A Switch to Vinylogous Reactivity of Vinyl Diazo Esters for the C-H Allylation of Benzamides by Merging Cobalt and Photoredox Catalysis
Khot, Nandkishor Prakash; Deo, Nitish Kumar; Kapur, Manmohan; Chemical Communications  (2022) –; doi:10.1039/D2CC05332B

data_7131028
_publ_section_title
;
 A Switch to Vinylogous Reactivity of Vinyl Diazo Esters for the C-H
 Allylation of Benzamides by Merging Cobalt and Photoredox Catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05332B
_journal_year                    2022
_chemical_formula_moiety         'C26 H28 N2 O3'
_chemical_formula_sum            'C26 H28 N2 O3'
_chemical_formula_weight         416.52
_chemical_name_systematic        Allylated
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-22 deposited with the CCDC.	2022-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                104.537(6)
_cell_angle_beta                 91.863(6)
_cell_angle_gamma                98.368(5)
_cell_formula_units_Z            2
_cell_length_a                   5.3986(8)
_cell_length_b                   11.9982(17)
_cell_length_c                   18.382(3)
_cell_measurement_reflns_used    5278
_cell_measurement_temperature    290
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.30
_cell_volume                     1137.3(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      290.0
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33092
_diffrn_reflns_theta_full        28.6988
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2162
_exptl_crystal_description       block
_exptl_crystal_F_000             444.2065
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.2939
_refine_diff_density_min         -0.2700
_refine_diff_density_rms         0.0498
_refine_ls_d_res_high            0.7400
_refine_ls_d_res_low             8.6638
_refine_ls_goodness_of_fit_ref   1.0290
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0290
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.2075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              15
_reflns_limit_k_min              -16
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                3636
_reflns_number_total             5871
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2cc05332b3.cif
_cod_data_source_block           TR1_a
_cod_database_code               7131028
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00C(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 N004(H004), C006(H006), C009(H009), C00I(H00I), C00K(H00K), C00M(H00M),
 C00O(H00O), C00Q(H00Q), C00R(H00R), C00T(H00u), C00U(H00v)
2.c Idealised Me refined as rotating group:
 C00L(H00c,H00d,H00e), C00N(H00f,H00g,H00h), C00P(H00j,H00l,H00n), C00S(H00p,
 H00s,H00t), C00V(H00w,H00x,H00y)
;
_olex2_submission_special_instructions 'No special instructions were received'