Literature DB >> 23476167

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

Bi-Yun Su1, Wen-Long Qin, Long Jiao, Jia-Xiang Wang.   

Abstract

There are two independent mol-ecules in the asymmetric unit of the title compound, C13H14N2, in which the dihedral angles formed by the pyrrole and benzene rings are 83.63 (8) and 87.84 (8)°. In the crystal, mol-ecules are linked via pairs of N-H⋯N hydrogen bonds, forming inversion dimers, which are further connected by C-H⋯π inter-actions.

Entities:  

Year:  2012        PMID： 23476167      PMCID： PMC3588931          DOI： 10.1107/S1600536812045849

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


Related literature

For general background to the imino­pyrrole unit, see: Britovsek et al. (2003 ▶); Dawson et al. (2000 ▶); Kazushi & Hayato (2005 ▶). For pyrrole monoimine, see: He et al. (2009 ▶); Su et al. (2009a ▶,b ▶).

Experimental

Crystal data

C13H14N2 M = 198.26 Triclinic, a = 10.120 (2) Å b = 10.400 (3) Å c = 11.726 (3) Å α = 79.138 (4)° β = 67.021 (4)° γ = 88.154 (4)° V = 1114.7 (5) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 296 K 0.38 × 0.29 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.973, T max = 0.988 5729 measured reflections 3981 independent reflections 2530 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.149 S = 1.03 3981 reflections 276 parameters 2 restraints H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.16 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 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045849/lx2269sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045849/lx2269Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812045849/lx2269Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H14N2Z = 4
Mr = 198.26F(000) = 424
Triclinic, P1Dx = 1.181 Mg m−3
Hall symbol: -P 1Melting point = 396.5–398.9 K
a = 10.120 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.400 (3) ÅCell parameters from 1216 reflections
c = 11.726 (3) Åθ = 2.3–25.2°
α = 79.138 (4)°µ = 0.07 mm−1
β = 67.021 (4)°T = 296 K
γ = 88.154 (4)°Block, colourless
V = 1114.7 (5) Å30.38 × 0.29 × 0.17 mm
Bruker APEXII CCD diffractometer3981 independent reflections
Radiation source: fine-focus sealed tube2530 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 25.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −9→12
Tmin = 0.973, Tmax = 0.988k = −12→12
5729 measured reflectionsl = −10→14
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.149w = 1/[σ2(Fo2) + (0.0703P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3981 reflectionsΔρmax = 0.19 e Å−3
276 parametersΔρmin = −0.16 e Å−3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (3)
Experimental. The purity and the composition of the compound were checked and characterized by Infrared spectrum, 1H NMR spectrum, mass spectrum, as well as elemental analysis. IR (KBr): νC═N 1645 cm-1. 1H NMR (400MHz, CDCl3): δ 7.36 (d, 1H, benzene ring aromatic H), 7.15 (t, 2H, benzene ring aromatic H), 7.88 (t, 1H, benzene ring aromatic H), 6.90 (d, 1H,pyrrole ring aromatic H), 6.71 (t, 1H, pyrrole ring aromatic H), 6.34 (d, 1H,pyrrole ring aromatic H), 2.48 (s, 3H, phenyl-CH3), 2.25 (s, 3H,-N═C(CH3)-). MS (EI): m/z 197 (M+). Anal. Calcd. for C13H14N2: C, 78.75; H, 7.12; N, 14.13. Found: C, 78.22; H, 6.95; N,14.68.
