#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/98/7219812.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7219812
loop_
_publ_author_name
'Kaur, Gurpreet'
'Choudhury, Angshuman Roy'
_publ_section_title
;
 A comprehensive understanding of the synthons involving C--H⋯F--C
 hydrogen bond(s) from structural and computational analyses
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              2949
_journal_paper_doi               10.1039/C5CE00215J
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-29T11:16:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.000(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.004(3)
_cell_length_b                   30.750(13)
_cell_length_c                   10.041(4)
_cell_measurement_reflns_used    1881
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.43
_cell_measurement_theta_min      2.44
_cell_volume                     2135.9(15)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5980
_diffrn_reflns_point_group_measured_fraction_full 0.717
_diffrn_reflns_point_group_measured_fraction_max 0.717
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.444
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0556 before and 0.0443 after correction.
        The Ratio of minimum to maximum transmission is 0.9133.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       THIN
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.04
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         2697
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0363P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0704
_reflns_number_gt                2393
_reflns_number_total             2697
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce00215j2.cif
_cod_data_source_block           82
_cod_depositor_comments
'Adding full bibliography for 7219787--7219816.cif.'
_cod_database_code               7219812
#BEGIN Tags that were not found in dictionaries:
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.986
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
F2 F 0.4396(3) 0.47040(6) 0.23456(19) 0.0272(5) Uani 1 d
F1 F 0.7394(3) 0.45896(6) 0.68518(18) 0.0259(5) Uani 1 d
F4 F 0.1649(3) 0.59122(6) 0.4325(2) 0.0341(5) Uani 1 d
C3 C 0.6631(5) 0.44013(11) 0.5662(3) 0.0201(8) Uani 1 d
F3 F 0.1894(3) 0.67652(7) 0.4797(3) 0.0463(7) Uani 1 d
C6 C 0.5130(5) 0.40219(11) 0.3284(4) 0.0237(8) Uani 1 d
H6 H 0.4623 0.3892 0.2444 0.028 Uiso 1 calc
C2 C 0.5887(5) 0.46777(11) 0.4617(4) 0.0182(7) Uani 1 d
C4 C 0.6640(5) 0.39550(11) 0.5594(4) 0.0239(8) Uani 1 d
H4 H 0.7154 0.3783 0.6351 0.029 Uiso 1 calc
C11 C 0.5269(6) 0.67545(12) 0.4873(4) 0.0325(9) Uani 1 d
H11 H 0.5345 0.7058 0.5046 0.039 Uiso 1 calc
C10 C 0.6910(6) 0.65134(12) 0.4776(4) 0.0314(10) Uani 1 d
H10 H 0.8132 0.6654 0.4873 0.038 Uiso 1 calc
C1 C 0.5964(5) 0.51502(11) 0.4814(3) 0.0203(8) Uani 1 d
H1 H 0.6927 0.5268 0.5489 0.024 Uiso 1 calc
C8 C 0.5027(5) 0.58571(10) 0.4387(3) 0.0184(8) Uani 1 d
C12 C 0.3536(6) 0.65417(12) 0.4713(4) 0.0292(9) Uani 1 d
C7 C 0.5139(5) 0.44631(11) 0.3432(4) 0.0202(8) Uani 1 d
C13 C 0.3406(5) 0.61038(12) 0.4465(4) 0.0249(8) Uani 1 d
N1 N 0.4784(4) 0.54088(9) 0.4113(3) 0.0197(6) Uani 1 d
C5 C 0.5871(5) 0.37671(11) 0.4376(3) 0.0228(8) Uani 1 d
