Rh(III)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides.
Chen, Longkun; Zhang, Mingshuai; Liu, Meichen; Liu, Zhuoyuan; Qiu, Yuetong; Zhang, Zhilai; Yu, Fuchao; Huang, Jiuzhong; Chemical communications (Cambridge, England) 60 (2024) 432–435; doi:10.1039/d3cc05266d

data_7132427
_publ_section_title
;
 Rh(III)-catalyzed selective mono- and dual-functionalization/cyclization
 of 1-aryl-5-aminopyrazoles with iodonium ylides.
;
_journal_issue                   4
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              432
_journal_page_last               435
_journal_paper_doi               10.1039/d3cc05266d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C32 H32 Br N3 O3 S, C H4 O'
_chemical_formula_sum            'C33 H36 Br N3 O4 S'
_chemical_formula_weight         650.62
_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             2023-06-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-02 deposited with the CCDC.	2023-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                113.225(5)
_cell_angle_beta                 97.316(5)
_cell_angle_gamma                101.109(6)
_cell_formula_units_Z            2
_cell_length_a                   9.915(3)
_cell_length_b                   13.033(4)
_cell_length_c                   14.176(4)
_cell_measurement_reflns_used    2231
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      2.37
_cell_volume                     1609.3(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9823
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         2.721
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.382
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0272 after correction.
The Ratio of minimum to maximum transmission is 0.8230.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         7049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0734P)^2^+1.1257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4176
_reflns_number_total             7049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05266d1.cif
_cod_data_source_block           230611yfc_0m
_cod_depositor_comments
'Adding full bibliography for 7132426--7132427.cif.'
_cod_original_cell_volume        1609.4(8)
_cod_database_code               7132427
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.770
_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 Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00R(H00C,H00D), C00S(H00E,H00F), C013(H01G,H01H)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), C00L(H00L), C00O(H00O), C00P(H00P), C00T(H00T), C00W(H00W),
 C00Z(H00Z), C012(H012)
2.c Idealised Me refined as rotating group:
 C00V(H00G,H00H,H00I), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F), C014(H01I,
 H01J,H01K), C015(H01L,H01M,H01N), C016(H01O,H01P,H01Q)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003), O00U(H00U)
;
_shelx_res_checksum              25244
_shelx_hkl_checksum              27932
_olex2_submission_special_instructions 'No special instructions were received'