(Z)-3-(9-Anthr-yl)-2-(4-nitro-1H-imidazol-1-yl)-1-p-tolyl-prop-2-en-1-one.

In the title mol-ecule, C(27)H(19)N(3)O(3), the imidazole and benzene rings make dihedral angles of 64.72 (4) and 64.02 (4)°, respectively, with the anthracene ring system (r.m.s. deviation = 0.043 Å). The nitro group is coplanar with the imidazole ring [dihedral angle = 1.1 (1)°]. The crystal packing is stabilized by weak π-π inter-actions with centroid-centroid distances of 3.7342 (10) and 3.7627 (9) Å.

Related literature

For the crystal structures of the chloro and bromo analogues, see: Wang et al. (2009 ▶); Lu et al. (2009 ▶). For general background to chalcones, see: Vogel et al. (2008 ▶). For the synthesis, see: Erhardt et al. (1985 ▶).

Experimental

Crystal data

C27H19N3O3

M = 433.45

Triclinic,

a = 7.9335 (9) Å

b = 11.2626 (13) Å

c = 13.0291 (15) Å

α = 75.454 (2)°

β = 85.763 (2)°

γ = 71.059 (2)°

V = 1065.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.36 × 0.23 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.968, T max = 0.991

12116 measured reflections

4621 independent reflections

3646 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.05

4621 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039221/ci2921sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039221/ci2921Isup2.hkl

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

C27H19N3O3	Z = 2
Mr = 433.45	F(000) = 452
Triclinic, P1	Dx = 1.351 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9335 (9) Å	Cell parameters from 5053 reflections
b = 11.2626 (13) Å	θ = 2.2–28.1°
c = 13.0291 (15) Å	µ = 0.09 mm−1
α = 75.454 (2)°	T = 298 K
β = 85.763 (2)°	Plate, yellow
γ = 71.059 (2)°	0.36 × 0.23 × 0.10 mm
V = 1065.8 (2) Å3

