The title molecule, C
13H
16N
4O
2S
2, 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
CCDC reference: 627648
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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-(1
H)-3a,5,8,9a-
tetraazaphenalene-4,7-dione
top
Crystal data top
C13H16N4O2S2 | F(000) = 680 |
Mr = 324.42 | Dx = 1.472 Mg m−3 |
Monoclinic, P21/n | Melting point: 468 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 10.155 (2) Å | Cell parameters from 26 reflections |
b = 10.261 (2) Å | θ = 5.2–12.5° |
c = 14.382 (3) Å | µ = 0.37 mm−1 |
β = 102.33 (2)° | T = 294 K |
V = 1464.0 (5) Å3 | Prism, red |
Z = 4 | 0.38 × 0.38 × 0.15 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.033 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.3° |
Graphite monochromator | h = −1→12 |
θ/2θ scans | k = −1→12 |
3740 measured reflections | l = −17→17 |
2863 independent reflections | 3 standard reflections every 97 reflections |
2180 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.219 | H-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 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.70 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.05802 (11) | 0.24344 (10) | 1.00511 (8) | 0.0542 (4) | |
S2 | 0.68811 (9) | 0.37682 (12) | 0.90859 (8) | 0.0564 (4) | |
N8 | 0.5167 (3) | 0.5599 (3) | 0.8313 (2) | 0.0441 (7) | |
N2 | 0.3013 (3) | 0.2146 (3) | 0.9682 (2) | 0.0395 (7) | |
N3a | 0.1811 (3) | 0.3994 (3) | 0.90311 (19) | 0.0349 (6) | |
N6a | 0.2859 (3) | 0.5701 (3) | 0.8380 (2) | 0.0396 (7) | |
C10 | 0.2940 (3) | 0.4487 (3) | 0.8793 (2) | 0.0347 (7) | |
O1 | 0.4982 (3) | 0.1660 (3) | 0.9267 (2) | 0.0614 (8) | |
O2 | 0.3847 (3) | 0.7336 (3) | 0.7718 (3) | 0.0668 (9) | |
C11 | 0.4125 (3) | 0.3816 (3) | 0.8957 (2) | 0.0374 (7) | |
C3 | 0.1864 (3) | 0.2865 (3) | 0.9576 (2) | 0.0382 (7) | |
C7 | 0.3963 (4) | 0.6271 (4) | 0.8106 (3) | 0.0464 (9) | |
C1 | 0.4134 (4) | 0.2480 (3) | 0.9295 (3) | 0.0410 (8) | |
C6 | 0.1608 (4) | 0.6463 (4) | 0.8200 (3) | 0.0541 (10) | |
H6A | 0.1611 | 0.7084 | 0.7692 | 0.065* | |
H6B | 0.1535 | 0.6942 | 0.8768 | 0.065* | |
C14 | 0.6321 (4) | 0.6243 (4) | 0.8015 (3) | 0.0597 (11) | |
H14A | 0.7134 | 0.6111 | 0.8500 | 0.072* | |
H14B | 0.6154 | 0.7173 | 0.7952 | 0.072* | |
C9 | 0.5357 (3) | 0.4395 (4) | 0.8776 (2) | 0.0400 (8) | |
