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_7161088
_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         'C34 H56 O8 P2'
_chemical_formula_sum            'C34 H56 O8 P2'
_chemical_formula_weight         654.72
_chemical_name_systematic        CYZ-391
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-01-18
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   25.8020(11)
_cell_length_b                   25.802
_cell_length_c                   31.0745(17)
_cell_measurement_reflns_used    8913
_cell_measurement_temperature    219
_cell_measurement_theta_max      27.700
_cell_measurement_theta_min      2.245
_cell_volume                     17916.0(12)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      219.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0933
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            41876
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.937
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.0479
_exptl_absorpt_correction_T_min  0.0177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_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    1.092
_exptl_crystal_description       block
_exptl_crystal_F_000             6372
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         7021
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+27.0796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4949
_reflns_number_total             7021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00078a2.cif
_cod_data_source_block           m16028_0m_sq
_cod_depositor_comments
'Adding full bibliography for 7161083--7161088.cif.'
_cod_original_cell_volume        17916.0(18)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7161088
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.985
_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, All O(H) groups
2. Restrained distances
 C015-H01P
 0.96 with sigma of 0.02
 C015-H01Q
 0.96 with sigma of 0.02
 C015-H01R
 0.96 with sigma of 0.02
 C010-H01B
 0.96 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00H(H00H)
3.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00N(H00N)
3.c Idealised Me refined as rotating group:
 C00S(H00B,H00G,H00I), C00T(H00J,H00K,H00L), C00V(H00M,H00O,H00P), C00X(H00T,
 H00U,H00V), C00Y(H00W,H00X,H00Y), C00Z(H00Z,H,HA), C011(H01D,H01E,H01F),
 C012(H01G,H01H,H01I), C014(H01M,H01N,H01O), C016(H01S,H01T,H01U), C017(H01V,
 H01W,H01X), C018(H01Y,HB,HC)
3.d Idealised tetrahedral OH refined as rotating group:
 O008(H008), O00A(H00A)
;
_shelx_res_checksum              6760
_shelx_fab_checksum              24282
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'