Copper-catalyzed coupling of oxime acetates and aryldiazonium salts: an azide-free strategy toward N-2-aryl-1,2,3-triazoles
Zhu, Chuanle; Zeng, Hao; Chen, Fulin; Liu, Chi; Zhu, Rui; Wu, Wanqing; Jiang, Huanfeng; Organic Chemistry Frontiers 5 (2018) 571–; doi:10.1039/C7QO00874K

data_1553917
_publ_section_title
;
 Copper-catalyzed coupling of oxime acetates and aryldiazonium salts: an
 azide-free strategy toward N-2-aryl-1,2,3-triazoles
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              571
_journal_paper_doi               10.1039/C7QO00874K
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C16 H15 N3 O2'
_chemical_formula_sum            'C16 H15 N3 O2'
_chemical_formula_weight         281.31
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-07-13 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                86.207(4)
_cell_angle_beta                 88.891(3)
_cell_angle_gamma                76.774(4)
_cell_formula_units_Z            2
_cell_length_a                   6.0881(2)
_cell_length_b                   7.8709(4)
_cell_length_c                   14.5993(7)
_cell_measurement_reflns_used    3460
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.2880
_cell_measurement_theta_min      5.7710
_cell_volume                     679.53(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -9.00  30.00   1.00    1.00    --  -40.98  57.00 120.00   39
  2  \w    -31.00  -2.00   1.00    1.00    --  -40.98 125.00  60.00   29
  3  \w    -61.00 -31.00   1.00    1.00    --  -40.98  57.00 120.00   30
  4  \w    -68.00  32.00   1.00    1.00    --  -40.98  57.00   0.00  100
  5  \w    -94.00 -65.00   1.00    1.00    --  -40.98 125.00  60.00   29
  6  \w   -106.00 -22.00   1.00    1.00    --  -40.98 -57.00-150.00   84
  7  \w     32.00  67.00   1.00    1.00    --   40.98-125.00-180.00   35
  8  \w     45.00 133.00   1.00    1.00    --  106.95 -61.00-150.00   88
  9  \w     94.00 121.00   1.00    1.00    --  106.95 -30.00 -60.00   27
 10  \w     91.00 178.00   1.00    1.00    --  106.95  30.00 -60.00   87
 11  \w    128.00 172.00   1.00    1.00    --  106.95 125.00-180.00   44
 12  \w     33.00 135.00   1.00    1.00    --  106.95 -30.00 -30.00  102
 13  \w     96.00 121.00   1.00    1.00    --  106.95-125.00   0.00   25
 14  \w     58.00 109.00   1.00    1.00    --  106.95 -94.00 -30.00   51
 15  \w     47.00  74.00   1.00    1.00    --  106.95-125.00   0.00   27
 16  \w     32.00 132.00   1.00    1.00    --  106.95 -30.00 120.00  100
 17  \w     58.00 106.00   1.00    1.00    --  106.95-125.00 150.00   48
 18  \w     25.00  61.00   1.00    1.00    --  106.95 -94.00 150.00   36
 19  \w     31.00  66.00   1.00    1.00    --  106.95 -30.00 -60.00   35
 20  \w     43.00 107.00   1.00    1.00    --  106.95 -94.00-180.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0800946000
_diffrn_orient_matrix_UB_12      0.1450259000
_diffrn_orient_matrix_UB_13      0.0465763000
_diffrn_orient_matrix_UB_21      0.0852652000
_diffrn_orient_matrix_UB_22      0.0632536000
_diffrn_orient_matrix_UB_23      -0.0932866000
_diffrn_orient_matrix_UB_31      -0.2321309000
_diffrn_orient_matrix_UB_32      0.1247228000
_diffrn_orient_matrix_UB_33      -0.0176794000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4426
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.359
_diffrn_reflns_theta_min         5.786
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.047
_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     192
_refine_ls_number_reflns         2640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0604P)^2^+0.1734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2486
_reflns_number_total             2640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00874k2.cif
_cod_data_source_block           exp_265
_cod_database_code               1553917
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.816
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C11(H11), C15(H15), C6(H6), C8(H8), C3(H3), C4(H4), C7(H7)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.720
_oxdiff_exptl_absorpt_empirical_full_min 0.570