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_4035135
_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         'C34 H32 O6'
_chemical_formula_sum            'C34 H32 O6'
_chemical_formula_weight         536.58
_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     dual
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.986(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7835(3)
_cell_length_b                   24.3459(5)
_cell_length_c                   11.8380(3)
_cell_measurement_reflns_used    6617
_cell_measurement_temperature    294.7(5)
_cell_measurement_theta_max      72.4230
_cell_measurement_theta_min      4.1480
_cell_volume                     2793.67(15)
_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      294.7(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

  2 omega  -35.00   66.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000   90.0000 101

  3 omega  -33.00   55.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000 -120.0000 88

  4 omega    1.00   75.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

  5 omega   20.00  104.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -30.0000 84

  6 omega   23.00   90.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  120.0000 67

  7 omega   40.00  135.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 95

  8 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

  9 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 10 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 11 omega   40.00   98.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 12 omega  100.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 78

 13 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 14 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 15 omega   81.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 16 omega   38.00  116.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 78

 17 omega   10.00   80.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 70
;
_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      -0.0491555000
_diffrn_orient_matrix_UB_12      -0.0563790000
_diffrn_orient_matrix_UB_13      -0.0627388000
_diffrn_orient_matrix_UB_21      -0.1510296000
_diffrn_orient_matrix_UB_22      0.0177639000
_diffrn_orient_matrix_UB_23      -0.0429520000
_diffrn_orient_matrix_UB_31      -0.0040758000
_diffrn_orient_matrix_UB_32      0.0225663000
_diffrn_orient_matrix_UB_33      -0.1232408000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16172
_diffrn_reflns_point_group_measured_fraction_full 0.858
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.510
_diffrn_reflns_theta_min         4.562
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84741
_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    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.313
_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   0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     742
_refine_ls_number_reflns         9135
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0679
_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^)+(0.1400P)^2^+0.2960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1837
_refine_ls_wR_factor_ref         0.1933
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    0.709
_reflns_Friedel_fraction_max     0.659
_reflns_number_gt                8281
_reflns_number_total             9135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01425_si_002.cif
_cod_data_source_block           fxm-zjl-44-asl
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C68 H63.97 O12'
_cod_original_formula_weight         1073.16
_cod_original_formula_moiety         '2(C34 H32 O6)'
_cod_original_formula_units_Z            2
_cod_database_code               4035135
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.92
_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. Others
 Sof(H01D)=Sof(O00L)=Sof(H00L)=1-FVAR(1)
 Sof(O00K)=Sof(H00K)=Sof(H01A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00H(H00H), C00U(H00U), C00W(H00W), C018(H018), C01F(H01F)
3.b Secondary CH2 refined with riding coordinates:
 C01T(H01g,H01h), C01Y(H01j,H01k)
3.c Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011), C012(H012),
 C013(H013), C015(H015), C016(H016), C017(H017), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E), C01I(H01I), C01L(H01L),
 C01M(H01M), C01N(H01N), C01O(H01O), C01P(H01P), C01Q(H01Q), C01R(H01R),
 C01S(H01S), C01U(H01U), C01W(H01W), C01Z(H01Z), C021(H021)
3.d Idealised Me refined as rotating group:
 C020(H02m,H02n,H02o), C022(H02a,H02b,H02c), C023(H02d,H02e,H02f), C024(H02p,
 H02q,H02r), C025(H02g,H02h,H02i), C026(H02s,H02t,H02u), C027(H02v,H02w,H02x),
 C028(H02j,H02k,H02l)
3.e Idealised tetrahedral OH refined as rotating group:
 O00G(H00G), O00K(H00K), O00L(H00L)
;
_olex2_date_sample_data_collection 2017-04-10
_olex2_submission_special_instructions 'No special instructions were received'