Quantitative crystal structure analysis in trifluoromethyl- and cyano-substituted N-phenylbenzamides.
Mandal, Koushik; Chopra, Deepak; Acta crystallographica Section B, Structural science, crystal engineering and materials 81 (2025) 266–282; doi:10.1107/S205252062500099X

data_2312793
_publ_section_title
;
 Quantitative crystal structure analysis in trifluoromethyl- and
 cyano-substituted N-phenylbenzamides.
;
_journal_issue                   2
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              266
_journal_page_last               282
_journal_paper_doi               10.1107/S205252062500099X
_journal_volume                  81
_journal_year                    2025
_chemical_formula_moiety         'C15 H9 F3 N2 O'
_chemical_formula_sum            'C15 H9 F3 N2 O'
_chemical_formula_weight         290.24
_chemical_name_systematic        3CN4T
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.5250(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7186(5)
_cell_length_b                   9.5567(10)
_cell_length_c                   28.0360(3)
_cell_measurement_reflns_used    1397
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.75
_cell_measurement_theta_min      2.25
_cell_volume                     1261.87(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_av_unetI/netI     0.1219
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            17649
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.132
_diffrn_reflns_theta_min         2.252
_diffrn_source_current           1.39
_diffrn_source_power             0.0695
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1184 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.7953.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_preparation       'Slow evaporation'
_exptl_crystal_recrystallization_method 'Slow evaporation from DCM'
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.1926
_refine_ls_R_factor_gt           0.1464
_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/[\s^2^(Fo^2^)+(0.0771P)^2^+9.0927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3182
_refine_ls_wR_factor_ref         0.3439
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2513
_reflns_number_total             3689
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {c5dc4b23-3b8a-4503-ae07-fb1a02efa890}
_cod_data_source_file            aw5098sup1.cif
_cod_data_source_block           3CN4T
_cod_depositor_comments
'Adding full bibliography for 2312792--2312801.cif.'
_cod_database_code               2312793
_cod_database_fobs_code          2312793
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
F3 \\sim H10 \\sim C12 \\sim N1 \\sim C14 \\sim H1 \\sim C11 \\sim C1 \\sim H11
\\sim C3 \\sim H13 \\sim H3 \\sim C10 \\sim C4 \\sim C8 \\sim H4 \\sim C5 \\sim
O1 \\sim C15 \\sim C2 \\sim C13 \\sim F2 \\sim H14 \\sim N2 \\sim C9 \\sim F1
\\sim H5 \\sim C7 \\sim H7 \\sim C6: within 2A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 2A
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_shelx_res_checksum              14282
_shelx_hkl_checksum              73683
_olex2_submission_special_instructions 'No special instructions were received'