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

In the title mol-ecule, C(26)H(16)BrN(3)O(3), the anthracene and benzene mean planes make dihedral angles of 63.79 (2) and 14.67 (2)°, respectively, with the plane of the imidazole ring. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules to form centrosymmetric dimers. Weak π-π stacking inter-actions, with centroid-centroid distances of 3.779 (2) and 3.826 (2) Å, supply additional stabilization. The crystal packing also exhibits short inter-molecular contacts between the nitro groups and Br atoms [Br⋯O = 3.114 (2) Å].

Related literature

For the crystal structure of the chloro analog of the title compound, see: Wang et al. (2009 ▶). For general background on the pharmacological activities of chalcones, see: Corréa et al. (2001 ▶); Jasinski et al. (2009 ▶); Nielsen et al. (1998 ▶); Vogel et al. (2008 ▶). For the synthetic details, see: Erhardt et al. (1985 ▶); Kranz et al. (1980 ▶).

Experimental

Crystal data

C26H16BrN3O3

M = 498.33

Triclinic,

a = 8.1438 (11) Å

b = 11.0916 (14) Å

c = 12.7979 (17) Å

α = 78.146 (2)°

β = 86.193 (2)°

γ = 70.768 (2)°

V = 1068.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.96 mm−1

T = 292 K

0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.775, T max = 0.828

6422 measured reflections

4315 independent reflections

3095 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.02

4315 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.67 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018352/lh2825sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018352/lh2825Isup2.hkl

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

C26H16BrN3O3	Z = 2
Mr = 498.33	F(000) = 504
Triclinic, P1	Dx = 1.549 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1438 (11) Å	Cell parameters from 2344 reflections
b = 11.0916 (14) Å	θ = 2.3–26.9°
c = 12.7979 (17) Å	µ = 1.96 mm−1
α = 78.146 (2)°	T = 292 K
β = 86.193 (2)°	Block, orange
γ = 70.768 (2)°	0.13 × 0.12 × 0.10 mm
V = 1068.2 (2) Å3

Bruker SMART APEX CCD area-detector diffractometer	4315 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	3095 reflections with I > 2σ(I)
graphite	Rint = 0.019
0.3° wide ω exposures scans	θmax = 26.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
Tmin = 0.775, Tmax = 0.828	k = −13→13
6422 measured reflections	l = −16→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) = 0.116	w = 1/[σ2(Fo2) + (0.0524P)2 + 0.6665P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.008
4315 reflections	Δρmax = 0.56 e Å−3
298 parameters	Δρmin = −0.67 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: 0.0078 (11)

