(Z)-3-(9-Anthryl)-1-(4-chloro-phen-yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one.

In the title compound, C(26)H(16)ClN(3)O(3), the dihedral angle between the anthracene mean plane and imidazole ring is 64.75 (2)°. In the crystal, π-π inter-actions between anthracene fragments lead to the formation of stacks of mol-ecules propagating in [100]. The short distance between the carbonyl groups of symmetry-related molecules [C⋯O = 2.985 (2) Å] indicates the existence of dipole-dipole inter-actions. The crystal packing also exhibits short inter-molecular contacts between the nitro groups and Cl atoms [Cl⋯O = 3.181 (2) Å].

Related literature

For general background, see: Corrêa et al. (2001 ▶); Daskiewicz et al. (2005 ▶); Sivakumar et al. (2009 ▶); Vogel et al. (2008 ▶). The synthesis was described by Erhardt et al. (1985 ▶).

Experimental

Crystal data

C26H16ClN3O3

M = 453.87

Triclinic,

a = 8.0511 (9) Å

b = 11.0406 (12) Å

c = 12.9274 (14) Å

α = 76.065 (2)°

β = 85.974 (2)°

γ = 71.258 (2)°

V = 1056.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 292 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.956, T max = 0.979

6168 measured reflections

4070 independent reflections

3354 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.04

4070 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014676/cv2548sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014676/cv2548Isup2.hkl

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

C26H16ClN3O3	Z = 2
Mr = 453.87	F(000) = 468
Triclinic, P1	Dx = 1.427 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0511 (9) Å	Cell parameters from 2837 reflections
b = 11.0406 (12) Å	θ = 1.4–25.3°
c = 12.9274 (14) Å	µ = 0.22 mm−1
α = 76.065 (2)°	T = 292 K
β = 85.974 (2)°	Block, orange
γ = 71.258 (2)°	0.16 × 0.12 × 0.10 mm
V = 1056.1 (2) Å3

Bruker SMART APEX CCD area-detector diffractometer	4070 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	3354 reflections with I > 2σ(I)
graphite	Rint = 0.014
0.3° wide ω exposures scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −9→9
Tmin = 0.956, Tmax = 0.979	k = −13→10
6168 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.4068P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4070 reflections	Δρmax = 0.56 e Å−3
299 parameters	Δρmin = −0.50 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.138 (5)

