5-(4-Ethoxy-benzyl)-1H-tetra-zole.

In the title mol-ecule, C(10)H(12)N(4)O, the tetra-zole and benzene rings form a dihedral angle of 67.52 (2)°. In the crystal, inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into chains along the a axis. The relatively short distance of 3.760 (3) Å between the centroids of the tetra-zole rings suggests the existence of π-π inter-actions.

Related literature

For details of the biological activities of sodium-glucose co-transporter 2 (SGLT2) inhibitors, see: Arakawa et al. (2001 ▶); Meng et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H12N4O

M = 204.24

Monoclinic,

a = 4.9291 (10) Å

b = 18.145 (4) Å

c = 11.363 (2) Å

β = 99.19 (3)°

V = 1003.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.34 × 0.06 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.969, T max = 0.996

6870 measured reflections

1768 independent reflections

1487 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.103

S = 1.10

1768 reflections

142 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055597/cv2684sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055597/cv2684Isup2.hkl

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

C10H12N4O	F(000) = 432
Mr = 204.24	Dx = 1.352 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3598 reflections
a = 4.9291 (10) Å	θ = 1.1–27.9°
b = 18.145 (4) Å	µ = 0.09 mm−1
c = 11.363 (2) Å	T = 113 K
β = 99.19 (3)°	Needle, colourless
V = 1003.2 (3) Å3	0.34 × 0.06 × 0.04 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	1768 independent reflections
Radiation source: rotating anode	1487 reflections with I > 2σ(I)
multilayer	Rint = 0.048
Detector resolution: 14.63 pixels mm-1	θmax = 25.0°, θmin = 2.1°
ω and φ scans	h = −5→5
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −21→19
Tmin = 0.969, Tmax = 0.996	l = −13→13
6870 measured reflections

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.067P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.004
1768 reflections	Δρmax = 0.24 e Å−3
142 parameters	Δρmin = −0.34 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.354 (18)

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
O1	0.09591 (18)	0.17311 (5)	0.48558 (8)	0.0241 (3)
N1	1.0194 (2)	0.48750 (6)	0.33955 (10)	0.0214 (3)
N2	0.9379 (2)	0.55573 (6)	0.36698 (11)	0.0252 (3)
N3	0.6749 (2)	0.55229 (5)	0.36251 (11)	0.0242 (3)
N4	0.5824 (2)	0.48270 (5)	0.33271 (10)	0.0211 (3)
C1	0.8013 (2)	0.44332 (7)	0.31894 (11)	0.0187 (3)
C2	0.8099 (3)	0.36438 (7)	0.28353 (12)	0.0225 (4)
H2A	0.9937	0.3456	0.3100	0.027*
H2B	0.7744	0.3613	0.1972	0.027*
C3	0.6058 (3)	0.31536 (7)	0.33333 (12)	0.0195 (3)
C4	0.5715 (3)	0.32048 (7)	0.45271 (12)	0.0234 (3)
H4	0.6676	0.3562	0.5012	0.028*
C5	0.3974 (3)	0.27333 (7)	0.49957 (12)	0.0243 (4)
H5	0.3739	0.2781	0.5788	0.029*
C6	0.2566 (2)	0.21864 (7)	0.42871 (12)	0.0198 (3)
C7	0.2858 (2)	0.21280 (7)	0.30957 (11)	0.0204 (3)
H7	0.1916	0.1766	0.2614	0.024*
C8	0.4583 (3)	0.26196 (7)	0.26324 (12)	0.0206 (3)
H8	0.4748	0.2588	0.1830	0.025*
C9	−0.0624 (3)	0.11821 (7)	0.41507 (12)	0.0244 (4)
H9A	0.0578	0.0838	0.3832	0.029*
H9B	−0.1819	0.1410	0.3490	0.029*
C10	−0.2311 (3)	0.07851 (8)	0.49534 (14)	0.0319 (4)
H10A	−0.1106	0.0560	0.5601	0.048*
H10B	−0.3407	0.0412	0.4505	0.048*
H10C	−0.3489	0.1131	0.5264	0.048*
H1	1.197 (2)	0.4782 (8)	0.3340 (13)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0280 (6)	0.0230 (5)	0.0223 (6)	−0.0068 (4)	0.0069 (4)	0.0006 (4)
N1	0.0145 (6)	0.0227 (6)	0.0272 (7)	0.0000 (5)	0.0042 (5)	0.0004 (5)
N2	0.0213 (6)	0.0226 (6)	0.0322 (7)	−0.0013 (5)	0.0056 (5)	−0.0012 (5)
N3	0.0212 (6)	0.0227 (6)	0.0292 (7)	−0.0017 (5)	0.0062 (5)	−0.0001 (5)
N4	0.0174 (6)	0.0204 (6)	0.0255 (7)	−0.0009 (5)	0.0037 (5)	−0.0005 (4)
C1	0.0161 (7)	0.0232 (7)	0.0170 (7)	−0.0019 (5)	0.0033 (5)	0.0031 (5)
C2	0.0184 (7)	0.0232 (7)	0.0270 (8)	0.0011 (5)	0.0066 (6)	−0.0001 (5)
C3	0.0165 (7)	0.0185 (7)	0.0239 (8)	0.0030 (5)	0.0042 (6)	0.0025 (5)
C4	0.0241 (8)	0.0220 (7)	0.0232 (8)	−0.0034 (5)	0.0009 (6)	−0.0033 (5)
C5	0.0292 (8)	0.0262 (7)	0.0177 (8)	−0.0028 (6)	0.0047 (6)	−0.0009 (5)
C6	0.0184 (7)	0.0182 (7)	0.0228 (8)	0.0006 (5)	0.0034 (6)	0.0033 (5)
C7	0.0200 (7)	0.0195 (7)	0.0211 (8)	−0.0007 (5)	0.0017 (6)	−0.0020 (5)
C8	0.0222 (7)	0.0220 (7)	0.0183 (8)	0.0036 (5)	0.0055 (6)	−0.0001 (5)
C9	0.0237 (7)	0.0204 (7)	0.0284 (9)	−0.0029 (6)	0.0022 (6)	0.0011 (5)
C10	0.0268 (8)	0.0277 (8)	0.0418 (10)	−0.0040 (6)	0.0077 (7)	0.0055 (6)

