5-Methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid.

The title compound, C(10)H(9)N(3)O(2), was synthesized from azido-benzene and ethyl acetyl-acetate. A pair of hydrogen bonds [2.617 (2) Å] inter-connects a pair of the carboxyl groups, forming an R(2) (2)(8) inversion dimer, a frequent motif in carboxylic acids. In the title structure, the bonding H atom in the aforementioned O-H⋯O hydrogen bond is significantly shifted towards the acceptor O atom [the donor and acceptor O-H distances are 1.25 (4) and 1.38 (4) Å, respectively]. A plot of the O⋯O versus O-H distances in compounds with paired carboxyl groups shows that the title structure belongs to the group of structures with abnormally long O-H distances with regard to the O⋯O contacts. The displacement of the bonding H atom towards the centre of the hydrogen bond is concomitant with more equal C-O bonding distances in the carboxyl group.

Related literature

For related literature, see: El Khadem et al. (1968 ▶); Olesen et al. (2003 ▶); Tian et al. (2005 ▶); Allen (2002 ▶); Etter et al. (1990 ▶); Radl et al. (2000 ▶).

Experimental

Crystal data

C10H9N3O2

M = 203.20

Monoclinic,

a = 23.616 (3) Å

b = 7.7189 (15) Å

c = 12.606 (2) Å

β = 113.18 (3)°

V = 2112.5 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.20 × 0.18 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.965, T max = 0.977

10370 measured reflections

2400 independent reflections

1583 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.148

S = 1.08

2400 reflections

141 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.18 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/S1600536808027311/fb2106sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027311/fb2106Isup2.hkl

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

C10H9N3O2	F000 = 848
Mr = 203.20	Dx = 1.278 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2025 reflections
a = 23.616 (3) Å	θ = 2.8–27.5º
b = 7.7189 (15) Å	µ = 0.09 mm−1
c = 12.606 (2) Å	T = 293 (2) K
β = 113.18 (3)º	Prism, colourless
V = 2112.5 (8) Å3	0.20 × 0.18 × 0.15 mm
Z = 8

Rigaku SCXmini diffractometer	2400 independent reflections
Radiation source: fine-focus sealed tube	1583 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.053
T = 293(2) K	θmax = 27.5º
ω scans	θmin = 2.8º
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	h = −30→30
Tmin = 0.965, Tmax = 0.977	k = −9→10
10370 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.4952P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2400 reflections	Δρmax = 0.14 e Å−3
141 parameters	Δρmin = −0.18 e Å−3
31 constraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.41473 (10)	0.1278 (3)	0.72134 (18)	0.0555 (5)
C2	0.34886 (9)	0.1172 (3)	0.69727 (16)	0.0491 (5)
C3	0.31868 (9)	0.1493 (2)	0.76949 (15)	0.0461 (5)
C4	0.20319 (9)	0.1379 (2)	0.72119 (16)	0.0466 (5)
C5	0.20037 (10)	0.0713 (3)	0.82132 (17)	0.0538 (5)
H5	0.2350	0.0218	0.8780	0.065*
C6	0.14517 (11)	0.0799 (3)	0.8352 (2)	0.0655 (6)
H6	0.1426	0.0364	0.9020	0.079*
C7	0.09414 (11)	0.1525 (3)	0.7506 (2)	0.0761 (7)
H7	0.0571	0.1574	0.7603	0.091*
C8	0.09745 (10)	0.2184 (3)	0.6509 (2)	0.0734 (7)
H8	0.0626	0.2666	0.5940	0.088*
C9	0.15210 (9)	0.2129 (3)	0.63569 (18)	0.0578 (5)
H9	0.1547	0.2585	0.5695	0.069*
C10	0.34155 (10)	0.2068 (3)	0.89199 (16)	0.0579 (6)
H10A	0.3099	0.2716	0.9041	0.087*
H10B	0.3773	0.2786	0.9091	0.087*
H10C	0.3522	0.1073	0.9417	0.087*
N1	0.30730 (8)	0.0743 (2)	0.58988 (14)	0.0577 (5)
N2	0.25230 (8)	0.0763 (2)	0.59058 (13)	0.0571 (5)
N3	0.25867 (7)	0.1228 (2)	0.70044 (13)	0.0475 (4)
O1	0.45271 (7)	0.1465 (2)	0.82345 (13)	0.0733 (5)
O2	0.43008 (7)	0.1161 (3)	0.63484 (13)	0.0799 (6)
H2	0.4867 (19)	0.125 (5)	0.661 (3)	0.193 (17)*

