Sc(OTf)3 Catalyzed [4 + 2]-Annulation Reaction between Electron-Rich Phenols and Donor-Acceptor Cyclopropanes: Synthesis of Polysubstituted Dihydronaphthols.
Luo, Yong-Chun; Ma, He; Hu, Xiu-Qin; Xu, Peng-Fei; The Journal of organic chemistry 82 (2017) 1013–1023; doi:10.1021/acs.joc.6b02566

data_4032125
_publ_section_title
;
 Sc(OTf)3 Catalyzed [4 + 2]-Annulation Reaction between Electron-Rich
 Phenols and Donor-Acceptor Cyclopropanes: Synthesis of Polysubstituted
 Dihydronaphthols.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1013
_journal_page_last               1023
_journal_paper_doi               10.1021/acs.joc.6b02566
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H22 O5'
_chemical_formula_sum            'C21 H22 O5'
_chemical_formula_weight         354.39
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
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Olex2 1.2
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_cell_length_b                   15.8764(19)
_cell_length_c                   9.4266(11)
_cell_measurement_reflns_used    938
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_cell_measurement_theta_max      66.9860
_cell_measurement_theta_min      7.7030
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
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_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega   -5.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 42

  2 omega   38.00  105.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 67

  3 omega  107.00  175.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 68

  4 omega  118.00  150.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 32

  5 omega  135.00  175.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 40

  6 omega  111.00  173.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  120.0000 62

  7 omega   47.00  120.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 73

  8 omega   47.00   92.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 45

  9 omega   36.00   92.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 56

 10 omega   30.00  125.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -120.0000 95

 11 omega   22.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 47

 12 omega   -5.00   79.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   60.0000 84

 13 omega   39.00   92.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 53

 14 omega   37.00   89.00   1.0000    1.5500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.1236358000
_diffrn_orient_matrix_UB_12      0.0773213000
_diffrn_orient_matrix_UB_13      0.0756534000
_diffrn_orient_matrix_UB_21      0.1968335000
_diffrn_orient_matrix_UB_22      -0.0222640000
_diffrn_orient_matrix_UB_23      -0.0644303000
_diffrn_orient_matrix_UB_31      -0.0954968000
_diffrn_orient_matrix_UB_32      0.0541776000
_diffrn_orient_matrix_UB_33      -0.1350679000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3262
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_diffrn_reflns_theta_max         70.22
_diffrn_reflns_theta_min         5.57
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.745
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_exptl_absorpt_correction_T_min  0.89693
_exptl_absorpt_correction_type   multi-scan
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.28
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
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_refine_ls_number_parameters     240
_refine_ls_number_reflns         2383
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_refine_ls_R_factor_all          0.0622
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.1226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                1960
_reflns_number_total             2383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02566_si_003.cif
_cod_data_source_block           luoych0717
_cod_depositor_comments          'Adding full bibliography for 4032125.cif.'
_cod_original_cell_volume        918.50(18)
_cod_database_code               4032125
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
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_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_date_sample_data_collection 2015-07-17
_olex2_submission_special_instructions 'No special instructions were received'