#------------------------------------------------------------------------------
#$Date: 2011-09-16 18:46:08 +0300 (Fri, 16 Sep 2011) $
#$Revision: 26025 $
#$URL: file:///home/coder/svn-repositories/cod/hkl/2/2215591.hkl $
#------------------------------------------------------------------------------
#
# 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_Fobs
loop_
_publ_author_name
'Liang, Guang'
'Yang, Shu-Lin'
'Wang, Xiao-Hui'
'Li, Yue-Ru'
'Li, Xiao-Kun'
_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_volume 63
_journal_year 2007
_chemical_formula_moiety ?
_chemical_formula_sum 'C18 H18 O S2'
_chemical_formula_weight 314.44
_chemical_melting_point ?
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_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
_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(4)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type '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 0.1177
_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
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_exptl_absorpt_coefficient_mu 0.334
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.6931
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.328
_exptl_crystal_density_meas ?
_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_diff_density_rms 0.069
_refine_ls_extinction_coef ?
_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/[\s^2^(Fo^2^)+(0.0606P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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 >2sigma(I)
_[local]_cod_data_source_file lh2505Isup2.hkl
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M P2(1)/n
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.66053(5) 0.60400(10) 1.02262(4) 0.0457(2) Uani 1 1 d . . .
S2 S 0.42563(4) 0.72792(11) 0.53701(4) 0.0500(2) Uani 1 1 d . . .
O1 O 0.46099(14) 0.1525(3) 0.78293(11) 0.0650(6) Uani 1 1 d . . .
C1 C 0.49669(17) 0.3352(4) 0.78007(14) 0.0441(6) Uani 1 1 d . . .
C2 C 0.48304(16) 0.4675(4) 0.70766(13) 0.0428(6) Uani 1 1 d . . .
C3 C 0.53608(18) 0.6800(5) 0.70181(15) 0.0529(7) Uani 1 1 d . . .
H3A H 0.4977 0.8077 0.7067 0.063 Uiso 1 1 calc R . .
H3B H 0.5541 0.6869 0.6516 0.063 Uiso 1 1 calc R . .
C4 C 0.61929(19) 0.6951(5) 0.76260(15) 0.0599(8) Uani 1 1 d . . .
H4A H 0.6625 0.5827 0.7528 0.072 Uiso 1 1 calc R . .
H4B H 0.6469 0.8409 0.7603 0.072 Uiso 1 1 calc R . .
C5 C 0.59505(19) 0.6594(5) 0.84138(14) 0.0540(7) Uani 1 1 d . . .
H5A H 0.6488 0.6735 0.8794 0.065 Uiso 1 1 calc R . .
H5B H 0.5530 0.7743 0.8514 0.065 Uiso 1 1 calc R . .
C6 C 0.55374(16) 0.4335(4) 0.84869(13) 0.0416(6) Uani 1 1 d . . .
C7 C 0.56103(16) 0.3136(4) 0.91373(14) 0.0417(6) Uani 1 1 d . . .
H7 H 0.5328 0.1750 0.9078 0.050 Uiso 1 1 calc R . .
C8 C 0.60433(16) 0.3593(4) 0.99076(14) 0.0405(6) Uani 1 1 d . . .
C9 C 0.60517(18) 0.2174(4) 1.05115(15) 0.0485(6) Uani 1 1 d . . .
H9 H 0.5785 0.0767 1.0465 0.058 Uiso 1 1 calc R . .
C10 C 0.64957(18) 0.3018(5) 1.12083(15) 0.0523(7) Uani 1 1 d . . .
H10 H 0.6549 0.2228 1.1666 0.063 Uiso 1 1 calc R . .
C11 C 0.68413(17) 0.5092(5) 1.11535(14) 0.0475(6) Uani 1 1 d . . .
C12 C 0.7374(2) 0.6518(5) 1.17666(16) 0.0664(8) Uani 1 1 d . . .
H12A H 0.7129 0.6373 1.2233 0.100 Uiso 1 1 calc R . .
H12B H 0.7343 0.8054 1.1606 0.100 Uiso 1 1 calc R . .
H12C H 0.7990 0.6038 1.1852 0.100 Uiso 1 1 calc R . .
