#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/51/2235173.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_2235173
loop_
_publ_author_name
'Zhang, Ya-Li'
'Xiang, Liu-Fang'
'Zou, Peng'
'Jin, Yi-Jun'
'Yang, Shu-Lin'
_publ_section_title
;
 (1E,4E)-1-(Thiophen-2-yl)-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-one
;
_journal_coeditor_code           NG5270
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1859
_journal_paper_doi               10.1107/S1600536812022465
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C18 H22 O S'
_chemical_formula_moiety         'C18 H22 O S'
_chemical_formula_sum            'C18 H22 O S'
_chemical_formula_weight         286.42
_chemical_name_systematic
;
(1E,4E)-1-(Thiophen-2-yl)-5-(2,6,6-trimethylcyclohex-1-en-1-
yl)penta-1,4-dien-3-one
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.082(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3401(17)
_cell_length_b                   6.9084(14)
_cell_length_c                   13.994(3)
_cell_measurement_reflns_used    2746
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.473
_cell_measurement_theta_min      4.912
_cell_volume                     801.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4888
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.166
_refine_ls_extinction_coef       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1711
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0910P)²+0.1463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                1555
_reflns_number_total             1711
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5270.cif
_cod_data_source_block           I
_cod_original_cell_volume        801.7(3)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2235173
_cod_database_fobs_code          2235173
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
S S1 1.08493(6) 0.2500 0.58526(4) 0.0487(3) Uani d S 1 2
O O1 0.4327(2) 0.2500 0.53246(12) 0.0817(7) Uani d S 1 2
C C1 1.2154(3) 0.2500 0.68697(16) 0.0521(6) Uani d S 1 2
H H1 1.3270 0.2500 0.6874 0.063 Uiso calc SR 1 2
C C2 1.1384(3) 0.2500 0.76737(16) 0.0533(6) Uani d S 1 2
H H2 1.1919 0.2500 0.8292 0.064 Uiso calc SR 1 2
C C3 0.9688(3) 0.2500 0.74818(15) 0.0464(5) Uani d S 1 2
H H3 0.8982 0.2500 0.7954 0.056 Uiso calc SR 1 2
C C4 0.9204(3) 0.2500 0.65023(14) 0.0416(5) Uani d S 1 2
C C5 0.7575(3) 0.2500 0.60586(16) 0.0463(5) Uani d S 1 2
H H5 0.6772 0.2500 0.6472 0.056 Uiso calc SR 1 2
C C6 0.7078(3) 0.2500 0.51249(15) 0.0504(6) Uani d S 1 2
H H6 0.7839 0.2500 0.4685 0.060 Uiso calc SR 1 2
C C7 0.5361(3) 0.2500 0.47694(16) 0.0525(6) Uani d S 1 2
C C8 0.4939(3) 0.2500 0.37222(15) 0.0537(6) Uani d S 1 2
H H8 0.5754 0.2500 0.3317 0.064 Uiso calc SR 1 2
C C9 0.3412(3) 0.2500 0.33499(15) 0.0478(5) Uani d S 1 2
H H9 0.2683 0.2500 0.3809 0.057 Uiso calc SR 1 2
C C10 0.2646(3) 0.2500 0.23645(14) 0.0442(5) Uani d S 1 2
