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

Wang, G.; Lu, Y.; Zhou, C.; Zhang, Y.

doi:10.1107/S1600536809014676

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1113

doi:10.1107/S1600536809014676

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

Guang-zhou Wang,^a Yi-hui Lu,^a Cheng-he Zhou ^a ^* and Yi-yi Zhang ^a

^aSchool of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 10 April 2009; accepted 20 April 2009; online 25 April 2009)

In the title compound, C₂₆H₁₆ClN₃O₃, the dihedral angle between the anthracene mean plane and imidazole ring is 64.75 (2)°. In the crystal, π–π interactions between anthracene fragments lead to the formation of stacks of molecules 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 interactions. The crystal packing also exhibits short intermolecular 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_r = 453.87
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.113
S = 1.04
4070 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Selected interatomic distances (Å)

C17⋯O1ⁱ	2.985 (2)
Cl1⋯O3ⁱⁱ	3.181 (3)
Cg1⋯Cg2ⁱⁱⁱ	3.746 (7)
Cg2⋯Cg2^iv	3.863 (8)
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x+1, y+1, z; (iii) -x+1, -y+2, -z+1; (iv) -x, -y+2, -z+1. Cg1 and Cg2 are the centroids of atoms C1/C2/C14/C7–C9 and C2–C7, respectively.

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.

Supporting information

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

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

checkCIF report

Comment top

Chalcones or 1,3-diaryl-2-propen-1-ones are natural or synthetic compounds belonging to the flavonoid family (Corrêa et al., 2001). They exhibit different kinds of biological activities, such as antimicrobial, anticancer, antiviral, ant-malarial, anti-inflammatory activities (Daskiewicz et al., 2005; Vogel et al., 2008; Sivakumar et al., 2009). Hence, chalcones are considered as a class of important therapeutic potentials. The title compound, (I), is part of our effort in order to contribute this research, and we report its crystal structure here.

In (I) (Fig. 1), the dihedral angle between the anthracene and imidazole rings is 64.75 (2)° and the nitroimidazole is slightly twisted away from the 4-chlorophenyl ring with a dihedral angle of 11.55 (2)°. In the crystal, the π-π interactions between the anthracene fragments (Table 1) lead to formation of stacks of the molecules propagated in direction [100]. The short distance between the carbonyl groups [C17···O1(1-x, 2-y, -z) 2.985 (2) Å] (Table 1) reveals an existence of dipole-dipole interactions. The crystal packing also exhibits short intermolecular contacts between the nitro groups and chlorine atoms [Cl···O 3.181 (2) Å] (Table 1).

Related literature top

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 top

Compound (I) was synthesized according to the procedure of Erhardt et al. (1985). A crystal of (I) suitable for X-ray analysis was grown from a mixture solution of chloroform and acetone by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

(Z)-3-(9-Anthryl)-1-(4-chlorophenyl)-2-(4-nitro-1H- imidazol-1-yl)prop-2-en-1-one top

Crystal data top

C₂₆H₁₆ClN₃O₃	Z = 2
M_r = 453.87	F(000) = 468
Triclinic, P1	D_x = 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

Data collection top

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 monochromator	R_int = 0.014
0.3° wide ω exposures scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −9→9
T_min = 0.956, T_max = 0.979	k = −13→10
6168 measured reflections	l = −15→15

Refinement top

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(F_o²) + (0.0441P)² + 0.4068P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4070 reflections	Δρ_max = 0.56 e Å⁻³
299 parameters	Δρ_min = −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)

Crystal data top

C₂₆H₁₆ClN₃O₃	γ = 71.258 (2)°
M_r = 453.87	V = 1056.1 (2) Å³
Triclinic, P1	Z = 2
a = 8.0511 (9) Å	Mo Kα radiation
b = 11.0406 (12) Å	µ = 0.22 mm⁻¹
c = 12.9274 (14) Å	T = 292 K
α = 76.065 (2)°	0.16 × 0.12 × 0.10 mm
β = 85.974 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4070 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3354 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.979	R_int = 0.014
6168 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.04	Δρ_max = 0.56 e Å⁻³
4070 reflections	Δρ_min = −0.50 e Å⁻³
299 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···Cg2^iv	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)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x+1, y+1, z; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₆ClN₃O₃
M_r	453.87
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	8.0511 (9), 11.0406 (12), 12.9274 (14)
α, β, γ (°)	76.065 (2), 85.974 (2), 71.258 (2)
V (Å³)	1056.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.956, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	6168, 4070, 3354
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.113, 1.04
No. of reflections	4070
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.50

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected interatomic distances (Å) top

C17···O1ⁱ	2.985 (2)	Cg1···Cg2ⁱⁱⁱ	3.746 (7)
Cl1···O3ⁱⁱ	3.181 (3)	Cg2···Cg2^iv	3.863 (8)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x+1, y+1, z; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+2, −z+1.

Acknowledgements

We thank Southwest University (grant Nos. SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (grant No. 2007BB5369) for financial support.

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Corrêa, R., Pereira, M. A. S., Santos, L. D., Filho, V. C., Santos, A. R. S. & Nunes, R. J. (2001). Arch. Pharm. Pharm. Med. Chem. 334, 332–334. Google Scholar
Daskiewicz, J. B., Depeint, F., Viornery, L., Bayet, C., Sarrazin, G. C., Comte, G., Gee, J. M., Johnson, I. T., Ndjoko, K., Hostettmann, K. & Barron, D. (2005). J. Med. Chem. 48, 2790–2804. Web of Science CrossRef PubMed CAS Google Scholar
Erhardt, H., Mildenberger, H., Handte, R., Sachse, B., Hartz, P. & Bürstell, H. (1985). German Patent No. DE3406908. Google Scholar
Sheldrick, G. M. (1997). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sivakumar, P. M., Priya, S. & Doble, M. (2009). Chem. Biol. Drug Des. 73, 403–415. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vogel, S., Ohmayer, S., Brunner, G. & Heilmann, J. (2008). Bioorg. Med. Chem. 16, 4286–4293. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 65| Part 5| May 2009| Page o1113

doi:10.1107/S1600536809014676

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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