Bruker SMART CCD area-detector diffractometer	4621 independent reflections
Radiation source: fine-focus sealed tube	3646 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −10→10
Tmin = 0.968, Tmax = 0.991	k = −14→14
12116 measured reflections	l = −16→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0696P)2 + 0.061P] where P = (Fo2 + 2Fc2)/3
4621 reflections	(Δ/σ)max = 0.012
299 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.23 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
C1	0.8022 (2)	0.80103 (14)	0.10371 (11)	0.0625 (4)
C2	0.9235 (2)	0.68461 (16)	0.09495 (12)	0.0655 (4)
H2	1.0443	0.6760	0.0895	0.079*
C3	0.86855 (18)	0.58070 (13)	0.09409 (10)	0.0542 (3)
H3	0.9521	0.5032	0.0871	0.065*
C4	0.68960 (16)	0.59098 (11)	0.10360 (9)	0.0443 (3)
C5	0.56700 (18)	0.70796 (12)	0.11149 (10)	0.0525 (3)
H5	0.4464	0.7164	0.1176	0.063*
C6	0.6231 (2)	0.81227 (13)	0.11031 (11)	0.0604 (4)
H6	0.5394	0.8911	0.1140	0.073*
C7	0.8646 (3)	0.91345 (19)	0.10604 (18)	0.1030 (7)
H7A	0.9884	0.8938	0.0878	0.155*
H7B	0.8486	0.9288	0.1759	0.155*
H7C	0.7964	0.9893	0.0559	0.155*
C8	0.63944 (15)	0.47439 (11)	0.10306 (9)	0.0429 (3)
C9	0.53578 (15)	0.42485 (10)	0.19465 (9)	0.0401 (3)
C10	0.51789 (15)	0.46279 (11)	0.28466 (9)	0.0424 (3)
H10	0.5567	0.5329	0.2825	0.051*
C11	0.55904 (19)	0.21206 (12)	0.15682 (10)	0.0547 (3)
H11	0.6800	0.1879	0.1413	0.066*
C12	0.29544 (19)	0.21363 (13)	0.18201 (9)	0.0522 (3)
C13	0.29627 (17)	0.32641 (12)	0.20011 (9)	0.0479 (3)
H13	0.2010	0.3902	0.2198	0.057*
C14	0.44576 (16)	0.41062 (12)	0.38765 (9)	0.0442 (3)
C15	0.31154 (16)	0.49758 (13)	0.43426 (9)	0.0497 (3)
C16	0.23060 (19)	0.62857 (14)	0.38169 (12)	0.0604 (4)
H16	0.2649	0.6593	0.3130	0.072*
C17	0.1035 (2)	0.71059 (18)	0.42967 (15)	0.0772 (5)
H17	0.0528	0.7965	0.3936	0.093*
C18	0.0482 (2)	0.6666 (2)	0.53315 (16)	0.0844 (6)
H18	−0.0377	0.7238	0.5655	0.101*
C19	0.1187 (2)	0.5429 (2)	0.58552 (13)	0.0770 (5)
H19	0.0799	0.5152	0.6538	0.092*
C20	0.25212 (18)	0.45250 (17)	0.53893 (10)	0.0587 (4)
C21	0.3253 (2)	0.32471 (18)	0.59118 (10)	0.0668 (4)
H21	0.2843	0.2958	0.6585	0.080*
C22	0.4581 (2)	0.23721 (15)	0.54715 (10)	0.0609 (4)
C23	0.5358 (3)	0.10705 (19)	0.60296 (13)	0.0849 (5)
H23	0.4934	0.0776	0.6698	0.102*
C24	0.6697 (3)	0.02531 (18)	0.56107 (15)	0.0961 (6)
H24	0.7168	−0.0604	0.5983	0.115*
C25	0.7395 (3)	0.06850 (16)	0.46106 (13)	0.0800 (5)
H25	0.8346	0.0116	0.4339	0.096*
C26	0.6691 (2)	0.19203 (13)	0.40416 (11)	0.0588 (4)
H26	0.7175	0.2190	0.3386	0.071*
C27	0.52314 (18)	0.28088 (13)	0.44281 (9)	0.0495 (3)
N1	0.46726 (13)	0.32578 (9)	0.18306 (7)	0.0428 (2)
N2	0.45809 (17)	0.14128 (11)	0.15594 (9)	0.0602 (3)
