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

Wu, J.-C.; Gao, S.-X.; Dong, W.-K.; Tong, J.-F.; Li, L.

doi:10.1107/S1600536809042147

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2784

https://doi.org/10.1107/S1600536809042147

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

Jian-Chao Wu,^a Su-Xia Gao,^b Wen-Kui Dong,^a ^* Jun-Feng Tong ^a and Li Li ^a

^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 ); Atwood & Harvey (2001 ); Dong et al. (2008 , 2009 ); He et al. (2008 ); Yeap et al. (2008 ).

Experimental

Crystal data

C₁₉H₂₂N₂O₂
M_r = 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 ) T_min = 0.968, T_max = 0.995
4227 measured reflections
1530 independent reflections
831 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.175
S = 1.12
1530 reflections
106 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯Cg1	0.96	2.73	3.614 (2)	153
Cg1 is the centroid of the C4–C9 ring.

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; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809042147/hg2578sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042147/hg2578Isup2.hkl

checkCIF report

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).

Structure description top

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

	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.
	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

C₁₉H₂₂N₂O₂	F(000) = 664
M_r = 310.39	D_x = 1.184 Mg m⁻³
Monoclinic, C2/c	Melting point = 329–330 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 29.843 (2) Å	Cell parameters from 780 reflections
b = 4.8668 (7) Å	θ = 2.8–25.2°
c = 12.1202 (11) Å	µ = 0.08 mm⁻¹
β = 98.568 (1)°	T = 298 K
V = 1740.7 (3) Å³	Needle-like, colorless
Z = 4	0.43 × 0.13 × 0.07 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	1530 independent reflections
Radiation source: fine-focus sealed tube	831 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
phi and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→25
T_min = 0.968, T_max = 0.995	k = −5→5
4227 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.071P)²] where P = (F_o² + 2F_c²)/3
1530 reflections	(Δ/σ)_max < 0.001
106 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₂₂N₂O₂	V = 1740.7 (3) Å³
M_r = 310.39	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 29.843 (2) Å	µ = 0.08 mm⁻¹
b = 4.8668 (7) Å	T = 298 K
c = 12.1202 (11) Å	0.43 × 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)
T_min = 0.968, T_max = 0.995	R_int = 0.062
4227 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.12	Δρ_max = 0.13 e Å⁻³
1530 reflections	Δρ_min = −0.20 e Å⁻³
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

	x	y	z	U_iso*/U_eq
N1	0.58112 (8)	0.7298 (5)	0.3832 (2)	0.0491 (7)
O1	0.54391 (7)	0.5473 (4)	0.36901 (16)	0.0562 (7)
C1	0.54272 (10)	0.4006 (7)	0.2661 (2)	0.0530 (9)
H1A	0.5691	0.2826	0.2691	0.064*
H1B	0.5426	0.5283	0.2046	0.064*
C2	0.5000	0.2312 (9)	0.2500	0.0532 (12)
H2	0.4999	0.1136	0.3146	0.064*
C3	0.58513 (10)	0.8441 (7)	0.4781 (2)	0.0493 (8)
H3	0.5646	0.7979	0.5258	0.059*
C4	0.62026 (9)	1.0435 (6)	0.5161 (2)	0.0436 (8)
C5	0.65245 (10)	1.1316 (7)	0.4504 (2)	0.0494 (8)
H5	0.6518	1.0609	0.3790	0.059*
C6	0.68507 (10)	1.3223 (7)	0.4909 (2)	0.0518 (9)
H6	0.7060	1.3778	0.4458	0.062*
C7	0.68736 (10)	1.4340 (6)	0.5977 (2)	0.0487 (8)
C8	0.65537 (11)	1.3458 (7)	0.6621 (2)	0.0558 (9)
H8	0.6561	1.4163	0.7336	0.067*
C9	0.62262 (10)	1.1564 (6)	0.6225 (2)	0.0518 (8)
H9	0.6016	1.1026	0.6678	0.062*
C10	0.72298 (11)	1.6435 (7)	0.6406 (3)	0.0653 (10)
H10A	0.7515	1.5904	0.6194	0.098*
H10B	0.7258	1.6534	0.7204	0.098*
H10C	0.7143	1.8201	0.6092	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0415 (15)	0.0518 (18)	0.0529 (15)	−0.0036 (13)	0.0040 (11)	−0.0018 (13)
O1	0.0463 (13)	0.0644 (16)	0.0579 (13)	−0.0126 (11)	0.0075 (10)	−0.0103 (12)
C1	0.0468 (19)	0.052 (2)	0.0585 (18)	0.0048 (17)	0.0032 (14)	−0.0096 (17)
C2	0.050 (3)	0.044 (3)	0.063 (3)	0.000	−0.001 (2)	0.000
C3	0.0466 (18)	0.054 (2)	0.0473 (17)	0.0002 (16)	0.0078 (13)	−0.0002 (16)
C4	0.0435 (18)	0.0414 (19)	0.0448 (16)	0.0022 (14)	0.0030 (13)	0.0016 (14)
C5	0.0487 (19)	0.058 (2)	0.0404 (15)	0.0010 (17)	0.0023 (14)	−0.0006 (15)
C6	0.0481 (19)	0.055 (2)	0.0524 (18)	0.0002 (17)	0.0069 (14)	0.0061 (16)
C7	0.053 (2)	0.0372 (19)	0.0520 (17)	0.0036 (16)	−0.0058 (15)	0.0032 (16)
C8	0.071 (2)	0.051 (2)	0.0448 (16)	0.0016 (18)	0.0070 (16)	−0.0050 (16)
C9	0.057 (2)	0.055 (2)	0.0456 (17)	−0.0020 (17)	0.0117 (14)	−0.0012 (16)
C10	0.069 (2)	0.050 (2)	0.071 (2)	−0.0028 (19)	−0.0081 (18)	0.0022 (18)