O1—C6	1.3753 (15)	C4—C5	1.3778 (18)
O1—C9	1.4296 (16)	C4—H4	0.9300
N1—C1	1.3313 (16)	C5—C6	1.3914 (18)
N1—N2	1.3533 (15)	C5—H5	0.9300
N1—H1	0.906 (9)	C6—C7	1.3881 (18)
N2—N3	1.2908 (16)	C7—C8	1.3922 (18)
N3—N4	1.3666 (14)	C7—H7	0.9300
N4—C1	1.3244 (16)	C8—H8	0.9300
C1—C2	1.4903 (18)	C9—C10	1.5113 (18)
C2—C3	1.5184 (17)	C9—H9A	0.9700
C2—H2A	0.9700	C9—H9B	0.9700
C2—H2B	0.9700	C10—H10A	0.9600
C3—C8	1.3845 (18)	C10—H10B	0.9600
C3—C4	1.3965 (18)	C10—H10C	0.9600
C6—O1—C9	117.34 (10)	C4—C5—H5	119.9
C1—N1—N2	109.29 (10)	C6—C5—H5	119.9
C1—N1—H1	129.7 (10)	O1—C6—C7	124.72 (12)
N2—N1—H1	120.9 (10)	O1—C6—C5	115.34 (11)
N3—N2—N1	106.26 (10)	C7—C6—C5	119.94 (12)
N2—N3—N4	110.35 (10)	C6—C7—C8	118.98 (12)
C1—N4—N3	106.37 (10)	C6—C7—H7	120.5
N4—C1—N1	107.74 (11)	C8—C7—H7	120.5
N4—C1—C2	127.53 (11)	C3—C8—C7	121.81 (12)
N1—C1—C2	124.71 (11)	C3—C8—H8	119.1
C1—C2—C3	114.42 (10)	C7—C8—H8	119.1
C1—C2—H2A	108.7	O1—C9—C10	107.31 (11)
C3—C2—H2A	108.7	O1—C9—H9A	110.3
C1—C2—H2B	108.7	C10—C9—H9A	110.3
C3—C2—H2B	108.7	O1—C9—H9B	110.3
H2A—C2—H2B	107.6	C10—C9—H9B	110.3
C8—C3—C4	118.14 (11)	H9A—C9—H9B	108.5
C8—C3—C2	120.93 (12)	C9—C10—H10A	109.5
C4—C3—C2	120.86 (12)	C9—C10—H10B	109.5
C5—C4—C3	120.89 (12)	H10A—C10—H10B	109.5
C5—C4—H4	119.6	C9—C10—H10C	109.5
C3—C4—H4	119.6	H10A—C10—H10C	109.5
C4—C5—C6	120.20 (13)	H10B—C10—H10C	109.5
C1—N1—N2—N3	−0.13 (14)	C2—C3—C4—C5	−176.44 (11)
N1—N2—N3—N4	0.10 (14)	C3—C4—C5—C6	1.3 (2)
N2—N3—N4—C1	−0.03 (14)	C9—O1—C6—C7	−3.22 (17)
N3—N4—C1—N1	−0.05 (14)	C9—O1—C6—C5	177.21 (11)
N3—N4—C1—C2	−178.47 (12)	C4—C5—C6—O1	177.84 (11)
N2—N1—C1—N4	0.12 (15)	C4—C5—C6—C7	−1.75 (19)
N2—N1—C1—C2	178.59 (12)	O1—C6—C7—C8	−179.16 (11)
N4—C1—C2—C3	−36.43 (19)	C5—C6—C7—C8	0.39 (18)
N1—C1—C2—C3	145.41 (13)	C4—C3—C8—C7	−1.88 (18)
C1—C2—C3—C8	138.01 (13)	C2—C3—C8—C7	175.05 (11)
C1—C2—C3—C4	−45.14 (17)	C6—C7—C8—C3	1.45 (19)
C8—C3—C4—C5	0.49 (19)	C6—O1—C9—C10	−177.01 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4i	0.91 (1)	1.90 (1)	2.7897 (16)	166 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4i	0.91 (1)	1.90 (1)	2.7897 (16)	166 (1)

Symmetry code: (i) .