1H-Benzotriazole-4-hy-droxy-benzoic acid (1/1).

The asymmetric unit of the title compound, C6H5N3·C7H6O3, comprises independent benzotriazole and 4-hydroxybenzoic acid molecules. The dihedral angle between the benzene ring and the benzotriazole ring system is 15.18 (7)°. The mean plane of the carb-oxyl group is twisted at an angle of 18.55 (1)° with respect to the benzene ring. The crystal structure is stabilized by weak inter-molecular N-H⋯N, O-H⋯N, O-H⋯O and C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For biological activities of benzotriazole derivates, see: Dubey et al. (2011 ▶); Gaikwad, et al. (2012 ▶). For reported structures, see: Sieroń (2007 ▶); Sudhahar et al.(2013 ▶); Yang et al. (2010 ▶).

Experimental

Crystal data

C6H5N3·C7H6O3

M = 257.25

Orthorhombic,

a = 17.3634 (13) Å

b = 11.4669 (9) Å

c = 6.0818 (4) Å

V = 1210.91 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.30 × 0.26 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.976

6611 measured reflections

2195 independent reflections

1925 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.074

S = 1.04

2195 reflections

174 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813026767/vm2200sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026767/vm2200Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813026767/vm2200Isup3.cml

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

C6H5N3·C7H6O3	F(000) = 536
Mr = 257.25	Dx = 1.411 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2578 reflections
a = 17.3634 (13) Å	θ = 2.1–25.2°
b = 11.4669 (9) Å	µ = 0.10 mm−1
c = 6.0818 (4) Å	T = 295 K
V = 1210.91 (15) Å3	Block, colourless
Z = 4	0.30 × 0.26 × 0.24 mm

Bruker Kappa APEXII CCD diffractometer	2195 independent reflections
Radiation source: fine-focus sealed tube	1925 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scan	θmax = 26.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→22
Tmin = 0.970, Tmax = 0.976	k = −13→14
6611 measured reflections	l = −7→4

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0362P)2 + 0.0577P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2195 reflections	Δρmax = 0.15 e Å−3
174 parameters	Δρmin = −0.11 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (2)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C7	0.37669 (8)	0.74471 (13)	0.7594 (3)	0.0363 (4)
C4	0.32444 (9)	0.79794 (14)	0.5984 (3)	0.0353 (4)
C3	0.30244 (10)	0.73727 (15)	0.4112 (3)	0.0457 (4)
H3	0.3204	0.6617	0.3895	0.055*
C2	0.25482 (10)	0.78675 (16)	0.2581 (3)	0.0492 (5)
H2	0.2416	0.7452	0.1323	0.059*
C1	0.22618 (9)	0.89793 (15)	0.2887 (3)	0.0385 (4)
C6	0.24605 (9)	0.95891 (15)	0.4762 (3)	0.0417 (4)
H6	0.2261	1.0331	0.4997	0.050*
C5	0.29535 (10)	0.91033 (14)	0.6286 (3)	0.0419 (4)
H5	0.3093	0.9528	0.7527	0.050*
N2	−0.00946 (8)	0.88952 (13)	0.2498 (3)	0.0477 (4)
C9	0.03383 (9)	0.72630 (14)	0.3824 (3)	0.0345 (4)
C8	0.05616 (10)	0.81341 (14)	0.5280 (3)	0.0366 (4)
C13	0.09730 (10)	0.78968 (17)	0.7199 (3)	0.0485 (5)
H13	0.1117	0.8480	0.8178	0.058*
C12	0.11490 (10)	0.67520 (17)	0.7544 (4)	0.0539 (5)
H12	0.1419	0.6551	0.8809	0.065*
C11	0.09398 (12)	0.58653 (16)	0.6071 (3)	0.0521 (5)
H11	0.1083	0.5101	0.6375	0.062*
C10	0.05347 (10)	0.60939 (14)	0.4216 (3)	0.0459 (4)
H10	0.0393	0.5504	0.3248	0.055*
N3	−0.00650 (8)	0.77773 (12)	0.2146 (2)	0.0418 (3)
N1	0.02792 (8)	0.91193 (12)	0.4377 (3)	0.0456 (4)
H1	0.0332	0.9803	0.4935	0.055*
O1	0.38942 (6)	0.63969 (10)	0.7712 (2)	0.0472 (3)
O2	0.40973 (7)	0.81933 (10)	0.8925 (2)	0.0504 (3)
H2A	0.4380	0.7843	0.9779	0.076*
O3	0.17907 (8)	0.94246 (11)	0.13231 (19)	0.0531 (4)
H3A	0.1627	1.0060	0.1729	0.080*

