#------------------------------------------------------------------------------
#$Date: 2024-11-05 04:06:29 +0200 (Tue, 05 Nov 2024) $
#$Revision: 295771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/95/7249539.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_7249539
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 H12 N2 O S'
_chemical_formula_weight         256.32
_chemical_name_systematic        Benzylsulfinyl-1H-benzo[d]imidazole
_space_group_crystal_system      hexagonal
_space_group_IT_number           172
_space_group_name_Hall           'P 64'
_space_group_name_H-M_alt        'P 64'
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   13.2625(10)
_cell_length_b                   13.2625(10)
_cell_length_c                   12.4674(10)
_cell_measurement_reflns_used    17959
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.46
_cell_measurement_theta_min      2.41
_cell_volume                     1899.1(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.951
_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  0.0778
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17934
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.744
_diffrn_reflns_theta_min         1.773
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       table
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 666 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0659
_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)+(0.0375P)²+0.0302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.888
_reflns_number_gt                2017
_reflns_number_total             3030
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra07088g2.cif
_cod_data_source_block           3B
_cod_database_code               7249539
_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   0.944
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z'
'y, -x+y, z+1/3'
'x-y, x, z+2/3'
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
C101 C 0.7020(4) 0.8347(4) 0.2363(3) 0.0559(13) Uani 1 1 d . . . . .
H10A H 0.692841 0.768538 0.277454 0.067 Uiso 1 1 calc R U . . .
H10B H 0.693264 0.886675 0.285256 0.067 Uiso 1 1 calc R U . . .
S102 S 0.84850(10) 0.91090(10) 0.17888(9) 0.0493(3) Uani 1 1 d . . . . .
O102 O 0.8487(3) 0.8396(3) 0.0865(3) 0.0644(9) Uani 1 1 d . . . . .
C111 C 0.6079(4) 0.7927(4) 0.1536(4) 0.0501(13) Uani 1 1 d . . . . .
C112 C 0.5789(4) 0.6937(4) 0.0955(4) 0.0648(14) Uani 1 1 d . . . . .
H112 H 0.615646 0.651251 0.110389 0.078 Uiso 1 1 calc R U . . .
C113 C 0.4960(4) 0.6564(6) 0.0153(5) 0.0818(17) Uani 1 1 d . . . . .
H113 H 0.478703 0.590064 -0.024013 0.098 Uiso 1 1 calc R U . . .
C114 C 0.4396(5) 0.7157(6) -0.0066(5) 0.0798(18) Uani 1 1 d . . . . .
H114 H 0.383199 0.689631 -0.059994 0.096 Uiso 1 1 calc R U . . .
C115 C 0.4661(5) 0.8139(6) 0.0502(5) 0.0810(18) Uani 1 1 d . . . . .
H115 H 0.427386 0.854540 0.035448 0.097 Uiso 1 1 calc R U . . .
C116 C 0.5516(4) 0.8538(5) 0.1309(4) 0.0667(16) Uani 1 1 d . . . . .
H116 H 0.570167 0.921301 0.168867 0.080 Uiso 1 1 calc R U . . .
C121 C 0.8389(4) 1.0277(4) 0.1180(3) 0.0402(10) Uani 1 1 d . . . . .
N122 N 0.8068(3) 1.0237(3) 0.0145(3) 0.0441(9) Uani 1 1 d . . . . .
H122 H 0.790(4) 0.969(4) -0.029(4) 0.053 Uiso 1 1 d . U . . .
C123 C 0.8167(3) 1.1289(4) -0.0079(3) 0.0426(11) Uani 1 1 d . . . . .
C124 C 0.7964(4) 1.1736(5) -0.1012(4) 0.0551(13) Uani 1 1 d . . . . .
H124 H 0.769473 1.129534 -0.163539 0.066 Uiso 1 1 calc R U . . .
C125 C 0.8182(5) 1.2863(5) -0.0963(5) 0.0653(15) Uani 1 1 d . . . . .
H125 H 0.804927 1.319223 -0.156711 0.078 Uiso 1 1 calc R U . . .
C126 C 0.8595(4) 1.3520(5) -0.0037(5) 0.0674(15) Uani 1 1 d . . . . .
H126 H 0.874367 1.428318 -0.004107 0.081 Uiso 1 1 calc R U . . .
