Palladium-catalyzed distal γ- and ε-benzylation, allylation and allenylation of enones.
Sah, Pooja; Kapur, Manmohan; Chemical communications (Cambridge, England) 61 (2025) 1874–1877; doi:10.1039/d4cc05607h

data_7134105
_publ_section_title
;
 Palladium-catalyzed distal &#x3b3;- and &#x3b5;-benzylation, allylation
 and allenylation of enones.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1874
_journal_page_last               1877
_journal_paper_doi               10.1039/d4cc05607h
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-26 deposited with the CCDC.	2024-12-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.579(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.151(3)
_cell_length_b                   14.019(7)
_cell_length_c                   7.211(3)
_cell_measurement_reflns_used    1420
_cell_measurement_temperature    99.00
_cell_measurement_theta_max      30.244
_cell_measurement_theta_min      2.906
_cell_volume                     618.9(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      99.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_av_unetI/netI     0.1445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10262
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.244
_diffrn_reflns_theta_min         2.906
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1433 before and 0.1010 after correction.
The Ratio of minimum to maximum transmission is 0.6137.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.189
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     274
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0684
_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^)+0.1485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_full    0.751
_reflns_Friedel_fraction_max     0.621
_reflns_number_gt                1775
_reflns_number_total             2984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05607h2.cif
_cod_data_source_block           PO_04NO
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'DUAL' was changed to
'dual' 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 

 Adding full bibliography for 7134105--7134106.cif.
;
_cod_database_code               7134105
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C13-C14 \\sim C13A-C12A
 with sigma of 0.02
 C15-C10 \\sim C11A-C10
 with sigma of 0.02
 C15-C14 \\sim C11A-C12A
 with sigma of 0.02
 C11-C12 \\sim C15A-C14A
 with sigma of 0.02
 C10-C11 \\sim C10-C15A
 with sigma of 0.02
 C15-C13 \\sim C11A-C13A
 with sigma of 0.04
 C13-C12 \\sim C13A-C14A
 with sigma of 0.02
 C11-C13 \\sim C15A-C13A
 with sigma of 0.04
 C10-C14 \\sim C10-C12A
 with sigma of 0.04
 C10-C12 \\sim C10-C14A
 with sigma of 0.04
 C14-C12 \\sim C12A-C14A
 with sigma of 0.04
 C14-O3 \\sim C12A-O1A
 with sigma of 0.04
 C12-O3 \\sim C14A-O1A
 with sigma of 0.04
 C13-O3 \\sim C13A-O1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 2A
4. Others
 Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(C15A)=Sof(H15C)=Sof(C13A)=
 Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C14A)=Sof(H14C)=Sof(O1A)=1-FVAR(1)
 Sof(C15)=Sof(H15B)=Sof(H15A)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C13)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(C12)=Sof(H12)=Sof(O3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10A), C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15B,H15A), C14(H14A,H14B), C11A(H11A,H11B), C12A(H12A,H12B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C2(H2), C11(H11), C12(H12), C15A(H15C), C14A(H14C)
;
_shelx_res_checksum              57550
_shelx_hkl_checksum              86253
_olex2_submission_original_sample_id PO_04NO
_olex2_submission_special_instructions 'No special instructions were received'