(E)-4-[(5-Methyl-2-fur-yl)methyl-ene-amino]benzene-sulfonic acid.

The title compound, C(12)H(11)NO(4)S, is a Schiff base derived from the condensation reaction of equimolar quanti-ties of sulfamide and furfural. The mol-ecule has a trans configuration with respect to the imine C=N double bond. The N atom is involved in an inter-molecular O-H-N hydrogen bond.

Related literature

For related literature, see: Abd El Rehim et al. (2001 ▶); Hariharan & Urbach (1969 ▶); Koning & Canti­lena (1994 ▶); Tarafder et al. (2002 ▶).

Experimental

Crystal data

C12H11NO4S

M = 265.28

Monoclinic,

a = 13.9761 (11) Å

b = 11.9820 (15) Å

c = 7.3266 (10) Å

β = 95.8010 (10)°

V = 1220.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 (2) K

0.23 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.940, T max = 0.961

6042 measured reflections

2156 independent reflections

1581 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.128

S = 1.05

2156 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026275/bx2168sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026275/bx2168Isup2.hkl

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

C12H11NO4S	F000 = 552
Mr = 265.28	Dx = 1.444 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 13.9761 (11) Å	Cell parameters from 1942 reflections
b = 11.9820 (15) Å	θ = 2.9–26.0º
c = 7.3266 (10) Å	µ = 0.27 mm−1
β = 95.8010 (10)º	T = 298 (2) K
V = 1220.6 (2) Å3	Flake, brown
Z = 4	0.23 × 0.20 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	2156 independent reflections
Radiation source: fine-focus sealed tube	1581 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −14→16
Tmin = 0.940, Tmax = 0.961	k = −14→9
6042 measured reflections	l = −8→8

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0528P)2 + 1.108P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2156 reflections	Δρmax = 0.44 e Å−3
165 parameters	Δρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.70555 (16)	0.62949 (19)	0.4602 (3)	0.0366 (6)
O1	0.22901 (17)	0.5894 (2)	0.3632 (3)	0.0621 (7)
H1	0.2437	0.5289	0.4103	0.093*
O2	0.27564 (15)	0.5149 (2)	0.0717 (3)	0.0596 (7)
O3	0.26181 (15)	0.71745 (19)	0.1207 (3)	0.0581 (7)
O4	0.90263 (14)	0.64516 (16)	0.5898 (3)	0.0409 (5)
S1	0.28904 (5)	0.60909 (6)	0.18999 (10)	0.0392 (2)
C1	0.41271 (19)	0.6154 (2)	0.2690 (3)	0.0323 (6)
C2	0.4477 (2)	0.7072 (2)	0.3712 (4)	0.0379 (7)
H2	0.4062	0.7648	0.3957	0.045*
C3	0.5434 (2)	0.7130 (2)	0.4362 (4)	0.0375 (7)
H3	0.5661	0.7736	0.5073	0.045*
C4	0.60639 (19)	0.6285 (2)	0.3960 (3)	0.0321 (6)
C5	0.5707 (2)	0.5367 (2)	0.2959 (4)	0.0389 (7)
H5	0.6120	0.4790	0.2711	0.047*
C6	0.4741 (2)	0.5301 (2)	0.2326 (4)	0.0389 (7)
H6	0.4508	0.4683	0.1656	0.047*
C7	0.7498 (2)	0.7230 (2)	0.4686 (4)	0.0381 (7)
H7	0.7155	0.7862	0.4270	0.046*
C8	0.8478 (2)	0.7368 (2)	0.5371 (4)	0.0383 (7)
C9	0.9011 (2)	0.8304 (3)	0.5670 (4)	0.0472 (8)
H9	0.8809	0.9033	0.5424	0.057*
C10	0.9932 (2)	0.7963 (3)	0.6424 (4)	0.0476 (8)
H10	1.0452	0.8426	0.6781	0.057*
C11	0.9918 (2)	0.6844 (3)	0.6528 (4)	0.0425 (7)
C12	1.0641 (2)	0.5993 (3)	0.7175 (5)	0.0583 (9)
H12A	1.1232	0.6355	0.7616	0.087*
H12B	1.0750	0.5505	0.6179	0.087*
H12C	1.0409	0.5568	0.8149	0.087*

	U11	U22	U33	U12	U13	U23
N1	0.0333 (13)	0.0386 (14)	0.0368 (13)	−0.0029 (10)	−0.0015 (10)	0.0024 (10)
O1	0.0497 (14)	0.0632 (16)	0.0740 (17)	−0.0002 (12)	0.0089 (13)	0.0110 (13)
O2	0.0425 (13)	0.0767 (17)	0.0577 (14)	−0.0077 (11)	−0.0044 (11)	−0.0265 (12)
O3	0.0416 (12)	0.0638 (15)	0.0671 (16)	0.0026 (11)	−0.0034 (11)	0.0290 (12)
O4	0.0364 (11)	0.0362 (11)	0.0490 (12)	−0.0018 (8)	−0.0017 (9)	0.0015 (9)
S1	0.0308 (4)	0.0463 (5)	0.0393 (4)	−0.0031 (3)	−0.0026 (3)	0.0019 (3)
C1	0.0306 (14)	0.0370 (15)	0.0288 (14)	−0.0035 (12)	0.0009 (11)	0.0023 (12)
C2	0.0352 (15)	0.0367 (16)	0.0418 (16)	0.0035 (12)	0.0041 (13)	−0.0049 (13)
C3	0.0384 (16)	0.0369 (16)	0.0362 (15)	−0.0046 (12)	−0.0003 (13)	−0.0077 (12)
C4	0.0321 (14)	0.0342 (15)	0.0293 (14)	−0.0023 (11)	−0.0008 (11)	0.0039 (11)
C5	0.0334 (15)	0.0353 (16)	0.0476 (17)	0.0026 (12)	0.0017 (13)	−0.0045 (13)
C6	0.0380 (16)	0.0345 (16)	0.0433 (17)	−0.0046 (12)	−0.0003 (13)	−0.0075 (13)
C7	0.0354 (15)	0.0371 (16)	0.0406 (16)	−0.0012 (13)	−0.0013 (13)	0.0033 (13)
C8	0.0375 (16)	0.0371 (16)	0.0394 (16)	−0.0013 (12)	−0.0012 (13)	0.0025 (13)
C9	0.0441 (18)	0.0349 (17)	0.060 (2)	−0.0035 (14)	−0.0054 (15)	0.0040 (15)
C10	0.0363 (17)	0.0469 (19)	0.057 (2)	−0.0104 (14)	−0.0080 (15)	−0.0009 (15)
C11	0.0327 (16)	0.0493 (19)	0.0443 (17)	−0.0026 (13)	−0.0020 (13)	0.0005 (14)
C12	0.0444 (19)	0.057 (2)	0.072 (2)	0.0109 (16)	−0.0017 (17)	0.0028 (18)