C5 | 0.0443 (4) | 0.5554 (4) | 0.7925 (3) | 0.0550 (10) | |
H5A | 0.0512 | 0.5078 | 0.7355 | 0.066* | |
H5B | −0.0395 | 0.6041 | 0.7795 | 0.066* | |
C12 | 0.3089 (4) | 0.0855 (4) | 1.0155 (3) | 0.0502 (9) | |
H12A | 0.2624 | 0.0897 | 1.0678 | 0.060* | |
H12B | 0.4025 | 0.0643 | 1.0417 | 0.060* | |
C4 | 0.0458 (4) | 0.4619 (4) | 0.8733 (3) | 0.0504 (9) | |
H4A | 0.0241 | 0.5082 | 0.9269 | 0.060* | |
H4B | −0.0221 | 0.3952 | 0.8536 | 0.060* | |
C13 | 0.2466 (5) | −0.0207 (4) | 0.9473 (4) | 0.0626 (11) | |
H13A | 0.1529 | −0.0019 | 0.9233 | 0.094* | |
H13B | 0.2553 | −0.1029 | 0.9800 | 0.094* | |
H13C | 0.2921 | −0.0249 | 0.8953 | 0.094* | |
C15 | 0.6525 (5) | 0.5708 (6) | 0.7086 (3) | 0.0764 (15) | |
H15A | 0.6702 | 0.4790 | 0.7149 | 0.115* | |
H15B | 0.7275 | 0.6139 | 0.6911 | 0.115* | |
H15C | 0.5727 | 0.5853 | 0.6602 | 0.115* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0516 (6) | 0.0480 (6) | 0.0707 (7) | −0.0029 (4) | 0.0306 (5) | 0.0017 (5) |
S2 | 0.0341 (5) | 0.0672 (7) | 0.0669 (7) | 0.0059 (4) | 0.0088 (4) | 0.0118 (5) |
N8 | 0.0387 (15) | 0.0413 (16) | 0.0520 (17) | −0.0033 (13) | 0.0091 (13) | 0.0039 (13) |
N2 | 0.0422 (15) | 0.0357 (15) | 0.0403 (15) | 0.0004 (12) | 0.0077 (12) | 0.0012 (12) |
N3a | 0.0319 (14) | 0.0348 (14) | 0.0391 (14) | 0.0051 (11) | 0.0097 (11) | −0.0018 (11) |
N6a | 0.0426 (15) | 0.0357 (15) | 0.0419 (15) | 0.0074 (12) | 0.0121 (12) | 0.0042 (12) |
C10 | 0.0407 (17) | 0.0328 (16) | 0.0310 (15) | 0.0049 (13) | 0.0085 (13) | −0.0025 (12) |
O1 | 0.0485 (16) | 0.0490 (16) | 0.090 (2) | 0.0170 (13) | 0.0211 (15) | 0.0146 (15) |
O2 | 0.069 (2) | 0.0495 (17) | 0.088 (2) | 0.0116 (14) | 0.0295 (17) | 0.0308 (16) |
C11 | 0.0348 (16) | 0.0379 (17) | 0.0371 (16) | 0.0017 (14) | 0.0024 (13) | −0.0026 (14) |
C3 | 0.0371 (17) | 0.0358 (17) | 0.0418 (17) | −0.0032 (14) | 0.0087 (14) | −0.0070 (14) |
C7 | 0.052 (2) | 0.0414 (19) | 0.0474 (19) | 0.0035 (16) | 0.0153 (16) | 0.0047 (16) |
C1 | 0.0384 (18) | 0.0377 (18) | 0.0465 (19) | 0.0042 (14) | 0.0080 (15) | 0.0010 (14) |
C6 | 0.054 (2) | 0.049 (2) | 0.062 (2) | 0.0189 (18) | 0.0186 (19) | 0.0163 (19) |
C14 | 0.048 (2) | 0.056 (2) | 0.074 (3) | −0.0132 (19) | 0.012 (2) | 0.008 (2) |
C9 | 0.0324 (16) | 0.047 (2) | 0.0386 (17) | −0.0003 (14) | 0.0035 (13) | −0.0087 (15) |
C5 | 0.0413 (19) | 0.062 (3) | 0.058 (2) | 0.0159 (18) | 0.0021 (17) | 0.009 (2) |
