2-[4-Benzyl-5-(2-fur­yl)-4H-1,2,4-triazol-3-ylsulfan­yl]acetamide

Zareef, M.; Iqbal, R.; Arfan, M.; Parvez, M.

doi:10.1107/S1600536808017170

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1259

doi:10.1107/S1600536808017170

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2-[4-Benzyl-5-(2-furyl)-4H-1,2,4-triazol-3-ylsulfanyl]acetamide

Muhammad Zareef,^a ^* Rashid Iqbal,^a Muhammad Arfan ^a and Masood Parvez ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: mzareef71@yahoo.com

(Received 29 May 2008; accepted 7 June 2008; online 13 June 2008)

In the title compound, C₁₅H₁₄N₄O₂S, the phenyl ring is inclined at 70.25 (6)° with respect to the approximately planar furyl–triazolsulfanyl–acetamide unit. In the crystal structure, molecules related by inversion centers form dimers via intermolecular N—H⋯O hydrogen bonds between acetamide groups, resulting in eight-membered rings with an R₂²(8) motif. In addition, the other H atom of the acetamide group is involved in an intermolecular hydrogen bond with an N atom of the triazole ring, resulting in chains extended along the c axis. The overall effect is the formation of a hydrogen-bonded two-dimensional framework perpendicular to the a axis.

Related literature

For related literature, see: Ahmad et al. (2001 ); Altman & Solomost (1993 ); Bernstein et al. (1994 ); Chai et al. (2003 ); Dege et al. (2004 ); Hashimoto et al. (1990 ); Kanazawa et al. (1988 ); Yildirim et al. (2004 ); Zareef, Iqbal & Parvez (2008 ); Zareef, Iqbal, Mirza et al. (2008 ); Öztürk et al. (2004 ).

Experimental

Crystal data

C₁₅H₁₄N₄O₂S
M_r = 314.36
Monoclinic, P 2₁ /c
a = 15.995 (9) Å
b = 7.261 (3) Å
c = 13.598 (8) Å
β = 105.46 (2)°
V = 1522.1 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 (2) K
0.24 × 0.08 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.948, T_max = 0.995
5255 measured reflections
3435 independent reflections
2449 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.105
S = 1.04
3435 reflections
206 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O2ⁱ	0.88 (2)	2.01 (2)	2.880 (2)	172 (2)
N4—H4B⋯N2ⁱⁱ	0.89 (2)	2.01 (2)	2.881 (3)	167 (2)
C9—H9B⋯O1	0.99	2.36	3.007 (3)	122
Symmetry codes: (i) -x, -y-1, -z+1; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017170/lh2638sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017170/lh2638Isup2.hkl

checkCIF report

Comment top

Derivatives of 1,2,4-triazole have significant importance for their broad-spectrum biological and pharmacological activities, such as fungicidal, herbicidal, anticonvulsant, antitumoral, inhibition of cholesterol (Chai et al., 2003; Kanazawa et al., 1988; Hashimoto et al., 1990). In addition, they have many applications in the agriculture domain (Altman & Solomost, 1993). In this paper, we report the synthesis and crystal structure of the title compound, (I).

The structure of the title compound (Fig. 1) is composed of a phenyl ring that is inclined at 70.25 (6)° with respect to a somewhat planar furyl-triazol-thio-acetamide moiety. The mean-planes of the furyl and triazole rings lie at 8.34 (13)° with respect to each other while the atoms in the thioacetamide group (S1/C7/C8/O2/N4) also form a plane which is inclined at 9.48 (10) and 3.45 (12)°, respectively, with furyl and triazole rings. Bond distances and bond angles in (I) agree well with the corresponding bond distances and bond angles reported in compounds closely related to (I) (Zareef, Iqbal & Parvez, 2008; Öztürk et al., 2004; Yildirim et al., 2004; Dege et al., 2004); in all these compounds, the mean-planes of the phenyl rings and the furyl-triazole moieties lie close to right angles. The molecules of (I) lying about inversion centers form dimers as a result of intermolecular N—H···O type hydrogen bonding between acetamide groups; the resulting eight membered rings exhibit an R₂²(8)-type motif (Bernstein et al., 1994). The second H-atom of the acetamide group is involved in an intermolecular hydrogen bond with N2 of the triazole ring thus resulting in a chain structure along the c-axis. The overall effect is the formation of a hydrogen-bonded two-dimensional framework perpendicular to the a-axis (Fig. 2). The structure is further stabilized by non-classical intramolecular interactions of the type C—H···O (Table 1).

Related literature top

For related literature, see: Ahmad et al. (2001); Altman & Solomost (1993); Bernstein et al. (1994); Chai et al. (2003); Dege et al. (2004); Hashimoto et al. (1990); Kanazawa et al. (1988); Yildirim et al. (2004); Zareef, Iqbal & Parvez (2008); Zareef, Iqbal, Mirza et al. (2008); Öztürk et al. (2004).

Experimental top

4-Benzyl-1-(2-furoyl)thiosemicarbazide (10 mmol) was dissolved in aqueous 4 N NaOH solution (50 ml). The solution was heated to reflux for 7 h, cooled and filtered. The filtrate was acidified to pH of 4–5, with 4 N HCl. The solid crude product, 4-benzyl-3-(2-furyl)-1H-1,2,4-triazole-5(4H)-thione, was filtered off, washed with water and recrystallized from aqueous ethanol (60%) (Ahmad et al., 2001). Ethyl S-ester of the triazole was prepared following the procedure reported earlier Zareef, Iqbal, Mirza & et al., 2008). Ethyl-[4-benzyl-5-(2-furyl)-(1,2,4-triazol-3-ylthio)]acetate (10 mmol) was dissolved in dry ethanol (60 ml). Dry ammonia gas was bubbled through the ester solution, with continuous stirring, for 5 hr. The progress of the reaction was monitored by TLC (silica; methanol: chloroform; 1:2). The excess solvent was distilled off under reduced pressure. The crude product was washed with cold water and recrystallized from aqueous ethanol (30%). Crystals of the title compound (I) were grown by slow evaporation of an ethanol solution over 9 days at room temperature (yield 77%).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of the title compound with displacement ellipsoids plotted at 50% probability level.
	Fig. 2. Hydrogen bonding interactions in the unit cell of (I) shown by dashed lines; H-atoms not involved in H-bonds have been omitted.

2-[4-Benzyl-5-(2-furyl)-4H-1,2,4-triazol-3-ylsulfanyl]acetamide top

Crystal data top

C₁₅H₁₄N₄O₂S	F(000) = 656
M_r = 314.36	D_x = 1.372 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 417–419 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.995 (9) Å	Cell parameters from 5255 reflections
b = 7.261 (3) Å	θ = 3.2–27.5°
c = 13.598 (8) Å	µ = 0.23 mm⁻¹
β = 105.46 (2)°	T = 173 K
V = 1522.1 (14) Å³	Plate, colorless
Z = 4	0.24 × 0.08 × 0.02 mm

Data collection top

Nonius KappaCCD diffractometer	3435 independent reflections
Radiation source: fine-focus sealed tube	2449 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −20→20
T_min = 0.948, T_max = 0.995	k = −9→7
5255 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.034P)² + 0.75P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3435 reflections	Δρ_max = 0.28 e Å⁻³
206 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (16)

Crystal data top

C₁₅H₁₄N₄O₂S	V = 1522.1 (14) Å³
M_r = 314.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.995 (9) Å	µ = 0.23 mm⁻¹
b = 7.261 (3) Å	T = 173 K
c = 13.598 (8) Å	0.24 × 0.08 × 0.02 mm
β = 105.46 (2)°

