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The title mol­ecule, C13H16N4O2S2, contains a fused three-ring system. The conformations of the rings are nearly envelope, nearly planar and envelope. The crystal packing reveals weak inter­molecular C—H...O hydrogen bonding and S...arene inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041286/fb2024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041286/fb2024Isup2.hkl
Contains datablock I

CCDC reference: 627648

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.068
  • wR factor = 0.219
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-NT (Bruker, 1997); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

5,8-Diethyl-6,9-dithioxo-2,3,5,6,8,9-hexahydro-(1H)-3a,5,8,9a- tetraazaphenalene-4,7-dione top
Crystal data top
C13H16N4O2S2F(000) = 680
Mr = 324.42Dx = 1.472 Mg m3
Monoclinic, P21/nMelting point: 468 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.155 (2) ÅCell parameters from 26 reflections
b = 10.261 (2) Åθ = 5.2–12.5°
c = 14.382 (3) ŵ = 0.37 mm1
β = 102.33 (2)°T = 294 K
V = 1464.0 (5) Å3Prism, red
Z = 40.38 × 0.38 × 0.15 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.033
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 2.3°
Graphite monochromatorh = 112
θ/2θ scansk = 112
3740 measured reflectionsl = 1717
2863 independent reflections3 standard reflections every 97 reflections
2180 reflections with I > 2σ(I) intensity decay: 1%
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)] = 0.068Hydrogen site location: difference Fourier map
wR(F2) = 0.219H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1273P)2 + 1.5323P]
where P = (Fo2 + 2Fc2)/3
2863 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 0.70 e Å3
64 constraints
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
S10.05802 (11)0.24344 (10)1.00511 (8)0.0542 (4)
S20.68811 (9)0.37682 (12)0.90859 (8)0.0564 (4)
N80.5167 (3)0.5599 (3)0.8313 (2)0.0441 (7)
N20.3013 (3)0.2146 (3)0.9682 (2)0.0395 (7)
N3a0.1811 (3)0.3994 (3)0.90311 (19)0.0349 (6)
N6a0.2859 (3)0.5701 (3)0.8380 (2)0.0396 (7)
C100.2940 (3)0.4487 (3)0.8793 (2)0.0347 (7)
O10.4982 (3)0.1660 (3)0.9267 (2)0.0614 (8)
O20.3847 (3)0.7336 (3)0.7718 (3)0.0668 (9)
C110.4125 (3)0.3816 (3)0.8957 (2)0.0374 (7)
C30.1864 (3)0.2865 (3)0.9576 (2)0.0382 (7)
C70.3963 (4)0.6271 (4)0.8106 (3)0.0464 (9)
C10.4134 (4)0.2480 (3)0.9295 (3)0.0410 (8)
C60.1608 (4)0.6463 (4)0.8200 (3)0.0541 (10)
H6A0.16110.70840.76920.065*
H6B0.15350.69420.87680.065*
C140.6321 (4)0.6243 (4)0.8015 (3)0.0597 (11)
H14A0.71340.61110.85000.072*
H14B0.61540.71730.79520.072*
C90.5357 (3)0.4395 (4)0.8776 (2)0.0400 (8)
