#------------------------------------------------------------------------------
#$Date: 2024-05-25 04:50:13 +0300 (Sat, 25 May 2024) $
#$Revision: 292030 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023140.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_2023140
loop_
_publ_author_name
'Naghiyev, Farid N.'
'Khrustalev, Victor N.'
'Akkurt, Mehmet'
'Huseynov, Elnur Z.'
'Bhattarai, Ajaya'
'Khalilov, Ali N.'
'Mamedov, İbrahim G.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of dimethyl
 2-oxo-4-(pyridin-2-yl)-6-(thiophen-2-yl)cyclohex-3-ene-1,3-dicarboxylate
;
_journal_coeditor_code           OI2007
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024004687
_journal_volume                  80
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C19 H17 N O5 S'
_chemical_formula_moiety         'C19 H17 N O5 S'
_chemical_formula_sum            'C19 H17 N O5 S'
_chemical_formula_weight         371.39
_chemical_name_systematic
;
Dimethyl
2-oxo-4-(pyridin-2-yl)-6-(thiophen-2-yl)cyclohex-3-ene-1,3-dicarboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                110.910(2)
_cell_angle_beta                 98.1280(10)
_cell_angle_gamma                96.0060(10)
_cell_formula_units_Z            1
_cell_length_a                   5.52600(10)
_cell_length_b                   8.50120(10)
_cell_length_c                   10.1076(2)
_cell_measurement_reflns_used    16321
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.366
_cell_measurement_theta_min      4.748
_cell_volume                     432.885(14)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18199
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.819
_diffrn_reflns_theta_min         4.773
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.936
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       prism
_exptl_crystal_F_000             194
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.175
_refine_ls_abs_structure_details
;
Flack x determined using 1675 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.003(7)
_refine_ls_extinction_coef       0.0131(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0226
_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)+(0.0337P)²+0.0970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0586
_reflns_number_gt                3524
_reflns_number_total             3530
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oi2007.cif
_cod_data_source_block           I
_cod_original_cell_volume        432.884(14)
_cod_database_code               2023140
_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   0.643
_shelx_estimated_absorpt_t_max   0.845
loop_
_space_group_symop_operation_xyz
'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
C C1 0.6259(4) 0.3716(2) 0.6011(2) 0.0132(4) Uani d 1 . .
C C2 0.7320(4) 0.3495(2) 0.46536(19) 0.0127(4) Uani d 1 . .
H H2 0.898999 0.422837 0.493270 0.015 Uiso calc 1 . .
C C3 0.5592(4) 0.4059(2) 0.36259(19) 0.0136(4) Uani d 1 . .
H H3 0.390686 0.337398 0.343691 0.016 Uiso calc 1 . .
C C4 0.5382(4) 0.5930(2) 0.4416(2) 0.0146(4) Uani d 1 . .
H H4A 0.703452 0.664844 0.465810 0.017 Uiso calc 1 . .
H H4B 0.425908 0.630379 0.377470 0.017 Uiso calc 1 . .
C C5 0.4396(3) 0.6170(2) 0.5780(2) 0.0134(4) Uani d 1 . .
C C6 0.4809(4) 0.5121(2) 0.64983(19) 0.0129(4) Uani d 1 . .
C C7 0.7580(4) 0.1653(2) 0.3869(2) 0.0142(4) Uani d 1 . .
C C8 1.0028(4) -0.0161(3) 0.2524(3) 0.0281(5) Uani d 1 . .
H H8A 0.894696 -0.044480 0.158603 0.042 Uiso calc 1 . .
H H8B 0.954145 -0.100288 0.293541 0.042 Uiso calc 1 . .
H H8C 1.175204 -0.017674 0.239795 0.042 Uiso calc 1 . .
C C9 0.6332(4) 0.3713(2) 0.2190(2) 0.0144(4) Uani d 1 . .
