Synthesis of benzosultams via an intramolecular sp2 C-H bond amination reaction of o-arylbenzenesulfonamides under metal-free conditions.
Li, Yuewen; Ding, Qiuping; Qiu, Guanyinsheng; Wu, Jie; Organic & biomolecular chemistry 12 (2014) 149–155; doi:10.1039/c3ob41810c

data_7153646
_publ_section_title
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 Synthesis of benzosultams via an intramolecular sp2 C-H bond amination
 reaction of o-arylbenzenesulfonamides under metal-free conditions.
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_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              149
_journal_page_last               155
_journal_paper_doi               10.1039/c3ob41810c
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C16 H16 I N O2 S'
_chemical_formula_weight         413.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.153(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.460(5)
_cell_length_b                   7.632(3)
_cell_length_c                   17.002(6)
_cell_measurement_reflns_used    957
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.006
_cell_measurement_theta_min      2.396
_cell_volume                     1616.5(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6934
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        5.70
_exptl_absorpt_coefficient_mu    2.114
_exptl_absorpt_correction_T_max  0.6772
_exptl_absorpt_correction_T_min  0.4497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.890
_refine_diff_density_min         -1.040
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.0155(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0934P)^2^+0.5778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1747
_reflns_number_gt                1945
_reflns_number_total             3166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41810c.txt
_cod_data_source_block           a30403a
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1616.3(11)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7153646