# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Masahito Ochiai' _publ_contact_author_email MOCHIAI@PH.TOKUSHIMA-U.AC.JP _publ_section_title ; Imido transfer of sulfonylimino-lambda3-bromane makes possible the synthesis of sulfonylimino-lambda3-iodanes ; loop_ _publ_author_name 'Masahito Ochiai' 'Satoko Hayashi' 'Kazunori Miyamoto' 'Waro Nakanishi' 'Aiko Nakano' 'Akira Yoshimura' #===END======================================================================== # Attachment 'New CIF-2.cif' #============================================================================== data_ANA-153 _database_code_depnum_ccdc_archive 'CCDC 692567' #============================================================================== _audit_creation_date 2008-10-27 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? # CHEMICAL DATA _chemical_formula_sum 'C8 H6 F3 I N2 O3 S ' _chemical_formula_moiety 'C8 H6 F3 I N2 O3 S ' _chemical_formula_weight 394.11 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.1853(4) _cell_length_b 14.2294(4) _cell_length_c 14.5837(4) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 2321.14(12) _cell_formula_units_Z 8 _cell_measurement_reflns_used 21547 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 93.1 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 2.255 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504.00 _exptl_absorpt_coefficient_mu 2.982 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.536 _exptl_absorpt_correction_T_max 0.551 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 22509 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_theta_max 27.43 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5281 _reflns_number_gt 5171 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0520 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5281 _refine_ls_number_parameters 326 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0225P)^2^+3.1855P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0020 _refine_diff_density_max 1.96 _refine_diff_density_min -0.40 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 2307 Friedel Pairs' _refine_ls_abs_structure_Flack 0.001(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.017 0.010 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; I I -0.474 1.812 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.390231(19) 0.514881(15) 0.604237(15) 0.01478(4) Uani 1.00 1 d . . . I2 I 0.676268(19) 0.375212(15) 0.851225(15) 0.01448(4) Uani 1.00 1 d . . . S1 S 0.50255(7) 0.33184(6) 0.53395(6) 0.01318(15) Uani 