# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2005 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Dr Viktor Zhdankin' _publ_contact_author_address ; Department of Chemistry University of Minnesota-Duluth Duluth MN 55812 UNITED STATES OF AMERICA ; _publ_contact_author_email VZHDANKI@D.UMN.EDU _publ_section_title ; Intra- and intermolecular interactions in the solid state structure of 2-iodylbenzenesulfonamides: first example of a heptacoordinated organic iodine(V) compound ; _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; loop_ _publ_author_name 'Viktor Zhdankin' 'Alexey Y. Koposov' 'Victor N. Nemykin' data_1 _database_code_depnum_ccdc_archive 'CCDC 268074' _audit_creation_date 05-06-14 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'sulf3 in P 1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.5196(15) _cell_length_b 8.1049(16) _cell_length_c 11.426(2) _cell_angle_alpha 101.53(3) _cell_angle_beta 96.26(3) _cell_angle_gamma 100.54(3) _cell_volume 663.1(3) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C12 H20 I1 N1 O3 S1 # Dc = 1.93 Fooo = 392.00 Mu = 25.73 M = 770.53 # Found Formula = C10 H12 I1 N1 O6 S1 # Dc = 2.01 FOOO = 392.00 Mu = 25.94 M = 802.36 _chemical_formula_sum 'C10 H12 I1 N1 O6 S1' _chemical_formula_moiety 'C10 H12 I1 N1 O6 S1' _chemical_compound_source ? _chemical_formula_weight 401.18 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 17.5 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_max 0.5 _exptl_crystal_density_diffrn 2.009 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 2.594 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.5778 _exptl_absorpt_correction_T_max 0.9993 _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q _computing_data_collection 'Rigaku AFC-7R' _computing_data_reduction 'TeXsan 1.10b' _computing_cell_refinement WinAFC _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _diffrn_standards_decay_% 5 _diffrn_ambient_temperature 293 _diffrn_reflns_number 3026 _reflns_number_total 3026 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 2931 # Number of reflections without Friedels Law is 3026 # Theoretical number of reflections is about 3034 _diffrn_reflns_theta_min 2.623 _diffrn_reflns_theta_max 27.458 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.458 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min -14 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 3.15 _oxford_diffrn_Wilson_scale 10.46 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -4.10 _refine_diff_density_max 2.66 _refine_ls_number_reflns 2931 _refine_ls_number_restraints 3 _refine_ls_number_parameters 344 #_refine_ls_R_factor_ref 0.0654 _refine_ls_wR_factor_ref 0.1514 _refine_ls_goodness_of_fit_ref 0.9737 #_reflns_number_all 3015 _refine_ls_R_factor_all 0.0658 _refine_ls_wR_factor_all 0.1524 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2931 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_gt 0.1514 _refine_ls_shift/su_max 0.003641 _refine_ls_abs_structure_Flack 0.42(13) _refine_ls_abs_structure_details 'Flack, 95 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 35.0 55.6 28.0 7.70 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens I1 I 0.3822(3) 0.4982(5) -0.9472(3) 0.0395 1.0000 Uani . . . . . . O2 O 0.5666(18) 0.468(2) -0.8457(11) 0.0576 1.0000 Uani . . . . . . C3 C 0.336(2) 0.2506(16) -1.0710(13) 0.0382 1.0000 Uani . . . . . . C4 C 0.3274(17) 0.2190(16) -1.1964(12) 0.0361 1.0000 Uani . . . . . . S5 S 0.3818(5) 0.3804(5) -1.2761(4) 0.0407 1.0000 Uani . . . . . . N6 N 0.6010(16) 0.4180(15) -1.2718(10) 0.0450 1.0000 Uani . . . . . . C7 C 0.691(2) 0.283(2) -1.3257(11) 0.0467 1.0000 Uani . . . . . . O9 O 0.3400(18) 0.5366(19) -1.2048(11) 0.0579 1.0000 Uani . . . . . . O10 O 0.2960(15) 0.3116(17) -1.3989(9) 0.0520 1.0000 Uani . . . . . . C11 C 0.286(3) 0.050(2) -1.2591(16) 0.0504 1.0000 Uani . . . . . . C12 C 0.258(4) -0.090(3) -1.204(3) 