Crystal structure of 2-{[(5-nitro-thio-phen-2-yl)methyl-idene]amino}-phenol.

The title compound, C11H8N2O3S, is roughly planar; the di-hedral angle between the planes of the thio-phene and benzene rings is 8.38 (10)°. An intra-molecular O-H⋯N hydrogen bond generates an S(5) ring motif. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of O-H⋯O hydrogen bonds with an R 2 (2)(22) graph-set motif. Aromatic π-π stacking inter-actions [centroid-centroid sep-ar-ations = 3.653 (3) and 3.852 (3) Å] link the dimers into a three-dimensional network.

Related literature

For Schiff bases as ligands, see: Aydoğan et al. (2001 ▸); Tanak et al. (2009 ▸). For related structures, see: Tanak et al. (2013 ▸, 2014 ▸).

Experimental

Crystal data

C11H8N2O3S

M = 248.25

Monoclinic,

a = 10.642 (5) Å

b = 7.043 (5) Å

c = 14.535 (5) Å

β = 93.566 (5)°

V = 1087.3 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.68 × 0.37 × 0.15 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▸) T min = 0.877, T max = 0.965

7883 measured reflections

2254 independent reflections

1696 reflections with I > 2σ(I)

R int = 0.114

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.100

S = 0.98

2254 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.89 e Å−3

Δρmin = −0.45 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▸); cell refinement: X-AREA ; data reduction: X-RED32 (Stoe & Cie, 2002 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015009202/hb7421sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009202/hb7421Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009202/hb7421Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015009202/hb7421fig1.tif

The mol­ecular structure of the title compound, showing 30% probability diplacement ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S2056989015009202/hb7421fig2.tif

Centrosymmetric dimer with a central (22) ring motif. Dashed lines indicate hydrogen bonds.

Click here for additional data file.

. DOI: 10.1107/S2056989015009202/hb7421fig3.tif

Packing diagram of the title compound.

CCDC reference: 1400935

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H8N2O3S	F(000) = 512
Mr = 248.25	Dx = 1.516 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 9881 reflections
a = 10.642 (5) Å	θ = 1.9–29.0°
b = 7.043 (5) Å	µ = 0.29 mm−1
c = 14.535 (5) Å	T = 293 K
β = 93.566 (5)°	Prism, dark brown
V = 1087.3 (10) Å3	0.68 × 0.37 × 0.15 mm
Z = 4

Stoe IPDS diffractometer	2254 independent reflections
Radiation source: fine-focus sealed tube	1696 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.114
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 1.9°
rotation method scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
Tmin = 0.877, Tmax = 0.965	l = −18→18
7883 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0675P)2] where P = (Fo2 + 2Fc2)/3
2254 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.89 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Experimental. 360 frames, detector distance = 80 mm

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	0.58190 (4)	0.11508 (6)	0.11107 (3)	0.04605 (16)
N2	0.41409 (13)	0.10939 (19)	0.27382 (9)	0.0449 (3)
N1	0.77113 (14)	0.1231 (2)	−0.00532 (10)	0.0532 (4)
C1	0.73710 (15)	0.1181 (2)	0.08813 (11)	0.0453 (4)
C4	0.62428 (15)	0.1069 (2)	0.22648 (11)	0.0460 (4)
C6	0.32806 (15)	0.1149 (2)	0.34380 (11)	0.0438 (4)
O2	0.68543 (14)	0.1159 (2)	−0.06611 (9)	0.0733 (4)
C5	0.53109 (16)	0.1040 (3)	0.29481 (12)	0.0496 (4)
C7	0.35846 (18)	0.1360 (3)	0.43745 (12)	0.0512 (4)
C3	0.75216 (17)	0.1053 (3)	0.24363 (13)	0.0625 (5)
O1	0.88152 (13)	0.1329 (3)	−0.02073 (10)	0.0807 (5)
C2	0.81816 (17)	0.1119 (3)	0.16344 (13)	0.0581 (5)
O3	0.16507 (15)	0.0835 (3)	0.22346 (11)	0.0904 (6)
C8	0.26579 (19)	0.1470 (3)	0.49960 (13)	0.0574 (5)
C11	0.20103 (17)	0.1045 (3)	0.31379 (13)	0.0584 (5)
C9	0.1415 (2)	0.1387 (3)	0.46888 (15)	0.0665 (5)
C10	0.1095 (2)	0.1179 (4)	0.37699 (17)	0.0748 (6)
H2	0.904 (2)	0.113 (3)	0.1586 (14)	0.068 (6)*
H3	0.787 (2)	0.107 (3)	0.2986 (17)	0.073 (7)*
H5	0.564 (2)	0.096 (3)	0.3560 (17)	0.079 (7)*
H7	0.447 (2)	0.150 (3)	0.4606 (13)	0.063 (6)*
H10	0.028 (3)	0.112 (4)	0.3543 (19)	0.100 (9)*
H9	0.080 (2)	0.151 (3)	0.5109 (16)	0.078 (7)*
H8	0.288 (2)	0.167 (3)	0.5609 (16)	0.069 (6)*
H1	0.227 (3)	0.069 (4)	0.198 (2)	0.097 (10)*

