#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:40:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178437 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/58/4025865.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025865
loop_
_publ_author_name
'Jarugu Narasimha Moorthy'
'Kalyan Senapati'
'Keshaba Nanda Parida'
_publ_contact_author_address
;Departmet of chemistry
Indian Institute of Technology - Kanpur
Kanpur - 208 016
INDIA
;
_publ_contact_author_email       moorthy@iitk.ac.in
_publ_contact_author_fax         +915122597436
_publ_contact_author_name        'Prof. J. N. Moorthy'
_publ_contact_author_phone       +915122597438
_publ_section_title
;
 6-Membered Pseudocyclic IBX Acids: Syntheses, X-ray Structural
 Characterizations, and Oxidation Reactivities in Common Organic Solvents
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8416
_journal_page_last               8421
_journal_paper_doi               10.1021/jo101639j
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C10 H11 I O4, C2 H F3 O2'
_chemical_formula_sum            'C12 H12 F3 I O6'
_chemical_formula_weight         436.12
_chemical_melting_point          435.1(10)
_chemical_name_common            '2-(2-iodylphenyl)-2-methylpropanoic acid'
_chemical_name_systematic
; 
 Pseudocyclic IBX Acid1
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.811(4)
_cell_angle_beta                 68.309(3)
_cell_angle_gamma                72.842(4)
_cell_formula_units_Z            4
_cell_length_a                   10.195(2)
_cell_length_b                   12.572(3)
_cell_length_c                   13.120(3)
_cell_measurement_reflns_used    4877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.24
_cell_volume                     1482.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7491
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    2.219
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.954
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blacks
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.162
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0449P)²+0.3984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                4526
_reflns_number_total             5063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101639j_si_001.cif
_cod_data_source_block           25augbm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '161-163 C' was changed to
'435.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025865
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 -0.11291(2) 0.628037(18) 0.459863(17) 0.01300(9) Uani 1 1 d . . .
I2 I 0.55217(2) 0.611774(18) 0.423155(18) 0.01300(9) Uani 1 1 d . . .
C25 C 0.3300(4) 0.8709(3) 0.3817(3) 0.0183(8) Uani 1 1 d . . .
O10 O 0.7506(3) 0.5342(2) 0.3739(2) 0.0164(5) Uani 1 1 d . . .
O4 O -0.3087(3) 0.7154(2) 0.5219(2) 0.0166(5) Uani 1 1 d . . .
O11 O 0.5034(3) 0.4943(2) 0.3853(2) 0.0170(5) Uani 1 1 d . . .
O3 O -0.0469(3) 0.6992(2) 0.5401(2) 0.0220(6) Uani 1 1 d . . .
O1 O 0.3856(3) 0.5181(2) 0.2378(2) 0.0218(6) Uani 1 1 d . . .
H1 H 0.4145 0.5077 0.2903 0.033 Uiso 1 1 calc R . .
O2 O 0.1717(3) 0.5218(2) 0.3694(2) 0.0183(6) Uani 1 1 d . . .
C18 C 0.5743(4) 0.7026(3) 0.2844(3) 0.0149(7) Uani 1 1 d . . .
C17 C 0.7038(4) 0.6505(3) 0.1937(3) 0.0175(8) Uani 1 1 d . . .
H17 H 0.7680 0.5795 0.1970 0.021 Uiso 1 1 calc R . .
C6 C -0.0594(4) 0.7083(3) 0.3136(3) 0.0144(7) Uani 1 1 d . . .
C1 C 0.0635(4) 0.6640(3) 0.2129(3) 0.0144(7) Uani 1 1 d . . .
O17 O 0.2969(3) 0.6968(2) 0.4466(2) 0.0188(6) Uani 1 1 d . . .
C21 C 0.2382(4) 0.7932(3) 0.4304(3) 0.0161(8) Uani 1 1 d . . .
O18 O 0.0973(3) 0.8327(2) 0.4531(2) 0.0224(6) Uani 1 1 d . . .
H18 H 0.0570 0.7838 0.4788 0.034 Uiso 1 1 calc R . .
C7 C 0.1769(4) 0.5450(3) 0.1860(3) 0.0160(8) Uani 1 1 d . . .
C9 C 0.2985(4) 0.5249(3) 0.0700(3) 0.0201(8) Uani 1 1 d . . .
H9A H 0.3502 0.5808 0.0624 0.030 Uiso 1 1 calc R . .
H9B H 0.2535 0.5313 0.0150 0.030 Uiso 1 1 calc R . .
H9C H 0.3699 0.4496 0.0583 0.030 Uiso 1 1 calc R . .
C3 C -0.0244(4) 0.8442(3) 0.1481(3) 0.0235(9) Uani 1 1 d . . .
H3 H -0.0108 0.8905 0.0902 0.028 Uiso 1 1 calc R . .
