#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/15/1551569.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_1551569
loop_
_publ_author_name
'SREENATHA, N. R.'
'LAKSHMINARAYANA, B. N.'
'GANESHA, D. P.'
'VIJAYSHANKAR, S.'
'NAGARAJU, S.'
_publ_section_title
;
 Crystal Structure and Hirshfeld Surfaces of
 (E)-1-(2-Hydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              23
_journal_paper_doi               10.2116/xraystruct.34.23
_journal_volume                  34
_journal_year                    2018
_chemical_formula_moiety         'C14 H12 O2 S'
_chemical_formula_sum            'C14 H12 O2 S'
_chemical_formula_weight         244.31
_chemical_name_common
(E)-1-(2-hydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 125.579(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2530(5)
_cell_length_b                   13.1530(14)
_cell_length_c                   14.1570(11)
_cell_measurement_reflns_used    2072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.52
_cell_volume                     1249.9(2)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'APEX (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics
'PLATON(Spek, 2003); ORTEP-II(Johnson, 1976)'
_computing_publication_material  'PLATON(Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.8403
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'APEX (Bruker, 1999)'
_diffrn_measurement_method       'SAINT (Bruker, 1999)'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2072
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.52
_diffrn_standards_interval_count 400
_diffrn_standards_interval_time  0
_diffrn_standards_number         2200
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al., 1967'
_exptl_crystal_colour            'light black'
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512.72
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.245
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0480
_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)+(0.1022P)²+0.2095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1616
_reflns_number_gt                1748
_reflns_number_total             2072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            34_23_1.txt
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/andrius/struct/COD-crude-data/automatic-downloads/current/J-STAGE/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 6524 2018-11-02 12:15:13Z antanas 
;
_cod_original_cell_volume        1249.87(18)
_cod_original_sg_symbol_H-M      p21/c
_cod_database_code               1551569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.31013(10) 0.98072(5) 0.26141(5) 0.0730(3) Uani 1 1 d .
O10 O 0.2413(3) 1.11453(14) -0.12065(15) 0.0767(5) Uani 1 1 d .
C8 C 0.2082(3) 1.09331(17) 0.03171(19) 0.0589(6) Uani 1 1 d .
H8 H 0.1594 1.1192 0.0718 0.071 Uiso 1 1 calc R
C7 C 0.3077(3) 1.00603(17) 0.0657(2) 0.0595(6) Uani 1 1 d .
H7 H 0.3523 0.9826 0.0225 0.071 Uiso 1 1 calc R
C9 C 0.1739(3) 1.14947(17) -0.06778(19) 0.0591(6) Uani 1 1 d .
C11 C 0.0654(3) 1.24592(17) -0.10452(18) 0.0576(5) Uani 1 1 d .
C5 C 0.3541(3) 0.94368(17) 0.16224(18) 0.0579(6) Uani 1 1 d .
C16 C 0.0261(4) 1.29571(19) -0.2047(2) 0.0660(6) Uani 1 1 d .
O17 O 0.0862(3) 1.25773(15) -0.26744(16) 0.0884(6) Uani 1 1 d .
H17 H 0.1467 1.2044 -0.2381 0.133 Uiso 1 1 calc R
C4 C 0.4356(4) 0.84835(19) 0.1887(2) 0.0682(6) Uani 1 1 d .
H4 H 0.4706 0.8146 0.1453 0.082 Uiso 1 1 calc R
C12 C -0.0015(4) 1.29316(18) -0.0447(2) 0.0668(6) Uani 1 1 d .
H12 H 0.0233 1.2623 0.0216 0.080 Uiso 1 1 calc R
C3 C 0.4610(4) 0.8067(2) 0.2871(2) 0.0760(7) Uani 1 1 d .
H3 H 0.5140 0.7423 0.3153 0.091 Uiso 1 1 calc R
C15 C -0.0784(4) 1.3869(2) -0.2409(2) 0.0797(8) Uani 1 1 d .
H15 H -0.1052 1.4190 -0.3072 0.096 Uiso 1 1 calc R
C2 C 0.4018(4) 0.8682(2) 0.3373(2) 0.0720(7) Uani 1 1 d .
C13 C -0.1030(4) 1.3839(2) -0.0811(3) 0.0821(8) Uani 1 1 d .
H13 H -0.1450 1.4141 -0.0394 0.099 Uiso 1 1 calc R
C14 C -0.1421(4) 1.4299(2) -0.1802(3) 0.0864(8) Uani 1 1 d .
