# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a20325b _database_code_depnum_ccdc_archive 'CCDC 885472' #TrackingRef 'web_deposit_cif_file_0_JunZhang_1339003489.a20325b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H27 Cl N O Rh' _chemical_formula_weight 543.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.671(7) _cell_length_b 19.299(12) _cell_length_c 21.860(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4924(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1010 _cell_measurement_theta_min 3.314 _cell_measurement_theta_max 24.360 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 0.824 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9076 _exptl_absorpt_correction_T_max 0.9370 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.59 _diffrn_reflns_number 22379 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.01 _reflns_number_total 5336 _reflns_number_gt 3481 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00013(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5336 _refine_ls_number_parameters 315 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _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 Rh1 Rh 0.362840(18) 0.112677(11) 0.400389(9) 0.03733(8) Uani 1 1 d . . . Cl1 Cl 0.32760(7) 0.23398(4) 0.40510(3) 0.0511(2) Uani 1 1 d . . . O1 O 0.58423(15) 0.15257(9) 0.55171(7) 0.0366(4) Uani 1 1 d . . . N1 N 0.40539(19) 0.12935(10) 0.53845(9) 0.0348(5) Uani 1 1 d . . . C1 C 0.4544(2) 0.12325(13) 0.47901(11) 0.0352(6) Uani 1 1 d . . . C2 C 0.4841(2) 0.14736(14) 0.57909(11) 0.0354(6) Uani 1 1 d . . . C3 C 0.5669(2) 0.13738(13) 0.48939(11) 0.0355(6) Uani 1 1 d . . . C4 C 0.2844(2) 0.11979(14) 0.55089(11) 0.0366(6) Uani 1 1 d . . . C5 C 0.2133(3) 0.17608(15) 0.55049(13) 0.0465(7) Uani 1 1 d . . . H5 H 0.2417 0.2195 0.5400 0.056 Uiso 1 1 calc R . . C6 C 0.0999(3) 0.16835(18) 0.56565(15) 0.0586(9) Uani 1 1 d . . . H6 H 0.0516 0.2067 0.5662 0.070 Uiso 1 1 calc R . . C7 C 0.0584(3) 0.1047(2) 0.57986(18) 0.0729(10) Uani 1 1 d . . . H7 H -0.0184 0.0995 0.5903 0.087 Uiso 1 1 calc R . . C8 C 0.1292(3) 0.0478(2) 0.5790(2) 0.0855(13) Uani 1 1 d . . . H8 H 0.0998 0.0043 0.5884 0.103 Uiso 1 1 calc R . . C9 C 0.2434(3) 0.05464(17) 0.56437(16) 0.0635(9) Uani 1 1 d . . . H9 H 0.2916 0.0163 0.5636 0.076 Uiso 1 1 calc R . . C10 C 0.4773(2) 0.16499(14) 0.64438(11) 0.0392(7) Uani 1 1 d . . . C11 C 0.5712(3) 0.19878(16) 0.66973(13) 0.0524(8) Uani 1 1 d . . . H11 H 0.6349 0.2088 0.6457 0.063 Uiso 1 1 calc R . . C12 C 0.5694(3) 0.2173(2) 0.73075(15) 0.0713(10) Uani 1 1 d . . . H12 H 0.6321 0.2401 0.7476 0.086 Uiso 1 1 calc R . . C13 C 0.4771(3) 0.2026(2) 0.76651(15) 0.0715(11) Uani 1 1 d . . . H13 H 0.4772 0.2151 0.8076 0.086 Uiso 1 1 calc R . . C14 C 0.3842(3) 0.16941(19) 0.74216(15) 0.0690(10) Uani 1 1 d . . . H14 H 0.3211 0.1596 0.7667 0.083 Uiso 1 1 calc R . . C15 C 0.3837(3) 0.15024(18) 0.68093(13) 0.0563(8) Uani 1 1 d . . . H15 H 0.3205 0.1275 0.6645 0.068 Uiso 1 1 calc R . . C16 C 0.6683(2) 0.14272(13) 0.45069(11) 0.0345(6) Uani 1 1 d . . . C17 C 0.6554(3) 0.14936(16) 0.38750(12) 0.0476(7) Uani 1 1 d . . . H17 H 0.5825 0.1493 0.3703 0.057 Uiso 1 1 calc R . . C18 C 0.7500(3) 0.15602(18) 0.35069(14) 0.0604(9) Uani 1 1 d . . . H18 H 0.7408 0.1600 0.3086 0.072 Uiso 1 1 calc R . . C19 C 0.8585(3) 0.15693(17) 0.37548(15) 0.0579(8) Uani 1 1 d . . . H19 H 0.9220 0.1616 0.3502 0.070 Uiso 1 1 calc R . . C20 C 0.8726(3) 0.15098(16) 0.43694(14) 0.0527(8) Uani 1 1 d . . . H20 H 0.9459 0.1521 0.4536 0.063 Uiso 1 1 calc R . . C21 C 0.7788(2) 0.14336(14) 0.47474(13) 0.0428(7) Uani 1 1 d . . . H21 H 0.7895 0.1386 0.5167 0.051 Uiso 1 1 calc R . . C22 C 0.4429(3) 0.01924(16) 0.37671(15) 0.0551(9) Uani 1 1 d D . . H22 H 0.5082(18) 0.0199(14) 0.3986(11) 0.048(9) Uiso 1 1 d D . . C23 C 0.3459(3) 0.00501(16) 0.41098(15) 0.0563(9) Uani 1 1 d . . . H23 H 0.354(2) -0.0032(14) 0.4538(12) 0.049(8) Uiso 1 1 d . . . C24 C 0.2340(4) -0.0204(2) 0.38635(18) 0.0883(13) Uani 1 1 d . . . H24A H 0.2450 -0.0670 0.3708 0.106 Uiso 1 1 calc R . . H24B H 0.1799 -0.0232 0.4199 0.106 Uiso 1 1 calc R . . C25 C 0.1825(4) 0.0221(2) 0.3373(2) 0.1166(18) Uani 1 1 d . . . H25A H 0.1002 0.0234 0.3434 0.140 Uiso 1 1 calc R . . H25B H 0.1966 -0.0006 0.2984 0.140 Uiso 1 1 calc R . . C26 C 0.2259(4) 0.09528(19) 0.33330(17) 0.0642(10) Uani 1 1 d . . . H26 H 0.175(3) 0.1309(16) 0.3425(13) 0.053(10) Uiso 1 1 d . . . C27 C 0.3231(4) 0.1130(2) 0.30315(14) 0.0609(9) Uani 1 1 d . . . H27 H 0.335(3) 0.1588(17) 0.2906(15) 0.068(11) Uiso 1 1 d . . . C28 C 0.4030(5) 0.0640(2) 0.27074(16) 0.1087(18) Uani 1 1 d . . . H28A H 0.3612 0.0422 0.2375 0.130 Uiso 1 1 calc R . . H28B H 0.4643 0.0910 0.2526 0.130 Uiso 1 1 calc R . . C29 C 0.4544(4) 0.0094(2) 0.30832(15) 0.0859(13) Uani 1 1 d . . . H29A H 0.5352 0.0063 0.2983 0.103 Uiso 1 1 calc R . . H29B H 0.4193 -0.0344 0.2973 0.103 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 Rh1 0.03972(13) 0.03841(13) 0.03386(12) 0.00357(10) -0.00757(10) 0.00068(10) Cl1 0.0594(5) 0.0440(4) 0.0499(4) -0.0003(3) -0.0030(4) 0.0102(3) O1 0.0354(10) 0.0449(11) 0.0296(9) -0.0021(8) 0.0009(8) -0.0025(9) N1 0.0339(12) 0.0351(13) 0.0354(11) 0.0024(9) -0.0021(10) -0.0004(10) C1 0.0391(15) 0.0353(15) 0.0311(13) 0.0035(11) -0.0013(12) -0.0003(12) C2 0.0352(15) 0.0361(15) 0.0348(14) 0.0038(12) 0.0011(12) 0.0008(12) C3 0.0453(17) 0.0348(15) 0.0266(13) 0.0024(11) -0.0019(12) 0.0013(12) C4 0.0314(14) 0.0424(17) 0.0359(14) 0.0035(13) -0.0024(11) -0.0037(12) C5 0.0441(18) 0.0405(18) 0.0548(18) 0.0047(14) 0.0037(15) 0.0014(14) C6 0.0422(19) 0.059(2) 0.075(2) 0.0008(17) 0.0005(17) 0.0074(16) C7 0.0381(19) 0.081(3) 0.099(3) -0.002(2) 0.0073(18) -0.0093(19) C8 0.059(2) 0.052(2) 0.145(4) 0.009(2) 0.015(2) -0.017(2) C9 0.050(2) 0.0401(19) 0.100(3) 0.0074(17) 0.0053(19) -0.0014(16) C10 0.0420(17) 0.0436(17) 0.0321(14) 0.0016(12) 0.0007(13) 0.0045(13) C11 0.053(2) 0.065(2) 0.0399(16) -0.0067(15) 0.0036(15) -0.0025(16) C12 0.067(2) 0.098(3) 