7-Diethyl-amino-2-propyl-sulfan-yl-3-(1H-1,2,4-triazol-1-yl)-4H-thio-chromen-4-one.

In the title compound, C(18)H(22)N(4)OS(2), the six-membered rings are almost coplanar, showing a dihedral angle between the mean planes of 9.0 (4)°, while the triazol ring is nearly perpendicular to the thio-chromen-4-one unit, making an angle of 89.8 (4)°. In the crystal, C-H⋯N hydrogen bonds link the mol-ecules in a stacked arrangement along the c axis.

Related literature

For related compounds, see: Nohara et al. (1977 ▶); Xiao et al. (2010 ▶); Liu et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H22N4OS2

M = 374.52

Monoclinic,

a = 21.937 (4) Å

b = 9.817 (2) Å

c = 19.059 (4) Å

β = 109.85 (3)°

V = 3860.6 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.918, T max = 0.944

3644 measured reflections

3549 independent reflections

2309 reflections with I > 2σ(I)

R int = 0.062

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.181

S = 1.00

3549 reflections

226 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; 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 class="Chemical">N (Spek, 2009) ▶; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015954/zq2162sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015954/zq2162Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015954/zq2162Isup3.cml

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

C18H22N4OS2	F(000) = 1584
Mr = 374.52	Dx = 1.289 Mg m−3
Monoclinic, C2/c	Melting point: 420 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 21.937 (4) Å	Cell parameters from 25 reflections
b = 9.817 (2) Å	θ = 9–13°
c = 19.059 (4) Å	µ = 0.29 mm−1
β = 109.85 (3)°	T = 293 K
V = 3860.6 (15) Å3	Block, yellow
Z = 8	0.30 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	2309 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
Graphite monochromator	θmax = 25.4°, θmin = 2.0°
ω/2θ scans	h = 0→26
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.918, Tmax = 0.944	l = −22→21
3644 measured reflections	3 standard reflections every 200 reflections
3549 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 2.5P] where P = (Fo2 + 2Fc2)/3
3549 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.46 e Å−3
1 restraint	Δρmin = −0.29 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
O	0.31273 (13)	0.6959 (3)	−0.19491 (12)	0.0685 (7)
S1	0.37800 (5)	0.93494 (9)	0.01442 (4)	0.0623 (3)
C1	0.34042 (17)	0.7137 (3)	0.06581 (16)	0.0521 (8)
H1A	0.3504	0.7653	0.1092	0.063*
N1	0.31682 (18)	0.5173 (3)	0.12929 (16)	0.0768 (10)
S2	0.42593 (6)	1.12341 (11)	−0.07537 (6)	0.0778 (4)
N2	0.37390 (13)	0.9341 (3)	−0.19835 (14)	0.0517 (7)
C2	0.31990 (18)	0.5786 (4)	0.06550 (18)	0.0575 (9)
C3	0.3029 (2)	0.5069 (4)	−0.00294 (19)	0.0647 (10)
H3A	0.2884	0.4175	−0.0051	0.078*
N3	0.42763 (15)	0.9017 (4)	−0.21445 (17)	0.0755 (10)
C4	0.30731 (19)	0.5662 (3)	−0.06570 (17)	0.0591 (9)
H4A	0.2953	0.5160	−0.1097	0.071*
N4	0.35895 (17)	1.0243 (4)	−0.30789 (17)	0.0752 (10)
C5	0.32941 (15)	0.7002 (3)	−0.06632 (15)	0.0460 (7)
C6	0.34602 (15)	0.7712 (3)	0.00137 (16)	0.0461 (7)
C7	0.33381 (16)	0.7573 (3)	−0.13516 (16)	0.0498 (8)
C8	0.36498 (16)	0.8890 (3)	−0.13097 (16)	0.0496 (8)
C9	0.38666 (17)	0.9716 (3)	−0.07033 (17)	0.0521 (8)
C10	0.3179 (3)	0.3638 (5)	0.1353 (3)	0.0961 (15)
H10A	0.3371	0.3251	0.1009	0.115*
H10B	0.3439	0.3366	0.1855	0.115*
C11	0.2543 (3)	0.3150 (7)	0.1184 (3)	0.122 (2)
H11A	0.2550	0.2174	0.1222	0.184*
H11B	0.2288	0.3414	0.0685	0.184*
H11C	0.2356	0.3527	0.1529	0.184*
C12	0.3326 (2)	0.5939 (5)	0.1989 (2)	0.0825 (13)
H12A	0.3115	0.5512	0.2304	0.099*
H12B	0.3154	0.6856	0.1878	0.099*
C13	0.4041 (3)	0.6019 (6)	0.2407 (3)	0.126 (2)
H13A	0.4117	0.6538	0.2856	0.189*
H13B	0.4253	0.6454	0.2101	0.189*
H13C	0.4212	0.5117	0.2533	0.189*
C14	0.4445 (2)	1.1997 (4)	0.0179 (2)	0.0828 (13)
H14A	0.4048	1.2114	0.0289	0.099*
H14B	0.4727	1.1394	0.0552	0.099*
C15	0.4759 (3)	1.3310 (5)	0.0208 (3)	0.1027 (16)
H15A	0.4476	1.3907	−0.0167	0.123*
H15B	0.5155	1.3188	0.0095	0.123*
C16	0.4921 (3)	1.3968 (5)	0.0972 (3)	0.1077 (17)
H16A	0.5126	1.4832	0.0972	0.162*
H16B	0.5209	1.3387	0.1343	0.162*
H16C	0.4529	1.4102	0.1082	0.162*
C17	0.4160 (2)	0.9580 (5)	−0.2799 (2)	0.0791 (13)
H17A	0.4453	0.9527	−0.3056	0.095*
C18	0.33441 (19)	1.0072 (4)	−0.25448 (18)	0.0632 (10)
H18A	0.2946	1.0417	−0.2556	0.076*

