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Two inclusion compounds of di­thio­biurea and tetra­propyl­ammonium and tetra­butyl­ammonium are characterized and reported, namely tetra­propyl­ammonium carbamo­thio­yl(carbamo­thioyl­amino)­aza­nide, C12H28N+·C2H5N4S2-, (1), and tetra­butyl­ammonium carbamo­thio­yl(carbamo­thioyl­amino)­aza­nide, C16H36N+·C2H5N4S2-, (2). The results show that in (1), the di­thio­biurea anion forms a dimer via N-H...N hydrogen bonds and the dimers are connected into wide hydrogen-bonded ribbons. The guest tetra­propyl­ammonium cation changes its character to become the host mol­ecule, generating pseudo-channels containing the aforementioned ribbons by C-H...S contacts, yielding the three-dimensional network structure. In comparison, in (2), the di­thio­biurea anions are linked via N-H...S inter­actions, producing one-dimensional chains which pack to generate two-dimensional hydrogen-bonded layers. These layers accommodate the guest tetra­butyl­ammonium cations, resulting in a sandwich-like layer structure with host-guest C-H...S contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615003095/yo3004sup1.cif
Contains datablocks 20090914a_0m, 091111a_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615003095/yo300420090914a_0msup2.hkl
Contains datablock 20090914a_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615003095/yo3004091111a_0msup3.hkl
Contains datablock 091111a_0m

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615003095/yo300420090914a_0msup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615003095/yo3004091111a_0msup5.cml
Supplementary material

CCDC references: 1049273; 1049272

Computing details top

For both compounds, data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008). Molecular graphics: SHELXTL (Sheldrick, 2008) and Marvinsketch (ChemAxon, 2010) for 20090914a_0m; SHELXTL (Sheldrick, 2008) for 091111a_0m. For both compounds, software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(20090914a_0m) Tetrapropylammonium carbamothioyl(carbamothioylamino)azanide top
Crystal data top
C12H28N+·C2H5N4S2F(000) = 736
Mr = 335.57Dx = 1.171 Mg m3
Dm = 0 Mg m3
Dm measured by not measured
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 4223 reflections
a = 10.1149 (5) Åθ = 2.7–27.6°
b = 8.1266 (4) ŵ = 0.28 mm1
c = 23.1765 (12) ÅT = 296 K
β = 91.889 (1)°Block, colorless
V = 1904.07 (17) Å30.27 × 0.21 × 0.19 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4421 independent reflections
Radiation source: fine-focus sealed tube3712 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
phi and ω scansθmax = 27.7°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1312
Tmin = 0.928, Tmax = 0.948k = 1010
9213 measured reflectionsl = 1830
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0661P)2 + 0.3666P]
where P = (Fo2 + 2Fc2)/3
4421 reflections(Δ/σ)max = 0.001
205 parametersΔρmax = 0.28 e Å3
5 restraintsΔρmin = 0.22 e Å3
Special details top

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

