(E)-N-(Anthracen-9-yl-methyl-idene)-4-nitro-aniline.

In the title molecule, C(21)H(14)N(2)O(2), the anthracenyl system is approximately planar [maximum deviation = 0.056 (4) Å] and is oriented at a dihedral angle of 73.6 (1)° with respect to the benzene ring. An intra-molecular C-H⋯N hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by C-H⋯π and π-π inter-actions [centroid-centroid distances of 3.688 (2), 3.656 (1) and 3.716 (2) Å].

Related literature

For applications of anthracene derivatives, see: de Silva et al. (1997 ▶); Klarner et al. (1998 ▶); Han et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Arumugam et al. (2011 ▶); Villalpando et al. (2010 ▶).

Experimental

Crystal data

C21H14N2O2

M = 326.34

Triclinic,

a = 8.3634 (4) Å

b = 8.9045 (4) Å

c = 11.5119 (6) Å

α = 75.235 (2)°

β = 84.544 (3)°

γ = 75.054 (2)°

V = 800.56 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2004 ▶) T min = 0.924, T max = 0.991

15391 measured reflections

2983 independent reflections

1870 reflections with I > 2σ(I)

R int = 0.151

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.306

S = 1.12

2983 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035859/im2315sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035859/im2315Isup2.hkl

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

C21H14N2O2	Z = 2
Mr = 326.34	F(000) = 340
Triclinic, P1	Dx = 1.354 Mg m−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3634 (4) Å	Cell parameters from 5007 reflections
b = 8.9045 (4) Å	θ = 2.5–25.3°
c = 11.5119 (6) Å	µ = 0.09 mm−1
α = 75.235 (2)°	T = 293 K
β = 84.544 (3)°	Flat, orange
γ = 75.054 (2)°	0.30 × 0.20 × 0.10 mm
V = 800.56 (7) Å3

Bruker APEXII diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
graphite	Rint = 0.151
ω and φ scan	θmax = 25.6°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −10→10
Tmin = 0.924, Tmax = 0.991	k = −10→10
15391 measured reflections	l = −13→13

