Benzotriazolium 4-methyl-benzene-sulfonate.

In the title molecular salt, C6H6N3 (+)·C7H7O3S(-), the components are linked by N-H⋯O hydrogen bonds into zigzag chains along [100]. These chains are further connected by weak C-H⋯O, C-H⋯π and π-π (centroid-to-centroid distances = 3.510, 3.701 and 3.754 Å) inter-actions into a three-dimensional network.

Related literature

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

Experimental

Crystal data

C6H6N3 +·C7H7O3S−

M = 291.32

Orthorhombic,

a = 12.2330 (5) Å

b = 13.4144 (6) Å

c = 16.3320 (9) Å

V = 2680.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 295 K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.937, T max = 0.951

45507 measured reflections

3889 independent reflections

2766 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.108

S = 1.08

3889 reflections

191 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.35 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/S1600536814003857/bt6963sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003857/bt6963Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003857/bt6963Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H6N3+·C7H7O3S−	F(000) = 1216
Mr = 291.32	Dx = 1.444 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9880 reflections
a = 12.2330 (5) Å	θ = 2.5–29.4°
b = 13.4144 (6) Å	µ = 0.25 mm−1
c = 16.3320 (9) Å	T = 295 K
V = 2680.1 (2) Å3	Block, colourless
Z = 8	0.26 × 0.24 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3889 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω and φ scan	θmax = 30.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.937, Tmax = 0.951	k = −18→18
45507 measured reflections	l = −22→23

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0359P)2 + 1.3937P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3889 reflections	Δρmax = 0.26 e Å−3
191 parameters	Δρmin = −0.35 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (5)

