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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o56.
Published online 2008 December 10. doi:  10.1107/S160053680803910X
PMCID: PMC2967970

(E)-N-(2,3,4-Trimeth­oxy-6-methyl­benzyl­idene)naphthalen-1-amine

Abstract

In the title compound, C21H21NO3, the dihedral angle between the naphthalene ring system and the substituted benzene ring is 55.7 (2)°. The mol­ecules are linked into a zigzag chain running along the b axis by C—H(...)O hydrogen bonds.

Related literature

For a related structure, see: Zhang (2008 [triangle]).

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Object name is e-65-00o56-scheme1.jpg

Experimental

Crystal data

  • C21H21NO3
  • M r = 335.39
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o56-efi1.jpg
  • a = 10.9225 (14) Å
  • b = 14.7630 (16) Å
  • c = 22.514 (2) Å
  • V = 3630.3 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 (2) K
  • 0.23 × 0.19 × 0.08 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.981, T max = 0.994
  • 17242 measured reflections
  • 3195 independent reflections
  • 1918 reflections with I > 2σ(I)
  • R int = 0.071

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.166
  • S = 1.07
  • 3195 reflections
  • 226 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803910X/ci2730sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803910X/ci2730Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The preparation, properties and applications of Schiff bases are important in the development of coordination chemistry. In this paper, the crystal structure of the title compound is reported.

Bond lengths and angles of the title molecule (Fig.1) agree with those observed in a related compound, (E)-N-(2,3,4-trimethoxy-6-methylbenzylidene)aniline (Zhang, 2008). The dihedral angle between the naphthalene ring system and the substituted benzene ring is 55.7 (2)°. One of the methoxy groups is coplanar (C10—O3—C5—C6 = 2.4 (4)°) with the attached ring whereas the other two methoxy groups are twisted (C8—O1—C3—C4 = -78.3 (4)° and C9—O2—C4—C3 = 109.1 (3)°).

The molecules are linked into a zigzag chain running along the b axis by C—H···O hydrogen bonds (Table 1).

Experimental

A mixture of 1-naphthylamine (0.715 g, 5 mmol) and 2,3,4-trimethoxy-6-methylbenzaldehyde (1.04 g, 5 mmol) in ethanol (30 ml) was refluxed for 2 h. After cooling, the precipitate obtained was filtered and dried. The crude product was (20 mg) was dissolved in ethanol (20 ml) and the solution was filtered to remove impurities, and then left for crystallization at room temperature. Single crystals suitable for X-ray crystal structure determination were obtained after a week.

Refinement

H atoms were positioned geometrically (C-H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids.

Crystal data

C21H21NO3F(000) = 1424
Mr = 335.39Dx = 1.227 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3424 reflections
a = 10.9225 (14) Åθ = 2.5–25.3°
b = 14.7630 (16) ŵ = 0.08 mm1
c = 22.514 (2) ÅT = 298 K
V = 3630.3 (7) Å3Plate, light yellow
Z = 80.23 × 0.19 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer3195 independent reflections
Radiation source: fine-focus sealed tube1918 reflections with I > 2σ(I)
graphiteRint = 0.071
[var phi] and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)h = −12→8
Tmin = 0.981, Tmax = 0.994k = −17→15
17242 measured reflectionsl = −26→25

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0824P)2] where P = (Fo2 + 2Fc2)/3
3195 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.25 e Å3

