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

Yu, T.; Yang, M.-D.; Pi, J.; Zhang, Y.-B.; Yu, J.-H.

doi:10.1107/S2056989015013730

organic compounds

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

Ting-ting Yu,^a,^b ^* Ming-Di Yang,^a,^b Jing-jing Pi,^a,^b Yu-Bin Zhang ^a,^b and Jian-Hua Yu ^a,^b

^aDeparment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and ^bKey Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: 806094151@qq.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 20 May 2015; accepted 20 July 2015; online 6 August 2015)

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.

Keywords: crystal structure; delocalised D—π—A electronic structure; hydrogen bonding.

CCDC reference: 1045501

1. Related literature

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

2. Experimental

2.1. Crystal data

C₁₈H₁₂N₄O₂
M_r = 316.32
Monoclinic, P 2₁ /c
a = 7.1792 (16) Å
b = 16.512 (4) Å
c = 12.771 (3) Å
β = 101.557 (3)°
V = 1483.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.25 × 0.2 × 0.18 mm

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

CCDC reference: 1045501

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2056989015013730/hb7432sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013730/hb7432Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015013730/hb7432Isup3.cml

checkCIF report

Synthesis and crystallization top

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.

Refinement top

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.

Related literature top

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

Structure description top

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

Synthesis and crystallization top

Refinement details top

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title molecule.
	Fig. 2. The extended structure of the title compound.

3-[4-(1H-Imidazol-1-yl)phenyl]-2-(4-nitrophenyl)prop-2-enenitrile top

Crystal data top

C₁₈H₁₂N₄O₂	Z = 4
M_r = 316.32	F(000) = 656
Monoclinic, P2₁/c	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0531P)² + 0.2091P] where P = (F_o² + 2F_c²)/3
2609 reflections	(Δ/σ)_max = 0.002
217 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₂N₄O₂	V = 1483.3 (6) Å³
M_r = 316.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1792 (16) Å	µ = 0.10 mm⁻¹
b = 16.512 (4) Å	T = 296 K
c = 12.771 (3) Å	0.25 × 0.2 × 0.18 mm
β = 101.557 (3)°

Data collection top

Bruker SMART CCD diffractometer	2609 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2081 reflections with I > 2σ(I)
T_min = 0.320, T_max = 0.439	R_int = 0.024
10392 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.07	Δρ_max = 0.18 e Å⁻³
2609 reflections	Δρ_min = −0.17 e Å⁻³
217 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
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 (Å²) top

	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) top

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) top

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.

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

This work was supported by the Graduate Students Innovative Program of Anhui University (grant Nos. J18515024, J18515019 and 201310357155).

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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