#------------------------------------------------------------------------------
#$Date: 2022-11-16 11:41:01 +0200 (Wed, 16 Nov 2022) $
#$Revision: 279321 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106117.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_8106117
loop_
_publ_author_name
'Guan, Xiao-Yu'
'Liu, Sheng-Shu'
'Zhang, Liang-Dong'
'Guo, Xin'
'Ma, Xuebing'
'Liu, Zhang-Qin'
_publ_section_title
;
 The crystal structure of
 N-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)-4-methylbenzenesulfonamide,
 C28H35N3S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              259
_journal_page_last               261
_journal_paper_doi               10.1515/ncrs-2017-0257
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C28 H35 N O3 S'
_chemical_formula_sum            'C28 H35 N O3 S'
_chemical_formula_weight         465.63
_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   mixed
_atom_sites_solution_primary     iterative
_cell_angle_alpha                86.651(4)
_cell_angle_beta                 86.653(4)
_cell_angle_gamma                75.323(4)
_cell_formula_units_Z            2
_cell_length_a                   10.3965(4)
_cell_length_b                   10.7525(5)
_cell_length_c                   12.2772(6)
_cell_measurement_reflns_used    5442
_cell_measurement_temperature    290.55(10)
_cell_measurement_theta_max      72.9440
_cell_measurement_theta_min      4.3960
_cell_volume                     1324.05(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.55(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     34.00 106.00   1.00    1.00    --   37.03  38.00 120.00   72
  2  ω    101.00 166.00   1.00    1.59    --  110.47 112.00  30.00   65
  3  ω    121.00 177.00   1.00    1.59    --  110.47  61.00 -90.00   56
  4  ω    146.00 177.00   1.00    1.59    --  110.47  45.00-120.00   31
  5  ω     92.00 174.00   1.00    1.59    --  110.47  30.00-180.00   82
  6  ω     95.00 123.00   1.00    1.59    --  110.47  45.00-120.00   28
  7  ω     85.00 132.00   1.00    1.59    --  110.47 -30.00 -60.00   47
  8  ω     83.00 109.00   1.00    1.59    --  110.47 -95.00-120.00   26
  9  ω     59.00 101.00   1.00    1.59    --  110.47 -95.00-150.00   42
 10  ω     48.00 103.00   1.00    1.59    --  110.47 -61.00 -90.00   55
 11  ω     44.00 131.00   1.00    1.59    --  110.47 -30.00-150.00   87
 12  ω     45.00 129.00   1.00    1.59    --  110.47 -61.00   0.00   84
 13  ω     73.00 109.00   1.00    1.59    --  110.47 -95.00  90.00   36
 14  ω     75.00 125.00   1.00    1.59    --  110.47 -77.00  90.00   50
 15  ω     63.00 116.00   1.00    1.59    --  110.47-112.00  30.00   53
 16  ω     52.00  77.00   1.00    1.59    --  110.47 -95.00 150.00   25
 17  ω     47.00 115.00   1.00    1.59    --  110.47 -45.00 120.00   68
 18  ω     65.00  90.00   1.00    1.00    --   37.03-126.00 150.00   25
 19  ω     25.00  61.00   1.00    1.00    --   37.03-126.00  90.00   36
 20  ω     21.00  75.00   1.00    1.00    --   37.03 -99.00 120.00   54
 21  ω     39.00  87.00   1.00    1.00    --   37.03-126.00   0.00   48
 22  ω     27.00  52.00   1.00    1.00    --   37.03-126.00 -60.00   25
 23  ω     30.00  67.00   1.00    1.00    --   37.03-126.00 -90.00   37
 24  ω     43.00  77.00   1.00    1.59    --  110.47 -30.00 -60.00   34
 25  ω    -50.00 -21.00   1.00    1.00    --  -37.03 -38.00-180.00   29
 26  ω   -100.00 -31.00   1.00    1.00    --  -37.03 -38.00 -60.00   69
 27  ω   -103.00 -76.00   1.00    1.00    --  -37.03 -38.00-180.00   27
 28  ω    -45.00  -4.00   1.00    1.00    --  -37.03 126.00 120.00   41
 29  ω    -87.00 -62.00   1.00    1.00    --  -37.03 126.00 120.00   25
 30  ω   -106.00  23.00   1.00    1.00    --  -37.03   0.00 -30.00  129
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0258674000
_diffrn_orient_matrix_UB_12      -0.0111828000
_diffrn_orient_matrix_UB_13      -0.1243152000
_diffrn_orient_matrix_UB_21      -0.0029146000
_diffrn_orient_matrix_UB_22      0.1440980000
_diffrn_orient_matrix_UB_23      -0.0119908000
_diffrn_orient_matrix_UB_31      0.1511092000
_diffrn_orient_matrix_UB_32      -0.0330404000
_diffrn_orient_matrix_UB_33      0.0152866000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9236
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.022
_diffrn_reflns_theta_min         3.610
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0728P)²+0.1893P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4575
_reflns_number_total             5153
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0257_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106117
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C20(H20)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_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 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.620
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.37458(4) 0.61008(3) 0.13843(3) 0.04190(13) Uani 1 1 d . . . . .