H5 H 0.5852 0.3459 0.429 0.027 Uiso 1 calc
C9 C 0.6791(5) 0.60715(11) 0.4540(3) 0.0248(8) Uani 1 d
H9 H 0.7935 0.5912 0.4481 0.03 Uiso 1 calc
F5 F -0.0603(3) 0.43734(6) 0.21015(19) 0.0290(5) Uani 1 d
F6 F 0.1939(3) 0.37352(6) 0.62402(19) 0.0292(5) Uani 1 d
C14 C 0.0308(5) 0.36121(10) 0.3439(4) 0.0204(7) Uani 1 d
H14 H -0.0653 0.36 0.2659 0.024 Uiso 1 calc
C20 C 0.1482(5) 0.40903(10) 0.5464(3) 0.0198(8) Uani 1 d
F8 F 0.3852(3) 0.27735(7) 0.2769(2) 0.0406(6) Uani 1 d
F7 F 0.2880(3) 0.20705(8) 0.1267(3) 0.0504(7) Uani 1 d
C15 C 0.0666(5) 0.40319(10) 0.4125(3) 0.0182(7) Uani 1 d
C17 C 0.0456(5) 0.48233(11) 0.3949(4) 0.0201(8) Uani 1 d
H17 H 0.0098 0.5074 0.3415 0.024 Uiso 1 calc
C19 C 0.1790(5) 0.44891(10) 0.6060(3) 0.0195(8) Uani 1 d
H19 H 0.2343 0.4514 0.6983 0.023 Uiso 1 calc
C21 C 0.0610(5) 0.28900(10) 0.3052(3) 0.0220(8) Uani 1 d
C18 C 0.1273(5) 0.48575(11) 0.5281(4) 0.0221(8) Uani 1 d
H18 H 0.1489 0.5137 0.5677 0.027 Uiso 1 calc
C25 C 0.1478(6) 0.22878(12) 0.1765(4) 0.0306(9) Uani 1 d
N2 N 0.1197(4) 0.32667(9) 0.3822(3) 0.0228(7) Uani 1 d
C23 C -0.1780(6) 0.23810(11) 0.2014(4) 0.0282(9) Uani 1 d
H23 H -0.3089 0.2288 0.1849 0.034 Uiso 1 calc
C16 C 0.0180(5) 0.44143(11) 0.3422(3) 0.0203(8) Uani 1 d
C24 C -0.0405(6) 0.21488(12) 0.1491(4) 0.0301(9) Uani 1 d
H24 H -0.0744 0.1898 0.0952 0.036 Uiso 1 calc
C26 C 0.1987(5) 0.26454(11) 0.2549(4) 0.0255(8) Uani 1 d
C22 C -0.1289(5) 0.27487(11) 0.2779(4) 0.0260(9) Uani 1 d
H22 H -0.2268 0.2908 0.3123 0.031 Uiso 1 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
F1 C3 C2 117.0(3)
F1 C3 C4 117.7(3)
C4 C3 C2 125.3(3)
C7 C6 C5 118.8(3)
C3 C2 C1 120.2(3)
C3 C2 C7 113.8(3)
C7 C2 C1 126.0(3)
C3 C4 C5 117.2(3)
C12 C11 C10 117.9(3)
C9 C10 C11 120.8(3)
N1 C1 C2 122.4(3)
C13 C8 N1 118.3(3)
C13 C8 C9 117.3(3)
C9 C8 N1 124.3(3)
F3 C12 C11 119.8(3)
F3 C12 C13 118.5(3)
C11 C12 C13 121.7(4)
F2 C7 C6 117.5(3)
F2 C7 C2 118.4(3)
C6 C7 C2 124.1(3)
F4 C13 C8 119.9(3)
F4 C13 C12 118.7(3)
C12 C13 C8 121.3(3)
C1 N1 C8 117.0(3)
C6 C5 C4 120.7(3)
C10 C9 C8 121.0(3)
N2 C14 C15 124.0(3)
F6 C20 C15 118.6(3)
F6 C20 C19 117.8(3)
C19 C20 C15 123.6(3)
C20 C15 C14 125.7(3)
C16 C15 C14 119.9(3)
C16 C15 C20 114.5(3)
C16 C17 C18 117.3(3)
C20 C19 C18 118.4(3)
C26 C21 N2 119.0(3)
C26 C21 C22 117.4(3)
C22 C21 N2 123.5(3)
C17 C18 C19 121.1(3)
F7 C25 C24 120.3(3)
F7 C25 C26 118.2(3)
C26 C25 C24 121.5(3)
C14 N2 C21 115.8(3)
C24 C23 C22 120.8(4)
F5 C16 C15 116.6(3)
F5 C16 C17 118.3(3)
C17 C16 C15 125.1(3)
C23 C24 C25 118.2(3)
F8 C26 C21 119.7(3)
F8 C26 C25 119.2(3)
C25 C26 C21 121.0(3)
C23 C22 C21 121.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F2 C7 1.354(4)
F1 C3 1.360(4)
F4 C13 1.352(4)
C3 C2 1.387(5)
C3 C4 1.374(5)
F3 C12 1.354(4)
C6 C7 1.365(5)
C6 C5 1.381(5)
C2 C1 1.466(5)
C2 C7 1.389(5)
C4 C5 1.383(5)
C11 C10 1.384(5)
C11 C12 1.366(5)
C10 C9 1.380(5)
C1 N1 1.276(4)
C8 C13 1.378(5)
C8 N1 1.411(4)
C8 C9 1.388(5)
C12 C13 1.370(5)
F5 C16 1.359(4)
F6 C20 1.350(4)
C14 C15 1.466(4)
C14 N2 1.260(4)
C20 C15 1.388(4)
C20 C19 1.367(4)
F8 C26 1.349(4)
F7 C25 1.347(4)
C15 C16 1.386(5)
C17 C18 1.374(5)
C17 C16 1.366(5)
C19 C18 1.392(5)
C21 N2 1.417(4)
C21 C26 1.380(5)
C21 C22 1.385(5)
C25 C24 1.373(5)
C25 C26 1.366(5)
C23 C24 1.368(5)
C23 C22 1.380(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200005
