2-(3-Ethyl-2,3,4,5-tetra­hydro-4-oxo-2-thio­xo-4-thia­zolidin-5-yl­idene)-1,2-di­hydro­ace­naphthyl­en-1-one

In the title compound, C₁₇H₁₁NO₂S₂, the thia­zolidinone moiety is almost coplanar with the ace­naphthyl­ene moiety. The molecular packing is influenced mainly by weak intra- and intermolecular C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.151
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.86

Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           69.19
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               2338
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2719
           Completeness (_total/calc)             85.99%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.86

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   1 ALERT level A = In general: serious problem
   2 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1997–2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

2-(3-Ethyl-2,3,4,5-tetrahydro-4-oxo-2-thioxo-4-thiazolidin-5-ylidene)- 1,2-dihydroacenaphthylen-1-one

Crystal data

C17H11NO2S2	F(000) = 672
Mr = 325.39	Dx = 1.480 Mg m^−3
Monoclinic, P21/c	Melting point: 483 K K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.5418 Å
a = 7.382 (5) Å	Cell parameters from 2248 reflections
b = 26.375 (5) Å	θ = 2.0–68.0°
c = 7.511 (5) Å	µ = 3.36 mm^−1
β = 92.911 (5)°	T = 293 K
V = 1460.5 (14) Å^3	Needle, orange
Z = 4	0.12 × 0.11 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	1427 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 69.2°, θmin = 3.4°
φ scans with κ offsets	h = −8→8
4416 measured reflections	k = −31→31
2338 independent reflections	l = −9→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0792P)^2 + 0.1394P] where P = (Fo^2 + 2Fc^2)/3
2338 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.24945 (12)	0.36221 (4)	0.16933 (13)	0.0567 (3)
S2	0.31324 (16)	0.47252 (4)	0.19844 (17)	0.0803 (4)
C9	0.5131 (4)	0.22481 (12)	0.2912 (5)	0.0482 (9)
O2	0.7115 (3)	0.32990 (10)	0.3940 (4)	0.0705 (8)
O1	0.0956 (3)	0.27197 (10)	0.0949 (4)	0.0719 (8)
C1	0.2213 (5)	0.24661 (13)	0.1580 (5)	0.0501 (9)
N1	0.5417 (4)	0.39931 (11)	0.3175 (4)	0.0578 (8)
C11	0.4093 (4)	0.18059 (13)	0.2474 (5)	0.0475 (9)
C14	0.5741 (5)	0.34747 (14)	0.3285 (5)	0.0526 (9)
C13	0.4153 (4)	0.31942 (12)	0.2469 (5)	0.0485 (9)
C2	0.2360 (4)	0.19139 (13)	0.1697 (4)	0.0496 (9)
C3	0.1202 (5)	0.15282 (14)	0.1220 (5)	0.0593 (10)
H3	0.0058	0.1594	0.0695	0.071*
