#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/63/2226312.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_2226312
loop_
_publ_author_name
'Wasilewska, Aleksandra'
'Saczewski, Franciszek'
'Gdaniec, Maria'
_publ_section_title
;
 5-Methyl-3,6,7,8a-tetrahydro-2H-diimidazo[1,2-c:1',2'-e]pyrido[1,2-a][1,3,5]triazin-5-ium
 iodide
;
_journal_coeditor_code           TK2676
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1486
_journal_paper_doi               10.1107/S1600536810019495
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H16 N5 +, I -'
_chemical_formula_moiety         'C12 H16 N5 +, I -'
_chemical_formula_sum            'C12 H16 I N5'
_chemical_formula_weight         357.20
_chemical_name_systematic
;
5-Methyl-3,6,7,8a-tetrahydro-2H-
diimidazo[1,2-c:1',2'-e]pyrido[1,2-a][1,3,5]triazin-5-ium
iodide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.204(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6299(2)
_cell_length_b                   15.3939(4)
_cell_length_c                   11.4503(3)
_cell_measurement_reflns_used    19213
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.26
_cell_measurement_theta_min      2.65
_cell_volume                     1343.89(6)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur-E CCD'
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            25955
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         32.36
_diffrn_reflns_theta_min         4.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.374
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.735
_refine_diff_density_min         -1.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         4406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0291
_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/[σ²(Fo²)+(0.0196P)²+3.1405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                4018
_reflns_number_total             4406
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2676.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226312
_cod_database_fobs_code          2226312
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
I I1 0.04305(2) 0.194494(11) 0.473423(14) 0.01657(5) Uani d . 1 . .
N N1 0.1806(3) 0.53774(16) 0.3251(2) 0.0209(5) Uani d . 1 . .
C C2 0.2057(4) 0.4944(2) 0.2120(2) 0.0222(5) Uani d . 1 . .
H H2A 0.2910 0.5272 0.1660 0.027 Uiso calc R 1 . .
H H2B 0.0931 0.4914 0.1663 0.027 Uiso calc R 1 . .
C C3 0.2755(4) 0.40179(19) 0.2385(2) 0.0206(5) Uani d . 1 . .
H H3A 0.1869 0.3569 0.2173 0.025 Uiso calc R 1 . .
H H3B 0.3846 0.3898 0.1973 0.025 Uiso calc R 1 . .
N N4 0.3083(3) 0.40681(15) 0.36610(19) 0.0155(4) Uani d . 1 . .
N N5 0.4690(3) 0.27675(15) 0.4159(2) 0.0162(4) Uani d . 1 . .
C C6 0.5326(4) 0.23510(18) 0.5250(2) 0.0189(5) Uani d . 1 . .
H H6A 0.6623 0.2316 0.5289 0.023 Uiso calc R 1 . .
H H6B 0.4837 0.1759 0.5322 0.023 Uiso calc R 1 . .
C C7 0.4659(4) 0.29506(18) 0.6205(2) 0.0201(5) Uani d . 1 . .
H H7A 0.3677 0.2679 0.6613 0.024 Uiso calc R 1 . .
H H7B 0.5609 0.3097 0.6785 0.024 Uiso calc R 1 . .
N N8 0.4068(3) 0.37245(14) 0.55467(19) 0.0147(4) Uani d . 1 . .
C C9 0.3144(4) 0.4560(2) 0.7238(2) 0.0202(5) Uani d . 1 . .
H H9 0.3752 0.4175 0.7759 0.024 Uiso calc R 1 . .
C C10 0.2718(4) 0.5354(2) 0.7605(3) 0.0237(6) Uani d . 1 . .
H H10 0.2938 0.5510 0.8400 0.028 Uiso calc R 1 . .
C C11 0.1922(4) 0.59810(19) 0.6798(3) 0.0237(6) Uani d . 1 . .
H H11 0.1462 0.6510 0.7082 0.028 Uiso calc R 1 . .
C C12 0.1842(4) 0.58081(18) 0.5651(3) 0.0197(5) Uani d . 1 . .
H H12 0.1363 0.6226 0.5118 0.024 Uiso calc R 1 . .
N N13 0.2459(3) 0.50171(14) 0.5233(2) 0.0162(4) Uani d . 1 . .
C C14 0.2675(3) 0.42666(17) 0.6013(2) 0.0151(4) Uani d . 1 . .
H H14 0.1556 0.3928 0.6010 0.018 Uiso calc R 1 . .
C C15 0.3916(3) 0.35088(16) 0.4392(2) 0.0136(4) Uani d . 1 . .
C C16 0.2403(3) 0.48697(17) 0.4045(2) 0.0156(5) Uani d . 1 . .
