(E)-1-[(2-Amino-5-nitro-phen-yl)iminio-meth-yl]naphthalen-2-olate.

The title Schiff base compound, C(17)H(13)N(3)O(3), crystallizes in a zwitterionic form and exists in a trans configuration about the C=N bond. The mol-ecule is slightly twisted, the dihedral angle between the benzene ring and naphthalene ring system being 10.80 (9)°. The nitro group is twisted relative to the plane of the benzene ring [dihedral angle = 8.88 (12)°]. Bifurcated intra-molecular N-H⋯N and N-H⋯O hydrogen bonds formed between iminium groups and amine N atoms and naphthalen-2-olate O atoms generate S(5) and S(6) ring motifs, respectively. In the crystal, neighbouring zwitterions are linked through weak C-H⋯O inter-actions, giving rise to screw chains along [010]. Mol-ecules in these chains are linked to those of an adjacent chains through N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions, forming sheets parallel to the ac plane. O⋯C [2.895 (3) Å] short contacts and π-π inter-actions [centroid-centroid distance = 3.8249 (19) Å] are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to Schiff bases and their applications, see: Eltayeb et al. (2007 ▶; 2008 ▶); Dao et al. (2000 ▶); Kagkelari et al. (2009 ▶); Karthikeyan et al. (2006 ▶); Sondhi et al. (2006 ▶); Sriram et al. (2006 ▶). For related structures, see: Eltayeb et al. (2009 ▶; 2010 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C17H13N3O3

M = 307.30

Monoclinic,

a = 10.369 (4) Å

b = 4.6442 (18) Å

c = 28.539 (9) Å

β = 103.548 (12)°

V = 1336.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.48 × 0.10 × 0.04 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.950, T max = 0.996

14018 measured reflections

3887 independent reflections

2341 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.151

S = 1.02

3887 reflections

220 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014923/sj2769sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014923/sj2769Isup2.hkl

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

C17H13N3O3	F(000) = 640
Mr = 307.30	Dx = 1.528 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3887 reflections
a = 10.369 (4) Å	θ = 1.5–30.0°
b = 4.6442 (18) Å	µ = 0.11 mm−1
c = 28.539 (9) Å	T = 100 K
β = 103.548 (12)°	Plate, red
V = 1336.1 (8) Å3	0.48 × 0.10 × 0.04 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	3887 independent reflections
Radiation source: sealed tube	2341 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→13
Tmin = 0.950, Tmax = 0.996	k = −6→6
14018 measured reflections	l = −39→40

