Pyridine-boryl radicals-mediated reductive homocoupling of para-quinone methides
Wang, Yan-Bo; Cui, Yan-Zhao; Li, He; Liu, Huiyi; Yuan, Hao-Qi; Zhou, Hao-Tian; Wang, Xiao-Sai; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00078A

data_7161085
_publ_section_title
;
 Pyridine-boryl radical-mediated reductive homocoupling of
 <i>para</i>-quinone methides.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3295
_journal_page_last               3300
_journal_paper_doi               10.1039/d6ob00078a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C44 H56 O2'
_chemical_formula_sum            'C44 H56 O2'
_chemical_formula_weight         616.88
_chemical_name_systematic        cyz-464
_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_creation_date             2025-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2026-01-13 deposited with the CCDC.	2026-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                70.076(3)
_cell_angle_beta                 89.930(3)
_cell_angle_gamma                75.343(3)
_cell_formula_units_Z            2
_cell_length_a                   11.5516(11)
_cell_length_b                   11.6796(12)
_cell_length_c                   15.6122(15)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    305
_cell_measurement_theta_max      25.081
_cell_measurement_theta_min      2.386
_cell_volume                     1907.5(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      305.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            54562
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.207
_diffrn_reflns_theta_max         25.207
_diffrn_reflns_theta_min         1.925
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.0912
_exptl_absorpt_correction_T_min  0.0528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1486 before and 0.0839 after correction.
The Ratio of minimum to maximum transmission is 0.5789.
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    1.074
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         6790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0517P)^2^+0.6459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4991
_reflns_number_total             6790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00078a2.cif
_cod_data_source_block           m17711_0m
_cod_depositor_comments
'Adding full bibliography for 7161083--7161088.cif.'
_cod_database_code               7161085
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C008(H008), C009(H009), C00G(H00G), C00I(H00I), C00P(H00P),
 C00R(H00R), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Z(H00Z),
 C012(H012), C014(H014)
2.b Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00C), C00Q(H00D,H00E,H00F), C00S(H00H,H00J,H00K), C00T(H00L,
 H00M,H00N), C00Y(H00O,H00Q,H00S), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F),
 C013(H01G,H01H,H01I), C015(H01J,H01K,H01L), C016(H01M,H01N,H01O), C017(H01P,
 H01Q,H01R), C018(H01S,H01T,H01U), C019(H01V,H01W,H01X), C01A(H01Y,H,HA)
;
_shelx_res_checksum              13850
_olex2_submission_special_instructions 'No special instructions were received'