Expeditious synthesis of multisubstituted indoles via multiple hydrogen transfers.
Yoshida, Taira; Mori, Keiji; Chemical communications (Cambridge, England) 54 (2018) 12686–12689; doi:10.1039/c8cc07009a

data_7122416
_publ_section_title
;
 Expeditious synthesis of multisubstituted indoles via multiple hydrogen
 transfers.
;
_journal_issue                   90
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12686
_journal_page_last               12689
_journal_paper_doi               10.1039/c8cc07009a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C15 H19 N O3'
_chemical_formula_weight         261.31
_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
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-08-08 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.872(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.093(2)
_cell_length_b                   7.5118(13)
_cell_length_c                   14.149(2)
_cell_measurement_reflns_used    1714
_cell_measurement_temperature    123
_cell_measurement_theta_max      24.43
_cell_measurement_theta_min      2.15
_cell_volume                     1390.8(4)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8016
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.396
_diffrn_reflns_theta_min         1.440
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1412 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5459
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0422P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_full    0.772
_reflns_Friedel_fraction_max     0.715
_reflns_number_gt                4264
_reflns_number_total             5459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07009a2.cif
_cod_data_source_block           shelxl_a
_cod_depositor_comments          'Adding full bibliography for 7122416.cif.'
_cod_original_cell_volume        1390.9(4)
_cod_database_code               7122416
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2014/6
_shelx_res_checksum              96872