#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/71/2227177.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227177
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Khan, Salman A.'
'Tahir, M. Nawaz'
_publ_section_title
;
 (E)-1-(2,5-Dimethyl-3-thienyl)-3-(2-hydroxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           BQ2228
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2259
_journal_page_last               o2260
_journal_paper_doi               10.1107/S1600536810031284
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H14 O2 S'
_chemical_formula_moiety         'C15 H14 O2 S'
_chemical_formula_sum            'C15 H14 O2 S'
_chemical_formula_weight         258.32
_chemical_name_systematic
;
(E)-1-(2,5-Dimethyl-3-thienyl)-3-(2-hydroxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.527(2)
_cell_angle_beta                 91.943(2)
_cell_angle_gamma                115.5510(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6095(3)
_cell_length_b                   7.7900(3)
_cell_length_c                   12.3109(7)
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.51
_cell_volume                     647.19(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.10
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11156
_diffrn_reflns_theta_full        28.63
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         2.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.228
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0376
_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)+(0.0593P)²+0.1362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                2720
_reflns_number_total             3174
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2228.cif
_cod_data_source_block           I
_cod_database_code               2227177
_cod_database_fobs_code          2227177
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.67628(6) 1.06807(5) 0.38493(3) 0.04750(10) Uani . . 1.000
O O1 0.75707(17) 0.38399(14) -0.02745(8) 0.0464(3) Uani . . 1.000
O O2 0.73309(16) 1.04466(13) 0.01642(8) 0.0461(3) Uani . . 1.000
C C1 0.79715(18) 0.57560(16) -0.16540(10) 0.0329(3) Uani . . 1.000
C C2 0.78885(19) 0.40687(17) -0.13253(10) 0.0343(3) Uani . . 1.000
C C3 0.8126(2) 0.26851(19) -0.20796(12) 0.0434(4) Uani . . 1.000
C C4 0.8396(3) 0.2929(2) -0.31564(12) 0.0504(5) Uani . . 1.000
C C5 0.8450(3) 0.4557(2) -0.35080(12) 0.0507(5) Uani . . 1.000
C C6 0.8256(2) 0.5950(2) -0.27561(11) 0.0427(4) Uani . . 1.000
C C7 0.77922(19) 0.73111(17) -0.09244(10) 0.0343(3) Uani . . 1.000
C C8 0.7412(2) 0.74553(17) 0.01224(11) 0.0370(3) Uani . . 1.000
C C9 0.72983(18) 0.92090(16) 0.06888(10) 0.0334(3) Uani . . 1.000
C C10 0.71496(18) 0.94215(17) 0.18852(10) 0.0337(3) Uani . . 1.000
C C11 0.7304(2) 0.81420(19) 0.25716(11) 0.0429(4) Uani . . 1.000
C C12 0.7131(2) 0.8629(2) 0.36472(12) 0.0478(4) Uani . . 1.000
C C13 0.7182(3) 0.7610(3) 0.45856(15) 0.0714(7) Uani . . 1.000
C C14 0.68407(19) 1.08881(17) 0.24864(10) 0.0360(4) Uani . . 1.000
C C15 0.6562(3) 1.2516(2) 0.21248(12) 0.0484(5) Uani . . 1.000
H H1 0.75495 0.28106 -0.01816 0.0696 Uiso . . 1.000
