#------------------------------------------------------------------------------
#$Date: 2024-11-05 04:06:29 +0200 (Tue, 05 Nov 2024) $
#$Revision: 295771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/95/7249537.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_7249537
loop_
_publ_author_name
'Capozzi, Maria Annunziata M.'
'Alvarez-Larena, Angel'
'Piniella Febrer, Joan F.'
'Cardellicchio, Cosimo'
_publ_section_title
;
 Investigation of the titanium-mediated catalytic enantioselective
 oxidation of aryl benzyl sulfides containing heterocyclic groups
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              35105
_journal_page_last               35113
_journal_paper_doi               10.1039/D4RA07088G
_journal_volume                  14
_journal_year                    2024
_chemical_formula_sum            'C14 H7 F5 N2 O S'
_chemical_formula_weight         346.28
_chemical_name_systematic
(2,3,4,5,6-pentafluorobenzylsulfinyl)-1H-benzo[d]imidazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2024-01-27 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.82(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1880(4)
_cell_length_b                   7.0323(4)
_cell_length_c                   12.3527(7)
_cell_measurement_reflns_used    6450
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.55
_cell_volume                     693.54(11)
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_collection       'SMART 5.6 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.13
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5473
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.509
_diffrn_reflns_theta_min         1.691
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       table
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.065(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0351
_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)+(0.0676P)²+0.0526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                3016
_reflns_number_total             3134
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra07088g2.cif
_cod_data_source_block           6B
_cod_original_cell_volume        693.55(10)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7249537
_shelx_shelxl_version_number     2016/6
_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   0.847
_shelx_estimated_absorpt_t_max   0.940
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_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
C1 C 0.2386(4) 0.5097(5) 0.4322(2) 0.0635(8) Uani 1 1 d . . . . .
H1A H 0.359733 0.519326 0.451174 0.076 Uiso 1 1 calc R U . . .
H1B H 0.208647 0.378831 0.412099 0.076 Uiso 1 1 calc R U . . .
O2 O -0.0262(2) 0.5170(3) 0.52113(17) 0.0570(5) Uani 1 1 d . . . . .
S2 S 0.15282(7) 0.57998(9) 0.55061(5) 0.04557(17) Uani 1 1 d . . . . .
C11 C 0.1681(3) 0.6389(5) 0.3366(2) 0.0590(7) Uani 1 1 d . . . . .
C12 C 0.2288(4) 0.8206(7) 0.3334(3) 0.0709(10) Uani 1 1 d . . . . .
C13 C 0.1652(6) 0.9453(8) 0.2482(4) 0.1028(18) Uani 1 1 d . . . . .
C14 C 0.0379(7) 0.8828(13) 0.1634(4) 0.125(3) Uani 1 1 d . . . . .
C15 C -0.0262(5) 0.7069(13) 0.1641(3) 0.110(2) Uani 1 1 d . . . . .
C16 C 0.0393(4) 0.5812(9) 0.2507(3) 0.0815(11) Uani 1 1 d . . . . .
F12 F 0.3522(3) 0.8817(4) 0.4161(2) 0.0893(7) Uani 1 1 d . . . . .
F13 F 0.2290(5) 1.1197(6) 0.2473(4) 0.1540(17) Uani 1 1 d . . . . .
F14 F -0.0254(5) 1.0015(9) 0.0798(3) 0.195(3) Uani 1 1 d . . . . .
F15 F -0.1490(3) 0.6464(9) 0.08141(19) 0.165(2) Uani 1 1 d . . . . .
F16 F -0.0250(3) 0.4067(6) 0.2501(3) 0.1129(10) Uani 1 1 d . . . . .
C21 C 0.2675(3) 0.4142(3) 0.6455(2) 0.0428(5) Uani 1 1 d . . . . .
N22 N 0.3660(3) 0.4774(3) 0.73652(18) 0.0450(4) Uani 1 1 d . . . . .
C23 C 0.4392(3) 0.3149(4) 0.78831(18) 0.0414(5) Uani 1 1 d . . . . .
C24 C 0.5556(3) 0.2935(5) 0.8890(2) 0.0541(6) Uani 1 1 d . . . . .
H24 H 0.596824 0.397874 0.932879 0.065 Uiso 1 1 calc R U . . .
C25 C 0.6069(4) 0.1102(6) 0.9208(2) 0.0680(9) Uani 1 1 d . . . . .