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
Br1	0.93749 (6)	0.89457 (4)	0.12755 (3)	0.06983 (18)
C1	0.4551 (4)	0.4031 (3)	0.3854 (2)	0.0356 (6)
C2	0.3193 (4)	0.4914 (3)	0.4320 (2)	0.0406 (7)
C3	0.2357 (4)	0.6217 (3)	0.3799 (3)	0.0496 (8)
H3	0.2699	0.6506	0.3111	0.060*
C4	0.1080 (5)	0.7050 (4)	0.4276 (4)	0.0691 (11)
H4	0.0565	0.7902	0.3917	0.083*
C5	0.0521 (5)	0.6637 (5)	0.5312 (4)	0.0740 (13)
H5	−0.0342	0.7224	0.5639	0.089*
C6	0.1223 (5)	0.5405 (5)	0.5832 (3)	0.0647 (11)
H6	0.0819	0.5144	0.6509	0.078*
C7	0.2583 (4)	0.4483 (4)	0.5363 (2)	0.0510 (9)
C8	0.3318 (5)	0.3209 (4)	0.5877 (3)	0.0570 (10)
H8	0.2893	0.2930	0.6543	0.068*
C9	0.4663 (5)	0.2335 (4)	0.5435 (3)	0.0545 (9)
C10	0.5444 (7)	0.1041 (4)	0.5990 (3)	0.0804 (14)
H10	0.5007	0.0765	0.6653	0.096*
C11	0.6795 (8)	0.0206 (5)	0.5582 (4)	0.0943 (17)
H11	0.7273	−0.0642	0.5957	0.113*
C12	0.7504 (7)	0.0613 (4)	0.4575 (4)	0.0792 (13)
H12	0.8461	0.0034	0.4305	0.095*
C13	0.6790 (5)	0.1839 (3)	0.4007 (3)	0.0538 (9)
H13	0.7270	0.2092	0.3353	0.065*
C14	0.5326 (4)	0.2738 (3)	0.4394 (2)	0.0415 (7)
C15	0.5261 (4)	0.4522 (3)	0.2830 (2)	0.0327 (6)
H15	0.5626	0.5235	0.2820	0.039*
C16	0.5458 (4)	0.4098 (2)	0.1916 (2)	0.0308 (6)
C17	0.3147 (4)	0.3086 (3)	0.1964 (2)	0.0391 (7)
H17	0.2215	0.3730	0.2185	0.047*
C18	0.5712 (5)	0.1936 (3)	0.1475 (3)	0.0456 (7)
H18	0.6886	0.1698	0.1296	0.055*
C19	0.3157 (5)	0.1937 (3)	0.1754 (2)	0.0448 (8)
C20	0.6441 (4)	0.4580 (3)	0.0995 (2)	0.0322 (6)
C21	0.7038 (4)	0.5703 (3)	0.1060 (2)	0.0332 (6)
C22	0.8822 (4)	0.5456 (3)	0.1056 (2)	0.0422 (7)
H22	0.9569	0.4628	0.1014	0.051*
C23	0.9499 (4)	0.6436 (3)	0.1113 (3)	0.0490 (8)
H23	1.0696	0.6267	0.1122	0.059*
C24	0.8383 (4)	0.7651 (3)	0.1157 (2)	0.0438 (7)
C25	0.6602 (4)	0.7937 (3)	0.1138 (2)	0.0426 (7)
H25	0.5861	0.8775	0.1155	0.051*
C26	0.5943 (4)	0.6947 (3)	0.1094 (2)	0.0389 (7)
H26	0.4746	0.7121	0.1087	0.047*
N1	0.4811 (3)	0.3085 (2)	0.17774 (18)	0.0342 (5)
N2	0.4740 (4)	0.1210 (2)	0.1464 (2)	0.0515 (7)
N3	0.1680 (5)	0.1482 (3)	0.1818 (3)	0.0663 (9)
O1	0.1909 (5)	0.0414 (3)	0.1602 (3)	0.1002 (11)
O2	0.0289 (5)	0.2194 (4)	0.2088 (3)	0.0920 (10)
O3	0.6822 (3)	0.4034 (2)	0.02424 (17)	0.0464 (5)

