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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1647.
Published online 2008 July 31. doi:  10.1107/S1600536808023751
PMCID: PMC2962231

(E,E)-N,N′-Bis­(4-methoxy­benzyl­idene)cyclo­hexane-1,2-diamine

Abstract

In the title compound, C22H26N2O2, the meth­oxy and the benzyl­idene groups are essentially coplanar, and the cyclo­hexane ring has a chair conformation. The two halves of the mol­ecule are related by a twofold rotation. The crystal structure is stabilized only by van der Waals inter­actions.

Related literature

For the chemistry of Schiff base derivatives, see: Negm & Zaki (2008 [triangle]); Feng et al. (2008 [triangle]); Lee & Do (2007 [triangle]).

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Object name is e-64-o1647-scheme1.jpg

Experimental

Crystal data

  • C22H26N2O2
  • M r = 350.45
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1647-efi3.jpg
  • a = 19.674 (3) Å
  • b = 5.4097 (9) Å
  • c = 18.662 (3) Å
  • V = 1986.2 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 298 (2) K
  • 0.35 × 0.30 × 0.20 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.978, T max = 0.985
  • 18603 measured reflections
  • 2262 independent reflections
  • 1588 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.154
  • S = 1.12
  • 2262 reflections
  • 118 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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 .

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808023751/wk2089sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023751/wk2089Isup2.hkl

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

supplementary crystallographic information

Comment

In the past five years, we have focused on the chemistry of schiff-base derivatives because of their biological behaviors and their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Negm & Zaki, 2008; Feng et al. 2008; Lee & Do, 2007). We report here the crystal structure of the title compound, (N1E,N2E)-N1,N2-bis(4-methoxybenzylidene)cyclohexane-1,2-diamine.

In the title compound (Fig.1), there is a rotation axis bisecting the molecule through the cyclohexane ring. The methoxy and the benzylidene groups are essentially coplanar, and the cyclohexane-1,2-diamine group is in the chair form. The C4=N1 bond length of 1.249 (2) Å is consistent with the value for a double bond. The crystal structure is stabilized only by van der Waals interactions.

Experimental

rac-Diaminocyclohexane (1.20 g, 10.5 mmol) and p-anisaldehyde (1.36 g, 10.0 mmol) were dissolved in ethanol (20 mL) under magnetic stirring. The mixture was heated to reflux for 12 h. After cooled to room temperature, the resulting content was put to a refrigerator to stand over night. Then, the precipitate was filtered off and recrystallized from ethanol affording colorless block crystals of this compound suitable for X-ray analysis were obtained.

Refinement

All H atoms attached to C atoms were fixed geometrically and treated as riding with C–H = 0.93 Å(aromatic), C–H = 0.98 Å(methine), 0.97 Å(methylene), C–H = 0.96 Å(methyl), with Uiso(H) =1.2Ueq(C except methyl C) and Uiso(H) =1.5Ueq(methyl C).

Figures

Fig. 1.
A view of the title compound with the atom numbering scheme, symmetry related atoms, (-x+1/2, -y+1/2, z) denoted by A. Displacement ellipsoids were drawn at the 30% probability level.

Crystal data

C22H26N2O2F000 = 752
Mr = 350.45Dx = 1.172 Mg m3
Orthorhombic, PccnMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 3131 reflections
a = 19.674 (3) Åθ = 3.0–27.4º
b = 5.4097 (9) ŵ = 0.08 mm1
c = 18.662 (3) ÅT = 298 (2) K
V = 1986.2 (6) Å3Block, colorless
Z = 40.35 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer2262 independent reflections
Radiation source: fine-focus sealed tube1588 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.060
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 298(2) Kθmin = 3.0º
ω scansh = −25→25
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −7→7
Tmin = 0.978, Tmax = 0.985l = −24→24
18603 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.154  w = 1/[σ2(Fo2) + (0.0572P)2 + 0.4317P] where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
2262 reflectionsΔρmax = 0.13 e Å3
118 parametersΔρmin = −0.14 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
O10.47992 (8)0.4625 (3)0.41000 (8)0.0713 (5)
N10.32205 (8)0.3062 (3)0.11039 (9)0.0558 (5)
C50.36446 (9)0.4561 (4)0.22382 (10)0.0493 (5)
C20.32123 (10)0.3262 (5)−0.02019 (11)0.0629 (6)
H2A0.34540.1699−0.02040.075*
H2B0.35470.4577−0.02030.075*
C70.45135 (10)0.2643 (4)0.29659 (11)0.0535 (5)
H70.48270.13800.30340.064*
C40.32303 (10)0.4677 (4)0.15823 (10)0.0553 (5)
H40.29550.60570.15190.066*
C80.44380 (10)0.4485 (4)0.34762 (10)0.0513 (5)
C60.41180 (10)0.2704 (4)0.23553 (10)0.0539 (5)
H60.41700.14670.20140.065*
C30.27888 (9)0.3439 (4)0.04791 (10)0.0532 (5)
H30.25920.51010.05060.064*
C100.35804 (10)0.6392 (4)0.27558 (11)0.0591 (5)
H100.32700.76660.26880.071*
C10.27826 (11)0.3452 (4)−0.08769 (11)0.0636 (6)
H1B0.25870.5095−0.09080.076*
H1A0.30690.3204−0.12940.076*
C110.52945 (14)0.2748 (6)0.42442 (13)0.0871 (8)
H11A0.55090.30760.46960.131*
H11B0.56310.27460.38720.131*
H11C0.50750.11640.42620.131*
C90.39688 (10)0.6346 (4)0.33659 (11)0.0595 (6)
H90.39160.75800.37080.071*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0718 (9)0.0912 (12)0.0509 (9)0.0097 (9)−0.0096 (7)−0.0121 (8)
N10.0534 (9)0.0608 (11)0.0532 (10)0.0022 (8)−0.0042 (8)−0.0036 (8)
C50.0448 (9)0.0533 (11)0.0497 (11)−0.0015 (9)0.0020 (8)−0.0005 (9)
C20.0514 (11)0.0790 (16)0.0583 (13)−0.0074 (10)0.0038 (10)0.0038 (11)
C70.0538 (11)0.0521 (12)0.0544 (11)0.0079 (9)0.0001 (10)−0.0009 (9)
C40.0490 (11)0.0572 (12)0.0597 (13)0.0051 (9)−0.0020 (9)0.0010 (10)
C80.0510 (10)0.0593 (12)0.0436 (10)−0.0043 (9)0.0035 (9)−0.0025 (9)
C60.0574 (11)0.0524 (12)0.0518 (11)0.0006 (9)0.0032 (10)−0.0101 (9)
C30.0528 (11)0.0543 (12)0.0524 (11)0.0028 (9)−0.0044 (9)0.0016 (9)
C100.0572 (12)0.0541 (12)0.0661 (13)0.0088 (10)0.0001 (10)−0.0060 (10)
C10.0680 (13)0.0694 (14)0.0535 (12)−0.0003 (11)0.0036 (10)0.0037 (10)
C110.0886 (17)0.110 (2)0.0625 (15)0.0236 (16)−0.0193 (13)0.0001 (14)
C90.0628 (12)0.0580 (13)0.0578 (13)0.0034 (10)0.0017 (10)−0.0148 (10)