Data collection top

Nonius KappaCCD diffractometer	3435 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	2449 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.995	R_int = 0.031
5255 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.28 e Å⁻³
3435 reflections	Δρ_min = −0.26 e Å⁻³
206 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
S1	0.12862 (3)	0.04606 (6)	0.49096 (4)	0.02689 (16)
O1	0.29228 (9)	0.72417 (18)	0.45345 (11)	0.0318 (4)
O2	0.07346 (10)	−0.29345 (18)	0.53495 (11)	0.0330 (4)
N1	0.14752 (11)	0.4036 (2)	0.28542 (12)	0.0290 (4)
N2	0.11490 (11)	0.2402 (2)	0.31391 (12)	0.0287 (4)
N3	0.19418 (10)	0.3766 (2)	0.45331 (11)	0.0219 (4)
N4	−0.01125 (12)	−0.3863 (2)	0.38142 (14)	0.0280 (4)
H4A	−0.0253 (14)	−0.489 (3)	0.4074 (17)	0.034*
H4B	−0.0375 (14)	−0.358 (3)	0.3169 (18)	0.034*
C1	0.23596 (13)	0.6584 (3)	0.36615 (16)	0.0279 (5)
C2	0.22942 (15)	0.7781 (3)	0.28834 (17)	0.0335 (5)
H2	0.1947	0.7646	0.2202	0.040*
C3	0.28508 (15)	0.9285 (3)	0.32900 (18)	0.0367 (5)
H3	0.2950	1.0347	0.2929	0.044*
C4	0.32076 (15)	0.8915 (3)	0.42773 (18)	0.0355 (5)
H4	0.3602	0.9699	0.4736	0.043*
C5	0.19400 (13)	0.4820 (3)	0.36896 (15)	0.0239 (4)
C6	0.14400 (13)	0.2270 (2)	0.41377 (15)	0.0236 (4)
C7	0.05176 (13)	−0.0836 (2)	0.39448 (15)	0.0243 (4)
H7A	−0.0038	−0.0160	0.3718	0.029*
H7B	0.0747	−0.1049	0.3346	0.029*
C8	0.03843 (13)	−0.2653 (3)	0.44313 (15)	0.0246 (4)
C9	0.23541 (13)	0.4072 (3)	0.56249 (14)	0.0250 (4)
H9A	0.1943	0.3721	0.6023	0.030*
H9B	0.2486	0.5399	0.5742	0.030*
C10	0.31828 (13)	0.2975 (3)	0.60034 (14)	0.0250 (4)
C11	0.32270 (15)	0.1562 (3)	0.66992 (16)	0.0355 (5)
H11	0.2734	0.1278	0.6934	0.043*
C12	0.39864 (17)	0.0557 (3)	0.70563 (19)	0.0484 (6)
H12	0.4012	−0.0407	0.7536	0.058*
C13	0.47022 (17)	0.0959 (4)	0.6714 (2)	0.0501 (7)
H13	0.5222	0.0273	0.6959	0.060*
C14	0.46651 (15)	0.2352 (3)	0.6017 (2)	0.0437 (6)
H14	0.5159	0.2621	0.5779	0.052*
C15	0.39075 (14)	0.3365 (3)	0.56616 (17)	0.0344 (5)
H15	0.3885	0.4329	0.5183	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0291 (3)	0.0266 (3)	0.0229 (3)	−0.0040 (2)	0.0033 (2)	0.0036 (2)
O1	0.0348 (8)	0.0264 (7)	0.0321 (8)	−0.0040 (6)	0.0055 (7)	0.0003 (6)
O2	0.0390 (9)	0.0298 (7)	0.0253 (8)	−0.0067 (7)	0.0000 (7)	0.0067 (6)
N1	0.0328 (10)	0.0305 (8)	0.0239 (9)	−0.0027 (8)	0.0080 (8)	0.0029 (7)
N2	0.0326 (10)	0.0296 (8)	0.0227 (9)	−0.0040 (8)	0.0051 (8)	0.0024 (7)
N3	0.0218 (9)	0.0233 (8)	0.0198 (8)	0.0000 (7)	0.0041 (7)	0.0006 (6)
N4	0.0366 (11)	0.0223 (8)	0.0234 (9)	−0.0018 (8)	0.0050 (8)	0.0033 (7)
C1	0.0263 (11)	0.0291 (10)	0.0292 (11)	0.0009 (9)	0.0093 (9)	−0.0014 (8)
C2	0.0378 (13)	0.0334 (11)	0.0302 (12)	−0.0015 (10)	0.0106 (10)	0.0049 (9)
C3	0.0428 (14)	0.0289 (11)	0.0433 (14)	−0.0009 (10)	0.0203 (11)	0.0070 (10)
C4	0.0368 (13)	0.0225 (10)	0.0505 (15)	−0.0056 (9)	0.0176 (12)	−0.0035 (9)
C5	0.0244 (10)	0.0256 (9)	0.0225 (10)	0.0027 (8)	0.0077 (9)	0.0012 (8)
C6	0.0224 (10)	0.0257 (9)	0.0224 (11)	0.0002 (8)	0.0053 (9)	−0.0011 (8)
C7	0.0263 (11)	0.0229 (9)	0.0230 (10)	−0.0020 (8)	0.0053 (9)	0.0013 (8)
C8	0.0253 (11)	0.0241 (9)	0.0241 (11)	0.0041 (8)	0.0060 (9)	0.0028 (8)
C9	0.0256 (11)	0.0289 (10)	0.0205 (10)	−0.0023 (9)	0.0060 (9)	−0.0022 (8)
C10	0.0251 (11)	0.0272 (10)	0.0200 (10)	−0.0004 (8)	0.0012 (9)	−0.0052 (8)
C11	0.0348 (13)	0.0403 (12)	0.0285 (12)	0.0038 (11)	0.0036 (10)	0.0031 (10)
C12	0.0476 (16)	0.0499 (14)	0.0406 (15)	0.0118 (13)	−0.0004 (12)	0.0127 (11)
C13	0.0333 (14)	0.0514 (14)	0.0559 (17)	0.0104 (12)	−0.0050 (13)	−0.0021 (13)
C14	0.0252 (12)	0.0450 (13)	0.0591 (17)	−0.0014 (11)	0.0081 (12)	−0.0083 (12)
C15	0.0284 (12)	0.0326 (11)	0.0412 (14)	−0.0018 (10)	0.0076 (10)	0.0009 (9)

