Acid-promoted transformations of 1-(diphenylphosphoryl)allenes: synthesis of novel 1,4-dihydrophosphinoline 1-oxides.
Bogachenkov, Alexander S.; Dogadina, Albina V.; Boyarskiy, Vadim P.; Vasilyev, Aleksander V.; Organic & biomolecular chemistry 13 (2015) 1333–1338; doi:10.1039/c4ob02269f

data_7154223
_publ_section_title
;
 Acid-promoted transformations of 1-(diphenylphosphoryl)allenes: synthesis
 of novel 1,4-dihydrophosphinoline 1-oxides.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1333
_journal_page_last               1338
_journal_paper_doi               10.1039/c4ob02269f
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C17 H16 Br O P'
_chemical_formula_sum            'C17 H16 Br O P'
_chemical_formula_weight         347.18
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_creation_date             2014-01-29
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.406(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.4116(8)
_cell_length_b                   10.1465(4)
_cell_length_c                   15.7185(8)
_cell_measurement_reflns_used    2579
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7960
_cell_measurement_theta_min      3.4700
_cell_volume                     3088.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9651
_diffrn_measured_fraction_theta_max 0.8218
_diffrn_measurement_details
;
  1 omega  -14.00   51.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777   38.0000    0.0000 65

  2 omega  -34.00   35.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777   57.0000   90.0000 69

  3 omega  -81.00   -7.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -57.0000  -90.0000 74
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0001814000
_diffrn_orient_matrix_UB_12      -0.0457279000
_diffrn_orient_matrix_UB_13      -0.0341694000
_diffrn_orient_matrix_UB_21      -0.0321463000
_diffrn_orient_matrix_UB_22      0.0255256000
_diffrn_orient_matrix_UB_23      -0.0271731000
_diffrn_orient_matrix_UB_31      0.0175455000
_diffrn_orient_matrix_UB_32      0.0462859000
_diffrn_orient_matrix_UB_33      -0.0188601000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10914
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.73
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.866
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0467P)^2^+6.2349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                3773
_reflns_number_total             5319
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02269f2.cif
_cod_data_source_block           exp_590
_cod_depositor_comments
'Adding full bibliography for 7154221--7154228.cif.'
_cod_database_code               7154223
_chemical_oxdiff_formula         'C17 h15 p1 br1 o1'
_reflns_odcompleteness_completeness 96.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32