4-Amino-N-(3-meth-oxy-pyrazin-2-yl)benzene-sulfonamide.

The overall mol-ecular geometry of the title compound, C(11)H(12)N(4)O(3)S, is bent, with a dihedral angle of 89.24 (5)° between the best planes through the two aromatic rings. Each mol-ecule behaves as a hydrogen-bond donor toward three different mol-ecules, through its amidic and the two aminic H atoms, and it behaves as a hydrogen-bond acceptor from two other mol-ecules via one of its sulfonamidic O atoms. In the crystal, mol-ecules linked by N-H⋯N and N-H⋯O hydrogen bonds form kinked layers parallel to (001), adjacent layers being connected by van der Waals inter-actions.

Related literature

The title compound is a prolonged-action drug known as sulfameth­oxy­pyrazine or sulfalene, traditionally used for the treatment of urinary tract infections and chronic bronchitis. It is also presently employed in combination with other drugs for the treatment of malaria and other diseases. For the pharmacological applications of the title compound, see: Adam & Hagelnur (2009 ▶); Penali & Jansen (2008 ▶). For the structure of a related anti­cancer drug, see: Liu et al. (1994 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H12N4O3S

M = 280.31

Orthorhombic,

a = 10.7589 (2) Å

b = 9.5652 (2) Å

c = 24.5586 (4) Å

V = 2527.35 (8) Å3

Z = 8

Cu Kα radiation

μ = 2.40 mm−1

T = 150 K

0.60 × 0.10 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur PX Ultra CCD diffractometer

Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2006 ▶) T min = 0.477, T max = 1.000

5771 measured reflections

2373 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.103

S = 1.14

2373 reflections

184 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038158/fl2318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038158/fl2318Isup2.hkl

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

C11H12N4O3S	F(000) = 1168
Mr = 280.31	Dx = 1.473 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4106 reflections
a = 10.7589 (2) Å	θ = 4.5–71.1°
b = 9.5652 (2) Å	µ = 2.40 mm−1
c = 24.5586 (4) Å	T = 150 K
V = 2527.35 (8) Å3	Elongated prism, colourless
Z = 8	0.60 × 0.10 × 0.10 mm

Oxford Diffraction Xcalibur PX Ultra CCD diffractometer	2373 independent reflections
Radiation source: fine-focus sealed tube	2103 reflections with I > 2σ(I)
Oxford Diffraction, Enhance ULTRA assembly	Rint = 0.016
Detector resolution: 8.1241 pixels mm-1	θmax = 71.2°, θmin = 5.5°
ω scans	h = −8→12
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2006)	k = −7→11
Tmin = 0.477, Tmax = 1.000	l = −28→29
5771 measured reflections

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0536P)2 + 1.4166P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.001
2373 reflections	Δρmax = 0.29 e Å−3
184 parameters	Δρmin = −0.41 e Å−3
0 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: 0.00110 (16)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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	0.45913 (4)	0.21136 (4)	0.376497 (16)	0.01994 (17)
O1	0.59274 (13)	0.21818 (13)	0.37730 (5)	0.0254 (3)
O2	0.40093 (12)	0.07918 (13)	0.38690 (5)	0.0263 (3)
N3	0.40614 (15)	0.31297 (15)	0.42568 (6)	0.0221 (3)
H3N	0.340 (2)	0.283 (2)	0.4404 (9)	0.026*
C1	0.42548 (17)	0.45781 (18)	0.42714 (7)	0.0217 (4)
C2	0.34037 (17)	0.53944 (18)	0.45771 (7)	0.0214 (4)
N1	0.34155 (15)	0.67589 (16)	0.45622 (6)	0.0258 (4)
C3	0.43419 (19)	0.7358 (2)	0.42669 (8)	0.0299 (4)
H3	0.4377	0.8347	0.4239	0.036*
C4	0.52204 (19)	0.6575 (2)	0.40095 (9)	0.0321 (5)
H4	0.5885	0.7035	0.3828	0.039*
N2	0.51757 (14)	0.51529 (17)	0.40040 (7)	0.0272 (4)
O3	0.25850 (12)	0.46696 (12)	0.48767 (5)	0.0255 (3)
C5	0.1764 (2)	0.5454 (2)	0.52249 (8)	0.0326 (5)
H51	0.1171 (12)	0.5941 (15)	0.5008 (3)	0.049*
H52	0.2235 (7)	0.6108 (14)	0.5432 (5)	0.049*
H53	0.1343 (12)	0.4832 (9)	0.5465 (5)	0.049*
C6	0.40661 (16)	0.27630 (17)	0.31414 (7)	0.0209 (4)
C7	0.47006 (16)	0.3858 (2)	0.28819 (8)	0.0242 (4)
H7	0.5409	0.4267	0.3049	0.029*
C8	0.42941 (17)	0.43368 (19)	0.23848 (7)	0.0252 (4)
H8	0.4723	0.5083	0.2212	0.030*
C9	0.32573 (16)	0.37426 (18)	0.21290 (7)	0.0230 (4)
C10	0.26457 (17)	0.2631 (2)	0.23915 (7)	0.0262 (4)
H10	0.1953	0.2201	0.2220	0.031*
C11	0.30361 (17)	0.21565 (18)	0.28935 (8)	0.0250 (4)
H11	0.2603	0.1418	0.3069	0.030*
N4	0.28793 (16)	0.42195 (19)	0.16322 (6)	0.0282 (4)
H41	0.321 (2)	0.501 (3)	0.1502 (10)	0.034*
H42	0.219 (2)	0.387 (2)	0.1469 (10)	0.034*

