#------------------------------------------------------------------------------
#$Date: 2024-05-11 04:50:57 +0300 (Sat, 11 May 2024) $
#$Revision: 291816 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023121.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_2023121
loop_
_publ_author_name
'Podrezova, Alexandra G.'
'Nikitina, Eugeniya V.'
'Grigoriev, Mikhail S.'
'Akkurt, Mehmet'
'Hasanov, Khudayar I.'
'Sadikhov, Nurlana D.'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (Z)-4-oxo-4-{phenyl[(thiophen-2-yl)methyl]amino}but-2-enoic acid
;
_journal_coeditor_code           JY2046
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024003967
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C15 H13 N O3 S'
_chemical_formula_moiety         'C15 H13 N O3 S'
_chemical_formula_sum            'C15 H13 N O3 S'
_chemical_formula_weight         287.32
_chemical_name_systematic
;
(Z)-4-Oxo-4-{phenyl[(thiophen-2-yl)methyl]amino}but-2-enoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 108.455(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8042(8)
_cell_length_b                   9.4258(8)
_cell_length_c                   15.4065(13)
_cell_measurement_reflns_used    4604
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.98
_cell_measurement_theta_min      2.79
_cell_volume                     1350.5(2)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX4 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker Kappa APEXII area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21582
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.232
_diffrn_reflns_theta_min         2.950
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       bulk
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.342
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4012
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0437P)²+0.4392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                3177
_reflns_number_total             4012
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jy2046.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023121
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.952
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.27590(14) 0.14305(14) 0.00355(9) 0.0182(3) Uani d 1 . .
C C2 1.15520(14) 0.20128(14) -0.07416(8) 0.0170(3) Uani d 1 . .
H H2 1.180897 0.219090 -0.127661 0.020 Uiso calc 1 . .
C C3 1.01839(14) 0.23331(14) -0.08348(8) 0.0158(2) Uani d 1 . .
H H3 0.964652 0.274345 -0.140347 0.019 Uiso calc 1 . .
C C4 0.93968(14) 0.21300(13) -0.01641(8) 0.0148(2) Uani d 1 . .
C C5 0.72253(14) 0.24616(15) 0.02527(9) 0.0182(3) Uani d 1 . .
H H5A 0.748802 0.153057 0.055723 0.022 Uiso calc 1 A 1
H H5B 0.619115 0.242997 -0.010667 0.022 Uiso calc 1 A 1
C C6 0.74604(14) 0.35914(14) 0.09688(8) 0.0158(2) Uani d 0.9466(17) B 1
C C7 0.6467(2) 0.4469(3) 0.11431(18) 0.0227(5) Uani d 0.9466(17) B 1
H H7 0.548211 0.447362 0.078155 0.027 Uiso calc 0.9466(17) B 1
C C8 0.70285(18) 0.53646(15) 0.19035(10) 0.0260(3) Uani d 0.9466(17) B 1
H H8 0.647063 0.602554 0.211255 0.031 Uiso calc 0.9466(17) B 1
C C9 0.84581(17) 0.51709(16) 0.23009(9) 0.0247(3) Uani d 0.9466(17) B 1
H H9 0.902561 0.568587 0.281969 0.030 Uiso calc 0.9466(17) B 1
S S1 0.91239(4) 0.38895(4) 0.17591(2) 0.01947(12) Uani d 0.9466(17) B 1
C C6A 0.74604(14) 0.35914(14) 0.09688(8) 0.0158(2) Uani d 0.0534(17) B 2
C C7A 0.866(2) 0.409(3) 0.1685(14) 0.0227(5) Uani d 0.0534(17) B 2
H H7A 0.959121 0.372099 0.176104 0.027 Uiso calc 0.0534(17) B 2
C C8A 0.84581(17) 0.51709(16) 0.23009(9) 0.0247(3) Uani d 0.0534(17) B 2
H H8A 0.912101 0.560641 0.282056 0.030 Uiso calc 0.0534(17) B 2
C C9A 0.70285(18) 0.53646(15) 0.19035(10) 0.0260(3) Uani d 0.0534(17) B 2
H H9A 0.654641 0.604979 0.215253 0.031 Uiso calc 0.0534(17) B 2
S S1A 0.6147(12) 0.4493(16) 0.1046(9) 0.01947(12) Uani d 0.0534(17) B 2
C C10 0.74377(13) 0.35644(14) -0.11738(8) 0.0145(2) Uani d 1 . .
