data_CRYSTALS_cif _audit_creation_date 05-06-01 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'XYZN file = SHELXL INS file, from DIRDIF out' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.946(4) _cell_length_b 9.383(3) _cell_length_c 17.097(4) _cell_angle_alpha 90 _cell_angle_beta 107.36(2) _cell_angle_gamma 90 _cell_volume 1829.1(10) _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x,y+1/2,-z+1/2' 'x,-y+1/2,z+1/2' 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' 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' _cell_formula_units_Z 4 # Given Formula = C16 H16 I2 O5 # Dc = 1.97 Fooo = 1032.00 Mu = 34.59 M = 542.11 # Found Formula = C16 H16 I2 O5 # Dc = 1.97 FOOO = 1032.00 Mu = 34.59 M = 542.11 _chemical_formula_sum 'C16 H16 I2 O5' _chemical_formula_moiety 'C16 H16 I2 O5' _chemical_compound_source ? _chemical_formula_weight 542.11 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _cell_measurement_temperature 298 _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.968 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 3.459 # Sheldrick geometric approximatio 0.38 0.50 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; Azimutal absorption correction (North et al, 1968) ; _exptl_absorpt_correction_T_min 0.38 _exptl_absorpt_correction_T_max 0.50 _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 'Win AFC' _computing_data_reduction 'TeXsan 10.3.b' _computing_cell_refinement 'Win AFC' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _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_% 92.70 _diffrn_ambient_temperature 298 _diffrn_reflns_number 4458 _reflns_number_total 4196 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 4196 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4203 _diffrn_reflns_theta_min 2.504 _diffrn_reflns_theta_max 27.521 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.521 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 0 _reflns_limit_h_min -15 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -2.59 _refine_diff_density_max 5.04 _refine_ls_number_reflns 2532 _refine_ls_number_restraints 0 _refine_ls_number_parameters 208 #_refine_ls_R_factor_ref 0.1249 _refine_ls_wR_factor_ref 0.3041 _refine_ls_goodness_of_fit_ref 1.3556 #_reflns_number_all 4155 _refine_ls_R_factor_all 0.1738 _refine_ls_wR_factor_all 2.5011 # 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 2532 _refine_ls_R_factor_gt 0.1249 _refine_ls_wR_factor_gt 0.3041 _refine_ls_shift/su_max 0.000039 # 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 '.' _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 ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.200 0.00 0.00 0.00 0.00 0.333 ; # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures have been sent by mail. ; _publ_contact_author_name 'Victor N. Nemykin' _publ_contact_author_address ; Department of Chemistry, University of Minnesota Duluth, 1039 University Drive, Duluth, MN, 55812. ; _publ_contact_author_phone '+1 218 7266729' _publ_contact_author_fax '+1 218 7267394' _publ_contact_author_email 'vnemykin@d.umn.edu' _publ_requested_journal 'Section C' _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' _publ_section_title # Title of paper ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Other, Anthony N.' # Author 1 ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Else, S. O.' # Author 2 ; ? # Address 2 ; ; ? # Footnote 2 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24, 351-359 Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 