#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/81/2228156.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228156
loop_
_publ_author_name
'Tian, Zhongzhen'
'Dong, Haijun'
'Li, Dongmei'
'Wang, Gaolei'
_publ_section_title
;
 1-[(1,3-Dithiolan-2-yl)methyl]-6-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-c]pyrimidine
;
_journal_coeditor_code           ZL2297
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2330
_journal_paper_doi               10.1107/S160053681003206X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H18 N4 O2 S2'
_chemical_formula_moiety         'C11 H18 N4 O2 S2'
_chemical_formula_sum            'C11 H18 N4 O2 S2'
_chemical_formula_weight         302.41
_chemical_name_systematic
;
1-[(1,3-Dithiolan-2-yl)methyl]-6-methyl-8-nitro-1,2,3,5,6,7-
hexahydroimidazo[1,2-c]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                80.4610(10)
_cell_angle_beta                 83.4970(10)
_cell_angle_gamma                68.0430(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0326(7)
_cell_length_b                   9.3521(8)
_cell_length_c                   10.1109(9)
_cell_measurement_reflns_used    4541
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.37
_cell_volume                     693.62(10)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7993
_diffrn_reflns_theta_full        27.66
_diffrn_reflns_theta_max         27.66
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.9335
_exptl_absorpt_correction_T_min  0.9059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.338
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0369
_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)+(0.0447P)²+0.2729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                2826
_reflns_number_total             3178
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zl2297.cif
_cod_data_source_block           I
_cod_database_code               2228156
_cod_database_fobs_code          2228156
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_disorder_assembly
_atom_site_disorder_group
C C1 0.92947(18) 0.16249(17) 0.65277(14) 0.0319(3) Uani d . 1 . .
C C2 1.0078(2) 0.10338(19) 0.78875(16) 0.0375(3) Uani d . 1 . .
H H2A 0.9189 0.1516 0.8570 0.045 Uiso calc R 1 . .
H H2B 1.0364 -0.0081 0.8074 0.045 Uiso calc R 1 . .
C C3 1.2634(3) 0.0458(2) 0.9163(2) 0.0549(5) Uani d . 1 . .
H H3A 1.2903 -0.0628 0.9137 0.082 Uiso calc R 1 . .
H H3B 1.1876 0.0770 0.9949 0.082 Uiso calc R 1 . .
H H3C 1.3731 0.0636 0.9189 0.082 Uiso calc R 1 . .
C C4 1.2876(2) 0.0997(2) 0.67697(17) 0.0409(4) Uani d . 1 . .
H H4A 1.3993 0.1141 0.6851 0.049 Uiso calc R 1 . .
H H4B 1.3154 -0.0077 0.6650 0.049 Uiso calc R 1 . .
C C5 1.2874(2) 0.2345(2) 0.43686(17) 0.0459(4) Uani d . 1 . .
H H5A 1.3595 0.1393 0.4003 0.055 Uiso calc R 1 . .
H H5B 1.3635 0.2914 0.4466 0.055 Uiso calc R 1 . .
C C6 1.1325(2) 0.3324(3) 0.35069(19) 0.0544(5) Uani d . 1 . .
H H6A 1.1106 0.4422 0.3466 0.065 Uiso calc R 1 . .
H H6B 1.1554 0.3050 0.2602 0.065 Uiso calc R 1 . .
C C7 1.02457(19) 0.22041(17) 0.54533(14) 0.0316(3) Uani d . 1 . .
C C8 0.7976(2) 0.40401(18) 0.38887(15) 0.0361(3) Uani d . 1 . .
H H8A 0.8020 0.5074 0.3646 0.043 Uiso calc R 1 . .
H H8B 0.7182 0.4057 0.4688 0.043 Uiso calc R 1 . .
C C9 0.7185(2) 0.36571(18) 0.27473(15) 0.0369(3) Uani d . 1 . .
H H9 0.7140 0.2614 0.3005 0.044 Uiso calc R 1 . .