C C10 0.5052(4) 0.2567(3) 0.0887(2) 0.0188(4) Uani d 1 . .
H H10 0.352786 0.185818 0.077251 0.023 Uiso calc 1 . .
C C11 0.6230(4) 0.2541(3) -0.0286(2) 0.0211(4) Uani d 1 . .
H H11 0.557058 0.181613 -0.126180 0.025 Uiso calc 1 . .
C C12 0.8386(4) 0.3654(3) 0.0135(2) 0.0198(4) Uani d 1 . .
H H12 0.941797 0.380424 -0.050162 0.024 Uiso calc 1 . .
C C13 0.2915(4) 0.7557(2) 0.6266(2) 0.0138(4) Uani d 1 . .
C C14 0.3097(4) 0.8926(2) 0.5803(2) 0.0170(4) Uani d 1 . .
H H14 0.419867 0.900060 0.517866 0.020 Uiso calc 1 . .
C C15 0.1640(4) 1.0168(2) 0.6273(2) 0.0193(4) Uani d 1 . .
H H15 0.173481 1.111309 0.597847 0.023 Uiso calc 1 . .
C C16 0.0042(4) 1.0017(3) 0.7177(2) 0.0192(4) Uani d 1 . .
H H16 -0.098664 1.084695 0.750789 0.023 Uiso calc 1 . .
C C17 -0.0018(4) 0.8619(3) 0.7589(2) 0.0182(4) Uani d 1 . .
H H17 -0.109760 0.852595 0.822018 0.022 Uiso calc 1 . .
C C18 0.3784(4) 0.5217(2) 0.7826(2) 0.0132(4) Uani d 1 . .
C C19 0.3964(4) 0.6765(3) 1.0269(2) 0.0222(4) Uani d 1 . .
H H19A 0.220812 0.685154 1.005687 0.033 Uiso calc 1 . .
H H19B 0.484406 0.781046 1.106272 0.033 Uiso calc 1 . .
H H19C 0.411825 0.578189 1.054703 0.033 Uiso calc 1 . .
N N1 0.1361(3) 0.7402(2) 0.71452(18) 0.0161(3) Uani d 1 . .
O O1 0.6615(3) 0.27874(17) 0.66693(15) 0.0178(3) Uani d 1 . .
O O2 0.5944(3) 0.04488(18) 0.35502(15) 0.0196(3) Uani d 1 . .
O O3 0.9794(3) 0.15282(18) 0.34916(15) 0.0188(3) Uani d 1 . .
O O4 0.2142(3) 0.41766(17) 0.78248(15) 0.0175(3) Uani d 1 . .
O O5 0.5031(3) 0.65445(18) 0.89989(14) 0.0168(3) Uani d 1 . .
S S1 0.90193(7) 0.47674(5) 0.19781(5) 0.01854(13) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 C1 C6 . . 121.66(16) ?
O1 C1 C2 . . 121.05(17) ?
C6 C1 C2 . . 117.28(15) ?
C7 C2 C1 . . 111.28(15) ?
C7 C2 C3 . . 108.90(15) ?
C1 C2 C3 . . 109.64(15) ?
C7 C2 H2 . . 109.0 ?
C1 C2 H2 . . 109.0 ?
C3 C2 H2 . . 109.0 ?
C9 C3 C4 . . 113.33(15) ?
C9 C3 C2 . . 113.64(16) ?
C4 C3 C2 . . 108.56(15) ?
C9 C3 H3 . . 107.0 ?
C4 C3 H3 . . 107.0 ?
C2 C3 H3 . . 107.0 ?
C5 C4 C3 . . 110.93(15) ?
C5 C4 H4A . . 109.5 ?
C3 C4 H4A . . 109.5 ?
C5 C4 H4B . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.0 ?
C6 C5 C13 . . 122.14(17) ?
C6 C5 C4 . . 120.52(17) ?
C13 C5 C4 . . 117.32(16) ?