H H3 0.81024 0.15882 -0.18542 0.0520 Uiso . . 1.000
H H4 0.85434 0.19895 -0.36531 0.0605 Uiso . . 1.000
H H5 0.86144 0.47102 -0.42384 0.0609 Uiso . . 1.000
H H6 0.83168 0.70550 -0.29889 0.0513 Uiso . . 1.000
H H7 0.79737 0.83780 -0.12429 0.0411 Uiso . . 1.000
H H8 0.72160 0.64484 0.04996 0.0445 Uiso . . 1.000
H H11 0.75059 0.70703 0.22980 0.0515 Uiso . . 1.000
H H13A 0.73513 0.64780 0.43117 0.1070 Uiso . . 1.000
H H13B 0.59731 0.72392 0.49126 0.1070 Uiso . . 1.000
H H13C 0.82534 0.84640 0.51317 0.1070 Uiso . . 1.000
H H15A 0.77811 1.34346 0.19316 0.0725 Uiso . . 1.000
H H15B 0.61341 1.31403 0.27168 0.0725 Uiso . . 1.000
H H15C 0.55936 1.20163 0.14942 0.0725 Uiso . . 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 S1 C14 . . . 93.47(7) no
C2 O1 H1 . . . 109.00 no
C2 C1 C7 . . . 124.39(11) no
C6 C1 C7 . . . 118.02(11) no
C2 C1 C6 . . . 117.59(12) no
O1 C2 C3 . . . 121.65(12) no
C1 C2 C3 . . . 120.04(12) no
O1 C2 C1 . . . 118.31(12) no
C2 C3 C4 . . . 120.50(13) no
C3 C4 C5 . . . 120.73(15) no
C4 C5 C6 . . . 118.88(14) no
C1 C6 C5 . . . 122.23(13) no
C1 C7 C8 . . . 130.57(12) no
C7 C8 C9 . . . 120.25(11) no
O2 C9 C10 . . . 121.58(12) no
C8 C9 C10 . . . 118.20(11) no
O2 C9 C8 . . . 120.22(11) no
C9 C10 C14 . . . 123.69(11) no
C11 C10 C14 . . . 111.61(11) no
C9 C10 C11 . . . 124.70(12) no
C10 C11 C12 . . . 114.24(13) no
S1 C12 C13 . . . 121.37(12) no
C11 C12 C13 . . . 128.61(15) no
S1 C12 C11 . . . 110.00(11) no
S1 C14 C15 . . . 118.86(10) no
C10 C14 C15 . . . 130.46(12) no
S1 C14 C10 . . . 110.68(10) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 121.00 no
C6 C5 H5 . . . 121.00 no
C1 C6 H6 . . . 119.00 no
C5 C6 H6 . . . 119.00 no
C1 C7 H7 . . . 115.00 no
C8 C7 H7 . . . 115.00 no
C7 C8 H8 . . . 120.00 no
C9 C8 H8 . . . 120.00 no
C10 C11 H11 . . . 123.00 no
C12 C11 H11 . . . 123.00 no
C12 C13 H13A . . . 109.00 no
C12 C13 H13B . . . 109.00 no
C12 C13 H13C . . . 109.00 no
H13A C13 H13B . . . 109.00 no
H13A C13 H13C . . . 110.00 no
H13B C13 H13C . . . 109.00 no
C14 C15 H15A . . . 109.00 no
C14 C15 H15B . . . 109.00 no
C14 C15 H15C . . . 109.00 no
H15A C15 H15B . . . 109.00 no
H15A C15 H15C . . . 109.00 no
H15B C15 H15C . . . 110.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C12 . . 1.7228(16) no
S1 C14 . . 1.7099(13) no
O1 C2 . . 1.3476(16) no
O2 C9 . . 1.2298(15) no
O1 H1 . . 0.8200 no
C1 C6 . . 1.4011(18) no
C1 C7 . . 1.4564(18) no
C1 C2 . . 1.4083(17) no
C2 C3 . . 1.393(2) no
C3 C4 . . 1.377(2) no
C4 C5 . . 1.384(2) no
C5 C6 . . 1.381(2) no
C7 C8 . . 1.3295(18) no
C8 C9 . . 1.4777(18) no
C9 C10 . . 1.4713(17) no
C10 C11 . . 1.4372(19) no
C10 C14 . . 1.3788(19) no
C11 C12 . . 1.349(2) no
C12 C13 . . 1.504(2) no
C14 C15 . . 1.498(2) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C7 H7 . . 0.9300 no
C8 H8 . . 0.9300 no
C11 H11 . . 0.9300 no
C13 H13A . . 0.9600 no
C13 H13B . . 0.9600 no
C13 H13C . . 0.9600 no
C15 H15A . . 0.9600 no
C15 H15B . . 0.9600 no
C15 H15C . . 0.9600 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 C4 3.686(2) . 2_665 no
S1 H4 3.1500 . 1_566 no
O1 O2 2.7067(14) . 1_545 no
O1 C8 2.8416(17) . . no
O1 C15 3.2790(18) . 1_545 no
O1 C9 3.3986(19) . 2_665 no
