#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/35/2013576.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_2013576
loop_
_publ_author_name
'Maria Gdaniec'
'Franciszek Sączewski'
'Zdzisław Brzozowski'
_publ_section_title
;2-Amino-6-(1-imidazolylmethyl)-4-(3,5,5-trimethyl-2-pyrazolin-1-yl)-1,3,5-triazine
 and
 2-amino-6-(1-benzimidazolylmethyl)-4-(3,5,5-trimethyl-2-pyrazolin-1-yl)-1,3,5-triazine
 hemihydrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o696
_journal_page_last               o699
_journal_paper_doi               10.1107/S0108270103025058
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C13 H18 N8'
_chemical_formula_moiety         'C13 H18 N8'
_chemical_formula_sum            'C13 H18 N8'
_chemical_formula_weight         286.35
_chemical_melting_point          .239E-238
_chemical_name_systematic
;
2-Amino-6-(1-imidazolylmethyl)-4-(3,5,5-trimethyl-2-pyrazolin-1-yl)-
1,3,5-triazine
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.221(5)
_cell_angle_beta                 105.342(5)
_cell_angle_gamma                106.191(6)
_cell_formula_units_Z            2
_cell_length_a                   8.2493(7)
_cell_length_b                   9.4564(7)
_cell_length_c                   9.7050(8)
_cell_measurement_reflns_used    3986
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     694.20(10)
_computing_cell_refinement
;
CrysAlis
;
_computing_data_collection
;
CrysAlis (Oxford Diffraction, 2000)
;
_computing_data_reduction
;
CrysAlis
;
_computing_molecular_graphics
;
Stereochemical Workstation (Siemens, 1989)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Kuma CCD diffractometer'
_diffrn_measurement_method       'ω 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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5098
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.2587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                2275
_reflns_number_total             2448
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa1035.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2013576
_cod_database_fobs_code          2013576
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 -0.26991(12) 0.56010(10) 0.10088(10) 0.0158(2) Uani d . 1 . . N
C2 -0.34077(15) 0.67102(13) 0.11629(13) 0.0195(2) Uani d . 1 . . C
H2 -0.3715(19) 0.6915(16) 0.2021(16) 0.024(4) Uiso d . 1 . . H
N3 -0.36353(14) 0.73997(11) 0.00153(11) 0.0234(2) Uani d . 1 . . N
C8 -0.24288(15) 0.55953(13) -0.03304(12) 0.0196(2) Uani d . 1 . . C
H8 -0.192(2) 0.4899(17) -0.0665(16) 0.025(4) Uiso d . 1 . . H
C9 -0.30161(16) 0.66924(13) -0.09244(13) 0.0216(3) Uani d . 1 . . C
H9 -0.308(2) 0.6976(17) -0.1889(17) 0.029(4) Uiso d . 1 . . H
C10 -0.21857(14) 0.46810(12) 0.20834(12) 0.0166(2) Uani d . 1 . . C
H10A -0.2778(18) 0.4747(15) 0.2816(15) 0.019(3) Uiso d . 1 . . H
H10B -0.258(2) 0.3644(17) 0.1640(16) 0.025(4) Uiso d . 1 . . H
