Literature DB >> 23284489

(E)-N-[(2-Eth-oxy-naphthalen-1-yl)methyl-idene]-2-ethyl-aniline.

Hakan Kargılı1, Mustafa Macit, Gökhan Alpaslan, Canan Kazak, Ahmet Erdönmez.   

Abstract

In the title compound, C(21)H(21)NO, the dihedral angle between the naphthalene ring system and the benzene ring is 64.61 (6)°. The mol-ecular structure is stabilized by an intra-molecular C-H⋯N hydrogen bond.

Entities:  

Year:  2012        PMID： 23284489      PMCID： PMC3515269          DOI： 10.1107/S1600536812043097

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


Related literature

For biological properties of Schiff bases, see: Lozier et al. (1975 ▶). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Vesek et al. (2012 ▶).

Experimental

Crystal data

C21H21NO M = 303.39 Monoclinic, a = 11.6011 (11) Å b = 20.457 (3) Å c = 7.4335 (7) Å β = 101.303 (8)° V = 1730.0 (3) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 296 K 0.71 × 0.55 × 0.36 mm

Data collection

Stoe IPDS-II diffractometer 14212 measured reflections 3403 independent reflections 1769 reflections with I > 2σ(I) R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.065 wR(F 2) = 0.211 S = 0.94 3403 reflections 209 parameters 16 restraints H-atom parameters constrained Δρmax = 0.45 e Å−3 Δρmin = −0.31 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043097/fj2600sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043097/fj2600Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812043097/fj2600Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H21NOF(000) = 648
Mr = 303.39Dx = 1.165 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10574 reflections
a = 11.6011 (11) Åθ = 1.8–27.9°
b = 20.457 (3) ŵ = 0.07 mm−1
c = 7.4335 (7) ÅT = 296 K
β = 101.303 (8)°Prism, yellow
V = 1730.0 (3) Å30.71 × 0.55 × 0.36 mm
Z = 4
Stoe IPDS-II diffractometer1769 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 26.0°, θmin = 1.8°
Detector resolution: 6.67 pixels mm-1h = −14→14
ω scansk = −25→25
14212 measured reflectionsl = −9→9
3403 independent reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211H-atom parameters constrained
S = 0.94w = 1/[σ2(Fo2) + (0.1288P)2] where P = (Fo2 + 2Fc2)/3
3403 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.45 e Å−3
16 restraintsΔρmin = −0.31 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C10.4025 (2)0.19226 (13)0.3272 (3)0.0619 (7)
C20.3508 (2)0.25280 (13)0.2813 (4)0.0664 (7)
C30.2305 (3)0.25814 (17)0.2024 (4)0.0784 (8)
H30.19760.29890.16860.094*
C40.1635 (3)0.20410 (18)0.1760 (4)0.0810 (9)
H40.08370.20850.12730.097*
C50.2097 (2)0.14074 (15)0.2197 (4)0.0707 (8)
C60.1392 (3)0.08513 (19)0.1902 (5)0.0905 (10)
H60.05970.08970.13950.109*
C70.1834 (3)0.0246 (2)0.2336 (5)0.1001 (11)
H70.1349−0.01200.21320.120*
C80.3027 (3)0.01776 (16)0.3093 (5)0.0901 (9)
H80.3332−0.02370.34020.108*
C90.3751 (3)0.07046 (14)0.3386 (4)0.0753 (8)
H90.45440.06450.38800.090*
C100.3315 (2)0.13437 (13)0.2950 (4)0.0620 (7)
