# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DBT100K
_database_code_depnum_ccdc_archive 'CCDC 1434221'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,2-Diazabicyclo(2.2.2)octane bis(thiourea)'
_chemical_name_common            '1,2-Diazabicyclo(2.2.2)octane bis(thiourea)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, 2(C H4 N2 S)'
_chemical_formula_sum            'C8 H20 N6 S2'
_chemical_formula_weight         264.44

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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'

_cell_length_a                   19.106(7)
_cell_length_b                   15.504(7)
_cell_length_c                   18.03(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.648(15)
_cell_angle_gamma                90.00
_cell_volume                     5315(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2272
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7124
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18174
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6091
_reflns_number_gt                4179
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1969P)²+3.7385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6091
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0972
_refine_ls_wR_factor_ref         0.2933
_refine_ls_wR_factor_gt          0.2683
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.005

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.21842(10) 0.54195(13) 0.05098(11) 0.0206(5) Uani 1 1 d . . .
N12 N 0.28767(11) 0.46679(13) -0.04610(11) 0.0225(5) Uani 1 1 d . . .
C15A C 0.2334(3) 0.6036(3) -0.0062(3) 0.0284(11) Uani 0.506(3) 1 d P A 1
H15A H 0.2612 0.6523 0.0166 0.034 Uiso 0.506(3) 1 calc PR A 1
H15B H 0.1889 0.6267 -0.0313 0.034 Uiso 0.506(3) 1 calc PR A 1
C16B C 0.3239(3) 0.5439(3) -0.0223(3) 0.0334(14) Uani 0.494(3) 1 d P A 2
H16A H 0.3261 0.5836 -0.0651 0.040 Uiso 0.494(3) 1 calc PR A 2
H16B H 0.3725 0.5302 -0.0017 0.040 Uiso 0.494(3) 1 calc PR A 2
C12B C 0.2782(3) 0.4065(3) 0.0128(3) 0.0288(12) Uani 0.494(3) 1 d P A 2
H12A H 0.3244 0.3883 0.0374 0.035 Uiso 0.494(3) 1 calc PR A 2
H12B H 0.2530 0.3546 -0.0077 0.035 Uiso 0.494(3) 1 calc PR A 2
C11A C 0.2853(3) 0.5117(3) 0.0905(2) 0.0264(11) Uani 0.506(3) 1 d P A 1
H11A H 0.2759 0.4715 0.1309 0.032 Uiso 0.506(3) 1 calc PR A 1
H11B H 0.3125 0.5613 0.1128 0.032 Uiso 0.506(3) 1 calc PR A 1
C13B C 0.1752(2) 0.5372(3) -0.0264(2) 0.0236(11) Uani 0.494(3) 1 d P A 2
H13A H 0.1306 0.5060 -0.0216 0.028 Uiso 0.494(3) 1 calc PR A 2
H13B H 0.1634 0.5963 -0.0442 0.028 Uiso 0.494(3) 1 calc PR A 2
C15B C 0.2837(3) 0.5868(4) 0.0378(3) 0.0333(13) Uani 0.494(3) 1 d P A 2
H15C H 0.3148 0.5889 0.0850 0.040 Uiso 0.494(3) 1 calc PR A 2
H15D H 0.2723 0.6469 0.0225 0.040 Uiso 0.494(3) 1 calc PR A 2
C12A C 0.3281(2) 0.4650(3) 0.0330(2) 0.0232(10) Uani 0.506(3) 1 d P A 1
H12C H 0.3743 0.4937 0.0316 0.028 Uiso 0.506(3) 1 calc PR A 1
H12D H 0.3367 0.4044 0.0487 0.028 Uiso 0.506(3) 1 calc PR A 1
C13A C 0.1791(3) 0.4687(3) 0.0217(3) 0.0318(12) Uani 0.506(3) 1 d P A 1
H13C H 0.1325 0.4874 -0.0018 0.038 Uiso 0.506(3) 1 calc PR A 1
H13D H 0.1717 0.4278 0.0623 0.038 Uiso 0.506(3) 1 calc PR A 1
C14B C 0.2170(3) 0.4901(3) -0.0843(3) 0.0275(11) Uani 0.494(3) 1 d P A 2
H14A H 0.1917 0.4374 -0.1028 0.033 Uiso 0.494(3) 1 calc PR A 2
H14B H 0.2225 0.5283 -0.1273 0.033 Uiso 0.494(3) 1 calc PR A 2
C14A C 0.2204(2) 0.4255(3) -0.0356(3) 0.0316(13) Uani 0.506(3) 1 d P A 1
H14C H 0.2294 0.3649 -0.0204 0.038 Uiso 0.506(3) 1 calc PR A 1
H14D H 0.1910 0.4247 -0.0840 0.038 Uiso 0.506(3) 1 calc PR A 1
C16A C 0.2749(3) 0.5577(3) -0.0631(3) 0.0241(10) Uani 0.506(3) 1 d P A 1
H16C H 0.2486 0.5625 -0.1131 0.029 Uiso 0.506(3) 1 calc PR A 1
H16D H 0.3207 0.5872 -0.0650 0.029 Uiso 0.506(3) 1 calc PR A 1
C11B C 0.2351(2) 0.4518(3) 0.0692(2) 0.0232(10) Uani 0.494(3) 1 d P A 2
H11C H 0.1906 0.4198 0.0720 0.028 Uiso 0.494(3) 1 calc PR A 2
H11D H 0.2618 0.4494 0.1191 0.028 Uiso 0.494(3) 1 calc PR A 2
N10 N 0.53561(10) 0.21383(13) -0.04313(10) 0.0213(5) Uani 1 1 d . . .
