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

The title zwitterion,, C16H11ClN2O, is approximately planar, the dihedral angle between the benzene ring and naphthalene ring system is 1.55 (13)°; an intra-molecular N-H⋯O hydrogen bond stabilizes the planar conformation. In the crystal, π-π stacking between the benzene ring and the naphthalene ring system of adjacent mol-ecules links the mol-ecules into supra-molecular chains running along the b axis, the centroid-centroid distance being 3.765 (2) Å.

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 ▶). Many azo compounds have been synthesized by diazo­tization and diazo-coupling reactions; for information, see: Wang et al. (2003 ▶). For a related structure, see: Elmali et al. (2001 ▶).

Experimental

Crystal data

C16H11ClN2O

M = 282.72

Monoclinic,

a = 16.340 (2) Å

b = 5.7665 (4) Å

c = 15.632 (2) Å

β = 113.604 (4)°

V = 1349.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.09 × 0.04 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

4488 measured reflections

2418 independent reflections

1289 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.185

S = 1.01

2418 reflections

171 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.28 e Å−3

Data collection: KappaCCD Reference Manual (Nonius, 1998 ▶); 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) global, I. DOI: 10.1107/S1600536813014931/xu5708sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014931/xu5708Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014931/xu5708Isup3.cml

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

C16H11ClN2O	F(000) = 584
Mr = 282.72	Dx = 1.391 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2548 reflections
a = 16.340 (2) Å	θ = 2.9–25.4°
b = 5.7665 (4) Å	µ = 0.28 mm−1
c = 15.632 (2) Å	T = 293 K
β = 113.604 (4)°	Needle, red
V = 1349.7 (3) Å3	0.09 × 0.04 × 0.02 mm
Z = 4

Nonius KappaCCD diffractometer	1289 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Horizonally mounted graphite crystal monochromator	θmax = 25.3°, θmin = 3.1°
Detector resolution: 9 pixels mm-1	h = −19→19
CCD rotation images, thick slices scans	k = −6→6
4488 measured reflections	l = −18→18
2418 independent 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0928P)2 + 0.1732P] where P = (Fo2 + 2Fc2)/3
2418 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl1	0.06364 (8)	−0.5972 (2)	0.37478 (9)	0.1078 (5)
O1	0.46478 (16)	0.1141 (4)	0.38441 (18)	0.0786 (9)
N1	0.33259 (17)	−0.1220 (4)	0.38634 (18)	0.0572 (9)
N2	0.27805 (17)	0.0115 (4)	0.32242 (17)	0.0528 (8)
C1	0.2977 (2)	−0.3084 (5)	0.4184 (2)	0.0535 (10)
C2	0.2070 (2)	−0.3500 (5)	0.3853 (2)	0.0583 (11)
C3	0.1771 (2)	−0.5415 (6)	0.4175 (2)	0.0667 (12)
C4	0.2351 (3)	−0.6891 (6)	0.4821 (3)	0.0746 (14)
C5	0.3258 (3)	−0.6464 (6)	0.5165 (2)	0.0708 (14)
C6	0.3578 (2)	−0.4547 (6)	0.4852 (2)	0.0666 (12)
C7	0.3117 (2)	0.1901 (5)	0.2907 (2)	0.0523 (11)
C8	0.4066 (2)	0.2395 (5)	0.3238 (2)	0.0613 (11)
C9	0.4306 (2)	0.4390 (6)	0.2841 (3)	0.0714 (14)
C10	0.3705 (3)	0.5765 (6)	0.2221 (3)	0.0670 (12)
C11	0.2759 (2)	0.5349 (5)	0.1888 (2)	0.0572 (11)
C12	0.2463 (2)	0.3361 (5)	0.2220 (2)	0.0504 (10)
C13	0.1542 (2)	0.2970 (5)	0.1879 (2)	0.0618 (11)
C14	0.0948 (2)	0.4492 (6)	0.1263 (3)	0.0730 (12)
C15	0.1241 (3)	0.6417 (6)	0.0963 (2)	0.0698 (14)
C16	0.2134 (3)	0.6844 (5)	0.1264 (2)	0.0684 (13)
H1	0.39440	−0.10220	0.40590	0.0690*
H2	0.16670	−0.25050	0.34200	0.0700*
H4	0.21350	−0.81740	0.50270	0.0900*
H5	0.36550	−0.74560	0.56060	0.0850*
H6	0.41880	−0.42450	0.50860	0.0800*
H9	0.49090	0.47380	0.30250	0.0860*
H10	0.39040	0.70430	0.19950	0.0800*
H13	0.13290	0.16620	0.20720	0.0740*
H14	0.03380	0.42060	0.10480	0.0870*
H15	0.08320	0.74400	0.05520	0.0840*
H16	0.23270	0.81510	0.10510	0.0820*

