Enantioselective Formal [4 + 2] Annulation of ortho-Quinone Methides with ortho-Hydroxyphenyl α,β-Unsaturated Compounds.
Zhang, Jianlin; Liu, Xiaohua; Guo, Songsong; He, Changqiang; Xiao, Wanlong; Lin, Lili; Feng, Xiaoming; The Journal of organic chemistry 83 (2018) 10175–10185; doi:10.1021/acs.joc.8b01425

data_4035136
_publ_section_title
;
 Enantioselective Formal [4 + 2] Annulation of ortho-Quinone Methides with
 ortho-Hydroxyphenyl \a,\b-Unsaturated Compounds.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10175
_journal_page_last               10185
_journal_paper_doi               10.1021/acs.joc.8b01425
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H20 O6'
_chemical_formula_sum            'C24 H20 O6'
_chemical_formula_weight         404.40
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.434(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8962(4)
_cell_length_b                   16.0389(4)
_cell_length_c                   11.6123(3)
_cell_measurement_reflns_used    7185
_cell_measurement_temperature    295.77(11)
_cell_measurement_theta_max      72.5170
_cell_measurement_theta_min      4.2060
_cell_volume                     1965.34(10)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.77(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -90.0000 94

  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -120.0000 74

  3 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -30.0000 84

  5 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  120.0000 94

  6 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  120.0000 94

  7 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   30.0000 84

  8 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -120.0000 94

  9 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   30.0000 67

 10 omega   40.00   98.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 11 omega   90.00  175.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

 12 omega   87.00  178.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

 13 omega   39.00  109.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 14 omega   70.00  178.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 108

 15 omega   40.00   98.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 16 omega   38.00   91.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 17 omega   40.00  135.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 95

 18 omega   91.00  176.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

 19 omega   41.00  126.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 85

 20 omega   91.00  176.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 85

 21 omega   37.00  146.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 109

 22 omega   38.00   88.00   1.0000    1.7400
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0431858000
_diffrn_orient_matrix_UB_12      0.0581266000
_diffrn_orient_matrix_UB_13      0.1080924000
_diffrn_orient_matrix_UB_21      0.1103164000
_diffrn_orient_matrix_UB_22      -0.0597492000
_diffrn_orient_matrix_UB_23      0.0533096000
_diffrn_orient_matrix_UB_31      0.0854157000
_diffrn_orient_matrix_UB_32      0.0476041000
_diffrn_orient_matrix_UB_33      -0.0651622000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16733
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.453
_diffrn_reflns_theta_min         4.803
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43229
_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    1.367
_exptl_crystal_description       irregular
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7281
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0975P)^2^+0.1296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                6826
_reflns_number_total             7281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01425_si_003.cif
_cod_data_source_block           fxm-zjl-q
_cod_original_cell_volume        1965.35(10)
_cod_database_code               4035136
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.45
_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. Rigid bond restraints
 C01B, C01G
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C01B \\sim C01G: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
4.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00I(H00I), C00M(H00M), C00O(H00O), C00S(H00S),
 C00U(H00U), C01C(H01H)
4.b Secondary CH2 refined with riding coordinates:
 C01D(H01B,H01C), C01I(H01L,H01M)
4.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00R(H00R), C00T(H00T), C00X(H00X), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C015(H015), C016(H016), C018(H018), C01A(H01A),
 C01E(H01E), C01F(H01I), C01G(H01J), C01H(H01K), C01J(H01N), C01L(H01O),
 C01M(H01P), C01N(H01Q)
4.d Idealised Me refined as rotating group:
 C01K(H01D,H01F,H01G), C01O(H01R,H01S,H01T)
4.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O008(H008)
;
_olex2_submission_special_instructions 'No special instructions were received'