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_7161029
_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         'C44 H38 N2 O5'
_chemical_formula_sum            'C44 H38 N2 O5'
_chemical_formula_weight         674.76
_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
_audit_creation_date             2025-04-09
_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                97.638(6)
_cell_angle_beta                 98.178(6)
_cell_angle_gamma                92.959(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6001(7)
_cell_length_b                   10.2098(10)
_cell_length_c                   21.2354(16)
_cell_measurement_reflns_used    2405
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      61.818
_cell_measurement_theta_min      4.250
_cell_volume                     1824.5(3)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 0.990
_diffrn_measured_fraction_theta_max 0.986
_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  0.1341
_diffrn_reflns_av_unetI/netI     0.2162
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21008
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.536
_diffrn_reflns_theta_min         4.250
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3889
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1260 before and 0.0820 after correction. The Ratio of minimum to maximum transmission is 0.5164. 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    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6654
_refine_ls_number_restraints     350
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.2303
_refine_ls_R_factor_gt           0.1427
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3905
_refine_ls_wR_factor_ref         0.4700
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2696
_reflns_number_total             6654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01818h2.cif
_cod_data_source_block           cu_20250408c_0m_a
_cod_database_code               7161029
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C26-C25 = C27-C25
 1.54 with sigma of 0.001
 C6-C1 \\sim C6-C1A \\sim C2-C1 \\sim C2A-C1A \\sim C6-C5 \\sim C6-C5A \\sim
C5-C4 \\sim C5A-C4A \\sim C4-C3 ~
 C3-C2 \\sim C4A-C3A \\sim C3A-C2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C5 \\sim C4 \\sim C1 \\sim C2 \\sim C3 \\sim C5A \\sim C4A \\sim C1A \\sim C2A
\\sim C3A \\sim C6: within 2A with sigma of 0.001 and sigma for terminal atoms
of 0.002 within 2A
O2 \\sim O1 \\sim C24 \\sim C25 \\sim C27 \\sim C26: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
O3 \\sim O4 \\sim C28 \\sim C29 \\sim C31 \\sim C30: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
4. Rigid body (RIGU) restrains
 C6, C1, C2, C3, C4, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C6, C1A, C2A, C3A, C4A, C5A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=
 Sof(C3A)=Sof(H3A)=1-FVAR(1)
 Sof(C5)=Sof(H5)=Sof(C4)=Sof(H4)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=
 Sof(H3)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C32(H32), C25(H25), C29(H29)
6.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B)
6.c Aromatic/amide H refined with riding coordinates:
 C41(H41), C33(H33), C34(H34), C38(H38), C40(H40), C39(H39), C20(H20),
 C19(H19), C23(H23), C22(H22), C21(H21), C5(H5), C4(H4), C1(H1), C2(H2), C3(H3),
  C4A(H4A), C5A(H5A), C1A(H1A), C2A(H2A), C3A(H3A)
6.d Fitted hexagon refined as free rotating group:
 C20(C19,C18,C23,C22,C21), C4A(C5A,C6,C1A,C2A,C3A)
6.e Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C31(H31A,H31B,
 H31C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              98916
_olex2_submission_special_instructions 'No special instructions were received'