Ethyl 2-{[7-fluoro-4-oxo-3-(1H-1,2,4-triazol-1-yl)-4H-thio-chromen-2-yl]sulfan-yl}acetate.

In the title compound, C(15)H(12)FN(3)O(3)S(2), the two six-membered rings are essentially coplanar, their mean plnes making a dihedral angle of 1.1 (2)°. The carbonyl C, the two attached non-fused C atoms and the S atom deviate from the plane of the benzene ring by -0.046 (5), -0.017 (5), 0.000 (6), 0.026 (4) Å, respectively. The angle between the mean planes of the triazole ring and the sulfur heterocycle is 53.3 (1)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules in a stacked arrangement along the a axis.

Related literature

For related compounds containing a 4H-thio­chromen-4-one fragment, see: Adams et al. (1991 ▶); Nakazumi et al. (1992 ▶); Weiss et al. (2008 ▶); Li et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12FN3O3S2

M = 365.40

Monoclinic,

a = 9.3890 (19) Å

b = 8.2430 (16) Å

c = 20.861 (4) Å

β = 100.72 (3)°

V = 1586.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.898, T max = 0.964

3053 measured reflections

2867 independent reflections

2186 reflections with I > 2σ(I)

R int = 0.013

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.151

S = 1.00

2867 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810027467/zq2047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027467/zq2047Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12FN3O3S2	F(000) = 752
Mr = 365.40	Dx = 1.530 Mg m−3
Monoclinic, P21/c	Melting point: 397 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3890 (19) Å	Cell parameters from 25 reflections
b = 8.2430 (16) Å	θ = 9–14°
c = 20.861 (4) Å	µ = 0.37 mm−1
β = 100.72 (3)°	T = 293 K
V = 1586.3 (5) Å3	Block, pink
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	2186 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
graphite	θmax = 25.3°, θmin = 2.0°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.898, Tmax = 0.964	l = −25→24
3053 measured reflections	3 standard reflections every 200 reflections
2867 independent reflections	intensity decay: 1%

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.170P] where P = (Fo2 + 2Fc2)/3
2867 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
F	0.2497 (3)	0.9099 (3)	−0.12075 (10)	0.0728 (7)
S1	−0.10898 (8)	0.52611 (10)	0.15706 (4)	0.0434 (3)
O1	0.3016 (2)	0.6102 (3)	0.23375 (11)	0.0473 (6)
N1	−0.5765 (3)	0.6974 (5)	0.09253 (17)	0.0721 (10)
C1	0.5439 (4)	0.6893 (6)	0.2766 (2)	0.0871 (15)
H1B	0.6065	0.7781	0.2928	0.131*
H1C	0.5738	0.6438	0.2388	0.131*
H1D	0.5494	0.6077	0.3098	0.131*
S2	0.06614 (8)	0.65095 (9)	0.06388 (3)	0.0375 (2)
O2	0.1081 (3)	0.7704 (3)	0.22875 (11)	0.0554 (6)
N2	−0.4048 (3)	0.5142 (4)	0.07917 (15)	0.0562 (8)
C2	0.3947 (4)	0.7475 (5)	0.2588 (2)	0.0614 (10)
H2B	0.3884	0.8312	0.2257	0.074*
H2C	0.3635	0.7935	0.2967	0.074*
N3	−0.3597 (3)	0.6709 (3)	0.07017 (13)	0.0472 (7)
O3	−0.3528 (3)	0.8531 (3)	−0.03655 (13)	0.0646 (7)
C3	0.1619 (3)	0.6420 (4)	0.21998 (13)	0.0372 (7)
C4	0.0790 (3)	0.4931 (3)	0.19245 (14)	0.0382 (7)
H4A	0.0840	0.4136	0.2271	0.046*
H4B	0.1269	0.4468	0.1593	0.046*
C5	−0.5331 (4)	0.5401 (6)	0.0927 (2)	0.0673 (11)
H5A	−0.5917	0.4556	0.1020	0.081*
C6	−0.4652 (4)	0.7752 (5)	0.07764 (19)	0.0601 (10)
H6A	−0.4601	0.8871	0.0729	0.072*
C7	−0.2261 (3)	0.6990 (4)	0.04953 (14)	0.0378 (7)
C8	−0.2363 (3)	0.7960 (4)	−0.00981 (15)	0.0428 (7)
C9	−0.1040 (3)	0.8222 (3)	−0.03656 (14)	0.0386 (7)
C10	−0.1155 (4)	0.9141 (4)	−0.09443 (15)	0.0473 (8)
H10A	−0.2052	0.9558	−0.1138	0.057*
C11	0.0020 (4)	0.9427 (4)	−0.12239 (16)	0.0521 (9)
H11A	−0.0068	1.0032	−0.1606	0.063*
C12	0.1336 (4)	0.8808 (4)	−0.09318 (16)	0.0490 (8)
C13	0.1538 (4)	0.7913 (4)	−0.03709 (15)	0.0432 (7)
H13A	0.2445	0.7502	−0.0188	0.052*
C14	0.0329 (3)	0.7637 (3)	−0.00815 (13)	0.0357 (7)
C15	−0.1023 (3)	0.6355 (3)	0.08501 (14)	0.0362 (7)

