##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-[(3,5-Di-tert-butyl-4-hydroxybenzyl)sulfanyl]benzoic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H28 O3 S'
_chemical_formula_sum     'C22 H28 O3 S'
_chemical_formula_iupac     'C22 H28 O3 S'
_chemical_formula_weight     372.50
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     18.1496(4)
_cell_length_b     5.68630(10)
_cell_length_c     20.2159(4)
_cell_angle_alpha     90.00
_cell_angle_beta     101.1720(10)
_cell_angle_gamma     90.00
_cell_volume     2046.83(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2170
_cell_measurement_theta_min     2.15
_cell_measurement_theta_max     21.42
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.209
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     800
_exptl_absorpt_coefficient_mu     0.176
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.941
_exptl_absorpt_correction_T_max     0.969
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15313
_diffrn_reflns_av_R_equivalents     0.0406
_diffrn_reflns_av_sigmaI/netI     0.0360
_diffrn_reflns_theta_min     2.05
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3610
_reflns_number_gt     2477
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0724
_refine_ls_R_factor_gt     0.0447
_refine_ls_wR_factor_gt     0.1079
_refine_ls_wR_factor_ref     0.1233
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_restrained_S_all     1.015
_refine_ls_number_reflns     3610
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0518P)²+0.6688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.316
_refine_diff_density_min     -0.166
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.08318(3) 0.07380(12) 0.38838(3) 0.0556(2) Uani d . 1 . .
    O O1 -0.08616(10) -0.4044(4) 0.44667(10) 0.0713(6) Uani d D 1 . .
    H H1 -0.0691(18) -0.500(5) 0.4773(14) 0.107 Uiso d D 1 . .
    O O2 0.03143(10) -0.2849(3) 0.45796(9) 0.0722(6) Uani d . 1 . .
    H H3 0.437(2) 0.532(6) 0.4727(18) 0.108 Uiso d . 1 . .
    O O3 0.42604(9) 0.4524(3) 0.44311(8) 0.0570(5) Uani d . 1 . .
    C C1 -0.03435(13) -0.2647(5) 0.43156(12) 0.0511(6) Uani d . 1 . .
    C C2 -0.06278(12) -0.0867(4) 0.37992(11) 0.0455(5) Uani d . 1 . .
    C C3 -0.13987(13) -0.0776(5) 0.35422(12) 0.0560(6) Uani d . 1 . .
    H H3A -0.1715 -0.1827 0.3704 0.067 Uiso calc R 1 . .
    C C4 -0.17013(14) 0.0820(5) 0.30591(13) 0.0602(7) Uani d . 1 . .
    H H4 -0.2217 0.0869 0.2898 0.072 Uiso calc R 1 . .
    C C5 -0.12312(14) 0.2351(5) 0.28141(13) 0.0617(7) Uani d . 1 . .
    H H5 -0.1431 0.3419 0.2478 0.074 Uiso calc R 1 . .
    C C6 -0.04738(14) 0.2318(5) 0.30594(12) 0.0555(6) Uani d . 1 . .
    H H6 -0.0168 0.3374 0.2887 0.067 Uiso calc R 1 . .
    C C7 -0.01457(12) 0.0736(4) 0.35630(11) 0.0453(5) Uani d . 1 . .
    C C8 0.11580(13) 0.3226(4) 0.34536(13) 0.0551(6) Uani d . 1 . .
    H H8A 0.1071 0.2936 0.2972 0.066 Uiso calc R 1 . .
    H H8B 0.0887 0.4637 0.3532 0.066 Uiso calc R 1 . .
    C C9 0.19819(13) 0.3541(4) 0.37237(12) 0.0476(6) Uani d . 1 . .
    C C10 0.25124(13) 0.2638(4) 0.33862(11) 0.0482(6) Uani d . 1 . .
    H H10 0.2348 0.1782 0.2993 0.058 Uiso calc R 1 . .
    C C11 0.32779(12) 0.2952(4) 0.36066(11) 0.0438(5) Uani d . 1 . .
    C C12 0.34993(12) 0.4227(4) 0.42063(11) 0.0424(5) Uani d . 1 . .
    C C13 0.29827(13) 0.5169(4) 0.45709(11) 0.0448(5) Uani d . 1 . .
