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#$Date: 2020-07-01 08:32:32 +0300 (Wed, 01 Jul 2020) $
#$Revision: 253605 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243459.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_2243459
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          'C5 H6 O2 S'
_chemical_formula_moiety         'C5 H6 O2 S'
_chemical_formula_sum            'C5 H6 O2 S'
_chemical_formula_weight         130.16
_chemical_name_systematic
;
3-Hydroxy-4-methyl-2H-thiophen-5-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.728(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1054(3)
_cell_length_b                   22.9727(13)
_cell_length_c                   6.1928(5)
_cell_measurement_reflns_used    1968
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.3560
_cell_measurement_theta_min      5.1810
_cell_volume                     567.37(7)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku XtaLAB AFC12'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2121
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.501
_diffrn_source                   'rotating anode'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.464
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2019)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.334
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         2121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0500
_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)+(0.0078P)²+1.3568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                1955
_reflns_number_total             2121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5954sup1.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243459
_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, y+1/2, -z+1/2'
'-x, -y, -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 0.6910(2) 0.70598(3) 0.55558(14) 0.0183(2) Uani d 1 . .
O O1 0.8610(6) 0.64486(10) 0.9223(4) 0.0231(6) Uani d 1 . .
O O2 0.0808(6) 0.58103(10) 0.2795(4) 0.0203(5) Uani d 1 . .
C C1 0.6862(8) 0.64503(13) 0.7309(5) 0.0164(7) Uani d 1 . .
C C2 0.4606(8) 0.60031(13) 0.6216(5) 0.0164(7) Uani d 1 . .
C C3 0.3060(8) 0.61502(12) 0.4117(5) 0.0155(6) Uani d 1 . .
C C4 0.3963(8) 0.67257(13) 0.3276(5) 0.0160(6) Uani d 1 . .
H H4A 0.1943 0.6972 0.2798 0.019 Uiso calc 1 . .
H H4B 0.4987 0.6669 0.1996 0.019 Uiso calc 1 . .
C C5 0.4138(10) 0.54539(13) 0.7423(6) 0.0213(7) Uani d 1 . .
H H5A 0.2293 0.5227 0.6513 0.032 Uiso calc 1 . .
H H5B 0.3611 0.5553 0.8842 0.032 Uiso calc 1 . .
H H5C 0.6206 0.5224 0.7701 0.032 Uiso calc 1 . .
H H1H 0.003(12) 0.597(2) 0.156(8) 0.045(14) 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 0.1246 0.1234 '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'
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'
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 . . 92.33(15) y
C3 O2 H1H . . 111(3) ?
O1 C1 C2 . . 127.8(3) ?
O1 C1 S1 . . 120.2(3) ?
C2 C1 S1 . . 112.0(2) y
C3 C2 C1 . . 112.2(3) y
C3 C2 C5 . . 127.2(3) ?
C1 C2 C5 . . 120.6(3) ?
O2 C3 C2 . . 123.0(3) ?
O2 C3 C4 . . 119.7(3) y
C2 C3 C4 . . 117.2(3) y
C3 C4 S1 . . 106.2(2) y
C3 C4 H4A . . 110.5 ?
S1 C4 H4A . . 110.5 ?
C3 C4 H4B . . 110.5 ?
S1 C4 H4B . . 110.5 ?
H4A C4 H4B . . 108.7 ?
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 ?
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 . 1.775(3) y
S1 C4 . 1.799(3) y
O1 C1 . 1.231(4) y
O2 C3 . 1.332(4) y
O2 H1H . 0.84(5) ?
C1 C2 . 1.440(4) y
C2 C3 . 1.347(4) y
C2 C5 . 1.502(4) y
C3 C4 . 1.499(4) y
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
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 1_454 0.84(5) 1.80(5) 2.629(3) 168(5)
C4 H4B O1 1_554 0.99 2.58 3.552(4) 169.1
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
C4 S1 C1 O1 . . . . 179.5(3) ?
C4 S1 C1 C2 . . . . -1.2(3) ?
O1 C1 C2 C3 . . . . 179.4(3) ?
S1 C1 C2 C3 . . . . 0.1(4) ?
O1 C1 C2 C5 . . . . 0.5(5) ?
S1 C1 C2 C5 . . . . -178.8(3) ?
C1 C2 C3 O2 . . . . -178.6(3) ?
C5 C2 C3 O2 . . . . 0.3(5) ?
C1 C2 C3 C4 . . . . 1.4(4) ?
C5 C2 C3 C4 . . . . -179.8(3) ?
O2 C3 C4 S1 . . . . 177.8(3) ?
C2 C3 C4 S1 . . . . -2.1(4) ?
C1 S1 C4 C3 . . . . 1.7(2) ?

_cod_database_fobs_code 2243459
