N-[Amino-(azido)-meth-ylidene]-4-methyl-benzene-sulfonamide.

In the title mol-ecule, C(8)H(10)N(5)O(2)S, the amino-(azido)-methyl and p-toluene-sulfonyl moieties are inclined almost at right angles with respect to each other, making a dihedral angle of 83.49 (6)°. An intra-molecular N-H⋯O hydrogen bond gives rise to the formation of six-membered ring with graph-set motif S(6). In the crystal, inter-molecular N-H⋯O hydrogen bonding is responsible for the formation of dimers about inversion centers, which are linked through another N-H⋯O inter-action along the b axis.

Related literature

For the synthesis, see: Arshad et al. (2009 ▶). For the biological activity of sulfonamides, see: Moree et al. (1991 ▶); Arshad et al. (2008 ▶); Gennarti et al. (1994 ▶). For related structures, see: Denny et al. (1980 ▶); Müller & Bärnighausen (1970 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H9N5O2S

M = 239.26

Triclinic,

a = 6.8986 (2) Å

b = 7.2146 (2) Å

c = 11.3771 (3) Å

α = 92.244 (1)°

β = 93.615 (1)°

γ = 110.505 (1)°

V = 528.18 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.34 × 0.17 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

8664 measured reflections

2549 independent reflections

2343 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.088

S = 1.09

2549 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026973/pv2426sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026973/pv2426Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026973/pv2426Isup3.cml

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

C8H9N5O2S	Z = 2
Mr = 239.26	F(000) = 248
Triclinic, P1	Dx = 1.504 Mg m−3
Hall symbol: -P 1	Melting point: 444(2) K
a = 6.8986 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.2146 (2) Å	Cell parameters from 7120 reflections
c = 11.3771 (3) Å	θ = 3.0–28.3°
α = 92.244 (1)°	µ = 0.30 mm−1
β = 93.615 (1)°	T = 296 K
γ = 110.505 (1)°	Needle, colourless
V = 528.18 (3) Å3	0.34 × 0.17 × 0.17 mm

Bruker APEXII CCD diffractometer	2343 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 28.3°, θmin = 3.2°
φ and ω scans	h = −9→9
8664 measured reflections	k = −9→9
2549 independent reflections	l = −15→14

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0384P)2 + 0.179P] where P = (Fo2 + 2Fc2)/3
2549 reflections	(Δ/σ)max = 0.004
152 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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 > 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. The reflection 0 0 1 has been omitted as this was obscured by beamstop.

	x	y	z	Uiso*/Ueq
S1	0.77484 (4)	0.16023 (4)	0.12702 (3)	0.02808 (11)
O1	0.70020 (17)	0.32207 (14)	0.13239 (11)	0.0459 (3)
O2	0.87648 (15)	0.13621 (15)	0.02394 (8)	0.0370 (2)
N1	0.57940 (16)	−0.03376 (15)	0.14825 (9)	0.0291 (2)
N2	0.7254 (2)	−0.27167 (18)	0.08497 (12)	0.0383 (3)
H2N	0.825 (3)	−0.194 (3)	0.0593 (18)	0.057*
H3N	0.710 (3)	−0.399 (3)	0.0848 (18)	0.057*
N3	0.40903 (18)	−0.37488 (16)	0.15282 (11)	0.0368 (3)
N4	0.27278 (18)	−0.32615 (17)	0.19944 (11)	0.0381 (3)
N5	0.1395 (2)	−0.3067 (2)	0.24161 (15)	0.0586 (4)
C1	1.3707 (4)	0.2513 (3)	0.55842 (19)	0.0833 (8)
H1A	1.3230	0.1326	0.6002	0.125*
H1B	1.3738	0.3624	0.6088	0.125*
H1C	1.5079	0.2718	0.5354	0.125*
C2	1.2249 (3)	0.2310 (2)	0.44945 (14)	0.0514 (4)
C3	1.0431 (3)	0.2697 (3)	0.45779 (14)	0.0578 (5)
H3	1.0116	0.3084	0.5309	0.069*
C4	0.9072 (3)	0.2521 (2)	0.35961 (14)	0.0468 (4)
H4	0.7868	0.2807	0.3664	0.056*
C5	0.95280 (19)	0.19123 (17)	0.25110 (11)	0.0301 (3)
C6	1.1336 (2)	0.1525 (2)	0.24079 (13)	0.0391 (3)
H6	1.1648	0.1128	0.1678	0.047*
C7	1.2684 (3)	0.1733 (3)	0.34053 (15)	0.0508 (4)
H7	1.3904	0.1478	0.3335	0.061*
C8	0.58221 (18)	−0.21318 (17)	0.12696 (10)	0.0275 (2)

