#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:31:17 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157812.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_7157812
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          502
_chemical_name_systematic        1,2-Bis(methanesulfonyl)benzene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1116(2)
_cell_length_b                   12.9234(3)
_cell_length_c                   7.4954(1)
_cell_measurement_reflns_used    27584
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.998
_cell_measurement_theta_min      2.558
_cell_volume                     979.47(3)
_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    SIR2004
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25073
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.998
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'Fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.93102
_exptl_absorpt_correction_T_min  0.91478
_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    1.589
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0279
_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)+(0.0501P)²+0.3128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1449
_reflns_number_total             1564
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob02083d2.cif
_cod_data_source_block           CY011
_cod_depositor_comments
'Adding full bibliography for 7157808--7157819.cif.'
_cod_database_code               7157812
_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   0.935
_shelx_estimated_absorpt_t_max   0.959
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y, -z-1/2'
'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 0.34431(2) 0.17920(2) 0.64552(3) 0.01507(10) Uani 1 1 d . . . . .
O1 O 0.21197(7) 0.21477(6) 0.60600(11) 0.02086(16) Uani 1 1 d . . . . .
O2 O 0.35754(7) 0.10146(6) 0.78251(10) 0.02046(17) Uani 1 1 d . . . . .
C1 C 0.43898(8) 0.29102(7) 0.70484(12) 0.01417(17) Uani 1 1 d . . . . .
C2 C 0.38080(10) 0.38493(7) 0.65793(13) 0.01756(19) Uani 1 1 d . . . . .
H2 H 0.3006(15) 0.3863(11) 0.594(2) 0.024(3) Uiso 1 1 d . . . . .
C3 C 0.44093(9) 0.47830(7) 0.70295(14) 0.0200(2) Uani 1 1 d . . . . .
H3 H 0.3989(16) 0.5428(12) 0.669(2) 0.026(4) Uiso 1 1 d . . . . .
C4 C 0.41521(11) 0.13554(8) 0.44509(14) 0.0209(2) Uani 1 1 d . . . . .
H4A H 0.3664(16) 0.0713(15) 0.417(2) 0.036(4) Uiso 1 1 d . . . . .
H4B H 0.5077(16) 0.1238(11) 0.462(2) 0.030(4) Uiso 1 1 d . . . . .
H4C H 0.4046(19) 0.1907(13) 0.360(2) 0.032(4) 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 116.94(4) . . ?
O2 S1 C4 110.30(5) . . ?
O1 S1 C4 107.73(5) . . ?
O2 S1 C1 109.63(4) . . ?
O1 S1 C1 106.81(4) . . ?
C4 S1 C1 104.68(5) . . ?
C2 C1 C1 119.43(5) . 7_657 ?
C2 C1 S1 114.50(7) . . ?
C1 C1 S1 126.05(3) 7_657 . ?
C3 C2 C1 120.60(9) . . ?
C3 C2 H2 118.9(9) . . ?
C1 C2 H2 120.5(9) . . ?
C3 C3 C2 119.94(6) 7_657 . ?
C3 C3 H3 120.8(9) 7_657 . ?
C2 C3 H3 119.3(10) . . ?
S1 C4 H4A 104.2(10) . . ?
S1 C4 H4B 109.6(10) . . ?
H4A C4 H4B 112.6(13) . . ?
S1 C4 H4C 106.5(10) . . ?
H4A C4 H4C 115.3(15) . . ?
H4B C4 H4C 108.3(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
S1 O2 1.4428(7) . ?
S1 O1 1.4456(7) . ?
S1 C4 1.7577(11) . ?
S1 C1 1.7896(9) . ?
C1 C2 1.3938(12) . ?
C1 C1 1.4075(17) 7_657 ?
C2 C3 1.3927(13) . ?
C2 H2 0.943(16) . ?
C3 C3 1.387(2) 7_657 ?
C3 H3 0.971(16) . ?
C4 H4A 0.987(18) . ?
C4 H4B 0.956(16) . ?
C4 H4C 0.963(16) . ?
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 C2 -143.14(7) . . . . ?
O1 S1 C1 C2 -15.52(8) . . . . ?
C4 S1 C1 C2 98.56(8) . . . . ?
O2 S1 C1 C1 35.33(12) . . . 7_657 ?
O1 S1 C1 C1 162.94(10) . . . 7_657 ?
C4 S1 C1 C1 -82.98(12) . . . 7_657 ?
C1 C1 C2 C3 -1.37(16) 7_657 . . . ?
S1 C1 C2 C3 177.21(8) . . . . ?
C1 C2 C3 C3 -0.71(18) . . . 7_657 ?