0.0607 1.0000 Uani . . . . . . C13 C 0.277(3) -0.050(4) -1.078(2) 0.0766 1.0000 Uani . . . . . . C14 C 0.307(3) 0.119(3) -1.0089(17) 0.0578 1.0000 Uani . . . . . . O15 O 0.1959(17) 0.4367(18) -0.8634(9) 0.0506 1.0000 Uani . . . . . . I16 I -0.1186(3) -0.4627(5) -0.9443(3) 0.0392 1.0000 Uani . . . . . . O17 O -0.3091(17) -0.4051(17) -1.0326(10) 0.0470 1.0000 Uani . . . . . . C18 C -0.051(2) -0.219(3) -0.8157(15) 0.0438 1.0000 Uani . . . . . . C19 C 0.0073(18) -0.1872(18) -0.6937(12) 0.0386 1.0000 Uani . . . . . . S20 S 0.0433(5) -0.3547(5) -0.6165(4) 0.0387 1.0000 Uani . . . . . . N21 N 0.2476(15) -0.3827(14) -0.6278(10) 0.0421 1.0000 Uani . . . . . . C22 C 0.4075(18) -0.2422(18) -0.5769(12) 0.0465 1.0000 Uani . . . . . . C23 C 0.441(2) -0.1232(19) -0.6658(13) 0.0466 1.0000 Uani . . . . . . O24 O 0.511(2) 0.040(2) -0.6046(13) 0.0579 1.0000 Uani . . . . . . C25 C 0.541(5) 0.158(5) -0.680(3) 0.0817 1.0000 Uani . . . . . . O26 O 0.418(2) -0.1660(15) -0.7713(10) 0.0619 1.0000 Uani . . . . . . C27 C 0.576(2) -0.321(2) -0.5533(18) 0.0604 1.0000 Uani . . . . . . O28 O -0.0778(14) -0.5103(16) -0.6823(9) 0.0457 1.0000 Uani . . . . . . O29 O 0.0364(15) -0.2900(16) -0.4915(9) 0.0498 1.0000 Uani . . . . . . C30 C 0.044(3) -0.017(3) -0.6203(17) 0.0505 1.0000 Uani . . . . . . C32 C -0.074(2) -0.083(3) -0.8699(15) 0.0505 1.0000 Uani . . . . . . O33 O 0.0497(19) -0.406(2) -1.0379(12) 0.0591 1.0000 Uani . . . . . . C1 C -0.034(3) 0.083(2) -0.8029(15) 0.0580 1.0000 Uani . . . . . . C26 C 0.024(3) 0.106(3) -0.680(3) 0.0559 1.0000 Uani . . . . . . O6 O 0.724(2) 0.013(2) -1.2944(14) 0.0633 1.0000 Uani . . . . . . C8 C 0.875(3) 0.361(3) -1.359(2) 0.0764 1.0000 Uani . . . . . . C2 C 0.731(2) 0.1702(19) -1.2366(13) 0.0467 1.0000 Uani . . . . . . C10 C 0.758(5) -0.117(3) -1.224(3) 0.0798 1.0000 Uani . . . . . . O1 O 0.765(2) 0.2236(17) -1.1276(11) 0.0596 1.0000 Uani . . . . . . H71 H 0.6106 0.2107 -1.4013 0.0554 1.0000 Uiso R . . . . . H111 H 0.2775 0.0278 -1.3497 0.0488 1.0000 Uiso R . . . . . H121 H 0.2300 -0.2123 -1.2536 0.0691 1.0000 Uiso R . . . . . H131 H 0.2703 -0.1443 -1.0314 0.0930 1.0000 Uiso R . . . . . H141 H 0.3107 0.1483 -0.9182 0.0734 1.0000 Uiso R . . . . . H221 H 0.3843 -0.1738 -0.4986 0.0496 1.0000 Uiso R . . . . . H251 H 0.6019 0.2752 -0.6303 0.0884 1.0000 Uiso R . . . . . H252 H 0.6383 0.1251 -0.7380 0.0884 1.0000 Uiso R . . . . . H253 H 0.4325 0.1620 -0.7335 0.0884 1.0000 Uiso R . . . . . H271 H 0.6864 -0.2292 -0.5180 0.0677 1.0000 Uiso R . . . . . H272 H 0.5975 -0.3928 -0.6306 0.0677 1.0000 Uiso R . . . . . H273 H 0.5524 -0.3984 -0.4947 0.0677 1.0000 Uiso R . . . . . H301 H 0.0840 0.0074 -0.5295 0.0531 1.0000 Uiso R . . . . . H321 H -0.1175 -0.1043 -0.9589 0.0534 1.0000 Uiso R . . . . . H11 H -0.0476 0.1837 -0.8405 0.0639 1.0000 Uiso R . . . . . H261 H 0.0626 0.2292 -0.6337 0.0697 1.0000 Uiso R . . . . . H81 H 0.9372 0.2691 -1.3971 0.0933 1.0000 Uiso R . . . . . H82 H 0.8577 0.4375 -1.4171 0.0933 1.0000 Uiso R . . . . . H83 H 0.9577 0.4335 -1.2838 0.0933 1.0000 Uiso R . . . . . H101 H 0.7525 -0.2333 -1.2780 0.0821 1.0000 Uiso R . . . . . H102 H 0.8853 -0.0788 -1.1739 0.0821 1.0000 Uiso R . . . . . H103 H 0.6670 -0.1306 -1.1670 0.0821 1.0000 Uiso R . . . . . H61 H 0.6676 0.5220 -1.2359 0.0539 1.0000 Uiso R . . . . . H211 H 0.2639 -0.4848 -0.6655 0.0498 1.0000 Uiso 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 0.0483(4) 0.0371(6) 0.0307(4) 0.0023(5) 0.0077(3) 0.0078(5) O2 0.056(6) 0.067(9) 0.040(5) 0.008(5) -0.010(5) 0.002(6) C3 0.051(7) 0.013(5) 0.038(7) -0.014(5) -0.003(5) 0.004(5) C4 0.026(5) 0.035(5) 0.041(6) 0.003(4) 0.004(5) -0.004(4) S5 0.0506(15) 0.0420(14) 0.0298(13) 0.0055(10) 0.0045(10) 0.0143(11) N6 0.059(6) 0.041(5) 0.034(5) 0.007(4) 0.009(4) 0.008(4) C7 0.055(7) 0.055(8) 0.029(6) 0.003(5) 0.005(5) 0.016(6) O9 0.078(7) 0.059(9) 0.058(7) 0.024(6) 0.034(6) 0.042(7) O10 0.050(6) 0.071(7) 0.030(4) 0.001(4) -0.006(4) 