Organocatalytic asymmetric formal arylation of benzofuran-2(3H)-ones with cooperative visible light photocatalysis.
Liu, Yang; Li, Jiangtao; Ye, Xinyi; Zhao, Xiaowei; Jiang, Zhiyong; Chemical communications (Cambridge, England) 52 (2016) 13955–13958; doi:10.1039/c6cc07105h

data_7125139
_publ_section_title
;
 Organocatalytic asymmetric formal arylation of benzofuran-2(3H)-ones with
 cooperative visible light photocatalysis.
;
_journal_issue                   97
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13955
_journal_page_last               13958
_journal_paper_doi               10.1039/c6cc07105h
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C31 H20 O4'
_chemical_formula_sum            'C31 H20 O4'
_chemical_formula_weight         456.47
_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             2016-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-21 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.366(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1942(8)
_cell_length_b                   6.6554(5)
_cell_length_c                   16.7572(13)
_cell_measurement_reflns_used    2881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7220
_cell_measurement_theta_min      4.1320
_cell_volume                     1184.85(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -48.00  36.00   1.00    1.00    --  -33.50  25.00 -64.00   84
  2  \w   -107.00 -74.00   1.00    1.00    --  -33.50 178.00 120.00   33
  3  \w    -48.00  21.00   1.00    1.00    --  -33.50  37.00  30.00   69
  4  \w     18.00  46.00   1.00    1.00    --   36.55  57.00  60.00   28
  5  \w      0.00  57.00   1.00    1.00    --   36.55 -99.00  60.00   57
  6  \w     25.00  51.00   1.00    1.00    --   36.55  37.00   0.00   26
  7  \w     73.00  99.00   1.00    1.00    --   36.55  37.00   0.00   26
  8  \w    -23.00  40.00   1.00    1.00    --   36.55 -57.00-180.00   63
  9  \w     37.00  63.00   1.00    1.00    --   36.55  57.00 120.00   26
 10  \w     43.00  69.00   1.00    1.00    --   36.55  19.00 150.00   26
 11  \w     33.00  70.00   1.00    1.00    --   36.55  57.00  90.00   37
 12  \w     63.00 102.00   1.00    1.00    --   36.55  37.00  30.00   39
 13  \w     72.00  98.00   1.00    1.00    --   36.55  57.00  60.00   26
 14  \w     18.00  66.00   1.00    1.00    --   36.55  57.00 -30.00   48
 15  \w     18.00  44.00   1.00    1.00    --   36.55  77.00  60.00   26
 16  \w      9.00 103.00   1.00    1.00    --   36.55  77.00 120.00   94
 17  \w     -3.00  34.00   1.00    1.00    --   36.55 -99.00 -30.00   37
 18  \w    114.00 175.00   1.00    5.00    --  108.00  77.00 -30.00   61
 19  \w     79.00 105.00   1.00    5.00    --  108.00  77.00 -30.00   26
 20  \w     79.00 105.00   1.00    5.00    --  108.00  77.00  30.00   26
 21  \w     38.00  81.00   1.00    5.00    --  108.00 -94.00-120.00   43
 22  \w     82.00 114.00   1.00    5.00    --  108.00  30.00  60.00   32
 23  \w     84.00 110.00   1.00    5.00    --  108.00  30.00  30.00   26
 24  \w    135.00 164.00   1.00    5.00    --  108.00  61.00   0.00   29
 25  \w     77.00 103.00   1.00    5.00    --  108.00 -94.00 -60.00   26
 26  \w     90.00 116.00   1.00    5.00    --  108.00  61.00 -30.00   26
 27  \w     79.00 105.00   1.00    5.00    --  108.00  77.00   0.00   26
 28  \w     83.00 109.00   1.00    5.00    --  108.00  30.00  90.00   26
 29  \w     82.00 155.00   1.00    5.00    --  108.00  30.00 120.00   73
 30  \w     89.00 114.00   1.00    5.00    --  108.00  61.00  60.00   25
 31  \w    122.00 166.00   1.00    5.00    --  108.00  77.00  60.00   44