C110.5272 (2)0.19292 (13)0.4136 (4)0.0642 (7)
H110.55780.23240.46330.077*
C120.7140 (2)0.15485 (13)0.5261 (4)0.0661 (7)
C130.7377 (3)0.18615 (15)0.6913 (4)0.0808 (9)
H130.67610.20400.73860.097*
C140.8499 (3)0.19186 (17)0.7886 (5)0.0958 (11)
H140.86400.21310.90150.115*
C150.9404 (3)0.16685 (18)0.7216 (5)0.0938 (10)
H151.01700.17120.78710.113*
C160.9191 (3)0.13519 (19)0.5575 (5)0.1005 (12)
H160.98190.11790.51240.121*
C170.8060 (3)0.12796 (18)0.4555 (5)0.0971 (10)
C180.7839 (4)0.0973 (4)0.2575 (7)0.184 (3)
H18A0.70150.10180.20100.221*
H18B0.82980.12080.18250.221*
C190.8162 (8)0.0289 (3)0.2652 (10)0.226 (3)
H19A0.80300.01130.14310.339*
H19B0.76920.00550.33660.339*
H19C0.89780.02450.32090.339*
C200.3711 (3)0.36953 (14)0.3110 (4)0.0817 (9)
H20A0.31330.37070.38920.098*
H20B0.33260.38120.18730.098*
C210.4679 (4)0.41565 (17)0.3792 (6)0.1107 (12)
H21A0.43690.45910.38000.166*
H21B0.52430.41420.30040.166*
H21C0.50540.40360.50150.166*
N10.59740 (19)0.14530 (11)0.4274 (3)0.0729 (7)
O10.42183 (17)0.30550 (9)0.3129 (3)0.0820 (6)
U11U22U33U12U13U23
C10.0527 (14)0.0783 (18)0.0563 (15)0.0040 (12)0.0148 (11)0.0010 (12)
C20.0592 (15)0.0801 (18)0.0615 (16)0.0058 (13)0.0162 (12)0.0046 (13)
C30.0663 (18)0.095 (2)0.0730 (19)0.0177 (15)0.0104 (14)0.0069 (15)
C40.0559 (16)0.112 (2)0.071 (2)0.0119 (16)0.0036 (14)−0.0018 (17)
C50.0571 (16)0.096 (2)0.0588 (17)−0.0025 (14)0.0121 (12)−0.0122 (14)
C60.0628 (18)0.116 (3)0.091 (2)−0.0098 (18)0.0125 (15)−0.018 (2)
C70.088 (2)0.104 (3)0.112 (3)−0.029 (2)0.029 (2)−0.025 (2)
C80.084 (2)0.080 (2)0.111 (3)−0.0078 (17)0.0304 (18)−0.0116 (18)
C90.0662 (17)0.0798 (19)0.082 (2)0.0005 (15)0.0195 (14)−0.0035 (15)
C100.0566 (15)0.0787 (18)0.0532 (15)0.0015 (12)0.0166 (11)−0.0037 (12)
C110.0578 (15)0.0722 (16)0.0633 (16)−0.0008 (12)0.0133 (12)0.0009 (12)
C120.0543 (14)0.0678 (16)0.0740 (19)−0.0001 (12)0.0075 (12)0.0007 (13)
C130.0674 (17)0.088 (2)0.084 (2)0.0005 (14)0.0091 (15)−0.0120 (16)
C140.077 (2)0.109 (3)0.094 (2)−0.0061 (18)−0.0013 (18)−0.0219 (19)
C150.0596 (18)0.112 (3)0.101 (3)−0.0172 (17)−0.0050 (17)0.009 (2)
C160.0576 (18)0.145 (3)0.097 (3)0.0103 (18)0.0111 (17)−0.006 (2)
C170.0582 (18)0.129 (3)0.101 (2)0.0164 (18)0.0087 (16)−0.0085 (19)
C180.085 (3)0.291 (5)0.168 (4)0.056 (4)0.005 (3)−0.116 (4)
C190.272 (7)0.219 (5)0.197 (6)−0.055 (5)0.071 (5)−0.055 (5)
C200.097 (2)0.079 (2)0.0715 (19)0.0159 (17)0.0227 (16)0.0117 (15)
C210.125 (3)0.084 (2)0.124 (3)−0.006 (2)0.027 (2)−0.006 (2)
N10.0529 (12)0.0801 (15)0.0832 (17)0.0061 (11)0.0072 (11)−0.0080 (12)
O10.0715 (12)0.0713 (13)0.1033 (16)0.0058 (10)0.0174 (11)0.0105 (10)
C1—C21.389 (4)C12—N11.420 (3)
C1—C101.435 (4)C13—C141.365 (4)
C1—C111.464 (3)C13—H130.9300
C2—O11.349 (3)C14—C151.348 (5)
C2—C31.408 (4)C14—H140.9300
C3—C41.344 (4)C15—C161.360 (5)
C3—H30.9300C15—H150.9300
C4—C51.416 (4)C16—C171.388 (4)
C4—H40.9300C16—H160.9300
C5—C61.393 (4)C17—C181.573 (5)
C5—C101.420 (4)C18—C191.449 (7)
C6—C71.356 (5)C18—H18A0.9700
C6—H60.9300C18—H18B0.9700
