Transition-metal-free regioselective and stereoselective C(sp2)–C(sp3) coupling of enamides with ethers or alkanes via photoredox-catalyzed cross-dehydrogenative coupling reactions
Tao, Ji-Yu; Wang, Ying-Xue; Zhang, Qing-Hong; Ni, Kun; Zhu, Tong-Hao; Zhao, Kai; Green Chemistry 24 (2022) 4004–4011; doi:10.1039/D2GC00472K

data_7244843
_publ_section_title
;
 Transition-metal-free regioselective and stereoselective C(sp2)--C(sp3)
 coupling of enamides with ethers or alkanes via photoredox-catalyzed
 cross-dehydrogenative coupling reactions
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              4004
_journal_page_last               4011
_journal_paper_doi               10.1039/D2GC00472K
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C19 H25 N O4'
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40
_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             2019-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-11 deposited with the CCDC.	2022-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.488(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4311(8)
_cell_length_b                   10.9478(4)
_cell_length_c                   17.3130(7)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.922
_cell_measurement_theta_min      3.51
_cell_volume                     3650.6(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      169.97
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0482
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39169
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.003
_diffrn_reflns_theta_min         4.041
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1085 before and 0.0643 after correction. The Ratio of minimum to maximum transmission is 0.7658. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+1.0687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5607
_reflns_number_total             6921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00472k2.cif
_cod_data_source_block           20190111sf
_cod_depositor_comments          'Adding full bibliography for 7244843.cif.'
_cod_database_code               7244843
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H7AA(0.5) H7AB(0.5) H7BC(0.5) H7BD(0.5) H10A(0.5) H10B(0.5)
 H10C(0.5) H10D(0.5) C9(0.5) H9A(0.5) H9B(0.5) C8(0.5) H8A(0.5) H8B(0.5)
 H7AC(0.5) H7AD(0.5) H7AE(0.5) H7AF(0.5) H10E(0.5) H10F(0.5) H10G(0.5)
 H10H(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) C9A(0.5) H9AA(0.5) H9AB(0.5)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C6A(H6A)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C7(H7BC,H7BD), C10(H10A,H10B), C10(H10C,H10D), C9(H9A,H9B),
 C8(H8A,H8B), C7A(H7AC,H7AD), C7A(H7AE,H7AF), C10A(H10E,H10F), C10A(H10G,H10H),
 C8A(H8AA,H8AB), C9A(H9AA,H9AB)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C5A(H5A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A)
3.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C3A(H3AA,H3AB,H3AC), C18A(H18D,H18E,H18F), C19A(H19D,H19E,H19F),
 C20A(H20D,H20E,H20F)
;
_shelx_res_checksum              3394
_olex2_submission_special_instructions 'No special instructions were received'