Geometric parameters (Å, º) top

N1—C3	1.268 (3)	C5—C6	1.381 (4)
N1—O1	1.412 (3)	C5—H5	0.9300
O1—C1	1.433 (3)	C6—C7	1.397 (4)
C1—C2	1.506 (4)	C6—H6	0.9300
C1—H1A	0.9700	C7—C8	1.388 (4)
C1—H1B	0.9700	C7—C10	1.508 (4)
C2—C1ⁱ	1.506 (4)	C8—C9	1.377 (4)
C2—H2	0.9700	C8—H8	0.9300
C3—C4	1.452 (4)	C9—H9	0.9300
C3—H3	0.9300	C10—H10A	0.9600
C4—C9	1.394 (4)	C10—H10B	0.9600
C4—C5	1.403 (4)	C10—H10C	0.9600

C3—N1—O1	110.7 (2)	C4—C5—H5	119.7
N1—O1—C1	109.6 (2)	C5—C6—C7	121.7 (3)
O1—C1—C2	107.2 (2)	C5—C6—H6	119.2
O1—C1—H1A	110.3	C7—C6—H6	119.2
C2—C1—H1A	110.3	C8—C7—C6	117.3 (3)
O1—C1—H1B	110.3	C8—C7—C10	121.6 (3)
C2—C1—H1B	110.3	C6—C7—C10	121.1 (3)
H1A—C1—H1B	108.5	C9—C8—C7	121.6 (3)
C1—C2—C1ⁱ	113.6 (4)	C9—C8—H8	119.2
C1—C2—H2	108.8	C7—C8—H8	119.2
C1ⁱ—C2—H2	108.8	C8—C9—C4	121.4 (3)
N1—C3—C4	123.2 (3)	C8—C9—H9	119.3
N1—C3—H3	118.4	C4—C9—H9	119.3
C4—C3—H3	118.4	C7—C10—H10A	109.5
C9—C4—C5	117.4 (3)	C7—C10—H10B	109.5
C9—C4—C3	119.4 (3)	H10A—C10—H10B	109.5
C5—C4—C3	123.2 (3)	C7—C10—H10C	109.5
C6—C5—C4	120.7 (3)	H10A—C10—H10C	109.5
C6—C5—H5	119.7	H10B—C10—H10C	109.5

C3—N1—O1—C1	−174.3 (2)	C4—C5—C6—C7	0.1 (5)
N1—O1—C1—C2	−174.5 (2)	C5—C6—C7—C8	−0.1 (4)
O1—C1—C2—C1ⁱ	65.14 (18)	C5—C6—C7—C10	−179.6 (3)
O1—N1—C3—C4	−179.6 (2)	C6—C7—C8—C9	−0.1 (4)
N1—C3—C4—C9	−179.1 (3)	C10—C7—C8—C9	179.4 (3)
N1—C3—C4—C5	1.2 (5)	C7—C8—C9—C4	0.3 (5)
C9—C4—C5—C6	0.2 (4)	C5—C4—C9—C8	−0.4 (4)
C3—C4—C5—C6	179.9 (3)	C3—C4—C9—C8	179.9 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···Cg1	0.96	2.73	3.614 (2)	153

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂N₂O₂
M_r	310.39
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	29.843 (2), 4.8668 (7), 12.1202 (11)
β (°)	98.568 (1)
V (Å³)	1740.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.43 × 0.13 × 0.07

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	4227, 1530, 831
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.175, 1.12
No. of reflections	1530
No. of parameters	106
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C10—H10C···Cg1	0.96	2.734	3.614 (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

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