organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-Benzyl-N-[(E)-(3,4,5-tri­meth­oxy­phen­yl)methyl­­idene]amine

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aGrupo de Investigacíon Heterocíclicos, Deparatmento de Química, Universidad de Valle, A.A. 25360 Cali, Colombia, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland, and cDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 - Jaén, Spain
*Correspondence e-mail: che562@abdn.ac.uk

(Received 2 October 2006; accepted 3 October 2006; online 18 October 2006)

In the title mol­ecule, C17H19NO3, the dihedral angle formed by the planes of the two benzene rings is 62.3 (1)°. There are no direction-specific inter­actions in the supra­molecular structure.

Comment

The bond lengths and angles in the title compound, (I)[link], show no unusual features. The central part of the mol­ecule is essentially planar, with only the methyl group at C241 and the phenyl group attached to atom C1 tilted out of the plane. This is shown by the leading torsion angles given in Table 1[link]. The dihedral angle formed by the planes of the two benzene rings is 62.3 (1)°.

[Scheme 1]
[Figure 1]
Figure 1
Mol­ecular structure of (I)[link] with the numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Experimental

A neat mixture of benzyl­amine (3.17 mmol) and 3,4,5-trimethoxy­benzaldehyde (3.11 mmol) was heated at 373 K for five minutes. After cooling, a white solid was obtained in quanti­tative yield. Crystals suitable for single-crystal X-ray diffraction were grown from ethanol (m.p. 367 K).

Crystal data
  • C17H19NO3

  • Mr = 285.33

  • Monoclinic, P 21 /c

  • a = 22.1302 (10) Å

  • b = 5.3140 (2) Å

  • c = 12.4571 (5) Å

  • β = 98.447 (2)°

  • V = 1449.06 (10) Å3

  • Z = 4

  • Dx = 1.308 Mg m−3

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 120 (2) K

  • Plate, colourless

  • 0.42 × 0.34 × 0.03 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.963, Tmax = 0.997

  • 14669 measured reflections

  • 3317 independent reflections

  • 2627 reflections with I > 2σ(I)

  • Rint = 0.055

  • θmax = 27.6°

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.154

  • S = 1.14

  • 3317 reflections

  • 193 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0543P)2 + 1.1271P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Selected torsion angles (°)

C2—N1—C1—C11 125.0 (2)
C1—N1—C2—C21 175.79 (18)
N1—C1—C11—C16 89.1 (2)
N1—C1—C11—C12 −91.1 (2)
N1—C2—C21—C26 172.26 (19)
N1—C2—C21—C22 −9.6 (3)
C22—C23—O23—C231 3.5 (3)
C24—C23—O23—C231 −176.53 (16)
C25—C24—O24—C241 72.8 (2)
C23—C24—O24—C241 −110.4 (2)
C26—C25—O25—C251 3.7 (3)
C24—C25—O25—C251 −176.98 (17)

H atoms were treated as riding, with C—H = 0.95, 0.99 and 0.98 Å for aromatic, methylene and methyl C, respectively; Uiso(H) = xUeq(C), where x = 1.5 for methyl and 1.2 for other H atoms.

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10, Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97; molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information


Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT; data reduction: DENZO & COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL & SHELXL97; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

N-benzyl-N-[(E)-(3,4,5-trimethoxyphenyl)methylidene]amine top
Crystal data top
C17H19NO3F(000) = 608
Mr = 285.33Dx = 1.308 Mg m3
Monoclinic, P21/cMelting point: 367 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 22.1302 (10) ÅCell parameters from 3317 reflections
b = 5.3140 (2) Åθ = 3.3–27.6°
c = 12.4571 (5) ŵ = 0.09 mm1
β = 98.447 (2)°T = 120 K
V = 1449.06 (10) Å3Plate, colourless
Z = 40.42 × 0.34 × 0.03 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
3317 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2627 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
Detector resolution: 9.091 pixels mm-1θmax = 27.6°, θmin = 3.3°
φ & ω scansh = 2828
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 66
Tmin = 0.963, Tmax = 0.997l = 1616
14669 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0543P)2 + 1.1271P]
where P = (Fo2 + 2Fc2)/3
3317 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

