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

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ISSN: 2056-9890

1,3-Bis[(4-methylbenzyl­idene)amino­­oxy]propane

aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and bSchool of Environmental Science and Municipal Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: dongwk@126.com

(Received 9 October 2009; accepted 14 October 2009; online 17 October 2009)

The title bis­oxime compound, C19H22N2O2, synthesized by the reaction of 4-methyl-2-hydroxy­benzaldehyde with 1,3-bis­(amino­oxy)propane in ethanol, adopts a V-shaped conformation. The dihedral angle between the rings is 84.59 (3)°. The mol­ecule is disposed about a crystallographic twofold rotation axis, with one C atom lying on the axis. In the crystal, mol­ecules are packed by C—H⋯π(Ph) inter­actions, forming chains.

Related literature

For bis­oximes and their applications, see: Akine et al. (2005[Akine, S., Taniguchi, T., Dong, W. K., Masubuchi, S. & Nabeshima, T. (2005). J. Org. Chem. 70, 1704-1711.]); Atwood & Harvey (2001[Atwood, D. A. & Harvey, M. (2001). Chem. Rev. 101, 37-52.]); Dong et al. (2008[Dong, W.-K., He, X.-N., Li, L., Lv, Z.-W. & Tong, J.-F. (2008). Acta Cryst. E64, o1405.], 2009[Dong, W.-K., Zhao, C.-Y., Sun, Y.-X., Tang, X.-L. & He, X.-N. (2009). Inorg. Chem. Commun. 12, 234-236.]); He et al. (2008[He, X.-N., Dong, W.-K., Bai, W.-J., Yan, H.-B. & Lv, Z.-W. (2008). Acta Cryst. E64, o1532.]); Yeap et al. (2008[Yeap, C. S., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o1854.]).

[Scheme 1]

Experimental

Crystal data
  • C19H22N2O2

  • Mr = 310.39

  • Monoclinic, C 2/c

  • a = 29.843 (2) Å

  • b = 4.8668 (7) Å

  • c = 12.1202 (11) Å

  • β = 98.568 (1)°

  • V = 1740.7 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.43 × 0.13 × 0.07 mm

Data collection
  • Siemens SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.968, Tmax = 0.995

  • 4227 measured reflections

  • 1530 independent reflections

  • 831 reflections with I > 2σ(I)

  • Rint = 0.062

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.175

  • S = 1.12

  • 1530 reflections

  • 106 parameters

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10CCg1 0.96 2.73 3.614 (2) 153
Cg1 is the centroid of the C4–C9 ring.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Much interest has been focused on bisoxime compounds, in which the large electronegativity of O atoms is expected to affect strongly the electronic properties of the nitrogen atoms, and exhibit high stability against imine metathesis reactions (Akine et al., 2005). Some of them or their metal complexes are used in wide field due to their variety of applications, especially for catalysis and biological processes, magnetism, and supramolecular architectures (Atwood et al., 2001; Yeap et al., 2008; Dong et al., 2008). Herein, the synthesis and structure of 4,4'-dimethyl-1,3-[propenedioxybis(nitrilomethylidyne)]dibenzene (I) is reported (Fig. 1).

The single-crystal structure of (I) is built up by discrete C19H22N2O2 molecules, in which all bond lengths are in normal ranges. The title compound adopts a V-shaped configuration with the dihedral angle between the two halves of the molecule is 85.82 (3)°. The molecules are disposed about a crystallographic two-fold rotation axis. This structure is similar to that observed in our previously reported salen-type bisoxime compounds (He et al., 2008). The packing of the molecule is controlled by C—H···π(Ph) interactions linking molecules into infinite supramolecular structure along b axis.

Related literature top

For bisoximes and their applications, see: Akine et al. (2005); Atwood & Harvey (2001); Dong et al. (2008, 2009); He et al. (2008); Yeap et al. (2008). Cg1 is the centroid of the C4–C9 ring.

Experimental top

4,4'-Dimethyl-1,3-[propenedioxybis(nitrilomethylidyne)]dibenzene was synthesized according to an analogous method reported earlier (Dong et al., 2009). To an ethanol solution (4 ml) of 4-methyl-2-hydroxybenzaldehyde (243.2 mg, 2.02 mmol) was added an ethanol solution (4 ml) of 1,3-bis(aminooxy)propane (108.3 mg, 1.02 mmol). The reaction mixture was stirred at 328–333 K for 14 h. After cool to room temperature, no precipitate was formed, which was concentrated to about 1 ml under reduced pressure. The precipitate formed was separated by filtration, and washed several times with n-hexane. The product was dried under vacuum to yield 189.4 mg of (I). Yield, 60.4%. m. p. 329–330 K. Anal. Calcd. for C19H22N2O2: C, 73.52; H, 7.14; N, 9.03. Found: C, 73.49; H, 7.01; N, 9.39.

Colorless needle-like single crystals suitable for X-ray diffraction studies were obtained after about four weeks by slow evaporation from an acetonitrile solution of (I).

Refinement top

Non-H atoms were refined anisotropically. H atoms were treated as riding atoms with distances C—H = 0.96 Å (CH3), 0.97 Å (CH2),0.93 Å (CH) and Uiso(H) = 1.2 Ueq(C).

