1-[(E)-4-(Phenyl-diazen-yl)phen-yl]-3-pyrroline-2,5-dione.

The title compound, C(16)H(11)N(3)O(2), displays a trans configuration with respect to the azo group. The mol-ecule is non-planar; the maleimide ring forms a dihedral angle of 42.35 (4)° with the benzene ring bonded to its N atom and the mean plane of this benzene ring is rotated by 21.46 (8)° with respect to the azo group mean plane, which, in turn, forms a dihedral angle of 24.48 (7)° with the 'terminal' benzene ring. Mol-ecules in the crystal are π-π stacked along the [100] direction with a mean inter-planar distance of 3.857 (1) Å. In addition, C-H⋯O inter-actions link them into double layers parallel to the ac plane.

Related literature

For studies of photo- and thermal isomerization of aromatic azo compounds, see: Serra & Terentjev (2008 ▶). For azocompounds based on maleimides, see: Mohammed & Mustapha (2010 ▶); Oishi et al. (2011 ▶). For the reactivity of the maleimide group, see: Knauf et al. (2004 ▶); Durmaz et al. (2006 ▶); Pounder et al. (2008 ▶).

Experimental

Crystal data

C16H11N3O2

M = 277.28

Triclinic,

a = 3.8571 (2) Å

b = 10.9189 (7) Å

c = 15.784 (1) Å

α = 78.297 (5)°

β = 87.301 (5)°

γ = 88.809 (5)°

V = 650.18 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.20 × 0.15 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.981, T max = 0.986

8689 measured reflections

2556 independent reflections

2189 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.03

2556 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681103193X/ya2141sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103193X/ya2141Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103193X/ya2141Isup3.cml

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

C16H11N3O2	Z = 2
Mr = 277.28	F(000) = 288
Triclinic, P1	Dx = 1.416 Mg m−3
Hall symbol: -P 1	Melting point: 442 K
a = 3.8571 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9189 (7) Å	Cell parameters from 2982 reflections
c = 15.784 (1) Å	θ = 2.9–29.3°
α = 78.297 (5)°	µ = 0.10 mm−1
β = 87.301 (5)°	T = 200 K
γ = 88.809 (5)°	Prism, orange
V = 650.18 (7) Å3	0.20 × 0.15 × 0.15 mm

Oxford Diffraction Xcalibur Eos diffractometer	2556 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2189 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 16.1593 pixels mm-1	θmax = 26.0°, θmin = 2.9°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
Tmin = 0.981, Tmax = 0.986	l = −19→19
8689 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.1268P] where P = (Fo2 + 2Fc2)/3
2556 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 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
N2	0.2043 (3)	0.69925 (10)	0.48218 (7)	0.0266 (3)
N1	−0.0181 (3)	0.74413 (10)	0.12701 (7)	0.0268 (3)
O1	−0.2299 (3)	0.94847 (8)	0.09406 (6)	0.0328 (3)
C6	−0.0493 (3)	0.62500 (12)	0.27614 (8)	0.0262 (3)
H6	−0.1515	0.5594	0.2574	0.031*
N3	0.2360 (3)	0.80091 (10)	0.50624 (7)	0.0273 (3)
C9	0.2492 (3)	0.82310 (12)	0.33156 (9)	0.0256 (3)
H9	0.3477	0.8894	0.3504	0.031*
C10	0.1985 (3)	0.83144 (12)	0.24472 (8)	0.0259 (3)
H10	0.2662	0.9027	0.2048	0.031*
C7	0.0096 (3)	0.61594 (12)	0.36306 (9)	0.0269 (3)
H7	−0.0471	0.5430	0.4026	0.032*
C5	0.0458 (3)	0.73313 (12)	0.21706 (8)	0.0240 (3)
C11	0.3041 (3)	0.78708 (12)	0.59567 (8)	0.0251 (3)
O2	0.1582 (3)	0.54706 (9)	0.10682 (7)	0.0440 (3)
C16	0.2175 (4)	0.88877 (13)	0.63313 (9)	0.0297 (3)
H16	0.1262	0.9613	0.5998	0.036*
C12	0.4561 (4)	0.68014 (13)	0.64430 (9)	0.0287 (3)
H12	0.5199	0.6130	0.6186	0.034*
C8	0.1530 (3)	0.71524 (12)	0.39132 (8)	0.0243 (3)
C13	0.5111 (4)	0.67469 (14)	0.73067 (9)	0.0334 (3)
H13	0.6139	0.6040	0.7634	0.040*
C4	−0.1609 (3)	0.84996 (12)	0.07348 (8)	0.0260 (3)
C3	0.0284 (4)	0.64799 (13)	0.08024 (9)	0.0306 (3)
C1	−0.2072 (4)	0.81469 (13)	−0.01158 (9)	0.0318 (3)
H1	−0.2962	0.8667	−0.0600	0.038*
C15	0.2678 (4)	0.88172 (14)	0.72036 (9)	0.0334 (3)
H15	0.2043	0.9486	0.7463	0.040*
C2	−0.1022 (4)	0.69835 (13)	−0.00739 (9)	0.0339 (3)
H2	−0.1085	0.6546	−0.0520	0.041*
C14	0.4132 (4)	0.77460 (14)	0.76871 (9)	0.0345 (3)
H14	0.4454	0.7696	0.8273	0.041*

