#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/98/7219810.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_7219810
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           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-25T19:07:09-00:00
_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                 130.149(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7505(4)
_cell_length_b                   3.75740(10)
_cell_length_c                   26.3533(7)
_cell_measurement_reflns_used    3159
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      3
_cell_volume                     1040.75(6)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
        XL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_solution
;
        XS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0256
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7150
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.67
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0613 before and 0.0424 after correction.
        The Ratio of minimum to maximum transmission is 0.7912.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.3542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                1533
_reflns_number_total             1827
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00215j2.cif
_cod_data_source_block           80
_cod_depositor_comments
'Adding full bibliography for 7219787--7219816.cif.'
_cod_original_cell_volume        1040.74(5)
_cod_database_code               7219810
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F3 F 0.03468(9) 0.7139(3) 0.21153(4) 0.0323(3) Uani 1 1 d .
F1 F 0.04508(8) 0.6672(3) -0.03761(4) 0.0272(3) Uani 1 1 d .
F2 F 0.48782(9) 1.2504(3) 0.04517(4) 0.0302(3) Uani 1 1 d .
F4 F 0.21622(9) 0.9697(3) 0.33473(4) 0.0313(3) Uani 1 1 d .
C4 C 0.17693(15) 0.8376(4) -0.06136(8) 0.0231(4) Uani 1 1 d .
H4 H 0.115 0.7531 -0.1055 0.028 Uiso 1 1 calc R
C7 C 0.35629(15) 1.0861(4) 0.06905(8) 0.0207(3) Uani 1 1 d .
H7 H 0.4182 1.1732 0.113 0.025 Uiso 1 1 calc R
C9 C 0.15664(15) 0.8565(4) 0.18035(8) 0.0221(4) Uani 1 1 d .
H9 H 0.0916 0.7672 0.1369 0.027 Uiso 1 1 calc R
C2 C 0.24252(14) 0.9351(4) 0.04861(7) 0.0194(3) Uani 1 1 d .
C10 C 0.14157(14) 0.8495(4) 0.22696(8) 0.0224(4) Uani 1 1 d .
C6 C 0.37673(15) 1.1061(4) 0.02452(8) 0.0223(4) Uani 1 1 d .
C12 C 0.34559(15) 1.1205(4) 0.30779(8) 0.0233(4) Uani 1 1 d .
H12 H 0.4096 1.2109 0.3513 0.028 Uiso 1 1 calc R
C1 C 0.21635(15) 0.9037(4) 0.09426(8) 0.0208(3) Uani 1 1 d .
H1 H 0.1397 0.7945 0.0795 0.025 Uiso 1 1 calc R
C3 C 0.15637(14) 0.8158(4) -0.01652(7) 0.0204(3) Uani 1 1 d .
N1 N 0.29520(12) 1.0212(3) 0.15339(6) 0.0220(3) Uani 1 1 d .
C8 C 0.26894(15) 0.9966(4) 0.19736(8) 0.0203(3) Uani 1 1 d .
C13 C 0.36288(15) 1.1282(4) 0.26125(8) 0.0223(4) Uani 1 1 d .
H13 H 0.4391 1.2236 0.2731 0.027 Uiso 1 1 calc R
C11 C 0.23529(16) 0.9812(4) 0.29032(8) 0.0226(4) Uani 1 1 d .
C5 C 0.29014(15) 0.9860(4) -0.04030(8) 0.0242(4) Uani 1 1 d .
H5 H 0.3077 1.0047 -0.0696 0.029 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F3 0.0274(5) 0.0448(6) 0.0298(5) -0.0033(4) 0.0207(5) -0.0075(5)
F1 0.0220(5) 0.0345(6) 0.0242(5) -0.0054(4) 0.0145(4) -0.0061(4)
F2 0.0268(5) 0.0391(6) 0.0310(5) -0.0046(4) 0.0215(5) -0.0075(4)
F4 0.0355(6) 0.0424(6) 0.0236(5) -0.0002(4) 0.0225(5) 0.0001(5)
C4 0.0256(9) 0.0219(8) 0.0193(8) -0.0003(6) 0.0134(7) 0.0031(7)
C7 0.0216(8) 0.0180(8) 0.0207(8) 0.0000(6) 0.0128(7) 0.0023(6)
C9 0.0234(8) 0.0216(8) 0.0190(8) -0.0011(6) 0.0127(7) -0.0001(7)
C2 0.0216(8) 0.0148(7) 0.0218(8) 0.0029(6) 0.0141(7) 0.0043(6)
C10 0.0211(8) 0.0214(8) 0.0264(8) 0.0021(7) 0.0161(7) 0.0003(7)
C6 0.0214(8) 0.0205(8) 0.0266(8) 0.0014(6) 0.0162(7) -0.0002(6)
C12 0.0262(9) 0.0214(8) 0.0186(8) -0.0011(6) 0.0128(7) 0.0008(7)
C1 0.0210(8) 0.0184(8) 0.0236(8) 0.0011(6) 0.0147(7) 0.0005(6)
C3 0.0174(8) 0.0183(8) 0.0235(8) 0.0009(6) 0.0122(7) 0.0006(6)
N1 0.0243(7) 0.0221(7) 0.0214(7) 0.0003(5) 0.0155(6) -0.0005(6)
C8 0.0236(8) 0.0175(7) 0.0213(8) 0.0015(6) 0.0152(7) 0.0018(6)
C13 0.0227(8) 0.0186(8) 0.0237(8) 0.0010(6) 0.0141(7) 0.0002(7)
C11 0.0291(9) 0.0216(8) 0.0219(8) 0.0035(6) 0.0185(8) 0.0047(7)
C5 0.0293(9) 0.0237(8) 0.0248(9) 0.0026(7) 0.0199(8) 0.0045(7)
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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C4 C5 118.45(14)
C6 C7 C2 119.03(14)
C10 C9 C8 119.44(14)
C7 C2 C1 121.32(14)
C3 C2 C7 117.14(13)
C3 C2 C1 121.54(14)
F3 C10 C9 120.15(14)
F3 C10 C11 119.02(13)
C9 C10 C11 120.83(14)
F2 C6 C7 118.39(13)
F2 C6 C5 118.28(13)
C7 C6 C5 123.33(14)
C11 C12 C13 119.45(14)
N1 C1 C2 120.72(14)
F1 C3 C4 117.98(13)
F1 C3 C2 118.30(13)
C4 C3 C2 123.72(14)
C1 N1 C8 120.79(14)
C9 C8 N1 124.71(14)
C13 C8 C9 119.38(14)
C13 C8 N1 115.90(13)
C12 C13 C8 120.35(14)
F4 C11 C10 118.81(14)
F4 C11 C12 120.64(14)
C12 C11 C10 120.55(14)
C6 C5 C4 118.33(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F3 C10 1.3471(17)
F1 C3 1.3658(17)
F2 C6 1.3609(18)
F4 C11 1.3552(17)
C4 C3 1.383(2)
C4 C5 1.389(2)
C7 C2 1.404(2)
C7 C6 1.374(2)
C9 C10 1.371(2)
C9 C8 1.404(2)
C2 C1 1.466(2)
C2 C3 1.389(2)
C10 C11 1.385(2)
C6 C5 1.384(2)
C12 C13 1.392(2)
C12 C11 1.373(2)
C1 N1 1.273(2)
N1 C8 1.4216(19)
C8 C13 1.394(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200003