N9 N 0.46547(10) 0.28869(13) 0.05305(10) 0.0201(5) Uani 1 1 d . . .
C8 C 0.57608(11) 0.21416(15) 0.02975(12) 0.0187(5) Uani 1 1 d . . .
H8A H 0.6215 0.2439 0.0264 0.022 Uiso 1 1 calc R . .
H8B H 0.5861 0.1541 0.0462 0.022 Uiso 1 1 calc R . .
C9 C 0.47697(14) 0.34884(16) -0.00870(13) 0.0252(6) Uani 1 1 d . . .
H9A H 0.5027 0.4005 0.0115 0.030 Uiso 1 1 calc R . .
H9B H 0.4311 0.3678 -0.0336 0.030 Uiso 1 1 calc R . .
C5 C 0.42728(13) 0.21343(18) 0.02134(15) 0.0297(6) Uani 1 1 d . . .
H5A H 0.3808 0.2317 -0.0025 0.036 Uiso 1 1 calc R . .
H5B H 0.4195 0.1722 0.0617 0.036 Uiso 1 1 calc R . .
C6 C 0.46894(13) 0.16817(17) -0.03730(14) 0.0265(6) Uani 1 1 d . . .
H6A H 0.4786 0.1075 -0.0224 0.032 Uiso 1 1 calc R . .
H6B H 0.4406 0.1681 -0.0864 0.032 Uiso 1 1 calc R . .
C7 C 0.53426(14) 0.26091(15) 0.08714(13) 0.0208(5) Uani 1 1 d . . .
H7A H 0.5280 0.2215 0.1292 0.025 Uiso 1 1 calc R . .
H7B H 0.5612 0.3118 0.1072 0.025 Uiso 1 1 calc R . .
C10 C 0.51982(13) 0.30355(15) -0.06592(12) 0.0231(6) Uani 1 1 d . . .
H10A H 0.4926 0.3041 -0.1156 0.028 Uiso 1 1 calc R . .
H10B H 0.5643 0.3353 -0.0697 0.028 Uiso 1 1 calc R . .
S3 S 0.05049(3) -0.00628(4) 0.15709(3) 0.0201(3) Uani 1 1 d . . .
N6 N 0.08640(13) 0.09627(15) 0.27194(11) 0.0331(6) Uani 1 1 d . . .
H6C H 0.1120 0.1366 0.2958 0.040 Uiso 1 1 calc R . .
H6D H 0.0510 0.0730 0.2925 0.040 Uiso 1 1 calc R . .
N5 N 0.15481(11) 0.10686(13) 0.17553(11) 0.0257(5) Uani 1 1 d . . .
H5C H 0.1797 0.1471 0.2003 0.031 Uiso 1 1 calc R . .
H5D H 0.1655 0.0908 0.1312 0.031 Uiso 1 1 calc R . .
C3 C 0.10119(13) 0.07050(14) 0.20488(13) 0.0224(5) Uani 1 1 d . . .
S2 S 0.29264(3) 0.25585(4) 0.15506(3) 0.0235(3) Uani 1 1 d . . .
N4 N 0.32903(10) 0.35220(14) 0.27413(10) 0.0218(5) Uani 1 1 d . . .
H4A H 0.3568 0.3882 0.3008 0.026 Uiso 1 1 calc R . .
H4B H 0.2902 0.3335 0.2913 0.026 Uiso 1 1 calc R . .
N3 N 0.40450(10) 0.35584(13) 0.18414(11) 0.0221(5) Uani 1 1 d . . .
H3A H 0.4313 0.3918 0.2120 0.027 Uiso 1 1 calc R . .
H3B H 0.4168 0.3396 0.1405 0.027 Uiso 1 1 calc R . .
C1 C 0.34564(11) 0.32617(14) 0.20795(12) 0.0173(5) Uani 1 1 d . . .
S4 S 0.19092(3) 0.25359(4) 0.34163(3) 0.0235(3) Uani 1 1 d . . .
