4-(4-Hy-droxy-methyl-1H-1,2,3-triazol-1-yl)benzoic acid.

In the title compound, C(10)H(9)N(3)O(3), there is a small twist between the benzene and triazole rings [dihedral angle = 6.32 (7)°]; the carb-oxy-lic acid residue is almost coplanar with the benzene ring to which it is attached [O-C-C-C torsion angle = 1.49 (19)°]. The main deviation from coplanarity of the non-H atoms is found for the hy-droxy group which is almost perpendicular to the remaining atoms [N-C-C-O torsion angle = -75.46 (16)°]. In the crystal, the presence of O-H⋯O (between carboxyl groups) and O-H⋯N (between the hy-droxy group and the triazole ring) hydrogen bonds leads to supra-molecular chains along [03[Formula: see text]]. The chains are connected into sheets via C-H⋯O(hy-droxy) inter-actions.

Related literature

For background to the fluorescence potential, see: McCaroll & Wandruzska (1997 ▶). For synthetic protocols, see: Rostovtsev et al. (2002 ▶); Ryu & Zhao (2005 ▶); Himo et al. (2005 ▶). For additional geometric analysis, see: Spek (2009 ▶).

Experimental

Crystal data

C10H9N3O3

M = 219.20

Triclinic,

a = 5.4641 (7) Å

b = 6.6596 (8) Å

c = 13.1898 (16) Å

α = 88.828 (2)°

β = 83.577 (2)°

γ = 75.828 (2)°

V = 462.42 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.684, T max = 0.746

5837 measured reflections

2099 independent reflections

1852 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.130

S = 1.08

2099 reflections

151 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022409/hb5906sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022409/hb5906Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022409/hb5906Isup3.cml

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

C10H9N3O3	Z = 2
Mr = 219.20	F(000) = 228
Triclinic, P1	Dx = 1.574 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4641 (7) Å	Cell parameters from 3318 reflections
b = 6.6596 (8) Å	θ = 3.1–30.7°
c = 13.1898 (16) Å	µ = 0.12 mm−1
α = 88.828 (2)°	T = 100 K
β = 83.577 (2)°	Block, yellow
γ = 75.828 (2)°	0.20 × 0.20 × 0.18 mm
V = 462.42 (10) Å3

