Literature DB >> 23125684

N-[1-(1H-Pyrrol-2-yl)ethyl-idene]aniline.

Bi-Yun Su1, Lei Li, Jia-Xiang Wang, Xuan-Yan Li.   

Abstract

There are two independent mol-ecules in the asymmetric unit of the title compound, C(12)H(12)N(2), 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 mol-ecules are equal [1.286 (2) Å] and indicate C=N character. In the crystal, each mol-ecule forms a dimer with an inversion-related mol-ecule through a pair of classical N-H⋯N hydrogen bonds.

Entities:  

Year:  2012        PMID： 23125684      PMCID： PMC3470240          DOI： 10.1107/S1600536812037695

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related 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

C12H12N2 M = 184.24 Triclinic, a = 8.2236 (14) Å b = 11.3306 (19) Å c = 11.913 (2) Å α = 95.984 (3)° β = 93.202 (3)° γ = 109.274 (3)° V = 1037.3 (3) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 296 K 0.37 × 0.25 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.974, T max = 0.987 5277 measured reflections 3655 independent reflections 2567 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.142 S = 1.10 3655 reflections 256 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.13 e Å−3 Data collection: APEX2 (Bruker,2008 ▶); cell refinement: 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 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037695/rk2378sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037695/rk2378Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812037695/rk2378Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C12H12N2Z = 4
Mr = 184.24F(000) = 392
Triclinic, P1Dx = 1.180 Mg m−3
Hall symbol: -P 1Melting point = 405.25–406.85 K
a = 8.2236 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3306 (19) ÅCell parameters from 1351 reflections
c = 11.913 (2) Åθ = 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) Å30.37 × 0.25 × 0.19 mm
Bruker APEXII CCD diffractometer3655 independent reflections
Radiation source: fine-focus sealed tube2567 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −9→9
Tmin = 0.974, Tmax = 0.987k = −9→13
5277 measured reflectionsl = −14→11
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.142w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
3655 reflectionsΔρmax = 0.20 e Å−3
256 parametersΔρmin = −0.13 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.043 (5)
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.
xyzUiso*/Ueq
N10.1204 (2)1.17200 (13)0.61426 (13)0.0613 (4)
H1A0.06271.12630.55340.074*
