Electrophilic Interaction of 2,3-Allenoates with PhSeCl. An Unexpected Highly Stereoselective Synthesis of 3-Phenylseleno-4-oxo-2(E)-alkenoates
Guofei Chen; Chunling Fu; Shengming Ma; Journal of Organic Chemistry 71 (2006) 9877–9879; doi:10.1021/jo061680c

data_4022176
_publ_section_title
;
 Electrophilic Interaction of 2,3-Allenoates with PhSeCl. An Unexpected
 Highly Stereoselective Synthesis of 3-Phenylseleno-4-oxo-2(E)-alkenoates
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9877
_journal_page_last               9879
_journal_paper_doi               10.1021/jo061680c
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C19 H17 Br O3 Se'
_chemical_formula_weight         452.20
_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                 99.145(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.775(3)
_cell_length_b                   6.0652(19)
_cell_length_c                   28.906(9)
_cell_measurement_reflns_used    1031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.361
_cell_measurement_theta_min      5.272
_cell_volume                     1865.0(10)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0984
_diffrn_reflns_av_sigmaI/netI    0.1617
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10370
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    4.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51989
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.742
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.742
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0518P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1364
_reflns_number_gt                1454
_reflns_number_total             4046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061680csi20060811_113313.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022176