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_7131953
_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         'C33 H26 N4 O2'
_chemical_formula_sum            'C33 H26 N4 O2'
_chemical_formula_weight         510.58
_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.cc2d4nhq
_audit_creation_date             2022-09-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-09-23 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.473(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1778(4)
_cell_length_b                   14.3635(4)
_cell_length_c                   13.5804(4)
_cell_measurement_reflns_used    8331
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.3760
_cell_measurement_theta_min      4.4500
_cell_volume                     2554.10(13)
_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      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 0.990
_diffrn_measured_fraction_theta_max 0.934
_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    -27.00  48.00   0.50    0.09    --   44.97 -70.00  21.00  150
  2  \w     68.00  93.00   0.50    0.37    --  105.71 -94.00  60.00   50
  3  \w     32.00  74.00   0.50    0.37    --  105.71 -70.00  21.00   84
  4  \w     40.00  72.00   0.50    0.37    --  105.71 -61.00  30.00   64
  5  \w     39.00  70.00   0.50    0.37    --  105.71 -61.00 -30.00   62
  6  \w     83.00 154.00   0.50    0.37    --  105.71  15.00 -60.00  142
  7  \w    145.00 172.00   0.50    0.37    --  105.71  45.00 -90.00   54
  8  \w    101.00 127.00   0.50    0.37    --  105.71  45.00 -90.00   52
  9  \w    112.00 137.00   0.50    0.37    --  105.71  70.00 152.00   50
 10  \w     46.00  71.00   0.50    0.09    --   44.97  70.00 152.00   50
 11  \w    -11.00  28.00   0.50    0.09    --  -44.97  70.00 152.00   78
 12  \w    -24.00  33.00   0.50    0.09    --  -44.97  19.00 150.00  114
 13  \w    -82.00 -26.00   0.50    0.37    -- -100.00  70.00 152.00  112
 14  \w    -64.00 -27.00   0.50    0.37    -- -100.00  61.00   0.00   74
 15  \w    -69.00 -39.00   0.50    0.37    -- -100.00  61.00 -30.00   60
 16  \w    -66.00 -40.00   0.50    0.37    -- -100.00  61.00 -60.00   52
 17  \w    -68.00 -27.00   0.50    0.37    -- -100.00  61.00-120.00   82
 18  \w    -69.00 -27.00   0.50    0.37    -- -100.00  61.00-150.00   84
 19  \w    -24.00  29.00   0.50    0.09    --  -44.97  19.00 -30.00  106
 20  \w    -68.00 -27.00   0.50    0.37    -- -100.00  61.00 120.00   82
 21  \w   -167.00-115.00   0.50    0.37    -- -100.00 -30.00  60.00  104
 22  \w   -175.00 -95.00   0.50    0.37    -- -100.00 -30.00  90.00  160
 23  \w   -158.00 -98.00   0.50    0.37    -- -100.00 -70.00  21.00  120
 24  \w   -106.00 -46.00   0.50    0.09    --  -44.97 -70.00  21.00  120
;
_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      0.1158436000
_diffrn_orient_matrix_UB_12      -0.0044473000
_diffrn_orient_matrix_UB_13      0.0326318000
_diffrn_orient_matrix_UB_21      0.0087444000
_diffrn_orient_matrix_UB_22      -0.0850321000
_diffrn_orient_matrix_UB_23      -0.0675846000
_diffrn_orient_matrix_UB_31      0.0193714000
_diffrn_orient_matrix_UB_32      0.0651490000
_diffrn_orient_matrix_UB_33      -0.0859503000
_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  0.0556
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15240
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.695
_diffrn_reflns_theta_min         4.432
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18850
_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 yellow'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0564
_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^)+(0.1013P)^2^+0.9588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4171
_reflns_number_total             4962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03253a2.cif
_cod_data_source_block           20220902-smq-f-47_auto
_cod_database_code               7131953
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_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:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C2(H2), C6(H6), C25(H25), C3(H3), C12(H12), C13(H13),
 C26(H26), C5(H5), C32(H32), C29(H29), C33(H33), C27(H27), C28(H28), C4(H4),
 C23(H23), C19(H19), C22(H22), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_shelx_res_checksum              47389
_shelx_hkl_checksum              53949
_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 3.535
_oxdiff_exptl_absorpt_empirical_full_min 0.571