Modular reductive radical-polar crossover-based acyl migration reactions of <i>N</i>-vinylimides with alkyl, silyl, and acyl radicals.
Jing, Yutao; Zhang, Li; Qiu, Li; Fang, Yewen; RSC advances 15 (2025) 11582–11586; doi:10.1039/d5ra01542a

data_7250663
_publ_section_title
;
 Modular reductive radical-polar crossover-based acyl migration reactions
 of <i>N</i>-vinylimides with alkyl, silyl, and acyl radicals.
;
_journal_issue                   15
_journal_name_full               'RSC advances'
_journal_page_first              11582
_journal_page_last               11586
_journal_paper_doi               10.1039/d5ra01542a
_journal_volume                  15
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         '8(C15 H21 N O2)'
_chemical_formula_sum            'C120 H168 N8 O16'
_chemical_formula_weight         1978.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_Int_Tables_number      9
_audit_creation_date             2024-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-01-07 deposited with the CCDC.	2025-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.381(3)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   13.6440(14)
_cell_length_b                   13.7725(11)
_cell_length_c                   16.2084(16)
_cell_measurement_reflns_used    5080
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.28
_cell_volume                     2936.7(5)
_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  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9734
_diffrn_measured_fraction_theta_max 0.9734
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15769
_diffrn_reflns_theta_full        24.9995
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6176
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1463 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.8288.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.1188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1072.4969
_refine_diff_density_max         0.3423
_refine_diff_density_min         -0.3899
_refine_diff_density_rms         0.0516
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.4(12)
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             9.5129
_refine_ls_goodness_of_fit_ref   1.0461
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    66
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5046
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.0458
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1031P)^2^+1.2479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1848
_reflns_Friedel_coverage         0.948
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                3721
_reflns_number_total             5046
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ra01542a2.cif
_cod_data_source_block           11_a
_cod_original_sg_symbol_Hall     ' C -2yc'
_cod_database_code               7250663
_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. Restrained distances
 H00V-H005
 2.45 with sigma of 0.01
3. Rigid bond restraints
 C1, C00R
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
4.a Ternary CH refined with riding coordinates:
 C00L(H00L), C00R(H2aa)
4.b Secondary CH2 refined with riding coordinates:
 C00E(H00a,H00b), C00J(H00z,H)
4.c Aromatic/amide H refined with riding coordinates:
 C00G(H00s), C00Q(H1aa), C00T(H3aa), C00N(H0aa), C00F(H00r), C00V(H00V),
 C00Y(H00Y), C00U(H00U), C00P(H00P), C00O(H00O), N004(H004), N005(H005)
4.d Idealised Me refined as rotating group:
 C00I(H00t,H00w,H00x), C00K(H00c,H00d,H00e), C00M(H00,Ha,Hb), C00S(H00f,H00g,
 H00h), C00W(H4aa,Hc,Hd), C00X(H00i,H00j,H00k), C00Z(H00m,H00n,H00q), C1(H1a,
 H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'