0.049(2) -0.0234(19) -0.0068(18) -0.003(2) C13 0.079(3) 0.099(3) 0.0360(18) -0.0146(18) -0.0024(18) 0.023(2) C14 0.066(3) 0.098(3) 0.0440(19) 0.0097(19) 0.0163(18) 0.015(2) C15 0.050(2) 0.078(2) 0.0411(17) 0.0040(16) 0.0038(14) -0.0022(17) C16 0.0390(16) 0.0316(14) 0.0329(14) -0.0008(12) 0.0008(12) 0.0006(11) C17 0.0484(19) 0.0574(19) 0.0369(16) 0.0015(14) 0.0026(13) 0.0018(15) C18 0.066(2) 0.076(2) 0.0396(17) 0.0016(16) 0.0116(17) 0.003(2) C19 0.055(2) 0.061(2) 0.0577(19) -0.0056(17) 0.0214(17) -0.0014(18) C20 0.0408(18) 0.060(2) 0.0575(19) -0.0072(16) 0.0020(15) -0.0018(15) C21 0.0437(18) 0.0448(17) 0.0399(15) -0.0020(13) -0.0001(13) -0.0020(14) C22 0.072(2) 0.0398(18) 0.0538(19) -0.0025(15) -0.0169(19) 0.0133(17) C23 0.078(3) 0.0423(18) 0.049(2) 0.0099(14) -0.0236(18) -0.0065(16) C24 0.102(3) 0.063(2) 0.100(3) 0.024(2) -0.041(3) -0.036(2) C25 0.112(4) 0.089(3) 0.148(4) 0.028(3) -0.078(3) -0.041(3) C26 0.070(3) 0.057(2) 0.065(2) 0.0076(18) -0.039(2) 0.000(2) C27 0.093(3) 0.052(2) 0.0380(16) 0.0020(17) -0.0204(18) 0.011(2) C28 0.183(5) 0.096(3) 0.048(2) -0.005(2) -0.002(3) 0.065(3) C29 0.124(4) 0.078(3) 0.056(2) -0.011(2) -0.004(2) 0.033(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 Rh1 C1 2.034(3) . ? Rh1 C22 2.096(3) . ? Rh1 C23 2.100(3) . ? Rh1 C27 2.176(3) . ? Rh1 C26 2.195(3) . ? Rh1 Cl1 2.3792(16) . ? O1 C2 1.317(3) . ? O1 C3 1.408(3) . ? N1 C2 1.324(3) . ? N1 C1 1.425(3) . ? N1 C4 1.450(3) . ? C1 C3 1.360(4) . ? C2 C10 1.469(4) . ? C3 C16 1.459(4) . ? C4 C5 1.367(4) . ? C4 C9 1.377(4) . ? C5 C6 1.373(4) . ? C6 C7 1.357(5) . ? C7 C8 1.374(5) . ? C8 C9 1.377(4) . ? C10 C15 1.382(4) . ? C10 C11 1.391(4) . ? C11 C12 1.381(4) . ? C12 C13 1.362(5) . ? C13 C14 1.367(5) . ? C14 C15 1.389(4) . ? C16 C21 1.393(4) . ? C16 C17 1.396(4) . ? C17 C18 1.373(4) . ? C18 C19 1.377(4) . ? C19 C20 1.358(4) . ? C20 C21 1.379(4) . ? C22 C23 1.385(5) . ? C22 C29 1.513(4) . ? C23 C24 1.496(5) . ? C24 C25 1.478(5) . ? C25 C26 1.503(5) . ? C26 C27 1.355(5) . ? C27 C28 1.504(5) . ? C28 C29 1.465(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Rh1 C22 93.48(12) . . ? C1 Rh1 C23 93.18(11) . . ? C22 Rh1 C23 38.54(13) . . ? C1 Rh1 C27 159.61(14) . . ? C22 Rh1 C27 81.72(13) . . ? C23 Rh1 C27 95.17(13) . . ? C1 Rh1 C26 164.24(15) . . ? C22 Rh1 C26 91.61(15) . . ? C23 Rh1 C26 81.60(13) . . ? C27 Rh1 C26 36.13(14) . . ? C1 Rh1 Cl1 87.45(7) . . ? C22 Rh1 Cl1 159.13(11) . . ? C23 Rh1 Cl1 162.29(11) . . ? C27 Rh1 Cl1 90.17(10) . . ? C26 Rh1 Cl1 93.07(10) . . ? C2 O1 C3 107.2(2) . . ? C2 N1 C1 110.8(2) . . ? C2 N1 C4 125.7(2) . . ? C1 N1 C4 123.5(2) . . ? C3 C1 N1 102.6(2) . . ? C3 C1 Rh1 131.94(19) . . ? N1 C1 Rh1 124.62(19) . . ? O1 C2 N1 109.3(2) . . ? O1 C2 C10 118.1(2) . . ? N1 C2 C10 132.5(3) . . ? C1 C3 O1 110.0(2) . . ? C1 C3 C16 134.5(2) . . ? O1 C3 C16 115.4(2) . . ? C5 C4 C9 121.1(3) . . ? C5 C4 N1 119.2(2) . . ? C9 C4 N1 119.6(3) . . ? C4 C5 C6 119.8(3) . . ? C7 C6 C5 119.9(3) . . ? C6 C7 C8 120.4(3) . . ? C7 C8 C9 120.6(3) . . ? C8 C9 C4 118.2(3) . . ? C15 C10 C11 119.3(3) . . ? C15 C10 C2 123.8(3) . . ? C11 C10 C2 116.9(3) . . ? C12 C11 C10 119.6(3) . . ? C13 C12 C11 120.8(3) . . ? C12 C13 C14 120.1(3) . . ? C13 C14 C15 120.2(3) . . ? C10 C15 C14 119.9(3) . . ? C21 C16 C17 118.2(2) . . ? C21 C16 C3 122.2(2) . . ? C17 C16 C3 119.5(2) . . ? C18 C17 C16 120.1(3) . . ? C17 C18 C19 120.7(3) . . ? C20 C19 C18 120.0(3) . . ? C19 C20 C21 120.4(3) . . ? C20 C21 C16 120.6(3) . . ? C23 C22 C29 125.6(3) . . ? C23 C22 Rh1 70.89(19) . . ? C29 C22 Rh1 113.0(2) . . ? C22 C23 C24 125.7(3) . . ? C22 C23 Rh1 70.57(18) . . ? C24 C23 Rh1 111.5(2) . . ? C25 C24 C23 115.7(3) . . ? C24 C25 C26 115.3(3) . . ? C27 C26 C25 123.1(4) . . ? C27 C26 Rh1 71.2(2) . . ? C25 C26 Rh1 110.5(2) . . ? C26 C27 C28 126.1(4) . . ? C26 C27 Rh1 72.71(19) . . ? C28 C27 Rh1 109.0(2) . . ? C29 C28 C27 116.2(3) . . ? C28 C29 C22 115.3(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.464 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.064 data_a20606b _database_code_depnum_ccdc_archive 'CCDC 885473' #TrackingRef 'web_deposit_cif_file_1_JunZhang_1339003489.a20606b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H29 Cl3 N Rh S' _chemical_formula_weight 644.86 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' 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' Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.677(9) _cell_length_b 12.049(15) _cell_length_c 16.55(2) _cell_angle_alpha 109.144(15) _cell_angle_beta 96.378(14) _cell_angle_gamma 97.420(15) _cell_volume 1415(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 930 _cell_measurement_theta_min 2.988 _cell_measurement_theta_max 27.152 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.981 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5770 _exptl_absorpt_correction_T_max 0.6666 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.93 _diffrn_reflns_number 5816 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4862 _reflns_number_gt 4484 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0825P)^2^+0.7925P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.042(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4862 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 Rh1 Rh 0.78974(3) 0.63538(2) 0.810739(17) 0.03507(16) Uani 1 1 d . . . Cl1 Cl 0.98446(13) 0.49136(8) 0.76813(7) 0.0475(3) Uani 1 1 d . . . S1 S 1.24723(14) 0.96108(9) 0.91066(6) 0.0473(3) Uani 1 1 d . . . N1 N 1.0274(4) 0.8332(3) 0.77969(19) 0.0375(7) Uani 1 1 d . . . C1 C 0.9964(5) 0.7758(3) 0.8401(2) 0.0351(7) Uani 1 1 d . . . C2 C 1.1523(5) 0.9326(3) 0.8071(2) 0.0423(8) Uani 1 1 d . . . C3 C 1.1098(5) 0.8373(3) 0.9167(2) 0.0389(8) Uani 1 1 d . . . C4 C 0.9230(5) 0.7876(3) 0.6929(2) 0.0407(8) Uani 1 1 d . . . C5 C 0.8168(6) 0.8581(4) 0.6651(3) 0.0546(10) Uani 1 1 d . . . H5 H 0.8158 0.9357 0.7007 0.065 Uiso 1 1 calc R . . C6 C 0.7130(7) 0.8108(5) 0.5837(3) 0.0683(13) Uani 1 1 d . . . H6 H 0.6402 0.8564 0.5650 0.082 Uiso 1 1 calc R . . C7 C 0.7169(7) 0.6959(5) 0.5301(3) 0.0675(13) Uani 1 1 d . . . H7 H 0.6475 0.6647 0.4753 0.081 Uiso 1 1 calc R . . C8 C 0.8236(7) 0.6279(4) 0.5581(3) 0.0605(12) Uani 1 1 d . . . H8 H 0.8251 0.5507 0.5218 0.073 Uiso 1 1 calc R . . C9 C 0.9293(6) 0.6726(3) 0.6396(3) 0.0476(9) Uani 1 1 d . . . H9 H 1.0023 0.6267 0.6578 0.057 Uiso 1 1 calc R . . C10 C 1.2106(5) 1.0117(3) 0.7589(3) 0.0465(9) Uani 1 1 d . . . C11 C 1.2171(7) 1.1339(4) 0.7975(3) 0.0582(11) Uani 1 1 d . . . H11 H 1.1794 1.1635 0.8508 0.070 Uiso 1 1 calc R . . C12 C 1.2791(8) 1.2121(4) 0.7573(4) 0.0745(15) Uani 1 1 d . . . H12 H 1.2811 1.2936 0.7826 0.089 Uiso 1 1 calc R . . C13 C 1.3383(8) 1.1664(5) 0.6787(4) 0.0814(17) Uani 1 1 d . . . H13 H 1.3846 1.2182 0.6522 0.098 Uiso 1 1 calc R . . C14 C 1.3292(8) 1.0457(5) 0.6397(3) 0.0768(15) Uani 1 1 d . . . H14 H 1.3659 1.0163 0.5861 0.092 Uiso 1 1 calc R . . C15 C 1.2656(7) 0.9672(4) 0.6795(3) 0.0582(11) Uani 1 1 d . . . H15 H 1.2602 0.8855 0.6531 0.070 Uiso 1 1 calc R . . C16 C 1.1364(5) 0.8122(3) 0.9990(2) 0.0393(8) Uani 1 1 d . . . C17 C 1.0613(6) 0.7020(4) 1.0027(3) 0.0517(10) Uani 1 1 d . . . H17 H 0.9913 0.6447 0.9537 0.062 Uiso 1 1 calc R . . C18 C 1.0906(7) 0.6774(4) 1.0792(3) 0.0613(12) Uani 1 1 d . . . H18 H 1.0379 0.6045 1.0811 0.074 Uiso 1 1 calc R . . C19 C 1.1974(7) 0.7607(4) 1.1524(3) 0.0606(11) Uani 1 1 d . . . H19 H 1.2189 0.7436 1.2030 0.073 Uiso 1 1 calc R . . C20 C 1.2714(7) 0.8690(4) 1.1492(3) 0.0616(12) Uani 1 1 d . . . H20 H 1.3430 0.9252 1.1983 0.074 Uiso 1 1 calc R . . C21 C 1.2413(6) 0.8959(4) 1.0742(3) 0.0506(10) Uani 1 1 d . . . H21 H 1.2911 0.9703 1.0739 0.061 Uiso 1 1 calc R . . C22 C 0.6559(6) 0.7440(4) 0.9011(3) 0.0488(9) Uani 1 1 d . . . H22 H 0.739(6) 0.806(4) 0.943(3) 0.055(12) Uiso 1 1 d . . . C23 C 0.6011(6) 0.7517(4) 0.8195(3) 0.0476(9) Uani 1 1 d . . . H23 H 0.655(7) 0.811(4) 0.805(3) 0.060(14) Uiso 1 1 d . . . C24 C 0.4218(6) 0.6894(4) 0.7610(3) 0.0560(10) Uani 1 1 d . . . H24A H 0.3324 0.6828 0.7970 0.067 Uiso 1 1 calc R . . H24B H 0.3860 0.7382 0.7279 0.067 Uiso 1 1 calc R . . C25 C 0.4281(6) 0.5653(4) 0.6984(3) 0.0558(10) Uani 1 1 d . . . H25A H 0.3097 0.5174 0.6840 0.067 Uiso 1 1 calc R . . H25B H 0.4617 0.5723 0.6453 0.067 Uiso 1 1 calc R . . C26 C 0.5567(5) 0.5014(4) 0.7341(3) 0.0467(9) Uani 1 1 d . . . H26 H 0.611(6) 0.443(4) 0.695(3) 0.045(11) Uiso 1 1 d . . . C27 C 0.5754(5) 0.4954(4) 0.8165(3) 0.0472(9) Uani 1 1 d . . . H27 H 0.649(6) 0.436(4) 0.829(3) 0.047(11) Uiso 1 1 d . . . C28 C 0.4628(6) 0.5477(4) 0.8847(3) 0.0562(11) Uani 1 1 d . . . H28A H 0.4441 0.4958 0.9182 0.067 Uiso 1 1 calc R . . H28B H 0.3473 0.5514 0.8562 0.067 Uiso 1 1 calc R . . C29 C 0.5520(6) 0.6734(4) 0.9459(3) 0.0577(11) Uani 1 1 d . . . H29A H 0.4611 0.7165 0.9706 0.069 Uiso 1 1 calc R . . H29B H 0.6317 0.6667 0.9932 0.069 Uiso 1 1 calc R . . C30 C 0.9064(9) 0.2353(5) 0.5795(5) 0.0904(18) Uani 1 1 d . . . H30A H 0.9986 0.2153 0.5444 0.108 Uiso 1 1 calc R . . H30B H 0.9613 0.2983 0.6334 0.108 Uiso 1 1 calc R . . Cl2 Cl 0.7459(3) 0.28892(19) 0.52458(13) 0.1160(7) Uani 1 1 d . . . Cl3 Cl 0.8203(5) 0.1127(2) 0.60170(16) 0.1669(13) 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 Rh1 0.0294(2) 0.0287(2) 0.0414(2) 0.00691(13) 0.00563(12) -0.00039(11) Cl1 0.0392(5) 0.0404(5) 0.0605(6) 0.0133(4) 0.0106(4) 0.0081(4) S1 0.0483(6) 0.0391(5) 0.0433(5) 0.0080(4) 0.0026(4) -0.0113(4) N1 0.0326(15) 0.0323(14) 0.0405(16) 0.0074(12) 0.0040(12) -0.0032(12) C1 0.0313(17) 0.0295(16) 0.0427(18) 0.0106(14) 0.0081(14) 0.0023(13) C2 0.043(2) 0.0358(18) 0.0410(19) 0.0078(15) 0.0063(16) -0.0019(15) C3 0.0388(19) 0.0312(17) 0.0395(18) 0.0057(14) 0.0068(15) -0.0022(14) C4 0.039(2) 0.0365(18) 0.0402(19) 0.0103(15) 0.0036(15) -0.0038(15) C5 0.056(3) 0.046(2) 0.057(2) 0.0132(19) 0.002(2) 0.0062(19) C6 0.067(3) 0.070(3) 0.065(3) 0.028(3) -0.010(2) 0.009(2) C7 0.072(3) 0.070(3) 0.047(2) 0.016(2) -0.012(2) -0.009(3) C8 0.073(3) 0.047(2) 0.046(2) 0.0037(19) 0.003(2) -0.004(2) C9 0.054(2) 0.0404(19) 0.043(2) 0.0097(16) 0.0050(17) 0.0052(17) C10 0.042(2) 0.0390(19) 0.051(2) 0.0137(17) 0.0016(17) -0.0078(16) C11 0.058(3) 0.039(2) 0.068(3) 0.012(2) 0.007(2) -0.0021(18) C12 0.088(4) 0.041(2) 0.087(4) 0.024(2) 0.005(3) -0.011(2) C13 0.091(4) 0.074(3) 0.081(4) 0.045(3) 0.004(3) -0.023(3) C14 0.091(4) 0.081(4) 0.058(3) 0.028(3) 0.020(3) -0.008(3) C15 0.069(3) 0.049(2) 0.051(2) 0.016(2) 0.012(2) -0.005(2) C16 0.0340(18) 0.0401(19) 0.0391(18) 0.0089(15) 0.0050(14) 0.0044(15) C17 0.056(2) 0.046(2) 0.045(2) 0.0128(18) 0.0012(18) -0.0029(18) C18 0.078(3) 0.054(3) 0.056(3) 0.025(2) 0.009(2) 0.012(2) C19 0.072(3) 0.067(3) 0.047(2) 0.021(2) 0.009(2) 0.024(2) C20 0.065(3) 0.063(3) 0.043(2) 0.003(2) -0.004(2) 0.013(2) C21 0.050(2) 0.044(2) 0.049(2) 0.0082(18) 0.0039(18) 0.0030(18) C22 0.043(2) 0.040(2) 0.051(2) -0.0002(18) 0.0099(18) 0.0046(17) C23 0.041(2) 0.0353(19) 0.067(3) 0.0167(19) 0.0126(19) 0.0089(16) C24 0.040(2) 0.066(3) 0.064(3) 0.024(2) 0.0067(19) 0.013(2) C25 0.038(2) 0.070(3) 0.051(2) 0.015(2) 0.0012(18) 0.0010(19) C26 0.0297(19) 0.040(2) 0.054(2) 0.0001(17) 0.0061(16) -0.0076(15) C27 0.037(2) 0.040(2) 0.062(2) 0.0174(18) 0.0084(18) -0.0008(16) C28 0.049(2) 0.063(3) 0.060(3) 0.028(2) 0.015(2) 0.001(2) C29 0.046(2) 0.070(3) 0.053(2) 0.014(2) 0.0165(19) 0.008(2) C30 0.076(4) 0.073(4) 0.100(4) 0.006(3) 0.011(3) -0.001(3) Cl2 0.1204(15) 0.1050(13) 0.0991(12) 0.0008(10) 0.0045(11) 0.0412(11) Cl3 0.230(3) 0.1338(19) 0.1046(15) 0.0514(14) -0.0155(17) -0.071(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 Rh1 C1 2.052(4) . ? Rh1 C22 2.100(4) . ? Rh1 C23 2.126(4) . ? Rh1 C26 2.196(4) . ? Rh1 C27 2.232(4) . ? Rh1 Cl1 2.418(2) . ? S1 C2 1.690(4) . ? S1 C3 1.750(4) . ? N1 C2 1.345(5) . ? N1 C1 1.415(5) . ? N1 C4 1.456(5) . ? C1 C3 1.374(5) . ? C2 C10 1.488(5) . ? C3 C16 1.487(5) . ? C4 C9 1.387(6) . ? C4 C5 1.397(6) . ? C5 C6 1.383(7) . ? C5 H5 0.9300 . ? C6 C7 1.384(7) . ? C6 H6 0.9300 . ? C7 C8 1.377(8) . ? C7 H7 0.9300 . ? C8 C9 