#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/02/2010295.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_2010295
loop_
_publ_author_name
'Declercq, Jean-Paul'
'Feneau-Dupont, Janine'
'Louis, Chantal'
'Hootelé, Claude'
_publ_section_title
;
 (Z)-(--)-(R)-β-Styryl p-tolyl sulfoxide
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1980
_journal_page_last               1981
_journal_paper_doi               10.1107/S0108270194007092
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C15 H14 O S'
_chemical_formula_sum            'C15 H14 O S'
_chemical_formula_weight         242.32
_chemical_name_systematic
;
(Z)-(-)-(R)-β-styryl p-tolyl sulfoxide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0610(10)
_cell_length_b                   11.4390(10)
_cell_length_c                   18.858(2)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49
_cell_measurement_theta_min      17
_cell_volume                     1307.5(3)
_computing_cell_refinement       'local program'
_computing_data_collection       'local program'
_computing_data_reduction        'local program'
_computing_molecular_graphics    'PLUTO (Motherwell & Clegg, 1978)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1994)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Huber four-circle diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2364
_diffrn_reflns_theta_max         67.46
_diffrn_reflns_theta_min         4.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    2.029
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.048
_refine_ls_goodness_of_fit_obs   1.083
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_restrained_S_obs      1.083
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_obs          0.0432
_refine_ls_shift/esd_max         -0.473
_refine_ls_shift/esd_mean        0.081
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
; calc w = 1/[\s^2^(F~o~^2^) + (0.0786P)^2^ + 0.0848P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1203
_refine_ls_wR_factor_obs         0.1164
_reflns_number_observed          2091
_reflns_number_total             2364
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            hr1014.cif
_cod_data_source_block           hoot931
_cod_original_cell_volume        1307.5(2)
_cod_database_code               2010295
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.1273(5) 0.8016(2) 0.58792(15) 0.0690(7) Uani d . 1 . C
H1 0.0664(5) 0.8680(2) 0.56729(15) 0.124(4) Uiso calc R 1 . H
C2 0.0548(4) 0.7015(3) 0.56282(15) 0.0675(7) Uani d . 1 . C
H2 -0.0281(4) 0.7028(3) 0.52133(15) 0.124(4) Uiso calc R 1 . H
S3 0.10574(12) 0.56359(6) 0.60339(3) 0.0672(2) Uani d . 1 . S
O4 -0.1215(4) 0.5191(2) 0.61637(14) 0.0963(7) Uani d . 1 . O
C5 0.2118(4) 0.4861(2) 0.52862(14) 0.0606(6) Uani d . 1 . C
C6 0.0865(5) 0.4701(3) 0.4684(2) 0.0755(8) Uani d . 1 . C
H6 -0.0535(5) 0.5029(3) 0.4655(2) 0.124(4) Uiso calc R 1 . H
C7 0.1675(6) 0.4061(3) 0.4130(2) 0.0853(9) Uani d . 1 . C
H7 0.0817(6) 0.3963(3) 0.3726(2) 0.124(4) Uiso calc R 1 . H
C8 0.3748(6) 0.3558(2) 0.4161(2) 0.0793(8) Uani d . 1 . C
C9 0.4950(6) 0.3707(3) 0.4766(2) 0.0836(9) Uani d . 1 . C
H9 0.6330(6) 0.3357(3) 0.4798(2) 0.124(4) Uiso calc R 1 . H
C10 0.4192(5) 0.4361(3) 0.5332(2) 0.0745(7) Uani d . 1 . C
H10 0.5056(5) 0.4462(3) 0.5735(2) 0.124(4) Uiso calc R 1 . H
C11 0.4611(9) 0.2842(3) 0.3548(2) 0.118(2) Uani d . 1 . C
H11A 0.3541(9) 0.2837(3) 0.3173(2) 0.124(4) Uiso calc R 1 . H
H11B 0.4877(9) 0.2055(3) 0.3703(2) 0.124(4) Uiso calc R 1 . H
H11C 0.5963(9) 0.3178(3) 0.3378(2) 0.124(4) Uiso calc R 1 . H
C12 0.2892(5) 0.8233(2) 0.64342(13) 0.0604(6) Uani d . 1 . C
C13 0.2562(5) 0.9143(2) 0.6913(2) 0.0775(8) Uani d . 1 . C
H13 0.1298(5) 0.9600(2) 0.6880(2) 0.124(4) Uiso calc R 1 . H
C14 0.4098(7) 0.9374(3) 0.7440(2) 0.0912(10) Uani d . 1 . C
H14 0.3852(7) 0.9979(3) 0.7759(2) 0.124(4) Uiso calc R 1 . H
C15 0.5967(7) 0.8718(3) 0.7491(2) 0.0901(10) Uani d . 1 . C
H15 0.6999(7) 0.8878(3) 0.7843(2) 0.124(4) Uiso calc R 1 . H
C16 0.6324(6) 0.7814(3) 0.7019(2) 0.0818(8) Uani d . 1 . C
H16 0.7596(6) 0.7363(3) 0.7054(2) 0.124(4) Uiso calc R 1 . H
C17 0.4803(5) 0.7580(2) 0.64969(14) 0.0652(7) Uani d . 1 . C
H17 0.5063(5) 0.6972(2) 0.61804(14) 0.124(4) Uiso calc R 1 . H
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'
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_publ_flag
C2 C1 C12 129.2(2) yes
C2 C1 H1 115.4(2) ?
