(E)-1-(4-Meth-oxy-anthracen-1-yl)-2-phenyl-diazene.

The title compound, C(21)H(16)N(2)O, has an E-conformation about the diazene N=N bond. It is reasonably planar with the phenyl ring being inclined to the mean plane of the anthracene moiety [planar to within 0.077 (3) Å] by 6.43 (10)°. The crystal structure is stabilized by C-H⋯π and weak π-π inter-actions [centroid-centroid distances of 3.7192 (16) and 3.8382 (15) Å], leading to the formation of two-dimensional networks stacking along [001] and lying parallel to (110).

Related literature

For background to sensing mol­ecules based on tautomeric switches, see: Nedeltcheva et al. (2009 ▶); Antonov et al. (2009 ▶, 2010 ▶). For investigations of the tautomerism of azodyes, see: Kelemen (1981 ▶). For the synthesis of the title compound, see: Nedeltcheva et al. (2010 ▶).

Experimental

Crystal data

C21H16N2O

M = 312.36

Orthorhombic,

a = 6.3021 (3) Å

b = 9.0481 (4) Å

c = 27.3935 (17) Å

V = 1562.03 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.54 × 0.32 × 0.12 mm

Data collection

STOE IPDS 2T diffractometer

12181 measured reflections

2584 independent reflections

2096 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.086

S = 1.10

2584 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010932/nc2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010932/nc2221Isup2.hkl

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

C21H16N2O	F(000) = 656
Mr = 312.36	Dx = 1.328 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8137 reflections
a = 6.3021 (3) Å	θ = 1.5–25.1°
b = 9.0481 (4) Å	µ = 0.08 mm−1
c = 27.3935 (17) Å	T = 150 K
V = 1562.03 (14) Å3	Block, red
Z = 4	0.54 × 0.32 × 0.12 mm

