Practical chemoselective aromatic substitution: the synthesis of N-(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of N-phenylbenzenesulfonamide
Yu, Xiao; Zhu, Wenjing; Liu, Hongyan; Liu, Yi; Li, Hongshuang; Han, Junfen; Duan, Guiyun; Bai, Zhushuang; Zhang, Pengfei; Xia, Chengcai; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01028C

data_7158754
_publ_section_title
;
 Practical chemoselective aromatic substitution: the synthesis of
 N-(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient
 nitration and halogenation of N-phenylbenzenesulfonamide
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01028C
_journal_year                    2022
_chemical_formula_moiety         'C12 H9 Br N2 O4 S'
_chemical_formula_sum            'C12 H9 Br N2 O4 S'
_chemical_formula_weight         357.18
_chemical_name_systematic        N-(4-bromo-2-nitrophenyl)benzenesulfonamide
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-11-19 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.652(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.609(6)
_cell_length_b                   8.728(5)
_cell_length_c                   29.627(17)
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.42
_cell_measurement_theta_min      2.43
_cell_volume                     2742(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            13522
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.433
_exptl_absorpt_coefficient_mu    3.164
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5220
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4825
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0778P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2902
_reflns_number_total             4825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01028c2.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H18 Br2 N4 O8 S2'
_cod_original_formula_weight         714.36
_cod_original_formula_moiety         C12H9BrN2O4S
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158754
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.493
_shelx_estimated_absorpt_t_max   0.556
_shelx_res_checksum              72972