#------------------------------------------------------------------------------
#$Date: 2022-01-26 00:50:45 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272225 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129610.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_7129610
loop_
_publ_author_name
'Hayakawa, Masahiro'
'Horike, Satoshi'
'Hijikata, Yuh'
'Yasui, Kosuke'
'Yamaguchi, Shigehiro'
'Fukazawa, Aiko'
_publ_section_title
;
 Late-Stage Modification of π-Electron Systems Based on Asymmetric
 Oxidation of a Medium-Sized Sulfur-Containing Ring
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06996A
_journal_year                    2022
_chemical_formula_sum            'C20 H20 S2'
_chemical_formula_weight         324.48
_chemical_name_common            TN-Napt
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.3275(4)
_cell_length_b                   8.1766(3)
_cell_length_c                   34.8684(13)
_cell_measurement_reflns_used    7988
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.1950
_cell_measurement_theta_min      2.1580
_cell_volume                     3229.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            24371
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.336
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.0586
_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)+(0.0272P)²+2.6134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2173
_reflns_number_total             3683
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06996a2.cif
_cod_data_source_block           5
_cod_database_code               7129610
_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.
;
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
C1 C 0.5607(2) 0.3949(3) 0.73990(8) 0.0272(7) Uani 1 1 d . . . . .
H1 H 0.490745 0.445774 0.730741 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6410(2) 0.3368(3) 0.71402(9) 0.0264(6) Uani 1 1 d . . . . .
C3 C 0.7442(3) 0.2555(3) 0.72811(8) 0.0288(6) Uani 1 1 d . . . . .
H2 H 0.799875 0.211689 0.710525 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7631(2) 0.2404(3) 0.76641(9) 0.0310(7) Uani 1 1 d . . . . .
H3 H 0.831698 0.184919 0.775124 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6833(2) 0.3050(3) 0.79361(8) 0.0266(7) Uani 1 1 d . . . . .
C6 C 0.7046(2) 0.2986(3) 0.83361(9) 0.0315(7) Uani 1 1 d . . . . .
H4 H 0.773927 0.246730 0.842987 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6267(3) 0.3660(3) 0.85867(9) 0.0347(7) Uani 1 1 d . . . . .
H5 H 0.642484 0.362464 0.885419 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5222(2) 0.4414(3) 0.84520(9) 0.0347(7) Uani 1 1 d . . . . .
H6 H 0.467993 0.487405 0.862954 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4990(2) 0.4484(3) 0.80696(9) 0.0318(7) Uani 1 1 d . . . . .
H7 H 0.428390 0.498899 0.798285 0.038 Uiso 1 1 calc R U . . .
C10 C 0.5786(2) 0.3814(3) 0.77996(9) 0.0265(6) Uani 1 1 d . . . . .
S1 S 0.53068(10) 0.50606(13) 0.65547(3) 0.0278(3) Uani 0.876(2) 1 d . U P A 1
C11 C 0.6260(2) 0.3587(3) 0.67275(9) 0.0267(6) Uani 1 1 d D . . . .
C12 C 0.6786(8) 0.2809(13) 0.6430(4) 0.036(2) Uani 0.876(2) 1 d D U P A 1
H8 H 0.734615 0.195983 0.646784 0.043 Uiso 0.876(2) 1 calc R U P A 1
C13 C 0.6450(2) 0.3341(3) 0.60544(9) 0.0291(7) Uani 1 1 d D . . . .
C14 C 0.5638(2) 0.4576(3) 0.60872(8) 0.0297(7) Uani 1 1 d D . . . .
S2 S 0.49747(13) 0.5693(2) 0.57121(4) 0.0328(3) Uani 0.876(2) 1 d D U P A 1
C15 C 0.3569(2) 0.4631(4) 0.56637(10) 0.0470(9) Uani 1 1 d . . . . .
H9 H 0.346051 0.390687 0.588851 0.056 Uiso 0.876(2) 1 calc R U P A 1
H10 H 0.292548 0.544932 0.566716 0.056 Uiso 0.876(2) 1 calc R U P A 1
H11 H 0.329621 0.394014 0.587934 0.056 Uiso 0.124(2) 1 calc R U P A 2
H12 H 0.300066 0.554491 0.564073 0.056 Uiso 0.124(2) 1 calc R U P A 2
C16 C 0.3459(3) 0.3602(4) 0.52978(10) 0.0494(9) Uani 1 1 d . . . . .
H13 H 0.273417 0.293038 0.531630 0.059 Uiso 1 1 calc R U . . .
H14 H 0.336137 0.435055 0.507681 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4491(3) 0.2483(4) 0.52182(9) 0.0457(9) Uani 1 1 d . . . . .
H15 H 0.518969 0.316671 0.515939 0.055 Uiso 1 1 calc R U . . .
