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_7120195
_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         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_weight         320.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-04-28 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.962(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8740(4)
_cell_length_b                   8.2225(2)
_cell_length_c                   11.5745(3)
_cell_measurement_reflns_used    4591
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      72.5400
_cell_measurement_theta_min      5.2630
_cell_volume                     1603.78(7)
_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      294.39(10)
_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 0.999
_diffrn_measurement_details
;
  1 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000  150.0000 101

  2 omega  -32.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -45.0000 -108.0000 86

  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -180.0000 84

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

  5 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  150.0000 88

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

  7 omega   19.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   45.0000   42.0000 86

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

  9 omega   39.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 10 omega   40.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 11 omega   91.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

 12 omega   81.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 13 omega   87.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 91

 14 omega   38.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 78

 15 omega   90.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 85

 16 omega  100.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 78

 17 omega   90.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

 18 omega   81.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 19 omega   81.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 20 omega   90.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

 21 omega   91.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 85

 22 omega   91.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 26

 23 omega   90.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 26

 24 omega   47.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 27

 25 omega   81.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 26

 26 omega   84.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 27 omega  100.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 29

 28 omega   88.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 61

 29 omega   90.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 26

 30 omega   43.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -108.0000 39

 31 omega   92.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 26

 32 omega   88.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 26

 33 omega   71.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 28

 34 omega  114.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 61
;
_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      0.0052628000
_diffrn_orient_matrix_UB_12      0.0936865000
_diffrn_orient_matrix_UB_13      -0.1145816000
_diffrn_orient_matrix_UB_21      0.0863404000
_diffrn_orient_matrix_UB_22      -0.0576365000
_diffrn_orient_matrix_UB_23      -0.0088783000
_diffrn_orient_matrix_UB_31      -0.0295882000
_diffrn_orient_matrix_UB_32      -0.1516655000
_diffrn_orient_matrix_UB_33      -0.0674929000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8300
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         5.250
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70586
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0508
_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^)+(0.1030P)^2^+0.0640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                2700
_reflns_number_total             2782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03211k2.cif
_cod_data_source_block           fxm-1118-2
_cod_original_cell_volume        1603.79(7)
_cod_database_code               7120195
_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
2.a Ternary CH refined with riding coordinates:
 C007(H007), C00B(H00B), C00I(H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00L(H00A,H00F,H00L)
;
_shelx_res_checksum              54463
_shelx_hkl_checksum              19047
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-19
_olex2_submission_special_instructions 'No special instructions were received'