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_7154222
_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         'C20 H21 O P'
_chemical_formula_sum            'C20 H18 O P'
_chemical_formula_weight         305.31
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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_date             2014-04-02
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.056(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0477(2)
_cell_length_b                   17.5321(4)
_cell_length_c                   9.9229(2)
_cell_measurement_reflns_used    3767
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8780
_cell_measurement_theta_min      5.0380
_cell_volume                     1571.78(6)
_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 10.3829
_diffrn_measured_fraction_theta_full 0.9403
_diffrn_measured_fraction_theta_max 0.9889
_diffrn_measurement_details
;
  1 omega  -27.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   60.0000 35

  2 omega  -48.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  150.0000 81

  3 omega  -37.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 26

  4 omega  -49.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 82

  5 omega   -1.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 25

  6 omega    1.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -180.0000 28

  7 omega  114.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 36

  8 omega   61.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 26

  9 omega   82.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 26

 10 omega   51.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 29

 11 omega  123.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 25

 12 omega   88.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 27

 13 omega   80.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 48

 14 omega  131.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 36

 15 omega  142.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -180.0000 26

 16 omega   66.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 48

 17 omega   82.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -180.0000 37

 18 omega   82.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 95

 19 omega   78.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 33

 20 omega  104.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 74

 21 omega   67.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -40.0000   -6.2262 26

 22 omega   36.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -120.0000 68

 23 omega   32.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1284076000
_diffrn_orient_matrix_UB_12      -0.0125675000
_diffrn_orient_matrix_UB_13      0.1060783000
_diffrn_orient_matrix_UB_21      -0.0444702000
_diffrn_orient_matrix_UB_22      0.0731825000
_diffrn_orient_matrix_UB_23      0.0736273000
_diffrn_orient_matrix_UB_31      -0.1031063000
_diffrn_orient_matrix_UB_32      -0.0469630000
_diffrn_orient_matrix_UB_33      0.0865345000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8790
_diffrn_reflns_theta_full        72.45
_diffrn_reflns_theta_max         72.45
_diffrn_reflns_theta_min         5.05
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64155
_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    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.8219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                2649
_reflns_number_total             3062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02269f2.cif
_cod_data_source_block           avv20a
_cod_depositor_comments
'Adding full bibliography for 7154221--7154228.cif.'
_cod_original_cell_volume        1571.78(7)
_cod_database_code               7154222
_chemical_oxdiff_formula         'C20 H18 o1 p1'
_reflns_odcompleteness_completeness 94.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95