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.34365 (4)0.08596 (5)0.061387 (18)0.04437 (13)
C10.42074 (13)0.26890 (17)0.04504 (6)0.0325 (3)
N10.53166 (13)0.26269 (16)0.01262 (6)0.0420 (3)
H1A0.5561 (19)0.1644 (16)0.0024 (8)0.063*
H1B0.5635 (19)0.3582 (16)0.0018 (8)0.063*
S20.10000 (4)0.55360 (5)0.162714 (17)0.04495 (13)
C20.23853 (14)0.55098 (17)0.12321 (6)0.0352 (3)
N20.38631 (12)0.41678 (14)0.06128 (5)0.0380 (3)
N30.27427 (12)0.41789 (15)0.09521 (6)0.0386 (3)
H30.2357 (17)0.3176 (15)0.0988 (8)0.058*
C30.80123 (15)0.11437 (17)0.14528 (7)0.0382 (3)
H3A0.88160.17310.13650.046*
H3B0.78470.13260.18580.046*
N40.31568 (15)0.68418 (18)0.11879 (7)0.0550 (4)
H4C0.3890 (15)0.678 (3)0.0970 (9)0.082*
H4D0.287 (2)0.7797 (18)0.1342 (9)0.082*
C40.68780 (17)0.1891 (2)0.10968 (8)0.0512 (4)
H4A0.60500.13840.11990.061*
H4B0.70070.16990.06890.061*
C50.6831 (2)0.3709 (2)0.12142 (10)0.0666 (6)
H5A0.61220.41960.09880.100*
H5B0.66870.38900.16170.100*
H5C0.76550.42020.11130.100*
N50.82528 (11)0.06813 (13)0.13643 (5)0.0311 (2)
C60.70202 (14)0.16815 (18)0.14756 (6)0.0374 (3)
H6A0.72440.28390.14480.045*
H6B0.63670.14440.11710.045*
C70.63904 (17)0.1394 (3)0.20511 (7)0.0556 (4)
H7A0.60520.02780.20660.067*
H7B0.70500.15260.23610.067*
C80.52761 (19)0.2596 (3)0.21317 (9)0.0653 (5)
H8A0.48930.24110.25000.098*
H8B0.46130.24440.18300.098*
H8C0.56120.37000.21160.098*
C90.93542 (13)0.12229 (18)0.17863 (6)0.0347 (3)
H9A0.94680.24030.17490.042*
H9B0.90730.10090.21750.042*
C101.06778 (15)0.0412 (2)0.17138 (8)0.0500 (4)
H10A1.10280.07260.13450.060*
H10B1.05710.07740.17160.060*
C111.16393 (18)0.0920 (3)0.21971 (9)0.0631 (5)
H11A1.24770.03940.21450.095*
H11B1.12970.05950.25610.095*
H11C1.17530.20930.21910.095*
C120.86552 (16)0.09391 (17)0.07440 (6)0.0381 (3)
H12A0.94480.02980.06840.046*
H12B0.79620.04950.04900.046*
C130.89181 (17)0.26855 (19)0.05607 (6)0.0429 (3)
H13A0.95180.32140.08380.052*
H13B0.80980.33040.05420.052*
C140.9530 (2)0.2654 (2)0.00323 (8)0.0639 (5)
H14A0.97020.37590.01550.096*
H14B0.89290.21340.03050.096*
H14C1.03450.20470.00100.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0529 (2)0.0309 (2)0.0504 (2)0.00418 (15)0.01684 (17)0.00244 (15)
C10.0330 (6)0.0336 (7)0.0308 (6)0.0015 (5)0.0015 (5)0.0014 (5)
N10.0410 (7)0.0367 (7)0.0491 (7)0.0002 (5)0.0146 (5)0.0035 (5)
S20.0448 (2)0.0460 (2)0.0449 (2)0.00209 (16)0.01526 (16)0.00844 (16)
C20.0379 (7)0.0340 (7)0.0339 (7)0.0005 (6)0.0031 (5)0.0027 (5)
N20.0380 (6)0.0327 (6)0.0442 (7)0.0031 (5)0.0131 (5)0.0039 (5)
N30.0377 (6)0.0319 (6)0.0470 (7)0.0050 (5)0.0132 (5)0.0056 (5)
C30.0423 (8)0.0247 (7)0.0471 (8)0.0011 (6)0.0060 (6)0.0039 (6)
N40.0576 (9)0.0383 (7)0.0704 (10)0.0113 (7)0.0246 (7)0.0139 (7)
C40.0521 (9)0.0346 (8)0.0657 (10)0.0090 (7)0.0161 (8)0.0023 (7)
C50.0623 (11)0.0336 (9)0.1022 (16)0.0082 (8)0.0226 (11)0.0045 (9)
N50.0359 (6)0.0258 (5)0.0314 (5)0.0009 (4)0.0016 (4)0.0002 (4)
C60.0389 (7)0.0325 (7)0.0408 (7)0.0034 (6)0.0002 (6)0.0026 (6)
C70.0501 (9)0.0646 (12)0.0527 (10)0.0091 (8)0.0128 (7)0.0119 (8)
C80.0542 (11)0.0719 (13)0.0712 (13)0.0073 (9)0.0212 (9)0.0033 (10)
