Self-assembly of N<i>H</i>-pyrazoles <i>via</i> intermolecular N—H···N hydrogen bonds
Bertolasi, Valerio; Gilli, Paola; Ferretti, Valeria; Gilli, Gastone; Fernàndez-Castaño, Cristina; Acta Crystallographica Section B 55 (1999) 985–993; doi:10.1107/S0108768199004966

data_2105618
_publ_section_title
;
 Self-assembly of N<i>H</i>-pyrazoles <i>via</i> intermolecular
 N---H&#x00B7;&#x00B7;&#x00B7;N hydrogen bonds
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              985
_journal_page_last               993
_journal_paper_doi               10.1107/S0108768199004966
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C8 H10 N4 O'
_chemical_formula_sum            'C8 H10 N4 O'
_chemical_formula_weight         178.20
_chemical_name_systematic
;
3-hydroxy-5-methyl-4-(3'-methylpyrazol-5'-yl)pyrazole
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.409(3)
_cell_length_b                   7.6190(10)
_cell_length_c                   13.544(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1693.3(8)
_computing_cell_refinement       'CAD4 Enraf-Nonius, 1984'
_computing_data_collection       'CAD4 Enraf-Nonius, 1984'
_computing_data_reduction        ' MolEN, C.K. Fair, Enraf-Nonius, 1990'
_computing_molecular_graphics    'ORTEPII, Johnson, 1976'
_computing_publication_material
' PARST (Nardelli, 1983, 1995), SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELX97, Sheldrick, 1997'
_computing_structure_solution    'SIR92, Altomare et al., 1994'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'Enraf Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0000
_diffrn_reflns_av_sigmaI/netI    .0425
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1841
_diffrn_reflns_theta_full        27.03
_diffrn_reflns_theta_max         27.03
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          .33
_exptl_crystal_size_mid          .26
_exptl_crystal_size_min          .23
_refine_diff_density_max         .270
_refine_diff_density_min         -.378
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          .1142
_refine_ls_R_factor_gt           .0696
_refine_ls_shift/su_max          .010
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1089P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1863
_reflns_number_gt                1100
_reflns_number_total             1841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            na0091.cif
_cod_data_source_block           P1
_cod_database_code               2105618