0.17565(12) -0.00244(14) 0.06477(7) 0.0394 1.0000 Uani . . . . . . I2 I 0.41682(12) -0.20076(14) 0.05431(7) 0.0376 1.0000 Uani . . . . . . O3 O 0.0998(14) 0.1650(17) 0.1249(9) 0.0475 1.0000 Uani . . . . . . O4 O 0.6473(19) -0.0719(19) 0.0516(14) 0.0782 1.0000 Uani . . . . . . O5 O 0.6042(15) -0.2707(16) 0.1056(10) 0.0517 1.0000 Uani . . . . . . O6 O 0.0795(19) 0.2692(18) 0.0050(10) 0.0659 1.0000 Uani . . . . . . O7 O 0.2408(11) -0.1785(15) 0.0228(9) 0.0373 1.0000 Uani . . . . . . C8 C 0.124(3) -0.223(2) 0.1770(16) 0.0609 1.0000 Uani . . . . . . C9 C 0.390(3) -0.513(3) 0.0710(15) 0.0616 1.0000 Uani . . . . . . C10 C 0.399(2) -0.385(3) 0.1965(11) 0.0448 1.0000 Uani . . . . . . C11 C 0.678(2) -0.174(3) 0.0930(11) 0.0434 1.0000 Uani . . . . . . C12 C 0.377(3) -0.642(3) 0.1131(19) 0.0719 1.0000 Uani . . . . . . C13 C 0.1883(15) -0.102(3) 0.1763(11) 0.0370 1.0000 Uani . . . . . . C14 C 0.025(3) 0.396(3) 0.106(2) 0.0834 1.0000 Uani . . . . . . C15 C 0.373(2) -0.635(3) 0.1919(19) 0.0690 1.0000 Uani . . . . . . C16 C 0.3980(17) -0.392(2) 0.1168(11) 0.0358 1.0000 Uani . . . . . . C17 C 0.283(3) -0.122(3) 0.3221(14) 0.0706 1.0000 Uani . . . . . . C18 C 0.210(2) -0.238(3) 0.3230(15) 0.0565 1.0000 Uani . . . . . . C19 C 0.383(2) -0.507(3) 0.2311(16) 0.0581 1.0000 Uani . . . . . . C20 C 0.127(3) -0.290(3) 0.2501(17) 0.0747 1.0000 Uani . . . . . . C21 C 0.068(2) 0.273(2) 0.0736(17) 0.0487 1.0000 Uani . . . . . . C22 C 0.802(2) -0.203(4) 0.1404(16) 0.0783 1.0000 Uani . . . . . . C24 C 0.260(2) -0.050(3) 0.2428(16) 0.0507 1.0000 Uani . . . . . . H81 H 0.0739 -0.2631 0.1238 0.0709 1.0000 Uiso R . . . . . H91 H 0.3924 -0.5117 0.0130 0.0711 1.0000 Uiso R . . . . . H101 H 0.4129 -0.2933 0.2275 0.0545 1.0000 Uiso R . . . . . H121 H 0.3722 -0.7361 0.0846 0.0812 1.0000 Uiso R . . . . . H151 H 0.3621 -0.7242 0.2207 0.0793 1.0000 Uiso R . . . . . H171 H 0.3466 -0.0906 0.3718 0.0805 1.0000 Uiso R . . . . . H181 H 0.2170 -0.2854 0.3767 0.0691 1.0000 Uiso R . . . . . H191 H 0.3771 -0.5054 0.2883 0.0672 1.0000 Uiso R . . . . . H201 H 0.0731 -0.3710 0.2519 0.0930 1.0000 Uiso R . . . . . H241 H 0.3020 0.0411 0.2400 0.0627 1.0000 Uiso R . . . . . H221 H 0.8517 -0.1305 0.1293 0.0935 1.0000 Uiso R . . . . . H222 H 0.8236 -0.2941 0.1244 0.0935 1.0000 Uiso R . . . . . H223 H 0.8094 -0.2035 0.1980 0.0935 1.0000 Uiso R . . . . . H141 H 0.0049 0.4692 0.0648 0.0978 1.0000 Uiso R . . . . . H142 H 0.0818 0.4322 0.1541 0.0978 1.0000 Uiso R . . . . . H143 H -0.0444 0.3675 0.1194 0.0978 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 0.0617(10) 0.0272(8) 0.0301(7) 0.0047(5) 0.0148(6) 0.0033(6) I2 0.0625(9) 0.0251(7) 0.0276(7) 0.0022(5) 0.0171(6) 0.0017(6) O3 0.074(10) 0.033(8) 0.038(8) 0.006(6) 0.022(8) 0.014(7) O4 0.111(15) 0.030(10) 0.110(16) 0.028(10) 0.058(13) 0.009(10) O5 0.073(11) 0.034(9) 0.044(9) 0.006(7) 0.012(8) -0.007(8) O6 0.114(15) 0.039(10) 0.040(9) 0.002(8) 0.015(10) 0.010(10) O7 0.039(7) 0.031(8) 0.042(7) -0.003(6) 0.011(6) 0.010(6) C8 0.12(2) 0.018(12) 0.045(13) 0.000(9) 0.019(14) -0.002(12) C9 0.088(18) 0.047(17) 0.044(13) -0.022(12) 0.009(13) 0.007(14) C10 0.076(14) 0.038(12) 0.024(9) 0.013(9) 0.021(10) 0.007(11) C11 0.065(14) 0.049(14) 0.021(9) -0.003(9) 0.020(9) 0.005(11) C12 0.10(2) 0.030(14) 0.069(18) -0.001(12) 0.009(17) -0.012(14) C13 0.032(9) 0.045(12) 0.035(10) 0.015(10) 0.012(8) 0.004(9) C14 0.11(2) 0.056(19) 0.08(2) -0.013(17) 0.022(17) 0.029(17) C15 0.068(16) 0.051(18) 0.08(2) 0.033(15) 0.016(15) 0.003(14) C16 0.052(11) 0.034(11) 0.027(9) 0.007(8) 0.019(8) 