organic compounds
H-imidazol-1-yl)phenyl]-2-(4-nitrophenyl)prop-2-enenitrile
of 3-[4-(1aDeparment 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
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 molecules are linked by weak C—H⋯O interactions, generating [001] C(6) chains.
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
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2.3. Refinement
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Data collection: SMART (Bruker, 2000); cell 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
https://doi.org/10.1107/S2056989015013730/hb7432sup1.cif
contains datablocks I, Global. DOI: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
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.
For chemical and photophysical background, see: Liu et al. (2006); Zheng et al. (2013). For a related structure, see: Li (2011).
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.
detailsCrystal data, data collection and structure
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 Uiso(H) = 1.2 Ueq.Data collection: SMART (Bruker, 2000); cell
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).Fig. 1. The molecular structure of the title molecule. | |
Fig. 2. The extended structure of the title compound. |
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 |
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 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 |
C18H12N4O2 | V = 1483.3 (6) Å3 |
Mr = 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)° |
Bruker SMART CCD diffractometer | 2609 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2081 reflections with I > 2σ(I) |
Tmin = 0.320, Tmax = 0.439 | Rint = 0.024 |
10392 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.18 e Å−3 |
2609 reflections | Δρmin = −0.17 e Å−3 |
217 parameters |
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 | ||
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* |
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) |
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) |
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. |
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).
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