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_4028690
_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         'C15 H13 Br2 N O4 S'
_chemical_formula_sum            'C15 H13 Br2 N O4 S'
_chemical_formula_weight         463.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.774(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8097(2)
_cell_length_b                   18.8010(3)
_cell_length_c                   7.3495(1)
_cell_measurement_reflns_used    16338
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2590
_cell_measurement_theta_min      3.5630
_cell_volume                     1591.45(4)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_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 0.995
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            34858
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         29.48
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    5.244
_exptl_absorpt_correction_T_max  0.710
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1910
_exptl_crystal_size_mid          0.1531
_exptl_crystal_size_min          0.0738
_refine_diff_density_max         1.927
_refine_diff_density_min         -1.887
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0200P)^2^+4.1289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                3870
_reflns_number_total             4186
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo401888f_si_003.cif
_cod_data_source_block           eva58
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028690