Bruker SMART APEX CCD diffractometer	2099 independent reflections
Radiation source: fine-focus sealed tube	1852 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.684, Tmax = 0.746	k = −8→8
5837 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0804P)2 + 0.1593P] where P = (Fo2 + 2Fc2)/3
2099 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.30 e Å−3
2 restraints	Δρmin = −0.33 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	−0.21174 (19)	−0.26084 (15)	0.47377 (8)	0.0193 (3)
H1O	−0.202 (4)	−0.376 (2)	0.5038 (14)	0.029*
O2	0.19712 (19)	−0.40260 (15)	0.41945 (7)	0.0187 (3)
O3	0.24825 (19)	0.81745 (15)	−0.07164 (7)	0.0188 (3)
H3O	0.219 (4)	0.9413 (17)	−0.0937 (14)	0.028*
N1	0.0479 (2)	0.47484 (17)	0.19947 (8)	0.0133 (3)
N2	−0.1613 (2)	0.63139 (18)	0.19229 (9)	0.0163 (3)
N3	−0.0881 (2)	0.76979 (18)	0.13169 (9)	0.0161 (3)
C1	0.0044 (3)	−0.2560 (2)	0.42301 (10)	0.0141 (3)
C2	0.0120 (2)	−0.06148 (19)	0.36720 (10)	0.0133 (3)
C3	−0.2008 (3)	0.1064 (2)	0.37192 (10)	0.0144 (3)
H3	−0.3530	0.0977	0.4123	0.017*
C4	−0.1908 (3)	0.2860 (2)	0.31786 (10)	0.0149 (3)
H4	−0.3345	0.4007	0.3214	0.018*
C5	0.0336 (2)	0.2951 (2)	0.25830 (10)	0.0131 (3)
C6	0.2481 (3)	0.1299 (2)	0.25451 (10)	0.0145 (3)
H6	0.4008	0.1394	0.2146	0.017*
C7	0.2373 (3)	−0.0480 (2)	0.30923 (10)	0.0148 (3)
H7	0.3831	−0.1608	0.3073	0.018*
C8	0.2538 (3)	0.5157 (2)	0.14328 (10)	0.0155 (3)
H8	0.4227	0.4318	0.1356	0.019*
C9	0.1648 (2)	0.7034 (2)	0.10030 (10)	0.0146 (3)
C10	0.3059 (3)	0.8278 (2)	0.03094 (10)	0.0171 (3)
H10A	0.2585	0.9739	0.0543	0.021*
H10B	0.4908	0.7740	0.0335	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0197 (5)	0.0161 (5)	0.0217 (5)	−0.0063 (4)	0.0026 (4)	0.0063 (4)
O2	0.0211 (5)	0.0135 (5)	0.0195 (5)	−0.0024 (4)	0.0010 (4)	0.0038 (4)
O3	0.0226 (5)	0.0145 (5)	0.0167 (5)	−0.0011 (4)	−0.0003 (4)	0.0049 (4)
N1	0.0136 (5)	0.0111 (5)	0.0149 (5)	−0.0028 (4)	−0.0013 (4)	0.0033 (4)
N2	0.0152 (6)	0.0136 (6)	0.0188 (6)	−0.0019 (4)	−0.0010 (4)	0.0050 (4)
N3	0.0167 (6)	0.0138 (5)	0.0175 (6)	−0.0039 (4)	−0.0008 (4)	0.0050 (4)
C1	0.0170 (6)	0.0132 (6)	0.0128 (6)	−0.0054 (5)	−0.0012 (5)	0.0011 (5)
C2	0.0162 (7)	0.0116 (6)	0.0129 (6)	−0.0050 (5)	−0.0017 (5)	0.0017 (5)
C3	0.0139 (6)	0.0150 (6)	0.0148 (6)	−0.0054 (5)	0.0003 (4)	0.0021 (5)
C4	0.0135 (6)	0.0137 (6)	0.0166 (6)	−0.0019 (5)	−0.0014 (5)	0.0025 (5)
C5	0.0159 (6)	0.0121 (6)	0.0124 (6)	−0.0056 (5)	−0.0020 (5)	0.0029 (5)
C6	0.0138 (6)	0.0139 (6)	0.0155 (6)	−0.0039 (5)	0.0001 (5)	0.0025 (5)
C7	0.0154 (6)	0.0123 (6)	0.0159 (6)	−0.0026 (5)	−0.0009 (5)	0.0018 (5)
C8	0.0142 (6)	0.0153 (6)	0.0165 (6)	−0.0042 (5)	0.0007 (5)	0.0031 (5)
C9	0.0148 (6)	0.0137 (6)	0.0154 (6)	−0.0039 (5)	−0.0016 (5)	0.0021 (5)
C10	0.0175 (6)	0.0166 (6)	0.0173 (7)	−0.0052 (5)	−0.0009 (5)	0.0048 (5)