H16 H 0.430995 0.183327 0.498602 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4819(3) 0.1303(4) 0.55418(9) 0.0408(8) Uani 1 1 d . . . . .
H17 H 0.452328 0.174657 0.578788 0.049 Uiso 1 1 calc R U . . .
H18 H 0.442267 0.024120 0.549670 0.049 Uiso 1 1 calc R U . . .
C19 C 0.6141(3) 0.1020(4) 0.55741(10) 0.0407(8) Uani 1 1 d . . . . .
H19 H 0.643276 0.061072 0.532425 0.049 Uiso 0.876(2) 1 calc R U P A 1
H20 H 0.627905 0.014912 0.576623 0.049 Uiso 0.876(2) 1 calc R U P A 1
H21 H 0.641479 0.036422 0.535259 0.049 Uiso 0.124(2) 1 calc R U P A 2
H22 H 0.631227 0.039527 0.581089 0.049 Uiso 0.124(2) 1 calc R U P A 2
C20 C 0.6898(13) 0.2566(16) 0.5691(2) 0.046(2) Uani 0.876(2) 1 d D U P A 1
H23 H 0.773130 0.223314 0.572678 0.055 Uiso 0.876(2) 1 calc R U P A 1
H24 H 0.687146 0.337918 0.548053 0.055 Uiso 0.876(2) 1 calc R U P A 1
S3 S 0.7093(18) 0.252(3) 0.6407(7) 0.041(3) Uani 0.124(2) 1 d . U P A 2
S4 S 0.682(3) 0.267(3) 0.5584(4) 0.055(4) Uani 0.124(2) 1 d D U P A 2
C21 C 0.553(3) 0.458(4) 0.6523(9) 0.033(5) Uani 0.124(2) 1 d D U P A 2
H25 H 0.496911 0.525867 0.664893 0.039 Uiso 0.124(2) 1 calc R U P A 2
C22 C 0.490(4) 0.546(6) 0.5798(13) 0.042(6) Uani 0.124(2) 1 d D U P A 2
H26 H 0.537881 0.559751 0.556283 0.050 Uiso 0.124(2) 1 calc R U P A 2
H27 H 0.473957 0.657136 0.589930 0.050 Uiso 0.124(2) 1 calc R U P A 2
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'
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
C2 C1 C10 122.0(3) . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 C11 122.1(3) . . ?
C3 C2 C11 119.4(2) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 121.7(3) . . ?
C4 C5 C6 122.6(3) . . ?
C4 C5 C10 118.2(3) . . ?
C6 C5 C10 119.2(3) . . ?
C7 C6 C5 120.5(3) . . ?
C6 C7 C8 120.4(3) . . ?
C9 C8 C7 120.4(3) . . ?
C8 C9 C10 120.9(3) . . ?
C9 C10 C1 122.4(2) . . ?
C9 C10 C5 118.6(3) . . ?
C1 C10 C5 118.9(3) . . ?
C14 S1 C11 91.94(14) . . ?
C12 C11 C2 130.3(5) . . ?
C21 C11 C2 131.3(16) . . ?
C21 C11 S3 107.3(17) . . ?
C2 C11 S3 121.4(8) . . ?
C12 C11 S1 109.6(5) . . ?
C2 C11 S1 120.2(2) . . ?
C11 C12 C13 116.2(6) . . ?
C14 C13 C12 109.1(4) . . ?
C14 C13 C20 127.4(5) . . ?
C12 C13 C20 123.5(6) . . ?
C14 C13 S3 123.9(8) . . ?
C14 C13 S4 117.5(9) . . ?
S3 C13 S4 118.6(11) . . ?
C13 C14 C22 132(2) . . ?
C13 C14 C21 98.0(7) . . ?
C22 C14 C21 129(2) . . ?
C13 C14 S1 113.3(2) . . ?
C13 C14 S2 127.3(2) . . ?
S1 C14 S2 119.41(17) . . ?
C14 S2 C15 101.19(15) . . ?
C16 C15 C22 121(2) . . ?
C16 C15 S2 114.2(2) . . ?
C17 C16 C15 115.0(3) . . ?
C16 C17 C18 115.8(3) . . ?
C19 C18 C17 112.9(3) . . ?
C18 C19 S4 110.8(10) . . ?
C18 C19 C20 115.6(5) . . ?
C13 C20 C19 111.7(8) . . ?
C13 S3 C11 92.2(8) . . ?
C19 S4 C13 100.0(13) . . ?
C11 C21 C14 118(2) . . ?
C14 C22 C15 119(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 C2 1.366(4) . ?
C1 C10 1.416(4) . ?
C2 C3 1.432(4) . ?
C2 C11 1.460(4) . ?
C3 C4 1.358(4) . ?
C4 C5 1.413(4) . ?
C5 C6 1.416(4) . ?
C5 C10 1.423(4) . ?
C6 C7 1.359(4) . ?
