Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes.
Bogachenkov, Alexander S.; Dogadina, Albina V.; Boyarskaya, Irina A.; Boyarskiy, Vadim P.; Vasilyev, Aleksander V.; Organic & biomolecular chemistry 14 (2016) 1370–1381; doi:10.1039/c5ob02143j

data_7154812
_publ_section_title
;
 Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted
 cyclization of 1-(diphenylphosphoryl)allenes.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1370
_journal_page_last               1381
_journal_paper_doi               10.1039/c5ob02143j
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C20 H23 O P'
_chemical_formula_sum            'C20 H23 O P'
_chemical_formula_weight         310.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-21 deposited with the CCDC.
2015-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2077(3)
_cell_length_b                   8.43855(16)
_cell_length_c                   12.5611(3)
_cell_measurement_reflns_used    7885
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1020
_cell_measurement_theta_min      5.8960
_cell_volume                     1717.98(6)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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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)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.000
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_diffrn_measurement_details
;
  1 omega  -69.00  -35.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -178.0000   30.0000 34

  2 omega  -45.00   -4.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   31.0000 -101.2190 41

  3 omega  -50.00   35.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000    0.0000 85

  4 omega   58.00  124.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -120.0000 66

  5 omega   42.00   73.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  -30.0000 31

  6 omega   35.00  115.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 80

  7 omega   81.00  106.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 25

  8 omega   91.00  167.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 76

  9 omega   38.00   90.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 52

 10 omega   55.00  126.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -30.0000 71

 11 omega   35.00   70.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 35

 12 omega  108.00  170.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -30.0000 62

 13 omega   67.00  106.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 39

 14 omega   38.00   78.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 40

 15 omega   47.00   81.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 34

 16 omega   45.00   70.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 25

 17 omega  -49.00   23.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 72

 18 omega  -49.00   34.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   90.0000 83

 19 omega  -42.00  -16.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -180.0000 26

 20 omega   14.00   40.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -       40.3787   77.0000  -30.0000 26

 21 omega   97.00  124.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 27

 22 omega   68.00  117.00   1.0000   28.5600
omega____ theta____ kappa____ phi______ frames
    -       40.3787   77.0000  -30.0000 49

 23 omega   45.00   80.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 35

 24 omega  109.00  145.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 36

 25 omega  128.00  178.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 50

 26 omega   86.00  153.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 67

 27 omega   79.00  108.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 29

 28 omega  147.00  173.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 26

 29 omega   85.00  124.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 39

 30 omega   77.00  115.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 38

 31 omega   56.00   85.00   1.0000  114.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0788555000
_diffrn_orient_matrix_UB_12      0.0986729000
_diffrn_orient_matrix_UB_13      -0.0172575000
_diffrn_orient_matrix_UB_21      0.0058250000
_diffrn_orient_matrix_UB_22      0.0297778000
_diffrn_orient_matrix_UB_23      0.1207694000
_diffrn_orient_matrix_UB_31      0.0527376000
_diffrn_orient_matrix_UB_32      -0.1507190000
_diffrn_orient_matrix_UB_33      0.0125099000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12466
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.955
_diffrn_reflns_theta_min         5.459
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83964
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.691
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1446 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1034P)^2^+0.4789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1360
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3178
_reflns_number_total             3205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02143j2.cif
_cod_data_source_block           103-129-2717_amr40
_cod_depositor_comments          'Adding full bibliography for 7154812.cif.'
_cod_original_cell_volume        1717.97(6)
_cod_database_code               7154812
_chemical_oxdiff_formula         'P O C20 H23'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C15(H15), C5(H5), C7(H7), C12(H12), C14(H14), C8(H8),
 C3(H3), C13(H13)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              42879
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'