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.059P)2 + 0.6347P] where P = (Fo2 + 2Fc2)/3
3887 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.82332 (14)	−0.0589 (3)	0.96873 (5)	0.0254 (4)
O2	1.22099 (15)	−0.6304 (4)	0.76236 (5)	0.0338 (4)
O3	1.09865 (15)	−0.2495 (4)	0.74798 (5)	0.0317 (4)
N1	0.92876 (16)	−0.1176 (4)	0.89879 (5)	0.0198 (4)
H1N1	0.911 (3)	−0.151 (6)	0.9315 (10)	0.053 (8)*
N2	1.08296 (18)	−0.4892 (5)	0.96268 (6)	0.0250 (4)
H1N2	1.068 (2)	−0.318 (6)	0.9746 (9)	0.038 (7)*
H2N2	1.134 (2)	−0.630 (6)	0.9828 (9)	0.036 (7)*
N3	1.15214 (17)	−0.4461 (4)	0.77485 (6)	0.0254 (4)
C1	1.02284 (18)	−0.2851 (5)	0.88271 (6)	0.0189 (4)
C2	1.09971 (19)	−0.4753 (5)	0.91675 (6)	0.0200 (4)
C3	1.1889 (2)	−0.6596 (5)	0.90188 (7)	0.0231 (5)
H3A	1.2383	−0.7889	0.9238	0.028*
C4	1.2048 (2)	−0.6533 (5)	0.85552 (7)	0.0234 (5)
H4A	1.2636	−0.7783	0.8458	0.028*
C5	1.13185 (19)	−0.4580 (5)	0.82357 (6)	0.0215 (4)
C6	1.04003 (19)	−0.2757 (5)	0.83600 (6)	0.0216 (4)
H6A	0.9907	−0.1492	0.8135	0.026*
C7	0.84656 (19)	0.0765 (5)	0.87499 (6)	0.0196 (4)
H7A	0.8514	0.1269	0.8439	0.023*
C8	0.75161 (19)	0.2092 (5)	0.89575 (6)	0.0194 (4)
C9	0.7424 (2)	0.1231 (5)	0.94325 (6)	0.0211 (4)
C10	0.6390 (2)	0.2452 (5)	0.96265 (6)	0.0243 (5)
H10A	0.6300	0.1872	0.9929	0.029*
C11	0.5547 (2)	0.4420 (5)	0.93792 (7)	0.0242 (5)
H11A	0.4894	0.5173	0.9518	0.029*
C12	0.56177 (19)	0.5396 (5)	0.89118 (6)	0.0208 (4)
C13	0.4720 (2)	0.7454 (5)	0.86662 (7)	0.0239 (5)
H13A	0.4088	0.8222	0.8814	0.029*
C14	0.4757 (2)	0.8357 (5)	0.82110 (7)	0.0252 (5)
H14A	0.4148	0.9701	0.8049	0.030*
C15	0.5722 (2)	0.7223 (5)	0.79976 (6)	0.0230 (5)
H15A	0.5758	0.7834	0.7691	0.028*
C16	0.66212 (19)	0.5223 (5)	0.82295 (6)	0.0214 (4)
H16A	0.7258	0.4515	0.8078	0.026*
C17	0.65970 (19)	0.4222 (5)	0.86945 (6)	0.0188 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0339 (8)	0.0264 (9)	0.0168 (6)	0.0063 (7)	0.0075 (6)	0.0041 (6)
O2	0.0391 (9)	0.0402 (11)	0.0257 (7)	0.0115 (8)	0.0148 (7)	−0.0053 (7)
O3	0.0429 (9)	0.0331 (10)	0.0218 (7)	0.0053 (8)	0.0127 (6)	0.0051 (7)
N1	0.0263 (8)	0.0187 (10)	0.0156 (7)	−0.0005 (7)	0.0069 (6)	−0.0004 (7)
N2	0.0335 (10)	0.0246 (11)	0.0176 (8)	0.0047 (9)	0.0075 (7)	0.0008 (8)
N3	0.0306 (9)	0.0270 (11)	0.0204 (8)	0.0009 (8)	0.0097 (7)	−0.0028 (7)
C1	0.0249 (9)	0.0159 (11)	0.0177 (8)	−0.0038 (8)	0.0085 (7)	−0.0033 (7)
C2	0.0245 (9)	0.0185 (12)	0.0177 (8)	−0.0038 (9)	0.0063 (7)	−0.0012 (8)
C3	0.0257 (10)	0.0203 (12)	0.0237 (9)	0.0012 (9)	0.0065 (8)	0.0008 (8)
C4	0.0260 (10)	0.0207 (12)	0.0249 (9)	0.0014 (9)	0.0086 (8)	−0.0032 (8)
C5	0.0250 (9)	0.0247 (13)	0.0160 (8)	−0.0022 (9)	0.0075 (7)	−0.0033 (8)
C6	0.0268 (9)	0.0208 (12)	0.0173 (8)	−0.0022 (9)	0.0053 (7)	−0.0005 (8)
C7	0.0262 (9)	0.0171 (11)	0.0155 (8)	−0.0028 (8)	0.0049 (7)	−0.0001 (7)
C8	0.0250 (9)	0.0178 (11)	0.0152 (8)	−0.0017 (8)	0.0046 (7)	−0.0003 (8)
C9	0.0284 (10)	0.0182 (11)	0.0165 (8)	−0.0003 (9)	0.0045 (7)	0.0000 (8)
C10	0.0343 (11)	0.0246 (13)	0.0158 (8)	0.0029 (10)	0.0098 (8)	0.0029 (8)
C11	0.0289 (10)	0.0241 (13)	0.0211 (9)	0.0016 (9)	0.0093 (8)	−0.0007 (8)
C12	0.0249 (9)	0.0190 (12)	0.0182 (8)	−0.0031 (9)	0.0047 (7)	−0.0005 (8)
C13	0.0270 (10)	0.0233 (13)	0.0218 (9)	0.0025 (9)	0.0063 (8)	0.0000 (8)
C14	0.0300 (10)	0.0233 (13)	0.0212 (9)	−0.0001 (9)	0.0035 (8)	0.0021 (8)
C15	0.0299 (10)	0.0232 (12)	0.0155 (8)	−0.0023 (9)	0.0046 (7)	0.0008 (8)
C16	0.0272 (10)	0.0205 (12)	0.0173 (8)	−0.0035 (9)	0.0069 (7)	−0.0011 (8)
C17	0.0238 (9)	0.0162 (11)	0.0160 (8)	−0.0039 (8)	0.0039 (7)	−0.0008 (7)

