Primary activation of <i>para</i>-quinone methides by chiral phosphoric acid for enantioselective construction of tetraarylmethanes.
Han, Zhengyu; Zhu, Biao; Zang, Yu; Zhang, Chaoshen; Dong, Xiu-Qin; Huang, Hai; Sun, Jianwei; Chemical science 15 (2024) 720–725; doi:10.1039/d3sc05014a

data_1570481
_publ_section_title
;
 Primary activation of <i>para</i>-quinone methides by chiral phosphoric
 acid for enantioselective construction of tetraarylmethanes.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              720
_journal_page_last               725
_journal_paper_doi               10.1039/d3sc05014a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H29 N O3, C H4 O'
_chemical_formula_sum            'C32 H33 N O4'
_chemical_formula_weight         495.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-10-26
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2022-12-14 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9813(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.02736(13)
_cell_length_b                   7.62610(7)
_cell_length_c                   13.31312(13)
_cell_measurement_reflns_used    7351
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.8080
_cell_measurement_theta_min      3.3410
_cell_volume                     1309.82(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_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    107.00 175.00   1.00    7.00    --  112.00  77.00  30.00   68
  2  \w    -65.00  12.00   1.00    3.00    --  -41.26  37.00  60.00   77
  3  \w   -114.00 -13.00   1.00    3.00    --  -41.26 -57.00  30.00  101
  4  \w    -46.00 124.00   1.00    3.00    --   41.26   0.00   0.00  170
  5  \w    117.00 178.00   1.00    7.00    --  112.00 111.00 120.00   61
  6  \w    128.00 176.00   1.00    7.00    --  112.00  77.00  60.00   48
  7  \w     36.00 106.00   1.00    7.00    --  112.00-111.00 -90.00   70
  8  \w     85.00 178.00   1.00    7.00    --  112.00  30.00-120.00   93
  9  \w     51.00 108.00   1.00    7.00    --  112.00-111.00 -30.00   57
 10  \w     29.00 103.00   1.00    7.00    --  112.00 -94.00 120.00   74
 11  \w     90.00 177.00   1.00    7.00    --  112.00  30.00 120.00   87
 12  \w     36.00 109.00   1.00    7.00    --  112.00-111.00  90.00   73
 13  \w     87.00 176.00   1.00    7.00    --  112.00  45.00-180.00   89
;
_diffrn_measurement_device       'kappa 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      0.0695254000
_diffrn_orient_matrix_UB_12      -0.1467843000
_diffrn_orient_matrix_UB_13      -0.0328838000
_diffrn_orient_matrix_UB_21      -0.0970618000
_diffrn_orient_matrix_UB_22      -0.1031077000
_diffrn_orient_matrix_UB_23      -0.0456619000
_diffrn_orient_matrix_UB_31      0.0019590000
_diffrn_orient_matrix_UB_32      0.0930341000
_diffrn_orient_matrix_UB_33      -0.1023846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8645
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.874
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 2273 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5291
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0358P)^2^+0.1781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0652
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                5170
_reflns_number_total             5291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05014a2.cif
_cod_data_source_block           sliu4cult_auto
_cod_depositor_comments          'Adding full bibliography for 1570481.cif.'
_cod_database_code               1570481
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C32 H33 N O4'
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.880
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C8(H8), C13(H13), C14(H14), C16(H16), C17(H17),
 C23(H23), C24(H24), C25(H25), C26(H26), C32(H32), C33(H33), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C27(H27A,H27B,H27C), C37(H37A,H37B,
 H37C), C1S(H1SA,H1SB,H1SC)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O1S(H1S)
;
_shelx_res_checksum              35510
_shelx_hkl_checksum              54992
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.257
_oxdiff_exptl_absorpt_empirical_full_min 0.891