	U11	U22	U33	U12	U13	U23
C7	0.0366 (8)	0.0325 (9)	0.0398 (9)	−0.0021 (6)	0.0031 (7)	−0.0020 (9)
C4	0.0346 (8)	0.0338 (8)	0.0376 (9)	−0.0022 (6)	0.0022 (7)	−0.0032 (7)
C3	0.0509 (10)	0.0377 (9)	0.0485 (11)	0.0083 (7)	−0.0051 (9)	−0.0119 (10)
C2	0.0575 (10)	0.0467 (10)	0.0434 (11)	0.0084 (8)	−0.0093 (10)	−0.0186 (9)
C1	0.0391 (8)	0.0405 (9)	0.0359 (9)	0.0005 (7)	−0.0001 (7)	−0.0029 (8)
C6	0.0480 (9)	0.0303 (8)	0.0468 (10)	0.0029 (7)	−0.0041 (8)	−0.0082 (7)
C5	0.0463 (9)	0.0375 (9)	0.0418 (10)	−0.0014 (7)	−0.0062 (8)	−0.0101 (8)
N2	0.0591 (9)	0.0351 (8)	0.0488 (9)	−0.0029 (6)	−0.0070 (8)	0.0017 (7)
C9	0.0379 (8)	0.0318 (8)	0.0336 (9)	−0.0030 (6)	−0.0001 (7)	−0.0033 (7)
C8	0.0397 (9)	0.0324 (9)	0.0376 (9)	−0.0030 (7)	0.0033 (7)	−0.0053 (7)
C13	0.0527 (10)	0.0538 (12)	0.0391 (10)	−0.0031 (8)	−0.0053 (8)	−0.0128 (10)
C12	0.0563 (11)	0.0610 (12)	0.0445 (11)	0.0052 (9)	−0.0124 (10)	0.0009 (11)
C11	0.0582 (11)	0.0405 (11)	0.0574 (12)	0.0063 (8)	−0.0091 (10)	0.0023 (10)
C10	0.0524 (10)	0.0326 (9)	0.0528 (12)	−0.0006 (7)	−0.0056 (10)	−0.0074 (9)
N3	0.0519 (8)	0.0330 (8)	0.0406 (8)	−0.0022 (6)	−0.0058 (7)	−0.0004 (7)
N1	0.0587 (9)	0.0295 (7)	0.0486 (9)	−0.0043 (6)	−0.0009 (8)	−0.0086 (7)
O1	0.0533 (7)	0.0323 (7)	0.0560 (8)	0.0004 (5)	−0.0065 (6)	−0.0008 (7)
O2	0.0630 (7)	0.0339 (7)	0.0542 (8)	0.0015 (5)	−0.0221 (7)	−0.0036 (6)
O3	0.0654 (8)	0.0509 (8)	0.0430 (7)	0.0145 (6)	−0.0147 (6)	−0.0089 (6)