0.016(5) C11 0.062(11) 0.039(7) 0.040(8) -0.008(6) 0.002(7) 0.005(7) C12 0.077(13) 0.023(7) 0.077(15) 0.004(7) 0.020(11) 0.002(7) C13 0.064(11) 0.085(18) 0.086(14) 0.024(13) 0.017(10) 0.020(10) C14 0.092(12) 0.036(8) 0.052(8) 0.021(7) 0.017(8) 0.014(8) O15 0.065(6) 0.045(7) 0.039(5) 0.003(4) 0.020(5) 0.003(5) I16 0.0462(4) 0.0367(6) 0.0314(4) 0.0036(5) 0.0042(3) 0.0062(5) O17 0.058(6) 0.039(5) 0.042(5) 0.007(4) 0.010(4) 0.007(4) C18 0.039(6) 0.059(11) 0.046(8) 0.029(8) 0.019(6) 0.017(6) C19 0.028(6) 0.042(6) 0.044(6) 0.009(5) 0.007(5) 0.004(5) S20 0.0483(14) 0.0369(13) 0.0311(13) 0.0075(10) 0.0066(10) 0.0097(10) N21 0.048(5) 0.037(5) 0.041(5) 0.005(4) 0.004(4) 0.011(4) C22 0.053(7) 0.045(7) 0.035(6) 0.004(5) -0.003(5) 0.007(5) C23 0.047(7) 0.047(7) 0.040(7) 0.000(5) 0.005(6) 0.006(6) O24 0.076(8) 0.049(8) 0.042(6) -0.001(5) -0.002(5) 0.015(6) C25 0.108(18) 0.069(17) 0.067(14) 0.019(13) 0.005(12) 0.015(13) O26 0.111(10) 0.038(5) 0.038(5) 0.004(4) 0.015(6) 0.019(6) C27 0.050(8) 0.057(10) 0.065(10) 0.007(8) -0.015(7) 0.011(7) O28 0.046(5) 0.039(6) 0.041(5) 0.005(4) -0.008(4) -0.006(4) O29 0.053(5) 0.066(6) 0.039(5) 0.020(4) 0.014(4) 0.022(5) C30 0.053(9) 0.046(8) 0.042(8) -0.001(6) -0.007(7) 0.005(7) C32 0.059(8) 0.049(10) 0.038(7) 0.006(6) 0.002(6) 0.004(6) O33 0.060(6) 0.061(9) 0.061(7) 0.019(6) 0.017(6) 0.014(6) C1 0.087(11) 0.027(6) 0.061(9) 0.018(7) 0.000(8) 0.011(7) C26 0.063(10) 0.039(10) 0.064(12) 0.005(9) 0.002(8) 0.016(8) O6 0.082(9) 0.046(7) 0.059(8) 0.009(6) -0.001(7) 0.018(7) C8 0.078(12) 0.082(13) 0.092(15) 0.040(12) 0.047(11) 0.033(9) C2 0.055(8) 0.041(6) 0.037(6) 0.004(5) -0.003(6) 0.001(6) C10 0.12(2) 0.047(12) 0.066(14) 0.001(9) -0.006(13) 0.030(12) O1 0.086(8) 0.051(6) 0.041(5) 0.008(4) -0.003(5) 0.023(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3076(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag I1 . O17 1_665 2.662(11) yes I1 . O2 . 1.793(12) yes I1 . C3 . 2.157(12) yes I1 . O15 . 1.832(11) yes C3 . C4 . 1.395(18) yes C3 . C14 . 1.39(2) yes C4 . S5 . 1.752(13) yes C4 . C11 . 1.37(2) yes S5 . N6 . 1.614(12) yes S5 . O9 . 1.467(13) yes S5 . O10 . 1.434(10) yes N6 . C7 . 1.456(19) yes N6 . H61 . 0.890 no C7 . C8 . 1.53(2) yes C7 . C2 . 1.54(2) yes C7 . H71 . 1.005 no C11 . C12 . 1.40(3) yes C11 . H111 . 1.007 no C12 . C13 . 1.39(4) yes C12 . H121 . 1.010 no C13 . C14 . 1.41(4) yes C13 . H131 . 1.013 no C14 . H141 . 1.012 no I16 . O17 . 1.845(13) yes I16 . C18 . 2.15(2) yes I16 . O33 . 1.799(13) yes C18 . C19 . 1.37(2) yes C18 . C32 . 1.40(3) yes C19 . S20 . 1.804(14) yes C19 . C30 . 1.42(2) yes S20 . N21 . 1.608(11) yes S20 . O28 . 1.427(10) yes S20 . O29 . 1.430(10) yes N21 . C22 . 1.471(16) yes N21 . H211 . 0.890 no C22 . C23 . 1.544(19) yes C22 . C27 . 1.54(2) yes C22 . H221 . 1.005 no C23 . O24 . 1.34(2) yes C23 . O26 . 1.170(18) yes O24 . C25 . 1.41(4) yes C25 . H251 . 0.997 no C25 . H252 . 1.074 no C25 . H253 . 0.977 no C27 . H271 . 0.995 no C27 . H272 . 1.002 no C27 . H273 . 1.011 no C30 . C26 . 1.34(3) yes C30 . H301 . 1.017 no C32 . C1 . 1.37(3) yes C32 . H321 . 1.004 no C1 . C26 . 1.38(3) yes C1 . H11 . 1.009 no C26 . H261 . 1.010 no O6 . C2 . 1.30(2) yes O6 . C10 . 1.49(3) yes C8 . H81 . 1.003 no C8 . H82 . 1.012 no C8 . H83 . 1.007 no C2 . O1 . 1.216(18) yes C10 . H101 . 1.009 no C10 . H102 . 1.021 no C10 . H103 . 1.004 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O17 1_665 I1 . O2 . 72.7(5) yes O17 1_665 I1 . C3 . 89.5(5) yes O2 . I1 . C3 . 97.2(7) yes O17 1_665 I1 . O15 . 170.0(5) yes O2 . I1 . O15 . 97.9(7) yes C3 . I1 . O15 . 95.1(6) yes I1 . C3 . C4 . 127.0(11) yes I1 . C3 . C14 . 110.2(12) yes C4 . C3 . C14 . 122.8(14) yes C3 . C4 . S5 . 123.9(10) yes C3 . C4 . C11 . 117.5(13) yes S5 . C4 . C11 . 118.5(12) yes C4 . S5 . N6 . 106.7(6) yes C4 . S5 . O9 . 106.2(7) yes N6 . S5 . O9 . 106.3(7) yes C4 . S5 . O10 . 107.2(7) yes N6 . S5 . O10 . 109.0(6) yes O9 . S5 . O10 . 