#------------------------------------------------------------------------------
#$Date: 2022-08-24 12:28:11 +0300 (Wed, 24 Aug 2022) $
#$Revision: 277384 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105700.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_8105700
loop_
_publ_author_name
'Wen, Ya-Xin'
'Guo, Ya-Fei'
'Dong, Le'
'Ma, Jun-Ying'
'Fan, Bing-You'
_publ_section_title
;
 Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one,
 C15H14O2S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              373
_journal_page_last               375
_journal_paper_doi               10.1515/ncrs-2022-0064
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C15 H14 O2 S'
_chemical_formula_sum            'C15 H14 O2 S'
_chemical_formula_weight         258.32
_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
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 96.125(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5881(11)
_cell_length_b                   7.3129(9)
_cell_length_c                   13.3284(11)
_cell_measurement_reflns_used    2301
_cell_measurement_temperature    288
_cell_measurement_theta_max      26.9080
_cell_measurement_theta_min      4.1120
_cell_volume                     1316.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      288
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -41.00  -4.00   1.00   10.00    --  -13.64 128.00 135.00   37
  2  ω    -13.00  21.00   1.00   10.00    --  -13.64 -99.00-120.00   34
  3  ω     -7.00  22.00   1.00   10.00    --  -13.64 -99.00  60.00   29
  4  ω    -44.00  68.00   1.00   10.00    --   15.05   0.00  60.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0087824000
_diffrn_orient_matrix_UB_12      -0.0933165000
_diffrn_orient_matrix_UB_13      -0.0124823000
_diffrn_orient_matrix_UB_21      0.0516661000
_diffrn_orient_matrix_UB_22      -0.0166028000
_diffrn_orient_matrix_UB_23      0.0055508000
_diffrn_orient_matrix_UB_31      -0.0018740000
_diffrn_orient_matrix_UB_32      -0.0205692000
_diffrn_orient_matrix_UB_33      0.0518179000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5547
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_min         3.450
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0570
_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)+(0.0501P)²+0.4696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2014
_reflns_number_total             2725
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0064_suppl.cif
_cod_data_source_block           2
_cod_database_code               8105700
_chemical_oxdiff_formula         C1H1O1N1
_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.
;
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.042
_oxdiff_exptl_absorpt_empirical_full_min 0.394
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_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 0.14502(5) 0.74734(11) 0.61439(5) 0.0502(2) Uani 1 1 d . . . . .
O1 O 0.12386(15) 0.2882(3) 0.45978(18) 0.0690(6) Uani 1 1 d . . . . .
H1 H 0.102(3) 0.400(8) 0.376(4) 0.17(2) Uiso 1 1 d . . . . .
O2 O 0.07901(15) 0.5401(4) 0.34290(13) 0.0642(6) Uani 1 1 d . . . . .
C1 C 0.33959(17) 0.7432(4) 0.56455(16) 0.0389(6) Uani 1 1 d . . . . .
H1A H 0.3176 0.6754 0.5075 0.047 Uiso 1 1 calc R U . . .
C2 C 0.27362(17) 0.7959(4) 0.62994(16) 0.0389(6) Uani 1 1 d . . . . .
C3 C 0.30661(18) 0.8987(4) 0.71634(16) 0.0448(7) Uani 1 1 d . . . . .
H3 H 0.2616 0.9345 0.7605 0.054 Uiso 1 1 calc R U . . .
C4 C 0.40301(19) 0.9461(4) 0.73587(17) 0.0474(7) Uani 1 1 d . . . . .
H4 H 0.4232 1.0146 0.7931 0.057 Uiso 1 1 calc R U . . .
C5 C 0.57510(19) 0.9388(4) 0.6891(2) 0.0548(8) Uani 1 1 d . . . . .
H5 H 0.5976 1.0050 0.7466 0.066 Uiso 1 1 calc R U . . .
C6 C 0.6399(2) 0.8874(5) 0.6241(2) 0.0631(9) Uani 1 1 d . . . . .
H6 H 0.7065 0.9176 0.6376 0.076 Uiso 1 1 calc R U . . .
C7 C 0.6073(2) 0.7887(5) 0.5366(2) 0.0622(9) Uani 1 1 d . . . . .
H7 H 0.6524 0.7553 0.4920 0.075 Uiso 1 1 calc R U . . .
C8 C 0.51042(19) 0.7414(4) 0.51634(19) 0.0491(7) Uani 1 1 d . . . . .
H8 H 0.4897 0.6760 0.4581 0.059 Uiso 1 1 calc R U . . .
C9 C 0.44101(17) 0.7910(4) 0.58321(16) 0.0387(6) Uani 1 1 d . . . . .
C10 C 0.47349(17) 0.8931(4) 0.67077(16) 0.0410(6) Uani 1 1 d . . . . .
C11 C 0.12970(16) 0.5916(4) 0.51345(17) 0.0415(6) Uani 1 1 d . . . . .
C12 C 0.14117(17) 0.4027(5) 0.5316(2) 0.0524(7) Uani 1 1 d . . . . .
C13 C 0.1742(2) 0.3276(6) 0.6336(3) 0.0793(10) Uani 1 1 d . . . . .
H13A H 0.1764 0.1965 0.6302 0.119 Uiso 1 1 calc R U . . .
H13B H 0.1284 0.3640 0.6800 0.119 Uiso 1 1 calc R U . . .
