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_7125138
_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_absolute_configuration ad
_chemical_formula_moiety         'C26 H18 O5'
_chemical_formula_sum            'C26 H18 O5'
_chemical_formula_weight         410.40
_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             2016-07-05
_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                 94.703(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9030(6)
_cell_length_b                   6.3446(4)
_cell_length_c                   16.4435(9)
_cell_measurement_reflns_used    2520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.2350
_cell_measurement_theta_min      4.4750
_cell_volume                     1029.68(11)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
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;
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omega____ theta____ kappa____ phi______ frames
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  2 omega  -62.00  -36.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  3 omega -105.00  -32.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -62.00    2.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -19.0000 -120.0000 64

  5 omega  -65.00  -39.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  6 omega   19.00   46.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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  7 omega   41.00   69.00   1.0000    2.5000
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  8 omega   66.00   96.00   1.0000    2.5000
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  9 omega   25.00   52.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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 10 omega   38.00  104.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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 11 omega    0.00   33.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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 12 omega   58.00  108.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 50

 13 omega   37.00   63.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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 14 omega  -32.00   25.00   1.0000    2.5000
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 15 omega   61.00  108.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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 16 omega    1.00   79.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
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 17 omega   22.00   73.00   1.0000    2.5000
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 18 omega   90.00  147.00   1.0000   13.5000
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 19 omega   57.00   91.00   1.0000   13.5000
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 20 omega  110.00  175.00   1.0000   13.5000
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 21 omega   84.00  110.00   1.0000   13.5000
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 22 omega  123.00  173.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 50

 23 omega   79.00  105.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

 24 omega   79.00  106.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 27

 25 omega   62.00  136.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 74

 26 omega   82.00  112.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 30

 27 omega   88.00  130.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 42

 28 omega  141.00  172.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 31

 29 omega   79.00  105.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 30 omega   63.00  125.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 62

 31 omega   89.00  122.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 33

 32 omega  121.00  175.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 54

 33 omega   90.00  117.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 27

 34 omega   79.00  105.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26

 35 omega   39.00   79.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 40

 36 omega   88.00  114.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 26

 37 omega   88.00  119.00   1.0000   13.5000
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    -      108.0000   61.0000   90.0000 31

 38 omega   88.00  114.00   1.0000   13.5000
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 39 omega   79.00  105.00   1.0000   13.5000
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 40 omega   64.00   97.00   1.0000   13.5000
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 41 omega   84.00  109.00   1.0000   13.5000
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 42 omega   39.00   90.00   1.0000   13.5000
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 43 omega   84.00  114.00   1.0000   13.5000
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 44 omega   88.00  114.00   1.0000   13.5000
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 45 omega  132.00  163.00   1.0000   13.5000
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 46 omega   80.00  106.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000   50.4830 26
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0336330000
_diffrn_orient_matrix_UB_12      0.0477037000
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_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_unetI/netI     0.0427
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_diffrn_reflns_number            7938
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_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            yellow
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_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 990 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0814P)^2^+0.0675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1377
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_reflns_Friedel_fraction_max     0.796
_reflns_number_gt                2876
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07105h2.cif
_cod_data_source_block           20160799
_cod_original_cell_volume        1029.67(10)
_cod_database_code               7125138
_chemical_oxdiff_formula         C1H1O1N1
_reflns_odcompleteness_completeness 99.90
_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
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              56146
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'