C50.0443 (4)0.5554 (4)0.7925 (3)0.0550 (10)
H5A0.05120.50780.73550.066*
H5B0.03950.60410.77950.066*
C120.3089 (4)0.0855 (4)1.0155 (3)0.0502 (9)
H12A0.26240.08971.06780.060*
H12B0.40250.06431.04170.060*
C40.0458 (4)0.4619 (4)0.8733 (3)0.0504 (9)
H4A0.02410.50820.92690.060*
H4B0.02210.39520.85360.060*
C130.2466 (5)0.0207 (4)0.9473 (4)0.0626 (11)
H13A0.15290.00190.92330.094*
H13B0.25530.10290.98000.094*
H13C0.29210.02490.89530.094*
C150.6525 (5)0.5708 (6)0.7086 (3)0.0764 (15)
H15A0.67020.47900.71490.115*
H15B0.72750.61390.69110.115*
H15C0.57270.58530.66020.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0516 (6)0.0480 (6)0.0707 (7)0.0029 (4)0.0306 (5)0.0017 (5)
S20.0341 (5)0.0672 (7)0.0669 (7)0.0059 (4)0.0088 (4)0.0118 (5)
N80.0387 (15)0.0413 (16)0.0520 (17)0.0033 (13)0.0091 (13)0.0039 (13)
N20.0422 (15)0.0357 (15)0.0403 (15)0.0004 (12)0.0077 (12)0.0012 (12)
N3a0.0319 (14)0.0348 (14)0.0391 (14)0.0051 (11)0.0097 (11)0.0018 (11)
N6a0.0426 (15)0.0357 (15)0.0419 (15)0.0074 (12)0.0121 (12)0.0042 (12)
C100.0407 (17)0.0328 (16)0.0310 (15)0.0049 (13)0.0085 (13)0.0025 (12)
O10.0485 (16)0.0490 (16)0.090 (2)0.0170 (13)0.0211 (15)0.0146 (15)
O20.069 (2)0.0495 (17)0.088 (2)0.0116 (14)0.0295 (17)0.0308 (16)
C110.0348 (16)0.0379 (17)0.0371 (16)0.0017 (14)0.0024 (13)0.0026 (14)
C30.0371 (17)0.0358 (17)0.0418 (17)0.0032 (14)0.0087 (14)0.0070 (14)
C70.052 (2)0.0414 (19)0.0474 (19)0.0035 (16)0.0153 (16)0.0047 (16)
C10.0384 (18)0.0377 (18)0.0465 (19)0.0042 (14)0.0080 (15)0.0010 (14)
C60.054 (2)0.049 (2)0.062 (2)0.0189 (18)0.0186 (19)0.0163 (19)
C140.048 (2)0.056 (2)0.074 (3)0.0132 (19)0.012 (2)0.008 (2)
C90.0324 (16)0.047 (2)0.0386 (17)0.0003 (14)0.0035 (13)0.0087 (15)
C50.0413 (19)0.062 (3)0.058 (2)0.0159 (18)0.0021 (17)0.009 (2)
C120.051 (2)0.041 (2)0.058 (2)0.0023 (16)0.0087 (18)0.0129 (17)
C40.0343 (17)0.056 (2)0.062 (2)0.0136 (16)0.0122 (16)0.0050 (18)
C130.060 (2)0.037 (2)0.085 (3)0.0010 (18)0.002 (2)0.006 (2)
C150.055 (3)0.122 (4)0.054 (2)0.015 (3)0.015 (2)0.013 (3)
Geometric parameters (Å, º) top
S1—C31.656 (4)C6—H6A0.9700
S2—C91.647 (3)C6—H6B0.9700
N8—C71.380 (5)C14—C151.499 (7)
N8—C91.397 (5)C14—H14A0.9700
N8—C141.487 (5)C14—H14B0.9700
N2—C31.361 (5)C5—C41.505 (6)
N2—C11.413 (5)C5—H5A0.9700
N2—C121.483 (5)C5—H5B0.9700
N3a—C101.362 (4)C12—C131.512 (6)
N3a—C31.393 (4)C12—H12A0.9700
N3a—C41.493 (4)C12—H12B0.9700
N6a—C101.376 (4)C4—H4A0.9700
N6a—C71.393 (5)C4—H4B0.9700
N6a—C61.467 (4)C13—H13A0.9600
C10—C111.363 (5)C13—H13B0.9600
O1—C11.210 (4)C13—H13C0.9600
O2—C71.221 (5)C15—H15A0.9600
C11—C11.454 (5)C15—H15B0.9600
C11—C91.457 (5)C15—H15C0.9600
C6—C51.492 (6)
C7—N8—C9124.8 (3)N8—C14—H14B109.4
C7—N8—C14115.6 (3)C15—C14—H14B109.4