C7—C81.395 (5)C19—H19A0.9600
C7—H70.9300C19—H19B0.9600
C8—C91.357 (4)C19—H19C0.9600
C8—H80.9300C20—O11.435 (3)
C9—C101.416 (4)C20—C211.478 (5)
C9—H90.9300C20—H20A0.9700
C11—N11.261 (3)C20—H20B0.9700
C11—H110.9300C21—H21A0.9600
C12—C131.364 (4)C21—H21B0.9600
C12—C171.392 (4)C21—H21C0.9600
C2—C1—C10119.3 (2)C15—C14—C13120.2 (3)
C2—C1—C11116.2 (2)C15—C14—H14119.9
C10—C1—C11124.5 (2)C13—C14—H14119.9
O1—C2—C1116.7 (2)C14—C15—C16119.6 (3)
O1—C2—C3122.2 (3)C14—C15—H15120.2
C1—C2—C3121.1 (3)C16—C15—H15120.2
C4—C3—C2119.7 (3)C15—C16—C17121.8 (3)
C4—C3—H3120.2C15—C16—H16119.1
C2—C3—H3120.2C17—C16—H16119.1
C3—C4—C5122.5 (3)C16—C17—C12117.7 (3)
C3—C4—H4118.7C16—C17—C18121.1 (3)
C5—C4—H4118.7C12—C17—C18120.9 (3)
C6—C5—C4121.8 (3)C19—C18—C17110.8 (5)
C6—C5—C10119.7 (3)C19—C18—H18A109.5
C4—C5—C10118.5 (3)C17—C18—H18A109.5
C7—C6—C5121.7 (3)C19—C18—H18B109.5
C7—C6—H6119.1C17—C18—H18B109.5
C5—C6—H6119.1H18A—C18—H18B108.1
C6—C7—C8119.1 (3)C18—C19—H19A109.5
C6—C7—H7120.4C18—C19—H19B109.5
C8—C7—H7120.4H19A—C19—H19B109.5
C9—C8—C7121.3 (3)C18—C19—H19C109.5
C9—C8—H8119.4H19A—C19—H19C109.5
C7—C8—H8119.4H19B—C19—H19C109.5
C8—C9—C10121.0 (3)O1—C20—C21107.3 (3)
C8—C9—H9119.5O1—C20—H20A110.3
C10—C9—H9119.5C21—C20—H20A110.3
C9—C10—C5117.2 (2)O1—C20—H20B110.3
C9—C10—C1123.8 (2)C21—C20—H20B110.3
C5—C10—C1118.9 (2)H20A—C20—H20B108.5
N1—C11—C1126.6 (3)C20—C21—H21A109.5
N1—C11—H11116.7C20—C21—H21B109.5
C1—C11—H11116.7H21A—C21—H21B109.5
C13—C12—C17119.4 (3)C20—C21—H21C109.5
C13—C12—N1122.2 (3)H21A—C21—H21C109.5
C17—C12—N1118.3 (3)H21B—C21—H21C109.5
C12—C13—C14121.4 (3)C11—N1—C12118.0 (2)
C12—C13—H13119.3C2—O1—C20119.5 (2)
C14—C13—H13119.3
C10—C1—C2—O1−179.4 (2)C11—C1—C10—C5176.3 (2)
C11—C1—C2—O13.0 (4)C2—C1—C11—N1−162.3 (3)
C10—C1—C2—C3−0.6 (4)C10—C1—C11—N120.3 (4)
C11—C1—C2—C3−178.2 (2)C17—C12—C13—C140.2 (5)
O1—C2—C3—C4−179.2 (3)N1—C12—C13—C14176.6 (3)
C1—C2—C3—C42.1 (4)C12—C13—C14—C150.6 (5)
C2—C3—C4—C5−1.9 (5)C13—C14—C15—C16−0.8 (6)
C3—C4—C5—C6−179.5 (3)C14—C15—C16—C170.3 (6)
C3—C4—C5—C100.3 (4)C15—C16—C17—C120.5 (6)
C4—C5—C6—C7−179.4 (3)C15—C16—C17—C18174.0 (5)
C10—C5—C6—C70.8 (5)C13—C12—C17—C16−0.7 (5)
C5—C6—C7—C8−0.2 (6)N1—C12—C17—C16−177.2 (3)
C6—C7—C8—C9−0.6 (6)C13—C12—C17—C18−174.2 (4)
C7—C8—C9—C100.7 (5)N1—C12—C17—C189.3 (6)
C8—C9—C10—C50.0 (4)C16—C17—C18—C1967.1 (7)
C8—C9—C10—C1178.2 (3)C12—C17—C18—C19−119.6 (5)
C6—C5—C10—C9−0.7 (4)C1—C11—N1—C12−176.3 (3)
C4—C5—C10—C9179.5 (3)C13—C12—N1—C1145.1 (4)
C6—C5—C10—C1−179.0 (3)C17—C12—N1—C11−138.6 (3)
C4—C5—C10—C11.2 (4)C1—C2—O1—C20−165.1 (2)
C2—C1—C10—C9−179.3 (3)C3—C2—O1—C2016.1 (4)
C11—C1—C10—C9−1.9 (4)C21—C20—O1—C2170.8 (3)
C2—C1—C10—C5−1.0 (4)
D—H···AD—HH···AD···AD—H···A
C9—H9···N10.932.322.961 (4)126
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C9—H9⋯N10.932.322.961 (4)126
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1.  (E)-(2,5-Difluoro-benz-yl)[(2-eth-oxy-naphthalen-1-yl)methyl-idene]amine.

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