H13C H 0.2389 0.3738 0.6562 0.119 Uiso 1 1 calc R U . . .
C14 C 0.09843(17) 0.6553(4) 0.41561(18) 0.0478(7) Uani 1 1 d . . . . .
C15 C 0.0846(2) 0.8509(5) 0.3894(2) 0.0712(9) Uani 1 1 d . . . . .
H15A H 0.0690 0.8630 0.3178 0.107 Uiso 1 1 calc R U . . .
H15B H 0.1444 0.9166 0.4104 0.107 Uiso 1 1 calc R U . . .
H15C H 0.0314 0.8998 0.4231 0.107 Uiso 1 1 calc R U . . .
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
C11 S1 C2 104.71(11) . .
C12 O1 H1 103(2) . .
C14 O2 H1 106(2) . .
C2 C1 H1A 119.7 . .
C2 C1 C9 120.6(2) . .
C9 C1 H1A 119.7 . .
C1 C2 S1 124.93(18) . .
C1 C2 C3 119.8(2) . .
C3 C2 S1 115.23(18) . .
C2 C3 H3 119.6 . .
C4 C3 C2 120.7(2) . .
C4 C3 H3 119.6 . .
C3 C4 H4 119.4 . .
C3 C4 C10 121.2(2) . .
C10 C4 H4 119.4 . .
C6 C5 H5 119.6 . .
C6 C5 C10 120.9(3) . .
C10 C5 H5 119.6 . .
C5 C6 H6 119.8 . .
C5 C6 C7 120.4(3) . .
C7 C6 H6 119.8 . .
C6 C7 H7 119.7 . .
C8 C7 C6 120.6(3) . .
C8 C7 H7 119.7 . .
C7 C8 H8 119.8 . .
C7 C8 C9 120.5(3) . .
C9 C8 H8 119.8 . .
C8 C9 C1 121.9(2) . .
C8 C9 C10 119.0(2) . .
C10 C9 C1 119.1(2) . .
C4 C10 C5 122.8(2) . .
C4 C10 C9 118.6(2) . .
C9 C10 C5 118.6(2) . .
C12 C11 S1 120.1(2) . .
C14 C11 S1 119.6(2) . .
C14 C11 C12 120.0(2) . .
O1 C12 C11 120.5(3) . .
O1 C12 C13 117.2(3) . .
C11 C12 C13 122.3(3) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O2 C14 C11 119.8(3) . .
O2 C14 C15 116.3(3) . .
C11 C14 C15 123.8(3) . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.773(2) .
S1 C11 1.758(3) .
O1 H1 1.40(5) .
O1 C12 1.274(3) .
O2 H1 1.14(6) .
O2 C14 1.290(3) .
C1 H1A 0.9300 .
C1 C2 1.371(3) .
C1 C9 1.418(3) .
C2 C3 1.408(3) .
C3 H3 0.9300 .
C3 C4 1.353(3) .
C4 H4 0.9300 .
C4 C10 1.413(3) .
C5 H5 0.9300 .
C5 C6 1.352(4) .
C5 C10 1.416(3) .
C6 H6 0.9300 .
C6 C7 1.403(4) .
C7 H7 0.9300 .
C7 C8 1.361(4) .
C8 H8 0.9300 .
C8 C9 1.412(4) .
C9 C10 1.416(3) .
C11 C12 1.409(4) .
C11 C14 1.407(3) .
C12 C13 1.490(4) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C15 1.479(4) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
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
S1 C2 C3 C4 -179.3(2) . . . .
S1 C11 C12 O1 175.39(18) . . . .
S1 C11 C12 C13 -5.0(3) . . . .
S1 C11 C14 O2 -174.14(18) . . . .
S1 C11 C14 C15 5.1(3) . . . .
C1 C2 C3 C4 -0.1(4) . . . .
C1 C9 C10 C4 -0.9(4) . . . .
C1 C9 C10 C5 179.5(2) . . . .
C2 S1 C11 C12 87.2(2) . . . .
C2 S1 C11 C14 -97.72(19) . . . .
C2 C1 C9 C8 -178.9(2) . . . .
C2 C1 C9 C10 0.4(4) . . . .
C2 C3 C4 C10 -0.4(4) . . . .
C3 C4 C10 C5 -179.5(3) . . . .
C3 C4 C10 C9 0.9(4) . . . .
C5 C6 C7 C8 -0.8(5) . . . .
C6 C5 C10 C4 -179.1(3) . . . .
C6 C5 C10 C9 0.5(4) . . . .
C6 C7 C8 C9 0.0(5) . . . .
C7 C8 C9 C1 -179.7(3) . . . .
C7 C8 C9 C10 1.0(4) . . . .
C8 C9 C10 C4 178.4(2) . . . .
C8 C9 C10 C5 -1.2(4) . . . .
C9 C1 C2 S1 179.19(19) . . . .
C9 C1 C2 C3 0.1(4) . . . .
C10 C5 C6 C7 0.5(5) . . . .
C11 S1 C2 C1 9.5(3) . . . .
C11 S1 C2 C3 -171.4(2) . . . .
C12 C11 C14 O2 0.9(3) . . . .
C12 C11 C14 C15 -179.9(2) . . . .
C14 C11 C12 O1 0.3(4) . . . .
C14 C11 C12 C13 179.9(2) . . . .
