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_7160352
_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 H8 N4 O2'
_chemical_formula_sum            'C14 H8 N4 O2'
_chemical_formula_weight         264.24
_chemical_melting_point          538.5(5)
_chemical_name_systematic
(E)-5-oxo-6-(2-oxo-2-phenylethylidene)-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile
_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
_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                 94.584(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1843(14)
_cell_length_b                   12.8448(14)
_cell_length_c                   6.8879(7)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.16
_cell_measurement_theta_min      2.22
_cell_volume                     1162.7(2)
_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      100(2)
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.943
_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  0.0454
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20407
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_min         2.217
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6776
_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    1.510
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetic acid'
_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0986
_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^)+(0.0455P)^2^+4.4273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2134
_refine_ls_wR_factor_ref         0.2157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2757
_reflns_number_total             2953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01911c3.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '538-539' was changed to
'538.5(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 

 Adding full bibliography for 7160352--7160354.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160352
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              43250