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_7246845
_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_absolute_configuration ab
_chemical_formula_moiety         'C27 H34 O5'
_chemical_formula_sum            'C27 H34 O5'
_chemical_formula_weight         438.54
_chemical_name_systematic        1
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2ff2lk
_audit_creation_date             2023-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-08 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.041(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4572(4)
_cell_length_b                   18.7701(7)
_cell_length_c                   11.9458(5)
_cell_measurement_reflns_used    11991
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.6130
_cell_measurement_theta_min      2.3060
_cell_volume                     2543.72(17)
_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
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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     99.00 128.00   0.50    0.50    --   42.30  65.00 -60.00   58
  2  \w    -47.00  20.00   0.50    0.50    --   42.30 -54.00 120.00  134
  3  \w     24.00  50.00   0.50    0.50    --   42.30 -77.00 150.00   52
  4  \w     53.00 128.00   0.50    0.50    --   42.30  65.00 150.00  150
  5  \w     23.00  68.00   0.50    0.50    --   42.30 -82.00  60.00   90
  6  \w     23.00  68.00   0.50    0.50    --   42.30 -54.00 120.00   90
  7  \w    -46.00  38.00   0.50    0.50    --   42.30 -82.00  90.00  168
  8  \w    -26.00   4.00   0.50    0.50    --   42.30 -65.00   0.00   60
  9  \w     93.00 119.00   0.50    0.50    --   42.30  77.00-120.00   52
 10  \w     31.00  56.00   0.50    0.50    --   42.30  82.00  30.00   50
 11  \w      8.00  70.00   0.50    0.50    --   42.30 -82.00 -30.00  124
 12  \w     11.00  68.00   0.50    0.50    --   42.30 -82.00  30.00  114
 13  \w    -47.00  63.00   0.50    0.50    --   42.30 -65.00 -60.00  220
 14  \w    -43.00   5.00   0.50    0.50    --   42.30 -82.00  60.00   96
 15  \w     36.00  69.00   0.50    0.50    --   42.30 -82.00 150.00   66
 16  \w    -36.00 -11.00   0.50    0.50    --   42.30 -82.00 -30.00   50
 17  \w     27.00  52.00   0.50    0.50    --   42.30  65.00 150.00   50
 18  \w     36.00  68.00   0.50    0.50    --   42.30 -82.00 -90.00   64
 19  \w    -43.00  20.00   0.50    0.50    --   42.30 -82.00-150.00  126
 20  \w     67.00 131.00   0.50    0.50    --   42.30  82.00  30.00  128
 21  \w     26.00  66.00   0.50    0.50    --   42.30 -82.00-150.00   80
 22  \w     27.00  58.00   0.50    0.50    --   42.30  77.00-120.00   62
 23  \w     58.00  83.00   0.50    0.50    --   42.30  65.00 -60.00   50
 24  \w     22.00  57.00   0.50    0.50    --   42.30  65.00 -60.00   70
 25  \w     45.00  70.00   0.50    0.50    --   42.30 -82.00  90.00   50
 26  \w     80.00 107.00   0.50    1.00    --   93.70 -82.00  30.00   54
 27  \w     30.00  74.00   0.50    1.00    --   93.70 -82.00  30.00   88
 28  \w      6.00 109.00   0.50    1.00    --   93.70 -82.00-120.00  206
 29  \w     67.00 122.00   0.50    1.00    --   93.70  42.00 150.00  110
 30  \w      5.00  95.00   0.50    1.00    --   93.70 -82.00 -30.00  180
 31  \w     80.00 106.00   0.50    1.00    --   93.70  68.00-150.00   52
 32  \w     82.00 107.00   0.50    1.00    --   93.70 -82.00 -90.00   50
 33  \w     30.00 102.00   0.50    1.00    --   93.70 -82.00   0.00  144
 34  \w     70.00  96.00   0.50    1.00    --   93.70 -82.00-180.00   52
 35  \w    138.00 164.00   0.50    1.00    --   93.70  50.00  90.00   52
 36  \w     59.00 129.00   0.50    1.00    --   93.70  33.00-150.00  140
 37  \w      4.00  66.00   0.50    1.00    --   93.70 -82.00-180.00  124
 38  \w     42.00 183.00   0.50    1.00    --   93.70  17.00 120.00  282
 39  \w     16.00  91.00   0.50    1.00    --   93.70 -82.00  60.00  150
 40  \w    111.00 180.00   0.50    1.00    --   93.70  33.00  30.00  138
 41  \w     66.00  91.00   0.50    1.00    --   93.70  50.00  90.00   50
 42  \w     65.00  91.00   0.50    1.00    --   93.70  33.00  30.00   52
