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)
Novikov, Egor M.; Guillen Campos, Jesus; Read de Alaniz, Javier; Fonari, Marina S.; Timofeeva, Tatiana V.; Acta Crystallographica Section E Crystallographic Communications 80 (2024) –; doi:10.1107/S2056989024006819

data_2023204
_publ_section_title
;
 Synthesis, molecular and crystal structures of
 4-amino-3,5-difluorobenzonitrile, ethyl 4-amino-3,5-difluorobenzoate, and
 diethyl 4,4&#x2032;-(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 <i>et al.</i>,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov <i>et al.</i>,  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       '\w and \f 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 <i>et al.</i>,  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/[\s^2^(Fo^2^)+3.0535P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            jq2034.cif
_cod_data_source_block           II
_cod_original_cell_volume        1825.6(6)
_cod_database_code               2023204
_shelx_hkl_checksum              90008
_shelx_res_checksum              61937