The crystal structure of 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol, C27H32O3S
Liu, Zhang-Qin; Tang, Min; Zhang, Liang-Dong; You, Peng-Sheng; Liu, Sheng-Shu; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 703–705; doi:10.1515/ncrs-2019-0059

data_8105826
_publ_section_title
;
 The crystal structure of
 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol, C27H32O3S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              703
_journal_page_last               705
_journal_paper_doi               10.1515/ncrs-2019-0059
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C27 H32 O3 S'
_chemical_formula_sum            'C27 H32 O3 S'
_chemical_formula_weight         436.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                73.6710(16)
_cell_angle_beta                 70.1267(17)
_cell_angle_gamma                70.7828(15)
_cell_formula_units_Z            4
_cell_length_a                   12.2441(2)
_cell_length_b                   14.9350(2)
_cell_length_c                   15.2081(3)
_cell_measurement_reflns_used    24773
_cell_measurement_temperature    297.1(2)
_cell_measurement_theta_max      72.9830
_cell_measurement_theta_min      4.0190
_cell_volume                     2424.41(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)[1]'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)[1]'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)[1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)[2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[2]'
_computing_structure_refinement  'XL (Sheldrick, 2008)[3]'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      297.1
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -91.00  -3.00   1.00    1.00    --  -37.03 126.00-180.00   88
  2  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00   0.00   95
  3  \w   -106.00  32.00   1.00    1.00    --  -37.03   0.00 150.00  138
  4  \w    -30.00  54.00   1.00    1.00    --   37.03 -57.00 -60.00   84
  5  \w     24.00  91.00   1.00    1.00    --   37.03-126.00  90.00   67
  6  \w    -30.00  54.00   1.00    1.00    --   37.03 -57.00  90.00   84
  7  \w     18.00 106.00   1.00    1.00    --   37.03  38.00 -90.00   88
  8  \w      1.00  76.00   1.00    1.00    --   37.03 -99.00  90.00   75
  9  \w     18.00 106.00   1.00    1.00    --   37.03  38.00-150.00   88
 10  \w     24.00  91.00   1.00    1.00    --   37.03-126.00 -60.00   67
 11  \w     24.00  91.00   1.00    1.00    --   37.03-126.00  30.00   67
 12  \w     24.00  91.00   1.00    1.00    --   37.03-126.00 150.00   67
 13  \w     18.00 106.00   1.00    1.00    --   37.03  38.00 120.00   88
 14  \w    -32.00  56.00   1.00    1.00    --   37.03 -38.00 150.00   88
 15  \w      1.00  76.00   1.00    1.00    --   37.03 -99.00-120.00   75
 16  \w     41.00 132.00   1.00    3.47    --  110.47 -30.00 -60.00   91
 17  \w     42.00 128.00   1.00    3.47    --  110.47 -45.00-180.00   86
 18  \w     41.00 109.00   1.00    3.47    --  110.47 -95.00   0.00   68
 19  \w     44.00 129.00   1.00    3.47    --  110.47 -61.00 -30.00   85
 20  \w     44.00 129.00   1.00    3.47    --  110.47 -61.00-120.00   85
 21  \w     41.00 116.00   1.00    3.47    --  110.47-112.00  90.00   75
 22  \w     42.00 128.00   1.00    3.47    --  110.47 -45.00  30.00   86
 23  \w     40.00 149.00   1.00    3.47    --  110.47 -15.00  90.00  109
 24  \w     41.00 109.00   1.00    3.47    --  110.47 -95.00 -90.00   68
 25  \w     41.00 116.00   1.00    3.47    --  110.47-112.00-120.00   75
 26  \w     93.00 178.00   1.00    3.47    --  110.47  45.00 -30.00   85
 27  \w     44.00 129.00   1.00    3.47    --  110.47 -61.00 120.00   85
 28  \w     41.00 116.00   1.00    3.47    --  110.47-112.00 150.00   75
 29  \w     41.00 178.00   1.00    3.47    --  110.47   0.00 120.00  137
 30  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00-180.00   95
 31  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00  60.00   95
 32  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00  90.00   95
 33  \w   -107.00  -8.00   1.00    1.00    --  -37.03 -19.00-120.00   99
 34  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00 120.00   95
 35  \w   -104.00 -20.00   1.00    1.00    --  -37.03 -57.00  30.00   84
 36  \w     10.00 105.00   1.00    1.00    --   37.03  77.00 -30.00   95
 37  \w     20.00 104.00   1.00    1.00    --   37.03  57.00 120.00   84
 38  \w    -30.00  54.00   1.00    1.00    --   37.03 -57.00 -90.00   84
 39  \w     20.00 104.00   1.00    1.00    --   37.03  57.00-120.00   84
 40  \w     10.00 105.00   1.00    1.00    --   37.03  77.00-150.00   95
 41  \w     10.00 105.00   1.00    1.00    --   37.03  77.00 -60.00   95
 42  \w     18.00 106.00   1.00    1.00    --   37.03  38.00 -30.00   88
 43  \w     89.00 178.00   1.00    3.47    --  110.47  30.00-180.00   89
 44  \w     72.00 178.00   1.00    3.47    --  110.47  15.00 -90.00  106
 45  \w     89.00 178.00   1.00    3.47    --  110.47  30.00-150.00   89
 46  \w     89.00 178.00   1.00    3.47    --  110.47  30.00  90.00   89
 47  \w     89.00 178.00   1.00    3.47    --  110.47  30.00  30.00   89
 48  \w     93.00 178.00   1.00    3.47    --  110.47  45.00 120.00   85
 49  \w     89.00 178.00   1.00    3.47    --  110.47  30.00 -60.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            42113
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.974
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
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    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     573
_refine_ls_number_reflns         8633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0718P)^2^+0.3782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1319
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7324
_reflns_number_total             8633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0059_suppl.cif
_cod_data_source_block           t
_cod_database_code               8105826
_shelx_estimated_absorpt_t_max   0.700
_shelx_estimated_absorpt_t_min   0.645
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H6A of O6
 At 1.5 times of:
  All C(H,H,H) groups, H3 of O3
2.a Ternary CH refined with riding coordinates:
 C7(H7), C34(H34)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
  C13(H13), C15(H15), C19(H19), C29(H29), C30(H30), C31(H31), C32(H32),
 C33(H33), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C46(H46)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C48(H48A,H48B,H48C), C49(H49A,
 H49B,H49C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C),
 C54(H54A,H54B,H54C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6A)
;
_shelx_res_checksum              77402
_shelx_hkl_checksum              68505
_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
;