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_1555089
_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         'C38 H34 P2'
_chemical_formula_sum            'C38 H34 P2'
_chemical_formula_weight         552.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_cell_angle_alpha                107.86(3)
_cell_angle_beta                 95.73(3)
_cell_angle_gamma                104.279(13)
_cell_formula_units_Z            2
_cell_length_a                   8.6263(9)
_cell_length_b                   12.097(2)
_cell_length_c                   16.023(6)
_cell_measurement_reflns_used    5011
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.3640
_cell_measurement_theta_min      4.0780
_cell_volume                     1514.1(7)
_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
;
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      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega    1.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   60.0000 34

  2 omega   32.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 29

  3 omega   36.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 27

  4 omega  -17.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 52

  5 omega  -70.00  -43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 27

  6 omega   66.00  123.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  150.0000 57

  7 omega  -12.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   90.0000 58

  8 omega   18.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -121.0000 -130.0000 93

  9 omega   17.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000    0.0000 59

 10 omega   57.00  124.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -120.0000 67

 11 omega   35.00  124.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 89

 12 omega   18.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -120.0000 41

 13 omega   51.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 62

 14 omega   91.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000    0.0000 85

 15 omega   48.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 37

 16 omega  103.00  128.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -60.0000 25

 17 omega   41.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 26

 18 omega   41.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 26

 19 omega  115.00  150.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  150.0000 35

 20 omega   40.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 41

 21 omega   51.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 38

 22 omega   46.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 40

 23 omega   42.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 57

 24 omega   50.00  116.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 66

 25 omega   41.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 57

 26 omega   45.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 26

 27 omega  148.00  174.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -60.0000 26

 28 omega  103.00  131.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 28

 29 omega   39.00   79.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 40

 30 omega   81.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 27

 31 omega   56.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 26

 32 omega   65.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  120.0000 113

 33 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 45

 34 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 90

 35 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 90

 36 omega   26.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   60.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0680275000
_diffrn_orient_matrix_UB_12      0.1320427000
_diffrn_orient_matrix_UB_13      0.0036177000
_diffrn_orient_matrix_UB_21      -0.0193682000
_diffrn_orient_matrix_UB_22      -0.0446018000
_diffrn_orient_matrix_UB_23      -0.1024937000
_diffrn_orient_matrix_UB_31      -0.1738749000
_diffrn_orient_matrix_UB_32      0.0124055000
_diffrn_orient_matrix_UB_33      -0.0083019000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10622
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.479
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94587
_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    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
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_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+0.2282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                4628
_reflns_number_total             5376
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01604_si_002.cif
_cod_data_source_block           201411253
_cod_original_cell_volume        1514.2(7)
_cod_database_code               1555089
_chemical_oxdiff_formula         C20H20N4P2
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
  C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'