N20.19520 (19)0.94813 (13)0.57233 (12)0.0557 (4)
N30.38995 (19)0.64751 (14)−0.01282 (12)0.0557 (4)
H3A0.44860.6007−0.03540.067*
N40.31361 (19)0.43111 (14)0.10218 (13)0.0569 (4)
C10.1184 (3)1.28776 (18)0.6531 (2)0.0780 (6)
H10.05391.33050.61920.094*
C20.2261 (3)1.3311 (2)0.7498 (2)0.0812 (7)
H20.25021.40890.79350.097*
C30.2940 (3)1.23792 (19)0.77152 (17)0.0699 (6)
H30.37101.24190.83320.084*
C40.2279 (2)1.13853 (16)0.68614 (15)0.0524 (5)
C50.2640 (2)1.02211 (16)0.66444 (14)0.0519 (5)
C60.3844 (3)0.9990 (2)0.75197 (17)0.0783 (6)
H6A0.32160.96650.81400.117*
H6B0.47571.07670.77930.117*
H6C0.43310.93890.71870.117*
C70.2301 (2)0.83354 (16)0.54888 (15)0.0525 (5)
C80.1630 (3)0.73360 (18)0.60871 (18)0.0726 (6)
H80.09760.74180.66840.087*
C90.1917 (3)0.62193 (19)0.5811 (2)0.0814 (7)
H90.14570.55530.62240.098*
C100.2873 (3)0.6075 (2)0.4936 (2)0.0781 (6)
H100.30720.53190.47560.094*
C110.3536 (3)0.7066 (2)0.43257 (19)0.0772 (6)
H110.41840.69800.37270.093*
C120.3241 (3)0.81884 (18)0.46002 (17)0.0664 (5)
H120.36830.88500.41790.080*
C130.4041 (3)0.76033 (19)−0.04693 (17)0.0651 (5)
H130.47830.8000−0.09820.078*
C140.2908 (3)0.8061 (2)0.00674 (18)0.0698 (6)
H140.27360.8820−0.00130.084*
C150.2060 (3)0.71803 (18)0.07579 (17)0.0627 (5)
H150.12180.72490.12250.075*
C160.2679 (2)0.61897 (16)0.06320 (14)0.0507 (4)
C170.2239 (2)0.50444 (16)0.11674 (14)0.0503 (4)
C180.0726 (3)0.47986 (18)0.18618 (16)0.0656 (5)
H18A−0.02590.41570.14460.098*
H18B0.04620.55600.20250.098*
H18C0.10060.45220.25590.098*
C190.2680 (2)0.31984 (17)0.15675 (16)0.0561 (5)
C200.3454 (3)0.3213 (2)0.26340 (17)0.0708 (6)
H200.42380.39610.30140.085*
C210.3063 (3)0.2120 (3)0.3132 (2)0.0850 (7)
H210.35810.21360.38510.102*
C220.1926 (3)0.1014 (2)0.2583 (2)0.0873 (7)
H220.16630.02830.29270.105*
C230.1175 (3)0.0987 (2)0.1524 (2)0.0869 (7)
H230.04040.02330.11470.104*
C240.1551 (3)0.2071 (2)0.10094 (19)0.0730 (6)
H240.10420.20420.02850.088*
U11U22U33U12U13U23
N10.0669 (10)0.0474 (9)0.0668 (10)0.0195 (8)−0.0074 (8)0.0011 (7)
N20.0601 (9)0.0484 (8)0.0593 (9)0.0191 (7)0.0030 (8)0.0102 (7)
N30.0549 (9)0.0621 (10)0.0579 (9)0.0271 (7)0.0110 (7)0.0155 (7)
N40.0530 (9)0.0618 (9)0.0627 (9)0.0236 (8)0.0156 (7)0.0197 (7)
C10.0800 (15)0.0517 (12)0.1002 (17)0.0274 (11)−0.0127 (13)−0.0059 (11)
C20.0714 (14)0.0616 (13)0.1009 (17)0.0213 (11)−0.0030 (13)−0.0218 (12)
C30.0603 (12)0.0749 (14)0.0679 (13)0.0209 (11)−0.0028 (10)−0.0087 (11)
C40.0485 (10)0.0518 (10)0.0555 (11)0.0150 (8)0.0054 (8)0.0070 (8)
C50.0497 (10)0.0543 (11)0.0520 (10)0.0155 (8)0.0071 (8)0.0141 (9)
C60.0889 (16)0.0862 (15)0.0665 (13)0.0400 (13)−0.0089 (12)0.0134 (11)