STOE IPDS 2T diffractometer	2096 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.072
graphite	θmax = 24.6°, θmin = 1.5°
Detector resolution: 6.67 pixels mm-1	h = −6→7
rotation method scans	k = −9→10
12181 measured reflections	l = −32→32
2584 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0342P)2 + 0.1352P] where P = (Fo2 + 2Fc2)/3
2584 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.3714 (4)	−0.0729 (3)	0.41632 (8)	0.0295 (6)
C2	0.2333 (4)	−0.0908 (3)	0.45491 (10)	0.0390 (7)
H2	0.2609	−0.0433	0.4852	0.047*
C3	0.0531 (5)	−0.1787 (3)	0.44947 (11)	0.0459 (8)
H3	−0.0422	−0.1911	0.4760	0.055*
C4	0.0136 (5)	−0.2471 (3)	0.40569 (10)	0.0428 (8)
H4	−0.1105	−0.3056	0.4018	0.051*
C5	0.1533 (5)	−0.2314 (3)	0.36735 (11)	0.0410 (7)
H5	0.1260	−0.2802	0.3373	0.049*
C6	0.3333 (4)	−0.1448 (3)	0.37242 (9)	0.0343 (6)
H6	0.4300	−0.1348	0.3460	0.041*
C7	0.8346 (4)	0.1413 (3)	0.39361 (8)	0.0279 (6)
C8	0.9818 (4)	0.1429 (3)	0.35326 (8)	0.0278 (6)
C9	0.9493 (4)	0.0641 (3)	0.31029 (8)	0.0308 (6)
H9	0.8233	0.0075	0.3067	0.037*
C10	1.0975 (4)	0.0660 (3)	0.27227 (8)	0.0287 (6)
C11	1.0656 (5)	−0.0128 (3)	0.22788 (8)	0.0335 (6)
H11	0.9396	−0.0689	0.2235	0.040*
C12	1.2126 (5)	−0.0087 (3)	0.19165 (8)	0.0352 (7)
H12	1.1875	−0.0608	0.1621	0.042*
C13	1.4030 (4)	0.0725 (3)	0.19757 (9)	0.0355 (7)
H13	1.5051	0.0736	0.1721	0.043*
C14	1.4408 (4)	0.1487 (3)	0.23939 (8)	0.0328 (6)
H14	1.5688	0.2032	0.2428	0.039*
C15	1.2913 (4)	0.1479 (3)	0.27795 (8)	0.0280 (6)
C16	1.3235 (4)	0.2270 (3)	0.32118 (8)	0.0290 (6)
H16	1.4516	0.2808	0.3253	0.035*
C17	1.1728 (4)	0.2290 (3)	0.35837 (8)	0.0258 (6)
C18	1.2018 (4)	0.3159 (3)	0.40158 (8)	0.0284 (6)
C19	1.0512 (4)	0.3180 (3)	0.43775 (8)	0.0302 (6)
H19	1.0691	0.3792	0.4656	0.036*
C20	0.8696 (4)	0.2281 (3)	0.43313 (8)	0.0322 (7)
H20	0.7677	0.2285	0.4587	0.039*
C21	1.4285 (5)	0.4842 (3)	0.44324 (8)	0.0410 (7)
H21A	1.3165	0.5585	0.4470	0.061*
H21B	1.5656	0.5337	0.4390	0.061*
H21C	1.4333	0.4217	0.4724	0.061*
N1	0.5491 (4)	0.0227 (3)	0.42517 (7)	0.0329 (5)
N2	0.6573 (3)	0.0465 (2)	0.38713 (7)	0.0301 (5)
O1	1.3851 (3)	0.3951 (2)	0.40156 (6)	0.0347 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0235 (15)	0.0275 (16)	0.0375 (13)	0.0038 (13)	0.0023 (11)	0.0052 (11)
C2	0.0385 (18)	0.0367 (19)	0.0418 (14)	−0.0030 (14)	0.0075 (13)	−0.0038 (13)
C3	0.0361 (18)	0.044 (2)	0.0573 (17)	−0.0027 (16)	0.0182 (15)	−0.0014 (15)
C4	0.0335 (19)	0.0329 (18)	0.0620 (19)	0.0001 (14)	0.0059 (15)	−0.0030 (14)
C5	0.0377 (18)	0.0352 (18)	0.0500 (16)	−0.0040 (15)	−0.0016 (14)	−0.0009 (13)
C6	0.0330 (16)	0.0341 (16)	0.0359 (13)	0.0017 (14)	0.0032 (12)	0.0043 (12)
C7	0.0220 (15)	0.0298 (16)	0.0319 (12)	0.0031 (13)	−0.0034 (11)	0.0060 (11)
C8	0.0294 (15)	0.0280 (15)	0.0260 (12)	0.0022 (13)	−0.0010 (11)	0.0037 (10)
C9	0.0253 (14)	0.0341 (16)	0.0330 (13)	−0.0021 (13)	−0.0042 (12)	0.0013 (11)
C10	0.0272 (15)	0.0274 (15)	0.0314 (12)	0.0005 (13)	−0.0018 (11)	0.0003 (11)
C11	0.0357 (16)	0.0324 (16)	0.0322 (13)	−0.0038 (13)	−0.0045 (12)	−0.0007 (11)
C12	0.0410 (17)	0.0361 (17)	0.0285 (12)	−0.0008 (14)	−0.0017 (12)	−0.0026 (12)
C13	0.0365 (17)	0.0337 (17)	0.0363 (14)	0.0002 (15)	0.0047 (12)	−0.0013 (12)
C14	0.0291 (16)	0.0315 (16)	0.0378 (13)	−0.0024 (13)	0.0033 (12)	0.0005 (11)
C15	0.0314 (15)	0.0253 (15)	0.0273 (12)	0.0023 (12)	−0.0010 (12)	0.0025 (11)
C16	0.0247 (15)	0.0283 (16)	0.0341 (13)	0.0011 (12)	−0.0026 (12)	0.0021 (10)
C17	0.0254 (15)	0.0260 (15)	0.0259 (12)	0.0007 (12)	−0.0028 (11)	0.0013 (10)
C18	0.0265 (15)	0.0275 (16)	0.0312 (12)	−0.0005 (12)	−0.0048 (12)	0.0023 (11)
C19	0.0316 (16)	0.0314 (16)	0.0276 (12)	0.0030 (13)	−0.0025 (12)	−0.0038 (11)
C20	0.0312 (16)	0.0368 (17)	0.0285 (13)	0.0060 (14)	0.0018 (12)	0.0003 (11)
C21	0.0461 (18)	0.0429 (18)	0.0340 (13)	−0.0091 (15)	−0.0066 (13)	−0.0066 (12)
N1	0.0315 (13)	0.0331 (13)	0.0342 (11)	0.0031 (11)	0.0053 (10)	0.0021 (9)
N2	0.0246 (12)	0.0333 (14)	0.0325 (11)	0.0033 (11)	0.0005 (10)	0.0042 (9)
O1	0.0350 (12)	0.0380 (11)	0.0311 (9)	−0.0086 (9)	−0.0036 (8)	−0.0065 (8)