O1 O 0.34559(13) 0.70809(10) 0.21666(11) 0.0539(3) Uani 1 1 d . . . . .
O2 O 0.40686(13) 0.64402(11) 0.02712(10) 0.0557(3) Uani 1 1 d . . . . .
O3 O 0.49517(15) -0.09069(12) 0.23403(15) 0.0724(5) Uani 1 1 d . . . . .
N1 N 0.49929(13) 0.49700(12) 0.17790(11) 0.0414(3) Uani 1 1 d . . . . .
H1 H 0.5344(19) 0.4554(19) 0.1250(16) 0.050 Uiso 1 1 d R . . . .
C1 C -0.0960(3) 0.3738(3) 0.1552(3) 0.0921(8) Uani 1 1 d . . . . .
H1A H -0.0951 0.3224 0.2219 0.138 Uiso 1 1 calc GR . . . .
H1B H -0.0893 0.3203 0.0942 0.138 Uiso 1 1 calc GR . . . .
H1C H -0.1776 0.4400 0.1532 0.138 Uiso 1 1 calc GR . . . .
C2 C 0.0201(2) 0.4345(2) 0.14956(18) 0.0630(5) Uani 1 1 d . . . . .
C3 C 0.0166(2) 0.5406(2) 0.2089(2) 0.0705(6) Uani 1 1 d . . . . .
C4 C 0.12393(18) 0.59517(18) 0.20531(17) 0.0587(4) Uani 1 1 d . . . . .
H4 H 0.1204 0.6665 0.2458 0.070 Uiso 1 1 calc R . . . .
C5 C 0.23583(16) 0.54356(14) 0.14166(13) 0.0433(3) Uani 1 1 d . . . . .
C6 C 0.2421(2) 0.43656(18) 0.08179(17) 0.0589(4) Uani 1 1 d . . . . .
H6 H 0.3182 0.4006 0.0396 0.071 Uiso 1 1 calc R . . . .
C7 C 0.1335(2) 0.38426(19) 0.08593(19) 0.0675(5) Uani 1 1 d . . . . .
H7 H 0.1367 0.3134 0.0449 0.081 Uiso 1 1 calc R . . . .
C8 C 0.49081(15) 0.43003(13) 0.28671(12) 0.0394(3) Uani 1 1 d . . . . .
H8 H 0.4056 0.4726 0.3225 0.047 Uiso 1 1 calc R . . . .
C9 C 0.60069(16) 0.44794(14) 0.35687(12) 0.0426(3) Uani 1 1 d . . . . .
C10 C 0.6348(2) 0.56477(18) 0.35266(17) 0.0622(5) Uani 1 1 d . . . . .
H10 H 0.5924 0.6312 0.3053 0.075 Uiso 1 1 calc R . . . .
C11 C 0.7311(3) 0.5832(2) 0.41812(18) 0.0736(6) Uani 1 1 d . . . . .
H11 H 0.7529 0.6621 0.4144 0.088 Uiso 1 1 calc R . . . .
C12 C 0.7950(2) 0.4870(2) 0.48847(17) 0.0670(5) Uani 1 1 d . . . . .
H12 H 0.8612 0.4995 0.5313 0.080 Uiso 1 1 calc R . . . .
