#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/61/2226189.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_2226189
loop_
_publ_author_name
'Thippeswamy, G. B.'
'Vijay Kumar, D.'
'Jayashree, B. S.'
'Sridhar, M. A.'
'Shashidhara Prasad, J.'
_publ_section_title
;
 1-(2-Hydroxy-5-methylphenyl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one
;
_journal_coeditor_code           JH2143
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1385
_journal_paper_doi               10.1107/S1600536810017058
_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         258.33
_chemical_name_systematic
;
1-(2-Hydroxy-5-methylphenyl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.6680(12)
_cell_length_b                   13.3750(8)
_cell_length_c                   14.5410(14)
_cell_measurement_reflns_used    4360
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      3.17
_cell_volume                     2658.2(4)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'XPRESS (MacScience, 2002)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and ORTEPII (Johnson, 1976)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MacScience DIPLabo 32001'
_diffrn_measurement_method       'ω 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  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4360
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.351
_refine_ls_extinction_coef       0.009975
_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   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1131P)²+0.2932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.1824
_reflns_number_gt                1742
_reflns_number_total             2335
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2143.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2226189
_cod_database_fobs_code          2226189
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'
'-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_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 S14 0.03308(6) 0.63213(6) 0.34076(5) 0.0917(3) Uani . . 1.000
O O1 -0.30633(16) 0.21283(14) 0.47357(17) 0.1086(9) Uani . . 1.000
O O10 -0.14602(14) 0.28250(13) 0.41732(14) 0.0902(7) Uani . . 1.000
C C2 -0.32536(19) 0.3053(2) 0.5061(2) 0.0824(9) Uani . . 1.000
C C3 -0.4133(2) 0.3227(3) 0.5511(2) 0.0998(11) Uani . . 1.000
C C4 -0.4358(2) 0.4136(3) 0.5850(2) 0.0968(13) Uani . . 1.000
C C5 -0.37207(18) 0.4947(2) 0.57621(16) 0.0817(9) Uani . . 1.000
C C6 -0.28521(17) 0.47858(19) 0.53026(16) 0.0714(8) Uani . . 1.000
C C7 -0.25907(16) 0.38552(17) 0.49421(16) 0.0681(8) Uani . . 1.000
C C8 -0.3971(2) 0.5955(3) 0.6154(2) 0.1067(14) Uani . . 1.000
C C9 -0.16789(18) 0.36901(17) 0.44277(16) 0.0692(8) Uani . . 1.000
C C11 -0.10438(16) 0.45228(18) 0.41721(15) 0.0685(8) Uani . . 1.000
C C12 -0.02561(16) 0.43481(19) 0.36459(17) 0.0702(8) Uani . . 1.000
C C13 0.04379(16) 0.5047(2) 0.32810(16) 0.0724(8) Uani . . 1.000
C C15 0.1358(3) 0.6508(3) 0.2772(2) 0.1040(12) Uani . . 1.000
C C16 0.1769(2) 0.5658(3) 0.2486(2) 0.0996(13) Uani . . 1.000
C C17 0.12548(19) 0.4798(2) 0.27636(17) 0.0830(9) Uani . . 1.000
C C18 0.1554(2) 0.3751(3) 0.2526(2) 0.1080(14) Uani . . 1.000
H H1 -0.25310 0.21280 0.44750 0.1630 Uiso calc R 1.000
H H3 -0.45760 0.27050 0.55800 0.1200 Uiso calc R 1.000
H H4 -0.49520 0.42260 0.61500 0.1160 Uiso calc R 1.000
H H6 -0.24220 0.53190 0.52300 0.0860 Uiso calc R 1.000
H H8A -0.35680 0.64560 0.58720 0.1600 Uiso calc R 1.000
H H8B -0.38590 0.59510 0.68060 0.1600 Uiso calc R 1.000
H H8C -0.46470 0.61010 0.60350 0.1600 Uiso calc R 1.000
H H11 -0.11840 0.51680 0.43720 0.0820 Uiso calc R 1.000
H H12 -0.01450 0.36810 0.34970 0.0840 Uiso calc R 1.000
H H15 0.16080 0.71380 0.26380 0.1250 Uiso calc R 1.000
H H16 0.23380 0.56360 0.21360 0.1200 Uiso calc R 1.000