1.391(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.383(6) . ? C10 C11 1.391(6) . ? C11 C12 1.386(7) . ? C11 H11 0.9300 . ? C12 C13 1.389(9) . ? C12 H12 0.9300 . ? C13 C14 1.372(8) . ? C13 H13 0.9300 . ? C14 C15 1.390(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C21 1.401(6) . ? C16 C17 1.401(6) . ? C17 C18 1.393(6) . ? C17 H17 0.9300 . ? C18 C19 1.384(7) . ? C18 H18 0.9300 . ? C19 C20 1.374(7) . ? C19 H19 0.9300 . ? C20 C21 1.385(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.405(6) . ? C22 C29 1.510(6) . ? C22 H22 0.94(5) . ? C23 C24 1.535(6) . ? C23 H23 0.89(5) . ? C24 C25 1.524(7) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.510(6) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.382(6) . ? C26 H26 0.96(4) . ? C27 C28 1.519(6) . ? C27 H27 1.03(4) . ? C28 C29 1.537(7) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 Cl3 1.706(7) . ? C30 Cl2 1.762(7) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Rh1 C22 89.72(17) . . ? C1 Rh1 C23 91.03(18) . . ? C22 Rh1 C23 38.82(18) . . ? C1 Rh1 C26 158.15(16) . . ? C22 Rh1 C26 97.41(18) . . ? C23 Rh1 C26 81.99(19) . . ? C1 Rh1 C27 164.93(16) . . ? C22 Rh1 C27 80.78(18) . . ? C23 Rh1 C27 88.85(19) . . ? C26 Rh1 C27 36.36(17) . . ? C1 Rh1 Cl1 91.92(14) . . ? C22 Rh1 Cl1 152.91(13) . . ? C23 Rh1 Cl1 167.88(13) . . ? C26 Rh1 Cl1 90.99(15) . . ? C27 Rh1 Cl1 91.32(15) . . ? C2 S1 C3 91.89(18) . . ? C2 N1 C1 117.0(3) . . ? C2 N1 C4 122.4(3) . . ? C1 N1 C4 120.6(3) . . ? C3 C1 N1 108.9(3) . . ? C3 C1 Rh1 130.2(3) . . ? N1 C1 Rh1 120.6(3) . . ? N1 C2 C10 128.8(3) . . ? N1 C2 S1 110.3(3) . . ? C10 C2 S1 120.8(3) . . ? C1 C3 C16 130.5(3) . . ? C1 C3 S1 111.8(3) . . ? C16 C3 S1 117.6(3) . . ? C9 C4 C5 121.1(4) . . ? C9 C4 N1 118.7(3) . . ? C5 C4 N1 120.2(3) . . ? C6 C5 C4 119.1(4) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 120.4(5) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 119.8(4) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 121.2(4) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C4 C9 C8 118.3(4) . . ? C4 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C15 C10 C11 119.9(4) . . ? C15 C10 C2 121.6(4) . . ? C11 C10 C2 118.4(4) . . ? C12 C11 C10 120.6(5) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 118.8(5) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 120.8(5) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.5(5) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C10 C15 C14 119.4(4) . . ? C10 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C21 C16 C17 117.8(4) . . ? C21 C16 C3 121.4(4) . . ? C17 C16 C3 120.8(3) . . ? C18 C17 C16 120.7(4) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C19 C18 C17 120.4(4) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C18 119.2(4) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C19 C20 C21 121.2(4) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C16 120.6(4) . . ? C20 C21 H21 119.7 . . ? C16 C21 H21 119.7 . . ? C23 C22 C29 126.6(4) . . ? C23 C22 Rh1 71.6(2) . . ? C29 C22 Rh1 111.4(3) . . ? C23 C22 H22 120(3) . . ? C29 C22 H22 109(3) . . ? Rh1 C22 H22 110(3) . . ? C22 C23 C24 125.1(4) . . ? C22 C23 Rh1 69.6(2) . . ? C24 C23 Rh1 112.6(3) . . ? C22 C23 H23 120(3) . . ? C24 C23 H23 113(3) . . ? Rh1 C23 H23 104(3) . . ? C25 C24 C23 113.1(4) . . ? C25 C24 H24A 109.0 . . ? C23 C24 H24A 109.0 . . ? C25 C24 H24B 109.0 . . ? C23 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C26 C25 C24 113.6(4) . . ? C26 C25 H25A 108.9 . . ? C24 C25 H25A 108.9 . . ? C26 C25 H25B 108.9 . . ? C24 C25 H25B 108.9 . . ? H25A C25 H25B 107.7 . . ? C27 C26 C25 125.9(4) . . ? C27 C26 Rh1 73.3(2) . . ? C25 C26 Rh1 107.5(3) . . ? C27 C26 H26 112(2) . . ? C25 C26 H26 120(3) . . ? Rh1 C26 H26 102(3) . . ? C26 C27 C28 125.1(4) . . ? C26 C27 Rh1 70.4(2) . . ? C28 C27 Rh1 111.3(3) . . ? C26 C27 H27 118(2) . . ? C28 C27 H27 115(2) . . ? Rh1 C27 H27 101(2) . . ? C27 C28 C29 111.7(4) . . ? C27 C28 H28A 109.3 . . ? C29 C28 H28A 109.3 . . ? C27 C28 H28B 109.3 . . ? C29 C28 H28B 109.3 . . ? H28A C28 H28B 107.9 . . ? C22 C29 C28 112.9(4) . . ? C22 C29 H29A 109.0 . . ? C28 C29 H29A 109.0 . . ? C22 C29 H29B 109.0 . . ? C28 C29 H29B 109.0 . . ? H29A C29 H29B 107.8 . . ? Cl3 C30 Cl2 113.3(4) . . ? Cl3 C30 H30A 108.9 . . ? Cl2 C30 H30A 108.9 . . ? Cl3 C30 H30B 108.9 . . ? Cl2 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? 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 C2 N1 C1 C3 -1.1(4) . . . . ? C4 N1 C1 C3 -179.1(3) . . . . ? C2 N1 C1 Rh1 172.8(3) . . . . ? C4 N1 C1 Rh1 -5.2(4) . . . . ? C22 Rh1 C1 C3 62.8(4) . . . . ? C23 Rh1 C1 C3 101.6(4) . . . . ? C26 Rh1 C1 C3 172.4(4) . . . . ? C27 Rh1 C1 C3 12.2(8) . . . . ? Cl1 Rh1 C1 C3 -90.1(3) . . . . ? C22 Rh1 C1 N1 -109.5(3) . . . . ? C23 Rh1 C1 N1 -70.7(3) . . . . ? C26 Rh1 C1 N1 0.0(6) . . . . ? C27 Rh1 C1 N1 -160.1(5) . . . . ? Cl1 Rh1 C1 N1 97.5(3) . . . . ? C1 N1 C2 C10 -178.9(4) . . . . ? C4 N1 C2 C10 -1.0(6) . . . . ? C1 N1 C2 S1 1.7(4) . . . . ? C4 N1 C2 S1 179.6(3) . . . . ? C3 S1 C2 N1 -1.4(3) . . . . ? C3 S1 C2 C10 179.2(3) . . . . ? N1 C1 C3 C16 -177.3(4) . . . . ? Rh1 C1 C3 C16 9.7(6) . . . . ? N1 C1 C3 S1 0.0(4) . . . . ? Rh1 C1 C3 S1 -173.1(2) . . . . ? C2 S1 C3 C1 0.8(3) . . . . ? C2 S1 C3 C16 178.5(3) . . . . ? C2 N1 C4 C9 121.6(4) . . . . ? C1 N1 C4 C9 -60.5(5) . . . . ? C2 N1 C4 C5 -59.4(5) . . . . ? C1 N1 C4 C5 118.5(4) . . . . ? C9 C4 C5 C6 1.7(7) . . . . ? N1 C4 C5 C6 -177.3(4) . . . . ? C4 C5 C6 C7 -1.1(8) . . . . ? C5 C6 C7 C8 0.5(8) . . . . ? C6 C7 C8 C9 -0.3(8) . . . . ? C5 C4 C9 C8 -1.5(6) . . . . ? N1 C4 C9 C8 177.4(4) . . . . ? C7 C8 C9 C4 0.8(7) . . . . ? N1 C2 C10 C15 -53.8(6) . . . . ? S1 C2 C10 C15 125.5(4) . . . . ? N1 C2 C10 C11 129.3(5) . . . . ? S1 C2 C10 C11 -51.4(5) . . . . ? C15 C10 C11 C12 -0.3(7) . . . . ? C2 C10 C11 C12 176.7(5) . . . . ? C10 C11 C12 C13 -1.4(8) . . . . ? C11 C12 C13 C14 2.5(9) . . . . ? C12 C13 C14 C15 -2.0(10) . . . . ? C11 C10 C15 C14 0.8(7) . . . . ? C2 C10 C15 C14 -176.0(5) . . . . ? C13 C14 C15 C10 