#------------------------------------------------------------------------------
#$Date: 2022-01-26 00:50:45 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272225 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129609.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_7129609
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            'C26 H22 O S2'
_chemical_formula_weight         414.55
_chemical_name_common            rac-oxTN-Pyrene
_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   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                91.4630(10)
_cell_angle_beta                 91.368(2)
_cell_angle_gamma                111.185(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0966(2)
_cell_length_b                   10.4919(2)
_cell_length_c                   11.1191(2)
_cell_measurement_reflns_used    9429
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.2720
_cell_measurement_theta_min      2.5520
_cell_volume                     988.55(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 0.995
_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  0.0193
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11206
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.833
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       platelet
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0470
_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)+(0.0497P)²+1.3672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3143
_reflns_number_total             3463
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06996a2.cif
_cod_data_source_block           rac-12
_cod_database_code               7129609
_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   0.967
_shelx_estimated_absorpt_t_max   0.978
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 0.54638(7) 0.91602(6) 0.77022(6) 0.02595(18) Uani 1 1 d . . . . .
S2 S 0.81634(8) 0.97929(7) 0.60340(7) 0.0344(2) Uani 1 1 d . . . . .
O3 O 0.8827(2) 1.0984(2) 0.6857(2) 0.0513(6) Uani 1 1 d . . . . .
C4 C 0.3541(3) 0.8294(2) 0.7198(2) 0.0254(5) Uani 1 1 d . . . . .
C5 C 0.3490(3) 0.7968(3) 0.6001(2) 0.0275(5) Uani 1 1 d . . . . .
H5 H 0.253143 0.748158 0.556459 0.033 Uiso 1 1 calc R U . . .
C6 C 0.4970(3) 0.8409(2) 0.5456(2) 0.0274(5) Uani 1 1 d . . . . .
C7 C 0.6141(3) 0.9081(2) 0.6281(2) 0.0276(5) Uani 1 1 d . . . . .
C8 C 0.8726(3) 0.8465(3) 0.6688(2) 0.0350(6) Uani 1 1 d . . . . .
H8A H 0.983980 0.864175 0.650058 0.042 Uiso 1 1 calc R U . . .
H8AB H 0.867706 0.854660 0.757414 0.042 Uiso 1 1 calc R U . . .
C9 C 0.7748(3) 0.6996(3) 0.6286(3) 0.0361(6) Uani 1 1 d . . . . .
H9A H 0.797690 0.637547 0.685530 0.043 Uiso 1 1 calc R U . . .
H9AB H 0.661815 0.686228 0.634568 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8013(4) 0.6575(3) 0.5031(3) 0.0407(7) Uani 1 1 d . . . . .
H10A H 0.748170 0.557006 0.493342 0.049 Uiso 1 1 calc R U . . .
H10B H 0.915769 0.678517 0.495444 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7450(3) 0.7223(3) 0.4001(2) 0.0389(7) Uani 1 1 d . . . . .
H11A H 0.778484 0.692274 0.323766 0.047 Uiso 1 1 calc R U . . .
H11B H 0.798883 0.822787 0.408882 0.047 Uiso 1 1 calc R U . . .
C12 C 0.5649(3) 0.6896(3) 0.3896(2) 0.0353(6) Uani 1 1 d . . . . .
H12A H 0.526587 0.652533 0.307269 0.042 Uiso 1 1 calc R U . . .
H12B H 0.512156 0.617338 0.446465 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5160(3) 0.8121(3) 0.4155(2) 0.0335(6) Uani 1 1 d . . . . .
H13A H 0.596069 0.894390 0.383042 0.040 Uiso 1 1 calc R U . . .
H13B H 0.414776 0.796588 0.371477 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2284(3) 0.8083(2) 0.8053(2) 0.0236(5) Uani 1 1 d . . . . .
C15 C 0.2353(3) 0.9162(2) 0.8839(2) 0.0266(5) Uani 1 1 d . . . . .
H15 H 0.319238 1.001713 0.878075 0.032 Uiso 1 1 calc R U . . .
C16 C 0.1251(3) 0.9027(2) 0.9691(2) 0.0254(5) Uani 1 1 d . . . . .
H16 H 0.134968 0.978015 1.022141 0.030 Uiso 1 1 calc R U . . .
C17 C -0.0016(3) 0.7798(2) 0.9788(2) 0.0235(5) Uani 1 1 d . . . . .
C18 C -0.1202(3) 0.7630(2) 1.0652(2) 0.0260(5) Uani 1 1 d . . . . .
H18 H -0.113149 0.837680 1.118163 0.031 Uiso 1 1 calc R U . . .
C19 C -0.2409(3) 0.6445(3) 1.0730(2) 0.0284(6) Uani 1 1 d . . . . .
H19 H -0.319925 0.637412 1.129490 0.034 Uiso 1 1 calc R U . . .
C20 C -0.2536(3) 0.5280(3) 0.9980(2) 0.0262(5) Uani 1 1 d . . . . .
