2-Phenyl-2H-1,2,3-triazole-4-carboxylic acid

In the title compound, C₉H₇N₃O₂, the dihedral angle between the triazole and phenyl ring planes is 4.72 (6)°. In the crystal structure, classical inversion dimers arise from O—H...O hydrogen bonds between carboxylic acid groups.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.043
• wR factor = 0.110
• Data-to-parameter ratio = 13.1

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S1. Comment

2-Substituted 1,2,3-triazole-4-carboxylic acids and their derivatives have received much attention duo to their biological activities (Olesen et al., 2003; Tian et al., 2005). We report herein the crystal structure of the title compound, (I), (Fig. 1).

The bond lengths and angles for (I) are within normal ranges (Himanshu, et al., 2002). The carboxyl group is inclined at an angle of 6.72 (11)° with respect to the attached triazole ring, and the dihedral angle between the triazole and phenyl planes is 4.72 (6)°. The classical hydrogen-bonded carboxylic acid dimers [O···O = 2.6295 (17) Å], characterized by an R²₂(8) pattern, predominantly stabilize the supramolecular assembly (Table 1).

Related literature

For related literature, see: Himanshu et al. (2002); Olesen et al. (2003); Tian et al. (2005). For the synthesis, see: Riebsomer & Sumrell (1948).

S2. Experimental

The title compound was prepared from phenyl-D-glucosazone according to the reported method (Riebsomer & Sumrell, 1948). Colourless prisms of (I) were obtained by slow evaporation of a 95% ethanol/water solution at room temperature.

S3. Refinement

H atoms were placed at calculated positions (C—H = 0.93 Å, O—H = 0.82 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(O).

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level for the non-hydrogen atoms.

2-Phenyl-2H-1,2,3-triazole-4-carboxylic acid

Crystal data

C9H7N3O2	F(000) = 392
Mr = 189.18	Dx = 1.404 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 582 reflections
a = 10.3239 (16) Å	θ = 2.5–22.5°
b = 5.2878 (8) Å	µ = 0.10 mm^−1
c = 16.762 (3) Å	T = 295 K
β = 102.059 (3)°	Prism, colourless
V = 894.9 (3) Å^3	0.24 × 0.14 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	1662 independent reflections
Radiation source: fine-focus sealed tube	1285 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.976, Tmax = 0.985	k = −6→6
4595 measured reflections	l = −20→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.1068P] where P = (Fo^2 + 2Fc^2)/3
1662 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.15199 (11)	−0.3925 (2)	1.02747 (7)	0.0582 (4)
O2	−0.00876 (11)	−0.2424 (3)	0.92851 (8)	0.0645 (4)
H2	−0.0504	−0.3605	0.9425	0.097*
N1	0.16466 (12)	0.1176 (3)	0.89183 (8)	0.0484 (4)
N2	0.27159 (12)	0.2601 (3)	0.89746 (8)	0.0473 (4)
N3	0.37074 (14)	0.2079 (3)	0.96051 (9)	0.0600 (4)
C1	0.10945 (15)	−0.2398 (3)	0.97275 (10)	0.0458 (4)
C2	0.19676 (15)	−0.0394 (3)	0.95531 (10)	0.0465 (4)
C3	0.32355 (17)	0.0180 (4)	0.99697 (12)	0.0590 (5)
H3	0.3687	−0.0645	1.0435	0.071*
C4	0.28259 (16)	0.4517 (3)	0.83914 (10)	0.0476 (4)
C5	0.18146 (18)	0.4835 (4)	0.77184 (11)	0.0624 (5)
H5	0.1064	0.3818	0.7641	0.075*
C6	0.1937 (2)	0.6685 (5)	0.71632 (12)	0.0737 (6)
H6	0.1262	0.6923	0.6707	0.088*
C7	0.3044 (2)	0.8186 (4)	0.72739 (12)	0.0691 (6)
H7	0.3118	0.9430	0.6894	0.083*
C8	0.40415 (19)	0.7846 (4)	0.79474 (12)	0.0642 (5)
H8	0.4792	0.8862	0.8021	0.077*
C9	0.39421 (16)	0.6013 (4)	0.85153 (11)	0.0556 (5)
H9	0.4616	0.5791	0.8974	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0524 (7)	0.0605 (8)	0.0577 (8)	−0.0031 (6)	0.0021 (6)	0.0080 (7)
O2	0.0465 (7)	0.0701 (10)	0.0718 (9)	−0.0097 (6)	0.0007 (6)	0.0139 (7)
N1	0.0399 (7)	0.0538 (9)	0.0511 (9)	−0.0042 (7)	0.0082 (6)	−0.0020 (7)
N2	0.0388 (7)	0.0517 (9)	0.0500 (8)	−0.0035 (6)	0.0062 (6)	−0.0020 (7)
N3	0.0431 (8)	0.0686 (11)	0.0621 (10)	−0.0061 (8)	−0.0028 (7)	0.0079 (8)
C1	0.0409 (9)	0.0513 (11)	0.0446 (9)	0.0018 (8)	0.0078 (7)	−0.0032 (8)
C2	0.0405 (9)	0.0506 (11)	0.0483 (9)	0.0020 (8)	0.0088 (7)	−0.0030 (8)
C3	0.0481 (10)	0.0658 (13)	0.0586 (11)	−0.0025 (9)	0.0010 (8)	0.0100 (10)
C4	0.0464 (9)	0.0495 (11)	0.0481 (9)	−0.0027 (8)	0.0125 (7)	−0.0047 (8)
C5	0.0547 (10)	0.0712 (14)	0.0574 (11)	−0.0120 (10)	0.0029 (9)	0.0051 (10)
C6	0.0723 (13)	0.0844 (17)	0.0585 (12)	−0.0112 (12)	0.0000 (10)	0.0109 (11)
C7	0.0805 (14)	0.0661 (14)	0.0612 (12)	−0.0103 (11)	0.0157 (10)	0.0084 (10)
C8	0.0627 (11)	0.0621 (13)	0.0693 (13)	−0.0147 (10)	0.0172 (10)	−0.0036 (10)
C9	0.0500 (10)	0.0593 (12)	0.0566 (11)	−0.0082 (9)	0.0089 (8)	−0.0051 (9)

