5-(2,6-Dimethoxy-phen-oxy)-2-methyl-sulfanylmethyl-2H-tetra-zole.

In the title mol-ecule, C(11)H(14)N(4)O(3)S, the tetra-zole and benzene rings are nearly perpendicular to each other, forming a dihedral angle of 104.93 (14)°. The crystal packing exhibits weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For a related crystal structure, see: Dabbagh et al. (2005 ▶).

Experimental

Crystal data

C11H14N4O3S

M = 282.32

Orthorhombic,

a = 12.1795 (5) Å

b = 11.0809 (4) Å

c = 9.9026 (4) Å

V = 1336.45 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 173 K

0.50 × 0.25 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.871, T max = 0.975

7950 measured reflections

2873 independent reflections

2670 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.067

S = 1.08

2873 reflections

175 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 1220 Friedel pairs

Flack parameter: 0.06 (6)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008 ▶); program(s) used to solve structure: SIR (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006138/cv2515sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006138/cv2515Isup2.hkl

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

C11H14N4O3S	F(000) = 592
Mr = 282.32	Dx = 1.403 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4562 reflections
a = 12.1795 (5) Å	θ = 2.8–27.8°
b = 11.0809 (4) Å	µ = 0.25 mm−1
c = 9.9026 (4) Å	T = 173 K
V = 1336.45 (9) Å3	Irregular, colourless
Z = 4	0.50 × 0.25 × 0.10 mm

Bruker X8 APEXII diffractometer	2873 independent reflections
Radiation source: fine-focus sealed tube	2670 reflections with I > 2σ(I)
graphite	Rint = 0.020
Area–detector scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→15
Tmin = 0.871, Tmax = 0.975	k = −14→14
7950 measured reflections	l = −12→12

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)] = 0.026	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.1529P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.002
2873 reflections	Δρmax = 0.18 e Å−3
175 parameters	Δρmin = −0.15 e Å−3
1 restraint	Absolute structure: Flack (1983), 1220 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (6)

