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#$Date: 2023-07-05 13:06:39 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284915 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/66/7246690.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_7246690
loop_
_publ_author_name
'Vaganova, Tamara A.'
'Gatilov, Yurij V.'
'Kryuchkova, Natalia A.'
'Pishchur, Denis P.'
'Zhukovets, Anastasia A.'
'Malykhin, Evgenij V.'
_publ_section_title
;
 How does the combination of the nitro group and fluorine atoms affect the
 (co)crystallization behaviour of arylenediamines?
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3284
_journal_page_last               3298
_journal_paper_doi               10.1039/D3CE00327B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C6 H5 F2 N3 O2'
_chemical_formula_sum            'C6 H5 F2 N3 O2'
_chemical_formula_weight         189.13
_chemical_melting_point          455.8
_chemical_name_systematic        2,4-difluoro-6-nitrobenzene-1,3-diamine
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 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
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.936(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6215(4)
_cell_length_b                   3.6750(2)
_cell_length_c                   13.2829(7)
_cell_measurement_reflns_used    3485
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.77
_cell_volume                     359.47(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0169
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4750
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.137
_diffrn_reflns_theta_min         2.766
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.8878
_exptl_absorpt_correction_T_min  0.8298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_description       block
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1592
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0257
_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)+(0.0574P)²+0.0158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1487
_reflns_number_total             1592
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00327b2.cif
_cod_data_source_block           B-mal131_3
_cod_depositor_comments
'Adding full bibliography for 7246683--7246691.cif.'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7246690
_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   0.933
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, 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 0.7383(3) 0.0016(6) 0.42369(17) 0.0423(4) Uani 1 1 d . . . . .
H1B H 0.720(4) -0.087(9) 0.357(3) 0.051(8) Uiso 1 1 d . . . . .
H1A H 0.839(5) -0.033(9) 0.474(3) 0.056(9) Uiso 1 1 d . . . . .
F1 F 0.4222(2) 0.0272(4) 0.27885(10) 0.0486(4) Uani 1 1 d . . . . .
O1 O 0.7393(2) 0.3893(6) 0.72017(12) 0.0530(5) Uani 1 1 d . . . . .
C1 C 0.5894(2) 0.2691(6) 0.55060(14) 0.0303(4) Uani 1 1 d . . . . .
C2 C 0.5921(3) 0.1370(5) 0.45065(15) 0.0286(4) Uani 1 1 d . . . . .
N2 N 0.1103(3) 0.2958(8) 0.3148(2) 0.0599(6) Uani 1 1 d . . . . .
H2B H 0.017(6) 0.397(12) 0.329(3) 0.069(11) Uiso 1 1 d . . . . .
H2A H 0.101(6) 0.205(10) 0.251(3) 0.070(11) Uiso 1 1 d . . . . .
F2 F 0.12177(19) 0.5661(5) 0.50760(15) 0.0589(5) Uani 1 1 d . . . . .
O2 O 0.8876(2) 0.1169(6) 0.62308(15) 0.0568(5) Uani 1 1 d . . . . .
C3 C 0.4266(3) 0.1550(6) 0.37553(14) 0.0338(5) Uani 1 1 d . . . . .
N3 N 0.7464(2) 0.2573(5) 0.63479(13) 0.0372(4) Uani 1 1 d . . . . .
C4 C 0.2671(3) 0.2916(6) 0.39067(16) 0.0357(5) Uani 1 1 d . . . . .
C5 C 0.2768(3) 0.4253(5) 0.49156(17) 0.0369(5) Uani 1 1 d . . . . .
C6 C 0.4304(3) 0.4143(6) 0.56983(16) 0.0339(4) Uani 1 1 d . . . . .
H6 H 0.430993 0.501720 0.635617 0.041 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1B 117(2) . . ?
C2 N1 H1A 117(2) . . ?
H1B N1 H1A 125(3) . . ?
C6 C1 N3 117.49(17) . . ?
C6 C1 C2 121.39(17) . . ?
N3 C1 C2 121.12(18) . . ?
N1 C2 C3 118.96(18) . . ?
N1 C2 C1 125.90(19) . . ?
C3 C2 C1 115.13(17) . . ?
C4 N2 H2B 118(3) . . ?
C4 N2 H2A 123(3) . . ?
H2B N2 H2A 120(4) . . ?
F1 C3 C4 117.12(17) . . ?
F1 C3 C2 117.21(18) . . ?
C4 C3 C2 125.67(18) . . ?
O1 N3 O2 121.24(17) . . ?
O1 N3 C1 118.80(18) . . ?
O2 N3 C1 119.95(18) . . ?
N2 C4 C3 122.7(2) . . ?
N2 C4 C5 121.6(2) . . ?
C3 C4 C5 115.68(17) . . ?
C6 C5 F2 120.5(2) . . ?
C6 C5 C4 122.91(19) . . ?
F2 C5 C4 116.58(18) . . ?
C5 C6 C1 119.19(19) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
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
N1 C2 1.350(3) . ?
N1 H1B 0.92(3) . ?
N1 H1A 0.89(4) . ?
F1 C3 1.360(2) . ?
O1 N3 1.247(3) . ?
C1 C6 1.406(3) . ?
C1 N3 1.412(2) . ?
C1 C2 1.419(3) . ?
C2 C3 1.394(3) . ?
N2 C4 1.351(3) . ?
N2 H2B 0.86(5) . ?
N2 H2A 0.90(4) . ?
F2 C5 1.356(2) . ?
O2 N3 1.239(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.411(3) . ?
C5 C6 1.351(3) . ?
C6 H6 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 N1 178.2(2) . . . . ?
N3 C1 C2 N1 -2.2(3) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
N3 C1 C2 C3 178.17(17) . . . . ?
N1 C2 C3 F1 1.1(3) . . . . ?
C1 C2 C3 F1 -179.21(16) . . . . ?
N1 C2 C3 C4 -178.8(2) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C6 C1 N3 O1 -3.1(3) . . . . ?
C2 C1 N3 O1 177.30(18) . . . . ?
C6 C1 N3 O2 176.7(2) . . . . ?
C2 C1 N3 O2 -2.9(3) . . . . ?
F1 C3 C4 N2 1.2(3) . . . . ?
C2 C3 C4 N2 -178.9(2) . . . . ?
F1 C3 C4 C5 -179.39(17) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
N2 C4 C5 C6 177.9(2) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
N2 C4 C5 F2 -1.6(3) . . . . ?
C3 C4 C5 F2 179.04(18) . . . . ?
F2 C5 C6 C1 -179.55(16) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
N3 C1 C6 C5 -179.07(17) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
