3-Phenyl-2-(1H-tetra-zol-1-yl)propanoic acid monohydrate.

In the title compound, C(10)H(10)N(4)O(2)·H(2)O, the dihedral angle between the tetra-zole and benzene rings is 63.24 (11)°. The crystal structure is stabilized by intra-molecular O-H⋯N and O-H⋯O hydrogen bonds.

Related literature

For background to the applications of tetra­zole metal derivatives, see: Gaponik et al. (2006 ▶); Zhao et al. (2008 ▶); Xiao et al. (2009 ▶).

Experimental

Crystal data

C10H10N4O2·H2O

M = 236.24

Orthorhombic,

a = 24.001 (4) Å

b = 8.3769 (19) Å

c = 5.7455 (11) Å

V = 1155.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.40 × 0.25 × 0.10 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.972, T max = 0.987

11450 measured reflections

1461 independent reflections

1237 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.098

S = 1.11

1461 reflections

155 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038468/rz2488sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038468/rz2488Isup2.hkl

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

C10H10N4O2·H2O	F(000) = 496
Mr = 236.24	Dx = 1.358 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2576 reflections
a = 24.001 (4) Å	θ = 2.4–27.5°
b = 8.3769 (19) Å	µ = 0.10 mm−1
c = 5.7455 (11) Å	T = 293 K
V = 1155.1 (4) Å3	Prism, colourless
Z = 4	0.40 × 0.25 × 0.10 mm

Rigaku SCXmini diffractometer	1461 independent reflections
Radiation source: fine-focus sealed tube	1237 reflections with I > 2σ(I)
graphite	Rint = 0.049
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.4°
ω scans	h = −30→31
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.972, Tmax = 0.987	l = −7→7
11450 measured 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.045P)2 + 0.0812P] where P = (Fo2 + 2Fc2)/3
1461 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.17 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	0.17744 (13)	0.5430 (3)	0.8029 (6)	0.0523 (7)
H1	0.1849	0.5834	0.6553	0.063*
C2	0.22253 (10)	0.8730 (3)	0.9938 (5)	0.0370 (5)
C3	0.16456 (9)	0.8029 (3)	1.0194 (5)	0.0385 (6)
H3	0.1523	0.8234	1.1793	0.046*
C4	0.12188 (11)	0.8794 (3)	0.8571 (6)	0.0494 (7)
H4A	0.1215	0.9937	0.8834	0.059*
H4B	0.1332	0.8612	0.6972	0.059*
C5	0.06378 (11)	0.8150 (3)	0.8910 (5)	0.0466 (6)
C6	0.03288 (12)	0.8572 (4)	1.0852 (6)	0.0605 (8)
H6	0.0480	0.9258	1.1957	0.073*
C7	−0.02045 (13)	0.7972 (4)	1.1151 (7)	0.0738 (11)
H7	−0.0410	0.8264	1.2455	0.089*
C8	−0.04305 (13)	0.6958 (4)	0.9550 (8)	0.0714 (10)
H8	−0.0787	0.6551	0.9767	0.086*
C9	−0.01295 (13)	0.6545 (4)	0.7634 (8)	0.0728 (10)
H9	−0.0282	0.5858	0.6535	0.087*
C10	0.03997 (12)	0.7138 (4)	0.7312 (6)	0.0617 (8)
H10	0.0600	0.6850	0.5991	0.074*
N1	0.16699 (8)	0.6303 (2)	0.9891 (4)	0.0398 (5)
N2	0.15902 (10)	0.5316 (3)	1.1690 (5)	0.0540 (7)
N3	0.16442 (12)	0.3885 (3)	1.0871 (5)	0.0611 (7)
N4	0.17577 (12)	0.3922 (3)	0.8561 (5)	0.0594 (7)
O1	0.26404 (6)	0.79317 (19)	0.9755 (4)	0.0431 (4)
O2	0.22055 (7)	1.02860 (19)	0.9997 (5)	0.0489 (4)
H2	0.2522	1.0647	0.9909	0.073*
O1W	0.31635 (8)	0.1603 (2)	0.9820 (4)	0.0574 (5)
H1A	0.3191	0.2341	0.8710	0.086*
H1B	0.3195	0.2313	1.1033	0.086*

	U11	U22	U33	U12	U13	U23
C1	0.0678 (18)	0.0421 (16)	0.0470 (17)	0.0014 (14)	0.0082 (15)	0.0055 (13)
C2	0.0443 (12)	0.0387 (12)	0.0281 (11)	−0.0003 (9)	−0.0035 (12)	0.0023 (13)
C3	0.0404 (12)	0.0343 (11)	0.0408 (15)	0.0011 (9)	0.0001 (11)	0.0066 (11)
C4	0.0468 (14)	0.0435 (14)	0.0579 (17)	0.0004 (11)	−0.0052 (13)	0.0097 (14)
C5	0.0420 (14)	0.0426 (14)	0.0553 (16)	0.0051 (11)	−0.0044 (13)	0.0077 (13)
C6	0.0555 (18)	0.0553 (17)	0.071 (2)	0.0057 (14)	0.0008 (17)	−0.0098 (16)
C7	0.058 (2)	0.081 (2)	0.082 (3)	0.0169 (17)	0.0193 (19)	−0.001 (2)
C8	0.0429 (15)	0.074 (2)	0.098 (3)	−0.0014 (14)	0.000 (2)	0.004 (2)
C9	0.055 (2)	0.078 (2)	0.086 (3)	−0.0076 (16)	−0.012 (2)	−0.012 (2)
C10	0.0507 (17)	0.072 (2)	0.0621 (19)	0.0008 (15)	−0.0013 (16)	−0.0097 (17)
N1	0.0407 (10)	0.0357 (10)	0.0429 (11)	−0.0008 (8)	0.0012 (11)	0.0081 (11)
N2	0.0709 (17)	0.0437 (14)	0.0473 (13)	0.0007 (12)	0.0061 (13)	0.0108 (12)
N3	0.0820 (18)	0.0393 (14)	0.0619 (16)	0.0022 (12)	0.0129 (15)	0.0076 (13)
N4	0.0760 (17)	0.0398 (14)	0.0624 (17)	0.0014 (12)	0.0127 (14)	0.0033 (13)
O1	0.0433 (10)	0.0469 (9)	0.0391 (9)	0.0032 (7)	0.0022 (9)	0.0037 (9)
O2	0.0489 (9)	0.0371 (9)	0.0607 (11)	−0.0051 (7)	−0.0016 (12)	−0.0002 (11)
O1W	0.0674 (12)	0.0484 (10)	0.0564 (11)	−0.0175 (8)	−0.0066 (13)	0.0071 (12)