C5 C6 C1 . . 122.52(16) ?
C5 C6 C18 . . 123.87(17) ?
C1 C6 C18 . . 113.58(15) ?
O2 C7 O3 . . 123.86(18) ?
O2 C7 C2 . . 124.32(18) ?
O3 C7 C2 . . 111.70(16) ?
O3 C8 H8A . . 109.5 ?
O3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C3 . . 126.53(18) ?
C10 C9 S1 . . 110.34(15) ?
C3 C9 S1 . . 123.13(14) ?
C9 C10 C11 . . 113.26(19) ?
C9 C10 H10 . . 123.4 ?
C11 C10 H10 . . 123.4 ?
C12 C11 C10 . . 112.96(18) ?
C12 C11 H11 . . 123.5 ?
C10 C11 H11 . . 123.5 ?
C11 C12 S1 . . 111.23(15) ?
C11 C12 H12 . . 124.4 ?
S1 C12 H12 . . 124.4 ?
N1 C13 C14 . . 122.33(18) ?
N1 C13 C5 . . 116.34(17) ?
C14 C13 C5 . . 121.32(17) ?
C15 C14 C13 . . 118.75(18) ?
C15 C14 H14 . . 120.6 ?
C13 C14 H14 . . 120.6 ?
C14 C15 C16 . . 119.19(19) ?
C14 C15 H15 . . 120.4 ?
C16 C15 H15 . . 120.4 ?
C15 C16 C17 . . 118.38(19) ?
C15 C16 H16 . . 120.8 ?
C17 C16 H16 . . 120.8 ?
N1 C17 C16 . . 123.48(19) ?
N1 C17 H17 . . 118.3 ?
C16 C17 H17 . . 118.3 ?
O4 C18 O5 . . 125.11(17) ?
O4 C18 C6 . . 123.28(18) ?
O5 C18 C6 . . 111.52(16) ?
O5 C19 H19A . . 109.5 ?
O5 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O5 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C17 N1 C13 . . 117.88(17) ?
C7 O3 C8 . . 114.76(16) ?
C18 O5 C19 . . 113.04(15) ?
C12 S1 C9 . . 92.21(10) ?
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 O1 . 1.215(2) ?
C1 C6 . 1.484(3) ?
C1 C2 . 1.526(2) ?
C2 C7 . 1.515(3) ?
C2 C3 . 1.546(3) ?
C2 H2 . 1.0000 ?
C3 C9 . 1.499(2) ?
C3 C4 . 1.529(2) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.509(3) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.353(3) ?
C5 C13 . 1.485(3) ?
C6 C18 . 1.508(2) ?
C7 O2 . 1.207(2) ?
C7 O3 . 1.335(2) ?
C8 O3 . 1.452(2) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.364(3) ?
C9 S1 . 1.733(2) ?
C10 C11 . 1.426(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.353(3) ?
C11 H11 . 0.9500 ?
C12 S1 . 1.725(2) ?
C12 H12 . 0.9500 ?
C13 N1 . 1.349(2) ?
C13 C14 . 1.400(3) ?
C14 C15 . 1.384(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.391(3) ?
C16 H16 . 0.9500 ?
C17 N1 . 1.335(3) ?
C17 H17 . 0.9500 ?
C18 O4 . 1.199(2) ?
C18 O5 . 1.344(2) ?
C19 O5 . 1.448(2) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
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
C3 H3 O3 1_455 1.00 2.64 3.625(2) 167.5 yes
C8 H8C O2 1_655 0.98 2.35 3.215(3) 146.2 yes
C11 H11 O1 1_554 0.95 2.62 3.193(2) 119.2 yes
C12 H12 O4 1_654 0.95 2.50 3.446(2) 179.5 yes
C14 H14 O2 1_565 0.95 2.61 3.468(2) 150.8 yes
C16 H16 O1 1_465 0.95 2.52 3.305(3) 140.4 yes
C19 H19B O2 1_566 0.98 2.64 3.584(3) 161.4 yes
C4 H4A Cg2 1_655 0.99 2.94 3.841(2) 152 yes
C19 H19C Cg1 1_556 0.98 2.78 3.659(3) 149 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
O1 C1 C2 C7 . . . . 29.2(3) ?