C11 -0.02085(14) 0.51495(12) 0.27983(11) 0.0147(2) Uani d . 1 . . C
N12 0.07247(12) 0.64972(10) 0.26682(10) 0.0158(2) Uani d . 1 . . N
C13 0.24811(14) 0.68346(12) 0.33291(11) 0.0141(2) Uani d . 1 . . C
N14 0.32704(12) 0.59229(10) 0.40704(10) 0.0157(2) Uani d . 1 . . N
C15 0.21596(15) 0.45886(12) 0.41085(12) 0.0160(2) Uani d . 1 . . C
N16 0.03863(12) 0.41319(10) 0.34899(10) 0.0175(2) Uani d . 1 . . N
N17 0.34780(12) 0.82098(10) 0.32232(10) 0.0150(2) Uani d . 1 . . N
N18 0.53309(12) 0.85415(10) 0.36745(10) 0.0154(2) Uani d . 1 . . N
C19 0.59850(14) 0.98209(12) 0.33292(11) 0.0158(2) Uani d . 1 . . C
C20 0.46406(14) 1.05579(12) 0.26466(12) 0.0173(2) Uani d . 1 . . C
H20B 0.4640(19) 1.1338(17) 0.3380(16) 0.025(4) Uiso d . 1 . . H
H20A 0.486(2) 1.1052(17) 0.1814(16) 0.026(4) Uiso d . 1 . . H
C21 0.29122(14) 0.92608(12) 0.22165(12) 0.0151(2) Uani d . 1 . . C
N22 0.28486(14) 0.36140(12) 0.48171(11) 0.0207(2) Uani d . 1 . . N
H22A 0.402(2) 0.3760(17) 0.5164(17) 0.029(4) Uiso d . 1 . . H
H22B 0.213(2) 0.272(2) 0.4791(17) 0.031(4) Uiso d . 1 . . H
C23 0.24984(16) 0.85702(14) 0.06468(12) 0.0209(3) Uani d . 1 . . C
H23C 0.143(2) 0.7707(17) 0.0389(16) 0.022(3) Uiso d . 1 . . H
H23A 0.350(2) 0.8280(17) 0.0501(17) 0.030(4) Uiso d . 1 . . H
H23B 0.231(2) 0.9330(17) 0.0028(17) 0.028(4) Uiso d . 1 . . H
C24 0.13763(15) 0.97313(13) 0.24606(13) 0.0197(2) Uani d . 1 . . C
H24C 0.1624(19) 1.0129(17) 0.3484(17) 0.027(4) Uiso d . 1 . . H
H24B 0.029(2) 0.8896(18) 0.2166(17) 0.031(4) Uiso d . 1 . . H
H24A 0.1239(19) 1.0538(16) 0.1864(15) 0.022(3) Uiso d . 1 . . H
C25 0.79186(15) 1.05026(14) 0.36078(14) 0.0227(3) Uani d . 1 . . C
H25C 0.835(2) 1.1468(19) 0.4246(18) 0.034(4) Uiso d . 1 . . H
H25B 0.855(2) 0.9820(18) 0.4030(17) 0.029(4) Uiso d . 1 . . H
H25A 0.819(2) 1.0740(18) 0.2710(18) 0.032(4) Uiso d . 1 . . H
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'
H H 0.0000 0.0000 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C8 106.52(9) ?
C2 N1 C10 126.95(10) ?
C8 N1 C10 126.34(9) ?
N3 C2 N1 112.49(10) ?
N3 C2 H2 126.4(9) ?
N1 C2 H2 121.1(9) ?
C2 N3 C9 104.38(10) ?
C9 C8 N1 105.95(10) ?
C9 C8 H8 133.2(9) ?
N1 C8 H8 120.9(9) ?
C8 C9 N3 110.64(10) ?
C8 C9 H9 128.5(9) ?
N3 C9 H9 120.9(9) ?
N1 C10 C11 112.83(9) ?
N1 C10 H10A 108.2(8) ?
C11 C10 H10A 109.1(8) ?
N1 C10 H10B 109.8(9) ?
C11 C10 H10B 109.0(9) ?
H10A C10 H10B 107.8(12) ?
N12 C11 N16 127.53(10) y
N12 C11 C10 117.39(9) ?
N16 C11 C10 115.08(9) ?
C11 N12 C13 114.03(9) y
N14 C13 N17 119.25(10) ?
N14 C13 N12 125.10(10) y
N17 C13 N12 115.65(9) ?
C15 N14 C13 114.31(9) y
N22 C15 N14 117.84(10) ?
N22 C15 N16 116.46(10) ?
N14 C15 N16 125.69(10) y
C11 N16 C15 113.34(9) y
C13 N17 N18 118.38(9) ?
C13 N17 C21 126.74(9) ?
N18 N17 C21 111.18(8) ?
C19 N18 N17 107.50(9) ?
N18 C19 C25 122.03(10) ?
N18 C19 C20 114.27(10) ?
C25 C19 C20 123.69(10) ?
C19 C20 C21 102.50(9) ?
C19 C20 H20B 108.7(8) ?