1.00 1 d . . . S2 S 0.44002(8) 0.41248(6) 0.94847(6) 0.01624(16) Uani 1.00 1 d . . . F1 F 0.6473(2) 0.46518(15) 0.47807(17) 0.0240(5) Uani 1.00 1 d . . . F2 F 0.71773(19) 0.32418(16) 0.46265(16) 0.0237(4) Uani 1.00 1 d . . . F3 F 0.5830(2) 0.37603(17) 0.36926(14) 0.0247(4) Uani 1.00 1 d . . . F4 F 0.4692(2) 0.23526(17) 0.99459(19) 0.0341(6) Uani 1.00 1 d . . . F5 F 0.2917(2) 0.28976(18) 1.0190(2) 0.0340(6) Uani 1.00 1 d . . . F6 F 0.4374(2) 0.3277(2) 1.10976(18) 0.0391(6) Uani 1.00 1 d . . . O1 O 0.4752(2) 0.24193(19) 0.49430(19) 0.0215(5) Uani 1.00 1 d . . . O2 O 0.5622(2) 0.33245(18) 0.62213(17) 0.0187(5) Uani 1.00 1 d . . . O3 O 0.3469(2) 0.63636(18) 0.71321(18) 0.0200(5) Uani 1.00 1 d . . . O4 O 0.3974(2) 0.38314(18) 0.86011(18) 0.0204(5) Uani 1.00 1 d . . . O5 O 0.3783(2) 0.4873(2) 0.9942(2) 0.0260(6) Uani 1.00 1 d . . . O6 O 0.8054(2) 0.35097(17) 0.72324(17) 0.0169(5) Uani 1.00 1 d . . . N1 N 0.3946(2) 0.4002(2) 0.5210(2) 0.0165(5) Uani 1.00 1 d . . . N2 N 0.2626(3) 0.6543(2) 0.8557(2) 0.0258(7) Uani 1.00 1 d . . . N3 N 0.5788(2) 0.4252(2) 0.9573(2) 0.0176(6) Uani 1.00 1 d . . . N4 N 0.8824(2) 0.4253(2) 0.5992(2) 0.0182(5) Uani 1.00 1 d . . . C1 C 0.6188(3) 0.3762(2) 0.4565(2) 0.0167(6) Uani 1.00 1 d . . . C2 C 0.2529(3) 0.4613(2) 0.6887(2) 0.0151(6) Uani 1.00 1 d . . . C3 C 0.2013(3) 0.3752(2) 0.6681(2) 0.0183(7) Uani 1.00 1 d . . . C4 C 0.1129(3) 0.3420(2) 0.7270(2) 0.0206(7) Uani 1.00 1 d . . . C5 C 0.0787(3) 0.3931(2) 0.8030(2) 0.0202(7) Uani 1.00 1 d . . . C6 C 0.1318(3) 0.4797(2) 0.8218(2) 0.0194(7) Uani 1.00 1 d . . . C7 C 0.2208(3) 0.5149(2) 0.7635(2) 0.0150(6) Uani 1.00 1 d . . . C8 C 0.2818(3) 0.6070(2) 0.7770(2) 0.0153(6) Uani 1.00 1 d . . . C9 C 0.4088(3) 0.3104(2) 1.0227(2) 0.0236(8) Uani 1.00 1 d . . . C10 C 0.6792(3) 0.5049(2) 0.7807(2) 0.0143(6) Uani 1.00 1 d . . . C11 C 0.6145(3) 0.5802(2) 0.8134(2) 0.0174(6) Uani 1.00 1 d . . . C12 C 0.6219(3) 0.6650(2) 0.7655(2) 0.0192(7) Uani 1.00 1 d . . . C13 C 0.6940(3) 0.6724(2) 0.6884(2) 0.0211(7) Uani 1.00 1 d . . . C14 C 0.7580(3) 0.5961(2) 0.6575(2) 0.0191(7) Uani 1.00 1 d . . . C15 C 0.7506(3) 0.5095(2) 0.7028(2) 0.0141(6) Uani 1.00 1 d . . . C16 C 0.8152(3) 0.4235(2) 0.6743(2) 0.0161(6) Uani 1.00 1 d . . . H2A H 0.2969 0.7092 0.8646 0.031 Uiso 1.00 1 c R . . H2B H 0.2159 0.6302 0.8982 0.031 Uiso 1.00 1 c R . . H3 H 0.2253 0.3402 0.6158 0.022 Uiso 1.00 1 c R . . H4 H 0.0756 0.2833 0.7146 0.025 Uiso 1.00 1 c R . . H4A H 0.9220 0.3748 0.5823 0.022 Uiso 1.00 1 c R . . H4B H 0.8875 0.4771 0.5665 0.022 Uiso 1.00 1 c R . . H5 H 