N-[(E)-4-(Methyl-sulfon-yl)benzyl-idene]-3-nitro-aniline.

In the title compound, C(14)H(12)N(2)O(4)S, the dihedral angle between the two aromatic rings is 35.65 (12)°. The crystal packing is stabilized by weak C-H⋯O hydrogen bonds and aromatic π-π ring stacking inter-actions [minimum ring centroid separation = 3.697 (3) Å].

Related literature

For pharmacological applications of Schiff bases, see: Venugopal & Jayashree (2008 ▶); Villar et al. (2004 ▶); Wadher et al. (2009 ▶). For similar structures, see: Qian & Cui (2009 ▶); Qian & Liu (2010 ▶). For comparative bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12N2O4S

M = 304.32

Monoclinic,

a = 12.707 (7) Å

b = 8.669 (5) Å

c = 14.257 (8) Å

β = 114.140 (5)°

V = 1433.2 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.25 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.942, T max = 0.951

9119 measured reflections

2525 independent reflections

1937 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.02

2525 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031539/zs2133sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031539/zs2133Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031539/zs2133Isup3.cml

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

C14H12N2O4S	F(000) = 632
Mr = 304.32	Dx = 1.410 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3721 reflections
a = 12.707 (7) Å	θ = 2.8–26.0°
b = 8.669 (5) Å	µ = 0.24 mm−1
c = 14.257 (8) Å	T = 296 K
β = 114.140 (5)°	Block, yellow
V = 1433.2 (14) Å3	0.25 × 0.23 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	2525 independent reflections
Radiation source: fine-focus sealed tube	1937 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→15
Tmin = 0.942, Tmax = 0.951	k = −10→9
9119 measured reflections	l = −16→16