C12	0.3961 (4)	0.26867 (13)	0.2382 (5)	0.0484 (9)
C8	0.6845 (5)	0.21850 (14)	0.3658 (5)	0.0560 (10)
H8	0.7577	0.2464	0.3938	0.067*
C10	0.4711 (5)	0.13139 (13)	0.2767 (5)	0.0534 (9)
C15	0.3819 (5)	0.41470 (13)	0.2348 (5)	0.0562 (10)
C6	0.6470 (5)	0.12590 (14)	0.3556 (5)	0.0600 (10)
H6	0.6947	0.0938	0.3781	0.072*
C4	0.1794 (5)	0.10254 (15)	0.1546 (5)	0.0664 (11)
H4	0.1008	0.0759	0.1256	0.080*
C5	0.3477 (5)	0.09190 (14)	0.2272 (5)	0.0617 (11)
H5	0.3825	0.0583	0.2447	0.074*
C7	0.7480 (5)	0.16844 (14)	0.3996 (5)	0.0608 (11)
H7	0.8631	0.1642	0.4538	0.073*
C16	0.6765 (5)	0.43519 (15)	0.3980 (6)	0.0682 (11)
H16A	0.7362	0.4199	0.5027	0.082*
H16B	0.6152	0.4656	0.4353	0.082*
C17	0.8163 (6)	0.44903 (17)	0.2669 (6)	0.0860 (14)
H17A	0.8818	0.4192	0.2353	0.129*
H17B	0.8991	0.4734	0.3201	0.129*
H17C	0.7569	0.4633	0.1618	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0507 (5)	0.0554 (6)	0.0633 (7)	0.0027 (4)	−0.0032 (5)	0.0048 (4)
S2	0.0796 (7)	0.0547 (7)	0.1057 (11)	0.0064 (5)	−0.0043 (7)	0.0071 (6)
C9	0.0444 (18)	0.056 (2)	0.044 (2)	−0.0009 (16)	−0.0018 (17)	−0.0010 (17)
O2	0.0597 (16)	0.0598 (17)	0.089 (2)	0.0015 (13)	−0.0251 (16)	0.0002 (15)
O1	0.0545 (15)	0.0635 (17)	0.095 (2)	0.0026 (13)	−0.0194 (15)	0.0051 (15)
C1	0.050 (2)	0.055 (2)	0.045 (3)	−0.0004 (17)	−0.0041 (18)	0.0018 (17)
N1	0.0527 (17)	0.0535 (19)	0.066 (2)	−0.0021 (14)	−0.0044 (17)	−0.0022 (15)
C11	0.0469 (18)	0.052 (2)	0.043 (2)	−0.0026 (16)	0.0006 (18)	−0.0044 (17)
C14	0.052 (2)	0.056 (2)	0.049 (3)	−0.0013 (17)	−0.0059 (19)	−0.0011 (17)
C13	0.0474 (18)	0.050 (2)	0.048 (2)	−0.0020 (15)	−0.0002 (18)	−0.0005 (17)
C2	0.0466 (19)	0.056 (2)	0.045 (3)	−0.0012 (16)	−0.0021 (18)	0.0026 (16)
C3	0.051 (2)	0.063 (3)	0.062 (3)	−0.0055 (18)	−0.0086 (19)	−0.0040 (19)
C12	0.0441 (18)	0.054 (2)	0.046 (2)	0.0028 (16)	−0.0010 (17)	0.0043 (17)
C8	0.050 (2)	0.057 (2)	0.060 (3)	0.0004 (17)	−0.0039 (19)	−0.0019 (18)
C10	0.060 (2)	0.053 (2)	0.047 (3)	0.0012 (17)	0.000 (2)	−0.0039 (17)
C15	0.054 (2)	0.056 (2)	0.059 (3)	0.0013 (17)	0.002 (2)	0.0005 (18)
C6	0.059 (2)	0.056 (2)	0.064 (3)	0.0070 (18)	−0.006 (2)	−0.0015 (19)
C4	0.066 (2)	0.061 (3)	0.071 (3)	−0.013 (2)	−0.003 (2)	−0.010 (2)
C5	0.068 (2)	0.050 (2)	0.067 (3)	−0.0017 (18)	0.003 (2)	−0.0047 (19)
C7	0.052 (2)	0.061 (3)	0.068 (3)	0.0071 (18)	−0.008 (2)	−0.001 (2)
C16	0.067 (2)	0.060 (2)	0.076 (3)	−0.005 (2)	−0.012 (2)	−0.006 (2)
C17	0.073 (3)	0.081 (3)	0.105 (4)	−0.008 (2)	0.010 (3)	−0.001 (3)

