Lewis Acid-Catalyzed Malonate Addition onto 3-Hydroxy-2-oxindoles: Mechanistic Consideration and Synthetic Approaches to the Pyrroloindoline Alkaloids.
Naresh Babu, K.; Kariyandi, Nikhil Raj; Saheeda M K, Saina; Kinthada, Lakshmana K.; Bisai, Alakesh; The Journal of organic chemistry 83 (2018) 12664–12682; doi:10.1021/acs.joc.8b02017

data_4035396
_publ_section_title
;
 Lewis Acid-Catalyzed Malonate Addition onto 3-Hydroxy-2-oxindoles:
 Mechanistic Consideration and Synthetic Approaches to the Pyrroloindoline
 Alkaloids.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12664
_journal_page_last               12682
_journal_paper_doi               10.1021/acs.joc.8b02017
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C42 H34 N2 O5'
_chemical_formula_weight         646.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                69.310(2)
_cell_angle_beta                 78.961(2)
_cell_angle_gamma                71.610(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4739(4)
_cell_length_b                   12.3578(6)
_cell_length_c                   15.9762(8)
_cell_measurement_reflns_used    7507
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      26.98
_cell_measurement_theta_min      2.45
_cell_volume                     1653.69(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1481
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            50399
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         2.275
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .09
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.2196
_refine_ls_R_factor_gt           0.0972
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2408
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3725
_reflns_number_total             7818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02017_si_001.cif
_cod_data_source_block           T1
_cod_database_code               4035396
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              30892
_shelx_hkl_checksum              58372