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0358P)2 + 0.9892P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2525 reflections	Δρmax = 0.28 e Å−3
192 parameters	Δρmin = −0.21 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: 0.0103 (10)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.01452 (18)	0.6909 (2)	0.10542 (17)	0.0405 (5)
C2	1.0352 (2)	0.5465 (3)	0.15075 (18)	0.0475 (6)
H2	1.1079	0.5208	0.2000	0.057*
C3	0.9452 (2)	0.4404 (3)	0.12122 (18)	0.0498 (6)
H3	0.9580	0.3433	0.1515	0.060*
C4	0.83654 (19)	0.4776 (3)	0.04718 (17)	0.0420 (5)
C5	0.8187 (2)	0.6221 (3)	0.00106 (19)	0.0507 (6)
H5	0.7467	0.6471	−0.0496	0.061*
C6	0.90665 (19)	0.7287 (3)	0.02969 (18)	0.0500 (6)
H6	0.8941	0.8253	−0.0013	0.060*
C7	0.7403 (2)	0.3652 (3)	0.01717 (18)	0.0479 (6)
H7	0.7518	0.2703	0.0503	0.058*
C8	0.5512 (2)	0.2885 (3)	−0.08472 (18)	0.0496 (6)
C9	0.5682 (2)	0.1309 (3)	−0.09320 (17)	0.0485 (6)
H9	0.6417	0.0912	−0.0765	0.058*
C10	0.4727 (2)	0.0354 (3)	−0.12720 (17)	0.0504 (6)
C11	0.3618 (2)	0.0891 (4)	−0.1524 (2)	0.0648 (8)
H11	0.2994	0.0217	−0.1736	0.078*
C12	0.3465 (2)	0.2452 (4)	−0.1451 (2)	0.0703 (8)
H12	0.2728	0.2841	−0.1621	0.084*
C13	0.4393 (2)	0.3445 (3)	−0.1129 (2)	0.0640 (7)
H13	0.4273	0.4499	−0.1099	0.077*
N1	0.64205 (17)	0.3974 (2)	−0.05349 (16)	0.0530 (5)
N2	0.4908 (2)	−0.1309 (3)	−0.13755 (16)	0.0634 (6)
O1	1.22903 (14)	0.7666 (2)	0.21956 (15)	0.0694 (6)
O2	1.13137 (15)	0.8930 (2)	0.05065 (14)	0.0609 (5)
C14	1.0752 (2)	0.9783 (3)	0.1990 (2)	0.0600 (7)
H14A	1.0613	0.9364	0.2552	0.090*
H14B	1.0048	1.0201	0.1486	0.090*
H14C	1.1320	1.0585	0.2238	0.090*
O4	0.5876 (2)	−0.1747 (2)	−0.12006 (19)	0.0886 (7)
O5	0.4073 (2)	−0.2168 (3)	−0.1646 (2)	0.1008 (8)
S1	1.12545 (5)	0.83166 (7)	0.14267 (5)	0.0477 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0409 (11)	0.0355 (12)	0.0461 (12)	0.0032 (10)	0.0189 (10)	−0.0023 (10)
C2	0.0451 (13)	0.0397 (13)	0.0495 (13)	0.0046 (11)	0.0109 (10)	0.0002 (11)
C3	0.0609 (15)	0.0332 (12)	0.0526 (14)	0.0031 (11)	0.0205 (12)	0.0031 (10)
C4	0.0447 (12)	0.0378 (13)	0.0455 (12)	−0.0008 (10)	0.0204 (10)	−0.0055 (10)
C5	0.0425 (13)	0.0461 (14)	0.0567 (14)	0.0027 (11)	0.0132 (11)	0.0048 (11)
C6	0.0482 (13)	0.0381 (13)	0.0581 (15)	0.0026 (11)	0.0161 (11)	0.0090 (11)
C7	0.0551 (14)	0.0400 (13)	0.0518 (14)	−0.0005 (11)	0.0250 (12)	−0.0037 (11)
C8	0.0471 (13)	0.0506 (15)	0.0488 (14)	−0.0002 (11)	0.0174 (11)	−0.0008 (11)
C9	0.0424 (12)	0.0519 (15)	0.0475 (13)	0.0001 (11)	0.0147 (10)	0.0013 (11)
C10	0.0514 (14)	0.0535 (15)	0.0433 (13)	−0.0007 (12)	0.0161 (11)	0.0014 (11)
C11	0.0479 (15)	0.081 (2)	0.0619 (17)	−0.0114 (14)	0.0186 (12)	−0.0038 (15)
C12	0.0443 (14)	0.084 (2)	0.0773 (19)	0.0097 (14)	0.0189 (13)	−0.0106 (17)
C13	0.0541 (15)	0.0622 (17)	0.0695 (17)	0.0086 (13)	0.0191 (13)	−0.0076 (14)
N1	0.0483 (12)	0.0473 (12)	0.0613 (13)	−0.0043 (10)	0.0202 (10)	−0.0040 (10)
N2	0.0696 (15)	0.0529 (14)	0.0540 (13)	−0.0085 (13)	0.0114 (11)	0.0022 (11)
O1	0.0432 (9)	0.0555 (11)	0.0905 (14)	0.0030 (8)	0.0081 (9)	0.0054 (10)
O2	0.0639 (11)	0.0529 (11)	0.0763 (12)	−0.0058 (9)	0.0392 (10)	0.0029 (9)
C14	0.0634 (16)	0.0438 (15)	0.0705 (17)	−0.0047 (12)	0.0249 (14)	−0.0131 (13)
O4	0.0781 (15)	0.0586 (13)	0.1134 (18)	0.0129 (11)	0.0232 (13)	0.0019 (12)
O5	0.0914 (16)	0.0647 (14)	0.1174 (19)	−0.0310 (13)	0.0134 (14)	−0.0079 (13)
S1	0.0405 (3)	0.0382 (3)	0.0612 (4)	0.0001 (3)	0.0177 (3)	−0.0009 (3)