120.7(8) yes S5 . N6 . C7 . 120.6(10) yes S5 . N6 . H61 . 119.658 no C7 . N6 . H61 . 119.714 no N6 . C7 . C8 . 110.9(15) yes N6 . C7 . C2 . 111.1(11) yes C8 . C7 . C2 . 106.7(13) yes N6 . C7 . H71 . 109.203 no C8 . C7 . H71 . 108.602 no C2 . C7 . H71 . 110.316 no C4 . C11 . C12 . 123.6(19) yes C4 . C11 . H111 . 117.305 no C12 . C11 . H111 . 119.048 no C11 . C12 . C13 . 116(2) yes C11 . C12 . H121 . 120.842 no C13 . C12 . H121 . 123.065 no C12 . C13 . C14 . 123(3) yes C12 . C13 . H131 . 120.647 no C14 . C13 . H131 . 116.163 no C13 . C14 . C3 . 116.6(18) yes C13 . C14 . H141 . 123.253 no C3 . C14 . H141 . 120.121 no O17 . I16 . C18 . 93.8(6) yes O17 . I16 . O33 . 95.9(6) yes C18 . I16 . O33 . 95.6(6) yes I1 1_445 O17 . I16 . 109.2(5) yes I16 . C18 . C19 . 128.3(12) yes I16 . C18 . C32 . 111.9(12) yes C19 . C18 . C32 . 119.8(18) yes C18 . C19 . S20 . 122.8(12) yes C18 . C19 . C30 . 121.3(15) yes S20 . C19 . C30 . 115.9(11) yes C19 . S20 . N21 . 107.3(6) yes C19 . S20 . O28 . 107.3(6) yes N21 . S20 . O28 . 106.5(7) yes C19 . S20 . O29 . 107.0(7) yes N21 . S20 . O29 . 107.6(6) yes O28 . S20 . O29 . 120.5(7) yes S20 . N21 . C22 . 121.0(9) yes S20 . N21 . H211 . 119.427 no C22 . N21 . H211 . 119.542 no N21 . C22 . C23 . 110.2(10) yes N21 . C22 . C27 . 108.6(12) yes C23 . C22 . C27 . 110.1(13) yes N21 . C22 . H221 . 109.013 no C23 . C22 . H221 . 109.413 no C27 . C22 . H221 . 109.492 no C22 . C23 . O24 . 110.2(13) yes C22 . C23 . O26 . 126.3(14) yes O24 . C23 . O26 . 123.4(16) yes C23 . O24 . C25 . 113.8(20) yes O24 . C25 . H251 . 110.422 no O24 . C25 . H252 . 110.335 no H251 . C25 . H252 . 104.022 no O24 . C25 . H253 . 114.440 no H251 . C25 . H253 . 111.573 no H252 . C25 . H253 . 105.420 no C22 . C27 . H271 . 110.522 no C22 . C27 . H272 . 109.907 no H271 . C27 . H272 . 109.706 no C22 . C27 . H273 . 109.237 no H271 . C27 . H273 . 109.017 no H272 . C27 . H273 . 108.412 no C19 . C30 . C26 . 114.7(19) yes C19 . C30 . H301 . 121.927 no C26 . C30 . H301 . 123.329 no C18 . C32 . C1 . 120.6(16) yes C18 . C32 . H321 . 120.916 no C1 . C32 . H321 . 118.451 no C32 . C1 . C26 . 116.2(18) yes C32 . C1 . H11 . 121.864 no C26 . C1 . H11 . 121.891 no C1 . C26 . C30 . 127(2) yes C1 . C26 . H261 . 115.235 no C30 . C26 . H261 . 117.412 no C2 . O6 . C10 . 118.9(18) yes C7 . C8 . H81 . 111.506 no C7 . C8 . H82 . 110.625 no H81 . C8 . H82 . 108.225 no C7 . C8 . H83 . 109.755 no H81 . C8 . H83 . 108.666 no H82 . C8 . H83 . 107.968 no C7 . C2 . O6 . 110.6(13) yes C7 . C2 . O1 . 123.5(14) yes O6 . C2 . O1 . 125.8(15) yes O6 . C10 . H101 . 112.284 no O6 . C10 . H102 . 110.192 no H101 . C10 . H102 . 107.130 no O6 . C10 . H103 . 111.111 no H101 . C10 . H103 . 108.435 no H102 . C10 . H103 . 107.490 no _chemical_name_common Alex-3 data_2 _database_code_depnum_ccdc_archive 'CCDC 268075' _audit_creation_date 05-06-10 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'SHELXL on TEXSAN' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 15.878(4) _cell_length_b 8.135(11) _cell_length_c 13.873(6) _cell_angle_alpha 90 _cell_angle_beta 105.53(3) _cell_angle_gamma 90 _cell_volume 1727(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C16 H16 I1 N1 O6 S1 # Dc = 1.84 Fooo = 880.00 Mu = 20.09 M = 954.55 # Found Formula = C13 H18 I1 N1 O6 S1 # Dc = 1.71 FOOO = 880.00 Mu = 20.01 M = 886.52 _chemical_formula_sum 'C13 H18 I1 N1 O6 S1' _chemical_formula_moiety 'C13 H18 I1 N1 O6 S1' _chemical_compound_source ? _chemical_formula_weight 443.26 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 18 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 2.001 # Sheldrick geometric approximatio 0.67 0.90 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; Azimutal absorption correction (North et al, 1968) ; _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.90 _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q _computing_data_collection 'Rigaku AFC-7R' _computing_data_reduction 'TeXsan 