A new modular indole synthesis. Construction of the highly strained CDEF parent tetracycle of nodulisporic acids A and B.
Smith, 3rd, Amos B; Kürti, Laszló; Davulcu, Akin H.; Organic letters 8 (2006) 2167–2170; doi:10.1021/ol0606536

data_1505986
_publ_section_title
;
 A new modular indole synthesis. Construction of the highly strained CDEF
 parent tetracycle of nodulisporic acids A and B.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2167
_journal_page_last               2170
_journal_paper_doi               10.1021/ol0606536
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.239(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.006(3)
_cell_length_b                   9.2753(16)
_cell_length_c                   17.100(4)
_cell_measurement_temperature    143(1)
_cell_volume                     2602.4(9)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21039
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5987
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.348
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.348
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.1162
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3065
_refine_ls_wR_factor_ref         0.3240
_reflns_number_gt                3631
_reflns_number_total             4521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0606536si20060316_113657.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_database_code               1505986