MS (IE 70 eV): m/z (%) 285 (45), 270 (6), 254 (5), 91 (100).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.17303 (7)0.3758 (3)0.49211 (13)0.0216 (4)
C10.12212 (9)0.2916 (4)0.54614 (17)0.0243 (4)
C20.21935 (9)0.2331 (4)0.50281 (15)0.0201 (4)
C110.10308 (8)0.4877 (4)0.62221 (16)0.0210 (4)
C120.12924 (9)0.4898 (4)0.73129 (17)0.0264 (5)
C130.11283 (10)0.6721 (4)0.80159 (18)0.0298 (5)
C140.06916 (10)0.8502 (4)0.76425 (19)0.0297 (5)
C150.04209 (10)0.8478 (4)0.65706 (19)0.0277 (5)
C160.05928 (9)0.6690 (4)0.58604 (17)0.0241 (4)
C210.27357 (8)0.2747 (4)0.44917 (15)0.0187 (4)
C220.27406 (8)0.4577 (4)0.36889 (15)0.0183 (4)
C230.32533 (9)0.4804 (4)0.31665 (15)0.0181 (4)
O230.33080 (6)0.6491 (3)0.23613 (11)0.0216 (3)
C2310.28149 (9)0.8224 (4)0.20817 (17)0.0228 (4)
C240.37622 (8)0.3231 (4)0.34585 (15)0.0179 (4)
O240.42718 (6)0.3559 (3)0.29596 (11)0.0211 (3)
C2410.43719 (9)0.1529 (4)0.22369 (17)0.0244 (4)
C250.37572 (8)0.1454 (4)0.42831 (15)0.0186 (4)
O250.42793 (6)0.0090 (3)0.45386 (11)0.0241 (3)
C2510.42837 (9)0.1839 (4)0.53421 (17)0.0235 (4)
C260.32410 (9)0.1194 (4)0.47905 (15)0.0201 (4)
H1A0.13420.13610.58760.029*
H1B0.08680.25040.49050.029*
H20.21910.08990.54840.024*
H120.15850.36540.75770.032*
H130.13160.67450.87520.036*
H140.05780.97430.81240.036*
H150.01170.96870.63180.033*
H160.04100.67020.51210.029*
H220.23990.56530.35010.022*
H23A0.27570.92140.27230.034*
H23B0.24400.72920.18230.034*
H23C0.29100.93540.15080.034*
H24A0.40490.15410.16080.037*
H24B0.43650.00790.26200.037*
H24C0.47700.17470.19920.037*
H25A0.39580.30530.51070.035*
H25B0.42170.10820.60330.035*
H25C0.46790.27020.54370.035*
H260.32330.00400.53400.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0199 (8)0.0253 (9)0.0207 (8)0.0002 (7)0.0066 (6)0.0010 (7)
C10.0197 (9)0.0266 (11)0.0281 (11)0.0033 (8)0.0092 (8)0.0024 (9)
C20.0219 (10)0.0207 (10)0.0183 (9)0.0010 (8)0.0045 (7)0.0008 (8)
C110.0158 (9)0.0226 (10)0.0259 (10)0.0043 (7)0.0070 (7)0.0001 (8)
C120.0211 (10)0.0291 (12)0.0293 (11)0.0012 (8)0.0049 (8)0.0008 (9)
C130.0307 (11)0.0354 (13)0.0240 (11)0.0077 (9)0.0068 (9)0.0029 (9)
C140.0338 (12)0.0250 (11)0.0341 (12)0.0054 (9)0.0174 (9)0.0038 (9)
C150.0235 (10)0.0231 (11)0.0385 (12)0.0000 (8)0.0118 (9)0.0027 (9)
C160.0213 (9)0.0247 (11)0.0268 (10)0.0044 (8)0.0053 (8)0.0028 (8)
C210.0192 (9)0.0200 (10)0.0171 (9)0.0016 (7)0.0039 (7)0.0041 (8)
C220.0175 (9)0.0189 (9)0.0184 (9)0.0018 (7)0.0018 (7)0.0018 (8)
C230.0210 (9)0.0168 (9)0.0166 (9)0.0014 (7)0.0032 (7)0.0017 (7)
O230.0212 (7)0.0220 (7)0.0229 (7)0.0033 (5)0.0072 (5)0.0049 (6)
C2310.0240 (10)0.0206 (10)0.0237 (10)0.0039 (8)0.0035 (8)0.0032 (8)
C240.0154 (9)0.0204 (10)0.0185 (9)0.0024 (7)0.0043 (7)0.0022 (8)
O240.0174 (7)0.0218 (7)0.0257 (7)0.0015 (5)0.0084 (5)0.0016 (6)
C2410.0235 (10)0.0245 (11)0.0271 (10)0.0027 (8)0.0099 (8)0.0022 (9)
C250.0156 (9)0.0196 (10)0.0197 (9)0.0013 (7)0.0003 (7)0.0021 (8)
O250.0170 (7)0.0289 (8)0.0265 (7)0.0051 (6)0.0033 (5)0.0078 (6)
C2510.0223 (10)0.0228 (10)0.0244 (10)0.0026 (8)0.0003 (8)0.0041 (8)
C260.0202 (9)0.0211 (10)0.0189 (9)0.0003 (7)0.0029 (7)0.0019 (8)
Geometric parameters (Å, º) top
N1—C21.266 (3)C22—H220.95
N1—C11.465 (2)C23—O231.364 (2)
C1—C111.510 (3)C23—C241.407 (3)
C1—H1A0.99O23—C2311.431 (2)
C1—H1B0.99C231—H23A0.98
C2—C211.473 (3)C231—H23B0.98
