Crystal structure of 3-[4-(1H-imidazol-1-yl)phen­yl]-2-(4-nitro­phen­yl)prop-2-ene­nitrile

Abstract

In the title compound, C₁₈H₁₂N₄O₂, which has a delocalized D—π—A electronic structure, the dihedral angles between the central benzene ring and the planes of the pendant imidazole and nitro­benzene rings are 37.65 (9) and 4.96 (7)°, respectively. In the centrosymmetric crystal structure, mol­ecules are linked by weak C—H⋯O inter­actions, generating [001] C(6) chains.

Related literature  

For chemical and photophysical background, see: Liu et al. (2006 ▸); Zheng et al. (2013 ▸). For a related structure, see: Li (2011 ▸).

Experimental  

Crystal data  

• C₁₈H₁₂N₄O₂

• M _r = 316.32

• Monoclinic,

• a = 7.1792 (16) Å

• b = 16.512 (4) Å

• c = 12.771 (3) Å

• β = 101.557 (3)°

• V = 1483.3 (6) ų

• Z = 4

• Mo Kα radiation

• μ = 0.10 mm⁻¹

• T = 296 K

• 0.25 × 0.2 × 0.18 mm

Data collection  

• Bruker SMART CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2000 ▸) T _min = 0.320, T _max = 0.439

• 10392 measured reflections

• 2609 independent reflections

• 2081 reflections with I > 2σ(I)

• R _int = 0.024

Refinement  

• R[F ² > 2σ(F ²)] = 0.036

• wR(F ²) = 0.105

• S = 1.07

• 2609 reflections

• 217 parameters

• H-atom parameters constrained

• Δρ_max = 0.18 e Å⁻³

• Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ▸); cell refinement: SAINT (Bruker, 2000 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

CCDC reference: 1045501

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C18H18O2i	0.93	2.54	3.464(2)	173

Symmetry code: (i) .

supplementary crystallographic information

S1. Synthesis and crystallization

3-(4-Imidazol-1-yl-phenyl)-2-(4-nitro-phenyl)-acrylo­nitrile was dissolved in ethanol solvent. Then added 4-nitro-benzo­nitrile into the solvent. When the two compounds were mixed completly, dropwise added a few piperidine into them. About seven hours later, we could get the title compound.

S2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å and U_iso(H) = 1.2 U_eq.

Figures

Fig. 1.

The molecular structure of the title molecule.

Fig. 2.

The extended structure of the title compound.

Crystal data

C18H12N4O2	Z = 4
Mr = 316.32	F(000) = 656
Monoclinic, P21/c	Dx = 1.416 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.1792 (16) Å	µ = 0.10 mm−1
b = 16.512 (4) Å	T = 296 K
c = 12.771 (3) Å	Block, red
β = 101.557 (3)°	0.25 × 0.2 × 0.18 mm
V = 1483.3 (6) Å3

Data collection

Bruker SMART CCD diffractometer	2609 independent reflections
Radiation source: sealed tube	2081 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.320, Tmax = 0.439	k = −19→17
10392 measured reflections	l = −15→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.2091P] where P = (Fo2 + 2Fc2)/3
2609 reflections	(Δ/σ)max = 0.002
217 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

