A cycloisomerization/Friedel-Crafts alkylation strategy for the synthesis of pyrano[3,4-b]indoles.
Medeiros, Matthew R.; Schaus, Scott E.; Porco, Jr, John A; Organic letters 13 (2011) 4012–4015; doi:10.1021/ol201532k

data_1502316
_publ_contact_author             'John A. Porco, Jr.'
_publ_section_title
;
 A cycloisomerization/Friedel-Crafts alkylation strategy for the synthesis
 of pyrano[3,4-b]indoles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              4012
_journal_page_last               4015
_journal_paper_doi               10.1021/ol201532k
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H24 Cl N O5 S'
_chemical_formula_sum            'C23 H24 Cl N O5 S'
_chemical_formula_weight         461.94
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_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-04-20 # Formatted by publCIF
;
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
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_cell_length_b                   9.5637(4)
_cell_length_c                   44.8293(18)
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.73
_cell_measurement_theta_min      3.94
_cell_volume                     2219.13(15)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'OLEX2 (Dolmanov, et al. 2009)'
_computing_publication_material  'PublCIF v.1.9.5_c (IUCr)'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\w & \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       5
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       52
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_diffrn_reflns_number            30718
_diffrn_reflns_theta_full        66.35
_diffrn_reflns_theta_max         66.35
_diffrn_reflns_theta_min         3.94
_diffrn_standards_decay_%        0
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_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.701
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_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.030(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0669P)^2^+0.4888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                3794
_reflns_number_total             3859
_reflns_threshold_expression     >2sigma(I)
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