C6 C1 C2 C7 . . . . -151.60(17) ?
O1 C1 C2 C3 . . . . 149.70(18) ?
C6 C1 C2 C3 . . . . -31.1(2) ?
C7 C2 C3 C9 . . . . -51.8(2) ?
C1 C2 C3 C9 . . . . -173.75(15) ?
C7 C2 C3 C4 . . . . -178.86(15) ?
C1 C2 C3 C4 . . . . 59.17(19) ?
C9 C3 C4 C5 . . . . 174.49(16) ?
C2 C3 C4 C5 . . . . -58.3(2) ?
C3 C4 C5 C6 . . . . 28.6(3) ?
C3 C4 C5 C13 . . . . -149.71(17) ?
C13 C5 C6 C1 . . . . 179.18(17) ?
C4 C5 C6 C1 . . . . 0.9(3) ?
C13 C5 C6 C18 . . . . 1.4(3) ?
C4 C5 C6 C18 . . . . -176.85(18) ?
O1 C1 C6 C5 . . . . 179.91(19) ?
C2 C1 C6 C5 . . . . 0.7(3) ?
O1 C1 C6 C18 . . . . -2.1(3) ?
C2 C1 C6 C18 . . . . 178.65(16) ?
C1 C2 C7 O2 . . . . 50.6(3) ?
C3 C2 C7 O2 . . . . -70.3(2) ?
C1 C2 C7 O3 . . . . -133.27(17) ?
C3 C2 C7 O3 . . . . 105.76(18) ?
C4 C3 C9 C10 . . . . -122.9(2) ?
C2 C3 C9 C10 . . . . 112.5(2) ?
C4 C3 C9 S1 . . . . 56.8(2) ?
C2 C3 C9 S1 . . . . -67.7(2) ?
C3 C9 C10 C11 . . . . 179.62(19) ?
S1 C9 C10 C11 . . . . -0.2(2) ?
C9 C10 C11 C12 . . . . 0.2(3) ?
C10 C11 C12 S1 . . . . -0.2(2) ?
C6 C5 C13 N1 . . . . -20.6(3) ?
C4 C5 C13 N1 . . . . 157.70(17) ?
C6 C5 C13 C14 . . . . 160.74(19) ?
C4 C5 C13 C14 . . . . -20.9(3) ?
N1 C13 C14 C15 . . . . 0.4(3) ?
C5 C13 C14 C15 . . . . 178.96(17) ?
C13 C14 C15 C16 . . . . -0.3(3) ?
C14 C15 C16 C17 . . . . 0.5(3) ?
C15 C16 C17 N1 . . . . -0.9(3) ?
C5 C6 C18 O4 . . . . 107.7(2) ?
C1 C6 C18 O4 . . . . -70.2(2) ?
C5 C6 C18 O5 . . . . -75.7(2) ?
C1 C6 C18 O5 . . . . 106.35(19) ?
C16 C17 N1 C13 . . . . 0.9(3) ?
C14 C13 N1 C17 . . . . -0.7(3) ?
C5 C13 N1 C17 . . . . -179.31(17) ?
O2 C7 O3 C8 . . . . 6.2(3) ?
C2 C7 O3 C8 . . . . -169.87(18) ?
O4 C18 O5 C19 . . . . -8.5(3) ?
C6 C18 O5 C19 . . . . 174.97(15) ?
C11 C12 S1 C9 . . . . 0.08(18) ?
C10 C9 S1 C12 . . . . 0.06(16) ?
C3 C9 S1 C12 . . . . -179.74(17) ?
