5-(2-Meth-oxy-phen-yl)-1,3,4-thia-diazol-2-yl 2-meth-oxy-benzoate hemihydrate.

In the title compound, C(17)H(14)N(2)O(4)S·0.5H(2)O, the mol-ecule, with the exception of the two meth-oxy-phenyl groups, is nearly planar with an r.m.s. deviation of 0.0305 Å. The two 2-meth-oxy-phenyl rings make dihedral angles of 4.1 (3) and 2.3 (3)° with the thia-diazole ring. In the crystal, inter-molecular C-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules.

Related literature

For general background to 1,3,4-thia­diazole derivatives, see: Matysiak & Opolski (2006 ▶). Alireza et al. (2005 ▶). Wang et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the synthesis, see: Kurzer (1971 ▶).

Experimental

Crystal data

C17H14N2O4S·0.5H2O

M = 356.37

Monoclinic,

a = 29.858 (6) Å

b = 14.542 (3) Å

c = 7.6710 (15) Å

β = 95.19 (3)°

V = 3317.1 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.22 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 = 0.936, T max = 0.978

3108 measured reflections

3050 independent reflections

1881 reflections with I > 2σ(I)

R int = 0.025

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.176

S = 1.00

3050 reflections

228 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994) ▶; 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010373/bq2283sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010373/bq2283Isup2.hkl