Structure description top

Much interest has been focused on bisoxime compounds, in which the large electronegativity of O atoms is expected to affect strongly the electronic properties of the nitrogen atoms, and exhibit high stability against imine metathesis reactions (Akine et al., 2005). Some of them or their metal complexes are used in wide field due to their variety of applications, especially for catalysis and biological processes, magnetism, and supramolecular architectures (Atwood et al., 2001; Yeap et al., 2008; Dong et al., 2008). Herein, the synthesis and structure of 4,4'-dimethyl-1,3-[propenedioxybis(nitrilomethylidyne)]dibenzene (I) is reported (Fig. 1).

The single-crystal structure of (I) is built up by discrete C19H22N2O2 molecules, in which all bond lengths are in normal ranges. The title compound adopts a V-shaped configuration with the dihedral angle between the two halves of the molecule is 85.82 (3)°. The molecules are disposed about a crystallographic two-fold rotation axis. This structure is similar to that observed in our previously reported salen-type bisoxime compounds (He et al., 2008). The packing of the molecule is controlled by C—H···π(Ph) interactions linking molecules into infinite supramolecular structure along b axis.

For bisoximes and their applications, see: Akine et al. (2005); Atwood & Harvey (2001); Dong et al. (2008, 2009); He et al. (2008); Yeap et al. (2008). Cg1 is the centroid of the C4–C9 ring.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL (Sheldrick, 2008); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecule structure of the title compound with atom numbering [Symmetry codes: -x, y, 1/2 - z]. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the supramolecular structure of the title compound. C—H···π(Ph) interactions are shown as dashed lines.
1,3-Bis[(4-methylbenzylidene)aminooxy]propane top
Crystal data top
C19H22N2O2F(000) = 664
Mr = 310.39Dx = 1.184 Mg m3
Monoclinic, C2/cMelting point = 329–330 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 29.843 (2) ÅCell parameters from 780 reflections
b = 4.8668 (7) Åθ = 2.8–25.2°
c = 12.1202 (11) ŵ = 0.08 mm1
β = 98.568 (1)°T = 298 K
V = 1740.7 (3) Å3Needle-like, colorless
Z = 40.43 × 0.13 × 0.07 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1530 independent reflections
Radiation source: fine-focus sealed tube831 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
phi and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3425
Tmin = 0.968, Tmax = 0.995k = 55
4227 measured reflectionsl = 1414
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.071P)2]
where P = (Fo2 + 2Fc2)/3
1530 reflections(Δ/σ)max < 0.001
106 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C19H22N2O2V = 1740.7 (3) Å3
Mr = 310.39Z = 4
Monoclinic, C2/cMo Kα radiation
a = 29.843 (2) ŵ = 0.08 mm1
b = 4.8668 (7) ÅT = 298 K
c = 12.1202 (11) Å0.43 × 0.13 × 0.07 mm
β = 98.568 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
1530 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
831 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.995Rint = 0.062
4227 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.175H-atom parameters constrained
S = 1.12Δρmax = 0.13 e Å3
1530 reflectionsΔρmin = 0.20 e Å3
106 parameters
Special details top