N4	0.1423 (2)	0.17060 (15)	0.18753 (10)	0.0718 (4)
O1	0.69016 (12)	0.41643 (9)	0.03388 (7)	0.0576 (3)
O2	0.1606 (2)	0.06711 (14)	0.16772 (11)	0.1051 (5)
O3	0.00028 (18)	0.24220 (15)	0.21342 (12)	0.0975 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0851 (10)	0.0617 (9)	0.0534 (8)	−0.0413 (8)	0.0181 (7)	−0.0175 (7)
C2	0.0631 (9)	0.0805 (10)	0.0669 (9)	−0.0393 (8)	0.0181 (7)	−0.0256 (8)
C3	0.0561 (8)	0.0585 (8)	0.0523 (7)	−0.0224 (6)	0.0110 (6)	−0.0185 (6)
C4	0.0526 (7)	0.0487 (7)	0.0330 (6)	−0.0207 (5)	0.0039 (5)	−0.0070 (5)
C5	0.0549 (7)	0.0518 (7)	0.0487 (7)	−0.0175 (6)	0.0043 (6)	−0.0088 (6)
C6	0.0793 (10)	0.0476 (7)	0.0520 (8)	−0.0192 (7)	0.0090 (7)	−0.0113 (6)
C7	0.1274 (17)	0.0883 (13)	0.1247 (16)	−0.0694 (13)	0.0351 (14)	−0.0441 (12)
C8	0.0430 (6)	0.0459 (6)	0.0378 (6)	−0.0122 (5)	−0.0015 (5)	−0.0083 (5)
C9	0.0436 (6)	0.0390 (6)	0.0385 (6)	−0.0150 (5)	−0.0023 (5)	−0.0078 (5)
C10	0.0473 (6)	0.0432 (6)	0.0399 (6)	−0.0189 (5)	−0.0012 (5)	−0.0094 (5)
C11	0.0663 (8)	0.0466 (7)	0.0539 (7)	−0.0195 (6)	0.0048 (6)	−0.0160 (6)
C12	0.0684 (9)	0.0562 (8)	0.0393 (6)	−0.0335 (7)	−0.0051 (6)	−0.0049 (5)
C13	0.0509 (7)	0.0533 (7)	0.0419 (6)	−0.0211 (6)	−0.0030 (5)	−0.0089 (5)
C14	0.0501 (7)	0.0566 (7)	0.0347 (6)	−0.0276 (6)	−0.0006 (5)	−0.0122 (5)
C15	0.0491 (7)	0.0693 (9)	0.0428 (6)	−0.0290 (6)	0.0004 (5)	−0.0216 (6)
C16	0.0582 (8)	0.0705 (9)	0.0604 (8)	−0.0221 (7)	0.0010 (6)	−0.0276 (7)
C17	0.0632 (9)	0.0857 (11)	0.0916 (12)	−0.0160 (8)	−0.0031 (8)	−0.0463 (10)
C18	0.0562 (9)	0.1257 (17)	0.0902 (13)	−0.0252 (10)	0.0098 (9)	−0.0667 (13)
C19	0.0564 (9)	0.1382 (17)	0.0592 (9)	−0.0450 (10)	0.0129 (7)	−0.0491 (11)
C20	0.0508 (7)	0.0984 (11)	0.0442 (7)	−0.0399 (7)	0.0042 (6)	−0.0274 (7)
C21	0.0708 (9)	0.1096 (13)	0.0367 (7)	−0.0552 (9)	0.0048 (6)	−0.0134 (8)
C22	0.0771 (10)	0.0761 (9)	0.0401 (7)	−0.0446 (8)	−0.0072 (6)	−0.0034 (6)
C23	0.1265 (16)	0.0850 (12)	0.0485 (8)	−0.0569 (12)	−0.0116 (9)	0.0089 (8)
C24	0.151 (2)	0.0634 (10)	0.0639 (11)	−0.0333 (12)	−0.0260 (12)	0.0091 (9)
C25	0.1040 (13)	0.0594 (9)	0.0676 (10)	−0.0148 (9)	−0.0201 (9)	−0.0081 (8)
C26	0.0715 (9)	0.0565 (8)	0.0480 (7)	−0.0221 (7)	−0.0097 (6)	−0.0065 (6)
C27	0.0603 (8)	0.0576 (8)	0.0378 (6)	−0.0308 (6)	−0.0062 (5)	−0.0065 (5)
N1	0.0501 (6)	0.0427 (5)	0.0385 (5)	−0.0179 (4)	−0.0008 (4)	−0.0105 (4)
N2	0.0837 (9)	0.0513 (6)	0.0546 (7)	−0.0321 (6)	0.0017 (6)	−0.0150 (5)
N4	0.0921 (10)	0.0831 (9)	0.0569 (7)	−0.0572 (9)	−0.0091 (7)	−0.0046 (7)
O1	0.0656 (6)	0.0654 (6)	0.0495 (5)	−0.0253 (5)	0.0130 (4)	−0.0253 (5)
O2	0.1427 (12)	0.1039 (10)	0.1091 (10)	−0.0885 (10)	−0.0031 (9)	−0.0309 (8)
O3	0.0747 (8)	0.1167 (11)	0.1149 (11)	−0.0555 (8)	0.0020 (7)	−0.0195 (8)