C C17 0.4863(4) 0.2302(2) 0.3064(3) 0.0242(6) Uani d . 1 . .
H H17A 0.3854 0.1916 0.2934 0.036 Uiso calc R 1 . .
H H17B 0.5944 0.1957 0.3102 0.036 Uiso calc R 1 . .
H H17C 0.4909 0.2719 0.2420 0.036 Uiso calc R 1 . .
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'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 N1 C2 . . 107.1(2) ?
N1 C2 C3 . . 107.4(2) ?
N1 C2 H2A . . 110.2 ?
C3 C2 H2A . . 110.2 ?
N1 C2 H2B . . 110.2 ?
C3 C2 H2B . . 110.2 ?
H2A C2 H2B . . 108.5 ?
N4 C3 C2 . . 101.0(2) ?
N4 C3 H3A . . 111.6 ?
C2 C3 H3A . . 111.6 ?
N4 C3 H3B . . 111.6 ?
C2 C3 H3B . . 111.6 ?
H3A C3 H3B . . 109.4 ?
C15 N4 C16 . . 122.4(2) ?
C15 N4 C3 . . 129.9(2) ?
C16 N4 C3 . . 107.6(2) ?
C15 N5 C17 . . 131.1(2) ?
C15 N5 C6 . . 110.0(2) ?
C17 N5 C6 . . 118.7(2) ?
N5 C6 C7 . . 103.6(2) ?
N5 C6 H6A . . 111.0 ?
C7 C6 H6A . . 111.0 ?
N5 C6 H6B . . 111.0 ?
C7 C6 H6B . . 111.0 ?
H6A C6 H6B . . 109.0 ?
N8 C7 C6 . . 103.0(2) ?
N8 C7 H7A . . 111.2 ?
C6 C7 H7A . . 111.2 ?
N8 C7 H7B . . 111.2 ?
C6 C7 H7B . . 111.2 ?
H7A C7 H7B . . 109.1 ?
C15 N8 C14 . . 117.1(2) ?
C15 N8 C7 . . 108.2(2) ?
C14 N8 C7 . . 119.1(2) ?
C10 C9 C14 . . 121.1(3) ?
C10 C9 H9 . . 119.4 ?
C14 C9 H9 . . 119.4 ?
C9 C10 C11 . . 120.5(3) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C12 C11 C10 . . 119.6(3) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C11 C12 N13 . . 120.4(3) ?
C11 C12 H12 . . 119.8 ?
N13 C12 H12 . . 119.8 ?
C16 N13 C12 . . 118.9(2) ?
C16 N13 C14 . . 118.1(2) ?
C12 N13 C14 . . 120.6(2) ?
N13 C14 N8 . . 107.0(2) ?
N13 C14 C9 . . 110.4(2) ?
N8 C14 C9 . . 111.1(2) ?
N13 C14 H14 . . 109.4 ?
N8 C14 H14 . . 109.4 ?
C9 C14 H14 . . 109.4 ?
N5 C15 N4 . . 129.4(2) ?
N5 C15 N8 . . 112.7(2) ?
N4 C15 N8 . . 117.9(2) ?
N1 C16 N13 . . 127.0(3) ?
N1 C16 N4 . . 116.1(2) ?
N13 C16 N4 . . 116.9(2) ?
N5 C17 H17A . . 109.5 ?
N5 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N5 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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 C16 . 1.270(3) ?
N1 C2 . 1.476(4) ?
C2 C3 . 1.547(4) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 N4 . 1.475(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
N4 C15 . 1.344(3) ?
N4 C16 . 1.415(3) ?
N5 C15 . 1.317(3) ?
N5 C17 . 1.455(4) ?
N5 C6 . 1.470(3) ?
C6 C7 . 1.533(4) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 N8 . 1.471(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
N8 C15 . 1.364(3) ?
N8 C14 . 1.468(3) ?
C9 C10 . 1.336(4) ?
C9 C14 . 1.504(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.453(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.340(4) ?
C11 H11 . 0.9500 ?
C12 N13 . 1.397(3) ?
C12 H12 . 0.9500 ?
N13 C16 . 1.378(3) ?
N13 C14 . 1.466(3) ?
C14 H14 . 1.0000 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
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
C3 H3B I1 4_665 0.99 3.15 4.007(3) 145
C6 H6A I1 1_655 0.99 3.05 4.010(3) 163
C9 H9 I1 4_666 0.95 3.08 4.025(3) 172
C12 H12 I1 3_566 0.95 3.14 3.887(3) 137
C17 H17C I1 4_665 0.98 3.16 4.025(3) 148
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2103823
