Diastereo- and enantioselective construction of an indole-based 2,3-dihydrobenzofuran scaffold via catalytic asymmetric [3+2] cyclizations of quinone monoimides with 3-vinylindoles.
Sun, Xiao-Xue; Zhang, Hong-Hao; Li, Guo-Hao; Meng, Li; Shi, Feng; Chemical communications (Cambridge, England) 52 (2016) 2968–2971; doi:10.1039/c5cc09145d

data_7118278
_publ_section_title
;
 Diastereo- and enantioselective construction of an indole-based
 2,3-dihydrobenzofuran scaffold via catalytic asymmetric [3+2]
 cyclizations of quinone monoimides with 3-vinylindoles.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2968
_journal_page_last               2971
_journal_paper_doi               10.1039/c5cc09145d
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H25 F N2 O3 S'
_chemical_formula_sum            'C30 H25 F N2 O3 S'
_chemical_formula_weight         512.58
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2015-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-10-17 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.446(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.552(3)
_cell_length_b                   17.133(8)
_cell_length_c                   13.413(6)
_cell_measurement_reflns_used    2749
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.305
_cell_measurement_theta_min      2.377
_cell_volume                     1273.6(11)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'bruker apexII'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7137
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.643
_diffrn_reflns_theta_min         1.930
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1021 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.8133.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 1248 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_coef       0.026(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5119
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0785
_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^)+(0.1471P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2371
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.843
_reflns_Friedel_fraction_max     0.760
_reflns_number_gt                3535
_reflns_number_total             5119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09145d2.cif
_cod_data_source_block           sf20150807_sxx_0m
_cod_depositor_comments          'Adding full bibliography for 7118278.cif.'
_cod_original_cell_volume        1273.7(11)
_cod_database_code               7118278
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C10(H10), C13(H13), C14(H14), C16(H16), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              33583
_olex2_submission_special_instructions 'No special instructions were received'