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.306	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
2983 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.43 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
C1	0.4268 (3)	−0.1323 (3)	0.7152 (2)	0.0507 (7)
C2	0.5139 (4)	−0.2566 (4)	0.8071 (2)	0.0622 (8)
H2	0.5912	−0.2354	0.8498	0.075*
C3	0.4872 (4)	−0.4052 (4)	0.8341 (3)	0.0725 (9)
H3	0.5463	−0.4840	0.8950	0.087*
C4	0.3730 (4)	−0.4430 (4)	0.7726 (3)	0.0746 (10)
H4	0.3553	−0.5455	0.7936	0.090*
C5	0.2885 (4)	−0.3314 (4)	0.6829 (3)	0.0673 (9)
H5	0.2134	−0.3579	0.6417	0.081*
C6	0.3125 (3)	−0.1725 (3)	0.6501 (2)	0.0532 (7)
C7	0.2314 (3)	−0.0591 (3)	0.5551 (2)	0.0549 (8)
H7	0.1599	−0.0875	0.5121	0.066*
C8	0.2524 (3)	0.0973 (3)	0.5211 (2)	0.0498 (7)
C9	0.1657 (3)	0.2116 (4)	0.4241 (2)	0.0621 (8)
H9	0.0979	0.1808	0.3798	0.075*
C10	0.1794 (4)	0.3636 (4)	0.3950 (3)	0.0703 (9)
H10	0.1211	0.4375	0.3312	0.084*
C11	0.2830 (4)	0.4104 (4)	0.4619 (3)	0.0675 (9)
H11	0.2904	0.5164	0.4427	0.081*
C12	0.3710 (3)	0.3050 (3)	0.5525 (2)	0.0588 (8)
H12	0.4395	0.3393	0.5939	0.071*
C13	0.3618 (3)	0.1421 (3)	0.5868 (2)	0.0487 (7)
C14	0.4501 (3)	0.0265 (3)	0.6825 (2)	0.0479 (7)
C15	0.5698 (3)	0.0602 (4)	0.7521 (3)	0.0584 (8)
H15	0.5835	0.0005	0.8311	0.070*
C16	0.7666 (3)	0.1767 (3)	0.7942 (2)	0.0553 (8)
C17	0.9203 (4)	0.1906 (4)	0.7470 (3)	0.0687 (9)
H17	0.9467	0.1877	0.6672	0.082*
C18	1.0355 (4)	0.2085 (4)	0.8158 (3)	0.0695 (9)
H18	1.1407	0.2147	0.7841	0.083*
C19	0.9936 (3)	0.2169 (3)	0.9316 (2)	0.0561 (8)
C20	0.8419 (3)	0.2054 (4)	0.9826 (2)	0.0597 (8)
H20	0.8168	0.2105	1.0622	0.072*
C21	0.7263 (3)	0.1859 (3)	0.9128 (2)	0.0589 (8)
H21	0.6214	0.1791	0.9451	0.071*
N1	0.6547 (3)	0.1602 (3)	0.7163 (2)	0.0647 (7)
N2	1.1188 (4)	0.2349 (4)	1.0045 (3)	0.0823 (9)
O1	1.0791 (4)	0.2499 (5)	1.1057 (3)	0.1296 (12)
O2	1.2591 (3)	0.2269 (4)	0.9629 (2)	0.1103 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0442 (15)	0.0651 (17)	0.0434 (14)	−0.0129 (12)	0.0062 (11)	−0.0174 (12)
