Zwitterionic (E)-1-[(4-nitro-phen-yl)iminio-meth-yl]naphthalen-2-olate.

The title compound, C(17)H(12)N(2)O(3), was synthesized by the reaction of 2-hy-droxy-1-naphthaldehyde with 4-nitro-benzenamine. These condense to form the Schiff base, which crystallizes in the zwitterionic form. In the structure, the keto-amino tautomer has a fairly short intra-molecular N-H⋯O hydrogen bond between the 2-naphthalenone and amino groups, with electron delocalization. The mol-ecule is essentially planar, with a dihedral angle of 1.96 (3)° between the ring systems. In the crystal, the mol-ecules are linked via inter-molecular C-H⋯O hydrogen bonds, forming a layer parallel to (101).

Related literature

For background to Schiff base compounds, see: Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶). For the pharmaceutical and medicinal activity of Schiff bases, see: Chen et al. (1997 ▶); Dao et al. (2000 ▶); Ren et al. (2002 ▶); Sriram et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For Schiff bases in coordination chemistry, see: Ali et al. (2008 ▶); Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For related structures, see: Fun et al. (2009 ▶); Nadeem et al. (2009 ▶); Eltayeb et al. (2008 ▶). For standard bond lengths see: Allen, (2002 ▶).

Experimental

Crystal data

C17H12N2O3

M = 292.29

Monoclinic,

a = 8.0503 (6) Å

b = 12.8174 (9) Å

c = 13.1833 (10) Å

β = 97.271 (5)°

V = 1349.37 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.15 × 0.06 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer

44074 measured reflections

7946 independent reflections

3658 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.190

S = 0.96

7946 reflections

207 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012359/bq2290sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012359/bq2290Isup2.hkl

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

C17H12N2O3	F(000) = 608
Mr = 292.29	Dx = 1.439 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5160 reflections
a = 8.0503 (6) Å	θ = 3.0–30.1°
b = 12.8174 (9) Å	µ = 0.10 mm−1
c = 13.1833 (10) Å	T = 296 K
β = 97.271 (5)°	Needle, red
V = 1349.37 (17) Å3	0.15 × 0.06 × 0.04 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3658 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.074
graphite	θmax = 39.3°, θmin = 3.0°
φ and ω scans	h = −14→12
44074 measured reflections	k = −20→22
7946 independent reflections	l = −20→23

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0963P)2] where P = (Fo2 + 2Fc2)/3
7946 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.26 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
O3	0.88419 (14)	−0.08384 (7)	0.31991 (8)	0.0392 (3)
O2	0.44266 (15)	−0.40551 (8)	0.79254 (8)	0.0426 (3)
O1	0.49601 (17)	−0.51766 (7)	0.67875 (9)	0.0500 (3)
N2	0.74356 (13)	−0.11314 (7)	0.47852 (8)	0.0264 (2)
N1	0.49499 (15)	−0.42784 (8)	0.71179 (9)	0.0320 (2)
C17	0.82974 (14)	0.16828 (9)	0.44636 (9)	0.0234 (2)
C8	0.82177 (14)	0.05641 (9)	0.42782 (9)	0.0234 (2)
C6	0.55083 (16)	−0.24287 (9)	0.68580 (10)	0.0274 (2)
H6	0.5057	−0.2275	0.7456	0.033*
C1	0.55862 (16)	−0.34487 (9)	0.65258 (10)	0.0259 (2)
C7	0.75161 (14)	−0.01080 (9)	0.49403 (10)	0.0245 (2)
C2	0.62367 (17)	−0.37057 (9)	0.56335 (10)	0.0300 (3)
H2	0.6267	−0.4396	0.5421	0.036*
C12	0.90181 (15)	0.23306 (9)	0.37664 (10)	0.0273 (2)
C16	0.76748 (16)	0.21715 (9)	0.52907 (10)	0.0293 (3)
H16	0.721	0.1766	0.5768	0.035*
C3	0.68369 (16)	−0.29201 (9)	0.50680 (10)	0.0290 (3)
H3	0.7278	−0.3079	0.4468	0.035*
C5	0.61127 (16)	−0.16388 (9)	0.62877 (10)	0.0265 (2)
H5	0.6069	−0.0949	0.6501	0.032*
C13	0.90891 (17)	0.34145 (10)	0.39091 (12)	0.0355 (3)
H13	0.9569	0.383	0.3446	0.043*
C10	0.96505 (18)	0.08390 (11)	0.27475 (11)	0.0352 (3)
H10	1.0122	0.0574	0.2193	0.042*
C4	0.67859 (14)	−0.18811 (9)	0.53937 (9)	0.0239 (2)
C9	0.88945 (16)	0.01310 (9)	0.34053 (10)	0.0280 (2)
C14	0.84615 (17)	0.38702 (10)	0.47216 (13)	0.0379 (3)
H14	0.8517	0.459	0.4812	0.045*
C15	0.77392 (17)	0.32417 (10)	0.54105 (12)	0.0346 (3)
H15	0.7296	0.3547	0.5957	0.041*
C11	0.96888 (17)	0.18704 (10)	0.29171 (11)	0.0336 (3)
H11	1.0168	0.2302	0.2467	0.04*
H7	0.704 (2)	0.0100 (13)	0.5544 (14)	0.043 (5)*
H2N	0.798 (3)	−0.1327 (18)	0.4091 (18)	0.080 (7)*

