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_4033153
_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         'C16 H18 N2 O6'
_chemical_formula_sum            'C16 H18 N2 O6'
_chemical_formula_weight         334.32
_chemical_melting_point          ?
_chemical_name_common
'isopropylamino nitrobenzoyl oxobut enoic acid ethyl ester'
_chemical_name_systematic
;
(Z)-4-(isopropylamino)-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 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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             2016-06-22T07:43:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.1780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1028(3)
_cell_length_b                   11.5412(3)
_cell_length_c                   10.4124(2)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.072
_cell_measurement_theta_min      4.83
_cell_volume                     1677.52(7)
_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      296(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest 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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20699
_diffrn_reflns_theta_full        68.15
_diffrn_reflns_theta_max         68.15
_diffrn_reflns_theta_min         5.76
_diffrn_source                   'micro-focus tube'
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  0.8641
_exptl_absorpt_correction_T_min  0.5609
_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            yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0144(18)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0839P)^2^+0.7365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1557
_reflns_number_gt                2568
_reflns_number_total             3062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02361_si_002.cif
_cod_data_source_block           test3old_2d
_cod_depositor_comments
;
The following automatic conversions were performed:

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

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

 Adding full bibliography for 4033150--4033158.cif.
;
_cod_original_cell_volume        1677.52(6)
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4033153