O1—C9	1.289 (2)	C7—C8	1.405 (3)
O2—N3	1.220 (2)	C7—H7A	0.9300
O3—N3	1.237 (2)	C8—C9	1.438 (3)
N1—C7	1.315 (3)	C8—C17	1.454 (3)
N1—C1	1.406 (2)	C9—C10	1.434 (3)
N1—H1N1	1.00 (3)	C10—C11	1.344 (3)
N2—C2	1.364 (2)	C10—H10A	0.9300
N2—H1N2	0.89 (3)	C11—C12	1.427 (3)
N2—H2N2	0.94 (3)	C11—H11A	0.9300
N3—C5	1.455 (2)	C12—C13	1.402 (3)
C1—C6	1.386 (2)	C12—C17	1.417 (3)
C1—C2	1.413 (3)	C13—C14	1.374 (3)
C2—C3	1.397 (3)	C13—H13A	0.9300
C3—C4	1.371 (3)	C14—C15	1.391 (3)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.380 (3)	C15—C16	1.372 (3)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.381 (3)	C16—C17	1.412 (3)
C6—H6A	0.9300	C16—H16A	0.9300
C7—N1—C1	128.76 (16)	C7—C8—C9	118.92 (18)
C7—N1—H1N1	110.5 (16)	C7—C8—C17	121.33 (16)
C1—N1—H1N1	120.5 (16)	C9—C8—C17	119.71 (17)
C2—N2—H1N2	113.4 (17)	O1—C9—C10	119.21 (17)
C2—N2—H2N2	116.1 (15)	O1—C9—C8	122.43 (18)
H1N2—N2—H2N2	120 (2)	C10—C9—C8	118.36 (18)
O2—N3—O3	123.00 (17)	C11—C10—C9	121.25 (17)
O2—N3—C5	118.54 (18)	C11—C10—H10A	119.4
O3—N3—C5	118.46 (17)	C9—C10—H10A	119.4
C6—C1—N1	123.48 (18)	C10—C11—C12	122.52 (19)
C6—C1—C2	120.14 (18)	C10—C11—H11A	118.7
N1—C1—C2	116.36 (16)	C12—C11—H11A	118.7
N2—C2—C3	120.35 (19)	C13—C12—C17	120.24 (17)
N2—C2—C1	120.83 (19)	C13—C12—C11	120.69 (18)
C3—C2—C1	118.74 (17)	C17—C12—C11	119.05 (18)
C4—C3—C2	121.19 (19)	C14—C13—C12	121.21 (19)
C4—C3—H3A	119.4	C14—C13—H13A	119.4
C2—C3—H3A	119.4	C12—C13—H13A	119.4
C3—C4—C5	118.71 (19)	C13—C14—C15	118.7 (2)
C3—C4—H4A	120.6	C13—C14—H14A	120.6
C5—C4—H4A	120.6	C15—C14—H14A	120.6
C4—C5—C6	122.52 (17)	C16—C15—C14	121.52 (18)
C4—C5—N3	118.49 (18)	C16—C15—H15A	119.2
C6—C5—N3	118.99 (18)	C14—C15—H15A	119.2
C5—C6—C1	118.63 (19)	C15—C16—C17	121.11 (19)
C5—C6—H6A	120.7	C15—C16—H16A	119.4
C1—C6—H6A	120.7	C17—C16—H16A	119.4
N1—C7—C8	121.09 (17)	C16—C17—C12	117.18 (18)
