One-pot synthesis of 2-hydroxymethylindoles via photoredox-catalyzed ketyl–ynamide coupling/1,3-allylic alcohol transposition
Wang, Ze-Shu; Chen, Yang-Bo; Wang, Kun; Xu, Zhou; Ye, Long-Wu; Green Chemistry 22 (2020) 4483–4488; doi:10.1039/D0GC01522A

data_7240671
_publ_section_title
;
 One-pot synthesis of 2-hydroxymethylindoles via photoredox-catalyzed
 ketyl--ynamide coupling/1,3-allylic alcohol transposition
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              4483
_journal_page_last               4488
_journal_paper_doi               10.1039/D0GC01522A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_sum            'C22 H19 N O3 S'
_chemical_formula_weight         377.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-04-22 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.1253(14)
_cell_angle_gamma                90
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_cell_length_b                   13.9511(2)
_cell_length_c                   14.2096(2)
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_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      4.4450
_cell_volume                     1781.14(4)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11842
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_min         4.483
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85052
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0315P)^2^+1.7059P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3015
_reflns_number_total             3171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc01522a2.cif
_cod_data_source_block           exp_936
_cod_depositor_comments
;Adding full bibliography for 7240671.cif.

 Adding full bibliography for 7240671.cif.
;
_cod_original_cell_volume        1781.13(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7240671
_shelx_estimated_absorpt_t_min   0.840
_shelx_estimated_absorpt_t_max   0.915
_shelxl_version_number           2013-2
_shelx_res_checksum              17768