#------------------------------------------------------------------------------
#$Date: 2024-04-27 04:54:49 +0300 (Sat, 27 Apr 2024) $
#$Revision: 291379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023093.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_2023093
loop_
_publ_author_name
'Yakovleva, Elizaveta D.'
'Shelukho, Evgeniya R.'
'Grigoriev, Mikhail S.'
'Hasanov, Khudayar I.'
'Sadikhova, Nurlana D.'
'Akkurt, Mehmet'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (Z)-4-({[2-(benzo[b]thiophen-3-yl)cyclopent-1-en-1-yl]methyl}(phenyl)amino)-4-oxobut-2-enoic
 acid
;
_journal_coeditor_code           NX2009
_journal_issue                   5
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024003232
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C24 H21 N O3 S'
_chemical_formula_moiety         'C24 H21 N O3 S'
_chemical_formula_sum            'C24 H21 N O3 S'
_chemical_formula_weight         403.48
_chemical_name_systematic
'(Z)-4-({[2-(Benzo[b]thiophen-3-yl)cyclopent-1-en-1-yl]methyl}(phenyl)amino)-4-oxobut-2-enoic acid'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                95.392(3)
_cell_angle_beta                 96.849(3)
_cell_angle_gamma                106.512(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4270(5)
_cell_length_b                   9.4386(4)
_cell_length_c                   12.3849(7)
_cell_measurement_reflns_used    2139
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.12
_cell_measurement_theta_min      2.70
_cell_volume                     1039.49(9)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13624
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         4.262
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       fragment
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0397P)²+0.1315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                2579
_reflns_number_total             4758
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nx2009.cif
_cod_data_source_block           I
_cod_database_code               2023093
_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   0.944
_shelx_estimated_absorpt_t_max   0.961
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.87037(7) 0.68170(6) 0.61573(5) 0.0594(2) Uani d 1 . .
O O21 0.1824(3) -0.0483(2) -0.14619(18) 0.1267(9) Uani d 1 . .
O O28 0.3378(2) 0.04844(18) 0.20444(14) 0.0791(6) Uani d 1 . .
O O29 0.1793(3) -0.0840(2) 0.0262(2) 0.1150(9) Uani d 1 . .
H H29 0.224(5) -0.045(4) 0.098(3) 0.158(16) Uiso d 1 . .
N N5 0.51977(19) 0.26204(18) 0.26864(14) 0.0485(5) Uani d 1 . .
C C1 0.5116(2) 0.2342(2) 0.38357(17) 0.0521(6) Uani d 1 . .
H H1A 0.415584 0.163072 0.386915 0.063 Uiso calc 1 . .
H H1B 0.517549 0.326562 0.428083 0.063 Uiso calc 1 . .
C C2 0.8233(2) 0.5180(2) 0.52668(18) 0.0512(6) Uani d 1 . .
H H2A 0.830032 0.515746 0.452274 0.061 Uiso calc 1 . .
C C3A 0.7750(2) 0.4286(2) 0.68961(17) 0.0406(5) Uani d 1 . .
C C3 0.7756(2) 0.3932(2) 0.57416(17) 0.0424(5) Uani d 1 . .
C C4 0.7341(2) 0.3332(2) 0.76803(19) 0.0500(6) Uani d 1 . .
H H4A 0.699452 0.230472 0.747835 0.060 Uiso calc 1 . .
C C5 0.7460(3) 0.3934(3) 0.8750(2) 0.0671(7) Uani d 1 . .
H H5A 0.718992 0.330231 0.927272 0.080 Uiso calc 1 . .
C C6 0.7974(3) 0.5468(3) 0.9073(2) 0.0763(8) Uani d 1 . .
H H6A 0.805046 0.584341 0.980612 0.092 Uiso calc 1 . .
C C7A 0.8246(2) 0.5832(2) 0.72381(18) 0.0466(5) Uani d 1 . .
C C7 0.8367(3) 0.6423(3) 0.8327(2) 0.0630(7) Uani d 1 . .
H H7A 0.870953 0.744824 0.854184 0.076 Uiso calc 1 . .
C C11 0.6337(2) 0.1755(2) 0.43046(17) 0.0436(5) Uani d 1 . .
C C12 0.7407(2) 0.2407(2) 0.51466(16) 0.0426(5) Uani d 1 . .
C C13 0.8318(3) 0.1381(2) 0.54573(19) 0.0552(6) Uani d 1 . .
