Crystal structure of (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
Dong, Le; Guo, Ya-Fei; Ma, Jun-Ying; Wang, Jun-Ling; Feng, Shu-Xiao; Huo, Hui-Kang; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 37–39; doi:10.1515/ncrs-2021-0365

data_8104955
_publ_section_title
;
 Crystal structure of
 (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              37
_journal_page_last               39
_journal_paper_doi               10.1515/ncrs-2021-0365
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C15 H20 O2 S'
_chemical_formula_sum            'C15 H20 O2 S'
_chemical_formula_weight         264.37
_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                 104.375(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8520(8)
_cell_length_b                   10.5864(8)
_cell_length_c                   11.2202(7)
_cell_measurement_reflns_used    4504
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.7640
_cell_measurement_theta_min      4.1480
_cell_volume                     1478.79(18)
_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 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -20.00  15.00   1.00    4.12    --  -13.80 -99.00 -90.00   35
  2  \w    -17.00  16.00   1.00    4.12    --  -13.80 -99.00  90.00   33
  3  \w    -36.00   5.00   1.00    4.12    --   15.21 -57.00 -90.00   41
  4  \w     42.00  88.00   1.00    4.12    --   15.21-178.00  60.00   46
  5  \w     -2.00  48.00   1.00    4.12    --   15.21  57.00 -90.00   50
  6  \w    -48.00  34.00   1.00    4.12    --   15.21 -77.00  60.00   82
  7  \w    -49.00  34.00   1.00    4.12    --   15.21 -38.00 120.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0465386000
_diffrn_orient_matrix_UB_12      0.0360674000
_diffrn_orient_matrix_UB_13      -0.0000951000
_diffrn_orient_matrix_UB_21      0.0259126000
_diffrn_orient_matrix_UB_22      0.0551577000
_diffrn_orient_matrix_UB_23      -0.0141459000
_diffrn_orient_matrix_UB_31      -0.0202266000
_diffrn_orient_matrix_UB_32      -0.0123358000
_diffrn_orient_matrix_UB_33      -0.0636717000
_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  0.0333
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11385
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.438
_diffrn_reflns_theta_min         3.379
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70055
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0655
_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/[\s^2^(Fo^2^)+(0.0948P)^2^+0.5133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1781
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2549
_reflns_number_total             3265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0365_suppl.cif
_cod_data_source_block           benliufen
_cod_original_cell_volume        1478.78(18)
_cod_database_code               8104955
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.945
_reflns_odcompleteness_completeness 99.65
_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, All O(H) groups
2. Restrained distances
 C13-C12 \\sim C14-C12 \\sim C15-C12
 with sigma of 0.02
 C14-C13 \\sim C15-C13 \\sim C15-C14
 with sigma of 0.02
 C13A-C12 \\sim C14A-C12 \\sim C15A-C12
 with sigma of 0.02
 C14A-C13A \\sim C15A-C13A \\sim C15A-C14A
 with sigma of 0.02
3. Rigid bond restraints
 C13, C14, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C13) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C13) = Uanis(C13A)
Uanis(C15) = Uanis(C15A)
Uanis(C14) = Uanis(C14A)
5. Others
 Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C13A)=Sof(H13D)=Sof(H13E)=
 Sof(H13F)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
6.a Riding coordinates:
 O1(H1)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F), C13A(H13D,H13E,H13F), C14A(H14D,
 H14E,H14F)
;