1,3-Bis[(4-methylbenzylidene)amino-oxy]propane.

The title bis-oxime compound, C(19)H(22)N(2)O(2), synthesized by the reaction of 4-methyl-2-hydroxy-benzaldehyde with 1,3-bis-(amino-oxy)propane in ethanol, adopts a V-shaped conformation. The dihedral angle between the rings is 84.59 (3)°. The mol-ecule is disposed about a crystallographic twofold rotation axis, with one C atom lying on the axis. In the crystal, mol-ecules are packed by C-H⋯π(Ph) inter-actions, 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 = 310.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 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

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042147/hg2578Isup2.hkl

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

C19H22N2O2	F(000) = 664
Mr = 310.39	Dx = 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

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

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(Fo2) + (0.071P)2] where P = (Fo2 + 2Fc2)/3
1530 reflections	(Δ/σ)max < 0.001
106 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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.