C7 C8 1.415(4) . ?
C8 C9 1.360(4) . ?
C9 C10 1.413(4) . ?
S1 C14 1.719(3) . ?
S1 C11 1.726(3) . ?
C11 C12 1.356(10) . ?
C11 C21 1.360(14) . ?
C11 S3 1.70(2) . ?
C12 C13 1.430(12) . ?
C13 C14 1.370(4) . ?
C13 C20 1.506(8) . ?
C13 S3 1.58(2) . ?
C13 S4 1.779(10) . ?
C14 C22 1.500(13) . ?
C14 C21 1.53(3) . ?
C14 S2 1.763(3) . ?
S2 C15 1.821(3) . ?
C15 C16 1.533(4) . ?
C15 C22 1.72(5) . ?
C16 C17 1.511(4) . ?
C17 C18 1.531(4) . ?
C18 C19 1.519(4) . ?
C19 S4 1.55(3) . ?
C19 C20 1.581(14) . ?
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
C10 C1 C2 C3 2.1(4) . . . . ?
C10 C1 C2 C11 -176.5(2) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C11 C2 C3 C4 176.8(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -176.4(3) . . . . ?
C3 C4 C5 C10 2.6(4) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C10 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C1 -176.2(3) . . . . ?
C8 C9 C10 C5 0.6(4) . . . . ?
C2 C1 C10 C9 176.7(2) . . . . ?
C2 C1 C10 C5 -0.1(4) . . . . ?
C4 C5 C10 C9 -179.2(2) . . . . ?
C6 C5 C10 C9 -0.1(4) . . . . ?
C4 C5 C10 C1 -2.3(4) . . . . ?
C6 C5 C10 C1 176.8(2) . . . . ?
C1 C2 C11 C12 -163.0(7) . . . . ?
C3 C2 C11 C12 18.5(8) . . . . ?
C1 C2 C11 C21 14(2) . . . . ?
C3 C2 C11 C21 -164(2) . . . . ?
C1 C2 C11 S3 -166.7(10) . . . . ?
C3 C2 C11 S3 14.8(11) . . . . ?
C1 C2 C11 S1 18.5(3) . . . . ?
C3 C2 C11 S1 -160.0(2) . . . . ?
C14 S1 C11 C12 0.4(6) . . . . ?
C14 S1 C11 C2 179.2(2) . . . . ?
C2 C11 C12 C13 -179.1(4) . . . . ?
S1 C11 C12 C13 -0.4(10) . . . . ?
C11 C12 C13 C14 0.2(10) . . . . ?
C11 C12 C13 C20 -177.0(9) . . . . ?
S3 C13 C14 C22 -177(3) . . . . ?
S4 C13 C14 C22 5(3) . . . . ?
S3 C13 C14 C21 -7.1(19) . . . . ?
S4 C13 C14 C21 174.4(19) . . . . ?
C12 C13 C14 S1 0.2(6) . . . . ?
C20 C13 C14 S1 177.2(7) . . . . ?
C12 C13 C14 S2 178.0(5) . . . . ?
C20 C13 C14 S2 -5.0(8) . . . . ?
C11 S1 C14 C13 -0.3(2) . . . . ?
C11 S1 C14 S2 -178.37(18) . . . . ?
C13 C14 S2 C15 98.2(3) . . . . ?
S1 C14 S2 C15 -84.1(2) . . . . ?
C14 S2 C15 C16 -108.8(2) . . . . ?
C22 C15 C16 C17 38.7(12) . . . . ?
S2 C15 C16 C17 48.9(3) . . . . ?
C15 C16 C17 C18 54.8(4) . . . . ?
C16 C17 C18 C19 -144.1(3) . . . . ?
C17 C18 C19 S4 50.2(6) . . . . ?
C17 C18 C19 C20 65.0(5) . . . . ?
C14 C13 C20 C19 -91.6(8) . . . . ?
C12 C13 C20 C19 85.0(10) . . . . ?
C18 C19 C20 C13 53.9(9) . . . . ?
C14 C13 S3 C11 6.0(16) . . . . ?
S4 C13 S3 C11 -175.5(13) . . . . ?
C21 C11 S3 C13 -2(2) . . . . ?
C2 C11 S3 C13 179.2(5) . . . . ?
C18 C19 S4 C13 72.9(13) . . . . ?
C14 C13 S4 C19 -105.3(12) . . . . ?
S3 C13 S4 C19 76.2(18) . . . . ?
C2 C11 C21 C14 177.0(11) . . . . ?
S3 C11 C21 C14 -2(3) . . . . ?
C13 C14 C21 C11 5(3) . . . . ?
C22 C14 C21 C11 176(3) . . . . ?
C13 C14 C22 C15 85(4) . . . . ?
C21 C14 C22 C15 -82(5) . . . . ?
C16 C15 C22 C14 -97(4) . . . . ?