1.10b' _computing_cell_refinement WinAFC _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _diffrn_standards_decay_% 60.70 _diffrn_ambient_temperature 293 _diffrn_reflns_number 4260 _reflns_number_total 4255 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 3036 # Number of reflections without Friedels Law is 4255 # Theoretical number of reflections is about 3979 _diffrn_reflns_theta_min 2.663 _diffrn_reflns_theta_max 27.532 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.532 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -20 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 3.31 _oxford_diffrn_Wilson_scale 12.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.87 _refine_diff_density_max 1.01 _refine_ls_number_reflns 3036 _refine_ls_number_restraints 1 _refine_ls_number_parameters 398 #_refine_ls_R_factor_ref 0.0574 _refine_ls_wR_factor_ref 0.1261 _refine_ls_goodness_of_fit_ref 0.9350 #_reflns_number_all 4238 _refine_ls_R_factor_all 0.0921 _refine_ls_wR_factor_all 0.1702 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3036 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_gt 0.1261 _refine_ls_shift/su_max 0.000331 _refine_ls_abs_structure_Flack -0.06(15) _refine_ls_abs_structure_details 'Flack, 1219 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 32.2 34.5 21.1 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens I1 I 2.00330(6) 0.5247(7) 0.99439(8) 0.0383 1.0000 Uani . . . . . . O2 O 2.0366(7) 0.3181(16) 0.9700(9) 0.0523 1.0000 Uani . . . . . . C3 C 1.8687(8) 0.512(3) 0.9083(11) 0.0443 1.0000 Uani . . . . . . C4 C 1.8419(9) 0.494(3) 0.8066(11) 0.0415 1.0000 Uani . . . . . . S5 S 1.9156(3) 0.4474(7) 0.7351(3) 0.0450 1.0000 Uani . . . . . . N6 N 1.9309(9) 0.2530(17) 0.7431(10) 0.0373 1.0000 Uani . . . . . . C7 C 1.8603(11) 0.141(2) 0.6988(14) 0.0418 1.0000 Uani . . . . . . C8 C 1.8075(12) 0.097(2) 0.7732(13) 0.0408 1.0000 Uani . . . . . . O9 O 1.7300(7) 0.034(3) 0.7234(9) 0.0653 1.0000 Uani . . . . . . C10 C 1.6731(13) -0.014(5) 0.7842(18) 0.1053 1.0000 Uani . . . . . . O11 O 1.8334(9) 0.1089(18) 0.8623(9) 0.0508 1.0000 Uani . . . . . . C12 C 1.8920(13) -0.013(3) 0.6571(13) 0.0528 1.0000 Uani . . . . . . C13 C 1.9293(12) 0.015(3) 0.5688(13) 0.0637 1.0000 Uani . . . . . . C14 C 1.8593(18) 0.081(4) 0.4785(12) 0.0792 1.0000 Uani . . . . . . C15 C 1.971(2) -0.145(4) 0.546(2) 0.1341 1.0000 Uani . . . . . . O16 O 1.9973(7) 0.528(2) 0.7867(8) 0.0548 1.0000 Uani . . . . . . O17 O 1.8729(9) 0.4891(18) 0.6331(8) 0.0593 1.0000 Uani . . . . . . C18 C 1.7508(11) 0.483(3) 0.7597(15) 0.0554 1.0000 Uani . . . . . . C19 C 1.6939(10) 0.506(3) 0.8178(15) 0.0642 1.0000 Uani . . . . . . C20 C 1.7225(12) 0.526(4) 0.9197(14) 0.0660 1.0000 Uani . . . . . . C21 C 1.8097(9) 0.536(3) 0.9643(11) 0.0541 1.0000 Uani . . . . . . O22 O 1.9808(8) 0.4993(19) 1.1147(7) 0.0532 1.0000 Uani . . . . . . C23 C 1.3384(10) 0.269(2) 0.7814(11) 0.0409 1.0000 Uani . . . . . . S24 S 1.4215(3) 0.2043(7) 0.7255(3) 0.0429 1.0000 Uani . . . . . . N25 N 1.4335(8) 0.015(2) 0.7444(10) 0.0446 1.0000 Uani . . . . . . C26 C 1.3634(11) -0.107(3) 0.7041(11) 0.0489 1.0000 Uani . . . . . . C27 C 1.3120(10) -0.135(3) 0.7817(13) 0.0425 1.0000 Uani . . . . . . O28 O 1.2326(9) -0.192(2) 0.7371(11) 0.0660 1.0000 Uani . . . . . . C29 C 1.1743(16) -0.225(4) 0.8024(18) 0.0951 1.0000 Uani . . . . . . O30 O 1.3384(7) -0.111(3) 0.8694(8) 0.0599 1.0000 Uani . . . . . . C31 C 1.3987(12) -0.265(2) 0.6737(13) 0.0486 1.0000 Uani . . . . . . C32 C 1.4402(11) -0.249(3) 0.5868(11) 0.0497 1.0000 Uani . . . . . . C33 C 1.3695(16) -0.218(5) 0.4914(13) 0.1117 1.0000 Uani . . . . . . C34 C 1.499(2) -0.387(4) 0.578(2) 0.1074 1.0000 Uani . . . . . . O35 O 1.5018(7) 0.2787(18) 0.7838(9) 0.0518 1.0000 Uani . . . . . . O36 O 1.3905(9) 0.2329(19) 0.6210(8) 0.0632 1.0000 Uani . . . . . . C37 C 1.3562(10) 0.324(2) 0.8760(12) 0.0416 1.0000 Uani . . . . . . I38 I 1.48891(6) 0.3698(7) 