C90.0377 (7)0.0356 (7)0.0307 (6)0.0046 (6)0.0012 (5)0.0022 (5)
C100.0353 (8)0.0516 (10)0.0630 (10)0.0045 (7)0.0010 (7)0.0106 (8)
C110.0406 (9)0.0837 (15)0.0641 (12)0.0054 (9)0.0091 (8)0.0006 (10)
C120.0517 (8)0.0337 (7)0.0287 (6)0.0003 (6)0.0004 (6)0.0027 (5)
C130.0545 (9)0.0371 (8)0.0374 (8)0.0047 (7)0.0051 (6)0.0006 (6)
C140.0901 (14)0.0614 (12)0.0411 (9)0.0120 (10)0.0140 (9)0.0048 (8)
Geometric parameters (Å, º) top
S1—C11.7266 (14)C6—H6A0.9700
C1—N21.3099 (17)C6—H6B0.9700
C1—N11.3717 (18)C7—C81.508 (2)
N1—H1A0.908 (9)C7—H7A0.9700
N1—H1B0.908 (9)C7—H7B0.9700
S2—C21.6990 (14)C8—H8A0.9600
C2—N31.3179 (18)C8—H8B0.9600
C2—N41.3403 (19)C8—H8C0.9600
N2—N31.4006 (16)C9—C101.507 (2)
N3—H30.909 (9)C9—H9A0.9700
C3—C41.518 (2)C9—H9B0.9700
C3—N51.5180 (16)C10—C111.516 (2)
C3—H3A0.9700C10—H10A0.9700
C3—H3B0.9700C10—H10B0.9700
N4—H4C0.912 (9)C11—H11A0.9600
N4—H4D0.905 (9)C11—H11B0.9600
C4—C51.503 (2)C11—H11C0.9600
C4—H4A0.9700C12—C131.508 (2)
C4—H4B0.9700C12—H12A0.9700
C5—H5A0.9600C12—H12B0.9700
C5—H5B0.9600C13—C141.526 (2)
C5—H5C0.9600C13—H13A0.9700
N5—C61.5175 (18)C13—H13B0.9700
N5—C121.5214 (17)C14—H14A0.9600
N5—C91.5231 (17)C14—H14B0.9600
C6—C71.515 (2)C14—H14C0.9600
N2—C1—N1114.91 (12)C8—C7—H7A109.6
N2—C1—S1126.91 (10)C6—C7—H7A109.6
N1—C1—S1118.16 (10)C8—C7—H7B109.6
C1—N1—H1A118.7 (13)C6—C7—H7B109.6
C1—N1—H1B118.4 (13)H7A—C7—H7B108.1
H1A—N1—H1B120.4 (18)C7—C8—H8A109.5
N3—C2—N4117.08 (13)C7—C8—H8B109.5
N3—C2—S2121.34 (11)H8A—C8—H8B109.5
N4—C2—S2121.58 (11)C7—C8—H8C109.5
C1—N2—N3113.26 (11)H8A—C8—H8C109.5
C2—N3—N2121.46 (12)H8B—C8—H8C109.5
C2—N3—H3124.5 (12)C10—C9—N5115.83 (12)
N2—N3—H3113.8 (12)C10—C9—H9A108.3
C4—C3—N5116.05 (12)N5—C9—H9A108.3
C4—C3—H3A108.3C10—C9—H9B108.3
N5—C3—H3A108.3N5—C9—H9B108.3
C4—C3—H3B108.3H9A—C9—H9B107.4
N5—C3—H3B108.3C9—C10—C11110.43 (15)
H3A—C3—H3B107.4C9—C10—H10A109.6
C2—N4—H4C118.8 (16)C11—C10—H10A109.6
C2—N4—H4D118.0 (15)C9—C10—H10B109.6
H4C—N4—H4D123 (2)C11—C10—H10B109.6
C5—C4—C3108.81 (14)H10A—C10—H10B108.1
C5—C4—H4A109.9C10—C11—H11A109.5
C3—C4—H4A109.9C10—C11—H11B109.5
C5—C4—H4B109.9H11A—C11—H11B109.5
C3—C4—H4B109.9C10—C11—H11C109.5
H4A—C4—H4B108.3H11A—C11—H11C109.5
C4—C5—H5A109.5H11B—C11—H11C109.5
C4—C5—H5B109.5C13—C12—N5116.82 (11)
H5A—C5—H5B109.5C13—C12—H12A108.1
C4—C5—H5C109.5N5—C12—H12A108.1
H5A—C5—H5C109.5C13—C12—H12B108.1
H5B—C5—H5C109.5N5—C12—H12B108.1
C6—N5—C3111.35 (11)H12A—C12—H12B107.3
C6—N5—C12109.50 (10)C12—C13—C14108.57 (13)
C3—N5—C12108.14 (10)C12—C13—H13A110.0
C6—N5—C9108.88 (10)C14—C13—H13A110.0
C3—N5—C9108.22 (10)C12—C13—H13B110.0
C12—N5—C9110.75 (11)C14—C13—H13B110.0
C7—C6—N5116.02 (12)H13A—C13—H13B108.4
C7—C6—H6A108.3C13—C14—H14A109.5
N5—C6—H6A108.3C13—C14—H14B109.5
C7—C6—H6B108.3H14A—C14—H14B109.5
N5—C6—H6B108.3C13—C14—H14C109.5
H6A—C6—H6B107.4H14A—C14—H14C109.5
C8—C7—C6110.29 (15)H14B—C14—H14C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.91 (1)2.67 (1)3.5641 (13)168 (2)
N1—H1B···N2ii0.91 (1)2.36 (1)3.2404 (18)165 (2)
N3—H3···S10.91 (1)2.36 (2)2.9016 (13)119 (1)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z.
