Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization Reactions Mediated by Iodine or Copper Dibromide.
Essid, I.; Laborde, C.; Legros, F.; Sevrain, N.; Touil, S.; Rolland, M.; Ayad, T.; Volle, J.-N.; Pirat, J.-L.; Virieux, D.; Organic letters  (2017) –; doi:10.1021/acs.orglett.7b00648

data_1546603
_publ_section_title
;
 Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization
 Reactions Mediated by Iodine or Copper Dibromide.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.7b00648
_journal_year                    2017
_chemical_formula_moiety         'C30 H22 Br2 O6 P2'
_chemical_formula_sum            'C30 H22 Br2 O6 P2'
_chemical_formula_weight         700.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           54
_space_group_name_Hall           '-P 2a 2ac'
_space_group_name_H-M_alt        'P c c a'
_symmetry_space_group_name_Hall  '-P 2a 2ac'
_symmetry_space_group_name_H-M   'P c c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.0189(6)
_cell_length_b                   14.0226(4)
_cell_length_c                   7.2637(2)
_cell_measurement_reflns_used    6560
_cell_measurement_temperature    175.00(14)
_cell_measurement_theta_max      67.3170
_cell_measurement_theta_min      3.1280
_cell_volume                     2752.04(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      175.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0143
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -108.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000 -179.0000  120.0000 74

  2 omega  -62.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000  -30.0000 98

  3 omega  -52.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  150.0000 87

  4 omega -108.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000 -179.0000  -30.0000 74

  5 omega   13.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315   38.0000  120.0000 93

  6 omega   17.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315   57.0000  -30.0000 87

  7 omega    7.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315   77.0000 -180.0000 98

  8 omega    7.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315   77.0000  120.0000 98

  9 omega    7.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315   77.0000    0.0000 98

 10 omega    7.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315   77.0000 -120.0000 98

 11 omega   17.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315   57.0000  -90.0000 87

 12 omega   -4.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315  -99.0000 -180.0000 80

 13 omega   53.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315 -179.0000  150.0000 57

 14 omega    7.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315   77.0000   60.0000 98

 15 omega   56.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6315  179.0000   30.0000 54

 16 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000 -180.0000 88

 17 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000   30.0000 98

 18 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000  120.0000 88

 19 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  150.0000 98

 20 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  120.0000 98

 21 omega   74.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   30.0000  -60.0000 97

 22 omega   30.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -95.0000   30.0000 79

 23 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000   90.0000 88

 24 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  -60.0000 98

 25 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000   90.0000 98

 26 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000   60.0000 98

 27 omega   30.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -95.0000  150.0000 79

 28 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000    0.0000 98

 29 omega   30.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -95.0000   90.0000 79

 30 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000  -90.0000 88

 31 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000  150.0000 88

 32 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000  -60.0000 88

 33 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000   60.0000 88

 34 omega   30.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -95.0000  -90.0000 79

 35 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000   30.0000 88

 36 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000 -180.0000 98

 37 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000    0.0000 88

 38 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000  -30.0000 88

 39 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  -90.0000 98

 40 omega   80.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   61.0000 -120.0000 88

 41 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  -30.0000 98

 42 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000 -150.0000 98

 43 omega   71.00  169.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000 -120.0000 98

 44 omega   29.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000 -112.0000    0.0000 86

 45 omega   31.00  129.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -77.0000 -180.0000 98

 46 omega   74.00  155.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   72.0000 -122.9193 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0484132000
_diffrn_orient_matrix_UB_12      0.0203184000
_diffrn_orient_matrix_UB_13      -0.1049655000
_diffrn_orient_matrix_UB_21      0.0252226000
_diffrn_orient_matrix_UB_22      -0.0289280000
_diffrn_orient_matrix_UB_23      -0.1817885000
_diffrn_orient_matrix_UB_31      -0.0164833000
_diffrn_orient_matrix_UB_32      -0.1040191000
_diffrn_orient_matrix_UB_33      0.0301360000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1683
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            51749
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.058
_diffrn_reflns_theta_min         3.152
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.690
_exptl_crystal_description       prism
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.810
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0558
_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^)+(0.1045P)^2^+1.0810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1680
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1891
_reflns_number_total             2514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00648_si_001.cif
_cod_data_source_block           vir1
_cod_database_code               1546603
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 P1 O1 Si1'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K)
2.b Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_olex2_submission_special_instructions 'No special instructions were received'