Geometric parameters (Å, º) top

S1—C6	1.740 (2)	C3—H3	0.9500
S1—C7	1.805 (2)	C4—H4	0.9500
O1—C1	1.371 (2)	C7—C8	1.516 (3)
O1—C4	1.375 (2)	C7—H7A	0.9900
O2—C8	1.242 (2)	C7—H7B	0.9900
N1—C5	1.310 (3)	C9—C10	1.514 (3)
N1—N2	1.392 (2)	C9—H9A	0.9900
N2—C6	1.316 (3)	C9—H9B	0.9900
N3—C6	1.372 (2)	C10—C11	1.385 (3)
N3—C5	1.378 (2)	C10—C15	1.388 (3)
N3—C9	1.472 (2)	C11—C12	1.389 (3)
N4—C8	1.324 (3)	C11—H11	0.9500
N4—H4A	0.88 (2)	C12—C13	1.377 (4)
N4—H4B	0.89 (2)	C12—H12	0.9500
C1—C2	1.351 (3)	C13—C14	1.376 (4)
C1—C5	1.452 (3)	C13—H13	0.9500
C2—C3	1.424 (3)	C14—C15	1.390 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.339 (3)	C15—H15	0.9500

C6—S1—C7	97.69 (9)	C8—C7—H7B	110.4
C1—O1—C4	105.85 (16)	S1—C7—H7B	110.4
C5—N1—N2	107.29 (16)	H7A—C7—H7B	108.6
C6—N2—N1	107.04 (15)	O2—C8—N4	124.19 (18)
C6—N3—C5	104.00 (16)	O2—C8—C7	120.25 (17)
C6—N3—C9	124.93 (15)	N4—C8—C7	115.56 (17)
C5—N3—C9	131.06 (16)	N3—C9—C10	112.32 (15)
C8—N4—H4A	118.8 (14)	N3—C9—H9A	109.1
C8—N4—H4B	121.1 (14)	C10—C9—H9A	109.1
H4A—N4—H4B	119 (2)	N3—C9—H9B	109.1
C2—C1—O1	110.49 (18)	C10—C9—H9B	109.1
C2—C1—C5	130.4 (2)	H9A—C9—H9B	107.9
O1—C1—C5	119.10 (17)	C11—C10—C15	119.0 (2)
C1—C2—C3	106.2 (2)	C11—C10—C9	120.18 (19)
C1—C2—H2	126.9	C15—C10—C9	120.82 (18)
C3—C2—H2	126.9	C10—C11—C12	120.6 (2)
C4—C3—C2	106.91 (19)	C10—C11—H11	119.7
C4—C3—H3	126.5	C12—C11—H11	119.7
C2—C3—H3	126.5	C13—C12—C11	119.9 (2)
C3—C4—O1	110.53 (19)	C13—C12—H12	120.0
C3—C4—H4	124.7	C11—C12—H12	120.0
O1—C4—H4	124.7	C14—C13—C12	120.1 (2)
N1—C5—N3	110.81 (17)	C14—C13—H13	120.0
N1—C5—C1	121.34 (18)	C12—C13—H13	120.0
N3—C5—C1	127.84 (18)	C13—C14—C15	120.1 (2)
N2—C6—N3	110.85 (16)	C13—C14—H14	119.9
N2—C6—S1	127.53 (15)	C15—C14—H14	119.9
N3—C6—S1	121.56 (14)	C10—C15—C14	120.3 (2)
C8—C7—S1	106.52 (13)	C10—C15—H15	119.9
C8—C7—H7A	110.4	C14—C15—H15	119.9
S1—C7—H7A	110.4