C12 C1 H1 115.41(14) ?
C1 C2 S3 124.0(2) yes
C1 C2 H2 118.0(2) ?
S3 C2 H2 117.99(10) ?
O4 S3 C2 102.30(10) yes
O4 S3 C5 107.10(10) yes
C2 S3 C5 99.40(10) yes
C6 C5 C10 119.8(3) yes
C6 C5 S3 121.2(2) yes
C10 C5 S3 118.9(2) yes
C7 C6 C5 120.2(3) yes
C7 C6 H6 119.9(2) ?
C5 C6 H6 119.9(2) ?
C6 C7 C8 121.1(3) yes
C6 C7 H7 119.4(2) ?
C8 C7 H7 119.5(2) ?
C9 C8 C7 117.9(3) yes
C9 C8 C11 121.5(4) yes
C7 C8 C11 120.5(4) yes
C8 C9 C10 122.4(3) yes
C8 C9 H9 118.8(2) ?
C10 C9 H9 118.8(2) ?
C5 C10 C9 118.5(3) yes
C5 C10 H10 120.7(2) ?
C9 C10 H10 120.8(2) ?
C8 C11 H11A 109.5(2) ?
C8 C11 H11B 109.4(2) ?
H11A C11 H11B 109.5 ?
C8 C11 H11C 109.5(2) ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C17 C12 C13 117.9(3) yes
C17 C12 C1 122.3(2) yes
C13 C12 C1 119.8(3) yes
C14 C13 C12 120.7(3) yes
C14 C13 H13 119.7(2) ?
C12 C13 H13 119.6(2) ?
C15 C14 C13 120.3(3) yes
C15 C14 H14 119.9(2) ?
C13 C14 H14 119.8(2) ?
C14 C15 C16 119.8(3) yes
C14 C15 H15 120.1(2) ?
C16 C15 H15 120.1(2) ?
C17 C16 C15 120.1(3) yes
C17 C16 H16 119.9(2) ?
C15 C16 H16 120.0(2) ?
C16 C17 C12 121.2(3) yes
C16 C17 H17 119.4(2) ?
C12 C17 H17 119.4(2) ?
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
C1 C2 . 1.315(4) yes
C1 C12 . 1.456(4) yes
C1 H1 . 0.93 ?
C2 S3 . 1.780(3) yes
C2 H2 . 0.93 ?
S3 O4 . 1.489(2) yes
S3 C5 . 1.785(3) yes
C5 C6 . 1.378(4) yes
C5 C10 . 1.384(4) yes
C6 C7 . 1.366(5) yes
C6 H6 . 0.93 ?
C7 C8 . 1.383(5) yes
C7 H7 . 0.93 ?
C8 C9 . 1.364(5) yes
C8 C11 . 1.511(5) yes
C9 C10 . 1.382(5) yes
C9 H9 . 0.93 ?
C10 H10 . 0.93 ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
C12 C17 . 1.383(4) yes
C12 C13 . 1.393(4) yes
C13 C14 . 1.387(5) yes
C13 H13 . 0.93 ?
C14 C15 . 1.362(5) yes
C14 H14 . 0.93 ?
C15 C16 . 1.382(5) yes
C15 H15 . 0.93 ?
C16 C17 . 1.375(4) yes
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
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
C12 C1 C2 S3 11.9(4)
C1 C2 S3 O4 121.9(3)
C1 C2 S3 C5 -128.2(3)
O4 S3 C5 C6 45.6(3)
C2 S3 C5 C6 -60.5(2)
O4 S3 C5 C10 -130.8(2)
C2 S3 C5 C10 123.1(2)
C10 C5 C6 C7 -0.8(4)
S3 C5 C6 C7 -177.1(3)
C5 C6 C7 C8 0.4(5)
C6 C7 C8 C9 0.8(5)
C6 C7 C8 C11 179.3(3)
C7 C8 C9 C10 -1.7(5)
C11 C8 C9 C10 179.9(3)
C6 C5 C10 C9 0.0(4)
S3 C5 C10 C9 176.4(2)
C8 C9 C10 C5 1.3(5)
C2 C1 C12 C17 40.6(4)
C2 C1 C12 C13 -141.0(3)
C17 C12 C13 C14 -0.6(4)
C1 C12 C13 C14 -179.1(3)
C12 C13 C14 C15 0.6(5)
C13 C14 C15 C16 -0.4(5)
C14 C15 C16 C17 0.3(5)
C15 C16 C17 C12 -0.3(5)
C13 C12 C17 C16 0.5(4)
C1 C12 C17 C16 178.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4787744
