organic compounds
N-[1-(1H-Pyrrol-2-yl)ethylidene]aniline
aCollege of Chemistry and Chemical Engineering, Xi'an ShiYou University, Xi'an, Shaanxi 710065, People's Republic of China
*Correspondence e-mail: subiyun@xsyu.edu.cn
There are two independent molecules in the 12H12N2, in which the pyrrole and benzene rings form dihedral angles of 72.37 (7) and 82.34 (8)°. The imino N—C bond lengths in the two molecules are equal [1.286 (2) Å] and indicate C=N character. In the crystal, each molecule forms a dimer with an inversion-related molecule through a pair of classical N—H⋯N hydrogen bonds.
of the title compound, CRelated literature
For general background to the iminopyrrole unit, see: Small et al. (1998); Su et al. (2009a,b); Britovsek et al. (2003); Dawson et al. (2000). For the pyrrole diimine unit, see: Matsuo et al. (2001) and for the pyrrole monoimine unit, see: He et al. (2009).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker,2008); cell SAINT (Bruker,2008); data reduction: SAINT; 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: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536812037695/rk2378sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037695/rk2378Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812037695/rk2378Isup3.cml
The 2-acetyl pyrrole (0.1313 g, 1.20 mmol), aniline (0.1118 g, 1.20 mmol) were placed in a 50 ml flask, after a few drops of acetic acid were added in, the mixture was subjected to radiation in a 800 W microwave oven for 2 min and 3 min on a medium-heat setting. The reaction was monitored by TLC, and the crude product was purified by silica gel νC═N 1653 cm-1. 1H NMR (400 MHz, CDCl3): δ 7.33 (t, H, benzene ring aromatic H), 7.15 (t, 2H, benzene ring aromatic H), 7.02 (d, 2H, benzene ring aromatic H), 6.97 (t, 1H, pyrrole ring aromatic H), 6.33 (d, 1H, pyrrole ring aromatic H), 6.10 (d, 1H, pyrrole ring aromatic H), 2.03 (s, 3H, -N═C(CH3)-). MS (EI): m/z 184 (M). Anal. Calcd for C12H12N2: C, 78.23; H, 6.57; N, 15.21. Found: C, 78.50; H, 7.01; N, 14.96.
(eluent: petroleum ether/ethyl acetate, 5:1 v/v), the colourless or light yellow crystals of the title compound were at last obtained by recrystallization from ethanol (yield 0.063 g, 28.4%). M.p. 405.25-406.85 K. The purity and the composition of the compound were checked and characterized by IR spectrum, 1H NMR spectrum, as well as elemental analysis. IR (KBr):Plate like colourless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.
All H atoms were placed at calculated positions and refined as riding, with C–H = 0.93-0.96Å, N–H = 0.86Å, and with Uiso(H) = 1.2Ueq(C, N) and Uiso(H) = 1.5Ueq(C) for methyl H atoms.
In recent years, the bis(imino)pyridine incorporated late transition metal catalysts have received considerable attention because of their antioxidant property and outstanding activity for olefin polymerization (Small et al., 1998; Su et al., 2009a,b). As the five-memberd ring substitute of pyridine six-memberd ring (Matsuo et al., 2001; He et al., 2009), pyrrole was frequently introduced into the skeleton of bis(imino)pyridine ligand to design new ligand and corresponding metal complexes (Britovsek et al., 2003; Dawson et al., 2000). Bis(imino)pyrrole was usually prepared from Schiff base condensation of 2,5-diacetylpyrrole and the aromatic amine (Matsuo et al., 2001). As a contribution to this research field, we report herein the synthesis of mono(imino)pyrrole from 2-acetyl pyrrole and aromatic anime, as well as the
of the title compound 2-(1-phenyliminoethyl)pyrrole.The
of the title compound (Fig. 1) comprises of two crystallographically independent molecules A and B. In each molecule the pyrrole ring and benzene ring are essentially perpendicular, with dihedral angles of 72.37 (7)° and 82.34 (8)° respectively. The benzene ring of molecules A are nearly parallel with the benzene ring of molecules B with dihedral angle of 14.33 (14)°, but pyrrole ring of molecules A forms a comparative large 39.42 (9)° dihedral angle with the pyrrole ring of molecules B. On the whole, bond lengths and angles in both molecules are equal in the s.u. range. The crystal packing is stabilized by N–H···N classical intermolecular hydrogen bonds (Table 1, Fig. 2).For general background to the iminopyrrole unit, see: Small et al. (1998); Su et al. (2009a,b); Britovsek et al. (2003); Dawson et al. (2000). For the pyrrole diimine unit, see: Matsuo et al. (2001) and for the pyrrole monoimine unit, see: He et al. (2009).