0.3(9) . . . . ? C1 C3 C16 C21 -170.5(4) . . . . ? S1 C3 C16 C21 12.3(5) . . . . ? C1 C3 C16 C17 11.5(6) . . . . ? S1 C3 C16 C17 -165.7(3) . . . . ? C21 C16 C17 C18 0.1(6) . . . . ? C3 C16 C17 C18 178.2(4) . . . . ? C16 C17 C18 C19 -1.3(7) . . . . ? C17 C18 C19 C20 1.3(8) . . . . ? C18 C19 C20 C21 -0.2(7) . . . . ? C19 C20 C21 C16 -1.1(7) . . . . ? C17 C16 C21 C20 1.1(6) . . . . ? C3 C16 C21 C20 -177.0(4) . . . . ? C1 Rh1 C22 C23 92.0(3) . . . . ? C26 Rh1 C22 C23 -67.3(3) . . . . ? C27 Rh1 C22 C23 -99.7(3) . . . . ? Cl1 Rh1 C22 C23 -174.3(2) . . . . ? C1 Rh1 C22 C29 -145.0(3) . . . . ? C23 Rh1 C22 C29 123.0(4) . . . . ? C26 Rh1 C22 C29 55.7(3) . . . . ? C27 Rh1 C22 C29 23.3(3) . . . . ? Cl1 Rh1 C22 C29 -51.3(5) . . . . ? C29 C22 C23 C24 0.5(7) . . . . ? Rh1 C22 C23 C24 103.9(4) . . . . ? C29 C22 C23 Rh1 -103.4(4) . . . . ? C1 Rh1 C23 C22 -88.3(3) . . . . ? C26 Rh1 C23 C22 112.5(3) . . . . ? C27 Rh1 C23 C22 76.7(3) . . . . ? Cl1 Rh1 C23 C22 167.6(5) . . . . ? C1 Rh1 C23 C24 151.1(3) . . . . ? C22 Rh1 C23 C24 -120.6(4) . . . . ? C26 Rh1 C23 C24 -8.1(3) . . . . ? C27 Rh1 C23 C24 -44.0(3) . . . . ? Cl1 Rh1 C23 C24 47.0(7) . . . . ? C22 C23 C24 C25 -90.1(5) . . . . ? Rh1 C23 C24 C25 -9.9(5) . . . . ? C23 C24 C25 C26 31.9(5) . . . . ? C24 C25 C26 C27 44.8(6) . . . . ? C24 C25 C26 Rh1 -36.9(4) . . . . ? C1 Rh1 C26 C27 -171.4(3) . . . . ? C22 Rh1 C26 C27 -63.3(3) . . . . ? C23 Rh1 C26 C27 -99.0(3) . . . . ? Cl1 Rh1 C26 C27 90.9(2) . . . . ? C1 Rh1 C26 C25 -48.2(5) . . . . ? C22 Rh1 C26 C25 59.9(3) . . . . ? C23 Rh1 C26 C25 24.2(3) . . . . ? C27 Rh1 C26 C25 123.2(4) . . . . ? Cl1 Rh1 C26 C25 -145.9(3) . . . . ? C25 C26 C27 C28 3.0(6) . . . . ? Rh1 C26 C27 C28 102.8(4) . . . . ? C25 C26 C27 Rh1 -99.8(4) . . . . ? C1 Rh1 C27 C26 167.7(5) . . . . ? C22 Rh1 C27 C26 116.2(3) . . . . ? C23 Rh1 C27 C26 78.0(3) . . . . ? Cl1 Rh1 C27 C26 -89.9(2) . . . . ? C1 Rh1 C27 C28 46.6(7) . . . . ? C22 Rh1 C27 C28 -5.0(3) . . . . ? C23 Rh1 C27 C28 -43.1(3) . . . . ? C26 Rh1 C27 C28 -121.1(4) . . . . ? Cl1 Rh1 C27 C28 149.0(3) . . . . ? C26 C27 C28 C29 -94.5(5) . . . . ? Rh1 C27 C28 C29 -14.0(5) . . . . ? C23 C22 C29 C28 43.8(6) . . . . ? Rh1 C22 C29 C28 -38.7(5) . . . . ? C27 C28 C29 C22 34.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.728 _refine_diff_density_min -1.245 _refine_diff_density_rms 0.138 data_a20614a _database_code_depnum_ccdc_archive 'CCDC 887373' #TrackingRef 'web_deposit_cif_file_0_JunZhang_1340016959.a20614a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 F3 N O3 S2' _chemical_formula_weight 463.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.645(3) _cell_length_b 14.571(5) _cell_length_c 15.150(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.947(5) _cell_angle_gamma 90.00 _cell_volume 2083.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 844 _cell_measurement_theta_min 2.697 _cell_measurement_theta_max 25.997 _exptl_crystal_description block _exptl_crystal_colour 'light yello' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9412 _exptl_absorpt_correction_T_max 0.9468 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.74 _diffrn_reflns_number 9226 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4056 _reflns_number_gt 2968 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0903P)^2^+0.5339P] 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 4056 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 N1 N 0.4346(2) 0.41988(14) 0.81074(13) 0.0438(5) Uani 1 1 d . . . O1 O 0.6286(2) 0.29295(14) 0.16437(15) 0.0694(6) Uani 1 1 d . . . O2 O 0.6986(3) 0.15946(17) 0.25797(16) 0.0838(7) Uani 1 1 d . . . O3 O 0.8550(3) 0.28753(19) 0.2672(2) 0.1104(11) Uani 1 1 d . . . S1 S 0.58575(8) 0.35651(5) 0.95193(5) 0.0569(2) Uani 1 1 d . . . S2 S 0.74168(7) 0.23784(5) 0.21408(5) 0.0541(2) Uani 1 1 d . . . F1 F 0.9244(3) 0.13084(15) 0.16224(18) 0.1078(8) Uani 1 1 d . . . F2 F 0.7234(4) 0.1365(2) 0.07185(17) 0.1317(11) Uani 1 1 d . . . F3 F 0.8661(3) 0.2472(2) 0.0778(2) 0.1563(14) Uani 1 1 d . . . C1 C 0.4589(3) 0.34264(17) 0.85847(16) 0.0436(6) Uani 1 1 d . . . C2 C 0.6109(3) 0.46938(17) 0.92587(16) 0.0447(6) Uani 1 1 d . . . C3 C 0.5191(3) 0.4952(2) 0.84748(15) 0.0480(6) Uani 1 1 d . . . H3 H 0.5137 0.5537 0.8225 0.058 Uiso 1 1 calc R . . C4 C 0.3446(3) 0.42958(16) 0.72066(16) 0.0431(6) Uani 1 1 d . . . C5 C 0.2539(3) 0.50343(19) 0.70457(17) 0.0518(6) Uani 1 1 d . . . H5 H 0.2434 0.5425 0.7513 0.062 Uiso 1 1 calc R . . C6 C 0.1788(3) 0.5185(2) 0.6178(2) 0.0639(8) Uani 1 1 d . . . H6 H 0.1177 0.5684 0.6055 0.077 Uiso 1 1 calc R . . C7 C 0.1945(3) 0.4596(2) 0.5497(2) 0.0662(8) Uani 1 1 d . . . H7 H 0.1432 0.4696 0.4915 0.079 Uiso 1 1 calc R . . C8 C 0.2854(3) 0.3859(2) 0.56706(18) 0.0604(7) Uani 1 1 d . . . H8 H 0.2949 0.3465 0.5204 0.073 Uiso 1 1 calc R . . C9 C 0.3624(3) 0.37006(19) 0.65307(17) 0.0504(6) Uani 1 1 d . . . H9 H 0.4245 0.3207 0.6651 0.060 Uiso 1 1 calc R . . C10 C 0.3904(3) 0.25316(17) 0.83913(16) 0.0452(6) Uani 1 1 d . . . C11 C 0.2472(3) 0.24451(19) 0.80235(19) 0.0545(7) Uani 1 1 d . . . H11 H 0.1918 0.2966 0.7871 0.065 Uiso 1 1 calc R . . C12 C 0.1867(3) 0.1585(2) 0.7883(2) 0.0677(8) Uani 1 1 d . . . H12 H 0.0908 0.1529 0.7624 0.081 Uiso 1 1 calc R . . C13 C 0.2670(4) 0.0814(2) 0.8124(2) 0.0691(9) Uani 1 1 d . . . H13 H 0.2253 0.0237 0.8031 0.083 Uiso 1 1 calc R . . C14 C 0.4075(4) 0.0889(2) 0.8499(2) 0.0682(9) Uani 1 1 d . . . H14 H 0.4612 0.0362 0.8663 0.082 Uiso 1 1 calc R . . C15 C 0.4709(3) 0.17402(19) 0.86365(19) 0.0568(7) Uani 1 1 d . . . H15 H 0.5670 0.1787 0.8892 0.068 Uiso 1 1 calc R . . C16 C 0.7256(3) 0.52401(18) 0.98005(16) 0.0468(6) Uani 1 1 d . . . C17 C 0.8114(3) 0.4881(2) 1.05694(19) 0.0639(8) Uani 1 1 d . . . H17 H 0.7923 0.4301 1.0772 0.077 Uiso 1 1 calc R . . C18 C 0.9253(4) 0.5379(3) 1.1038(2) 0.0770(10) Uani 1 1 d . . . H18 H 0.9825 0.5133 1.1554 0.092 Uiso 1 1 calc R . . C19 C 0.9540(4) 0.6231(3) 1.0744(3) 0.0778(10) Uani 1 1 d . . . H19 H 1.0314 0.6561 1.1054 0.093 Uiso 1 1 calc R . . C20 