N1—C7	1.278 (3)	C4—C5	1.386 (4)
N1—C4	1.418 (3)	C5—C6	1.385 (4)
O1—S1	1.608 (2)	C5—H5	0.9300
O1—H1	0.8200	C6—H6	0.9300
O2—S1	1.424 (2)	C7—C8	1.420 (4)
O3—S1	1.431 (2)	C7—H7	0.9300
O4—C11	1.368 (3)	C8—C9	1.352 (4)
O4—C8	1.372 (3)	C9—C10	1.409 (4)
S1—C1	1.768 (3)	C9—H9	0.9300
C1—C6	1.377 (4)	C10—C11	1.344 (4)
C1—C2	1.392 (4)	C10—H10	0.9300
C2—C3	1.375 (4)	C11—C12	1.478 (4)
C2—H2	0.9300	C12—H12A	0.9600
C3—C4	1.394 (4)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
C7—N1—C4	118.4 (2)	C1—C6—C5	119.9 (3)
S1—O1—H1	109.5	C1—C6—H6	120.0
C11—O4—C8	106.5 (2)	C5—C6—H6	120.0
O2—S1—O3	119.29 (15)	N1—C7—C8	124.3 (3)
O2—S1—O1	108.48 (14)	N1—C7—H7	117.8
O3—S1—O1	105.76 (13)	C8—C7—H7	117.8
O2—S1—C1	107.28 (13)	C9—C8—O4	109.6 (2)
O3—S1—C1	107.07 (13)	C9—C8—C7	130.5 (3)
O1—S1—C1	108.60 (13)	O4—C8—C7	119.9 (2)
C6—C1—C2	119.9 (3)	C8—C9—C10	106.9 (3)
C6—C1—S1	120.9 (2)	C8—C9—H9	126.6
C2—C1—S1	119.2 (2)	C10—C9—H9	126.6
C3—C2—C1	120.2 (3)	C11—C10—C9	107.1 (3)
C3—C2—H2	119.9	C11—C10—H10	126.5
C1—C2—H2	119.9	C9—C10—H10	126.5
C2—C3—C4	120.2 (3)	C10—C11—O4	110.0 (3)
C2—C3—H3	119.9	C10—C11—C12	133.9 (3)
C4—C3—H3	119.9	O4—C11—C12	116.1 (3)
C5—C4—C3	119.2 (3)	C11—C12—H12A	109.5
C5—C4—N1	118.0 (2)	C11—C12—H12B	109.5
C3—C4—N1	122.8 (2)	H12A—C12—H12B	109.5
C6—C5—C4	120.6 (3)	C11—C12—H12C	109.5
C6—C5—H5	119.7	H12A—C12—H12C	109.5
C4—C5—H5	119.7	H12B—C12—H12C	109.5
O2—S1—C1—C6	−8.0 (3)	C2—C1—C6—C5	−0.8 (4)
O3—S1—C1—C6	−137.2 (2)	S1—C1—C6—C5	−179.9 (2)
O1—S1—C1—C6	109.0 (2)	C4—C5—C6—C1	0.0 (4)
O2—S1—C1—C2	172.8 (2)	C4—N1—C7—C8	177.3 (3)
O3—S1—C1—C2	43.7 (3)	C11—O4—C8—C9	−0.2 (3)
O1—S1—C1—C2	−70.1 (2)	C11—O4—C8—C7	−178.6 (3)
C6—C1—C2—C3	−0.1 (4)	N1—C7—C8—C9	−174.2 (3)
S1—C1—C2—C3	179.1 (2)	N1—C7—C8—O4	3.8 (4)
C1—C2—C3—C4	1.7 (4)	O4—C8—C9—C10	−0.3 (4)
C2—C3—C4—C5	−2.4 (4)	C7—C8—C9—C10	177.9 (3)
C2—C3—C4—N1	−179.6 (2)	C8—C9—C10—C11	0.6 (4)
C7—N1—C4—C5	146.0 (3)	C9—C10—C11—O4	−0.8 (4)
C7—N1—C4—C3	−36.9 (4)	C9—C10—C11—C12	179.8 (4)
C3—C4—C5—C6	1.6 (4)	C8—O4—C11—C10	0.7 (3)
N1—C4—C5—C6	178.8 (2)	C8—O4—C11—C12	−179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	2.21	3.025 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.21	3.025 (3)	176

Symmetry code: (i) .