C1—C2	1.379 (3)	C11—H11	0.9500
C1—C6	1.389 (3)	C12—C13	1.416 (4)
C1—N1	1.435 (3)	C12—H12	0.9500
C2—C3	1.394 (4)	C13—C14	1.358 (3)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.373 (4)	C14—C15	1.415 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.378 (4)	C15—C16	1.398 (3)
C4—H4	0.9500	C16—C17	1.393 (3)
C5—C6	1.386 (4)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.433 (3)
C6—H6	0.9500	C18—O1	1.359 (3)
C7—C20	1.356 (3)	C18—C19	1.372 (3)
C7—N2	1.420 (3)	C19—C20	1.409 (4)
C7—C8	1.443 (3)	C19—H19	0.9500
C8—C9	1.391 (3)	C20—H20	0.9500
C8—C17	1.441 (4)	C21—O1	1.424 (3)
C9—C10	1.399 (3)	C21—H21A	0.9800
C9—H9	0.9500	C21—H21B	0.9800
C10—C11	1.423 (3)	C21—H21C	0.9800
C10—C15	1.437 (4)	N1—N2	1.264 (3)
C11—C12	1.358 (4)
C2—C1—C6	120.0 (3)	C13—C12—H12	119.7
C2—C1—N1	115.7 (2)	C14—C13—C12	120.6 (2)
C6—C1—N1	124.3 (2)	C14—C13—H13	119.7
C1—C2—C3	120.0 (3)	C12—C13—H13	119.7
C1—C2—H2	120.0	C13—C14—C15	120.7 (3)
C3—C2—H2	120.0	C13—C14—H14	119.7
C4—C3—C2	119.9 (3)	C15—C14—H14	119.7
C4—C3—H3	120.1	C16—C15—C14	122.2 (2)
C2—C3—H3	120.1	C16—C15—C10	118.6 (2)
C3—C4—C5	120.2 (3)	C14—C15—C10	119.2 (2)
C3—C4—H4	119.9	C17—C16—C15	121.8 (2)
C5—C4—H4	119.9	C17—C16—H16	119.1
C4—C5—C6	120.3 (3)	C15—C16—H16	119.1
C4—C5—H5	119.8	C16—C17—C18	121.6 (2)
C6—C5—H5	119.8	C16—C17—C8	119.4 (2)
C5—C6—C1	119.6 (3)	C18—C17—C8	118.9 (2)
C5—C6—H6	120.2	O1—C18—C19	125.5 (2)
C1—C6—H6	120.2	O1—C18—C17	113.4 (2)
C20—C7—N2	125.3 (2)	C19—C18—C17	121.0 (2)
C20—C7—C8	120.1 (2)	C18—C19—C20	119.3 (2)
N2—C7—C8	114.6 (2)	C18—C19—H19	120.4
C9—C8—C17	118.8 (2)	C20—C19—H19	120.4
C9—C8—C7	123.2 (2)	C7—C20—C19	122.5 (2)
C17—C8—C7	117.9 (2)	C7—C20—H20	118.7
C8—C9—C10	121.7 (2)	C19—C20—H20	118.7
C8—C9—H9	119.2	O1—C21—H21A	109.5
C10—C9—H9	119.2	O1—C21—H21B	109.5
C9—C10—C11	122.4 (2)	H21A—C21—H21B	109.5
C9—C10—C15	119.5 (2)	O1—C21—H21C	109.5
C11—C10—C15	118.1 (2)	H21A—C21—H21C	109.5
C12—C11—C10	121.0 (3)	H21B—C21—H21C	109.5