	U11	U22	U33	U12	U13	U23
Br1	0.0870 (3)	0.0579 (2)	0.0872 (3)	−0.0537 (2)	0.0032 (2)	−0.01466 (19)
C1	0.0423 (17)	0.0457 (16)	0.0284 (14)	−0.0269 (14)	0.0004 (12)	−0.0071 (12)
C2	0.0426 (18)	0.0551 (19)	0.0351 (16)	−0.0264 (15)	0.0010 (13)	−0.0159 (14)
C3	0.048 (2)	0.056 (2)	0.0514 (19)	−0.0203 (17)	0.0012 (15)	−0.0194 (16)
C4	0.058 (2)	0.073 (3)	0.079 (3)	−0.012 (2)	−0.004 (2)	−0.036 (2)
C5	0.049 (2)	0.108 (4)	0.079 (3)	−0.021 (2)	0.009 (2)	−0.057 (3)
C6	0.047 (2)	0.119 (4)	0.047 (2)	−0.040 (2)	0.0134 (17)	−0.038 (2)
C7	0.0468 (19)	0.089 (3)	0.0349 (17)	−0.0403 (19)	0.0018 (14)	−0.0203 (17)
C8	0.065 (2)	0.090 (3)	0.0297 (17)	−0.049 (2)	0.0024 (16)	−0.0047 (18)
C9	0.074 (3)	0.065 (2)	0.0363 (17)	−0.044 (2)	−0.0098 (17)	0.0023 (16)
C10	0.124 (4)	0.070 (3)	0.050 (2)	−0.049 (3)	−0.018 (2)	0.016 (2)
C11	0.156 (5)	0.054 (3)	0.061 (3)	−0.030 (3)	−0.026 (3)	0.016 (2)
C12	0.101 (3)	0.050 (2)	0.076 (3)	−0.008 (2)	−0.019 (2)	−0.009 (2)
C13	0.069 (2)	0.0462 (19)	0.0451 (19)	−0.0187 (18)	−0.0118 (17)	−0.0038 (15)
C14	0.0523 (19)	0.0446 (17)	0.0352 (16)	−0.0268 (15)	−0.0055 (14)	−0.0043 (13)
C15	0.0364 (16)	0.0331 (14)	0.0342 (15)	−0.0187 (12)	0.0007 (12)	−0.0065 (11)
C16	0.0360 (15)	0.0274 (13)	0.0345 (15)	−0.0171 (12)	−0.0003 (11)	−0.0066 (11)
C17	0.0398 (17)	0.0420 (16)	0.0412 (16)	−0.0219 (14)	−0.0027 (13)	−0.0052 (13)
C18	0.054 (2)	0.0340 (16)	0.0535 (19)	−0.0187 (14)	0.0031 (15)	−0.0123 (13)
C19	0.062 (2)	0.0461 (17)	0.0374 (16)	−0.0354 (17)	−0.0100 (15)	0.0011 (13)
C20	0.0317 (15)	0.0346 (14)	0.0327 (15)	−0.0129 (12)	0.0002 (12)	−0.0087 (12)
C21	0.0422 (17)	0.0358 (15)	0.0265 (14)	−0.0207 (13)	0.0045 (11)	−0.0049 (11)
C22	0.0423 (18)	0.0411 (16)	0.0498 (18)	−0.0197 (14)	0.0098 (14)	−0.0162 (14)
C23	0.0414 (18)	0.058 (2)	0.061 (2)	−0.0303 (16)	0.0103 (15)	−0.0203 (16)
C24	0.061 (2)	0.0409 (17)	0.0423 (17)	−0.0348 (16)	0.0083 (14)	−0.0084 (13)
C25	0.054 (2)	0.0329 (15)	0.0429 (17)	−0.0188 (14)	0.0001 (14)	−0.0040 (13)
C26	0.0395 (17)	0.0380 (16)	0.0430 (17)	−0.0178 (14)	0.0032 (13)	−0.0082 (13)
N1	0.0426 (14)	0.0311 (12)	0.0362 (12)	−0.0203 (11)	−0.0023 (10)	−0.0079 (10)
N2	0.075 (2)	0.0366 (14)	0.0513 (16)	−0.0297 (15)	−0.0045 (14)	−0.0068 (12)
N3	0.088 (3)	0.070 (2)	0.063 (2)	−0.061 (2)	−0.0171 (19)	0.0032 (16)
O1	0.133 (3)	0.089 (2)	0.121 (3)	−0.087 (2)	−0.009 (2)	−0.0254 (19)
O2	0.074 (2)	0.101 (2)	0.121 (3)	−0.063 (2)	−0.002 (2)	−0.007 (2)
O3	0.0553 (14)	0.0526 (13)	0.0437 (12)	−0.0285 (11)	0.0144 (10)	−0.0226 (10)

