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#$Date: 2021-09-06 13:22:30 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268641 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/29/7242981.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_7242981
loop_
_publ_author_name
'Vaganova, Tamara A.'
'Gatilov, Yurij V.'
'Malykhin, Sergey E.'
'Pishchur, Denis P.'
'Sukhov, Maxim'
'Zakharov, Boris A.'
'Boldyreva, Elena V.'
'Malykhin, Evgenij V.'
_publ_section_title
;
 Co-crystals of polyhalogenated diaminobenzonitriles with 18-crown-6:
 effect of fluorine on the stoichiometry and supramolecular structure
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              4767
_journal_page_last               4781
_journal_paper_doi               10.1039/D1CE00530H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C7 H5 F2 N3'
_chemical_formula_sum            'C7 H5 F2 N3'
_chemical_formula_weight         169.14
_chemical_melting_point          408
_chemical_name_systematic
;
2,4-diamino-3,5-difluorobenzonitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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
;
2021-04-08 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                107.270(4)
_cell_angle_beta                 100.818(3)
_cell_angle_gamma                107.844(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1619(5)
_cell_length_b                   7.5769(6)
_cell_length_c                   7.6716(5)
_cell_measurement_reflns_used    3328
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.61
_cell_measurement_theta_min      2.92
_cell_volume                     360.19(5)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.938
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7318
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.947
_diffrn_reflns_theta_min         2.921
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       plate
_exptl_crystal_F_000             172
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1963
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0847P)²+0.0541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1457
_reflns_number_total             1963
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00530h2.cif
_cod_data_source_block           B-B_Mal
_cod_depositor_comments
'Adding full bibliography for 7242975--7242982.cif.'
_cod_database_code               7242981
_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   0.920
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.12801(17) 0.61949(14) 0.22543(13) 0.0543(3) Uani 1 1 d . . . . .
N3 N -0.0280(2) 0.2077(2) 0.09826(18) 0.0464(3) Uani 1 1 d D . . . .
H3A H -0.059(3) 0.269(3) 0.026(3) 0.064(6) Uiso 1 1 d D . . . .
H3B H -0.099(4) 0.087(3) 0.083(4) 0.089(8) Uiso 1 1 d D . . . .
C1 C 0.34074(19) 0.56434(19) 0.66368(17) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.5594(3) 0.7899(2) 1.0123(2) 0.0658(5) Uani 1 1 d . . . . .
F2 F 0.07855(16) 0.03918(12) 0.34850(13) 0.0529(3) Uani 1 1 d . . . . .
N2 N 0.3685(2) 0.86255(18) 0.5924(2) 0.0483(4) Uani 1 1 d D . . . .
H2A H 0.406(4) 0.937(4) 0.724(3) 0.093(8) Uiso 1 1 d D . . . .
H2B H 0.304(4) 0.917(4) 0.515(4) 0.097(9) Uiso 1 1 d D . . . .
C2 C 0.29583(19) 0.65811(18) 0.53796(18) 0.0317(3) Uani 1 1 d . . . . .
C3 C 0.1760(2) 0.53298(19) 0.35034(18) 0.0328(3) Uani 1 1 d . . . . .
C4 C 0.09580(19) 0.32556(19) 0.28238(17) 0.0316(3) Uani 1 1 d . . . . .
C5 C 0.1499(2) 0.24295(19) 0.41480(19) 0.0343(3) Uani 1 1 d . . . . .
C6 C 0.2674(2) 0.3550(2) 0.60086(19) 0.0359(3) Uani 1 1 d . . . . .
H6 H 0.298265 0.293593 0.684601 0.030(4) Uiso 1 1 calc R . . . .
C7 C 0.4623(2) 0.6866(2) 0.8583(2) 0.0424(4) 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 N3 H3A 116.4(15) . . ?
C4 N3 H3B 114.1(18) . . ?
H3A N3 H3B 125(2) . . ?
C6 C1 C2 120.96(11) . . ?
C6 C1 C7 120.35(12) . . ?
C2 C1 C7 118.68(12) . . ?
C2 N2 H2A 115.8(17) . . ?
C2 N2 H2B 118.5(18) . . ?
H2A N2 H2B 113(2) . . ?
N2 C2 C3 120.53(12) . . ?
N2 C2 C1 122.85(12) . . ?
C3 C2 C1 116.60(11) . . ?
F1 C3 C4 117.32(11) . . ?
F1 C3 C2 117.98(11) . . ?
C4 C3 C2 124.66(12) . . ?
N3 C4 C3 122.84(12) . . ?
N3 C4 C5 121.70(12) . . ?
C3 C4 C5 115.47(12) . . ?
F2 C5 C6 120.25(12) . . ?
F2 C5 C4 116.27(12) . . ?
C6 C5 C4 123.48(12) . . ?
C5 C6 C1 118.78(12) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C1 177.60(17) . . ?
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 C3 1.3615(15) . ?
N3 C4 1.3690(17) . ?
N3 H3A 0.862(16) . ?
N3 H3B 0.862(17) . ?
C1 C6 1.4020(18) . ?
C1 C2 1.4031(18) . ?
C1 C7 1.4292(18) . ?
N1 C7 1.140(2) . ?
F2 C5 1.3625(15) . ?
N2 C2 1.3730(16) . ?
N2 H2A 0.936(17) . ?
N2 H2B 0.944(17) . ?
C2 C3 1.3908(18) . ?
C3 C4 1.3855(18) . ?
C4 C5 1.3972(19) . ?
C5 C6 1.3630(18) . ?
C6 H6 0.9300 . ?