	U11	U22	U33	U12	U13	U23
O3	0.0597 (6)	0.0256 (4)	0.0362 (5)	−0.0031 (4)	0.0217 (5)	−0.0042 (4)
O2	0.0637 (7)	0.0342 (5)	0.0348 (5)	−0.0030 (5)	0.0249 (5)	0.0036 (4)
O1	0.0847 (9)	0.0207 (4)	0.0502 (7)	−0.0069 (5)	0.0308 (6)	0.0002 (4)
N2	0.0325 (5)	0.0198 (4)	0.0283 (5)	−0.0011 (4)	0.0097 (4)	0.0016 (4)
N1	0.0419 (6)	0.0241 (5)	0.0322 (6)	−0.0016 (4)	0.0134 (5)	0.0031 (4)
C17	0.0224 (5)	0.0216 (5)	0.0260 (6)	−0.0003 (4)	0.0023 (4)	0.0025 (4)
C8	0.0253 (5)	0.0215 (5)	0.0235 (5)	−0.0003 (4)	0.0044 (4)	0.0014 (4)
C6	0.0332 (6)	0.0226 (5)	0.0282 (6)	−0.0006 (4)	0.0111 (5)	−0.0012 (4)
C1	0.0320 (6)	0.0206 (4)	0.0264 (6)	−0.0007 (4)	0.0089 (5)	0.0015 (4)
C7	0.0256 (5)	0.0212 (5)	0.0271 (6)	−0.0002 (4)	0.0052 (4)	0.0017 (4)
C2	0.0395 (7)	0.0196 (5)	0.0335 (6)	0.0000 (4)	0.0148 (5)	−0.0022 (4)
C12	0.0257 (5)	0.0236 (5)	0.0329 (6)	−0.0022 (4)	0.0054 (5)	0.0037 (4)
C16	0.0334 (6)	0.0251 (5)	0.0302 (6)	−0.0001 (5)	0.0073 (5)	−0.0012 (4)
C3	0.0369 (6)	0.0222 (5)	0.0306 (6)	−0.0001 (4)	0.0151 (5)	−0.0018 (4)
C5	0.0326 (6)	0.0193 (4)	0.0290 (6)	−0.0019 (4)	0.0097 (5)	−0.0026 (4)
C13	0.0334 (6)	0.0245 (5)	0.0499 (9)	−0.0044 (5)	0.0108 (6)	0.0053 (5)
C10	0.0471 (8)	0.0325 (6)	0.0291 (6)	−0.0030 (5)	0.0164 (6)	0.0009 (5)
C4	0.0268 (5)	0.0201 (4)	0.0259 (6)	−0.0012 (4)	0.0075 (4)	0.0005 (4)
C9	0.0334 (6)	0.0257 (5)	0.0259 (6)	−0.0012 (4)	0.0076 (5)	−0.0006 (4)
C14	0.0357 (7)	0.0220 (5)	0.0565 (9)	−0.0029 (5)	0.0079 (7)	−0.0021 (6)
C15	0.0367 (7)	0.0260 (6)	0.0413 (8)	0.0011 (5)	0.0059 (6)	−0.0060 (5)
C11	0.0382 (7)	0.0319 (6)	0.0329 (7)	−0.0054 (5)	0.0129 (6)	0.0046 (5)

