#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/54/7055428.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_7055428
loop_
_publ_author_name
'Panini, Piyush'
'Gonnade, Rajesh G.'
'Chopra, Deepak'
_publ_section_title
;
 Experimental and computational analysis of supramolecular motifs
 involving Csp2(aromatic)--F and CF3groups in organic solids
;
_journal_issue                   6
_journal_name_full               'New J. Chem.'
_journal_page_first              4981
_journal_paper_doi               10.1039/C5NJ03211C
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C14 H9 F4 N O'
_chemical_formula_sum            'C14 H9 F4 N O'
_chemical_formula_weight         283.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-03-09 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.70(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.214(7)
_cell_length_b                   5.1860(12)
_cell_length_c                   16.020(4)
_cell_measurement_reflns_used    1835
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.57
_cell_volume                     2317.0(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Mercury
_computing_publication_material  Mercury
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2013)'
_computing_structure_solution    'SIR 92'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_min         2.572
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       rod
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0444P)²+2.0826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2360
_reflns_number_total             2856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj03211c2.cif
_cod_data_source_block           2F3T
_cod_depositor_comments
'Adding full bibliography for 7055417--7055429.cif.'
_cod_original_cell_volume        2317.1(9)
_cod_database_code               7055428
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_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'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 1.12692(3) 1.10512(16) 0.79693(5) 0.0237(2) Uani 1 1 d . .
F4 F 0.73225(3) 0.85494(19) 0.87700(7) 0.0362(3) Uani 1 1 d . .
F3 F 0.73991(3) 0.5275(2) 0.79904(6) 0.0355(3) Uani 1 1 d . .
F2 F 0.75326(3) 0.4907(2) 0.93373(6) 0.0370(3) Uani 1 1 d . .
O1 O 0.97197(3) 1.11862(18) 0.88689(6) 0.0218(2) Uani 1 1 d . .
N1 N 0.98985(4) 0.6914(2) 0.88013(7) 0.0163(2) Uani 1 1 d . .
H1 H 0.9777 0.5349 0.8786 0.020 Uiso 1 1 calc R U
C9 C 1.10811(5) 0.9146(3) 0.83955(8) 0.0176(3) Uani 1 1 d . .
C8 C 1.05916(5) 0.9136(3) 0.83841(8) 0.0167(3) Uani 1 1 d . .
H8 H 1.0394 1.0449 0.8102 0.020 Uiso 1 1 calc R U
C7 C 1.03972(4) 0.7132(2) 0.88015(8) 0.0148(3) Uani 1 1 d . .
C13 C 0.95916(4) 0.8920(2) 0.88230(8) 0.0158(3) Uani 1 1 d . .
C1 C 0.90765(4) 0.8190(2) 0.87905(8) 0.0150(3) Uani 1 1 d . .
C6 C 0.88780(5) 0.6041(2) 0.83453(8) 0.0165(3) Uani 1 1 d . .
H6 H 0.9075 0.4930 0.8075 0.020 Uiso 1 1 calc R U
C5 C 0.83937(5) 0.5526(3) 0.82975(8) 0.0172(3) Uani 1 1 d . .
H5 H 0.8256 0.4081 0.7986 0.021 Uiso 1 1 calc R U
C4 C 0.81107(4) 0.7137(3) 0.87072(8) 0.0167(3) Uani 1 1 d . .
C14 C 0.75932(5) 0.6480(3) 0.86960(9) 0.0213(3) Uani 1 1 d . .
C2 C 0.87886(5) 0.9804(2) 0.91924(8) 0.0169(3) Uani 1 1 d . .
H2 H 0.8924 1.1276 0.9491 0.020 Uiso 1 1 calc R U
C3 C 0.83057(5) 0.9270(3) 0.91579(8) 0.0183(3) Uani 1 1 d . .
H3 H 0.8109 1.0354 0.9440 0.022 Uiso 1 1 calc R U
C12 C 1.06925(5) 0.5220(3) 0.92079(8) 0.0170(3) Uani 1 1 d . .
H12 H 1.0558 0.3847 0.9487 0.020 Uiso 1 1 calc R U
C11 C 1.11837(5) 0.5326(3) 0.92041(8) 0.0191(3) Uani 1 1 d . .
H11 H 1.1384 0.4020 0.9483 0.023 Uiso 1 1 calc R U
C10 C 1.13845(5) 0.7308(3) 0.87991(8) 0.0188(3) Uani 1 1 d . .
H10 H 1.1721 0.7398 0.8799 0.023 Uiso 1 1 calc R U
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 0.0000 0.0000 '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'
O O 0.0106 0.0060 '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
C13 N1 C7 125.32(11)
C13 N1 H1 117.3
C7 N1 H1 117.3
F1 C9 C10 118.65(12)
F1 C9 C8 117.66(12)
C10 C9 C8 123.68(12)
C9 C8 C7 117.58(12)
C9 C8 H8 121.2
C7 C8 H8 121.2
C12 C7 C8 120.33(11)
C12 C7 N1 117.98(11)
C8 C7 N1 121.65(11)
O1 C13 N1 123.49(12)
O1 C13 C1 121.32(12)
N1 C13 C1 115.18(11)
C2 C1 C6 120.05(12)
C2 C1 C13 117.66(11)
C6 C1 C13 122.23(11)
C5 C6 C1 119.97(12)
C5 C6 H6 120.0
C1 C6 H6 120.0
C6 C5 C4 119.48(12)
C6 C5 H5 120.3
C4 C5 H5 120.3
C5 C4 C3 120.98(12)
C5 C4 C14 119.19(12)
C3 C4 C14 119.77(12)
F4 C14 F3 106.56(11)
F4 C14 F2 106.26(11)
F3 C14 F2 106.25(12)
F4 C14 C4 112.77(12)
F3 C14 C4 113.04(11)
F2 C14 C4 111.46(11)
C3 C2 C1 120.13(12)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 119.38(12)
C2 C3 H3 120.3
C4 C3 H3 120.3
C11 C12 C7 119.83(12)
C11 C12 H12 120.1
C7 C12 H12 120.1
C10 C11 C12 120.80(12)
C10 C11 H11 119.6
C12 C11 H11 119.6
C9 C10 C11 117.78(12)
C9 C10 H10 121.1
C11 C10 H10 121.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C9 1.3539(15)
F4 C14 1.3326(17)
F3 C14 1.3346(16)
F2 C14 1.3428(17)
O1 C13 1.2284(16)
N1 C13 1.3575(17)
N1 C7 1.4116(16)
N1 H1 0.8800
C9 C10 1.3756(19)
C9 C8 1.3786(18)
C8 C7 1.3925(18)
C8 H8 0.9500
C7 C12 1.3918(18)
C13 C1 1.4952(18)
C1 C2 1.3902(18)
C1 C6 1.3942(18)
C6 C5 1.3831(18)
C6 H6 0.9500
C5 C4 1.3872(18)
C5 H5 0.9500
C4 C3 1.3887(18)
C4 C14 1.4966(18)
C2 C3 1.3833(18)
C2 H2 0.9500
C3 H3 0.9500
C12 C11 1.3877(19)
C12 H12 0.9500
C11 C10 1.3818(19)
C11 H11 0.9500
C10 H10 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
F1 C9 C8 C7 178.11(11)
C10 C9 C8 C7 -0.50(19)
C9 C8 C7 C12 -0.31(18)
C9 C8 C7 N1 -177.93(11)
C13 N1 C7 C12 146.64(12)
C13 N1 C7 C8 -35.69(18)
C7 N1 C13 O1 -2.0(2)
C7 N1 C13 C1 178.18(11)
O1 C13 C1 C2 -29.59(18)
N1 C13 C1 C2 150.18(12)
O1 C13 C1 C6 147.56(13)
N1 C13 C1 C6 -32.66(17)
C2 C1 C6 C5 0.54(19)
C13 C1 C6 C5 -176.55(12)
C1 C6 C5 C4 -1.11(19)
C6 C5 C4 C3 0.60(19)
C6 C5 C4 C14 -176.37(12)
C5 C4 C14 F4 -152.92(12)
C3 C4 C14 F4 30.07(17)
C5 C4 C14 F3 -31.95(18)
C3 C4 C14 F3 151.04(12)
C5 C4 C14 F2 87.66(15)
C3 C4 C14 F2 -89.35(15)
C6 C1 C2 C3 0.56(19)
C13 C1 C2 C3 177.78(11)
C1 C2 C3 C4 -1.07(19)
C5 C4 C3 C2 0.50(19)
C14 C4 C3 C2 177.45(12)
C8 C7 C12 C11 0.62(18)
N1 C7 C12 C11 178.33(11)
C7 C12 C11 C10 -0.14(19)
F1 C9 C10 C11 -177.63(11)
C8 C9 C10 C11 0.96(19)
C12 C11 C10 C9 -0.62(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 1810434