C 0.8691(4) 0.6597(2) 0.9995(3) 0.0792(10) Uani 1 1 d . . . H20 H 0.8887 0.7179 0.9800 0.095 Uiso 1 1 calc R . . C21 C 0.7546(3) 0.6116(2) 0.9524(2) 0.0651(8) Uani 1 1 d . . . H21 H 0.6966 0.6377 0.9019 0.078 Uiso 1 1 calc R . . C22 C 0.8181(4) 0.1859(2) 0.1280(3) 0.0762(10) 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 N1 0.0467(12) 0.0448(11) 0.0385(10) -0.0022(9) 0.0055(9) 0.0015(9) O1 0.0647(13) 0.0628(13) 0.0796(14) 0.0107(11) 0.0119(11) 0.0168(10) O2 0.0798(16) 0.0930(17) 0.0843(16) 0.0380(13) 0.0302(13) 0.0092(13) O3 0.0761(16) 0.0821(17) 0.154(3) -0.0428(18) -0.0206(17) 0.0002(14) S1 0.0633(5) 0.0562(4) 0.0477(4) 0.0027(3) 0.0033(3) 0.0026(3) S2 0.0483(4) 0.0534(4) 0.0599(4) 0.0004(3) 0.0091(3) 0.0026(3) F1 0.1041(17) 0.0929(15) 0.138(2) 0.0234(14) 0.0527(15) 0.0504(14) F2 0.180(3) 0.124(2) 0.0827(16) -0.0353(15) 0.0072(17) 0.036(2) F3 0.186(3) 0.137(2) 0.191(3) 0.087(2) 0.143(3) 0.063(2) C1 0.0447(14) 0.0477(14) 0.0393(12) 0.0026(10) 0.0109(10) 0.0084(10) C2 0.0478(14) 0.0477(14) 0.0389(12) -0.0009(10) 0.0096(10) 0.0044(11) C3 0.0440(13) 0.0631(16) 0.0344(12) -0.0102(11) 0.0027(10) 0.0048(12) C4 0.0455(13) 0.0411(12) 0.0402(12) 0.0027(10) 0.0032(10) -0.0035(10) C5 0.0537(15) 0.0491(15) 0.0500(15) 0.0010(12) 0.0047(12) 0.0013(12) C6 0.0597(17) 0.0606(17) 0.0637(18) 0.0139(15) -0.0045(14) 0.0036(14) C7 0.0674(19) 0.077(2) 0.0467(15) 0.0118(15) -0.0066(14) -0.0090(16) C8 0.0720(19) 0.0654(18) 0.0421(14) -0.0055(13) 0.0076(13) -0.0107(15) C9 0.0536(15) 0.0515(15) 0.0451(14) 0.0007(11) 0.0082(12) 0.0001(12) C10 0.0527(15) 0.0436(13) 0.0423(13) 0.0046(10) 0.0166(11) 0.0069(11) C11 0.0508(16) 0.0496(15) 0.0644(17) 0.0049(12) 0.0148(13) 0.0094(12) C12 0.0616(19) 0.0614(19) 0.081(2) 0.0022(16) 0.0169(16) -0.0044(15) C13 0.082(2) 0.0505(17) 0.080(2) 0.0008(15) 0.0276(18) -0.0048(15) C14 0.091(2) 0.0454(16) 0.074(2) 0.0110(14) 0.0311(18) 0.0189(15) C15 0.0580(17) 0.0577(16) 0.0566(16) 0.0095(13) 0.0164(13) 0.0157(13) C16 0.0476(14) 0.0508(14) 0.0425(13) -0.0060(11) 0.0105(11) 0.0031(11) C17 0.0687(19) 0.0673(18) 0.0500(16) -0.0027(14) -0.0006(14) 0.0032(15) C18 0.069(2) 0.093(3) 0.0589(19) -0.0131(18) -0.0090(16) 0.0020(19) C19 0.0554(19) 0.093(3) 0.084(2) -0.034(2) 0.0106(17) -0.0105(18) C20 0.070(2) 0.070(2) 0.098(3) -0.0154(19) 0.017(2) -0.0147(17) C21 0.0604(18) 0.0621(18) 0.0696(19) 0.0000(15) 0.0064(15) -0.0042(14) C22 0.091(2) 0.061(2) 0.086(2) 0.0205(18) 0.040(2) 0.0211(18) _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 N1 C1 1.332(3) . ? N1 C3 1.411(3) . ? N1 C4 1.465(3) . ? O1 S2 1.436(2) . ? O2 S2 1.426(2) . ? O3 S2 1.415(2) . ? S1 C1 1.681(3) . ? S1 C2 1.720(3) . ? S2 C22 1.794(4) . ? F1 C22 1.321(4) . ? F2 C22 1.324(5) . ? F3 C22 1.317(4) . ? C1 C10 1.463(4) . ? C2 C3 1.379(3) . ? C2 C16 1.468(4) . ? C4 C5 1.376(4) . ? C4 C9 1.379(4) . ? C5 C6 1.380(4) . ? C6 C7 1.374(4) . ? C7 C8 1.376(4) . ? C8 C9 1.379(4) . ? C10 C11 1.384(4) . ? C10 C15 1.397(3) . ? C11 C12 1.380(4) . ? C12 C13 1.371(4) . ? C13 C14 1.361(5) . ? C14 C15 1.380(4) . ? C16 C17 1.385(4) . ? C16 C21 1.389(4) . ? C17 C18 1.384(4) . ? C18 C19 1.367(5) . ? C19 C20 1.362(5) . ? C20 C21 1.376(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C3 114.9(2) . . ? C1 N1 C4 126.2(2) . . ? C3 N1 C4 118.4(2) . . ? C1 S1 C2 91.97(12) . . ? O3 S2 O2 114.20(19) . . ? O3 S2 O1 115.18(16) . . ? O2 S2 O1 115.43(14) . . ? O3 S2 C22 104.15(19) . . ? O2 S2 C22 101.80(15) . . ? O1 S2 C22 103.68(15) . . ? N1 C1 C10 128.5(2) . . ? N1 C1 S1 111.80(18) . . ? C10 C1 S1 119.70(18) . . ? C3 C2 C16 127.5(2) . . ? C3 C2 S1 111.3(2) . . ? C16 C2 S1 121.06(19) . . ? C2 C3 N1 110.1(2) . . ? C5 C4 C9 122.1(2) . . ? C5 C4 N1 118.2(2) . . ? C9 C4 N1 119.4(2) . . ? C4 C5 C6 118.8(3) . . ? C7 C6 C5 119.8(3) . . ? C6 C7 C8 120.6(3) . . ? C7 C8 C9 120.5(3) . . ? C8 C9 C4 118.1(3) . . ? C11 C10 C15 119.0(2) . . ? C11 C10 C1 122.2(2) . . ? C15 C10 C1 118.6(2) . . ? C12 C11 C10 120.0(3) . . ? C13 C12 C11 120.4(3) . . ? C14 C13 C12 120.3(3) . . ? C13 C14 C15 120.5(3) . . ? C14 C15 C10 119.8(3) . . ? C17 C16 C21 118.6(3) . . ? C17 C16 C2 121.0(3) . . ? C21 C16 C2 120.3(2) . . ? C18 C17 C16 120.4(3) . . ? C19 C18 C17 120.1(3) . . ? C20 C19 C18 120.0(3) . . ? C19 C20 C21 120.8(3) . . ? C20 C21 C16 120.1(3) . . ? F3 C22 F1 107.5(3) . . ? F3 C22 F2 106.0(4) . . ? F1 C22 F2 107.4(3) . . ? F3 C22 S2 112.3(3) . . ? F1 C22 S2 111.9(3) . . ? F2 C22 S2 111.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C1 C10 -179.9(2) . . . . ? C4 N1 C1 C10 -8.4(4) . . . . ? C3 N1 C1 S1 0.4(3) . . . . ? C4 N1 C1 S1 171.84(19) . . . . ? C2 S1 C1 N1 -1.2(2) . . . . ? C2 S1 C1 C10 179.0(2) . . . . ? C1 S1 C2 C3 1.7(2) . . . . ? C1 S1 C2 C16 -173.9(2) . . . . ? C16 C2 C3 N1 173.5(2) . . . . ? S1 C2 C3 N1 -1.7(3) . . . . ? C1 N1 C3 C2 0.9(3) . . . . ? C4 N1 C3 C2 -171.3(2) . . . . ? C1 N1 C4 C5 136.0(3) . . . . ? C3 N1 C4 C5 -52.8(3) . . . . ? C1 N1 C4 C9 -49.9(4) . . . . ? C3 N1 C4 C9 121.3(3) . . . . ? C9 C4 C5 C6 -0.3(4) . . . . ? N1 C4 C5 C6 173.7(2) . . . . ? C4 C5 C6 C7 0.7(4) . . . . ? C5 C6 C7 C8 -0.5(5) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C7 C8 C9 C4 0.5(4) . . . . ? C5 C4 C9 C8 -0.3(4) . . . . ? N1 C4 C9 C8 -174.2(2) . . . . ? N1 C1 C10 C11 -37.9(4) . . . . ? S1 C1 C10 C11 141.8(2) . . . . ? N1 C1 C10 C15 146.0(3) . . . . ? S1 C1 C10 C15 -34.3(3) . . . . ? C15 C10 C11 C12 -1.6(4) . . . . ? C1 C10 C11 C12 -177.7(3) . . . . ? C10 C11 C12 C13 1.4(5) . . . . ? C11 C12 C13 C14 -0.4(5) . . . . ? C12 C13 C14 C15 -0.3(5) . . . . ? C13 C14 C15 C10 0.1(4) . . . . ? C11 C10 C15 C14 0.9(4) . . . . ? C1 C10 C15 C14 177.1(2) . . . . ? C3 C2 C16 C17 -178.8(3) . . . . ? S1 C2 C16 C17 -4.0(3) . . . . ? C3 C2 C16 C21 -2.1(4) . . . . ? S1 C2 C16 C21 172.7(2) . . . . ? C21 C16 C17 C18 -1.4(4) . . . . ? C2 C16 C17 C18 175.4(3) . . . . ? C16 C17 C18 C19 0.0(5) . . . . ? C17 C18 C19 C20 1.0(5) . . . . ? C18 C19 C20 C21 -0.4(5) . . . . ? C19 C20 C21 C16 -1.0(5) . . . . ? C17 C16 C21 C20 1.9(4) . . . . ? C2 C16 C21 C20 -174.9(3) . . . . ? O3 S2 C22 F3 -61.1(3) . . . . ? O2 S2 C22 F3 180.0(3) . . . . ? O1 S2 C22 F3 59.8(3) . . . . ? O3 S2 C22 F1 60.0(3) . . . . ? O2 S2 C22 F1 -59.0(3) . . . . ? O1 S2 C22 F1 -179.1(3) . . . . ? O3 S2 C22 F2 -179.8(3) . . . . ? O2 S2 C22 F2 61.2(3) . . . . ? O1 S2 C22 F2 -58.