#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/20/2212077.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_2212077
loop_
_publ_author_name
'Liepa, Andris J.'
'Jahangiri, Saba'
'Fallon, Gary D.'
'Forsyth, Craig M.'
_publ_section_title
(2,3-Dimethyl-7,7-dioxo-7H-4-oxa-7λ⁶-thia-1,6,7a-triazainden-5-yl)diethyamine
_journal_coeditor_code           BX2052
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o887
_journal_page_last               o888
_journal_paper_doi               10.1107/S1600536807002814
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H16 N4 O3 S'
_chemical_formula_moiety         'C10 H16 N4 O3 S'
_chemical_formula_sum            'C10 H16 N4 O3 S'
_chemical_formula_weight         272.33
_chemical_name_systematic
;
(2,3-Dimethyl-7,7-dioxo-7H-4-oxa-7λ⁶-thia-1,6,7a-triazainden-5-
yl)dimethyamine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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
_cell_angle_beta                 128.7100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2639(2)
_cell_length_b                   8.67920(10)
_cell_length_c                   16.0670(2)
_cell_measurement_reflns_used    14079
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      3.4
_cell_volume                     2531.46(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ? ω?'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13225
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         3.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.408
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0344
_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)+(0.0407P)²+2.3884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                2598
_reflns_number_total             3127
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2052.cif
_cod_data_source_block           III
_cod_original_cell_volume        2531.45(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2212077
_cod_database_fobs_code          2212077
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C C1 0.14139(7) 0.41820(17) -0.02212(11) 0.0181(3) Uani d . 1
C C2 0.21233(8) 0.40115(17) 0.07865(11) 0.0173(3) Uani d . 1
C C3 0.23427(7) 0.54927(16) 0.10941(11) 0.0153(3) Uani d . 1
C C4 0.31690(7) 0.75313(16) 0.20357(11) 0.0152(3) Uani d . 1
C C5 0.09132(9) 0.28981(19) -0.09285(13) 0.0263(3) Uani d . 1
H H5A 0.0447 0.3326 -0.1554 0.039 Uiso calc R 1
H H5B 0.0817 0.2232 -0.0535 0.039 Uiso calc R 1
H H5C 0.1147 0.2294 -0.1159 0.039 Uiso calc R 1
C C6 0.25349(9) 0.25738(17) 0.13652(13) 0.0255(3) Uani d . 1
H H6A 0.2990 0.2839 0.2073 0.038 Uiso calc R 1
H H6B 0.2657 0.2024 0.0961 0.038 Uiso calc R 1
H H6C 0.2229 0.1914 0.1442 0.038 Uiso calc R 1
C C7 0.41776(8) 0.93523(17) 0.29780(11) 0.0194(3) Uani d . 1
H H7A 0.3934 0.9793 0.2260 0.023 Uiso calc R 1
H H7B 0.4708 0.9238 0.3331 0.023 Uiso calc R 1
C C8 0.40855(9) 1.04482(18) 0.36213(12) 0.0237(3) Uani d . 1
H H8A 0.3560 1.0584 0.3264 0.036 Uiso calc R 1
H H8B 0.4305 1.1447 0.3680 0.036 Uiso calc R 1
H H8C 0.4332 1.0022 0.4336 0.036 Uiso calc R 1
C C9 0.43435(8) 0.66410(18) 0.36755(11) 0.0222(3) Uani d . 1
H H9A 0.4046 0.5965 0.3771 0.027 Uiso calc R 1
H H9B 0.4720 0.7153 0.4366 0.027 Uiso calc R 1
C C10 0.47249(10) 0.5667(2) 0.33708(15) 0.0404(5) Uani d . 1
H H10A 0.4355 0.5137 0.2696 0.061 Uiso calc R 1
H H10B 0.5039 0.4903 0.3931 0.061 Uiso calc R 1
H H10C 0.5028 0.6328 0.3288 0.061 Uiso calc R 1
N N1 0.12129(6) 0.56412(14) -0.05076(9) 0.0181(3) Uani d . 1
N N2 0.18075(6) 0.64600(14) 0.03280(9) 0.0165(2) Uani d . 1
N N3 0.27323(6) 0.85779(14) 0.13312(10) 0.0194(3) Uani d . 1
N N4 0.38609(6) 0.78223(14) 0.28681(9) 0.0174(3) Uani d . 1
O O1 0.29785(5) 0.60370(11) 0.20127(7) 0.0174(2) Uani d . 1
O O2 0.16421(6) 0.89955(12) -0.05500(8) 0.0216(2) Uani d . 1
O O3 0.14768(6) 0.88804(12) 0.08010(9) 0.0245(3) Uani d . 1
S S1 0.187146(18) 0.83864(4) 0.04381(3) 0.01520(10) 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
N1 C1 C2 113.56(12)
N1 C1 C5 120.61(13)
C2 C1 C5 125.83(13)
C3 C2 C1 102.73(12)
C3 C2 C6 128.08(13)
C1 C2 C6 129.19(13)
C2 C3 N2 109.39(12)
C2 C3 O1 128.96(13)
N2 C3 O1 121.65(12)
N3 C4 N4 122.64(13)
N3 C4 O1 125.14(12)
N4 C4 O1 112.22(12)
C1 C5 H5A 109.5
C1 C5 H5B 109.5
H5A C5 H5B 109.5
C1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C2 C6 H6A 109.5
C2 C6 H6B 109.5
H6A C6 H6B 109.5
C2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N4 C7 C8 111.94(12)
N4 C7 H7A 109.2
C8 C7 H7A 109.2
N4 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N4 C9 C10 112.48(13)
N4 C9 H9A 109.1
C10 C9 H9A 109.1
N4 C9 H9B 109.1
C10 C9 H9B 109.1
H9A C9 H9B 107.8
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C1 N1 N2 103.46(11)
C3 N2 N1 110.86(12)
C3 N2 S1 123.27(10)
N1 N2 S1 125.83(9)
C4 N3 S1 124.84(10)
C4 N4 C9 122.16(12)
C4 N4 C7 119.59(12)
C9 N4 C7 118.19(11)
C3 O1 C4 118.24(11)
O2 S1 O3 117.14(7)
O2 S1 N3 110.59(7)
O3 S1 N3 111.76(7)
O2 S1 N2 107.81(6)
O3 S1 N2 107.77(6)
N3 S1 N2 100.30(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3286(19)
C1 C2 1.4230(19)
C1 C5 1.495(2)
C2 C3 1.357(2)
C2 C6 1.492(2)
C3 N2 1.3614(17)
C3 O1 1.3634(16)
C4 N3 1.3039(18)
C4 N4 1.3233(17)
C4 O1 1.3636(17)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 N4 1.4747(19)
C7 C8 1.515(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 N4 1.4741(18)
C9 C10 1.512(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
N1 N2 1.3778(16)
N2 S1 1.6781(12)
N3 S1 1.5821(12)
O2 S1 1.4230(11)
O3 S1 1.4270(11)
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
C9 H9A O3 4_545 0.99 2.50 3.4782(19) 168
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125492
