New catalytic system for aminohalogenation of beta-methyl-beta-nitrostyrenes to give opposite regiochemistry.
Zhi, San-Jun; Sun, Hao; Zhang, Guangqian; Li, Guigen; Pan, Yi; Organic & biomolecular chemistry 8 (2010) 628–631; doi:10.1039/b914944a

data_7153228
_publ_section_title
;
 New catalytic system for aminohalogenation of
 beta-methyl-beta-nitrostyrenes to give opposite regiochemistry.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              628
_journal_page_last               631
_journal_paper_doi               10.1039/b914944a
_journal_volume                  8
_journal_year                    2010
_chemical_formula_iupac          'C16 H17 Cl N2 O4 S'
_chemical_formula_moiety         'C16 H17 Cl N2 O4 S'
_chemical_formula_sum            'C16 H17 Cl N2 O4 S'
_chemical_formula_weight         368.83
_chemical_melting_point          423.2
_chemical_name_systematic
;
<i>N</i>-(2-Chloro-2-nitro-1-phenylpropyl)-4-methylbenzenesulfonamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.8254(8)
_cell_length_b                   19.610(2)
_cell_length_c                   22.533(3)
_cell_measurement_reflns_used    7468
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.26
_cell_volume                     3457.8(7)
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material
'SHELXTL (Bruker, 2000) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXTL (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17527
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.06P)^2^+0.58P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                2467
_reflns_number_total             3396
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b914944a.txt
_cod_data_source_block           I
_cod_database_code               7153228