0.0187 0.3692 0.8427 0.024 Uiso 1.00 1 c R . . H6 H 0.1076 0.5148 0.8741 0.023 Uiso 1.00 1 c R . . H11 H 0.5664 0.5746 0.8667 0.021 Uiso 1.00 1 c R . . H12 H 0.5774 0.7179 0.7859 0.023 Uiso 1.00 1 c R . . H13 H 0.6991 0.7305 0.6566 0.025 Uiso 1.00 1 c R . . H14 H 0.8076 0.6022 0.6050 0.023 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I1 0.01461(10) 0.01533(11) 0.01439(10) 0.00015(8) 0.00143(9) -0.00074(8) I2 0.01475(10) 0.01434(10) 0.01435(10) 0.00006(8) 0.00023(9) 0.00097(8) S1 0.0127(3) 0.0127(3) 0.0141(3) -0.0010(3) 0.0003(3) 0.0006(3) S2 0.0163(3) 0.0154(3) 0.0170(4) -0.0010(3) 0.0022(3) 0.0019(3) F1 0.0236(12) 0.0177(11) 0.0307(12) -0.0051(8) 0.0065(9) 0.0011(9) F2 0.0149(10) 0.0265(11) 0.0297(12) 0.0063(8) 0.0029(9) -0.0008(9) F3 0.0267(11) 0.0340(12) 0.0134(10) 0.0032(9) 0.0022(8) -0.0015(9) F4 0.0433(15) 0.0201(12) 0.0388(14) 0.0050(10) 0.0004(12) 0.0081(10) F5 0.0293(13) 0.0322(13) 0.0405(14) -0.0113(10) 0.0127(11) 0.0091(11) F6 0.0541(16) 0.0441(15) 0.0192(11) -0.0062(12) 0.0013(12) 0.0103(11) O1 0.0218(13) 0.0137(12) 0.0289(14) -0.0031(10) -0.0035(11) -0.0042(10) O2 0.0205(12) 0.0204(12) 0.0153(13) -0.0006(10) -0.0028(9) 0.0025(9) O3 0.0226(13) 0.0164(12) 0.0210(12) -0.0039(10) 0.0025(10) -0.0033(10) O4 0.0167(11) 0.0227(12) 0.0219(12) -0.0022(10) -0.0035(10) 0.0032(11) O5 0.0235(13) 0.0239(14) 0.0306(15) 0.0014(12) 0.0093(11) -0.0022(11) O6 0.0184(12) 0.0131(11) 0.0194(12) 0.0027(9) 0.0016(10) 0.0009(9) N1 0.0125(13) 0.0218(15) 0.0152(13) 0.0037(11) -0.0022(12) -0.0035(11) N2 0.047(2) 0.0088(13) 0.0211(16) 0.0055(13) -0.0214(16) -0.0068(12) N3 0.0154(14) 0.0253(16) 0.0121(14) -0.0025(11) 0.0025(11) -0.0027(12) N4 0.0172(13) 0.0245(15) 0.0130(13) 0.0076(12) 0.0034(13) -0.0039(12) C1 0.0150(15) 0.0178(16) 0.0172(16) 0.0006(14) 0.0046(13) -0.0008(13) C2 0.0139(16) 0.0179(17) 0.0135(16) 0.0020(12) 0.0003(12) 0.0034(13) C3 0.0177(16) 0.0217(17) 0.0156(16) 0.0016(14) -0.0014(12) -0.0042(13) C4 0.0206(17) 0.0185(17) 0.0227(18) -0.0046(15) -0.0020(16) 0.0006(14) C5 0.0146(16) 0.026(2) 0.0201(17) -0.0014(13) 0.0046(13) 0.0050(15) C6 0.0213(17) 0.0214(17) 0.0156(16) 0.0043(14) -0.0009(13) -0.0039(14) C7 0.0131(14) 0.0150(15) 0.0170(16) 0.0016(13) -0.0055(12) 0.0023(13) C8 0.0172(15) 0.0137(16) 0.0150(16) 0.0052(12) -0.0015(13) -0.0007(12) C9 0.027(2) 0.0228(19) 0.0207(18) -0.0043(15) 0.0005(16) 0.0081(15) C10 0.0164(14) 0.0118(15) 0.0146(15) -0.0010(13) -0.0032(13) 0.0004(12) C11 0.0160(15) 0.0227(17) 0.0135(15) 0.0004(14) -0.0008(14) -0.0033(13) C12 0.0201(17) 0.0154(16) 0.0222(18) 