#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224190.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224190
loop_
_publ_author_name
'Baidya, Mahiuddin'
'Mayr, Herbert'
'Mayer, Peter'
_publ_section_title
;
 Benzhydryl phenyl sulfone
;
_journal_coeditor_code           DS2011
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3224
_journal_paper_doi               10.1107/S1600536809050363
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H16 O2 S'
_chemical_formula_moiety         'C19 H16 O2 S'
_chemical_formula_sum            'C19 H16 O2 S'
_chemical_formula_weight         308.395
_chemical_name_common            'Benzhydryl Phenyl Sulfone'
_chemical_name_systematic
;
Benzhydryl phenyl sulfone
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.3250(4)
_cell_length_b                   5.79790(10)
_cell_length_c                   16.4983(4)
_cell_measurement_reflns_used    6504
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     1561.58(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 2004)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method
'CCD; rotation images; thick slices, phi/omega-scan'
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11675
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.31177(5)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.279
_refine_ls_abs_structure_details 'Flack (1983), 1646 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.2163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                3136
_reflns_number_total             3499
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ds2011.cif
_cod_data_source_block           I
_cod_database_code               2224190
_cod_database_fobs_code          2224190
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
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 0.06340(2) 0.12898(6) 0.26302(3) 0.02887(10) Uani d . 1 . .
O O1 0.08669(8) 0.1945(2) 0.34378(7) 0.0408(3) Uani d . 1 . .
O O2 0.03981(7) -0.10715(19) 0.24877(8) 0.0384(3) Uani d . 1 . .
C C1 -0.01788(10) 0.3229(3) 0.23092(10) 0.0276(3) Uani d . 1 . .
H H1 0.0034 0.4820 0.2409 0.033 Uiso calc R 1 . .
C C2 -0.03155(9) 0.3073(3) 0.14009(10) 0.0272(3) Uani d . 1 . .
C C3 -0.06491(11) 0.1160(3) 0.10143(11) 0.0347(4) Uani d . 1 . .
H H3 -0.0816 -0.0139 0.1324 0.042 Uiso calc R 1 . .
C C4 -0.07391(11) 0.1141(3) 0.01781(12) 0.0405(4) Uani d . 1 . .
H H4 -0.0964 -0.0180 -0.0080 0.049 Uiso calc R 1 . .
C C5 -0.05082(12) 0.2999(4) -0.02807(12) 0.0428(4) Uani d . 1 . .
H H5 -0.0576 0.2970 -0.0853 0.051 Uiso calc R 1 . .
C C6 -0.01740(12) 0.4927(4) 0.00955(13) 0.0451(5) Uani d . 1 . .
H H6 -0.0008 0.6218 -0.0218 0.054 Uiso calc R 1 . .
C C7 -0.00847(11) 0.4955(3) 0.09276(11) 0.0363(4) Uani d . 1 . .
H H7 0.0138 0.6283 0.1182 0.044 Uiso calc R 1 . .
C C8 -0.09145(10) 0.2969(3) 0.28610(9) 0.0304(4) Uani d . 1 . .
C C9 -0.14154(12) 0.1021(3) 0.28814(12) 0.0431(4) Uani d . 1 . .
H H9 -0.1290 -0.0274 0.2551 0.052 Uiso calc R 1 . .
C C10 -0.20970(13) 0.0971(4) 0.33832(13) 0.0500(5) Uani d . 1 . .
H H10 -0.2444 -0.0343 0.3383 0.060 Uiso calc R 1 . .
C C11 -0.22748(13) 0.2805(4) 0.38811(13) 0.0531(5) Uani d . 1 . .
H H11 -0.2740 0.2751 0.4227 0.064 Uiso calc R 1 . .
C C12 -0.17763(14) 0.4719(4) 0.38771(14) 0.0547(5) Uani d . 1 . .
H H12 -0.1895 0.5985 0.4223 0.066 Uiso calc R 1 . .
C C13 -0.10994(12) 0.4802(3) 0.33668(11) 0.0406(4) Uani d . 1 . .
H H13 -0.0760 0.6133 0.3365 0.049 Uiso calc R 1 . .
C C14 0.14411(10) 0.2005(3) 0.19613(10) 0.0292(3) Uani d . 1 . .
C C15 0.18653(11) 0.4044(3) 0.20890(12) 0.0407(4) Uani d . 1 . .
H H15 0.1739 0.5002 0.2539 0.049 Uiso calc R 1 . .
C C16 0.24784(12) 0.4662(3) 0.15468(14) 0.0479(5) Uani d . 1 . .
H H16 0.2775 0.6055 0.1623 0.057 Uiso calc R 1 . .
C C17 0.26549(12) 0.3259(4) 0.09010(13) 0.0503(5) Uani d . 1 . .
H H17 0.3075 0.3691 0.0532 0.060 Uiso calc R 1 . .
C C18 0.22315(13) 0.1231(4) 0.07798(14) 0.0517(5) Uani d . 1 . .
H H18 0.2364 0.0267 0.0333 0.062 Uiso calc R 1 . .
C C19 0.16122(12) 0.0598(3) 0.13093(12) 0.0403(4) Uani d . 1 . .
H H19 0.1311 -0.0782 0.1224 0.048 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 118.23(7) ?
O1 S1 C14 . . 108.64(8) ?
O2 S1 C14 . . 108.67(8) ?
O1 S1 C1 . . 107.45(8) ?
O2 S1 C1 . . 110.16(7) ?
C14 S1 C1 . . 102.53(8) ?
C8 C1 C2 . . 118.10(14) ?
