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_7156130
_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         'C27 H21 Cl N4 O2'
_chemical_formula_sum            'C27 H21 Cl N4 O2'
_chemical_formula_weight         468.93
_chemical_melting_point          406.5(5)
_chemical_name_systematic
'Ethyl 5'-(4-chlorophenyl)-1',2-diphenyl-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_cell_setting           triclinic
_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                84.40(6)
_cell_angle_beta                 71.46(7)
_cell_angle_gamma                80.99(5)
_cell_formula_units_Z            2
_cell_length_a                   8.803(6)
_cell_length_b                   10.863(6)
_cell_length_c                   12.961(11)
_cell_measurement_reflns_used    7278
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      65.3191
_cell_measurement_theta_min      3.5899
_cell_volume                     1159.1(15)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_l_min       -15
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_diffrn_reflns_theta_full        66.09
_diffrn_reflns_theta_max         66.09
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_max  1.29544
_exptl_absorpt_correction_T_min  0.60462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         3935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0496
_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^)+(0.1040P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                3040
_reflns_number_total             3935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02725g2.cif
_cod_data_source_block           dc_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '406-407' was changed to '406.5(5)' -
the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

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

 Adding full bibliography for 7156128--7156130.cif.
;
_cod_original_cell_volume        1159.1(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7156130