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	0.56871 (11)	0.77249 (11)	0.88143 (15)	0.0219 (3)
C2	0.65815 (12)	0.75439 (12)	0.96546 (15)	0.0236 (3)
C3	0.74485 (12)	0.83700 (14)	0.96021 (18)	0.0282 (3)
H3	0.8075	0.8264	1.0161	0.034*
C4	0.73884 (12)	0.93401 (13)	0.87333 (17)	0.0296 (3)
H4	0.7984	0.9893	0.8700	0.035*
C5	0.64873 (13)	0.95357 (13)	0.79062 (17)	0.0279 (3)
H5	0.6460	1.0215	0.7322	0.033*
C6	0.56210 (12)	0.87112 (12)	0.79505 (15)	0.0244 (3)
C7	0.74036 (16)	0.64203 (15)	1.1436 (2)	0.0417 (4)
H7A	0.8086	0.6213	1.0966	0.063*
H7B	0.7216	0.5776	1.2073	0.063*
H7C	0.7503	0.7179	1.1930	0.063*
C8	0.45668 (14)	0.97946 (14)	0.6331 (2)	0.0388 (4)
H8A	0.4621	1.0539	0.6861	0.058*
H8B	0.3848	0.9761	0.5887	0.058*
H8C	0.5148	0.9782	0.5646	0.058*
C9	0.39202 (11)	0.70979 (11)	0.94053 (14)	0.0213 (3)
C10	0.12256 (13)	0.65157 (14)	1.0324 (2)	0.0334 (3)
H10A	0.0972	0.6804	1.1217	0.040*
H10B	0.1216	0.5622	1.0341	0.040*
C11	0.05905 (16)	0.59888 (17)	0.77160 (19)	0.0451 (4)
H11A	0.1360	0.6080	0.7445	0.068*
H11B	0.0113	0.6157	0.6941	0.068*
H11C	0.0464	0.5162	0.8031	0.068*
N1	0.30621 (9)	0.63680 (9)	0.92891 (14)	0.0250 (3)
N2	0.23531 (10)	0.69247 (10)	1.01082 (14)	0.0266 (3)
N3	0.27358 (11)	0.79161 (11)	1.06706 (16)	0.0328 (3)
N4	0.37580 (11)	0.80385 (11)	1.02308 (15)	0.0298 (3)
O1	0.65369 (8)	0.65558 (9)	1.04724 (12)	0.0297 (2)
O2	0.46880 (9)	0.87735 (9)	0.72061 (12)	0.0316 (3)
O3	0.48597 (8)	0.68410 (8)	0.87649 (10)	0.0231 (2)
S1	0.02856 (3)	0.70315 (4)	0.90562 (6)	0.04717 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0180 (6)	0.0215 (6)	0.0261 (8)	−0.0025 (5)	0.0015 (6)	−0.0033 (5)
C2	0.0226 (7)	0.0245 (6)	0.0237 (8)	0.0029 (5)	0.0009 (6)	−0.0048 (5)
C3	0.0182 (7)	0.0354 (7)	0.0310 (9)	−0.0003 (5)	−0.0019 (6)	−0.0091 (6)
C4	0.0239 (7)	0.0294 (7)	0.0354 (9)	−0.0069 (5)	0.0059 (6)	−0.0086 (6)
C5	0.0292 (7)	0.0237 (6)	0.0308 (8)	−0.0041 (5)	0.0051 (6)	−0.0009 (6)
C6	0.0239 (7)	0.0249 (6)	0.0243 (8)	0.0007 (5)	0.0008 (6)	−0.0018 (5)
C7	0.0426 (10)	0.0425 (8)	0.0400 (10)	0.0014 (8)	−0.0177 (9)	0.0046 (8)
C8	0.0417 (9)	0.0323 (8)	0.0425 (10)	−0.0001 (7)	−0.0069 (9)	0.0140 (7)
C9	0.0203 (6)	0.0197 (5)	0.0238 (8)	0.0018 (5)	−0.0028 (6)	0.0026 (5)
C10	0.0221 (7)	0.0346 (7)	0.0436 (9)	−0.0046 (6)	0.0078 (7)	−0.0024 (7)
C11	0.0453 (11)	0.0475 (10)	0.0423 (11)	−0.0133 (8)	−0.0079 (9)	0.0117 (8)
N1	0.0201 (5)	0.0251 (5)	0.0298 (7)	−0.0018 (4)	0.0008 (5)	−0.0012 (5)
N2	0.0209 (6)	0.0257 (6)	0.0332 (8)	−0.0011 (5)	0.0028 (5)	−0.0010 (5)
N3	0.0267 (6)	0.0288 (6)	0.0430 (9)	−0.0028 (5)	0.0053 (6)	−0.0072 (5)
N4	0.0244 (6)	0.0267 (6)	0.0382 (8)	−0.0030 (5)	0.0022 (6)	−0.0059 (5)
O1	0.0279 (6)	0.0299 (5)	0.0312 (6)	0.0007 (4)	−0.0075 (5)	0.0025 (4)
O2	0.0296 (6)	0.0292 (5)	0.0361 (7)	−0.0045 (4)	−0.0102 (5)	0.0098 (4)
O3	0.0187 (5)	0.0204 (4)	0.0302 (6)	−0.0028 (3)	−0.0003 (4)	−0.0023 (4)
S1	0.02395 (18)	0.0424 (2)	0.0752 (4)	0.00636 (16)	−0.0048 (2)	0.0022 (2)

