#------------------------------------------------------------------------------
#$Date: 2020-07-01 08:32:32 +0300 (Wed, 01 Jul 2020) $
#$Revision: 253605 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243458.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243458
loop_
_publ_author_name
'Nashawi, Asma'
'Lawson, Christopher P.'
'Abdel-Sattar, M. Omar'
'ter Horst, Joop H.'
'Coxon, Geoffrey D.'
'Kennedy, Alan R.'
_publ_section_title
;
 Synthesis and crystal structures of
 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one and
 3-hydroxy-4-methyl-2H-thiophen-5-one
;
_journal_coeditor_code           LH5954
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1158
_journal_page_last               1162
_journal_paper_doi               10.1107/S2056989020008269
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C6 H8 O2 S'
_chemical_formula_moiety         'C6 H8 O2 S'
_chemical_formula_sum            'C6 H8 O2 S'
_chemical_formula_weight         144.18
_chemical_name_systematic
;
3-Hydroxy-2,4-dimethyl-2H-thiophen-5-one
;
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2860(10)
_cell_length_b                   11.4809(8)
_cell_length_c                   12.6469(10)
_cell_measurement_reflns_used    1393
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.7690
_cell_measurement_theta_min      7.0090
_cell_volume                     1348.3(2)
_computing_cell_refinement
;
CrysalisPro (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysalisPro (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysalisPro (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020) and ORTEP-3 for WIndows (Farrugia,
2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1994)
;
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4293
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         73.014
_diffrn_reflns_theta_min         7.003
_diffrn_source                   'sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.633
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_correction_T_min  0.323
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2019)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       rod
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.287
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0531
_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)+(0.0810P)²+0.8472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1482
_reflns_number_gt                1115
_reflns_number_total             1323
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5954sup1.cif
_cod_data_source_block           4
_cod_database_code               2243458
_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.
;
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.84281(8) 0.16688(5) 0.67914(5) 0.0327(3) Uani d 1 . .
O O1 0.6506(2) 0.17209(14) 0.52486(16) 0.0311(5) Uani d 1 . .
O O2 0.9490(2) 0.48890(16) 0.62458(16) 0.0329(5) Uani d 1 . .
C C3 0.8868(3) 0.3850(2) 0.6199(2) 0.0283(6) Uani d 1 . .
C C6 0.9207(4) 0.3465(3) 0.8144(2) 0.0374(7) Uani d 1 . .
H H6A 0.9733 0.4199 0.8231 0.056 Uiso calc 1 . .
H H6B 0.9571 0.2890 0.8651 0.056 Uiso calc 1 . .
H H6C 0.8179 0.3597 0.8271 0.056 Uiso calc 1 . .
C C2 0.7822(3) 0.3476(2) 0.5539(2) 0.0272(6) Uani d 1 . .
C C1 0.7427(3) 0.2288(2) 0.57332(19) 0.0281(6) Uani d 1 . .
C C5 0.7097(3) 0.4157(2) 0.4680(2) 0.0330(6) Uani d 1 . .
H H5A 0.6367 0.4670 0.4990 0.049 Uiso calc 1 . .
H H5B 0.6636 0.3619 0.4182 0.049 Uiso calc 1 . .
H H5C 0.7815 0.4627 0.4304 0.049 Uiso calc 1 . .
C C4 0.9423(3) 0.3008(2) 0.7017(2) 0.0302(6) Uani d 1 . .
H H4 1.0472 0.2864 0.6892 0.036 Uiso calc 1 . .
H H1H 0.914(5) 0.542(3) 0.581(3) 0.053(11) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C4 . . 92.62(12) y
C3 O2 H1H . . 116(3) ?
O2 C3 C2 . . 128.8(2) ?
O2 C3 C4 . . 113.4(2) y
C2 C3 C4 . . 117.8(2) y
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C3 C2 C1 . . 112.3(2) y
C3 C2 C5 . . 127.3(2) ?
C1 C2 C5 . . 120.4(2) ?
O1 C1 C2 . . 126.3(2) ?
O1 C1 S1 . . 121.6(2) ?
C2 C1 S1 . . 112.1(2) y
C2 C5 H5A . . 109.5 ?
C2 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C2 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C3 C4 C6 . . 112.0(2) ?
C3 C4 S1 . . 105.16(18) y
C6 C4 S1 . . 111.7(2) ?
C3 C4 H4 . . 109.3 ?
C6 C4 H4 . . 109.3 ?
S1 C4 H4 . . 109.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.778(3) y
S1 C4 . 1.816(3) y
O1 C1 . 1.238(3) y
O2 C3 . 1.326(3) y
O2 H1H . 0.88(4) ?
C3 C2 . 1.351(4) y
C3 C4 . 1.507(4) y
C6 C4 . 1.532(4) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C2 C1 . 1.434(4) y
C2 C5 . 1.498(4) ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C4 H4 . 1.0000 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H1H O1 7_765 0.88(4) 1.77(4) 2.621(3) 164(4)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C3 C2 C1 . . . . -180.0(2) ?
C4 C3 C2 C1 . . . . -0.9(3) ?
O2 C3 C2 C5 . . . . 0.2(5) ?
C4 C3 C2 C5 . . . . 179.2(2) ?
C3 C2 C1 O1 . . . . -179.8(3) ?
C5 C2 C1 O1 . . . . 0.0(4) ?
C3 C2 C1 S1 . . . . 0.4(3) ?
C5 C2 C1 S1 . . . . -179.8(2) ?
C4 S1 C1 O1 . . . . -179.6(2) ?
C4 S1 C1 C2 . . . . 0.2(2) ?
O2 C3 C4 C6 . . . . 58.8(3) ?
C2 C3 C4 C6 . . . . -120.4(3) ?
O2 C3 C4 S1 . . . . -179.77(18) ?
C2 C3 C4 S1 . . . . 1.0(3) ?
C1 S1 C4 C3 . . . . -0.64(19) ?
C1 S1 C4 C6 . . . . 121.0(2) ?

_cod_database_fobs_code 2243458