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

	x	y	z	Uiso*/Ueq
N1	0.33343 (18)	0.36839 (7)	0.53687 (9)	0.0409 (3)
C11	0.2512 (2)	0.49937 (9)	0.03244 (11)	0.0373 (3)
C16	0.1639 (2)	0.65848 (9)	−0.23484 (11)	0.0433 (4)
C7	0.2711 (2)	0.47837 (9)	0.23353 (10)	0.0380 (3)
C14	0.2517 (2)	0.52940 (9)	−0.15944 (11)	0.0441 (4)
H14	0.2917	0.4765	−0.1669	0.053*
C9	0.3390 (2)	0.36047 (9)	0.34742 (11)	0.0412 (4)
H9	0.3709	0.3059	0.3557	0.049*
C4	0.3103 (2)	0.40518 (9)	0.43461 (10)	0.0379 (3)
C13	0.2195 (2)	0.55534 (8)	−0.06072 (11)	0.0370 (3)
C5	0.2614 (2)	0.48643 (9)	0.42196 (11)	0.0458 (4)
H5	0.2416	0.5167	0.4802	0.055*
C10	0.2475 (2)	0.52285 (9)	0.13288 (11)	0.0404 (4)
H10	0.2257	0.5780	0.1395	0.048*
C6	0.2421 (2)	0.52205 (9)	0.32260 (11)	0.0438 (4)
H6	0.2091	0.5765	0.3147	0.053*
C8	0.3203 (2)	0.39658 (9)	0.24824 (11)	0.0421 (4)
H8	0.3408	0.3661	0.1904	0.050*
N4	0.1372 (2)	0.71310 (10)	−0.32681 (11)	0.0563 (4)
C18	0.1554 (2)	0.63447 (9)	−0.05281 (11)	0.0441 (4)
H18	0.1308	0.6527	0.0120	0.053*
C15	0.2251 (2)	0.58088 (10)	−0.24634 (11)	0.0481 (4)
H15	0.2484	0.5632	−0.3117	0.058*
O2	0.0835 (2)	0.78255 (8)	−0.31500 (10)	0.0736 (4)
O1	0.1702 (2)	0.68742 (9)	−0.41145 (10)	0.0818 (5)
C17	0.1280 (2)	0.68607 (9)	−0.13928 (12)	0.0461 (4)
H17	0.0859	0.7388	−0.1331	0.055*
N3	0.3111 (3)	0.35246 (9)	−0.02129 (11)	0.0666 (5)
C12	0.2850 (2)	0.41644 (10)	0.00623 (11)	0.0448 (4)
N2	0.4589 (2)	0.29296 (8)	0.67745 (10)	0.0579 (4)
C1	0.4684 (2)	0.31340 (9)	0.57988 (12)	0.0496 (4)
H1	0.5579	0.2926	0.5436	0.059*
C3	0.2306 (3)	0.38325 (10)	0.61467 (12)	0.0562 (5)
H3	0.1281	0.4184	0.6103	0.067*
C2	0.3083 (3)	0.33654 (10)	0.69857 (12)	0.0603 (5)
H2	0.2653	0.3342	0.7625	0.072*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
