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#$Date: 2021-02-05 01:31:17 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157814.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_7157814
loop_
_publ_author_name
'Ichikawa, Yuki'
'Hiramatsu, Michiaki'
'Mita, Yusuke'
'Makishima, Makoto'
'Matsumoto, Yotaro'
'Masumoto, Yui'
'Muranaka, Atsuya'
'Uchiyama, Masanobu'
'Hashimoto, Yuichi'
'Ishikawa, Minoru'
_publ_section_title
;
 meta-Non-flat substituents: a novel molecular design to improve
 aqueous solubility in small molecule drug discovery.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              446
_journal_page_last               456
_journal_paper_doi               10.1039/d0ob02083d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C8 H10 O4 S2'
_chemical_formula_sum            'C8 H10 O4 S2'
_chemical_formula_weight         234.28
_chemical_melting_point          474
_chemical_name_systematic        1,3-Bis(methanesulfonyl)benzene
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.3238(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8295(5)
_cell_length_b                   6.9792(2)
_cell_length_c                   7.9202(2)
_cell_measurement_reflns_used    13083
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.404
_cell_measurement_theta_min      2.286
_cell_volume                     984.74(5)
_computing_cell_refinement       HKL2000
_computing_data_collection       CrystalClear
_computing_data_reduction        HKL2000
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.404
_diffrn_reflns_theta_min         2.286
_diffrn_source                   'Fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  0.96605
_exptl_absorpt_correction_T_min  0.95530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0306
_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)+(0.0417P)²+0.6189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1255
_reflns_number_total             1479
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob02083d2.cif
_cod_data_source_block           CY010
_cod_depositor_comments
'Adding full bibliography for 7157808--7157819.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7157814
_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   0.964
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S1 S 0.36143(2) 0.74435(4) 0.88488(4) 0.01920(11) Uani 1 1 d . . . . .
O1 O 0.32391(6) 0.61769(16) 0.99803(13) 0.0268(2) Uani 1 1 d . . . . .
O2 O 0.38780(6) 0.92736(15) 0.94697(14) 0.0295(3) Uani 1 1 d . . . . .
C1 C 0.43958(7) 0.61771(18) 0.80906(15) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.5000 0.7200(3) 0.7500 0.0202(4) Uani 1 2 d S T P . .
H2 H 0.5000 0.858(4) 0.7500 0.038(7) Uiso 1 2 d S . P . .
C3 C 0.43916(7) 0.41871(18) 0.81071(17) 0.0190(3) Uani 1 1 d . . . . .
H3 H 0.3979(9) 0.353(3) 0.850(2) 0.021(4) Uiso 1 1 d . . . . .
C4 C 0.5000 0.3198(3) 0.7500 0.0226(4) Uani 1 2 d S T P . .
H4 H 0.5000 0.178(4) 0.7500 0.030(6) Uiso 1 2 d S . P . .
C5 C 0.30177(8) 0.7827(2) 0.70541(19) 0.0227(3) Uani 1 1 d . . . . .
H5A H 0.2583(12) 0.834(3) 0.747(3) 0.037(5) Uiso 1 1 d . . . . .
H5B H 0.2932(10) 0.667(3) 0.653(2) 0.026(4) Uiso 1 1 d . . . . .
H5C H 0.3248(11) 0.872(3) 0.634(2) 0.032(5) 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 0.0033 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
O2 S1 O1 118.97(7) . . ?
O2 S1 C5 108.59(7) . . ?
O1 S1 C5 108.33(7) . . ?
O2 S1 C1 107.89(6) . . ?
O1 S1 C1 107.17(6) . . ?
C5 S1 C1 105.03(6) . . ?
C3 C1 C2 121.45(12) . . ?
C3 C1 S1 119.35(10) . . ?
C2 C1 S1 119.20(10) . . ?
C1 C2 C1 118.12(17) . 2_656 ?
C1 C2 H2 120.94(8) . . ?
C1 C2 H2 120.94(8) 2_656 . ?
C4 C3 C1 119.31(13) . . ?
C4 C3 H3 120.6(11) . . ?
C1 C3 H3 120.0(11) . . ?
C3 C4 C3 120.34(17) . 2_656 ?
C3 C4 H4 119.83(8) . . ?
C3 C4 H4 119.83(8) 2_656 . ?
S1 C5 H5A 105.1(12) . . ?
S1 C5 H5B 108.3(11) . . ?
H5A C5 H5B 112.1(17) . . ?
S1 C5 H5C 108.7(11) . . ?
H5A C5 H5C 110.0(16) . . ?
H5B C5 H5C 112.2(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 O2 1.4407(11) . ?
S1 O1 1.4425(10) . ?
S1 C5 1.7610(15) . ?
S1 C1 1.7751(12) . ?
C1 C3 1.3889(17) . ?
C1 C2 1.3893(15) . ?
C2 C1 1.3893(15) 2_656 ?
C2 H2 0.96(3) . ?
C3 C4 1.3881(16) . ?
C3 H3 0.931(17) . ?
C4 C3 1.3881(16) 2_656 ?
C4 H4 0.99(3) . ?
C5 H5A 0.93(2) . ?
C5 H5B 0.918(19) . ?
C5 H5C 0.949(19) . ?
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
O2 S1 C1 C3 152.32(11) . . . . ?
O1 S1 C1 C3 23.08(13) . . . . ?
C5 S1 C1 C3 -91.99(12) . . . . ?
O2 S1 C1 C2 -27.41(10) . . . . ?
O1 S1 C1 C2 -156.64(8) . . . . ?
C5 S1 C1 C2 88.29(10) . . . . ?
C3 C1 C2 C1 0.43(9) . . . 2_656 ?
S1 C1 C2 C1 -179.85(10) . . . 2_656 ?
C2 C1 C3 C4 -0.85(18) . . . . ?
S1 C1 C3 C4 179.43(7) . . . . ?
C1 C3 C4 C3 0.42(9) . . . 2_656 ?
