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_4103942
_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         'C14 H24 I N O'
_chemical_formula_sum            'C14 H24 I N O'
_chemical_formula_weight         349.24
_space_group_IT_number           19
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.28670(10)
_cell_length_b                   10.3536(2)
_cell_length_c                   19.1306(3)
_cell_measurement_reflns_used    7360
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.5406
_cell_measurement_theta_min      4.2649
_cell_volume                     1443.28(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      150(2)
_diffrn_detector_area_resol_mean 8.2640
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.964
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6255
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         73.86
_diffrn_reflns_theta_min         4.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    17.308
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.851
_refine_diff_density_min         -1.482
_refine_diff_density_rms         0.194
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(12)
_refine_ls_extinction_coef       0.0028(3)
_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   1.148
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0768P)^2^+3.8182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                2753
_reflns_number_total             2773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809919t_si_003.cif
_cod_data_source_block           (-)-8
_cod_database_code               4103942