N1	0.0543 (8)	0.0397 (7)	0.0291 (6)	−0.0003 (6)	0.0094 (5)	0.0024 (5)
C11	0.0401 (8)	0.0386 (8)	0.0334 (7)	−0.0035 (6)	0.0078 (6)	0.0014 (6)
C16	0.0444 (9)	0.0498 (9)	0.0355 (8)	−0.0052 (7)	0.0075 (6)	0.0098 (7)
C7	0.0425 (8)	0.0386 (8)	0.0322 (7)	−0.0036 (6)	0.0062 (6)	−0.0001 (6)
C14	0.0549 (10)	0.0432 (8)	0.0363 (8)	0.0002 (7)	0.0137 (7)	−0.0001 (6)
C9	0.0526 (9)	0.0356 (8)	0.0356 (8)	−0.0009 (7)	0.0097 (7)	0.0000 (6)
C4	0.0441 (9)	0.0398 (8)	0.0295 (7)	−0.0026 (6)	0.0066 (6)	0.0015 (6)
C13	0.0376 (8)	0.0414 (8)	0.0319 (7)	−0.0054 (6)	0.0071 (6)	0.0008 (6)
C5	0.0640 (11)	0.0425 (9)	0.0312 (7)	0.0033 (7)	0.0100 (7)	−0.0040 (6)
C10	0.0490 (9)	0.0375 (8)	0.0348 (8)	−0.0009 (6)	0.0084 (6)	0.0018 (6)
C6	0.0600 (10)	0.0355 (8)	0.0354 (8)	0.0036 (7)	0.0080 (7)	0.0014 (6)
C8	0.0556 (9)	0.0402 (8)	0.0315 (7)	−0.0008 (7)	0.0116 (6)	−0.0033 (6)
N4	0.0608 (9)	0.0647 (10)	0.0443 (8)	−0.0025 (8)	0.0127 (7)	0.0175 (7)
C18	0.0555 (10)	0.0446 (9)	0.0333 (7)	−0.0009 (7)	0.0115 (7)	−0.0002 (6)
C15	0.0576 (10)	0.0577 (10)	0.0315 (8)	−0.0041 (8)	0.0152 (7)	0.0016 (7)
O2	0.0926 (11)	0.0641 (9)	0.0665 (8)	0.0148 (7)	0.0215 (7)	0.0280 (7)
O1	0.1185 (12)	0.0900 (10)	0.0419 (7)	0.0087 (9)	0.0283 (7)	0.0193 (6)
C17	0.0548 (10)	0.0412 (8)	0.0420 (8)	−0.0010 (7)	0.0085 (7)	0.0040 (6)
N3	0.1093 (14)	0.0488 (9)	0.0411 (8)	0.0102 (8)	0.0134 (8)	−0.0023 (7)
C12	0.0594 (10)	0.0468 (10)	0.0280 (7)	−0.0003 (8)	0.0081 (7)	0.0032 (6)
N2	0.0896 (11)	0.0457 (8)	0.0374 (7)	0.0032 (7)	0.0100 (7)	0.0066 (6)
C1	0.0659 (11)	0.0437 (9)	0.0390 (8)	0.0049 (8)	0.0102 (7)	0.0048 (7)
C3	0.0763 (12)	0.0558 (10)	0.0417 (9)	0.0094 (9)	0.0247 (8)	0.0039 (7)
C2	0.0971 (14)	0.0522 (10)	0.0362 (8)	−0.0022 (10)	0.0245 (9)	0.0046 (7)