	U11	U22	U33	U12	U13	U23
S	0.0234 (3)	0.0165 (2)	0.0200 (2)	0.00331 (15)	0.00297 (15)	0.00145 (15)
O1	0.0264 (7)	0.0259 (7)	0.0240 (7)	0.0062 (5)	0.0027 (5)	0.0034 (5)
O2	0.0363 (8)	0.0165 (6)	0.0262 (6)	0.0009 (5)	0.0048 (6)	0.0012 (5)
N3	0.0267 (8)	0.0169 (7)	0.0225 (7)	−0.0006 (6)	0.0063 (6)	−0.0002 (6)
C1	0.0259 (9)	0.0183 (8)	0.0209 (8)	−0.0016 (7)	−0.0015 (7)	0.0012 (7)
C2	0.0265 (9)	0.0189 (8)	0.0189 (8)	−0.0013 (7)	−0.0027 (7)	0.0007 (7)
N1	0.0320 (8)	0.0175 (7)	0.0278 (8)	−0.0020 (6)	−0.0023 (6)	−0.0015 (6)
C3	0.0345 (10)	0.0197 (9)	0.0353 (10)	−0.0051 (8)	−0.0028 (8)	−0.0001 (8)
C4	0.0319 (10)	0.0261 (10)	0.0385 (11)	−0.0091 (8)	0.0046 (8)	0.0001 (9)
N2	0.0278 (8)	0.0221 (8)	0.0316 (9)	−0.0051 (6)	0.0046 (7)	−0.0007 (7)
O3	0.0325 (7)	0.0194 (6)	0.0244 (6)	0.0011 (5)	0.0081 (5)	−0.0001 (5)
C5	0.0431 (12)	0.0291 (10)	0.0255 (9)	0.0060 (9)	0.0122 (9)	−0.0003 (8)
C6	0.0233 (9)	0.0178 (8)	0.0216 (9)	0.0022 (6)	0.0021 (7)	0.0015 (7)
C7	0.0220 (9)	0.0251 (9)	0.0255 (9)	−0.0018 (7)	−0.0018 (7)	0.0021 (8)
C8	0.0249 (9)	0.0249 (9)	0.0258 (9)	−0.0021 (7)	0.0008 (7)	0.0048 (8)
C9	0.0241 (9)	0.0228 (9)	0.0222 (8)	0.0029 (7)	0.0010 (7)	−0.0001 (7)
C10	0.0255 (9)	0.0246 (9)	0.0285 (9)	−0.0037 (8)	−0.0027 (8)	−0.0002 (8)
C11	0.0263 (9)	0.0205 (9)	0.0282 (9)	−0.0013 (7)	0.0019 (7)	0.0027 (7)
N4	0.0276 (8)	0.0325 (9)	0.0247 (8)	−0.0050 (7)	−0.0044 (7)	0.0057 (7)

