Direct alkylation of indoles and amines by tert-enamides: facile access to pharmaceutically active 2-oxo-1-pyrrolidine analogues.
Jiang, Ran; Xu, Hai-Yan; Xu, Xiao-Ping; Chu, Xue-Qiang; Ji, Shun-Jun; Organic & biomolecular chemistry 9 (2011) 5659–5669; doi:10.1039/c1ob05546a

data_7151948
_publ_section_title
;
 Direct alkylation of indoles and amines by tert-enamides: facile
 access to pharmaceutically active 2-oxo-1-pyrrolidine analogues.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5659
_journal_page_last               5669
_journal_paper_doi               10.1039/c1ob05546a
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C12 H15 Cl N2 O'
_chemical_formula_sum            'C12 H15 Cl N2 O'
_chemical_formula_weight         238.71
_chemical_name_common            1-(1-(4-chlorophenyl)ethyl)pyrrolidin-2-one
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 111.894(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.180(3)
_cell_length_b                   9.4995(18)
_cell_length_c                   12.049(3)
_cell_measurement_reflns_used    4774
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1187.4(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7217
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.072(8)
_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   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0812P)^2^+0.0102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                2020
_reflns_number_total             2692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05546a.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        1187.4(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151948