0.0031(14) -0.0023(15) -0.0056(14) C13 0.027(2) 0.0143(16) 0.0221(18) -0.0007(14) -0.0048(15) 0.0023(14) C14 0.0204(17) 0.0198(17) 0.0173(17) -0.0012(13) -0.0003(14) 0.0006(14) C15 0.0154(15) 0.0121(15) 0.0149(16) -0.0012(12) -0.0018(12) -0.0021(12) C16 0.0122(15) 0.0171(16) 0.0189(17) 0.0000(13) -0.0023(13) -0.0021(13) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 I1 O3 2.398(2) yes . . I1 N1 2.034(2) yes . . I1 C2 2.111(3) yes . . I2 O6 2.385(2) yes . . I2 N3 2.022(3) yes . . I2 C10 2.113(3) yes . . S1 O1 1.437(2) yes . . S1 O2 1.449(2) yes . . S1 N1 1.563(3) yes . . S1 C1 1.835(3) yes . . S2 O4 1.436(2) yes . . S2 O5 1.434(2) yes . . S2 N3 1.569(3) yes . . S2 C9 1.844(4) yes . . F1 C1 1.343(4) yes . . F2 C1 1.334(4) yes . . F3 C1 1.334(4) yes . . F4 C9 1.330(4) yes . . F5 C9 1.344(4) yes . . F6 C9 1.333(4) yes . . O3 C8 1.254(4) yes . . O6 C16 1.259(4) yes . . N2 C8 1.347(4) yes . . N4 C16 1.329(4) yes . . C2 C3 1.388(5) yes . . C2 C7 1.379(5) yes . . C3 C4 1.392(5) yes . . C4 C5 1.380(5) yes . . C5 C6 1.395(5) yes . . C6 C7 1.402(5) yes . . C7 C8 1.490(5) yes . . C10 C11 1.377(4) yes . . C10 C15 1.391(4) yes . . C11 C12 1.396(5) yes . . C12 C13 1.389(5) yes . . C13 C14 1.375(5) yes . . C14 C15 1.401(4) yes . . C15 C16 1.480(4) yes . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O3 I1 N1 168.13(10) yes . . . O3 I1 C2 74.13(11) yes . . . N1 I1 C2 94.35(12) yes . . . O6 I2 N3 167.45(10) yes . . . O6 I2 C10 74.70(11) yes . . . N3 I2 C10 94.20(13) yes . . . O1 S1 O2 117.43(16) yes . . . O1 S1 N1 109.95(16) yes . . . O1 S1 C1 102.11(16) yes . . . O2 S1 N1 117.37(15) yes . . . O2 S1 C1 102.57(15) yes . . . N1 S1 C1 105.03(16) yes . . . O4 S2 O5 118.28(16) yes . . . O4 S2 N3 115.85(16) yes . . . O4 S2 C9 103.57(17) yes . . . O5 S2 N3 110.62(17) yes . . . O5 S2 C9 102.76(17) yes . . . N3 S2 C9 103.31(18) yes . . . I1 O3 C8 111.7(2) yes . . . I2 O6 C16 112.2(2) yes . . . I1 N1 S1 116.47(16) yes . . . I2 N3 S2 115.44(17) yes . . . S1 C1 F1 110.4(2) yes . . . S1 C1 F2 110.8(2) yes . . . S1 C1 F3 111.9(2) yes . . . F1 C1 F2 108.1(2) yes . . . F1 C1 F3 107.2(2) yes . . . F2 C1 F3 108.2(2) yes . . . I1 C2 C3 119.7(2) yes . . . I1 C2 C7 116.9(2) yes . . . C3 C2 C7 123.4(3) yes . . . C2 C3 C4 117.5(3) yes . . . C3 C4 C5 120.9(3) yes . . . C4 C5 C6 120.4(3) yes . . . C5 C6 C7 119.8(3) yes . . . C2 C7 C6 117.9(3) yes . . . C2 C7 C8 118.1(3) yes . . . C6 C7 C8 123.9(3) yes . . . O3 C8 N2 123.9(3) yes . . . O3 C8 C7 117.5(3) yes . . . N2 C8 C7 118.6(3) yes . . . S2 C9 F4 110.9(2) yes . . . S2 C9 F5 