	U11	U22	U33	U12	U13	U23
S1	0.0373 (2)	0.0531 (3)	0.0481 (2)	−0.00158 (18)	0.00516 (15)	0.00117 (19)
N2	0.0434 (7)	0.0456 (8)	0.0468 (7)	−0.0009 (6)	0.0106 (5)	−0.0022 (6)
N1	0.0513 (8)	0.0589 (9)	0.0506 (8)	−0.0077 (7)	0.0128 (6)	0.0009 (7)
C1	0.0413 (8)	0.0481 (9)	0.0475 (8)	−0.0043 (7)	0.0102 (6)	−0.0017 (7)
C4	0.0415 (8)	0.0509 (10)	0.0463 (8)	−0.0008 (7)	0.0083 (6)	−0.0016 (7)
C6	0.0416 (8)	0.0412 (8)	0.0496 (8)	0.0020 (7)	0.0113 (6)	0.0011 (7)
O2	0.0625 (8)	0.1093 (12)	0.0482 (7)	−0.0094 (8)	0.0035 (6)	0.0076 (7)
C5	0.0433 (9)	0.0598 (11)	0.0463 (9)	0.0000 (8)	0.0086 (7)	−0.0012 (8)
C7	0.0498 (9)	0.0535 (11)	0.0510 (9)	0.0034 (8)	0.0087 (7)	0.0005 (8)
C3	0.0435 (9)	0.0957 (16)	0.0482 (10)	−0.0015 (9)	0.0028 (7)	−0.0021 (10)
O1	0.0533 (8)	0.1232 (14)	0.0681 (9)	−0.0151 (8)	0.0234 (7)	−0.0032 (9)
C2	0.0368 (8)	0.0814 (13)	0.0567 (10)	−0.0030 (9)	0.0072 (7)	−0.0037 (9)
O3	0.0490 (8)	0.160 (2)	0.0621 (9)	0.0045 (10)	0.0003 (7)	−0.0177 (10)
C8	0.0652 (11)	0.0581 (12)	0.0506 (10)	0.0055 (9)	0.0174 (9)	0.0026 (8)
C11	0.0448 (9)	0.0739 (13)	0.0572 (10)	−0.0007 (9)	0.0077 (7)	−0.0046 (9)
C9	0.0600 (11)	0.0721 (14)	0.0707 (13)	0.0035 (10)	0.0295 (10)	0.0010 (10)
C10	0.0410 (10)	0.1066 (19)	0.0783 (14)	−0.0021 (11)	0.0147 (9)	−0.0058 (13)

