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_2015651
_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          'C9 H10 N4'
_chemical_formula_moiety         'C9 H10 N4'
_chemical_formula_sum            'C9 H10 N4'
_chemical_formula_weight         174.21
_chemical_melting_point          467.5(5)
_chemical_name_systematic
;
4-amino-3-methyl-5-phenyl-4H-1,2,4-triazole
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.1062(8)
_cell_length_b                   7.3981(11)
_cell_length_c                   19.653(4)
_cell_measurement_reflns_used    4368
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.75
_cell_volume                     887.8(3)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0796
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4368
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.216
_refine_ls_abs_structure_details 'Flack (1983), 660 Friedel pairs'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       0.056(11)
_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   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0683P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                1556
_reflns_number_total             1692
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            my3010.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '467-468' was changed to '467.5(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 '467-468' was changed to '467.5(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     P2ac2ab
_cod_database_code               2015651
_cod_database_fobs_code          2015651