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_2016165
_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 3-nitro-4-[(5-phenyl-1<i>H</i>-pyrazol-3-yl)amino]benzoate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 121.071(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.0506(4)
_cell_length_b                   5.4210(11)
_cell_length_c                   20.7251(12)
_cell_measurement_reflns_used    3420
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.06
_cell_volume                     2988.0(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33526
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+4.6327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                2488
_reflns_number_total             3420
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk3149.cif
_cod_data_source_block           II
_cod_original_cell_volume        2988.1(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2016165
_cod_database_fobs_code          2016165