Substrate-controlled product-selectivity in the reaction of the Bestmann-Ohira reagent with N-unprotected isatin-derived olefins.
Gupta, Ashis Kumar; Ahamad, Shakir; Gupta, Ekta; Kant, Ruchir; Mohanan, Kishor; Organic & biomolecular chemistry 13 (2015) 9783–9788; doi:10.1039/c5ob01382h

data_7154628
_publ_section_title
;
 Substrate-controlled product-selectivity in the reaction of the
 Bestmann-Ohira reagent with N-unprotected isatin-derived olefins.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9783
_journal_page_last               9788
_journal_paper_doi               10.1039/c5ob01382h
_journal_volume                  13
_journal_year                    2015
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C19 H20 N3 O5 P'
_chemical_formula_sum            'C19 H20 N3 O5 P'
_chemical_formula_weight         401.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-03-27 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.651(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.390(3)
_cell_length_b                   9.5870(16)
_cell_length_c                   14.773(3)
_cell_measurement_reflns_used    2695
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      3.2
_cell_volume                     1942.1(7)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)''
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12702
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         3.18
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.4382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                3020
_reflns_number_total             3517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01382h2.cif
_cod_data_source_block           xxx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154628--7154629.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154628