#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/43/2234327.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234327
loop_
_publ_author_name
'Legault, Claude Y.'
'Prévost, Julie'
_publ_section_title
;
 1-Fluoro-3,3-dimethyl-1,3-dihydro-1λ³-benzo[d][1,2]iodoxole
;
_journal_coeditor_code           LH5436
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1238
_journal_paper_doi               10.1107/S1600536812012822
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C9 H10 F I O'
_chemical_formula_moiety         'C9 H10 F I O'
_chemical_formula_sum            'C9 H10 F I O'
_chemical_formula_weight         280.07
_chemical_name_systematic
;
1-Fluoro-3,3-dimethyl-1,3-dihydro-1λ³-benzo[d][1,2]iodoxole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                83.13(5)
_cell_angle_beta                 79.01(5)
_cell_angle_gamma                78.27(6)
_cell_formula_units_Z            4
_cell_length_a                   7.983(6)
_cell_length_b                   10.188(8)
_cell_length_c                   11.691(5)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     910.7(11)
_computing_cell_refinement       'DIFRAC (Flack et al., 1992)'
_computing_data_collection       'DIFRAC (Flack et al., 1992)'
_computing_data_reduction        'NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3408
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.55
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    3.481
_exptl_absorpt_correction_T_max  0.4215
_exptl_absorpt_correction_T_min  0.3365
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(NRCVAX; Gabe et al., 1989]'
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    2.043
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.64
_refine_diff_density_min         -1.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.4620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                2833
_reflns_number_total             3408
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5436.cif
_cod_data_source_block           I
_cod_original_cell_volume        910.6(11)
_cod_database_code               2234327
_cod_database_fobs_code          2234327
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.5725(6) 0.6621(4) 0.4130(4) 0.0211(9) Uani d . 1 1
C C2 0.7221(6) 0.5801(5) 0.4421(4) 0.0272(10) Uani d . 1 1
H H2 0.8038 0.5305 0.3853 0.033 Uiso calc R 1 1
C C3 0.7484(7) 0.5727(5) 0.5550(5) 0.0339(12) Uani d . 1 1
H H3 0.849 0.5164 0.5777 0.041 Uiso calc R 1 1
C C4 0.6295(6) 0.6467(5) 0.6364(4) 0.0288(11) Uani d . 1 1
H H4 0.6489 0.6399 0.7148 0.035 Uiso calc R 1 1
C C5 0.4833(6) 0.7300(5) 0.6056(4) 0.0270(10) Uani d . 1 1
H H5 0.4045 0.7827 0.6617 0.032 Uiso calc R 1 1
C C6 0.4513(6) 0.7368(4) 0.4917(4) 0.0227(9) Uani d . 1 1
C C7 0.2966(6) 0.8263(4) 0.4478(4) 0.0227(9) Uani d . 1 1
C C8 0.3279(7) 0.9700(5) 0.4218(4) 0.0299(11) Uani d . 1 1
H H8A 0.2272 1.0273 0.3935 0.045 Uiso calc R 1 1
H H8B 0.4316 0.9723 0.3618 0.045 Uiso calc R 1 1
H H8C 0.3451 1.0031 0.4933 0.045 Uiso calc R 1 1
C C9 0.1276(6) 0.8183(5) 0.5324(4) 0.0309(11) Uani d . 1 1
H H9A 0.0311 0.8776 0.5008 0.046 Uiso calc R 1 1
H H9B 0.1353 0.8467 0.6081 0.046 Uiso calc R 1 1
H H9C 0.1077 0.7255 0.5426 0.046 Uiso calc R 1 1
C C10 -0.0885(6) 0.8468(4) 0.0402(4) 0.0215(9) Uani d . 1 1
C C11 -0.2429(6) 0.9114(5) 0.0057(5) 0.0320(12) Uani d . 1 1
H H11 -0.3264 0.9704 0.0542 0.038 Uiso calc R 1 1
C C12 -0.2712(6) 0.8866(5) -0.1023(5) 0.0308(11) Uani d . 1 1
H H12 -0.3758 0.9292 -0.1291 0.037 Uiso calc R 1 1
C C13 -0.1484(6) 0.8006(5) -0.1711(4) 0.0302(11) Uani d . 1 1
H H13 -0.1687 0.7844 -0.2452 0.036 Uiso calc R 1 1
C C14 0.0050(6) 0.7373(4) -0.1332(4) 0.0245(10) Uani d . 1 1
H H14 0.0887 0.678 -0.1814 0.029 Uiso calc R 1 1
