3-Phenyl-2-(1H-tetra­zol-1-yl)propanoic acid monohydrate

Xiao, J.; Zhao, H.

doi:10.1107/S1600536810038468

organic compounds

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Volume 66| Part 10| October 2010| Page o2690

doi:10.1107/S1600536810038468

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3-Phenyl-2-(1H-tetrazol-1-yl)propanoic acid monohydrate

Jie Xiao ^a and Hong Zhao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: zhaohong@seu.edu.cn

(Received 13 September 2010; accepted 26 September 2010; online 30 September 2010)

In the title compound, C₁₀H₁₀N₄O₂·H₂O, the dihedral angle between the tetrazole and benzene rings is 63.24 (11)°. The crystal structure is stabilized by intramolecular 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_r = 236.24
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.098
S = 1.11
1461 reflections
155 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Recently tetrazoles have been area of interest of coordination chemistry because of various applications of their metal derivatives (Gaponik et al., 2006; Zhao et al., 2008). A great variety of tetrazoles, especially substituted ones, are investigated as ligands. Recently, we have reported a few tetrazole compounds (Xiao et al., 2009). As an extension of our work on the structural characterization of tetrazole compounds, the structure of the title compound is reported here.

In the molecule of the title compound (Fig. 1) bond lengths and angles have normal values. The dihedral angle between the planes of the tetrazole and phenyl rings is 63.24 (0.11)°. The crystal structure (Fig. 2) is stabilized by intramolecular O—H···N and O—H···O hydrogen bonds (Table 1).

Related literature top

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

Experimental top

2-Amino-3-phenylpropanoic acid (1.65 g, 10 mmol) and triethoxymethane (2.96 g, 20 mmol) was added to a mixture of sodium azide (0.65 g, 10 mmol) in acetic acid. After 3 h at 80°C, the mixture was cooled to room temperature and poured into 50 ml HCl (30%) to afford a white precipitate of the title compound. Colourless crystals suitable for X-ray diffraction were obtained after 3 days by slow evaporation of an ethanol solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound, showing the structure down the c axis. Intermolecular hydrogen bonds are shown as dashed lines.

3-Phenyl-2-(1H-tetrazol-1-yl)propanoic acid monohydrate top

Crystal data top

C₁₀H₁₀N₄O₂·H₂O	F(000) = 496
M_r = 236.24	D_x = 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

Data collection top

Rigaku SCXmini diffractometer	1461 independent reflections
Radiation source: fine-focus sealed tube	1237 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −30→31
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.972, T_max = 0.987	l = −7→7
11450 measured reflections

Refinement top

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(F_o²) + (0.045P)² + 0.0812P] where P = (F_o² + 2F_c²)/3
1461 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₀H₁₀N₄O₂·H₂O	V = 1155.1 (4) Å³
M_r = 236.24	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 24.001 (4) Å	µ = 0.10 mm⁻¹
b = 8.3769 (19) Å	T = 293 K
c = 5.7455 (11) Å	0.40 × 0.25 × 0.10 mm

Data collection top

Rigaku SCXmini diffractometer	1461 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1237 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.987	R_int = 0.049
11450 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.098	H-atom parameters constrained
S = 1.11	Δρ_max = 0.15 e Å⁻³
1461 reflections	Δρ_min = −0.17 e Å⁻³
155 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) −x+1/2, y, z+1/2; (iii) −x+1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₄O₂·H₂O
M_r	236.24
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	24.001 (4), 8.3769 (19), 5.7455 (11)
V (Å³)	1155.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.25 × 0.10

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.972, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	11450, 1461, 1237
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.098, 1.11
No. of reflections	1461
No. of parameters	155
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1Wⁱ	0.82	1.74	2.552 (2)	173.9
O1W—H1B···N4ⁱⁱ	0.92	1.98	2.903 (4)	177.3
O1W—H1A···N3ⁱⁱⁱ	0.89	2.12	3.003 (3)	171.3

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y, z+1/2; (iii) −x+1/2, y, z−1/2.

Acknowledgements

This work was supported by the Young Researchers fund of Southeast University (grant No. 4007041027).

References

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