#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/55/2215591.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_2215591
loop_
_publ_author_name
'Guang Liang'
'Shu-Lin Yang'
'Xiao-Hui Wang'
'Yue-Ru Li'
'Xiao-Kun Li'
_publ_section_title
;
 (2E,6E)-2,6-Bis[(5-methylthiophen-2-yl)methylene]cyclohexanone
;
_journal_coeditor_code           LH2505
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4118
_journal_page_last               o4118
_journal_paper_doi               10.1107/S160053680704531X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H18 O S2'
_chemical_formula_moiety         'C18 H18 O S2'
_chemical_formula_sum            'C18 H18 O S2'
_chemical_formula_weight         314.44
_chemical_melting_point          439.0(10)
_chemical_name_systematic
;
(2E,6E)-2,6-Bis[(5-methylthiophen-2-yl)methylene]cyclohexanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 99.204(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0631(19)
_cell_length_b                   5.9790(8)
_cell_length_c                   17.689(2)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.872
_cell_measurement_theta_min      4.665
_cell_volume                     1572.6(3)
_computing_cell_refinement       'SAINT (Siemens, 1994)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1994)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1999)'
_computing_publication_material  'SHELXTL (Sheldrick, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.1177
_diffrn_reflns_av_sigmaI/netI    0.1018
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8803
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0606P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2425
_reflns_number_total             3419
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2505.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '438-440K' was changed to '439.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '438-440K' was changed to '439.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1572.6(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215591
_cod_database_fobs_code          2215591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
S S1 0.66053(5) 0.60400(10) 1.02262(4) 0.0457(2) Uani d . 1
S S2 0.42563(4) 0.72792(11) 0.53701(4) 0.0500(2) Uani d . 1
O O1 0.46099(14) 0.1525(3) 0.78293(11) 0.0650(6) Uani d . 1
C C1 0.49669(17) 0.3352(4) 0.78007(14) 0.0441(6) Uani d . 1
C C2 0.48304(16) 0.4675(4) 0.70766(13) 0.0428(6) Uani d . 1
C C3 0.53608(18) 0.6800(5) 0.70181(15) 0.0529(7) Uani d . 1
H H3A 0.4977 0.8077 0.7067 0.063 Uiso calc R 1
H H3B 0.5541 0.6869 0.6516 0.063 Uiso calc R 1
C C4 0.61929(19) 0.6951(5) 0.76260(15) 0.0599(8) Uani d . 1
H H4A 0.6625 0.5827 0.7528 0.072 Uiso calc R 1
H H4B 0.6469 0.8409 0.7603 0.072 Uiso calc R 1
C C5 0.59505(19) 0.6594(5) 0.84138(14) 0.0540(7) Uani d . 1
H H5A 0.6488 0.6735 0.8794 0.065 Uiso calc R 1
H H5B 0.5530 0.7743 0.8514 0.065 Uiso calc R 1
C C6 0.55374(16) 0.4335(4) 0.84869(13) 0.0416(6) Uani d . 1
C C7 0.56103(16) 0.3136(4) 0.91373(14) 0.0417(6) Uani d . 1
H H7 0.5328 0.1750 0.9078 0.050 Uiso calc R 1
C C8 0.60433(16) 0.3593(4) 0.99076(14) 0.0405(6) Uani d . 1
C C9 0.60517(18) 0.2174(4) 1.05115(15) 0.0485(6) Uani d . 1
H H9 0.5785 0.0767 1.0465 0.058 Uiso calc R 1
C C10 0.64957(18) 0.3018(5) 1.12083(15) 0.0523(7) Uani d . 1
H H10 0.6549 0.2228 1.1666 0.063 Uiso calc R 1
C C11 0.68413(17) 0.5092(5) 1.11535(14) 0.0475(6) Uani d . 1
C C12 0.7374(2) 0.6518(5) 1.17666(16) 0.0664(8) Uani d . 1
H H12A 0.7129 0.6373 1.2233 0.100 Uiso calc R 1
H H12B 0.7343 0.8054 1.1606 0.100 Uiso calc R 1
H H12C 0.7990 0.6038 1.1852 0.100 Uiso calc R 1
C C13 0.42223(17) 0.3906(4) 0.64973(14) 0.0449(6) Uani d . 1
H H13 0.3942 0.2582 0.6604 0.054 Uiso calc R 1
C C14 0.39269(16) 0.4772(4) 0.57379(13) 0.0431(6) Uani d . 1
C C15 0.33238(17) 0.3723(4) 0.51864(15) 0.0491(6) Uani d . 1
H H15 0.3056 0.2361 0.5266 0.059 Uiso calc R 1
C C16 0.31508(17) 0.4888(5) 0.44959(15) 0.0515(6) Uani d . 1
H H16 0.2764 0.4359 0.4071 0.062 Uiso calc R 1
C C17 0.35950(16) 0.6853(4) 0.44977(14) 0.0457(6) Uani d . 1
C C18 0.3575(2) 0.8562(5) 0.38763(16) 0.0616(8) Uani d . 1
H H18A 0.3248 0.7977 0.3407 0.092 Uiso calc R 1
H H18B 0.4179 0.8909 0.3807 0.092 Uiso calc R 1
H H18C 0.3285 0.9894 0.4016 0.092 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
C11 S1 C8 92.72(12)
C17 S2 C14 92.81(12)
O1 C1 C6 121.2(2)
O1 C1 C2 120.6(2)
C6 C1 C2 118.2(2)
C13 C2 C1 117.2(2)
C13 C2 C3 122.6(2)
C1 C2 C3 120.2(2)
C2 C3 C4 112.7(2)
C2 C3 H3A 109.0
C4 C3 H3A 109.0
C2 C3 H3B 109.0
C4 C3 H3B 109.0
H3A C3 H3B 107.8
C5 C4 C3 110.5(2)
C5 C4 H4A 109.5
C3 C4 H4A 109.5
C5 C4 H4B 109.5
C3 C4 H4B 109.5
H4A C4 H4B 108.1
C6 C5 C4 111.8(2)
C6 C5 H5A 109.3
C4 C5 H5A 109.3
C6 C5 H5B 109.3
C4 C5 H5B 109.3
H5A C5 H5B 107.9
C7 C6 C1 116.3(2)
C7 C6 C5 125.1(2)
C1 C6 C5 118.5(2)
C6 C7 C8 132.2(2)
C6 C7 H7 113.9
C8 C7 H7 113.9
C9 C8 C7 124.7(2)
C9 C8 S1 109.08(19)
C7 C8 S1 126.15(18)
C8 C9 C10 114.2(2)
C8 C9 H9 122.9
C10 C9 H9 122.9
C11 C10 C9 113.7(2)
C11 C10 H10 123.1
C9 C10 H10 123.1
C10 C11 C12 129.3(2)
C10 C11 S1 110.32(19)
C12 C11 S1 120.4(2)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C2 C13 C14 131.3(2)
C2 C13 H13 114.4
C14 C13 H13 114.4
C15 C14 C13 124.6(2)
C15 C14 S2 108.91(19)
C13 C14 S2 126.47(18)
C14 C15 C16 113.8(2)
C14 C15 H15 123.1
C16 C15 H15 123.1
C17 C16 C15 114.1(2)
C17 C16 H16 122.9
C15 C16 H16 122.9
C16 C17 C18 129.7(2)
C16 C17 S2 110.30(19)
C18 C17 S2 120.0(2)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.718(2)
S1 C8 1.738(2)
S2 C17 1.717(2)
S2 C14 1.738(2)
O1 C1 1.222(3)
C1 C6 1.491(3)
C1 C2 1.491(3)
C2 C13 1.342(3)
C2 C3 1.513(3)
C3 C4 1.518(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.511(4)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.501(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.345(3)
C7 C8 1.440(3)
C7 H7 0.9300
C8 C9 1.363(3)
C9 C10 1.399(4)
C9 H9 0.9300
C10 C11 1.355(4)
C10 H10 0.9300
C11 C12 1.506(4)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 C14 1.442(3)
C13 H13 0.9300
C14 C15 1.374(3)
C15 C16 1.394(4)
C15 H15 0.9300
C16 C17 1.352(4)
C16 H16 0.9300
C17 C18 1.497(4)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 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
O1 C1 C2 C13 7.8(4)
C6 C1 C2 C13 -171.3(2)
O1 C1 C2 C3 -172.7(3)
C6 C1 C2 C3 8.2(3)
C13 C2 C3 C4 -161.9(3)
C1 C2 C3 C4 18.6(4)
C2 C3 C4 C5 -52.5(3)
C3 C4 C5 C6 60.4(3)
O1 C1 C6 C7 -2.1(4)
C2 C1 C6 C7 177.1(2)
O1 C1 C6 C5 -179.6(3)
C2 C1 C6 C5 -0.4(3)
C4 C5 C6 C7 149.1(3)
C4 C5 C6 C1 -33.6(3)
C1 C6 C7 C8 -175.5(2)
C5 C6 C7 C8 1.8(4)
C6 C7 C8 C9 179.8(2)
C6 C7 C8 S1 1.9(4)
C11 S1 C8 C9 0.4(2)
C11 S1 C8 C7 178.6(2)
C7 C8 C9 C10 -178.3(2)
S1 C8 C9 C10 -0.1(3)
C8 C9 C10 C11 -0.4(3)
C9 C10 C11 C12 -178.7(3)
C9 C10 C11 S1 0.6(3)
C8 S1 C11 C10 -0.6(2)
C8 S1 C11 C12 178.8(2)
C1 C2 C13 C14 179.4(2)
C3 C2 C13 C14 -0.1(4)
C2 C13 C14 C15 176.4(3)
C2 C13 C14 S2 -4.2(4)
C17 S2 C14 C15 -0.5(2)
C17 S2 C14 C13 -180.0(2)
C13 C14 C15 C16 -179.6(2)
S2 C14 C15 C16 0.9(3)
C14 C15 C16 C17 -1.1(3)
C15 C16 C17 C18 -179.2(3)
C15 C16 C17 S2 0.7(3)
C14 S2 C17 C16 -0.1(2)
C14 S2 C17 C18 179.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1825679
2 PubChem 2445714