C C15 0.0367(6) 0.7600(4) -0.0255(4) 0.0212(9) Uani d . 1 1
C C16 0.1966(6) 0.6918(4) 0.0259(4) 0.0204(9) Uani d . 1 1
C C17 0.3625(6) 0.6881(5) -0.0644(4) 0.0267(10) Uani d . 1 1
H H17A 0.4625 0.6434 -0.0281 0.04 Uiso calc R 1 1
H H17B 0.3763 0.7802 -0.0937 0.04 Uiso calc R 1 1
H H17C 0.3554 0.6384 -0.1296 0.04 Uiso calc R 1 1
C C18 0.1750(6) 0.5513(4) 0.0787(4) 0.0274(10) Uani d . 1 1
H H18A 0.2784 0.5075 0.1118 0.041 Uiso calc R 1 1
H H18B 0.1601 0.4985 0.0178 0.041 Uiso calc R 1 1
H H18C 0.0726 0.5574 0.1406 0.041 Uiso calc R 1 1
F F1 0.7418(4) 0.5802(3) 0.1913(3) 0.0372(7) Uani d . 1 1
F F2 -0.2633(4) 0.9676(3) 0.2491(3) 0.0437(8) Uani d . 1 1
I I1 0.50006(4) 0.68702(3) 0.24847(2) 0.02221(10) Uani d . 1 1
I I2 -0.01657(4) 0.86419(3) 0.20011(2) 0.02531(10) Uani d . 1 1
O O1 0.2750(4) 0.7761(3) 0.3428(3) 0.0283(7) Uani d . 1 1
O O2 0.2131(4) 0.7722(3) 0.1146(3) 0.0250(7) Uani d . 1 1
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 0 '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'
O O 0.0106 0.006 '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
C6 C1 C2 123.2(4)
C6 C1 I1 111.5(3)
C2 C1 I1 125.3(4)
C3 C2 C1 117.9(5)
H2 C2 C1 121.0
C2 C3 C4 120.4(5)
C5 C4 C3 120.9(4)
C4 C5 C6 119.7(5)
C1 C6 C5 117.7(4)
C1 C6 C7 118.1(4)
C5 C6 C7 124.2(4)
O1 C7 C6 108.1(4)
O1 C7 C8 109.8(4)
C6 C7 C8 109.9(4)
O1 C7 C9 104.8(4)
C6 C7 C9 112.1(4)
C8 C7 C9 111.8(4)
C15 C10 C11 124.0(4)
C15 C10 I2 111.0(3)
C11 C10 I2 124.9(4)
C10 C11 C12 117.4(5)
H11 C11 C10 121.3
C13 C12 C11 120.3(5)
C12 C13 C14 120.6(5)
C15 C14 C13 120.4(4)
C10 C15 C14 117.3(4)
C10 C15 C16 118.2(4)
C14 C15 C16 124.5(4)
O2 C16 C15 107.5(3)
O2 C16 C18 110.3(4)
C15 C16 C18 109.6(4)
O2 C16 C17 106.0(3)
C15 C16 C17 111.9(4)
C18 C16 C17 111.3(4)
O1 I1 F1 166.40(12)
O1 I1 C1 80.58(16)
F1 I1 C1 86.21(16)
O2 I2 F2 166.81(13)
O2 I2 C10 80.30(16)
F2 I2 C10 87.13(16)
C7 O1 I1 113.7(3)
C16 O2 I2 113.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.374(6) ?
C1 C2 1.386(6) ?
C1 I1 2.085(4) y
C2 C3 1.367(7) ?
C2 H2 0.950 ?
C3 C4 1.382(7) ?
C4 C5 1.378(7) ?
C5 C6 1.394(6) ?
C6 C7 1.514(6) ?
C7 O1 1.437(5) ?
C7 C8 1.521(6) ?
C7 C9 1.523(6) ?
C10 C15 1.372(6) ?
C10 C11 1.382(6) ?
C10 I2 2.094(5) y
C11 H11 0.950 ?
C11 C12 1.385(7) ?
C12 C13 1.377(7) ?
C13 C14 1.389(7) ?
C14 C15 1.385(6) ?
C15 C16 1.519(6) ?
C16 O2 1.437(5) ?
C16 C18 1.519(6) ?
C16 C17 1.525(6) ?
F1 I1 2.045(3) y
F2 I2 2.046(3) y
I1 O1 2.022(3) y
I2 O2 2.017(3) y
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
C6 C1 C2 C3 0.7(7)
I1 C1 C2 C3 -178.5(4)
C1 C2 C3 C4 -0.8(7)
C2 C3 C4 C5 -0.6(8)
C3 C4 C5 C6 2.1(7)
C2 C1 C6 C5 0.8(7)
I1 C1 C6 C5 -179.8(3)
C2 C1 C6 C7 177.8(4)
I1 C1 C6 C7 -2.8(5)
C4 C5 C6 C1 -2.2(7)
C4 C5 C6 C7 -179.0(4)
C1 C6 C7 O1 21.8(5)
C5 C6 C7 O1 -161.3(4)
C1 C6 C7 C8 -98.0(5)
C5 C6 C7 C8 78.8(5)
C1 C6 C7 C9 136.9(4)
C5 C6 C7 C9 -46.3(6)
C15 C10 C11 C12 -0.3(7)
I2 C10 C11 C12 -178.8(3)
C10 C11 C12 C13 0.0(7)
C11 C12 C13 C14 0.2(7)
C12 C13 C14 C15 -0.1(7)
C11 C10 C15 C14 0.4(6)
I2 C10 C15 C14 179.0(3)
C11 C10 C15 C16 -177.4(4)
I2 C10 C15 C16 1.2(5)
C13 C14 C15 C10 -0.2(6)
C13 C14 C15 C16 177.5(4)
C10 C15 C16 O2 -22.0(5)
C14 C15 C16 O2 160.3(4)
C10 C15 C16 C18 97.9(5)
C14 C15 C16 C18 -79.8(5)
C10 C15 C16 C17 -138.1(4)
C14 C15 C16 C17 44.3(6)
C6 C1 I1 O1 -11.4(3)
C2 C1 I1 O1 168.0(4)
C6 C1 I1 F1 171.9(3)
C2 C1 I1 F1 -8.8(4)
C15 C10 I2 O2 13.5(3)
C11 C10 I2 O2 -167.8(4)
C15 C10 I2 F2 -170.5(3)
C11 C10 I2 F2 8.2(4)
C6 C7 O1 I1 -31.0(4)
C8 C7 O1 I1 89.0(4)
C9 C7 O1 I1 -150.7(3)
F1 I1 O1 C7 38.2(7)
C1 I1 O1 C7 24.4(3)
C15 C16 O2 I2 33.1(4)
C18 C16 O2 I2 -86.4(4)
C17 C16 O2 I2 153.0(3)
F2 I2 O2 C16 -44.7(7)
C10 I2 O2 C16 -26.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657619