C1—C2	1.378 (2)	C13—H13	0.93
C1—C6	1.383 (2)	C14—C27	1.4085 (18)
C1—C7	1.509 (2)	C14—C15	1.4099 (17)
C2—C3	1.3779 (19)	C15—C16	1.414 (2)
C2—H2	0.93	C15—C20	1.4327 (18)
C3—C4	1.3852 (18)	C16—C17	1.361 (2)
C3—H3	0.93	C16—H16	0.93
C4—C5	1.3835 (18)	C17—C18	1.405 (3)
C4—C8	1.4923 (16)	C17—H17	0.93
C5—C6	1.3814 (18)	C18—C19	1.339 (3)
C5—H5	0.93	C18—H18	0.93
C6—H6	0.93	C19—C20	1.429 (2)
C7—H7A	0.96	C19—H19	0.93
C7—H7B	0.96	C20—C21	1.377 (2)
C7—H7C	0.96	C21—C22	1.390 (2)
C8—O1	1.2133 (13)	C21—H21	0.93
C8—C9	1.4933 (16)	C22—C23	1.415 (2)
C9—C10	1.3289 (15)	C22—C27	1.4426 (18)
C9—N1	1.4332 (14)	C23—C24	1.344 (3)
C10—C14	1.4772 (15)	C23—H23	0.93
C10—H10	0.93	C24—C25	1.411 (3)
C11—N2	1.3029 (17)	C24—H24	0.93
C11—N1	1.3657 (16)	C25—C26	1.355 (2)
C11—H11	0.93	C25—H25	0.93
C12—C13	1.3510 (17)	C26—C27	1.418 (2)
C12—N2	1.3551 (18)	C26—H26	0.93
C12—N4	1.4381 (18)	N4—O2	1.2174 (17)
C13—N1	1.3563 (15)	N4—O3	1.2346 (18)
C2—C1—C6	118.62 (13)	C14—C15—C20	119.28 (13)
C2—C1—C7	120.37 (15)	C16—C15—C20	117.91 (12)
C6—C1—C7	121.01 (15)	C17—C16—C15	121.32 (15)
C1—C2—C3	120.94 (14)	C17—C16—H16	119.3
C1—C2—H2	119.5	C15—C16—H16	119.3
C3—C2—H2	119.5	C16—C17—C18	120.57 (18)
C2—C3—C4	120.40 (13)	C16—C17—H17	119.7
C2—C3—H3	119.8	C18—C17—H17	119.7
C4—C3—H3	119.8	C19—C18—C17	120.34 (16)
C5—C4—C3	118.92 (12)	C19—C18—H18	119.8
C5—C4—C8	123.45 (11)	C17—C18—H18	119.8
C3—C4—C8	117.62 (11)	C18—C19—C20	121.48 (16)
C6—C5—C4	120.24 (13)	C18—C19—H19	119.3
C6—C5—H5	119.9	C20—C19—H19	119.3
C4—C5—H5	119.9	C21—C20—C19	122.36 (14)
C5—C6—C1	120.85 (13)	C21—C20—C15	119.29 (13)
C5—C6—H6	119.6	C19—C20—C15	118.35 (15)
C1—C6—H6	119.6	C20—C21—C22	122.53 (12)
C1—C7—H7A	109.5	C20—C21—H21	118.7
C1—C7—H7B	109.5	C22—C21—H21	118.7
H7A—C7—H7B	109.5	C21—C22—C23	121.93 (14)
C1—C7—H7C	109.5	C21—C22—C27	119.26 (13)
H7A—C7—H7C	109.5	C23—C22—C27	118.78 (16)
H7B—C7—H7C	109.5	C24—C23—C22	121.12 (16)
O1—C8—C4	121.31 (10)	C24—C23—H23	119.4
O1—C8—C9	120.52 (11)	C22—C23—H23	119.4
C4—C8—C9	118.02 (10)	C23—C24—C25	120.55 (16)
C10—C9—N1	121.36 (10)	C23—C24—H24	119.7
C10—C9—C8	122.61 (10)	C25—C24—H24	119.7
N1—C9—C8	115.87 (9)	C26—C25—C24	120.61 (18)
C9—C10—C14	129.89 (10)	C26—C25—H25	119.7
C9—C10—H10	115.1	C24—C25—H25	119.7
C14—C10—H10	115.1	C25—C26—C27	121.12 (14)
N2—C11—N1	112.40 (13)	C25—C26—H26	119.4
N2—C11—H11	123.8	C27—C26—H26	119.4