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
C1	0.90878 (12)	0.03041 (12)	0.16244 (9)	0.0333 (3)
C2	0.81836 (14)	0.05952 (13)	0.20733 (11)	0.0418 (4)
H2	0.7961	0.1258	0.2066	0.050*
C3	0.76102 (15)	−0.00918 (15)	0.25324 (11)	0.0460 (4)
H3	0.6998	0.0114	0.2824	0.055*
C4	0.79293 (15)	−0.10826 (14)	0.25669 (11)	0.0432 (4)
C5	0.88410 (16)	−0.13637 (13)	0.21152 (12)	0.0475 (4)
H5	0.9074	−0.2023	0.2132	0.057*
C6	0.94106 (15)	−0.06856 (13)	0.16406 (11)	0.0429 (4)
H6	1.0009	−0.0894	0.1333	0.051*
C7	0.73032 (19)	−0.18330 (17)	0.30695 (13)	0.0633 (6)
H7A	0.6711	−0.2097	0.2750	0.095*
H7B	0.7017	−0.1515	0.3550	0.095*
H7C	0.7783	−0.2366	0.3228	0.095*
C8	0.67586 (12)	0.01515 (12)	0.03229 (10)	0.0344 (3)
C9	0.67158 (15)	0.11875 (12)	0.02304 (11)	0.0414 (4)
H9	0.7228	0.1535	−0.0079	0.050*
C10	0.58772 (16)	0.16563 (14)	0.06224 (12)	0.0486 (4)
H10	0.5809	0.2344	0.0569	0.058*
C11	0.51133 (16)	0.11404 (15)	0.11036 (12)	0.0504 (5)
H11	0.4563	0.1499	0.1363	0.061*
C12	0.51505 (15)	0.01289 (14)	0.12041 (11)	0.0448 (4)
H12	0.4647	−0.0211	0.1526	0.054*
C13	0.59940 (13)	−0.03593 (12)	0.07916 (10)	0.0349 (3)
N1	0.71524 (13)	−0.14630 (11)	0.02730 (11)	0.0486 (4)
N2	0.74412 (12)	−0.05667 (11)	0.00306 (10)	0.0430 (3)
N3	0.62856 (13)	−0.13358 (11)	0.07344 (10)	0.0425 (3)
O1	0.93251 (11)	0.11850 (10)	0.02148 (8)	0.0524 (3)
O2	1.09402 (10)	0.08554 (10)	0.10320 (9)	0.0507 (3)
O3	0.96735 (11)	0.21352 (9)	0.14451 (8)	0.0507 (3)
S1	0.98089 (3)	0.11794 (3)	0.10202 (3)	0.03644 (12)
H2A	0.8027 (13)	−0.0538 (18)	−0.0271 (13)	0.075 (8)*
H3A	0.5961 (17)	−0.1848 (12)	0.0946 (13)	0.068 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0331 (8)	0.0359 (8)	0.0310 (8)	0.0049 (6)	−0.0028 (6)	−0.0038 (6)
C2	0.0387 (8)	0.0433 (9)	0.0434 (9)	0.0115 (7)	−0.0001 (7)	−0.0048 (7)
C3	0.0345 (8)	0.0616 (11)	0.0419 (9)	0.0035 (8)	0.0046 (7)	−0.0070 (9)
C4	0.0439 (9)	0.0508 (10)	0.0349 (9)	−0.0100 (8)	−0.0045 (7)	−0.0063 (7)
C5	0.0605 (12)	0.0349 (8)	0.0471 (10)	0.0004 (8)	0.0034 (9)	−0.0053 (7)
C6	0.0455 (9)	0.0392 (9)	0.0440 (9)	0.0079 (7)	0.0083 (8)	−0.0063 (7)
C7	0.0662 (14)	0.0698 (14)	0.0539 (12)	−0.0192 (11)	0.0060 (10)	0.0002 (11)
C8	0.0292 (7)	0.0383 (8)	0.0356 (8)	−0.0036 (6)	−0.0033 (6)	0.0015 (6)
C9	0.0429 (9)	0.0369 (8)	0.0443 (9)	−0.0090 (7)	0.0000 (7)	0.0052 (7)
C10	0.0580 (11)	0.0344 (8)	0.0534 (11)	−0.0022 (8)	−0.0013 (9)	−0.0022 (8)
C11	0.0490 (10)	0.0524 (11)	0.0499 (11)	0.0039 (9)	0.0062 (9)	−0.0123 (9)
C12	0.0415 (9)	0.0531 (10)	0.0399 (9)	−0.0085 (8)	0.0070 (7)	−0.0001 (8)
C13	0.0349 (8)	0.0343 (8)	0.0356 (8)	−0.0063 (6)	−0.0049 (6)	0.0023 (6)
N1	0.0438 (8)	0.0392 (8)	0.0628 (10)	0.0038 (7)	−0.0060 (8)	0.0024 (7)
N2	0.0329 (7)	0.0426 (8)	0.0536 (9)	0.0011 (6)	0.0020 (7)	0.0027 (7)
N3	0.0429 (8)	0.0352 (7)	0.0496 (9)	−0.0059 (6)	−0.0045 (7)	0.0072 (6)
O1	0.0532 (8)	0.0656 (9)	0.0383 (7)	0.0041 (7)	−0.0027 (6)	0.0063 (6)
O2	0.0346 (6)	0.0543 (7)	0.0631 (9)	0.0069 (6)	0.0037 (6)	0.0067 (6)
O3	0.0629 (8)	0.0335 (6)	0.0558 (8)	0.0072 (6)	−0.0009 (7)	0.0004 (5)
S1	0.0347 (2)	0.0360 (2)	0.0387 (2)	0.00720 (16)	−0.00031 (16)	0.00142 (16)

