data_chan171 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 I N O3 S' _chemical_formula_sum 'C22 H18 I N O3 S' _chemical_formula_weight 503.33 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' 'I' 'I' -0.4742 1.8119 '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 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 10.2734(3) _cell_length_b 17.7404(4) _cell_length_c 14.0160(3) _cell_angle_alpha 90.00 _cell_angle_beta 129.9040(10) _cell_angle_gamma 90.00 _cell_volume 1959.59(8) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 9962 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 33.16 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5388 _exptl_absorpt_correction_T_max 0.6021 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 31818 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 33.29 _reflns_number_total 7517 _reflns_number_gt 6667 _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^)+(0.0206P)^2^+1.0036P] 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 7517 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0532 _refine_ls_wR_factor_gt 0.0515 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.010 _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 I1 I 0.863022(11) 1.034299(5) 0.314437(8) 0.02011(3) Uani 1 1 d . . . S1 S 0.54256(4) 0.814405(17) 0.28421(3) 0.01518(6) Uani 1 1 d . . . O1 O 0.45440(13) 0.92000(6) 0.08175(9) 0.01974(19) Uani 1 1 d . . . O2 O 0.57586(14) 0.79495(6) 0.39698(10) 0.0220(2) Uani 1 1 d . . . O3 O 0.39314(13) 0.78683(6) 0.16840(10) 0.0225(2) Uani 1 1 d . . . N1 N 0.52974(14) 0.90903(6) 0.27654(10) 0.01377(19) Uani 1 1 d . . . C1 C 0.58669(16) 0.96077(7) 0.37541(11) 0.0127(2) Uani 1 1 d . . . C2 C 0.66834(16) 0.94640(8) 0.49948(12) 0.0157(2) Uani 1 1 d . . . H2 H 0.6915 0.8964 0.5307 0.019 Uiso 1 1 calc R . . C3 C 0.71506(17) 1.00842(8) 0.57651(12) 0.0174(2) Uani 1 1 d . . . H3 H 0.7726 1.0004 0.6623 0.021 Uiso 1 1 calc R . . C4 C 0.67958(18) 1.08161(8) 0.53104(12) 0.0183(2) Uani 1 1 d . . . H4 H 0.7102 1.1228 0.5852 0.022 Uiso 1 1 calc R . . C5 C 0.59917(17) 1.09489(7) 0.40624(12) 0.0166(2) Uani 1 1 d . . . H5 H 0.5754 1.1449 0.3747 0.020 Uiso 1 1 calc R . . C6 C 0.55468(16) 1.03382(7) 0.32927(11) 0.0132(2) Uani 1 1 d . . . C7 C 0.48568(16) 1.03355(7) 0.19639(11) 0.0132(2) Uani 1 1 d . . . C8 C 0.30368(16) 1.06250(7) 0.09929(12) 0.0133(2) Uani 1 1 d . . . C9 C 0.20271(17) 1.07833(7) 0.13104(13) 0.0172(2) Uani 1 1 d . . . H9 H 0.2495 1.0747 0.2153 0.021 Uiso 1 1 calc R . . C10 C 0.03360(18) 1.09941(8) 0.03987(14) 0.0215(3) Uani 1 1 d . . . H10 H -0.0350 1.1088 0.0620 0.026 Uiso 1 1 calc R . . C11 C -0.03486(18) 1.10666(8) -0.08281(14) 0.0220(3) Uani 1 1 d . . . H11 H -0.1498 1.1216 -0.1447 0.026 Uiso 1 1 calc R . . C12 C 0.06577(18) 1.09196(8) -0.11469(13) 0.0212(3) Uani 1 1 d . . . H12 H 0.0197 1.0973 -0.1986 0.025 Uiso 1 1 calc R . . C13 C 0.23326(17) 1.06946(8) -0.02466(12) 0.0176(2) Uani 1 1 d . . . H13 H 0.3005 1.0587 -0.0477 0.021 Uiso 1 1 calc R . . C14 C 0.60520(16) 1.07526(8) 0.18381(12) 0.0163(2) Uani 