C7—O1	1.2265 (18)	C9—N3	1.371 (2)
C7—O2	1.3102 (19)	C9—C8	1.390 (2)
C7—C4	1.468 (2)	C9—C10	1.404 (2)
C4—C3	1.388 (2)	C8—N1	1.348 (2)
C4—C5	1.396 (2)	C8—C13	1.395 (3)
C3—C2	1.369 (2)	C13—C12	1.364 (3)
C3—H3	0.9300	C13—H13	0.9300
C2—C1	1.381 (2)	C12—C11	1.403 (3)
C2—H2	0.9300	C12—H12	0.9300
C1—O3	1.3545 (19)	C11—C10	1.355 (3)
C1—C6	1.381 (2)	C11—H11	0.9300
C6—C5	1.380 (2)	C10—H10	0.9300
C6—H6	0.9300	N1—H1	0.8600
C5—H5	0.9300	O2—H2A	0.8200
N2—N3	1.3008 (19)	O3—H3A	0.8200
N2—N1	1.339 (2)
O1—C7—O2	121.74 (15)	N3—C9—C10	131.39 (15)
O1—C7—C4	123.97 (15)	C8—C9—C10	120.69 (16)
O2—C7—C4	114.28 (13)	N1—C8—C9	103.95 (15)
C3—C4—C5	118.12 (15)	N1—C8—C13	133.65 (17)
C3—C4—C7	120.59 (15)	C9—C8—C13	122.39 (16)
C5—C4—C7	121.30 (15)	C12—C13—C8	115.53 (17)
C2—C3—C4	121.11 (16)	C12—C13—H13	122.2
C2—C3—H3	119.4	C8—C13—H13	122.2
C4—C3—H3	119.4	C13—C12—C11	122.75 (19)
C3—C2—C1	120.55 (16)	C13—C12—H12	118.6
C3—C2—H2	119.7	C11—C12—H12	118.6
C1—C2—H2	119.7	C10—C11—C12	121.73 (17)
O3—C1—C2	118.07 (15)	C10—C11—H11	119.1
O3—C1—C6	122.67 (15)	C12—C11—H11	119.1
C2—C1—C6	119.26 (16)	C11—C10—C9	116.89 (16)
C5—C6—C1	120.36 (15)	C11—C10—H10	121.6
C5—C6—H6	119.8	C9—C10—H10	121.6
C1—C6—H6	119.8	N2—N3—C9	108.75 (14)
C6—C5—C4	120.56 (15)	N2—N1—C8	111.29 (14)
C6—C5—H5	119.7	N2—N1—H1	124.4
C4—C5—H5	119.7	C8—N1—H1	124.4
N3—N2—N1	108.09 (14)	C7—O2—H2A	109.5
N3—C9—C8	107.91 (14)	C1—O3—H3A	109.5
O1—C7—C4—C3	−18.0 (2)	N3—C9—C8—C13	178.84 (16)
O2—C7—C4—C3	161.82 (15)	C10—C9—C8—C13	−1.3 (3)
O1—C7—C4—C5	161.86 (16)	N1—C8—C13—C12	179.32 (19)
O2—C7—C4—C5	−18.3 (2)	C9—C8—C13—C12	0.6 (3)
C5—C4—C3—C2	1.3 (3)	C8—C13—C12—C11	0.6 (3)
C7—C4—C3—C2	−178.86 (17)	C13—C12—C11—C10	−1.2 (3)
C4—C3—C2—C1	−1.3 (3)	C12—C11—C10—C9	0.5 (3)
C3—C2—C1—O3	−179.75 (16)	N3—C9—C10—C11	−179.47 (17)
C3—C2—C1—C6	−0.1 (3)	C8—C9—C10—C11	0.6 (2)
O3—C1—C6—C5	−178.87 (16)	N1—N2—N3—C9	−0.20 (18)
C2—C1—C6—C5	1.5 (3)	C8—C9—N3—N2	0.25 (18)
C1—C6—C5—C4	−1.5 (3)	C10—C9—N3—N2	−179.65 (18)
C3—C4—C5—C6	0.1 (2)	N3—N2—N1—C8	0.09 (19)
C7—C4—C5—C6	−179.74 (16)	C9—C8—N1—N2	0.06 (18)
N3—C9—C8—N1	−0.18 (17)	C13—C8—N1—N2	−178.79 (18)
C10—C9—C8—N1	179.72 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.86	2.20	2.982 (2)	152
O2—H2A···N3ii	0.82	1.87	2.6817 (19)	169
O3—H3A···O1iii	0.82	1.88	2.6912 (17)	171
C13—H13···O3iv	0.93	2.49	3.373 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.86	2.20	2.982 (2)	152
O2—H2A⋯N3ii	0.82	1.87	2.6817 (19)	169
O3—H3A⋯O1iii	0.82	1.88	2.6912 (17)	171
C13—H13⋯O3iv	0.93	2.49	3.373 (2)	159

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