N1—C7—H7A	119.5	C16—C17—C8	123.74 (18)
C8—C7—H7A	119.5	C12—C17—C8	119.08 (16)
C7—N1—C1—C6	−2.5 (3)	C17—C8—C9—O1	−178.14 (19)
C7—N1—C1—C2	179.1 (2)	C7—C8—C9—C10	−175.65 (19)
C6—C1—C2—N2	−179.3 (2)	C17—C8—C9—C10	2.0 (3)
N1—C1—C2—N2	−0.8 (3)	O1—C9—C10—C11	178.1 (2)
C6—C1—C2—C3	−2.4 (3)	C8—C9—C10—C11	−2.0 (3)
N1—C1—C2—C3	176.07 (18)	C9—C10—C11—C12	0.5 (3)
N2—C2—C3—C4	178.5 (2)	C10—C11—C12—C13	−179.9 (2)
C1—C2—C3—C4	1.6 (3)	C10—C11—C12—C17	1.1 (3)
C2—C3—C4—C5	0.8 (3)	C17—C12—C13—C14	0.6 (3)
C3—C4—C5—C6	−2.4 (3)	C11—C12—C13—C14	−178.3 (2)
C3—C4—C5—N3	178.11 (19)	C12—C13—C14—C15	−1.0 (3)
O2—N3—C5—C4	8.4 (3)	C13—C14—C15—C16	0.5 (3)
O3—N3—C5—C4	−171.70 (19)	C14—C15—C16—C17	0.4 (3)
O2—N3—C5—C6	−171.2 (2)	C15—C16—C17—C12	−0.8 (3)
O3—N3—C5—C6	8.8 (3)	C15—C16—C17—C8	179.5 (2)
C4—C5—C6—C1	1.5 (3)	C13—C12—C17—C16	0.3 (3)
N3—C5—C6—C1	−178.97 (19)	C11—C12—C17—C16	179.27 (19)
N1—C1—C6—C5	−177.46 (19)	C13—C12—C17—C8	179.96 (19)
C2—C1—C6—C5	0.9 (3)	C11—C12—C17—C8	−1.0 (3)
C1—N1—C7—C8	175.18 (19)	C7—C8—C17—C16	−3.2 (3)
N1—C7—C8—C9	−1.9 (3)	C9—C8—C17—C16	179.21 (19)
N1—C7—C8—C17	−179.45 (19)	C7—C8—C17—C12	177.07 (19)
C7—C8—C9—O1	4.3 (3)	C9—C8—C17—C12	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	1.01 (3)	1.61 (3)	2.505 (2)	146 (3)
N1—H1N1···N2	1.01 (3)	2.39 (3)	2.737 (3)	100 (2)
N2—H1N2···O1i	0.89 (3)	2.47 (3)	3.219 (3)	142.0 (19)
N2—H2N2···O1ii	0.95 (3)	1.98 (3)	2.879 (3)	158.6 (19)
C6—H6A···O3iii	0.93	2.57	3.489 (3)	168
C15—H15A···O2iv	0.93	2.51	3.161 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	1.01 (3)	1.61 (3)	2.505 (2)	146 (3)
N1—H1N1⋯N2	1.01 (3)	2.39 (3)	2.737 (3)	100 (2)
N2—H1N2⋯O1i	0.89 (3)	2.47 (3)	3.219 (3)	142.0 (19)
N2—H2N2⋯O1ii	0.95 (3)	1.98 (3)	2.879 (3)	158.6 (19)
C6—H6A⋯O3iii	0.93	2.57	3.489 (3)	168
C15—H15A⋯O2iv	0.93	2.51	3.161 (3)	127

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