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 > 2sigma(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
N10.37284 (18)0.91215 (17)0.19040 (14)0.0510 (5)
H10.44260.95790.12890.061*
N20.34013 (18)0.93166 (17)−0.03844 (14)0.0507 (5)
N30.14266 (18)0.49423 (17)0.80750 (14)0.0541 (5)
H30.06620.51110.86780.065*
N40.16015 (18)0.41253 (17)1.04284 (14)0.0498 (5)
C10.3590 (3)0.8857 (2)0.31132 (18)0.0626 (6)
H1A0.42260.91370.34220.075*
C20.2371 (3)0.8118 (3)0.3801 (2)0.0689 (7)
H20.20160.77980.46660.083*
C30.1742 (3)0.7922 (2)0.2987 (2)0.0633 (6)
H3A0.08880.74450.32080.076*
C40.2595 (2)0.8553 (2)0.18026 (17)0.0473 (5)
C50.2429 (2)0.8691 (2)0.06202 (19)0.0491 (5)
C60.1083 (2)0.8091 (3)0.0660 (2)0.0724 (7)
H6A0.03920.87520.06910.109*
H6B0.06960.74120.13960.109*
H6C0.12990.7724−0.00820.109*
C70.3199 (2)0.95209 (18)−0.15330 (18)0.0502 (5)
C80.3676 (2)0.8647 (2)−0.2347 (2)0.0562 (6)
C90.3553 (3)0.8960 (3)−0.3496 (2)0.0681 (7)
H90.38700.8379−0.40520.082*
C100.2981 (3)1.0095 (3)−0.3841 (2)0.0753 (8)
H100.28981.0276−0.46170.090*
C110.2530 (3)1.0965 (3)−0.3044 (2)0.0712 (7)
H110.21541.1749−0.32840.085*
C120.2627 (2)1.06875 (19)−0.18953 (19)0.0589 (6)
H120.23111.1280−0.13520.071*
C130.4357 (3)0.7415 (3)−0.2007 (2)0.0795 (8)
H13A0.45500.6895−0.26450.119*
H13B0.37160.6927−0.12090.119*
H13C0.52400.7633−0.19490.119*
C140.1659 (3)0.5221 (3)0.68454 (19)0.0672 (7)
H140.10230.56220.65080.081*
C150.2975 (3)0.4818 (3)0.6179 (2)0.0707 (7)
H150.34100.48980.53070.085*
C160.3551 (2)0.4261 (2)0.70452 (19)0.0630 (6)
H160.44420.38900.68560.076*
C170.2584 (2)0.4353 (2)0.82227 (17)0.0462 (5)
C180.2667 (2)0.3960 (2)0.94336 (19)0.0475 (5)
C190.4037 (2)0.3381 (3)0.9440 (2)0.0737 (8)
H19A0.46990.40680.93580.111*
H19B0.44500.29300.87470.111*
H19C0.38430.27751.02190.111*
C200.1708 (2)0.37695 (19)1.16170 (18)0.0489 (5)
C210.1223 (2)0.2549 (2)1.23561 (19)0.0544 (6)
C220.1255 (3)0.2295 (3)1.3541 (2)0.0698 (7)
H220.09410.14721.40470.084*
C230.1739 (3)0.3221 (3)1.3993 (2)0.0791 (8)
H230.17500.30261.47960.095*
C240.2206 (3)0.4433 (3)1.3258 (2)0.0766 (8)
H240.25280.50681.35640.092*
C250.2199 (2)0.4712 (2)1.2078 (2)0.0611 (6)
H250.25240.55351.15770.073*
C260.0651 (3)0.1542 (3)1.1890 (2)0.0790 (8)
H26A−0.02390.18151.18310.119*
H26B0.04910.07191.24670.119*
H26C0.13330.14441.10730.119*
U11U22U33U12U13U23
N10.0470 (10)0.0660 (12)0.0362 (9)−0.0026 (9)−0.0132 (8)−0.0066 (8)
N20.0493 (11)0.0624 (12)0.0430 (9)−0.0007 (9)−0.0207 (8)−0.0098 (8)
N30.0512 (11)0.0680 (12)0.0406 (9)0.0081 (9)−0.0185 (8)−0.0047 (8)
N40.0497 (11)0.0586 (11)0.0420 (9)0.0077 (8)−0.0210 (8)−0.0060 (8)
C10.0668 (16)0.0836 (18)0.0405 (12)−0.0020 (13)−0.0240 (11)−0.0119 (11)
C20.0707 (17)0.0882 (19)0.0382 (12)−0.0102 (14)−0.0159 (12)0.0010 (12)
C30.0568 (14)0.0754 (17)0.0507 (13)−0.0094 (12)−0.0173 (11)−0.0019 (11)
