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_7128624
_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         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 103.6050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6486(3)
_cell_length_b                   6.0185(2)
_cell_length_c                   15.9086(6)
_cell_measurement_reflns_used    9352
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      68.54
_cell_measurement_theta_min      2.86
_cell_volume                     711.77(5)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      125.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0679
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11863
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.531
_diffrn_reflns_theta_min         2.858
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5043
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1453 before and 0.0913 after correction.
The Ratio of minimum to maximum transmission is 0.6696.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0646P)^2^+0.0867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2523
_reflns_number_total             2592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03048e2.cif
_cod_data_source_block           12
_cod_depositor_comments
'Adding full bibliography for 7128624--7128625.cif.'
_cod_database_code               7128624
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C2(H2), C5(H5), C14(H14), C12(H12), C11(H11), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              30801
_olex2_submission_special_instructions 'No special instructions were received'