Rh(III)-catalyzed cyclization of 5-amino-pyrazoles with maleimides to pyrazoloquinazolines.
Guo, Ting-Ting; Zhao, Qing-Sheng; Yang, Shu; Chen, Tian-Tian; Liu, Jin; Yan, Sheng-Jiao; Chemical communications (Cambridge, England) 61 (2025) 16846–16849; doi:10.1039/d5cc04547a

data_7135036
_publ_section_title
;
 Rh(III)-catalyzed cyclization of 5-amino-pyrazoles with maleimides to
 pyrazoloquinazolines.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16846
_journal_page_last               16849
_journal_paper_doi               10.1039/d5cc04547a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C21 H17 Cl N4 O2, 2(H2 O)'
_chemical_formula_sum            'C21 H21 Cl N4 O4'
_chemical_formula_weight         428.87
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-11-13
_audit_creation_method
;
FinalCif V89 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-08-06 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.563(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5672(9)
_cell_length_b                   35.984(3)
_cell_length_c                   5.9462(4)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.21
_cell_volume                     2037.4(3)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            27229
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.420
_diffrn_reflns_theta_min         2.139
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1323 before and 0.0968 after correction.
The Ratio of minimum to maximum transmission is 0.7758.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.406
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.1120
_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^)+(0.0045P)^2^+14.2552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2267
_refine_ls_wR_factor_ref         0.2344
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4241
_reflns_number_total             5069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04547a2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7135035--7135037.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7135036
_shelx_shelxl_version_number     2018/3
_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,H) groups
2.a Riding coordinates:
 O4(H4A,H4B)
2.b Free rotating group:
 O3(H3A,H3B)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C13(H13), C15(H15), C16(H16),
  C19(H19)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.965
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              43443