Geometric parameters (Å, °)

O1—C81.366 (2)C4—H40.9300
O1—C111.433 (3)C8—C91.381 (3)
N1—C41.249 (2)C6—H60.9300
N1—C31.457 (2)C3—C3i1.525 (4)
C5—C101.389 (3)C3—H30.9800
C5—C61.387 (3)C10—C91.371 (3)
C5—C41.472 (3)C10—H100.9300
C2—C31.523 (3)C1—C1i1.516 (4)
C2—C11.521 (3)C1—H1B0.9700
C2—H2A0.9700C1—H1A0.9700
C2—H2B0.9700C11—H11A0.9600
C7—C61.380 (3)C11—H11B0.9600
C7—C81.386 (3)C11—H11C0.9600
C7—H70.9300C9—H90.9300
C8—O1—C11118.35 (17)N1—C3—C2109.88 (15)
C4—N1—C3118.88 (17)C3i—C3—C2111.46 (14)
C10—C5—C6117.90 (18)N1—C3—H3108.5
C10—C5—C4119.83 (18)C3i—C3—H3108.5
C6—C5—C4122.25 (18)C2—C3—H3108.5
C3—C2—C1112.52 (16)C9—C10—C5120.92 (19)
C3—C2—H2A109.1C9—C10—H10119.5
C1—C2—H2A109.1C5—C10—H10119.5
C3—C2—H2B109.1C1i—C1—C2111.22 (15)
C1—C2—H2B109.1C1i—C1—H1B109.4
H2A—C2—H2B107.8C2—C1—H1B109.4
C6—C7—C8119.32 (19)C1i—C1—H1A109.4
C6—C7—H7120.3C2—C1—H1A109.4
C8—C7—H7120.3H1B—C1—H1A108.0
N1—C4—C5124.96 (19)O1—C11—H11A109.5
N1—C4—H4117.5O1—C11—H11B109.5
C5—C4—H4117.5H11A—C11—H11B109.5
O1—C8—C9115.75 (17)O1—C11—H11C109.5
O1—C8—C7124.70 (18)H11A—C11—H11C109.5
C9—C8—C7119.55 (18)H11B—C11—H11C109.5
C7—C6—C5121.71 (18)C8—C9—C10120.61 (19)
C7—C6—H6119.1C8—C9—H9119.7
C5—C6—H6119.1C10—C9—H9119.7
N1—C3—C3i109.94 (14)
C3—N1—C4—C5−179.41 (17)C4—N1—C3—C3i−112.3 (2)
C10—C5—C4—N1−175.8 (2)C4—N1—C3—C2124.6 (2)
C6—C5—C4—N16.0 (3)C1—C2—C3—N1175.80 (18)
C11—O1—C8—C9−179.9 (2)C1—C2—C3—C3i53.7 (3)
C11—O1—C8—C70.1 (3)C6—C5—C10—C9−0.6 (3)
C6—C7—C8—O1−179.97 (18)C4—C5—C10—C9−178.92 (19)
C6—C7—C8—C90.0 (3)C3—C2—C1—C1i−54.7 (3)
C8—C7—C6—C5−0.1 (3)O1—C8—C9—C10179.73 (18)
C10—C5—C6—C70.4 (3)C7—C8—C9—C10−0.3 (3)
C4—C5—C6—C7178.64 (18)C5—C10—C9—C80.6 (3)

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: WK2089).

References

  • Feng, Y., Wang, C., Xu, J., Xu, L., Liao, D., Yan, S. & Jiang, Z. (2008). Inorg. Chem. Commun.11, 549–552.
  • Lee, J., Kim, Y. & Do, Y. (2007). Inorg. Chem.46, 7701–7703. [PubMed]
  • Negm, N.-A. & Zaki, M.-F. (2008). Colloid Surf. B, 64, 179–183. [PubMed]
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography