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#$Date: 2022-02-04 21:19:41 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272610 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/41/7244180.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_7244180
loop_
_publ_author_name
'Vaganova, Tamara A.'
'Benassi, Enrico'
'Gatilov, Yurij V.'
'Chuikov, Igor P.'
'Pishchur, Denis P.'
'Malykhin, Evgenij V.'
_publ_section_title
;
 Polyhalogenated aminobenzonitriles vs. their co-crystals with 18-crown-6:
 amino group position as a tool to control crystal packing and solid-state
 fluorescence
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              987
_journal_page_last               1001
_journal_paper_doi               10.1039/D1CE01469B
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C7 H3 F3 N2'
_chemical_formula_sum            'C7 H3 F3 N2'
_chemical_formula_weight         172.11
_chemical_melting_point          369
_chemical_name_systematic        4-amino-2,3,5-trifluorobenzonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-10-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.061(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.7360(7)
_cell_length_b                   8.4997(17)
_cell_length_c                   10.654(2)
_cell_measurement_reflns_used    1346
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      3.07
_cell_volume                     336.43(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2291
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.828
_diffrn_reflns_theta_min         3.073
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_correction_T_min  0.8193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       prism
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.815
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1092
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.813
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0325
_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/[σ²(Fo²)+(0.0977P)²+0.0066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_full    0.713
_reflns_Friedel_fraction_max     0.674
_reflns_number_gt                990
_reflns_number_total             1092
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01469b2.cif
_cod_data_source_block           C-M96
_cod_depositor_comments
'Adding full bibliography for 7244175--7244182.cif.'
_cod_original_cell_volume        336.44(12)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7244180
_shelx_shelxl_version_number     2018/3
_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   0.942
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3925(5) 0.7631(2) 0.08363(17) 0.0417(5) Uani 1 1 d . . . . .
N1 N 0.2035(9) 1.2956(3) 0.1873(3) 0.0415(7) Uani 1 1 d D . . . .
H2 H 0.218(11) 1.367(4) 0.248(3) 0.049(11) Uiso 1 1 d D . . . .
H1 H 0.064(10) 1.309(5) 0.115(3) 0.050(10) Uiso 1 1 d D . . . .
C1 C 0.6246(7) 0.8507(3) 0.2867(3) 0.0270(6) Uani 1 1 d . . . . .
F2 F 0.1187(4) 1.0452(3) 0.02198(14) 0.0412(5) Uani 1 1 d . . . . .
C2 C 0.4398(8) 0.8796(3) 0.1691(3) 0.0281(7) Uani 1 1 d . . . . .
N2 N 0.8991(7) 0.5768(4) 0.3355(2) 0.0430(7) Uani 1 1 d . . . . .
F3 F 0.5587(6) 1.2408(2) 0.42038(18) 0.0460(6) Uani 1 1 d . . . . .
C3 C 0.3018(7) 1.0255(4) 0.1365(2) 0.0283(7) Uani 1 1 d . . . . .
C4 C 0.3348(8) 1.1523(3) 0.2194(3) 0.0292(7) Uani 1 1 d . . . . .
C5 C 0.5219(8) 1.1188(4) 0.3380(3) 0.0309(7) Uani 1 1 d . . . . .
C6 C 0.6632(8) 0.9760(3) 0.3725(3) 0.0293(7) Uani 1 1 d . . . . .
H6 H 0.787206 0.961216 0.454218 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7733(8) 0.6984(4) 0.3150(3) 0.0316(7) Uani 1 1 d . . . . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 H2 116(3) . . ?
C4 N1 H1 120(3) . . ?
H2 N1 H1 122(4) . . ?
C2 C1 C6 117.5(3) . . ?
C2 C1 C7 119.8(3) . . ?
C6 C1 C7 122.7(3) . . ?
F1 C2 C3 118.4(2) . . ?
F1 C2 C1 119.9(3) . . ?
C3 C2 C1 121.7(3) . . ?
F2 C3 C2 118.9(3) . . ?
F2 C3 C4 118.8(3) . . ?
C2 C3 C4 122.2(2) . . ?
N1 C4 C3 122.4(3) . . ?
N1 C4 C5 123.0(3) . . ?
C3 C4 C5 114.6(3) . . ?
F3 C5 C6 119.9(2) . . ?
F3 C5 C4 115.7(3) . . ?
C6 C5 C4 124.4(3) . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N2 C7 C1 178.2(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.344(3) . ?
N1 C4 1.344(4) . ?
N1 H2 0.89(2) . ?
N1 H1 0.89(2) . ?
C1 C2 1.387(4) . ?
C1 C6 1.401(4) . ?
C1 C7 1.429(4) . ?
F2 C3 1.345(3) . ?
C2 C3 1.373(4) . ?
N2 C7 1.147(4) . ?
F3 C5 1.356(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.407(4) . ?
C5 C6 1.359(4) . ?
C6 H6 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 -179.4(2) . . . . ?
C7 C1 C2 F1 1.9(4) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C7 C1 C2 C3 -178.0(3) . . . . ?
F1 C2 C3 F2 1.4(4) . . . . ?
C1 C2 C3 F2 -178.6(2) . . . . ?
F1 C2 C3 C4 179.3(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
F2 C3 C4 N1 -2.9(4) . . . . ?
C2 C3 C4 N1 179.2(3) . . . . ?
F2 C3 C4 C5 178.3(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
N1 C4 C5 F3 1.0(4) . . . . ?
C3 C4 C5 F3 179.8(3) . . . . ?
N1 C4 C5 C6 -178.8(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
F3 C5 C6 C1 -179.8(2) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C7 C1 C6 C5 178.4(3) . . . . ?
