Lewis acid-switched regiodivergent <i>N</i><sup>1</sup>/<i>N</i><sup>2</sup>-alkylation of ben-zotriazoles with α-hydroxyl diazo compounds.
Jiang, Jingjing; Zhang, Jinghan; Huang, Nan; Xu, Haocheng; Liu, Xintao; Li, Jiayin; Zhou, Xinlong; Zhao, Jingjing; Li, Pan; Chemical communications (Cambridge, England) 62 (2026) 3279–3282; doi:10.1039/d5cc07167d

data_7135474
_publ_section_title
;
 Lewis acid-switched regiodivergent
 <i>N</i><sup>1</sup>/<i>N</i><sup>2</sup>-alkylation of ben-zotriazoles
 with &#x3b1;-hydroxyl diazo compounds.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3279
_journal_page_last               3282
_journal_paper_doi               10.1039/d5cc07167d
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C21 H22 N6 O'
_chemical_formula_sum            'C21 H22 N6 O'
_chemical_formula_weight         374.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2nt6rg
_audit_creation_date             2024-06-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-25 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.946(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1428(19)
_cell_length_b                   10.6392(10)
_cell_length_c                   19.4801(19)
_cell_measurement_reflns_used    2334
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      19.980
_cell_measurement_theta_min      2.559
_cell_volume                     3881.5(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2457
_diffrn_reflns_av_unetI/netI     0.1801
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36233
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.945
_diffrn_reflns_theta_max         24.945
_diffrn_reflns_theta_min         2.137
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              Microfocus
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.2586
_exptl_absorpt_correction_T_min  0.1729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1694 before and 0.0969 after correction.
The Ratio of minimum to maximum transmission is 0.6686.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0098(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         6738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.2350
_refine_ls_R_factor_gt           0.1122
_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^)+(0.1153P)^2^+6.3278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2650
_refine_ls_wR_factor_ref         0.3328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2786
_reflns_number_total             6738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc07167d2.cif
_cod_data_source_block           m14243_0m
_cod_database_code               7135474
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.992
_diffrn_source_source            'Incoatc Ius 3.0 '
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C19(H19A,H19B), C32(H32A,H32B), C41(H41A,
 H41B), C5(H5A,H5B), C25(H25A,H25B), C34(H34A,H34B), C39(H39A,H39B), C42(H42A,
 H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C20(H20), C23(H23), C31(H31), C35(H35), C36(H36), C38(H38),
 C40(H40), C2(H2), C3(H3), C17(H17), C21(H21), C27(H27), C28(H28), C29(H29),
 C30(H30), C33(H33)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              83627
_shelx_hkl_checksum              17641
_olex2_submission_special_instructions 'No special instructions were received'