C C11 0.1024(3) 0.2500 0.22224(15) 0.0439(5) Uani d S 1 2
C C12 0.0090(3) 0.2500 0.12463(18) 0.0631(7) Uani d S 1 2
C C13 0.1137(5) 0.3120(7) 0.0454(2) 0.0749(18) Uani d PD 0.50 1
C C14 0.2610(5) 0.1876(8) 0.0579(2) 0.0745(19) Uani d PD 0.50 1
C C15 0.3698(3) 0.2500 0.15222(17) 0.0624(7) Uani d S 1 2
C C16 -0.0078(3) 0.2500 0.30125(17) 0.0516(6) Uani d S 1 2
H H16A -0.0320 0.3810 0.3175 0.077 Uiso calc PR 0.50 1
H H16B 0.0445 0.1857 0.3569 0.077 Uiso calc PR 0.50 1
H H16C -0.1060 0.1833 0.2796 0.077 Uiso calc PR 0.50 1
C C17 0.4761(3) 0.0695(4) 0.15515(17) 0.0931(8) Uani d . 1 1
H H17A 0.5515 0.0723 0.2119 0.140 Uiso calc R 1 1
H H17B 0.5338 0.0669 0.0993 0.140 Uiso calc R 1 1
H H17C 0.4099 -0.0440 0.1560 0.140 Uiso calc R 1 1
H H14A 0.317(4) 0.2500 0.005(2) 0.091(11) Uiso d SD 1 2
H H12A -0.061(3) 0.137(3) 0.1184(16) 0.077(6) Uiso d . 1 1
H H14B 0.253(8) 0.046(3) 0.061(5) 0.13(3) Uiso d PD 0.50 1
H H13A 0.060(4) 0.2500 -0.0122(18) 0.096(11) Uiso d SD 1 2
H H13B 0.159(5) 0.445(3) 0.048(3) 0.052(11) Uiso d PD 0.50 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
C1 S1 C4 . . 91.89(10)
C2 C1 S1 . . 112.24(18)
C2 C1 H1 . . 123.9
S1 C1 H1 . . 123.9
C1 C2 C3 . . 113.3(2)
C1 C2 H2 . . 123.3
C3 C2 H2 . . 123.3
C4 C3 C2 . . 111.63(19)
C4 C3 H3 . . 124.2
C2 C3 H3 . . 124.2
C3 C4 C5 . . 126.24(19)
C3 C4 S1 . . 110.90(16)
C5 C4 S1 . . 122.86(16)
C6 C5 C4 . . 127.5(2)
C6 C5 H5 . . 116.2
C4 C5 H5 . . 116.2
C5 C6 C7 . . 121.74(19)
C5 C6 H6 . . 119.1
C7 C6 H6 . . 119.1
O1 C7 C6 . . 121.0(2)
O1 C7 C8 . . 121.6(2)
C6 C7 C8 . . 117.42(19)
C9 C8 C7 . . 120.7(2)
C9 C8 H8 . . 119.6
C7 C8 H8 . . 119.6
C8 C9 C10 . . 132.8(2)
C8 C9 H9 . . 113.6
C10 C9 H9 . . 113.6
C11 C10 C9 . . 118.22(19)
C11 C10 C15 . . 122.08(19)
C9 C10 C15 . . 119.7(2)
C10 C11 C12 . . 123.5(2)
C10 C11 C16 . . 124.87(19)
C12 C11 C16 . . 111.65(19)
C11 C12 C13 . . 112.1(2)
C11 C12 C13 . 4_565 112.1(2)
C13 C12 C13 . 4_565 32.2(4)
C11 C12 H12A . . 109.2(14)
C13 C12 H12A . . 122.5(13)
C13 C12 H12A 4_565 . 95.3(13)
C13 C13 C14 4_565 4_565 90.1(3)
C13 C13 C14 4_565 . 54.9(3)
C14 C13 C14 4_565 . 35.2(5)
C13 C13 C12 4_565 . 73.90(18)
C14 C13 C12 4_565 . 122.3(3)
C14 C13 C12 . . 106.1(3)
C13 C13 H13A 4_565 . 64.1(7)
C14 C13 H13A 4_565 . 119(2)
C14 C13 H13A . . 98.3(16)
C12 C13 H13A . . 103(2)
C13 C13 H13B 4_565 . 158(3)
C14 C13 H13B 4_565 . 68(3)
C14 C13 H13B . . 103(3)
C12 C13 H13B . . 118(2)
H13A C13 H13B . . 125(3)
C14 C14 C13 4_565 4_565 89.9(3)
C14 C14 C13 4_565 . 54.9(3)
C13 C14 C13 4_565 . 35.0(4)
C14 C14 C15 4_565 . 74.18(19)
C13 C14 C15 4_565 . 126.7(3)
C13 C14 C15 . . 109.5(3)
C14 C14 H14A 4_565 . 64.9(6)
C13 C14 H14A 4_565 . 115(2)
C13 C14 H14A . . 96.0(16)
C15 C14 H14A . . 103(2)
C14 C14 H14B 4_565 . 175(4)
C13 C14 H14B 4_565 . 86(4)
C13 C14 H14B . . 121(4)
C15 C14 H14B . . 106(4)
H14A C14 H14B . . 119(4)
C17 C15 C17 . 4_565 109.3(3)
C17 C15 C10 . . 110.80(14)