H H13A 0.806912 0.098031 0.612696 0.066 Uiso calc 1 . .
H H13B 0.938174 0.189892 0.555652 0.066 Uiso calc 1 . .
C C14 0.7866(3) 0.0148(2) 0.4478(2) 0.0598(6) Uani d 1 . .
H H14A 0.861755 0.031363 0.399435 0.072 Uiso calc 1 . .
H H14B 0.775219 -0.081812 0.472422 0.072 Uiso calc 1 . .
C C15 0.6382(3) 0.0221(2) 0.38884(19) 0.0554(6) Uani d 1 . .
H H15A 0.635418 0.009946 0.309899 0.066 Uiso calc 1 . .
H H15B 0.554836 -0.054219 0.407358 0.066 Uiso calc 1 . .
C C21 0.2336(4) -0.0081(3) -0.0502(3) 0.0835(9) Uani d 1 . .
C C22 0.3591(3) 0.1295(3) -0.0208(2) 0.0683(7) Uani d 1 . .
H H22A 0.388556 0.174848 -0.081361 0.082 Uiso calc 1 . .
C C23 0.4395(3) 0.2030(3) 0.07372(19) 0.0645(7) Uani d 1 . .
H H23A 0.513533 0.290349 0.068407 0.077 Uiso calc 1 . .
C C24 0.4279(3) 0.1656(2) 0.18604(19) 0.0556(6) Uani d 1 . .
C C31 0.6267(2) 0.3994(2) 0.25315(16) 0.0423(5) Uani d 1 . .
C C32 0.7609(3) 0.3991(2) 0.22026(18) 0.0520(6) Uani d 1 . .
H H32A 0.784507 0.310332 0.207993 0.062 Uiso calc 1 . .
C C33 0.8601(3) 0.5327(3) 0.2057(2) 0.0636(7) Uani d 1 . .
H H33A 0.949957 0.533354 0.181491 0.076 Uiso calc 1 . .
C C34 0.8276(3) 0.6634(3) 0.2264(2) 0.0708(8) Uani d 1 . .
H H34A 0.895368 0.752805 0.216795 0.085 Uiso calc 1 . .
C C35 0.6957(4) 0.6629(3) 0.2613(2) 0.0696(8) Uani d 1 . .
H H35A 0.674317 0.752324 0.276532 0.083 Uiso calc 1 . .
C C36 0.5938(3) 0.5303(2) 0.2740(2) 0.0593(6) Uani d 1 . .
H H36A 0.503131 0.530002 0.296694 0.071 Uiso calc 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
C2 S1 C7A . . 90.81(10) ?
C21 O29 H29 . . 116(2) ?
C24 N5 C31 . . 123.48(18) ?
C24 N5 C1 . . 120.39(19) ?
C31 N5 C1 . . 116.08(16) ?
N5 C1 C11 . . 112.78(18) ?
N5 C1 H1A . . 109.0 ?
C11 C1 H1A . . 109.0 ?
N5 C1 H1B . . 109.0 ?
C11 C1 H1B . . 109.0 ?
H1A C1 H1B . . 107.8 ?
C3 C2 S1 . . 114.34(17) ?
C3 C2 H2A . . 122.8 ?
S1 C2 H2A . . 122.8 ?
C4 C3A C7A . . 118.37(19) ?
C4 C3A C3 . . 129.57(19) ?
C7A C3A C3 . . 112.06(18) ?
C2 C3 C3A . . 111.32(18) ?
C2 C3 C12 . . 123.2(2) ?
C3A C3 C12 . . 125.29(18) ?
C5 C4 C3A . . 119.1(2) ?
C5 C4 H4A . . 120.5 ?
C3A C4 H4A . . 120.5 ?
C4 C5 C6 . . 121.6(2) ?
C4 C5 H5A . . 119.2 ?
C6 C5 H5A . . 119.2 ?
C7 C6 C5 . . 120.7(2) ?
C7 C6 H6A . . 119.7 ?
C5 C6 H6A . . 119.7 ?
C7 C7A C3A . . 121.8(2) ?
C7 C7A S1 . . 126.71(17) ?
C3A C7A S1 . . 111.46(16) ?
C6 C7 C7A . . 118.5(2) ?
C6 C7 H7A . . 120.8 ?
C7A C7 H7A . . 120.8 ?
C12 C11 C1 . . 126.95(18) ?
