Catalytic Asymmetric [2+2] Cycloaddition between Quinones and Fulvenes and a Subsequent Stereoselective Isomerization to 2,3-Dihydrobenzofurans
Zheng, Haifeng; Xu, Chaoran; Wang, Yan; Kang, Tengfei; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Chem. Commun.  (2017) –; doi:10.1039/C7CC03211K

data_7120196
_publ_section_title
;
 Catalytic Asymmetric [2+2] Cycloaddition between Quinones and Fulvenes
 and a Subsequent Stereoselective Isomerization to 2,3-Dihydrobenzofurans
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03211K
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H18 O6'
_chemical_formula_sum            'C22 H18 O6'
_chemical_formula_weight         378.36
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-04-28 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.936(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.67071(16)
_cell_length_b                   13.2339(2)
_cell_length_c                   9.6030(2)
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    125
_cell_measurement_theta_max      72.3830
_cell_measurement_theta_min      4.9860
_cell_volume                     897.76(4)
_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      125
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -180.0000 94

  2 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000  -60.0000 101

  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

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

  5 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

  6 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 94

  7 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 84

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

  9 omega   57.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 93

 10 omega   57.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -90.0000 93

 11 omega   88.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  136.0000   44.0000 88

 12 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 13 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 14 omega   87.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 91

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

 16 omega   38.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 17 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

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

 19 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

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

 21 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 22 omega   41.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 85

 23 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000 -150.0000 88

 24 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

 25 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 94

 26 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   90.0000 88

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

 28 omega  -33.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000    0.0000 75
;
_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      0.0409383000
_diffrn_orient_matrix_UB_12      -0.1137128000
_diffrn_orient_matrix_UB_13      0.0288829000
_diffrn_orient_matrix_UB_21      -0.1933250000
_diffrn_orient_matrix_UB_22      -0.0248409000
_diffrn_orient_matrix_UB_23      -0.1260898000
_diffrn_orient_matrix_UB_31      0.0921264000
_diffrn_orient_matrix_UB_32      -0.0014679000
_diffrn_orient_matrix_UB_33      -0.1167359000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8864
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         5.001
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64115
_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    1.400
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0887P)^2^+0.0553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3173
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03211k2.cif
_cod_data_source_block           fxm-zhf-iso-125k
_cod_original_cell_volume        897.77(4)
_cod_database_code               7120196
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C00J(H00J), C00N(H00N)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00K(H00K), C00M(H00M), C00O(H00O),
 C00Q(H00Q), C00R(H00R), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00C), C00P(H00D,H00H,H00I)
2.d Idealised tetrahedral OH refined as rotating group:
 O005(H005)
;
_shelx_res_checksum              70833
_shelx_hkl_checksum              2973
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-28
_olex2_submission_special_instructions 'No special instructions were received'