O3—C9	1.2714 (15)	C2—H2	0.93
O2—N1	1.2274 (14)	C12—C13	1.4021 (17)
O1—N1	1.2312 (14)	C12—C11	1.4304 (18)
N2—C7	1.3279 (15)	C16—C15	1.3810 (17)
N2—C4	1.3951 (14)	C16—H16	0.93
N2—H2N	1.09 (2)	C3—C4	1.4015 (16)
N1—C1	1.4504 (14)	C3—H3	0.93
C17—C16	1.4039 (16)	C5—C4	1.3931 (16)
C17—C12	1.4163 (15)	C5—H5	0.93
C17—C8	1.4546 (16)	C13—C14	1.372 (2)
C8—C7	1.3957 (15)	C13—H13	0.93
C8—C9	1.4450 (16)	C10—C11	1.3405 (18)
C6—C1	1.3827 (17)	C10—C9	1.4421 (17)
C6—C5	1.3855 (16)	C10—H10	0.93
C6—H6	0.93	C14—C15	1.395 (2)
C1—C2	1.3866 (16)	C14—H14	0.93
C7—H7	0.962 (19)	C15—H15	0.93
C2—C3	1.3763 (16)	C11—H11	0.93
C7—N2—C4	127.33 (10)	C17—C16—H16	119.3
C7—N2—H2N	109.9 (12)	C2—C3—C4	120.22 (11)
C4—N2—H2N	122.8 (12)	C2—C3—H3	119.9
O2—N1—O1	122.91 (11)	C4—C3—H3	119.9
O2—N1—C1	118.62 (10)	C6—C5—C4	119.81 (10)
O1—N1—C1	118.47 (10)	C6—C5—H5	120.1
C16—C17—C12	117.28 (11)	C4—C5—H5	120.1
C16—C17—C8	123.91 (10)	C14—C13—C12	120.93 (12)
C12—C17—C8	118.81 (10)	C14—C13—H13	119.5
C7—C8—C9	118.96 (10)	C12—C13—H13	119.5
C7—C8—C17	121.07 (10)	C11—C10—C9	121.53 (12)
C9—C8—C17	119.96 (10)	C11—C10—H10	119.2
C1—C6—C5	119.07 (10)	C9—C10—H10	119.2
C1—C6—H6	120.5	C5—C4—N2	123.17 (10)
C5—C6—H6	120.5	C5—C4—C3	120.04 (10)
C6—C1—C2	122.04 (11)	N2—C4—C3	116.79 (10)
C6—C1—N1	119.32 (10)	O3—C9—C10	119.44 (11)
C2—C1—N1	118.64 (10)	O3—C9—C8	122.68 (11)
N2—C7—C8	121.95 (11)	C10—C9—C8	117.87 (11)
N2—C7—H7	112.6 (10)	C13—C14—C15	119.19 (12)
C8—C7—H7	125.4 (10)	C13—C14—H14	120.4
C3—C2—C1	118.81 (11)	C15—C14—H14	120.4
C3—C2—H2	120.6	C16—C15—C14	120.79 (12)
C1—C2—H2	120.6	C16—C15—H15	119.6
C13—C12—C17	120.46 (11)	C14—C15—H15	119.6
C13—C12—C11	120.03 (11)	C10—C11—C12	122.29 (11)
C17—C12—C11	119.50 (11)	C10—C11—H11	118.9
C15—C16—C17	121.34 (11)	C12—C11—H11	118.9
C15—C16—H16	119.3
C16—C17—C8—C7	−0.89 (19)	C1—C6—C5—C4	0.0 (2)
C12—C17—C8—C7	−179.83 (12)	C17—C12—C13—C14	−0.2 (2)
C16—C17—C8—C9	−179.95 (12)	C11—C12—C13—C14	−179.64 (14)
C12—C17—C8—C9	1.11 (18)	C6—C5—C4—N2	−179.26 (12)
C5—C6—C1—C2	−0.6 (2)	C6—C5—C4—C3	0.6 (2)
C5—C6—C1—N1	−179.78 (12)	C7—N2—C4—C5	−0.3 (2)
O2—N1—C1—C6	−3.2 (2)	C7—N2—C4—C3	179.85 (12)
O1—N1—C1—C6	176.80 (13)	C2—C3—C4—C5	−0.6 (2)
O2—N1—C1—C2	177.56 (13)	C2—C3—C4—N2	179.28 (12)
O1—N1—C1—C2	−2.4 (2)	C11—C10—C9—O3	177.94 (14)
C4—N2—C7—C8	179.22 (12)	C11—C10—C9—C8	−1.8 (2)
C9—C8—C7—N2	−0.77 (19)	C7—C8—C9—O3	1.8 (2)
C17—C8—C7—N2	−179.84 (11)	C17—C8—C9—O3	−179.16 (12)
C6—C1—C2—C3	0.6 (2)	C7—C8—C9—C10	−178.46 (12)
N1—C1—C2—C3	179.80 (12)	C17—C8—C9—C10	0.62 (19)
C16—C17—C12—C13	−0.20 (19)	C12—C13—C14—C15	−0.2 (2)
C8—C17—C12—C13	178.81 (12)	C17—C16—C15—C14	−1.4 (2)
C16—C17—C12—C11	179.27 (12)	C13—C14—C15—C16	1.0 (2)
C8—C17—C12—C11	−1.71 (18)	C9—C10—C11—C12	1.3 (2)
C12—C17—C16—C15	0.98 (19)	C13—C12—C11—C10	−179.98 (14)
C8—C17—C16—C15	−177.98 (13)	C17—C12—C11—C10	0.5 (2)
C1—C2—C3—C4	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	1.09 (2)	1.57 (2)	2.5287 (15)	143 (2)
C5—H5···O2i	0.93	2.59	3.5136 (16)	173
C16—H16···O2i	0.93	2.53	3.4455 (17)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3	1.09 (2)	1.57 (2)	2.5287 (15)	143 (2)
C5—H5⋯O2i	0.93	2.59	3.5136 (16)	173
C16—H16⋯O2i	0.93	2.53	3.4455 (17)	169

Symmetry code: (i) .