C40.0446 (12)0.0539 (13)0.0447 (11)0.0020 (10)−0.0188 (10)−0.0092 (10)
C50.0465 (12)0.0529 (13)0.0485 (12)0.0058 (10)−0.0204 (10)−0.0081 (10)
C60.0546 (15)0.099 (2)0.0655 (15)−0.0131 (13)−0.0301 (12)−0.0033 (14)
C70.0441 (12)0.0617 (14)0.0469 (11)−0.0025 (10)−0.0198 (10)−0.0101 (10)
C80.0521 (13)0.0617 (15)0.0578 (13)−0.0028 (11)−0.0231 (11)−0.0140 (11)
C90.0709 (16)0.089 (2)0.0518 (13)0.0025 (14)−0.0272 (12)−0.0235 (13)
C100.0771 (18)0.106 (2)0.0484 (13)0.0019 (16)−0.0318 (13)−0.0121 (14)
C110.0731 (17)0.0820 (18)0.0615 (14)0.0102 (14)−0.0348 (13)−0.0030 (13)
C120.0620 (15)0.0655 (16)0.0542 (13)0.0093 (12)−0.0272 (11)−0.0147 (11)
C130.093 (2)0.0716 (18)0.0840 (17)0.0206 (15)−0.0420 (15)−0.0266 (14)
C140.0681 (16)0.0907 (19)0.0418 (12)0.0079 (14)−0.0256 (11)−0.0023 (12)
C150.0711 (17)0.096 (2)0.0401 (12)0.0057 (14)−0.0187 (12)−0.0096 (12)
C160.0558 (14)0.0799 (17)0.0514 (13)0.0084 (12)−0.0185 (11)−0.0143 (12)
C170.0457 (12)0.0503 (13)0.0423 (11)0.0044 (10)−0.0181 (9)−0.0068 (9)
C180.0471 (12)0.0495 (13)0.0497 (12)0.0050 (10)−0.0232 (10)−0.0097 (10)
C190.0567 (15)0.106 (2)0.0635 (14)0.0267 (14)−0.0295 (12)−0.0191 (14)
C200.0426 (12)0.0603 (14)0.0442 (11)0.0097 (10)−0.0195 (9)−0.0069 (10)
C210.0506 (13)0.0588 (15)0.0515 (13)0.0090 (11)−0.0210 (10)−0.0041 (11)
C220.0703 (17)0.0769 (18)0.0546 (14)0.0055 (14)−0.0248 (12)0.0057 (13)
C230.0847 (19)0.106 (2)0.0515 (14)0.0099 (17)−0.0372 (14)−0.0048 (15)
C240.090 (2)0.089 (2)0.0695 (16)0.0069 (16)−0.0487 (15)−0.0221 (15)
C250.0683 (16)0.0643 (16)0.0566 (13)0.0023 (12)−0.0324 (12)−0.0078 (11)
C260.092 (2)0.0623 (17)0.0823 (17)−0.0068 (14)−0.0358 (15)−0.0085 (13)
N1—C11.344 (2)C11—H110.9300
N1—C41.362 (3)C12—H120.9300
N1—H10.8600C13—H13A0.9600
N2—C51.275 (3)C13—H13B0.9600
N2—C71.416 (2)C13—H13C0.9600
N3—C141.342 (2)C14—C151.355 (3)
N3—C171.360 (2)C14—H140.9300
N3—H30.8600C15—C161.388 (3)
N4—C181.278 (2)C15—H150.9300
N4—C201.418 (2)C16—C171.364 (3)
C1—C21.347 (3)C16—H160.9300
C1—H1A0.9300C17—C181.436 (3)
C2—C31.383 (3)C18—C191.496 (3)
C2—H20.9300C19—H19A0.9600
C3—C41.364 (3)C19—H19B0.9600
C3—H3A0.9300C19—H19C0.9600
C4—C51.441 (3)C20—C211.377 (3)
C5—C61.497 (3)C20—C251.3927 (10)
C6—H6A0.9600C21—C221.378 (3)
C6—H6B0.9600C21—C261.494 (3)
C6—H6C0.9600C22—C231.369 (4)
C7—C81.382 (3)C22—H220.9300
C7—C121.3925 (10)C23—C241.366 (4)
C8—C91.378 (3)C23—H230.9300
C8—C131.497 (3)C24—C251.362 (3)
C9—C101.360 (3)C24—H240.9300
C9—H90.9300C25—H250.9300
C10—C111.364 (3)C26—H26A0.9600
C10—H100.9300C26—H26B0.9600
C11—C121.366 (3)C26—H26C0.9600
C1—N1—C4109.55 (18)H13A—C13—H13B109.5
C1—N1—H1125.2C8—C13—H13C109.5
C4—N1—H1125.2H13A—C13—H13C109.5
C5—N2—C7119.54 (18)H13B—C13—H13C109.5
C14—N3—C17109.63 (17)N3—C14—C15108.52 (19)
C14—N3—H3125.2N3—C14—H14125.7
C17—N3—H3125.2C15—C14—H14125.7
C18—N4—C20119.24 (17)C14—C15—C16106.91 (19)
N1—C1—C2108.3 (2)C14—C15—H15126.5
N1—C1—H1A125.9C16—C15—H15126.5
C2—C1—H1A125.9C17—C16—C15108.2 (2)
C1—C2—C3107.55 (19)C17—C16—H16125.9
C1—C2—H2126.2C15—C16—H16125.9
C3—C2—H2126.2N3—C17—C16106.70 (17)
C4—C3—C2108.0 (2)N3—C17—C18122.69 (17)