O2 O1 2.7067(14) . 1_565 no
O2 C3 3.4160(17) . 1_565 no
O2 C15 2.919(2) . . no
O2 C7 3.3745(19) . 2_775 no
O1 H15A 2.7900 . 1_545 no
O1 H15C 2.8800 . 1_545 no
O1 H8 2.2400 . . no
O2 H1 1.8900 . 1_565 no
O2 H3 2.7600 . 1_565 no
O2 H15A 2.8300 . . no
O2 H15C 2.6200 . . no
O2 H7 2.4000 . . no
O2 H15C 2.7700 . 2_675 no
C2 C10 3.583(2) . 2_665 no
C3 O2 3.4160(17) . 1_545 no
C3 C14 3.559(2) . 2_665 no
C4 S1 3.686(2) . 2_665 no
C6 C14 3.442(2) . 2_775 no
C7 C9 3.5138(19) . 2_775 no
C7 O2 3.3745(19) . 2_775 no
C8 O1 2.8416(17) . . no
C9 O1 3.3986(19) . 2_665 no
C9 C7 3.5138(19) . 2_775 no
C10 C2 3.583(2) . 2_665 no
C14 C3 3.559(2) . 2_665 no
C14 C6 3.442(2) . 2_775 no
C15 O2 2.919(2) . . no
C15 O1 3.2790(18) . 1_565 no
C1 H15A 3.0600 . 2_775 no
C2 H8 2.9000 . . no
C5 H15A 3.0500 . 2_775 no
C6 H15A 2.9600 . 2_775 no
C7 H15C 2.9200 . 2_675 no
C8 H11 2.7400 . . no
C9 H15C 3.0600 . . no
C9 H1 3.0800 . 1_565 no
C11 H8 2.6800 . . no
C15 H1 2.9800 . 1_565 no
H1 O2 1.8900 . 1_545 no
H1 C9 3.0800 . 1_545 no
H1 C15 2.9800 . 1_545 no
H1 H3 2.2700 . . no
H1 H15A 2.5600 . 1_545 no
H1 H15C 2.5800 . 1_545 no
H3 O2 2.7600 . 1_545 no
H3 H1 2.2700 . . no
H4 S1 3.1500 . 1_544 no
H6 H7 2.3200 . . no
H7 O2 2.4000 . . no
H7 H6 2.3200 . . no
H7 H15C 2.6000 . 2_675 no
H8 O1 2.2400 . . no
H8 C2 2.9000 . . no
H8 C11 2.6800 . . no
H8 H11 2.1800 . . no
H11 C8 2.7400 . . no
H11 H8 2.1800 . . no
H11 H13A 2.5900 . . no
H13A H11 2.5900 . . no
H15A O1 2.7900 . 1_565 no
H15A O2 2.8300 . . no
H15A H1 2.5600 . 1_565 no
H15A C1 3.0600 . 2_775 no
H15A C5 3.0500 . 2_775 no
H15A C6 2.9600 . 2_775 no
H15C O1 2.8800 . 1_565 no
H15C O2 2.6200 . . no
H15C C9 3.0600 . . no
H15C H1 2.5800 . 1_565 no
H15C O2 2.7700 . 2_675 no
H15C C7 2.9200 . 2_675 no
H15C H7 2.6000 . 2_675 no
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
O1 H1 O2 1_545 0.82 1.8900 2.7067(14) 174 yes
C8 H8 O1 . 0.93 2.2400 2.8416(17) 122 yes
C15 H15A Cg2 2_775 0.96 2.79 3.652(2) 150 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
C14 S1 C12 C11 . . . . 0.02(16) no
C14 S1 C12 C13 . . . . -178.73(15) no
C12 S1 C14 C10 . . . . -0.21(12) no
C12 S1 C14 C15 . . . . 179.18(14) no
C6 C1 C2 O1 . . . . -178.51(14) no
C6 C1 C2 C3 . . . . 1.3(2) no
C7 C1 C2 O1 . . . . 1.8(2) no
C7 C1 C2 C3 . . . . -178.36(14) no
C2 C1 C6 C5 . . . . 0.1(2) no
C7 C1 C6 C5 . . . . 179.74(16) no
C2 C1 C7 C8 . . . . -4.6(3) no
C6 C1 C7 C8 . . . . 175.77(16) no
O1 C2 C3 C4 . . . . 178.23(16) no
C1 C2 C3 C4 . . . . -1.6(2) no
C2 C3 C4 C5 . . . . 0.4(3) no
C3 C4 C5 C6 . . . . 0.9(3) no
C4 C5 C6 C1 . . . . -1.2(3) no
C1 C7 C8 C9 . . . . -179.80(15) no
C7 C8 C9 O2 . . . . 8.3(2) no
C7 C8 C9 C10 . . . . -171.60(14) no
O2 C9 C10 C11 . . . . -173.33(14) no
O2 C9 C10 C14 . . . . 6.7(2) no
C8 C9 C10 C11 . . . . 6.6(2) no
C8 C9 C10 C14 . . . . -173.36(14) no
C9 C10 C11 C12 . . . . 179.67(14) no
C14 C10 C11 C12 . . . . -0.37(19) no
C9 C10 C14 S1 . . . . -179.69(11) no
C9 C10 C14 C15 . . . . 1.0(3) no
C11 C10 C14 S1 . . . . 0.36(16) no
C11 C10 C14 C15 . . . . -178.95(16) no
C10 C11 C12 S1 . . . . 0.21(18) no
C10 C11 C12 C13 . . . . 178.83(17) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745737