N7 N 0.15164(10) 0.35374(14) 0.22580(11) 0.0229(5) Uani 1 1 d . . .
H7C H 0.1245 0.3925 0.2017 0.027 Uiso 1 1 calc R . .
H7D H 0.1872 0.3314 0.2049 0.027 Uiso 1 1 calc R . .
N8 N 0.08481(11) 0.36380(14) 0.32400(12) 0.0260(5) Uani 1 1 d . . .
H8C H 0.0582 0.4025 0.2991 0.031 Uiso 1 1 calc R . .
H8D H 0.0756 0.3481 0.3689 0.031 Uiso 1 1 calc R . .
C2 C 0.13900(11) 0.32898(15) 0.29360(13) 0.0189(5) Uani 1 1 d . . .
S1 S 0.44889(3) 0.01579(4) 0.34402(3) 0.0215(3) Uani 1 1 d . . .
N2 N 0.40966(13) 0.10931(14) 0.22353(11) 0.0308(5) Uani 1 1 d . . .
H2A H 0.3815 0.1448 0.1968 0.037 Uiso 1 1 calc R . .
H2B H 0.4483 0.0905 0.2061 0.037 Uiso 1 1 calc R . .
N1 N 0.33544(11) 0.11309(13) 0.31533(11) 0.0251(5) Uani 1 1 d . . .
H1A H 0.3078 0.1486 0.2879 0.030 Uiso 1 1 calc R . .
H1B H 0.3242 0.0970 0.3594 0.030 Uiso 1 1 calc R . .
C4 C 0.39383(13) 0.08403(14) 0.29029(12) 0.0222(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C13A 1.434(5) . ?
N11 C15A 1.455(5) . ?
N11 C11B 1.464(5) . ?
N11 C15B 1.468(5) . ?
N11 C11A 1.477(5) . ?
N11 C13B 1.551(5) . ?
N12 C16B 1.426(5) . ?
N12 C12B 1.440(5) . ?
N12 C16A 1.458(5) . ?
N12 C14A 1.465(4) . ?
N12 C14B 1.498(5) . ?
N12 C12A 1.554(5) . ?
C15A C16A 1.532(6) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16B C15B 1.538(6) . ?
C16B H16A 0.9900 . ?
C16B H16B 0.9900 . ?
C12B C11B 1.540(6) . ?
C12B H12A 0.9900 . ?
C12B H12B 0.9900 . ?
C11A C12A 1.560(6) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C13B C14B 1.559(6) . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A C14A 1.516(6) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14B H14A 0.9900 . ?
C14B H14B 0.9900 . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
N10 C8 1.458(3) . ?
N10 C6 1.470(3) . ?
N10 C10 1.473(3) . ?
N9 C7 1.460(3) . ?
N9 C5 1.462(3) . ?
N9 C9 1.485(3) . ?
C8 C7 1.548(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.547(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C5 C6 1.552(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
S3 C3 1.713(2) . ?
N6 C3 1.330(3) . ?
N6 H6C 0.8800 . ?
N6 H6D 0.8800 . ?
N5 C3 1.324(3) . ?
N5 H5C 0.8800 . ?
N5 H5D 0.8800 . ?
S2 C1 1.713(2) . ?
N4 C1 1.327(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N3 C1 1.325(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
S4 C2 1.712(2) . ?
N7 C2 1.326(3) . ?
N7 H7C 0.8800 . ?
N7 H7D 0.8800 . ?
N8 C2 1.332(3) . ?
N8 H8C 0.8800 . ?
N8 H8D 0.8800 . ?
S1 C4 1.722(3) . ?
N2 C4 1.329(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N1 C4 1.323(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13A N11 C15A 113.0(3) . . ?
C13A N11 C11B 54.7(3) . . ?
C15A N11 C11B 137.1(3) . . ?
C13A N11 C15B 137.6(3) . . ?
C15A N11 C15B 49.0(3) . . ?
C11B N11 C15B 108.6(3) . . ?
C13A N11 C11A 108.9(3) . . ?
C15A N11 C11A 109.2(3) . . ?
C11B N11 C11A 55.2(3) . . ?
C15B N11 C11A 61.3(3) . . ?
C13A N11 C13B 54.4(3) . . ?
C15A N11 C13B 61.2(3) . . ?
C11B N11 C13B 104.0(3) . . ?
C15B N11 C13B 105.2(3) . . ?
C11A N11 C13B 141.0(3) . . ?
C16B N12 C12B 114.5(4) . . ?
C16B N12 C16A 47.1(3) . . ?
C12B N12 C16A 138.8(3) . . ?
C16B N12 C14A 137.2(3) . . ?
C12B N12 C14A 56.3(3) . . ?
C16A N12 C14A 108.6(3) . . ?
C16B N12 C14B 109.0(3) . . ?
C12B N12 C14B 108.9(3) . . ?
C16A N12 C14B 63.0(3) . . ?