	U11	U22	U33	U12	U13	U23
N2	0.0303 (6)	0.0253 (6)	0.0246 (6)	0.0005 (4)	−0.0026 (5)	−0.0062 (5)
N1	0.0366 (6)	0.0216 (6)	0.0225 (6)	0.0040 (5)	−0.0046 (5)	−0.0052 (4)
O1	0.0456 (6)	0.0215 (5)	0.0303 (5)	0.0056 (4)	−0.0011 (4)	−0.0038 (4)
C6	0.0319 (7)	0.0201 (6)	0.0276 (7)	−0.0005 (5)	−0.0036 (5)	−0.0070 (5)
N3	0.0327 (6)	0.0253 (6)	0.0242 (6)	0.0025 (5)	−0.0027 (5)	−0.0056 (5)
C9	0.0281 (7)	0.0222 (7)	0.0277 (7)	−0.0009 (5)	−0.0005 (5)	−0.0079 (5)
C10	0.0292 (7)	0.0218 (7)	0.0257 (7)	0.0001 (5)	0.0016 (5)	−0.0031 (5)
C7	0.0330 (7)	0.0201 (6)	0.0263 (7)	0.0012 (5)	−0.0006 (5)	−0.0019 (5)
C5	0.0272 (7)	0.0231 (7)	0.0218 (6)	0.0057 (5)	−0.0017 (5)	−0.0055 (5)
C11	0.0263 (6)	0.0254 (7)	0.0238 (7)	−0.0025 (5)	−0.0023 (5)	−0.0049 (5)
O2	0.0742 (8)	0.0275 (6)	0.0324 (6)	0.0184 (5)	−0.0128 (5)	−0.0105 (4)
C16	0.0344 (7)	0.0245 (7)	0.0304 (7)	0.0009 (5)	−0.0034 (6)	−0.0060 (6)
C12	0.0317 (7)	0.0238 (7)	0.0315 (7)	0.0005 (5)	−0.0048 (6)	−0.0065 (6)
C8	0.0250 (6)	0.0245 (7)	0.0232 (7)	0.0033 (5)	−0.0017 (5)	−0.0048 (5)
C13	0.0360 (8)	0.0311 (8)	0.0313 (8)	−0.0013 (6)	−0.0109 (6)	0.0002 (6)
C4	0.0288 (7)	0.0229 (7)	0.0250 (7)	0.0000 (5)	−0.0011 (5)	−0.0021 (5)
C3	0.0424 (8)	0.0247 (7)	0.0258 (7)	0.0038 (6)	−0.0046 (6)	−0.0076 (5)
C1	0.0404 (8)	0.0289 (7)	0.0254 (7)	−0.0006 (6)	−0.0083 (6)	−0.0023 (6)
C15	0.0366 (8)	0.0341 (8)	0.0328 (8)	−0.0014 (6)	−0.0009 (6)	−0.0148 (6)
C2	0.0484 (9)	0.0303 (8)	0.0248 (7)	0.0001 (6)	−0.0070 (6)	−0.0085 (6)
C14	0.0371 (8)	0.0430 (9)	0.0246 (7)	−0.0071 (6)	−0.0062 (6)	−0.0080 (6)

