Palladium-catalyzed (<i>Z</i>)-selective allylation of phosphine oxides with vinylethylene carbonates to construct phosphorus allyl alcohols.
Huang, Hua; Wu, Yi-Qi; Han, Lu-Yao; Jiang, Lu; Zhang, Zhuo-Zhuo; Zhang, Xiang; Han, Bo; Huang, Wei; Li, Jun-Long; Organic & biomolecular chemistry 22 (2024) 3068–3072; doi:10.1039/d4ob00354c

data_7159859
_publ_section_title
;
 Palladium-catalyzed (<i>Z</i>)-selective allylation of phosphine oxides
 with vinylethylene carbonates to construct phosphorus allyl alcohols.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3068
_journal_page_last               3072
_journal_paper_doi               10.1039/d4ob00354c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C22 H20 Cl O2 P'
_chemical_formula_sum            'C22 H20 Cl O2 P'
_chemical_formula_weight         382.80
_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     dual
_audit_creation_date             2022-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-11 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.9972(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.74906(11)
_cell_length_b                   19.4433(5)
_cell_length_c                   17.5592(4)
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.0920
_cell_measurement_theta_min      5.1690
_cell_volume                     1958.01(8)
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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   -107.00   3.00   1.00    4.68    --  -34.98 -19.00 150.00  110
  2  \w     23.00  90.00   1.00    4.68    --   34.98-125.00  30.00   67
  3  \w    -33.00  53.00   1.00    4.68    --   34.98 -57.00  60.00   86
  4  \w      6.00 104.00   1.00    4.68    --   34.98  77.00 -90.00   98
  5  \w      1.00  75.00   1.00    4.68    --   34.98 -99.00-120.00   74
  6  \w     13.00 106.00   1.00    4.68    --   34.98  38.00  30.00   93
  7  \w     87.00 177.00   1.00   18.73    --  106.90  45.00-120.00   90
  8  \w     36.00 113.00   1.00   18.73    --  106.90-111.00 -90.00   77
  9  \w    100.00 178.00   1.00   18.73    --  106.90 111.00 150.00   78
 10  \w     36.00 113.00   1.00   18.73    --  106.90-111.00-120.00   77
 11  \w     81.00 178.00   1.00   18.73    --  106.90  30.00-150.00   97
 12  \w     36.00 113.00   1.00   18.73    --  106.90-111.00  60.00   77
 13  \w     81.00 178.00   1.00   18.73    --  106.90  30.00 -60.00   97
 14  \w     41.00 110.00   1.00   18.73    --  106.90 -94.00  90.00   69
 15  \w     44.00 126.00   1.00   18.73    --  106.90 -45.00  60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0237675000
_diffrn_orient_matrix_UB_12      -0.0453122000
_diffrn_orient_matrix_UB_13      0.0720600000
_diffrn_orient_matrix_UB_21      -0.0339780000
_diffrn_orient_matrix_UB_22      0.0638682000
_diffrn_orient_matrix_UB_23      0.0499998000
_diffrn_orient_matrix_UB_31      -0.2654000000
_diffrn_orient_matrix_UB_32      -0.0122243000
_diffrn_orient_matrix_UB_33      -0.0061534000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10742
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.318
_diffrn_reflns_theta_min         4.548
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63218
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0618
_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^)+(0.1300P)^2^+0.2018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3033
_reflns_number_total             3732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00354c2.cif
_cod_data_source_block           ljl-hh-0924
_cod_depositor_comments          'Adding full bibliography for 7159859.cif.'
_cod_original_cell_volume        1958.00(8)
_cod_database_code               7159859
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.92
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00C(H00C,H00D), C00I(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00D(H00E), C00E(H00F), C00F(H00G),
 C00H(H00H), C00J(H00K), C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O),
 C00O(H00P), C00P(H00Q), C00Q(H00R)
2.c Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_shelx_res_checksum              96904
_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 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.644