C2	0.0615 (18)	0.076 (2)	0.0457 (15)	−0.0128 (14)	−0.0012 (13)	−0.0120 (13)
C3	0.087 (2)	0.070 (2)	0.0511 (17)	−0.0134 (17)	0.0044 (16)	−0.0059 (14)
C4	0.094 (3)	0.0552 (19)	0.073 (2)	−0.0245 (17)	0.0155 (18)	−0.0117 (15)
C5	0.0660 (19)	0.073 (2)	0.0698 (19)	−0.0249 (15)	0.0068 (15)	−0.0235 (16)
C6	0.0498 (16)	0.0619 (18)	0.0498 (15)	−0.0148 (13)	0.0074 (12)	−0.0187 (12)
C7	0.0490 (16)	0.0723 (19)	0.0503 (15)	−0.0204 (13)	−0.0009 (12)	−0.0218 (13)
C8	0.0412 (14)	0.0648 (17)	0.0423 (14)	−0.0115 (12)	0.0031 (11)	−0.0139 (12)
C9	0.0511 (17)	0.084 (2)	0.0502 (16)	−0.0143 (14)	−0.0074 (13)	−0.0139 (14)
C10	0.0645 (19)	0.076 (2)	0.0576 (18)	−0.0116 (15)	−0.0089 (15)	0.0030 (15)
C11	0.068 (2)	0.0588 (18)	0.0694 (19)	−0.0151 (15)	−0.0038 (15)	−0.0043 (14)
C12	0.0550 (17)	0.0650 (19)	0.0568 (17)	−0.0172 (13)	−0.0026 (13)	−0.0125 (13)
C13	0.0416 (14)	0.0623 (17)	0.0439 (14)	−0.0133 (12)	0.0062 (11)	−0.0176 (12)
C14	0.0405 (14)	0.0615 (17)	0.0428 (14)	−0.0133 (11)	0.0018 (11)	−0.0145 (12)
C15	0.0498 (16)	0.0717 (19)	0.0539 (16)	−0.0151 (14)	−0.0036 (12)	−0.0143 (13)
C16	0.0581 (17)	0.0556 (16)	0.0545 (16)	−0.0139 (12)	−0.0105 (13)	−0.0144 (12)
C17	0.0637 (19)	0.092 (2)	0.0553 (17)	−0.0213 (16)	0.0017 (14)	−0.0260 (15)
C18	0.0506 (17)	0.093 (2)	0.0633 (19)	−0.0197 (15)	0.0002 (14)	−0.0130 (15)
C19	0.0501 (16)	0.0639 (18)	0.0532 (16)	−0.0140 (13)	−0.0131 (13)	−0.0079 (12)
C20	0.0564 (18)	0.0771 (19)	0.0485 (15)	−0.0161 (14)	−0.0053 (13)	−0.0191 (13)
C21	0.0469 (15)	0.073 (2)	0.0600 (17)	−0.0187 (13)	0.0002 (13)	−0.0191 (14)
N1	0.0692 (16)	0.0745 (17)	0.0572 (14)	−0.0250 (13)	−0.0087 (12)	−0.0182 (12)
N2	0.068 (2)	0.113 (2)	0.0676 (18)	−0.0334 (16)	−0.0227 (15)	−0.0059 (16)
O1	0.100 (2)	0.225 (4)	0.093 (2)	−0.056 (2)	−0.0209 (17)	−0.069 (2)
O2	0.0675 (17)	0.169 (3)	0.097 (2)	−0.0584 (17)	−0.0212 (15)	0.0007 (17)

