P(NMe2)3-mediated reductive [1+4] annulation of isatins with enones: a facile synthesis of spirooxindole-dihydrofurans
Rong Zhou; Kai Zhang; Yusong Chen; Qiang Meng; Yiyi Liu; Ruifeng Li; Zhengjie He; Chem.Commun. 51 (2015) 14663–; doi:10.1039/C5cc03676C

data_7117814
_publ_section_title
;
 P(NMe2)3-mediated reductive [1+4] annulation of isatins with enones: a
 facile synthesis of spirooxindole-dihydrofurans
;
_journal_name_full               Chem.Commun.
_journal_page_first              14663
_journal_paper_doi               10.1039/C5cc03676C
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C31 H22 Br N O3'
_chemical_formula_weight         536.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-02 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.016(3)
_cell_length_b                   11.906(2)
_cell_length_c                   15.221(3)
_cell_measurement_reflns_used    6384
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8545
_cell_measurement_theta_min      1.3595
_cell_volume                     2677.8(9)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26056
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_T_max  0.7657
_exptl_absorpt_correction_T_min  0.7049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       0.0043(4)
_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   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                5030
_reflns_number_total             6429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03676c2.cif
_cod_data_source_block           shelxl_sqd
_cod_original_cell_volume        2677.7(9)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7117814
_platon_squeeze_void_probe_radius 1.20