N2—N3	1.2539 (15)	C11—C16	1.3879 (19)
N2—C8	1.4320 (16)	C11—C12	1.3952 (19)
N1—C3	1.4046 (17)	O2—C3	1.2044 (17)
N1—C4	1.4049 (17)	C16—C15	1.3860 (19)
N1—C5	1.4346 (16)	C16—H16	0.9300
O1—C4	1.2062 (16)	C12—C13	1.3786 (19)
C6—C7	1.3845 (18)	C12—H12	0.9300
C6—C5	1.3918 (18)	C13—C14	1.386 (2)
C6—H6	0.9300	C13—H13	0.9300
N3—C11	1.4252 (16)	C4—C1	1.4893 (19)
C9—C10	1.3781 (18)	C3—C2	1.4882 (19)
C9—C8	1.3960 (18)	C1—C2	1.315 (2)
C9—H9	0.9300	C1—H1	0.9300
C10—C5	1.3893 (18)	C15—C14	1.384 (2)
C10—H10	0.9300	C15—H15	0.9300
C7—C8	1.3874 (18)	C2—H2	0.9300
C7—H7	0.9300	C14—H14	0.9300
N3—N2—C8	112.96 (11)	C13—C12—H12	120.2
C3—N1—C4	109.32 (10)	C11—C12—H12	120.2
C3—N1—C5	125.35 (11)	C7—C8—C9	119.91 (12)
C4—N1—C5	125.18 (11)	C7—C8—N2	117.05 (11)
C7—C6—C5	119.44 (12)	C9—C8—N2	123.01 (11)
C7—C6—H6	120.3	C12—C13—C14	119.98 (13)
C5—C6—H6	120.3	C12—C13—H13	120.0
N2—N3—C11	113.94 (11)	C14—C13—H13	120.0
C10—C9—C8	120.04 (12)	O1—C4—N1	125.76 (12)
C10—C9—H9	120.0	O1—C4—C1	128.12 (12)
C8—C9—H9	120.0	N1—C4—C1	106.12 (11)
C9—C10—C5	119.80 (12)	O2—C3—N1	125.56 (12)
C9—C10—H10	120.1	O2—C3—C2	128.17 (13)
C5—C10—H10	120.1	N1—C3—C2	106.24 (11)
C6—C7—C8	120.25 (12)	C2—C1—C4	109.21 (12)
C6—C7—H7	119.9	C2—C1—H1	125.4
C8—C7—H7	119.9	C4—C1—H1	125.4
C10—C5—C6	120.52 (12)	C14—C15—C16	119.64 (13)
C10—C5—N1	119.59 (11)	C14—C15—H15	120.2
C6—C5—N1	119.88 (11)	C16—C15—H15	120.2
C16—C11—C12	120.39 (12)	C1—C2—C3	109.09 (12)
C16—C11—N3	116.13 (11)	C1—C2—H2	125.5
C12—C11—N3	123.46 (12)	C3—C2—H2	125.5
C15—C16—C11	119.71 (13)	C15—C14—C13	120.69 (13)
C15—C16—H16	120.1	C15—C14—H14	119.7
C11—C16—H16	120.1	C13—C14—H14	119.7
C13—C12—C11	119.52 (13)
C8—N2—N3—C11	−177.11 (10)	C10—C9—C8—N2	178.76 (11)
C8—C9—C10—C5	1.12 (19)	N3—N2—C8—C7	−160.38 (12)
C5—C6—C7—C8	1.8 (2)	N3—N2—C8—C9	21.50 (18)
C9—C10—C5—C6	−1.5 (2)	C11—C12—C13—C14	0.5 (2)
C9—C10—C5—N1	177.72 (11)	C3—N1—C4—O1	−179.48 (13)
C7—C6—C5—C10	0.0 (2)	C5—N1—C4—O1	4.7 (2)
C7—C6—C5—N1	−179.20 (11)	C3—N1—C4—C1	0.59 (15)
C3—N1—C5—C10	140.32 (14)	C5—N1—C4—C1	−175.19 (12)
C4—N1—C5—C10	−44.57 (18)	C4—N1—C3—O2	176.90 (15)
C3—N1—C5—C6	−40.51 (19)	C5—N1—C3—O2	−7.3 (2)
C4—N1—C5—C6	134.60 (14)	C4—N1—C3—C2	−1.19 (16)
N2—N3—C11—C16	−157.20 (12)	C5—N1—C3—C2	174.57 (12)
N2—N3—C11—C12	24.26 (18)	O1—C4—C1—C2	−179.59 (14)
C12—C11—C16—C15	−3.0 (2)	N1—C4—C1—C2	0.34 (16)
N3—C11—C16—C15	178.44 (12)	C11—C16—C15—C14	1.8 (2)
C16—C11—C12—C13	1.8 (2)	C4—C1—C2—C3	−1.07 (17)
N3—C11—C12—C13	−179.72 (12)	O2—C3—C2—C1	−176.60 (16)
C6—C7—C8—C9	−2.2 (2)	N1—C3—C2—C1	1.43 (17)
C6—C7—C8—N2	179.63 (11)	C16—C15—C14—C13	0.5 (2)
C10—C9—C8—C7	0.7 (2)	C12—C13—C14—C15	−1.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.93	2.54	3.3841 (18)	152
C10—H10···O1ii	0.93	2.54	3.2464 (16)	133
C13—H13···O2iii	0.93	2.54	3.4248 (18)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.93	2.54	3.3841 (18)	152
C10—H10⋯O1ii	0.93	2.54	3.2464 (16)	133
C13—H13⋯O2iii	0.93	2.54	3.4248 (18)	160

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