C14A N12 C14B 53.3(3) . . ?
C16B N12 C12A 63.7(3) . . ?
C12B N12 C12A 53.0(3) . . ?
C16A N12 C12A 105.6(3) . . ?
C14A N12 C12A 103.7(3) . . ?
C14B N12 C12A 140.4(3) . . ?
N11 C15A C16A 108.7(4) . . ?
N11 C15A H15A 109.9 . . ?
C16A C15A H15A 109.9 . . ?
N11 C15A H15B 109.9 . . ?
C16A C15A H15B 109.9 . . ?
H15A C15A H15B 108.3 . . ?
N12 C16B C15B 108.2(4) . . ?
N12 C16B H16A 110.0 . . ?
C15B C16B H16A 110.1 . . ?
N12 C16B H16B 110.1 . . ?
C15B C16B H16B 110.0 . . ?
H16A C16B H16B 108.4 . . ?
N12 C12B C11B 107.8(4) . . ?
N12 C12B H12A 110.2 . . ?
C11B C12B H12A 110.1 . . ?
N12 C12B H12B 110.2 . . ?
C11B C12B H12B 110.2 . . ?
H12A C12B H12B 108.5 . . ?
N11 C11A C12A 108.2(3) . . ?
N11 C11A H11A 110.1 . . ?
C12A C11A H11A 110.1 . . ?
N11 C11A H11B 110.1 . . ?
C12A C11A H11B 110.1 . . ?
H11A C11A H11B 108.4 . . ?
C14B C13B N11 111.2(3) . . ?
C14B C13B H13A 109.4 . . ?
N11 C13B H13A 109.4 . . ?
C14B C13B H13B 109.4 . . ?
N11 C13B H13B 109.4 . . ?
H13A C13B H13B 108.0 . . ?
N11 C15B C16B 113.6(4) . . ?
N11 C15B H15C 108.8 . . ?
C16B C15B H15C 108.8 . . ?
N11 C15B H15D 108.8 . . ?
C16B C15B H15D 108.8 . . ?
H15C C15B H15D 107.7 . . ?
N12 C12A C11A 110.8(3) . . ?
N12 C12A H12C 109.5 . . ?
C11A C12A H12C 109.5 . . ?
N12 C12A H12D 109.5 . . ?
C11A C12A H12D 109.5 . . ?
H12C C12A H12D 108.1 . . ?
N11 C13A C14A 108.2(3) . . ?
N11 C13A H13C 110.1 . . ?
C14A C13A H13C 110.1 . . ?
N11 C13A H13D 110.1 . . ?
C14A C13A H13D 110.1 . . ?
H13C C13A H13D 108.4 . . ?
N12 C14B C13B 107.6(3) . . ?
N12 C14B H14A 110.2 . . ?
C13B C14B H14A 110.2 . . ?
N12 C14B H14B 110.2 . . ?
C13B C14B H14B 110.2 . . ?
H14A C14B H14B 108.5 . . ?
N12 C14A C13A 114.7(3) . . ?
N12 C14A H14C 108.6 . . ?
C13A C14A H14C 108.6 . . ?
N12 C14A H14D 108.6 . . ?
C13A C14A H14D 108.6 . . ?
H14C C14A H14D 107.6 . . ?
N12 C16A C15A 113.2(3) . . ?
N12 C16A H16C 108.9 . . ?
C15A C16A H16C 108.9 . . ?
N12 C16A H16D 108.9 . . ?
C15A C16A H16D 108.9 . . ?
H16C C16A H16D 107.7 . . ?
N11 C11B C12B 113.9(3) . . ?
N11 C11B H11C 108.8 . . ?
C12B C11B H11C 108.8 . . ?
N11 C11B H11D 108.8 . . ?
C12B C11B H11D 108.8 . . ?
H11C C11B H11D 107.7 . . ?
C8 N10 C6 108.89(18) . . ?
C8 N10 C10 108.9(2) . . ?
C6 N10 C10 108.63(19) . . ?
C7 N9 C5 108.8(2) . . ?
C7 N9 C9 107.89(19) . . ?
C5 N9 C9 108.2(2) . . ?
N10 C8 C7 109.95(19) . . ?
N10 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
N10 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N9 C9 C10 110.00(19) . . ?
N9 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N9 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N9 C5 C6 110.95(18) . . ?
N9 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N9 C5 H5B 109.5 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
N10 C6 C5 109.69(19) . . ?
N10 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N10 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N9 C7 C8 111.0(2) . . ?
N9 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N9 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N10 C10 C9 110.47(18) . . ?
N10 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N10 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C3 N6 H6C 120.0 . . ?
C3 N6 H6D 120.0 . . ?
H6C N6 H6D 120.0 . . ?
C3 N5 H5C 120.0 . . ?
C3 N5 H5D 120.0 . . ?