C1—N4	1.301 (4)	C6—H6	0.9300
C1—N1	1.320 (4)	C7—C8	1.365 (5)
C1—H1	0.9300	C7—H7	0.9300
C2—O1	1.205 (3)	C8—C9	1.362 (6)
C2—O2	1.305 (3)	C8—H8	0.9300
C2—C3	1.517 (3)	C9—C10	1.376 (4)
C3—N1	1.457 (3)	C9—H9	0.9300
C3—C4	1.526 (4)	C10—H10	0.9300
C3—H3	0.9800	N1—N2	1.337 (3)
C4—C5	1.508 (4)	N2—N3	1.294 (4)
C4—H4A	0.9700	N3—N4	1.355 (4)
C4—H4B	0.9700	O2—H2	0.8200
C5—C10	1.374 (4)	O1W—H1A	0.8904
C5—C6	1.385 (4)	O1W—H1B	0.9193
C6—C7	1.385 (4)
N4—C1—N1	110.0 (3)	C5—C6—H6	119.9
N4—C1—H1	125.0	C7—C6—H6	119.9
N1—C1—H1	125.0	C8—C7—C6	120.6 (3)
O1—C2—O2	126.0 (2)	C8—C7—H7	119.7
O1—C2—C3	123.48 (19)	C6—C7—H7	119.7
O2—C2—C3	110.55 (18)	C9—C8—C7	119.5 (3)
N1—C3—C2	109.64 (18)	C9—C8—H8	120.3
N1—C3—C4	111.7 (2)	C7—C8—H8	120.3
C2—C3—C4	113.2 (2)	C8—C9—C10	120.4 (3)
N1—C3—H3	107.3	C8—C9—H9	119.8
C2—C3—H3	107.3	C10—C9—H9	119.8
C4—C3—H3	107.3	C5—C10—C9	121.1 (3)
C5—C4—C3	113.1 (2)	C5—C10—H10	119.4
C5—C4—H4A	109.0	C9—C10—H10	119.4
C3—C4—H4A	109.0	C1—N1—N2	108.12 (19)
C5—C4—H4B	109.0	C1—N1—C3	130.9 (2)
C3—C4—H4B	109.0	N2—N1—C3	121.0 (2)
H4A—C4—H4B	107.8	N3—N2—N1	106.1 (2)
C10—C5—C6	118.2 (3)	N2—N3—N4	110.8 (3)
C10—C5—C4	121.2 (3)	C1—N4—N3	105.0 (3)
C6—C5—C4	120.5 (3)	C2—O2—H2	109.5
C5—C6—C7	120.1 (3)	H1A—O1W—H1B	95.0
O1—C2—C3—N1	−7.0 (4)	C4—C5—C10—C9	179.6 (3)
O2—C2—C3—N1	174.4 (2)	C8—C9—C10—C5	0.3 (5)
O1—C2—C3—C4	−132.5 (3)	N4—C1—N1—N2	0.8 (3)
O2—C2—C3—C4	48.9 (3)	N4—C1—N1—C3	179.4 (2)
N1—C3—C4—C5	58.4 (3)	C2—C3—N1—C1	−68.8 (3)
C2—C3—C4—C5	−177.2 (2)	C4—C3—N1—C1	57.5 (3)
C3—C4—C5—C10	−106.6 (3)	C2—C3—N1—N2	109.7 (3)
C3—C4—C5—C6	73.5 (3)	C4—C3—N1—N2	−124.0 (3)
C10—C5—C6—C7	0.3 (5)	C1—N1—N2—N3	−0.4 (3)
C4—C5—C6—C7	−179.9 (3)	C3—N1—N2—N3	−179.2 (2)
C5—C6—C7—C8	0.3 (5)	N1—N2—N3—N4	0.0 (3)
C6—C7—C8—C9	−0.6 (6)	N1—C1—N4—N3	−0.8 (4)
C7—C8—C9—C10	0.3 (6)	N2—N3—N4—C1	0.5 (4)
C6—C5—C10—C9	−0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1Wi	0.82	1.74	2.552 (2)	174
O1W—H1B···N4ii	0.92	1.98	2.903 (4)	177
O1W—H1A···N3iii	0.89	2.12	3.003 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1Wi	0.82	1.74	2.552 (2)	174
O1W—H1B⋯N4ii	0.92	1.98	2.903 (4)	177
O1W—H1A⋯N3iii	0.89	2.12	3.003 (3)	171

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