Regio- and diastereoselective construction of 1′,2′-(dihydrospiro[indoline-3,3′-pyrrol]-2′-yl)acrylates through phosphine-catalyzed [4 + 1] annulation of Morita‒Baylis‒Hillman carbonates with oxindole-derived α,β-unsaturated imines
Lei, Yu; Zhang, Xiao-Nan; Yang, Xue-Yan; Xu, Qin; Shi, Min; RSC Adv. 5 (2015) 49657–; doi:10.1039/C5RA09147K

data_7220674
_publ_section_title
;
 Regio- and diastereoselective construction of
 1&#x2032;,2&#x2032;-(dihydrospiro[indoline-3,3&#x2032;-pyrrol]-2&#x2032;-yl)acrylates
 through phosphine-catalyzed [4 + 1] annulation of Morita--Baylis--Hillman
 carbonates with oxindole-derived \a,\b-unsaturated imines
;
_journal_issue                   61
_journal_name_full               'RSC Adv.'
_journal_page_first              49657
_journal_paper_doi               10.1039/C5RA09147K
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C41 H49 Br Cl2 N2 O5 S'
_chemical_formula_weight         832.69
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-09-17 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.462(4)
_cell_length_b                   12.7234(15)
_cell_length_c                   11.2553(14)
_cell_measurement_reflns_used    1586
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.347
_cell_measurement_theta_min      5.026
_cell_volume                     4219.1(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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_unetI/netI     0.1324
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24104
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.600
_exptl_absorpt_coefficient_mu    1.194
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
 Flack x determined using 1303 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.042(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         7814
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0787P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.882
_reflns_friedel_fraction_full    0.986
_reflns_friedel_fraction_max     0.986
_reflns_number_gt                4022
_reflns_number_total             7814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra09147k2.cif
_cod_data_source_block           cd214510
_cod_original_cell_volume        4219.2(9)
_cod_database_code               7220674
_shelxl_version_number           2013-4
_shelx_res_checksum              21466