B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed site-selective <i>N</i><sup>1</sup>-alkylation of benzotriazoles with diazoalkanes.
Zhao, Yunbo; Mandal, Dipendu; Guo, Jing; Wu, Yile; Stephan, Douglas W.; Chemical communications (Cambridge, England) 57 (2021) 7758–7761; doi:10.1039/d1cc03048e

data_7128625
_publ_section_title
;
 B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed site-selective
 <i>N</i><sup>1</sup>-alkylation of benzotriazoles with diazoalkanes.
;
_journal_issue                   63
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7758
_journal_page_last               7761
_journal_paper_doi               10.1039/d1cc03048e
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C24 H5 B F15 N3'
_chemical_formula_sum            'C24 H5 B F15 N3'
_chemical_formula_weight         631.12
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-09 deposited with the CCDC.	2021-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                78.261(3)
_cell_angle_beta                 82.173(3)
_cell_angle_gamma                68.054(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3197(6)
_cell_length_b                   10.9741(8)
_cell_length_c                   13.6352(10)
_cell_measurement_reflns_used    627
_cell_measurement_temperature    161.0
_cell_measurement_theta_max      50.51
_cell_measurement_theta_min      3.29
_cell_volume                     1128.07(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      161.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.965
_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  0.0559
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32673
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.149
_diffrn_reflns_theta_min         3.318
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.807
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5886
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1099 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.7816.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         4151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.5170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3639
_reflns_number_total             4151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03048e2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7128624--7128625.cif.'
_cod_database_code               7128625
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C23(H23), C22(H22)
;
_shelx_res_checksum              10127
_olex2_submission_special_instructions 'No special instructions were received'