H25 H 0.683559 0.092057 0.987785 0.082 Uiso 1 1 calc R U . . .
C26 C 0.5488(4) -0.0451(5) 0.8571(3) 0.0671(8) Uani 1 1 d . . . . .
H26 H 0.588291 -0.164932 0.881952 0.080 Uiso 1 1 calc R U . . .
C27 C 0.4333(4) -0.0305(4) 0.7569(3) 0.0562(6) Uani 1 1 d . . . . .
H27 H 0.393650 -0.136447 0.714101 0.067 Uiso 1 1 calc R U . . .
C28 C 0.3801(3) 0.1540(4) 0.7243(2) 0.0421(5) Uani 1 1 d . . . . .
N29 N 0.2693(3) 0.2227(3) 0.63168(18) 0.0455(5) Uani 1 1 d . . . . .
H29 H 0.209(5) 0.163(6) 0.588(3) 0.065(10) 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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
C11 C1 S2 108.5(2) . . ?
C11 C1 H1A 110.0 . . ?
S2 C1 H1A 110.0 . . ?
C11 C1 H1B 110.0 . . ?
S2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
O2 S2 C21 108.27(11) . . ?
O2 S2 C1 104.76(14) . . ?
C21 S2 C1 96.35(12) . . ?
C12 C11 C16 118.1(4) . . ?
C12 C11 C1 120.5(3) . . ?
C16 C11 C1 121.5(4) . . ?
F12 C12 C11 119.6(3) . . ?
F12 C12 C13 118.1(5) . . ?
C11 C12 C13 122.3(4) . . ?
F13 C13 C14 121.3(5) . . ?
F13 C13 C12 120.5(6) . . ?
C14 C13 C12 118.1(5) . . ?
F14 C14 C15 119.6(7) . . ?
F14 C14 C13 119.1(8) . . ?
C15 C14 C13 121.3(4) . . ?
F15 C15 C14 121.2(5) . . ?
F15 C15 C16 118.7(7) . . ?
C14 C15 C16 120.1(5) . . ?
F16 C16 C11 120.5(4) . . ?
F16 C16 C15 119.5(5) . . ?
C11 C16 C15 120.0(6) . . ?
N22 C21 N29 115.0(2) . . ?
N22 C21 S2 118.80(19) . . ?
N29 C21 S2 126.13(19) . . ?
C21 N22 C23 103.8(2) . . ?
N22 C23 C24 130.0(2) . . ?
N22 C23 C28 110.3(2) . . ?
C24 C23 C28 119.8(2) . . ?
C25 C24 C23 117.2(3) . . ?
C25 C24 H24 121.4 . . ?
C23 C24 H24 121.4 . . ?
C26 C25 C24 122.3(2) . . ?
C26 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
C25 C26 C27 122.4(3) . . ?
C25 C26 H26 118.8 . . ?
C27 C26 H26 118.8 . . ?
C26 C27 C28 115.7(3) . . ?
C26 C27 H27 122.1 . . ?
C28 C27 H27 122.1 . . ?
N29 C28 C27 132.0(2) . . ?
N29 C28 C23 105.4(2) . . ?
C27 C28 C23 122.6(2) . . ?
C21 N29 C28 105.5(2) . . ?
C21 N29 H29 127(3) . . ?
C28 N29 H29 126(3) . . ?
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
C1 C11 1.500(4) . ?
C1 S2 1.826(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O2 S2 1.4966(18) . ?
S2 C21 1.768(2) . ?
C11 C12 1.375(6) . ?
C11 C16 1.380(5) . ?
C12 F12 1.338(5) . ?
C12 C13 1.381(5) . ?
C13 F13 1.334(7) . ?
C13 C14 1.376(10) . ?
C14 F14 1.339(5) . ?
C14 C15 1.344(11) . ?
C15 F15 1.334(6) . ?
C15 C16 1.400(7) . ?
C16 F16 1.335(7) . ?
C21 N22 1.308(3) . ?
C21 N29 1.358(3) . ?
N22 C23 1.380(3) . ?
C23 C24 1.397(3) . ?
C23 C28 1.404(3) . ?
C24 C25 1.385(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.369(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.384(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.399(4) . ?
C27 H27 0.9300 . ?
C28 N29 1.380(3) . ?
N29 H29 0.77(4) . ?
