Three-component tandem benzyl-C(sp<sup>3</sup>)-H functionalization <i>via</i> thermally generated arynes with phenazine.
Zhang, Yajuan; Chai, Fuxiang; Hu, Qiong; Chang, Meng; Qiang, Ruihua; Hu, Yimin; Organic & biomolecular chemistry 24 (2026) 1231–1236; doi:10.1039/d5ob01818h

data_7161030
_publ_section_title
;
 Three-component tandem benzyl-C(sp<sup>3</sup>)-H functionalization
 <i>via</i> thermally generated arynes with phenazine.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1231
_journal_page_last               1236
_journal_paper_doi               10.1039/d5ob01818h
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         '2(C52 H48 N2 O4)'
_chemical_formula_sum            'C104 H96 N4 O8'
_chemical_formula_weight         1529.84
_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             2025-06-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-10-07 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                84.7720(10)
_cell_angle_beta                 88.0100(10)
_cell_angle_gamma                73.9620(10)
_cell_formula_units_Z            2
_cell_length_a                   12.4510(3)
_cell_length_b                   13.0800(3)
_cell_length_c                   27.5697(6)
_cell_measurement_reflns_used    9100
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      67.737
_cell_measurement_theta_min      3.220
_cell_volume                     4297.05(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            76448
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.314
_diffrn_reflns_theta_min         1.609
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5814
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0985 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.7720.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       block
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1077
_refine_ls_number_reflns         15733
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0956P)^2^+0.0846P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10922
_reflns_number_total             15733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01818h2.cif
_cod_data_source_block           cu_20250421x_0m_a
_cod_original_cell_volume        4297.06(17)
_cod_database_code               7161030
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.854
_olex2_refinement_description
;
1. Restrained distances
 H96B-H88
 2 with sigma of 0.001
 C24A-C23 \\sim C24-C23 \\sim C25-C23 \\sim C25A-C23
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
C23 \\sim C24 \\sim C25 \\sim C24A \\sim C25A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C72 \\sim C71 \\sim C73: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
3. Rigid body (RIGU) restrains
 C23, C25, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C23, C25A, C24A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 Sof(H23A)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C25A)=Sof(H25D)=
 Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(H23)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=
 Sof(H25C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C75(H75), C71(H71), C19(H19), C23(H23), C23(H23A)
5.b Secondary CH2 refined with riding coordinates:
 C66(H66A,H66B), C68(H68A,H68B), C14(H14A,H14B), C16(H16A,H16B), C96(H96A,
 H96B), C44(H44A,H44B)
5.c Me refined with riding coordinates:
 C104(H10A,H10B,H10C)
5.d Aromatic/amide H refined with riding coordinates:
 C63(H63), C11(H11), C98(H98), C78(H78), C33(H33), C82(H82), C91(H91),
 C81(H81), C27(H27), C102(H102), C53(H53), C85(H85), C31(H31), C34(H34),
 C36(H36), C80(H80), C88(H88), C1(H1), C79(H79), C46(H46), C54(H54), C94(H94),
 C57(H57), C42(H42), C100(H100), C5(H5), C50(H50), C35(H35), C30(H30), C28(H28),
  C48(H48), C92(H92), C29(H29), C86(H86), C87(H87), C3(H3), C39(H39), C2(H2),
 C93(H93), C4(H4), C55(H55), C41(H41), C40(H40), C56(H56)
5.e Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C51(H51A,H51B,H51C), C77(H77A,H77B,H77C), C73(H73A,H73B,
 H73C), C76(H76A,H76B,H76C), C103(H10D,H10E,H10F), C21(H21A,H21B,H21C),
 C20(H20A,H20B,H20C), C72(H72A,H72B,H72C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C24A(H24D,H24E,H24F), C25A(H25D,H25E,H25F)
;
_shelx_res_checksum              91358
_olex2_submission_special_instructions 'No special instructions were received'