#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:31:27 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292816 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/30/7133078.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_7133078
loop_
_publ_author_name
'Wakabayashi, Ryota'
'Wang, Shuo'
'Kurogi, Takashi'
'Yorimitsu, Hideki'
_publ_section_title
;
 Arylation of benzazoles at the 4 positions by activation of their
 2-methylsulfinyl groups.
;
_journal_issue                   48
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6166
_journal_page_last               6169
_journal_paper_doi               10.1039/d4cc01918k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C14 H11 N O S2'
_chemical_formula_weight         273.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-19 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                93.577(2)
_cell_angle_beta                 100.035(3)
_cell_angle_gamma                113.048(3)
_cell_formula_units_Z            4
_cell_length_a                   9.6697(4)
_cell_length_b                   10.5598(4)
_cell_length_c                   13.8151(4)
_cell_measurement_reflns_used    12488
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      74.3570
_cell_measurement_theta_min      4.5920
_cell_volume                     1264.85(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Yadokari-XG (Wakita,Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type
;
Rigaku Pilatus 200K
;
_diffrn_measurement_method       'profile data from ω-scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17386
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.492
_diffrn_reflns_theta_min         4.599
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    3.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethylacetate/hexane'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0297
_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)+(0.0385P)²+0.4892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0797
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4501
_reflns_number_total             4911
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc01918k2.cif
_cod_data_source_block           Wang20230130
_cod_depositor_comments          'Adding full bibliography for 7133078.cif.'
_cod_original_cell_volume        1264.84(9)
_cod_database_code               7133078
_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, -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
S1 S 0.59465(5) 0.45314(4) 0.13546(3) 0.03577(10) Uani 1 1 d . . . . .
N1 N 0.56324(14) 0.28068(13) -0.01771(10) 0.0311(3) Uani 1 1 d . . . . .
C1 C 0.9507(2) 0.55534(18) 0.16274(14) 0.0452(4) Uani 1 1 d . . . . .
H1 H 0.926326 0.632445 0.146799 0.068 Uiso 1 1 calc R U . . .
H1A H 1.060182 0.583916 0.174877 0.068 Uiso 1 1 calc R U . . .
H1B H 0.914504 0.524209 0.221086 0.068 Uiso 1 1 calc R U . . .
S2 S 0.85937(4) 0.41612(4) 0.06089(3) 0.04071(11) Uani 1 1 d . . . . .
C2 C 0.66517(18) 0.37509(15) 0.05265(12) 0.0320(3) Uani 1 1 d . . . . .
C3 C 0.41498(17) 0.26049(15) -0.00864(11) 0.0305(3) Uani 1 1 d . . . . .
C4 C 0.27922(18) 0.16521(16) -0.07249(12) 0.0335(3) Uani 1 1 d . . . . .
C5 C 0.14161(19) 0.16210(19) -0.05317(13) 0.0420(4) Uani 1 1 d . . . . .
H5 H 0.049321 0.099500 -0.093723 0.050 Uiso 1 1 calc R U . . .
C6 C 0.1374(2) 0.2498(2) 0.02508(14) 0.0463(4) Uani 1 1 d . . . . .
H6 H 0.042715 0.244054 0.035353 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2702(2) 0.34460(19) 0.08732(13) 0.0405(4) Uani 1 1 d . . . . .
H7 H 0.267423 0.404050 0.138793 0.049 Uiso 1 1 calc R U . . .
C8 C 0.40905(18) 0.34774(16) 0.06998(12) 0.0332(3) Uani 1 1 d . . . . .
C9 C 0.28205(16) 0.07504(16) -0.15867(12) 0.0319(3) Uani 1 1 d . . . . .
C10 C 0.32625(19) -0.03435(17) -0.14737(13) 0.0385(4) Uani 1 1 d . . . . .
H10 H 0.355027 -0.052898 -0.083852 0.046 Uiso 1 1 calc R U . . .
C11 C 0.32833(18) -0.11637(17) -0.22882(12) 0.0373(3) Uani 1 1 d . . . . .
H11 H 0.355869 -0.190586 -0.219724 0.045 Uiso 1 1 calc R U . . .
C12 C 0.28956(16) -0.08816(16) -0.32355(12) 0.0331(3) Uani 1 1 d . . . . .
C13 C 0.2436(2) 0.01971(18) -0.33660(13) 0.0408(4) Uani 1 1 d . . . . .
