4-[(4-Meth-oxy-benzyl-idene)amino]-benzene-sulfonamide.

The title Schiff base compound, C(14)H(14)N(2)O(3)S, is non-planar, with a dihedral angle of 24.16 (7)° between the benzene rings. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds link the mol-ecules into a layer parallel to (011). Intra- and inter-layer C-H⋯O inter-actions and π-π inter-actions [centroid-centroid distances = 3.8900 (9) and 3.9355 (8) Å] are also present.

Related literature

For general background to the applications of sulfanilamide Schiff bases, see: Gupta et al. (2003 ▶); Khalil et al. (2009 ▶); Nagpal & Singh (2004 ▶); Sharaby (2007 ▶); Wu et al. (2004 ▶).

Experimental

Crystal data

C14H14N2O3S

M = 290.33

Monoclinic,

a = 16.3315 (5) Å

b = 11.1597 (3) Å

c = 7.6876 (3) Å

β = 100.661 (1)°

V = 1376.92 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 200 K

0.60 × 0.33 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.90, T max = 0.97

10501 measured reflections

3383 independent reflections

2821 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.095

S = 1.08

3383 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.39 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 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018818/hy2541sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018818/hy2541Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018818/hy2541Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812018818/hy2541Isup4.cml

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

C14H14N2O3S	F(000) = 608
Mr = 290.33	Dx = 1.401 Mg m−3
Monoclinic, P21/c	Melting point: 473.15 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.3315 (5) Å	Cell parameters from 118 reflections
b = 11.1597 (3) Å	θ = 3.1–29.3°
c = 7.6876 (3) Å	µ = 0.24 mm−1
β = 100.661 (1)°	T = 200 K
V = 1376.92 (8) Å3	Platelet, yellow
Z = 4	0.60 × 0.33 × 0.12 mm

Bruker APEXII CCD diffractometer	3383 independent reflections
Radiation source: sealed tube	2821 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.3333 pixels mm-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −14→14
Tmin = 0.90, Tmax = 0.97	l = −10→8
10501 measured 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0391P)2 + 0.7392P] where P = (Fo2 + 2Fc2)/3
3383 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.39 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
S1	0.663198 (19)	0.87003 (3)	0.83688 (5)	0.02211 (10)
O1	−0.04751 (7)	0.67929 (13)	0.0325 (2)	0.0479 (4)
O2	0.68589 (6)	0.74895 (9)	0.88958 (16)	0.0306 (3)
O3	0.66935 (7)	0.96150 (10)	0.96956 (16)	0.0333 (3)
N1	0.31032 (7)	0.85378 (10)	0.45630 (17)	0.0231 (2)
N2	0.72148 (7)	0.90797 (11)	0.69963 (17)	0.0248 (3)
H2A	0.719	0.8559	0.6172	0.03*
H2B	0.7141	0.9792	0.6628	0.03*
C1	0.27140 (8)	0.75396 (13)	0.4333 (2)	0.0250 (3)
H1	0.2986	0.6843	0.4867	0.03*
C2	−0.10221 (11)	0.7766 (2)	−0.0293 (3)	0.0553 (6)
H2C	−0.0756	0.8292	−0.1044	0.083*
H2D	−0.1142	0.8221	0.0721	0.083*
H2E	−0.1543	0.7451	−0.0979	0.083*
C11	0.18743 (8)	0.74102 (13)	0.3295 (2)	0.0257 (3)
C12	0.15750 (9)	0.62521 (14)	0.2867 (2)	0.0319 (3)
H12	0.1914	0.558	0.3275	0.038*
C13	0.07929 (10)	0.60763 (15)	0.1859 (2)	0.0365 (4)
H13	0.0598	0.5287	0.1558	0.044*
C14	0.02902 (9)	0.70602 (16)	0.1285 (2)	0.0335 (4)
C15	0.05726 (9)	0.82138 (15)	0.1709 (2)	0.0344 (4)
H15	0.0228	0.8884	0.1321	0.041*
C16	0.13644 (9)	0.83808 (14)	0.2707 (2)	0.0310 (3)
H16	0.1561	0.9171	0.2993	0.037*
C21	0.39382 (8)	0.85383 (12)	0.55004 (19)	0.0206 (3)
C22	0.44881 (8)	0.75989 (12)	0.5357 (2)	0.0225 (3)
H22	0.43	0.6923	0.4643	0.027*
C23	0.53057 (8)	0.76496 (12)	0.6253 (2)	0.0223 (3)
H23	0.5675	0.7002	0.6176	0.027*
C24	0.55836 (8)	0.86504 (11)	0.72618 (19)	0.0199 (3)
C25	0.50485 (9)	0.96019 (12)	0.7391 (2)	0.0244 (3)
H25	0.5244	1.0287	0.8077	0.029*
C26	0.42248 (8)	0.95441 (12)	0.6508 (2)	0.0246 (3)
H26	0.3857	1.0192	0.6592	0.03*

