#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/94/2209460.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_2209460
loop_
_publ_author_name
'Hai-Lian Xiao'
'Fang-Fang Jian'
_publ_section_title
;
 (E)-2-Acetyl-3-hydroxy-N-phenylbut-2-enethioamide
;
_journal_coeditor_code           CV2062
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2854
_journal_page_last               o2855
_journal_paper_doi               10.1107/S1600536806020216
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H13 N O2 S'
_chemical_formula_moiety         'C12 H13 N O2 S'
_chemical_formula_sum            'C12 H13 N O2 S'
_chemical_formula_weight         235.29
_chemical_name_systematic
;
(E)-2-Acetyl-3-hydroxy-N-phenylbut-2-enethioamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.249(2)
_cell_length_b                   10.506(2)
_cell_length_c                   10.376(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_cell_volume                     1226.3(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_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  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5616
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.290
_refine_ls_abs_structure_details 'Flack (1983), 1126 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.13(13)
_refine_ls_extinction_coef       0.122(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0475
_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)+(0.1117P)²+0.097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                2117
_reflns_number_total             2675
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2062.cif
_cod_data_source_block           I
_cod_database_code               2209460
_cod_database_fobs_code          2209460
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'
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 0.16955(6) 0.58156(9) 1.06940(6) 0.0664(3) Uani d . 1
O O1 0.54099(17) 0.5478(3) 0.8619(3) 0.0869(9) Uani d . 1
O O2 0.5025(2) 0.3352(3) 0.9541(3) 0.0890(9) Uani d D 1
N N1 0.15784(17) 0.4859(2) 0.83058(19) 0.0473(5) Uani d . 1
H H1A 0.1999 0.4576 0.7676 0.057 Uiso calc R 1
C C1 -0.0449(2) 0.5711(3) 0.8645(3) 0.0658(8) Uani d . 1
H H1B -0.0202 0.6229 0.9321 0.079 Uiso calc R 1
C C2 -0.1633(2) 0.5720(3) 0.8240(4) 0.0717(8) Uani d . 1
H H2A -0.2174 0.6257 0.8645 0.086 Uiso calc R 1
C C3 -0.2008(2) 0.4954(3) 0.7262(3) 0.0676(8) Uani d . 1
H H3A -0.2800 0.4969 0.7004 0.081 Uiso calc R 1
C C4 -0.1210(3) 0.4156(4) 0.6653(3) 0.0710(9) Uani d . 1
H H4A -0.1463 0.3625 0.5991 0.085 Uiso calc R 1
C C5 -0.0051(2) 0.4153(3) 0.7029(3) 0.0593(7) Uani d . 1
H H5A 0.0487 0.3624 0.6609 0.071 Uiso calc R 1
C C6 0.0345(2) 0.4927(2) 0.8031(2) 0.0461(5) Uani d . 1
C C7 0.22133(18) 0.5149(2) 0.9355(2) 0.0436(5) Uani d . 1
C C8 0.3500(2) 0.4823(3) 0.9221(2) 0.0492(5) Uani d . 1
C C9 0.4301(2) 0.5731(4) 0.8716(3) 0.0621(7) Uani d . 1
C C10 0.3910(3) 0.7012(4) 0.8276(4) 0.0807(10) Uani d . 1
H H10A 0.4584 0.7481 0.7965 0.121 Uiso calc R 1