C127 C 0.8794(4) 1.3082(5) 0.0889(5) 0.0613(13) Uani 1 1 d . . . . .
H127 H 0.906695 1.353224 0.150711 0.074 Uiso 1 1 calc R U . . .
C128 C 0.8567(4) 1.1931(4) 0.0864(3) 0.0455(11) Uani 1 1 d . . . . .
N129 N 0.8704(3) 1.1277(3) 0.1650(3) 0.0487(9) 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'
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'
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
C111 C101 S102 113.2(3) . . ?
C111 C101 H10A 108.9 . . ?
S102 C101 H10A 108.9 . . ?
C111 C101 H10B 108.9 . . ?
S102 C101 H10B 108.9 . . ?
H10A C101 H10B 107.8 . . ?
O102 S102 C121 104.2(2) . . ?
O102 S102 C101 106.9(2) . . ?
C121 S102 C101 97.4(2) . . ?
C112 C111 C116 118.6(5) . . ?
C112 C111 C101 120.1(5) . . ?
C116 C111 C101 121.3(5) . . ?
C111 C112 C113 121.1(5) . . ?
C111 C112 H112 119.5 . . ?
C113 C112 H112 119.5 . . ?
C114 C113 C112 120.5(6) . . ?
C114 C113 H113 119.7 . . ?
C112 C113 H113 119.7 . . ?
C113 C114 C115 119.7(6) . . ?
C113 C114 H114 120.1 . . ?
C115 C114 H114 120.1 . . ?
C114 C115 C116 120.3(6) . . ?
C114 C115 H115 119.8 . . ?
C116 C115 H115 119.8 . . ?
C111 C116 C115 119.8(6) . . ?
C111 C116 H116 120.1 . . ?
C115 C116 H116 120.1 . . ?
N129 C121 N122 113.7(4) . . ?
N129 C121 S102 124.2(3) . . ?
N122 C121 S102 121.9(3) . . ?
C121 N122 C123 106.7(4) . . ?
C121 N122 H122 126(3) . . ?
C123 N122 H122 127(3) . . ?
N122 C123 C124 131.8(4) . . ?
N122 C123 C128 105.4(4) . . ?
C124 C123 C128 122.8(4) . . ?
C125 C124 C123 116.5(5) . . ?
C125 C124 H124 121.8 . . ?
C123 C124 H124 121.8 . . ?
C124 C125 C126 121.5(5) . . ?
C124 C125 H125 119.2 . . ?
C126 C125 H125 119.2 . . ?
C127 C126 C125 122.3(5) . . ?
C127 C126 H126 118.9 . . ?
C125 C126 H126 118.9 . . ?
C126 C127 C128 117.3(5) . . ?
C126 C127 H127 121.3 . . ?
C128 C127 H127 121.3 . . ?
N129 C128 C123 110.2(4) . . ?
N129 C128 C127 130.2(4) . . ?
C123 C128 C127 119.6(5) . . ?
C121 N129 C128 104.1(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
C101 C111 1.496(6) . ?
C101 S102 1.829(5) . ?
C101 H10A 0.9700 . ?
C101 H10B 0.9700 . ?
S102 O102 1.490(3) . ?
S102 C121 1.786(5) . ?
C111 C112 1.375(7) . ?
C111 C116 1.377(7) . ?
C112 C113 1.381(7) . ?
C112 H112 0.9300 . ?
C113 C114 1.357(8) . ?
C113 H113 0.9300 . ?
C114 C115 1.364(8) . ?
C114 H114 0.9300 . ?
C115 C116 1.407(7) . ?
C115 H115 0.9300 . ?
C116 H116 0.9300 . ?
C121 N129 1.312(5) . ?
C121 N122 1.352(5) . ?
N122 C123 1.364(5) . ?
N122 H122 0.84(5) . ?
C123 C124 1.392(6) . ?
C123 C128 1.392(6) . ?
C124 C125 1.374(7) . ?
C124 H124 0.9300 . ?
C125 C126 1.384(8) . ?
C125 H125 0.9300 . ?
C126 C127 1.376(7) . ?
C126 H126 0.9300 . ?
C127 C128 1.401(6) . ?
C127 H127 0.9300 . ?
C128 N129 1.379(5) . ?