1 1 d . . . H14A H 0.6034 1.1298 0.1979 0.020 Uiso 1 1 calc R . . H14B H 0.5637 1.0688 0.0981 0.020 Uiso 1 1 calc R . . C15 C 0.48564(16) 0.94876(7) 0.17218(12) 0.0145(2) Uani 1 1 d . . . C16 C 0.71916(16) 0.79337(7) 0.29655(12) 0.0148(2) Uani 1 1 d . . . C17 C 0.87961(17) 0.79904(7) 0.41228(12) 0.0181(2) Uani 1 1 d . . . H17 H 0.8931 0.8157 0.4826 0.022 Uiso 1 1 calc R . . C18 C 1.01985(18) 0.78003(8) 0.42353(13) 0.0207(3) Uani 1 1 d . . . H18 H 1.1303 0.7842 0.5021 0.025 Uiso 1 1 calc R . . C19 C 1.00089(18) 0.75492(7) 0.32099(14) 0.0204(3) Uani 1 1 d . . . C20 C 1.1529(2) 0.72974(9) 0.33527(18) 0.0305(3) Uani 1 1 d . . . H20A H 1.2569 0.7417 0.4194 0.046 Uiso 1 1 calc R . . H20B H 1.1538 0.7559 0.2742 0.046 Uiso 1 1 calc R . . H20C H 1.1465 0.6752 0.3216 0.046 Uiso 1 1 calc R . . C21 C 0.83853(19) 0.75178(8) 0.20528(14) 0.0209(3) Uani 1 1 d . . . H21 H 0.8250 0.7362 0.1345 0.025 Uiso 1 1 calc R . . C22 C 0.69620(18) 0.77094(8) 0.19162(13) 0.0186(2) Uani 1 1 d . . . H22 H 0.5859 0.7688 0.1125 0.022 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 I1 0.01284(4) 0.02723(5) 0.01690(4) 0.00200(3) 0.00800(3) 0.00220(3) S1 0.01340(13) 0.01093(12) 0.01805(14) 0.00006(11) 0.00864(12) -0.00048(10) O1 0.0233(5) 0.0195(4) 0.0140(4) -0.0006(4) 0.0109(4) 0.0044(4) O2 0.0284(5) 0.0159(4) 0.0267(5) 0.0047(4) 0.0200(5) 0.0006(4) O3 0.0142(4) 0.0175(4) 0.0260(5) -0.0053(4) 0.0085(4) -0.0033(4) N1 0.0154(5) 0.0113(4) 0.0123(4) 0.0004(4) 0.0078(4) 0.0012(4) C1 0.0125(5) 0.0125(5) 0.0128(5) -0.0003(4) 0.0080(4) -0.0002(4) C2 0.0144(6) 0.0180(5) 0.0133(5) 0.0033(4) 0.0082(5) 0.0006(4) C3 0.0154(6) 0.0246(6) 0.0115(5) -0.0002(5) 0.0084(5) -0.0020(5) C4 0.0197(6) 0.0198(6) 0.0152(5) -0.0038(5) 0.0111(5) -0.0036(5) C5 0.0189(6) 0.0136(5) 0.0174(5) -0.0006(5) 0.0117(5) -0.0007(4) C6 0.0135(5) 0.0135(5) 0.0119(5) 0.0014(4) 0.0078(4) 0.0007(4) C7 0.0141(5) 0.0126(5) 0.0122(5) 0.0020(4) 0.0082(4) 0.0015(4) C8 0.0134(5) 0.0106(5) 0.0145(5) 0.0019(4) 0.0082(5) 0.0011(4) C9 0.0184(6) 0.0150(5) 0.0205(6) 0.0022(5) 0.0135(5) 0.0018(5) C10 0.0194(6) 0.0170(6) 0.0304(7) 0.0000(5) 0.0170(6) 0.0017(5) C11 0.0136(6) 0.0167(6) 0.0256(7) 0.0018(5) 0.0079(5) 0.0028(5) C12 0.0173(6) 0.0213(6) 0.0158(6) 0.0033(5) 0.0064(5) 0.0022(5) C13 0.0149(6) 0.0207(6) 0.0145(5) 0.0022(5) 0.0082(5) 0.0020(5) C14 0.0131(5) 0.0201(6) 0.0146(5) 0.0045(5) 0.0083(5) 0.0022(4) C15 0.0133(5) 0.0145(5) 0.0129(5) 0.0020(4) 0.0072(5) 0.0027(4) C16 0.0138(5) 0.0104(5) 0.0157(5) 0.0001(4) 0.0074(5) 0.0010(4) C17 0.0156(6) 0.0169(6) 0.0153(5) -0.0011(5) 0.0069(5) 0.0012(5) C18 0.0132(6) 0.0183(6) 0.0205(6) -0.0002(5) 0.0061(5) 0.0015(5) C19 0.0192(6) 0.0125(5) 0.0295(7) -0.0011(5) 0.0156(6) 0.0010(5) C20 0.0256(8) 0.0223(7) 0.0474(10) -0.0054(7) 0.0252(8) 0.0009(6) C21 0.0229(7) 0.0175(6) 0.0234(6) -0.0053(5) 0.0153(6) -0.0020(5) C22 0.0166(6) 0.0177(6) 0.0152(6) -0.0024(5) 0.0074(5) -0.0011(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 I1 C14 2.1619(13) . ? S1 O3 1.4260(11) . ? S1 O2 1.4286(10) . ? S1 N1 1.6820(11) . ? S1 C16 1.7488(13) . ? O1 C15 1.2033(15) . ? N1 C15 1.4112(16) . ? N1 C1 1.4368(16) . ? C1 C2 1.3861(17) . ? C1 C6 1.3903(17) . ? C2 C3 1.3933(19) . ? C2 H2 0.9500 . