Hydrogen-bonded chains of rings in methyl 4-[(5-methyl-1<i>H</i>-pyrazol-3-yl)amino]-3-nitrobenzoate and hydrogen-bonded sheets in methyl 1-(5-methyl-1<i>H</i>-pyrazol-3-yl)-1<i>H</i>-benzimidazole-5-carboxylate
Portilla, Jaime; Mata, Ernesto G.; Nogueras, Manuel; Cobo, Justo; Low, John N.; Glidewell, Christopher; Acta Crystallographica Section C 63 (2007) o38–o41; doi:10.1107/S0108270106044611

data_2015764
_publ_section_title
;
 Hydrogen-bonded chains of rings in methyl
 4-[(5-methyl-1<i>H</i>-pyrazol-3-yl)amino]-3-nitrobenzoate and
 hydrogen-bonded sheets in methyl
 1-(5-methyl-1<i>H</i>-pyrazol-3-yl)-1<i>H</i>-benzimidazole-5-carboxylate
;
_journal_coeditor_code           SQ3044
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o38
_journal_page_last               o41
_journal_paper_doi               10.1107/S0108270106044611
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H12 N4 O4'
_chemical_formula_moiety         'C12 H12 N4 O4'
_chemical_formula_sum            'C12 H12 N4 O4'
_chemical_formula_weight         276.26
_chemical_name_systematic
;
methyl 4-[(5-methyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                85.690(4)
_cell_angle_beta                 83.500(4)
_cell_angle_gamma                84.015(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9233(3)
_cell_length_b                   8.8858(6)
_cell_length_c                   11.7819(6)
_cell_measurement_reflns_used    2829
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      3.48
_cell_volume                     611.51(6)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12027
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         3.48
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0711P)^2^+0.097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2117
_reflns_number_total             2829
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sq3044.cif
_cod_data_source_block           I
_cod_database_code               2015764
_cod_database_fobs_code          2015764