109.5(2) yes . . . S2 C9 F6 111.6(2) yes . . . F4 C9 F5 107.9(3) yes . . . F4 C9 F6 108.6(3) yes . . . F5 C9 F6 108.2(3) yes . . . I2 C10 C11 120.2(2) yes . . . I2 C10 C15 116.6(2) yes . . . C11 C10 C15 123.2(3) yes . . . C10 C11 C12 117.9(3) yes . . . C11 C12 C13 120.3(3) yes . . . C12 C13 C14 120.5(3) yes . . . C13 C14 C15 120.6(3) yes . . . C10 C15 C14 117.4(3) yes . . . C10 C15 C16 118.1(3) yes . . . C14 C15 C16 124.5(3) yes . . . O6 C16 N4 122.1(3) yes . . . O6 C16 C15 118.5(3) yes . . . N4 C16 C15 119.4(3) yes . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O3 I1 N1 S1 -118.9(4) ? . . . . N1 I1 O3 C8 25.9(6) ? . . . . O3 I1 C2 C3 174.4(3) ? . . . . O3 I1 C2 C7 -6.6(2) ? . . . . C2 I1 O3 C8 11.7(2) ? . . . . N1 I1 C2 C3 -2.7(2) ? . . . . N1 I1 C2 C7 176.3(2) ? . . . . C2 I1 N1 S1 -105.15(19) ? . . . . O6 I2 N3 S2 120.3(4) ? . . . . N3 I2 O6 C16 -28.7(5) ? . . . . O6 I2 C10 C11 -179.5(3) ? . . . . O6 I2 C10 C15 -0.8(2) ? . . . . C10 I2 O6 C16 -0.3(2) ? . . . . N3 I2 C10 C11 -5.5(3) ? . . . . N3 I2 C10 C15 173.3(2) ? . . . . C10 I2 N3 S2 92.9(2) ? . . . . O1 S1 N1 I1 161.32(16) ? . . . . O1 S1 C1 F1 173.8(2) ? . . . . O1 S1 C1 F2 -66.4(2) ? . . . . O1 S1 C1 F3 54.4(2) ? . . . . O2 S1 N1 I1 23.6(2) ? . . . . O2 S1 C1 F1 -64.2(2) ? . . . . O2 S1 C1 F2 55.6(2) ? . . . . O2 S1 C1 F3 176.5(2) ? . . . . N1 S1 C1 F1 59.0(2) ? . . . . N1 S1 C1 F2 178.8(2) ? . . . . N1 S1 C1 F3 -60.3(2) ? . . . . C1 S1 N1 I1 -89.51(19) ? . . . . O4 S2 N3 I2 -11.0(2) ? . . . . O4 S2 C9 F4 62.1(3) ? . . . . O4 S2 C9 F5 -56.8(3) ? . . . . O4 S2 C9 F6 -176.6(2) ? . . . . O5 S2 N3 I2 -149.16(17) ? . . . . O5 S2 C9 F4 -174.2(2) ? . . . . O5 S2 C9 F5 66.8(3) ? . . . . O5 S2 C9 F6 -52.9(3) ? . . . . N3 S2 C9 F4 -59.1(3) ? . . . . N3 S2 C9 F5 -178.0(2) ? . . . . N3 S2 C9 F6 62.2(3) ? . . . . C9 S2 N3 I2 101.5(2) ? . . . . I1 O3 C8 N2 166.7(2) ? . . . . I1 O3 C8 C7 -14.3(3) ? . . . . I2 O6 C16 N4 -179.7(2) ? . . . . I2 O6 C16 C15 1.2(3) ? . . . . I1 C2 C3 C4 178.7(2) ? . . . . I1 C2 C7 C6 -178.5(2) ? . . . . I1 C2 C7 C8 2.0(4) ? . . . . C3 C2 C7 C6 0.5(5) ? . . . . C3 C2 C7 C8 -179.0(3) ? . . . . C7 C2 C3 C4 -0.3(5) ? . . . . C2 C3 C4 C5 -0.2(5) ? . . . . C3 C4 C5 C6 0.5(5) ? . . . . C4 C5 C6 C7 -0.3(5) ? . . . . C5 C6 C7 C2 -0.2(5) ? . . . . C5 C6 C7 C8 179.3(3) ? . . . . C2 C7 C8 O3 9.5(4) ? . . . . C2 C7 C8 N2 -171.5(3) ? . . . . C6 C7 C8 O3 -170.0(3) ? . . . . C6 C7 C8 N2 9.0(5) ? . . . . I2 C10 C11 C12 178.4(2) ? . . . . I2 C10 C15 C14 -177.2(2) ? . . . . I2 C10 C15 C16 1.7(4) ? . . . . C11 C10 C15 C14 1.5(5) ? . . . . C11 