#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/30/2233071.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2233071
loop_
_publ_author_name
'Wang, Qian'
'Wang, Sheng'
'Wang, Yuan Yuan'
'Wang, Ying'
_publ_section_title
;
 2-(4H-1,2,4-Triazol-4-yl)pyrimidine
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o53
_journal_paper_doi               10.1107/S1600536811051968
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H5 N5'
_chemical_formula_moiety         'C6 H5 N5'
_chemical_formula_sum            'C6 H5 N5'
_chemical_formula_weight         147.15
_chemical_name_systematic
;
2-(4H-1,2,4-Triazol-4-yl)pyrimidine
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.233(2)
_cell_angle_beta                 80.755(2)
_cell_angle_gamma                69.837(2)
_cell_formula_units_Z            2
_cell_length_a                   5.6929(10)
_cell_length_b                   7.7355(14)
_cell_length_c                   8.6102(15)
_cell_measurement_reflns_used    786
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.57
_cell_volume                     328.04(10)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0100
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1803
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             152
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0346
_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/[σ²(Fo²)+(0.0595P)²+0.0336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                916
_reflns_number_total             1154
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            aa2030.cif
_cod_data_source_block           I
_cod_database_code               2233071
_cod_database_fobs_code          2233071
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.5226(2) 0.81660(19) 0.85375(15) 0.0447(4) Uani d . 1 1
N N2 0.2458(2) 0.66148(18) 0.82287(15) 0.0450(4) Uani d . 1 1
N N3 0.20693(19) 0.75348(16) 1.05328(14) 0.0371(3) Uani d . 1 1
N N4 0.0968(3) 0.8138(2) 1.28772(16) 0.0564(4) Uani d . 1 1
N N5 -0.0695(2) 0.7314(2) 1.26282(16) 0.0543(4) Uani d . 1 1
C C1 0.3340(2) 0.74312(19) 0.89977(17) 0.0349(3) Uani d . 1 1
C C2 0.3638(3) 0.6558(2) 0.6765(2) 0.0526(4) Uani d . 1 1
H H2 0.3095 0.6009 0.6157 0.063 Uiso calc R 1 1
C C3 0.5620(3) 0.7281(2) 0.61289(19) 0.0525(4) Uani d . 1 1
H H3 0.6422 0.7236 0.5109 0.063 Uiso calc R 1 1
C C4 0.6357(3) 0.8070(2) 0.7069(2) 0.0511(4) Uani d . 1 1
H H4 0.7702 0.8562 0.6671 0.061 Uiso calc R 1 1
C C5 0.2575(3) 0.8247(2) 1.16196(19) 0.0483(4) Uani d . 1 1
H H5 0.3898 0.8746 1.1478 0.058 Uiso calc R 1 1
C C6 0.0005(3) 0.6975(2) 1.12413(19) 0.0464(4) Uani d . 1 1
H H6 -0.0795 0.6422 1.0787 0.056 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0397(6) 0.0550(8) 0.0439(7) -0.0210(6) 0.0051(5) -0.0192(6)
N2 0.0507(7) 0.0556(8) 0.0394(7) -0.0242(6) 0.0061(5) -0.0245(6)
N3 0.0385(6) 0.0415(7) 0.0347(7) -0.0148(5) 0.0037(5) -0.0172(5)
N4 0.0665(9) 0.0667(9) 0.0457(8) -0.0241(7) 0.0086(6) -0.0314(7)
N5 0.0534(8) 0.0674(10) 0.0471(8) -0.0232(7) 0.0136(6) -0.0278(7)
C1 0.0347(7) 0.0347(8) 0.0336(7) -0.0089(6) 0.0000(5) -0.0126(6)
C2 0.0641(10) 0.0598(10) 0.0415(9) -0.0213(8) 0.0045(7) -0.0266(8)
C3 0.0561(10) 0.0581(10) 0.0371(9) -0.0134(8) 0.0107(7) -0.0190(8)
C4 0.0415(8) 0.0609(10) 0.0456(9) -0.0190(8) 0.0097(7) -0.0151(8)
C5 0.0556(9) 0.0580(10) 0.0448(9) -0.0256(8) 0.0040(7) -0.0278(8)
C6 0.0430(8) 0.0593(10) 0.0449(9) -0.0233(7) 0.0090(6) -0.0245(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C4 114.10(13)
C1 N2 C2 114.64(13)
C6 N3 C5 103.94(12)
C6 N3 C1 127.43(12)
C5 N3 C1 128.61(12)
C5 N4 N5 106.86(12)
C6 N5 N4 107.05(12)
N2 C1 N1 129.15(13)
N2 C1 N3 115.06(12)
N1 C1 N3 115.79(12)
N2 C2 C3 122.41(14)
N2 C2 H2 118.8
C3 C2 H2 118.8
C4 C3 C2 116.74(14)
C4 C3 H3 121.6
C2 C3 H3 121.6
N1 C4 C3 122.95(14)
N1 C4 H4 118.5
C3 C4 H4 118.5
N4 C5 N3 111.03(13)
N4 C5 H5 124.5
N3 C5 H5 124.5
N5 C6 N3 111.12(13)
N5 C6 H6 124.4
N3 C6 H6 124.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3199(18)
N1 C4 1.3407(19)
N2 C1 1.3185(18)
N2 C2 1.3386(18)
N3 C6 1.3624(18)
N3 C5 1.3629(18)
N3 C1 1.4184(17)
N4 C5 1.2965(19)
N4 N5 1.3915(19)
N5 C6 1.2927(19)
C2 C3 1.373(2)
C2 H2 0.9300
C3 C4 1.368(2)
C3 H3 0.9300
C4 H4 0.9300
C5 H5 0.9300
C6 H6 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N4 N5 C6 0.04(17)
C2 N2 C1 N1 -1.0(2)
C2 N2 C1 N3 178.77(12)
C4 N1 C1 N2 0.8(2)
C4 N1 C1 N3 -179.02(12)
C6 N3 C1 N2 -3.3(2)
C5 N3 C1 N2 178.33(13)
C6 N3 C1 N1 176.55(13)
C5 N3 C1 N1 -1.8(2)
C1 N2 C2 C3 0.5(2)
N2 C2 C3 C4 0.2(2)
C1 N1 C4 C3 0.0(2)
C2 C3 C4 N1 -0.4(2)
N5 N4 C5 N3 0.04(18)
C6 N3 C5 N4 -0.10(17)
C1 N3 C5 N4 178.59(13)
N4 N5 C6 N3 -0.11(17)
C5 N3 C6 N5 0.13(17)
C1 N3 C6 N5 -178.59(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24185771
