Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801003828/ya6008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801003828/ya6008Isup2.hkl |
CCDC reference: 162808
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.
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.
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.
Fig. 1. The molecular structure of N-ethyldithiophthalimide shown with 50% probability displacement ellipsoids. |
C10H9NS2 | F(000) = 432 |
Mr = 207.32 | Dx = 1.336 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yab | Cell parameters from 100 reflections |
a = 7.6119 (5) Å | θ = 10.0–16.9° |
b = 8.8460 (4) Å | µ = 0.47 mm−1 |
c = 15.611 (1) Å | T = 293 K |
β = 101.321 (5)° | Plate, brown |
V = 1030.71 (11) Å3 | 0.71 × 0.53 × 0.12 mm |
Z = 4 |
CAD-4 diffractometer | Rint = 0.043 |
ω–2θ scans | θmax = 27.9°, θmin = 1.3° |
Absorption correction: analytical (Alcock, 1974) | h = −10→10 |
Tmin = 0.754, Tmax = 0.934 | k = −11→11 |
9710 measured reflections | l = −20→20 |
2470 independent reflections | 3 standard reflections every 333.3 min |
1816 reflections with F > 2.5σ(F) | intensity decay: 6.3% |
Refinement on F | 28 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.045 | All H-atom parameters refined |
wR(F2) = 0.048 | REGINA (Wang & Robertson, 1985), see below |
S = 0.60 | (Δ/σ)max = 0.042 |
1810 reflections | Δρmax = 0.38 e Å−3 |
154 parameters | Δρmin = −0.30 e Å−3 |
C10H9NS2 | V = 1030.71 (11) Å3 |
Mr = 207.32 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 7.6119 (5) Å | µ = 0.47 mm−1 |
b = 8.8460 (4) Å | T = 293 K |
c = 15.611 (1) Å | 0.71 × 0.53 × 0.12 mm |
β = 101.321 (5)° |
CAD-4 diffractometer | 1816 reflections with F > 2.5σ(F) |
Absorption correction: analytical (Alcock, 1974) | Rint = 0.043 |
Tmin = 0.754, Tmax = 0.934 | 3 standard reflections every 333.3 min |
9710 measured reflections | intensity decay: 6.3% |
2470 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 28 restraints |
wR(F2) = 0.048 | All H-atom parameters refined |
S = 0.60 | Δρmax = 0.38 e Å−3 |
1810 reflections | Δρmin = −0.30 e Å−3 |
154 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.51714 (11) | 0.19164 (10) | 0.87964 (5) | 0.0695 (4) | |
S2 | 0.60542 (16) | 0.66304 (8) | 0.67544 (6) | 0.0861 (5) | |
N | 0.5494 (3) | 0.4443 (2) | 0.78680 (14) | 0.0544 (10) | |
C1 | 0.5512 (3) | 0.2872 (3) | 0.79524 (15) | 0.0474 (10) | |
C2 | 0.5889 (3) | 0.4889 (3) | 0.70841 (16) | 0.0515 (11) | |
C3 | 0.6129 (3) | 0.3506 (2) | 0.66075 (14) | 0.0426 (9) | |
C4 | 0.5906 (3) | 0.2286 (2) | 0.71389 (14) | 0.0421 (9) | |
C5 | 0.6042 (3) | 0.0815 (2) | 0.68534 (17) | 0.0517 (11) | |
C6 | 0.6409 (4) | 0.0605 (3) | 0.60288 (18) | 0.0580 (12) | |
C7 | 0.6624 (4) | 0.1822 (3) | 0.54987 (16) | 0.0566 (12) | |
C8 | 0.6487 (3) | 0.3295 (3) | 0.57847 (15) | 0.0503 (11) | |
C9 | 0.5044 (5) | 0.5493 (4) | 0.8523 (2) | 0.0782 (18) | |