H13 H 0.215361 0.038328 -0.400193 0.049 Uiso 1 1 calc R U . . .
C14 C 0.23984(19) 0.09970(17) -0.25443(13) 0.0393(4) Uani 1 1 d . . . . .
H14 H 0.208300 0.171545 -0.263750 0.047 Uiso 1 1 calc R U . . .
O1 O 0.29431(14) -0.16275(13) -0.40663(9) 0.0415(3) Uani 1 1 d . . . . .
H1C H 0.342(3) -0.212(2) -0.3922(16) 0.056(6) Uiso 1 1 d . . . . .
S3 S 0.57081(5) 0.59410(4) 0.39160(3) 0.03672(10) Uani 1 1 d . . . . .
N2 N 0.55614(15) 0.34254(13) 0.36911(9) 0.0328(3) Uani 1 1 d . . . . .
S4 S 0.84927(5) 0.51648(5) 0.42440(3) 0.04185(11) Uani 1 1 d . . . . .
C15 C 0.9298(2) 0.70309(19) 0.45011(16) 0.0536(5) Uani 1 1 d . . . . .
H15 H 0.909865 0.740234 0.390134 0.080 Uiso 1 1 calc R U . . .
H15A H 1.038902 0.737637 0.475166 0.080 Uiso 1 1 calc R U . . .
H15B H 0.883626 0.731086 0.498766 0.080 Uiso 1 1 calc R U . . .
C16 C 0.65211(19) 0.47254(16) 0.39383(11) 0.0347(3) Uani 1 1 d . . . . .
C17 C 0.40537(18) 0.33088(16) 0.34596(11) 0.0314(3) Uani 1 1 d . . . . .
C18 C 0.27404(18) 0.20556(16) 0.31123(12) 0.0346(3) Uani 1 1 d . . . . .
C19 C 0.13251(19) 0.21400(18) 0.29177(13) 0.0406(4) Uani 1 1 d . . . . .
H19 H 0.044068 0.132969 0.268176 0.049 Uiso 1 1 calc R U . . .
C20 C 0.1182(2) 0.34022(18) 0.30643(14) 0.0419(4) Uani 1 1 d . . . . .
H20 H 0.020771 0.340683 0.294992 0.050 Uiso 1 1 calc R U . . .
C21 C 0.24617(19) 0.46399(17) 0.33753(12) 0.0371(3) Uani 1 1 d . . . . .
H21 H 0.236911 0.548180 0.345930 0.045 Uiso 1 1 calc R U . . .
C22 C 0.39002(18) 0.45829(16) 0.35596(11) 0.0325(3) Uani 1 1 d . . . . .
C23 C 0.28928(17) 0.07258(16) 0.28685(12) 0.0334(3) Uani 1 1 d . . . . .
C24 C 0.26877(18) 0.02247(16) 0.18758(12) 0.0358(3) Uani 1 1 d . . . . .
H24 H 0.241802 0.070189 0.138540 0.043 Uiso 1 1 calc R U . . .
C25 C 0.28775(18) -0.09709(16) 0.16038(12) 0.0348(3) Uani 1 1 d . . . . .
H25 H 0.272425 -0.129622 0.093565 0.042 Uiso 1 1 calc R U . . .
C26 C 0.32945(16) -0.16808(15) 0.23252(12) 0.0318(3) Uani 1 1 d . . . . .
C27 C 0.3455(2) -0.12255(17) 0.33184(13) 0.0395(4) Uani 1 1 d . . . . .
H27 H 0.369312 -0.172243 0.380509 0.047 Uiso 1 1 calc R U . . .
C28 C 0.3261(2) -0.00268(17) 0.35844(13) 0.0406(4) Uani 1 1 d . . . . .
H28 H 0.337896 0.027820 0.425201 0.049 Uiso 1 1 calc R U . . .
O2 O 0.35605(13) -0.28345(11) 0.20887(9) 0.0379(3) Uani 1 1 d . . . . .
H2 H 0.373(3) -0.283(3) 0.1490(19) 0.074(8) 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 0.0181 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'
S S 0.3331 0.5567 '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
C8 S1 C2 88.67(7) . . ?
C2 N1 C3 110.56(13) . . ?
C2 S2 C1 102.98(8) . . ?
N1 C2 S2 119.89(11) . . ?
N1 C2 S1 116.39(11) . . ?
S2 C2 S1 123.72(9) . . ?
N1 C3 C4 124.83(14) . . ?
N1 C3 C8 114.59(14) . . ?
C4 C3 C8 120.56(13) . . ?
C5 C4 C3 116.67(15) . . ?
C5 C4 C9 121.54(15) . . ?
C3 C4 C9 121.77(13) . . ?
C4 C5 C6 122.18(17) . . ?
C7 C6 C5 121.44(15) . . ?
C6 C7 C8 117.16(16) . . ?
C7 C8 C3 121.98(15) . . ?
C7 C8 S1 128.27(13) . . ?
C3 C8 S1 109.75(11) . . ?
C14 C9 C10 117.81(15) . . ?
C14 C9 C4 119.73(14) . . ?
C10 C9 C4 122.46(14) . . ?
C11 C10 C9 121.29(15) . . ?
C12 C11 C10 120.10(15) . . ?
O1 C12 C11 122.72(14) . . ?
O1 C12 C13 117.73(14) . . ?
C11 C12 C13 119.55(15) . . ?
C12 C13 C14 119.70(15) . . ?
C13 C14 C9 121.51(15) . . ?
C22 S3 C16 88.97(7) . . ?
C16 N2 C17 110.50(13) . . ?
C16 S4 C15 102.91(9) . . ?
N2 C16 S4 119.89(12) . . ?
N2 C16 S3 116.21(12) . . ?
S4 C16 S3 123.89(9) . . ?
N2 C17 C18 125.14(14) . . ?
N2 C17 C22 114.76(14) . . ?
C18 C17 C22 120.06(14) . . ?
C19 C18 C17 117.11(14) . . ?
C19 C18 C23 121.74(15) . . ?
C17 C18 C23 120.86(14) . . ?
C18 C19 C20 122.26(16) . . ?
C21 C20 C19 121.14(16) . . ?
C20 C21 C22 117.57(15) . . ?
C21 C22 C17 121.75(15) . . ?
C21 C22 S3 128.73(12) . . ?
C17 C22 S3 109.53(12) . . ?
C24 C23 C28 118.10(15) . . ?
C24 C23 C18 118.49(14) . . ?
C28 C23 C18 123.40(15) . . ?
C25 C24 C23 121.23(15) . . ?
C26 C25 C24 119.96(15) . . ?
O2 C26 C25 121.78(14) . . ?
O2 C26 C27 118.47(14) . . ?
C25 C26 C27 119.75(14) . . ?
C26 C27 C28 119.84(15) . . ?
C27 C28 C23 121.04(16) . . ?
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
S1 C8 1.7385(17) . ?
S1 C2 1.7458(15) . ?
N1 C2 1.298(2) . ?
N1 C3 1.3939(18) . ?
C1 S2 1.7925(18) . ?
S2 C2 1.7347(16) . ?
C3 C4 1.402(2) . ?
C3 C8 1.404(2) . ?
C4 C5 1.391(2) . ?
C4 C9 1.488(2) . ?
C5 C6 1.396(3) . ?
C6 C7 1.375(3) . ?
C7 C8 1.392(2) . ?
C9 C14 1.387(2) . ?
C9 C10 1.388(2) . ?
C10 C11 1.384(2) . ?
C11 C12 1.381(2) . ?
C12 O1 1.3689(19) . ?
C12 C13 1.386(2) . ?
C13 C14 1.386(2) . ?
S3 C22 1.7332(16) . ?
S3 C16 1.7475(16) . ?
N2 C16 1.302(2) . ?
N2 C17 1.391(2) . ?
S4 C16 1.7408(17) . ?
S4 C15 1.7973(19) . ?
C17 C18 1.409(2) . ?
C17 C22 1.411(2) . ?
C18 C19 1.387(2) . ?
C18 C23 1.492(2) . ?
C19 C20 1.399(2) . ?
C20 C21 1.379(2) . ?
C21 C22 1.395(2) . ?
C23 C24 1.390(2) . ?
C23 C28 1.391(2) . ?
C24 C25 1.384(2) . ?
C25 C26 1.381(2) . ?
C26 O2 1.3719(18) . ?
C26 C27 1.387(2) . ?
C27 C28 1.387(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 S2 177.87(10) . . . . ?
C3 N1 C2 S1 -1.60(16) . . . . ?