C10 C15 C16 -179.6(3) ? . . . . C15 C10 C11 C12 -0.3(5) ? . . . . C10 C11 C12 C13 -0.9(5) ? . . . . C11 C12 C13 C14 0.7(5) ? . . . . C12 C13 C14 C15 0.7(5) ? . . . . C13 C14 C15 C10 -1.7(5) ? . . . . C13 C14 C15 C16 179.5(3) ? . . . . C10 C15 C16 O6 -2.0(4) ? . . . . C10 C15 C16 N4 178.9(3) ? . . . . C14 C15 C16 O6 176.8(3) ? . . . . C14 C15 C16 N4 -2.3(5) ? . . . . #===END======================================================================== # Attachment 'New CIF-1.cif' #============================================================================== data_kmi11963 _database_code_depnum_ccdc_archive 'CCDC 692568' #============================================================================== _audit_creation_date 2008-10-27 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? # CHEMICAL DATA _chemical_formula_sum 'C9 H7 F3 I N O3 S ' _chemical_formula_moiety 'C9 H7 F3 I N O3 S ' _chemical_formula_weight 393.12 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2+Z 3 1/2+X,1/2-Y,+Z 4 -X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 10.1845(3) _cell_length_b 19.9169(5) _cell_length_c 5.9157(2) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1199.96(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10138 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 93.1 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 2.176 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752.00 _exptl_absorpt_coefficient_mu 2.881 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.531 _exptl_absorpt_correction_T_max 0.562 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 10351 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_theta_max 27.41 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2720 _reflns_number_gt 2661 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0154 _refine_ls_wR_factor_ref 0.0379 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2720 _refine_ls_number_parameters 165 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0199P)^2^+0.1576P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0020 _refine_diff_density_max 0.63 _refine_diff_density_min -0.28 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1228 Friedel Pairs' _refine_ls_abs_structure_Flack -0.023(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.017 0.010 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; I I -0.474 1.812 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.957403(9) 0.087216(5) 0.55401(5) 0.01422(4) Uani 1.00 1 d . . . S1 S 0.80838(4) -0.04469(2) 0.56906(11) 