0.005(10) C17 0.11(2) 0.07(2) 0.030(11) -0.003(12) 0.010(13) -0.010(17) C18 0.085(17) 0.047(15) 0.039(12) 0.014(11) 0.020(12) -0.013(13) C19 0.078(17) 0.047(16) 0.046(14) 0.013(12) 0.013(12) -0.001(13) C20 0.12(2) 0.060(19) 0.046(14) 0.001(13) 0.033(16) -0.003(17) C21 0.053(13) 0.029(13) 0.072(17) -0.004(11) 0.031(12) 0.001(10) C22 0.040(12) 0.16(3) 0.041(13) -0.003(17) 0.013(10) -0.024(16) C24 0.066(15) 0.032(12) 0.057(14) 0.000(10) 0.024(12) -0.017(11) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 0.2644(11) 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 . I2 . 3.479(2) yes I1 . O3 . 2.214(15) yes I1 . O7 . 2.045(13) yes I1 . C13 . 2.089(18) yes I2 . O5 . 2.245(17) yes I2 . O7 . 2.020(13) yes I2 . C16 . 2.13(2) yes O3 . C21 . 1.32(3) yes O4 . C11 . 1.18(3) yes O5 . C11 . 1.33(3) yes O6 . C21 . 1.22(3) yes C8 . C13 . 1.37(3) yes C8 . C20 . 1.39(4) yes C8 . H81 . 1.000 no C9 . C12 . 1.44(4) yes C9 . C16 . 1.37(3) yes C9 . H91 . 1.000 no C10 . C16 . 1.36(3) yes C10 . C19 . 1.33(3) yes C10 . H101 . 1.000 no C11 . C22 . 1.48(3) yes C12 . C15 . 1.36(4) yes C12 . H121 . 1.000 no C13 . C24 . 1.30(3) yes C14 . C21 . 1.44(3) yes C14 . H141 . 0.960 no C14 . H142 . 0.960 no C14 . H143 . 0.960 no C15 . C19 . 1.36(4) yes C15 . H151 . 1.000 no C17 . C18 . 1.40(4) yes C17 . C24 . 1.46(3) yes C17 . H171 . 1.000 no C18 . C20 . 1.43(4) yes C18 . H181 . 1.000 no C19 . H191 . 1.000 no C20 . H201 . 1.000 no C22 . H221 . 0.960 no C22 . H222 . 0.960 no C22 . H223 . 0.960 no C24 . H241 . 1.000 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 I2 . I1 . O3 . 149.7(4) yes O3 . I1 . O7 . 170.9(6) yes I2 . I1 . C13 . 88.4(5) yes O3 . I1 . C13 . 79.8(7) yes O7 . I1 . C13 . 91.5(7) yes I1 . I2 . O5 . 151.7(4) yes O5 . I2 . O7 . 166.4(6) yes I1 . I2 . C16 . 102.2(5) yes O5 . I2 . C16 . 78.5(7) yes O7 . I2 . C16 . 87.9(7) yes I1 . O3 . C21 . 108.2(13) yes I2 . O5 . C11 . 111.9(14) yes I1 . O7 . I2 . 117.7(7) yes C13 . C8 . C20 . 121(3) yes C13 . C8 . H81 . 119.081 no C20 . C8 . H81 . 119.677 no C12 . C9 . C16 . 114(2) yes C12 . C9 . H91 . 123.139 no C16 . C9 . H91 . 122.451 no C16 . C10 . C19 . 117(2) yes C16 . C10 . H101 . 121.549 no C19 . C10 . H101 . 121.843 no O5 . C11 . O4 . 123(2) yes O5 . C11 . C22 . 113(2) yes O4 . C11 . C22 . 124(3) yes C9 . C12 . C15 . 119(3) yes C9 . C12 . H121 . 119.662 no C15 . C12 . H121 . 120.889 no C8 . C13 . I1 . 119.4(16) yes C8 . C13 . C24 . 122(2) yes I1 . C13 . C24 . 118.6(17) yes C21 . C14 . H141 . 109.213 no C21 . C14 . H142 . 111.469 no H141 . C14 . H142 . 109.476 no C21 . C14 . H143 . 107.696 no H141 . C14 . H143 . 109.476 no H142 . C14 . H143 . 109.476 no C12 . C15 . C19 . 121(2) yes C12 . C15 . H151 . 119.440 no C19 . C15 . H151 . 119.994 no I2 . C16 . C9 . 114.4(16) yes I2 . C16 . C10 . 119.5(17) yes C9 . C16 . C10 . 126(2) yes C18 . C17 . C24 . 115(2) yes C18 . C17 . H171 . 122.518 no C24 . C17 . H171 . 122.381 no C17 . C18 . C20 . 122(2) yes C17 . C18 . H181 . 118.399 no C20 . C18 . H181 . 119.524 no C15 . C19 . C10 . 123(2) yes C15 . C19 . H191 . 118.321 no C10 . C19 . H191 . 118.930 no C18 . C20 . C8 . 117(3) yes C18 . C20 . H201 . 121.303 no C8 . C20 . H201 . 121.744 no C14 . C21 . O3 . 115(2) yes C14 . C21 . O6 . 123(3) yes O3 . C21 . O6 . 121(2) yes C11 . C22 . H221 . 109.931 no C11 . C22 . H222 . 108.544 no H221 . C22 . H222 . 109.476 no C11 . C22 . H223 . 109.921 no H221 . C22 . H223 . 109.476 no H222 . C22 . H223 . 109.476 no C17 . C24 . C13 . 122(2) yes C17 . C24 . H241 . 118.758 no C13 . C24 . H241 . 119.272 no