Diastereoselective aldol-type interception of phenolic oxonium ylides for the direct assembly of 2,2-disubstituted dihydrobenzofurans.
Hong, Kemiao; Yang, Xiangji; Zhang, Zhijing; Xie, Xiongda; Lv, Xin; Xu, Xinfang; Hu, Wenhao; Organic & biomolecular chemistry 20 (2022) 4635–4639; doi:10.1039/d2ob00723a

data_7158702
_publ_section_title
;
 Diastereoselective aldol-type interception of phenolic oxonium ylides for
 the direct assembly of 2,2-disubstituted dihydrobenzofurans.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4635
_journal_page_last               4639
_journal_paper_doi               10.1039/d2ob00723a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C25 H21 N O5'
_chemical_formula_sum            'C25 H21 N O5'
_chemical_formula_weight         415.43
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-11-28 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                75.339(2)
_cell_angle_beta                 70.665(2)
_cell_angle_gamma                78.677(2)
_cell_formula_units_Z            4
_cell_length_a                   11.8311(3)
_cell_length_b                   12.9022(3)
_cell_length_c                   14.4374(3)
_cell_measurement_reflns_used    13315
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9230
_cell_measurement_theta_min      3.5720
_cell_volume                     1996.47(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_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    -68.00  11.00   0.50    0.20    --  -46.62  74.00 -80.00  158
  2  \w    -24.00  10.00   0.50    0.20    --  -46.62  19.00-150.00   68
  3  \w    -24.00  28.00   0.50    0.20    --  -46.62  19.00-120.00  104
  4  \w     46.00  97.00   0.50    0.20    --   46.62  74.00 -80.00  102
  5  \w     86.00 176.00   0.50    1.50    --  105.44  74.00 -80.00  180
  6  \w    135.00 176.00   0.50    1.50    --  105.44  30.00  60.00   82
  7  \w    135.00 174.00   0.50    1.50    --  105.44   0.00  90.00   78
  8  \w     91.00 130.00   0.50    1.50    --  105.44  30.00  60.00   78
  9  \w     97.00 123.00   0.50    1.50    --  105.44   0.00  90.00   52
 10  \w     69.00 107.00   0.50    1.50    --  105.44 -77.00   0.00   76
 11  \w     61.00 111.00   0.50    1.50    --  105.44-125.00  30.00  100
 12  \w     85.00 111.00   0.50    1.50    --  105.44-125.00 120.00   52
 13  \w     41.00  66.00   0.50    1.50    --  105.44 -74.00 151.00   50
 14  \w     46.00 105.00   0.50    1.50    --  105.44 -94.00  90.00  118
 15  \w     35.00  61.00   0.50    1.50    --  105.44   0.00  90.00   52
 16  \w     34.00  64.00   0.50    1.50    --  105.44 -77.00   0.00   60
 17  \w     33.00  73.00   0.50    1.50    --  105.44 -61.00 -60.00   80
 18  \w     33.00  71.00   0.50    1.50    --  105.44 -61.00 -90.00   76
 19  \w     41.00  67.00   0.50    1.50    --  105.44 -61.00-150.00   52
 20  \w     53.00  79.00   0.50    1.50    --  105.44 -94.00-180.00   52
 21  \w     52.00 110.00   0.50    1.50    --  105.44-125.00-150.00  116
 22  \w     34.00 111.00   0.50    1.50    --  105.44-125.00-120.00  154
 23  \w     39.00 110.00   0.50    1.50    --  105.44-125.00 -60.00  142
 24  \w     38.00 111.00   0.50    1.50    --  105.44-125.00  60.00  146
 25  \w     38.00  63.00   0.50    1.50    --  105.44 -94.00 150.00   50
 26  \w     23.00  94.00   0.50    0.20    --   46.62-125.00  30.00  142
 27  \w    -25.00  53.00   0.50    0.20    --   46.62 -74.00 151.00  156
 28  \w    103.00 167.00   0.50    1.50    --  105.44  61.00 -30.00  128
 29  \w     90.00 177.00   0.50    1.50    --  105.44  30.00-150.00  174
 30  \w    -69.00 -44.00   0.50    1.50    -- -100.00  74.00 -80.00   50
 31  \w    -89.00 -53.00   0.50    1.50    -- -100.00 125.00 -90.00   72
 32  \w   -112.00 -69.00   0.50    1.50    -- -100.00 125.00 -60.00   86
 33  \w    -66.00 -29.00   0.50    1.50    -- -100.00  61.00  90.00   74
 34  \w    -66.00 -28.00   0.50    1.50    -- -100.00  61.00 120.00   76
 35  \w   -110.00 -85.00   0.50    1.50    -- -100.00 -45.00  90.00   50
 36  \w   -117.00 -52.00   0.50    0.20    --  -46.62 -74.00 151.00  130
 37  \w    -99.00 -74.00   0.50    0.20    --  -46.62-125.00 -60.00   50
 38  \w   -160.00-135.00   0.50    1.50    -- -100.00 -45.00  90.00   50
 39  \w   -167.00 -80.00   0.50    1.50    -- -100.00 -74.00 151.00  174
 40  \w   -170.00 -90.00   0.50    1.50    -- -100.00 -45.00-150.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0147471000
_diffrn_orient_matrix_UB_12      0.0681476000
_diffrn_orient_matrix_UB_13      0.0777528000
_diffrn_orient_matrix_UB_21      -0.1280368000
_diffrn_orient_matrix_UB_22      -0.0316152000
_diffrn_orient_matrix_UB_23      0.0549236000
_diffrn_orient_matrix_UB_31      0.0522095000
_diffrn_orient_matrix_UB_32      -0.0991182000
_diffrn_orient_matrix_UB_33      0.0654011000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25831
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.296
_diffrn_reflns_theta_min         3.313
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00060(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         8018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0423P)^2^+0.7206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7044
_reflns_number_total             8018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00723a2.cif
_cod_data_source_block           hongkm_210701
_cod_depositor_comments          'Adding full bibliography for 7158702.cif.'
_cod_original_cell_volume        1996.48(9)
_cod_database_code               7158702
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.797
_reflns_odcompleteness_completeness 99.87
_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 C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C1E(H1EA,H1EB), C1J(H1JA,H1JB), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C17(H17), C19(H19), C1A(H1A), C1B(H1B), C1H(H1H),
 C1I(H1I), C1K(H1K), C1L(H1L), C1M(H1M), C1N(H1N), C1O(H1O), C1P(H1P), C1Q(H1Q),
  C1R(H1R), C1S(H1S), C1T(H1T), C1V(H1V), C1W(H1W), C1X(H1X), C1Y(H1Y),
 C1Z(H1Z), C20(H20), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C1U(H1UA,H1UB,H1UC), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_shelx_res_checksum              3001
_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 2.258
_oxdiff_exptl_absorpt_empirical_full_min 0.377