Geometric parameters (Å, º)

S1—C13	1.743 (4)	C3—C4	1.414 (5)
S1—C15	1.751 (4)	C3—H3	0.93
S2—C15	1.626 (4)	C8—C7	1.420 (5)
C9—C8	1.367 (5)	C8—H8	0.93
C9—C11	1.425 (4)	C10—C6	1.407 (5)
C9—C12	1.486 (4)	C10—C5	1.421 (5)
O2—C14	1.198 (4)	C6—C7	1.378 (5)
O1—C1	1.220 (4)	C6—H6	0.93
C1—C2	1.463 (5)	C4—C5	1.360 (6)
C1—C12	1.513 (5)	C4—H4	0.93
N1—C15	1.367 (5)	C5—H5	0.93
N1—C14	1.390 (4)	C7—H7	0.93
N1—C16	1.480 (5)	C16—C17	1.507 (5)
C11—C10	1.389 (5)	C16—H16A	0.97
C11—C2	1.408 (5)	C16—H16B	0.97
C14—C13	1.491 (5)	C17—H17A	0.96
C13—C12	1.347 (4)	C17—H17B	0.96
C2—C3	1.365 (5)	C17—H17C	0.96
C13—S1—C15	92.61 (18)	C11—C10—C6	116.8 (3)
C8—C9—C11	118.1 (3)	C11—C10—C5	116.3 (4)
C8—C9—C12	135.9 (3)	C6—C10—C5	126.9 (3)
C11—C9—C12	106.1 (3)	N1—C15—S2	127.5 (3)
O1—C1—C2	128.5 (3)	N1—C15—S1	110.5 (3)
O1—C1—C12	124.1 (3)	S2—C15—S1	122.0 (2)
C2—C1—C12	107.5 (3)	C7—C6—C10	119.6 (3)
C15—N1—C14	117.4 (3)	C7—C6—H6	120.2
C15—N1—C16	122.9 (3)	C10—C6—H6	120.2
C14—N1—C16	119.7 (3)	C5—C4—C3	122.1 (4)
C10—C11—C2	122.6 (3)	C5—C4—H4	119.0
C10—C11—C9	124.0 (3)	C3—C4—H4	119.0
C2—C11—C9	113.4 (3)	C4—C5—C10	120.9 (3)
O2—C14—N1	123.0 (3)	C4—C5—H5	119.5
O2—C14—C13	127.5 (3)	C10—C5—H5	119.5
N1—C14—C13	109.5 (3)	C6—C7—C8	123.0 (4)
C12—C13—C14	126.2 (3)	C6—C7—H7	118.5
C12—C13—S1	123.8 (3)	C8—C7—H7	118.5
C14—C13—S1	109.9 (2)	N1—C16—C17	110.9 (3)
C3—C2—C11	120.1 (3)	N1—C16—H16A	109.5
C3—C2—C1	133.1 (3)	C17—C16—H16A	109.5
C11—C2—C1	106.8 (3)	N1—C16—H16B	109.5
C2—C3—C4	118.0 (4)	C17—C16—H16B	109.5
C2—C3—H3	121.0	H16A—C16—H16B	108.0
C4—C3—H3	121.0	C16—C17—H17A	109.5
C13—C12—C9	134.6 (3)	C16—C17—H17B	109.5
C13—C12—C1	119.1 (3)	H17A—C17—H17B	109.5
C9—C12—C1	106.3 (3)	C16—C17—H17C	109.5
C9—C8—C7	118.5 (3)	H17A—C17—H17C	109.5
C9—C8—H8	120.8	H17B—C17—H17C	109.5
C7—C8—H8	120.8
C8—C9—C11—C10	0.3 (6)	C11—C9—C12—C13	179.1 (4)
C12—C9—C11—C10	−179.9 (3)	C8—C9—C12—C1	178.5 (4)
C8—C9—C11—C2	−179.3 (3)	C11—C9—C12—C1	−1.2 (4)
C12—C9—C11—C2	0.4 (4)	O1—C1—C12—C13	2.1 (5)
C15—N1—C14—O2	178.0 (4)	C2—C1—C12—C13	−178.6 (3)
C16—N1—C14—O2	−3.4 (5)	O1—C1—C12—C9	−177.7 (3)
C15—N1—C14—C13	−1.6 (4)	C2—C1—C12—C9	1.6 (4)
C16—N1—C14—C13	177.0 (3)	C11—C9—C8—C7	−1.5 (5)
O2—C14—C13—C12	2.5 (6)	C12—C9—C8—C7	178.8 (4)
N1—C14—C13—C12	−177.9 (3)	C2—C11—C10—C6	−179.9 (3)
O2—C14—C13—S1	−179.7 (3)	C9—C11—C10—C6	0.5 (5)
N1—C14—C13—S1	−0.2 (4)	C2—C11—C10—C5	−1.4 (5)
C15—S1—C13—C12	179.1 (3)	C9—C11—C10—C5	179.0 (3)
C15—S1—C13—C14	1.3 (3)	C14—N1—C15—S2	−177.9 (3)
C10—C11—C2—C3	0.9 (5)	C16—N1—C15—S2	3.6 (5)
C9—C11—C2—C3	−179.4 (3)	C14—N1—C15—S1	2.6 (4)
C10—C11—C2—C1	−179.1 (3)	C16—N1—C15—S1	−175.9 (3)
C9—C11—C2—C1	0.6 (4)	C13—S1—C15—N1	−2.1 (3)
O1—C1—C2—C3	−2.1 (7)	C13—S1—C15—S2	178.3 (2)
C12—C1—C2—C3	178.7 (4)	C11—C10—C6—C7	0.0 (5)
O1—C1—C2—C11	177.9 (4)	C5—C10—C6—C7	−178.4 (4)
C12—C1—C2—C11	−1.3 (4)	C2—C3—C4—C5	−1.6 (6)
C11—C2—C3—C4	0.6 (5)	C3—C4—C5—C10	1.2 (6)
C1—C2—C3—C4	−179.4 (3)	C11—C10—C5—C4	0.3 (6)
C14—C13—C12—C9	−3.2 (7)	C6—C10—C5—C4	178.7 (4)
S1—C13—C12—C9	179.3 (3)	C10—C6—C7—C8	−1.2 (6)
C14—C13—C12—C1	177.1 (3)	C9—C8—C7—C6	2.0 (6)
S1—C13—C12—C1	−0.3 (5)	C15—N1—C16—C17	−93.0 (4)
C8—C9—C12—C13	−1.2 (8)	C14—N1—C16—C17	88.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2^i	0.93	2.50	3.423 (5)	172
C7—H7···O1^ii	0.93	2.59	3.290 (5)	132
C8—H8···O2	0.93	2.23	2.952 (4)	134

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x+1, −y+1/2, z+1/2.