Special details

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.1079 (2)0.32182 (15)0.65758 (10)0.0437 (6)
O1−0.20286 (18)0.26652 (12)0.57093 (9)0.0494 (6)
O2−0.34730 (17)0.11513 (12)0.58640 (8)0.0463 (5)
O3−0.29401 (19)−0.00497 (13)0.67264 (8)0.0521 (6)
C10.0044 (3)0.30050 (17)0.63498 (12)0.0404 (7)
H1−0.02710.33930.60630.048*
C2−0.0689 (2)0.22122 (17)0.64990 (12)0.0374 (7)
C3−0.1715 (3)0.20404 (17)0.61366 (11)0.0360 (7)
C4−0.2445 (2)0.12749 (19)0.62117 (11)0.0354 (7)
C5−0.2172 (3)0.06808 (17)0.66764 (12)0.0382 (7)
C6−0.1196 (3)0.08606 (19)0.70516 (12)0.0429 (8)
H6−0.10400.04670.73650.051*
C7−0.0440 (3)0.16116 (18)0.69743 (12)0.0397 (7)
C8−0.1737 (5)0.2453 (3)0.51222 (15)0.1067 (17)
H8A−0.10210.20760.51140.160*
H8B−0.15790.30010.49050.160*
H8C−0.24090.21360.49430.160*
C9−0.3371 (3)0.0441 (2)0.54325 (14)0.0654 (10)
H9A−0.26050.04950.52270.098*
H9B−0.40320.04870.51530.098*
H9C−0.3408−0.01360.56290.098*
C10−0.2751 (4)−0.0653 (2)0.72126 (16)0.0843 (13)
H10A−0.1990−0.09690.71600.126*
H10B−0.3410−0.10830.72290.126*
H10C−0.2725−0.03150.75760.126*
C110.0612 (3)0.1741 (2)0.73974 (14)0.0616 (10)
H11A0.13700.16490.71900.092*
H11B0.05480.13130.77170.092*
H11C0.05900.23450.75550.092*
C120.1640 (3)0.40259 (17)0.63702 (12)0.0367 (7)
C130.1017 (3)0.48289 (18)0.63178 (13)0.0450 (8)
H130.01910.48550.64150.054*
C140.1619 (3)0.56103 (19)0.61192 (15)0.0539 (9)
H140.11810.61480.60860.065*
C150.2820 (3)0.56022 (19)0.59751 (14)0.0530 (8)
H150.31980.61300.58430.064*
C160.3507 (3)0.47867 (18)0.60249 (13)0.0423 (7)
C170.2925 (3)0.39934 (17)0.62421 (11)0.0375 (7)
C180.3634 (3)0.32002 (19)0.63141 (13)0.0463 (8)
H180.32720.26810.64690.056*
C190.4841 (3)0.3187 (2)0.61596 (15)0.0582 (9)
H190.52940.26590.62090.070*
C200.5401 (3)0.3956 (2)0.59289 (15)0.0613 (9)
H200.62200.39340.58180.074*
C210.4760 (3)0.4741 (2)0.58642 (14)0.0562 (9)
H210.51480.52520.57130.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0416 (16)0.0425 (14)0.0471 (15)−0.0020 (12)−0.0009 (13)0.0028 (11)
O10.0476 (13)0.0498 (12)0.0507 (13)0.0062 (10)−0.0107 (10)0.0102 (10)
O20.0382 (12)0.0539 (12)0.0468 (12)0.0001 (9)−0.0099 (10)−0.0034 (10)
O30.0574 (15)0.0524 (12)0.0465 (12)−0.0163 (11)−0.0104 (10)0.0093 (10)
C10.0432 (19)0.0409 (16)0.0370 (16)0.0035 (14)−0.0001 (15)−0.0002 (12)
C20.0364 (17)0.0391 (15)0.0367 (16)0.0038 (13)−0.0001 (14)−0.0028 (13)
C30.0373 (17)0.0377 (15)0.0332 (15)0.0073 (13)0.0001 (14)0.0003 (12)
C40.0285 (15)0.0461 (16)0.0315 (15)0.0027 (13)−0.0040 (13)−0.0034 (12)
C50.0368 (18)0.0422 (16)0.0357 (16)−0.0041 (13)−0.0011 (14)0.0002 (13)
C60.0488 (19)0.0471 (17)0.0328 (16)−0.0029 (15)−0.0055 (15)0.0091 (13)
C70.0406 (18)0.0445 (16)0.0341 (15)−0.0010 (14)−0.0075 (14)0.0040 (13)
C80.198 (5)0.085 (3)0.038 (2)0.004 (3)0.004 (3)0.012 (2)
C90.062 (2)0.087 (2)0.0472 (19)−0.015 (2)−0.0120 (18)−0.0113 (18)
C100.102 (3)0.079 (3)0.072 (2)−0.041 (2)−0.030 (2)0.036 (2)
C110.057 (2)0.071 (2)0.057 (2)−0.0187 (17)−0.0196 (18)0.0195 (17)
C120.0378 (17)0.0367 (15)0.0357 (16)0.0000 (13)−0.0035 (14)−0.0031 (12)
C130.0394 (18)0.0420 (17)0.0534 (19)0.0042 (14)−0.0036 (15)−0.0067 (13)
C140.051 (2)0.0357 (17)0.075 (2)0.0031 (15)−0.0084 (19)−0.0022 (15)
C150.053 (2)0.0359 (17)0.070 (2)−0.0102 (15)−0.0104 (18)0.0042 (15)
C160.0410 (18)0.0396 (16)0.0462 (17)−0.0063 (14)−0.0066 (15)−0.0045 (13)
C170.0373 (17)0.0382 (16)0.0369 (16)−0.0005 (14)−0.0074 (14)−0.0061 (12)
C180.045 (2)0.0382 (16)0.0555 (19)0.0033 (14)−0.0038 (16)−0.0039 (14)
C190.044 (2)0.054 (2)0.077 (2)0.0105 (16)−0.0064 (19)−0.0060 (17)
C200.0356 (19)0.063 (2)0.085 (3)−0.0022 (17)0.0030 (19)−0.0095 (19)
C210.0411 (19)0.0558 (19)0.072 (2)−0.0134 (16)−0.0018 (18)0.0003 (16)

