Phosphine-catalyzed Highly Diastereoselective [3+2] Cyclization of Isatin Derived Electron-deficient Alkenes with -Allenic Esters
Xiu-Chun Zhang; Shu-Hua Cao; Yin Wei; Min Shi; Chem.Commun. 47 (2011) 1548–; doi:10.1039/c0cc04289g

data_7105901
_publ_section_title
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 Phosphine-catalyzed Highly Diastereoselective [3+2] Cyclization of Isatin
 Derived Electron-deficient Alkenes with -Allenic Esters
;
_journal_name_full               Chem.Commun.
_journal_page_first              1548
_journal_paper_doi               10.1039/c0cc04289g
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C23 H16 Br N O2'
_chemical_formula_weight         418.28
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.032(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2650(17)
_cell_length_b                   13.415(3)
_cell_length_c                   16.413(3)
_cell_measurement_reflns_used    3397
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.953
_cell_measurement_theta_min      4.967
_cell_volume                     1818.6(6)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9725
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    2.278
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48225
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                2619
_reflns_number_total             3572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC04289G.TXT
_cod_data_source_block           cd201470
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7105901