C70.0519 (10)0.0509 (10)0.0556 (10)0.0183 (8)0.0031 (8)0.0092 (8)
C80.0878 (15)0.0604 (12)0.0798 (14)0.0309 (11)0.0335 (12)0.0210 (10)
C90.1039 (18)0.0574 (13)0.0943 (16)0.0343 (12)0.0340 (14)0.0233 (11)
C100.0847 (16)0.0590 (13)0.0935 (16)0.0301 (12)0.0134 (13)0.0005 (12)
C110.0715 (14)0.0779 (15)0.0800 (15)0.0235 (12)0.0208 (12)−0.0006 (12)
C120.0682 (13)0.0598 (12)0.0673 (13)0.0145 (10)0.0140 (10)0.0109 (10)
C130.0620 (12)0.0718 (13)0.0703 (13)0.0282 (10)0.0107 (10)0.0277 (10)
C140.0744 (14)0.0705 (13)0.0780 (14)0.0382 (11)0.0132 (11)0.0213 (11)
C150.0641 (12)0.0711 (13)0.0634 (12)0.0339 (10)0.0145 (10)0.0142 (10)
C160.0457 (10)0.0615 (11)0.0473 (10)0.0208 (8)0.0051 (8)0.0084 (8)
C170.0472 (10)0.0583 (11)0.0457 (10)0.0188 (8)0.0033 (8)0.0055 (8)
C180.0647 (12)0.0725 (13)0.0672 (12)0.0293 (10)0.0216 (10)0.0146 (10)
C190.0474 (10)0.0639 (12)0.0649 (12)0.0248 (9)0.0165 (9)0.0176 (9)
C200.0742 (14)0.0770 (14)0.0659 (13)0.0280 (11)0.0095 (11)0.0200 (11)
C210.0857 (17)0.1045 (19)0.0803 (15)0.0435 (15)0.0171 (13)0.0376 (14)
C220.0747 (16)0.0889 (18)0.118 (2)0.0381 (14)0.0315 (15)0.0529 (16)
C230.0701 (15)0.0685 (14)0.121 (2)0.0177 (11)0.0122 (14)0.0271 (14)
C240.0618 (13)0.0717 (14)0.0846 (15)0.0196 (11)0.0001 (11)0.0195 (11)
N1—C11.350 (2)C10—C111.378 (3)
N1—C41.365 (2)C10—H100.9300
N1—H1A0.8600C11—C121.381 (3)
N2—C51.286 (2)C11—H110.9300
N2—C71.423 (2)C12—H120.9300
N3—C131.352 (2)C13—C141.364 (3)
N3—C161.371 (2)C13—H130.9300
N3—H3A0.8600C14—C151.391 (3)
N4—C171.286 (2)C14—H140.9300
N4—C191.428 (2)C15—C161.376 (2)
C1—C21.355 (3)C15—H150.9300
C1—H10.9300C16—C171.453 (2)
C2—C31.387 (3)C17—C181.498 (2)
C2—H20.9300C18—H18A0.9600
C3—C41.376 (2)C18—H18B0.9600
C3—H30.9300C18—H18C0.9600
C4—C51.446 (2)C19—C241.381 (3)
C5—C61.500 (3)C19—C201.385 (3)
C6—H6A0.9600C20—C211.379 (3)
C6—H6B0.9600C20—H200.9300
C6—H6C0.9600C21—C221.363 (3)
C7—C121.373 (3)C21—H210.9300
C7—C81.376 (3)C22—C231.366 (3)
C8—C91.373 (3)C22—H220.9300
C8—H80.9300C23—C241.381 (3)
C9—C101.368 (3)C23—H230.9300
C9—H90.9300C24—H240.9300
C1—N1—C4109.71 (17)C12—C11—H11119.9
C1—N1—H1A125.1C7—C12—C11120.60 (19)
C4—N1—H1A125.1C7—C12—H12119.7
C5—N2—C7119.64 (15)C11—C12—H12119.7
C13—N3—C16109.70 (15)N3—C13—C14108.30 (18)
C13—N3—H3A125.2N3—C13—H13125.9
C16—N3—H3A125.2C14—C13—H13125.9
C17—N4—C19118.11 (15)C13—C14—C15107.20 (18)
N1—C1—C2108.44 (19)C13—C14—H14126.4
N1—C1—H1125.8C15—C14—H14126.4
C2—C1—H1125.8C16—C15—C14108.33 (17)
C1—C2—C3107.24 (18)C16—C15—H15125.8
C1—C2—H2126.4C14—C15—H15125.8
C3—C2—H2126.4N3—C16—C15106.47 (15)
