Acyl-oxyallenes as α, β-Unsaturated Ketone Surrogates for Giese Radical Addition
Jin, Jiarong; Li, Xin; Luo, Yicheng; Chen, Jian-Fu; Tang, Wenjun; Du, Kang; Chemical Science  (2025) –; doi:10.1039/D5SC08002A

data_1576287
_publ_section_title
;
 Acyl-oxyallenes as \a, \b-Unsaturated Ketone Surrogates for Giese Radical
 Addition
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC08002A
_journal_year                    2025
_chemical_formula_moiety         'C34 H34 N O'
_chemical_formula_sum            'C34 H34 N O'
_chemical_formula_weight         472.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2lstlt
_audit_creation_date             2024-10-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-03 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                72.825(2)
_cell_angle_beta                 80.564(2)
_cell_angle_gamma                69.791(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2433(5)
_cell_length_b                   11.6116(7)
_cell_length_c                   13.7296(8)
_cell_measurement_reflns_used    2934
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      24.54
_cell_measurement_theta_min      2.53
_cell_volume                     1318.05(13)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-4 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12578
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         1.934
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0662 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.8855.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5985
_refine_ls_number_restraints     181
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0622P)^2^+0.4220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1777
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3317
_reflns_number_total             5985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08002a2.cif
_cod_data_source_block           241025lu_lgpz214150_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               1576287
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C15A-C14 \\sim C15-C14
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C15 \\sim C15A \\sim C16 \\sim C16A \\sim C17 \\sim C17A \\sim C18 \\sim C18A
\\sim C19 \\sim C19A \\sim C20 \\sim C20A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=
 Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=1-FVAR(1)
 Sof(H14)=Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=
 Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C14(H14), C14(H14A), C21(H21), C22(H22)
5.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C16(H16), C16A(H16A), C17(H17), C17A(H17A), C18(H18),
 C18A(H18A), C19(H19), C19A(H19A), C20(H20), C20A(H20A), C30(H30), C31(H31),
 C32(H32), C33(H33), C34(H34)
;
_shelx_res_checksum              39855
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU