1-Methane-sulfonyl-1H-1,2,3-benzotriazole.

The mol-ecular geometry of the title compound, C(7)H(7)N(3)O(2)S, does not differ much from that of the previously reported 4-toluene-sulfonyl analogue. Unlike the latter compound, however, mol-ecules of the title compound associate primarily via π-π stacking inter-actions of their benzene rings [centroid-centroid distance = 3.5865 (8) Å], forming columnar stacks along the crystallographic 2(1) axes. These stacks are inter-connected via weak C-H⋯O and C-H⋯N hydrogen bonds.

Related literature

For crystal structure of 1-(p-toluene­sulfon­yl)-1H-1,2,3-benzotriazole, see: Rodríguez et al. (2005 ▶). For the preparation of the title compound and examples of its synthetic use, see: Katritzky et al. (1992 ▶, 2000 ▶).

Experimental

Crystal data

C7H7N3O2S

M = 197.22

Monoclinic,

a = 9.3685 (3) Å

b = 7.0627 (2) Å

c = 12.4994 (3) Å

β = 92.984 (2)°

V = 825.93 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 150 K

0.50 × 0.30 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer

14989 measured reflections

1886 independent reflections

1674 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.09

1886 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.42 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040778/im2237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040778/im2237Isup2.hkl

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

C7H7N3O2S	F(000) = 408
Mr = 197.22	Dx = 1.586 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2027 reflections
a = 9.3685 (3) Å	θ = 1.0–27.5°
b = 7.0627 (2) Å	µ = 0.36 mm−1
c = 12.4994 (3) Å	T = 150 K
β = 92.984 (2)°	Block, colourless
V = 825.93 (4) Å3	0.50 × 0.30 × 0.25 mm
Z = 4

Nonius KappaCCD diffractometer	1674 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
horizontally mounted graphite crystal	θmax = 27.5°, θmin = 2.2°
Detector resolution: 9.091 pixels mm-1	h = −12→12
ω and π scans to fill the Ewald sphere	k = −9→9
14989 measured reflections	l = −16→16
1886 independent reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.2983P] where P = (Fo2 + 2Fc2)/3
1886 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two least-squares 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 least-squares planes.

Refinement. Refinement of F2 against all diffractions. 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
S	0.39056 (3)	0.07483 (5)	0.36695 (2)	0.02263 (12)
O1	0.32920 (11)	−0.04099 (16)	0.44586 (8)	0.0318 (3)
O2	0.51042 (11)	0.01011 (18)	0.31253 (8)	0.0337 (3)
N1	0.25880 (13)	0.10614 (17)	0.27080 (9)	0.0236 (3)
N2	0.29032 (13)	0.10541 (18)	0.16344 (9)	0.0274 (3)
N3	0.17185 (13)	0.11648 (19)	0.10673 (9)	0.0289 (3)
C3A	0.05897 (15)	0.1243 (2)	0.17395 (11)	0.0233 (3)
C4	−0.08866 (16)	0.1336 (2)	0.14889 (12)	0.0290 (3)
H4	−0.1253	0.1381	0.0784	0.035*
C5	−0.17615 (16)	0.1359 (2)	0.23349 (12)	0.0295 (3)
H5	−0.2746	0.1413	0.2200	0.035*
C6	−0.12050 (16)	0.1302 (2)	0.34029 (12)	0.0290 (3)
H6	−0.1837	0.1318	0.3953	0.035*
C7	0.02458 (16)	0.1222 (2)	0.36641 (11)	0.0273 (3)
H7	0.0611	0.1199	0.4370	0.033*
C7A	0.11237 (14)	0.11801 (19)	0.27980 (11)	0.0218 (3)
C8	0.41970 (16)	0.3025 (2)	0.41766 (11)	0.0277 (3)
H8A	0.4901	0.2977	0.4762	0.042*
H8B	0.3319	0.3521	0.4424	0.042*
H8C	0.4531	0.3828	0.3623	0.042*

