Tandem gold-catalyzed dehydrative cyclization/diels-alder reactions: facile access to indolocarbazole alkaloids.
Borrero, Nicholas V.; DeRatt, Lindsey G.; Ferreira Barbosa, Lais; Abboud, Khalil A.; Aponick, Aaron; Organic letters 17 (2015) 1754–1757; doi:10.1021/acs.orglett.5b00528

data_1554871
_publ_section_title
;
 Tandem gold-catalyzed dehydrative cyclization/diels-alder reactions:
 facile access to indolocarbazole alkaloids.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1754
_journal_page_last               1757
_journal_paper_doi               10.1021/acs.orglett.5b00528
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C15 H21 N O3'
_chemical_formula_weight         263.33
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2010-03-29 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.198(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1627(4)
_cell_length_b                   14.8595(12)
_cell_length_c                   17.7219(14)
_cell_measurement_reflns_used    4197
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     1351.59(19)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2 (Bruker, 2008)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL (Bruker, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w 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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15805
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL  v6.12 (Bruker 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0586P)^2^+0.4225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1072
_reflns_number_gt                2759
_reflns_number_total             3102
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol5b00528_si_002.cif
_cod_data_source_block           borr1
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1554871