0.01548(8) Uani 1.00 1 d . . . F1 F 0.64249(13) -0.03078(7) 0.9071(2) 0.0246(2) Uani 1.00 1 d . . . F2 F 0.55456(11) -0.06384(7) 0.5934(2) 0.0257(4) Uani 1.00 1 d . . . F3 F 0.61415(12) 0.03982(6) 0.6333(2) 0.0241(2) Uani 1.00 1 d . . . O1 O 0.98384(18) 0.20937(8) 0.4553(3) 0.0250(3) Uani 1.00 1 d . . . O2 O 0.82565(15) -0.11368(7) 0.6404(2) 0.0247(3) Uani 1.00 1 d . . . O3 O 0.79046(16) -0.03079(8) 0.3313(2) 0.0259(3) Uani 1.00 1 d . . . N1 N 0.91244(17) -0.00091(8) 0.6986(3) 0.0148(3) Uani 1.00 1 d . . . C1 C 0.8518(2) 0.14398(10) 0.7959(3) 0.0162(3) Uani 1.00 1 d . . . C2 C 0.7933(2) 0.11255(10) 0.9777(3) 0.0181(4) Uani 1.00 1 d . . . C3 C 0.7170(2) 0.15061(11) 1.1230(3) 0.0222(4) Uani 1.00 1 d . . . C4 C 0.6999(2) 0.21924(11) 1.0915(4) 0.0260(5) Uani 1.00 1 d . . . C5 C 0.7628(2) 0.25062(11) 0.9114(4) 0.0252(4) Uani 1.00 1 d . . . C6 C 0.8406(2) 0.21366(10) 0.7626(3) 0.0202(4) Uani 1.00 1 d . . . C7 C 0.9136(2) 0.24524(9) 0.5742(6) 0.0233(4) Uani 1.00 1 d . . . C8 C 0.9027(2) 0.31911(11) 0.5322(6) 0.0379(6) Uani 1.00 1 d . . . C9 C 0.6457(2) -0.02375(11) 0.6834(3) 0.0185(4) Uani 1.00 1 d . . . H2 H 0.8051 0.0658 1.0026 0.022 Uiso 1.00 1 c R . . H3 H 0.6754 0.1293 1.2475 0.027 Uiso 1.00 1 c R . . H4 H 0.6460 0.2444 1.1915 0.031 Uiso 1.00 1 c R . . H5 H 0.7527 0.2976 0.8897 0.030 Uiso 1.00 1 c R . . H8A H 0.8110 0.3307 0.5014 0.045 Uiso 1.00 1 c R . . H8B H 0.9571 0.3313 0.4018 0.045 Uiso 1.00 1 c R . . H8C H 0.9331 0.3437 0.6659 0.045 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I1 0.01593(7) 0.01018(6) 0.01654(7) 0.00116(3) 0.00256(8) 0.00101(8) S1 0.01542(19) 0.01382(18) 0.0172(2) -0.00079(15) -0.0005(2) -0.0029(2) F1 0.0275(7) 0.0259(6) 0.0204(6) -0.0019(5) 0.0060(5) 0.0021(5) F2 0.0176(5) 0.0257(6) 0.0336(13) -0.0073(4) -0.0049(5) 0.0018(6) F3 0.0203(5) 0.0164(5) 0.0355(7) 0.0032(4) -0.0025(5) 0.0046(4) O1 0.0292(8) 0.0162(7) 0.0296(8) 0.0002(7) 0.0115(7) 0.0043(6) O2 0.0233(7) 0.0114(6) 0.0395(9) -0.0013(6) -0.0035(6) -0.0037(6) O3 0.0255(8) 0.0363(9) 0.0161(7) -0.0062(7) -0.0011(6) -0.0044(6) N1 0.0163(8) 0.0101(7) 0.0182(8) -0.0007(6) -0.0011(7) 0.0019(6) C1 0.0164(9) 0.0140(9) 0.0180(9) 0.0028(7) 0.0019(8) -0.0033(7) C2 0.0211(10) 0.0137(9) 0.0197(9) -0.0014(8) -0.0003(7) -0.0016(7) C3 0.0246(10) 0.0237(10) 0.0182(10) -0.0048(9) 0.0053(8) -0.0007(7) C4 0.0292(10) 0.0222(9) 0.0266(15) 0.0033(8) 0.0091(10) -0.0066(9) C5 0.0301(12) 0.0146(10) 0.0310(12) 0.0035(8) 0.0075(10) -0.0031(8) C6 0.0231(10) 0.0148(9) 0.0228(11) 0.0010(8) 0.0039(8) 0.0011(7) C7 0.0265(9) 0.0154(8) 0.0281(13) 