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_7161026
_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         'C46 H34 F2 N2 O4, 0.5[C6H6], 1[C6H6]'
_chemical_formula_sum            'C55 H43 F2 N2 O4'
_chemical_formula_weight         833.91
_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     iterative
_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                76.822(2)
_cell_angle_beta                 73.368(2)
_cell_angle_gamma                73.606(2)
_cell_formula_units_Z            2
_cell_length_a                   11.8312(3)
_cell_length_b                   13.2147(3)
_cell_length_c                   15.2145(4)
_cell_measurement_reflns_used    7060
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      66.48
_cell_measurement_theta_min      3.07
_cell_volume                     2158.32(10)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37186
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.395
_diffrn_reflns_theta_min         3.071
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5631
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1044 before and 0.0761 after correction.
The Ratio of minimum to maximum transmission is 0.7477.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dull light green'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             874
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7916
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1139P)^2^+0.1738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.2001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4868
_reflns_number_total             7916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01818h2.cif
_cod_data_source_block           cu_20250323b_0m
_cod_database_code               7161026
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.891
_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. Uiso/Uaniso restraints and constraints
C46 \\sim C45 \\sim C44 \\sim C43 \\sim C41 \\sim C42 \\sim C40: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F1 \\sim C3: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B), C40(H40A,H40B)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C29(H29), C19(H19), C23(H23), C38(H38), C30(H30), C22(H22),
 C20(H20), C32(H32), C1(H1), C31(H31), C5(H5), C2(H2), C35(H35), C37(H37),
 C46(H46), C4(H4), C36(H36), C42(H42), C45(H45), C44(H44), C43(H43)
3.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C25(H25A,H25B,H25C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              84746
_shelx_fab_checksum              99838
_olex2_submission_special_instructions 'No special instructions were received'