Synthesis, crystal structure and Hirshfeld surface analysis of 5-oxo-N-phenyl-3-(thiophen-2-yl)-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxamide
Aliyeva, Khatira N.; Hökelek, Tuncer; Khrustalev, Victor N.; Rzayev, Rovnag M.; Bhattarai, Ajaya; Maharramov, Abel M.; Shikhaliyev, Namig G.; Acta Crystallographica Section E Crystallographic Communications 81 (2025) –; doi:10.1107/S205698902500057X

data_2023363
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 5-oxo-N-phenyl-3-(thiophen-2-yl)-2,3,4,5-tetrahydro-[1,1&#x2032;-biphenyl]-4-carboxamide
;
_journal_coeditor_code           WM5747
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S205698902500057X
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C23 H19 N O2 S'
_chemical_formula_moiety         'C23 H19 N O2 S'
_chemical_formula_sum            'C23 H19 N O2 S'
_chemical_formula_weight         373.45
_chemical_name_systematic
5-Oxo-<i>N</i>-phenyl-3-(thiophen-2-yl)-2,3,4,5-tetrahydro-[1,1'-biphenyl]-4-carboxamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.4160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1416(5)
_cell_length_b                   12.8991(4)
_cell_length_c                   19.0656(5)
_cell_measurement_reflns_used    9482
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.46
_cell_measurement_theta_min      2.24
_cell_volume                     3787.71(19)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            44070
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.589
_diffrn_reflns_theta_min         2.147
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.647
_refine_ls_abs_structure_details
;
Refined as an inversion twin;
Flack <i>x</i> determined using 5763 quotients
[(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
;
_refine_ls_abs_structure_Flack   0.37(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         13781
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+3.9600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                12646
_reflns_number_total             13781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5747.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2023363
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.972
_shelx_hkl_checksum              16379
_shelx_res_checksum              75995