C5—N1—N2—C6	−0.5 (2)	C9—N3—C6—N2	178.80 (17)
C4—O1—C1—C2	0.4 (2)	C5—N3—C6—S1	176.91 (14)
C4—O1—C1—C5	−179.59 (18)	C9—N3—C6—S1	−3.8 (3)
O1—C1—C2—C3	0.1 (2)	C7—S1—C6—N2	−7.9 (2)
C5—C1—C2—C3	−180.0 (2)	C7—S1—C6—N3	175.14 (16)
C1—C2—C3—C4	−0.5 (3)	C6—S1—C7—C8	172.23 (13)
C2—C3—C4—O1	0.7 (3)	S1—C7—C8—O2	4.6 (2)
C1—O1—C4—C3	−0.7 (2)	S1—C7—C8—N4	−175.01 (15)
N2—N1—C5—N3	0.2 (2)	C6—N3—C9—C10	79.9 (2)
N2—N1—C5—C1	−178.64 (17)	C5—N3—C9—C10	−101.0 (2)
C6—N3—C5—N1	0.2 (2)	N3—C9—C10—C11	−113.1 (2)
C9—N3—C5—N1	−179.06 (18)	N3—C9—C10—C15	66.9 (2)
C6—N3—C5—C1	178.91 (19)	C15—C10—C11—C12	0.4 (3)
C9—N3—C5—C1	−0.3 (3)	C9—C10—C11—C12	−179.5 (2)
C2—C1—C5—N1	7.9 (3)	C10—C11—C12—C13	−0.3 (4)
O1—C1—C5—N1	−172.15 (18)	C11—C12—C13—C14	−0.1 (4)
C2—C1—C5—N3	−170.7 (2)	C12—C13—C14—C15	0.4 (4)
O1—C1—C5—N3	9.3 (3)	C11—C10—C15—C14	−0.2 (3)
N1—N2—C6—N3	0.6 (2)	C9—C10—C15—C14	179.81 (19)
N1—N2—C6—S1	−176.61 (15)	C13—C14—C15—C10	−0.2 (3)
C5—N3—C6—N2	−0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2ⁱ	0.88 (2)	2.01 (2)	2.880 (2)	172 (2)
N4—H4B···N2ⁱⁱ	0.89 (2)	2.01 (2)	2.881 (3)	167 (2)
C9—H9B···O1	0.99	2.36	3.007 (3)	122

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₄O₂S
M_r	314.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	15.995 (9), 7.261 (3), 13.598 (8)
β (°)	105.46 (2)
V (Å³)	1522.1 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.24 × 0.08 × 0.02

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.948, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	5255, 3435, 2449
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.105, 1.04
No. of reflections	3435
No. of parameters	206
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.26

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2ⁱ	0.88 (2)	2.01 (2)	2.880 (2)	172 (2)
N4—H4B···N2ⁱⁱ	0.89 (2)	2.01 (2)	2.881 (3)	167 (2)
C9—H9B···O1	0.99	2.36	3.007 (3)	122

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

References

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Volume 64| Part 7| July 2008| Page o1259

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