(091111a_0m) Tetrabutylammonium carbamothioyl(carbamothioylamino)azanide top
Crystal data top
C16H36N+·C2H5N4S2V = 1167.10 (2) Å3
Mr = 391.68Z = 2
Triclinic, P1F(000) = 432
Hall symbol: -P 1Dx = 1.115 Mg m3
a = 9.4151 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6835 (1) ŵ = 0.24 mm1
c = 13.4189 (1) ÅT = 296 K
α = 77.679 (1)°Block, colorless
β = 89.246 (1)°0.19 × 0.14 × 0.14 mm
γ = 77.692 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5403 independent reflections
Radiation source: fine-focus sealed tube3695 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
phi and ω scansθmax = 27.7°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1212
Tmin = 0.956, Tmax = 0.967k = 126
11214 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0838P)2 + 0.3749P]
where P = (Fo2 + 2Fc2)/3
5403 reflections(Δ/σ)max < 0.001
236 parametersΔρmax = 0.52 e Å3
20 restraintsΔρmin = 0.29 e Å3
Special details top

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

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.1655 (3)0.8046 (3)0.11557 (18)0.0520 (6)
N10.1797 (3)0.9408 (3)0.1021 (2)0.0795 (8)
H1A0.25170.96620.13550.119*
H1B0.12971.01560.05190.119*
S10.04522 (8)0.75318 (7)0.04598 (5)0.0614 (2)
C20.3982 (3)0.6469 (3)0.3276 (2)0.0561 (6)
N20.2494 (2)0.7077 (2)0.18816 (16)0.0552 (5)
H2A0.25340.61000.20620.083*
S20.37415 (8)0.47084 (8)0.35586 (6)0.0691 (2)
C30.8377 (3)0.4756 (2)0.33086 (16)0.0448 (5)
H3A0.73740.52780.32960.054*
H3B0.85890.41150.39760.054*
N30.3398 (2)0.7510 (2)0.25023 (17)0.0573 (5)
C40.9349 (3)0.5832 (3)0.31777 (18)0.0508 (5)
H4A0.92380.63980.24830.061*
H4B1.03560.53150.32930.061*
N40.4954 (3)0.6832 (3)0.3868 (2)0.0764 (7)
H4C0.47130.78030.38840.115*
H4D0.51510.62770.45230.115*
C50.8988 (3)0.6838 (3)0.39106 (19)0.0547 (6)
H5A0.79830.73590.37910.066*
H5B0.90900.62700.46050.066*
N50.85265 (19)0.38372 (19)0.25057 (13)0.0408 (4)
C60.9962 (3)0.7913 (3)0.3792 (2)0.0669 (7)
H6A0.96930.85340.42640.100*
H6B0.98560.84840.31080.100*
H6C1.09550.74020.39290.100*
C71.0086 (2)0.3057 (2)0.24445 (17)0.0460 (5)
H7A1.06670.37730.22170.055*
H7B1.01290.24830.19290.055*
C81.0769 (3)0.2073 (3)0.34292 (19)0.0557 (6)
H8A1.07280.26330.39520.067*
H8B1.02130.13330.36540.067*
C91.2329 (3)0.1357 (3)0.3307 (2)0.0657 (7)
H9A1.23570.07160.28390.079*
H9B1.28560.20940.30080.079*
C101.3076 (4)0.0508 (4)0.4292 (3)0.0934 (11)