Data collection: APEX2 (Bruker,2008); cell
SAINT (Bruker,2008); data reduction: SAINT (Bruker,2008); 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: publCIF (Westrip, 2010).C12H12N2 | Z = 4 |
Mr = 184.24 | F(000) = 392 |
Triclinic, P1 | Dx = 1.180 Mg m−3 |
Hall symbol: -P 1 | Melting point = 405.25–406.85 K |
a = 8.2236 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.3306 (19) Å | Cell parameters from 1351 reflections |
c = 11.913 (2) Å | θ = 2.4–25.1° |
α = 95.984 (3)° | µ = 0.07 mm−1 |
β = 93.202 (3)° | T = 296 K |
γ = 109.274 (3)° | Block, colourless |
V = 1037.3 (3) Å3 | 0.37 × 0.25 × 0.19 mm |
Bruker APEXII CCD diffractometer | 3655 independent reflections |
Radiation source: fine-focus sealed tube | 2567 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 25.1°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −9→9 |
Tmin = 0.974, Tmax = 0.987 | k = −9→13 |
5277 measured reflections | l = −14→11 |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
3655 reflections | Δρmax = 0.20 e Å−3 |
256 parameters | Δρmin = −0.13 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: 0.043 (5) |
C12H12N2 | γ = 109.274 (3)° |
Mr = 184.24 | V = 1037.3 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.2236 (14) Å | Mo Kα radiation |
b = 11.3306 (19) Å | µ = 0.07 mm−1 |
c = 11.913 (2) Å | T = 296 K |
α = 95.984 (3)° | 0.37 × 0.25 × 0.19 mm |
β = 93.202 (3)° |
Bruker APEXII CCD diffractometer | 3655 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2567 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.987 | Rint = 0.023 |
5277 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.20 e Å−3 |
3655 reflections | Δρmin = −0.13 e Å−3 |
256 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 | 0.1204 (2) | 1.17200 (13) | 0.61426 (13) | 0.0613 (4) | |
H1A | 0.0627 | 1.1263 | 0.5534 | 0.074* | |
N2 | 0.19520 (19) | 0.94813 (13) | 0.57233 (12) | 0.0557 (4) | |
N3 | 0.38995 (19) | 0.64751 (14) | −0.01282 (12) | 0.0557 (4) | |
H3A | 0.4486 | 0.6007 | −0.0354 | 0.067* | |
N4 | 0.31361 (19) | 0.43111 (14) | 0.10218 (13) | 0.0569 (4) | |
C1 | 0.1184 (3) | 1.28776 (18) | 0.6531 (2) | 0.0780 (6) | |
H1 | 0.0539 | 1.3305 | 0.6192 | 0.094* | |
C2 | 0.2261 (3) | 1.3311 (2) | 0.7498 (2) | 0.0812 (7) | |
H2 | 0.2502 | 1.4089 | 0.7935 | 0.097* | |
C3 | 0.2940 (3) | 1.23792 (19) | 0.77152 (17) | 0.0699 (6) | |
H3 | 0.3710 | 1.2419 | 0.8332 | 0.084* | |
