N-(5-Eth-oxy-1,3,4-thia-diazol-2-yl)benzamide.

In the title compound, C(11)H(11)N(3)O(2)S, the dihedral angle between the thia-diazole and phenyl rings is 28.08 (7)°. In the crystal, mol-ecules are linked into an inversion dimer by a pair of inter-molecular N-H⋯N hydrogen bonds with an R(2) (2)(8) graph-set motif.

Related literature

For the structures and reactivity of thia­diazole derivatives, see: Cho et al. (1996 ▶); Parkanyi et al. (1989 ▶).

Experimental

Crystal data

C11H11N3O2S

M = 249.29

Monoclinic,

a = 3.9797 (5) Å

b = 20.138 (3) Å

c = 14.4305 (18) Å

β = 92.036 (2)°

V = 1155.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.27 × 0.12 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.956, T max = 0.965

22225 measured reflections

2891 independent reflections

1287 reflections with I > 2σ(I)

R int = 0.114

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.081

S = 0.74

2891 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002978/is5058sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002978/is5058Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002978/is5058Isup3.cml

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

C11H11N3O2S	F(000) = 520
Mr = 249.29	Dx = 1.433 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1448 reflections
a = 3.9797 (5) Å	θ = 2.8–18.7°
b = 20.138 (3) Å	µ = 0.27 mm−1
c = 14.4305 (18) Å	T = 296 K
β = 92.036 (2)°	Needle, colourless
V = 1155.8 (2) Å3	0.27 × 0.12 × 0.11 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1287 reflections with I > 2σ(I)
graphite	Rint = 0.114
φ and ω scans	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→5
Tmin = 0.956, Tmax = 0.965	k = −26→26
22225 measured reflections	l = −19→19
2891 independent reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 0.74	w = 1/[σ2(Fo2) + (0.0257P)2] where P = (Fo2 + 2Fc2)/3
2891 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.19 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
S1	0.39663 (15)	0.34946 (3)	0.62317 (4)	0.04682 (18)
C2	0.2359 (5)	0.42298 (9)	0.57867 (14)	0.0375 (5)
N3	0.2325 (5)	0.42812 (8)	0.48901 (12)	0.0467 (5)
N4	0.3654 (5)	0.37174 (8)	0.44715 (11)	0.0473 (5)
C5	0.4558 (5)	0.32859 (10)	0.50836 (14)	0.0411 (5)
N6	0.1165 (5)	0.47337 (9)	0.63320 (12)	0.0433 (5)
H6	0.021 (6)	0.5057 (12)	0.6040 (16)	0.082 (9)*
C7	0.1183 (5)	0.46904 (10)	0.72786 (14)	0.0398 (5)
O8	0.2192 (4)	0.41880 (7)	0.76704 (9)	0.0545 (4)
C9	−0.0024 (5)	0.52767 (10)	0.77924 (14)	0.0399 (5)
C10	−0.1415 (6)	0.51700 (12)	0.86450 (15)	0.0549 (7)
H10	−0.1629	0.4739	0.8868	0.066*
C11	−0.2486 (6)	0.56979 (13)	0.91657 (16)	0.0608 (7)
H11	−0.3439	0.5623	0.9736	0.073*
C12	−0.2143 (6)	0.63343 (13)	0.88413 (16)	0.0621 (7)
H12	−0.288	0.6691	0.919	0.075*
C13	−0.0712 (6)	0.64450 (11)	0.80031 (16)	0.0606 (7)
H13	−0.0444	0.6877	0.7791	0.073*
C14	0.0330 (6)	0.59171 (10)	0.74726 (15)	0.0491 (6)
H14	0.1268	0.5994	0.6901	0.059*
O15	0.5894 (4)	0.26919 (7)	0.49063 (10)	0.0541 (4)
C16	0.6596 (6)	0.25697 (10)	0.39481 (14)	0.0516 (6)
H16A	0.8359	0.2865	0.3751	0.062*
H16B	0.4597	0.2649	0.3559	0.062*
C17	0.7689 (6)	0.18619 (11)	0.38643 (15)	0.0639 (7)
H17A	0.8181	0.1769	0.3231	0.096*
H17B	0.5922	0.1574	0.4057	0.096*
H17C	0.9666	0.1789	0.4251	0.096*

