Direct oxidative nitration of aromatic sulfonamides under mild conditions
Ying-Xiu Li; Lian-Hua Li; Yan-Fang Yang; Hui-Liang Hua; Xiao-Biao Yan; Lian-Biao Zhao; Jin-Bang Zhang; Fa-Jin Ji; Yong-Min Liang; Chem.Commun. 50 (2014) 9936–; doi:10.1039/C4cc03784G

data_7115499
_publ_section_title
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 Direct oxidative nitration of aromatic sulfonamides under mild conditions
;
_journal_name_full               Chem.Commun.
_journal_page_first              9936
_journal_paper_doi               10.1039/C4cc03784G
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C14 H14 N2 O4 S'
_chemical_formula_sum            'C14 H14 N2 O4 S'
_chemical_formula_weight         306.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-02
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                92.665(13)
_cell_angle_beta                 97.218(15)
_cell_angle_gamma                107.79(2)
_cell_formula_units_Z            2
_cell_length_a                   7.277(2)
_cell_length_b                   9.1288(18)
_cell_length_c                   11.6854(14)
_cell_measurement_reflns_used    1514
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5160
_cell_measurement_theta_min      3.5230
_cell_volume                     730.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.8788
_diffrn_measurement_details
;
  1 omega  -88.00  -61.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  178.0000  120.0000 18

  2 omega  -18.00   25.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000 -180.0000 29

  3 omega   -3.00   97.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   38.0000 -150.0000 67

  4 omega    0.00   90.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000   60.0000 60

  5 omega   27.00   54.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -77.0000   60.0000 18

  6 omega  -48.00   48.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -57.0000  -90.0000 64
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0736515000
_diffrn_orient_matrix_UB_12      -0.0705928000
_diffrn_orient_matrix_UB_13      -0.0207837000
_diffrn_orient_matrix_UB_21      0.0722598000
_diffrn_orient_matrix_UB_22      -0.0320702000
_diffrn_orient_matrix_UB_23      -0.0146391000
_diffrn_orient_matrix_UB_31      0.0082900000
_diffrn_orient_matrix_UB_32      -0.0265101000
_diffrn_orient_matrix_UB_33      0.0559276000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4654
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.0748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1545
_reflns_number_gt                2076
_reflns_number_total             2864
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03784g2.cif
_cod_data_source_block           liyx1129
_cod_database_code               7115499
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;