C21 C -0.3730(3) 0.4013(3) 1.0099(2) 0.0304(6) Uani 1 1 d . . . . .
H21 H -0.452121 0.391877 1.066921 0.036 Uiso 1 1 calc R U . . .
C22 C -0.3777(3) 0.2897(3) 0.9402(2) 0.0316(6) Uani 1 1 d . . . . .
H22 H -0.459606 0.203780 0.950071 0.038 Uiso 1 1 calc R U . . .
C23 C -0.2656(3) 0.3006(3) 0.8563(2) 0.0286(6) Uani 1 1 d . . . . .
H23 H -0.270136 0.222222 0.809445 0.034 Uiso 1 1 calc R U . . .
C24 C -0.1449(3) 0.4262(2) 0.8393(2) 0.0248(5) Uani 1 1 d . . . . .
C25 C -0.0262(3) 0.4413(2) 0.7547(2) 0.0265(5) Uani 1 1 d . . . . .
H25 H -0.030095 0.364584 0.705672 0.032 Uiso 1 1 calc R U . . .
C26 C 0.0922(3) 0.5622(2) 0.7422(2) 0.0254(5) Uani 1 1 d . . . . .
H26 H 0.169635 0.568782 0.684457 0.030 Uiso 1 1 calc R U . . .
C27 C 0.1041(3) 0.6810(2) 0.8140(2) 0.0226(5) Uani 1 1 d . . . . .
C28 C -0.0116(3) 0.6683(2) 0.9006(2) 0.0217(5) Uani 1 1 d . . . . .
C29 C -0.1376(3) 0.5411(2) 0.9124(2) 0.0229(5) 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'
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
C7 S1 C4 91.20(12) . . ?
O3 S2 C7 107.19(12) . . ?
O3 S2 C8 105.45(13) . . ?
C7 S2 C8 97.94(13) . . ?
C5 C4 C14 131.4(2) . . ?
C5 C4 S1 110.27(19) . . ?
C14 C4 S1 118.29(18) . . ?
C4 C5 C6 115.0(2) . . ?
C7 C6 C5 110.4(2) . . ?
C7 C6 C13 126.7(2) . . ?
C5 C6 C13 122.9(2) . . ?
C6 C7 S1 113.13(19) . . ?
C6 C7 S2 127.0(2) . . ?
S1 C7 S2 119.81(15) . . ?
C9 C8 S2 116.63(19) . . ?
C10 C9 C8 115.7(3) . . ?
C9 C10 C11 117.0(2) . . ?
C10 C11 C12 115.8(3) . . ?
C13 C12 C11 114.4(2) . . ?
C6 C13 C12 115.3(2) . . ?
C15 C14 C27 119.0(2) . . ?
C15 C14 C4 118.7(2) . . ?
C27 C14 C4 122.2(2) . . ?
C16 C15 C14 122.1(2) . . ?
C15 C16 C17 120.7(2) . . ?
C16 C17 C28 118.6(2) . . ?
C16 C17 C18 122.2(2) . . ?
C28 C17 C18 119.3(2) . . ?
C19 C18 C17 121.3(2) . . ?
C18 C19 C20 121.3(2) . . ?
C21 C20 C29 119.2(2) . . ?
C21 C20 C19 122.1(2) . . ?
C29 C20 C19 118.7(2) . . ?
C22 C21 C20 120.7(3) . . ?
C23 C22 C21 120.9(2) . . ?
C22 C23 C24 120.6(2) . . ?
C23 C24 C29 118.8(2) . . ?
C23 C24 C25 122.2(2) . . ?
C29 C24 C25 118.9(2) . . ?
C26 C25 C24 121.4(2) . . ?
C25 C26 C27 121.6(2) . . ?
C14 C27 C28 118.7(2) . . ?
C14 C27 C26 123.1(2) . . ?
C28 C27 C26 118.2(2) . . ?
C17 C28 C27 120.9(2) . . ?
C17 C28 C29 119.0(2) . . ?
C27 C28 C29 120.1(2) . . ?
C20 C29 C24 119.8(2) . . ?
C20 C29 C28 120.4(2) . . ?
C24 C29 C28 119.8(2) . . ?
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 C7 1.721(3) . ?
S1 C4 1.726(2) . ?
S2 O3 1.461(2) . ?
S2 C7 1.749(3) . ?
S2 C8 1.812(3) . ?
C4 C5 1.361(4) . ?
C4 C14 1.463(4) . ?
C5 C6 1.413(4) . ?
C6 C7 1.360(4) . ?
C6 C13 1.497(4) . ?
C8 C9 1.524(4) . ?
C9 C10 1.504(4) . ?
C10 C11 1.517(4) . ?
C11 C12 1.549(4) . ?
C12 C13 1.527(4) . ?
C14 C15 1.394(3) . ?
C14 C27 1.411(3) . ?
C15 C16 1.369(4) . ?