C C10 0.7343(3) 0.5774(2) 0.0715(2) 0.0580(5) Uani d . 1 . .
H H10A 0.7905 0.6289 0.1179 0.070 Uiso calc R 1 . .
H H10B 0.7517 0.6059 -0.0244 0.070 Uiso calc R 1 . .
C C11 0.5376(3) 0.6301(2) 0.1105(2) 0.0553(5) Uani d . 1 . .
H H11A 0.4723 0.6319 0.0349 0.066 Uiso calc R 1 . .
H H11B 0.4967 0.7350 0.1334 0.066 Uiso calc R 1 . .
N N1 0.78451(16) 0.12503(15) 0.63650(13) 0.0351(3) Uani d . 1 . .
N N2 1.17052(18) 0.13662(16) 0.79623(13) 0.0379(3) Uani d . 1 . .
N N3 1.19480(17) 0.20279(17) 0.56373(13) 0.0392(3) Uani d . 1 . .
N N4 0.97815(17) 0.29393(16) 0.42032(13) 0.0371(3) Uani d . 1 . .
O O1 0.71913(17) 0.14805(16) 0.52435(12) 0.0489(3) Uani d . 1 . .
O O2 0.72085(16) 0.06008(15) 0.73842(12) 0.0468(3) Uani d . 1 . .
S S1 0.83905(6) 0.36969(6) 0.11346(4) 0.04884(14) Uani d . 1 . .
S S2 0.49010(6) 0.50283(6) 0.25217(5) 0.05506(15) Uani d . 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N1 C1 C7 . . 123.33(13) ?
N1 C1 C2 . . 114.77(12) ?
C7 C1 C2 . . 120.49(12) ?
N2 C2 C1 . . 112.09(12) ?
N2 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
N2 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
N2 C3 H3A . . 109.5 ?
N2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
N2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N3 C4 N2 . . 107.66(13) ?
N3 C4 H4A . . 110.2 ?
N2 C4 H4A . . 110.2 ?
N3 C4 H4B . . 110.2 ?
N2 C4 H4B . . 110.2 ?
H4A C4 H4B . . 108.5 ?
N3 C5 C6 . . 101.87(13) ?
N3 C5 H5A . . 111.4 ?
C6 C5 H5A . . 111.4 ?
N3 C5 H5B . . 111.4 ?
C6 C5 H5B . . 111.4 ?
H5A C5 H5B . . 109.3 ?
N4 C6 C5 . . 103.53(13) ?
N4 C6 H6A . . 111.1 ?
C5 C6 H6A . . 111.1 ?
N4 C6 H6B . . 111.1 ?
C5 C6 H6B . . 111.1 ?
H6A C6 H6B . . 109.0 ?
N3 C7 N4 . . 110.27(13) ?
N3 C7 C1 . . 117.58(13) ?
N4 C7 C1 . . 132.15(13) ?
N4 C8 C9 . . 113.81(13) ?
N4 C8 H8A . . 108.8 ?
C9 C8 H8A . . 108.8 ?
N4 C8 H8B . . 108.8 ?
C9 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
C8 C9 S1 . . 115.71(11) ?
C8 C9 S2 . . 109.68(11) ?
S1 C9 S2 . . 106.91(8) ?
C8 C9 H9 . . 108.1 ?
S1 C9 H9 . . 108.1 ?
S2 C9 H9 . . 108.1 ?
C11 C10 S1 . . 110.59(13) ?
C11 C10 H10A . . 109.5 ?
S1 C10 H10A . . 109.5 ?
C11 C10 H10B . . 109.5 ?
S1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
C10 C11 S2 . . 111.27(13) ?
C10 C11 H11A . . 109.4 ?
S2 C11 H11A . . 109.4 ?
C10 C11 H11B . . 109.4 ?
S2 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
O1 N1 O2 . . 120.14(12) ?
O1 N1 C1 . . 122.24(13) ?
O2 N1 C1 . . 117.56(12) ?
C4 N2 C3 . . 110.33(14) ?