	U11	U22	U33	U12	U13	U23
Cl1	0.0856 (8)	0.1168 (9)	0.1281 (10)	−0.0275 (6)	0.0501 (7)	0.0075 (7)
O1	0.0545 (15)	0.0780 (15)	0.0954 (19)	0.0021 (12)	0.0218 (14)	0.0107 (14)
N1	0.0531 (16)	0.0556 (14)	0.0611 (17)	−0.0055 (13)	0.0212 (14)	−0.0046 (14)
N2	0.0587 (16)	0.0505 (13)	0.0489 (15)	−0.0023 (12)	0.0213 (13)	−0.0068 (12)
C1	0.066 (2)	0.0448 (16)	0.0501 (18)	−0.0040 (14)	0.0237 (17)	−0.0070 (14)
C2	0.067 (2)	0.0518 (17)	0.059 (2)	−0.0067 (16)	0.0284 (17)	−0.0001 (16)
C3	0.076 (2)	0.068 (2)	0.063 (2)	−0.0122 (18)	0.035 (2)	−0.0072 (18)
C4	0.111 (3)	0.056 (2)	0.065 (2)	−0.010 (2)	0.044 (2)	−0.0048 (18)
C5	0.096 (3)	0.058 (2)	0.056 (2)	0.0043 (19)	0.028 (2)	0.0039 (17)
C6	0.072 (2)	0.066 (2)	0.058 (2)	−0.0013 (17)	0.0222 (18)	−0.0094 (17)
C7	0.055 (2)	0.0517 (17)	0.0529 (18)	−0.0054 (14)	0.0244 (16)	−0.0074 (15)
C8	0.059 (2)	0.0605 (19)	0.067 (2)	−0.0076 (17)	0.0281 (18)	−0.0088 (17)
C9	0.058 (2)	0.077 (2)	0.086 (3)	−0.0100 (19)	0.036 (2)	−0.003 (2)
C10	0.076 (2)	0.063 (2)	0.071 (2)	−0.0154 (18)	0.039 (2)	−0.0017 (17)
C11	0.070 (2)	0.0540 (17)	0.0536 (19)	−0.0028 (16)	0.0310 (17)	−0.0088 (15)
C12	0.0576 (19)	0.0468 (16)	0.0502 (18)	−0.0044 (14)	0.0251 (15)	−0.0082 (14)
C13	0.060 (2)	0.0612 (19)	0.062 (2)	−0.0075 (16)	0.0220 (18)	−0.0024 (17)
C14	0.058 (2)	0.082 (2)	0.069 (2)	0.0026 (19)	0.0149 (18)	−0.003 (2)
C15	0.078 (3)	0.063 (2)	0.059 (2)	0.0111 (19)	0.0177 (19)	0.0035 (17)
C16	0.097 (3)	0.0522 (19)	0.057 (2)	0.0012 (18)	0.032 (2)	0.0015 (17)

