Electrochemical intramolecular N(sp2)–H/N(sp3)–H coupling for the synthesis of 1H-indazoles
Zhong, Qiang; Wang, Pei-Long; Gao, Hui; Ma, Fang; Yang, Youqing; Li, Hongji; Green Chemistry 25 (2023) 3982–3988; doi:10.1039/D3GC00380A

data_7246709
_publ_section_title
;
 Electrochemical intramolecular N(sp2)--H/N(sp3)--H coupling for the
 synthesis of 1H-indazoles
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              3982
_journal_page_last               3988
_journal_paper_doi               10.1039/D3GC00380A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C20 H18 N2 O2 S'
_chemical_formula_sum            'C19 H19 N3 O2 S'
_chemical_formula_weight         353.43
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2022-11-27 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 97.84(4)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            4
_cell_length_a                   11.349(8)
_cell_length_b                   10.096(7)
_cell_length_c                   15.893(11)
_cell_measurement_reflns_used    888
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      3.09
_cell_volume                     1804(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            72878
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         2.587
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0568 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.9140.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0640P)^2^+0.4740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3506
_reflns_number_total             4089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc00380a2.cif
_cod_data_source_block           2_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7246708--7246709.cif.'
_cod_database_code               7246709
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              50847
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'