	U11	U22	U33	U12	U13	U23
C1	0.0557 (12)	0.0670 (14)	0.0444 (12)	0.0033 (10)	0.0201 (10)	0.0024 (10)
C2	0.0508 (11)	0.0572 (12)	0.0404 (11)	0.0029 (9)	0.0190 (9)	0.0016 (8)
C3	0.0505 (11)	0.0472 (11)	0.0407 (10)	0.0013 (8)	0.0182 (9)	0.0020 (8)
C4	0.0488 (10)	0.0506 (11)	0.0416 (11)	−0.0023 (9)	0.0190 (9)	−0.0050 (8)
C5	0.0562 (12)	0.0617 (13)	0.0443 (11)	−0.0008 (9)	0.0206 (10)	−0.0031 (9)
C6	0.0660 (14)	0.0826 (16)	0.0573 (14)	−0.0081 (12)	0.0343 (12)	−0.0071 (11)
C7	0.0548 (14)	0.102 (2)	0.0797 (17)	−0.0006 (13)	0.0350 (14)	−0.0096 (15)
C8	0.0528 (13)	0.0884 (18)	0.0717 (16)	0.0117 (12)	0.0165 (12)	0.0013 (13)
C9	0.0566 (13)	0.0654 (14)	0.0481 (12)	0.0046 (10)	0.0169 (10)	0.0026 (10)
C10	0.0580 (12)	0.0714 (15)	0.0429 (11)	−0.0024 (10)	0.0184 (10)	−0.0071 (10)
N1	0.0544 (10)	0.0770 (12)	0.0430 (10)	0.0019 (9)	0.0208 (8)	−0.0018 (8)
N2	0.0567 (11)	0.0774 (13)	0.0381 (9)	−0.0015 (8)	0.0196 (8)	−0.0064 (8)
N3	0.0505 (9)	0.0554 (10)	0.0372 (8)	0.0005 (7)	0.0178 (7)	−0.0002 (7)
O1	0.0532 (9)	0.1133 (14)	0.0506 (9)	−0.0020 (8)	0.0176 (8)	−0.0084 (8)
O2	0.0585 (10)	0.1372 (16)	0.0504 (9)	0.0041 (9)	0.0282 (8)	0.0032 (9)

C1—O1	1.254 (2)	C6—H6	0.9300
C1—O2	1.281 (2)	C7—C8	1.386 (3)
C1—C2	1.465 (3)	C7—H7	0.9300
C2—N1	1.364 (3)	C8—C9	1.378 (3)
C2—C3	1.382 (3)	C8—H8	0.9300
C3—N3	1.356 (2)	C9—H9	0.9300
C3—C10	1.489 (3)	C10—H10A	0.9600
C4—C5	1.389 (3)	C10—H10B	0.9600
C4—C9	1.389 (3)	C10—H10C	0.9600
C4—N3	1.438 (2)	N1—N2	1.302 (2)
C5—C6	1.384 (3)	N2—N3	1.380 (2)
C5—H5	0.9300	O2—H2	1.25 (4)
C6—C7	1.376 (3)
O1—C1—O2	123.66 (19)	C8—C7—H7	119.7
O1—C1—C2	119.41 (19)	C9—C8—C7	120.3 (2)
O2—C1—C2	116.94 (19)	C9—C8—H8	119.8
N1—C2—C3	109.96 (17)	C7—C8—H8	119.8
N1—C2—C1	120.64 (17)	C8—C9—C4	118.7 (2)
C3—C2—C1	129.38 (19)	C8—C9—H9	120.7
N3—C3—C2	103.29 (16)	C4—C9—H9	120.7
N3—C3—C10	124.88 (17)	C3—C10—H10A	109.5
C2—C3—C10	131.79 (18)	C3—C10—H10B	109.5
C5—C4—C9	121.47 (19)	H10A—C10—H10B	109.5
C5—C4—N3	120.56 (18)	C3—C10—H10C	109.5
C9—C4—N3	117.90 (17)	H10A—C10—H10C	109.5
C6—C5—C4	118.8 (2)	H10B—C10—H10C	109.5
C6—C5—H5	120.6	N2—N1—C2	108.68 (15)
C4—C5—H5	120.6	N1—N2—N3	107.15 (15)
C7—C6—C5	120.2 (2)	C3—N3—N2	110.92 (15)
C7—C6—H6	119.9	C3—N3—C4	131.92 (16)
C5—C6—H6	119.9	N2—N3—C4	117.15 (15)
C6—C7—C8	120.5 (2)	C1—O2—H2	113.8 (15)
C6—C7—H7	119.7

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	1.25 (4)	1.38 (4)	2.617 (2)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	1.25 (4)	1.38 (4)	2.617 (2)	173 (3)

Symmetry code: (i) .