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_7131951
_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 H26 N4 O2'
_chemical_formula_sum            'C29 H26 N4 O2'
_chemical_formula_weight         462.54
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2byqdf
_audit_creation_date             2022-05-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-18 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0222(2)
_cell_length_b                   8.7354(2)
_cell_length_c                   22.4535(3)
_cell_measurement_reflns_used    10018
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.1530
_cell_measurement_theta_min      3.9300
_cell_volume                     2348.05(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_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     97.00 172.00   0.50    0.05    --  104.88 104.00 159.00  150
  2  \w    107.00 175.00   0.50    0.05    --  104.88  61.00 120.00  136
  3  \w     30.00 114.00   0.50    0.05    --   45.56  57.00-120.00  168
  4  \w    -12.00  31.00   0.50    0.05    --  -45.56  19.00-150.00   86
  5  \w    -75.00 -28.00   0.50    0.05    -- -100.00  77.00 -30.00   94
  6  \w    -69.00 -27.00   0.50    0.05    -- -100.00  61.00 -30.00   84
  7  \w    -62.00 -29.00   0.50    0.05    -- -100.00  61.00 -60.00   66
  8  \w    -68.00 -28.00   0.50    0.05    -- -100.00  61.00-180.00   80
  9  \w    -50.00 -23.00   0.50    0.05    --  -45.56 125.00-180.00   54
 10  \w   -153.00-128.00   0.50    0.05    -- -100.00-104.00  57.00   50
 11  \w   -161.00-123.00   0.50    0.05    -- -100.00 -15.00-150.00   76
 12  \w   -111.00 -80.00   0.50    0.05    -- -100.00 -15.00-150.00   62
 13  \w    -97.00 -27.00   0.50    0.05    -- -100.00 104.00 159.00  140
 14  \w    -65.00 -40.00   0.50    0.05    --  -45.56 104.00 159.00   50
 15  \w     32.00  57.00   0.50    0.05    --  104.88 -61.00-180.00   50
 16  \w     42.00  67.00   0.50    0.05    --  104.88 -61.00  60.00   50
 17  \w     32.00  59.00   0.50    0.05    --  104.88 -61.00  90.00   54
 18  \w     36.00  72.00   0.50    0.05    --  104.88 -61.00  30.00   72
 19  \w     38.00  72.00   0.50    0.05    --  104.88 -61.00 -60.00   68
 20  \w     -8.00  42.00   0.50    0.05    --   45.56 -38.00 -60.00  100
 21  \w      3.00  84.00   0.50    0.05    --   45.56-104.00  57.00  162
 22  \w     69.00 100.00   0.50    0.05    --  104.88-104.00  57.00   62
 23  \w     80.00 105.00   0.50    0.05    --  104.88 -94.00  60.00   50
 24  \w     46.00  88.00   0.50    0.05    --  104.88 -94.00 120.00   84
;
_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      -0.1079637000
_diffrn_orient_matrix_UB_12      0.0531786000
_diffrn_orient_matrix_UB_13      -0.0364354000
_diffrn_orient_matrix_UB_21      -0.0506205000
_diffrn_orient_matrix_UB_22      -0.1606719000
_diffrn_orient_matrix_UB_23      0.0058743000
_diffrn_orient_matrix_UB_31      -0.0483586000
_diffrn_orient_matrix_UB_32      0.0495200000
_diffrn_orient_matrix_UB_33      0.0582084000
_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  0.0447
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15430
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.300
_diffrn_reflns_theta_min         3.954
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00127(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0458P)^2^+0.6865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4098
_reflns_number_total             4632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03253a2.cif
_cod_data_source_block           shimq_220425_auto
_cod_database_code               7131951
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.825
_shelx_estimated_absorpt_t_min   0.800
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C34(H34), C21(H21), C3(H3), C30(H30), C4(H4), C33(H33),
 C32(H32), C31(H31), C14(H14), C18(H18), C17(H17), C16(H16), C15(H15)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              1864
_shelx_hkl_checksum              53824
_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 2.289
_oxdiff_exptl_absorpt_empirical_full_min 0.337