H10A1.40630.00820.41700.140*
H10B1.25760.02420.45840.140*
H10C1.30700.11390.47560.140*
C110.7537 (2)0.2781 (2)0.28053 (17)0.0459 (5)
H11A0.78490.21960.34780.055*
H11B0.65590.33300.28560.055*
C120.7484 (3)0.1778 (3)0.2089 (2)0.0575 (6)
H12A0.71580.23460.14130.069*
H12B0.84520.12060.20390.069*
C130.6462 (3)0.0780 (3)0.2465 (2)0.0636 (7)
H13A0.55010.13570.25280.076*
H13B0.67980.02070.31370.076*
C140.6360 (4)0.0226 (4)0.1757 (3)0.0863 (10)
H14A0.57020.08360.20260.129*
H14B0.73050.08150.17040.129*
H14C0.60090.03350.10940.129*
C150.8085 (3)0.4789 (3)0.14491 (16)0.0477 (5)
H15A0.87470.54410.12810.057*
H15B0.82130.41720.09580.057*
C160.6547 (3)0.5682 (3)0.13219 (19)0.0636 (7)
H16A0.58770.50370.14800.076*
H16B0.64100.63030.18100.076*
C170.6181 (6)0.6586 (7)0.0289 (3)0.1396 (19)0.50
H17A0.51320.67480.02130.168*0.50
H17B0.63890.75160.03180.168*0.50
C17'0.6181 (6)0.6586 (7)0.0289 (3)0.1396 (19)0.50
H17C0.58150.59690.00800.168*0.50
H17D0.53430.73240.03790.168*0.50
C180.6688 (11)0.6318 (16)0.0595 (5)0.111 (4)0.603 (18)
H18A0.62620.71110.11400.167*0.603 (18)
H18B0.64410.54460.06990.167*0.603 (18)
H18C0.77260.62040.05850.167*0.603 (18)
C18'0.6962 (13)0.728 (2)0.0374 (10)0.108 (6)0.397 (18)
H18D0.63620.78100.09630.162*0.397 (18)
H18E0.77510.66010.05750.162*0.397 (18)
H18F0.73440.79440.00690.162*0.397 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0593 (15)0.0493 (13)0.0442 (12)0.0090 (11)0.0071 (11)0.0061 (10)
N10.102 (2)0.0591 (14)0.0760 (16)0.0251 (14)0.0338 (14)0.0011 (12)
S10.0777 (5)0.0597 (4)0.0492 (4)0.0228 (3)0.0015 (3)0.0089 (3)
C20.0431 (13)0.0590 (15)0.0602 (14)0.0031 (11)0.0018 (11)0.0076 (12)
N20.0584 (12)0.0501 (11)0.0579 (12)0.0137 (10)0.0002 (10)0.0112 (10)
S20.0654 (5)0.0599 (4)0.0760 (5)0.0102 (3)0.0091 (4)0.0040 (3)
C30.0476 (12)0.0504 (12)0.0353 (10)0.0055 (10)0.0032 (9)0.0124 (9)
N30.0522 (12)0.0549 (12)0.0645 (13)0.0131 (10)0.0031 (10)0.0107 (10)
C40.0556 (14)0.0555 (14)0.0455 (12)0.0147 (11)0.0056 (10)0.0179 (10)
N40.0762 (17)0.0691 (15)0.0792 (16)0.0137 (13)0.0220 (13)0.0064 (13)
C50.0643 (16)0.0546 (14)0.0494 (13)0.0154 (12)0.0086 (11)0.0181 (11)
N50.0437 (10)0.0440 (10)0.0352 (8)0.0105 (8)0.0028 (7)0.0088 (7)
C60.0796 (19)0.0664 (17)0.0652 (16)0.0243 (15)0.0112 (14)0.0295 (14)
C70.0431 (12)0.0516 (13)0.0452 (11)0.0100 (10)0.0070 (9)0.0151 (10)