C C11 0.76237(15) 0.50178(15) -0.11112(9) 0.0218(3) Uani d 1 . .
H H11 0.815581 0.544184 -0.054609 0.026 Uiso calc 1 . .
C C12 0.70262(17) 0.58569(16) -0.18818(11) 0.0281(3) Uani d 1 . .
H H12 0.714737 0.685746 -0.184435 0.034 Uiso calc 1 . .
C C13 0.62523(15) 0.52269(17) -0.27055(10) 0.0264(3) Uani d 1 . .
H H13 0.585703 0.579641 -0.323445 0.032 Uiso calc 1 . .
C C14 0.60560(15) 0.37755(17) -0.27577(9) 0.0248(3) Uani d 1 . .
H H14 0.551520 0.335301 -0.332142 0.030 Uiso calc 1 . .
C C15 0.66448(14) 0.29248(16) -0.19901(9) 0.0205(3) Uani d 1 . .
H H15 0.650653 0.192624 -0.202446 0.025 Uiso calc 1 . .
N N1 0.80705(11) 0.26905(12) -0.03776(7) 0.0152(2) Uani d 1 . .
O O1 1.24869(11) 0.08523(11) 0.07469(6) 0.0217(2) Uani d 1 . .
H H1 1.153(3) 0.100(2) 0.0707(15) 0.065(7) Uiso d 1 . .
O O2 1.39697(11) 0.14995(13) -0.00031(7) 0.0295(3) Uani d 1 . .
O O3 0.99128(10) 0.14570(10) 0.05663(6) 0.0200(2) Uani d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 121.40(12) ?
O2 C1 C2 . . 118.76(12) ?
O1 C1 C2 . . 119.85(12) ?
C3 C2 C1 . . 132.93(12) ?
C3 C2 H2 . . 113.5 ?
C1 C2 H2 . . 113.5 ?
C2 C3 C4 . . 128.36(12) ?
C2 C3 H3 . . 115.8 ?
C4 C3 H3 . . 115.8 ?
O3 C4 N1 . . 120.25(11) ?
O3 C4 C3 . . 122.70(12) ?
N1 C4 C3 . . 117.04(11) ?
N1 C5 C6 . . 113.11(10) ?
N1 C5 C6A . . 113.11(10) ?
N1 C5 H5A . . 109.0 ?
C6 C5 H5A . . 109.0 ?
N1 C5 H5B . . 109.0 ?
C6 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
C7 C6 C5 . . 128.44(15) ?
C7 C6 S1 . . 109.66(13) ?
C5 C6 S1 . . 121.83(10) ?
C6 C7 C8 . . 114.29(17) ?
C6 C7 H7 . . 122.9 ?
C8 C7 H7 . . 122.9 ?
C9 C8 C7 . . 111.84(15) ?
C9 C8 H8 . . 124.1 ?
C7 C8 H8 . . 124.1 ?
C8 C9 S1 . . 112.04(11) ?
C8 C9 H9 . . 124.0 ?
S1 C9 H9 . . 124.0 ?
C9 S1 C6 . . 92.17(7) ?
C7A C6A C5 . . 135.0(9) ?
C7A C6A S1A . . 104.9(9) ?
C5 C6A S1A . . 120.0(4) ?
C6A C7A C8A . . 119.6(16) ?
C6A C7A H7A . . 120.2 ?
C8A C7A H7A . . 120.2 ?
C9A C8A C7A . . 97.8(8) ?
C9A C8A H8A . . 131.1 ?
C7A C8A H8A . . 131.1 ?
C8A C9A S1A . . 121.9(4) ?
C8A C9A H9A . . 119.1 ?
S1A C9A H9A . . 119.1 ?
C9A S1A C6A . . 95.8(6) ?
C11 C10 C15 . . 121.14(12) ?
C11 C10 N1 . . 119.64(11) ?
C15 C10 N1 . . 119.22(12) ?
C10 C11 C12 . . 119.57(13) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C13 C12 C11 . . 119.80(14) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C14 C13 C12 . . 120.18(13) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.54(13) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C10 C15 C14 . . 118.76(13) ?
C10 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C4 N1 C10 . . 123.64(10) ?
C4 N1 C5 . . 118.81(11) ?
C10 N1 C5 . . 117.49(10) ?
C1 O1 H1 . . 110.4(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.2089(16) ?
C1 O1 . 1.3246(16) ?
