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#$Date: 2023-06-29 13:42:48 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284607 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/32/7713245.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_7713245
loop_
_publ_author_name
'Bennetts, Jason D.'
'Barwise, Lachlan'
'Sharp-Bucknall, Lachlan'
'White, Keith F.'
'Hogan, Conor F.'
'Dutton, Jason L.'
_publ_section_title
;
 Structural verification and new reactivity for Stang's reagent,
 [PhI(CN)][OTf].
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8536
_journal_page_last               8539
_journal_paper_doi               10.1039/d3dt01765f
_journal_volume                  52
_journal_year                    2023
_chemical_formula_sum            'C8 H5 F3 I N O3 S'
_chemical_formula_weight         379.09
_chemical_name_common            'Stang's reagent'
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-20 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.386(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6343(2)
_cell_length_b                   12.3673(6)
_cell_length_c                   16.8451(9)
_cell_measurement_reflns_used    4667
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      71.0
_cell_measurement_theta_min      4.43
_cell_volume                     1170.35(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2021/3 (Sheldrick, 2021)'
_computing_structure_solution    'SHELXT-2021/3 (Sheldrick, 2021)'
_diffrn_ambient_temperature      175(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11171
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.299
_diffrn_reflns_theta_min         4.440
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    23.57
_exptl_absorpt_correction_T_max  0.669
_exptl_absorpt_correction_T_min  0.276
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.151
_exptl_crystal_description       rod
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.709
_refine_diff_density_min         -2.389
_refine_diff_density_rms         0.262
_refine_ls_extinction_coef       0.0018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1627P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.2369
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1575
_reflns_number_total             2264
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01765f2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7713245
_shelx_shelxl_version_number     2018/3
_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.
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.50177(12) 0.53214(6) 0.36389(5) 0.0495(4) Uani 1 1 d . . . . .
S2 S 0.9049(5) 0.3573(3) 0.4576(2) 0.0470(8) Uani 1 1 d . . . . .
O2 O 0.7013(13) 0.3577(8) 0.5022(6) 0.057(2) Uani 1 1 d . . . . .
F1 F 1.0976(19) 0.2088(8) 0.3757(7) 0.089(3) Uani 1 1 d . . . . .
O1 O 0.8693(14) 0.4196(8) 0.3831(6) 0.057(2) Uani 1 1 d . . . . .
F3 F 0.947(2) 0.1494(8) 0.4793(7) 0.094(3) Uani 1 1 d . . . . .
O3 O 1.1320(14) 0.3727(9) 0.5002(6) 0.063(3) Uani 1 1 d . . . . .
F2 F 0.720(2) 0.1945(9) 0.3766(7) 0.098(3) Uani 1 1 d . . . . .
C6 C 0.500(2) 0.4648(9) 0.2485(10) 0.053(3) Uani 1 1 d . . . . .
C5 C 0.671(2) 0.4994(12) 0.2016(11) 0.058(4) Uani 1 1 d . . . . .
H5 H 0.790827 0.549062 0.220605 0.069 Uiso 1 1 calc R U . . .
C2 C 0.326(2) 0.3515(12) 0.1492(10) 0.064(4) Uani 1 1 d . . . . .
H2 H 0.209956 0.299716 0.130953 0.077 Uiso 1 1 calc R U . . .
N1 N 0.061(2) 0.6776(12) 0.3027(7) 0.066(3) Uani 1 1 d . . . . .
C7 C 0.214(2) 0.6247(12) 0.3256(9) 0.058(3) Uani 1 1 d . . . . .
C4 C 0.328(2) 0.3909(11) 0.2260(9) 0.057(3) Uani 1 1 d . . . . .
H4 H 0.214809 0.367647 0.261378 0.069 Uiso 1 1 calc R U . . .
C3 C 0.662(3) 0.4582(13) 0.1237(12) 0.072(5) Uani 1 1 d . . . . .
H3 H 0.776319 0.480943 0.088560 0.086 Uiso 1 1 calc R U . . .
C8 C 0.915(3) 0.2204(12) 0.4195(10) 0.065(4) Uani 1 1 d . . . . .
C1 C 0.493(2) 0.3866(13) 0.0985(9) 0.062(4) Uani 1 1 d . . . . .
H1 H 0.487320 0.360046 0.045444 0.075 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
C7 I1 C6 89.0(5) . . ?
O2 S2 O3 117.5(6) . . ?
O2 S2 O1 112.7(5) . . ?
O3 S2 O1 114.6(6) . . ?
O2 S2 C8 103.9(7) . . ?
O3 S2 C8 104.4(7) . . ?
O1 S2 C8 101.2(7) . . ?
C5 C6 C4 124.7(16) . . ?
C5 C6 I1 117.1(10) . . ?
C4 C6 I1 118.3(11) . . ?
C6 C5 C3 116.8(13) . . ?
C4 C2 C1 120.6(13) . . ?
N1 C7 I1 177.4(14) . . ?
C6 C4 C2 116.8(14) . . ?
C1 C3 C5 120.5(14) . . ?
F2 C8 F1 108.8(14) . . ?
F2 C8 F3 108.2(14) . . ?
F1 C8 F3 106.7(12) . . ?
F2 C8 S2 112.0(11) . . ?
F1 C8 S2 110.4(11) . . ?
F3 C8 S2 110.7(11) . . ?
C3 C1 C2 120.6(15) . . ?
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 C7 2.047(13) . ?
I1 C6 2.115(16) . ?
S2 O2 1.418(9) . ?
S2 O3 1.431(9) . ?
S2 O1 1.472(10) . ?
S2 C8 1.813(16) . ?
F1 C8 1.317(18) . ?
F3 C8 1.337(18) . ?
F2 C8 1.310(18) . ?
C6 C5 1.36(2) . ?
C6 C4 1.364(17) . ?
C5 C3 1.40(2) . ?
C2 C4 1.38(2) . ?
C2 C1 1.39(2) . ?
N1 C7 1.127(17) . ?
C3 C1 1.35(2) . ?
