#------------------------------------------------------------------------------
#$Date: 2022-01-26 00:50:45 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272225 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129617.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_7129617
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 O S2'
_chemical_formula_weight         340.48
_chemical_name_common            (S)-oxTN-1Napt
_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   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                 105.656(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.23910(10)
_cell_length_b                   15.9453(2)
_cell_length_c                   7.41670(10)
_cell_measurement_reflns_used    10801
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.1100
_cell_measurement_theta_min      2.5500
_cell_volume                     824.34(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0111
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10819
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.555
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93794
_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            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0199
_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)+(0.0383P)²+0.1084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0547
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3741
_reflns_number_total             3763
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06996a2.cif
_cod_data_source_block           S-9
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129617
_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   0.912
_shelx_estimated_absorpt_t_max   0.981
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 0.2232(2) 0.61216(10) 0.1997(2) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.2843(3) 0.62968(11) 0.0430(2) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.399718 0.604992 0.030791 0.027 Uiso 1 1 calc R U . . .
C3 C 0.1803(3) 0.68305(12) -0.0992(2) 0.0268(4) Uani 1 1 d . . . . .
H3 H 0.228189 0.695377 -0.203571 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0124(3) 0.71696(11) -0.0881(3) 0.0254(4) Uani 1 1 d . . . . .
H4 H -0.059231 0.751309 -0.187107 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0577(2) 0.70164(10) 0.0704(2) 0.0201(3) Uani 1 1 d . . . . .
C6 C -0.2335(3) 0.73639(11) 0.0821(3) 0.0254(4) Uani 1 1 d . . . . .
H6 H -0.306848 0.769637 -0.018150 0.030 Uiso 1 1 calc R U . . .
C7 C -0.2994(2) 0.72274(11) 0.2360(3) 0.0254(3) Uani 1 1 d . . . . .
H7 H -0.417898 0.746513 0.241954 0.031 Uiso 1 1 calc R U . . .
C9 C -0.0223(2) 0.63791(10) 0.3768(2) 0.0184(3) Uani 1 1 d . . . . .
H9 H 0.047968 0.604301 0.477965 0.022 Uiso 1 1 calc R U . . .
C8 C -0.1919(2) 0.67348(11) 0.3860(2) 0.0223(3) Uani 1 1 d . . . . .
H8 H -0.237196 0.664962 0.493517 0.027 Uiso 1 1 calc R U . . .
C10 C 0.0504(2) 0.65028(10) 0.2194(2) 0.0162(3) Uani 1 1 d . . . . .
S11 S 0.38550(5) 0.45482(2) 0.25225(5) 0.01800(9) Uani 1 1 d . . . . .
C12 C 0.3330(2) 0.55078(10) 0.3364(2) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.3995(2) 0.55378(11) 0.5268(2) 0.0185(3) Uani 1 1 d . . . . .
H13 H 0.385888 0.601709 0.598240 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4913(2) 0.47850(10) 0.6091(2) 0.0175(3) Uani 1 1 d . . . . .
C15 C 0.4942(2) 0.42000(10) 0.4756(2) 0.0166(3) Uani 1 1 d . . . . .
S16 S 0.61541(5) 0.32335(2) 0.51373(5) 0.01727(9) Uani 1 1 d . . . . .
C17 C 0.8271(3) 0.35478(11) 0.4420(3) 0.0237(3) Uani 1 1 d . . . . .
H17A H 0.924636 0.310032 0.480457 0.028 Uiso 1 1 calc R U . . .
H17B H 0.791207 0.357350 0.303519 0.028 Uiso 1 1 calc R U . . .
C18 C 0.9211(3) 0.43780(11) 0.5167(3) 0.0277(4) Uani 1 1 d . . . . .
H18A H 1.006953 0.454633 0.439297 0.033 Uiso 1 1 calc R U . . .
H18B H 0.819461 0.480921 0.499636 0.033 Uiso 1 1 calc R U . . .
C19 C 1.0367(3) 0.43835(13) 0.7210(3) 0.0340(4) Uani 1 1 d . . . . .
H19A H 1.101164 0.493485 0.747964 0.041 Uiso 1 1 calc R U . . .