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.427 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.056 data_a20614b _database_code_depnum_ccdc_archive 'CCDC 887374' #TrackingRef 'web_deposit_cif_file_1_JunZhang_1340016959.a20614b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H18 F3 N O4 S2' _chemical_formula_weight 493.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.594(6) _cell_length_b 10.726(9) _cell_length_c 15.412(12) _cell_angle_alpha 106.631(9) _cell_angle_beta 98.221(10) _cell_angle_gamma 103.331(10) _cell_volume 1140.7(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 784 _cell_measurement_theta_min 2.830 _cell_measurement_theta_max 27.150 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9134 _exptl_absorpt_correction_T_max 0.9393 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 7.14 _diffrn_reflns_number 4714 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3924 _reflns_number_gt 3154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.20(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3924 _refine_ls_number_parameters 304 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0978 _refine_ls_wR_factor_ref 0.2740 _refine_ls_wR_factor_gt 0.2606 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.160 _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 S1 S 0.10694(12) 0.91000(9) 0.40464(6) 0.0491(4) Uani 1 1 d . . . S2 S 0.82157(15) 0.12879(10) 0.26815(7) 0.0582(4) Uani 1 1 d . . . N1 N 0.1791(4) 0.8895(3) 0.24899(19) 0.0428(7) Uani 1 1 d . . . O1 O -0.5868(4) 0.4128(3) 0.1082(2) 0.0739(9) Uani 1 1 d . . . O2 O 0.6645(5) 0.1667(4) 0.2411(3) 0.0865(11) Uani 1 1 d . . . O3 O 0.9123(7) 0.0703(4) 0.2011(3) 0.1122(15) Uani 1 1 d . . . O4 O 0.7976(7) 0.0547(5) 0.3293(4) 0.1232(17) Uani 1 1 d . . . F1 F 1.0254(6) 0.3618(4) 0.2795(4) 0.1380(17) Uani 1 1 d . . . F2 F 0.9276(7) 0.3679(5) 0.3949(3) 0.1545(19) Uani 1 1 d . . . F3 F 1.1440(6) 0.2764(4) 0.3714(4) 0.159(2) Uani 1 1 d . . . C1 C 0.0560(5) 0.8300(3) 0.2894(2) 0.0419(8) Uani 1 1 d . . . C2 C 0.2951(5) 1.0294(3) 0.3978(2) 0.0425(8) Uani 1 1 d . . . C3 C 0.3112(5) 1.0029(3) 0.3096(2) 0.0443(8) Uani 1 1 d D . . C4 C 0.1804(5) 0.8398(4) 0.1520(2) 0.0460(8) Uani 1 1 d . . . C5 C 0.1818(7) 0.9271(4) 0.1017(3) 0.0637(11) Uani 1 1 d . . . H5 H 0.1802 1.0159 0.1296 0.076 Uiso 1 1 calc R . . C6 C 0.1857(8) 0.8808(6) 0.0096(3) 0.0808(14) Uani 1 1 d . . . H6 H 0.1880 0.9389 -0.0253 0.097 Uiso 1 1 calc R . . C7 C 0.1864(7) 0.7491(6) -0.0316(3) 0.0806(15) Uani 1 1 d . . . H7 H 0.1883 0.7180 -0.0943 0.097 Uiso 1 1 calc R . . C8 C 0.1842(6) 0.6655(5) 0.0188(3) 0.0702(13) Uani 1 1 d . . . H8 H 0.1840 0.5764 -0.0098 0.084 Uiso 1 1 calc R . . C9 C 0.1823(5) 0.7085(4) 0.1113(3) 0.0571(10) Uani 1 1 d . . . H9 H 0.1823 0.6501 0.1458 0.069 Uiso 1 1 calc R . . C10 C -0.1065(5) 0.7170(3) 0.2419(2) 0.0406(8) Uani 1 1 d . . . C11 C -0.2250(5) 0.7184(3) 0.1648(2) 0.0447(8) Uani 1 1 d . . . H11 H -0.1969 0.7910 0.1427 0.054 Uiso 1 1 calc R . . C12 C -0.3801(5) 0.6153(4) 0.1223(3) 0.0505(9) Uani 1 1 d . . . H12 H -0.4570 0.6162 0.0699 0.061 Uiso 1 1 calc R . . C13 C -0.4277(5) 0.5065(3) 0.1555(3) 0.0502(9) Uani 1 1 d . . . C14 C -0.3110(5) 0.5043(4) 0.2300(3) 0.0509(9) Uani 1 1 d . . . H14 H -0.3387 0.4309 0.2514 0.061 Uiso 1 1 calc R . . C15 C -0.1536(5) 0.6086(4) 0.2740(3) 0.0503(9) Uani 1 1 d . . . H15 H -0.0771 0.6069 0.3262 0.060 Uiso 1 1 calc R . . C16 C -0.6398(8) 0.2940(5) 0.1347(5) 0.0981(19) Uani 1 1 d . . . H16A H -0.5424 0.2507 0.1331 0.147 Uiso 1 1 calc R . . H16B H -0.7516 0.2322 0.0922 0.147 Uiso 1 1 calc R . . H16C H -0.6610 0.3197 0.1964 0.147 Uiso 1 1 calc R . . C17 C 0.4061(5) 1.1387(3) 0.4811(2) 0.0444(8) Uani 1 1 d . . . C18 C 0.3940(5) 1.1371(4) 0.5684(3) 0.0506(9) Uani 1 1 d . . . H18 H 0.3136 1.0627 0.5754 0.061 Uiso 1 1 calc R . . C19 C 0.4980(6) 1.2427(4) 0.6457(3) 0.0604(11) Uani 1 1 d . . . H19 H 0.4865 1.2403 0.7045 0.073 Uiso 1 1 calc R . . C20 C 0.6181(6) 1.3512(5) 0.6365(3) 0.0706(12) Uani 1 1 d . . . H20 H 0.6881 1.4234 0.6889 0.085 Uiso 1 1 calc R . . C21 C 0.6354(7) 1.3539(5) 0.5512(3) 0.0781(14) Uani 1 1 d . . . H21 H 0.7204 1.4275 0.5459 0.094 Uiso 1 1 calc R . . C22 C 0.5303(6) 1.2503(4) 0.4714(3) 0.0638(11) Uani 1 1 d . . . H22 H 0.5417 1.2546 0.4130 0.077 Uiso 1 1 calc R . . C23 C 0.9833(8) 0.2860(5) 0.3396(5) 0.0962(19) Uani 1 1 d . . . H3 H 0.404(5) 1.050(4) 0.289(3) 0.070(13) Uiso 1 1 d 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 S1 0.0489(6) 0.0434(6) 0.0476(6) 0.0127(4) 0.0070(4) 0.0047(4) S2 0.0645(7) 0.0502(7) 0.0691(7) 0.0295(5) 0.0203(5) 0.0184(5) N1 0.0412(15) 0.0370(14) 0.0440(15) 0.0101(12) 0.0023(12) 0.0080(12) O1 0.0572(17) 0.0497(16) 0.096(2) 0.0242(16) -0.0044(15) -0.0081(14) O2 0.0597(19) 0.077(2) 0.123(3) 0.043(2) 0.0083(18) 0.0136(16) O3 0.124(3) 0.089(3) 0.124(3) 0.018(3) 0.054(3) 0.038(3) O4 0.135(4) 0.109(3) 0.161(4) 0.107(3) 0.034(3) 0.024(3) F1 0.107(3) 0.088(2) 0.230(5) 0.082(3) 0.040(3) 0.010(2) F2 0.161(4) 0.113(3) 0.132(3) -0.026(3) 0.014(3) 0.026(3) F3 0.096(3) 0.103(3) 0.235(6) 0.046(3) -0.059(3) 0.021(2) C1 0.0416(17) 0.0342(16) 0.0487(19) 0.0133(14) 0.0064(14) 0.0115(14) C2 0.0422(18) 0.0334(16) 0.0473(19) 0.0126(14) 0.0038(14) 0.0070(14) C3 0.0383(18) 0.0389(18) 0.051(2) 0.0137(15) 0.0064(14) 0.0067(15) C4 0.0394(18) 0.0454(19) 0.0471(19) 0.0096(15) 0.0076(14) 0.0092(15) C5 0.081(3) 0.055(2) 0.054(2) 0.0203(18) 0.018(2) 0.014(2) C6 0.094(4) 0.096(4) 0.060(3) 0.036(3) 0.022(2) 0.024(3) C7 0.079(3) 0.104(4) 0.049(2) 0.010(3) 0.019(2) 0.024(3) C8 0.062(3) 0.069(3) 0.062(3) -0.006(2) 0.012(2) 0.022(2) C9 0.052(2) 0.054(2) 0.058(2) 0.0095(18) 0.0076(17) 0.0168(18) C10 0.0424(17) 0.0364(16) 