 32  \w     81.00 107.00   1.00    5.00    --  108.00  77.00 -60.00   26
 33  \w     89.00 161.00   1.00    5.00    --  108.00  61.00 -60.00   72
 34  \w     79.00 105.00   1.00    5.00    --  108.00  77.00  60.00   26
 35  \w     82.00 114.00   1.00    5.00    --  108.00  30.00   0.00   32
 36  \w     80.00 107.00   1.00    5.00    --  108.00  77.00  90.00   27
 37  \w    101.00 172.00   1.00    5.00    --  108.00 111.00 120.00   71
 38  \w     89.00 124.00   1.00    5.00    --  108.00  61.00  30.00   35
 39  \w     88.00 176.00   1.00    5.00    --  108.00  61.00  90.00   88
 40  \w    113.00 176.00   1.00    5.00    --  108.00  77.00  30.00   63
 41  \w     91.00 117.00   1.00    5.00    --  108.00  45.00   0.00   26
 42  \w     39.00  98.00   1.00    5.00    --  108.00 -45.00  30.00   59
 43  \w     89.00 129.00   1.00    5.00    --  108.00  61.00   0.00   40
 44  \w     48.00 115.00   1.00    5.00    --  108.00-111.00-150.00   67
 45  \w    -66.00 -40.00   1.00    1.00    --  -33.50 -77.00  60.00   26
 46  \w     17.00  43.00   1.00    1.00    --   36.47  77.00   0.00   26
 47  \w     82.00 107.00   1.00    1.00    --   36.47  37.00 120.00   25
 48  \w     88.00 114.00   1.00    5.00    --  108.00  61.00  30.00   26
 49  \w     88.00 113.00   1.00    5.00    --  108.00  45.00  30.00   25
 50  \w     88.00 113.00   1.00    5.00    --  108.00  45.00 -30.00   25
 51  \w     80.00 105.00   1.00    1.00    --   36.47  57.00-120.00   25
 52  \w     84.00 109.00   1.00    5.00    --  108.00 -94.00 -30.00   25
 53  \w     37.00  62.00   1.00    5.00    --  108.00 -30.00 120.00   25
 54  \w     37.00  62.00   1.00    5.00    --  108.00 -30.00-180.00   25
 55  \w     63.00  89.00   1.00    5.00    --  108.00 -45.00 -60.00   26
 56  \w     53.00  79.00   1.00    5.00    --  108.00 -30.00  60.00   26
 57  \w    112.00 137.00   1.00    5.00    --  108.00 -77.00 -60.00   25
 58  \w     57.00  82.00   1.00    1.00    --   36.47 178.00-180.00   25
 59  \w      9.00  35.00   1.00    1.00    --   36.47  77.00  90.00   26
 60  \w     18.00  44.00   1.00    1.00    --   36.47  77.00   0.00   26
 61  \w     74.00 100.00   1.00    1.00    --   36.47 178.00-120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1259917000
_diffrn_orient_matrix_UB_12      -0.0700729000
_diffrn_orient_matrix_UB_13      -0.0626438000
_diffrn_orient_matrix_UB_21      0.0666907000
_diffrn_orient_matrix_UB_22      -0.0464386000
_diffrn_orient_matrix_UB_23      -0.0654945000
_diffrn_orient_matrix_UB_31      0.0266018000
_diffrn_orient_matrix_UB_32      -0.2157185000
_diffrn_orient_matrix_UB_33      0.0344775000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10438
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.765
_diffrn_reflns_theta_min         4.161
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       needle
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(19)
_refine_ls_extinction_coef       0.0014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0400P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0996
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                3321
_reflns_number_total             4140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07105h2.cif
_cod_data_source_block           ly8020x
_cod_database_code               7125139
_chemical_oxdiff_formula         C1H11O3
_reflns_odcompleteness_completeness 99.83
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
;
_shelx_res_checksum              35548
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.828
_oxdiff_exptl_absorpt_empirical_full_min 0.496