Regioselective unusual formation of spirocyclic 4-{2'-benzo(2',3'-dihydro)furo}- 9-methyl-2,3,9-trihydrothiopyrano[2,3-b]indole by 4-exo-trig aryl radical cyclization and rearrangement.
Majumdar, K. C.; Alam, S.; Organic letters 8 (2006) 4059–4062; doi:10.1021/ol061531g

data_1506160
_publ_section_title
;
 Regioselective unusual formation of spirocyclic
 4-{2'-benzo(2',3'-dihydro)furo}-
 9-methyl-2,3,9-trihydrothiopyrano[2,3-b]indole by 4-exo-trig aryl radical
 cyclization and rearrangement.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4059
_journal_page_last               4062
_journal_paper_doi               10.1021/ol061531g
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C18 H17 N O S'
_chemical_formula_weight         295.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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                 93.6850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.64940(10)
_cell_length_b                   20.1371(2)
_cell_length_c                   13.3458(2)
_cell_measurement_temperature    273(2)
_cell_volume                     1515.11(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24754
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.212
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0024(11)
_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   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0470P)^2^+0.3842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                3078
_reflns_number_total             3755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061531gsi20060717_064741.cif
_cod_data_source_block           sg-394
_cod_database_code               1506160