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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/7/24/41/7244178.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_7244178
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          367
_chemical_name_systematic        4-amino-2,3,6-trifluorobenzonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 96.846(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5702(5)
_cell_length_b                   5.8303(3)
_cell_length_c                   15.8912(11)
_cell_measurement_reflns_used    3475
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.58
_cell_volume                     696.38(8)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7627
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.582
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_correction_T_min  0.8518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1587
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0455
_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)+(0.0536P)²+0.4947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1084
_reflns_number_total             1587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01469b2.cif
_cod_data_source_block           B-M98
_cod_depositor_comments
'Adding full bibliography for 7244175--7244182.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7244178
_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   0.909
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_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_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
N1 N 0.1954(3) 0.7122(4) -0.04119(14) 0.0601(6) Uani 1 1 d D . . . .
H2 H 0.126(4) 0.838(4) -0.042(2) 0.090(11) Uiso 1 1 d D . . . .
H1 H 0.237(4) 0.652(5) -0.0874(14) 0.079(9) Uiso 1 1 d D . . . .
F1 F 0.1179(2) 0.6271(3) 0.24816(9) 0.0683(5) Uani 1 1 d . . . . .
C1 C 0.2740(3) 0.3394(4) 0.18427(14) 0.0443(5) Uani 1 1 d . . . . .
F2 F 0.0639(2) 0.8648(3) 0.10155(10) 0.0658(5) Uani 1 1 d . . . . .
N2 N 0.3198(4) 0.1005(5) 0.32108(15) 0.0786(8) Uani 1 1 d . . . . .
C2 C 0.1821(3) 0.5452(4) 0.17898(13) 0.0448(5) Uani 1 1 d . . . . .
C3 C 0.1559(3) 0.6649(4) 0.10457(14) 0.0447(5) Uani 1 1 d . . . . .
F3 F 0.4301(2) 0.0658(3) 0.11504(10) 0.0694(5) Uani 1 1 d . . . . .
C4 C 0.2210(3) 0.5873(4) 0.03148(14) 0.0439(5) Uani 1 1 d . . . . .
C5 C 0.3138(3) 0.3791(4) 0.03593(14) 0.0469(5) Uani 1 1 d . . . . .
H5 H 0.358432 0.320379 -0.011676 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3377(3) 0.2641(4) 0.11077(15) 0.0474(5) Uani 1 1 d . . . . .
C7 C 0.3001(3) 0.2096(5) 0.26080(17) 0.0563(6) 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 118(2) . . ?
C4 N1 H1 117(2) . . ?
H2 N1 H1 124(3) . . ?
C2 C1 C6 116.5(2) . . ?
C2 C1 C7 121.9(2) . . ?
C6 C1 C7 121.6(2) . . ?
F1 C2 C3 119.9(2) . . ?
F1 C2 C1 119.2(2) . . ?
C3 C2 C1 121.0(2) . . ?
F2 C3 C2 119.37(19) . . ?
F2 C3 C4 118.8(2) . . ?
C2 C3 C4 121.8(2) . . ?
N1 C4 C3 120.4(2) . . ?
N1 C4 C5 121.8(2) . . ?
C3 C4 C5 117.7(2) . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
F3 C6 C5 118.8(2) . . ?
F3 C6 C1 117.3(2) . . ?
C5 C6 C1 123.9(2) . . ?
N2 C7 C1 178.3(3) . . ?
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
N1 C4 1.360(3) . ?
N1 H2 0.898(18) . ?
N1 H1 0.903(17) . ?
F1 C2 1.342(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.387(3) . ?
C1 C7 1.426(3) . ?
F2 C3 1.355(2) . ?
N2 C7 1.145(3) . ?
C2 C3 1.367(3) . ?
C3 C4 1.390(3) . ?
F3 C6 1.349(3) . ?
C4 C5 1.400(3) . ?
C5 C6 1.358(3) . ?
C5 H5 0.9300 . ?
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 -179.71(19) . . . . ?
C7 C1 C2 F1 1.1(3) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C7 C1 C2 C3 -178.9(2) . . . . ?
F1 C2 C3 F2 -0.5(3) . . . . ?
C1 C2 C3 F2 179.44(19) . . . . ?
F1 C2 C3 C4 179.57(19) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
F2 C3 C4 N1 1.2(3) . . . . ?
C2 C3 C4 N1 -178.9(2) . . . . ?
F2 C3 C4 C5 -179.31(18) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
N1 C4 C5 C6 178.8(2) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 F3 -178.80(19) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 F3 178.97(18) . . . . ?
C7 C1 C6 F3 -1.8(3) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 178.8(2) . . . . ?