0.97252(7) 0.0402 1.0000 Uani . . . . . . O39 O 1.4505(7) 0.4276(19) 1.0802(9) 0.0576 1.0000 Uani . . . . . . O40 O 1.5096(8) 0.568(2) 0.9267(10) 0.0564 1.0000 Uani . . . . . . C41 C 1.2927(11) 0.370(4) 0.9219(13) 0.0622 1.0000 Uani . . . . . . C42 C 1.2047(11) 0.343(4) 0.8691(15) 0.0689 1.0000 Uani . . . . . . C43 C 1.1856(11) 0.288(3) 0.7699(16) 0.0611 1.0000 Uani . . . . . . C44 C 1.2514(12) 0.252(3) 0.7246(15) 0.0591 1.0000 Uani . . . . . . H71 H 1.8206 0.1984 0.6426 0.0585 1.0000 Uiso R . . . . . H101 H 1.6236 -0.0748 0.7412 0.1204 1.0000 Uiso R . . . . . H102 H 1.7050 -0.0854 0.8390 0.1204 1.0000 Uiso R . . . . . H103 H 1.6516 0.0836 0.8115 0.1204 1.0000 Uiso R . . . . . H121 H 1.9379 -0.0628 0.7105 0.0624 1.0000 Uiso R . . . . . H122 H 1.8426 -0.0890 0.6364 0.0624 1.0000 Uiso R . . . . . H131 H 1.9758 0.0982 0.5888 0.0812 1.0000 Uiso R . . . . . H141 H 1.8824 0.0865 0.4196 0.0949 1.0000 Uiso R . . . . . H142 H 1.8412 0.1910 0.4937 0.0949 1.0000 Uiso R . . . . . H143 H 1.8082 0.0075 0.4636 0.0949 1.0000 Uiso R . . . . . H151 H 1.9719 -0.1458 0.4761 0.1658 1.0000 Uiso R . . . . . H152 H 2.0304 -0.1528 0.5902 0.1658 1.0000 Uiso R . . . . . H153 H 1.9356 -0.2375 0.5593 0.1658 1.0000 Uiso R . . . . . H181 H 1.7293 0.4608 0.6878 0.0645 1.0000 Uiso R . . . . . H191 H 1.6309 0.5056 0.7855 0.0738 1.0000 Uiso R . . . . . H201 H 1.6803 0.5351 0.9596 0.0874 1.0000 Uiso R . . . . . H211 H 1.8304 0.5585 1.0362 0.0699 1.0000 Uiso R . . . . . H261 H 1.3234 -0.0589 0.6444 0.0622 1.0000 Uiso R . . . . . H291 H 1.1247 -0.2930 0.7667 0.1255 1.0000 Uiso R . . . . . H292 H 1.2062 -0.2815 0.8639 0.1255 1.0000 Uiso R . . . . . H293 H 1.1525 -0.1194 0.8199 0.1255 1.0000 Uiso R . . . . . H311 H 1.4434 -0.3065 0.7318 0.0632 1.0000 Uiso R . . . . . H312 H 1.3504 -0.3442 0.6546 0.0632 1.0000 Uiso R . . . . . H321 H 1.4766 -0.1498 0.5997 0.0672 1.0000 Uiso R . . . . . H331 H 1.3949 -0.2184 0.4342 0.1249 1.0000 Uiso R . . . . . H332 H 1.3417 -0.1119 0.4953 0.1249 1.0000 Uiso R . . . . . H333 H 1.3256 -0.3056 0.4828 0.1249 1.0000 Uiso R . . . . . H411 H 1.3083 0.4192 0.9889 0.0833 1.0000 Uiso R . . . . . H421 H 1.1577 0.3646 0.9009 0.0916 1.0000 Uiso R . . . . . H431 H 1.1243 0.2735 0.7317 0.0736 1.0000 Uiso R . . . . . H441 H 1.2374 0.2145 0.6550 0.0712 1.0000 Uiso R . . . . . H341 H 1.5166 -0.3743 0.5158 0.1283 1.0000 Uiso R . . . . . H342 H 1.5503 -0.3821 0.6360 0.1283 1.0000 Uiso R . . . . . H343 H 1.4677 -0.4907 0.5775 0.1283 1.0000 Uiso R . . . . . H44 H 1.4839 -0.0325 0.8156 0.0500 1.0000 Uiso R . . . . . H61 H 1.9897 0.2084 0.7786 0.0440 1.0000 Uiso 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 0.0314(4) 0.0495(6) 0.0371(5) -0.0019(5) 0.0144(3) -0.0048(5) O2 0.040(6) 0.062(10) 0.063(7) -0.002(6) 0.028(5) -0.002(6) C3 0.008(5) 0.077(13) 0.049(8) -0.016(11) 0.009(5) -0.007(8) C4 0.025(7) 0.067(14) 0.033(8) -0.009(8) 0.008(6) -0.001(8) S5 0.044(2) 0.059(3) 0.038(2) -0.002(2) 0.0208(18) -0.008(2) N6 0.037(7) 0.023(8) 0.053(8) 0.002(6) 0.015(6) 0.009(6) C7 0.036(9) 0.043(11) 0.051(10) -0.006(7) 0.021(8) -0.007(7) C8 0.039(9) 0.042(10) 0.041(10) 0.006(7) 0.009(8) -0.002(8) O9 0.040(6) 0.109(13) 0.052(7) -0.003(11) 0.021(5) -0.011(10) C10 0.047(11) 0.20(4) 0.082(15) -0.01(2) 0.033(11) -0.041(18) O11 0.053(8) 0.073(9) 0.029(6) 0.005(5) 0.015(6) -0.005(6) C12 0.062(11) 0.060(14) 0.037(8) -0.006(8) 0.014(8) 0.005(9) C13 0.059(10) 0.096(16) 0.050(9) 0.002(13) 0.038(8) 0.016(13) C14 0.110(18) 0.11(2) 0.019(7) -0.002(10) 0.018(9) -0.008(17) C15 0.19(3) 0.13(3) 0.12(2) -0.02(2) 0.11(2) 0.05(3) O16 0.045(6) 0.067(9) 0.061(7) -0.002(8) 0.029(5) -0.029(8) O17 0.072(8) 0.074(11) 0.033(6) 0.015(6) 0.016(5) -0.004(7) C18 0.041(9) 0.064(14) 0.053(10) -0.007(9) -0.003(8) 0.006(8) C19 0.024(7) 0.098(18) 0.073(12) -0.025(14) 0.017(7) -0.009(10) C20 0.052(9) 0.091(16) 0.067(11) -0.017(16) 0.035(9) -0.020(14) C21 0.032(7) 0.101(16) 0.035(7) -0.019(12) 0.019(6) -0.021(11) O22 