H5C N5 H5D 120.0 . . ?
N5 C3 N6 118.5(2) . . ?
N5 C3 S3 121.07(19) . . ?
N6 C3 S3 120.39(19) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N4 C1 N3 118.1(2) . . ?
N4 C1 S2 120.90(17) . . ?
N3 C1 S2 120.98(18) . . ?
C2 N7 H7C 120.0 . . ?
C2 N7 H7D 120.0 . . ?
H7C N7 H7D 120.0 . . ?
C2 N8 H8C 120.0 . . ?
C2 N8 H8D 120.0 . . ?
H8C N8 H8D 120.0 . . ?
N7 C2 N8 118.8(2) . . ?
N7 C2 S4 120.99(17) . . ?
N8 C2 S4 120.24(19) . . ?
C4 N2 H2A 120.0 . . ?
C4 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C4 N2 118.9(2) . . ?
N1 C4 S1 120.42(19) . . ?
N2 C4 S1 120.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         1.008
_refine_diff_density_min         -2.306
_refine_diff_density_rms         0.144
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DBT298K
_database_code_depnum_ccdc_archive 'CCDC 1434222'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,2-Diazabicyclo(2.2.2)octane bis(thiourea)'
_chemical_name_common            '1,2-Diazabicyclo(2.2.2)octane bis(thiourea)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H12 N2, 2(C H4 N2 S)'
_chemical_formula_sum            'C8 H20 N6 S2'
_chemical_formula_weight         264.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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'

_cell_length_a                   9.685(6)
_cell_length_b                   7.867(5)
_cell_length_c                   18.241(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.266(11)
_cell_angle_gamma                90.00
_cell_volume                     1384.0(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5134
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         27.45
_reflns_number_total             1589
_reflns_number_gt                1061
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1589
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.893
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.60488(5) 0.00484(6) 0.65797(3) 0.0431(2) Uani 1 1 d . . .
N1 N 0.6766(2) 0.2001(2) 0.77348(10) 0.0557(5) Uani 1 1 d . . .
H1A H 0.7296 0.2749 0.7984 0.067 Uiso 1 1 calc R . .
H1B H 0.6030 0.1589 0.7922 0.067 Uiso 1 1 calc R . .
N2 N 0.81872(19) 0.2136(2) 0.68115(10) 0.0517(5) Uani 1 1 d . . .
H2A H 0.8700 0.2883 0.7072 0.062 Uiso 1 1 calc R . .
H2B H 0.8416 0.1821 0.6376 0.062 Uiso 1 1 calc R . .
N3 N 0.93115(19) 0.0739(2) 0.54826(9) 0.0489(5) Uani 1 1 d . . .
C1 C 0.7077(2) 0.1491(2) 0.70739(11) 0.0405(5) Uani 1 1 d . . .
C2 C 0.9541(8) -0.1060(7) 0.5637(3) 0.0714(17) Uani 0.50 1 d P . .
H2C H 0.8665 -0.1625 0.5647 0.086 Uiso 0.50 1 d PR . .
H2D H 1.0024 -0.1151 0.6119 0.086 Uiso 0.50 1 d PR . .
C3 C 1.0541(8) 0.1604(10) 0.5344(5) 0.097(3) Uani 0.50 1 d P . .
H3A H 1.1106 0.1674 0.5804 0.117 Uiso 0.50 1 d PR . .
H3B H 1.0336 0.2742 0.5179 0.117 Uiso 0.50 1 d PR . .
C4 C 0.8438(6) 0.0669(9) 0.4729(3) 0.0693(14) Uani 0.50 1 d P . .
H4A H 0.8183 0.1800 0.4572 0.083 Uiso 0.50 1 d PR . .
H4B H 0.7606 0.0035 0.4780 0.083 Uiso 0.50 1 d PR . .
C5 C 0.9291(7) -0.0220(8) 0.4151(3) 0.0762(18) Uani 0.50 1 d P . .
H5A H 0.9420 0.0557 0.3758 0.091 Uiso 0.50 1 d PR . .
H5B H 0.8808 -0.1203 0.3949 0.091 Uiso 0.50 1 d PR . .
C6 C 1.0417(8) -0.1965(8) 0.5089(3) 0.0755(18) Uani 0.50 1 d P . .
H6A H 0.9907 -0.2917 0.4875 0.091 Uiso 0.50 1 d PR . .
H6B H 1.1276 -0.2373 0.5330 0.091 Uiso 0.50 1 d PR . .
C7 C 1.1393(9) 0.0643(13) 0.4793(5) 0.108(3) Uani 0.50 1 d P . .
H7A H 1.2280 0.0293 0.5021 0.130 Uiso 0.50 1 d PR . .
H7B H 1.1546 0.1407 0.4398 0.130 Uiso 0.50 1 d PR . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.711(2) . ?