C4 N2 C2 . . 110.28(12) ?
C3 N2 C2 . . 109.41(13) ?
C7 N3 C4 . . 120.45(13) ?
C7 N3 C5 . . 110.88(13) ?
C4 N3 C5 . . 122.79(13) ?
C7 N4 C8 . . 123.79(12) ?
C7 N4 C6 . . 108.50(12) ?
C8 N4 C6 . . 117.02(13) ?
C10 S1 C9 . . 93.94(8) ?
C11 S2 C9 . . 98.01(8) ?
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
C1 N1 . 1.3686(18) ?
C1 C7 . 1.408(2) ?
C1 C2 . 1.509(2) ?
C2 N2 . 1.4642(19) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N2 . 1.463(2) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 N3 . 1.444(2) ?
C4 N2 . 1.448(2) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 N3 . 1.452(2) ?
C5 C6 . 1.508(2) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 N4 . 1.488(2) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 N3 . 1.3455(18) ?
C7 N4 . 1.3552(19) ?
C8 N4 . 1.4640(19) ?
C8 C9 . 1.529(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 S1 . 1.8019(16) ?
C9 S2 . 1.8169(16) ?
C9 H9 . 0.9800 ?
C10 C11 . 1.495(3) ?
C10 S1 . 1.802(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 S2 . 1.8068(19) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
N1 O1 . 1.2559(17) ?
N1 O2 . 1.2641(17) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 N2 . . . . 175.52(13) ?
C7 C1 C2 N2 . . . . 8.6(2) ?
N3 C5 C6 N4 . . . . -20.74(19) ?
N1 C1 C7 N3 . . . . -157.53(14) ?
C2 C1 C7 N3 . . . . 8.2(2) ?
N1 C1 C7 N4 . . . . 22.3(3) ?
C2 C1 C7 N4 . . . . -171.97(15) ?
N4 C8 C9 S1 . . . . -62.50(16) ?
N4 C8 C9 S2 . . . . 176.50(10) ?
S1 C10 C11 S2 . . . . 28.7(2) ?
C7 C1 N1 O1 . . . . -4.1(2) ?
C2 C1 N1 O1 . . . . -170.58(14) ?
C7 C1 N1 O2 . . . . 173.30(14) ?
C2 C1 N1 O2 . . . . 6.8(2) ?
N3 C4 N2 C3 . . . . -174.80(13) ?
N3 C4 N2 C2 . . . . 64.22(16) ?
C1 C2 N2 C4 . . . . -44.99(17) ?
C1 C2 N2 C3 . . . . -166.51(14) ?
N4 C7 N3 C4 . . . . -166.78(14) ?
C1 C7 N3 C4 . . . . 13.1(2) ?
N4 C7 N3 C5 . . . . -13.07(19) ?
C1 C7 N3 C5 . . . . 166.80(14) ?
N2 C4 N3 C7 . . . . -49.50(19) ?
N2 C4 N3 C5 . . . . 159.98(14) ?
C6 C5 N3 C7 . . . . 21.40(19) ?
C6 C5 N3 C4 . . . . 174.39(16) ?
N3 C7 N4 C8 . . . . -144.85(14) ?
C1 C7 N4 C8 . . . . 35.3(2) ?
N3 C7 N4 C6 . . . . -1.68(19) ?
C1 C7 N4 C6 . . . . 178.48(17) ?
C9 C8 N4 C7 . . . . -127.28(15) ?
C9 C8 N4 C6 . . . . 92.38(18) ?
C5 C6 N4 C7 . . . . 14.7(2) ?
C5 C6 N4 C8 . . . . 160.67(14) ?
C11 C10 S1 C9 . . . . -42.36(16) ?
C8 C9 S1 C10 . . . . -82.86(13) ?
S2 C9 S1 C10 . . . . 39.62(10) ?
C10 C11 S2 C9 . . . . -0.91(17) ?
C8 C9 S2 C11 . . . . 99.63(12) ?
S1 C9 S2 C11 . . . . -26.54(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745778