	U11	U22	U33	U12	U13	U23
S1	0.01897 (16)	0.02111 (17)	0.02420 (19)	−0.00156 (11)	−0.00138 (12)	0.00123 (13)
O1	0.0217 (5)	0.0634 (9)	0.0533 (9)	−0.0056 (5)	−0.0072 (5)	−0.0087 (7)
O2	0.0250 (5)	0.0263 (5)	0.0377 (7)	0.0009 (4)	−0.0015 (4)	0.0113 (5)
O3	0.0301 (5)	0.0363 (6)	0.0304 (6)	−0.0027 (4)	−0.0023 (4)	−0.0097 (5)
N1	0.0194 (5)	0.0234 (6)	0.0252 (6)	0.0002 (4)	0.0007 (4)	0.0015 (5)
N2	0.0224 (5)	0.0197 (5)	0.0314 (7)	−0.0027 (4)	0.0029 (5)	0.0025 (5)
C1	0.0216 (6)	0.0235 (6)	0.0284 (8)	−0.0005 (5)	0.0010 (5)	0.0029 (5)
C2	0.0239 (8)	0.0838 (16)	0.0532 (13)	0.0076 (9)	−0.0063 (8)	−0.0003 (12)
C11	0.0198 (6)	0.0279 (7)	0.0282 (8)	−0.0023 (5)	0.0013 (5)	0.0010 (6)
C12	0.0263 (7)	0.0282 (7)	0.0391 (9)	−0.0030 (6)	0.0005 (6)	0.0016 (7)
C13	0.0282 (7)	0.0346 (8)	0.0440 (10)	−0.0092 (6)	−0.0002 (7)	−0.0053 (7)
C14	0.0188 (6)	0.0477 (9)	0.0323 (9)	−0.0032 (6)	0.0005 (6)	−0.0036 (7)
C15	0.0226 (7)	0.0388 (9)	0.0398 (10)	0.0041 (6)	0.0008 (6)	0.0013 (7)
C16	0.0234 (7)	0.0292 (7)	0.0388 (9)	−0.0004 (6)	0.0014 (6)	0.0009 (7)
C21	0.0191 (6)	0.0199 (6)	0.0217 (7)	−0.0003 (5)	0.0013 (5)	0.0036 (5)
C22	0.0218 (6)	0.0191 (6)	0.0259 (7)	−0.0024 (5)	0.0026 (5)	−0.0029 (5)
C23	0.0202 (6)	0.0193 (6)	0.0274 (7)	0.0002 (5)	0.0045 (5)	−0.0008 (5)
C24	0.0183 (5)	0.0192 (6)	0.0213 (7)	−0.0016 (4)	0.0014 (5)	0.0022 (5)
C25	0.0254 (6)	0.0176 (6)	0.0281 (7)	−0.0009 (5)	0.0000 (5)	−0.0023 (5)
C26	0.0238 (6)	0.0190 (6)	0.0297 (8)	0.0026 (5)	0.0015 (5)	−0.0011 (5)