C1—C2	1.418 (4)	C11—H11	0.9300
C1—C14	1.428 (4)	C12—C13	1.423 (4)
C1—C6	1.432 (4)	C12—H12	0.9300
C2—C3	1.352 (4)	C13—C14	1.415 (4)
C2—H2	0.9300	C14—C15	1.471 (4)
C3—C4	1.394 (5)	C15—N1	1.245 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.344 (5)	C16—C17	1.370 (4)
C4—H4	0.9300	C16—C21	1.393 (4)
C5—C6	1.430 (4)	C16—N1	1.414 (3)
C5—H5	0.9300	C17—C18	1.367 (4)
C6—C7	1.379 (4)	C17—H17	0.9300
C7—C8	1.399 (4)	C18—C19	1.361 (4)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.415 (4)	C19—C20	1.364 (4)
C8—C13	1.430 (4)	C19—N2	1.466 (4)
C9—C10	1.341 (4)	C20—C21	1.385 (4)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.412 (4)	C21—H21	0.9300
C10—H10	0.9300	N2—O1	1.212 (4)
C11—C12	1.342 (4)	N2—O2	1.216 (4)
C2—C1—C14	123.9 (2)	C11—C12—H12	119.2
C2—C1—C6	117.0 (2)	C13—C12—H12	119.2
C14—C1—C6	119.0 (2)	C14—C13—C12	124.0 (2)
C3—C2—C1	121.4 (3)	C14—C13—C8	119.4 (2)
C3—C2—H2	119.3	C12—C13—C8	116.6 (2)
C1—C2—H2	119.3	C13—C14—C1	120.3 (2)
C2—C3—C4	121.5 (3)	C13—C14—C15	123.2 (2)
C2—C3—H3	119.3	C1—C14—C15	116.5 (2)
C4—C3—H3	119.3	N1—C15—C14	126.8 (3)
C5—C4—C3	120.1 (3)	N1—C15—H15	116.6
C5—C4—H4	119.9	C14—C15—H15	116.6
C3—C4—H4	119.9	C17—C16—C21	119.2 (2)
C4—C5—C6	120.8 (3)	C17—C16—N1	117.1 (2)
C4—C5—H5	119.6	C21—C16—N1	123.6 (2)
C6—C5—H5	119.6	C18—C17—C16	120.9 (3)
C7—C6—C5	121.2 (3)	C18—C17—H17	119.6
C7—C6—C1	119.6 (2)	C16—C17—H17	119.6
C5—C6—C1	119.2 (3)	C19—C18—C17	118.9 (3)
C6—C7—C8	122.5 (2)	C19—C18—H18	120.5
C6—C7—H7	118.8	C17—C18—H18	120.5
C8—C7—H7	118.8	C18—C19—C20	122.6 (3)
C7—C8—C9	121.2 (2)	C18—C19—N2	118.3 (3)
C7—C8—C13	119.1 (2)	C20—C19—N2	119.1 (3)
C9—C8—C13	119.7 (2)	C19—C20—C21	118.2 (3)
C10—C9—C8	121.3 (3)	C19—C20—H20	120.9
C10—C9—H9	119.3	C21—C20—H20	120.9
C8—C9—H9	119.3	C20—C21—C16	120.1 (3)
C9—C10—C11	119.4 (3)	C20—C21—H21	119.9
C9—C10—H10	120.3	C16—C21—H21	119.9
C11—C10—H10	120.3	C15—N1—C16	120.0 (2)
C12—C11—C10	121.4 (3)	O1—N2—O2	123.0 (3)
C12—C11—H11	119.3	O1—N2—C19	118.2 (3)
C10—C11—H11	119.3	O2—N2—C19	118.7 (3)
C11—C12—C13	121.6 (3)
C14—C1—C2—C3	−179.8 (2)	C8—C13—C14—C1	−1.7 (4)
C6—C1—C2—C3	−1.6 (4)	C12—C13—C14—C15	−4.1 (4)
C1—C2—C3—C4	0.1 (5)	C8—C13—C14—C15	177.7 (2)
C2—C3—C4—C5	1.1 (5)	C2—C1—C14—C13	177.9 (2)
C3—C4—C5—C6	−0.7 (5)	C6—C1—C14—C13	−0.2 (4)
C4—C5—C6—C7	177.4 (3)	C2—C1—C14—C15	−1.5 (4)
C4—C5—C6—C1	−0.8 (4)	C6—C1—C14—C15	−179.6 (2)
C2—C1—C6—C7	−176.3 (2)	C13—C14—C15—N1	−28.3 (4)
C14—C1—C6—C7	2.0 (4)	C1—C14—C15—N1	151.1 (3)
C2—C1—C6—C5	2.0 (4)	C21—C16—C17—C18	2.0 (5)
C14—C1—C6—C5	−179.8 (2)	N1—C16—C17—C18	179.4 (3)
C5—C6—C7—C8	179.9 (2)	C16—C17—C18—C19	−1.8 (5)
C1—C6—C7—C8	−1.8 (4)	C17—C18—C19—C20	1.2 (5)
C6—C7—C8—C9	−179.2 (2)	C17—C18—C19—N2	179.6 (3)
C6—C7—C8—C13	0.0 (4)	C18—C19—C20—C21	−0.7 (5)
C7—C8—C9—C10	176.7 (3)	N2—C19—C20—C21	−179.0 (2)
C13—C8—C9—C10	−2.4 (4)	C19—C20—C21—C16	0.8 (4)
C8—C9—C10—C11	0.4 (4)	C17—C16—C21—C20	−1.4 (4)
C9—C10—C11—C12	1.4 (5)	N1—C16—C21—C20	−178.6 (2)
C10—C11—C12—C13	−1.1 (5)	C14—C15—N1—C16	−179.1 (2)
C11—C12—C13—C14	−179.2 (2)	C17—C16—N1—C15	136.4 (3)
C11—C12—C13—C8	−1.0 (4)	C21—C16—N1—C15	−46.3 (4)
C7—C8—C13—C14	1.8 (4)	C18—C19—N2—O1	176.6 (3)
C9—C8—C13—C14	−179.0 (2)	C20—C19—N2—O1	−4.9 (5)
C7—C8—C13—C12	−176.5 (2)	C18—C19—N2—O2	−6.7 (5)
C9—C8—C13—C12	2.7 (4)	C20—C19—N2—O2	171.8 (3)
C12—C13—C14—C1	176.5 (2)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N1	0.93	2.37	2.980 (4)	123
C20—H20···Cg1i	0.93	2.86	3.717 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N1	0.93	2.37	2.980 (4)	123
C20—H20⋯Cg1i	0.93	2.86	3.717 (3)	154

Symmetry code: (i) .