C80.0474 (13)0.0631 (15)0.0525 (13)0.0030 (11)0.0018 (11)0.0125 (12)
C90.0547 (15)0.0749 (18)0.0655 (16)0.0027 (13)0.0019 (13)0.0271 (14)
C100.071 (2)0.101 (3)0.085 (2)0.0294 (18)0.0154 (17)0.017 (2)
C110.0449 (12)0.0470 (12)0.0443 (11)0.0124 (10)0.0031 (9)0.0041 (10)
C120.0658 (16)0.0560 (14)0.0567 (14)0.0247 (12)0.0094 (12)0.0141 (12)
C130.0670 (17)0.0617 (16)0.0653 (16)0.0273 (13)0.0049 (13)0.0076 (13)
C140.109 (3)0.072 (2)0.092 (2)0.0485 (19)0.0015 (19)0.0193 (18)
C150.0593 (14)0.0509 (13)0.0343 (10)0.0187 (11)0.0013 (10)0.0051 (9)
C160.0684 (17)0.0625 (16)0.0498 (14)0.0029 (13)0.0064 (12)0.0005 (12)
C170.118 (3)0.172 (4)0.078 (2)0.020 (3)0.001 (2)0.035 (3)
C17'0.118 (3)0.172 (4)0.078 (2)0.020 (3)0.001 (2)0.035 (3)
C180.109 (6)0.142 (9)0.062 (4)0.002 (6)0.008 (4)0.003 (4)
C18'0.120 (9)0.132 (12)0.064 (6)0.049 (8)0.018 (5)0.021 (7)
Geometric parameters (Å, º) top
C1—N11.327 (3)C9—C101.494 (4)
C1—N21.330 (3)C9—H9A0.9700
C1—S11.694 (3)C9—H9B0.9700
N1—H1A0.9197C10—H10A0.9600
N1—H1B0.9243C10—H10B0.9600
C2—N31.315 (3)C10—H10C0.9600
C2—N41.367 (3)C11—C121.514 (3)
C2—S21.728 (3)C11—H11A0.9700
N2—N31.382 (3)C11—H11B0.9700
N2—H2A0.9183C12—C131.513 (3)
C3—C41.510 (3)C12—H12A0.9700
C3—N51.524 (3)C12—H12B0.9700
C3—H3A0.9700C13—C141.515 (4)
C3—H3B0.9700C13—H13A0.9700
C4—C51.514 (3)C13—H13B0.9700
C4—H4A0.9700C14—H14A0.9600
C4—H4B0.9700C14—H14B0.9600
N4—H4C0.9241C14—H14C0.9600
N4—H4D0.9248C15—C161.512 (4)
C5—C61.510 (3)C15—H15A0.9700
C5—H5A0.9700C15—H15B0.9700
C5—H5B0.9700C16—C171.474 (4)
N5—C71.512 (3)C16—H16A0.9700
N5—C111.515 (3)C16—H16B0.9700
N5—C151.525 (3)C17—C181.329 (8)
C6—H6A0.9600C17—H17A0.9700
C6—H6B0.9600C17—H17B0.9700
C6—H6C0.9600C18—H18A0.9600
C7—C81.514 (3)C18—H18B0.9600
C7—H7A0.9700C18—H18C0.9600
C7—H7B0.9700C18'—H18D0.9600
C8—C91.508 (3)C18'—H18E0.9600
C8—H8A0.9700C18'—H18F0.9600
C8—H8B0.9700
N1—C1—N2117.0 (2)C10—C9—H9B109.0
N1—C1—S1122.7 (2)C8—C9—H9B109.0
N2—C1—S1120.27 (19)H9A—C9—H9B107.8
C1—N1—H1A122.0C9—C10—H10A109.5
C1—N1—H1B123.9C9—C10—H10B109.5
H1A—N1—H1B113.4H10A—C10—H10B109.5
N3—C2—N4114.4 (2)C9—C10—H10C109.5
N3—C2—S2127.3 (2)H10A—C10—H10C109.5
N4—C2—S2118.1 (2)H10B—C10—H10C109.5
C1—N2—N3120.4 (2)C12—C11—N5115.72 (18)
C1—N2—H2A127.5C12—C11—H11A108.3
N3—N2—H2A112.0N5—C11—H11A108.3
C4—C3—N5114.96 (17)C12—C11—H11B108.3
C4—C3—H3A108.5N5—C11—H11B108.3
N5—C3—H3A108.5H11A—C11—H11B107.4