	U11	U22	U33	U12	U13	U23
S1	0.0621 (4)	0.0364 (3)	0.0421 (3)	0.0089 (3)	0.0035 (3)	0.0037 (3)
C2	0.0460 (14)	0.0303 (12)	0.0362 (12)	0.0008 (10)	0.0005 (10)	−0.0005 (10)
N3	0.0673 (14)	0.0351 (11)	0.0377 (11)	0.0110 (9)	0.0004 (9)	−0.0021 (9)
N4	0.0638 (14)	0.0364 (11)	0.0417 (11)	0.0106 (9)	0.0004 (9)	−0.0033 (9)
C5	0.0478 (15)	0.0334 (12)	0.0420 (13)	0.0021 (11)	0.0024 (11)	−0.0026 (11)
N6	0.0624 (14)	0.0343 (11)	0.0330 (11)	0.0088 (10)	−0.0004 (9)	0.0006 (9)
C7	0.0406 (14)	0.0376 (13)	0.0411 (13)	−0.0021 (10)	0.0011 (10)	0.0030 (11)
O8	0.0763 (12)	0.0425 (9)	0.0445 (9)	0.0106 (8)	0.0006 (8)	0.0078 (7)
C9	0.0428 (14)	0.0421 (13)	0.0348 (12)	0.0002 (11)	−0.0010 (10)	−0.0013 (11)
C10	0.0631 (18)	0.0525 (16)	0.0492 (15)	−0.0006 (13)	0.0017 (12)	−0.0016 (12)
C11	0.0647 (18)	0.0749 (19)	0.0436 (15)	−0.0008 (15)	0.0128 (12)	−0.0064 (14)
C12	0.0724 (19)	0.0667 (19)	0.0470 (16)	0.0162 (15)	−0.0007 (13)	−0.0157 (14)
C13	0.090 (2)	0.0438 (15)	0.0480 (15)	0.0117 (14)	−0.0032 (14)	−0.0036 (13)
C14	0.0667 (17)	0.0426 (14)	0.0381 (13)	0.0023 (12)	0.0013 (11)	−0.0005 (11)
O15	0.0777 (12)	0.0369 (9)	0.0483 (10)	0.0159 (8)	0.0091 (8)	−0.0015 (7)
C16	0.0564 (17)	0.0477 (15)	0.0510 (15)	0.0077 (12)	0.0056 (12)	−0.0087 (12)
C17	0.0682 (18)	0.0512 (16)	0.0720 (18)	0.0097 (13)	−0.0032 (14)	−0.0174 (13)

S1—C2	1.727 (2)	C11—C12	1.373 (3)
S1—C5	1.733 (2)	C11—H11	0.93
C2—N3	1.298 (2)	C12—C13	1.373 (3)
C2—N6	1.379 (2)	C12—H12	0.93
N3—N4	1.399 (2)	C13—C14	1.382 (3)
N4—C5	1.282 (2)	C13—H13	0.93
C5—O15	1.337 (2)	C14—H14	0.93
N6—C7	1.368 (2)	O15—C16	1.442 (2)
N6—H6	0.86 (2)	C16—C17	1.496 (3)
C7—O8	1.220 (2)	C16—H16A	0.97
C7—C9	1.483 (3)	C16—H16B	0.97
C9—C14	1.379 (3)	C17—H17A	0.96
C9—C10	1.384 (3)	C17—H17B	0.96
C10—C11	1.378 (3)	C17—H17C	0.96
C10—H10	0.93
C2—S1—C5	85.05 (10)	C10—C11—H11	120.1
N3—C2—N6	121.25 (18)	C11—C12—C13	120.1 (2)
N3—C2—S1	115.45 (15)	C11—C12—H12	120
N6—C2—S1	123.31 (16)	C13—C12—H12	120
C2—N3—N4	112.03 (16)	C12—C13—C14	120.3 (2)
C5—N4—N3	110.73 (17)	C12—C13—H13	119.8
N4—C5—O15	125.34 (19)	C14—C13—H13	119.8
N4—C5—S1	116.75 (16)	C9—C14—C13	119.9 (2)
O15—C5—S1	117.92 (15)	C9—C14—H14	120.1
C7—N6—C2	122.22 (19)	C13—C14—H14	120.1
C7—N6—H6	121.7 (16)	C5—O15—C16	115.34 (15)
C2—N6—H6	115.7 (16)	O15—C16—C17	107.87 (17)
O8—C7—N6	120.35 (19)	O15—C16—H16A	110.1
O8—C7—C9	122.38 (19)	C17—C16—H16A	110.1
N6—C7—C9	117.26 (19)	O15—C16—H16B	110.1
C14—C9—C10	119.5 (2)	C17—C16—H16B	110.1
C14—C9—C7	122.6 (2)	H16A—C16—H16B	108.4
C10—C9—C7	117.9 (2)	C16—C17—H17A	109.5
C11—C10—C9	120.4 (2)	C16—C17—H17B	109.5
C11—C10—H10	119.8	H17A—C17—H17B	109.5
C9—C10—H10	119.8	C16—C17—H17C	109.5
C12—C11—C10	119.8 (2)	H17A—C17—H17C	109.5
C12—C11—H11	120.1	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N3i	0.86 (2)	2.12 (2)	2.967 (3)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯N3i	0.86 (2)	2.12 (2)	2.967 (3)	169 (2)

Symmetry code: (i) .