N1 C1 1.331(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.318(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C7 1.356(6) 5_756 ?
N3 C3 1.414(6) . ?
N3 C2 1.456(6) . ?
N3 C6 1.462(5) 5_756 ?
N3 C5 1.509(6) 5_756 ?
N3 C4 1.548(5) . ?
C2 C7 1.187(11) 5_756 ?
C2 C5 1.537(11) 5_756 ?
C2 C6 1.543(7) . ?
C2 C3 1.834(9) 5_756 ?
C2 H2C 0.9599 . ?
C2 H2D 0.9601 . ?
C3 C6 1.197(10) 5_756 ?
C3 C5 1.424(11) 5_756 ?
C3 C7 1.555(8) . ?
C3 C2 1.834(9) 5_756 ?
C3 H3A 0.9599 . ?
C3 H3B 0.9599 . ?
C4 C7 1.352(13) 5_756 ?
C4 C6 1.520(11) 5_756 ?
C4 C5 1.562(7) . ?
C4 H4A 0.9601 . ?
C4 H4B 0.9599 . ?
C5 C3 1.424(11) 5_756 ?
C5 N3 1.509(6) 5_756 ?
C5 C2 1.537(11) 5_756 ?
C5 H5A 0.9599 . ?
C5 H5B 0.9599 . ?
C6 C3 1.197(10) 5_756 ?
C6 N3 1.462(5) 5_756 ?
C6 C4 1.520(11) 5_756 ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C7 C2 1.187(11) 5_756 ?
C7 C4 1.352(13) 5_756 ?
C7 N3 1.356(6) 5_756 ?
C7 H7A 0.9601 . ?
C7 H7B 0.9597 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C7 N3 C3 136.4(3) 5_756 . ?
C7 N3 C2 49.8(5) 5_756 . ?
C3 N3 C2 112.7(5) . . ?
C7 N3 C6 112.5(6) 5_756 5_756 ?
C3 N3 C6 49.2(5) . 5_756 ?
C2 N3 C6 138.1(3) . 5_756 ?
C7 N3 C5 110.3(6) 5_756 5_756 ?
C3 N3 C5 58.2(5) . 5_756 ?
C2 N3 C5 62.4(4) . 5_756 ?
C6 N3 C5 106.3(4) 5_756 5_756 ?
C7 N3 C4 55.0(6) 5_756 . ?
C3 N3 C4 105.0(5) . . ?
C2 N3 C4 101.4(4) . . ?
C6 N3 C4 60.6(4) 5_756 . ?
C5 N3 C4 141.1(3) 5_756 . ?
N2 C1 N1 118.21(19) . . ?
N2 C1 S1 121.26(15) . . ?
N1 C1 S1 120.53(16) . . ?
C7 C2 N3 60.7(5) 5_756 . ?
C7 C2 C5 118.9(6) 5_756 5_756 ?
N3 C2 C5 60.5(3) . 5_756 ?
C7 C2 C6 97.6(6) 5_756 . ?
N3 C2 C6 114.0(4) . . ?
C5 C2 C6 91.7(5) 5_756 . ?
C7 C2 C3 57.3(5) 5_756 5_756 ?
N3 C2 C3 92.7(4) . 5_756 ?
C5 C2 C3 111.3(4) 5_756 5_756 ?
C6 C2 C3 40.4(4) . 5_756 ?
C7 C2 H2C 61.3 5_756 . ?
N3 C2 H2C 109.5 . . ?
C5 C2 H2C 158.4 5_756 . ?
C6 C2 H2C 109.9 . . ?
C3 C2 H2C 87.3 5_756 . ?
C7 C2 H2D 154.5 5_756 . ?
N3 C2 H2D 107.6 . . ?
C5 C2 H2D 62.2 5_756 . ?
C6 C2 H2D 107.9 . . ?
C3 C2 H2D 148.2 5_756 . ?
H2C C2 H2D 107.7 . . ?
C6 C3 N3 67.5(4) 5_756 . ?
C6 C3 C5 130.1(6) 5_756 5_756 ?
N3 C3 C5 64.3(4) . 5_756 ?
C6 C3 C7 96.5(7) 5_756 . ?
N3 C3 C7 112.8(4) . . ?
C5 C3 C7 90.6(7) 5_756 . ?
C6 C3 C2 56.6(5) 5_756 5_756 ?
N3 C3 C2 95.7(4) . 5_756 ?
C5 C3 C2 116.3(5) 5_756 5_756 ?
C7 C3 C2 39.9(5) . 5_756 ?
C6 C3 H3A 155.3 5_756 . ?
N3 C3 H3A 107.1 . . ?
C5 C3 H3A 57.2 5_756 . ?
C7 C3 H3A 107.5 . . ?
C2 C3 H3A 146.7 5_756 . ?
C6 C3 H3B 56.3 5_756 . ?
N3 C3 H3B 110.6 . . ?