H H10B 0.3556 0.7462 0.8985 0.121 Uiso calc R 1
H H10C 0.3338 0.6921 0.7596 0.121 Uiso calc R 1
C C11 0.3930(3) 0.3631(3) 0.9603(3) 0.0647(8) Uani d . 1
C C12 0.3130(4) 0.2610(4) 1.0124(5) 0.0943(12) Uani d . 1
H H12A 0.3594 0.1870 1.0331 0.141 Uiso calc R 1
H H12B 0.2545 0.2393 0.9487 0.141 Uiso calc R 1
H H12C 0.2740 0.2914 1.0887 0.141 Uiso calc R 1
H H2 0.535(4) 0.400(3) 0.918(5) 0.093(16) Uiso d D 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0511(4) 0.1127(6) 0.0354(3) 0.0220(4) -0.0027(3) -0.0153(3)
O1 0.0387(9) 0.148(2) 0.0742(16) -0.0044(12) 0.0069(9) -0.0040(15)
O2 0.0664(15) 0.107(2) 0.094(2) 0.0397(15) -0.0058(14) -0.0130(17)
N1 0.0382(9) 0.0674(12) 0.0362(9) 0.0040(9) 0.0018(7) -0.0052(9)
C1 0.0464(13) 0.0745(18) 0.077(2) 0.0081(13) -0.0083(13) -0.0202(17)
C2 0.0443(13) 0.0829(19) 0.088(2) 0.0156(15) -0.0048(14) -0.0085(18)
C3 0.0394(13) 0.102(2) 0.0618(17) -0.0053(14) -0.0092(11) 0.0116(17)
C4 0.0553(14) 0.108(2) 0.0496(14) -0.0198(17) -0.0045(12) -0.0076(17)
C5 0.0478(12) 0.0872(18) 0.0428(12) -0.0064(14) 0.0040(10) -0.0126(14)
C6 0.0407(11) 0.0578(14) 0.0397(11) -0.0012(10) 0.0003(9) 0.0045(11)
C7 0.0382(11) 0.0586(12) 0.0339(10) 0.0024(9) -0.0003(9) 0.0011(10)
C8 0.0398(11) 0.0725(15) 0.0353(10) 0.0058(10) -0.0005(9) -0.0058(11)
C9 0.0440(12) 0.101(2) 0.0417(12) -0.0040(14) 0.0006(10) -0.0012(15)
C10 0.0640(18) 0.096(2) 0.082(2) -0.0207(17) 0.0007(17) 0.017(2)
C11 0.0622(16) 0.0814(18) 0.0504(15) 0.0225(15) -0.0073(12) -0.0103(14)
C12 0.097(3) 0.071(2) 0.115(3) 0.009(2) 0.002(3) 0.014(2)
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'
N N 0.0061 0.0033 '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 O2 H2 104(3)
C7 N1 C6 132.4(2)
C7 N1 H1A 113.8
C6 N1 H1A 113.8
C6 C1 C2 119.0(3)
C6 C1 H1B 120.5
C2 C1 H1B 120.5
C3 C2 C1 121.0(3)
C3 C2 H2A 119.5
C1 C2 H2A 119.5
C2 C3 C4 119.8(3)
C2 C3 H3A 120.1
C4 C3 H3A 120.1
C5 C4 C3 119.6(3)
C5 C4 H4A 120.2
C3 C4 H4A 120.2
C4 C5 C6 121.2(3)
C4 C5 H5A 119.4
C6 C5 H5A 119.4
C1 C6 C5 119.3(2)
C1 C6 N1 125.0(2)
C5 C6 N1 115.6(2)
N1 C7 C8 112.9(2)
N1 C7 S1 126.13(17)
C8 C7 S1 120.92(17)
C11 C8 C9 119.2(2)
C11 C8 C7 120.9(2)
C9 C8 C7 119.9(2)
O1 C9 C8 120.7(3)
O1 C9 C10 116.9(3)
C8 C9 C10 122.4(3)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O2 C11 C8 121.9(3)
O2 C11 C12 115.8(3)
C8 C11 C12 122.3(3)
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.662(2)
O1 C9 1.279(3)
O2 C11 1.268(4)
O2 H2 0.858(10)
N1 C7 1.337(3)
N1 C6 1.419(3)
N1 H1A 0.8600
C1 C6 1.372(4)
C1 C2 1.397(4)
C1 H1B 0.9300
C2 C3 1.363(5)
C2 H2A 0.9300
C3 C4 1.382(5)
C3 H3A 0.9300
C4 C5 1.361(4)
C4 H4A 0.9300
C5 C6 1.393(4)
C5 H5A 0.9300
C7 C8 1.494(3)
C8 C11 1.400(4)
C8 C9 1.413(4)
C9 C10 1.488(5)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.501(5)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
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
N1 H1A S1 2_564 0.86 2.56 3.408(2) 169.1 yes
O2 H2 O1 . 0.858(10) 1.66(2) 2.468(5) 156(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179154
