Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles].
You, Yong; Cui, Bao-Dong; Zhou, Ming-Qiang; Zuo, Jian; Zhao, Jian-Qiang; Xu, Xiao-Ying; Zhang, Xiao-Mei; Yuan, Wei-Cheng; The Journal of organic chemistry 80 (2015) 5951–5957; doi:10.1021/acs.joc.5b00597

data_4031027
_publ_section_title
;
 Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of
 3-Pyrrolyl-oxindoles and \a,\b-Unsaturated Aldehydes for the Construction
 of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles].
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5951
_journal_page_last               5957
_journal_paper_doi               10.1021/acs.joc.5b00597
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H17 Br N2 O'
_chemical_formula_weight         405.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 111.054(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9653(5)
_cell_length_b                   11.0573(5)
_cell_length_c                   19.3517(6)
_cell_measurement_reflns_used    8432
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.6880
_cell_measurement_theta_min      4.4865
_cell_volume                     3986.9(3)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16720
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.852
_diffrn_reflns_theta_min         4.491
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.897
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.270
_platon_squeeze_details
;
;
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2788 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.040(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7196
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.0549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                6629
_reflns_number_total             7196
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00597_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 4031027.cif.'
_cod_database_code               4031027
_shelx_estimated_absorpt_t_min   0.422
_shelx_estimated_absorpt_t_max   0.508
_shelxl_version_number           2013-4
_shelx_res_checksum              94793
_shelx_hkl_checksum              79258