Regio- and stereoselective C(sp2)–H acylation of enamides with aldehydes via transition-metal-free photoredox catalysis
Zhao, Kai; Zhang, Xiao-Chen; Tao, Ji-Yu; Wu, Xian-Dan; Wu, Jia-Xu; Li, Wei-Ming; Zhu, Tong-Hao; Loh, Teck-Peng; Green Chemistry 22 (2020) 5497–5503; doi:10.1039/D0GC01947J

data_7240920
_publ_section_title
;
 Regio- and stereoselective C(sp2)--H acylation of enamides with aldehydes
 via transition-metal-free photoredox catalysis
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              5497
_journal_page_last               5503
_journal_paper_doi               10.1039/D0GC01947J
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C21 H15 N O'
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-06 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.090(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5135(6)
_cell_length_b                   11.7884(4)
_cell_length_c                   18.8103(7)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.102
_cell_measurement_theta_min      3.909
_cell_volume                     3059.2(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29402
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.078
_diffrn_reflns_theta_min         3.908
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1909 before and 0.1078 after correction. The Ratio of minimum to maximum transmission is 0.6486. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0731
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1371P)^2^+0.6294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4281
_reflns_number_total             5830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc01947j2.cif
_cod_data_source_block           191029sf_0m
_cod_depositor_comments
;Adding full bibliography for 7240916--7240920.cif.

 Adding full bibliography for 7240916--7240920.cif.
;
_cod_database_code               7240920
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), N1A(H1A),
  C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C10A(H10A), C11A(H11A), C12A(H12A),
 C13A(H13A), C14A(H14A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A),
 C21A(H21A)
;
_shelx_res_checksum              13682
_olex2_submission_special_instructions 'No special instructions were received'