Two isomeric reaction products: hydrogen-bonded sheets in methyl 4-(5-amino-3-phenyl-1<i>H</i>-pyrazol-1-yl)-3-nitrobenzoate and hydrogen-bonded chains of edge-fused rings in methyl 3-nitro-4-[(5-phenyl-1<i>H</i>-pyrazol-3-yl)amino]benzoate
Portilla, Jaime; Mata, Ernesto G.; Cobo, Justo; Low, John N.; Glidewell, Christopher; Acta Crystallographica Section C 63 (2007) o510–o513; doi:10.1107/S010827010703346X

data_2016164
_publ_section_title
;
 Two isomeric reaction products: hydrogen-bonded sheets in methyl
 4-(5-amino-3-phenyl-1<i>H</i>-pyrazol-1-yl)-3-nitrobenzoate and
 hydrogen-bonded chains of edge-fused rings in methyl
 3-nitro-4-[(5-phenyl-1<i>H</i>-pyrazol-3-yl)amino]benzoate
;
_journal_coeditor_code           SK3149
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o510
_journal_page_last               o513
_journal_paper_doi               10.1107/S010827010703346X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H14 N4 O4'
_chemical_formula_moiety         'C17 H14 N4 O4'
_chemical_formula_sum            'C17 H14 N4 O4'
_chemical_formula_weight         338.32
_chemical_name_systematic
;
methyl 4-(5-amino-3-phenyl-1<i>H</i>-pyrazol-1-yl)-3-nitrobenzoate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 100.699(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3516(8)
_cell_length_b                   7.5202(4)
_cell_length_c                   17.1564(13)
_cell_measurement_reflns_used    3597
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.19
_cell_volume                     1565.89(18)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg <i>et al.</i>,  2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg <i>et al.</i>,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement
'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR2004 (Burla <i>et al.</i>,  2005) and WinGX (Farrugia, 1999)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37526
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.389
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0883P)^2^+0.9526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1775
_reflns_number_gt                2266
_reflns_number_total             3597
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk3149.cif
_cod_data_source_block           I
_cod_original_cell_volume        1565.90(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016164
_cod_database_fobs_code          2016164