(E)-1-(3-Formyl-phen-yl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium.

In the title zwitterion, C17H12N2O2, the dihedral angle between the benzene ring and naphthalene ring system is 11.76 (7)° and an intra-molecular N-H⋯O hydrogen bond exists. In the crystal, molecules are linked via pairs of C-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For general background to the use of azo compounds as dyes, pigments and advanced materials, see: Lee et al. (2004 ▶); Oueslati et al. (2004 ▶). For a related structure, see: Xu et al. (2010 ▶).

Experimental

Crystal data

C17H12N2O2

M = 276.29

Monoclinic,

a = 5.601 (4) Å

b = 7.780 (5) Å

c = 29.70 (2) Å

β = 94.624 (16)°

V = 1290.0 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.09 × 0.04 × 0.01 mm

Data collection

Nonius KappaCCD diffractometer

16470 measured reflections

3964 independent reflections

2155 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.154

S = 1.01

3963 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: KappaCCD Server Software (Nonius, 1999 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813024112/xu5735sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024112/xu5735Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024112/xu5735Isup3.cml

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

C17H12N2O2	F(000) = 576
Mr = 276.29	Dx = 1.423 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3964 reflections
a = 5.601 (4) Å	θ = 1.3–30.7°
b = 7.780 (5) Å	µ = 0.10 mm−1
c = 29.70 (2) Å	T = 293 K
β = 94.624 (16)°	Needle, red
V = 1290.0 (15) Å3	0.09 × 0.04 × 0.01 mm
Z = 4

Nonius KappaCCD diffractometer	2155 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 30.7°, θmin = 1.4°
CCD rotation images, thick slices scans	h = −7→7
16470 measured reflections	k = −11→11
3964 independent reflections	l = −42→42

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) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.068P)2 + 0.0107P] where P = (Fo2 + 2Fc2)/3
3963 reflections	(Δ/σ)max = 0.002
194 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	1.1128 (2)	0.36260 (19)	0.05566 (4)	0.0354 (4)
O2	−0.0805 (2)	0.98626 (19)	0.12237 (5)	0.0382 (4)
N1	0.7771 (3)	0.5614 (2)	0.07936 (5)	0.0262 (4)
N2	0.8540 (3)	0.53524 (19)	0.12186 (5)	0.0244 (3)
C1	0.5770 (3)	0.6695 (2)	0.06949 (6)	0.0236 (4)
C2	0.4368 (3)	0.7287 (2)	0.10308 (6)	0.0233 (4)
H2	0.4746	0.6980	0.1331	0.028*
C3	0.2409 (3)	0.8333 (2)	0.09152 (6)	0.0252 (4)
C4	0.1826 (4)	0.8796 (3)	0.04653 (6)	0.0311 (5)
H4	0.0514	0.9500	0.0388	0.037*
C5	0.3226 (4)	0.8194 (3)	0.01347 (7)	0.0339 (5)
H5	0.2836	0.8488	−0.0166	0.041*
C6	0.5206 (4)	0.7156 (3)	0.02464 (6)	0.0307 (5)
H6	0.6147	0.6772	0.0023	0.037*
C7	1.0448 (3)	0.4360 (2)	0.13145 (6)	0.0244 (4)
C8	1.1796 (3)	0.3516 (2)	0.09708 (6)	0.0275 (4)
C9	1.3961 (3)	0.2599 (2)	0.11294 (7)	0.0299 (4)
H9	1.4850	0.2050	0.0921	0.036*
C10	1.4711 (3)	0.2523 (2)	0.15691 (7)	0.0289 (4)
H10	1.6132	0.1947	0.1654	0.035*
C11	1.3401 (3)	0.3301 (2)	0.19198 (6)	0.0260 (4)
C12	1.1257 (3)	0.4201 (2)	0.17941 (6)	0.0231 (4)
C13	0.9988 (3)	0.4950 (2)	0.21333 (6)	0.0262 (4)
H13	0.8574	0.5543	0.2054	0.031*
C14	1.0815 (3)	0.4817 (2)	0.25807 (6)	0.0291 (4)
H14	0.9957	0.5322	0.2801	0.035*
C15	1.2930 (4)	0.3929 (2)	0.27070 (7)	0.0306 (5)
H15	1.3478	0.3842	0.3010	0.037*
C16	1.4203 (3)	0.3179 (2)	0.23791 (6)	0.0289 (4)
H16	1.5610	0.2586	0.2464	0.035*
C17	0.0939 (4)	0.8931 (2)	0.12780 (7)	0.0299 (4)
H17	0.1386	0.8564	0.1571	0.036*
H1	0.862 (5)	0.511 (4)	0.0554 (10)	0.079 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0355 (8)	0.0430 (8)	0.0283 (8)	0.0046 (7)	0.0063 (6)	−0.0055 (6)
O2	0.0316 (8)	0.0381 (8)	0.0459 (9)	0.0057 (7)	0.0096 (7)	−0.0013 (7)
N1	0.0251 (8)	0.0315 (9)	0.0222 (8)	0.0016 (7)	0.0040 (7)	0.0001 (7)
N2	0.0250 (8)	0.0244 (8)	0.0240 (8)	−0.0036 (6)	0.0036 (6)	0.0014 (6)
C1	0.0221 (9)	0.0239 (9)	0.0250 (9)	−0.0017 (7)	0.0026 (7)	0.0012 (7)
C2	0.0228 (9)	0.0274 (9)	0.0197 (9)	−0.0023 (7)	0.0005 (7)	0.0001 (7)
C3	0.0236 (9)	0.0261 (9)	0.0261 (10)	−0.0037 (8)	0.0020 (7)	−0.0011 (8)
C4	0.0278 (10)	0.0339 (11)	0.0312 (11)	0.0044 (8)	−0.0003 (8)	0.0035 (8)
C5	0.0372 (12)	0.0425 (12)	0.0217 (9)	0.0040 (9)	0.0002 (8)	0.0050 (9)
C6	0.0325 (11)	0.0360 (11)	0.0246 (10)	0.0001 (9)	0.0079 (8)	0.0002 (8)
C7	0.0225 (9)	0.0224 (9)	0.0289 (10)	−0.0012 (7)	0.0048 (8)	0.0007 (7)
C8	0.0281 (10)	0.0258 (10)	0.0295 (10)	−0.0039 (8)	0.0081 (8)	−0.0015 (8)
C9	0.0253 (10)	0.0283 (10)	0.0374 (12)	0.0005 (8)	0.0104 (8)	−0.0037 (8)
C10	0.0210 (10)	0.0240 (9)	0.0422 (12)	0.0018 (8)	0.0055 (8)	0.0026 (8)
C11	0.0223 (9)	0.0221 (9)	0.0339 (10)	−0.0032 (7)	0.0037 (8)	0.0015 (8)
C12	0.0203 (9)	0.0223 (9)	0.0270 (10)	−0.0033 (7)	0.0029 (7)	0.0018 (7)
C13	0.0254 (9)	0.0252 (9)	0.0284 (10)	0.0016 (8)	0.0056 (8)	0.0014 (8)
C14	0.0327 (11)	0.0278 (10)	0.0272 (10)	0.0004 (8)	0.0049 (8)	0.0004 (8)
C15	0.0368 (11)	0.0270 (10)	0.0271 (10)	−0.0039 (8)	−0.0035 (9)	0.0036 (8)
C16	0.0248 (10)	0.0250 (10)	0.0362 (11)	−0.0001 (8)	−0.0021 (8)	0.0044 (8)
C17	0.0293 (10)	0.0297 (10)	0.0310 (11)	0.0003 (8)	0.0040 (8)	−0.0023 (8)

