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The title compound, C10H9NS2, represents the first structurally studied derivative of di­thio­phthal­imide. The C=S bond lengths are 1.629 (3) and 1.637 (3) Å; other geometric parameters are very close to the analogous values observed in the phthal­imide structures. The least-square planes of the di­thio­phthal­imide parts of the mol­ecules in the crystal are parallel; these parts do not form any short contacts, leaving space for the ethyl groups pointing out of the plane [the `out-of-plane torsion angles' C-N-C-C being equal to 90.7 (4) and -91.6 (4)°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801003828/ya6008sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801003828/ya6008Isup2.hkl
Contains datablock I

CCDC reference: 162808

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.048
  • Data-to-parameter ratio = 11.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry




Comment top

No comment

Experimental top

A mixture of 42 mmol of phthalimide and 14 mmol of P4S10 in 50 ml of xylene was heated to reflux. After 20 h, the mixture was cooled to 293 K and excess P4S10 was filtered off. Xylene was removed under reduced pressure. The residue was dissolved in acetone, filtered and dried. The separation of dithiophthalimide from thiophthalimide was made by column chromatography on silica gel in hexane. The crystals were prepared by recrystallization from hot methanol.

Refinement top

H atoms were found in the difference Fourier map and were refined isotropically with restrained C—H bonds [prescribed value was 1.04 (1) Å] and C–C–H (or N–C–H) angles [prescribed values were 109.5 (5)° for ethyl and 120.0 (5)° for phthalimide H atoms]. A REGINA (Wang & Robertson, 1985) weighting scheme using the normal equation of the second order was applied for individual reflections so that weight = A(0,0) + A(1,0) V(F) + A(0,1) V(S) + A(2,0) V(F)2 + A(0,2) V(S)2 + A(1,1) V(F)V(S), where V(F) = Fobs/Fobs(max), Fobs(max) = 187.37 and V(S) = (sinθ/λ)/[sinθ/λ(max)], sinθ/λ(max) = 0.6582. The parameters were: A(0,0) = 2.850259, A(1,0) = -0.0428708, A(0,1) = -5.150394, A(2,0) = 0.0017199, A(0,2) = 2.617157 and A(1,1) = -0.0495276. The final geometric parameters are given in Table 1, while the molecular geometry and labeling scheme are presented in Fig. 1.

Computing details top

Data collection: CAD04 Software (Enraf-Nonius, 1989); cell refinement: Xtal3.6 LATCON (Hall et al., 1999); data reduction: Xtal DIFDAT SORTRF ADDREF, (Hall et al., 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: Xtal3.6 CRYLSQ; molecular graphics: Xtal3.6 ORTEP; software used to prepare material for publication: Xtal3.6 BONDLA CIFIO.

