Photocatalytic remote alkenylation of hydroxamides with enamides: synthesis of trisubstituted enamides <i>via</i> a radical pathway.
Wang, Yu-Ting; Zou, Xiao; Xu, Peng-Cheng; Chen, Dai-Xiang; Zhang, Yue; Yan, Sheng-Hu; Zuo, Hang-Dong; Organic & biomolecular chemistry 23 (2025) 7914–7918; doi:10.1039/d5ob01116g

data_7160677
_publ_section_title
;
 Photocatalytic remote alkenylation of hydroxamides with enamides:
 synthesis of trisubstituted enamides <i>via</i> a radical pathway.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7914
_journal_page_last               7918
_journal_paper_doi               10.1039/d5ob01116g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C27 H35 Cl N2 O2'
_chemical_formula_sum            'C27 H35 Cl N2 O2'
_chemical_formula_weight         455.02
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-25
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-26 deposited with the CCDC.	2025-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8380(2)
_cell_length_b                   20.1962(5)
_cell_length_c                   26.7858(7)
_cell_measurement_reflns_used    7293
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      56.36
_cell_measurement_theta_min      3.30
_cell_volume                     5322.1(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            49968
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.576
_diffrn_reflns_theta_min         3.300
_exptl_absorpt_coefficient_mu    1.450
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6007
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1528 before and 0.0735 after correction.
The Ratio of minimum to maximum transmission is 0.7976.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4814
_refine_ls_number_restraints     324
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1698
_refine_ls_R_factor_gt           0.1427
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3151
_refine_ls_wR_factor_ref         0.3431
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2636
_reflns_number_total             4814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01116g2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160677.cif.'
_cod_database_code               7160677
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.791
_shelx_estimated_absorpt_t_min   0.741
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23-Cl2
 1.751 with sigma of 0.02
 C3-Cl2
 2.618 with sigma of 0.02
 C24-Cl1
 2.571 with sigma of 0.02
 C22-C10 \\sim C27-C10
 with sigma of 0.02
3. Restrained planarity
 C3, C7, C13, C23, C25, C27, Cl2
 with sigma of 0.1
 C22, C24, C26, C28, C30, C32, Cl1
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C22)=Sof(C24)=Sof(H24)=Sof(C26)=Sof(C28)=Sof(H28)=Sof(C30)=Sof(H30)=
 Sof(C32)=Sof(H32)=Sof(Cl1)=1-FVAR(1)
 Sof(C23)=Sof(C3)=Sof(H3)=Sof(C25)=Sof(H25)=Sof(C13)=Sof(H13)=Sof(C27)=Sof(C7)=
 Sof(H7)=Sof(Cl2)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C20(H20A,H20B)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C11(H11), C15(H15), C24(H24), C28(H28), C30(H30),
 C32(H32), C3(H3), C25(H25), C13(H13), C7(H7), C31(H31)
7.c Fitted hexagon refined as free rotating group:
 C22(C24,C26,C28,C30,C32), C23(C3,C25,C13,C27,C7)
7.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C),
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
;
_olex2_submission_special_instructions 'No special instructions were received'