Redox condensation of <i>o</i>-halonitrobenzenes, sulfur and isothiocyanates: access to 2-aminobenzothiazoles.
Nguyen, Le Anh; Mac, Dinh Hung; Retailleau, Pascal; Nguyen, Thanh Binh; Organic & biomolecular chemistry 22 (2024) 8586–8590; doi:10.1039/d4ob01512f

data_7160163
_publ_section_title
;
 Redox condensation of <i>o</i>-halonitrobenzenes, sulfur and
 isothiocyanates: access to 2-aminobenzothiazoles.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8586
_journal_page_last               8590
_journal_paper_doi               10.1039/d4ob01512f
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H8 N2 O4 S'
_chemical_formula_sum            'C12 H8 N2 O4 S'
_chemical_formula_weight         276.26
_chemical_name_systematic        '2,2'-Dinitrodiphenyl sulfide'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
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;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2024-08-14 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.850(3)
_cell_length_b                   7.9040(16)
_cell_length_c                   19.553(5)
_cell_measurement_reflns_used    1771
_cell_measurement_temperature    293(20)
_cell_measurement_theta_max      25.5390
_cell_measurement_theta_min      2.7960
_cell_volume                     1213.2(6)
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_computing_data_collection
'CrysAlisPro system (CCD 43.134a 64-bit (release 09-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.134a (Rigaku OD, 2024)'
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_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9141
_diffrn_reflns_point_group_measured_fraction_full 0.994
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_diffrn_reflns_theta_full        22.463
_diffrn_reflns_theta_max         22.463
_diffrn_reflns_theta_min         2.780
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.134a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       platelet
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1569
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0755P)^2^+0.9836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1460
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1358
_reflns_number_total             1569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01512f2.cif
_cod_data_source_block           B21870F0
_cod_depositor_comments          'Adding full bibliography for 7160163.cif.'
_cod_database_code               7160163
_shelx_res_checksum              10165