	U11	U22	U33	U12	U13	U23
F	0.0870 (16)	0.0758 (15)	0.0678 (14)	−0.0063 (13)	0.0462 (12)	0.0109 (12)
S1	0.0411 (4)	0.0490 (5)	0.0400 (4)	−0.0036 (4)	0.0071 (3)	0.0107 (3)
O1	0.0433 (12)	0.0353 (12)	0.0611 (14)	−0.0009 (10)	0.0037 (10)	−0.0065 (10)
N1	0.0419 (17)	0.088 (3)	0.088 (2)	−0.0022 (17)	0.0173 (16)	0.019 (2)
C1	0.052 (2)	0.074 (3)	0.128 (4)	−0.007 (2)	−0.003 (2)	−0.028 (3)
S2	0.0376 (4)	0.0383 (4)	0.0366 (4)	0.0003 (3)	0.0071 (3)	0.0057 (3)
O2	0.0633 (15)	0.0396 (13)	0.0589 (15)	0.0130 (11)	−0.0001 (11)	−0.0129 (11)
N2	0.0419 (16)	0.0521 (18)	0.072 (2)	−0.0130 (13)	0.0024 (14)	0.0184 (15)
C2	0.055 (2)	0.045 (2)	0.083 (3)	−0.0150 (17)	0.0077 (19)	−0.0131 (18)
N3	0.0371 (14)	0.0473 (16)	0.0551 (16)	−0.0067 (12)	0.0029 (12)	0.0093 (13)
O3	0.0485 (14)	0.0726 (18)	0.0679 (16)	0.0057 (13)	−0.0015 (12)	0.0296 (14)
C3	0.0488 (18)	0.0330 (16)	0.0290 (14)	0.0022 (14)	0.0051 (12)	0.0027 (12)
C4	0.0441 (16)	0.0322 (16)	0.0368 (15)	0.0017 (13)	0.0038 (13)	0.0026 (13)
C5	0.044 (2)	0.078 (3)	0.076 (3)	−0.017 (2)	0.0012 (18)	0.025 (2)
C6	0.0440 (19)	0.058 (2)	0.081 (3)	0.0040 (18)	0.0176 (18)	0.013 (2)
C7	0.0348 (15)	0.0327 (16)	0.0456 (16)	−0.0044 (13)	0.0067 (12)	0.0033 (13)
C8	0.0470 (18)	0.0354 (16)	0.0426 (16)	−0.0047 (14)	−0.0004 (14)	0.0027 (14)
C9	0.0526 (18)	0.0261 (15)	0.0355 (15)	−0.0016 (13)	0.0038 (13)	−0.0009 (12)
C10	0.063 (2)	0.0363 (17)	0.0384 (16)	−0.0023 (16)	−0.0007 (15)	0.0038 (14)
C11	0.084 (3)	0.0357 (18)	0.0392 (17)	−0.0022 (18)	0.0171 (17)	0.0065 (14)
C12	0.069 (2)	0.0382 (18)	0.0451 (18)	−0.0060 (16)	0.0244 (16)	−0.0024 (15)
C13	0.0524 (18)	0.0377 (17)	0.0427 (16)	−0.0012 (15)	0.0168 (14)	−0.0017 (14)
C14	0.0496 (18)	0.0242 (14)	0.0333 (15)	−0.0043 (13)	0.0074 (13)	−0.0022 (12)
C15	0.0419 (16)	0.0294 (15)	0.0373 (15)	−0.0054 (13)	0.0077 (12)	−0.0009 (12)