C4 | 0.2279 (2) | 1.13853 (16) | 0.68614 (15) | 0.0524 (5) | |
C5 | 0.2640 (2) | 1.02211 (16) | 0.66444 (14) | 0.0519 (5) | |
C6 | 0.3844 (3) | 0.9990 (2) | 0.75197 (17) | 0.0783 (6) | |
H6A | 0.3216 | 0.9665 | 0.8140 | 0.117* | |
H6B | 0.4757 | 1.0767 | 0.7793 | 0.117* | |
H6C | 0.4331 | 0.9389 | 0.7187 | 0.117* | |
C7 | 0.2301 (2) | 0.83354 (16) | 0.54888 (15) | 0.0525 (5) | |
C8 | 0.1630 (3) | 0.73360 (18) | 0.60871 (18) | 0.0726 (6) | |
H8 | 0.0976 | 0.7418 | 0.6684 | 0.087* | |
C9 | 0.1917 (3) | 0.62193 (19) | 0.5811 (2) | 0.0814 (7) | |
H9 | 0.1457 | 0.5553 | 0.6224 | 0.098* | |
C10 | 0.2873 (3) | 0.6075 (2) | 0.4936 (2) | 0.0781 (6) | |
H10 | 0.3072 | 0.5319 | 0.4756 | 0.094* | |
C11 | 0.3536 (3) | 0.7066 (2) | 0.43257 (19) | 0.0772 (6) | |
H11 | 0.4184 | 0.6980 | 0.3727 | 0.093* | |
C12 | 0.3241 (3) | 0.81884 (18) | 0.46002 (17) | 0.0664 (5) | |
H12 | 0.3683 | 0.8850 | 0.4179 | 0.080* | |
C13 | 0.4041 (3) | 0.76033 (19) | −0.04693 (17) | 0.0651 (5) | |
H13 | 0.4783 | 0.8000 | −0.0982 | 0.078* | |
C14 | 0.2908 (3) | 0.8061 (2) | 0.00674 (18) | 0.0698 (6) | |
H14 | 0.2736 | 0.8820 | −0.0013 | 0.084* | |
C15 | 0.2060 (3) | 0.71803 (18) | 0.07579 (17) | 0.0627 (5) | |
H15 | 0.1218 | 0.7249 | 0.1225 | 0.075* | |
C16 | 0.2679 (2) | 0.61897 (16) | 0.06320 (14) | 0.0507 (4) | |
C17 | 0.2239 (2) | 0.50444 (16) | 0.11674 (14) | 0.0503 (4) | |
C18 | 0.0726 (3) | 0.47986 (18) | 0.18618 (16) | 0.0656 (5) | |
H18A | −0.0259 | 0.4157 | 0.1446 | 0.098* | |
H18B | 0.0462 | 0.5560 | 0.2025 | 0.098* | |
H18C | 0.1006 | 0.4522 | 0.2559 | 0.098* | |
C19 | 0.2680 (2) | 0.31984 (17) | 0.15675 (16) | 0.0561 (5) | |
C20 | 0.3454 (3) | 0.3213 (2) | 0.26340 (17) | 0.0708 (6) | |
H20 | 0.4238 | 0.3961 | 0.3014 | 0.085* | |
C21 | 0.3063 (3) | 0.2120 (3) | 0.3132 (2) | 0.0850 (7) | |
H21 | 0.3581 | 0.2136 | 0.3851 | 0.102* | |
C22 | 0.1926 (3) | 0.1014 (2) | 0.2583 (2) | 0.0873 (7) | |
H22 | 0.1663 | 0.0283 | 0.2927 | 0.105* | |
C23 | 0.1175 (3) | 0.0987 (2) | 0.1524 (2) | 0.0869 (7) | |
H23 | 0.0404 | 0.0233 | 0.1147 | 0.104* | |
C24 | 0.1551 (3) | 0.2071 (2) | 0.10094 (19) | 0.0730 (6) | |
H24 | 0.1042 | 0.2042 | 0.0285 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0669 (10) | 0.0474 (9) | 0.0668 (10) | 0.0195 (8) | −0.0074 (8) | 0.0011 (7) |
N2 | 0.0601 (9) | 0.0484 (8) | 0.0593 (9) | 0.0191 (7) | 0.0030 (8) | 0.0102 (7) |
N3 | 0.0549 (9) | 0.0621 (10) | 0.0579 (9) | 0.0271 (7) | 0.0110 (7) | 0.0155 (7) |
