F1 0.065(5) 0.063(6) 0.063(5) 0.026(4) 0.023(4) 0.034(4) F2 0.080(5) 0.114(9) 0.081(5) 0.046(6) 0.062(5) 0.043(6) F3 0.028(3) 0.111(9) 0.139(11) 0.028(7) 0.016(4) -0.015(4) C35 0.021(8) 0.082(19) 0.055(13) 0.027(12) 0.017(8) 0.000(10) F6 0.050(9) 0.086(15) 0.079(12) 0.031(11) 0.030(9) 0.049(10) F4 0.084(12) 0.16(3) 0.112(15) 0.067(18) 0.075(12) 0.048(15) F5 0.031(6) 0.122(18) 0.130(15) 0.010(13) 0.010(7) -0.015(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 Bi1 N1 2.448(3) . ? Bi1 Cl1 2.5116(8) . ? Bi1 Cl2 2.5269(8) . ? Bi1 N2 2.626(3) . ? Bi1 O1 2.652(3) . ? S1 O2 1.415(3) . ? S1 O1 1.436(3) . ? S1 O3 1.452(3) . ? S1 C35 1.77(2) . ? S1 C34 1.867(13) . ? N3 C25 1.344(4) . ? N3 C21 1.350(4) . ? C21 C22 1.391(5) . ? C21 C20 1.505(5) . ? N1 C1 1.286(4) . ? N1 C33 1.441(4) . ? C33 C32 1.390(4) . ? C33 C28 1.394(5) . ? C28 C29 1.389(5) . ? C28 C27 1.510(5) . ? C29 C30 1.387(5) . ? C29 H29A 0.9500 . ? C30 C31 1.392(6) . ? C30 H30A 0.9500 . ? C31 C32 1.387(5) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? C27 C26 1.545(5) . ? C27 H27B 0.9900 . ? C27 H27A 0.9900 . ? C26 C25 1.498(5) . ? C26 H26B 0.9900 . ? C26 H26A 0.9900 . ? C25 C24 1.391(5) . ? C22 C23 1.381(6) . ? C22 H22A 0.9500 . ? C23 C24 1.379(6) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C20 C19 1.546(5) . ? C20 H20B 0.9900 . ? C20 H20A 0.9900 . ? C19 C18 1.508(5) . ? C19 H19B 0.9900 . ? C19 H19A 0.9900 . ? C18 C17 1.390(5) . ? C18 C13 1.406(5) . ? C17 C16 1.383(6) . ? C17 H17A 0.9500 . ? C16 C15 1.379(6) . ? C16 H16A 0.9500 . ? C15 C14 1.383(5) . ? C15 H15A 0.9500 . ? C14 C13 1.390(5) . ? C14 H14A 0.9500 . ? C13 N2 1.436(4) . ? N2 C2 1.280(4) . ? C2 C3 1.470(4) . ? C2 C1 1.520(4) . ? C3 C4 1.379(5) . ? C3 C8 1.416(5) . ? C8 C7 1.406(4) . ? C8 C12 1.418(5) . ? C7 C9 1.412(5) . ? C7 C6 1.418(5) . ? C6 C5 1.369(5) . ? C6 H6A 0.9500 . ? C5 C4 1.419(5) . ? C5 H5A 0.9500 . ? C4 H4A 0.9500 . ? C9 C10 1.374(6) . ? C9 H9A 0.9500 . ? C10 C11 1.427(5) . ? C10 H10A 0.9500 . ? C11 C12 1.374(5) . ? C11 H11A 0.9500 . ? C12 C1 1.469(4) . ? Cl3 C100 1.751(6) . ? Cl4 C100 1.741(6) . ? C100 H10B 0.9900 . ? C100 H10C 0.9900 . ? Cl5 C200 1.685(6) . ? Cl6 C200 1.742(6) . ? C200 H20C 0.9900 . ? C200 H20D 0.9900 . ? C34 F2 1.307(15) . ? C34 F1 1.314(17) . ? C34 F3 1.346(13) . ? C35 