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
C1	0.4503 (2)	0.91044 (16)	0.38505 (12)	0.0381 (4)
C2	0.3150 (2)	0.99845 (18)	0.43057 (13)	0.0427 (4)
C3	0.2324 (3)	1.13103 (19)	0.37653 (16)	0.0532 (5)
H3	0.2673	1.1618	0.3078	0.064*
C4	0.1039 (3)	1.2135 (2)	0.4233 (2)	0.0690 (6)
H4	0.0521	1.2999	0.3863	0.083*
C5	0.0482 (3)	1.1702 (3)	0.5267 (2)	0.0758 (7)
H5	−0.0389	1.2284	0.5581	0.091*
C6	0.1195 (3)	1.0455 (3)	0.58072 (18)	0.0671 (6)
H6	0.0806	1.0181	0.6491	0.080*
C7	0.2544 (2)	0.9537 (2)	0.53486 (14)	0.0507 (5)
C8	0.3284 (3)	0.8240 (2)	0.58804 (14)	0.0570 (5)
H8	0.2870	0.7948	0.6553	0.068*
C9	0.4618 (3)	0.7360 (2)	0.54475 (14)	0.0528 (5)
C10	0.5404 (4)	0.6035 (2)	0.60138 (18)	0.0751 (7)
H10	0.4981	0.5739	0.6682	0.090*
C11	0.6738 (4)	0.5211 (2)	0.5604 (2)	0.0864 (8)
H11	0.7210	0.4345	0.5983	0.104*
C12	0.7438 (4)	0.5643 (2)	0.45999 (19)	0.0730 (7)
H12	0.8385	0.5065	0.4332	0.088*
C13	0.6736 (3)	0.68926 (18)	0.40237 (15)	0.0516 (5)
H13	0.7218	0.7164	0.3368	0.062*
C14	0.5276 (2)	0.77936 (17)	0.44076 (13)	0.0428 (4)
C15	0.5225 (2)	0.96316 (15)	0.28220 (12)	0.0370 (4)
H15	0.5605	1.0348	0.2804	0.044*
C16	0.5410 (2)	0.92308 (15)	0.19171 (12)	0.0351 (4)
C17	0.6425 (2)	0.97302 (15)	0.10011 (12)	0.0364 (4)
C18	0.6982 (2)	1.08892 (16)	0.10310 (12)	0.0372 (4)
C19	0.5813 (2)	1.21059 (17)	0.10958 (14)	0.0442 (4)
H19	0.4615	1.2227	0.1122	0.053*
C20	0.6414 (3)	1.31410 (18)	0.11219 (15)	0.0503 (5)
H20	0.5631	1.3961	0.1153	0.060*
C21	0.8197 (3)	1.29305 (19)	0.11011 (15)	0.0532 (5)
C22	0.9379 (3)	1.1743 (2)	0.10195 (16)	0.0563 (5)
H22	1.0576	1.1626	0.0995	0.068*
C23	0.8762 (2)	1.07254 (18)	0.09746 (15)	0.0474 (4)
H23	0.9550	0.9922	0.0906	0.057*
C24	0.5604 (3)	0.70649 (17)	0.15237 (15)	0.0488 (4)
H24	0.6791	0.6812	0.1360	0.059*
C25	0.2993 (3)	0.70981 (18)	0.17933 (14)	0.0480 (4)
C26	0.3024 (2)	0.82478 (17)	0.19785 (13)	0.0425 (4)
H26	0.2098	0.8902	0.2183	0.051*
Cl1	0.90255 (10)	1.41713 (6)	0.11994 (6)	0.0886 (3)
N1	0.47212 (18)	0.82266 (13)	0.17975 (10)	0.0378 (3)
N2	0.4588 (2)	0.63534 (15)	0.15188 (13)	0.0554 (4)
N3	0.1473 (3)	0.6670 (2)	0.18554 (14)	0.0685 (5)
O1	0.68863 (17)	0.91581 (12)	0.02841 (10)	0.0486 (3)
O2	0.0083 (3)	0.7406 (2)	0.21193 (17)	0.0925 (6)
O3	0.1648 (3)	0.5612 (2)	0.16539 (18)	0.1061 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0429 (9)	0.0474 (9)	0.0326 (8)	−0.0239 (7)	−0.0008 (7)	−0.0116 (7)
