4-Guanidinobenzene-sulfonic acid.

IN THE ZWITTERIONIC TITLE COMPOUND (SYSTEMATIC NAME: 4-{[amino(inimio)methyl]amino}benzenesulfonate), C(7)H(9)N(3)O(3)S, the dihedral angle between the plane of the guanidine grouping and the benzene ring system is 44.87 (7)°. The crystal packing is stabilized by inter-molecular N-H⋯O hydrogen bonds involving all the potential donors.

Related literature

For the synthesis, see: Hofbens & Rath (1981 ▶). For the effect of guanidine salts on protein structure and their inhibitory effect on various physiological activities, see: Miyake et al. (2008 ▶).

Experimental

Crystal data

C7H9N3O3S

M = 215.24

Orthorhombic,

a = 7.9967 (9) Å

b = 11.9200 (13) Å

c = 19.721 (2) Å

V = 1879.8 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.35 × 0.3 × 0.2 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.902, T max = 0.944

10292 measured reflections

2156 independent reflections

1544 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.02

2156 reflections

163 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.31 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012355/bq2128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012355/bq2128Isup2.hkl

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

C7H9N3O3S	Dx = 1.521 Mg m−3
Mr = 215.24	Melting point > 300 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2125 reflections
a = 7.9967 (9) Å	θ = 3.2–25.9°
b = 11.9200 (13) Å	µ = 0.33 mm−1
c = 19.721 (2) Å	T = 296 K
V = 1879.8 (4) Å3	Block, colourless
Z = 8	0.35 × 0.3 × 0.2 mm
F(000) = 896

Bruker SMART APEXII CCD diffractometer	2156 independent reflections
Radiation source: fine-focus sealed tube	1544 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.902, Tmax = 0.944	k = −15→13
10292 measured reflections	l = −24→25

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.054P)2 + 0.6089P] where P = (Fo2 + 2Fc2)/3
2156 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0397 (3)	0.48689 (18)	0.26624 (10)	0.0329 (5)
C2	0.0470 (3)	0.53779 (18)	0.32882 (11)	0.0338 (5)
C3	0.1174 (2)	0.64333 (17)	0.33506 (10)	0.0316 (5)
C4	0.1778 (3)	0.69826 (18)	0.27833 (11)	0.0356 (5)
C5	0.1684 (3)	0.64822 (17)	0.21529 (11)	0.0346 (5)
C6	0.1005 (2)	0.54177 (16)	0.20961 (10)	0.0291 (4)
C7	0.1541 (3)	0.65879 (18)	0.45879 (10)	0.0349 (5)
H1	−0.006 (3)	0.4173 (19)	0.2604 (12)	0.044 (6)*
H2	−0.004 (3)	0.504 (2)	0.3685 (11)	0.043 (6)*
H3	0.230 (3)	0.765 (2)	0.2812 (11)	0.045 (7)*
H4	0.210 (3)	0.6900 (18)	0.1779 (13)	0.043 (6)*
H5	0.101 (3)	0.767 (2)	0.3958 (12)	0.049 (7)*
H6	0.253 (3)	0.523 (2)	0.4302 (14)	0.055 (8)*
H7	0.236 (3)	0.529 (2)	0.5062 (14)	0.058 (8)*
H8	0.178 (3)	0.700 (2)	0.5536 (15)	0.072 (9)*
H9	0.098 (3)	0.787 (2)	0.5079 (13)	0.052 (8)*
N1	0.1200 (3)	0.70124 (16)	0.39801 (10)	0.0412 (5)
N2	0.2066 (3)	0.55499 (17)	0.46566 (11)	0.0439 (5)
N3	0.1313 (3)	0.7218 (2)	0.51347 (11)	0.0532 (6)
O1	0.21174 (19)	0.38280 (13)	0.13149 (8)	0.0451 (4)
O2	−0.07907 (17)	0.43211 (12)	0.12279 (7)	0.0376 (4)
O3	0.1335 (2)	0.55807 (12)	0.07941 (8)	0.0494 (5)
S1	0.09167 (7)	0.47441 (4)	0.12971 (2)	0.03204 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0413 (11)	0.0274 (11)	0.0300 (11)	−0.0057 (9)	−0.0014 (9)	0.0013 (8)
C2	0.0401 (10)	0.0355 (12)	0.0258 (11)	−0.0029 (9)	0.0007 (9)	0.0027 (9)
C3	0.0386 (10)	0.0276 (10)	0.0287 (11)	0.0059 (9)	−0.0034 (9)	−0.0024 (8)
C4	0.0467 (12)	0.0233 (10)	0.0368 (12)	−0.0024 (9)	−0.0033 (10)	−0.0017 (9)
C5	0.0451 (11)	0.0260 (11)	0.0327 (12)	−0.0013 (10)	0.0034 (10)	0.0034 (9)
C6	0.0348 (10)	0.0256 (10)	0.0268 (10)	0.0012 (8)	−0.0011 (8)	−0.0012 (8)
C7	0.0442 (11)	0.0343 (11)	0.0262 (11)	0.0069 (10)	−0.0028 (9)	−0.0045 (9)
N1	0.0665 (13)	0.0261 (10)	0.0311 (10)	0.0095 (9)	−0.0096 (9)	−0.0053 (8)
N2	0.0691 (13)	0.0396 (11)	0.0231 (10)	0.0176 (10)	−0.0035 (10)	−0.0027 (8)
N3	0.0846 (16)	0.0421 (13)	0.0329 (12)	0.0172 (12)	−0.0051 (11)	−0.0121 (10)
O1	0.0532 (9)	0.0373 (9)	0.0448 (10)	0.0100 (7)	0.0017 (7)	−0.0085 (7)
O2	0.0465 (8)	0.0309 (8)	0.0355 (9)	−0.0020 (7)	−0.0086 (7)	−0.0012 (6)
O3	0.0869 (12)	0.0336 (9)	0.0278 (8)	−0.0105 (9)	0.0088 (8)	0.0034 (6)
S1	0.0474 (3)	0.0247 (3)	0.0240 (3)	−0.0011 (2)	0.0010 (2)	−0.00080 (19)