0.0012(7) 0.0048(13) 0.0006(11) C8 0.0488(13) 0.0159(9) 0.0490(17) 0.0034(9) 0.0206(17) 0.0094(13) C9 0.0179(9) 0.0149(9) 0.0228(11) -0.0010(7) 0.0003(8) 0.0013(8) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR2002 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 I1 N1 2.0056(16) yes . . I1 C1 2.117(2) yes . . S1 O2 1.4481(14) yes . . S1 O3 1.4450(17) yes . . S1 N1 1.5720(17) yes . . S1 C9 1.837(2) yes . . F1 C9 1.331(2) yes . . F2 C9 1.335(2) yes . . F3 C9 1.340(2) yes . . O1 C7 1.232(3) yes . . C1 C2 1.379(3) yes . . C1 C6 1.406(2) yes . . C2 C3 1.385(3) yes . . C3 C4 1.391(3) yes . . C4 C5 1.391(3) yes . . C5 C6 1.395(3) yes . . C6 C7 1.480(3) yes . . C7 C8 1.496(2) yes . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 N1 I1 C1 93.61(7) yes . . . O2 S1 O3 118.73(9) yes . . . O2 S1 N1 107.60(9) yes . . . O2 S1 C9 102.57(9) yes . . . O3 S1 N1 116.97(9) yes . . . O3 S1 C9 101.59(9) yes . . . N1 S1 C9 107.61(9) yes . . . I1 N1 S1 115.55(9) yes . . . I1 C1 C2 120.26(14) yes . . . I1 C1 C6 118.26(15) yes . . . C2 C1 C6 121.47(19) yes . . . C1 C2 C3 118.54(18) yes . . . C2 C3 C4 121.7(2) yes . . . C3 C4 C5 119.1(2) yes . . . C4 C5 C6 120.5(2) yes . . . C1 C6 C5 118.6(2) yes . . . C1 C6 C7 118.96(18) yes . . . C5 C6 C7 122.44(18) yes . . . O1 C7 C6 118.39(17) yes . . . O1 C7 C8 121.2(2) yes . . . C6 C7 C8 120.4(2) yes . . . S1 C9 F1 111.37(14) yes . . . S1 C9 F2 110.14(14) yes . . . S1 C9 F3 110.46(14) yes . . . F1 C9 F2 108.44(17) yes . . . F1 C9 F3 108.28(17) yes . . . F2 C9 F3 108.06(17) yes . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N1 I1 C1 C2 3.97(18) ? . . . . N1 I1 C1 C6 -174.53(16) ? . . . . C1 I1 N1 S1 106.52(10) ? . . . . O2 S1 N1 I1 157.85(9) ? . . . . O2 S1 C9 F1 59.18(16) ? . . . . O2 S1 C9 F2 -61.18(16) ? . . . . O2 S1 C9 F3 179.53(14) ? . . . . O3 S1 N1 I1 21.20(13) ? . . . . O3 S1 C9 F1 -177.56(14) ? . . . . O3 S1 C9 F2 62.08(16) ? . . . . O3 S1 C9 F3 -57.21(16) ? . . . . N1 S1 C9 F1 -54.14(17) ? . . . . N1 S1 C9 F2 -174.50(14) ? . . . . N1 S1 C9 F3 66.21(16) ? . . . . C9 S1 N1 I1 -92.25(11) ? . . . . I1 C1 C2 C3 -175.31(15) ? . . . . I1 C1 C6 C5 175.11(17) ? . . . . I1 C1 C6 C7 -6.0(2) ? . . . . C2 C1 C6 C5 -3.4(3) ? . . . . C2 C1 C6 C7 175.5(2) ? . . . . C6 C1 C2 C3 3.1(3) ? . . . . C1 C2 C3 C4 -0.9(3) ? . . . . C2 C3 C4 C5 -1.1(3) ? . . . . C3 C4 C5 C6 0.9(3) ? . . . . C4 C5 C6 C1 1.3(3) ? . . . . C4 C5 C6 C7 -177.5(2) ? . . . . C1 C6 C7 O1 -1.4(3) ? . . . . C1 C6 C7 C8 179.3(2) ? . . . . C5 C6 C7 O1 177.5(2) ? . . . . C5 C6 C7 C8 -1.9(3) ? . . . .