C1—O3	1.4062 (15)	C7—H7B	0.9800
C9—O3	1.3388 (17)	C7—H7C	0.9800
N2—C10	1.4618 (19)	C8—O2	1.4330 (18)
S1—C10	1.792 (2)	C8—H8A	0.9800
C6—O2	1.3562 (18)	C8—H8B	0.9800
C2—O1	1.3630 (17)	C8—H8C	0.9800
C1—C2	1.385 (2)	C9—N1	1.3265 (17)
C1—C6	1.390 (2)	C9—N4	1.3393 (18)
C2—C3	1.399 (2)	C10—H10A	0.9900
C3—C4	1.379 (2)	C10—H10B	0.9900
C3—H3	0.9500	C11—S1	1.798 (2)
C4—C5	1.386 (2)	C11—H11A	0.9800
C4—H4	0.9500	C11—H11B	0.9800
C5—C6	1.3964 (19)	C11—H11C	0.9800
C5—H5	0.9500	N1—N2	1.3357 (17)
C7—O1	1.431 (2)	N2—N3	1.3169 (17)
C7—H7A	0.9800	N3—N4	1.3260 (18)
C9—O3—C1	116.61 (10)	O2—C8—H8B	109.5
N2—C10—S1	113.52 (12)	H8A—C8—H8B	109.5
C10—S1—C11	100.37 (9)	O2—C8—H8C	109.5
C2—C1—C6	121.93 (12)	H8A—C8—H8C	109.5
C2—C1—O3	118.92 (12)	H8B—C8—H8C	109.5
C6—C1—O3	118.99 (12)	N1—C9—O3	120.17 (11)
O1—C2—C1	116.22 (12)	N1—C9—N4	114.28 (12)
O1—C2—C3	125.32 (13)	O3—C9—N4	125.50 (12)
C1—C2—C3	118.47 (13)	N2—C10—H10A	108.9
C4—C3—C2	119.57 (14)	S1—C10—H10A	108.9
C4—C3—H3	120.2	N2—C10—H10B	108.9
C2—C3—H3	120.2	S1—C10—H10B	108.9
C3—C4—C5	122.18 (13)	H10A—C10—H10B	107.7
C3—C4—H4	118.9	S1—C11—H11A	109.5
C5—C4—H4	118.9	S1—C11—H11B	109.5
C4—C5—C6	118.51 (14)	H11A—C11—H11B	109.5
C4—C5—H5	120.7	S1—C11—H11C	109.5
C6—C5—H5	120.7	H11A—C11—H11C	109.5
O2—C6—C1	115.02 (12)	H11B—C11—H11C	109.5
O2—C6—C5	125.64 (13)	C9—N1—N2	100.09 (11)
C1—C6—C5	119.33 (14)	N3—N2—N1	114.41 (12)
O1—C7—H7A	109.5	N3—N2—C10	121.96 (13)
O1—C7—H7B	109.5	N1—N2—C10	123.56 (12)
H7A—C7—H7B	109.5	N2—N3—N4	106.18 (12)
O1—C7—H7C	109.5	N3—N4—C9	105.04 (12)
H7A—C7—H7C	109.5	C2—O1—C7	116.81 (12)
H7B—C7—H7C	109.5	C6—O2—C8	117.09 (12)
O2—C8—H8A	109.5
C6—C1—O3—C9	−79.52 (17)	N4—C9—N1—N2	−0.13 (16)
N4—C9—O3—C1	−9.6 (2)	C9—N1—N2—N3	0.54 (16)
C6—C1—C2—O1	178.73 (13)	C9—N1—N2—C10	177.63 (14)
O3—C1—C2—O1	−5.86 (18)	S1—C10—N2—N3	93.31 (17)
C6—C1—C2—C3	−1.4 (2)	S1—C10—N2—N1	−83.56 (15)
O3—C1—C2—C3	174.02 (13)	N1—N2—N3—N4	−0.76 (18)
O1—C2—C3—C4	−179.56 (14)	C10—N2—N3—N4	−177.90 (15)
C1—C2—C3—C4	0.6 (2)	N2—N3—N4—C9	0.60 (17)
C2—C3—C4—C5	0.5 (2)	N1—C9—N4—N3	−0.31 (17)
C3—C4—C5—C6	−0.7 (2)	O3—C9—N4—N3	−177.81 (14)
C2—C1—C6—O2	−179.07 (13)	C1—C2—O1—C7	−174.19 (14)
O3—C1—C6—O2	5.51 (18)	C3—C2—O1—C7	5.9 (2)
C2—C1—C6—C5	1.2 (2)	C1—C6—O2—C8	178.13 (14)
O3—C1—C6—C5	−174.26 (13)	C5—C6—O2—C8	−2.1 (2)
C4—C5—C6—O2	−179.84 (14)	N1—C9—O3—C1	173.03 (12)
C4—C5—C6—C1	−0.1 (2)	C2—C1—O3—C9	104.93 (14)
O3—C9—N1—N2	177.52 (12)	N2—C10—S1—C11	78.85 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1i	0.99	2.45	3.4277 (19)	170
C11—H11C···O3i	0.98	2.45	3.421 (2)	172
C11—H11B···O1ii	0.98	2.52	3.471 (2)	163
C10—H10A···O2iii	0.99	2.52	3.312 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1i	0.99	2.45	3.4277 (19)	170
C11—H11C⋯O3i	0.98	2.45	3.421 (2)	172
C11—H11B⋯O1ii	0.98	2.52	3.471 (2)	163
C10—H10A⋯O2iii	0.99	2.52	3.312 (2)	137

Symmetry codes: (i) ; (ii) ; (iii) .