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_7154225
_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         '2(C8.5 H9.5 O P0.5)'
_chemical_formula_sum            'C17 H19 O2 P'
_chemical_formula_weight         286.29
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.515(2)
_cell_length_b                   14.5644(7)
_cell_length_c                   5.7956(4)
_cell_measurement_reflns_used    4505
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7370
_cell_measurement_theta_min      5.0450
_cell_volume                     2997.8(3)
_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)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -126.00  -78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000 -180.0000 48

  2 omega  -11.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   30.0000 44

  3 omega  -50.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 83

  4 omega   69.00   96.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 27

  5 omega   36.00   63.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 27

  6 omega   99.00  139.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  128.0000  -52.0000 40

  7 omega   39.00   97.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 58

  8 omega  102.00  130.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 28

  9 omega  143.00  170.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 27

 10 omega   70.00  109.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 39

 11 omega  115.00  147.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000    0.0000 32

 12 omega   37.00   69.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 32

 13 omega   77.00  109.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 32

 14 omega   97.00  166.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 69

 15 omega   77.00  146.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 69

 16 omega   68.00   93.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 25

 17 omega   30.00   63.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 33

 18 omega   58.00   83.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 25

 19 omega   46.00   71.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 25

 20 omega   37.00   71.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 34

 21 omega -107.00  -63.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -144.0000   63.0000 44

 22 omega   86.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000    0.0000 29

 23 omega   21.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  -60.0000 27

 24 omega  134.00  166.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 32

 25 omega  134.00  161.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 27

 26 omega   32.00   63.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 31

 27 omega  105.00  143.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -120.0000 38

 28 omega   97.00  143.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  120.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0403799000
_diffrn_orient_matrix_UB_12      -0.0386527000
_diffrn_orient_matrix_UB_13      -0.0033635000
_diffrn_orient_matrix_UB_21      0.0004372000
_diffrn_orient_matrix_UB_22      -0.0064771000
_diffrn_orient_matrix_UB_23      0.2654668000
_diffrn_orient_matrix_UB_31      -0.0158345000
_diffrn_orient_matrix_UB_32      0.0981881000
_diffrn_orient_matrix_UB_33      0.0161358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16589
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.149
_diffrn_reflns_theta_min         3.925
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58725
_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_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       needle
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+4.4754P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1799
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2732
_reflns_number_total             3265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02269f2.cif
_cod_data_source_block           asb_421
_cod_depositor_comments
'Adding full bibliography for 7154221--7154228.cif.'
_cod_database_code               7154225
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 94.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O13A-H14A
 1.8 with sigma of 0.02
 O13-H14
 1.8 with sigma of 0.02
 O14-H14
 0.9 with sigma of 0.02
 C5A-H5AB = C5A-H5AC = C5A-H5AA
 0.95 with sigma of 0.02
 C1A-H1AA = C1A-H1AB
 0.95 with sigma of 0.02
 C1A-H1AC
 0.95 with sigma of 0.02
 C1-H1B = C1-H1A = C1-H1C
 0.95 with sigma of 0.02
 H1B-C2
 2.1 with sigma of 0.02
 H1A-C2
 2.1 with sigma of 0.02
 H1C-C2
 2.1 with sigma of 0.02
 H1B-H1C
 1.6 with sigma of 0.02
 C5-H5B = C5-H5A
 0.95 with sigma of 0.02
 H5B-H5A
 1.6 with sigma of 0.02
 H5A-C2
 2.1 with sigma of 0.02
 H5B-C2
 2.1 with sigma of 0.02
 C5-H5C
 0.95 with sigma of 0.02
3. Others
 Fixed Sof: O14A(0.5) H14A(0.5) C1A(0.5) H1AB(0.5) H1AC(0.5) C5A(0.5)
 H5AA(0.5) H5AB(0.5) H5AC(0.5) H9A(0.5) H9AA(0.5) C7A(0.5) H7A(0.5) C8A(0.5)
 H8A(0.5) C10B(0.5) H10B(0.5) C11B(0.5) H11B(0.5) C7B(0.5) H7B(0.5) C8B(0.5)
 H8B(0.5) C10A(0.5) H10A(0.5) C11A(0.5) H11A(0.5) O14(0.5) H14(0.5) C1(0.5)
 H1A(0.5) H1B(0.5) H1C(0.5) C2(0.5) C5(0.5) H5A(0.5) H5B(0.5) H5C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C9A(H9A), C9A(H9AA), C7A(H7A), C8A(H8A), C10B(H10B),
 C11B(H11B), C7B(H7B), C8B(H8B), C10A(H10A), C11A(H11A), C4(H4), C7(H7), C8(H8),
  C9(H9), C10(H10), C11(H11)
;