	U11	U22	U33	U12	U13	U23
O	0.101 (2)	0.0720 (17)	0.0323 (11)	−0.0199 (14)	0.0227 (12)	−0.0092 (11)
S1	0.0961 (7)	0.0541 (5)	0.0374 (4)	−0.0189 (5)	0.0236 (4)	−0.0066 (4)
C1	0.075 (2)	0.0510 (19)	0.0301 (15)	−0.0042 (17)	0.0170 (15)	−0.0023 (14)
N1	0.126 (3)	0.0677 (18)	0.0389 (15)	−0.019 (2)	0.0313 (17)	0.0017 (14)
S2	0.1058 (9)	0.0682 (7)	0.0592 (6)	−0.0306 (6)	0.0277 (6)	−0.0010 (5)
N2	0.0590 (16)	0.0614 (17)	0.0362 (13)	−0.0001 (14)	0.0179 (12)	0.0061 (13)
C2	0.077 (2)	0.055 (2)	0.0401 (17)	−0.0026 (17)	0.0192 (16)	0.0015 (15)
C3	0.101 (3)	0.0449 (19)	0.0478 (19)	−0.0168 (19)	0.0249 (19)	−0.0029 (16)
N3	0.065 (2)	0.112 (3)	0.0568 (19)	0.0182 (19)	0.0302 (16)	0.0236 (18)
C4	0.089 (3)	0.0506 (19)	0.0336 (16)	−0.0120 (18)	0.0158 (16)	−0.0052 (15)
N4	0.082 (2)	0.096 (3)	0.0488 (17)	0.004 (2)	0.0244 (17)	0.0219 (17)
C5	0.0582 (19)	0.0483 (18)	0.0303 (14)	−0.0025 (15)	0.0133 (13)	−0.0011 (13)
C6	0.0564 (19)	0.0463 (17)	0.0336 (14)	0.0001 (14)	0.0129 (13)	−0.0008 (13)
C7	0.063 (2)	0.0542 (19)	0.0323 (15)	−0.0034 (16)	0.0159 (14)	−0.0033 (14)
C8	0.060 (2)	0.0570 (19)	0.0323 (15)	−0.0012 (16)	0.0167 (14)	0.0056 (14)
C9	0.064 (2)	0.0488 (19)	0.0397 (17)	−0.0095 (16)	0.0117 (15)	0.0002 (14)
C10	0.146 (5)	0.086 (2)	0.060 (3)	−0.022 (3)	0.040 (3)	0.009 (2)
C11	0.140 (5)	0.142 (5)	0.081 (4)	−0.004 (4)	0.033 (3)	0.006 (3)
C12	0.132 (4)	0.078 (3)	0.043 (2)	−0.009 (3)	0.037 (2)	0.0025 (19)
C13	0.162 (6)	0.125 (5)	0.059 (3)	0.014 (4)	−0.003 (3)	0.006 (3)
C14	0.107 (3)	0.068 (3)	0.069 (3)	−0.022 (2)	0.024 (2)	−0.003 (2)
C15	0.116 (4)	0.083 (3)	0.094 (4)	−0.010 (3)	0.016 (3)	−0.003 (3)
C16	0.135 (5)	0.082 (3)	0.089 (4)	−0.010 (3)	0.016 (3)	−0.024 (3)
C17	0.076 (3)	0.117 (4)	0.053 (2)	0.008 (3)	0.033 (2)	0.023 (2)
C18	0.069 (2)	0.077 (2)	0.0439 (18)	0.007 (2)	0.0201 (17)	0.0133 (18)