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

C17H14N2O4S·0.5H2O	F(000) = 1464
Mr = 356.37	Dx = 1.407 Mg m−3
Monoclinic, C2/c	Melting point: 520 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 29.858 (6) Å	Cell parameters from 25 reflections
b = 14.542 (3) Å	θ = 9–13°
c = 7.6710 (15) Å	µ = 0.22 mm−1
β = 95.19 (3)°	T = 293 K
V = 3317.1 (12) Å3	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1881 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 25.4°, θmin = 1.4°
ω/2θ scans	h = 0→35
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
Tmin = 0.936, Tmax = 0.978	l = −9→9
3108 measured reflections	3 standard reflections every 200 reflections
3050 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.098P)2] where P = (Fo2 + 2Fc2)/3
3050 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.28 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
C1	0.05152 (13)	0.3419 (3)	0.6081 (4)	0.0711 (11)
H1	0.0270	0.3110	0.6471	0.085*
C2	0.04737 (17)	0.3882 (4)	0.4474 (5)	0.0932 (16)
H2	0.0195	0.3907	0.3827	0.112*
C3	0.08311 (19)	0.4293 (3)	0.3852 (5)	0.0898 (14)
H3	0.0800	0.4570	0.2755	0.108*
C4	0.12303 (15)	0.4305 (3)	0.4795 (4)	0.0698 (11)
H4	0.1472	0.4607	0.4363	0.084*
C5	0.12879 (12)	0.3875 (2)	0.6401 (4)	0.0525 (9)
C6	0.09271 (11)	0.3426 (2)	0.7089 (4)	0.0490 (8)
C7	0.09536 (10)	0.2968 (2)	0.8806 (4)	0.0441 (7)
C8	0.10712 (11)	0.2309 (3)	1.1613 (5)	0.0540 (9)
C9	0.16054 (10)	0.2020 (2)	1.4126 (4)	0.0438 (7)
C10	0.16644 (9)	0.1570 (2)	1.5889 (3)	0.0385 (7)
C11	0.20815 (11)	0.1655 (2)	1.6793 (4)	0.0527 (8)
H11	0.2302	0.1989	1.6288	0.063*
C12	0.21841 (13)	0.1272 (3)	1.8389 (5)	0.0630 (10)
H12	0.2469	0.1350	1.8966	0.076*
C13	0.18718 (14)	0.0778 (3)	1.9137 (5)	0.0707 (11)
H13	0.1945	0.0503	2.0220	0.085*
C14	0.14490 (13)	0.0674 (2)	1.8324 (4)	0.0597 (10)
H14	0.1235	0.0336	1.8861	0.072*
C15	0.13365 (10)	0.1075 (2)	1.6690 (4)	0.0419 (7)
C16	0.20649 (14)	0.4248 (3)	0.6754 (6)	0.1006 (16)
H16A	0.2114	0.3935	0.5687	0.151*
H16B	0.2323	0.4173	0.7582	0.151*
H16C	0.2017	0.4891	0.6517	0.151*
C17	0.05776 (12)	0.0530 (3)	1.6602 (5)	0.0806 (13)
H17A	0.0673	−0.0086	1.6895	0.121*
H17B	0.0310	0.0510	1.5811	0.121*
H17C	0.0517	0.0851	1.7649	0.121*
N1	0.06100 (9)	0.2548 (2)	0.9303 (3)	0.0558 (8)
N2	0.06703 (10)	0.2169 (2)	1.0882 (4)	0.0720 (9)
O1	0.16829 (8)	0.38751 (17)	0.7453 (3)	0.0615 (7)
O2	0.11766 (6)	0.19761 (15)	1.3039 (3)	0.0518 (6)
O3	0.19112 (7)	0.24147 (19)	1.3498 (3)	0.0691 (8)
O4	0.09264 (7)	0.10003 (17)	1.5783 (3)	0.0561 (6)
S	0.14064 (3)	0.29401 (7)	1.03358 (11)	0.0554 (3)
O1W	0.0000	0.1206 (3)	0.2500	0.1159 (19)
H1W	0.019 (3)	0.159 (6)	0.167 (12)	0.40 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.073 (3)	0.091 (3)	0.048 (2)	0.003 (2)	0.0013 (19)	0.009 (2)
C2	0.102 (4)	0.126 (4)	0.048 (2)	0.029 (3)	−0.017 (2)	0.006 (3)
C3	0.134 (4)	0.093 (4)	0.043 (2)	0.019 (3)	0.009 (3)	0.021 (2)
C4	0.120 (3)	0.055 (2)	0.0386 (19)	−0.004 (2)	0.028 (2)	0.0050 (17)
C5	0.077 (2)	0.045 (2)	0.0388 (17)	−0.0061 (17)	0.0212 (17)	0.0022 (15)
C6	0.058 (2)	0.058 (2)	0.0316 (15)	−0.0035 (16)	0.0110 (14)	0.0026 (15)
C7	0.0462 (17)	0.0501 (19)	0.0380 (16)	−0.0056 (15)	0.0142 (13)	0.0003 (14)
C8	0.0469 (19)	0.061 (2)	0.056 (2)	−0.0099 (17)	0.0134 (16)	−0.0026 (18)
C9	0.0421 (16)	0.0516 (19)	0.0399 (16)	−0.0055 (15)	0.0158 (13)	0.0057 (15)
C10	0.0419 (16)	0.0449 (18)	0.0302 (14)	−0.0043 (14)	0.0117 (12)	0.0022 (13)
C11	0.0518 (19)	0.063 (2)	0.0444 (18)	0.0056 (17)	0.0107 (15)	0.0064 (16)
C12	0.060 (2)	0.075 (3)	0.053 (2)	0.014 (2)	−0.0012 (18)	0.0072 (19)
C13	0.094 (3)	0.069 (3)	0.048 (2)	0.013 (2)	−0.001 (2)	0.0129 (19)
C14	0.087 (3)	0.052 (2)	0.0433 (18)	−0.007 (2)	0.0264 (19)	0.0063 (16)
C15	0.0541 (17)	0.0398 (17)	0.0337 (15)	0.0006 (15)	0.0149 (14)	−0.0012 (13)
C16	0.099 (3)	0.110 (4)	0.100 (3)	−0.052 (3)	0.049 (3)	−0.003 (3)
C17	0.071 (2)	0.099 (3)	0.077 (3)	−0.038 (2)	0.031 (2)	−0.006 (2)
N1	0.0557 (17)	0.074 (2)	0.0391 (15)	−0.0111 (15)	0.0085 (13)	0.0099 (14)
N2	0.068 (2)	0.090 (3)	0.0583 (19)	−0.0133 (19)	0.0061 (16)	0.0060 (18)
O1	0.0687 (16)	0.0657 (17)	0.0538 (14)	−0.0200 (13)	0.0250 (13)	0.0021 (12)
O2	0.0355 (11)	0.0463 (13)	0.0756 (16)	−0.0102 (10)	0.0167 (11)	−0.0032 (12)
O3	0.0611 (15)	0.100 (2)	0.0479 (14)	−0.0212 (14)	0.0167 (11)	0.0271 (13)
O4	0.0523 (13)	0.0682 (16)	0.0502 (13)	−0.0190 (12)	0.0183 (11)	0.0020 (11)
S	0.0537 (5)	0.0621 (6)	0.0523 (5)	−0.0108 (4)	0.0158 (4)	0.0026 (4)
O1W	0.083 (3)	0.086 (3)	0.187 (6)	0.000	0.060 (3)	0.000

