Halonium Ion Triggered Rearrangement of Unsaturated Benzo-Annulated Bi- and Tricyclic Sulfonamides
Kimberly Geoghegan; Shaun Smullen; Paul Evans; Journal of Organic Chemistry 78 (2013) 10443–10451; doi:10.1021/jo401888f

data_4028689
_publ_section_title
;
 Halonium Ion Triggered Rearrangement of Unsaturated Benzo-Annulated Bi-
 and Tricyclic Sulfonamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10443
_journal_page_last               10451
_journal_paper_doi               10.1021/jo401888f
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C12 H11 N O4 S'
_chemical_formula_sum            'C12 H11 N O4 S'
_chemical_formula_weight         265.28
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.205(2)
_cell_angle_beta                 104.131(3)
_cell_angle_gamma                100.355(2)
_cell_formula_units_Z            4
_cell_length_a                   8.7295(3)
_cell_length_b                   9.9483(2)
_cell_length_c                   13.9369(4)
_cell_measurement_reflns_used    15477
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.8252
_cell_measurement_theta_min      4.5729
_cell_volume                     1139.85(6)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) 
(compiled May 16 2011,17:55:39) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) 
(compiled May 16 2011,17:55:39) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) 
(compiled May 16 2011,17:55:39) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32389
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         77.03
_diffrn_reflns_theta_min         4.58
_exptl_absorpt_coefficient_mu    2.613
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) 
(compiled May 16 2011,17:55:39) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2222
_exptl_crystal_size_mid          0.1045
_exptl_crystal_size_min          0.0262
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+2.1016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1388
_reflns_number_gt                4373
_reflns_number_total             4641
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo401888f_si_002.cif
_cod_data_source_block           eva56
_cod_database_code               4028689