    C C14 0.22284(13) 0.4794(4) 0.43102(12) 0.0506(6) Uani d . 1 . .
    H H14 0.1874 0.5410 0.4539 0.061 Uiso calc R 1 . .
    C C15 0.32235(14) 0.6534(4) 0.52338(12) 0.0545(6) Uani d . 1 . .
    C C16 0.25557(18) 0.7412(8) 0.55221(18) 0.1132(14) Uani d . 1 . .
    H H16A 0.2253 0.8436 0.5202 0.170 Uiso calc R 1 . .
    H H16B 0.2735 0.8257 0.5933 0.170 Uiso calc R 1 . .
    H H16C 0.2259 0.6096 0.5613 0.170 Uiso calc R 1 . .
    C C17 0.3697(2) 0.4965(6) 0.57768(14) 0.0901(10) Uani d . 1 . .
    H H17A 0.3393 0.3695 0.5886 0.135 Uiso calc R 1 . .
    H H17B 0.3876 0.5883 0.6174 0.135 Uiso calc R 1 . .
    H H17C 0.4117 0.4342 0.5609 0.135 Uiso calc R 1 . .
    C C18 0.36869(19) 0.8726(5) 0.51428(16) 0.0828(9) Uani d . 1 . .
    H H18A 0.4140 0.8260 0.5000 0.124 Uiso calc R 1 . .
    H H18B 0.3812 0.9555 0.5563 0.124 Uiso calc R 1 . .
    H H18C 0.3399 0.9734 0.4808 0.124 Uiso calc R 1 . .
    C C19 0.38448(14) 0.1959(4) 0.31979(11) 0.0518(6) Uani d . 1 . .
    C C20 0.34466(17) 0.0547(6) 0.25871(14) 0.0856(10) Uani d . 1 . .
    H H20A 0.3111 0.1559 0.2290 0.128 Uiso calc R 1 . .
    H H20B 0.3166 -0.0712 0.2736 0.128 Uiso calc R 1 . .
    H H20C 0.3813 -0.0092 0.2352 0.128 Uiso calc R 1 . .
    C C21 0.42732(18) 0.3964(5) 0.29384(16) 0.0828(10) Uani d . 1 . .
    H H21A 0.4538 0.4857 0.3313 0.124 Uiso calc R 1 . .
    H H21B 0.3925 0.4970 0.2651 0.124 Uiso calc R 1 . .
    H H21C 0.4625 0.3326 0.2688 0.124 Uiso calc R 1 . .
    C C22 0.43946(16) 0.0255(5) 0.36205(14) 0.0700(8) Uani d . 1 . .
    H H22A 0.4747 -0.0302 0.3358 0.105 Uiso calc R 1 . .
    H H22B 0.4123 -0.1054 0.3754 0.105 Uiso calc R 1 . .
    H H22C 0.4660 0.1050 0.4015 0.105 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C7 . 1.767(2) ?
    S1 C8 . 1.819(2) ?
    O1 C1 . 1.311(3) ?
    O1 H1 . 0.837(18) ?
    O2 C1 . 1.215(3) ?
    O3 C12 . 1.378(3) ?
    O3 H3 . 0.75(3) ?
    C1 C2 . 1.474(3) ?
    C2 C3 . 1.396(3) ?
    C2 C7 . 1.409(3) ?
    C3 C4 . 1.368(3) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.377(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.368(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.402(3) ?
    C6 H6 . 0.9300 ?
    C8 C9 . 1.500(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C14 . 1.381(3) ?
    C9 C10 . 1.382(3) ?
    C10 C11 . 1.386(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.403(3) ?
    C11 C19 . 1.546(3) ?
    C12 C13 . 1.406(3) ?
    C13 C14 . 1.385(3) ?
    C13 C15 . 1.537(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.527(4) ?
    C15 C18 . 1.535(4) ?
    C15 C17 . 1.541(4) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C19 C22 . 1.528(3) ?
    C19 C21 . 1.529(4) ?
    C19 C20 . 1.532(4) ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
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
    C7 S1 C8 . . 102.81(11) ?
    C1 O1 H1 . . 113(2) ?
    C12 O3 H3 . . 115(3) ?
