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_7131954
_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         'C34 H28 N4 O2'
_chemical_formula_sum            'C34 H28 N4 O2'
_chemical_formula_weight         524.60
_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_block_doi                 10.5517/ccdc.csd.cc2dm81c
_audit_creation_date             2022-11-29
_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                90
_cell_angle_beta                 90.4500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.84990(10)
_cell_length_b                   16.04180(10)
_cell_length_c                   19.52990(10)
_cell_measurement_reflns_used    32643
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.4350
_cell_measurement_theta_min      2.2450
_cell_volume                     5278.82(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.958
_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     77.00  82.00   0.50    0.50    --  105.85 -70.00  90.00   10
  2  \w     28.00  33.00   0.50    0.13    --   44.84 -70.00  90.00   10
  3  \w    -23.00 -18.00   0.50    0.13    --  -44.84  70.00   0.00   10
  4  \w    -23.00 -18.00   0.50    0.13    --  -44.84  70.00  90.00   10
  5  \w    -79.00 -74.00   0.50    0.50    -- -100.00  70.00   0.00   10
  6  \w    -79.00 -74.00   0.50    0.50    -- -100.00  70.00  90.00   10
  7  \w     67.00 118.00   0.50    0.33    --   44.84 144.00 104.00  102
  8  \w   -168.00 -72.00   0.50    1.00    -- -100.00-140.00 137.00  192
  9  \w   -174.00-147.00   0.50    1.00    -- -100.00   5.00-164.00   54
 10  \w     38.00 125.00   0.50    1.00    --  105.85-144.00  50.00  174
 11  \w    150.00 175.00   0.50    1.00    --  105.85  -5.00  19.00   50
 12  \w    -24.00  17.00   0.50    0.33    --  -44.84  19.00 -30.00   82
 13  \w    -16.00  63.00   0.50    0.33    --   44.84 -57.00-120.00  158
 14  \w     -8.00  25.00   0.50    0.33    --   44.84 -19.00 -90.00   66
 15  \w    -69.00 -42.00   0.50    1.00    -- -100.00  61.00  60.00   54
 16  \w   -160.00 -87.00   0.50    1.00    -- -100.00 -94.00 -30.00  146
 17  \w     58.00 111.00   0.50    1.00    --  105.85-125.00 -30.00  106
 18  \w    120.00 163.00   0.50    1.00    --  105.85  61.00 -60.00   86
 19  \w     66.00  91.00   0.50    0.33    --   44.84 144.00 104.00   50
 20  \w     87.00 113.00   0.50    0.25    --   44.84  38.00 -30.00   52
 21  \w     -3.00  31.00   0.50    0.25    --  -44.84  19.00  90.00   68
 22  \w     53.00 116.00   0.50    0.25    --   44.84  57.00-150.00  126
 23  \w   -112.00 -85.00   0.50    0.50    -- -100.00 -45.00-120.00   54
 24  \w   -168.00-129.00   0.50    0.50    -- -100.00 -30.00 150.00   78
 25  \w   -126.00 -82.00   0.50    0.50    -- -100.00 -30.00 150.00   88
 26  \w   -160.00-120.00   0.50    0.50    -- -100.00 -45.00-120.00   80
 27  \w     33.00  59.00   0.50    0.50    --  105.85-125.00   0.00   52
 28  \w     57.00  87.00   0.50    0.50    --  105.85 -94.00 -90.00   60
 29  \w     33.00  73.00   0.50    0.50    --  105.85 -61.00  60.00   80
 30  \w    113.00 168.00   0.50    0.50    --  105.85  30.00  60.00  110
 31  \w     42.00  67.00   0.50    0.50    --  105.85 -61.00  90.00   50
 32  \w     40.00  66.00   0.50    0.50    --  105.85 -61.00 -60.00   52
 33  \w     75.00 107.00   0.50    0.50    --  105.85 -77.00 150.00   64
 34  \w     65.00 111.00   0.50    0.50    --  105.85-125.00   0.00   92
 35  \w     42.00  69.00   0.50    0.50    --  105.85 -61.00-180.00   54
 36  \w    -80.00 -55.00   0.50    0.25    --  -44.84 127.00 -64.00   50
;
_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      -0.0201347000
_diffrn_orient_matrix_UB_12      -0.0022200000
_diffrn_orient_matrix_UB_13      0.0767476000
_diffrn_orient_matrix_UB_21      -0.0890066000
_diffrn_orient_matrix_UB_22      0.0066132000
_diffrn_orient_matrix_UB_23      -0.0178096000
_diffrn_orient_matrix_UB_31      -0.0056921000
_diffrn_orient_matrix_UB_32      -0.0958274000
_diffrn_orient_matrix_UB_33      -0.0030484000
_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  0.0155
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40763
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.668
_diffrn_reflns_theta_min         2.622
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84819
_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    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     725
_refine_ls_number_reflns         10510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0266P)^2^+3.6824P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10252
_reflns_number_total             10510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03253a2.cif
_cod_data_source_block           pre_20221129-smq-1_auto
_cod_database_code               7131954
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.777
_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:
 C62(H62A,H62B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C44(H44), C22(H22), C57(H57), C11(H11), C52(H52), C24(H24), C61(H61),
 C53(H53), C15(H15), C6(H6), C50(H50), C51(H51), C25(H25), C36(H36), C23(H23),
 C19(H19), C64(H64), C2(H2), C59(H59), C60(H60), C58(H58), C5(H5), C40(H40),
 C30(H30), C68(H68), C34(H34), C16(H16), C37(H37), C32(H32), C65(H65), C31(H31),
  C4(H4), C66(H66), C3(H3), C38(H38), C67(H67), C18(H18), C33(H33), C39(H39),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C10(H10A,H10B,H10C), C43(H43A,H43B,H43C), C13(H13A,H13B,
 H13C)
;
_shelx_res_checksum              21852
_shelx_hkl_checksum              54005
_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 1.466
_oxdiff_exptl_absorpt_empirical_full_min 0.778