N1—C11—H11	123.8	C14—C27—C26	123.60 (11)
C13—C12—N2	112.85 (11)	C14—C27—C22	118.59 (13)
C13—C12—N4	125.76 (14)	C26—C27—C22	117.70 (12)
N2—C12—N4	121.39 (13)	C13—N1—C11	106.73 (10)
C12—C13—N1	104.50 (11)	C13—N1—C9	125.53 (10)
C12—C13—H13	127.7	C11—N1—C9	127.71 (11)
N1—C13—H13	127.7	C11—N2—C12	103.51 (11)
C27—C14—C15	121.01 (11)	O2—N4—O3	124.53 (15)
C27—C14—C10	120.56 (11)	O2—N4—C12	118.72 (16)
C15—C14—C10	118.04 (11)	O3—N4—C12	116.74 (13)
C14—C15—C16	122.80 (11)
C6—C1—C2—C3	−0.8 (2)	C14—C15—C20—C19	178.69 (11)
C7—C1—C2—C3	179.16 (15)	C16—C15—C20—C19	−1.83 (17)
C1—C2—C3—C4	−0.9 (2)	C19—C20—C21—C22	−178.42 (12)
C2—C3—C4—C5	1.47 (19)	C15—C20—C21—C22	1.3 (2)
C2—C3—C4—C8	−179.46 (11)	C20—C21—C22—C23	178.14 (14)
C3—C4—C5—C6	−0.28 (18)	C20—C21—C22—C27	0.1 (2)
C8—C4—C5—C6	−179.29 (11)	C21—C22—C23—C24	−176.94 (16)
C4—C5—C6—C1	−1.5 (2)	C27—C22—C23—C24	1.1 (3)
C2—C1—C6—C5	2.0 (2)	C22—C23—C24—C25	1.6 (3)
C7—C1—C6—C5	−177.96 (14)	C23—C24—C25—C26	−2.0 (3)
C5—C4—C8—O1	127.74 (13)	C24—C25—C26—C27	−0.5 (2)
C3—C4—C8—O1	−51.28 (16)	C15—C14—C27—C26	−174.16 (11)
C5—C4—C8—C9	−56.71 (15)	C10—C14—C27—C26	−1.40 (18)
C3—C4—C8—C9	124.27 (12)	C15—C14—C27—C22	2.01 (17)
O1—C8—C9—C10	161.69 (12)	C10—C14—C27—C22	174.76 (11)
C4—C8—C9—C10	−13.90 (17)	C25—C26—C27—C14	179.39 (13)
O1—C8—C9—N1	−13.70 (16)	C25—C26—C27—C22	3.2 (2)
C4—C8—C9—N1	170.72 (10)	C21—C22—C27—C14	−1.75 (18)
N1—C9—C10—C14	5.68 (19)	C23—C22—C27—C14	−179.84 (13)
C8—C9—C10—C14	−169.46 (11)	C21—C22—C27—C26	174.64 (12)
N2—C12—C13—N1	0.92 (14)	C23—C22—C27—C26	−3.45 (19)
N4—C12—C13—N1	−178.45 (11)	C12—C13—N1—C11	−0.61 (13)
C9—C10—C14—C27	59.15 (18)	C12—C13—N1—C9	−178.63 (10)
C9—C10—C14—C15	−127.88 (14)	N2—C11—N1—C13	0.13 (14)
C27—C14—C15—C16	179.91 (11)	N2—C11—N1—C9	178.09 (10)
C10—C14—C15—C16	6.98 (17)	C10—C9—N1—C13	54.97 (16)
C27—C14—C15—C20	−0.64 (17)	C8—C9—N1—C13	−129.58 (11)
C10—C14—C15—C20	−173.57 (10)	C10—C9—N1—C11	−122.63 (14)
C14—C15—C16—C17	−178.85 (12)	C8—C9—N1—C11	52.83 (15)
C20—C15—C16—C17	1.70 (19)	N1—C11—N2—C12	0.41 (14)
C15—C16—C17—C18	−0.4 (2)	C13—C12—N2—C11	−0.83 (14)
C16—C17—C18—C19	−0.7 (2)	N4—C12—N2—C11	178.56 (11)
C17—C18—C19—C20	0.5 (2)	C13—C12—N4—O2	178.97 (13)
C18—C19—C20—C21	−179.54 (14)	N2—C12—N4—O2	−0.34 (19)
C18—C19—C20—C15	0.8 (2)	C13—C12—N4—O3	−1.7 (2)
C14—C15—C20—C21	−1.03 (17)	N2—C12—N4—O3	178.98 (13)
C16—C15—C20—C21	178.45 (12)