N4 | 0.0530 (9) | 0.0618 (9) | 0.0627 (9) | 0.0236 (8) | 0.0156 (7) | 0.0197 (7) |
C1 | 0.0800 (15) | 0.0517 (12) | 0.1002 (17) | 0.0274 (11) | −0.0127 (13) | −0.0059 (11) |
C2 | 0.0714 (14) | 0.0616 (13) | 0.1009 (17) | 0.0213 (11) | −0.0030 (13) | −0.0218 (12) |
C3 | 0.0603 (12) | 0.0749 (14) | 0.0679 (13) | 0.0209 (11) | −0.0028 (10) | −0.0087 (11) |
C4 | 0.0485 (10) | 0.0518 (10) | 0.0555 (11) | 0.0150 (8) | 0.0054 (8) | 0.0070 (8) |
C5 | 0.0497 (10) | 0.0543 (11) | 0.0520 (10) | 0.0155 (8) | 0.0071 (8) | 0.0141 (9) |
C6 | 0.0889 (16) | 0.0862 (15) | 0.0665 (13) | 0.0400 (13) | −0.0089 (12) | 0.0134 (11) |
C7 | 0.0519 (10) | 0.0509 (10) | 0.0556 (10) | 0.0183 (8) | 0.0031 (8) | 0.0092 (8) |
C8 | 0.0878 (15) | 0.0604 (12) | 0.0798 (14) | 0.0309 (11) | 0.0335 (12) | 0.0210 (10) |
C9 | 0.1039 (18) | 0.0574 (13) | 0.0943 (16) | 0.0343 (12) | 0.0340 (14) | 0.0233 (11) |
C10 | 0.0847 (16) | 0.0590 (13) | 0.0935 (16) | 0.0301 (12) | 0.0134 (13) | 0.0005 (12) |
C11 | 0.0715 (14) | 0.0779 (15) | 0.0800 (15) | 0.0235 (12) | 0.0208 (12) | −0.0006 (12) |
C12 | 0.0682 (13) | 0.0598 (12) | 0.0673 (13) | 0.0145 (10) | 0.0140 (10) | 0.0109 (10) |
C13 | 0.0620 (12) | 0.0718 (13) | 0.0703 (13) | 0.0282 (10) | 0.0107 (10) | 0.0277 (10) |
C14 | 0.0744 (14) | 0.0705 (13) | 0.0780 (14) | 0.0382 (11) | 0.0132 (11) | 0.0213 (11) |
C15 | 0.0641 (12) | 0.0711 (13) | 0.0634 (12) | 0.0339 (10) | 0.0145 (10) | 0.0142 (10) |
C16 | 0.0457 (10) | 0.0615 (11) | 0.0473 (10) | 0.0208 (8) | 0.0051 (8) | 0.0084 (8) |
C17 | 0.0472 (10) | 0.0583 (11) | 0.0457 (10) | 0.0188 (8) | 0.0033 (8) | 0.0055 (8) |
C18 | 0.0647 (12) | 0.0725 (13) | 0.0672 (12) | 0.0293 (10) | 0.0216 (10) | 0.0146 (10) |
C19 | 0.0474 (10) | 0.0639 (12) | 0.0649 (12) | 0.0248 (9) | 0.0165 (9) | 0.0176 (9) |
C20 | 0.0742 (14) | 0.0770 (14) | 0.0659 (13) | 0.0280 (11) | 0.0095 (11) | 0.0200 (11) |
C21 | 0.0857 (17) | 0.1045 (19) | 0.0803 (15) | 0.0435 (15) | 0.0171 (13) | 0.0376 (14) |
C22 | 0.0747 (16) | 0.0889 (18) | 0.118 (2) | 0.0381 (14) | 0.0315 (15) | 0.0529 (16) |
C23 | 0.0701 (15) | 0.0685 (14) | 0.121 (2) | 0.0177 (11) | 0.0122 (14) | 0.0271 (14) |
C24 | 0.0618 (13) | 0.0717 (14) | 0.0846 (15) | 0.0196 (11) | 0.0001 (11) | 0.0195 (11) |
N1—C1 | 1.350 (2) | C10—C11 | 1.378 (3) |
N1—C4 | 1.365 (2) | C10—H10 | 0.9300 |
N1—H1A | 0.8600 | C11—C12 | 1.381 (3) |
N2—C5 | 1.286 (2) | C11—H11 | 0.9300 |