C4—C3—C2108.29 (18)N3—C16—C17123.18 (15)
C4—C3—H3125.9C15—C16—C17130.35 (16)
C2—C3—H3125.9N4—C17—C16119.49 (16)
N1—C4—C3106.31 (16)N4—C17—C18124.21 (16)
N1—C4—C5122.82 (16)C16—C17—C18116.31 (15)
C3—C4—C5130.76 (18)C17—C18—H18A109.5
N2—C5—C4118.71 (16)C17—C18—H18B109.5
N2—C5—C6124.98 (17)H18A—C18—H18B109.5
C4—C5—C6116.29 (16)C17—C18—H18C109.5
C5—C6—H6A109.5H18A—C18—H18C109.5
C5—C6—H6B109.5H18B—C18—H18C109.5
H6A—C6—H6B109.5C24—C19—C20118.90 (19)
C5—C6—H6C109.5C24—C19—N4120.50 (18)
H6A—C6—H6C109.5C20—C19—N4120.46 (17)
H6B—C6—H6C109.5C21—C20—C19120.0 (2)
C12—C7—C8118.78 (17)C21—C20—H20120.0
C12—C7—N2119.48 (16)C19—C20—H20120.0
C8—C7—N2121.62 (17)C22—C21—C20120.7 (2)
C9—C8—C7120.61 (19)C22—C21—H21119.6
C9—C8—H8119.7C20—C21—H21119.6
C7—C8—H8119.7C23—C22—C21119.7 (2)
C10—C9—C8120.8 (2)C23—C22—H22120.2
C10—C9—H9119.6C21—C22—H22120.2
C8—C9—H9119.6C22—C23—C24120.5 (2)
C9—C10—C11119.0 (2)C22—C23—H23119.7
C9—C10—H10120.5C24—C23—H23119.7
C11—C10—H10120.5C19—C24—C23120.2 (2)
C10—C11—C12120.2 (2)C19—C24—H24119.9
C10—C11—H11119.9C23—C24—H24119.9
C4—N1—C1—C20.7 (2)C16—N3—C13—C14−0.1 (2)
N1—C1—C2—C3−0.9 (3)N3—C13—C14—C150.2 (2)
C1—C2—C3—C40.8 (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—N30.2 (2)
C2—C3—C4—C5175.84 (19)C14—C15—C16—C17179.27 (18)
C7—N2—C5—C4179.53 (15)C19—N4—C17—C16179.47 (15)
C7—N2—C5—C61.0 (3)C19—N4—C17—C18−0.9 (3)
N1—C4—C5—N21.6 (3)N3—C16—C17—N47.2 (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—C64.6 (3)C15—C16—C17—C188.6 (3)
C5—N2—C7—C12−112.9 (2)C17—N4—C19—C2492.6 (2)
C5—N2—C7—C871.2 (2)C17—N4—C19—C20−91.9 (2)
C12—C7—C8—C91.0 (3)C24—C19—C20—C21−1.4 (3)
N2—C7—C8—C9176.9 (2)N4—C19—C20—C21−177.05 (18)
C7—C8—C9—C10−0.1 (4)C19—C20—C21—C220.4 (3)
C8—C9—C10—C11−0.5 (4)C20—C21—C22—C230.5 (4)
C9—C10—C11—C120.2 (3)C21—C22—C23—C24−0.4 (4)
C8—C7—C12—C11−1.2 (3)C20—C19—C24—C231.5 (3)
N2—C7—C12—C11−177.28 (17)N4—C19—C24—C23177.15 (18)
C10—C11—C12—C70.6 (3)C22—C23—C24—C19−0.7 (3)
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.383.150 (2)150
N3—H3A···N4ii0.862.273.065 (2)153
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1A⋯N2i 0.862.383.150 (2)150
N3—H3A⋯N4ii 0.862.273.065 (2)153

Symmetry codes: (i) ; (ii) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Iron and cobalt ethylene polymerization catalysts: variations on the central donor.

Authors:  George J P Britovsek; Vernon C Gibson; Olivier D Hoarau; Stefan K Spitzmesser; Andrew J P White; David J Williams
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  2 in total

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