Geometric parameters (Å, °)

N1—C11.279 (4)C10—H10A0.96
N1—C121.418 (3)C10—H10B0.96
O1—C31.376 (3)C10—H10C0.96
O1—C81.395 (4)C11—H11A0.96
O2—C41.381 (3)C11—H11B0.96
O2—C91.434 (3)C11—H11C0.96
O3—C51.371 (3)C12—C131.372 (4)
O3—C101.426 (3)C12—C171.434 (4)
C1—C21.457 (4)C13—C141.401 (4)
C1—H10.93C13—H130.93
C2—C31.410 (4)C14—C151.351 (4)
C2—C71.416 (4)C14—H140.93
C3—C41.393 (4)C15—C161.423 (4)
C4—C51.397 (4)C15—H150.93
C5—C61.386 (4)C16—C211.417 (4)
C6—C71.393 (4)C16—C171.419 (4)
C6—H60.93C17—C181.413 (4)
C7—C111.505 (4)C18—C191.364 (4)
C8—H8A0.96C18—H180.93
C8—H8B0.96C19—C201.390 (4)
C8—H8C0.96C19—H190.93
C9—H9A0.96C20—C211.362 (4)
C9—H9B0.96C20—H200.93
C9—H9C0.96C21—H210.93
C1—N1—C12117.3 (2)O3—C10—H10C109.5
C3—O1—C8117.1 (2)H10A—C10—H10C109.5
C4—O2—C9114.7 (2)H10B—C10—H10C109.5
C5—O3—C10117.8 (2)C7—C11—H11A109.5
N1—C1—C2126.3 (3)C7—C11—H11B109.5
N1—C1—H1116.9H11A—C11—H11B109.5
C2—C1—H1116.9C7—C11—H11C109.5
C3—C2—C7118.5 (2)H11A—C11—H11C109.5
C3—C2—C1116.6 (2)H11B—C11—H11C109.5
C7—C2—C1124.9 (3)C13—C12—N1122.7 (3)
O1—C3—C4119.1 (2)C13—C12—C17119.8 (3)
O1—C3—C2118.8 (2)N1—C12—C17117.4 (2)
C4—C3—C2122.0 (2)C12—C13—C14120.4 (3)
O2—C4—C3120.2 (2)C12—C13—H13119.8
O2—C4—C5121.0 (2)C14—C13—H13119.8
C3—C4—C5118.6 (2)C15—C14—C13121.6 (3)
O3—C5—C6124.8 (2)C15—C14—H14119.2
O3—C5—C4115.2 (2)C13—C14—H14119.2
C6—C5—C4120.0 (3)C14—C15—C16120.0 (3)
C5—C6—C7122.2 (2)C14—C15—H15120.0
C5—C6—H6118.9C16—C15—H15120.0
C7—C6—H6118.9C21—C16—C17118.7 (3)
C6—C7—C2118.6 (3)C21—C16—C15121.9 (3)
C6—C7—C11118.3 (2)C17—C16—C15119.3 (3)
C2—C7—C11123.0 (3)C18—C17—C16118.6 (3)
O1—C8—H8A109.5C18—C17—C12122.8 (3)
O1—C8—H8B109.5C16—C17—C12118.7 (2)
H8A—C8—H8B109.5C19—C18—C17120.8 (3)
O1—C8—H8C109.5C19—C18—H18119.6
H8A—C8—H8C109.5C17—C18—H18119.6
H8B—C8—H8C109.5C18—C19—C20120.6 (3)
