7-Diethyl­amino-2-propyl­sulfan­yl-3-(1H-1,2,4-triazol-1-yl)-4H-thio­chromen-4-one

Li, C.; Yu, G.Y.; Tian, X.; Li, S.; Xiao, T.

doi:10.1107/S1600536812015954

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1435

doi:10.1107/S1600536812015954

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7-Diethylamino-2-propylsulfanyl-3-(1H-1,2,4-triazol-1-yl)-4H-thiochromen-4-one

Chen Li,^a Guang Yan Yu,^a Xin Tian,^a Song Li ^a and Tao Xiao ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: taoxiao@njut.edu.cn

(Received 10 April 2012; accepted 12 April 2012; online 18 April 2012)

In the title compound, C₁₈H₂₂N₄OS₂, 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 thiochromen-4-one unit, making an angle of 89.8 (4)°. In the crystal, C—H⋯N hydrogen bonds link the molecules 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_r = 374.52
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.181
S = 1.00
3549 reflections
226 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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) $[x, -y+2, z+{\script{1\over 2}}]$ .

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 (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812015954/zq2162sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812015954/zq2162Isup3.cml

checkCIF report

Comment top

The title compound is the key intermediate in the synthesis of a new kind of antiallergic drugs (Nohara et al., 1977). The crystal structure determination has been carried out in order to elucidate its molecular conformation (Fig. 1).

The molecular structure of the title compound, C₁₈H₂₂O₁N₄S₂, exhibits bond lengths and angles within normal ranges (Allen et al., 1987; Xiao et al., 2010; Liu et al., 2011). The six-membered rings A (C1—C6) and B (S1/C6—C9) are almost coplanar, showing a dihedral angle between the mean planes of 9.0 (4)°. The dihedral angle between the ring A (C1—C6) and C (N2/N3/N4/C17/C18) is 83.0 (4)° while the dihedral angle between the ring B (S1/C6—C9) and C (N2/N3/N4/C17—C18) is 89.8 (4)°.

In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 2) link the molecules in a stacked arrangement along the c axis (Fig. 2).

Related literature top

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 top

Diethylamine (13.8 ml, 134.4 mmol) was added to a solution of 2-(allylthio)-7-fluoro-3-(1H-1,2,4-triazol-1-yl)-4H-thiochromen-4-one (5 g, 15.7 mmol) in DMSO (30 ml) containing NaOH (1.8 g, 45 mmol). The yellow solution was stirred for about 12 h at room temperature. After completion of the reaction, the solution was poured into water (50 ml). The crystalline product was isolated by filtration and washed with water (300 ml). The precipitate was recrystallized with acetone and a yellow deposit was obtained (m.p. 420 K). Crystals suitable for X-ray analysis were obtained by dissolving the crude product (1.0 g) in ethanol (30 ml) and then allowing the solution to evaporate slowly at room temperature for about 7 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

7-Diethylamino-2-propylsulfanyl-3-(1H-1,2,4-triazol-1-yl)-4H- thiochromen-4-one top

Crystal data top

C₁₈H₂₂N₄OS₂	F(000) = 1584
M_r = 374.52	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	2309 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 25.4°, θ_min = 2.0°
ω/2θ scans	h = 0→26
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
T_min = 0.918, T_max = 0.944	l = −22→21
3644 measured reflections	3 standard reflections every 200 reflections
3549 independent reflections	intensity decay: 1%

Refinement top

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(F_o²) + (0.1P)² + 2.5P] where P = (F_o² + 2F_c²)/3
3549 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.46 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₈H₂₂N₄OS₂	V = 3860.6 (15) Å³
M_r = 374.52	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.937 (4) Å	µ = 0.29 mm⁻¹
b = 9.817 (2) Å	T = 293 K
c = 19.059 (4) Å	0.30 × 0.20 × 0.20 mm
β = 109.85 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2309 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.062
T_min = 0.918, T_max = 0.944	3 standard reflections every 200 reflections
3644 measured reflections	intensity decay: 1%
3549 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	1 restraint
wR(F²) = 0.181	H-atom parameters constrained
S = 1.00	Δρ_max = 0.46 e Å⁻³
3549 reflections	Δρ_min = −0.29 e Å⁻³
226 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₄OS₂
M_r	374.52
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.937 (4), 9.817 (2), 19.059 (4)
β (°)	109.85 (3)
V (Å³)	3860.6 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.918, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	3644, 3549, 2309
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.181, 1.00
No. of reflections	3549
No. of parameters	226
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.29

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N4ⁱ	0.9300	2.5700	3.451 (5)	159.00

Symmetry code: (i) x, −y+2, z+1/2.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Liu, D., Xiao, T., Li, Y., Yu, G. & Li, C. (2011). Acta Cryst. E67, o1777. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nohara, A., Kuriki, H., Saijo, T., Sugihara, H., Kanno, M. & Sanno, Y. (1977). J. Med. Chem. 20, 141–145. CrossRef PubMed CAS Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xiao, T., Li, Y., Liu, D. & Yu, G. (2010). Acta Cryst. E66, o2213. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Page o1435

doi:10.1107/S1600536812015954

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

7-Di­ethyl­amino-2-propyl­sulfan­yl-3-(1H-1,2,4-triazol-1-yl)-4H-thio­chromen-4-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

7-Diethylamino-2-propylsulfanyl-3-(1H-1,2,4-triazol-1-yl)-4H-thiochromen-4-one