	U11	U22	U33	U12	U13	U23
S1	0.02984 (17)	0.02068 (16)	0.03386 (18)	0.00862 (11)	0.00265 (11)	0.00626 (11)
O1	0.0493 (6)	0.0259 (5)	0.0674 (7)	0.0189 (4)	0.0042 (5)	0.0108 (5)
O2	0.0366 (5)	0.0402 (5)	0.0313 (5)	0.0090 (4)	0.0053 (4)	0.0083 (4)
N1	0.0278 (5)	0.0233 (5)	0.0357 (5)	0.0081 (4)	0.0037 (4)	0.0035 (4)
N2	0.0397 (6)	0.0250 (5)	0.0526 (7)	0.0129 (5)	0.0117 (5)	0.0047 (5)
N3	0.0366 (6)	0.0243 (5)	0.0458 (6)	0.0054 (4)	0.0072 (5)	0.0039 (4)
N4	0.0360 (6)	0.0283 (5)	0.0438 (6)	0.0028 (4)	0.0057 (5)	0.0077 (5)
N5	0.0480 (8)	0.0493 (8)	0.0766 (10)	0.0108 (6)	0.0250 (7)	0.0119 (7)
C1	0.0957 (16)	0.0691 (13)	0.0535 (11)	−0.0045 (12)	−0.0346 (11)	0.0146 (10)
C2	0.0585 (10)	0.0377 (8)	0.0402 (8)	−0.0029 (7)	−0.0128 (7)	0.0082 (6)
C3	0.0735 (12)	0.0533 (10)	0.0311 (7)	0.0038 (8)	0.0057 (7)	−0.0045 (7)
C4	0.0470 (8)	0.0470 (8)	0.0410 (8)	0.0101 (7)	0.0089 (6)	−0.0059 (6)
C5	0.0334 (6)	0.0212 (5)	0.0317 (6)	0.0045 (4)	0.0024 (5)	0.0021 (4)
C6	0.0391 (7)	0.0417 (7)	0.0366 (7)	0.0153 (6)	−0.0015 (5)	−0.0002 (6)
C7	0.0441 (8)	0.0537 (9)	0.0513 (9)	0.0154 (7)	−0.0110 (7)	0.0039 (7)
C8	0.0301 (6)	0.0233 (5)	0.0271 (5)	0.0073 (4)	−0.0009 (4)	0.0036 (4)

S1—O1	1.4324 (10)	C1—H1B	0.9600
S1—O2	1.4387 (10)	C1—H1C	0.9600
S1—N1	1.6064 (10)	C2—C7	1.376 (3)
S1—C5	1.7648 (13)	C2—C3	1.385 (3)
N1—C8	1.3147 (15)	C3—C4	1.384 (3)
N2—C8	1.3104 (17)	C3—H3	0.9300
N2—H2N	0.80 (2)	C4—C5	1.385 (2)
N2—H3N	0.89 (2)	C4—H4	0.9300
N3—N4	1.2523 (17)	C5—C6	1.381 (2)
N3—C8	1.4034 (15)	C6—C7	1.389 (2)
N4—N5	1.112 (2)	C6—H6	0.9300
C1—C2	1.515 (2)	C7—H7	0.9300
C1—H1A	0.9600
O1—S1—O2	117.13 (6)	C3—C2—C1	120.33 (19)
O1—S1—N1	105.65 (6)	C4—C3—C2	121.43 (15)
O2—S1—N1	112.85 (6)	C4—C3—H3	119.3
O1—S1—C5	107.75 (6)	C2—C3—H3	119.3
O2—S1—C5	107.55 (6)	C3—C4—C5	119.15 (16)
N1—S1—C5	105.20 (6)	C3—C4—H4	120.4
C8—N1—S1	121.49 (9)	C5—C4—H4	120.4
C8—N2—H2N	120.4 (15)	C6—C5—C4	120.34 (13)
C8—N2—H3N	119.0 (13)	C6—C5—S1	120.58 (10)
H2N—N2—H3N	120.6 (19)	C4—C5—S1	119.08 (11)
N4—N3—C8	113.81 (11)	C5—C6—C7	119.34 (14)
N5—N4—N3	171.56 (14)	C5—C6—H6	120.3
C2—C1—H1A	109.5	C7—C6—H6	120.3
C2—C1—H1B	109.5	C2—C7—C6	121.31 (16)
H1A—C1—H1B	109.5	C2—C7—H7	119.3
C2—C1—H1C	109.5	C6—C7—H7	119.3
H1A—C1—H1C	109.5	N2—C8—N1	130.52 (12)
H1B—C1—H1C	109.5	N2—C8—N3	111.45 (11)
C7—C2—C3	118.41 (15)	N1—C8—N3	118.03 (11)
C7—C2—C1	121.3 (2)
O1—S1—N1—C8	166.90 (10)	O1—S1—C5—C4	41.58 (13)
O2—S1—N1—C8	37.71 (12)	O2—S1—C5—C4	168.70 (11)
C5—S1—N1—C8	−79.26 (11)	N1—S1—C5—C4	−70.78 (12)
C8—N3—N4—N5	−177.3 (11)	C4—C5—C6—C7	0.6 (2)
C7—C2—C3—C4	−0.2 (3)	S1—C5—C6—C7	−178.38 (12)
C1—C2—C3—C4	−179.94 (16)	C3—C2—C7—C6	−0.5 (3)
C2—C3—C4—C5	1.0 (3)	C1—C2—C7—C6	179.26 (16)
C3—C4—C5—C6	−1.2 (2)	C5—C6—C7—C2	0.3 (2)
C3—C4—C5—S1	177.75 (12)	S1—N1—C8—N2	−2.0 (2)
O1—S1—C5—C6	−139.43 (11)	S1—N1—C8—N3	177.16 (9)
O2—S1—C5—C6	−12.31 (13)	N4—N3—C8—N2	176.19 (12)
N1—S1—C5—C6	108.21 (11)	N4—N3—C8—N1	−3.12 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2i	0.80 (2)	2.24 (2)	2.9459 (16)	148 (2)
N2—H3N···O1ii	0.89 (2)	2.08 (2)	2.9481 (15)	164 (2)
N2—H2N···O2	0.80 (2)	2.34 (2)	2.8862 (16)	127 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O2i	0.80 (2)	2.24 (2)	2.9459 (16)	148 (2)
N2—H3N⋯O1ii	0.89 (2)	2.08 (2)	2.9481 (15)	164 (2)
N2—H2N⋯O2	0.80 (2)	2.34 (2)	2.8862 (16)	127 (2)

Symmetry codes: (i) ; (ii) .