Cl1—C3	1.731 (4)	C11—C16	1.393 (5)
O1—C8	1.266 (4)	C11—C12	1.421 (4)
N1—N2	1.293 (4)	C12—C13	1.399 (5)
N1—C1	1.400 (4)	C13—C14	1.375 (5)
N2—C7	1.352 (4)	C14—C15	1.364 (5)
N1—H1	0.9400	C15—C16	1.364 (7)
C1—C2	1.381 (5)	C2—H2	0.9300
C1—C6	1.395 (4)	C4—H4	0.9300
C2—C3	1.382 (5)	C5—H5	0.9300
C3—C4	1.370 (5)	C6—H6	0.9300
C4—C5	1.381 (7)	C9—H9	0.9300
C5—C6	1.393 (5)	C10—H10	0.9300
C7—C8	1.453 (5)	C13—H13	0.9300
C7—C12	1.444 (4)	C14—H14	0.9300
C8—C9	1.434 (5)	C15—H15	0.9300
C9—C10	1.331 (6)	C16—H16	0.9300
C10—C11	1.440 (6)
N2—N1—C1	118.7 (3)	C7—C12—C11	118.9 (3)
N1—N2—C7	118.8 (3)	C7—C12—C13	123.5 (3)
C1—N1—H1	121.00	C12—C13—C14	120.9 (3)
N2—N1—H1	120.00	C13—C14—C15	120.9 (4)
N1—C1—C6	117.8 (3)	C14—C15—C16	120.2 (3)
C2—C1—C6	120.2 (3)	C11—C16—C15	120.9 (3)
N1—C1—C2	121.9 (3)	C1—C2—H2	120.00
C1—C2—C3	119.0 (3)	C3—C2—H2	121.00
Cl1—C3—C4	119.2 (3)	C3—C4—H4	120.00
Cl1—C3—C2	119.2 (3)	C5—C4—H4	120.00
C2—C3—C4	121.6 (3)	C4—C5—H5	120.00
C3—C4—C5	119.6 (4)	C6—C5—H5	120.00
C4—C5—C6	120.0 (3)	C1—C6—H6	120.00
C1—C6—C5	119.5 (3)	C5—C6—H6	120.00
C8—C7—C12	121.1 (3)	C8—C9—H9	119.00
N2—C7—C8	123.5 (3)	C10—C9—H9	119.00
N2—C7—C12	115.4 (3)	C9—C10—H10	119.00
C7—C8—C9	116.2 (3)	C11—C10—H10	119.00
O1—C8—C9	121.9 (3)	C12—C13—H13	119.00
O1—C8—C7	121.9 (3)	C14—C13—H13	120.00
C8—C9—C10	122.9 (4)	C13—C14—H14	120.00
C9—C10—C11	122.4 (4)	C15—C14—H14	120.00
C12—C11—C16	119.6 (3)	C14—C15—H15	120.00
C10—C11—C12	118.4 (3)	C16—C15—H15	120.00
C10—C11—C16	122.0 (3)	C11—C16—H16	120.00
C11—C12—C13	117.6 (3)	C15—C16—H16	120.00
C1—N1—N2—C7	−179.3 (3)	N2—C7—C12—C13	−1.3 (4)
N2—N1—C1—C2	−1.5 (4)	C8—C7—C12—C11	−1.9 (4)
N2—N1—C1—C6	178.0 (3)	C8—C7—C12—C13	−179.8 (3)
N1—N2—C7—C8	0.8 (4)	O1—C8—C9—C10	−178.3 (4)
N1—N2—C7—C12	−177.7 (3)	C7—C8—C9—C10	1.5 (5)
N1—C1—C2—C3	177.8 (3)	C8—C9—C10—C11	−0.7 (6)
C6—C1—C2—C3	−1.7 (5)	C9—C10—C11—C12	−1.6 (6)
N1—C1—C6—C5	−177.9 (3)	C9—C10—C11—C16	177.7 (4)
C2—C1—C6—C5	1.6 (5)	C10—C11—C12—C7	2.8 (4)
C1—C2—C3—Cl1	−178.9 (2)	C10—C11—C12—C13	−179.2 (3)
C1—C2—C3—C4	0.8 (5)	C16—C11—C12—C7	−176.5 (3)
Cl1—C3—C4—C5	179.9 (3)	C16—C11—C12—C13	1.5 (4)
C2—C3—C4—C5	0.2 (6)	C10—C11—C16—C15	−179.6 (3)
C3—C4—C5—C6	−0.3 (6)	C12—C11—C16—C15	−0.4 (5)
C4—C5—C6—C1	−0.7 (5)	C7—C12—C13—C14	176.4 (3)
N2—C7—C8—O1	1.1 (5)	C11—C12—C13—C14	−1.6 (5)
N2—C7—C8—C9	−178.7 (3)	C12—C13—C14—C15	0.4 (5)
C12—C7—C8—O1	179.6 (3)	C13—C14—C15—C16	0.8 (6)
C12—C7—C8—C9	−0.2 (4)	C14—C15—C16—C11	−0.8 (5)
N2—C7—C12—C11	176.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.94	1.82	2.564 (4)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.94	1.82	2.564 (4)	135