0.0415(17) 0.0117(13) 0.0080(13) 0.0108(14) C11 0.0478(19) 0.0365(17) 0.0506(19) 0.0154(14) 0.0086(15) 0.0142(15) C12 0.0464(19) 0.0454(19) 0.052(2) 0.0135(16) -0.0008(15) 0.0085(16) C13 0.049(2) 0.0361(18) 0.060(2) 0.0130(16) 0.0082(16) 0.0072(16) C14 0.051(2) 0.0390(18) 0.065(2) 0.0235(17) 0.0112(17) 0.0108(16) C15 0.050(2) 0.046(2) 0.057(2) 0.0241(17) 0.0049(16) 0.0137(17) C16 0.070(3) 0.058(3) 0.147(6) 0.043(3) -0.004(3) -0.013(2) C17 0.0398(18) 0.0371(17) 0.050(2) 0.0100(15) 0.0038(14) 0.0081(15) C18 0.0473(19) 0.052(2) 0.051(2) 0.0158(17) 0.0068(15) 0.0164(17) C19 0.062(2) 0.069(3) 0.046(2) 0.0071(18) 0.0067(17) 0.029(2) C20 0.063(3) 0.058(2) 0.063(3) -0.006(2) 0.004(2) 0.005(2) C21 0.075(3) 0.057(2) 0.068(3) 0.004(2) 0.002(2) -0.017(2) C22 0.069(3) 0.051(2) 0.050(2) 0.0096(17) 0.0043(18) -0.0077(19) C23 0.077(4) 0.054(3) 0.149(6) 0.023(3) 0.011(4) 0.025(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 S1 C1 1.679(4) . ? S1 C2 1.724(4) . ? S2 O2 1.393(4) . ? S2 O4 1.402(4) . ? S2 O3 1.402(4) . ? S2 C23 1.777(6) . ? N1 C1 1.337(4) . ? N1 C3 1.370(4) . ? N1 C4 1.439(5) . ? O1 C13 1.331(5) . ? O1 C16 1.435(6) . ? F1 C23 1.419(8) . ? F2 C23 1.235(7) . ? F3 C23 1.287(6) . ? C1 C10 1.439(5) . ? C2 C3 1.337(5) . ? C2 C17 1.451(5) . ? C3 H3 0.92(2) . ? C4 C9 1.373(5) . ? C4 C5 1.375(6) . ? C5 C6 1.370(7) . ? C5 H5 0.9300 . ? C6 C7 1.374(7) . ? C6 H6 0.9300 . ? C7 C8 1.344(7) . ? C7 H7 0.9300 . ? C8 C9 1.371(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.383(5) . ? C10 C11 1.390(5) . ? C11 C12 1.343(5) . ? C11 H11 0.9300 . ? C12 C13 1.397(5) . ? C12 H12 0.9300 . ? C13 C14 1.357(5) . ? C14 C15 1.363(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.367(5) . ? C17 C22 1.402(5) . ? C18 C19 1.368(5) . ? C18 H18 0.9300 . ? C19 C20 1.359(7) . ? C19 H19 0.9300 . ? C20 C21 1.347(7) . ? C20 H20 0.9300 . ? C21 C22 1.383(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C2 91.69(17) . . ? O2 S2 O4 112.8(3) . . ? O2 S2 O3 119.9(3) . . ? O4 S2 O3 110.4(3) . . ? O2 S2 C23 103.0(3) . . ? O4 S2 C23 103.2(3) . . ? O3 S2 C23 105.6(3) . . ? C1 N1 C3 113.6(3) . . ? C1 N1 C4 124.6(3) . . ? C3 N1 C4 121.7(3) . . ? C13 O1 C16 118.2(4) . . ? N1 C1 C10 125.7(3) . . ? N1 C1 S1 111.2(2) . . ? C10 C1 S1 123.0(3) . . ? C3 C2 C17 130.2(3) . . ? C3 C2 S1 109.8(2) . . ? C17 C2 S1 120.0(3) . . ? C2 C3 N1 113.6(3) . . ? C2 C3 H3 126(3) . . ? N1 C3 H3 121(3) . . ? C9 C4 C5 121.1(4) . . ? C9 C4 N1 120.3(3) . . ? C5 C4 N1 118.6(3) . . ? C6 C5 C4 118.8(4) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C7 120.4(5) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 119.8(4) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 121.5(4) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 118.5(4) . . ? C8 C9 H9 120.8 . . ? C4 C9 H9 120.8 . . ? C15 C10 C11 118.5(3) . . ? C15 C10 C1 121.4(3) . . ? C11 C10 C1 120.0(3) . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? O1 C13 C14 126.3(4) . . ? O1 C13 C12 114.9(3) . . ? C14 C13 C12 118.8(3) . . ? C13 C14 C15 120.7(3) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C14 C15 C10 120.7(3) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 118.8(3) . . ? C18 C17 C2 122.6(3) . . ? C22 C17 C2 118.6(3) . . ? C17 C18 C19 121.3(4) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C20 C19 C18 120.0(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 119.8(4) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 121.9(4) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C21 C22 C17 118.1(4) . . ? C21 C22 H22 120.9 . . ? C17 C22 H22 120.9 . . ? F2 C23 F3 114.7(7) . . ? F2 C23 F1 98.4(5) . . ? F3 C23 F1 101.7(5) . . ? F2 C23 S2 118.4(5) . . ? F3 C23 S2 114.2(4) . . ? F1 C23 S2 106.0(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 C3 N1 C1 C10 174.2(3) . . . . ? C4 N1 C1 C10 -7.5(5) . . . . ? C3 N1 C1 S1 -2.5(4) . . . . ? C4 N1 C1 S1 175.8(2) . . . . ? C2 S1 C1 N1 1.6(3) . . . . ? C2 S1 C1 C10 -175.1(3) . . . . ? C1 S1 C2 C3 -0.4(3) . . . . ? C1 S1 C2 C17 178.7(3) . . . . ? C17 C2 C3 N1 -179.9(3) . . . . ? S1 C2 C3 N1 -0.9(4) . . . . ? C1 N1 C3 C2 2.2(4) . . . . ? C4 N1 C3 C2 -176.2(3) . . . . ? C1 N1 C4 C9 -53.7(5) . . . . ? C3 N1 C4 C9 124.4(4) . . . . ? C1 N1 C4 C5 127.0(4) . . . . ? C3 N1 C4 C5 -54.8(5) . . . . ? C9 C4 C5 C6 -0.2(6) . . . . ? N1 C4 C5 C6 179.1(4) . . . . ? C4 C5 C6 C7 0.6(7) . . . . ? C5 C6 C7 C8 -0.4(8) . . . . ? C6 C7 C8 C9 -0.3(8) . . . . ? C7 C8 C9 C4 0.8(6) . . . . ? C5 C4 C9 C8 -0.5(6) . . . . ? N1 C4 C9 C8 -179.8(3) . . . . ? N1 C1 C10 C15 135.5(4) . . . . ? S1 C1 C10 C15 -48.2(4) . . . . ? N1 C1 C10 C11 -47.8(5) . . . . ? S1 C1 C10 C11 128.4(3) . . . . ? C15 C10 C11 C12 -1.0(5) . . . . ? C1 C10 C11 C12 -177.7(3) . . . . ? C10 C11 C12 C13 1.5(6) . . . . ? C16 O1 C13 C14 -2.8(7) . . . . ? C16 O1 C13 C12 176.4(4) . . . . ? C11 C12 C13 O1 178.5(4) . . . . ? C11 C12 C13 C14 -2.2(6) . . . . ? O1 C13 C14 C15 -178.4(4) . . . . ? C12 C13 C14 C15 2.4(6) . . . . ? C13 C14 C15 C10 -2.0(6) . . . . ? C11 C10 C15 C14 1.2(5) . . . . ? C1 C10 C15 C14 177.9(3) . . . . ? C3 C2 C17 C18 -166.9(4) . . . . ? S1 C2 C17 C18 14.2(5) . . . . ? C3 C2 C17 C22 13.2(6) . . . . ? S1 C2 C17 C22 -165.7(3) . . . . ? C22 C17 C18 C19 1.1(5) . . . . ? C2 C17 C18 C19 -178.8(3) . . . . ? C17 C18 C19 C20 -0.9(6) . . . . ? C18 C19 C20 C21 -0.5(7) . . . . ? C19 C20 C21 C22 1.8(8) . . . . ? C20 C21 C22 C17 -1.5(8) . . . . ? C18 C17 C22 C21 0.1(6) . . . . ? C2 C17 C22 C21 180.0(4) . . . . ? O2 S2 C23 F2 41.8(7) . . . . ? O4 S2 C23 F2 -75.7(7) . . . . ? O3 S2 C23 F2 168.3(6) . . . . ? O2 S2 C23 F3 -178.4(6) . . . . ? O4 S2 C23 F3 64.1(7) . . . . ? O3 S2 C23 F3 -51.8(7) . . . . ? O2 S2 C23 F1 -67.3(4) . . . . ? O4 S2 C23 F1 175.2(4) . . . . ? O3 S2 C23 F1 59.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C3 H3 O2 0.92(2) 2.41(2) 3.331(5) 176(4) 1_565 C18 H18 O4 0.93 2.32 3.157(6) 149.7 2_666 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.955 _refine_diff_density_min -0.877 _refine_diff_density_rms 0.157