Ph3P-mediated highly selective C(α)–P coupling of quinone monoacetals with R2P(O)H: convenient and practical synthesis of ortho-phosphinyl phenols
Shen, Ruwei; Zhang, Ming; Xiao, Jing; Dong, Chao; Han, Li-Biao; Green Chemistry 20 (2018) 5111–; doi:10.1039/C8GC02918K

data_7237092
_publ_section_title
;
 Ph3P-mediated highly selective C(\a)--P coupling of quinone monoacetals
 with R2P(O)H: convenient and practical synthesis of ortho-phosphinyl
 phenols
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              5111
_journal_paper_doi               10.1039/C8GC02918K
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 O5 P'
_chemical_formula_sum            'C20 H19 O5 P'
_chemical_formula_weight         370.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-10 deposited with the CCDC.
2018-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4510(7)
_cell_length_b                   18.5872(10)
_cell_length_c                   7.9138(5)
_cell_measurement_reflns_used    7835
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3175
_cell_measurement_theta_min      3.2346
_cell_volume                     1831.48(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -70.00    2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  126.0000   92.0000 72

  2 omega  -17.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   77.0000  120.0000 97

  3 omega  -14.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000   60.0000 89

  4 omega  -14.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000 -120.0000 83

  5 omega  -53.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -77.0000   30.0000 99

  6 omega  -56.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -77.0000  -90.0000 102

  7 omega  -13.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000  -30.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0173542000
_diffrn_orient_matrix_UB_12      0.0231741000
_diffrn_orient_matrix_UB_13      -0.0657460000
_diffrn_orient_matrix_UB_21      -0.0535779000
_diffrn_orient_matrix_UB_22      0.0026476000
_diffrn_orient_matrix_UB_23      -0.0298431000
_diffrn_orient_matrix_UB_31      -0.0086189000
_diffrn_orient_matrix_UB_32      0.0301988000
_diffrn_orient_matrix_UB_33      0.0530989000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25295
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_min         3.241
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.4196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3013
_reflns_number_total             3352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc02918k2.cif
_cod_data_source_block           180315_zm_zju_1
_cod_database_code               7237092
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o P'
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.918
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              2555
_olex2_submission_special_instructions 'No special instructions were received'