4-[(4-Meth­oxy­benzyl­idene)amino]­benzene­sulfonamide

Idemudia, O.G.; Sadimenko, A.P.; Afolayan, A.J.; Hosten, E.C.

doi:10.1107/S1600536812018818

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1599

doi:10.1107/S1600536812018818

Open

access

4-[(4-Methoxybenzylidene)amino]benzenesulfonamide

Omoruyi G. Idemudia,^a ^* Alexander P. Sadimenko,^a Anthony J. Afolayan ^a and Eric C. Hosten ^b

^aDepartment of Chemistry, University of Fort Hare, Private Bag X1314, Alice 5700, South Africa, and ^bDepartment of Chemistry, Nelson Mandela Metropolitan University, PO Box 77000, Port Elizabeth 6031, South Africa
^*Correspondence e-mail: idemudiaog@yahoo.com

(Received 18 April 2012; accepted 26 April 2012; online 2 May 2012)

The title Schiff base compound, C₁₄H₁₄N₂O₃S, 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 molecules into a layer parallel to (011). Intra- and interlayer C—H⋯O interactions and π–π interactions [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_r = 290.33
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.095
S = 1.08
3383 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018818/hy2541sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812018818/hy2541Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812018818/hy2541Isup4.cml

checkCIF report

Comment top

Biological applications of sulfa compounds either alone or as metal complexes are well known (Gupta et al., 2003; Nagpal & Singh, 2004). Their chelating powers towards metal ions tend to increase on forming a Schiff base by way of reaction with a carbonyl (Khalil et al., 2009; Sharaby, 2007; Wu et al., 2004). Herein, we report a new sulfanilamide Schiff base (Fig. 1), as part of our look at developing better chelating ligands from biologically active amine compounds.

The least-squares planes through the phenyl rings of the benzenesulfonamide and methoxybenzaldehyde groups have a dihedral angle of 24.16 (7)°. In the crystal, the molecules are stacked along the c axis and linked by N—H···O and N—H···N hydrogen bonds (Table 1 and Fig. 2) into a layer parallel to (0 1 1) (Fig. 3). The least-squares planes through adjacent two methoxybenzaldehyde phenyl rings (C11–C16) are almost parallel with a dihedral angle of 3.97° and a centroid-to-centroid distance of 3.8900 (9) Å. The centroid-to-centroid distance between adjacent two benzenesulfonamide phenyl rings (C21–C26) is 3.9355 (8) Å. C22—H22···π interaction occurs with the adjacent C21–C26 ring (H···Cg distance = 2.81 Å). Intra- and interlayer C—H···O interactions are also observed.

Related literature top

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 top

A mixture of (4-aminobenzenesulfonamide)sulfadiazine and 4-methoxybenzaldehyde (anisaldehyde) (molar ratio 1:1) in methanol was refluxed for 15 h. The resultant pale yellow precipitate was isolated by filtration and recrystalized from methanol. Yield 68% and melting point 199–201°C. Single crystals suitable for X-ray analysis were obtained from methanol by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Hydrogen bonds in the title compound. [Symmetry codes: (i) x, -y+3/2, z-1/2; (ii) -x+1, -y+2, -z+1; (iii) -x+1, y-1/2, -z+3/2; (iv) x-1, y, z-1.]
	Fig. 3. Crystal packing of the title compound viewed along [0 1 0].

4-[(4-Methoxybenzylidene)amino]benzenesulfonamide top

Crystal data top

C₁₄H₁₄N₂O₃S	F(000) = 608
M_r = 290.33	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	3383 independent reflections
Radiation source: sealed tube	2821 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.3°, θ_min = 2.2°
ϕ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −14→14
T_min = 0.90, T_max = 0.97	l = −10→8
10501 measured reflections

Refinement top

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(F_o²) + (0.0391P)² + 0.7392P] where P = (F_o² + 2F_c²)/3
3383 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₃S	V = 1376.92 (8) Å³
M_r = 290.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.3315 (5) Å	µ = 0.24 mm⁻¹
b = 11.1597 (3) Å	T = 200 K
c = 7.6876 (3) Å	0.60 × 0.33 × 0.12 mm
β = 100.661 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3383 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2821 reflections with I > 2σ(I)
T_min = 0.90, T_max = 0.97	R_int = 0.017
10501 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.08	Δρ_max = 0.41 e Å⁻³
3383 reflections	Δρ_min = −0.39 e Å⁻³
182 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.98	2.59	3.415 (2)	141

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+2, −z+1; (iii) −x+1, y−1/2, −z+3/2; (iv) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₃S
M_r	290.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	16.3315 (5), 11.1597 (3), 7.6876 (3)
β (°)	100.661 (1)
V (Å³)	1376.92 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.60 × 0.33 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.90, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	10501, 3383, 2821
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.095, 1.08
No. of reflections	3383
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Acknowledgements

The authors thank the Department of Chemistry and Govan Mbeki Research and Development Centre (GMRDC), University of Fort Hare, for their support.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gupta, M. K., Singh, H. L., Varshney, S. & Varshney, A. K. (2003). Bioinorg. Chem. Appl. 1, 309–320. CrossRef CAS Google Scholar
Khalil, R. A., Jalil, A. H. & Abd-Alrazzak, A. Y. (2009). Iran. Chem. Soc. 6, 345–352. CrossRef CAS Google Scholar
Nagpal, P. & Singh, R. V. (2004). Appl. Organomet. Chem. 18, 221–226. Web of Science CrossRef CAS Google Scholar
Sharaby, C. M. (2007). Spectrochim. Acta Part A, 66, 1271–1278. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, C. Y., Chen, L. H., Hwang, W. S., Chen, H. S., Chen, H. S. & Hung, C. H. (2004). J. Organomet. Chem. 689, 2192–2200. Web of Science CSD CrossRef CAS Google Scholar