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_7154227
_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         'C23 H23 O2 P'
_chemical_formula_sum            'C23 H23 O2 P'
_chemical_formula_weight         362.38
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.4889(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.58114(14)
_cell_length_b                   17.2730(2)
_cell_length_c                   11.63272(16)
_cell_measurement_reflns_used    6751
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9290
_cell_measurement_theta_min      4.6280
_cell_volume                     1904.07(4)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega -106.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -120.0000 95

  2 omega  -45.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   30.0000 81

  3 omega   63.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 56

  4 omega    6.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -180.0000 31

  5 omega  136.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 35

  6 omega   37.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 52

  7 omega   55.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 36

  8 omega   98.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -90.0000 25

  9 omega   89.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 43

 10 omega   77.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000    0.0000 29

 11 omega  110.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 66

 12 omega   72.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 26

 13 omega   44.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -69.0000 -145.0000 40

 14 omega  120.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 58

 15 omega  129.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 46

 16 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -90.0000 26

 17 omega   86.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 26

 18 omega   42.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 32

 19 omega   84.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 25

 20 omega   44.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 26

 21 omega   38.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 48

 22 omega   72.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 25

 23 omega   36.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 52

 24 omega  153.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 25

 25 omega   30.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0392613000
_diffrn_orient_matrix_UB_12      -0.0131288000
_diffrn_orient_matrix_UB_13      -0.1318006000
_diffrn_orient_matrix_UB_21      -0.1038441000
_diffrn_orient_matrix_UB_22      0.0685185000
_diffrn_orient_matrix_UB_23      -0.0069513000
_diffrn_orient_matrix_UB_31      0.1188051000
_diffrn_orient_matrix_UB_32      0.0555415000
_diffrn_orient_matrix_UB_33      -0.0225669000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11157
_diffrn_reflns_theta_full        72.45
_diffrn_reflns_theta_max         72.45
_diffrn_reflns_theta_min         4.62
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85167
_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    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0459P)^2^+0.9906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                3479
_reflns_number_total             3751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02269f2.cif
_cod_data_source_block           ed_22
_cod_depositor_comments
'Adding full bibliography for 7154221--7154228.cif.'
_cod_original_cell_volume        1904.07(5)
_cod_database_code               7154227
_chemical_oxdiff_formula         'P O2 C25 H20'
_reflns_odcompleteness_completeness 93.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C22(H22), C2(H2), C26(H26), C23(H23), C17(H17), C10(H10), C19(H19),
 C14(H14), C12(H12), C20(H20), C25(H25), C13(H13), C24(H24), C18(H18), C11(H11)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'