C8 C1 S1 . . 110.02(11) ?
C2 C1 S1 . . 110.99(11) ?
C8 C1 H1 . . 105.6 ?
C2 C1 H1 . . 105.6 ?
S1 C1 H1 . . 105.6 ?
C3 C2 C7 . . 118.25(15) ?
C3 C2 C1 . . 123.92(15) ?
C7 C2 C1 . . 117.83(14) ?
C4 C3 C2 . . 120.27(16) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C5 C4 C3 . . 120.94(18) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 119.59(18) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C7 C6 C5 . . 119.67(18) ?
C7 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
C6 C7 C2 . . 121.27(17) ?
C6 C7 H7 . . 119.4 ?
C2 C7 H7 . . 119.4 ?
C13 C8 C9 . . 118.64(17) ?
C13 C8 C1 . . 117.33(15) ?
C9 C8 C1 . . 124.03(15) ?
C10 C9 C8 . . 120.08(19) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C11 C10 C9 . . 120.67(19) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C12 . . 119.74(19) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C11 C12 C13 . . 120.05(19) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C8 C13 C12 . . 120.79(18) ?
C8 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C19 C14 C15 . . 121.46(17) ?
C19 C14 S1 . . 119.94(13) ?
C15 C14 S1 . . 118.53(13) ?
C14 C15 C16 . . 118.82(18) ?
C14 C15 H15 . . 120.6 ?
C16 C15 H15 . . 120.6 ?
C17 C16 C15 . . 119.91(18) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.89(19) ?
C16 C17 H17 . . 119.6 ?
C18 C17 H17 . . 119.6 ?
C17 C18 C19 . . 120.03(19) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C14 C19 C18 . . 118.88(18) ?
C14 C19 H19 . . 120.6 ?
C18 C19 H19 . . 120.6 ?
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 O1 . 1.4366(13) ?
S1 O2 . 1.4415(12) ?
S1 C14 . 1.7681(17) ?
S1 C1 . 1.8180(16) ?
C1 C8 . 1.514(2) ?
C1 C2 . 1.518(2) ?
C1 H1 . 1.0000 ?
C2 C3 . 1.390(2) ?
C2 C7 . 1.394(2) ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.369(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.390(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.381(3) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C13 . 1.385(2) ?
C8 C9 . 1.395(3) ?
C9 C10 . 1.387(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.374(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.376(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.390(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 C19 . 1.379(2) ?
C14 C15 . 1.386(2) ?
C15 C16 . 1.389(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.371(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.378(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.386(3) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
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
_geom_hbond_publ_flag
C1 H1 O2 1_565 1.00 2.46 3.449(2) 171 yes
C4 H4 O1 2_554 0.95 2.66 3.390(2) 134 yes
C7 H7 O2 1_565 0.95 2.68 3.543(2) 152 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C8 . . . . -61.76(13) ?
O2 S1 C1 C8 . . . . 68.31(13) ?
C14 S1 C1 C8 . . . . -176.16(11) ?
O1 S1 C1 C2 . . . . 165.65(11) ?
O2 S1 C1 C2 . . . . -64.28(13) ?
C14 S1 C1 C2 . . . . 51.25(12) ?
C8 C1 C2 C3 . . . . -59.0(2) ?
S1 C1 C2 C3 . . . . 69.33(18) ?
C8 C1 C2 C7 . . . . 121.61(17) ?
S1 C1 C2 C7 . . . . -110.03(15) ?
C7 C2 C3 C4 . . . . 0.6(3) ?
C1 C2 C3 C4 . . . . -178.76(17) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C3 C4 C5 C6 . . . . 0.4(3) ?
C4 C5 C6 C7 . . . . -0.5(3) ?
C5 C6 C7 C2 . . . . 0.7(3) ?
C3 C2 C7 C6 . . . . -0.7(3) ?
C1 C2 C7 C6 . . . . 178.68(17) ?
C2 C1 C8 C13 . . . . -120.05(16) ?
S1 C1 C8 C13 . . . . 111.14(15) ?
C2 C1 C8 C9 . . . . 59.2(2) ?
S1 C1 C8 C9 . . . . -69.59(19) ?
C13 C8 C9 C10 . . . . 1.9(3) ?
C1 C8 C9 C10 . . . . -177.35(17) ?
C8 C9 C10 C11 . . . . -1.8(3) ?
C9 C10 C11 C12 . . . . 0.6(3) ?
C10 C11 C12 C13 . . . . 0.5(3) ?
C9 C8 C13 C12 . . . . -0.9(3) ?
C1 C8 C13 C12 . . . . 178.46(18) ?
C11 C12 C13 C8 . . . . -0.3(3) ?
O1 S1 C14 C19 . . . . 144.32(14) ?
O2 S1 C14 C19 . . . . 14.45(16) ?
C1 S1 C14 C19 . . . . -102.16(15) ?
O1 S1 C14 C15 . . . . -38.52(16) ?
O2 S1 C14 C15 . . . . -168.39(13) ?
C1 S1 C14 C15 . . . . 75.01(15) ?
C19 C14 C15 C16 . . . . -0.3(3) ?
S1 C14 C15 C16 . . . . -177.45(15) ?
C14 C15 C16 C17 . . . . -0.2(3) ?
C15 C16 C17 C18 . . . . 0.0(3) ?
C16 C17 C18 C19 . . . . 0.7(3) ?
C15 C14 C19 C18 . . . . 1.0(3) ?
S1 C14 C19 C18 . . . . 178.09(15) ?
C17 C18 C19 C14 . . . . -1.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 195822