C12 | 0.051 (2) | 0.041 (2) | 0.058 (2) | 0.0023 (16) | 0.0087 (18) | 0.0129 (17) |
C4 | 0.0343 (17) | 0.056 (2) | 0.062 (2) | 0.0136 (16) | 0.0122 (16) | 0.0050 (18) |
C13 | 0.060 (2) | 0.037 (2) | 0.085 (3) | 0.0010 (18) | 0.002 (2) | 0.006 (2) |
C15 | 0.055 (3) | 0.122 (4) | 0.054 (2) | −0.015 (3) | 0.015 (2) | 0.013 (3) |
Geometric parameters (Å, º) top
S1—C3 | 1.656 (4) | C6—H6A | 0.9700 |
S2—C9 | 1.647 (3) | C6—H6B | 0.9700 |
N8—C7 | 1.380 (5) | C14—C15 | 1.499 (7) |
N8—C9 | 1.397 (5) | C14—H14A | 0.9700 |
N8—C14 | 1.487 (5) | C14—H14B | 0.9700 |
N2—C3 | 1.361 (5) | C5—C4 | 1.505 (6) |
N2—C1 | 1.413 (5) | C5—H5A | 0.9700 |
N2—C12 | 1.483 (5) | C5—H5B | 0.9700 |
N3a—C10 | 1.362 (4) | C12—C13 | 1.512 (6) |
N3a—C3 | 1.393 (4) | C12—H12A | 0.9700 |
N3a—C4 | 1.493 (4) | C12—H12B | 0.9700 |
N6a—C10 | 1.376 (4) | C4—H4A | 0.9700 |
N6a—C7 | 1.393 (5) | C4—H4B | 0.9700 |
N6a—C6 | 1.467 (4) | C13—H13A | 0.9600 |
C10—C11 | 1.363 (5) | C13—H13B | 0.9600 |
O1—C1 | 1.210 (4) | C13—H13C | 0.9600 |
O2—C7 | 1.221 (5) | C15—H15A | 0.9600 |
C11—C1 | 1.454 (5) | C15—H15B | 0.9600 |
C11—C9 | 1.457 (5) | C15—H15C | 0.9600 |
C6—C5 | 1.492 (6) | | |
| | | |
C7—N8—C9 | 124.8 (3) | N8—C14—H14B | 109.4 |
C7—N8—C14 | 115.6 (3) | C15—C14—H14B | 109.4 |
C9—N8—C14 | 119.6 (3) | H14A—C14—H14B | 108.0 |
C3—N2—C1 | 124.6 (3) | N8—C9—C11 | 114.1 (3) |
C3—N2—C12 | 119.6 (3) | N8—C9—S2 | 120.0 (3) |
C1—N2—C12 | 115.5 (3) | C11—C9—S2 | 125.8 (3) |
C10—N3a—C3 | 121.1 (3) | C6—C5—C4 | 108.5 (3) |
C10—N3a—C4 | 122.7 (3) | C6—C5—H5A | 110.0 |
C3—N3a—C4 | 116.2 (3) | C4—C5—H5A | 110.0 |
C10—N6a—C7 | 121.7 (3) | C6—C5—H5B | 110.0 |
C10—N6a—C6 | 121.9 (3) | C4—C5—H5B | 110.0 |
C7—N6a—C6 | 116.4 (3) | H5A—C5—H5B | 108.4 |
N3a—C10—C11 | 121.9 (3) | N2—C12—C13 | 111.9 (3) |
N3a—C10—N6a | 118.0 (3) | N2—C12—H12A | 109.2 |
C11—C10—N6a | 120.1 (3) | C13—C12—H12A | 109.2 |
C10—C11—C1 | 118.4 (3) | N2—C12—H12B | 109.2 |
C10—C11—C9 | 121.6 (3) | C13—C12—H12B | 109.2 |
C1—C11—C9 | 120.0 (3) | H12A—C12—H12B | 107.9 |
N2—C3—N3a | 116.3 (3) | N3a—C4—C5 | 110.6 (3) |
N2—C3—S1 | 122.7 (3) | N3a—C4—H4A | 109.5 |
N3a—C3—S1 | 121.0 (3) | C5—C4—H4A | 109.5 |
O2—C7—N8 | 122.7 (4) | N3a—C4—H4B | 109.5 |
O2—C7—N6a | 120.0 (4) | C5—C4—H4B | 109.5 |
N8—C7—N6a | 117.3 (3) | H4A—C4—H4B | 108.1 |