C21 C20 H20B 112.0(9) ?
C19 C20 H20A 114.4(9) ?
C21 C20 H20A 112.3(9) ?
H20B C20 H20A 107.0(12) ?
N17 C21 C24 113.65(9) ?
N17 C21 C23 109.68(9) ?
C24 C21 C23 111.33(9) ?
N17 C21 C20 99.27(8) ?
C24 C21 C20 112.11(9) ?
C23 C21 C20 110.21(9) ?
C15 N22 H22A 123.3(10) ?
C15 N22 H22B 117.6(10) ?
H22A N22 H22B 117.9(14) ?
C21 C23 H23C 110.3(8) ?
C21 C23 H23A 110.5(9) ?
H23C C23 H23A 110.4(13) ?
C21 C23 H23B 107.9(9) ?
H23C C23 H23B 110.0(12) ?
H23A C23 H23B 107.7(13) ?
C21 C24 H24C 111.1(9) ?
C21 C24 H24B 110.6(9) ?
H24C C24 H24B 109.6(13) ?
C21 C24 H24A 107.1(8) ?
H24C C24 H24A 108.5(12) ?
H24B C24 H24A 109.9(12) ?
C19 C25 H25C 111.1(10) ?
C19 C25 H25B 110.4(9) ?
H25C C25 H25B 110.5(13) ?
C19 C25 H25A 110.3(10) ?
H25C C25 H25A 105.1(13) ?
H25B C25 H25A 109.4(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.3545(15) ?
N1 C8 . 1.3756(15) ?
N1 C10 . 1.4484(14) ?
C2 N3 . 1.3191(16) ?
C2 H2 . 0.957(15) ?
N3 C9 . 1.3815(16) ?
C8 C9 . 1.3577(17) ?
C8 H8 . 0.959(15) ?
C9 H9 . 0.980(16) ?
C10 C11 . 1.5171(15) ?
C10 H10A . 0.971(14) ?
C10 H10B . 0.976(15) ?
C11 N12 . 1.3248(14) y
C11 N16 . 1.3338(14) y
N12 C13 . 1.3565(14) y
C13 N14 . 1.3489(14) y
C13 N17 . 1.3570(14) y
N14 C15 . 1.3459(14) y
C15 N22 . 1.3424(15) y
C15 N16 . 1.3567(15) y
N17 N18 . 1.4105(12) y
N17 C21 . 1.5121(13) ?
N18 C19 . 1.2823(15) y
C19 C25 . 1.4872(15) ?
C19 C20 . 1.4996(15) ?
C20 C21 . 1.5375(15) ?
C20 H20B . 0.996(15) ?
C20 H20A . 0.988(15) ?
C21 C24 . 1.5234(15) ?
C21 C23 . 1.5337(16) ?
N22 H22A . 0.905(17) ?
N22 H22B . 0.881(18) ?
C23 H23C . 0.980(15) ?
C23 H23A . 0.984(16) ?
C23 H23B . 0.980(16) ?
C24 H24C . 0.988(15) ?
C24 H24B . 0.974(17) ?
C24 H24A . 0.997(15) ?
C25 H25C . 0.991(17) ?
C25 H25B . 0.982(16) ?
C25 H25A . 0.977(17) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N22 H22A N14 2_666 0.905(17) 2.085(17) 2.9906(14) 179.0(15)
N22 H22A N18 2_666 0.905(17) 2.626(16) 3.0712(14) 111.2(12)
C2 H2 N18 1_455 0.957(15) 2.574(15) 3.4491(15) 152.1(12)
C20 H20A N3 2_575 0.988(15) 2.547(15) 3.3782(15) 141.6(11)
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
_geom_torsion_publ_flag
N16 C11 C10 N1 -162.58(9) ?
N12 C11 C10 N1 17.25(14) y
C11 C10 N1 C2 -101.91(12) y
C11 C10 N1 C8 72.46(14) ?
N17 N18 C19 C20 2.52(13) y
N18 C19 C20 C21 -16.22(13) y
C19 C20 C21 N17 20.89(10) y
C20 C21 N17 N18 -21.73(11) y
C21 N17 N18 C19 13.10(12) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 355098