C2	0.0408 (9)	0.0578 (11)	0.0399 (9)	−0.0234 (8)	0.0005 (7)	−0.0200 (8)
C3	0.0511 (11)	0.0579 (12)	0.0554 (11)	−0.0168 (9)	−0.0008 (9)	−0.0223 (9)
C4	0.0561 (13)	0.0703 (14)	0.0842 (16)	−0.0094 (11)	−0.0040 (11)	−0.0377 (13)
C5	0.0495 (13)	0.108 (2)	0.0832 (17)	−0.0176 (13)	0.0071 (11)	−0.0576 (16)
C6	0.0482 (12)	0.119 (2)	0.0535 (12)	−0.0369 (13)	0.0112 (9)	−0.0440 (13)
C7	0.0441 (10)	0.0823 (14)	0.0407 (9)	−0.0335 (10)	0.0028 (8)	−0.0241 (10)
C8	0.0605 (12)	0.0901 (16)	0.0345 (9)	−0.0445 (12)	0.0046 (8)	−0.0135 (10)
C9	0.0681 (13)	0.0633 (12)	0.0366 (9)	−0.0377 (10)	−0.0063 (8)	−0.0040 (8)
C10	0.113 (2)	0.0690 (15)	0.0459 (12)	−0.0430 (15)	−0.0093 (12)	0.0035 (11)
C11	0.137 (3)	0.0527 (13)	0.0578 (14)	−0.0232 (15)	−0.0204 (15)	0.0063 (11)
C12	0.0934 (18)	0.0528 (12)	0.0627 (14)	−0.0081 (12)	−0.0162 (12)	−0.0099 (10)
C13	0.0619 (12)	0.0490 (10)	0.0441 (10)	−0.0177 (9)	−0.0071 (9)	−0.0085 (8)
C14	0.0505 (10)	0.0486 (10)	0.0365 (9)	−0.0249 (8)	−0.0043 (7)	−0.0089 (7)
C15	0.0408 (9)	0.0366 (8)	0.0385 (8)	−0.0177 (7)	−0.0019 (7)	−0.0091 (7)
C16	0.0384 (9)	0.0322 (8)	0.0376 (8)	−0.0142 (6)	−0.0030 (6)	−0.0083 (6)
C17	0.0361 (8)	0.0373 (8)	0.0358 (8)	−0.0104 (7)	−0.0018 (6)	−0.0092 (7)
C18	0.0439 (9)	0.0390 (8)	0.0318 (8)	−0.0178 (7)	0.0038 (6)	−0.0080 (6)
C19	0.0456 (10)	0.0416 (9)	0.0458 (9)	−0.0154 (8)	0.0034 (7)	−0.0092 (7)
C20	0.0647 (12)	0.0386 (9)	0.0493 (10)	−0.0194 (8)	0.0072 (9)	−0.0107 (8)
C21	0.0713 (13)	0.0516 (11)	0.0508 (11)	−0.0378 (10)	0.0146 (9)	−0.0169 (9)
C22	0.0508 (11)	0.0676 (13)	0.0648 (12)	−0.0333 (10)	0.0149 (9)	−0.0256 (10)
C23	0.0452 (10)	0.0499 (10)	0.0526 (10)	−0.0186 (8)	0.0091 (8)	−0.0195 (8)
C24	0.0616 (12)	0.0385 (9)	0.0507 (10)	−0.0185 (8)	0.0026 (8)	−0.0152 (8)
C25	0.0647 (12)	0.0497 (10)	0.0391 (9)	−0.0343 (9)	−0.0065 (8)	−0.0038 (8)
C26	0.0461 (10)	0.0467 (9)	0.0402 (9)	−0.0221 (8)	−0.0022 (7)	−0.0089 (7)
Cl1	0.1041 (5)	0.0745 (4)	0.1183 (6)	−0.0626 (4)	0.0236 (4)	−0.0392 (4)
N1	0.0449 (8)	0.0364 (7)	0.0372 (7)	−0.0181 (6)	−0.0005 (6)	−0.0107 (6)
N2	0.0803 (12)	0.0435 (9)	0.0524 (9)	−0.0313 (8)	−0.0009 (8)	−0.0133 (7)
N3	0.0902 (15)	0.0785 (13)	0.0566 (10)	−0.0601 (12)	−0.0108 (10)	−0.0030 (9)
O1	0.0552 (8)	0.0524 (7)	0.0465 (7)	−0.0217 (6)	0.0111 (6)	−0.0232 (6)
O2	0.0715 (12)	0.1073 (15)	0.1141 (15)	−0.0560 (11)	0.0001 (11)	−0.0155 (12)
O3	0.1425 (18)	0.1018 (14)	0.1193 (16)	−0.0927 (14)	−0.0026 (13)	−0.0342 (12)