Br1—C24	1.899 (3)	C15—C16	1.329 (4)
C1—C2	1.405 (4)	C15—H15	0.9300
C1—C14	1.410 (4)	C16—N1	1.434 (3)
C1—C15	1.471 (4)	C16—C20	1.487 (4)
C2—C3	1.419 (5)	C17—C19	1.353 (4)
C2—C7	1.436 (4)	C17—N1	1.359 (4)
C3—C4	1.349 (5)	C17—H17	0.9300
C3—H3	0.9300	C18—N2	1.305 (4)
C4—C5	1.408 (6)	C18—N1	1.365 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.341 (6)	C19—N2	1.351 (4)
C5—H5	0.9300	C19—N3	1.442 (4)
C6—C7	1.432 (5)	C20—O3	1.211 (3)
C6—H6	0.9300	C20—C21	1.497 (4)
C7—C8	1.379 (5)	C21—C26	1.382 (4)
C8—C9	1.379 (5)	C21—C22	1.387 (4)
C8—H8	0.9300	C22—C23	1.387 (4)
C9—C10	1.417 (5)	C22—H22	0.9300
C9—C14	1.444 (5)	C23—C24	1.365 (5)
C10—C11	1.338 (7)	C23—H23	0.9300
C10—H10	0.9300	C24—C25	1.380 (5)
C11—C12	1.426 (7)	C25—C26	1.384 (4)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.358 (5)	C26—H26	0.9300
C12—H12	0.9300	N3—O1	1.222 (4)
C13—C14	1.415 (5)	N3—O2	1.224 (5)
C13—H13	0.9300
C2—C1—C14	121.2 (3)	C16—C15—H15	115.2
C2—C1—C15	118.2 (3)	C1—C15—H15	115.2
C14—C1—C15	120.3 (3)	C15—C16—N1	121.6 (2)
C1—C2—C3	123.1 (3)	C15—C16—C20	122.8 (2)
C1—C2—C7	119.1 (3)	N1—C16—C20	115.5 (2)
C3—C2—C7	117.7 (3)	C19—C17—N1	104.3 (3)
C4—C3—C2	121.8 (4)	C19—C17—H17	127.8
C4—C3—H3	119.1	N1—C17—H17	127.8
C2—C3—H3	119.1	N2—C18—N1	112.3 (3)
C3—C4—C5	120.4 (4)	N2—C18—H18	123.9
C3—C4—H4	119.8	N1—C18—H18	123.9
C5—C4—H4	119.8	N2—C19—C17	112.9 (3)
C6—C5—C4	120.6 (4)	N2—C19—N3	121.2 (3)
C6—C5—H5	119.7	C17—C19—N3	125.9 (4)
C4—C5—H5	119.7	O3—C20—C16	120.7 (2)
C5—C6—C7	121.2 (4)	O3—C20—C21	121.2 (2)
C5—C6—H6	119.4	C16—C20—C21	118.0 (2)
C7—C6—H6	119.4	C26—C21—C22	119.1 (3)
C8—C7—C2	119.4 (3)	C26—C21—C20	124.6 (3)
C8—C7—C6	122.3 (3)	C22—C21—C20	116.3 (3)
C2—C7—C6	118.3 (3)	C23—C22—C21	120.5 (3)
C9—C8—C7	122.1 (3)	C23—C22—H22	119.8
C9—C8—H8	118.9	C21—C22—H22	119.8
C7—C8—H8	118.9	C24—C23—C22	119.0 (3)
C8—C9—C10	121.4 (4)	C24—C23—H23	120.5
C8—C9—C14	120.0 (3)	C22—C23—H23	120.5
C10—C9—C14	118.6 (4)	C23—C24—C25	122.0 (3)
C11—C10—C9	121.5 (4)	C23—C24—Br1	117.4 (2)
C11—C10—H10	119.2	C25—C24—Br1	120.6 (2)
C9—C10—H10	119.2	C26—C25—C24	118.4 (3)
C10—C11—C12	120.2 (4)	C26—C25—H25	120.8
C10—C11—H11	119.9	C24—C25—H25	120.8
C12—C11—H11	119.9	C21—C26—C25	121.0 (3)
C13—C12—C11	120.4 (4)	C21—C26—H26	119.5
C13—C12—H12	119.8	C25—C26—H26	119.5
