#------------------------------------------------------------------------------
#$Date: 2019-11-24 21:51:20 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239521 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/67/4516762.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_4516762
loop_
_publ_author_name
'Brantley, Johnathan N.'
'Samant, Andrew V.'
'Toste, F. Dean'
_publ_section_title
;
 Isolation and Reactivity of Trifluoromethyl Iodonium Salts.
;
_journal_issue                   5
_journal_name_full               'ACS central science'
_journal_page_first              341
_journal_page_last               350
_journal_paper_doi               10.1021/acscentsci.6b00119
_journal_volume                  2
_journal_year                    2016
_chemical_formula_sum            'C12 H13 Cl F3 I O2'
_chemical_formula_weight         408.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.868(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2059(11)
_cell_length_b                   13.8263(13)
_cell_length_c                   9.0501(9)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.35
_cell_volume                     1397.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            53119
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.388
_diffrn_reflns_theta_min         1.824
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.512
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.774
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0370P)²+1.4333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2317
_reflns_number_total             2574
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oc6b00119_si_006.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516762
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.633
_shelx_estimated_absorpt_t_max   0.824
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.6728(3) 0.3710(2) 0.3150(3) 0.0143(6) Uani 1 1 d . .
C2 C 0.5648(3) 0.3222(2) 0.3008(3) 0.0162(6) Uani 1 1 d . .
H2 H 0.5404 0.2851 0.3814 0.019 Uiso 1 1 calc R U
C3 C 0.4921(3) 0.3271(2) 0.1692(4) 0.0172(7) Uani 1 1 d . .
H3 H 0.4173 0.2945 0.1587 0.021 Uiso 1 1 calc R U
C4 C 0.5311(3) 0.3808(2) 0.0532(3) 0.0161(6) Uani 1 1 d . .
H4 H 0.4831 0.3845 -0.0383 0.019 Uiso 1 1 calc R U
C5 C 0.6402(3) 0.4293(2) 0.0705(3) 0.0159(6) Uani 1 1 d . .
H5 H 0.6652 0.4650 -0.0112 0.019 Uiso 1 1 calc R U
C6 C 0.7150(3) 0.4281(2) 0.2025(3) 0.0140(6) Uani 1 1 d . .
C7 C 0.8328(3) 0.4849(2) 0.2108(3) 0.0152(6) Uani 1 1 d . .
C8 C 0.8477(3) 0.5480(2) 0.0753(3) 0.0203(7) Uani 1 1 d . .
H8A H 0.7741 0.5849 0.0506 0.030 Uiso 1 1 calc R U
H8B H 0.8639 0.5068 -0.0088 0.030 Uiso 1 1 calc R U
H8C H 0.9147 0.5927 0.0971 0.030 Uiso 1 1 calc R U
C9 C 0.9422(3) 0.4202(2) 0.2323(4) 0.0183(7) Uani 1 1 d . .
H9A H 1.0149 0.4599 0.2355 0.028 Uiso 1 1 calc R U
H9B H 0.9419 0.3743 0.1497 0.028 Uiso 1 1 calc R U
H9C H 0.9406 0.3845 0.3257 0.028 Uiso 1 1 calc R U
C10 C 0.6731(3) 0.4593(2) 0.6286(3) 0.0176(7) Uani 1 1 d . .
C11 C 0.7728(3) 0.6253(2) 0.3512(4) 0.0229(7) Uani 1 1 d . .
C12 C 0.8155(4) 0.6876(3) 0.4802(4) 0.0327(9) Uani 1 1 d . .
H12A H 0.8755 0.7334 0.4497 0.049 Uiso 1 1 calc R U
H12B H 0.8514 0.6469 0.5608 0.049 Uiso 1 1 calc R U
H12C H 0.7477 0.7234 0.5147 0.049 Uiso 1 1 calc R U
F1 F 0.62268(16) 0.51954(13) 0.5267(2) 0.0209(4) Uani 1 1 d . .
F2 F 0.74681(17) 0.51090(13) 0.7206(2) 0.0233(4) Uani 1 1 d . .
F3 F 0.58715(17) 0.42328(14) 0.7043(2) 0.0256(4) Uani 1 1 d . .
Cl1 Cl 0.86149(7) 0.18826(6) 0.35259(8) 0.01901(17) Uani 1 1 d . .
I1 I 0.76903(2) 0.34149(2) 0.52317(2) 0.01385(9) Uani 1 1 d . .
O1 O 0.6892(2) 0.64435(17) 0.2629(3) 0.0257(6) Uani 1 1 d . .
O2 O 0.84120(19) 0.54596(16) 0.3476(2) 0.0187(5) Uani 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 0.0060 '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
C2 C1 C6 123.7(3)
C2 C1 I1 111.2(2)
C6 C1 I1 125.0(2)
C1 C2 C3 120.1(3)
C1 C2 H2 120.0
C3 C2 H2 120.0
C4 C3 C2 118.5(3)
C4 C3 H3 120.7
C2 C3 H3 120.7
C3 C4 C5 120.2(3)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 123.1(3)
C4 C5 H5 118.5
C6 C5 H5 118.5
C5 C6 C1 114.4(3)
C5 C6 C7 119.1(3)
C1 C6 C7 126.5(3)
O2 C7 C9 103.5(2)
O2 C7 C8 109.9(2)
C9 C7 C8 107.3(2)
O2 C7 C6 108.9(2)
C9 C7 C6 112.8(2)
C8 C7 C6 114.0(3)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
F3 C10 F2 108.5(2)
F3 C10 F1 108.0(2)
F2 C10 F1 107.6(2)
F3 C10 I1 110.3(2)
F2 C10 I1 111.5(2)
F1 C10 I1 110.82(19)
O1 C11 O2 125.2(3)
O1 C11 C12 124.7(3)
O2 C11 C12 110.1(3)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C1 I1 C10 90.68(11)
C11 O2 C7 119.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.382(4)
C1 C6 1.401(4)
C1 I1 2.129(3)
C2 C3 1.387(5)
C2 H2 0.9500
C3 C4 1.385(4)
C3 H3 0.9500
C4 C5 1.393(4)
C4 H4 0.9500
C5 C6 1.400(4)
C5 H5 0.9500
C6 C7 1.533(4)
C7 O2 1.494(4)
C7 C9 1.518(4)
C7 C8 1.525(4)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 F3 1.325(4)
C10 F2 1.330(4)
C10 F1 1.332(4)
C10 I1 2.212(3)
C11 O1 1.207(4)
C11 O2 1.340(4)
C11 C12 1.497(5)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