C4—C3—H3A126.0C16—C17—C18130.61 (19)
C2—C3—H3A126.0N4—C18—C17119.61 (18)
N1—C4—C3106.62 (18)N4—C18—C19123.84 (18)
N1—C4—C5122.36 (18)C17—C18—C19116.54 (18)
C3—C4—C5131.0 (2)C18—C19—H19A109.5
N2—C5—C4119.52 (19)C18—C19—H19B109.5
N2—C5—C6123.74 (18)H19A—C19—H19B109.5
C4—C5—C6116.74 (19)C18—C19—H19C109.5
C5—C6—H6A109.5H19A—C19—H19C109.5
C5—C6—H6B109.5H19B—C19—H19C109.5
H6A—C6—H6B109.5C21—C20—C25120.03 (19)
C5—C6—H6C109.5C21—C20—N4120.84 (17)
H6A—C6—H6C109.5C25—C20—N4118.90 (19)
H6B—C6—H6C109.5C20—C21—C22118.1 (2)
C8—C7—C12119.60 (18)C20—C21—C26120.66 (19)
C8—C7—N2121.35 (16)C22—C21—C26121.2 (2)
C12—C7—N2118.78 (17)C23—C22—C21121.8 (2)
C9—C8—C7118.4 (2)C23—C22—H22119.1
C9—C8—C13120.9 (2)C21—C22—H22119.1
C7—C8—C13120.72 (19)C24—C23—C22119.7 (2)
C10—C9—C8121.8 (2)C24—C23—H23120.1
C10—C9—H9119.1C22—C23—H23120.1
C8—C9—H9119.1C25—C24—C23120.0 (2)
C9—C10—C11119.8 (2)C25—C24—H24120.0
C9—C10—H10120.1C23—C24—H24120.0
C11—C10—H10120.1C24—C25—C20120.4 (2)
C10—C11—C12120.1 (2)C24—C25—H25119.8
C10—C11—H11119.9C20—C25—H25119.8
C12—C11—H11119.9C21—C26—H26A109.5
C11—C12—C7120.3 (2)C21—C26—H26B109.5
C11—C12—H12119.8H26A—C26—H26B109.5
C7—C12—H12119.8C21—C26—H26C109.5
C8—C13—H13A109.5H26A—C26—H26C109.5
C8—C13—H13B109.5H26B—C26—H26C109.5
C4—N1—C1—C20.0 (3)C17—N3—C14—C15−0.2 (3)
N1—C1—C2—C30.0 (3)N3—C14—C15—C160.7 (3)
C1—C2—C3—C4−0.1 (3)C14—C15—C16—C17−0.9 (3)
C1—N1—C4—C3−0.1 (2)C14—N3—C17—C16−0.4 (3)
C1—N1—C4—C5178.53 (18)C14—N3—C17—C18178.8 (2)
C2—C3—C4—N10.1 (3)C15—C16—C17—N30.8 (3)
C2—C3—C4—C5−178.4 (2)C15—C16—C17—C18−178.3 (2)
C7—N2—C5—C4−176.19 (16)C20—N4—C18—C17−178.17 (18)
C7—N2—C5—C62.9 (3)C20—N4—C18—C191.2 (3)
N1—C4—C5—N23.2 (3)N3—C17—C18—N42.2 (3)
C3—C4—C5—N2−178.6 (2)C16—C17—C18—N4−178.8 (2)
N1—C4—C5—C6−176.01 (19)N3—C17—C18—C19−177.2 (2)
C3—C4—C5—C62.3 (3)C16—C17—C18—C191.8 (4)
C5—N2—C7—C8−91.5 (2)C18—N4—C20—C21−93.6 (2)
C5—N2—C7—C1294.5 (3)C18—N4—C20—C2591.8 (2)
C12—C7—C8—C9−0.7 (3)C25—C20—C21—C22−0.7 (3)
N2—C7—C8—C9−174.6 (2)N4—C20—C21—C22−175.18 (18)
C12—C7—C8—C13177.2 (2)C25—C20—C21—C26178.1 (2)
N2—C7—C8—C133.2 (3)N4—C20—C21—C263.6 (3)
C7—C8—C9—C100.0 (4)C20—C21—C22—C230.7 (3)
C13—C8—C9—C10−177.8 (3)C26—C21—C22—C23−178.1 (2)
C8—C9—C10—C110.9 (4)C21—C22—C23—C24−0.1 (4)
C9—C10—C11—C12−1.2 (4)C22—C23—C24—C25−0.5 (4)
C10—C11—C12—C70.5 (4)C23—C24—C25—C200.5 (4)
C8—C7—C12—C110.4 (3)C21—C20—C25—C240.1 (3)
N2—C7—C12—C11174.5 (2)N4—C20—C25—C24174.74 (19)
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.862.273.070 (3)154
N3—H3···N4ii0.862.303.108 (2)156
C1—H1A···Cg1iii0.932.703.488 (4)143
C14—H14···Cg2iv0.932.753.531 (3)142
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7–C12 and C20–C25 rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1⋯N2i 0.862.273.070 (3)154
N3—H3⋯N4ii 0.862.303.108 (2)156
C1—H1A⋯Cg1iii 0.932.703.488 (4)143
C14—H14⋯Cg2iv 0.932.753.531 (3)142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  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
Journal:  Inorg Chem       Date:  2003-06-02       Impact factor: 5.165
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.