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#$Date: 2024-07-20 04:58:36 +0300 (Sat, 20 Jul 2024) $
#$Revision: 293488 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/32/2023203.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023203
loop_
_publ_author_name
'Novikov, Egor M.'
'Guillen Campos, Jesus'
'Read de Alaniz, Javier'
'Fonari, Marina S.'
'Timofeeva, Tatiana V.'
_publ_section_title
;
 Synthesis, molecular and crystal structures of
 4-amino-3,5-difluorobenzonitrile, ethyl 4-amino-3,5-difluorobenzoate, and
 diethyl 4,4′-(diazene-1,2-diyl)bis(3,5-difluorobenzoate)
;
_journal_coeditor_code           JQ2034
_journal_issue                   8
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024006819
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C7 H4 F2 N2'
_chemical_formula_moiety         'C7 H4 F2 N2'
_chemical_formula_sum            'C7 H4 F2 N2'
_chemical_formula_weight         154.12
_chemical_name_systematic
;
4-Amino-3,5-difluorobenzonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.604(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.7283(4)
_cell_length_b                   10.5275(12)
_cell_length_c                   16.9073(19)
_cell_measurement_reflns_used    4913
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      31.206
_cell_measurement_theta_min      2.281
_cell_volume                     661.46(13)
_computing_cell_refinement
;
SAINT-Plus V8.40b (Bruker, 2019)
;
_computing_data_collection
;
APEX2 Ver. 2019.11-0. (Bruker, 2019)
;
_computing_data_reduction
;
SAINT-Plus V8.40b (Bruker, 2019)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL  (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11242
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.650
_diffrn_reflns_theta_min         2.281
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           43.0
_diffrn_source_power             1.634
_diffrn_source_voltage           38.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0467
_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)+(0.0659P)²+0.2291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                1775
_reflns_number_total             2140
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jq2034.cif
_cod_data_source_block           I
_cod_database_code               2023203
_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   0.953
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.8337(2) 0.47654(7) 0.39927(5) 0.0311(2) Uani d 1 . .
F F2 0.3651(2) 0.80481(8) 0.23493(4) 0.0314(2) Uani d 1 . .
N N2 0.6762(3) 0.56770(11) 0.24999(7) 0.0276(3) Uani d 1 . .
N N1 0.2518(4) 0.89360(14) 0.57454(7) 0.0379(3) Uani d 1 . .
C C6 0.4379(3) 0.75726(11) 0.30925(7) 0.0206(2) Uani d 1 . .
C C4 0.6741(3) 0.59252(11) 0.39189(7) 0.0207(2) Uani d 1 . .
C C5 0.6003(3) 0.63732(11) 0.31445(6) 0.0194(2) Uani d 1 . .
C C2 0.4317(3) 0.77685(12) 0.44923(7) 0.0217(2) Uani d 1 . .
C C7 0.3518(3) 0.82791(11) 0.37357(7) 0.0215(2) Uani d 1 . .
H H7 0.241446 0.908931 0.366727 0.026 Uiso calc 1 . .
C C3 0.5960(3) 0.65780(12) 0.45866(7) 0.0224(2) Uani d 1 . .
H H3 0.652163 0.622977 0.509999 0.027 Uiso calc 1 . .
C C1 0.3337(4) 0.84385(13) 0.51849(8) 0.0267(3) Uani d 1 . .
H H2A 0.671(6) 0.602(2) 0.2066(14) 0.047(6) Uiso d 1 . .
H H2B 0.814(5) 0.500(2) 0.2560(12) 0.036(5) Uiso d 1 . .
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N2 H2A . . 119.3(15) ?
C5 N2 H2B . . 120.1(13) ?
H2A N2 H2B . . 115.7(19) ?
F2 C6 C5 . . 116.31(10) ?
F2 C6 C7 . . 119.29(11) ?
C7 C6 C5 . . 124.39(11) ?
F1 C4 C5 . . 116.14(10) ?
F1 C4 C3 . . 119.63(10) ?
C3 C4 C5 . . 124.23(11) ?
N2 C5 C6 . . 123.49(11) ?
N2 C5 C4 . . 122.01(11) ?
C4 C5 C6 . . 114.49(10) ?
C7 C2 C3 . . 120.55(11) ?
C7 C2 C1 . . 120.46(11) ?
C3 C2 C1 . . 118.95(11) ?
C6 C7 C2 . . 117.98(11) ?
C6 C7 H7 . . 121.0 ?
C2 C7 H7 . . 121.0 ?
C4 C3 C2 . . 118.35(10) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
N1 C1 C2 . . 177.81(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C4 . 1.3596(14) ?
F2 C6 . 1.3596(13) ?
N2 C5 . 1.3617(15) ?
N2 H2A . 0.82(2) ?
N2 H2B . 0.88(2) ?
N1 C1 . 1.1455(18) ?
C6 C5 . 1.4000(16) ?
C6 C7 . 1.3765(16) ?
C4 C5 . 1.3982(16) ?
C4 C3 . 1.3726(16) ?
C2 C7 . 1.3975(17) ?
C2 C3 . 1.3984(17) ?
C2 C1 . 1.4390(17) ?
C7 H7 . 0.9500 ?
C3 H3 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A N1 4_675 0.82(2) 2.28(2) 3.0297(17) 153(2)
N2 H2B F2 2_645 0.88(2) 2.38(2) 3.2526(15) 173.9(19)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C4 C5 N2 . . . . 1.45(17) ?
F1 C4 C5 C6 . . . . -179.65(10) ?
F1 C4 C3 C2 . . . . -179.98(10) ?
F2 C6 C5 N2 . . . . -1.79(17) ?
F2 C6 C5 C4 . . . . 179.34(10) ?
F2 C6 C7 C2 . . . . -179.65(10) ?
C5 C6 C7 C2 . . . . 0.04(18) ?
C5 C4 C3 C2 . . . . 0.06(18) ?
C7 C6 C5 N2 . . . . 178.51(12) ?
C7 C6 C5 C4 . . . . -0.36(17) ?
C7 C2 C3 C4 . . . . -0.41(17) ?
C3 C4 C5 N2 . . . . -178.59(12) ?
C3 C4 C5 C6 . . . . 0.31(17) ?
C3 C2 C7 C6 . . . . 0.36(17) ?
C1 C2 C7 C6 . . . . -177.28(11) ?
C1 C2 C3 C4 . . . . 177.26(11) ?