N2—C7 | 1.423 (2) | C12—H12 | 0.9300 |
N3—C13 | 1.352 (2) | C13—C14 | 1.364 (3) |
N3—C16 | 1.371 (2) | C13—H13 | 0.9300 |
N3—H3A | 0.8600 | C14—C15 | 1.391 (3) |
N4—C17 | 1.286 (2) | C14—H14 | 0.9300 |
N4—C19 | 1.428 (2) | C15—C16 | 1.376 (2) |
C1—C2 | 1.355 (3) | C15—H15 | 0.9300 |
C1—H1 | 0.9300 | C16—C17 | 1.453 (2) |
C2—C3 | 1.387 (3) | C17—C18 | 1.498 (2) |
C2—H2 | 0.9300 | C18—H18A | 0.9600 |
C3—C4 | 1.376 (2) | C18—H18B | 0.9600 |
C3—H3 | 0.9300 | C18—H18C | 0.9600 |
C4—C5 | 1.446 (2) | C19—C24 | 1.381 (3) |
C5—C6 | 1.500 (3) | C19—C20 | 1.385 (3) |
C6—H6A | 0.9600 | C20—C21 | 1.379 (3) |
C6—H6B | 0.9600 | C20—H20 | 0.9300 |
C6—H6C | 0.9600 | C21—C22 | 1.363 (3) |
C7—C12 | 1.373 (3) | C21—H21 | 0.9300 |
C7—C8 | 1.376 (3) | C22—C23 | 1.366 (3) |
C8—C9 | 1.373 (3) | C22—H22 | 0.9300 |
C8—H8 | 0.9300 | C23—C24 | 1.381 (3) |
C9—C10 | 1.368 (3) | C23—H23 | 0.9300 |
C9—H9 | 0.9300 | C24—H24 | 0.9300 |
C1—N1—C4 | 109.71 (17) | C12—C11—H11 | 119.9 |
C1—N1—H1A | 125.1 | C7—C12—C11 | 120.60 (19) |
C4—N1—H1A | 125.1 | C7—C12—H12 | 119.7 |
C5—N2—C7 | 119.64 (15) | C11—C12—H12 | 119.7 |
C13—N3—C16 | 109.70 (15) | N3—C13—C14 | 108.30 (18) |
C13—N3—H3A | 125.2 | N3—C13—H13 | 125.9 |
C16—N3—H3A | 125.2 | C14—C13—H13 | 125.9 |
C17—N4—C19 | 118.11 (15) | C13—C14—C15 | 107.20 (18) |
N1—C1—C2 | 108.44 (19) | C13—C14—H14 | 126.4 |
N1—C1—H1 | 125.8 | C15—C14—H14 | 126.4 |
C2—C1—H1 | 125.8 | C16—C15—C14 | 108.33 (17) |
C1—C2—C3 | 107.24 (18) | C16—C15—H15 | 125.8 |
C1—C2—H2 | 126.4 | C14—C15—H15 | 125.8 |
C3—C2—H2 | 126.4 | N3—C16—C15 | 106.47 (15) |
C4—C3—C2 | 108.29 (18) | N3—C16—C17 | 123.18 (15) |
C4—C3—H3 | 125.9 | C15—C16—C17 | 130.35 (16) |
C2—C3—H3 | 125.9 | N4—C17—C16 | 119.49 (16) |
N1—C4—C3 | 106.31 (16) | N4—C17—C18 | 124.21 (16) |
N1—C4—C5 | 122.82 (16) | C16—C17—C18 | 116.31 (15) |
C3—C4—C5 | 130.76 (18) | C17—C18—H18A | 109.5 |
N2—C5—C4 | 118.71 (16) | C17—C18—H18B | 109.5 |
N2—C5—C6 | 124.98 (17) | H18A—C18—H18B | 109.5 |
C4—C5—C6 | 116.29 (16) | C17—C18—H18C | 109.5 |
C5—C6—H6A | 109.5 | H18A—C18—H18C | 109.5 |
C5—C6—H6B | 109.5 | H18B—C18—H18C | 109.5 |
H6A—C6—H6B | 109.5 | C24—C19—C20 | 118.90 (19) |
C5—C6—H6C | 109.5 | C24—C19—N4 | 120.50 (18) |
H6A—C6—H6C | 109.5 | C20—C19—N4 | 120.46 (17) |
H6B—C6—H6C | 109.5 | C21—C20—C19 | 120.0 (2) |
C12—C7—C8 | 118.78 (17) | C21—C20—H20 | 120.0 |
C12—C7—N2 | 119.48 (16) | C19—C20—H20 | 120.0 |
