Asymmetric Construction of Tertiary/Secondary Carbon–Phosphorus Bonds via Bifunctional Phosphonium Salt Catalyzed 1,6-Addition
Chen, Yuan; Yu, Zhaoyuan; Jiang, Zhiyu; Tan, Jian-Ping; Wu, Jia-Hong; Lan, Yu; Ren, Xiaoyu; Wang, Tianli; ACS Catalysis 11 (2021) 14168–14180; doi:10.1021/acscatal.1c03149

data_4519162
_publ_section_title
;
 Asymmetric Construction of Tertiary/Secondary Carbon--Phosphorus Bonds
 via Bifunctional Phosphonium Salt Catalyzed 1,6-Addition
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              14168
_journal_page_last               14180
_journal_paper_doi               10.1021/acscatal.1c03149
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H21 O3 P'
_chemical_formula_sum            'C25 H21 O3 P'
_chemical_formula_weight         400.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7720(4)
_cell_length_b                   13.7803(6)
_cell_length_c                   13.8713(6)
_cell_measurement_reflns_used    5689
_cell_measurement_temperature    292.08(18)
_cell_measurement_theta_max      72.7250
_cell_measurement_theta_min      4.0700
_cell_volume                     2059.08(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      292.08(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_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    -55.00  33.00   1.00    1.00    --  -36.04  38.00  90.00   88
  2  \w   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00 150.00   84
  3  \w   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00-120.00   84
  4  \w    -53.00  31.00   1.00    1.00    --  -36.04  57.00-180.00   84
  5  \w     23.00  89.00   1.00    1.00    --   36.04-125.00-150.00   66
  6  \w     23.00  89.00   1.00    1.00    --   36.04-125.00  60.00   66
  7  \w      1.00  28.00   1.00    1.00    --   36.04  92.00 -97.45   27
  8  \w     82.00 176.00   1.00    1.00    --  108.71  77.00 150.00   94
  9  \w     39.00 109.00   1.00    1.00    --  108.71 -94.00 150.00   70
 10  \w    100.00 178.00   1.00    1.00    --  108.71 111.00 -90.00   78
 11  \w     39.00 100.00   1.00    1.00    --  108.71 -94.00 -90.00   61
 12  \w     91.00 117.00   1.00    1.00    --  108.71  61.00-180.00   26
 13  \w     71.00 101.00   1.00    1.00    --  108.71  15.00-150.00   30
 14  \w     96.00 122.00   1.00    1.00    --  108.71  45.00-180.00   26
 15  \w     92.00 130.00   1.00    1.00    --  108.71  61.00-150.00   38
 16  \w     82.00 108.00   1.00    1.00    --  108.71  77.00-180.00   26
 17  \w     39.00 106.00   1.00    1.00    --  108.71 -94.00 -30.00   67
 18  \w    132.00 158.00   1.00    1.00    --  108.71  61.00-150.00   26
 19  \w     87.00 150.00   1.00    1.00    --  108.71  30.00-150.00   63
 20  \w     91.00 177.00   1.00    1.00    --  108.71  49.00  88.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0806114000
_diffrn_orient_matrix_UB_12      -0.0481619000
_diffrn_orient_matrix_UB_13      -0.0784005000
_diffrn_orient_matrix_UB_21      0.0242699000
_diffrn_orient_matrix_UB_22      -0.0867263000
_diffrn_orient_matrix_UB_23      0.0676305000
_diffrn_orient_matrix_UB_31      -0.1156837000
_diffrn_orient_matrix_UB_32      -0.0514290000
_diffrn_orient_matrix_UB_33      -0.0402648000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11277
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.559
_diffrn_reflns_theta_min         4.523
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0608
_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^)+(0.1158P)^2^+0.2148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                3738
_reflns_number_total             3920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03149_si_003.cif
_cod_data_source_block           wtl-jzy-190401-ys
_cod_original_cell_volume        2059.06(14)
_cod_database_code               4519162
_reflns_odcompleteness_completeness 98.96
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_shelx_res_checksum              67676
_shelx_hkl_checksum              99720
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-01
_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 1.564
_oxdiff_exptl_absorpt_empirical_full_min 0.627