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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/2/02/32/2023204.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_2023204
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          'C9 H9 F2 N O2'
_chemical_formula_moiety         'C9 H9 F2 N O2'
_chemical_formula_sum            'C9 H9 F2 N O2'
_chemical_formula_weight         201.17
_chemical_name_systematic
;
Ethyl 4-amino-3,5-difluorobenzoate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.877(3)
_cell_length_b                   8.9995(18)
_cell_length_c                   13.635(3)
_cell_measurement_reflns_used    3255
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      23.384
_cell_measurement_theta_min      2.645
_cell_volume                     1825.5(7)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.1139
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29363
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.253
_diffrn_reflns_theta_min         2.645
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.209
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0599
_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)+3.0535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                1265
_reflns_number_total             1665
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jq2034.cif
_cod_data_source_block           II
_cod_original_cell_volume        1825.6(6)
_cod_database_code               2023204
_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+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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 0.54938(12) 0.31169(18) 0.35054(15) 0.0396(5) Uani d 1 . .
F F2 0.26856(12) 0.4861(2) 0.45376(15) 0.0403(5) Uani d 1 . .
O O2 0.58679(14) 0.8516(2) 0.34897(17) 0.0327(6) Uani d 1 . .
O O1 0.45423(15) 0.9500(2) 0.39457(17) 0.0365(6) Uani d 1 . .
N N1 0.3767(2) 0.2502(3) 0.4064(2) 0.0374(8) Uani d 1 . .
C C6 0.35426(19) 0.5153(3) 0.4228(2) 0.0284(7) Uani d 1 . .
C C1 0.4077(2) 0.3925(3) 0.4014(2) 0.0275(7) Uani d 1 . .
C C4 0.4707(2) 0.6876(3) 0.3866(2) 0.0253(7) Uani d 1 . .
C C2 0.4942(2) 0.4276(3) 0.3721(2) 0.0274(7) Uani d 1 . .
C C7 0.5012(2) 0.8429(3) 0.3781(2) 0.0278(7) Uani d 1 . .
C C3 0.5275(2) 0.5693(3) 0.3645(2) 0.0279(7) Uani d 1 . .
H H3 0.587797 0.586326 0.344706 0.033 Uiso calc 1 . .
C C5 0.3829(2) 0.6589(3) 0.4160(2) 0.0279(7) Uani d 1 . .
H H5 0.343351 0.738484 0.431279 0.034 Uiso calc 1 . .
C C8 0.6241(2) 1.0007(3) 0.3392(3) 0.0350(8) Uani d 1 . .
H H8A 0.625203 1.051356 0.403614 0.042 Uiso calc 1 . .
H H8B 0.587471 1.060564 0.293261 0.042 Uiso calc 1 . .
C C9 0.7174(2) 0.9825(4) 0.3006(3) 0.0468(10) Uani d 1 . .
H H9A 0.715460 0.928930 0.238005 0.070 Uiso calc 1 . .
H H9B 0.753448 0.926045 0.347797 0.070 Uiso calc 1 . .
H H9C 0.744541 1.080539 0.290498 0.070 Uiso calc 1 . .
H H1A 0.414(2) 0.179(4) 0.399(3) 0.043(11) Uiso d 1 . .
H H1B 0.326(3) 0.237(4) 0.435(3) 0.045(12) 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 . . 116.4(2) ?
C1 N1 H1A . . 118(2) ?
C1 N1 H1B . . 117(2) ?
H1A N1 H1B . . 122(3) ?
F2 C6 C1 . . 116.4(3) ?
C5 C6 F2 . . 119.6(3) ?
C5 C6 C1 . . 124.0(3) ?
N1 C1 C6 . . 122.9(3) ?
N1 C1 C2 . . 122.9(3) ?
C2 C1 C6 . . 114.2(3) ?
C3 C4 C7 . . 121.4(3) ?
C5 C4 C7 . . 119.2(3) ?
C5 C4 C3 . . 119.4(3) ?
F1 C2 C1 . . 116.7(3) ?
F1 C2 C3 . . 118.7(3) ?
C3 C2 C1 . . 124.7(3) ?
O2 C7 C4 . . 111.9(3) ?
O1 C7 O2 . . 123.9(3) ?
O1 C7 C4 . . 124.2(3) ?
C4 C3 H3 . . 120.8 ?
C2 C3 C4 . . 118.4(3) ?
C2 C3 H3 . . 120.8 ?
C6 C5 C4 . . 119.3(3) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
O2 C8 H8A . . 110.4 ?
O2 C8 H8B . . 110.4 ?
O2 C8 C9 . . 106.6(3) ?
H8A C8 H8B . . 108.6 ?
C9 C8 H8A . . 110.4 ?
C9 C8 H8B . . 110.4 ?
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 . 1.360(3) ?
F2 C6 . 1.368(3) ?
O2 C7 . 1.336(4) ?
O2 C8 . 1.458(4) ?
O1 C7 . 1.212(4) ?
N1 C1 . 1.363(4) ?
N1 H1A . 0.86(4) ?
N1 H1B . 0.86(4) ?
C6 C1 . 1.392(4) ?
C6 C5 . 1.365(4) ?
C1 C2 . 1.385(4) ?
C4 C7 . 1.474(4) ?
C4 C3 . 1.392(4) ?
C4 C5 . 1.390(4) ?
C2 C3 . 1.372(4) ?
C3 H3 . 0.9500 ?
C5 H5 . 0.9500 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C8 C9 . 1.493(5) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
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
N1 H1A O1 1_545 0.85(3) 2.15(4) 2.942(3) 155(3)
C8 H8B F1 1_565 0.99 2.46 3.015(3) 115
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 . . . . 179.9(3) ?
F2 C6 C1 N1 . . . . 2.6(5) ?
F2 C6 C1 C2 . . . . -178.9(3) ?
F2 C6 C5 C4 . . . . 178.6(3) ?
N1 C1 C2 F1 . . . . -1.7(5) ?
N1 C1 C2 C3 . . . . 178.9(3) ?
C6 C1 C2 F1 . . . . 179.8(3) ?
C6 C1 C2 C3 . . . . 0.4(5) ?
C1 C6 C5 C4 . . . . -0.4(5) ?
C1 C2 C3 C4 . . . . -0.7(5) ?
C7 O2 C8 C9 . . . . -176.7(3) ?
C7 C4 C3 C2 . . . . -178.7(3) ?
C7 C4 C5 C6 . . . . 179.2(3) ?
C3 C4 C7 O2 . . . . -0.8(4) ?
C3 C4 C7 O1 . . . . 178.6(3) ?
C3 C4 C5 C6 . . . . 0.1(5) ?
C5 C6 C1 N1 . . . . -178.3(3) ?
C5 C6 C1 C2 . . . . 0.2(5) ?
C5 C4 C7 O2 . . . . -179.9(3) ?
C5 C4 C7 O1 . . . . -0.5(5) ?
C5 C4 C3 C2 . . . . 0.4(5) ?
C8 O2 C7 O1 . . . . 1.3(4) ?
C8 O2 C7 C4 . . . . -179.3(3) ?
