Investigation of noncovalent interactions in organofluorine compounds with C–F bonds in different electronic environments
Das, Prantika; Bhandary, Subhrajyoti; Mathew, Dona; Dutta, Arnab; Dhabhai, Kanu Priya; Seth, Saikat Kumar; Chopra, Deepak; CrystEngComm 28 (2026) 1494–1507; doi:10.1039/D5CE00838G

data_7251496
_publ_section_title
;
 Investigation of noncovalent interactions in organofluorine compounds
 with C--F bonds in different electronic environments
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1494
_journal_page_last               1507
_journal_paper_doi               10.1039/D5CE00838G
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C10 H11 F2 N O'
_chemical_formula_sum            'C10 H11 F2 N O'
_chemical_formula_weight         199.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2025-08-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-08-28 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0624(7)
_cell_length_b                   9.4612(6)
_cell_length_c                   8.6588(4)
_cell_measurement_reflns_used    3963
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.86
_cell_measurement_theta_min      2.74
_cell_volume                     988.18(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      103.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8140
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.036
_diffrn_reflns_theta_min         2.736
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1526 before and 0.0791 after correction.
The Ratio of minimum to maximum transmission is 0.7547.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 668 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.1184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.541
_reflns_Friedel_fraction_full    0.809
_reflns_Friedel_fraction_max     0.613
_reflns_number_gt                2058
_reflns_number_total             2362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00838g2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7251494--7251497.cif.'
_cod_database_code               7251496
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              66111
_olex2_submission_special_instructions 'No special instructions were received'