C8—C7—N2 | 121.62 (17) | C22—C21—C20 | 120.7 (2) |
C9—C8—C7 | 120.61 (19) | C22—C21—H21 | 119.6 |
C9—C8—H8 | 119.7 | C20—C21—H21 | 119.6 |
C7—C8—H8 | 119.7 | C23—C22—C21 | 119.7 (2) |
C10—C9—C8 | 120.8 (2) | C23—C22—H22 | 120.2 |
C10—C9—H9 | 119.6 | C21—C22—H22 | 120.2 |
C8—C9—H9 | 119.6 | C22—C23—C24 | 120.5 (2) |
C9—C10—C11 | 119.0 (2) | C22—C23—H23 | 119.7 |
C9—C10—H10 | 120.5 | C24—C23—H23 | 119.7 |
C11—C10—H10 | 120.5 | C19—C24—C23 | 120.2 (2) |
C10—C11—C12 | 120.2 (2) | C19—C24—H24 | 119.9 |
C10—C11—H11 | 119.9 | C23—C24—H24 | 119.9 |
C4—N1—C1—C2 | 0.7 (2) | C16—N3—C13—C14 | −0.1 (2) |
N1—C1—C2—C3 | −0.9 (3) | N3—C13—C14—C15 | 0.2 (2) |
C1—C2—C3—C4 | 0.8 (2) | C13—C14—C15—C16 | −0.2 (2) |
C1—N1—C4—C3 | −0.2 (2) | C13—N3—C16—C15 | −0.1 (2) |
C1—N1—C4—C5 | −176.80 (17) | C13—N3—C16—C17 | −179.24 (16) |
C2—C3—C4—N1 | −0.3 (2) | C14—C15—C16—N3 | 0.2 (2) |
C2—C3—C4—C5 | 175.84 (19) | C14—C15—C16—C17 | 179.27 (18) |
C7—N2—C5—C4 | 179.53 (15) | C19—N4—C17—C16 | 179.47 (15) |
C7—N2—C5—C6 | 1.0 (3) | C19—N4—C17—C18 | −0.9 (3) |
N1—C4—C5—N2 | 1.6 (3) | N3—C16—C17—N4 | 7.2 (3) |
C3—C4—C5—N2 | −174.05 (19) | C15—C16—C17—N4 | −171.75 (18) |
N1—C4—C5—C6 | −179.77 (17) | N3—C16—C17—C18 | −172.52 (16) |
C3—C4—C5—C6 | 4.6 (3) | C15—C16—C17—C18 | 8.6 (3) |
C5—N2—C7—C12 | −112.9 (2) | C17—N4—C19—C24 | 92.6 (2) |
C5—N2—C7—C8 | 71.2 (2) | C17—N4—C19—C20 | −91.9 (2) |
C12—C7—C8—C9 | 1.0 (3) | C24—C19—C20—C21 | −1.4 (3) |
N2—C7—C8—C9 | 176.9 (2) | N4—C19—C20—C21 | −177.05 (18) |
C7—C8—C9—C10 | −0.1 (4) | C19—C20—C21—C22 | 0.4 (3) |
C8—C9—C10—C11 | −0.5 (4) | C20—C21—C22—C23 | 0.5 (4) |
C9—C10—C11—C12 | 0.2 (3) | C21—C22—C23—C24 | −0.4 (4) |
C8—C7—C12—C11 | −1.2 (3) | C20—C19—C24—C23 | 1.5 (3) |
N2—C7—C12—C11 | −177.28 (17) | N4—C19—C24—C23 | 177.15 (18) |
C10—C11—C12—C7 | 0.6 (3) | C22—C23—C24—C19 | −0.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N2i | 0.86 | 2.38 | 3.150 (2) | 150 |
N3—H3A···N4ii | 0.86 | 2.27 | 3.065 (2) | 153 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C12H12N2 |
Mr | 184.24 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.2236 (14), 11.3306 (19), 11.913 (2) |
α, β, γ (°) | 95.984 (3), 93.202 (3), 109.274 (3) |
V (Å3) | 1037.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.37 × 0.25 × 0.19 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.974, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5277, 3655, 2567 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.142, 1.10 |