F6 1.33(3) . ? C35 F4 1.33(3) . ? C35 F5 1.34(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Bi1 Cl1 85.28(7) . . ? N1 Bi1 Cl2 82.75(6) . . ? Cl1 Bi1 Cl2 91.08(3) . . ? N1 Bi1 N2 66.68(8) . . ? Cl1 Bi1 N2 78.92(6) . . ? Cl2 Bi1 N2 148.35(6) . . ? N1 Bi1 O1 159.11(9) . . ? Cl1 Bi1 O1 87.71(8) . . ? Cl2 Bi1 O1 77.73(7) . . ? N2 Bi1 O1 130.97(9) . . ? O2 S1 O1 115.5(2) . . ? O2 S1 O3 117.1(2) . . ? O1 S1 O3 110.28(18) . . ? O2 S1 C35 97.7(10) . . ? O1 S1 C35 119.1(14) . . ? O3 S1 C35 95.1(10) . . ? O2 S1 C34 107.4(4) . . ? O1 S1 C34 97.4(6) . . ? O3 S1 C34 106.8(5) . . ? C35 S1 C34 21.9(10) . . ? S1 O1 Bi1 104.53(15) . . ? C25 N3 C21 118.8(3) . . ? N3 C21 C22 122.0(3) . . ? N3 C21 C20 116.7(3) . . ? C22 C21 C20 121.2(3) . . ? C1 N1 C33 120.2(3) . . ? C1 N1 Bi1 118.8(2) . . ? C33 N1 Bi1 120.66(19) . . ? C32 C33 C28 121.9(3) . . ? C32 C33 N1 118.9(3) . . ? C28 C33 N1 119.2(3) . . ? C29 C28 C33 117.3(3) . . ? C29 C28 C27 121.2(3) . . ? C33 C28 C27 121.4(3) . . ? C30 C29 C28 122.1(4) . . ? C30 C29 H29A 119.0 . . ? C28 C29 H29A 119.0 . . ? C29 C30 C31 119.4(3) . . ? C29 C30 H30A 120.3 . . ? C31 C30 H30A 120.3 . . ? C32 C31 C30 120.0(3) . . ? C32 C31 H31A 120.0 . . ? C30 C31 H31A 120.0 . . ? C31 C32 C33 119.4(3) . . ? C31 C32 H32A 120.3 . . ? C33 C32 H32A 120.3 . . ? C28 C27 C26 113.0(3) . . ? C28 C27 H27B 109.0 . . ? C26 C27 H27B 109.0 . . ? C28 C27 H27A 109.0 . . ? C26 C27 H27A 109.0 . . ? H27B C27 H27A 107.8 . . ? C25 C26 C27 112.2(3) . . ? C25 C26 H26B 109.2 . . ? C27 C26 H26B 109.2 . . ? C25 C26 H26A 109.2 . . ? C27 C26 H26A 109.2 . . ? H26B C26 H26A 107.9 . . ? N3 C25 C24 121.8(3) . . ? N3 C25 C26 116.9(3) . . ? C24 C25 C26 121.3(3) . . ? C23 C22 C21 118.9(4) . . ? C23 C22 H22A 120.6 . . ? C21 C22 H22A 120.6 . . ? C24 C23 C22 119.2(4) . . ? C24 C23 H23A 120.4 . . ? C22 C23 H23A 120.4 . . ? C23 C24 C25 119.3(4) . . ? C23 C24 H24A 120.3 . . ? C25 C24 H24A 120.3 . . ? C21 C20 C19 111.0(3) . . ? C21 C20 H20B 109.4 . . ? C19 C20 H20B 109.4 . . ? C21 C20 H20A 109.4 . . ? C19 C20 H20A 109.4 . . ? H20B C20 H20A 108.0 . . ? C18 C19 C20 110.3(3) . . ? C18 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? C18 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? H19B C19 H19A 108.1 . . ? C17 C18 C13 117.4(4) . . ? C17 C18 C19 