Synthesis of 4-aryl-3,4-dihydrocoumarins and 4-aryl-4H-chromenes via Er(OTf)3-catalyzed cascade reactions of p-quinone methides with 1,3-dicarbonyl compounds
Bao, Xiaobo; Yu, Wei; Wang, Lilin; Dong, Xu; Wang, Guoli; Chen, Weilin; Li, Fei; Chen, Dongyin; RSC Advances 13 (2023) 15942–15946; doi:10.1039/D3RA02267F

data_7246846
_publ_section_title
;
 Synthesis of 4-aryl-3,4-dihydrocoumarins and 4-aryl-4H-chromenes via
 Er(OTf)3-catalyzed cascade reactions of p-quinone methides with
 1,3-dicarbonyl compounds
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              15942
_journal_page_last               15946
_journal_paper_doi               10.1039/D3RA02267F
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C32 H42 O4'
_chemical_formula_sum            'C32 H42 O4'
_chemical_formula_weight         490.65
_chemical_name_systematic        1
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2fgfkx
_audit_creation_date             2023-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.3630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.6928(2)
_cell_length_b                   14.67570(10)
_cell_length_c                   21.8092(3)
_cell_measurement_reflns_used    16469
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0150
_cell_measurement_theta_min      2.0260
_cell_volume                     5903.21(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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     18.00 123.00   0.50    0.50    --   42.00  65.00   0.00  210
  2  \w     74.00 111.00   0.50    0.50    --   42.00  82.00 -60.00   74
  3  \w     29.00  66.00   0.50    0.50    --   42.00 -82.00 -90.00   74
  4  \w    -47.00  -5.00   0.50    0.50    --   42.00 -82.00 120.00   84
  5  \w     43.00  85.00   0.50    0.50    --   42.00 -21.00  90.00   84
  6  \w     17.00  65.00   0.50    0.50    --   42.00  82.00 -60.00   96
  7  \w    -47.00  -5.00   0.50    0.50    --   42.00 -21.00  90.00   84
  8  \w    -42.00  64.00   0.50    0.50    --   42.00 -82.00  90.00  212
  9  \w      3.00  69.00   0.50    0.50    --   42.00 -82.00-180.00  132
 10  \w     10.00  68.00   0.50    0.50    --   42.00 -82.00 120.00  116
 11  \w    -47.00 -20.00   0.50    0.50    --   42.00 -82.00 -60.00   54
 12  \w    -15.00  29.00   0.50    0.50    --   42.00 -82.00 -60.00   88
 13  \w     23.00  63.00   0.50    0.50    --   42.00 -65.00-180.00   80
 14  \w    -32.00  -6.00   0.50    0.50    --   42.00 -65.00-180.00   52
 15  \w    -23.00  66.00   0.50    0.50    --   42.00 -77.00  30.00  178
 16  \w     -1.00  30.00   0.50    0.50    --   42.00 -21.00  90.00   62
 17  \w    -28.00  -3.00   0.50    0.50    --   42.00 -82.00 -30.00   50
 18  \w     40.00  65.00   0.50    0.50    --   42.00  65.00-150.00   50
 19  \w     41.00  69.00   0.50    0.50    --   42.00 -82.00 -30.00   56
 20  \w     91.00 130.00   0.50    0.50    --   42.00 -21.00  90.00   78
 21  \w      4.00 108.00   0.50    0.50    --   93.70 -59.00  90.00  208
 22  \w      4.00 109.00   0.50    0.50    --   93.70 -59.00 -90.00  210
 23  \w      4.00  69.00   0.50    0.50    --   93.70 -33.00 -90.00  130
 24  \w     26.00 120.00   0.50    0.50    --   93.70 -82.00  90.00  188
 25  \w     59.00  99.00   0.50    0.50    --   93.70 -82.00 -30.00   80
 26  \w     41.00  90.00   0.50    0.50    --   93.70 -82.00-180.00   98
 27  \w      4.00 104.00   0.50    0.50    --   93.70 -82.00  30.00  200
 28  \w     19.00  60.00   0.50    0.50    --   93.70 -33.00 -60.00   82
 29  \w     67.00 126.00   0.50    0.50    --   93.70 -33.00 -60.00  118
 30  \w     71.00 102.00   0.50    0.50    --   93.70 -82.00 120.00   62