C1—C2	1.376 (3)	C7—N2	1.313 (3)
C1—C6	1.383 (3)	C7—N3	1.327 (3)
C1—H1	0.91 (2)	C7—N1	1.329 (3)
C2—C3	1.384 (3)	N1—H5	0.80 (3)
C2—H2	0.97 (2)	N2—H6	0.88 (3)
C3—C4	1.383 (3)	N2—H7	0.89 (3)
C3—N1	1.421 (3)	N3—H8	0.91 (3)
C4—C5	1.381 (3)	N3—H9	0.83 (3)
C4—H3	0.90 (2)	O1—S1	1.4546 (15)
C5—C6	1.385 (3)	O2—S1	1.4619 (15)
C5—H4	0.95 (2)	O3—S1	1.4457 (15)
C6—S1	1.770 (2)
C2—C1—C6	120.1 (2)	N2—C7—N3	119.6 (2)
C2—C1—H1	122.0 (15)	N2—C7—N1	121.1 (2)
C6—C1—H1	117.9 (15)	N3—C7—N1	119.3 (2)
C1—C2—C3	119.9 (2)	C7—N1—C3	127.30 (19)
C1—C2—H2	121.6 (14)	C7—N1—H5	117.4 (18)
C3—C2—H2	118.4 (14)	C3—N1—H5	115.2 (18)
C4—C3—C2	120.0 (2)	C7—N2—H6	117.3 (17)
C4—C3—N1	118.13 (19)	C7—N2—H7	120.1 (17)
C2—C3—N1	121.70 (19)	H6—N2—H7	117 (2)
C5—C4—C3	120.3 (2)	C7—N3—H8	119.0 (18)
C5—C4—H3	117.6 (14)	C7—N3—H9	117.9 (19)
C3—C4—H3	122.0 (14)	H8—N3—H9	121 (3)
C4—C5—C6	119.3 (2)	O3—S1—O1	112.45 (10)
C4—C5—H4	116.9 (14)	O3—S1—O2	112.95 (10)
C6—C5—H4	123.7 (14)	O1—S1—O2	111.09 (9)
C1—C6—C5	120.40 (19)	O3—S1—C6	106.78 (9)
C1—C6—S1	119.37 (15)	O1—S1—C6	107.02 (9)
C5—C6—S1	120.22 (15)	O2—S1—C6	106.07 (9)
C6—C1—C2—C3	−0.9 (3)	N2—C7—N1—C3	6.7 (4)
C1—C2—C3—C4	1.1 (3)	N3—C7—N1—C3	−171.9 (2)
C1—C2—C3—N1	176.8 (2)	C4—C3—N1—C7	−141.9 (2)
C2—C3—C4—C5	−0.1 (3)	C2—C3—N1—C7	42.3 (3)
N1—C3—C4—C5	−176.0 (2)	C1—C6—S1—O3	169.46 (17)
C3—C4—C5—C6	−1.1 (3)	C5—C6—S1—O3	−10.8 (2)
C2—C1—C6—C5	−0.2 (3)	C1—C6—S1—O1	−69.91 (18)
C2—C1—C6—S1	179.46 (16)	C5—C6—S1—O1	109.79 (18)
C4—C5—C6—C1	1.2 (3)	C1—C6—S1—O2	48.76 (18)
C4—C5—C6—S1	−178.46 (16)	C5—C6—S1—O2	−131.54 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H5···O2i	0.80 (3)	2.00 (3)	2.802 (2)	171 (2)
N2—H6···O2ii	0.88 (3)	2.02 (3)	2.851 (2)	158 (2)
N2—H7···O3iii	0.89 (3)	2.07 (3)	2.913 (3)	160 (2)
N3—H8···O1iii	0.91 (3)	2.03 (3)	2.924 (3)	167 (3)
N3—H9···O3iv	0.83 (3)	2.34 (3)	2.928 (3)	129 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H5⋯O2i	0.80 (3)	2.00 (3)	2.802 (2)	171 (2)
N2—H6⋯O2ii	0.88 (3)	2.02 (3)	2.851 (2)	158 (2)
N2—H7⋯O3iii	0.89 (3)	2.07 (3)	2.913 (3)	160 (2)
N3—H8⋯O1iii	0.91 (3)	2.03 (3)	2.924 (3)	167 (3)
N3—H9⋯O3iv	0.83 (3)	2.34 (3)	2.928 (3)	129 (2)

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