H H18A 0.14980 0.33340 0.30610 0.1620 Uiso calc R 1.000
H H18B 0.22200 0.37500 0.23160 0.1620 Uiso calc R 1.000
H H18C 0.11370 0.34980 0.20490 0.1620 Uiso calc R 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'
N N 0.0061 0.0033 '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
C13 S14 C15 . . . 90.98(16) yes
C2 O1 H1 . . . 109.00 no
O1 C2 C7 . . . 121.9(2) yes
C3 C2 C7 . . . 119.0(3) no
O1 C2 C3 . . . 119.1(3) yes
C2 C3 C4 . . . 121.4(3) no
C3 C4 C5 . . . 121.7(3) no
C4 C5 C6 . . . 117.4(3) no
C4 C5 C8 . . . 121.3(2) no
C6 C5 C8 . . . 121.3(2) no
C5 C6 C7 . . . 122.8(2) no
C2 C7 C6 . . . 117.8(2) no
C6 C7 C9 . . . 122.8(2) no
C2 C7 C9 . . . 119.4(2) no
O10 C9 C11 . . . 119.2(2) yes
C7 C9 C11 . . . 121.3(2) no
O10 C9 C7 . . . 119.5(2) yes
C9 C11 C12 . . . 119.3(2) no
C11 C12 C13 . . . 129.0(2) no
S14 C13 C12 . . . 123.37(18) yes
C12 C13 C17 . . . 125.2(2) no
S14 C13 C17 . . . 111.37(19) yes
S14 C15 C16 . . . 113.1(3) yes
C15 C16 C17 . . . 113.4(3) no
C13 C17 C18 . . . 124.7(2) no
C16 C17 C18 . . . 124.1(2) no
C13 C17 C16 . . . 111.2(2) no
C2 C3 H3 . . . 119.00 no
C4 C3 H3 . . . 119.00 no
C3 C4 H4 . . . 119.00 no
C5 C4 H4 . . . 119.00 no
C5 C6 H6 . . . 119.00 no
C7 C6 H6 . . . 119.00 no
C5 C8 H8A . . . 109.00 no
C5 C8 H8B . . . 109.00 no
C5 C8 H8C . . . 109.00 no
H8A C8 H8B . . . 110.00 no
H8A C8 H8C . . . 109.00 no
H8B C8 H8C . . . 109.00 no
C9 C11 H11 . . . 120.00 no
C12 C11 H11 . . . 120.00 no
C11 C12 H12 . . . 116.00 no
C13 C12 H12 . . . 116.00 no
S14 C15 H15 . . . 123.00 no
C16 C15 H15 . . . 124.00 no
C15 C16 H16 . . . 123.00 no
C17 C16 H16 . . . 123.00 no
C17 C18 H18A . . . 110.00 no
C17 C18 H18B . . . 109.00 no
C17 C18 H18C . . . 110.00 no
H18A C18 H18B . . . 109.00 no
H18A C18 H18C . . . 109.00 no
H18B C18 H18C . . . 109.00 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
S14 C13 . . 1.721(3) yes
S14 C15 . . 1.699(4) yes
O1 C2 . . 1.350(3) yes
O10 C9 . . 1.251(3) yes
O1 H1 . . 0.8200 no
C2 C7 . . 1.415(3) no
C2 C3 . . 1.388(4) no
C3 C4 . . 1.348(5) no
C4 C5 . . 1.397(4) no
C5 C6 . . 1.379(3) no
C5 C8 . . 1.503(5) no
C6 C7 . . 1.397(3) no
C7 C9 . . 1.470(3) no
C9 C11 . . 1.460(3) no
C11 C12 . . 1.341(3) no
C12 C13 . . 1.434(3) no
C13 C17 . . 1.387(3) no
C15 C16 . . 1.335(5) no
C16 C17 . . 1.407(5) no
C17 C18 . . 1.499(5) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C6 H6 . . 0.9300 no
C8 H8A . . 0.9600 no
C8 H8B . . 0.9600 no
C8 H8C . . 0.9600 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C15 H15 . . 0.9300 no
C16 H16 . . 0.9300 no
C18 H18A . . 0.9600 no
C18 H18B . . 0.9600 no
C18 H18C . . 0.9600 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 O10 . 0.8200 1.7900 2.518(3) 147.00 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
C15 S14 C13 C12 . . . . -177.8(2) no
C15 S14 C13 C17 . . . . 0.4(2) no
C13 S14 C15 C16 . . . . -0.7(3) no
O1 C2 C7 C6 . . . . 180.0(2) no
C3 C2 C7 C6 . . . . 1.1(4) no
C3 C2 C7 C9 . . . . -177.1(2) no
O1 C2 C7 C9 . . . . 1.8(4) no
O1 C2 C3 C4 . . . . 179.9(3) no
C7 C2 C3 C4 . . . . -1.3(4) no
C2 C3 C4 C5 . . . . 0.3(5) no
C3 C4 C5 C8 . . . . -179.1(3) no
C3 C4 C5 C6 . . . . 0.8(4) no
C8 C5 C6 C7 . . . . 179.0(2) no
C4 C5 C6 C7 . . . . -0.9(4) no
C5 C6 C7 C2 . . . . -0.1(4) no
C5 C6 C7 C9 . . . . 178.1(2) no
C2 C7 C9 C11 . . . . 170.9(2) no
C6 C7 C9 C11 . . . . -7.2(4) no
C2 C7 C9 O10 . . . . -6.3(4) no
C6 C7 C9 O10 . . . . 175.6(2) no
O10 C9 C11 C12 . . . . 2.1(3) no
C7 C9 C11 C12 . . . . -175.2(2) no
C9 C11 C12 C13 . . . . 177.0(2) no
C11 C12 C13 S14 . . . . -4.3(4) no
C11 C12 C13 C17 . . . . 177.8(2) no
S14 C13 C17 C16 . . . . 0.0(3) no
C12 C13 C17 C16 . . . . 178.1(2) no
C12 C13 C17 C18 . . . . -1.7(4) no
S14 C13 C17 C18 . . . . -179.8(2) no
S14 C15 C16 C17 . . . . 0.8(4) no
C15 C16 C17 C13 . . . . -0.5(4) no
C15 C16 C17 C18 . . . . 179.4(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745062