C12—C11—H11	119.5	N2—N1—C1	112.59 (19)
C10—C11—H11	119.5	N1—N2—C7	115.1 (2)
C11—C12—C13	120.5 (2)	C18—O1—C21	117.5 (2)
C11—C12—H12	119.7
C6—C1—C2—C3	−1.3 (4)	C11—C10—C15—C14	0.7 (4)
N1—C1—C2—C3	178.4 (3)	C14—C15—C16—C17	178.1 (2)
C1—C2—C3—C4	0.0 (4)	C10—C15—C16—C17	−0.4 (4)
C2—C3—C4—C5	1.1 (4)	C15—C16—C17—C18	−176.9 (2)
C3—C4—C5—C6	−0.9 (4)	C15—C16—C17—C8	2.5 (4)
C4—C5—C6—C1	−0.5 (4)	C9—C8—C17—C16	−2.4 (3)
C2—C1—C6—C5	1.6 (4)	C7—C8—C17—C16	176.7 (2)
N1—C1—C6—C5	−178.2 (3)	C9—C8—C17—C18	177.0 (2)
C20—C7—C8—C9	−175.8 (3)	C7—C8—C17—C18	−3.9 (3)
N2—C7—C8—C9	3.0 (4)	C16—C17—C18—O1	1.0 (3)
C20—C7—C8—C17	5.1 (4)	C8—C17—C18—O1	−178.4 (2)
N2—C7—C8—C17	−176.1 (2)	C16—C17—C18—C19	179.4 (2)
C17—C8—C9—C10	0.3 (4)	C8—C17—C18—C19	0.0 (4)
C7—C8—C9—C10	−178.8 (2)	O1—C18—C19—C20	−179.1 (2)
C8—C9—C10—C11	−179.3 (3)	C17—C18—C19—C20	2.7 (4)
C8—C9—C10—C15	1.7 (4)	N2—C7—C20—C19	178.8 (2)
C9—C10—C11—C12	−180.0 (3)	C8—C7—C20—C19	−2.6 (4)
C15—C10—C11—C12	−1.0 (4)	C18—C19—C20—C7	−1.5 (4)
C10—C11—C12—C13	0.9 (4)	C2—C1—N1—N2	−173.3 (2)
C11—C12—C13—C14	−0.6 (4)	C6—C1—N1—N2	6.5 (3)
C12—C13—C14—C15	0.4 (4)	C1—N1—N2—C7	179.6 (2)
C13—C14—C15—C16	−179.0 (3)	C20—C7—N2—N1	−13.9 (4)
C13—C14—C15—C10	−0.4 (4)	C8—C7—N2—N1	167.4 (2)
C9—C10—C15—C16	−1.7 (4)	C19—C18—O1—C21	2.2 (4)
C11—C10—C15—C16	179.3 (2)	C17—C18—O1—C21	−179.5 (2)
C9—C10—C15—C14	179.7 (2)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C7,C8,C17–C20 and C8–C10,C15–C17) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···Cg1i	0.98	2.83	3.646 (4)	141
C12—H12···Cg2ii	0.95	2.80	3.681 (4)	154
C11—H11···Cg3ii	0.95	2.83	3.543 (3)	132

Table 1

C—H⋯π interactions (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C7,C8,C17–C20 and C8–C10,C15–C17) rings, respectively.

C—H⋯Cg	C—H	H⋯Cg	C⋯Cg	C—H⋯Cg
C21—H21A⋯Cg1i	0.98	2.83	3.646 (4)	141
C12—H12⋯Cg2ii	0.95	2.80	3.681 (4)	154
C11—H11⋯Cg3ii	0.95	2.83	3.543 (3)	132

Symmetry codes: (i) ; (ii) .