122.7(3) . . ? C13 C18 C19 119.9(3) . . ? C16 C17 C18 121.5(4) . . ? C16 C17 H17A 119.3 . . ? C18 C17 H17A 119.3 . . ? C15 C16 C17 120.1(4) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C16 C15 C14 120.4(4) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C15 C14 C13 119.2(4) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C14 C13 C18 121.5(3) . . ? C14 C13 N2 119.9(3) . . ? C18 C13 N2 118.6(3) . . ? C2 N2 C13 119.1(3) . . ? C2 N2 Bi1 113.6(2) . . ? C13 N2 Bi1 126.8(2) . . ? N2 C2 C3 133.7(3) . . ? N2 C2 C1 119.2(3) . . ? C3 C2 C1 106.9(3) . . ? C4 C3 C8 119.1(3) . . ? C4 C3 C2 134.8(3) . . ? C8 C3 C2 106.1(3) . . ? C7 C8 C3 123.1(3) . . ? C7 C8 C12 122.8(3) . . ? C3 C8 C12 114.0(3) . . ? C8 C7 C9 116.7(3) . . ? C8 C7 C6 116.2(3) . . ? C9 C7 C6 127.1(3) . . ? C5 C6 C7 120.9(3) . . ? C5 C6 H6A 119.6 . . ? C7 C6 H6A 119.6 . . ? C6 C5 C4 122.3(3) . . ? C6 C5 H5A 118.8 . . ? C4 C5 H5A 118.8 . . ? C3 C4 C5 118.4(3) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? C10 C9 C7 120.5(3) . . ? C10 C9 H9A 119.7 . . ? C7 C9 H9A 119.7 . . ? C9 C10 C11 122.5(4) . . ? C9 C10 H10A 118.7 . . ? C11 C10 H10A 118.7 . . ? C12 C11 C10 117.9(4) . . ? C12 C11 H11A 121.1 . . ? C10 C11 H11A 121.1 . . ? C11 C12 C8 119.6(3) . . ? C11 C12 C1 134.4(3) . . ? C8 C12 C1 106.0(3) . . ? N1 C1 C12 132.7(3) . . ? N1 C1 C2 120.2(3) . . ? C12 C1 C2 107.0(3) . . ? Cl4 C100 Cl3 113.2(3) . . ? Cl4 C100 H10B 108.9 . . ? Cl3 C100 H10B 108.9 . . ? Cl4 C100 H10C 108.9 . . ? Cl3 C100 H10C 108.9 . . ? H10B C100 H10C 107.8 . . ? Cl5 C200 Cl6 113.4(4) . . ? Cl5 C200 H20C 108.9 . . ? Cl6 C200 H20C 108.9 . . ? Cl5 C200 H20D 108.9 . . ? Cl6 C200 H20D 108.9 . . ? H20C C200 H20D 107.7 . . ? F2 C34 F1 108.2(10) . . ? F2 C34 F3 109.0(10) . . ? F1 C34 F3 107.7(11) . . ? F2 C34 S1 113.2(8) . . ? F1 C34 S1 111.3(9) . . ? F3 C34 S1 107.4(8) . . ? F6 C35 F4 111(2) . . ? F6 C35 F5 108(2) . . ? F4 C35 F5 106.8(19) . . ? F6 C35 S1 109.4(15) . . ? F4 C35 S1 108.3(17) . . ? F5 C35 S1 113.0(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 O1 Bi1 131.0(2) . . . . ? O3 S1 O1 Bi1 -4.6(2) . . . . ? C35 S1 O1 Bi1 -113.0(9) . . . . ? C34 S1 O1 Bi1 -115.7(4) . . . . ? N1 Bi1 O1 S1 -147.1(2) . . . . ? Cl1 Bi1 O1 S1 -76.72(16) . . . . ? Cl2 Bi1 O1 S1 -168.32(18) . . . . ? N2 Bi1 O1 S1 -3.6(2) . . . . ? C25 N3 C21 C22 -1.7(5) . . . . ? C25 N3 C21 C20 176.5(3) . . . . ? Cl1 Bi1 N1 C1 69.6(2) . . . . ? Cl2 Bi1 N1 C1 161.3(2) . . . . ? N2 Bi1 N1 C1 -10.4(2) . . . . ? O1 Bi1 N1 C1 140.4(3) . . . . ? Cl1 Bi1 N1 C33 -103.3(2) . . . . ? Cl2 Bi1 N1 C33 -11.6(2) . . . . ? N2 Bi1 N1 C33 176.7(2) . . . . ? O1 Bi1 N1 C33 -32.5(4) . . . . ? C1 N1 C33 C32 -78.9(4) . . . . ? Bi1 N1 C33 C32 93.9(3) . . . . ? C1 N1 C33 C28 103.2(4) . . . . ? Bi1 N1 C33 C28 -84.0(3) . . . . ? C32 C33 C28 C29 1.5(5) . . . . ? N1 C33 C28 C29 179.3(3) . . . . ? C32 C33 C28 C27 -175.7(3) . . . . ? N1 C33 C28 C27 2.1(5) . . . . ? C33 C28 C29 C30 -0.8(5) . . . . ? C27 C28 C29 C30 176.4(3) . . . . ? C28 C29 C30 C31 0.0(5) . . . . ? C29 C30 C31 C32 0.2(5) . . . . ? C30 C31 C32 C33 0.5(5) . . . . ? C28 C33 C32 C31 -1.4(5) . . . . ? N1 C33 C32 C31 -179.2(3) . . . . ? C29 C28 C27 C26 -82.4(4) . . . . ? C33 C28 C27 C26 94.7(4) . . . . ? C28 C27 C26 C25 -147.8(3) . . . . ? C21 N3 C25 C24 0.2(5) . . . . ? C21 N3 C25 C26 -178.0(3) . . . . ? C27 C26 C25 N3 68.1(4) . . . . ? C27 C26 C25 C24 -110.1(4) . . . . ? N3 C21 C22 C23 2.0(6) . . . . ? C20 C21 C22 C23 -176.1(4) . . . . ? C21 C22 C23 C24 -0.6(7) . . . . ? C22 C23 C24 C25 -0.9(7) . . . . ? N3 C25 C24 C23 1.1(6) . . . . ? C26 C25 C24 C23 179.2(4) . . . . ? N3 C21 C20 C19 -79.5(4) . . . . ? C22 C21 C20 C19 98.7(4) . . . . ? C21 C20 C19 C18 157.1(3) . . . . ? C20 C19 C18 C17 91.9(4) . . . . ? C20 C19 C18 C13 -84.7(4) . . . . ? C13 C18 C17 C16 0.8(6) . . . . ? C19 C18 C17 C16 -175.9(4) . . . . ? C18 C17 C16 C15 -0.2(7) . . . . ? C17 C16 C15 C14 0.0(7) . . . . ? C16 C15 C14 C13 -0.4(6) . . . . ? C15 C14 C13 C18 1.0(6) . . . . ? C15 C14 C13 N2 179.5(3) . . . . ? C17 C18 C13 C14 -1.2(5) . . . . ? C19 C18 C13 C14 175.6(3) . . . . ? C17 C18 C13 N2 -179.7(3) . . . . ? C19 C18 C13 N2 -2.9(5) . . . . ? C14 C13 N2 C2 75.5(4) . . . . ? C18 C13 N2 C2 -106.0(4) . . . . ? C14 C13 N2 Bi1 -95.9(3) . . . . ? C18 C13 N2 Bi1 82.6(4) . . . . ? N1 Bi1 N2 C2 9.7(2) . . . . ? Cl1 Bi1 N2 C2 -79.9(2) . . . . ? Cl2 Bi1 N2 C2 -6.2(3) . . . . ? O1 Bi1 N2 C2 -156.9(2) . . . . ? N1 Bi1 N2 C13 -178.5(3) . . . . ? Cl1 Bi1 N2 C13 91.9(3) . . . . ? Cl2 Bi1 N2 C13 165.6(2) . . . . ? O1 Bi1 N2 C13 14.9(3) . . . . ? C13 N2 C2 C3 4.4(6) . . . . ? Bi1 N2 