C13 C 0.42223(17) 0.3906(4) 0.64973(14) 0.0449(6) Uani 1 1 d . . .
H13 H 0.3942 0.2582 0.6604 0.054 Uiso 1 1 calc R . .
C14 C 0.39269(16) 0.4772(4) 0.57379(13) 0.0431(6) Uani 1 1 d . . .
C15 C 0.33238(17) 0.3723(4) 0.51864(15) 0.0491(6) Uani 1 1 d . . .
H15 H 0.3056 0.2361 0.5266 0.059 Uiso 1 1 calc R . .
C16 C 0.31508(17) 0.4888(5) 0.44959(15) 0.0515(6) Uani 1 1 d . . .
H16 H 0.2764 0.4359 0.4071 0.062 Uiso 1 1 calc R . .
C17 C 0.35950(16) 0.6853(4) 0.44977(14) 0.0457(6) Uani 1 1 d . . .
C18 C 0.3575(2) 0.8562(5) 0.38763(16) 0.0616(8) Uani 1 1 d . . .
H18A H 0.3248 0.7977 0.3407 0.092 Uiso 1 1 calc R . .
H18B H 0.4179 0.8909 0.3807 0.092 Uiso 1 1 calc R . .
H18C H 0.3285 0.9894 0.4016 0.092 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0494(4) 0.0454(4) 0.0407(4) 0.0017(3) 0.0025(3) -0.0035(3)
S2 0.0466(4) 0.0566(4) 0.0437(4) 0.0006(3) -0.0021(3) -0.0097(3)
O1 0.0870(16) 0.0497(11) 0.0512(12) 0.0022(9) -0.0104(10) -0.0167(10)
C1 0.0469(15) 0.0414(14) 0.0422(14) -0.0019(10) 0.0012(11) -0.0026(11)
C2 0.0405(14) 0.0490(14) 0.0383(13) -0.0025(11) 0.0043(10) -0.0016(11)
C3 0.0497(16) 0.0669(17) 0.0391(14) 0.0048(12) -0.0023(11) -0.0130(13)
C4 0.0556(18) 0.0796(19) 0.0416(16) 0.0056(13) -0.0016(12) -0.0251(15)
C5 0.0581(18) 0.0630(17) 0.0378(14) 0.0037(12) -0.0015(12) -0.0171(13)
C6 0.0391(14) 0.0456(14) 0.0396(13) -0.0006(10) 0.0044(10) -0.0003(11)
C7 0.0390(14) 0.0408(13) 0.0446(14) 0.0004(10) 0.0047(11) -0.0001(10)
C8 0.0342(13) 0.0420(14) 0.0445(14) 0.0030(10) 0.0034(10) 0.0010(10)
C9 0.0440(15) 0.0463(15) 0.0533(16) 0.0093(11) 0.0020(12) -0.0019(11)
C10 0.0539(17) 0.0612(17) 0.0401(15) 0.0123(12) 0.0018(12) 0.0029(13)
C11 0.0440(15) 0.0577(16) 0.0393(14) 0.0004(11) 0.0015(11) 0.0059(12)
C12 0.071(2) 0.080(2) 0.0450(17) -0.0083(14) -0.0024(14) -0.0059(17)
C13 0.0434(14) 0.0484(15) 0.0425(14) -0.0023(11) 0.0052(11) -0.0041(11)
C14 0.0372(13) 0.0494(14) 0.0424(14) -0.0046(11) 0.0050(10) -0.0036(11)
C15 0.0403(15) 0.0564(16) 0.0490(15) -0.0031(12) 0.0028(11) -0.0085(12)
C16 0.0414(15) 0.0676(17) 0.0421(15) -0.0093(12) -0.0038(11) -0.0013(13)
C17 0.0363(14) 0.0595(16) 0.0398(14) -0.0023(11) 0.0018(10) -0.0005(12)
C18 0.0581(19) 0.073(2) 0.0516(17) 0.0088(14) 0.0025(14) 0.0001(15)
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_
_audit_creation_method
SHELXL-97
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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_
_refln_index_h
_refln_index_k
_refln_index_l
_refln_F_squared_calc
_refln_F_squared_meas
_refln_F_squared_sigma
_refln_observed_status
2 0 0 12680.40 13930.46 114.85 o