C10 | 0.6685 (6) | 0.5957 (6) | 0.9175 (3) | 0.110 (3) | |
H5 | 0.589 (4) | −0.0093 (10) | 0.7247 (9) | 0.067 (8)* | |
H6 | 0.648 (5) | −0.0485 (11) | 0.5793 (10) | 0.081 (10)* | |
H7 | 0.680 (4) | 0.1630 (8) | 0.4868 (9) | 0.063 (8)* | |
H8 | 0.650 (4) | 0.4192 (11) | 0.5369 (8) | 0.072 (9)* | |
H91 | 0.4445 (15) | 0.6453 (12) | 0.8208 (6) | 0.104 (13)* | |
H92 | 0.4145 (14) | 0.4975 (13) | 0.8851 (6) | 0.089 (11)* | |
H101 | 0.6326 (17) | 0.673 (3) | 0.9612 (16) | 0.15 (2)* | |
H102 | 0.725 (3) | 0.5010 (16) | 0.9515 (18) | 0.19 (3)* | |
H103 | 0.761 (2) | 0.645 (4) | 0.8849 (8) | 0.14 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0668 (4) | 0.0877 (5) | 0.0572 (4) | −0.0011 (4) | 0.0201 (3) | 0.0174 (3) |
S2 | 0.1327 (8) | 0.0366 (3) | 0.0911 (6) | −0.0041 (4) | 0.0273 (5) | 0.0006 (3) |
N | 0.0575 (11) | 0.0505 (10) | 0.0562 (11) | 0.0018 (9) | 0.0133 (9) | −0.0083 (9) |
C1 | 0.0395 (10) | 0.0544 (12) | 0.0477 (10) | −0.0013 (10) | 0.0074 (8) | 0.0016 (9) |
C2 | 0.0578 (13) | 0.0403 (10) | 0.0558 (12) | −0.0008 (10) | 0.0100 (10) | −0.0050 (9) |
C3 | 0.0409 (10) | 0.0364 (9) | 0.0498 (11) | −0.0030 (8) | 0.0067 (8) | −0.0011 (8) |
C4 | 0.0372 (9) | 0.0415 (10) | 0.0463 (10) | −0.0026 (8) | 0.0052 (8) | 0.0005 (8) |
C5 | 0.0514 (13) | 0.0391 (10) | 0.0622 (13) | −0.0015 (9) | 0.0054 (10) | 0.0018 (10) |
C6 | 0.0594 (14) | 0.0448 (11) | 0.0673 (15) | 0.0029 (11) | 0.0061 (12) | −0.0115 (11) |
C7 | 0.0565 (13) | 0.0604 (14) | 0.0535 (12) | −0.0006 (11) | 0.0125 (10) | −0.0122 (11) |
C8 | 0.0519 (12) | 0.0498 (12) | 0.0499 (11) | −0.0042 (10) | 0.0117 (9) | 0.0015 (10) |
C9 | 0.087 (2) | 0.080 (2) | 0.0724 (18) | 0.0107 (18) | 0.0266 (16) | −0.0223 (16) |
C10 | 0.107 (3) | 0.128 (4) | 0.094 (3) | −0.007 (3) | 0.018 (2) | −0.057 (3) |
S1—C1 | 1.629 (3) | C6—C7 | 1.387 (4) |
S2—C2 | 1.637 (3) | C6—H6 | 1.037 (12) |
N—C1 | 1.395 (3) | C7—C8 | 1.389 (4) |
N—C2 | 1.374 (4) | C7—H7 | 1.034 (16) |
N—C9 | 1.471 (4) | C8—H8 | 1.026 (12) |
C1—C4 | 1.457 (3) | C9—C10 | 1.505 (6) |
C2—C3 | 1.462 (3) | C9—H91 | 1.041 (11) |
C3—C4 | 1.392 (3) | C9—H92 | 1.038 (12) |
C3—C8 | 1.377 (3) | C10—H101 | 1.04 (3) |
C4—C5 | 1.386 (3) | C10—H102 | 1.040 (19) |
C5—C6 | 1.382 (4) | C10—H103 | 1.04 (2) |
C5—H5 | 1.031 (13) | ||
C1—N—C2 | 111.7 (2) | C7—C6—H6 | 119.3 (11) |
C1—N—C9 | 124.2 (2) | C6—C7—C8 | 120.8 (2) |
C2—N—C9 | 124.0 (2) | C6—C7—H7 | 119.6 (5) |
S1—C1—N | 126.4 (2) | C8—C7—H7 | 119.5 (5) |
S1—C1—C4 | 127.8 (2) | C3—C8—C7 | 117.9 (2) |
N—C1—C4 | 105.8 (2) | C3—C8—H8 | 120.9 (9) |
S2—C2—N | 126.5 (2) | C7—C8—H8 | 120.8 (8) |
S2—C2—C3 | 127.0 (2) | N—C9—C10 | 111.5 (3) |
N—C2—C3 | 106.5 (2) | N—C9—H91 | 109.0 (6) |
C2—C3—C4 | 107.7 (2) | N—C9—H92 | 109.3 (7) |
C2—C3—C8 | 130.9 (2) | C10—C9—H91 | 109.0 (7) |
C4—C3—C8 | 121.4 (2) | C10—C9—H92 | 109.1 (6) |
C1—C4—C3 | 108.3 (2) | H91—C9—H92 | 108.9 (9) |