	U11	U22	U33	U12	U13	U23
S	0.02097 (19)	0.0276 (2)	0.01921 (18)	0.00087 (12)	0.00002 (12)	0.00117 (12)
O1	0.0327 (6)	0.0361 (6)	0.0263 (5)	−0.0063 (5)	−0.0026 (4)	0.0100 (4)
O2	0.0245 (5)	0.0461 (7)	0.0306 (5)	0.0088 (5)	0.0010 (4)	−0.0071 (5)
N1	0.0209 (6)	0.0317 (6)	0.0183 (5)	0.0002 (5)	0.0016 (4)	0.0007 (4)
N2	0.0275 (6)	0.0369 (7)	0.0180 (5)	−0.0017 (5)	0.0030 (4)	0.0007 (5)
N3	0.0264 (6)	0.0402 (7)	0.0201 (6)	−0.0023 (5)	0.0002 (5)	0.0017 (5)
C3A	0.0252 (7)	0.0222 (7)	0.0223 (6)	−0.0016 (5)	−0.0002 (5)	0.0008 (5)
C4	0.0266 (7)	0.0293 (7)	0.0304 (7)	−0.0015 (6)	−0.0052 (6)	0.0009 (6)
C5	0.0220 (7)	0.0251 (7)	0.0413 (8)	−0.0012 (6)	0.0005 (6)	0.0008 (6)
C6	0.0263 (7)	0.0262 (7)	0.0352 (8)	0.0000 (6)	0.0100 (6)	0.0008 (6)
C7	0.0290 (7)	0.0294 (7)	0.0238 (7)	0.0010 (6)	0.0038 (5)	0.0010 (6)
C7A	0.0212 (6)	0.0217 (6)	0.0225 (6)	0.0001 (5)	0.0005 (5)	0.0006 (5)
C8	0.0301 (7)	0.0290 (7)	0.0239 (6)	−0.0017 (6)	0.0001 (5)	−0.0003 (6)

S—O2	1.4185 (10)	C4—H4	0.9300
S—O1	1.4254 (11)	C5—C6	1.408 (2)
S—N1	1.6919 (12)	C5—H5	0.9300
S—C8	1.7444 (15)	C6—C7	1.382 (2)
N1—C7A	1.3848 (17)	C6—H6	0.9300
N1—N2	1.3890 (16)	C7—C7A	1.3936 (19)
N2—N3	1.2878 (17)	C7—H7	0.9300
N3—C3A	1.3856 (18)	C8—H8A	0.9600
C3A—C7A	1.3905 (18)	C8—H8B	0.9600
C3A—C4	1.4037 (19)	C8—H8C	0.9600
C4—C5	1.371 (2)
O2—S—O1	120.31 (7)	C4—C5—H5	119.2
O2—S—N1	105.55 (6)	C6—C5—H5	119.2
O1—S—N1	105.13 (6)	C7—C6—C5	122.41 (14)
O2—S—C8	111.01 (7)	C7—C6—H6	118.8
O1—S—C8	109.79 (7)	C5—C6—H6	118.8
N1—S—C8	103.43 (6)	C6—C7—C7A	115.48 (13)
C7A—N1—N2	109.87 (11)	C6—C7—H7	122.3
C7A—N1—S	129.75 (9)	C7A—C7—H7	122.3
N2—N1—S	120.12 (9)	N1—C7A—C3A	103.50 (11)
N3—N2—N1	108.12 (11)	N1—C7A—C7	133.75 (13)
N2—N3—C3A	109.37 (11)	C3A—C7A—C7	122.74 (13)
N3—C3A—C7A	109.12 (12)	S—C8—H8A	109.5
N3—C3A—C4	129.85 (13)	S—C8—H8B	109.5
C7A—C3A—C4	121.02 (13)	H8A—C8—H8B	109.5
C5—C4—C3A	116.74 (13)	S—C8—H8C	109.5
C5—C4—H4	121.6	H8A—C8—H8C	109.5
C3A—C4—H4	121.6	H8B—C8—H8C	109.5
C4—C5—C6	121.60 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.55	3.270 (2)	135
C6—H6···O1ii	0.93	2.55	3.451 (2)	164
C8—H8B···N3iii	0.96	2.61	3.446 (2)	145
C8—H8C···O2iv	0.96	2.40	3.325 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.55	3.270 (2)	135
C6—H6⋯O1ii	0.93	2.55	3.451 (2)	164
C8—H8B⋯N3iii	0.96	2.61	3.446 (2)	145
C8—H8C⋯O2iv	0.96	2.40	3.325 (2)	161

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