A chemo- and regiocontrolled approach to bipyrazoles and pyridones via the reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with hydrazines.
Obydennov, D. L.; Khammatova, L. R.; Eltsov, O. S.; Sosnovskikh, V. Y.; Organic & biomolecular chemistry 16 (2018) 1692–1707; doi:10.1039/c7ob02725g

data_7156128
_publ_section_title
;
 A chemo- and regiocontrolled approach to bipyrazoles and pyridones via
 the reaction of ethyl 5-acyl-4-pyrone-2-carboxylates with hydrazines.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1692
_journal_page_last               1707
_journal_paper_doi               10.1039/c7ob02725g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         C18H20N4O3
_chemical_formula_sum            'C18 H20 N4 O3'
_chemical_formula_weight         340.38
_chemical_melting_point          411.5(5)
_chemical_name_systematic
'Ethyl 3'-(4- methoxyphenyl)-1',2-dimethyl-1'H,2H-3,4'-bipyrazole-5-carboxylate'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-08-16 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                65.802(7)
_cell_angle_beta                 70.156(6)
_cell_angle_gamma                75.680(6)
_cell_formula_units_Z            2
_cell_length_a                   8.7419(6)
_cell_length_b                   10.7719(7)
_cell_length_c                   10.9487(7)
_cell_measurement_temperature    293(2)
_cell_volume                     877.51(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.878
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8223
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.68
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.090
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH-H2O'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4776
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1070P)^2^+0.0600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1901
_reflns_number_gt                3174
_reflns_number_total             4776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02725g2.cif
_cod_data_source_block           exp_872
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '411--412 ' was changed to '411.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156128--7156130.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7156128