C16 C 0.7398(4) 0.7023(4) 0.0976(3) 0.0248(9) Uani 1 1 d . . .
H16 H 0.8293 0.6684 0.0354 0.030 Uiso 1 1 calc R . .
C10 C 0.2462(4) 0.5270(3) 0.2730(3) 0.0152(8) Uani 1 1 d . . .
C2 C 0.0755(4) 0.7369(3) 0.1314(3) 0.0196(8) Uani 1 1 d . . .
H2 H 0.1554 0.7118 0.0615 0.023 Uiso 1 1 calc R . .
C5 C -0.1592(4) 0.8153(3) 0.3314(3) 0.0184(8) Uani 1 1 d . . .
H5 H -0.2390 0.8415 0.4013 0.022 Uiso 1 1 calc R . .
C8 C 0.0975(4) 0.4568(3) 0.1939(3) 0.0180(8) Uani 1 1 d . . .
H8A H 0.1711 0.3817 0.1730 0.027 Uiso 1 1 calc R . .
H8B H 0.0445 0.4699 0.1438 0.027 Uiso 1 1 calc R . .
H8C H 0.0264 0.4624 0.2698 0.027 Uiso 1 1 calc R . .
C4 C -0.1437(4) 0.8845(3) 0.2485(3) 0.0217(8) Uani 1 1 d . . .
H4 H -0.2128 0.9575 0.2598 0.026 Uiso 1 1 calc R . .
C15 C 0.6418(4) 0.8046(4) 0.0951(3) 0.0256(9) Uani 1 1 d . . .
H15 H 0.6642 0.8413 0.0304 0.031 Uiso 1 1 calc R . .
F4 F 0.0473(3) 0.89933(19) 0.7245(2) 0.0318(6) Uani 1 1 d . . .
F2 F 0.5232(3) 0.0927(2) 0.0776(2) 0.0410(7) Uani 1 1 d . . .
F5 F 0.0065(4) 0.8938(2) 0.8955(2) 0.0504(8) Uani 1 1 d . . .
F3 F 0.5795(3) 0.2434(2) 0.0495(2) 0.0449(7) Uani 1 1 d . . .
O7 O 0.1540(3) 0.6841(2) 0.6796(2) 0.0257(6) Uani 1 1 d . . .
H7 H 0.1994 0.6149 0.6675 0.039 Uiso 1 1 calc R . .
F1 F 0.7396(3) 0.0937(3) 0.0578(2) 0.0586(9) Uani 1 1 d . . .
O6 O 0.4039(3) 0.2312(3) 0.2688(3) 0.0382(8) Uani 1 1 d . . .
C11 C 0.5436(4) 0.1845(3) 0.2261(3) 0.0242(9) Uani 1 1 d . . .
O8 O 0.1249(3) 0.6658(2) 0.8578(2) 0.0318(7) Uani 1 1 d . . .
C14 C 0.1097(4) 0.7180(3) 0.7847(3) 0.0217(8) Uani 1 1 d . . .
F6 F -0.1315(3) 0.8445(2) 0.8284(2) 0.0448(7) Uani 1 1 d . . .
O5 O 0.6321(4) 0.1673(3) 0.2702(3) 0.0478(9) Uani 1 1 d . . .
C13 C 0.0089(5) 0.8402(3) 0.8077(3) 0.0261(9) Uani 1 1 d . . .
C12 C 0.5991(5) 0.1527(4) 0.1010(3) 0.0272(9) Uani 1 1 d . . .
C19 C 0.3722(4) 0.9075(3) 0.4766(3) 0.0216(8) Uani 1 1 d . . .
H19A H 0.2812 0.9462 0.5404 0.032 Uiso 1 1 calc R . .
H19B H 0.4314 0.9582 0.4503 0.032 Uiso 1 1 calc R . .
H19C H 0.4302 0.8411 0.4982 0.032 Uiso 1 1 calc R . .
C23 C 0.4726(4) 0.8068(3) 0.2841(3) 0.0156(8) Uani 1 1 d . . .
C24 C 0.5121(4) 0.8538(3) 0.1854(3) 0.0236(9) Uani 1 1 d . . .
H24 H 0.4464 0.9231 0.1801 0.028 Uiso 1 1 calc R . .
C26 C 0.2340(5) 0.9768(3) 0.3551(4) 0.0284(10) Uani 1 1 d . . .
H26A H 0.2096 0.9577 0.2934 0.043 Uiso 1 1 calc R . .
H26B H 0.2888 1.0310 0.3347 0.043 Uiso 1 1 calc R . .
H26C H 0.1420 1.0097 0.4201 0.043 Uiso 1 1 calc R . .
H1F H 0.367(7) 0.245(5) 0.339(6) 0.08(2) Uiso 1 1 d . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 I1 O4 96.62(12) . . ?
O3 I1 C6 100.11(13) . . ?
O4 I1 C6 95.65(13) . . ?
