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

Guang-Zhou Wang; Bo Fang; Cheng-He Zhou

doi:10.1107/S1600536809039221

. 2009 Oct 3;65(Pt 11):o2619. doi: 10.1107/S1600536809039221

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

Guang-Zhou Wang ^a, Bo Fang ^a, Cheng-He Zhou ^a,^*

PMCID: PMC2971385 PMID: 21578235

Abstract

In the title molecule, C₂₇H₁₉N₃O₃, 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 interactions 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 _r = 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
Δρ_max = 0.18 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-65-o2619-sup1.cif^{(22.7KB, cif)}

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

e-65-o2619-Isup2.hkl^{(226.4KB, hkl)}

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

Acknowledgments

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

supplementary crystallographic information

Comment

Chalcones or 1,3-diaryl-2-propen-1-ones are natural or synthetic compounds belonging to the flavonoid family (Vogel et al., 2008). They exhibit diverse kinds of biological activities. Hence, chalcones are considered as an important class of therapeutic agents. A series of chalcone derivatives containing a imidazole ring have been synthesized in our lab and crystal structues of some of them have been reported (Lu et al., 2009; Wang et al., 2009). We report here the crystal structure of the title compound.

In the molecular structure of the title compound (Fig. 1), the imidazole and benzene ring of the tolyl group form 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 structure is stabilized by weak π-π interactions between imidazole and benzene ring of the tolyl group (centroid to centroid distance = 3.7627 (9) Å) and those between the rings of the anthracene ring system (centroid to centroid distance = 3.7342 (10) Å).

Experimental

The title compound was synthesized according to the procedure of Erhardt et al. (1985). Single crystals suitable for X-ray analysis was grown from a chloroform solution by slow evaporation at room temperature.

Figures

Fig. 1. — The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C₂₇H₁₉N₃O₃	Z = 2
M_r = 433.45	F(000) = 452
Triclinic, P1	D_x = 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

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Data collection

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

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Refinement

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(F_o²) + (0.0696P)² + 0.061P] where P = (F_o² + 2F_c²)/3
4621 reflections	(Δ/σ)_max = 0.012
299 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

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Special details

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.

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

	x	y	z	U_iso*/U_eq
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)

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Atomic displacement parameters (Å²)

	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)

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Geometric parameters (Å, °)

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)

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2921).

References

Bruker (2001). SMART and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
Erhardt, H., Mildenberger, H., Handte, R., Sachse, B., Hartz, P. & Bürstell, H. (1985). German Patent No. DE3406908.
Lu, Y.-H., Wang, G.-Z., Zhou, C.-H. & Zhang, Y.-Y. (2009). Acta Cryst. E65, o1396. [DOI] [PMC free article] [PubMed]
Sheldrick, G. M. (1997). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Vogel, S., Ohmayer, S., Brunner, G. & Heilmann, J. (2008). Bioorg. Med. Chem.16, 4286–4293. [DOI] [PubMed]
Wang, G., Lu, Y., Zhou, C. & Zhang, Y. (2009). Acta Cryst. E65, o1113. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-65-o2619-sup1.cif^{(22.7KB, cif)}

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

e-65-o2619-Isup2.hkl^{(226.4KB, hkl)}

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

[bb1] Bruker (2001). SMART and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.

[bb2] Erhardt, H., Mildenberger, H., Handte, R., Sachse, B., Hartz, P. & Bürstell, H. (1985). German Patent No. DE3406908.

[bb3] Lu, Y.-H., Wang, G.-Z., Zhou, C.-H. & Zhang, Y.-Y. (2009). Acta Cryst. E65, o1396. [DOI] [PMC free article] [PubMed]

[bb4] Sheldrick, G. M. (1997). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.

[bb5] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb6] Vogel, S., Ohmayer, S., Brunner, G. & Heilmann, J. (2008). Bioorg. Med. Chem.16, 4286–4293. [DOI] [PubMed]

[bb7] Wang, G., Lu, Y., Zhou, C. & Zhang, Y. (2009). Acta Cryst. E65, o1113. [DOI] [PMC free article] [PubMed]

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Guang-Zhou Wang

Bo Fang

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Abstract

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Experimental

Crystal data

Data collection

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Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

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Figures

Fig. 1.

Crystal data

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

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

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

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

Atomic displacement parameters (Å²)