C1—C6	1.392 (5)	C10—C15	1.401 (4)
C1—C2	1.401 (5)	C11—C12	1.355 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.347 (6)	C12—C13	1.346 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.338 (5)	C13—C14	1.365 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.378 (5)	C14—C15	1.396 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—O1	1.367 (4)	C15—O4	1.357 (4)
C5—C6	1.403 (4)	C16—O1	1.412 (4)
C6—C7	1.472 (4)	C16—H16A	0.9600
C7—N1	1.282 (4)	C16—H16B	0.9600
C7—S	1.709 (3)	C16—H16C	0.9600
C8—O2	1.212 (4)	C17—O4	1.437 (4)
C8—N2	1.291 (4)	C17—H17A	0.9600
C8—S	1.726 (4)	C17—H17B	0.9600
C9—O3	1.214 (3)	C17—H17C	0.9600
C9—O2	1.465 (4)	N1—N2	1.328 (4)
C9—C10	1.499 (4)	O1W—H1W	1.05 (8)
C10—C11	1.375 (4)
C6—C1—C2	119.2 (4)	C10—C11—H11	118.7
C6—C1—H1	120.4	C13—C12—C11	119.7 (4)
C2—C1—H1	120.4	C13—C12—H12	120.1
C3—C2—C1	121.0 (4)	C11—C12—H12	120.1
C3—C2—H2	119.5	C12—C13—C14	120.8 (3)
C1—C2—H2	119.5	C12—C13—H13	119.6
C4—C3—C2	120.7 (4)	C14—C13—H13	119.6
C4—C3—H3	119.7	C13—C14—C15	120.1 (3)
C2—C3—H3	119.7	C13—C14—H14	119.9
C3—C4—C5	120.7 (4)	C15—C14—H14	119.9
C3—C4—H4	119.6	O4—C15—C14	124.1 (3)
C5—C4—H4	119.6	O4—C15—C10	116.8 (3)
O1—C5—C4	124.0 (3)	C14—C15—C10	119.2 (3)
O1—C5—C6	115.4 (3)	O1—C16—H16A	109.5
C4—C5—C6	120.6 (4)	O1—C16—H16B	109.5
C1—C6—C5	117.7 (3)	H16A—C16—H16B	109.5
C1—C6—C7	117.8 (3)	O1—C16—H16C	109.5
C5—C6—C7	124.5 (3)	H16A—C16—H16C	109.5
N1—C7—C6	120.2 (3)	H16B—C16—H16C	109.5
N1—C7—S	112.9 (2)	O4—C17—H17A	109.5
C6—C7—S	126.9 (2)	O4—C17—H17B	109.5
O2—C8—N2	118.9 (3)	H17A—C17—H17B	109.5
O2—C8—S	127.5 (3)	O4—C17—H17C	109.5
N2—C8—S	113.6 (3)	H17A—C17—H17C	109.5
O3—C9—O2	116.4 (3)	H17B—C17—H17C	109.5
O3—C9—C10	122.2 (3)	C7—N1—N2	115.0 (3)
O2—C9—C10	121.3 (2)	C8—N2—N1	112.0 (3)
C11—C10—C15	117.5 (3)	C5—O1—C16	117.3 (3)
C11—C10—C9	116.3 (3)	C8—O2—C9	129.7 (3)
C15—C10—C9	126.2 (3)	C15—O4—C17	118.0 (3)
C12—C11—C10	122.6 (3)	C7—S—C8	86.50 (16)
C12—C11—H11	118.7
C6—C1—C2—C3	3.4 (7)	C13—C14—C15—O4	179.4 (3)
C1—C2—C3—C4	−3.2 (8)	C13—C14—C15—C10	0.9 (5)
C2—C3—C4—C5	1.9 (7)	C11—C10—C15—O4	179.8 (3)
C3—C4—C5—O1	−178.6 (4)	C9—C10—C15—O4	−0.4 (4)
C3—C4—C5—C6	−0.8 (6)	C11—C10—C15—C14	−1.6 (4)
C2—C1—C6—C5	−2.3 (5)	C9—C10—C15—C14	178.2 (3)
C2—C1—C6—C7	177.3 (3)	C6—C7—N1—N2	−179.3 (3)
O1—C5—C6—C1	179.0 (3)	S—C7—N1—N2	−0.5 (4)
C4—C5—C6—C1	1.0 (5)	O2—C8—N2—N1	−177.8 (3)
O1—C5—C6—C7	−0.5 (5)	S—C8—N2—N1	−0.1 (4)
C4—C5—C6—C7	−178.4 (3)	C7—N1—N2—C8	0.4 (5)
C1—C6—C7—N1	2.8 (5)	C4—C5—O1—C16	−7.5 (5)
C5—C6—C7—N1	−177.7 (3)	C6—C5—O1—C16	174.6 (3)
C1—C6—C7—S	−175.8 (3)	N2—C8—O2—C9	179.1 (3)
C5—C6—C7—S	3.7 (5)	S—C8—O2—C9	1.8 (5)
O3—C9—C10—C11	2.2 (5)	O3—C9—O2—C8	−3.4 (5)
O2—C9—C10—C11	179.9 (3)	C10—C9—O2—C8	178.8 (3)
O3—C9—C10—C15	−177.7 (3)	C14—C15—O4—C17	4.1 (5)
O2—C9—C10—C15	0.1 (5)	C10—C15—O4—C17	−177.4 (3)
C15—C10—C11—C12	0.9 (5)	N1—C7—S—C8	0.4 (3)
C9—C10—C11—C12	−179.0 (3)	C6—C7—S—C8	179.1 (3)
C10—C11—C12—C13	0.7 (6)	O2—C8—S—C7	177.3 (4)
C11—C12—C13—C14	−1.4 (6)	N2—C8—S—C7	−0.2 (3)
C12—C13—C14—C15	0.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N2i	1.05 (9)	1.81 (9)	2.821 (4)	159 (7)
C11—H11···O3ii	0.93	2.50	3.324 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N2i	1.05 (9)	1.81 (9)	2.821 (4)	159 (7)
C11—H11⋯O3ii	0.93	2.50	3.324 (4)	148

Symmetry codes: (i) ; (ii) .