Rh(II)-catalysed <i>N</i><sup>2</sup>-selective arylation of benzotriazoles and indazoles using quinoid carbenes <i>via</i> 1,5-H shift.
Sarkar, Souradip; Bhunya, Sourav; Pan, Subarna; Datta, Arnadeep; Roy, Lisa; Samanta, Rajarshi; Chemical communications (Cambridge, England) 60 (2024) 4727–4730; doi:10.1039/d4cc00823e

data_7132915
_publ_section_title
;
 Rh(II)-catalysed <i>N</i><sup>2</sup>-selective arylation of
 benzotriazoles and indazoles using quinoid carbenes <i>via</i> 1,5-H
 shift.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4727
_journal_page_last               4730
_journal_paper_doi               10.1039/d4cc00823e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C16 H11 N3 O'
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_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2g0f42
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-21 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.741
_cell_length_b                   17.187
_cell_length_c                   18.371
_cell_measurement_reflns_used    3590
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1
_cell_measurement_theta_min      2.4
_cell_volume                     1181.192
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16018
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.113
_diffrn_reflns_theta_min         2.370
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1045 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         3590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0668P)^2^+0.4526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                2988
_reflns_number_total             3590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00823e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
Adding full bibliography for 7132915--7132916.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         130.64
_cod_original_formula_units_Z            8
_cod_original_cell_volume        1181.2
_cod_original_formula_sum        'C8 H5.50 N1.50 O0.50'
_cod_database_code               7132915
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              4869
_shelx_hkl_checksum              49366