C2 C3 176.8(3) . . . . ? C13 N2 C2 C1 178.8(3) . . . . ? Bi1 N2 C2 C1 -8.8(4) . . . . ? N2 C2 C3 C4 -1.5(7) . . . . ? C1 C2 C3 C4 -176.4(4) . . . . ? N2 C2 C3 C8 175.8(4) . . . . ? C1 C2 C3 C8 0.9(3) . . . . ? C4 C3 C8 C7 0.6(5) . . . . ? C2 C3 C8 C7 -177.2(3) . . . . ? C4 C3 C8 C12 177.8(3) . . . . ? C2 C3 C8 C12 0.0(4) . . . . ? C3 C8 C7 C9 178.6(3) . . . . ? C12 C8 C7 C9 1.7(5) . . . . ? C3 C8 C7 C6 -0.5(5) . . . . ? C12 C8 C7 C6 -177.4(3) . . . . ? C8 C7 C6 C5 0.0(5) . . . . ? C9 C7 C6 C5 -179.0(4) . . . . ? C7 C6 C5 C4 0.3(6) . . . . ? C8 C3 C4 C5 -0.2(5) . . . . ? C2 C3 C4 C5 176.8(4) . . . . ? C6 C5 C4 C3 -0.2(6) . . . . ? C8 C7 C9 C10 -0.1(6) . . . . ? C6 C7 C9 C10 179.0(4) . . . . ? C7 C9 C10 C11 -1.4(7) . . . . ? C9 C10 C11 C12 1.2(7) . . . . ? C10 C11 C12 C8 0.4(6) . . . . ? C10 C11 C12 C1 -177.1(4) . . . . ? C7 C8 C12 C11 -1.9(5) . . . . ? C3 C8 C12 C11 -179.1(3) . . . . ? C7 C8 C12 C1 176.2(3) . . . . ? C3 C8 C12 C1 -1.0(4) . . . . ? C33 N1 C1 C12 -0.6(5) . . . . ? Bi1 N1 C1 C12 -173.6(3) . . . . ? C33 N1 C1 C2 -176.5(3) . . . . ? Bi1 N1 C1 C2 10.6(4) . . . . ? C11 C12 C1 N1 3.0(7) . . . . ? C8 C12 C1 N1 -174.7(4) . . . . ? C11 C12 C1 C2 179.2(4) . . . . ? C8 C12 C1 C2 1.5(4) . . . . ? N2 C2 C1 N1 -0.5(5) . . . . ? C3 C2 C1 N1 175.3(3) . . . . ? N2 C2 C1 C12 -177.3(3) . . . . ? C3 C2 C1 C12 -1.5(3) . . . . ? O2 S1 C34 F2 62.9(9) . . . . ? O1 S1 C34 F2 -56.9(9) . . . . ? O3 S1 C34 F2 -170.8(8) . . . . ? C35 S1 C34 F2 129(3) . . . . ? O2 S1 C34 F1 -175.1(8) . . . . ? O1 S1 C34 F1 65.2(9) . . . . ? O3 S1 C34 F1 -48.7(10) . . . . ? C35 S1 C34 F1 -109(3) . . . . ? O2 S1 C34 F3 -57.4(9) . . . . ? O1 S1 C34 F3 -177.2(8) . . . . ? O3 S1 C34 F3 68.9(9) . . . . ? C35 S1 C34 F3 9(2) . . . . ? O2 S1 C35 F6 177.6(17) . . . . ? O1 S1 C35 F6 53(2) . . . . ? O3 S1 C35 F6 -64.1(19) . . . . ? C34 S1 C35 F6 60(3) . . . . ? O2 S1 C35 F4 56.5(19) . . . . ? O1 S1 C35 F4 -69(2) . . . . ? O3 S1 C35 F4 174.8(19) . . . . ? C34 S1 C35 F4 -61(3) . . . . ? O2 S1 C35 F5 -61.6(18) . . . . ? O1 S1 C35 F5 173.4(15) . . . . ? O3 S1 C35 F5 56.7(18) . . . . ? C34 S1 C35 F5 -180(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 34.34 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.679 _refine_diff_density_min -1.723 _refine_diff_density_rms 0.148