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) top
xyzUiso*/Ueq
N10.58112 (8)0.7298 (5)0.3832 (2)0.0491 (7)
O10.54391 (7)0.5473 (4)0.36901 (16)0.0562 (7)
C10.54272 (10)0.4006 (7)0.2661 (2)0.0530 (9)
H1A0.56910.28260.26910.064*
H1B0.54260.52830.20460.064*
C20.50000.2312 (9)0.25000.0532 (12)
H20.49990.11360.31460.064*
C30.58513 (10)0.8441 (7)0.4781 (2)0.0493 (8)
H30.56460.79790.52580.059*
C40.62026 (9)1.0435 (6)0.5161 (2)0.0436 (8)
C50.65245 (10)1.1316 (7)0.4504 (2)0.0494 (8)
H50.65181.06090.37900.059*
C60.68507 (10)1.3223 (7)0.4909 (2)0.0518 (9)
H60.70601.37780.44580.062*
C70.68736 (10)1.4340 (6)0.5977 (2)0.0487 (8)
C80.65537 (11)1.3458 (7)0.6621 (2)0.0558 (9)
H80.65611.41630.73360.067*
C90.62262 (10)1.1564 (6)0.6225 (2)0.0518 (8)
H90.60161.10260.66780.062*
C100.72298 (11)1.6435 (7)0.6406 (3)0.0653 (10)
H10A0.75151.59040.61940.098*
H10B0.72581.65340.72040.098*
H10C0.71431.82010.60920.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0415 (15)0.0518 (18)0.0529 (15)0.0036 (13)0.0040 (11)0.0018 (13)
O10.0463 (13)0.0644 (16)0.0579 (13)0.0126 (11)0.0075 (10)0.0103 (12)
C10.0468 (19)0.052 (2)0.0585 (18)0.0048 (17)0.0032 (14)0.0096 (17)
C20.050 (3)0.044 (3)0.063 (3)0.0000.001 (2)0.000
C30.0466 (18)0.054 (2)0.0473 (17)0.0002 (16)0.0078 (13)0.0002 (16)
C40.0435 (18)0.0414 (19)0.0448 (16)0.0022 (14)0.0030 (13)0.0016 (14)
C50.0487 (19)0.058 (2)0.0404 (15)0.0010 (17)0.0023 (14)0.0006 (15)
C60.0481 (19)0.055 (2)0.0524 (18)0.0002 (17)0.0069 (14)0.0061 (16)
C70.053 (2)0.0372 (19)0.0520 (17)0.0036 (16)0.0058 (15)0.0032 (16)
C80.071 (2)0.051 (2)0.0448 (16)0.0016 (18)0.0070 (16)0.0050 (16)
C90.057 (2)0.055 (2)0.0456 (17)0.0020 (17)0.0117 (14)0.0012 (16)
C100.069 (2)0.050 (2)0.071 (2)0.0028 (19)0.0081 (18)0.0022 (18)
Geometric parameters (Å, º) top
N1—C31.268 (3)C5—C61.381 (4)
N1—O11.412 (3)C5—H50.9300
O1—C11.433 (3)C6—C71.397 (4)
C1—C21.506 (4)C6—H60.9300
C1—H1A0.9700C7—C81.388 (4)
C1—H1B0.9700C7—C101.508 (4)
C2—C1i1.506 (4)C8—C91.377 (4)
C2—H20.9700C8—H80.9300
C3—C41.452 (4)C9—H90.9300
C3—H30.9300C10—H10A0.9600
C4—C91.394 (4)C10—H10B0.9600
C4—C51.403 (4)C10—H10C0.9600
C3—N1—O1110.7 (2)C4—C5—H5119.7
N1—O1—C1109.6 (2)C5—C6—C7121.7 (3)
O1—C1—C2107.2 (2)C5—C6—H6119.2
O1—C1—H1A110.3C7—C6—H6119.2
C2—C1—H1A110.3C8—C7—C6117.3 (3)
O1—C1—H1B110.3C8—C7—C10121.6 (3)
C2—C1—H1B110.3C6—C7—C10121.1 (3)
H1A—C1—H1B108.5C9—C8—C7121.6 (3)
C1—C2—C1i113.6 (4)C9—C8—H8119.2
C1—C2—H2108.8C7—C8—H8119.2
C1i—C2—H2108.8C8—C9—C4121.4 (3)
N1—C3—C4123.2 (3)C8—C9—H9119.3
N1—C3—H3118.4C4—C9—H9119.3
C4—C3—H3118.4C7—C10—H10A109.5
C9—C4—C5117.4 (3)C7—C10—H10B109.5
C9—C4—C3119.4 (3)H10A—C10—H10B109.5
C5—C4—C3123.2 (3)C7—C10—H10C109.5
C6—C5—C4120.7 (3)H10A—C10—H10C109.5
C6—C5—H5119.7H10B—C10—H10C109.5
C3—N1—O1—C1174.3 (2)C4—C5—C6—C70.1 (5)
N1—O1—C1—C2174.5 (2)C5—C6—C7—C80.1 (4)
O1—C1—C2—C1i65.14 (18)C5—C6—C7—C10179.6 (3)
O1—N1—C3—C4179.6 (2)C6—C7—C8—C90.1 (4)
N1—C3—C4—C9179.1 (3)C10—C7—C8—C9179.4 (3)
N1—C3—C4—C51.2 (5)C7—C8—C9—C40.3 (5)
C9—C4—C5—C60.2 (4)C5—C4—C9—C80.4 (4)
C3—C4—C5—C6179.9 (3)C3—C4—C9—C8179.9 (3)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10C···Cg10.962.733.614 (2)153

Experimental details

Crystal data
Chemical formulaC19H22N2O2
Mr310.39
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)29.843 (2), 4.8668 (7), 12.1202 (11)
β (°) 98.568 (1)
V3)1740.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.43 × 0.13 × 0.07
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.968, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
4227, 1530, 831
Rint0.062
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.175, 1.12
No. of reflections1530
No. of parameters106
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.20

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10C···Cg10.962.7343.614 (2)152.86
 

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0904–11) and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

References

First citationAkine, S., Taniguchi, T., Dong, W. K., Masubuchi, S. & Nabeshima, T. (2005). J. Org. Chem. 70, 1704–1711.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationAtwood, D. A. & Harvey, M. (2001). Chem. Rev. 101, 37–52.  Web of Science CrossRef PubMed CAS Google Scholar
First citationDong, W.-K., He, X.-N., Li, L., Lv, Z.-W. & Tong, J.-F. (2008). Acta Cryst. E64, o1405.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationDong, W.-K., Zhao, C.-Y., Sun, Y.-X., Tang, X.-L. & He, X.-N. (2009). Inorg. Chem. Commun. 12, 234–236.  Web of Science CSD CrossRef CAS Google Scholar
First citationHe, X.-N., Dong, W.-K., Bai, W.-J., Yan, H.-B. & Lv, Z.-W. (2008). Acta Cryst. E64, o1532.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationYeap, C. S., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o1854.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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