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.3943(18) . ? C4 H4 0.9500 . ? C5 C6 1.3833(17) . ? C5 H5 0.9500 . ? C6 C7 1.5091(17) . ? C7 C8 1.5320(18) . ? C7 C14 1.5376(18) . ? C7 C15 1.5420(17) . ? C8 C13 1.3943(18) . ? C8 C9 1.3948(17) . ? C9 C10 1.394(2) . ? C9 H9 0.9500 . ? C10 C11 1.384(2) . ? C10 H10 0.9500 . ? C11 C12 1.389(2) . ? C11 H11 0.9500 . ? C12 C13 1.3880(19) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C16 C17 1.3885(18) . ? C16 C22 1.3899(18) . ? C17 C18 1.3867(19) . ? C17 H17 0.9500 . ? C18 C19 1.394(2) . ? C18 H18 0.9500 . ? C19 C21 1.395(2) . ? C19 C20 1.509(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.390(2) . ? C21 H21 0.9500 . ? C22 H22 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 O3 S1 O2 119.70(7) . . ? O3 S1 N1 106.66(6) . . ? O2 S1 N1 105.38(6) . . ? O3 S1 C16 109.29(6) . . ? O2 S1 C16 110.01(6) . . ? N1 S1 C16 104.66(6) . . ? C15 N1 C1 110.00(10) . . ? C15 N1 S1 121.64(9) . . ? C1 N1 S1 127.53(9) . . ? C2 C1 C6 121.81(11) . . ? C2 C1 N1 129.56(11) . . ? C6 C1 N1 108.57(10) . . ? C1 C2 C3 117.22(12) . . ? C1 C2 H2 121.4 . . ? C3 C2 H2 121.4 . . ? C4 C3 C2 121.63(12) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 120.25(12) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 118.65(12) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C1 120.41(11) . . ? C5 C6 C7 128.57(11) . . ? C1 C6 C7 110.77(10) . . ? C6 C7 C8 115.77(10) . . ? C6 C7 C14 111.26(10) . . ? C8 C7 C14 110.25(10) . . ? C6 C7 C15 102.02(10) . . ? C8 C7 C15 107.68(10) . . ? C14 C7 C15 109.37(10) . . ? C13 C8 C9 118.82(12) . . ? C13 C8 C7 119.91(11) . . ? C9 C8 C7 121.17(11) . . ? C10 C9 C8 120.41(13) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 120.34(13) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.48(13) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 120.40(13) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C8 120.53(13) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C7 C14 I1 112.07(8) . . ? C7 C14 H14A 109.2 . . ? I1 C14 H14A 109.2 . . ? C7 C14 H14B 109.2 . . ? I1 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? O1 C15 N1 124.85(12) . . ? O1 C15 C7 127.42(12) . . ? N1 C15 C7 107.72(10) . . ? C17 C16 C22 121.69(12) . . ? C17 C16 S1 118.62(10) . . ? C22 C16 S1 119.69(10) . . ? C18 C17 C16 118.91(13) . . ? C18 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? C17 C18 C19 120.85(13) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C21 118.93(13) . . ? C18 C19 C20 120.64(14) . . ? C21 C19 C20 120.42(14) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C19 121.22(13) . . ? C22 C21 H21 119.4 . . ? C19 C21 H21 119.4 . . ? C21 C22 C16 118.35(13) . . ? C21 C22 H22 120.8 . . ? C16 C22 H22 120.8 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 33.29 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.524 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.072