O11 I2 O10 93.98(11) . . ?
O11 I2 C18 102.91(13) . . ?
O10 I2 C18 94.07(13) . . ?
O11 I2 O17 77.34(10) . . ?
O10 I2 O17 166.62(10) . . ?
C18 I2 O17 78.25(11) . . ?
C21 C25 C26 110.0(3) . . ?
C21 C25 C23 110.0(3) . . ?
C26 C25 C23 114.6(3) . . ?
C21 C25 C19 105.5(3) . . ?
C26 C25 C19 107.1(3) . . ?
C23 C25 C19 109.1(3) . . ?
C17 C18 C23 122.9(3) . . ?
C17 C18 I2 112.6(3) . . ?
C23 C18 I2 124.5(3) . . ?
C18 C17 C16 120.0(4) . . ?
C5 C6 C1 123.2(3) . . ?
C5 C6 I1 110.4(3) . . ?
C1 C6 I1 126.4(3) . . ?
C2 C1 C6 114.4(3) . . ?
C2 C1 C7 119.5(3) . . ?
C6 C1 C7 126.1(3) . . ?
C21 O17 I2 127.3(2) . . ?
O17 C21 O18 121.9(3) . . ?
O17 C21 C25 121.4(3) . . ?
O18 C21 C25 116.7(3) . . ?
C9 C7 C10 110.3(3) . . ?
C9 C7 C8 107.8(3) . . ?
C10 C7 C8 107.2(3) . . ?
C9 C7 C1 112.7(3) . . ?
C10 C7 C1 108.6(3) . . ?
C8 C7 C1 110.2(3) . . ?
C4 C3 C2 120.8(4) . . ?
C15 C16 C17 118.3(4) . . ?
O2 C10 O1 123.2(3) . . ?
O2 C10 C7 121.0(3) . . ?
O1 C10 C7 115.8(3) . . ?
C3 C2 C1 123.0(4) . . ?
C4 C5 C6 120.6(4) . . ?
C5 C4 C3 118.1(4) . . ?
C24 C15 C16 120.8(4) . . ?
O5 C11 O6 128.7(4) . . ?
O5 C11 C12 119.7(4) . . ?
O6 C11 C12 111.6(4) . . ?
O8 C14 O7 129.6(4) . . ?
O8 C14 C13 121.4(4) . . ?
O7 C14 C13 108.4(3) . . ?
F4 C13 F5 107.2(3) . . ?
F4 C13 F6 106.6(3) . . ?
F5 C13 F6 106.8(3) . . ?
F4 C13 C14 113.7(3) . . ?
F5 C13 C14 111.9(3) . . ?
F6 C13 C14 110.2(3) . . ?
F1 C12 F3 108.2(4) . . ?
F1 C12 F2 107.5(4) . . ?
F3 C12 F2 106.3(3) . . ?
F1 C12 C11 112.3(4) . . ?
F3 C12 C11 111.0(3) . . ?
F2 C12 C11 111.2(3) . . ?
C24 C23 C18 114.9(3) . . ?
C24 C23 C25 119.2(3) . . ?
C18 C23 C25 125.9(3) . . ?
C15 C24 C23 123.2(4) . . ?
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 O3 1.802(3) . ?
I1 O4 1.835(2) . ?
I1 C6 2.130(3) . ?
I2 O11 1.816(2) . ?
I2 O10 1.826(2) . ?
I2 C18 2.122(3) . ?
I2 O17 2.404(2) . ?
C25 C21 1.527(5) . ?
C25 C26 1.528(5) . ?
C25 C23 1.530(5) . ?
C25 C19 1.568(5) . ?
O1 C10 1.291(4) . ?
O2 C10 1.224(4) . ?
C18 C17 1.387(5) . ?
C18 C23 1.411(5) . ?
C17 C16 1.394(5) . ?
C6 C5 1.385(5) . ?
C6 C1 1.413(5) . ?
C1 C2 1.400(5) . ?
C1 C7 1.542(5) . ?
O17 C21 1.239(4) . ?
C21 O18 1.290(4) . ?
C7 C9 1.530(5) . ?
C7 C10 1.534(5) . ?
C7 C8 1.538(5) . ?
C3 C4 1.388(6) . ?
C3 C2 1.389(6) . ?
C16 C15 1.385(6) . ?
C5 C4 1.383(5) . ?
C15 C24 1.378(6) . ?
F4 C13 1.323(5) . ?
F2 C12 1.334(5) . ?
F5 C13 1.325(5) . ?
F3 C12 1.326(5) . ?
O7 C14 1.310(5) . ?
F1 C12 1.303(5) . ?
O6 C11 1.267(5) . ?
C11 O5 1.211(5) . ?
C11 C12 1.537(6) . ?
O8 C14 1.192(5) . ?
C14 C13 1.533(6) . ?
F6 C13 1.339(5) . ?
C23 C24 1.392(5) . ?