S1—C1	1.7054 (18)	C7—C8	1.380 (3)
S1—C4	1.7107 (18)	C7—H7	0.99 (2)
N2—C5	1.264 (2)	C3—C2	1.399 (3)
N2—C6	1.411 (2)	C3—H3	0.86 (2)
N1—O1	1.212 (2)	C2—H2	0.92 (2)
N1—O2	1.231 (2)	O3—C11	1.353 (2)
N1—C1	1.428 (2)	O3—H1	0.78 (3)
C1—C2	1.352 (3)	C8—C9	1.370 (3)
C4—C3	1.368 (3)	C8—H8	0.92 (2)
C4—C5	1.447 (2)	C11—C10	1.383 (3)
C6—C7	1.387 (3)	C9—C10	1.366 (3)
C6—C11	1.396 (2)	C9—H9	0.93 (2)
C5—H5	0.94 (2)	C10—H10	0.91 (3)
C1—S1—C4	89.58 (8)	C4—C3—C2	113.16 (17)
C5—N2—C6	120.03 (15)	C4—C3—H3	122.7 (16)
O1—N1—O2	123.60 (15)	C2—C3—H3	124.1 (16)
O1—N1—C1	118.92 (15)	C1—C2—C3	110.35 (16)
O2—N1—C1	117.48 (15)	C1—C2—H2	121.6 (13)
C2—C1—N1	125.76 (16)	C3—C2—H2	128.0 (13)
C2—C1—S1	114.73 (13)	C11—O3—H1	106 (2)
N1—C1—S1	119.50 (13)	C9—C8—C7	119.92 (19)
C3—C4—C5	126.26 (16)	C9—C8—H8	120.7 (14)
C3—C4—S1	112.18 (13)	C7—C8—H8	119.3 (14)
C5—C4—S1	121.56 (13)	O3—C11—C10	118.94 (18)
C7—C6—C11	118.31 (16)	O3—C11—C6	121.26 (17)
C7—C6—N2	126.03 (16)	C10—C11—C6	119.80 (18)
C11—C6—N2	115.62 (15)	C10—C9—C8	120.01 (18)
N2—C5—C4	122.75 (16)	C10—C9—H9	120.7 (14)
N2—C5—H5	122.4 (15)	C8—C9—H9	119.3 (14)
C4—C5—H5	114.9 (15)	C9—C10—C11	120.9 (2)
C8—C7—C6	121.03 (18)	C9—C10—H10	122.2 (18)
C8—C7—H7	118.6 (12)	C11—C10—H10	116.8 (18)
C6—C7—H7	120.3 (12)
O1—N1—C1—C2	−4.2 (3)	C5—C4—C3—C2	−179.07 (19)
O2—N1—C1—C2	175.3 (2)	S1—C4—C3—C2	0.4 (2)
O1—N1—C1—S1	177.06 (14)	N1—C1—C2—C3	−179.06 (17)
O2—N1—C1—S1	−3.4 (2)	S1—C1—C2—C3	−0.3 (2)
C4—S1—C1—C2	0.44 (16)	C4—C3—C2—C1	0.0 (3)
C4—S1—C1—N1	179.27 (14)	C6—C7—C8—C9	−0.6 (3)
C1—S1—C4—C3	−0.44 (16)	C7—C6—C11—O3	−179.9 (2)
C1—S1—C4—C5	179.02 (15)	N2—C6—C11—O3	2.3 (3)
C5—N2—C6—C7	7.5 (3)	C7—C6—C11—C10	0.9 (3)
C5—N2—C6—C11	−174.84 (17)	N2—C6—C11—C10	−176.96 (19)
C6—N2—C5—C4	−177.11 (16)	C7—C8—C9—C10	0.6 (3)
C3—C4—C5—N2	178.60 (19)	C8—C9—C10—C11	0.1 (4)
S1—C4—C5—N2	−0.8 (3)	O3—C11—C10—C9	179.8 (2)
C11—C6—C7—C8	−0.1 (3)	C6—C11—C10—C9	−0.9 (4)
N2—C6—C7—C8	177.44 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O2i	0.78 (3)	2.54 (3)	3.192 (3)	141 (3)
O3—H1···N2	0.78 (3)	2.23 (3)	2.711 (2)	121 (3)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O3H1O2i	0.78(3)	2.54(3)	3.192(3)	141(3)
O3H1N2	0.78(3)	2.23(3)	2.711(2)	121(3)

Symmetry code: (i) .