N—H···N and C—H···π interactions in 4-amino-3-methyl-5-(<i>p</i>-tolyl)-4<i>H</i>-1,2,4-triazole and 4-amino-3-methyl-5-phenyl-4<i>H</i>-1,2,4-triazole
Şahin, Onur; Büyükgüngör, Orhan; Şaşmaz, Selami; Gümrükçüoǧlu, Nurhan; Kantar, Cihan; Acta Crystallographica Section C 62 (2006) o643–o646; doi:10.1107/S0108270106037668

data_2015650
_publ_section_title
;
 N---H&#x00B7;&#x00B7;&#x00B7;N and C---H&#x00B7;&#x00B7;&#x00B7;\p
 interactions in
 4-amino-3-methyl-5-(<i>p</i>-tolyl)-4<i>H</i>-1,2,4-triazole and
 4-amino-3-methyl-5-phenyl-4<i>H</i>-1,2,4-triazole
;
_journal_coeditor_code           MY3010
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o643
_journal_page_last               o646
_journal_paper_doi               10.1107/S0108270106037668
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H12 N4'
_chemical_formula_moiety         'C10 H12 N4'
_chemical_formula_sum            'C10 H12 N4'
_chemical_formula_weight         188.24
_chemical_melting_point          488.5(5)
_chemical_name_systematic
;
4-amino-3-methyl-5-(p-tolyl)-4H-1,2,4-triazole
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   16.4033(11)
_cell_length_b                   16.4033(11)
_cell_length_c                   15.7192(12)
_cell_measurement_reflns_used    7427
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.76
_cell_volume                     4229.5(5)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics
;ORTEP-3 for Windows (Farrugia, 1997)
and Mercury (Macrae <i>et al.</i>,  2006)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS-II'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7427
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'square prism'
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.51
_refine_diff_density_max         0.11
_refine_diff_density_min         -0.11
_refine_ls_extinction_coef       0.0019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.2861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                1511
_reflns_number_total             2082
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            my3010.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '488-489' was changed to '488.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '488-489' was changed to '488.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     -I4ad
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               2015650
_cod_database_fobs_code          2015650