C16 C17 1.393(3) . ?
C17 C28 1.414(3) . ?
C17 C18 1.428(4) . ?
C18 C19 1.335(4) . ?
C19 C20 1.430(4) . ?
C20 C21 1.391(4) . ?
C20 C29 1.409(4) . ?
C21 C22 1.376(4) . ?
C22 C23 1.375(4) . ?
C23 C24 1.398(3) . ?
C24 C29 1.417(3) . ?
C24 C25 1.418(4) . ?
C25 C26 1.348(3) . ?
C26 C27 1.431(3) . ?
C27 C28 1.417(3) . ?
C28 C29 1.422(3) . ?
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
C7 S1 C4 C5 0.8(2) . . . . ?
C7 S1 C4 C14 -176.8(2) . . . . ?
C14 C4 C5 C6 176.6(2) . . . . ?
S1 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C13 178.6(2) . . . . ?
C5 C6 C7 S1 0.8(3) . . . . ?
C13 C6 C7 S1 -177.9(2) . . . . ?
C5 C6 C7 S2 179.25(19) . . . . ?
C13 C6 C7 S2 0.5(4) . . . . ?
C4 S1 C7 C6 -0.9(2) . . . . ?
C4 S1 C7 S2 -179.52(16) . . . . ?
O3 S2 C7 C6 148.6(2) . . . . ?
C8 S2 C7 C6 -102.5(2) . . . . ?
O3 S2 C7 S1 -33.05(19) . . . . ?
C8 S2 C7 S1 75.90(17) . . . . ?
O3 S2 C8 C9 159.2(2) . . . . ?
C7 S2 C8 C9 48.8(2) . . . . ?
S2 C8 C9 C10 73.2(3) . . . . ?
C8 C9 C10 C11 -68.8(3) . . . . ?
C9 C10 C11 C12 -63.3(4) . . . . ?
C10 C11 C12 C13 112.5(3) . . . . ?
C7 C6 C13 C12 80.5(3) . . . . ?
C5 C6 C13 C12 -98.0(3) . . . . ?
C11 C12 C13 C6 -84.9(3) . . . . ?
C5 C4 C14 C15 -134.4(3) . . . . ?
S1 C4 C14 C15 42.6(3) . . . . ?
C5 C4 C14 C27 48.1(4) . . . . ?
S1 C4 C14 C27 -134.9(2) . . . . ?
C27 C14 C15 C16 -0.1(4) . . . . ?
C4 C14 C15 C16 -177.7(2) . . . . ?
C14 C15 C16 C17 -1.3(4) . . . . ?
C15 C16 C17 C28 1.5(4) . . . . ?
C15 C16 C17 C18 -178.9(2) . . . . ?
C16 C17 C18 C19 179.9(2) . . . . ?
C28 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 2.1(4) . . . . ?
C18 C19 C20 C21 175.9(2) . . . . ?
C18 C19 C20 C29 -1.6(4) . . . . ?
C29 C20 C21 C22 0.5(4) . . . . ?
C19 C20 C21 C22 -177.0(2) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 C29 1.8(3) . . . . ?
C22 C23 C24 C25 179.3(2) . . . . ?
C23 C24 C25 C26 -177.8(2) . . . . ?
C29 C24 C25 C26 -0.3(4) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C15 C14 C27 C28 1.4(3) . . . . ?
C4 C14 C27 C28 178.9(2) . . . . ?
C15 C14 C27 C26 -176.2(2) . . . . ?
C4 C14 C27 C26 1.3(4) . . . . ?
C25 C26 C27 C14 178.4(2) . . . . ?
C25 C26 C27 C28 0.8(3) . . . . ?
C16 C17 C28 C27 -0.2(3) . . . . ?
C18 C17 C28 C27 -179.8(2) . . . . ?
C16 C17 C28 C29 178.0(2) . . . . ?
C18 C17 C28 C29 -1.7(3) . . . . ?
C14 C27 C28 C17 -1.3(3) . . . . ?
C26 C27 C28 C17 176.5(2) . . . . ?
C14 C27 C28 C29 -179.4(2) . . . . ?
C26 C27 C28 C29 -1.6(3) . . . . ?
C21 C20 C29 C24 0.6(3) . . . . ?
C19 C20 C29 C24 178.2(2) . . . . ?
C21 C20 C29 C28 -178.2(2) . . . . ?
C19 C20 C29 C28 -0.6(3) . . . . ?
C23 C24 C29 C20 -1.8(3) . . . . ?
C25 C24 C29 C20 -179.4(2) . . . . ?
C23 C24 C29 C28 177.0(2) . . . . ?
C25 C24 C29 C28 -0.5(3) . . . . ?
C17 C28 C29 C20 2.2(3) . . . . ?
C27 C28 C29 C20 -179.6(2) . . . . ?
C17 C28 C29 C24 -176.6(2) . . . . ?
C27 C28 C29 C24 1.5(3) . . . . ?