S1—O3	1.4333 (11)	C12—H12	0.95
S1—O2	1.4393 (10)	C13—C14	1.393 (2)
S1—N2	1.6032 (13)	C13—H13	0.95
S1—C24	1.7663 (13)	C14—C15	1.386 (2)
O1—C14	1.3617 (17)	C15—C16	1.389 (2)
O1—C2	1.430 (2)	C15—H15	0.95
N1—C1	1.2786 (18)	C16—H16	0.95
N1—C21	1.4196 (16)	C21—C26	1.3945 (19)
N2—H2A	0.8551	C21—C22	1.3978 (18)
N2—H2B	0.8452	C22—C23	1.3856 (18)
C1—C11	1.4607 (18)	C22—H22	0.95
C1—H1	0.95	C23—C24	1.3875 (19)
C2—H2C	0.98	C23—H23	0.95
C2—H2D	0.98	C24—C25	1.3904 (18)
C2—H2E	0.98	C25—C26	1.3916 (19)
C11—C16	1.390 (2)	C25—H25	0.95
C11—C12	1.399 (2)	C26—H26	0.95
C12—C13	1.380 (2)
O3—S1—O2	119.20 (7)	C14—C13—H13	120.1
O3—S1—N2	107.96 (7)	O1—C14—C15	124.27 (15)
O2—S1—N2	106.25 (7)	O1—C14—C13	115.28 (15)
O3—S1—C24	107.42 (6)	C15—C14—C13	120.44 (14)
O2—S1—C24	106.39 (6)	C14—C15—C16	119.35 (15)
N2—S1—C24	109.38 (6)	C14—C15—H15	120.3
C14—O1—C2	117.90 (15)	C16—C15—H15	120.3
C1—N1—C21	118.48 (12)	C15—C16—C11	121.04 (15)
S1—N2—H2A	110.9	C15—C16—H16	119.5
S1—N2—H2B	113.8	C11—C16—H16	119.5
H2A—N2—H2B	114.0	C26—C21—C22	119.53 (12)
N1—C1—C11	123.66 (13)	C26—C21—N1	118.32 (12)
N1—C1—H1	118.2	C22—C21—N1	122.04 (12)
C11—C1—H1	118.2	C23—C22—C21	120.29 (12)
O1—C2—H2C	109.5	C23—C22—H22	119.9
O1—C2—H2D	109.5	C21—C22—H22	119.9
H2C—C2—H2D	109.5	C22—C23—C24	119.74 (12)
O1—C2—H2E	109.5	C22—C23—H23	120.1
H2C—C2—H2E	109.5	C24—C23—H23	120.1
H2D—C2—H2E	109.5	C23—C24—C25	120.64 (12)
C16—C11—C12	118.77 (13)	C23—C24—S1	118.85 (10)
C16—C11—C1	123.09 (13)	C25—C24—S1	120.51 (10)
C12—C11—C1	118.13 (13)	C24—C25—C26	119.57 (13)
C13—C12—C11	120.67 (14)	C24—C25—H25	120.2
C13—C12—H12	119.7	C26—C25—H25	120.2
C11—C12—H12	119.7	C25—C26—C21	120.19 (12)
C12—C13—C14	119.73 (15)	C25—C26—H26	119.9
C12—C13—H13	120.1	C21—C26—H26	119.9
C21—N1—C1—C11	−175.87 (13)	C26—C21—C22—C23	1.9 (2)
N1—C1—C11—C16	−11.2 (2)	N1—C21—C22—C23	178.05 (13)
N1—C1—C11—C12	168.42 (16)	C21—C22—C23—C24	−1.5 (2)
C16—C11—C12—C13	0.9 (3)	C22—C23—C24—C25	0.3 (2)
C1—C11—C12—C13	−178.67 (16)	C22—C23—C24—S1	−179.27 (11)
C11—C12—C13—C14	−1.1 (3)	O3—S1—C24—C23	−163.03 (12)
C2—O1—C14—C15	0.3 (3)	O2—S1—C24—C23	−34.34 (13)
C2—O1—C14—C13	179.64 (17)	N2—S1—C24—C23	80.04 (12)
C12—C13—C14—O1	−178.90 (16)	O3—S1—C24—C25	17.41 (14)
C12—C13—C14—C15	0.4 (3)	O2—S1—C24—C25	146.11 (12)
O1—C14—C15—C16	179.57 (16)	N2—S1—C24—C25	−99.52 (13)
C13—C14—C15—C16	0.3 (3)	C23—C24—C25—C26	0.5 (2)
C14—C15—C16—C11	−0.4 (3)	S1—C24—C25—C26	180.00 (11)
C12—C11—C16—C15	−0.2 (2)	C24—C25—C26—C21	0.0 (2)
C1—C11—C16—C15	179.39 (15)	C22—C21—C26—C25	−1.2 (2)
C1—N1—C21—C26	−148.41 (14)	N1—C21—C26—C25	−177.44 (13)
C1—N1—C21—C22	35.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.09	2.9280 (17)	166
N2—H2B···N1ii	0.85	2.08	2.9233 (17)	173
C1—H1···O3iii	0.95	2.55	3.4466 (18)	157
C2—H2E···O2iv	0.98	2.59	3.415 (2)	141