C5 C3 H3B 157.5 5_756 . ?
C7 C3 H3B 110.9 . . ?
C2 C3 H3B 85.5 5_756 . ?
H3A C3 H3B 107.8 . . ?
C7 C4 C6 109.2(5) 5_756 5_756 ?
C7 C4 N3 55.2(4) 5_756 . ?
C6 C4 N3 56.9(3) 5_756 . ?
C7 C4 C5 93.1(5) 5_756 . ?
C6 C4 C5 91.6(5) 5_756 . ?
N3 C4 C5 109.6(4) . . ?
C7 C4 H4A 155.8 5_756 . ?
C6 C4 H4A 66.8 5_756 . ?
N3 C4 H4A 109.6 . . ?
C5 C4 H4A 110.7 . . ?
C7 C4 H4B 66.0 5_756 . ?
C6 C4 H4B 158.3 5_756 . ?
N3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.3 . . ?
C3 C5 N3 57.5(3) 5_756 5_756 ?
C3 C5 C2 107.5(5) 5_756 5_756 ?
N3 C5 C2 57.1(3) 5_756 5_756 ?
C3 C5 C4 86.8(5) 5_756 . ?
N3 C5 C4 109.3(4) 5_756 . ?
C2 C5 C4 87.7(4) 5_756 . ?
C3 C5 H5A 162.6 5_756 . ?
N3 C5 H5A 109.2 5_756 . ?
C2 C5 H5A 68.1 5_756 . ?
C4 C5 H5A 109.4 . . ?
C3 C5 H5B 69.9 5_756 . ?
N3 C5 H5B 109.8 5_756 . ?
C2 C5 H5B 161.1 5_756 . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.5 . . ?
C3 C6 N3 63.3(4) 5_756 5_756 ?
C3 C6 C4 119.3(6) 5_756 5_756 ?
N3 C6 C4 62.5(4) 5_756 5_756 ?
C3 C6 C2 83.0(5) 5_756 . ?
N3 C6 C2 107.6(4) 5_756 . ?
C4 C6 C2 89.0(5) 5_756 . ?
C3 C6 H6A 65.0 5_756 . ?
N3 C6 H6A 110.1 5_756 . ?
C4 C6 H6A 161.7 5_756 . ?
C2 C6 H6A 109.3 . . ?
C3 C6 H6B 165.7 5_756 . ?
N3 C6 H6B 110.0 5_756 . ?
C4 C6 H6B 62.6 5_756 . ?
C2 C6 H6B 111.2 . . ?
H6A C6 H6B 108.6 . . ?
C2 C7 C4 132.5(7) 5_756 5_756 ?
C2 C7 N3 69.5(5) 5_756 5_756 ?
C4 C7 N3 69.7(5) 5_756 5_756 ?
C2 C7 C3 82.8(8) 5_756 . ?
C4 C7 C3 89.6(6) 5_756 . ?
N3 C7 C3 110.5(4) 5_756 . ?
C2 C7 H7A 164.4 5_756 . ?
C4 C7 H7A 56.7 5_756 . ?
N3 C7 H7A 109.3 5_756 . ?
C3 C7 H7A 111.5 . . ?
C2 C7 H7B 59.5 5_756 . ?
C4 C7 H7B 160.9 5_756 . ?
N3 C7 H7B 109.4 5_756 . ?
C3 C7 H7B 108.0 . . ?
H7A C7 H7B 108.2 . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 C2 C7 -132.4(5) . . . 5_756 ?
C6 N3 C2 C7 -78.9(8) 5_756 . . 5_756 ?
C5 N3 C2 C7 -162.7(5) 5_756 . . 5_756 ?
C4 N3 C2 C7 -20.6(4) . . . 5_756 ?
C7 N3 C2 C5 162.7(5) 5_756 . . 5_756 ?
C3 N3 C2 C5 30.4(4) . . . 5_756 ?
C6 N3 C2 C5 83.8(7) 5_756 . . 5_756 ?
C4 N3 C2 C5 142.2(4) . . . 5_756 ?
C7 N3 C2 C6 85.2(7) 5_756 . . . ?
C3 N3 C2 C6 -47.2(8) . . . . ?
C6 N3 C2 C6 6.2(12) 5_756 . . . ?
C5 N3 C2 C6 -77.6(7) 5_756 . . . ?
C4 N3 C2 C6 64.6(7) . . . . ?
C7 N3 C2 C3 49.7(4) 5_756 . . 5_756 ?
C3 N3 C2 C3 -82.7(6) . . . 5_756 ?
C6 N3 C2 C3 -29.2(9) 5_756 . . 5_756 ?
C5 N3 C2 C3 -113.0(4) 5_756 . . 5_756 ?
C4 N3 C2 C3 29.1(4) . . . 5_756 ?
C7 N3 C3 C6 80.0(11) 5_756 . . 5_756 ?
