Palladium-catalyzed C-P cross-coupling of allenic alcohols with <i>H</i>-phosphonates leading to 2-phosphinoyl-1,3-butadienes.
Hu, Shanshan; Sun, Wenyu; Chen, Junhong; Li, Sipei; Zhao, Runmin; Xu, Pengxiang; Gao, Yuxing; Zhao, Yufen; Chemical communications (Cambridge, England) 57 (2021) 339–342; doi:10.1039/d0cc07022j

data_7127433
_publ_section_title
;
 Palladium-catalyzed C-P cross-coupling of allenic alcohols with
 <i>H</i>-phosphonates leading to 2-phosphinoyl-1,3-butadienes.
;
_journal_issue                   3
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              339
_journal_page_last               342
_journal_paper_doi               10.1039/d0cc07022j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         '4(C23 H28 Cl O3 P), 3(H2 O)'
_chemical_formula_sum            'C92 H118 Cl4 O15 P4'
_chemical_formula_weight         1729.54
_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   mixed
_audit_creation_date             2020-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-29 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                99.134(3)
_cell_angle_beta                 92.375(2)
_cell_angle_gamma                111.125(3)
_cell_formula_units_Z            1
_cell_length_a                   9.6365(3)
_cell_length_b                   11.8750(5)
_cell_length_c                   21.5769(6)
_cell_measurement_reflns_used    6930
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.5070
_cell_measurement_theta_min      4.0490
_cell_volume                     2260.90(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00 -46.00   1.00    1.50    --  -40.88 178.00 -30.00   64
  2  \w   -109.00 -25.00   1.00    1.50    --  -40.88 -37.00-150.00   84
  3  \w   -113.00 -15.00   1.00    1.50    --  -40.88 -37.00 -60.00   98
  4  \w     24.00  83.00   1.00    1.50    --   40.88 -99.00-120.00   59
  5  \w     58.00  91.00   1.00    1.50    --   40.88 178.00-120.00   33
  6  \w     60.00 108.00   1.00    6.00    --  101.16 -94.00   0.00   48
  7  \w     41.00 115.00   1.00    6.00    --  101.16-125.00-150.00   74
  8  \w     23.00 109.00   1.00    6.00    --  101.16 -94.00 -90.00   86
  9  \w     84.00 118.00   1.00    6.00    --  101.16 -45.00 -60.00   34
 10  \w     35.00  80.00   1.00    6.00    --  101.16 -45.00 -60.00   45
 11  \w     79.00 164.00   1.00    6.00    --  101.16  77.00 -90.00   85
 12  \w    127.00 175.00   1.00    6.00    --  101.16 125.00-120.00   48
 13  \w    102.00 171.00   1.00    6.00    --  101.16 125.00 -30.00   69
 14  \w     88.00 118.00   1.00    6.00    --  101.16 -61.00-150.00   30
 15  \w     76.00 169.00   1.00    6.00    --  101.16  30.00  60.00   93
 16  \w    106.00 162.00   1.00    6.00    --  101.16 125.00-150.00   56
 17  \w    109.00 135.00   1.00    6.00    --  101.16 125.00   0.00   26
 18  \w     95.00 159.00   1.00    6.00    --  101.16  45.00 -30.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0286085000
_diffrn_orient_matrix_UB_12      0.1152447000
_diffrn_orient_matrix_UB_13      0.0299968000
_diffrn_orient_matrix_UB_21      -0.0461701000
_diffrn_orient_matrix_UB_22      -0.0565158000
_diffrn_orient_matrix_UB_23      0.0590228000
_diffrn_orient_matrix_UB_31      0.1635956000
_diffrn_orient_matrix_UB_32      0.0596919000
_diffrn_orient_matrix_UB_33      0.0301121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15104
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.549
_diffrn_reflns_theta_min         4.062
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             918
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         8402
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0795P)^2^+0.4808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7281
_reflns_number_total             8402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07022j2.cif
_cod_data_source_block           exp_11076
_cod_depositor_comments          'Adding full bibliography for 7127433.cif.'
_cod_database_code               7127433
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C O N P'
_shelx_estimated_absorpt_t_max   0.798
_shelx_estimated_absorpt_t_min   0.538
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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, All O(H,H) groups
2. Restrained distances
 C48-C44 \\sim C47-C44 \\sim C44-C46 \\sim C44-C45
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C44 \\sim C48 \\sim C46 \\sim C45 \\sim C47: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(H44A)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(C46)=Sof(H46A)=Sof(H46B)=
 Sof(H46C)=1-FVAR(1)
 Sof(H44)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=Sof(C47)=Sof(H47A)=Sof(H47B)=
 Sof(H47C)=FVAR(1)
 Fixed Sof: O4(0.5) H4A(0.5) H4B(0.5)
5.a Free rotating group:
 O8(H8A,H8B), O4(H4A,H4B)
5.b Ternary CH refined with riding coordinates:
 C41(H41), C21(H21), C44(H44A), C44(H44), C18(H18)
5.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C36(H36), C10(H10), C31(H31), C16(H16), C26(H26), C34(H34),
 C37(H37), C30(H30), C7(H7), C3(H3), C13(H13), C11(H11), C8(H8), C33(H33),
 C39(H39), C14(H14), C40(H40)
5.d X=CH2 refined with riding coordinates:
 C24(H24A,H24B), C1(H1A,H1B)
5.e Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C28(H28A,H28B,H28C), C42(H42A,H42B,H42C), C19(H19A,H19B,
 H19C), C43(H43A,H43B,H43C), C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C23(H23A,
 H23B,H23C), C48(H48A,H48B,H48C), C46(H46A,H46B,H46C), C45(H45A,H45B,H45C),
 C47(H47A,H47B,H47C)
;
_shelx_res_checksum              7999
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.505
_oxdiff_exptl_absorpt_empirical_full_min 0.785