Silver-Catalyzed Pyrazole Migration and Cycloaddition Reaction of Diazo Pyrazoleamides with Ketimines
Shi, Maoqing; Niu, Gejun; Zhang, Tianyuan; Xu, Aimin; Zheng, Rimei; yusuf, abdulla; Shi, Taoda; Hu, Wenhao; Qian, Yu; Chemical Communications  (2023) –; doi:10.1039/D3CC03253A

data_7131952
_publ_section_title
;
 Silver-Catalyzed Pyrazole Migration and Cycloaddition Reaction of Diazo
 Pyrazoleamides with Ketimines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03253A
_journal_year                    2023
_chemical_formula_moiety         'C29 H29 Cl N4 O2'
_chemical_formula_sum            'C29 H29 Cl N4 O2'
_chemical_formula_weight         501.01
_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_block_doi                 10.5517/ccdc.csd.cc2dm7t3
_audit_creation_date             2022-10-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-29 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                86.694(3)
_cell_angle_beta                 71.741(4)
_cell_angle_gamma                86.666(3)
_cell_formula_units_Z            2
_cell_length_a                   9.9599(5)
_cell_length_b                   11.0330(3)
_cell_length_c                   11.8000(5)
_cell_measurement_reflns_used    10157
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3240
_cell_measurement_theta_min      3.9410
_cell_volume                     1228.24(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.947
_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     95.00 132.00   0.50    0.08    --  105.22 125.00-150.00   74
  2  \w    137.00 170.00   0.50    0.08    --  105.22 125.00-150.00   66
  3  \w     28.00  63.00   0.50    0.08    --   44.84 -57.00   0.00   70
  4  \w    -26.00  13.00   0.50    0.08    --   44.84 -43.00 136.00   78
  5  \w     18.00  45.00   0.50    0.08    --   44.84 -43.00 136.00   54
  6  \w     43.00  96.00   0.50    0.08    --   44.84-125.00   0.00  106
  7  \w     80.00 112.00   0.50    0.08    --  105.22-125.00 120.00   64
  8  \w     34.00  75.00   0.50    0.08    --  105.22-125.00 120.00   82
  9  \w     52.00 110.00   0.50    0.08    --  105.22-125.00  30.00  116
 10  \w     87.00 112.00   0.50    0.08    --  105.22-125.00 -30.00   50
 11  \w     33.00  63.00   0.50    0.08    --  105.22 -94.00  60.00   60
 12  \w     43.00  68.00   0.50    0.08    --  105.22-125.00 -30.00   50
 13  \w     86.00 111.00   0.50    0.08    --  105.22-125.00 -90.00   50
 14  \w     37.00  99.00   0.50    0.08    --  105.22-125.00-120.00  124
 15  \w     40.00 102.00   0.50    0.08    --  105.22 -94.00-120.00  124
 16  \w     69.00  96.00   0.50    0.08    --  105.22 -94.00  60.00   54
 17  \w     32.00  70.00   0.50    0.08    --  105.22 -61.00  90.00   76
 18  \w     39.00  68.00   0.50    0.08    --  105.22 -61.00 150.00   58
 19  \w     32.00  64.00   0.50    0.08    --  105.22 -61.00   0.00   64
 20  \w     44.00  69.00   0.50    0.08    --  105.22 -61.00 -90.00   50
 21  \w     80.00 111.00   0.50    0.08    --  105.22  15.00  30.00   62
 22  \w    135.00 176.00   0.50    0.08    --  105.22  15.00  30.00   82
 23  \w     86.00 162.00   0.50    0.08    --  105.22  43.00 -72.00  152
 24  \w     28.00 116.00   0.50    0.08    --   44.84  43.00 -72.00  176
 25  \w     -7.00  31.00   0.50    0.08    --  -44.84  19.00  60.00   76
 26  \w    -98.00 -73.00   0.50    0.08    -- -100.00  77.00  90.00   50
 27  \w    -46.00  29.00   0.50    0.08    --  -44.84  43.00 -72.00  150
 28  \w    -94.00 -41.00   0.50    0.08    -- -100.00  77.00-180.00  106
 29  \w   -175.00 -75.00   0.50    0.08    -- -100.00 -15.00-150.00  200
 30  \w   -130.00-104.00   0.50    0.08    -- -100.00 -77.00-120.00   52
 31  \w   -103.00 -74.00   0.50    0.08    -- -100.00 -77.00-120.00   58
 32  \w   -149.00 -82.00   0.50    0.08    -- -100.00 -45.00   0.00  134
 33  \w   -143.00-104.00   0.50    0.08    -- -100.00 -45.00  90.00   78
 34  \w   -168.00-104.00   0.50    0.08    -- -100.00 -43.00 136.00  128
 35  \w   -119.00 -28.00   0.50    0.08    --  -44.84 -43.00 136.00  182
 36  \w   -107.00 -27.00   0.50    0.08    -- -100.00 105.00 -58.41  160
 37  \w    -64.00 -35.00   0.50    0.08    -- -100.00 125.00 120.00   58
 38  \w   -105.00 -77.00   0.50    0.08    -- -100.00 125.00 120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0935321000
_diffrn_orient_matrix_UB_12      0.0745131000
_diffrn_orient_matrix_UB_13      -0.0631115000
_diffrn_orient_matrix_UB_21      0.1114741000
_diffrn_orient_matrix_UB_22      0.0978988000
_diffrn_orient_matrix_UB_23      -0.0391711000
_diffrn_orient_matrix_UB_31      0.0734970000
_diffrn_orient_matrix_UB_32      -0.0667894000
_diffrn_orient_matrix_UB_33      -0.1158255000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12880
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.346
_diffrn_reflns_theta_min         3.948
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0841
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+13.4077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2449
_refine_ls_wR_factor_ref         0.2461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4534
_reflns_number_total             4815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03253a2.cif
_cod_data_source_block           20221026-smq-2_auto
_cod_database_code               7131952
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.852
_shelx_estimated_absorpt_t_min   0.628
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C23(H23), C15(H15), C26(H26), C21(H21), C22(H22), C3(H3A), C25(H25),
 C28(H28), C12(H12), C19(H19), C20(H20), C13(H13), C29(H29), C14(H14)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C1(H1A,H1B,H1C), C5(H5A,H5B,H5C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              54412
_shelx_hkl_checksum              67474
_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 2.848
_oxdiff_exptl_absorpt_empirical_full_min 0.546