C17 C15 C10 4_565 . 110.80(14)
C17 C15 C14 . 4_565 121.7(2)
C17 C15 C14 4_565 4_565 94.6(2)
C10 C15 C14 . 4_565 108.4(2)
C17 C15 C14 . . 94.6(2)
C17 C15 C14 4_565 . 121.7(2)
C10 C15 C14 . . 108.4(2)
C14 C15 C14 4_565 . 31.6(4)
C11 C16 H16A . . 109.5
C11 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C11 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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C1 . 1.698(2)
S1 C4 . 1.724(2)
O1 C7 . 1.220(3)
C1 C2 . 1.353(3)
C1 H1 . 0.9300
C2 C3 . 1.411(3)
C2 H2 . 0.9300
C3 C4 . 1.387(3)
C3 H3 . 0.9300
C4 C5 . 1.433(3)
C5 C6 . 1.328(3)
C5 H5 . 0.9300
C6 C7 . 1.465(3)
C6 H6 . 0.9300
C7 C8 . 1.470(3)
C8 C9 . 1.324(3)
C8 H8 . 0.9300
C9 C10 . 1.457(3)
C9 H9 . 0.9300
C10 C11 . 1.346(3)
C10 C15 . 1.542(3)
C11 C12 . 1.499(3)
C11 C16 . 1.511(3)
C12 C13 . 1.543(5)
C12 C13 4_565 1.543(5)
C12 H12A . 0.97(2)
C13 C13 4_565 0.856(10)
C13 C14 4_565 1.222(6)
C13 C14 . 1.494(6)
C13 H13A . 0.979(18)
C13 H13B . 0.994(19)
C14 C14 4_565 0.862(11)
C14 C13 4_565 1.222(6)
C14 C15 . 1.580(4)
C14 H14A . 1.015(18)
C14 H14B . 0.99(2)
C15 C17 . 1.528(3)
C15 C17 4_565 1.528(3)
C15 C14 4_565 1.580(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
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_4
_geom_torsion
C4 S1 C1 C2 . . 0.0
S1 C1 C2 C3 . . 0.0
C1 C2 C3 C4 . . 0.0
C2 C3 C4 C5 . . 180.0
C2 C3 C4 S1 . . 0.0
C1 S1 C4 C3 . . 0.0
C1 S1 C4 C5 . . 180.0
C3 C4 C5 C6 . . 180.0
S1 C4 C5 C6 . . 0.0
C4 C5 C6 C7 . . 180.0
C5 C6 C7 O1 . . 0.0
C5 C6 C7 C8 . . 180.0
O1 C7 C8 C9 . . 0.0
C6 C7 C8 C9 . . 180.0
C7 C8 C9 C10 . . 180.0
C8 C9 C10 C11 . . 180.0
C8 C9 C10 C15 . . 0.0
C9 C10 C11 C12 . . 180.0
C15 C10 C11 C12 . . 0.0
C9 C10 C11 C16 . . 0.0
C15 C10 C11 C16 . . 180.0
C10 C11 C12 C13 . . -17.4(2)
C16 C11 C12 C13 . . 162.6(2)
C10 C11 C12 C13 . 4_565 17.4(2)
C16 C11 C12 C13 . 4_565 -162.6(2)
C11 C12 C13 C13 . 4_565 96.72(10)
C11 C12 C13 C14 . 4_565 17.1(6)
C13 C12 C13 C14 4_565 4_565 -79.6(5)
C11 C12 C13 C14 . . 51.6(4)
C13 C12 C13 C14 4_565 . -45.1(3)
C13 C13 C14 C14 4_565 4_565 180.0
C12 C13 C14 C14 . 4_565 -123.8(3)
C14 C13 C14 C13 4_565 4_565 180.0
C12 C13 C14 C13 . 4_565 56.2(3)
C13 C13 C14 C15 4_565 . -127.0(4)
C14 C13 C14 C15 4_565 . 53.0(4)
C12 C13 C14 C15 . . -70.7(4)
C11 C10 C15 C17 . . -119.22(17)
C9 C10 C15 C17 . . 60.78(17)
C11 C10 C15 C17 . 4_565 119.22(17)
C9 C10 C15 C17 . 4_565 -60.78(17)
C11 C10 C15 C14 . 4_565 16.7(2)
C9 C10 C15 C14 . 4_565 -163.3(2)
C11 C10 C15 C14 . . -16.7(2)
C9 C10 C15 C14 . . 163.3(2)
C14 C14 C15 C17 4_565 . -150.87(16)
C13 C14 C15 C17 4_565 . 131.5(6)
C13 C14 C15 C17 . . 166.3(3)
C14 C14 C15 C17 4_565 4_565 -34.77(18)
C13 C14 C15 C17 4_565 4_565 -112.4(5)
C13 C14 C15 C17 . 4_565 -77.6(4)
C14 C14 C15 C10 4_565 . 95.42(9)
C13 C14 C15 C10 4_565 . 17.8(6)
C13 C14 C15 C10 . . 52.6(4)
C13 C14 C15 C14 4_565 4_565 -77.6(6)
C13 C14 C15 C14 . 4_565 -42.8(4)
