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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/2/02/32/2023205.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_2023205
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_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          'C18 H14 F4 N2 O4'
_chemical_formula_moiety         'C18 H14 F4 N2 O4'
_chemical_formula_sum            'C18 H14 F4 N2 O4'
_chemical_formula_weight         398.31
_chemical_name_systematic
;
Diethyl 4,4'-(diazene-1,2-diyl)bis(3,5-difluorobenzoate)
;
_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
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                99.330(8)
_cell_angle_beta                 99.431(8)
_cell_angle_gamma                96.442(7)
_cell_formula_units_Z            1
_cell_length_a                   4.6106(17)
_cell_length_b                   8.839(3)
_cell_length_c                   10.969(4)
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.36
_cell_volume                     430.7(3)
_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
;
SHELXS  (Sheldrick, 2008)
;
_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 0.990
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       'ω and φ 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  0.0231
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3269
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.915
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           43.0
_diffrn_source_power             1.634
_diffrn_source_voltage           38.0
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.293
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0466
_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)+(0.0945P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                1414
_reflns_number_total             1913
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jq2034.cif
_cod_data_source_block           III
_cod_database_code               2023205
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.3292(3) 0.83917(13) 0.96263(11) 0.0332(3) Uani d 1 . .
F F2 0.2359(3) 0.43669(13) 1.19462(11) 0.0352(3) Uani d 1 . .
O O1 -0.2904(3) 0.84303(16) 1.39751(13) 0.0308(4) Uani d 1 . .
O O2 -0.1813(3) 1.04412(15) 1.30209(12) 0.0261(3) Uani d 1 . .
N N1 0.4466(3) 0.55792(18) 0.98505(15) 0.0256(4) Uani d 1 . .
C C1 0.2996(4) 0.6346(2) 1.07526(16) 0.0206(4) Uani d 1 . .
C C2 0.2364(4) 0.7829(2) 1.05820(17) 0.0235(4) Uani d 1 . .
C C3 0.0879(4) 0.8714(2) 1.13506(17) 0.0229(4) Uani d 1 . .
C C4 -0.0091(4) 0.8109(2) 1.23300(17) 0.0212(4) Uani d 1 . .
C C5 0.0423(4) 0.6636(2) 1.25239(17) 0.0232(4) Uani d 1 . .
H H5 -0.028030 0.621698 1.318322 0.028 Uiso calc 1 . .
C C6 0.1961(4) 0.5799(2) 1.17490(17) 0.0223(4) Uani d 1 . .
C C7 -0.1761(4) 0.8990(2) 1.32022(17) 0.0223(4) Uani d 1 . .
C C8 -0.3390(4) 1.1407(2) 1.38246(19) 0.0277(4) Uani d 1 . .
H H8A -0.296123 1.121791 1.469698 0.033 Uiso calc 1 . .
H H8B -0.556011 1.116299 1.351234 0.033 Uiso calc 1 . .
C C9 -0.2333(5) 1.3059(2) 1.3787(2) 0.0347(5) Uani d 1 . .
H H9A -0.274544 1.322754 1.291824 0.052 Uiso calc 1 . .
H H9B -0.018988 1.329046 1.411153 0.052 Uiso calc 1 . .
H H9C -0.337013 1.374039 1.430782 0.052 Uiso calc 1 . .
H H3 0.060(4) 0.969(2) 1.117(2) 0.027(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'
O O 0.0106 0.0060 '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
C7 O2 C8 . . 116.47(14) ?
N1 N1 C1 2_667 . 114.4(2) ?
C2 C1 N1 . . 115.52(16) ?
C6 C1 N1 . . 128.64(16) ?
C6 C1 C2 . . 115.76(16) ?
F1 C2 C1 . . 117.69(16) ?
F1 C2 C3 . . 119.19(16) ?
C3 C2 C1 . . 123.11(17) ?
C2 C3 C4 . . 118.52(17) ?
C2 C3 H3 . . 116.6(13) ?
C4 C3 H3 . . 124.9(13) ?
C3 C4 C5 . . 120.65(17) ?
C3 C4 C7 . . 121.92(17) ?
C5 C4 C7 . . 117.42(17) ?
C4 C5 H5 . . 120.5 ?
C6 C5 C4 . . 119.07(17) ?
C6 C5 H5 . . 120.5 ?
F2 C6 C1 . . 119.66(16) ?
F2 C6 C5 . . 117.43(16) ?
C5 C6 C1 . . 122.86(17) ?
O1 C7 O2 . . 124.89(17) ?
O1 C7 C4 . . 123.19(18) ?
O2 C7 C4 . . 111.91(16) ?
O2 C8 H8A . . 110.3 ?
O2 C8 H8B . . 110.3 ?
O2 C8 C9 . . 107.28(15) ?
H8A C8 H8B . . 108.5 ?
C9 C8 H8A . . 110.3 ?
C9 C8 H8B . . 110.3 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9B . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
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 C2 . 1.341(2) ?
F2 C6 . 1.345(2) ?
O1 C7 . 1.211(2) ?
O2 C7 . 1.332(2) ?
O2 C8 . 1.463(2) ?
N1 N1 2_667 1.252(3) ?
N1 C1 . 1.415(2) ?
C1 C2 . 1.409(3) ?
C1 C6 . 1.395(3) ?
C2 C3 . 1.373(3) ?
C3 C4 . 1.389(3) ?
C3 H3 . 0.94(2) ?
C4 C5 . 1.392(3) ?
C4 C7 . 1.500(2) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.373(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C8 C9 . 1.496(3) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
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 C2 C3 C4 . . . . 179.45(15) ?
N1 N1 C1 C2 2_667 . . . 166.37(19) ?
N1 N1 C1 C6 2_667 . . . -17.2(3) ?
N1 C1 C2 F1 . . . . -2.4(2) ?
N1 C1 C2 C3 . . . . 178.22(15) ?
N1 C1 C6 F2 . . . . 0.7(3) ?
N1 C1 C6 C5 . . . . -176.52(16) ?
C1 C2 C3 C4 . . . . -1.1(3) ?
C2 C1 C6 F2 . . . . 177.21(15) ?
C2 C1 C6 C5 . . . . -0.1(3) ?
C2 C3 C4 C5 . . . . -0.2(3) ?
C2 C3 C4 C7 . . . . -179.22(14) ?
C3 C4 C5 C6 . . . . 1.4(3) ?
C3 C4 C7 O1 . . . . 171.84(16) ?
C3 C4 C7 O2 . . . . -8.3(2) ?
C4 C5 C6 F2 . . . . -178.54(14) ?
C4 C5 C6 C1 . . . . -1.2(3) ?
C5 C4 C7 O1 . . . . -7.2(3) ?
C5 C4 C7 O2 . . . . 172.65(14) ?
C6 C1 C2 F1 . . . . -179.32(14) ?
C6 C1 C2 C3 . . . . 1.3(3) ?
C7 O2 C8 C9 . . . . 161.06(16) ?
C7 C4 C5 C6 . . . . -179.59(14) ?
C8 O2 C7 O1 . . . . -0.2(3) ?
C8 O2 C7 C4 . . . . 179.99(13) ?