C2—H20.95C231—H23C0.98
C11—C161.394 (3)C24—O241.376 (2)
C11—C121.397 (3)C24—C251.397 (3)
C12—C131.390 (3)O24—C2411.443 (2)
C12—H120.95C241—H24A0.98
C13—C141.384 (3)C241—H24B0.98
C13—H130.95C241—H24C0.98
C14—C151.381 (3)C25—O251.361 (2)
C14—H140.95C25—C261.391 (3)
C15—C161.389 (3)O25—C2511.432 (2)
C15—H150.95C251—H25A0.98
C16—H160.95C251—H25B0.98
C21—C261.395 (3)C251—H25C0.98
C21—C221.396 (3)C26—H260.95
C22—C231.394 (3)
C2—N1—C1115.73 (17)O23—C23—C22124.54 (17)
N1—C1—C11112.45 (17)O23—C23—C24115.24 (16)
N1—C1—H1A109.1C22—C23—C24120.23 (17)
C11—C1—H1A109.1C23—O23—C231117.07 (14)
N1—C1—H1B109.1O23—C231—H23A109.5
C11—C1—H1B109.1O23—C231—H23B109.5
H1A—C1—H1B107.8H23A—C231—H23B109.5
N1—C2—C21124.27 (18)O23—C231—H23C109.5
N1—C2—H2117.9H23A—C231—H23C109.5
C21—C2—H2117.9H23B—C231—H23C109.5
C16—C11—C12118.58 (19)O24—C24—C25120.88 (17)
C16—C11—C1121.29 (18)O24—C24—C23119.08 (17)
C12—C11—C1120.14 (19)C25—C24—C23119.96 (16)
C13—C12—C11120.6 (2)C24—O24—C241113.47 (15)
C13—C12—H12119.7O24—C241—H24A109.5
C11—C12—H12119.7O24—C241—H24B109.5
C14—C13—C12120.0 (2)H24A—C241—H24B109.5
C14—C13—H13120.0O24—C241—H24C109.5
C12—C13—H13120.0H24A—C241—H24C109.5
C15—C14—C13120.1 (2)H24B—C241—H24C109.5
C15—C14—H14120.0O25—C25—C26124.48 (17)
C13—C14—H14120.0O25—C25—C24115.71 (16)
C14—C15—C16120.1 (2)C26—C25—C24119.81 (17)
C14—C15—H15119.9C25—O25—C251117.58 (15)
C16—C15—H15119.9O25—C251—H25A109.5
C15—C16—C11120.6 (2)O25—C251—H25B109.5
C15—C16—H16119.7H25A—C251—H25B109.5
C11—C16—H16119.7O25—C251—H25C109.5
C26—C21—C22120.85 (17)H25A—C251—H25C109.5
C26—C21—C2117.68 (17)H25B—C251—H25C109.5
C22—C21—C2121.45 (17)C25—C26—C21119.95 (18)
C23—C22—C21119.17 (17)C25—C26—H26120.0
C23—C22—H22120.4C21—C26—H26120.0
C21—C22—H22120.4
C2—N1—C1—C11125.0 (2)C22—C23—O23—C2313.5 (3)
C1—N1—C2—C21175.79 (18)C24—C23—O23—C231176.53 (16)
N1—C1—C11—C1689.1 (2)O23—C23—C24—O242.5 (3)
N1—C1—C11—C1291.1 (2)C22—C23—C24—O24177.52 (17)
C16—C11—C12—C131.4 (3)O23—C23—C24—C25179.29 (17)
C1—C11—C12—C13178.87 (18)C22—C23—C24—C250.8 (3)
C11—C12—C13—C141.5 (3)C25—C24—O24—C24172.8 (2)
C12—C13—C14—C150.4 (3)C23—C24—O24—C241110.4 (2)
C13—C14—C15—C161.0 (3)O24—C24—C25—O250.7 (3)
C14—C15—C16—C111.1 (3)C23—C24—C25—O25177.41 (17)
C12—C11—C16—C150.0 (3)O24—C24—C25—C26178.67 (17)
C1—C11—C16—C15179.81 (18)C23—C24—C25—C262.0 (3)
N1—C2—C21—C26172.26 (19)C26—C25—O25—C2513.7 (3)
N1—C2—C21—C229.6 (3)C24—C25—O25—C251176.98 (17)
C26—C21—C22—C231.5 (3)O25—C25—C26—C21177.84 (18)
C2—C21—C22—C23176.64 (17)C24—C25—C26—C211.5 (3)
C21—C22—C23—O23179.02 (17)C22—C21—C26—C250.2 (3)
C21—C22—C23—C240.9 (3)C2—C21—C26—C25177.91 (17)
 

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England. The authors thank the staff for all their help and advice. JC thanks the Consejería de Innovacíon, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. RA and LS thank COLCIENCIAS, UNIVALLE (Universidad del Valle, Colombia), and RA also thanks AUIP for supporting a research fellowship.

References

First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
First citationHooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10, Crystallography Centre, Chemistry Department, NUI Galway, Ireland.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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