Theoretical and experimental investigation of the polyeletrophilic β-enamino diketone: straightforward and highly regioselective synthesis of 1,4,5-trisubstituted pyrazoles and pyrazolo[3,4-d]pyridazinones
da Silva, Michael J. V.; Silva, Raí G. M.; Melo, Ulisses Z.; Gonçalves, Davana S.; Back, Davi F.; Moura, Sidnei; Pontes, Rodrigo M.; Basso, Ernani A.; Gauze, Gisele F.; Rosa, Fernanda A.; RSC Adv. 6 (2016) 290–; doi:10.1039/C5RA12968K

data_7223607
_publ_section_title
;
 Theoretical and experimental investigation of the polyeletrophilic
 \b-enamino diketone: straightforward and highly regioselective synthesis
 of 1,4,5-trisubstituted pyrazoles and pyrazolo[3,4-d]pyridazinones
;
_journal_issue                   1
_journal_name_full               'RSC Adv.'
_journal_page_first              290
_journal_paper_doi               10.1039/C5RA12968K
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C16 H16 N2 O5'
_chemical_formula_sum            'C16 H16 N2 O5'
_chemical_formula_weight         316.31
_chemical_melting_point          311
_chemical_name_common
5-carboxyethyl-4-[4ethoxy(oxo)acetyl]-1-phenyl-1H-pyrazol
_chemical_name_systematic
;
5-carboxyethyl-4-[4ethoxy(oxo)acetyl]-1-phenyl-1H-pyrazol
;
_space_group_IT_number           2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2015-09-16T18:59:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-09-18 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                67.3590(10)
_cell_angle_beta                 80.1190(10)
_cell_angle_gamma                81.5650(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3305(2)
_cell_length_b                   10.6140(3)
_cell_length_c                   11.3269(3)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.236
_cell_volume                     798.16(4)
_computing_cell_refinement       'BRUKER SANT'
_computing_data_collection       'Bruker Instrument Service v2012.10.0.0'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR, Bo'
_computing_publication_material  'APEX2 (version 2012.10-0; Bruker, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker X8 Kappa APEX II diffractometer'
_diffrn_measurement_method       '0.5 \% \w & \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23956
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.96
_diffrn_source                   'sealed ceramic X ray tube'
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.8854
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.572
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.04
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.1903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.128
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                3020
_reflns_number_total             3670
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra12968k2.cif
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '311K' was changed to '311' - the
value should be numeric and without a unit designator.

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7223607