H19B H 1.138487 0.395314 0.737308 0.041 Uiso 1 1 calc R U . . .
C20 C 0.9280(3) 0.42255(12) 0.8674(3) 0.0303(4) Uani 1 1 d . . . . .
H20A H 1.023260 0.414203 0.989878 0.036 Uiso 1 1 calc R U . . .
H20B H 0.855936 0.369398 0.835301 0.036 Uiso 1 1 calc R U . . .
C21 C 0.7866(3) 0.49087(12) 0.8913(3) 0.0293(4) Uani 1 1 d . . . . .
H21A H 0.812986 0.504399 1.026158 0.035 Uiso 1 1 calc R U . . .
H21B H 0.810929 0.542200 0.826227 0.035 Uiso 1 1 calc R U . . .
C22 C 0.5735(3) 0.46761(12) 0.8167(2) 0.0237(3) Uani 1 1 d . . . . .
H22A H 0.557030 0.408337 0.849031 0.028 Uiso 1 1 calc R U . . .
H22B H 0.498498 0.502523 0.881960 0.028 Uiso 1 1 calc R U . . .
O23 O 0.51300(19) 0.26356(8) 0.36469(19) 0.0263(3) 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
C2 C1 C10 119.15(15) . . ?
C2 C1 C12 118.52(15) . . ?
C10 C1 C12 122.24(13) . . ?
C1 C2 C3 121.79(16) . . ?
C4 C3 C2 120.29(16) . . ?
C3 C4 C5 120.56(16) . . ?
C6 C5 C4 120.78(16) . . ?
C6 C5 C10 119.53(15) . . ?
C4 C5 C10 119.69(16) . . ?
C7 C6 C5 120.76(16) . . ?
C6 C7 C8 120.27(16) . . ?
C8 C9 C10 121.33(15) . . ?
C9 C8 C7 120.09(16) . . ?
C9 C10 C5 117.99(15) . . ?
C9 C10 C1 123.58(14) . . ?
C5 C10 C1 118.40(14) . . ?
C15 S11 C12 91.49(8) . . ?
C13 C12 C1 131.41(14) . . ?
C13 C12 S11 110.70(12) . . ?
C1 C12 S11 117.86(11) . . ?
C12 C13 C14 114.00(15) . . ?
C15 C14 C13 111.18(14) . . ?
C15 C14 C22 125.79(15) . . ?
C13 C14 C22 123.03(14) . . ?
C14 C15 S11 112.63(12) . . ?
C14 C15 S16 125.96(13) . . ?
S11 C15 S16 121.06(9) . . ?
O23 S16 C15 108.27(8) . . ?
O23 S16 C17 104.34(8) . . ?
C15 S16 C17 97.72(8) . . ?
C18 C17 S16 117.47(13) . . ?
C19 C18 C17 116.05(16) . . ?
C18 C19 C20 117.25(15) . . ?
C19 C20 C21 116.93(17) . . ?
C22 C21 C20 114.99(15) . . ?
C14 C22 C21 114.96(15) . . ?
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 1.379(2) . ?
C1 C10 1.433(2) . ?
C1 C12 1.478(2) . ?
C2 C3 1.405(3) . ?
C3 C4 1.353(3) . ?
C4 C5 1.422(2) . ?
C5 C6 1.412(3) . ?
C5 C10 1.427(2) . ?
C6 C7 1.368(3) . ?
C7 C8 1.412(3) . ?
C9 C8 1.371(2) . ?
C9 C10 1.418(2) . ?
S11 C15 1.7226(16) . ?
S11 C12 1.7330(16) . ?
C12 C13 1.364(2) . ?
C13 C14 1.427(2) . ?
C14 C15 1.365(2) . ?
C14 C22 1.504(2) . ?
C15 S16 1.7581(16) . ?
S16 O23 1.4960(13) . ?
S16 C17 1.8230(18) . ?
C17 C18 1.523(2) . ?
C18 C19 1.521(3) . ?
C19 C20 1.524(3) . ?
C20 C21 1.538(3) . ?
C21 C22 1.537(3) . ?