O1—C1	1.2982 (16)	C3—C4	1.3891 (18)
O1—H1O	0.848 (9)	C3—H3	0.9500
O2—C1	1.2456 (17)	C4—C5	1.3939 (18)
O3—C10	1.4299 (17)	C4—H4	0.9500
O3—H3O	0.852 (9)	C5—C6	1.3944 (18)
N1—N2	1.3562 (15)	C6—C7	1.3852 (18)
N1—C8	1.3579 (17)	C6—H6	0.9500
N1—C5	1.4266 (16)	C7—H7	0.9500
N2—N3	1.3141 (16)	C8—C9	1.3624 (19)
N3—C9	1.3627 (17)	C8—H8	0.9500
C1—C2	1.4838 (18)	C9—C10	1.4970 (18)
C2—C7	1.3961 (18)	C10—H10A	0.9900
C2—C3	1.3985 (18)	C10—H10B	0.9900
C1—O1—H1O	110.8 (14)	C4—C5—N1	120.37 (12)
C10—O3—H3O	106.1 (13)	C6—C5—N1	118.51 (12)
N2—N1—C8	110.82 (11)	C7—C6—C5	119.59 (12)
N2—N1—C5	121.00 (11)	C7—C6—H6	120.2
C8—N1—C5	128.16 (11)	C5—C6—H6	120.2
N3—N2—N1	106.38 (11)	C6—C7—C2	119.94 (12)
N2—N3—C9	109.65 (11)	C6—C7—H7	120.0
O2—C1—O1	123.72 (12)	C2—C7—H7	120.0
O2—C1—C2	120.44 (12)	N1—C8—C9	104.78 (12)
O1—C1—C2	115.84 (12)	N1—C8—H8	127.6
C7—C2—C3	120.00 (12)	C9—C8—H8	127.6
C7—C2—C1	118.69 (12)	C8—C9—N3	108.36 (11)
C3—C2—C1	121.31 (12)	C8—C9—C10	129.04 (12)
C4—C3—C2	120.37 (12)	N3—C9—C10	122.59 (12)
C4—C3—H3	119.8	O3—C10—C9	110.65 (11)
C2—C3—H3	119.8	O3—C10—H10A	109.5
C3—C4—C5	118.94 (12)	C9—C10—H10A	109.5
C3—C4—H4	120.5	O3—C10—H10B	109.5
C5—C4—H4	120.5	C9—C10—H10B	109.5
C4—C5—C6	121.12 (12)	H10A—C10—H10B	108.1
C8—N1—N2—N3	0.21 (15)	C8—N1—C5—C6	−5.0 (2)
C5—N1—N2—N3	−178.52 (11)	C4—C5—C6—C7	1.2 (2)
N1—N2—N3—C9	−0.04 (15)	N1—C5—C6—C7	−178.62 (11)
O2—C1—C2—C7	1.3 (2)	C5—C6—C7—C2	0.4 (2)
O1—C1—C2—C7	−178.57 (11)	C3—C2—C7—C6	−1.5 (2)
O2—C1—C2—C3	−178.67 (12)	C1—C2—C7—C6	178.55 (12)
O1—C1—C2—C3	1.49 (19)	N2—N1—C8—C9	−0.29 (15)
C7—C2—C3—C4	1.0 (2)	C5—N1—C8—C9	178.32 (12)
C1—C2—C3—C4	−179.03 (11)	N1—C8—C9—N3	0.26 (15)
C2—C3—C4—C5	0.6 (2)	N1—C8—C9—C10	179.62 (13)
C3—C4—C5—C6	−1.7 (2)	N2—N3—C9—C8	−0.14 (16)
C3—C4—C5—N1	178.15 (11)	N2—N3—C9—C10	−179.55 (12)
N2—N1—C5—C4	−6.43 (19)	C8—C9—C10—O3	105.27 (16)
C8—N1—C5—C4	175.08 (12)	N3—C9—C10—O3	−75.46 (16)
N2—N1—C5—C6	173.44 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2i	0.85 (1)	1.77 (2)	2.6119 (14)	173.(2)
O3—H3O···N3ii	0.85 (1)	1.96 (1)	2.7995 (16)	169 (2)
C6—H6···O3iii	0.95	2.60	3.5309 (19)	167
C8—H8···O3iii	0.95	2.23	3.1262 (18)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2i	0.85 (1)	1.77 (2)	2.6119 (14)	173 (2)
O3—H3o⋯N3ii	0.85 (1)	1.96 (1)	2.7995 (16)	169 (2)
C6—H6⋯O3iii	0.95	2.60	3.5309 (19)	167
C8—H8⋯O3iii	0.95	2.23	3.1262 (18)	158

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