O—C7	1.231 (4)	C8—C9	1.358 (4)
S1—C9	1.727 (3)	C10—C11	1.405 (7)
S1—C6	1.738 (3)	C10—H10A	0.9700
C1—C6	1.394 (4)	C10—H10B	0.9700
C1—C2	1.400 (5)	C11—H11A	0.9600
C1—H1A	0.9300	C11—H11B	0.9600
N1—C2	1.378 (4)	C11—H11C	0.9600
N1—C12	1.460 (5)	C12—C13	1.502 (7)
N1—C10	1.512 (6)	C12—H12A	0.9700
S2—C9	1.740 (3)	C12—H12B	0.9700
S2—C14	1.843 (4)	C13—H13A	0.9600
N2—C18	1.335 (4)	C13—H13B	0.9600
N2—N3	1.353 (4)	C13—H13C	0.9600
N2—C8	1.433 (4)	C14—C15	1.454 (6)
C2—C3	1.416 (5)	C14—H14A	0.9700
C3—C4	1.363 (4)	C14—H14B	0.9700
C3—H3A	0.9300	C15—C16	1.520 (6)
N3—C17	1.308 (4)	C15—H15A	0.9700
C4—C5	1.404 (4)	C15—H15B	0.9700
C4—H4A	0.9300	C16—H16A	0.9600
N4—C18	1.314 (4)	C16—H16B	0.9600
N4—C17	1.350 (5)	C16—H16C	0.9600
C5—C6	1.401 (4)	C17—H17A	0.9300
C5—C7	1.460 (4)	C18—H18A	0.9300
C7—C8	1.452 (5)
C9—S1—C6	103.07 (15)	C10—C11—H11A	109.5
C6—C1—C2	120.3 (3)	C10—C11—H11B	109.5
C6—C1—H1A	119.9	H11A—C11—H11B	109.5
C2—C1—H1A	119.9	C10—C11—H11C	109.5
C2—N1—C12	120.6 (3)	H11A—C11—H11C	109.5
C2—N1—C10	119.8 (3)	H11B—C11—H11C	109.5
C12—N1—C10	116.9 (3)	N1—C12—C13	113.0 (4)
C9—S2—C14	104.25 (17)	N1—C12—H12A	109.0
C18—N2—N3	108.8 (3)	C13—C12—H12A	109.0
C18—N2—C8	129.4 (3)	N1—C12—H12B	109.0
N3—N2—C8	121.7 (3)	C13—C12—H12B	109.0
N1—C2—C1	121.4 (3)	H12A—C12—H12B	107.8
N1—C2—C3	121.3 (3)	C12—C13—H13A	109.5
C1—C2—C3	117.3 (3)	C12—C13—H13B	109.5
C4—C3—C2	121.4 (3)	H13A—C13—H13B	109.5
C4—C3—H3A	119.3	C12—C13—H13C	109.5
C2—C3—H3A	119.3	H13A—C13—H13C	109.5
C17—N3—N2	102.4 (3)	H13B—C13—H13C	109.5
C3—C4—C5	122.4 (3)	C15—C14—S2	110.1 (3)
C3—C4—H4A	118.8	C15—C14—H14A	109.6
C5—C4—H4A	118.8	S2—C14—H14A	109.6
C18—N4—C17	101.6 (3)	C15—C14—H14B	109.6
C6—C5—C4	116.2 (3)	S2—C14—H14B	109.6
C6—C5—C7	124.1 (3)	H14A—C14—H14B	108.2
C4—C5—C7	119.7 (3)	C14—C15—C16	111.5 (4)
C1—C6—C5	122.4 (3)	C14—C15—H15A	109.3
C1—C6—S1	113.6 (2)	C16—C15—H15A	109.3
C5—C6—S1	123.9 (2)	C14—C15—H15B	109.3
