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_4032299
_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_formula_moiety         'C21 H22 O4'
_chemical_formula_sum            'C21 H22 O4'
_chemical_formula_weight         338.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.703(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4415(4)
_cell_length_b                   19.8456(10)
_cell_length_c                   12.5838(7)
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    294.06(10)
_cell_measurement_theta_max      24.3740
_cell_measurement_theta_min      3.5280
_cell_volume                     1779.98(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.06(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   35.00   78.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8197  178.0000 -120.0000 43

  2 omega   68.00   96.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8197 -178.0000  -30.0000 28

  3 omega  -52.00   19.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8197  -19.0000 -150.0000 71

  4 omega  -12.00   14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -30.0000 26

  5 omega    8.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  -60.0000 30

  6 omega  -37.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000    0.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0323306000
_diffrn_orient_matrix_UB_12      0.0321960000
_diffrn_orient_matrix_UB_13      -0.0216498000
_diffrn_orient_matrix_UB_21      0.0243862000
_diffrn_orient_matrix_UB_22      -0.0076071000
_diffrn_orient_matrix_UB_23      -0.0491878000
_diffrn_orient_matrix_UB_31      -0.0909319000
_diffrn_orient_matrix_UB_32      -0.0134803000
_diffrn_orient_matrix_UB_33      -0.0240082000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8124
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.7688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1796
_reflns_number_gt                2335
_reflns_number_total             3497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02566_si_002.cif
_cod_data_source_block           luoych_1204
_cod_database_code               4032299
_chemical_oxdiff_formula         'C104 H20 S8 O8'
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Fixed Sof: O3(0.7) O3'(0.3)
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C15(H15), C13(H13), C2(H2A), C14(H14)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C20(H20A,H20B,
 H20C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'