Reaction of Phospholes with Aldimines: A One-Step Synthesis of Chelating, Alpha-C2-Bridged Biphospholes.
Hu, Zhengsong; Li, Zongyang; Zhao, Kang; Tian, Rongqiang; Duan, Zheng; Mathey, François; Organic letters 17 (2015) 3518–3520; doi:10.1021/acs.orglett.5b01604

data_1555090
_publ_section_title
;
 Reaction of Phospholes with Aldimines: A One-Step Synthesis of Chelating,
 Alpha-C2-Bridged Biphospholes.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3518
_journal_page_last               3520
_journal_paper_doi               10.1021/acs.orglett.5b01604
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C32 H32 O P2'
_chemical_formula_sum            'C32 H32 O P2'
_chemical_formula_weight         494.51
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-30
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_alpha                90
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_cell_length_c                   17.7877(5)
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.0820
_cell_measurement_theta_min      5.2530
_cell_volume                     2635.5(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
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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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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  1 omega  -70.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 38

  2 omega  -72.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 35

  3 omega  -16.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 56

  4 omega   33.00   59.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -90.0000 26

  5 omega   35.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000 -150.0000 86

  6 omega   -4.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -30.0000 79

  7 omega   96.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -150.0000 27

  8 omega   35.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 86

  9 omega   45.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 53

 10 omega   61.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 27

 11 omega   43.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 47

 12 omega   53.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 27

 13 omega   39.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 30

 14 omega   87.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 28

 15 omega   41.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  120.0000 65

 16 omega   42.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 52

 17 omega   57.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 50

 18 omega   47.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 41

 19 omega  103.00  165.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  120.0000 62

 20 omega  -21.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 82

 21 omega  -18.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -86.0000  -52.0000 53
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0088960000
_diffrn_orient_matrix_UB_12      0.0637275000
_diffrn_orient_matrix_UB_13      -0.0798665000
_diffrn_orient_matrix_UB_21      -0.1053398000
_diffrn_orient_matrix_UB_22      0.0249928000
_diffrn_orient_matrix_UB_23      -0.0092762000
_diffrn_orient_matrix_UB_31      0.0244011000
_diffrn_orient_matrix_UB_32      0.1308953000
_diffrn_orient_matrix_UB_33      0.0407200000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9840
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.102
_diffrn_reflns_theta_max         67.102
_diffrn_reflns_theta_min         3.114
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91252
_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
;
;
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1048
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_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0608P)^2^+0.5338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3996
_reflns_number_total             4705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01604_si_001.cif
_cod_data_source_block           20150589
_cod_database_code               1555090
_chemical_oxdiff_formula         C20H20N4O4P1
_shelx_estimated_absorpt_t_max   0.777
_shelx_estimated_absorpt_t_min   0.732
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Ternary CH refined with riding coordinates:
 C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C27(H27), C28(H28), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              69397
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'