C9—N8—C14119.6 (3)H14A—C14—H14B108.0
C3—N2—C1124.6 (3)N8—C9—C11114.1 (3)
C3—N2—C12119.6 (3)N8—C9—S2120.0 (3)
C1—N2—C12115.5 (3)C11—C9—S2125.8 (3)
C10—N3a—C3121.1 (3)C6—C5—C4108.5 (3)
C10—N3a—C4122.7 (3)C6—C5—H5A110.0
C3—N3a—C4116.2 (3)C4—C5—H5A110.0
C10—N6a—C7121.7 (3)C6—C5—H5B110.0
C10—N6a—C6121.9 (3)C4—C5—H5B110.0
C7—N6a—C6116.4 (3)H5A—C5—H5B108.4
N3a—C10—C11121.9 (3)N2—C12—C13111.9 (3)
N3a—C10—N6a118.0 (3)N2—C12—H12A109.2
C11—C10—N6a120.1 (3)C13—C12—H12A109.2
C10—C11—C1118.4 (3)N2—C12—H12B109.2
C10—C11—C9121.6 (3)C13—C12—H12B109.2
C1—C11—C9120.0 (3)H12A—C12—H12B107.9
N2—C3—N3a116.3 (3)N3a—C4—C5110.6 (3)
N2—C3—S1122.7 (3)N3a—C4—H4A109.5
N3a—C3—S1121.0 (3)C5—C4—H4A109.5
O2—C7—N8122.7 (4)N3a—C4—H4B109.5
O2—C7—N6a120.0 (4)C5—C4—H4B109.5
N8—C7—N6a117.3 (3)H4A—C4—H4B108.1
O1—C1—N2119.0 (3)C12—C13—H13A109.5
O1—C1—C11126.7 (4)C12—C13—H13B109.5
N2—C1—C11114.3 (3)H13A—C13—H13B109.5
N6a—C6—C5108.8 (3)C12—C13—H13C109.5
N6a—C6—H6A109.9H13A—C13—H13C109.5
C5—C6—H6A109.9H13B—C13—H13C109.5
N6a—C6—H6B109.9C14—C15—H15A109.5
C5—C6—H6B109.9C14—C15—H15B109.5
H6A—C6—H6B108.3H15A—C15—H15B109.5
N8—C14—C15111.2 (4)C14—C15—H15C109.5
N8—C14—H14A109.4H15A—C15—H15C109.5
C15—C14—H14A109.4H15B—C15—H15C109.5
C3—N3a—C10—C119.3 (5)C6—N6a—C7—N8176.8 (3)
C4—N3a—C10—C11170.9 (3)C3—N2—C1—O1165.3 (4)
C3—N3a—C10—N6a170.4 (3)C12—N2—C1—O18.8 (5)
C4—N3a—C10—N6a9.4 (5)C3—N2—C1—C1114.2 (5)
C7—N6a—C10—N3a179.4 (3)C12—N2—C1—C11171.7 (3)
C6—N6a—C10—N3a0.4 (5)C10—C11—C1—O1161.5 (4)
C7—N6a—C10—C110.9 (5)C9—C11—C1—O116.7 (6)
C6—N6a—C10—C11179.3 (3)C10—C11—C1—N217.9 (5)
N3a—C10—C11—C17.1 (5)C9—C11—C1—N2163.9 (3)
N6a—C10—C11—C1173.2 (3)C10—N6a—C6—C535.9 (5)
N3a—C10—C11—C9174.7 (3)C7—N6a—C6—C5143.8 (3)
N6a—C10—C11—C95.0 (5)C7—N8—C14—C1598.1 (5)
C1—N2—C3—N3a0.9 (5)C9—N8—C14—C1582.2 (5)
C12—N2—C3—N3a172.9 (3)C7—N8—C9—C115.4 (5)
C1—N2—C3—S1179.6 (3)C14—N8—C9—C11175.0 (3)
C12—N2—C3—S16.5 (4)C7—N8—C9—S2173.3 (3)
C10—N3a—C3—N213.3 (4)C14—N8—C9—S26.3 (5)
C4—N3a—C3—N2166.9 (3)C10—C11—C9—N87.9 (5)
C10—N3a—C3—S1167.2 (2)C1—C11—C9—N8170.3 (3)
C4—N3a—C3—S112.6 (4)C10—C11—C9—S2170.7 (3)
C9—N8—C7—O2178.4 (4)C1—C11—C9—S211.1 (5)
C14—N8—C7—O21.2 (6)N6a—C6—C5—C460.4 (4)
C9—N8—C7—N6a0.1 (5)C3—N2—C12—C1383.1 (4)
C14—N8—C7—N6a179.7 (3)C1—N2—C12—C1391.3 (4)
C10—N6a—C7—O2178.0 (3)C10—N3a—C4—C517.4 (5)
C6—N6a—C7—O21.7 (5)C3—N3a—C4—C5162.7 (3)
C10—N6a—C7—N83.4 (5)C6—C5—C4—N3a51.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O1i0.972.573.240 (5)126
C6—H6A···O20.972.282.669 (5)103
C12—H12A···S10.972.612.996 (4)104
C14—H14A···S20.972.582.961 (4)104
C14—H14B···O20.972.302.701 (5)104
Symmetry code: (i) x+1, y, z+2.
 

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