C1 S2 C2 N1 176.78(13) . . . . ?
C1 S2 C2 S1 -3.79(12) . . . . ?
C8 S1 C2 N1 0.49(12) . . . . ?
C8 S1 C2 S2 -178.96(10) . . . . ?
C2 N1 C3 C4 -179.60(14) . . . . ?
C2 N1 C3 C8 2.21(18) . . . . ?
N1 C3 C4 C5 -178.43(14) . . . . ?
C8 C3 C4 C5 -0.3(2) . . . . ?
N1 C3 C4 C9 -0.4(2) . . . . ?
C8 C3 C4 C9 177.71(14) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C9 C4 C5 C6 -177.48(15) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
C6 C7 C8 C3 1.3(2) . . . . ?
C6 C7 C8 S1 -179.31(13) . . . . ?
N1 C3 C8 C7 177.67(14) . . . . ?
C4 C3 C8 C7 -0.6(2) . . . . ?
N1 C3 C8 S1 -1.84(16) . . . . ?
C4 C3 C8 S1 179.89(11) . . . . ?
C2 S1 C8 C7 -178.71(15) . . . . ?
C2 S1 C8 C3 0.76(11) . . . . ?
C5 C4 C9 C14 68.8(2) . . . . ?
C3 C4 C9 C14 -109.21(17) . . . . ?
C5 C4 C9 C10 -111.45(18) . . . . ?
C3 C4 C9 C10 70.6(2) . . . . ?
C14 C9 C10 C11 0.0(2) . . . . ?
C4 C9 C10 C11 -179.79(15) . . . . ?
C9 C10 C11 C12 1.6(2) . . . . ?
C10 C11 C12 O1 177.83(15) . . . . ?
C10 C11 C12 C13 -2.2(2) . . . . ?
O1 C12 C13 C14 -178.79(15) . . . . ?
C11 C12 C13 C14 1.2(2) . . . . ?
C12 C13 C14 C9 0.4(3) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C4 C9 C14 C13 178.82(15) . . . . ?
C17 N2 C16 S4 -178.93(11) . . . . ?
C17 N2 C16 S3 -0.09(17) . . . . ?
C15 S4 C16 N2 179.07(13) . . . . ?
C15 S4 C16 S3 0.32(13) . . . . ?
C22 S3 C16 N2 0.97(13) . . . . ?
C22 S3 C16 S4 179.76(11) . . . . ?
C16 N2 C17 C18 176.45(14) . . . . ?
C16 N2 C17 C22 -1.15(18) . . . . ?
N2 C17 C18 C19 -179.89(14) . . . . ?
C22 C17 C18 C19 -2.4(2) . . . . ?
N2 C17 C18 C23 -6.0(2) . . . . ?
C22 C17 C18 C23 171.50(14) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C23 C18 C19 C20 -174.45(15) . . . . ?
C18 C19 C20 C21 2.6(3) . . . . ?
C19 C20 C21 C22 -1.4(3) . . . . ?
C20 C21 C22 C17 -1.7(2) . . . . ?
C20 C21 C22 S3 177.76(13) . . . . ?
N2 C17 C22 C21 -178.64(14) . . . . ?
C18 C17 C22 C21 3.6(2) . . . . ?
N2 C17 C22 S3 1.84(16) . . . . ?
C18 C17 C22 S3 -175.89(12) . . . . ?
C16 S3 C22 C21 179.02(15) . . . . ?
C16 S3 C22 C17 -1.51(11) . . . . ?
C19 C18 C23 C24 71.3(2) . . . . ?
C17 C18 C23 C24 -102.34(18) . . . . ?
C19 C18 C23 C28 -110.08(19) . . . . ?
C17 C18 C23 C28 76.3(2) . . . . ?
C28 C23 C24 C25 -1.5(2) . . . . ?
C18 C23 C24 C25 177.26(14) . . . . ?
C23 C24 C25 C26 -0.7(2) . . . . ?
C24 C25 C26 O2 -177.07(14) . . . . ?
C24 C25 C26 C27 2.8(2) . . . . ?
O2 C26 C27 C28 177.15(14) . . . . ?
C25 C26 C27 C28 -2.7(2) . . . . ?
C26 C27 C28 C23 0.5(3) . . . . ?
C24 C23 C28 C27 1.5(2) . . . . ?
C18 C23 C28 C27 -177.11(15) . . . . ?
