Copper-catalyzed multiple oxidation and cycloaddition of aryl–alkyl ketones (alcohols) for the synthesis of 4-acyl- and 4-diketo-1,2,3-triazoles
Huang, Liangfeng; Zheng, Lei; Zhou, Zhongzhen; Chen, Yunfeng; Chemical Communications  (2022) –; doi:10.1039/D1CC06477K

data_7129740
_publ_section_title
;
 Copper-catalyzed multiple oxidation and cycloaddition of aryl--alkyl
 ketones (alcohols) for the synthesis of 4-acyl- and
 4-diketo-1,2,3-triazoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06477K
_journal_year                    2022
_chemical_formula_moiety         'C17 H13 N3 O2'
_chemical_formula_sum            'C17 H13 N3 O2'
_chemical_formula_weight         291.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-16 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.383(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.683(5)
_cell_length_b                   32.548(15)
_cell_length_c                   8.787(4)
_cell_measurement_reflns_used    1572
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.134
_cell_measurement_theta_min      2.402
_cell_volume                     3053(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2156
_diffrn_reflns_av_unetI/netI     0.2844
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33354
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.346
_diffrn_reflns_theta_min         1.908
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0993 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.7092. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         10129
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.3600
_refine_ls_R_factor_gt           0.0972
_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^)+(0.0856P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.2722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2314
_reflns_number_total             10129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06477k2.cif
_cod_data_source_block           mo_210620c_0m
_cod_database_code               7129740
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C15A, C16A, C17A, C12A, C13A, C14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C11B(H11C,H11D)
3.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C10A(H10A), C15A(H15A),
 C14A(H14A), C13A(H13A), C17A(H17A), C16A(H16A), C1B(H1B), C2B(H2B), C3B(H3B),
 C4B(H4B), C5B(H5B), C10B(H10B), C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B),
  C17B(H17B)
;
_shelx_res_checksum              56136
_olex2_submission_special_instructions 'No special instructions were received'