C1—C2	1.385 (3)	C9—C10	1.383 (3)
C1—C6	1.393 (3)	C9—H9	0.9300
C1—S1	1.773 (2)	C10—C11	1.384 (4)
C2—C3	1.391 (3)	C10—N2	1.477 (3)
C2—H2	0.9300	C11—C12	1.377 (4)
C3—C4	1.391 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.378 (4)
C4—C5	1.390 (3)	C12—H12	0.9300
C4—C7	1.483 (3)	C13—H13	0.9300
C5—C6	1.377 (3)	N2—O4	1.212 (3)
C5—H5	0.9300	N2—O5	1.222 (3)
C6—H6	0.9300	O1—S1	1.4394 (18)
C7—N1	1.274 (3)	O2—S1	1.446 (2)
C7—H7	0.9300	C14—S1	1.757 (3)
C8—C9	1.396 (4)	C14—H14A	0.9600
C8—C13	1.398 (3)	C14—H14B	0.9600
C8—N1	1.415 (3)	C14—H14C	0.9600
C2—C1—C6	120.9 (2)	C9—C10—N2	117.9 (2)
C2—C1—S1	120.43 (17)	C11—C10—N2	119.1 (2)
C6—C1—S1	118.68 (17)	C12—C11—C10	118.1 (3)
C1—C2—C3	118.7 (2)	C12—C11—H11	121.0
C1—C2—H2	120.6	C10—C11—H11	121.0
C3—C2—H2	120.6	C11—C12—C13	120.8 (3)
C4—C3—C2	121.0 (2)	C11—C12—H12	119.6
C4—C3—H3	119.5	C13—C12—H12	119.6
C2—C3—H3	119.5	C12—C13—C8	120.7 (3)
C5—C4—C3	119.2 (2)	C12—C13—H13	119.7
C5—C4—C7	120.0 (2)	C8—C13—H13	119.7
C3—C4—C7	120.9 (2)	C7—N1—C8	120.8 (2)
C6—C5—C4	120.6 (2)	O4—N2—O5	123.4 (3)
C6—C5—H5	119.7	O4—N2—C10	118.2 (2)
C4—C5—H5	119.7	O5—N2—C10	118.4 (3)
C5—C6—C1	119.6 (2)	S1—C14—H14A	109.5
C5—C6—H6	120.2	S1—C14—H14B	109.5
C1—C6—H6	120.2	H14A—C14—H14B	109.5
N1—C7—C4	120.7 (2)	S1—C14—H14C	109.5
N1—C7—H7	119.7	H14A—C14—H14C	109.5
C4—C7—H7	119.7	H14B—C14—H14C	109.5
C9—C8—C13	119.4 (2)	O1—S1—O2	117.69 (12)
C9—C8—N1	123.0 (2)	O1—S1—C14	109.00 (13)
C13—C8—N1	117.5 (2)	O2—S1—C14	108.15 (13)
C10—C9—C8	118.1 (2)	O1—S1—C1	109.01 (11)
C10—C9—H9	120.9	O2—S1—C1	108.14 (11)
C8—C9—H9	120.9	C14—S1—C1	103.97 (12)
C9—C10—C11	123.0 (3)
C6—C1—C2—C3	−1.7 (4)	C10—C11—C12—C13	−0.5 (4)
S1—C1—C2—C3	178.49 (18)	C11—C12—C13—C8	−1.4 (5)
C1—C2—C3—C4	0.4 (4)	C9—C8—C13—C12	2.5 (4)
C2—C3—C4—C5	1.1 (4)	N1—C8—C13—C12	179.3 (2)
C2—C3—C4—C7	−179.0 (2)	C4—C7—N1—C8	177.8 (2)
C3—C4—C5—C6	−1.4 (4)	C9—C8—N1—C7	−38.7 (4)
C7—C4—C5—C6	178.7 (2)	C13—C8—N1—C7	144.5 (2)
C4—C5—C6—C1	0.1 (4)	C9—C10—N2—O4	−3.1 (4)
C2—C1—C6—C5	1.4 (4)	C11—C10—N2—O4	176.4 (2)
S1—C1—C6—C5	−178.75 (19)	C9—C10—N2—O5	177.9 (2)
C5—C4—C7—N1	2.7 (3)	C11—C10—N2—O5	−2.6 (4)
C3—C4—C7—N1	−177.3 (2)	C2—C1—S1—O1	1.1 (2)
C13—C8—C9—C10	−1.5 (4)	C6—C1—S1—O1	−178.74 (19)
N1—C8—C9—C10	−178.2 (2)	C2—C1—S1—O2	130.2 (2)
C8—C9—C10—C11	−0.4 (4)	C6—C1—S1—O2	−49.7 (2)
C8—C9—C10—N2	179.1 (2)	C2—C1—S1—C14	−115.1 (2)
C9—C10—C11—C12	1.4 (4)	C6—C1—S1—C14	65.1 (2)
N2—C10—C11—C12	−178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14C···O1i	0.96	2.42	3.380 (3)	178
C12—H12···O5ii	0.93	2.59	3.273 (4)	131
C6—H6···O2iii	0.93	2.52	3.442 (3)	169
C5—H5···O4iv	0.93	2.41	3.249 (3)	150
C2—H2···O1	0.93	2.58	2.948 (3)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14C⋯O1i	0.96	2.42	3.380 (3)	178
C12—H12⋯O5ii	0.93	2.59	3.273 (4)	131
C6—H6⋯O2iii	0.93	2.52	3.442 (3)	169
C5—H5⋯O4iv	0.93	2.41	3.249 (3)	150

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