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_2312794
_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        4CN3T
_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
_atom_sites_solution_primary     intrinsic
_audit_creation_date             2024-12-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.72(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.77(2)
_cell_length_b                   19.92(2)
_cell_length_c                   7.226(9)
_cell_measurement_reflns_used    599
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.86
_cell_measurement_theta_min      2.17
_cell_volume                     2702(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_unetI/netI     0.3911
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         2.045
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1240 before and 0.0905 after correction.
The Ratio of minimum to maximum transmission is 0.7582.
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    1.427
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_preparation       'Sublimation method'
_exptl_crystal_recrystallization_method 'Sublimation method'
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         5133
_refine_ls_number_restraints     373
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.3098
_refine_ls_R_factor_gt           0.1500
_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^)+(0.1794P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3392
_refine_ls_wR_factor_ref         0.4411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1569
_reflns_number_total             5133
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {4df92cfa-0f4a-4919-985a-bc7fe26f55e6}
_cod_data_source_file            aw5098sup1.cif
_cod_data_source_block           4CN3T
_cod_depositor_comments
'Adding full bibliography for 2312792--2312801.cif.'
_cod_original_cell_volume        2702(6)
_cod_database_code               2312794
_cod_database_fobs_code          2312794
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.561
 0.439
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim F4 \\sim F5
\\sim F6 \\sim N1 \\sim N2 \\sim O1 \\sim C16 \\sim C17 \\sim C18 \\sim C19
\\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27
\\sim C28 \\sim C29 \\sim C30 \\sim F7 \\sim F8 \\sim F9 \\sim N3 \\sim N4
\\sim O2: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
within 2A
C30 \\sim F7 \\sim F8 \\sim F9 \\sim F10 \\sim F11 \\sim F12: within 2A with
sigma of 0.002 and sigma for terminal atoms of 0.004 within 2A
C15 \\sim F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6: within 2A with sigma
of 0.002 and sigma for terminal atoms of 0.004 within 2A
5. Others
 Sof(F1)=Sof(F2)=Sof(F3)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(F10)=Sof(F11)=Sof(F12)=1-FVAR(2)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C21(H21), C22(H22), C25(H25), C27(H27), C28(H28), C29(H29),
  N3(H3)
;
_shelx_res_checksum              21770
_shelx_hkl_checksum              29962
_olex2_submission_special_instructions 'No special instructions were received'