C11—C12—H12	119.8	C17—N1—C18	106.8 (2)
C12—C13—C14	121.0 (4)	C17—N1—C16	125.3 (2)
C12—C13—H13	119.5	C18—N1—C16	128.0 (2)
C14—C13—H13	119.5	C18—N2—C19	103.7 (3)
C1—C14—C13	123.7 (3)	O1—N3—O2	124.9 (4)
C1—C14—C9	118.1 (3)	O1—N3—C19	117.7 (4)
C13—C14—C9	118.1 (3)	O2—N3—C19	117.4 (3)
C16—C15—C1	129.6 (2)
C14—C1—C2—C3	−179.0 (3)	C1—C15—C16—C20	−170.6 (3)
C15—C1—C2—C3	6.7 (4)	N1—C17—C19—N2	1.0 (3)
C14—C1—C2—C7	−0.3 (4)	N1—C17—C19—N3	−178.9 (3)
C15—C1—C2—C7	−174.6 (2)	C15—C16—C20—O3	168.5 (3)
C1—C2—C3—C4	−178.6 (3)	N1—C16—C20—O3	−8.1 (4)
C7—C2—C3—C4	2.6 (5)	C15—C16—C20—C21	−7.7 (4)
C2—C3—C4—C5	−0.7 (5)	N1—C16—C20—C21	175.6 (2)
C3—C4—C5—C6	−1.4 (6)	O3—C20—C21—C26	118.6 (3)
C4—C5—C6—C7	1.5 (6)	C16—C20—C21—C26	−65.2 (4)
C1—C2—C7—C8	−1.2 (4)	O3—C20—C21—C22	−59.7 (4)
C3—C2—C7—C8	177.6 (3)	C16—C20—C21—C22	116.5 (3)
C1—C2—C7—C6	178.7 (3)	C26—C21—C22—C23	1.7 (4)
C3—C2—C7—C6	−2.5 (4)	C20—C21—C22—C23	−180.0 (3)
C5—C6—C7—C8	−179.5 (3)	C21—C22—C23—C24	−1.0 (5)
C5—C6—C7—C2	0.5 (5)	C22—C23—C24—C25	−0.4 (5)
C2—C7—C8—C9	1.9 (5)	C22—C23—C24—Br1	178.3 (2)
C6—C7—C8—C9	−178.0 (3)	C23—C24—C25—C26	1.2 (5)
C7—C8—C9—C10	177.8 (3)	Br1—C24—C25—C26	−177.4 (2)
C7—C8—C9—C14	−1.1 (5)	C22—C21—C26—C25	−0.9 (4)
C8—C9—C10—C11	−177.3 (4)	C20—C21—C26—C25	−179.1 (3)
C14—C9—C10—C11	1.7 (6)	C24—C25—C26—C21	−0.5 (4)
C9—C10—C11—C12	0.9 (7)	C19—C17—N1—C18	−0.3 (3)
C10—C11—C12—C13	−1.6 (7)	C19—C17—N1—C16	−178.5 (2)
C11—C12—C13—C14	−0.4 (6)	N2—C18—N1—C17	−0.5 (3)
C2—C1—C14—C13	−174.5 (3)	N2—C18—N1—C16	177.6 (3)
C15—C1—C14—C13	−0.3 (4)	C15—C16—N1—C17	53.4 (4)
C2—C1—C14—C9	1.1 (4)	C20—C16—N1—C17	−129.9 (3)
C15—C1—C14—C9	175.3 (3)	C15—C16—N1—C18	−124.4 (3)
C12—C13—C14—C1	178.5 (3)	C20—C16—N1—C18	52.4 (4)
C12—C13—C14—C9	3.0 (5)	N1—C18—N2—C19	1.0 (3)
C8—C9—C14—C1	−0.4 (4)	C17—C19—N2—C18	−1.3 (4)
C10—C9—C14—C1	−179.4 (3)	N3—C19—N2—C18	178.6 (3)
C8—C9—C14—C13	175.4 (3)	N2—C19—N3—O1	0.2 (5)
C10—C9—C14—C13	−3.6 (5)	C17—C19—N3—O1	−180.0 (3)
C2—C1—C15—C16	−126.2 (3)	N2—C19—N3—O2	179.8 (3)
C14—C1—C15—C16	59.4 (4)	C17—C19—N3—O2	−0.3 (5)
C1—C15—C16—N1	5.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O3i	0.93	2.56	3.303 (4)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O3i	0.93	2.56	3.303 (4)	137

Symmetry code: (i) .