C1—C2	1.408 (2)	C15—H15	0.9300
C1—C14	1.408 (2)	C16—N1	1.4318 (19)
C1—C15	1.477 (2)	C16—C17	1.488 (2)
C2—C3	1.421 (3)	C17—O1	1.2162 (19)
C2—C7	1.429 (2)	C17—C18	1.495 (2)
C3—C4	1.355 (3)	C18—C23	1.384 (2)
C3—H3	0.9300	C18—C19	1.389 (2)
C4—C5	1.402 (4)	C19—C20	1.384 (2)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.341 (4)	C20—C21	1.378 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.432 (3)	C21—C22	1.374 (3)
C6—H6	0.9300	C21—Cl1	1.7382 (18)
C7—C8	1.384 (3)	C22—C23	1.380 (3)
C8—C9	1.385 (3)	C22—H22	0.9300
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.425 (3)	C24—N2	1.305 (2)
C9—C14	1.439 (2)	C24—N1	1.369 (2)
C10—C11	1.336 (4)	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.355 (2)
C11—C12	1.415 (4)	C25—N2	1.360 (3)
C11—H11	0.9300	C25—N3	1.437 (3)
C12—C13	1.357 (3)	C26—N1	1.364 (2)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.422 (3)	N3—O3	1.219 (3)
C13—H13	0.9300	N3—O2	1.235 (3)
C15—C16	1.330 (2)
C17···O1i	2.985 (2)	Cg1···Cg2iii	3.746 (7)
Cl1···O3ii	3.181 (3)	Cg2···Cg2iv	3.863 (8)
C2—C1—C14	121.15 (15)	C16—C15—H15	115.3
C2—C1—C15	117.97 (15)	C1—C15—H15	115.3
C14—C1—C15	120.54 (15)	C15—C16—N1	121.23 (14)
C1—C2—C3	122.84 (16)	C15—C16—C17	122.54 (14)
C1—C2—C7	119.41 (17)	N1—C16—C17	116.12 (13)
C3—C2—C7	117.74 (17)	O1—C17—C16	120.77 (14)
C4—C3—C2	121.3 (2)	O1—C17—C18	120.97 (14)
C4—C3—H3	119.4	C16—C17—C18	118.09 (13)
C2—C3—H3	119.4	C23—C18—C19	119.23 (15)
C3—C4—C5	120.8 (2)	C23—C18—C17	117.30 (15)
C3—C4—H4	119.6	C19—C18—C17	123.47 (15)
C5—C4—H4	119.6	C20—C19—C18	120.67 (17)
C6—C5—C4	120.4 (2)	C20—C19—H19	119.7
C6—C5—H5	119.8	C18—C19—H19	119.7
C4—C5—H5	119.8	C21—C20—C19	118.55 (17)
C5—C6—C7	121.2 (2)	C21—C20—H20	120.7
C5—C6—H6	119.4	C19—C20—H20	120.7
C7—C6—H6	119.4	C22—C21—C20	121.89 (17)
C8—C7—C2	119.04 (17)	C22—C21—Cl1	117.65 (16)
C8—C7—C6	122.40 (19)	C20—C21—Cl1	120.45 (15)
C2—C7—C6	118.6 (2)	C21—C22—C23	118.98 (18)
C7—C8—C9	122.41 (17)	C21—C22—H22	120.5
C7—C8—H8	118.8	C23—C22—H22	120.5
C9—C8—H8	118.8	C22—C23—C18	120.63 (17)
C8—C9—C10	121.97 (19)	C22—C23—H23	119.7
C8—C9—C14	119.60 (18)	C18—C23—H23	119.7
C10—C9—C14	118.4 (2)	N2—C24—N1	112.21 (18)
C11—C10—C9	121.4 (2)	N2—C24—H24	123.9
C11—C10—H10	119.3	N1—C24—H24	123.9
C9—C10—H10	119.3	C26—C25—N2	112.81 (16)
C10—C11—C12	120.6 (2)	C26—C25—N3	125.7 (2)
C10—C11—H11	119.7	N2—C25—N3	121.48 (18)
C12—C11—H11	119.7	C25—C26—N1	104.26 (16)
C13—C12—C11	120.5 (2)	C25—C26—H26	127.9
