Asymmetric C2-C3 Cyclopentannulation of the Indole Ring
José Barluenga; Eva Tudela; Alfredo Ballesteros; Miguel Tomás; Journal of the American Chemical Society 131 (2009) 2096–2097; doi:10.1021/ja809919t

data_4103941
_publ_section_title
;
 Asymmetric C2-C3 Cyclopentannulation of the Indole Ring
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2096
_journal_page_last               2097
_journal_paper_doi               10.1021/ja809919t
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H14 Br N O'
_chemical_formula_sum            'C18 H14 Br N O'
_chemical_formula_weight         340.21
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 100.1250(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.71950(10)
_cell_length_b                   8.75940(10)
_cell_length_c                   18.32450(10)
_cell_measurement_reflns_used    12879
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7362
_cell_measurement_theta_min      3.1035
_cell_volume                     2957.90(4)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_molecular_graphics    'PLATON (Spek, 2006)'
_computing_publication_material  'SHELXL-97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.2640
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type
;
 Oxford Diffraction Xcalibur Nova
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14881
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         73.88
_diffrn_reflns_theta_min         4.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.761
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.78138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.031(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5641
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0225
_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^)+(0.0303P)^2^+4.2468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0677
_reflns_number_gt                5385
_reflns_number_total             5641
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809919t_si_002.cif
_cod_data_source_block           (-)-4f
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4103941