No. of reflections | 3655 |
No. of parameters | 256 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.13 |
Computer programs: APEX2 (Bruker,2008), SAINT (Bruker,2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N2i | 0.86 | 2.38 | 3.150 (2) | 149.6 |
N3—H3A···N4ii | 0.86 | 2.27 | 3.065 (2) | 153.2 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z. |
Acknowledgements
This work was supported by the Natural Science Basic Research Plan in Shaanxi Province (No. 2009JQ2006), the Scientific Research Plan Project of Shaanxi Education Department (12 J K0620) and the Important Science & Technology Specific Projects of the Innovative Program of Shaanxi Province (No. 2010ZDKG-46).
References
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In recent years, the bis(imino)pyridine incorporated late transition metal catalysts have received considerable attention because of their antioxidant property and outstanding activity for olefin polymerization (Small et al., 1998; Su et al., 2009a,b). As the five-memberd ring substitute of pyridine six-memberd ring (Matsuo et al., 2001; He et al., 2009), pyrrole was frequently introduced into the skeleton of bis(imino)pyridine ligand to design new ligand and corresponding metal complexes (Britovsek et al., 2003; Dawson et al., 2000). Bis(imino)pyrrole was usually prepared from Schiff base condensation of 2,5-diacetylpyrrole and the aromatic amine (Matsuo et al., 2001). As a contribution to this research field, we report herein the synthesis of mono(imino)pyrrole from 2-acetyl pyrrole and aromatic anime, as well as the crystal structure of the title compound 2-(1-phenyliminoethyl)pyrrole.
The asymmetric unit of the title compound (Fig. 1) comprises of two crystallographically independent molecules A and B. In each molecule the pyrrole ring and benzene ring are essentially perpendicular, with dihedral angles of 72.37 (7)° and 82.34 (8)° respectively. The benzene ring of molecules A are nearly parallel with the benzene ring of molecules B with dihedral angle of 14.33 (14)°, but pyrrole ring of molecules A forms a comparative large 39.42 (9)° dihedral angle with the pyrrole ring of molecules B. On the whole, bond lengths and angles in both molecules are equal in the s.u. range. The crystal packing is stabilized by N–H···N classical intermolecular hydrogen bonds (Table 1, Fig. 2).