C13—C12—H12	119.7	N1—C26—H26	127.9
C11—C12—H12	119.7	C26—N1—C24	106.95 (14)
C12—C13—C14	121.0 (2)	C26—N1—C16	125.02 (14)
C12—C13—H13	119.5	C24—N1—C16	128.00 (15)
C14—C13—H13	119.5	C24—N2—C25	103.77 (15)
C1—C14—C13	123.55 (16)	O3—N3—O2	124.9 (2)
C1—C14—C9	118.36 (17)	O3—N3—C25	118.1 (2)
C13—C14—C9	118.00 (17)	O2—N3—C25	116.95 (19)
C16—C15—C1	129.36 (14)
C14—C1—C2—C3	−179.34 (15)	C1—C15—C16—C17	−169.86 (16)
C15—C1—C2—C3	7.3 (2)	C15—C16—C17—O1	164.24 (16)
C14—C1—C2—C7	−0.4 (2)	N1—C16—C17—O1	−12.1 (2)
C15—C1—C2—C7	−173.69 (14)	C15—C16—C17—C18	−11.0 (2)
C1—C2—C3—C4	−179.21 (18)	N1—C16—C17—C18	172.64 (13)
C7—C2—C3—C4	1.8 (3)	O1—C17—C18—C23	−54.0 (2)
C2—C3—C4—C5	−0.1 (3)	C16—C17—C18—C23	121.27 (17)
C3—C4—C5—C6	−1.0 (3)	O1—C17—C18—C19	125.09 (18)
C4—C5—C6—C7	0.4 (3)	C16—C17—C18—C19	−59.7 (2)
C1—C2—C7—C8	−1.1 (2)	C23—C18—C19—C20	−1.1 (3)
C3—C2—C7—C8	177.93 (16)	C17—C18—C19—C20	179.92 (15)
C1—C2—C7—C6	178.61 (15)	C18—C19—C20—C21	−1.1 (3)
C3—C2—C7—C6	−2.3 (2)	C19—C20—C21—C22	2.2 (3)
C5—C6—C7—C8	−178.96 (19)	C19—C20—C21—Cl1	−176.77 (14)
C5—C6—C7—C2	1.3 (3)	C20—C21—C22—C23	−1.1 (3)
C2—C7—C8—C9	1.3 (3)	Cl1—C21—C22—C23	177.95 (15)
C6—C7—C8—C9	−178.43 (17)	C21—C22—C23—C18	−1.2 (3)
C7—C8—C9—C10	178.23 (19)	C19—C18—C23—C22	2.2 (3)
C7—C8—C9—C14	0.0 (3)	C17—C18—C23—C22	−178.67 (16)
C8—C9—C10—C11	−177.3 (2)	N2—C25—C26—N1	0.8 (2)
C14—C9—C10—C11	0.9 (3)	N3—C25—C26—N1	−178.49 (16)
C9—C10—C11—C12	1.5 (4)	C25—C26—N1—C24	−0.45 (18)
C10—C11—C12—C13	−1.7 (4)	C25—C26—N1—C16	−178.48 (14)
C11—C12—C13—C14	−0.6 (3)	N2—C24—N1—C26	0.0 (2)
C2—C1—C14—C13	−174.85 (16)	N2—C24—N1—C16	177.96 (15)
C15—C1—C14—C13	−1.7 (2)	C15—C16—N1—C26	53.9 (2)
C2—C1—C14—C9	1.6 (2)	C17—C16—N1—C26	−129.70 (16)
C15—C1—C14—C9	174.79 (14)	C15—C16—N1—C24	−123.73 (19)
C12—C13—C14—C1	179.44 (18)	C17—C16—N1—C24	52.7 (2)
C12—C13—C14—C9	3.0 (3)	N1—C24—N2—C25	0.4 (2)
C8—C9—C14—C1	−1.5 (2)	C26—C25—N2—C24	−0.8 (2)
C10—C9—C14—C1	−179.75 (17)	N3—C25—N2—C24	178.53 (16)
C8—C9—C14—C13	175.20 (17)	C26—C25—N3—O3	179.18 (19)
C10—C9—C14—C13	−3.1 (3)	N2—C25—N3—O3	0.0 (3)
C2—C1—C15—C16	−126.63 (19)	C26—C25—N3—O2	−1.4 (3)
C14—C1—C15—C16	60.0 (2)	N2—C25—N3—O2	179.44 (19)
C1—C15—C16—N1	6.3 (3)

Table 1

Selected interatomic distances (Å)

C17⋯O1i	2.985 (2)
Cl1⋯O3ii	3.181 (3)
Cg1⋯Cg2iii	3.746 (7)
Cg2⋯Cg2iv	3.863 (8)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of atoms C1/C2/C14/C7–C9 and C2–C7, respectively.