 31  \w     65.00  90.00   0.50    0.50    --   93.70 -82.00 150.00   50
 32  \w    118.00 144.00   0.50    0.50    --   93.70  68.00-180.00   52
 33  \w     34.00 104.00   0.50    0.50    --   93.70 -82.00-150.00  140
 34  \w      4.00 105.00   0.50    0.50    --   93.70 -82.00 -90.00  202
 35  \w     70.00  96.00   0.50    0.50    --   93.70 -82.00   0.00   52
 36  \w     75.00 100.00   0.50    0.50    --   93.70 -82.00  60.00   50
 37  \w      5.00  63.00   0.50    0.50    --   93.70 -82.00  60.00  116
 38  \w     63.00  88.00   0.50    0.50    --   93.70 -82.00-120.00   50
 39  \w     12.00  57.00   0.50    0.50    --   93.70 -77.00-120.00   90
 40  \w      4.00 182.00   0.50    0.50    --   93.70   0.00   0.00  356
 41  \w     12.00  38.00   0.50    0.50    --   93.70 -82.00-120.00   52
 42  \w     91.00 135.00   0.50    0.50    --   93.70  33.00-180.00   88
 43  \w      8.00 121.00   0.50    0.50    --   93.70 -33.00  90.00  226
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0574128000
_diffrn_orient_matrix_UB_12      0.0561333000
_diffrn_orient_matrix_UB_13      -0.0266782000
_diffrn_orient_matrix_UB_21      0.0452621000
_diffrn_orient_matrix_UB_22      0.0075266000
_diffrn_orient_matrix_UB_23      0.0654280000
_diffrn_orient_matrix_UB_31      0.0403569000
_diffrn_orient_matrix_UB_32      -0.0884416000
_diffrn_orient_matrix_UB_33      -0.0113969000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28471
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.115
_diffrn_reflns_theta_min         3.849
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull greenish green'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00135(9)
_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   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5373
_refine_ls_number_restraints     495
_refine_ls_restrained_S_all      1.413
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0725P)^2^+2.9105P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4691
_reflns_number_total             5373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra02267f2.cif
_cod_data_source_block           mzl_auto
_cod_database_code               7246846
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.967
_diffrn_oxdiff_digest_frames
;
01c30b2523971ee83ec29f7799c1c8522700029b493
;
_diffrn_oxdiff_digest_hkl
;
01377fb9a0c05181699eb3a735108a66bfcc41
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H1-H8A
 2 with sigma of 0.002
 H1-H10C
 2 with sigma of 0.002
3. Rigid bond restraints
 C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C13 \\sim C7 \\sim C25 \\sim C12 \\sim C15 \\sim C24 \\sim C6 \\sim C26 \\sim
C16 \\sim C14 \\sim C5 \\sim C9 \\sim C27 \\sim C21 \\sim C23 \\sim C10 \\sim
C17 \\sim C2 \\sim C32 \\sim C28 \\sim C8 \\sim C20 \\sim C19 \\sim C18 \\sim
C11 \\sim C29 \\sim C31 \\sim C30 \\sim C3 \\sim C22 \\sim C1 \\sim C4: within
2.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
5.a Ternary CH refined with riding coordinates:
 C15(H15), C27(H27)
5.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C32(H32A,H32B), C28(H28A,H28B), C29(H29A,H29B), C31(H31A,
 H31B), C30(H30A,H30B)
5.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C17(H17), C20(H20), C19(H19), C18(H18)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C3(H3A,H3B,H3C),
 C22(H22A,H22B,H22C), C1(H1A,H1B,H1C), C4(H4A,H4B,H4C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              82797
_shelx_hkl_checksum              38530
_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 2.665
_oxdiff_exptl_absorpt_empirical_full_min 0.760