ANRORC type rearrangement/intermolecular cyclocondensation cascade of 5,6-dicyano-3-(2-oxo-2-ethyl)pyrazin-2(1<i>H</i>)-ones with hydrazine hydrate for the synthesis of 2-(pyrazol-3-yl)imidazo[4,5-<i>d</i>]pyridazines.
Mamedov, Vakhid A.; Galimullina, Venera R.; Qu, Zheng-Wang; Zhu, Hui; Syakaev, Victor V.; Nikolaeva, Dariya V.; Rizvanov, Il'dar Kh; Gubaidullin, Aidar T.; Sinyashin, Oleg G.; Grimme, Stefan; Organic & biomolecular chemistry 23 (2025) 2180–2189; doi:10.1039/d4ob01911c

data_7160354
_publ_section_title
;
 ANRORC type rearrangement/intermolecular cyclocondensation cascade of
 5,6-dicyano-3-(2-oxo-2-ethyl)pyrazin-2(1<i>H</i>)-ones with hydrazine
 hydrate for the synthesis of
 2-(pyrazol-3-yl)imidazo[4,5-<i>d</i>]pyridazines.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2180
_journal_page_last               2189
_journal_paper_doi               10.1039/d4ob01911c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C14 H12 N8, C3 H7 N O, 0.5(H2 O)'
_chemical_formula_sum            'C17 H20 N9 O1.5'
_chemical_formula_weight         374.42
_chemical_melting_point          495.5(5)
_chemical_name_systematic
'2-(5-Phenyl-1H-pyrazol-3-yl)-5H-imidazo[4,5-d]pyridazine-4,7-diamine hydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-07-27 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.179(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.826(3)
_cell_length_b                   10.5319(13)
_cell_length_c                   16.192(2)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    162(2)
_cell_measurement_theta_max      34.66
_cell_measurement_theta_min      2.32
_cell_volume                     3766.2(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      162(2)
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            84574
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.804
_diffrn_reflns_theta_min         1.844
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       prism
_exptl_crystal_F_000             1576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetic acid'
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         8114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0818P)^2^+0.6279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6405
_reflns_number_total             8114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01911c3.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '495-496' was changed to
'495.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel

 Adding full bibliography for 7160352--7160354.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_moiety     '2(C14 H12 N8), 2(C3 H7 N O), H2 O'
_cod_original_formula_sum        'C34 H40 N18 O3'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     748.84
_cod_database_code               7160354
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              59290