O1—C8	1.260 (2)	C7—C8	1.472 (3)
O2—C17	1.217 (2)	C8—C9	1.453 (3)
N1—N2	1.316 (2)	C9—C10	1.340 (3)
N1—C1	1.413 (2)	C9—H9	0.9300
N1—H1	0.97 (3)	C10—C11	1.454 (3)
N2—C7	1.331 (2)	C10—H10	0.9300
C1—C6	1.391 (3)	C11—C16	1.405 (3)
C1—C2	1.397 (3)	C11—C12	1.414 (3)
C2—C3	1.387 (3)	C12—C13	1.405 (3)
C2—H2	0.9300	C13—C14	1.375 (3)
C3—C4	1.397 (3)	C13—H13	0.9300
C3—C17	1.483 (3)	C14—C15	1.396 (3)
C4—C5	1.387 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.382 (3)
C5—C6	1.390 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—C12	1.465 (3)
N2—N1—C1	118.93 (16)	C10—C9—C8	121.69 (18)
N2—N1—H1	119.8 (17)	C10—C9—H9	119.2
C1—N1—H1	121.2 (17)	C8—C9—H9	119.2
N1—N2—C7	119.34 (16)	C9—C10—C11	122.90 (18)
C6—C1—C2	120.10 (17)	C9—C10—H10	118.6
C6—C1—N1	117.88 (17)	C11—C10—H10	118.6
C2—C1—N1	122.02 (17)	C16—C11—C12	119.23 (17)
C3—C2—C1	119.72 (17)	C16—C11—C10	121.81 (18)
C3—C2—H2	120.1	C12—C11—C10	118.96 (18)
C1—C2—H2	120.1	C13—C12—C11	118.94 (17)
C2—C3—C4	120.49 (17)	C13—C12—C7	121.84 (17)
C2—C3—C17	118.60 (17)	C11—C12—C7	119.20 (17)
C4—C3—C17	120.91 (18)	C14—C13—C12	120.71 (18)
C5—C4—C3	119.22 (19)	C14—C13—H13	119.6
C5—C4—H4	120.4	C12—C13—H13	119.6
C3—C4—H4	120.4	C13—C14—C15	120.62 (18)
C4—C5—C6	120.87 (18)	C13—C14—H14	119.7
C4—C5—H5	119.6	C15—C14—H14	119.7
C6—C5—H5	119.6	C16—C15—C14	119.64 (18)
C5—C6—C1	119.59 (18)	C16—C15—H15	120.2
C5—C6—H6	120.2	C14—C15—H15	120.2
C1—C6—H6	120.2	C15—C16—C11	120.86 (18)
N2—C7—C12	115.93 (16)	C15—C16—H16	119.6
N2—C7—C8	123.94 (17)	C11—C16—H16	119.6
C12—C7—C8	120.07 (17)	O2—C17—C3	125.28 (19)
O1—C8—C9	121.63 (17)	O2—C17—H17	117.4
O1—C8—C7	121.23 (18)	C3—C17—H17	117.4
C9—C8—C7	117.11 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.97 (3)	1.83 (3)	2.577 (3)	133 (3)
C6—H6···O1i	0.93	2.41	3.327 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.97 (3)	1.83 (3)	2.577 (3)	133 (3)
C6—H6⋯O1i	0.93	2.41	3.327 (4)	168

Symmetry code: (i) .