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_7220673
_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_formula_sum            'C30 H28 N2 O5 S'
_chemical_formula_weight         528.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2014-08-14 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2726(8)
_cell_length_b                   14.2499(8)
_cell_length_c                   13.8765(8)
_cell_measurement_reflns_used    5601
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.63
_cell_measurement_theta_min      2.44
_cell_volume                     2592.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.0325
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.603
_diffrn_reflns_theta_min         1.976
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.250
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_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         7925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.053
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.3671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5205
_reflns_number_total             7925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra09147k2.cif
_cod_data_source_block           mo_dm14435_0m
_cod_database_code               7220673
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.967
_shelxl_version_number           2014-3
_shelx_res_checksum              98099