C13 C 0.7603(2) 0.3719(2) 0.49488(18) 0.0715(6) Uani 1 1 d . . . . .
H13 H 0.8024 0.3062 0.5430 0.086 Uiso 1 1 calc R . . . .
C14 C 0.6626(2) 0.35281(18) 0.42984(16) 0.0596(5) Uani 1 1 d . . . . .
H14 H 0.6388 0.2749 0.4358 0.072 Uiso 1 1 calc R . . . .
C15 C 0.48921(15) 0.29087(13) 0.27380(12) 0.0391(3) Uani 1 1 d . . . . .
C16 C 0.59633(15) 0.20696(14) 0.22223(13) 0.0416(3) Uani 1 1 d . . . . .
H16 H 0.6691 0.2373 0.1962 0.050 Uiso 1 1 calc R . . . .
C17 C 0.59836(15) 0.07907(14) 0.20823(14) 0.0436(3) Uani 1 1 d . . . . .
C18 C 0.48673(16) 0.03679(14) 0.24856(14) 0.0461(4) Uani 1 1 d . . . . .
C19 C 0.37650(16) 0.11821(14) 0.30173(13) 0.0433(3) Uani 1 1 d . . . . .
C20 C 0.38113(15) 0.24569(14) 0.31201(12) 0.0412(3) Uani 1 1 d . . . . .
H20 H 0.3089 0.3021 0.3457 0.049 Uiso 1 1 calc R . . . .
C21 C 0.25509(18) 0.07070(16) 0.34815(16) 0.0538(4) Uani 1 1 d . . . . .
C22 C 0.1497(2) 0.1785(2) 0.4031(2) 0.0698(6) Uani 1 1 d . . . . .
H22A H 0.1869 0.2067 0.4640 0.105 Uiso 1 1 calc GR . . . .
H22B H 0.0743 0.1467 0.4282 0.105 Uiso 1 1 calc GR . . . .
H22C H 0.1220 0.2495 0.3514 0.105 Uiso 1 1 calc GR . . . .
C23 C 0.1845(2) 0.0261(2) 0.2563(2) 0.0711(6) Uani 1 1 d . . . . .
H23A H 0.143(3) 0.101(3) 0.198(2) 0.107 Uiso 1 1 d R . . . .
H23B H 0.107(3) -0.002(3) 0.286(2) 0.107 Uiso 1 1 d R . . . .
C24 C 0.2996(3) -0.0381(2) 0.4352(2) 0.0855(7) Uani 1 1 d . . . . .
H24A H 0.3624 -0.1090 0.4025 0.128 Uiso 1 1 calc GR . . . .
H24B H 0.2236 -0.0660 0.4649 0.128 Uiso 1 1 calc GR . . . .
H24C H 0.3406 -0.0072 0.4925 0.128 Uiso 1 1 calc GR . . . .
C25 C 0.71867(19) -0.01083(17) 0.14991(19) 0.0604(5) Uani 1 1 d . . . . .
C26 C 0.6749(3) -0.0591(3) 0.0464(3) 0.1101(11) Uani 1 1 d . . . . .
H26A H 0.6163 -0.1136 0.0664 0.165 Uiso 1 1 calc GR . . . .
H26B H 0.7517 -0.1069 0.0062 0.165 Uiso 1 1 calc GR . . . .
H26C H 0.6291 0.0131 0.0018 0.165 Uiso 1 1 calc GR . . . .
C27 C 0.7828(2) -0.1228(2) 0.2279(3) 0.1060(11) Uani 1 1 d . . . . .
H27A H 0.8083 -0.0896 0.2920 0.159 Uiso 1 1 calc GR . . . .
H27B H 0.8602 -0.1760 0.1922 0.159 Uiso 1 1 calc GR . . . .
H27C H 0.7202 -0.1730 0.2484 0.159 Uiso 1 1 calc GR . . . .
C28 C 0.8260(2) 0.0586(2) 0.1138(3) 0.0876(8) Uani 1 1 d . . . . .
H28A H 0.7909 0.1273 0.0618 0.131 Uiso 1 1 calc GR . . . .