C4—C3—H3B108.5C13—C12—C11110.9 (2)
N5—C3—H3B108.5C13—C12—H12A109.5
H3A—C3—H3B107.5C11—C12—H12A109.5
C2—N3—N2112.9 (2)C13—C12—H12B109.5
C3—C4—C5111.59 (19)C11—C12—H12B109.5
C3—C4—H4A109.3H12A—C12—H12B108.0
C5—C4—H4A109.3C12—C13—C14112.5 (2)
C3—C4—H4B109.3C12—C13—H13A109.1
C5—C4—H4B109.3C14—C13—H13A109.1
H4A—C4—H4B108.0C12—C13—H13B109.1
C2—N4—H4C111.7C14—C13—H13B109.1
C2—N4—H4D117.1H13A—C13—H13B107.8
H4C—N4—H4D110.2C13—C14—H14A109.5
C6—C5—C4112.0 (2)C13—C14—H14B109.5
C6—C5—H5A109.2H14A—C14—H14B109.5
C4—C5—H5A109.2C13—C14—H14C109.5
C6—C5—H5B109.2H14A—C14—H14C109.5
C4—C5—H5B109.2H14B—C14—H14C109.5
H5A—C5—H5B107.9C16—C15—N5116.05 (19)
C7—N5—C11111.42 (17)C16—C15—H15A108.3
C7—N5—C3111.24 (16)N5—C15—H15A108.3
C11—N5—C3106.71 (16)C16—C15—H15B108.3
C7—N5—C15106.36 (16)N5—C15—H15B108.3
C11—N5—C15110.61 (16)H15A—C15—H15B107.4
C3—N5—C15110.57 (16)C17—C16—C15113.8 (3)
C5—C6—H6A109.5C17—C16—H16A108.8
C5—C6—H6B109.5C15—C16—H16A108.8
H6A—C6—H6B109.5C17—C16—H16B108.8
C5—C6—H6C109.5C15—C16—H16B108.8
H6A—C6—H6C109.5H16A—C16—H16B107.7
H6B—C6—H6C109.5C18—C17—C16128.3 (6)
N5—C7—C8115.42 (18)C18—C17—H17A105.2
N5—C7—H7A108.4C16—C17—H17A105.2
C8—C7—H7A108.4C18—C17—H17B105.2
N5—C7—H7B108.4C16—C17—H17B105.2
C8—C7—H7B108.4H17A—C17—H17B105.9
H7A—C7—H7B107.5C17—C18—H18A109.5
C9—C8—C7112.1 (2)C17—C18—H18B109.5
C9—C8—H8A109.2H18A—C18—H18B109.5
C7—C8—H8A109.2C17—C18—H18C109.5
C9—C8—H8B109.2H18A—C18—H18C109.5
C7—C8—H8B109.2H18B—C18—H18C109.5
H8A—C8—H8B107.9H18D—C18'—H18E109.5
C10—C9—C8113.1 (2)H18D—C18'—H18F109.5
C10—C9—H9A109.0H18E—C18'—H18F109.5
C8—C9—H9A109.0
N1—C1—N2—N34.0 (4)N5—C7—C8—C9179.0 (2)
S1—C1—N2—N3175.09 (17)C7—C8—C9—C10173.7 (3)
N4—C2—N3—N2176.0 (2)C7—N5—C11—C1260.0 (2)
S2—C2—N3—N20.5 (3)C3—N5—C11—C12178.4 (2)
C1—N2—N3—C2170.1 (2)C15—N5—C11—C1258.1 (3)
N5—C3—C4—C5172.01 (19)N5—C11—C12—C13179.9 (2)
C3—C4—C5—C6179.5 (2)C11—C12—C13—C14179.1 (2)
C4—C3—N5—C755.1 (2)C7—N5—C15—C16179.8 (2)
C4—C3—N5—C11176.80 (19)C11—N5—C15—C1658.7 (3)
C4—C3—N5—C1562.8 (2)C3—N5—C15—C1659.3 (2)
C11—N5—C7—C861.1 (2)N5—C15—C16—C17179.6 (3)
C3—N5—C7—C857.9 (2)C15—C16—C17—C1831.3 (12)
C15—N5—C7—C8178.31 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···S1i0.922.583.484 (3)164
N4—H4D···S2ii0.922.693.576 (3)161
N2—H2A···S20.922.322.902 (2)121
Symmetry codes: (i) x, y+2, z; (ii) x+1, y+1, z+1.
 

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