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_4033158
_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         'C19 H15 N3 O5'
_chemical_formula_sum            'C19 H15 N3 O5'
_chemical_formula_weight         365.34
_chemical_melting_point          ?
_chemical_name_common
3-carboxyehyl-4-formyl-5-(4-nitrophenyl)1-phenyl-1H-pyrazol
_chemical_name_systematic
;
3-carboxyehyl-4-formyl-5-(4-nitrophenyl)1-phenyl-1H-pyrazol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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             2015-11-16T15:43:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 119.40(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.51(2)
_cell_length_b                   7.656(8)
_cell_length_c                   18.984(15)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      24.43
_cell_measurement_theta_min      2.467
_cell_volume                     3483(5)
_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      299(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 Kappa APEX II diffractometer'
_diffrn_measurement_method       '0.5 \% \w & \f scans'
_diffrn_radiation_monochromator  'graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51679
_diffrn_reflns_theta_full        30.59
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         2.46
_diffrn_source                   'sealed ceramic X ray tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9734
_exptl_absorpt_correction_T_min  0.9725
_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            yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0631
_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^)+(0.0647P)^2^+1.9750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                2871
_reflns_number_total             5346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02361_si_002.cif
_cod_data_source_block           test2_3a
_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_cell_volume        3484(6)
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4033158