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_7161027
_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 H35 Cl N2 O4'
_chemical_formula_sum            'C46 H35 Cl N2 O4'
_chemical_formula_weight         715.21
_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             2025-06-30
_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                112.6600(10)
_cell_angle_beta                 105.0610(10)
_cell_angle_gamma                98.3290(10)
_cell_formula_units_Z            2
_cell_length_a                   10.3480(2)
_cell_length_b                   13.4185(3)
_cell_length_c                   15.4355(3)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      68.297
_cell_measurement_theta_min      3.307
_cell_volume                     1836.32(7)
_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 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 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0533
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28852
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.434
_diffrn_reflns_theta_min         3.306
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4230
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1257 before and 0.0794 after correction. The Ratio of minimum to maximum transmission is 0.5617. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         6725
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0927P)^2^+0.5580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.1908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5249
_reflns_number_total             6725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01818h2.cif
_cod_data_source_block           cu_20250515e_0m_a
_cod_database_code               7161027
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.829
_shelx_estimated_absorpt_t_min   0.809
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
C21 \\sim C22 \\sim C23 \\sim C18 \\sim C19 \\sim C20: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C40(H40A,H40B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C38(H38), C16(H16), C29(H29), C35(H35), C37(H37), C32(H32), C1(H1), C5(H5),
 C46(H46), C19(H19), C36(H36), C23(H23), C30(H30), C42(H42), C4(H4), C45(H45),
 C3(H3), C2(H2), C31(H31), C20(H20), C21(H21), C22(H22), C43(H43)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              34020
_olex2_submission_special_instructions 'No special instructions were received'