Unconventional Method for Synthesis of 3-Carboxyethyl-4-formyl(hydroxy)-5-aryl-N-arylpyrazoles.
da Silva, Michael J. V.; Poletto, Julia; Jacomini, Andrey P.; Pianoski, Karlos E.; Gonçalves, Davana S; Ribeiro, Gessica M.; de S Melo, Samara M; Back, Davi F.; Moura, Sidnei; Rosa, Fernanda A.; The Journal of organic chemistry 82 (2017) 12590–12602; doi:10.1021/acs.joc.7b02361

data_4033150
_publ_section_title
;
 Unconventional Method for Synthesis of
 3-Carboxyethyl-4-formyl(hydroxy)-5-aryl-N-arylpyrazoles.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12590
_journal_page_last               12602
_journal_paper_doi               10.1021/acs.joc.7b02361
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C14 H14 N2 O6'
_chemical_formula_sum            'C14 H14 N2 O6'
_chemical_formula_weight         306.27
_chemical_melting_point          ?
_chemical_name_common
'methylamino nitrobenzoyl oxobut enoic acid ethyl ester'
_chemical_name_systematic
;
(Z)-4(methylamino)-3-(4-nitrobenzoyl)2-oxobut-3-enoic acid ethyl ester
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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             2016-06-07T13:13:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.693(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1293(11)
_cell_length_b                   11.8856(16)
_cell_length_c                   13.6282(18)
_cell_measurement_reflns_used    3132
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.279
_cell_measurement_theta_min      2.784
_cell_volume                     1465.4(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '2\% \f & \w scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.098
_diffrn_reflns_av_unetI/netI     0.1205
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7555
_diffrn_reflns_theta_full        27.19
_diffrn_reflns_theta_max         27.19
_diffrn_reflns_theta_min         2.28
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   multi-scan
_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    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0063(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0766
_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^)+(0.0587P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.165
_reflns_number_gt                1817
_reflns_number_total             3257
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02361_si_002.cif
_cod_data_source_block           test55_2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

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

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

 Adding full bibliography for 4033150--4033158.cif.
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4033150