0.063(7) 0.071(10) 0.030(5) 0.000(6) 0.021(5) -0.013(7) C23 0.037(8) 0.046(10) 0.046(9) 0.004(9) 0.023(6) -0.008(8) S24 0.046(2) 0.046(3) 0.043(2) 0.0010(19) 0.0237(18) -0.007(2) N25 0.042(6) 0.044(8) 0.048(7) 0.009(8) 0.014(5) -0.010(8) C26 0.045(8) 0.075(15) 0.032(7) 0.001(9) 0.021(6) 0.002(10) C27 0.037(8) 0.041(9) 0.062(10) -0.014(10) 0.035(7) -0.028(9) O28 0.054(8) 0.087(12) 0.067(8) -0.021(8) 0.033(7) -0.030(8) C29 0.084(16) 0.14(2) 0.086(16) -0.015(19) 0.059(13) -0.054(18) O30 0.039(6) 0.103(12) 0.043(7) -0.002(9) 0.021(5) -0.001(9) C31 0.055(10) 0.054(13) 0.045(9) -0.014(8) 0.028(8) 0.008(9) C32 0.056(9) 0.064(13) 0.036(8) -0.020(8) 0.027(7) -0.020(9) C33 0.087(16) 0.21(4) 0.034(9) 0.019(19) 0.016(10) -0.01(2) C34 0.16(3) 0.11(2) 0.075(17) 0.037(15) 0.07(2) 0.06(2) O35 0.038(6) 0.054(7) 0.072(7) -0.017(8) 0.031(5) -0.024(6) O36 0.089(10) 0.073(11) 0.034(6) 0.006(6) 0.028(6) 0.001(8) C37 0.029(7) 0.058(14) 0.040(9) 0.014(7) 0.014(6) 0.003(7) I38 0.0338(5) 0.0460(6) 0.0451(6) -0.0078(6) 0.0181(4) -0.0012(5) O39 0.041(6) 0.086(11) 0.049(7) -0.018(7) 0.016(5) 0.020(6) O40 0.045(6) 0.070(10) 0.062(7) -0.010(8) 0.028(6) -0.002(7) C41 0.044(9) 0.092(15) 0.059(10) 0.015(14) 0.029(8) 0.012(13) C42 0.028(7) 0.12(2) 0.074(12) 0.004(14) 0.032(8) -0.001(11) C43 0.034(8) 0.063(13) 0.086(14) 0.026(13) 0.016(9) 0.003(10) C44 0.049(10) 0.072(15) 0.051(10) -0.006(11) 0.004(8) -0.006(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2833(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag I1 . O2 2_957 2.552(15) yes I1 . O2 . 1.821(14) yes I1 . C3 . 2.154(12) yes I1 . O22 . 1.810(10) yes C3 . C4 . 1.37(2) yes C3 . C21 . 1.382(19) yes C4 . S5 . 1.766(15) yes C4 . C18 . 1.42(2) yes S5 . N6 . 1.599(14) yes S5 . O16 . 1.459(11) yes S5 . O17 . 1.436(12) yes N6 . C7 . 1.45(2) yes N6 . H61 . 1.000 no C7 . C8 . 1.54(2) yes C7 . C12 . 1.52(2) yes C7 . H71 . 0.980 no C8 . O9 . 1.34(2) yes C8 . O11 . 1.20(2) yes O9 . C10 . 1.45(2) yes C10 . H101 . 0.981 no C10 . H102 . 0.982 no C10 . H103 . 0.981 no C12 . C13 . 1.51(2) yes C12 . H121 . 0.977 no C12 . H122 . 0.981 no C13 . C14 . 1.53(3) yes C13 . C15 . 1.53(4) yes C13 . H131 . 0.983 no C14 . H141 . 0.982 no C14 . H142 . 0.982 no C14 . H143 . 0.982 no C15 . H151 . 0.980 no C15 . H152 . 0.980 no C15 . H153 . 0.980 no C18 . C19 . 1.38(3) yes C18 . H181 . 0.980 no C19 . C20 . 1.37(3) yes C19 . H191 . 0.980 no C20 . C21 . 1.36(2) yes C20 . H201 . 0.980 no C21 . H211 . 0.980 no C23 . S24 . 1.779(16) yes C23 . C37 . 1.34(2) yes C23 . C44 . 1.40(2) yes S24 . N25 . 1.567(18) yes S24 . O35 . 1.448(11) yes S24 . O36 . 1.420(12) yes N25 . C26 . 1.48(2) yes N25 . H44 . 1.157 no C26 . C27 . 1.533(19) yes C26 . C31 . 1.51(3) yes C26 . H261 . 0.980 no C27 . O28 . 1.329(19) yes C27 . O30 . 1.193(18) yes O28 . C29 . 1.48(2) yes C29 . H291 . 0.982 no C29 . H292 . 0.982 no C29 . H293 . 0.980 no C31 . C32 . 1.53(2) yes C31 . H311 . 0.981 no C31 . H312 . 0.984 no C32 . C33 . 1.51(3) yes C32 . C34 . 1.49(3) yes C32 . H321 . 0.981 no C33 . H331 . 0.981 no C33 . H332 . 0.980 no C33 . H333 . 0.980 no C34 . H341 . 0.979 no C34 . H342 . 0.980 no C34 . H343 . 0.979 no C37 . I38 . 2.204(15) yes C37 . C41 . 1.38(2) yes I38 . O39 . 1.820(11) yes I38 . O40 . 1.793(17) yes C41 . C42 . 1.41(2) yes C41 . H411 . 0.980 no C42 . C43 . 1.40(3) yes C42 . H421 . 0.979 no C43 . C44 . 1.39(3) yes C43 . H431 . 0.983 no C44 . H441 . 0.980 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 2_957 I1 . O2 . 177.6(2) yes O2 2_957 I1 . C3 . 83.7(7) yes O2 . I1 . C3 . 98.5(8) yes O2 2_957 I1 . O22 . 78.9(6) yes O2 . I1 . O22 . 101.8(7) yes C3 . I1 . O22 . 95.4(6) yes I1 2_947 O2 . I1 . 136.7(6) yes I1 . C3 . C4 . 124.4(10) yes I1 . C3 . C21 . 113.8(10) yes C4 . C3 . C21 . 121.6(12) yes C3 . C4 . S5 . 122.2(11) yes C3 . C4 . C18 . 118.5(14) yes S5 . C4 . C18 . 118.3(13) yes C4 . S5 . N6 . 106.5(9) yes C4 . S5 . O16 . 105.3(8) yes N6 . S5 . O16 . 