Figures top
[Figure 1] Fig. 1. The molecular structure of N-ethyldithiophthalimide shown with 50% probability displacement ellipsoids.
N-ethyldithiophthalimide top
Crystal data top
C10H9NS2F(000) = 432
Mr = 207.32Dx = 1.336 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yabCell parameters from 100 reflections
a = 7.6119 (5) Åθ = 10.0–16.9°
b = 8.8460 (4) ŵ = 0.47 mm1
c = 15.611 (1) ÅT = 293 K
β = 101.321 (5)°Plate, brown
V = 1030.71 (11) Å30.71 × 0.53 × 0.12 mm
Z = 4
Data collection top
CAD-4
diffractometer
Rint = 0.043
ω–2θ scansθmax = 27.9°, θmin = 1.3°
Absorption correction: analytical
(Alcock, 1974)
h = 1010
Tmin = 0.754, Tmax = 0.934k = 1111
9710 measured reflectionsl = 2020
2470 independent reflections3 standard reflections every 333.3 min
1816 reflections with F > 2.5σ(F) intensity decay: 6.3%
Refinement top
Refinement on F28 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.045All H-atom parameters refined
wR(F2) = 0.048 REGINA (Wang & Robertson, 1985), see below
S = 0.60(Δ/σ)max = 0.042
1810 reflectionsΔρmax = 0.38 e Å3
154 parametersΔρmin = 0.30 e Å3
Crystal data top
C10H9NS2V = 1030.71 (11) Å3
Mr = 207.32Z = 4
Monoclinic, P21/aMo Kα radiation
a = 7.6119 (5) ŵ = 0.47 mm1
b = 8.8460 (4) ÅT = 293 K
c = 15.611 (1) Å0.71 × 0.53 × 0.12 mm
β = 101.321 (5)°
Data collection top
CAD-4
diffractometer
1816 reflections with F > 2.5σ(F)
Absorption correction: analytical
(Alcock, 1974)
Rint = 0.043
Tmin = 0.754, Tmax = 0.9343 standard reflections every 333.3 min
9710 measured reflections intensity decay: 6.3%
2470 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04528 restraints
wR(F2) = 0.048All H-atom parameters refined
S = 0.60Δρmax = 0.38 e Å3
1810 reflectionsΔρmin = 0.30 e Å3
154 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.51714 (11)0.19164 (10)0.87964 (5)0.0695 (4)
S20.60542 (16)0.66304 (8)0.67544 (6)0.0861 (5)
N0.5494 (3)0.4443 (2)0.78680 (14)0.0544 (10)
C10.5512 (3)0.2872 (3)0.79524 (15)0.0474 (10)
C20.5889 (3)0.4889 (3)0.70841 (16)0.0515 (11)
C30.6129 (3)0.3506 (2)0.66075 (14)0.0426 (9)
C40.5906 (3)0.2286 (2)0.71389 (14)0.0421 (9)
C50.6042 (3)0.0815 (2)0.68534 (17)0.0517 (11)
C60.6409 (4)0.0605 (3)0.60288 (18)0.0580 (12)
C70.6624 (4)0.1822 (3)0.54987 (16)0.0566 (12)
C80.6487 (3)0.3295 (3)0.57847 (15)0.0503 (11)
C90.5044 (5)0.5493 (4)0.8523 (2)0.0782 (18)
C100.6685 (6)0.5957 (6)0.9175 (3)0.110 (3)
H50.589 (4)0.0093 (10)0.7247 (9)0.067 (8)*
H60.648 (5)0.0485 (11)0.5793 (10)0.081 (10)*
H70.680 (4)0.1630 (8)0.4868 (9)0.063 (8)*
H80.650 (4)0.4192 (11)0.5369 (8)0.072 (9)*
H910.4445 (15)0.6453 (12)0.8208 (6)0.104 (13)*
H920.4145 (14)0.4975 (13)0.8851 (6)0.089 (11)*
H1010.6326 (17)0.673 (3)0.9612 (16)0.15 (2)*
H1020.725 (3)0.5010 (16)0.9515 (18)0.19 (3)*
H1030.761 (2)0.645 (4)0.8849 (8)0.14 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0668 (4)0.0877 (5)0.0572 (4)0.0011 (4)0.0201 (3)0.0174 (3)
S20.1327 (8)0.0366 (3)0.0911 (6)0.0041 (4)0.0273 (5)0.0006 (3)
N0.0575 (11)0.0505 (10)0.0562 (11)0.0018 (9)0.0133 (9)0.0083 (9)
C10.0395 (10)0.0544 (12)0.0477 (10)0.0013 (10)0.0074 (8)0.0016 (9)
C20.0578 (13)0.0403 (10)0.0558 (12)0.0008 (10)0.0100 (10)0.0050 (9)
C30.0409 (10)0.0364 (9)0.0498 (11)0.0030 (8)0.0067 (8)0.0011 (8)
C40.0372 (9)0.0415 (10)0.0463 (10)0.0026 (8)0.0052 (8)0.0005 (8)
C50.0514 (13)0.0391 (10)0.0622 (13)0.0015 (9)0.0054 (10)0.0018 (10)
C60.0594 (14)0.0448 (11)0.0673 (15)0.0029 (11)0.0061 (12)0.0115 (11)
C70.0565 (13)0.0604 (14)0.0535 (12)0.0006 (11)0.0125 (10)0.0122 (11)
C80.0519 (12)0.0498 (12)0.0499 (11)0.0042 (10)0.0117 (9)0.0015 (10)
C90.087 (2)0.080 (2)0.0724 (18)0.0107 (18)0.0266 (16)0.0223 (16)
C100.107 (3)0.128 (4)0.094 (3)0.007 (3)0.018 (2)0.057 (3)
Geometric parameters (Å, º) top
S1—C11.629 (3)C6—C71.387 (4)
S2—C21.637 (3)C6—H61.037 (12)
N—C11.395 (3)C7—C81.389 (4)
N—C21.374 (4)C7—H71.034 (16)
N—C91.471 (4)C8—H81.026 (12)
C1—C41.457 (3)C9—C101.505 (6)
C2—C31.462 (3)C9—H911.041 (11)
C3—C41.392 (3)C9—H921.038 (12)
C3—C81.377 (3)C10—H1011.04 (3)
C4—C51.386 (3)C10—H1021.040 (19)
C5—C61.382 (4)C10—H1031.04 (2)
C5—H51.031 (13)
C1—N—C2111.7 (2)C7—C6—H6119.3 (11)
C1—N—C9124.2 (2)C6—C7—C8120.8 (2)
C2—N—C9124.0 (2)C6—C7—H7119.6 (5)
S1—C1—N126.4 (2)C8—C7—H7119.5 (5)
S1—C1—C4127.8 (2)C3—C8—C7117.9 (2)
N—C1—C4105.8 (2)C3—C8—H8120.9 (9)
S2—C2—N126.5 (2)C7—C8—H8120.8 (8)
S2—C2—C3127.0 (2)N—C9—C10111.5 (3)
N—C2—C3106.5 (2)N—C9—H91109.0 (6)
C2—C3—C4107.7 (2)N—C9—H92109.3 (7)
C2—C3—C8130.9 (2)C10—C9—H91109.0 (7)
C4—C3—C8121.4 (2)C10—C9—H92109.1 (6)
C1—C4—C3108.3 (2)H91—C9—H92108.9 (9)
C1—C4—C5131.0 (2)C9—C10—H101109.4 (9)
C3—C4—C5120.7 (2)C9—C10—H102109.5 (12)
C4—C5—C6117.8 (2)C9—C10—H103109.4 (8)
C4—C5—H5121.0 (9)H101—C10—H102109 (2)
C6—C5—H5121.1 (9)H101—C10—H103110 (2)
C5—C6—C7121.4 (2)H102—C10—H103109 (2)
C5—C6—H6119.3 (11)
C2—N—C1—S1178.03 (18)C4—C3—C8—C70.1 (3)
C2—N—C1—C41.6 (3)C4—C3—C8—H8172.5 (19)
C9—N—C1—S14.0 (4)C1—C4—C5—C6178.9 (2)
C9—N—C1—C4176.3 (2)C1—C4—C5—H51.9 (19)
C1—N—C2—S2178.14 (19)C3—C4—C5—C60.2 (3)
C1—N—C2—C31.9 (3)C3—C4—C5—H5179.4 (19)
C9—N—C2—S23.9 (4)C4—C5—C6—C70.5 (4)
C9—N—C2—C3176.1 (2)C4—C5—C6—H6178 (2)
C1—N—C9—C1090.7 (4)H5—C5—C6—C7179.7 (18)
C1—N—C9—H91148.9 (7)H5—C5—C6—H63 (3)
C1—N—C9—H9229.9 (7)C5—C6—C7—C80.4 (4)
C2—N—C9—C1091.6 (4)C5—C6—C7—H7175.3 (18)
C2—N—C9—H9128.9 (8)H6—C6—C7—C8178 (2)
C2—N—C9—H92147.8 (6)H6—C6—C7—H72 (3)
S1—C1—C4—C3178.95 (17)C6—C7—C8—C30.2 (4)
S1—C1—C4—C52.2 (4)C6—C7—C8—H8173 (2)
N—C1—C4—C30.7 (2)H7—C7—C8—C3175.6 (18)
N—C1—C4—C5178.1 (2)H7—C7—C8—H83 (3)
S2—C2—C3—C4178.66 (19)N—C9—C10—H101177.7 (17)
S2—C2—C3—C82.1 (4)N—C9—C10—H10262.4 (17)
N—C2—C3—C41.4 (3)N—C9—C10—H10358 (2)
N—C2—C3—C8177.8 (2)H91—C9—C10—H10157.2 (19)
C2—C3—C4—C10.4 (2)H91—C9—C10—H102177.2 (18)
C2—C3—C4—C5179.4 (2)H91—C9—C10—H10363 (2)
C8—C3—C4—C1178.9 (2)H92—C9—C10—H10161.6 (19)
C8—C3—C4—C50.1 (3)H92—C9—C10—H10258.4 (18)
C2—C3—C8—C7179.2 (2)H92—C9—C10—H103178 (2)
C2—C3—C8—H87 (2)