C1 C2 . 1.4960(18) ?
C2 C3 . 1.3375(18) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.4848(17) ?
C3 H3 . 0.9500 ?
C4 O3 . 1.2507(15) ?
C4 N1 . 1.3444(16) ?
C5 N1 . 1.4783(16) ?
C5 C6 . 1.4978(18) ?
C5 C6A . 1.4978(18) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.368(3) ?
C6 S1 . 1.7217(13) ?
C7 C8 . 1.407(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.353(2) ?
C8 H8 . 0.9500 ?
C9 S1 . 1.7108(15) ?
C9 H9 . 0.9500 ?
C6A C7A . 1.414(17) ?
C6A S1A . 1.579(12) ?
C7A C8A . 1.447(18) ?
C7A H7A . 0.9500 ?
C8A C9A . 1.353(2) ?
C8A H8A . 0.9500 ?
C9A S1A . 1.563(12) ?
C9A H9A . 0.9500 ?
C10 C11 . 1.3813(19) ?
C10 C15 . 1.3895(17) ?
C10 N1 . 1.4444(16) ?
C11 C12 . 1.392(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.389(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.380(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.394(2) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
O1 H1 . 0.93(3) ?
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 O3 . 0.93(3) 1.59(3) 2.5153(15) 172(2) yes
C5 H5B O2 1_455 0.99 2.40 3.2201(19) 140 yes
C9 H9 O3 2_755 0.95 2.48 3.3904(16) 160 no
C14 H14 O2 4_465 0.95 2.56 3.4261(17) 152 no
C15 H15 Cg2 4_554 0.95 3.00 3.504(6) 115 no
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
O2 C1 C2 C3 . . . . -165.63(15) ?
O1 C1 C2 C3 . . . . 14.4(2) ?
C1 C2 C3 C4 . . . . -3.2(2) ?
C2 C3 C4 O3 . . . . -8.5(2) ?
C2 C3 C4 N1 . . . . 172.40(13) ?
N1 C5 C6 C7 . . . . 121.71(19) ?
N1 C5 C6 S1 . . . . -61.84(14) ?
C5 C6 C7 C8 . . . . 176.46(15) ?
S1 C6 C7 C8 . . . . -0.3(2) ?
C6 C7 C8 C9 . . . . 0.6(3) ?
C7 C8 C9 S1 . . . . -0.54(19) ?
C8 C9 S1 C6 . . . . 0.30(12) ?
C7 C6 S1 C9 . . . . 0.02(15) ?
C5 C6 S1 C9 . . . . -177.02(11) ?
N1 C5 C6A C7A . . . . -61.1(16) ?
N1 C5 C6A S1A . . . . 121.4(7) ?
C5 C6A C7A C8A . . . . -175.6(8) ?
S1A C6A C7A C8A . . . . 2(2) ?
C6A C7A C8A C9A . . . . -2(2) ?
C7A C8A C9A S1A . . . . 0.9(13) ?
C8A C9A S1A C6A . . . . 0.2(10) ?
C7A C6A S1A C9A . . . . -1.3(15) ?
C5 C6A S1A C9A . . . . 176.9(3) ?
C15 C10 C11 C12 . . . . -1.0(2) ?
N1 C10 C11 C12 . . . . 179.31(12) ?
C10 C11 C12 C13 . . . . -0.1(2) ?
C11 C12 C13 C14 . . . . 1.0(2) ?
C12 C13 C14 C15 . . . . -0.8(2) ?
C11 C10 C15 C14 . . . . 1.2(2) ?
N1 C10 C15 C14 . . . . -179.09(11) ?
C13 C14 C15 C10 . . . . -0.3(2) ?
O3 C4 N1 C10 . . . . 175.49(11) ?
C3 C4 N1 C10 . . . . -5.36(17) ?
O3 C4 N1 C5 . . . . -1.68(17) ?
C3 C4 N1 C5 . . . . 177.47(11) ?
C11 C10 N1 C4 . . . . -90.21(15) ?
C15 C10 N1 C4 . . . . 90.09(15) ?
C11 C10 N1 C5 . . . . 87.00(15) ?
C15 C10 N1 C5 . . . . -92.71(14) ?
C6 C5 N1 C4 . . . . 89.91(14) ?
C6A C5 N1 C4 . . . . 89.91(14) ?
C6 C5 N1 C10 . . . . -87.43(13) ?
C6A C5 N1 C10 . . . . -87.43(13) ?