 43  \w     89.00 115.00   0.50    1.00    --   93.70  82.00  30.00   52
 44  \w     64.00  96.00   0.50    1.00    --   93.70 -82.00 120.00   64
 45  \w     70.00 101.00   0.50    1.00    --   93.70 -82.00 150.00   62
 46  \w      7.00  55.00   0.50    1.00    --   93.70 -82.00 120.00   96
 47  \w      4.00  95.00   0.50    1.00    --   93.70 -82.00-150.00  182
 48  \w     10.00  57.00   0.50    1.00    --   93.70 -82.00 -90.00   94
 49  \w     21.00  98.00   0.50    1.00    --   93.70 -82.00  90.00  154
 50  \w      4.00  97.00   0.50    1.00    --   93.70 -82.00 -60.00  186
 51  \w    133.00 181.00   0.50    1.00    --   93.70  42.00 150.00   96
 52  \w     18.00  76.00   0.50    1.00    --   93.70 -68.00 120.00  116
 53  \w     70.00  95.00   0.50    1.00    --   93.70 -82.00 -75.35   50
 54  \w      4.00  59.00   0.50    1.00    --   93.70 -82.00 -75.35  110
;
_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      -0.0970470000
_diffrn_orient_matrix_UB_12      -0.0237064000
_diffrn_orient_matrix_UB_13      0.0692763000
_diffrn_orient_matrix_UB_21      -0.0918323000
_diffrn_orient_matrix_UB_22      0.0036578000
_diffrn_orient_matrix_UB_23      -0.1072827000
_diffrn_orient_matrix_UB_31      0.0249290000
_diffrn_orient_matrix_UB_32      -0.0783844000
_diffrn_orient_matrix_UB_33      -0.0258812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28077
_diffrn_reflns_point_group_measured_fraction_full 0.807
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.006
_diffrn_reflns_theta_min         3.737
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50949
_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            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         7449
_refine_ls_number_restraints     598
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0798
_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^)+(0.1733P)^2^+0.0710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2385
_reflns_Friedel_coverage         0.563
_reflns_Friedel_fraction_full    0.603
_reflns_Friedel_fraction_max     0.599
_reflns_number_gt                6132
_reflns_number_total             7449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra02267f2.cif
_cod_data_source_block           10c_auto
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C54 H68 O10'
_cod_original_formula_weight         877.08
_cod_original_formula_moiety         '2(C27 H34 O5)'
_cod_original_formula_units_Z            2
_cod_database_code               7246845
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.952
_diffrn_oxdiff_digest_frames
;
01241b951efb5b9a46bcfe13e3bad78ef7000310137
;
_diffrn_oxdiff_digest_hkl
;
0118d0e8ce237b6e0451ffdedd95dbe739a3c8
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7(4)
 0.3(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H8A,H8B,H8C} of C8
 At 1.5 times of:
  All O(H) groups, {H53A,H53B,H53C} of C53, {H54A,H54B,H54C} of C54, {H6A,H6B,
  H6C} of C6, {H4A,H4B,H4C} of C4, {H3A,H3B,H3C} of C3, {H26A,H26B,H26C} of C26,
   {H27A,H27B,H27C} of C27, {H1A,H1B,H1C} of C1, {H5A,H5B,H5C} of C5, {H31A,
  H31B,H31C} of C31, {H35A,H35B,H35C} of C35, {H32A,H32B,H32C} of C32, {H28A,
  H28B,H28C} of C28, {H30A,H30B,H30C} of C30, {H34A,H34B,H34C} of C34
3. Restrained distances
 H1C-H1
 2 with sigma of 0.002
 H1-H4A
 2 with sigma of 0.002
 H6-H31A
 2 with sigma of 0.002
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54: within 2.5A with sigma of
0.004 and sigma for terminal atoms of 0.008
5.a Ternary CH refined with riding coordinates:
 C21(H21), C23(H23), C25(H25), C48(H48), C50(H50), C52(H52)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C39(H39),
 C40(H40), C42(H42), C43(H43), C44(H44), C45(H45)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,
 H6B,H6C), C8(H8A,H8B,H8C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C),
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O6(H6)
;
_shelx_res_checksum              4557
_shelx_hkl_checksum              86502
_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 2.233
_oxdiff_exptl_absorpt_empirical_full_min 0.599