C2 N3 C3 C6 134.9(5) . . . 5_756 ?
C5 N3 C3 C6 166.7(5) 5_756 . . 5_756 ?
C4 N3 C3 C6 25.3(5) . . . 5_756 ?
C7 N3 C3 C5 -86.7(11) 5_756 . . 5_756 ?
C2 N3 C3 C5 -31.8(4) . . . 5_756 ?
C6 N3 C3 C5 -166.7(5) 5_756 . . 5_756 ?
C4 N3 C3 C5 -141.4(4) . . . 5_756 ?
C7 N3 C3 C7 -7.7(19) 5_756 . . . ?
C2 N3 C3 C7 47.2(11) . . . . ?
C6 N3 C3 C7 -87.7(9) 5_756 . . . ?
C5 N3 C3 C7 79.1(9) 5_756 . . . ?
C4 N3 C3 C7 -62.3(10) . . . . ?
C7 N3 C3 C2 29.8(13) 5_756 . . 5_756 ?
C2 N3 C3 C2 84.7(6) . . . 5_756 ?
C6 N3 C3 C2 -50.2(4) 5_756 . . 5_756 ?
C5 N3 C3 C2 116.5(5) 5_756 . . 5_756 ?
C4 N3 C3 C2 -24.9(5) . . . 5_756 ?
C3 N3 C4 C7 136.6(5) . . . 5_756 ?
C2 N3 C4 C7 19.1(4) . . . 5_756 ?
C6 N3 C4 C7 158.4(5) 5_756 . . 5_756 ?
C5 N3 C4 C7 79.0(8) 5_756 . . 5_756 ?
C7 N3 C4 C6 -158.4(5) 5_756 . . 5_756 ?
C3 N3 C4 C6 -21.8(4) . . . 5_756 ?
C2 N3 C4 C6 -139.3(4) . . . 5_756 ?
C5 N3 C4 C6 -79.4(7) 5_756 . . 5_756 ?
C7 N3 C4 C5 -79.7(6) 5_756 . . . ?
C3 N3 C4 C5 56.9(6) . . . . ?
C2 N3 C4 C5 -60.6(6) . . . . ?
C6 N3 C4 C5 78.7(5) 5_756 . . . ?
C5 N3 C4 C5 -0.7(11) 5_756 . . . ?
C7 C4 C5 C3 0.3(6) 5_756 . . 5_756 ?
C6 C4 C5 C3 109.6(5) 5_756 . . 5_756 ?
N3 C4 C5 C3 54.3(6) . . . 5_756 ?
C7 C4 C5 N3 -53.6(7) 5_756 . . 5_756 ?
C6 C4 C5 N3 55.8(5) 5_756 . . 5_756 ?
N3 C4 C5 N3 0.5(7) . . . 5_756 ?
C7 C4 C5 C2 -107.4(5) 5_756 . . 5_756 ?
C6 C4 C5 C2 2.0(4) 5_756 . . 5_756 ?
N3 C4 C5 C2 -53.3(5) . . . 5_756 ?
C7 C2 C6 C3 -2.2(8) 5_756 . . 5_756 ?
N3 C2 C6 C3 -63.5(8) . . . 5_756 ?
C5 C2 C6 C3 -121.7(6) 5_756 . . 5_756 ?
C7 C2 C6 N3 56.9(9) 5_756 . . 5_756 ?
N3 C2 C6 N3 -4.4(9) . . . 5_756 ?
C5 C2 C6 N3 -62.6(6) 5_756 . . 5_756 ?
C3 C2 C6 N3 59.1(4) 5_756 . . 5_756 ?
C7 C2 C6 C4 117.5(7) 5_756 . . 5_756 ?
N3 C2 C6 C4 56.3(6) . . . 5_756 ?
C5 C2 C6 C4 -2.0(4) 5_756 . . 5_756 ?
C3 C2 C6 C4 119.7(6) 5_756 . . 5_756 ?
C6 C3 C7 C2 2.2(8) 5_756 . . 5_756 ?
N3 C3 C7 C2 70.5(10) . . . 5_756 ?
C5 C3 C7 C2 132.7(7) 5_756 . . 5_756 ?
C6 C3 C7 C4 -130.8(7) 5_756 . . 5_756 ?
N3 C3 C7 C4 -62.5(9) . . . 5_756 ?
C5 C3 C7 C4 -0.3(6) 5_756 . . 5_756 ?
C2 C3 C7 C4 -133.0(7) 5_756 . . 5_756 ?
C6 C3 C7 N3 -62.7(11) 5_756 . . 5_756 ?
N3 C3 C7 N3 5.6(14) . . . 5_756 ?
C5 C3 C7 N3 67.8(10) 5_756 . . 5_756 ?
C2 C3 C7 N3 -64.9(6) 5_756 . . 5_756 ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046