O2—C9—H9A109.5C18—C19—H19119.7
O2—C9—H9B109.5C20—C19—H19119.7
H9A—C9—H9B109.5C21—C20—C19120.6 (3)
O2—C9—H9C109.5C21—C20—H20119.7
H9A—C9—H9C109.5C19—C20—H20119.7
H9B—C9—H9C109.5C20—C21—C16120.6 (3)
O3—C10—H10A109.5C20—C21—H21119.7
O3—C10—H10B109.5C16—C21—H21119.7
H10A—C10—H10B109.5
C12—N1—C1—C2−179.6 (2)C1—C2—C7—C6−177.7 (3)
N1—C1—C2—C3−171.3 (3)C3—C2—C7—C11−178.5 (3)
N1—C1—C2—C78.5 (4)C1—C2—C7—C111.7 (4)
C8—O1—C3—C4−78.3 (4)C1—N1—C12—C1347.2 (4)
C8—O1—C3—C2103.9 (3)C1—N1—C12—C17−135.8 (3)
C7—C2—C3—O1174.0 (2)N1—C12—C13—C14179.2 (3)
C1—C2—C3—O1−6.2 (4)C17—C12—C13—C142.3 (4)
C7—C2—C3—C4−3.7 (4)C12—C13—C14—C15−0.2 (5)
C1—C2—C3—C4176.1 (2)C13—C14—C15—C16−0.2 (5)
C9—O2—C4—C3109.1 (3)C14—C15—C16—C21178.3 (3)
C9—O2—C4—C5−76.4 (3)C14—C15—C16—C17−1.7 (4)
O1—C3—C4—O2−0.5 (4)C21—C16—C17—C182.8 (4)
C2—C3—C4—O2177.2 (2)C15—C16—C17—C18−177.2 (3)
O1—C3—C4—C5−175.2 (2)C21—C16—C17—C12−176.2 (3)
C2—C3—C4—C52.5 (4)C15—C16—C17—C123.8 (4)
C10—O3—C5—C62.4 (4)C13—C12—C17—C18176.9 (3)
C10—O3—C5—C4−176.5 (3)N1—C12—C17—C18−0.1 (4)
O2—C4—C5—O34.6 (4)C13—C12—C17—C16−4.1 (4)
C3—C4—C5—O3179.2 (2)N1—C12—C17—C16178.8 (2)
O2—C4—C5—C6−174.4 (2)C16—C17—C18—C19−2.2 (4)
C3—C4—C5—C60.2 (4)C12—C17—C18—C19176.8 (3)
O3—C5—C6—C7179.4 (3)C17—C18—C19—C200.1 (5)
C4—C5—C6—C7−1.7 (4)C18—C19—C20—C211.3 (5)
C5—C6—C7—C20.6 (4)C19—C20—C21—C16−0.7 (5)
C5—C6—C7—C11−178.9 (3)C17—C16—C21—C20−1.4 (5)
C3—C2—C7—C62.1 (4)C15—C16—C21—C20178.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13···O3i0.932.563.489 (4)178

Symmetry codes: (i) −x−1/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2730).

References

  • Bruker (1997). SADABS, SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, H. (2008). Acta Cryst. E64, o1219. [PMC free article] [PubMed]

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