S—O2	1.4338 (13)	C5—H51	0.9522
S—O1	1.4392 (14)	C5—H52	0.9522
S—N3	1.6519 (15)	C5—H53	0.9522
S—C6	1.7466 (17)	C6—C11	1.391 (3)
N3—C1	1.401 (2)	C6—C7	1.403 (3)
N3—H3N	0.85 (2)	C7—C8	1.375 (3)
C1—N2	1.310 (2)	C7—H7	0.9500
C1—C2	1.418 (3)	C8—C9	1.401 (3)
C2—N1	1.306 (2)	C8—H8	0.9500
C2—O3	1.341 (2)	C9—N4	1.365 (2)
N1—C3	1.359 (3)	C9—C10	1.407 (3)
C3—C4	1.361 (3)	C10—C11	1.379 (3)
C3—H3	0.9500	C10—H10	0.9500
C4—N2	1.361 (3)	C11—H11	0.9500
C4—H4	0.9500	N4—H41	0.90 (3)
O3—C5	1.440 (2)	N4—H42	0.91 (3)
O2—S—O1	118.28 (8)	H51—C5—H52	109.5
O2—S—N3	103.76 (8)	O3—C5—H53	109.5
O1—S—N3	107.94 (8)	H51—C5—H53	109.5
O2—S—C6	109.19 (8)	H52—C5—H53	109.5
O1—S—C6	108.60 (8)	C11—C6—C7	120.01 (16)
N3—S—C6	108.68 (8)	C11—C6—S	119.54 (13)
C1—N3—S	123.30 (13)	C7—C6—S	120.41 (14)
C1—N3—H3N	116.6 (15)	C8—C7—C6	119.81 (17)
S—N3—H3N	113.7 (15)	C8—C7—H7	120.1
N2—C1—N3	120.97 (16)	C6—C7—H7	120.1
N2—C1—C2	121.51 (16)	C7—C8—C9	121.07 (17)
N3—C1—C2	117.51 (16)	C7—C8—H8	119.5
N1—C2—O3	122.59 (16)	C9—C8—H8	119.5
N1—C2—C1	121.94 (17)	N4—C9—C8	120.18 (17)
O3—C2—C1	115.46 (15)	N4—C9—C10	121.54 (17)
C2—N1—C3	116.31 (17)	C8—C9—C10	118.27 (16)
N1—C3—C4	121.68 (18)	C11—C10—C9	121.07 (17)
N1—C3—H3	119.2	C11—C10—H10	119.5
C4—C3—H3	119.2	C9—C10—H10	119.5
N2—C4—C3	121.98 (18)	C10—C11—C6	119.76 (17)
N2—C4—H4	119.0	C10—C11—H11	120.1
C3—C4—H4	119.0	C6—C11—H11	120.1
C1—N2—C4	116.19 (17)	C9—N4—H41	118.9 (15)
C2—O3—C5	117.34 (14)	C9—N4—H42	121.1 (15)
O3—C5—H51	109.5	H41—N4—H42	118 (2)
O3—C5—H52	109.5
O2—S—N3—C1	−170.84 (15)	C1—C2—O3—C5	175.49 (16)
O1—S—N3—C1	62.86 (16)	O2—S—C6—C11	13.30 (17)
C6—S—N3—C1	−54.74 (17)	O1—S—C6—C11	143.57 (14)
S—N3—C1—N2	−22.2 (2)	N3—S—C6—C11	−99.25 (15)
S—N3—C1—C2	156.57 (13)	O2—S—C6—C7	−164.57 (14)
N2—C1—C2—N1	7.2 (3)	O1—S—C6—C7	−34.30 (17)
N3—C1—C2—N1	−171.57 (16)	N3—S—C6—C7	82.88 (16)
N2—C1—C2—O3	−173.32 (16)	C11—C6—C7—C8	0.6 (3)
N3—C1—C2—O3	7.9 (2)	S—C6—C7—C8	178.47 (14)
O3—C2—N1—C3	176.25 (16)	C6—C7—C8—C9	−0.5 (3)
C1—C2—N1—C3	−4.4 (3)	C7—C8—C9—N4	−179.05 (17)
C2—N1—C3—C4	−1.1 (3)	C7—C8—C9—C10	−0.5 (3)
N1—C3—C4—N2	4.3 (3)	N4—C9—C10—C11	179.95 (17)
N3—C1—N2—C4	174.85 (17)	C8—C9—C10—C11	1.5 (3)
C2—C1—N2—C4	−3.9 (3)	C9—C10—C11—C6	−1.3 (3)
C3—C4—N2—C1	−1.5 (3)	C7—C6—C11—C10	0.3 (3)
N1—C2—O3—C5	−5.1 (2)	S—C6—C11—C10	−177.59 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N1i	0.85 (2)	2.24 (2)	3.063 (2)	164 (2)
N4—H42···O1ii	0.91 (3)	2.19 (3)	3.033 (2)	154 (2)
N4—H41···O1iii	0.90 (3)	2.37 (3)	3.266 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N1i	0.85 (2)	2.24 (2)	3.063 (2)	164 (2)
N4—H42⋯O1ii	0.91 (3)	2.19 (3)	3.033 (2)	154 (2)
N4—H41⋯O1iii	0.90 (3)	2.37 (3)	3.266 (2)	176 (2)

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