Organocatalyzed enantioselective formal [4 + 2] cycloaddition of 2,3-disubstituted indole and methyl vinyl ketone.
Cai, Quan; You, Shu-Li; Organic letters 14 (2012) 3040–3043; doi:10.1021/ol301114z

data_1507822
_publ_section_title
;
 Organocatalyzed enantioselective formal [4 + 2] cycloaddition of
 2,3-disubstituted indole and methyl vinyl ketone.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3040
_journal_page_last               3043
_journal_paper_doi               10.1021/ol301114z
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H24 Br N O2'
_chemical_formula_weight         390.31
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 95.959(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.237(6)
_cell_length_b                   7.803(5)
_cell_length_c                   11.166(6)
_cell_measurement_reflns_used    2687
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.471
_cell_measurement_theta_min      5.139
_cell_volume                     887.1(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5210
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    2.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51202
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.232
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(8)
_refine_ls_extinction_coef       0.136(5)
_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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0239P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0856
_reflns_number_gt                2921
_reflns_number_total             3363
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301114z_si_002.cif
_cod_data_source_block           cd211211
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 1507822.cif.
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_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1507822