C1—C4—C5 | 131.0 (2) | C9—C10—H101 | 109.4 (9) |
C3—C4—C5 | 120.7 (2) | C9—C10—H102 | 109.5 (12) |
C4—C5—C6 | 117.8 (2) | C9—C10—H103 | 109.4 (8) |
C4—C5—H5 | 121.0 (9) | H101—C10—H102 | 109 (2) |
C6—C5—H5 | 121.1 (9) | H101—C10—H103 | 110 (2) |
C5—C6—C7 | 121.4 (2) | H102—C10—H103 | 109 (2) |
C5—C6—H6 | 119.3 (11) | ||
C2—N—C1—S1 | 178.03 (18) | C4—C3—C8—C7 | −0.1 (3) |
C2—N—C1—C4 | −1.6 (3) | C4—C3—C8—H8 | 172.5 (19) |
C9—N—C1—S1 | −4.0 (4) | C1—C4—C5—C6 | 178.9 (2) |
C9—N—C1—C4 | 176.3 (2) | C1—C4—C5—H5 | −1.9 (19) |
C1—N—C2—S2 | −178.14 (19) | C3—C4—C5—C6 | 0.2 (3) |
C1—N—C2—C3 | 1.9 (3) | C3—C4—C5—H5 | 179.4 (19) |
C9—N—C2—S2 | 3.9 (4) | C4—C5—C6—C7 | −0.5 (4) |
C9—N—C2—C3 | −176.1 (2) | C4—C5—C6—H6 | −178 (2) |
C1—N—C9—C10 | 90.7 (4) | H5—C5—C6—C7 | −179.7 (18) |
C1—N—C9—H91 | −148.9 (7) | H5—C5—C6—H6 | 3 (3) |
C1—N—C9—H92 | −29.9 (7) | C5—C6—C7—C8 | 0.4 (4) |
C2—N—C9—C10 | −91.6 (4) | C5—C6—C7—H7 | −175.3 (18) |
C2—N—C9—H91 | 28.9 (8) | H6—C6—C7—C8 | 178 (2) |
C2—N—C9—H92 | 147.8 (6) | H6—C6—C7—H7 | 2 (3) |
S1—C1—C4—C3 | −178.95 (17) | C6—C7—C8—C3 | −0.2 (4) |
S1—C1—C4—C5 | 2.2 (4) | C6—C7—C8—H8 | −173 (2) |
N—C1—C4—C3 | 0.7 (2) | H7—C7—C8—C3 | 175.6 (18) |
N—C1—C4—C5 | −178.1 (2) | H7—C7—C8—H8 | 3 (3) |
S2—C2—C3—C4 | 178.66 (19) | N—C9—C10—H101 | 177.7 (17) |
S2—C2—C3—C8 | −2.1 (4) | N—C9—C10—H102 | −62.4 (17) |
N—C2—C3—C4 | −1.4 (3) | N—C9—C10—H103 | 58 (2) |
N—C2—C3—C8 | 177.8 (2) | H91—C9—C10—H101 | 57.2 (19) |
C2—C3—C4—C1 | 0.4 (2) | H91—C9—C10—H102 | 177.2 (18) |
C2—C3—C4—C5 | 179.4 (2) | H91—C9—C10—H103 | −63 (2) |
C8—C3—C4—C1 | −178.9 (2) | H92—C9—C10—H101 | −61.6 (19) |
C8—C3—C4—C5 | 0.1 (3) | H92—C9—C10—H102 | 58.4 (18) |
C2—C3—C8—C7 | −179.2 (2) | H92—C9—C10—H103 | 178 (2) |
C2—C3—C8—H8 | −7 (2) |
Experimental details
Crystal data | |
Chemical formula | C10H9NS2 |
Mr | 207.32 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 293 |
a, b, c (Å) | 7.6119 (5), 8.8460 (4), 15.611 (1) |
β (°) | 101.321 (5) |
V (Å3) | 1030.71 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.47 |
Crystal size (mm) | 0.71 × 0.53 × 0.12 |
Data collection | |
Diffractometer | CAD-4 diffractometer |
Absorption correction | Analytical (Alcock, 1974) |
Tmin, Tmax | 0.754, 0.934 |
No. of measured, independent and observed [F > 2.5σ(F)] reflections | 9710, 2470, 1816 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.048, 0.60 |
No. of reflections | 1810 |
No. of parameters | 154 |
No. of restraints | 28 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 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.
S1—C1 | 1.629 (3) | C3—C4 | 1.392 (3) |
S2—C2 | 1.637 (3) | C3—C8 | 1.377 (3) |
N—C1 | 1.395 (3) | C4—C5 | 1.386 (3) |
N—C2 | 1.374 (4) | C5—C6 | 1.382 (4) |
N—C9 | 1.471 (4) | C6—C7 | 1.387 (4) |
C1—C4 | 1.457 (3) | C7—C8 | 1.389 (4) |
C2—C3 | 1.462 (3) | C9—C10 | 1.505 (6) |
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