108.1(9) yes C4 . S5 . O17 . 107.1(8) yes N6 . S5 . O17 . 109.0(8) yes O16 . S5 . O17 . 120.0(8) yes S5 . N6 . C7 . 120.5(11) yes S5 . N6 . H61 . 119.778 no C7 . N6 . H61 . 119.714 no N6 . C7 . C8 . 111.2(15) yes N6 . C7 . C12 . 112.5(14) yes C8 . C7 . C12 . 111.2(15) yes N6 . C7 . H71 . 107.252 no C8 . C7 . H71 . 107.106 no C12 . C7 . H71 . 107.373 no C7 . C8 . O9 . 109.5(15) yes C7 . C8 . O11 . 125.2(17) yes O9 . C8 . O11 . 125.2(17) yes C8 . O9 . C10 . 115.8(15) yes O9 . C10 . H101 . 107.883 no O9 . C10 . H102 . 109.794 no H101 . C10 . H102 . 109.735 no O9 . C10 . H103 . 109.827 no H101 . C10 . H103 . 109.762 no H102 . C10 . H103 . 109.813 no C7 . C12 . C13 . 115.1(18) yes C7 . C12 . H121 . 108.049 no C13 . C12 . H121 . 107.651 no C7 . C12 . H122 . 108.060 no C13 . C12 . H122 . 108.327 no H121 . C12 . H122 . 109.585 no C12 . C13 . C14 . 111.1(16) yes C12 . C13 . C15 . 108(2) yes C14 . C13 . C15 . 113(2) yes C12 . C13 . H131 . 107.605 no C14 . C13 . H131 . 108.575 no C15 . C13 . H131 . 108.064 no C13 . C14 . H141 . 110.217 no C13 . C14 . H142 . 109.348 no H141 . C14 . H142 . 109.348 no C13 . C14 . H143 . 109.752 no H141 . C14 . H143 . 109.053 no H142 . C14 . H143 . 109.104 no C13 . C15 . H151 . 109.179 no C13 . C15 . H152 . 108.959 no H151 . C15 . H152 . 110.122 no C13 . C15 . H153 . 108.597 no H151 . C15 . H153 . 109.931 no H152 . C15 . H153 . 110.021 no C4 . C18 . C19 . 118.1(16) yes C4 . C18 . H181 . 120.856 no C19 . C18 . H181 . 121.053 no C18 . C19 . C20 . 122.0(16) yes C18 . C19 . H191 . 118.815 no C20 . C19 . H191 . 119.119 no C19 . C20 . C21 . 119.4(16) yes C19 . C20 . H201 . 120.183 no C21 . C20 . H201 . 120.356 no C3 . C21 . C20 . 119.8(14) yes C3 . C21 . H211 . 120.292 no C20 . C21 . H211 . 119.892 no S24 . C23 . C37 . 122.6(12) yes S24 . C23 . C44 . 117.4(14) yes C37 . C23 . C44 . 120.0(15) yes C23 . S24 . N25 . 106.9(8) yes C23 . S24 . O35 . 106.1(8) yes N25 . S24 . O35 . 105.6(8) yes C23 . S24 . O36 . 107.6(8) yes N25 . S24 . O36 . 109.0(9) yes O35 . S24 . O36 . 121.0(8) yes S24 . N25 . C26 . 123.3(12) yes S24 . N25 . H44 . 119.657 no C26 . N25 . H44 . 112.212 no N25 . C26 . C27 . 108.8(13) yes N25 . C26 . C31 . 112.2(14) yes C27 . C26 . C31 . 112.2(18) yes N25 . C26 . H261 . 107.707 no C27 . C26 . H261 . 107.749 no C31 . C26 . H261 . 108.064 no C26 . C27 . O28 . 110.0(14) yes C26 . C27 . O30 . 125.7(13) yes O28 . C27 . O30 . 124.2(14) yes C27 . O28 . C29 . 116.6(15) yes O28 . C29 . H291 . 109.956 no O28 . C29 . H292 . 110.705 no H291 . C29 . H292 . 109.324 no O28 . C29 . H293 . 108.278 no H291 . C29 . H293 . 109.244 no H292 . C29 . H293 . 109.308 no C26 . C31 . C32 . 114.9(17) yes C26 . C31 . H311 . 107.883 no C32 . C31 . H311 . 107.917 no C26 . C31 . H312 . 108.259 no C32 . C31 . H312 . 108.213 no H311 . C31 . H312 . 109.607 no C31 . C32 . C33 . 109.3(15) yes C31 . C32 . C34 . 114.6(17) yes C33 . C32 . C34 . 113(2) yes C31 . C32 . H321 . 106.475 no C33 . C32 . H321 . 106.721 no C34 . C32 . H321 . 106.405 no C32 . C33 . H331 . 109.832 no C32 . C33 . H332 . 109.801 no H331 . C33 . H332 . 109.467 no C32 . C33 . H333 . 109.002 no H331 . C33 . H333 . 109.427 no H332 . C33 . H333 . 109.296 no C32 . C34 . H341 . 109.026 no C32 . C34 . H342 . 107.656 no H341 . C34 . H342 . 110.461 no C32 . C34 . H343 . 108.727 no H341 . C34 . H343 . 110.497 no H342 . C34 . H343 . 110.400 no C23 . C37 . I38 . 124.5(11) yes C23 . C37 . C41 . 123.5(15) yes I38 . C37 . C41 . 111.9(13) yes C37 . I38 . O39 . 93.8(6) yes C37 . I38 . O40 . 99.9(6) yes O39 . I38 . O40 . 101.1(7) yes C37 . C41 . C42 . 117.6(19) yes C37 . C41 . H411 . 121.108 no C42 . C41 . H411 . 121.325 no C41 . C42 . C43 . 119.0(16) yes C41 . C42 . H421 . 120.433 no C43 . C42 . H421 . 120.582 no C42 . C43 . C44 . 121.4(16) yes C42 . C43 . H431 . 119.467 no C44 . C43 . H431 . 119.142 no C23 . C44 . C43 . 118.3(18) yes C23 . C44 . H441 . 120.859 no C43 . C44 . H441 . 120.884 no