C1—C2	1.383 (2)	C8—C9	1.399 (2)
C1—C6	1.385 (2)	C9—C10	1.363 (3)
C1—S1	1.7694 (17)	C9—H9	0.9300
C2—C3	1.380 (3)	C10—C11	1.404 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.386 (3)	C11—C12	1.368 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.389 (3)	C12—C13	1.395 (2)
C4—C7	1.508 (3)	C12—H12	0.9300
C5—C6	1.383 (3)	C13—N3	1.361 (2)
C5—H5	0.9300	N1—N3	1.312 (2)
C6—H6	0.9300	N1—N2	1.314 (2)
C7—H7A	0.9600	N2—H2A	0.871 (9)
C7—H7B	0.9600	N3—H3A	0.866 (9)
C7—H7C	0.9600	O1—S1	1.4423 (14)
C8—N2	1.361 (2)	O2—S1	1.4507 (13)
C8—C13	1.389 (2)	O3—S1	1.4673 (13)
C2—C1—C6	119.24 (16)	C10—C9—H9	122.1
C2—C1—S1	120.46 (13)	C8—C9—H9	122.1
C6—C1—S1	120.29 (13)	C9—C10—C11	122.46 (17)
C3—C2—C1	120.40 (16)	C9—C10—H10	118.8
C3—C2—H2	119.8	C11—C10—H10	118.8
C1—C2—H2	119.8	C12—C11—C10	122.29 (18)
C2—C3—C4	121.28 (16)	C12—C11—H11	118.9
C2—C3—H3	119.4	C10—C11—H11	118.9
C4—C3—H3	119.4	C11—C12—C13	115.62 (16)
C3—C4—C5	117.69 (17)	C11—C12—H12	122.2
C3—C4—C7	121.27 (18)	C13—C12—H12	122.2
C5—C4—C7	121.04 (18)	N3—C13—C8	105.09 (15)
C6—C5—C4	121.57 (17)	N3—C13—C12	132.75 (16)
C6—C5—H5	119.2	C8—C13—C12	122.16 (15)
C4—C5—H5	119.2	N3—N1—N2	105.75 (14)
C5—C6—C1	119.81 (16)	N1—N2—C8	112.14 (15)
C5—C6—H6	120.1	N1—N2—H2A	115.6 (16)
C1—C6—H6	120.1	C8—N2—H2A	132.3 (16)
C4—C7—H7A	109.5	N1—N3—C13	112.12 (14)
C4—C7—H7B	109.5	N1—N3—H3A	119.8 (16)
H7A—C7—H7B	109.5	C13—N3—H3A	128.1 (16)
C4—C7—H7C	109.5	O1—S1—O2	113.90 (8)
H7A—C7—H7C	109.5	O1—S1—O3	112.36 (8)
H7B—C7—H7C	109.5	O2—S1—O3	111.30 (8)
N2—C8—C13	104.90 (14)	O1—S1—C1	107.91 (8)
N2—C8—C9	133.48 (16)	O2—S1—C1	105.62 (7)
C13—C8—C9	121.62 (15)	O3—S1—C1	105.06 (8)
C10—C9—C8	115.83 (16)
C6—C1—C2—C3	0.1 (3)	N2—C8—C13—C12	179.46 (15)
S1—C1—C2—C3	178.81 (13)	C9—C8—C13—C12	−0.8 (3)
C1—C2—C3—C4	0.9 (3)	C11—C12—C13—N3	−179.15 (18)
C2—C3—C4—C5	−0.7 (3)	C11—C12—C13—C8	1.2 (3)
C2—C3—C4—C7	179.93 (18)	N3—N1—N2—C8	−0.8 (2)
C3—C4—C5—C6	−0.5 (3)	C13—C8—N2—N1	0.63 (19)
C7—C4—C5—C6	178.86 (18)	C9—C8—N2—N1	−179.05 (18)
C4—C5—C6—C1	1.5 (3)	N2—N1—N3—C13	0.6 (2)
C2—C1—C6—C5	−1.2 (3)	C8—C13—N3—N1	−0.21 (19)
S1—C1—C6—C5	180.00 (14)	C12—C13—N3—N1	−179.87 (18)
N2—C8—C9—C10	179.18 (18)	C2—C1—S1—O1	−89.85 (15)
C13—C8—C9—C10	−0.4 (3)	C6—C1—S1—O1	88.90 (15)
C8—C9—C10—C11	1.2 (3)	C2—C1—S1—O2	147.97 (14)
C9—C10—C11—C12	−0.8 (3)	C6—C1—S1—O2	−33.28 (16)
C10—C11—C12—C13	−0.5 (3)	C2—C1—S1—O3	30.22 (15)
N2—C8—C13—N3	−0.24 (17)	C6—C1—S1—O3	−151.04 (14)
C9—C8—C13—N3	179.48 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.87 (1)	1.82 (1)	2.661 (2)	161 (2)
N3—H3A···O3ii	0.87 (1)	1.77 (1)	2.6326 (19)	176 (2)
C3—H3···O2iii	0.93	2.48	3.359 (2)	158
C12—H12···Cg1iv	0.93	2.66	3.500 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.87 (1)	1.82 (1)	2.661 (2)	161 (2)
N3—H3A⋯O3ii	0.87 (1)	1.77 (1)	2.6326 (19)	176 (2)
C3—H3⋯O2iii	0.93	2.48	3.359 (2)	158
C12—H12⋯Cg1iv	0.93	2.66	3.500 (2)	150

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