C12 C11 C15 . . 112.06(18) ?
C1 C11 C15 . . 120.81(18) ?
C11 C12 C3 . . 127.71(18) ?
C11 C12 C13 . . 111.02(17) ?
C3 C12 C13 . . 121.27(17) ?
C12 C13 C14 . . 103.43(17) ?
C12 C13 H13A . . 111.1 ?
C14 C13 H13A . . 111.1 ?
C12 C13 H13B . . 111.1 ?
C14 C13 H13B . . 111.1 ?
H13A C13 H13B . . 109.0 ?
C15 C14 C13 . . 105.85(18) ?
C15 C14 H14A . . 110.6 ?
C13 C14 H14A . . 110.6 ?
C15 C14 H14B . . 110.6 ?
C13 C14 H14B . . 110.6 ?
H14A C14 H14B . . 108.7 ?
C11 C15 C14 . . 103.55(17) ?
C11 C15 H15A . . 111.1 ?
C14 C15 H15A . . 111.1 ?
C11 C15 H15B . . 111.1 ?
C14 C15 H15B . . 111.1 ?
H15A C15 H15B . . 109.0 ?
O21 C21 O29 . . 121.5(3) ?
O21 C21 C22 . . 118.3(3) ?
O29 C21 C22 . . 120.2(2) ?
C23 C22 C21 . . 133.7(3) ?
C23 C22 H22A . . 113.2 ?
C21 C22 H22A . . 113.2 ?
C22 C23 C24 . . 129.1(2) ?
C22 C23 H23A . . 115.5 ?
C24 C23 H23A . . 115.5 ?
O28 C24 N5 . . 120.6(2) ?
O28 C24 C23 . . 122.1(2) ?
N5 C24 C23 . . 117.3(2) ?
C36 C31 C32 . . 120.5(2) ?
C36 C31 N5 . . 118.8(2) ?
C32 C31 N5 . . 120.68(18) ?
C31 C32 C33 . . 119.0(2) ?
C31 C32 H32A . . 120.5 ?
C33 C32 H32A . . 120.5 ?
C34 C33 C32 . . 120.6(2) ?
C34 C33 H33A . . 119.7 ?
C32 C33 H33A . . 119.7 ?
C33 C34 C35 . . 119.9(2) ?
C33 C34 H34A . . 120.1 ?
C35 C34 H34A . . 120.1 ?
C34 C35 C36 . . 120.3(2) ?
C34 C35 H35A . . 119.8 ?
C36 C35 H35A . . 119.8 ?
C31 C36 C35 . . 119.6(2) ?
C31 C36 H36A . . 120.2 ?
C35 C36 H36A . . 120.2 ?
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
S1 C2 . 1.725(2) ?
S1 C7A . 1.728(2) ?
O21 C21 . 1.210(3) ?
O28 C24 . 1.247(3) ?
O29 C21 . 1.305(4) ?
O29 H29 . 0.93(4) ?
N5 C24 . 1.338(3) ?
N5 C31 . 1.443(3) ?
N5 C1 . 1.478(3) ?
C1 C11 . 1.495(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.352(3) ?
C2 H2A . 0.9300 ?
C3A C4 . 1.399(3) ?
C3A C7A . 1.406(3) ?
C3A C3 . 1.439(3) ?
C3 C12 . 1.482(3) ?
C4 C5 . 1.370(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.391(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.361(4) ?
C6 H6A . 0.9300 ?
C7A C7 . 1.389(3) ?
C7 H7A . 0.9300 ?
C11 C12 . 1.326(3) ?
C11 C15 . 1.505(3) ?
C12 C13 . 1.512(3) ?
C13 C14 . 1.529(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.522(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C21 C22 . 1.468(4) ?
C22 C23 . 1.329(3) ?
C22 H22A . 0.9300 ?
C23 C24 . 1.476(3) ?
C23 H23A . 0.9300 ?
C31 C36 . 1.367(3) ?
C31 C32 . 1.375(3) ?
C32 C33 . 1.382(3) ?
C32 H32A . 0.9300 ?
C33 C34 . 1.362(3) ?
C33 H33A . 0.9300 ?
C34 C35 . 1.363(4) ?
C34 H34A . 0.9300 ?
C35 C36 . 1.380(4) ?
C35 H35A . 0.9300 ?
C36 H36A . 0.9300 ?
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
O29 H29 O28 . 0.93(4) 1.60(4) 2.510(3) 164(4) yes
C32 H32A O21 2_655 0.93 2.63 3.556(3) 170.9 yes
C2 H2A Cg4 . 0.93 2.72 3.579(2) 154 yes
C33 H33A Cg3 2_766 0.93 2.54 3.408(3) 155 yes
C33 H33A Cg5 2_766 0.93 2.64 3.353(3) 133 no
C36 H36A Cg3 2_666 0.93 2.79 3.535(3) 138 yes
C36 H36A Cg5 2_666 0.93 2.75 3.623(3) 157 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
C24 N5 C1 C11 . . . . 102.2(2) ?
C31 N5 C1 C11 . . . . -80.0(2) ?
C7A S1 C2 C3 . . . . -0.32(18) ?
S1 C2 C3 C3A . . . . 0.4(2) ?
S1 C2 C3 C12 . . . . -175.16(15) ?
C4 C3A C3 C2 . . . . -179.9(2) ?
C7A C3A C3 C2 . . . . -0.4(2) ?
C4 C3A C3 C12 . . . . -4.4(3) ?
C7A C3A C3 C12 . . . . 175.13(19) ?
C7A C3A C4 C5 . . . . -0.9(3) ?
C3 C3A C4 C5 . . . . 178.6(2) ?
C3A C4 C5 C6 . . . . 0.1(4) ?
C4 C5 C6 C7 . . . . 0.5(4) ?
C4 C3A C7A C7 . . . . 1.3(3) ?
C3 C3A C7A C7 . . . . -178.3(2) ?
C4 C3A C7A S1 . . . . 179.73(15) ?
C3 C3A C7A S1 . . . . 0.1(2) ?
C2 S1 C7A C7 . . . . 178.4(2) ?
C2 S1 C7A C3A . . . . 0.09(16) ?
C5 C6 C7 C7A . . . . -0.1(4) ?
C3A C7A C7 C6 . . . . -0.8(3) ?
S1 C7A C7 C6 . . . . -178.9(2) ?
N5 C1 C11 C12 . . . . 117.2(2) ?
N5 C1 C11 C15 . . . . -68.1(3) ?
C1 C11 C12 C3 . . . . -7.6(4) ?
C15 C11 C12 C3 . . . . 177.3(2) ?
C1 C11 C12 C13 . . . . 173.2(2) ?
C15 C11 C12 C13 . . . . -1.9(3) ?
C2 C3 C12 C11 . . . . -64.0(3) ?
C3A C3 C12 C11 . . . . 121.0(2) ?
C2 C3 C12 C13 . . . . 115.1(2) ?
C3A C3 C12 C13 . . . . -59.9(3) ?
C11 C12 C13 C14 . . . . 13.8(3) ?
C3 C12 C13 C14 . . . . -165.47(19) ?
C12 C13 C14 C15 . . . . -19.8(2) ?
C12 C11 C15 C14 . . . . -10.9(3) ?
C1 C11 C15 C14 . . . . 173.7(2) ?
C13 C14 C15 C11 . . . . 18.7(2) ?
O21 C21 C22 C23 . . . . -179.9(3) ?
O29 C21 C22 C23 . . . . 0.3(5) ?
C21 C22 C23 C24 . . . . 0.9(5) ?
C31 N5 C24 O28 . . . . 179.9(2) ?
C1 N5 C24 O28 . . . . -2.5(3) ?
C31 N5 C24 C23 . . . . 0.6(3) ?
C1 N5 C24 C23 . . . . 178.22(19) ?
C22 C23 C24 O28 . . . . 3.1(4) ?
C22 C23 C24 N5 . . . . -177.6(2) ?
C24 N5 C31 C36 . . . . 102.1(2) ?
C1 N5 C31 C36 . . . . -75.6(2) ?
C24 N5 C31 C32 . . . . -79.3(3) ?
C1 N5 C31 C32 . . . . 103.1(2) ?
C36 C31 C32 C33 . . . . -1.8(3) ?
N5 C31 C32 C33 . . . . 179.64(19) ?
C31 C32 C33 C34 . . . . 1.8(3) ?
C32 C33 C34 C35 . . . . -0.4(4) ?
C33 C34 C35 C36 . . . . -1.0(4) ?
C32 C31 C36 C35 . . . . 0.4(3) ?
N5 C31 C36 C35 . . . . 179.0(2) ?
C34 C35 C36 C31 . . . . 1.0(4) ?