H14 H -0.2125 1.4907 -0.2057 0.104 Uiso 1 1 calc R
C6 C 0.4044(5) 0.8495(3) 0.4430(3) 0.1061(11) Uani 1 1 d .
H6A H 0.4103 0.7777 0.4568 0.159 Uiso 1 1 calc R
H6B H 0.2856 0.8770 0.4306 0.159 Uiso 1 1 calc R
H6C H 0.5190 0.8818 0.5092 0.159 Uiso 1 1 calc R
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
C5 S1 C2 92.34(12)
C7 C8 C9 121.1(2)
C7 C8 H8 119.5
C9 C8 H8 119.5
C8 C7 C5 127.0(2)
C8 C7 H7 116.5
C5 C7 H7 116.5
O10 C9 C11 119.9(2)
O10 C9 C8 119.1(2)
C11 C9 C8 121.0(2)
C12 C11 C16 117.4(2)
C12 C11 C9 123.1(2)
C16 C11 C9 119.5(2)
C4 C5 C7 126.7(2)
C4 C5 S1 109.98(18)
C7 C5 S1 123.34(18)
O17 C16 C15 117.9(2)
O17 C16 C11 122.2(2)
C15 C16 C11 119.9(2)
C16 O17 H17 109.5
C5 C4 C3 113.4(2)
C5 C4 H4 123.3
C3 C4 H4 123.3
C13 C12 C11 121.9(2)
C13 C12 H12 119.0
C11 C12 H12 119.0
C2 C3 C4 113.7(2)
C2 C3 H3 123.1
C4 C3 H3 123.1
C14 C15 C16 120.6(2)
C14 C15 H15 119.7
C16 C15 H15 119.7
C3 C2 C6 129.0(3)
C3 C2 S1 110.56(19)
C6 C2 S1 120.5(2)
C12 C13 C14 119.5(3)
C12 C13 H13 120.3
C14 C13 H13 120.3
C15 C14 C13 120.7(3)
C15 C14 H14 119.6
C13 C14 H14 119.6
C2 C6 H6A 109.5
C2 C6 H6B 109.5
H6A C6 H6B 109.5
C2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.712(2)
S1 C2 1.723(3)
O10 C9 1.251(3)
C8 C7 1.328(3)
C8 C9 1.465(3)
C8 H8 0.9300
C7 C5 1.442(3)
C7 H7 0.9300
C9 C11 1.463(3)
C11 C12 1.397(3)
C11 C16 1.418(3)
C5 C4 1.368(3)
C16 O17 1.340(3)
C16 C15 1.390(4)
O17 H17 0.8200
C4 C3 1.395(4)
C4 H4 0.9300
C12 C13 1.374(4)
C12 H12 0.9300
C3 C2 1.342(4)
C3 H3 0.9300
C15 C14 1.363(4)
C15 H15 0.9300
C2 C6 1.506(4)
C13 C14 1.383(4)
C13 H13 0.9300
C14 H14 0.9300
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 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
C9 C8 C7 C5 179.2(2)
C7 C8 C9 O10 -0.5(3)
C7 C8 C9 C11 -179.6(2)
O10 C9 C11 C12 -175.3(2)
C8 C9 C11 C12 3.8(3)
O10 C9 C11 C16 4.2(3)
C8 C9 C11 C16 -176.8(2)
C8 C7 C5 C4 171.7(2)
C8 C7 C5 S1 -7.7(3)
C2 S1 C5 C4 0.09(18)
C2 S1 C5 C7 179.55(19)
C12 C11 C16 O17 179.0(2)
C9 C11 C16 O17 -0.4(3)
C12 C11 C16 C15 -1.1(3)
C9 C11 C16 C15 179.4(2)
C7 C5 C4 C3 -179.3(2)
S1 C5 C4 C3 0.1(3)
C16 C11 C12 C13 0.5(4)
C9 C11 C12 C13 179.9(2)
C5 C4 C3 C2 -0.4(3)
O17 C16 C15 C14 -179.5(2)
C11 C16 C15 C14 0.7(4)
C4 C3 C2 C6 179.4(3)
C4 C3 C2 S1 0.4(3)
C5 S1 C2 C3 -0.3(2)
C5 S1 C2 C6 -179.4(2)
C11 C12 C13 C14 0.5(4)
C16 C15 C14 C13 0.4(4)
C12 C13 C14 C15 -1.0(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 163409620