Experimental details

Crystal data
Chemical formulaC10H9NS2
Mr207.32
Crystal system, space groupMonoclinic, P21/a
Temperature (K)293
a, b, c (Å)7.6119 (5), 8.8460 (4), 15.611 (1)
β (°) 101.321 (5)
V3)1030.71 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.47
Crystal size (mm)0.71 × 0.53 × 0.12
Data collection
DiffractometerCAD-4
diffractometer
Absorption correctionAnalytical
(Alcock, 1974)
Tmin, Tmax0.754, 0.934
No. of measured, independent and
observed [F > 2.5σ(F)] reflections
9710, 2470, 1816
Rint0.043
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.048, 0.60
No. of reflections1810
No. of parameters154
No. of restraints28
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.38, 0.30

Computer programs: CAD04 Software (Enraf-Nonius, 1989), Xtal3.6 LATCON (Hall et al., 1999), Xtal DIFDAT SORTRF ADDREF, (Hall et al., 1999), SIR97 (Altomare et al., 1999), Xtal3.6 CRYLSQ, Xtal3.6 ORTEP, Xtal3.6 BONDLA CIFIO.

Selected bond lengths (Å) top
S1—C11.629 (3)C3—C41.392 (3)
S2—C21.637 (3)C3—C81.377 (3)
N—C11.395 (3)C4—C51.386 (3)
N—C21.374 (4)C5—C61.382 (4)
N—C91.471 (4)C6—C71.387 (4)
C1—C41.457 (3)C7—C81.389 (4)
C2—C31.462 (3)C9—C101.505 (6)
 

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