Geometric parameters (Å, º)

O1—C1	1.2320 (19)	C4—C9	1.377 (2)
O2—C1	1.2889 (18)	C4—C5	1.378 (2)
O2—H2	0.8200	C5—C6	1.374 (3)
N1—N2	1.3235 (18)	C5—H5	0.9300
N1—C2	1.336 (2)	C6—C7	1.372 (3)
N2—N3	1.3376 (18)	C6—H6	0.9300
N2—C4	1.428 (2)	C7—C8	1.372 (3)
N3—C3	1.320 (2)	C7—H7	0.9300
C1—C2	1.460 (2)	C8—C9	1.377 (3)
C2—C3	1.383 (2)	C8—H8	0.9300
C3—H3	0.9300	C9—H9	0.9300
C1—O2—H2	109.5	C5—C4—N2	119.47 (15)
N2—N1—C2	103.47 (12)	C6—C5—C4	118.69 (18)
N1—N2—N3	115.33 (14)	C6—C5—H5	120.7
N1—N2—C4	122.63 (13)	C4—C5—H5	120.7
N3—N2—C4	122.02 (13)	C7—C6—C5	120.82 (19)
C3—N3—N2	103.15 (14)	C7—C6—H6	119.6
O1—C1—O2	124.68 (16)	C5—C6—H6	119.6
O1—C1—C2	119.06 (15)	C8—C7—C6	119.75 (19)
O2—C1—C2	116.26 (15)	C8—C7—H7	120.1
N1—C2—C3	108.47 (15)	C6—C7—H7	120.1
N1—C2—C1	123.37 (14)	C7—C8—C9	120.66 (18)
C3—C2—C1	128.12 (16)	C7—C8—H8	119.7
N3—C3—C2	109.58 (16)	C9—C8—H8	119.7
N3—C3—H3	125.2	C8—C9—C4	118.74 (17)
C2—C3—H3	125.2	C8—C9—H9	120.6
C9—C4—C5	121.34 (17)	C4—C9—H9	120.6
C9—C4—N2	119.19 (15)
C2—N1—N2—N3	−0.43 (19)	N1—N2—C4—C9	176.55 (15)
C2—N1—N2—C4	177.77 (14)	N3—N2—C4—C9	−5.4 (2)
N1—N2—N3—C3	0.4 (2)	N1—N2—C4—C5	−3.3 (2)
C4—N2—N3—C3	−177.78 (16)	N3—N2—C4—C5	174.78 (16)
N2—N1—C2—C3	0.24 (18)	C9—C4—C5—C6	0.2 (3)
N2—N1—C2—C1	−177.93 (15)	N2—C4—C5—C6	−179.94 (18)
O1—C1—C2—N1	172.56 (15)	C4—C5—C6—C7	0.1 (3)
O2—C1—C2—N1	−7.5 (2)	C5—C6—C7—C8	−0.2 (3)
O1—C1—C2—C3	−5.2 (3)	C6—C7—C8—C9	−0.1 (3)
O2—C1—C2—C3	174.74 (17)	C7—C8—C9—C4	0.4 (3)
N2—N3—C3—C2	−0.3 (2)	C5—C4—C9—C8	−0.5 (3)
N1—C2—C3—N3	0.0 (2)	N2—C4—C9—C8	179.67 (16)
C1—C2—C3—N3	178.07 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	1.81	2.6295 (17)	176

Symmetry code: (i) −x, −y−1, −z+2.