F—C12	1.345 (4)	N3—C7	1.419 (4)
S1—C15	1.764 (3)	O3—C8	1.226 (4)
S1—C4	1.802 (3)	C3—C4	1.509 (4)
O1—C3	1.316 (4)	C4—H4A	0.9700
O1—C2	1.466 (4)	C4—H4B	0.9700
N1—C6	1.311 (4)	C5—H5A	0.9300
N1—C5	1.359 (5)	C6—H6A	0.9300
C1—C2	1.462 (5)	C7—C15	1.361 (4)
C1—H1B	0.9600	C7—C8	1.461 (4)
C1—H1C	0.9600	C8—C9	1.469 (4)
C1—H1D	0.9600	C9—C14	1.397 (4)
S2—C15	1.723 (3)	C9—C10	1.412 (4)
S2—C14	1.745 (3)	C10—C11	1.361 (5)
O2—C3	1.201 (4)	C10—H10A	0.9300
N2—C5	1.305 (5)	C11—C12	1.370 (5)
N2—N3	1.383 (4)	C11—H11A	0.9300
C2—H2B	0.9700	C12—C13	1.366 (5)
C2—H2C	0.9700	C13—C14	1.400 (4)
N3—C6	1.342 (4)	C13—H13A	0.9300
C15—S1—C4	103.82 (14)	N1—C5—H5A	121.8
C3—O1—C2	115.3 (3)	N1—C6—N3	110.6 (4)
C6—N1—C5	102.4 (3)	N1—C6—H6A	124.7
C2—C1—H1B	109.5	N3—C6—H6A	124.7
C2—C1—H1C	109.5	C15—C7—N3	119.1 (3)
H1B—C1—H1C	109.5	C15—C7—C8	125.8 (3)
C2—C1—H1D	109.5	N3—C7—C8	115.1 (3)
H1B—C1—H1D	109.5	O3—C8—C7	120.5 (3)
H1C—C1—H1D	109.5	O3—C8—C9	121.1 (3)
C15—S2—C14	103.51 (15)	C7—C8—C9	118.4 (3)
C5—N2—N3	101.2 (3)	C14—C9—C10	117.7 (3)
C1—C2—O1	108.4 (3)	C14—C9—C8	124.3 (3)
C1—C2—H2B	110.0	C10—C9—C8	117.9 (3)
O1—C2—H2B	110.0	C11—C10—C9	121.4 (3)
C1—C2—H2C	110.0	C11—C10—H10A	119.3
O1—C2—H2C	110.0	C9—C10—H10A	119.3
H2B—C2—H2C	108.4	C10—C11—C12	118.7 (3)
C6—N3—N2	109.3 (3)	C10—C11—H11A	120.7
C6—N3—C7	130.1 (3)	C12—C11—H11A	120.7
N2—N3—C7	120.3 (3)	F—C12—C13	117.9 (3)
O2—C3—O1	124.9 (3)	F—C12—C11	118.6 (3)
O2—C3—C4	125.0 (3)	C13—C12—C11	123.5 (3)
O1—C3—C4	110.1 (2)	C12—C13—C14	117.6 (3)
C3—C4—S1	115.4 (2)	C12—C13—H13A	121.2
C3—C4—H4A	108.4	C14—C13—H13A	121.2
S1—C4—H4A	108.4	C9—C14—C13	121.1 (3)
C3—C4—H4B	108.4	C9—C14—S2	123.5 (2)
S1—C4—H4B	108.4	C13—C14—S2	115.4 (2)
H4A—C4—H4B	107.5	C7—C15—S2	124.3 (2)
N2—C5—N1	116.4 (3)	C7—C15—S1	119.8 (2)
N2—C5—H5A	121.8	S2—C15—S1	115.82 (17)
C3—O1—C2—C1	175.4 (3)	C7—C8—C9—C10	179.1 (3)
C5—N2—N3—C6	−1.3 (4)	C14—C9—C10—C11	1.1 (4)
C5—N2—N3—C7	−175.4 (3)	C8—C9—C10—C11	−179.6 (3)
C2—O1—C3—O2	−2.9 (5)	C9—C10—C11—C12	−0.2 (5)
C2—O1—C3—C4	177.9 (3)	C10—C11—C12—F	−179.7 (3)
O2—C3—C4—S1	11.9 (4)	C10—C11—C12—C13	−0.1 (5)
O1—C3—C4—S1	−168.9 (2)	F—C12—C13—C14	179.0 (3)
C15—S1—C4—C3	70.5 (2)	C11—C12—C13—C14	−0.6 (5)
N3—N2—C5—N1	0.9 (5)	C10—C9—C14—C13	−1.8 (4)
C6—N1—C5—N2	−0.1 (5)	C8—C9—C14—C13	178.9 (3)
C5—N1—C6—N3	−0.8 (4)	C10—C9—C14—S2	179.0 (2)
N2—N3—C6—N1	1.4 (4)	C8—C9—C14—S2	−0.2 (4)
C7—N3—C6—N1	174.8 (3)	C12—C13—C14—C9	1.6 (4)
C6—N3—C7—C15	131.6 (4)	C12—C13—C14—S2	−179.2 (2)
N2—N3—C7—C15	−55.7 (4)	C15—S2—C14—C9	0.6 (3)
C6—N3—C7—C8	−48.6 (5)	C15—S2—C14—C13	−178.6 (2)
N2—N3—C7—C8	124.1 (3)	N3—C7—C15—S2	176.7 (2)
C15—C7—C8—O3	−177.0 (3)	C8—C7—C15—S2	−3.0 (5)
N3—C7—C8—O3	3.3 (4)	N3—C7—C15—S1	−2.2 (4)
C15—C7—C8—C9	3.4 (5)	C8—C7—C15—S1	178.1 (2)
N3—C7—C8—C9	−176.4 (3)	C14—S2—C15—C7	0.9 (3)
O3—C8—C9—C14	178.7 (3)	C14—S2—C15—S1	179.85 (16)
C7—C8—C9—C14	−1.6 (4)	C4—S1—C15—C7	−171.9 (2)
O3—C8—C9—C10	−0.6 (5)	C4—S1—C15—S2	9.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2i	0.97	2.47	3.199 (4)	131
C4—H4B···S2	0.97	2.59	2.963 (3)	103
C11—H11A···O2ii	0.93	2.43	3.276 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2i	0.97	2.47	3.199 (4)	131
C11—H11A⋯O2ii	0.93	2.43	3.276 (4)	151

Symmetry codes: (i) ; (ii) .