O—C7—C8	120.6 (3)	C16—C15—H15B	109.3
O—C7—C5	121.6 (3)	H15A—C15—H15B	108.0
C8—C7—C5	117.8 (3)	C15—C16—H16A	109.5
C9—C8—N2	117.6 (3)	C15—C16—H16B	109.5
C9—C8—C7	126.9 (3)	H16A—C16—H16B	109.5
N2—C8—C7	115.5 (3)	C15—C16—H16C	109.5
C8—C9—S1	123.6 (3)	H16A—C16—H16C	109.5
C8—C9—S2	120.1 (3)	H16B—C16—H16C	109.5
S1—C9—S2	116.33 (18)	N3—C17—N4	115.7 (3)
C11—C10—N1	109.5 (5)	N3—C17—H17A	122.1
C11—C10—H10A	109.8	N4—C17—H17A	122.1
N1—C10—H10A	109.8	N4—C18—N2	111.4 (3)
C11—C10—H10B	109.8	N4—C18—H18A	124.3
N1—C10—H10B	109.8	N2—C18—H18A	124.3
H10A—C10—H10B	108.2
C12—N1—C2—C1	2.4 (6)	N3—N2—C8—C9	90.7 (4)
C10—N1—C2—C1	−158.5 (4)	C18—N2—C8—C7	89.7 (4)
C12—N1—C2—C3	−178.1 (4)	N3—N2—C8—C7	−88.7 (4)
C10—N1—C2—C3	21.0 (6)	O—C7—C8—C9	175.5 (3)
C6—C1—C2—N1	177.0 (3)	C5—C7—C8—C9	−5.4 (5)
C6—C1—C2—C3	−2.5 (5)	O—C7—C8—N2	−5.1 (5)
N1—C2—C3—C4	−178.5 (4)	C5—C7—C8—N2	173.9 (3)
C1—C2—C3—C4	1.0 (6)	N2—C8—C9—S1	178.3 (2)
C18—N2—N3—C17	−0.3 (4)	C7—C8—C9—S1	−2.3 (5)
C8—N2—N3—C17	178.4 (3)	N2—C8—C9—S2	−2.0 (4)
C2—C3—C4—C5	0.7 (6)	C7—C8—C9—S2	177.4 (3)
C3—C4—C5—C6	−0.8 (5)	C6—S1—C9—C8	6.2 (4)
C3—C4—C5—C7	179.2 (4)	C6—S1—C9—S2	−173.5 (2)
C2—C1—C6—C5	2.5 (5)	C14—S2—C9—C8	179.0 (3)
C2—C1—C6—S1	−175.3 (3)	C14—S2—C9—S1	−1.2 (3)
C4—C5—C6—C1	−0.7 (5)	C2—N1—C10—C11	−98.6 (5)
C7—C5—C6—C1	179.2 (3)	C12—N1—C10—C11	99.8 (5)
C4—C5—C6—S1	176.8 (3)	C2—N1—C12—C13	−82.1 (5)
C7—C5—C6—S1	−3.2 (5)	C10—N1—C12—C13	79.4 (5)
C9—S1—C6—C1	174.2 (3)	C9—S2—C14—C15	−178.2 (4)
C9—S1—C6—C5	−3.6 (3)	S2—C14—C15—C16	−179.9 (4)
C6—C5—C7—O	−172.8 (3)	N2—N3—C17—N4	−0.1 (5)
C4—C5—C7—O	7.2 (5)	C18—N4—C17—N3	0.5 (5)
C6—C5—C7—C8	8.2 (5)	C17—N4—C18—N2	−0.6 (5)
C4—C5—C7—C8	−171.9 (3)	N3—N2—C18—N4	0.6 (5)
C18—N2—C8—C9	−90.9 (4)	C8—N2—C18—N4	−177.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N4i	0.93	2.57	3.451 (5)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N4i	0.93	2.57	3.451 (5)	159

Symmetry code: (i) .