    O2 C1 O1 . . 121.9(2) ?
    O2 C1 C2 . . 123.7(2) ?
    O1 C1 C2 . . 114.4(2) ?
    C3 C2 C7 . . 119.6(2) ?
    C3 C2 C1 . . 118.5(2) ?
    C7 C2 C1 . . 121.9(2) ?
    C4 C3 C2 . . 121.7(2) ?
    C4 C3 H3A . . 119.2 ?
    C2 C3 H3A . . 119.2 ?
    C3 C4 C5 . . 119.0(2) ?
    C3 C4 H4 . . 120.5 ?
    C5 C4 H4 . . 120.5 ?
    C6 C5 C4 . . 120.7(2) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C5 C6 C7 . . 121.9(2) ?
    C5 C6 H6 . . 119.1 ?
    C7 C6 H6 . . 119.1 ?
    C6 C7 C2 . . 117.2(2) ?
    C6 C7 S1 . . 121.41(18) ?
    C2 C7 S1 . . 121.41(18) ?
    C9 C8 S1 . . 108.23(17) ?
    C9 C8 H8A . . 110.1 ?
    S1 C8 H8A . . 110.1 ?
    C9 C8 H8B . . 110.1 ?
    S1 C8 H8B . . 110.1 ?
    H8A C8 H8B . . 108.4 ?
    C14 C9 C10 . . 118.3(2) ?
    C14 C9 C8 . . 120.6(2) ?
    C10 C9 C8 . . 121.1(2) ?
    C9 C10 C11 . . 123.0(2) ?
    C9 C10 H10 . . 118.5 ?
    C11 C10 H10 . . 118.5 ?
    C10 C11 C12 . . 116.5(2) ?
    C10 C11 C19 . . 120.7(2) ?
    C12 C11 C19 . . 122.8(2) ?
    O3 C12 C11 . . 116.68(19) ?
    O3 C12 C13 . . 120.53(19) ?
    C11 C12 C13 . . 122.8(2) ?
    C14 C13 C12 . . 116.9(2) ?
    C14 C13 C15 . . 120.2(2) ?
    C12 C13 C15 . . 122.9(2) ?
    C9 C14 C13 . . 122.5(2) ?
    C9 C14 H14 . . 118.7 ?
    C13 C14 H14 . . 118.7 ?
    C16 C15 C18 . . 105.9(3) ?
    C16 C15 C13 . . 112.7(2) ?
    C18 C15 C13 . . 112.0(2) ?
    C16 C15 C17 . . 107.0(3) ?
    C18 C15 C17 . . 108.2(2) ?
    C13 C15 C17 . . 110.7(2) ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C15 C17 H17A . . 109.5 ?
    C15 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C15 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C15 C18 H18A . . 109.5 ?
    C15 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C15 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C22 C19 C21 . . 110.1(2) ?
    C22 C19 C20 . . 105.9(2) ?
    C21 C19 C20 . . 107.8(2) ?
    C22 C19 C11 . . 111.29(19) ?
    C21 C19 C11 . . 110.3(2) ?
    C20 C19 C11 . . 111.3(2) ?
    C19 C20 H20A . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C19 C21 H21A . . 109.5 ?
    C19 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C19 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C19 C22 H22A . . 109.5 ?
    C19 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C19 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
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
    O1 H1 O2 3_546 0.837(18) 1.825(18) 2.661(2) 178(4)
data_global
_journal_date_recd_electronic     2010-06-10
_journal_date_accepted     2010-06-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     o1787
_journal_page_last     o1787
_journal_paper_category     QO
_journal_coeditor_code     PK2249
_publ_contact_author_name     'Hamid Khaledi'
_publ_contact_author_address
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email     'khaledi@siswa.um.edu.my'
_publ_contact_author_fax     '+603-79674193'
_publ_contact_author_phone     '+603-79674246'
_publ_section_title
;
2-[(3,5-Di-tert-butyl-4-hydroxybenzyl)sulfanyl]benzoic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Alhadi, Abeer A.' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
    'Khaledi, Hamid' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
    'Mohd Ali, Hapipah' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
    'Olmstead, Marilyn M.' .
;
Department of Chemistry, University of California, One Shields Avenue, Davis,
CA 95616, USA
;