H28B H 0.9008 -0.0010 0.0806 0.131 Uiso 1 1 calc GR . . . .
H28C H 0.8539 0.0932 0.1761 0.131 Uiso 1 1 calc GR . . . .
H23C H 0.239(3) -0.046(3) 0.215(2) 0.090(8) Uiso 1 1 d . . . . .
H3A H -0.064(3) 0.579(3) 0.256(2) 0.089(8) Uiso 1 1 d . . . . .
H3 H 0.425(3) -0.103(3) 0.244(2) 0.081(8) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 '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
O1 S1 O2 118.74(7) . .
O1 S1 N1 108.75(7) . .
O1 S1 C5 106.84(8) . .
O2 S1 N1 106.06(7) . .
O2 S1 C5 108.89(8) . .
N1 S1 C5 107.04(7) . .
C8 N1 S1 119.51(10) . .
C3 C2 C1 120.9(2) . .
C3 C2 C7 118.33(18) . .
C7 C2 C1 120.8(2) . .
C2 C3 C4 121.0(2) . .
C5 C4 C3 119.76(18) . .
C4 C5 S1 120.25(13) . .
C4 C5 C6 120.38(17) . .
C6 C5 S1 119.35(13) . .
C7 C6 C5 118.89(18) . .
C6 C7 C2 121.65(19) . .
N1 C8 C9 109.59(12) . .
N1 C8 C15 110.54(12) . .
C15 C8 C9 114.64(12) . .
C10 C9 C8 120.08(15) . .
C14 C9 C8 121.48(14) . .
C14 C9 C10 118.33(16) . .
C11 C10 C9 120.55(19) . .
C12 C11 C10 120.87(19) . .
C11 C12 C13 119.09(18) . .
C12 C13 C14 120.40(19) . .
C9 C14 C13 120.71(17) . .
C16 C15 C8 120.40(13) . .
C20 C15 C8 120.77(13) . .
C20 C15 C16 118.82(13) . .
C15 C16 C17 122.15(14) . .
C16 C17 C18 117.26(14) . .
C16 C17 C25 120.62(15) . .
C18 C17 C25 122.12(14) . .
O3 C18 C17 114.70(15) . .
O3 C18 C19 122.80(15) . .
C17 C18 C19 122.48(14) . .
C18 C19 C21 122.37(14) . .
C20 C19 C18 117.01(14) . .
C20 C19 C21 120.62(15) . .
C15 C20 C19 122.27(14) . .
C22 C21 C19 111.71(14) . .
C22 C21 C23 105.84(17) . .
C23 C21 C19 110.98(17) . .
C24 C21 C19 109.75(16) . .
C24 C21 C22 107.38(18) . .
C24 C21 C23 111.07(18) . .
C26 C25 C17 109.99(18) . .
C27 C25 C17 109.98(19) . .
C27 C25 C26 111.5(2) . .
C28 C25 C17 111.72(15) . .
C28 C25 C26 106.8(2) . .
C28 C25 C27 106.82(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4309(12) .
S1 O2 1.4365(12) .
S1 N1 1.6125(13) .
S1 C5 1.7626(16) .
O3 C18 1.3727(18) .
N1 C8 1.4889(19) .
C1 C2 1.508(3) .
C2 C3 1.381(3) .
C2 C7 1.382(3) .
C3 C4 1.383(3) .
C4 C5 1.375(2) .
C5 C6 1.387(2) .
C6 C7 1.381(3) .
C8 C9 1.526(2) .
C8 C15 1.5183(19) .
C9 C10 1.387(2) .
C9 C14 1.375(2) .
C10 C11 1.379(3) .
C11 C12 1.368(3) .
C12 C13 1.372(3) .
C13 C14 1.390(3) .
C15 C16 1.389(2) .
C15 C20 1.381(2) .
C16 C17 1.391(2) .
C17 C18 1.405(2) .
C17 C25 1.541(2) .
C18 C19 1.406(2) .
C19 C20 1.397(2) .
C19 C21 1.545(2) .
C21 C22 1.537(3) .
C21 C23 1.542(3) .
C21 C24 1.537(3) .
C25 C26 1.535(4) .
C25 C27 1.531(3) .
C25 C28 1.525(3) .