O1—C1—N2 | 119.0 (3) | C12—C13—H13A | 109.5 |
O1—C1—C11 | 126.7 (4) | C12—C13—H13B | 109.5 |
N2—C1—C11 | 114.3 (3) | H13A—C13—H13B | 109.5 |
N6a—C6—C5 | 108.8 (3) | C12—C13—H13C | 109.5 |
N6a—C6—H6A | 109.9 | H13A—C13—H13C | 109.5 |
C5—C6—H6A | 109.9 | H13B—C13—H13C | 109.5 |
N6a—C6—H6B | 109.9 | C14—C15—H15A | 109.5 |
C5—C6—H6B | 109.9 | C14—C15—H15B | 109.5 |
H6A—C6—H6B | 108.3 | H15A—C15—H15B | 109.5 |
N8—C14—C15 | 111.2 (4) | C14—C15—H15C | 109.5 |
N8—C14—H14A | 109.4 | H15A—C15—H15C | 109.5 |
C15—C14—H14A | 109.4 | H15B—C15—H15C | 109.5 |
| | | |
C3—N3a—C10—C11 | 9.3 (5) | C6—N6a—C7—N8 | 176.8 (3) |
C4—N3a—C10—C11 | −170.9 (3) | C3—N2—C1—O1 | −165.3 (4) |
C3—N3a—C10—N6a | −170.4 (3) | C12—N2—C1—O1 | 8.8 (5) |
C4—N3a—C10—N6a | 9.4 (5) | C3—N2—C1—C11 | 14.2 (5) |
C7—N6a—C10—N3a | −179.4 (3) | C12—N2—C1—C11 | −171.7 (3) |
C6—N6a—C10—N3a | 0.4 (5) | C10—C11—C1—O1 | 161.5 (4) |
C7—N6a—C10—C11 | 0.9 (5) | C9—C11—C1—O1 | −16.7 (6) |
C6—N6a—C10—C11 | −179.3 (3) | C10—C11—C1—N2 | −17.9 (5) |
N3a—C10—C11—C1 | 7.1 (5) | C9—C11—C1—N2 | 163.9 (3) |
N6a—C10—C11—C1 | −173.2 (3) | C10—N6a—C6—C5 | −35.9 (5) |
N3a—C10—C11—C9 | −174.7 (3) | C7—N6a—C6—C5 | 143.8 (3) |
N6a—C10—C11—C9 | 5.0 (5) | C7—N8—C14—C15 | −98.1 (5) |
C1—N2—C3—N3a | 0.9 (5) | C9—N8—C14—C15 | 82.2 (5) |
C12—N2—C3—N3a | −172.9 (3) | C7—N8—C9—C11 | 5.4 (5) |
C1—N2—C3—S1 | −179.6 (3) | C14—N8—C9—C11 | −175.0 (3) |
C12—N2—C3—S1 | 6.5 (4) | C7—N8—C9—S2 | −173.3 (3) |
C10—N3a—C3—N2 | −13.3 (4) | C14—N8—C9—S2 | 6.3 (5) |
C4—N3a—C3—N2 | 166.9 (3) | C10—C11—C9—N8 | −7.9 (5) |
C10—N3a—C3—S1 | 167.2 (2) | C1—C11—C9—N8 | 170.3 (3) |
C4—N3a—C3—S1 | −12.6 (4) | C10—C11—C9—S2 | 170.7 (3) |
C9—N8—C7—O2 | 178.4 (4) | C1—C11—C9—S2 | −11.1 (5) |
C14—N8—C7—O2 | −1.2 (6) | N6a—C6—C5—C4 | 60.4 (4) |
C9—N8—C7—N6a | −0.1 (5) | C3—N2—C12—C13 | 83.1 (4) |
C14—N8—C7—N6a | −179.7 (3) | C1—N2—C12—C13 | −91.3 (4) |
C10—N6a—C7—O2 | 178.0 (3) | C10—N3a—C4—C5 | 17.4 (5) |
C6—N6a—C7—O2 | −1.7 (5) | C3—N3a—C4—C5 | −162.7 (3) |
C10—N6a—C7—N8 | −3.4 (5) | C6—C5—C4—N3a | −51.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12B···O1i | 0.97 | 2.57 | 3.240 (5) | 126 |
C6—H6A···O2 | 0.97 | 2.28 | 2.669 (5) | 103 |
C12—H12A···S1 | 0.97 | 2.61 | 2.996 (4) | 104 |
C14—H14A···S2 | 0.97 | 2.58 | 2.961 (4) | 104 |
C14—H14B···O2 | 0.97 | 2.30 | 2.701 (5) | 104 |
Symmetry code: (i) −x+1, −y, −z+2. |