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_2023203
_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_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 <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
;
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       '\f and \w 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 <i>et al.</i>,  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/[\s^2^(Fo^2^)+(0.0659P)^2^+0.2291P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            jq2034.cif
_cod_data_source_block           I
_cod_database_code               2023203
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.984
_shelx_hkl_checksum              70618
_shelx_res_checksum              46252