Geometric parameters (Å, º)

N1—C1	1.361 (2)	C13—C18	1.395 (2)
N1—C3	1.3736 (19)	C5—C6	1.380 (2)
N1—C4	1.4197 (17)	C5—H5	0.9300
C11—C10	1.3455 (19)	C10—H10	0.9300
C11—C12	1.442 (2)	C6—H6	0.9300
C11—C13	1.4876 (19)	C8—H8	0.9300
C16—C15	1.372 (2)	N4—O1	1.2277 (18)
C16—C17	1.375 (2)	N4—O2	1.2287 (18)
C16—N4	1.4626 (19)	C18—C17	1.377 (2)
C7—C6	1.3971 (19)	C18—H18	0.9300
C7—C8	1.399 (2)	C15—H15	0.9300
C7—C10	1.4606 (18)	C17—H17	0.9300
C14—C15	1.381 (2)	N3—C12	1.141 (2)
C14—C13	1.3939 (19)	N2—C1	1.306 (2)
C14—H14	0.9300	N2—C2	1.370 (2)
C9—C8	1.3820 (19)	C1—H1	0.9300
C9—C4	1.3853 (19)	C3—C2	1.347 (2)
C9—H9	0.9300	C3—H3	0.9300
C4—C5	1.388 (2)	C2—H2	0.9300
C1—N1—C3	105.65 (12)	C5—C6—C7	121.66 (14)
C1—N1—C4	126.83 (13)	C5—C6—H6	119.2
C3—N1—C4	127.46 (13)	C7—C6—H6	119.2
C10—C11—C12	122.11 (13)	C9—C8—C7	121.00 (13)
C10—C11—C13	123.67 (13)	C9—C8—H8	119.5
C12—C11—C13	114.22 (12)	C7—C8—H8	119.5
C15—C16—C17	121.71 (13)	O1—N4—O2	123.44 (14)
C15—C16—N4	118.88 (13)	O1—N4—C16	118.48 (15)
C17—C16—N4	119.41 (15)	O2—N4—C16	118.08 (14)
C6—C7—C8	117.63 (12)	C17—C18—C13	121.15 (14)
C6—C7—C10	116.55 (13)	C17—C18—H18	119.4
C8—C7—C10	125.82 (12)	C13—C18—H18	119.4
C15—C14—C13	121.12 (14)	C16—C15—C14	118.97 (14)
C15—C14—H14	119.4	C16—C15—H15	120.5
C13—C14—H14	119.4	C14—C15—H15	120.5
C8—C9—C4	120.27 (13)	C16—C17—C18	119.00 (15)
C8—C9—H9	119.9	C16—C17—H17	120.5
C4—C9—H9	119.9	C18—C17—H17	120.5
C9—C4—C5	119.76 (13)	N3—C12—C11	175.48 (15)
C9—C4—N1	120.17 (13)	C1—N2—C2	104.24 (14)
C5—C4—N1	120.06 (12)	N2—C1—N1	112.88 (15)
C14—C13—C18	118.02 (13)	N2—C1—H1	123.6
C14—C13—C11	120.40 (13)	N1—C1—H1	123.6
C18—C13—C11	121.58 (12)	C2—C3—N1	106.02 (15)
C6—C5—C4	119.68 (13)	C2—C3—H3	127.0
C6—C5—H5	120.2	N1—C3—H3	127.0
C4—C5—H5	120.2	C3—C2—N2	111.20 (14)
C11—C10—C7	132.31 (14)	C3—C2—H2	124.4
C11—C10—H10	113.8	N2—C2—H2	124.4
C7—C10—H10	113.8
C8—C9—C4—C5	0.4 (2)	C10—C7—C8—C9	179.97 (14)
C8—C9—C4—N1	−178.68 (13)	C15—C16—N4—O1	0.2 (2)
C1—N1—C4—C9	38.6 (2)	C17—C16—N4—O1	179.89 (15)
C3—N1—C4—C9	−144.54 (16)	C15—C16—N4—O2	−179.52 (15)
C1—N1—C4—C5	−140.54 (16)	C17—C16—N4—O2	0.2 (2)
C3—N1—C4—C5	36.3 (2)	C14—C13—C18—C17	−1.2 (2)
C15—C14—C13—C18	1.4 (2)	C11—C13—C18—C17	179.44 (14)
C15—C14—C13—C11	−179.21 (14)	C17—C16—C15—C14	−0.1 (2)
C10—C11—C13—C14	170.92 (14)	N4—C16—C15—C14	179.55 (14)
C12—C11—C13—C14	−9.6 (2)	C13—C14—C15—C16	−0.8 (2)
C10—C11—C13—C18	−9.7 (2)	C15—C16—C17—C18	0.4 (2)
C12—C11—C13—C18	169.74 (14)	N4—C16—C17—C18	−179.33 (14)
C9—C4—C5—C6	−0.2 (2)	C13—C18—C17—C16	0.3 (2)
N1—C4—C5—C6	178.97 (14)	C10—C11—C12—N3	−178 (2)
C12—C11—C10—C7	−0.7 (3)	C13—C11—C12—N3	3 (2)
C13—C11—C10—C7	178.73 (14)	C2—N2—C1—N1	0.59 (19)
C6—C7—C10—C11	−174.72 (15)	C3—N1—C1—N2	−0.18 (19)
C8—C7—C10—C11	5.5 (3)	C4—N1—C1—N2	177.24 (14)
C4—C5—C6—C7	−0.1 (2)	C1—N1—C3—C2	−0.32 (18)
C8—C7—C6—C5	0.1 (2)	C4—N1—C3—C2	−177.72 (14)
C10—C7—C6—C5	−179.70 (14)	N1—C3—C2—N2	0.7 (2)
C4—C9—C8—C7	−0.5 (2)	C1—N2—C2—C3	−0.8 (2)
C6—C7—C8—C9	0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2i	0.93	2.54	3.464 (2)	173

Symmetry code: (i) x, −y+3/2, z+1/2.