2,2'-[1,1'-(Propane-1,3-diyldioxy-dinitrilo)diethyl-idyne]diphenol.

The title compound, C(19)H(22)N(2)O(4), was synthesized by the reaction of 2'-hydroxy-acetophenone with 1,3-bis-(amino-oxy)propane in ethanol. Intra-molecular O-H⋯N and weak C-H⋯O hydrogen bonds stabilize the three-dimensional structure. A twofold rotation axis passes through the molecule.

Related literature

For related literature, see: Atkins et al. (1985 ▶); Atwood (1997 ▶); Costes et al. (2000 ▶); Dong & Feng (2006 ▶); Dong et al. (2006a ▶,b ▶, 2007a ▶,b ▶,c ▶,d ▶); Duan et al. (2007 ▶); Katsuki (1995 ▶); Lacroix (2001 ▶); Venkataramanan et al. (2005 ▶); Yu et al. (2008 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

C19H22N2O4

M = 342.39

Orthorhombic,

a = 7.4595 (15) Å

b = 25.459 (2) Å

c = 4.5938 (8) Å

V = 872.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.40 × 0.19 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.985

3761 measured reflections

880 independent reflections

601 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.162

S = 1.12

880 reflections

114 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012701/hg2386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012701/hg2386Isup2.hkl

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

C19H22N2O4	F000 = 364
Mr = 342.39	Dx = 1.303 Mg m−3
Orthorhombic, Pba2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2 -2ab	Cell parameters from 1047 reflections
a = 7.4595 (15) Å	θ = 2.4–22.9º
b = 25.459 (2) Å	µ = 0.09 mm−1
c = 4.5938 (8) Å	T = 298 (2) K
V = 872.4 (2) Å3	Needle-shaped, colorless
Z = 2	0.40 × 0.19 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	880 independent reflections
Radiation source: fine-focus sealed tube	601 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.080
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→4
Tmin = 0.964, Tmax = 0.985	k = −30→28
3761 measured reflections	l = −5→5

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.09P)2] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
880 reflections	Δρmax = 0.18 e Å−3
114 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
N1	0.7665 (5)	0.07883 (13)	0.2794 (9)	0.0424 (10)
O1	0.6235 (4)	0.06405 (11)	0.0997 (8)	0.0497 (10)
O2	1.0675 (4)	0.06514 (11)	0.5410 (10)	0.0613 (12)
H2	0.9857	0.0579	0.4284	0.092*
C1	0.6621 (6)	0.01443 (16)	−0.0329 (12)	0.0447 (13)
H1A	0.6845	−0.0120	0.1148	0.054*
H1B	0.7671	0.0171	−0.1564	0.054*
C2	0.5000	0.0000	−0.2107 (16)	0.0479 (18)
H2A	0.5305	−0.0294	−0.3353	0.058*	0.50
H2B	0.4695	0.0294	−0.3353	0.058*	0.50
C3	0.5696 (7)	0.15361 (18)	0.3585 (17)	0.0660 (17)
H3A	0.5088	0.1406	0.1891	0.099*
H3B	0.5989	0.1900	0.3308	0.099*
H3C	0.4931	0.1500	0.5254	0.099*
C4	0.7390 (6)	0.12265 (17)	0.4060 (10)	0.0406 (12)
C5	0.8802 (6)	0.14197 (16)	0.5999 (11)	0.0380 (11)
C6	1.0350 (6)	0.11254 (15)	0.6663 (11)	0.0396 (12)
C7	1.1585 (6)	0.1310 (2)	0.8622 (13)	0.0540 (15)
H7	1.2586	0.1107	0.9065	0.065*
C8	1.1363 (6)	0.1787 (2)	0.9934 (16)	0.0582 (15)
H8	1.2207	0.1908	1.1263	0.070*
C9	0.9884 (8)	0.2086 (2)	0.9277 (16)	0.0649 (18)
H9	0.9733	0.2414	1.0135	0.078*
C10	0.8645 (7)	0.19013 (18)	0.7369 (13)	0.0521 (15)
H10	0.7646	0.2108	0.6966	0.063*

	U11	U22	U33	U12	U13	U23
N1	0.038 (2)	0.047 (2)	0.043 (2)	−0.0020 (17)	−0.005 (2)	0.002 (2)
O1	0.0458 (18)	0.0516 (19)	0.052 (2)	−0.0039 (14)	−0.0123 (19)	−0.0063 (18)
O2	0.053 (2)	0.054 (2)	0.077 (3)	0.0138 (15)	−0.018 (2)	−0.0045 (19)
C1	0.048 (3)	0.041 (2)	0.045 (3)	−0.004 (2)	0.005 (3)	−0.001 (2)
C2	0.068 (5)	0.046 (3)	0.030 (4)	−0.007 (3)	0.000	0.000
C3	0.051 (3)	0.060 (3)	0.087 (5)	0.009 (2)	−0.021 (4)	−0.015 (3)
C4	0.038 (2)	0.042 (2)	0.042 (3)	0.000 (2)	−0.005 (2)	0.004 (2)
C5	0.035 (2)	0.045 (2)	0.034 (3)	−0.001 (2)	−0.001 (2)	0.004 (2)
C6	0.035 (2)	0.042 (2)	0.042 (3)	−0.002 (2)	−0.002 (2)	0.010 (2)
C7	0.036 (3)	0.066 (3)	0.060 (4)	0.002 (2)	−0.015 (3)	0.009 (3)
C8	0.046 (3)	0.072 (3)	0.057 (4)	−0.015 (3)	−0.011 (3)	−0.001 (3)
C9	0.057 (3)	0.056 (3)	0.082 (5)	−0.003 (3)	−0.017 (4)	−0.016 (3)
C10	0.043 (3)	0.056 (3)	0.057 (4)	0.006 (2)	−0.004 (3)	0.003 (3)

N1—C4	1.275 (5)	C3—H3B	0.9600
N1—O1	1.400 (5)	C3—H3C	0.9600
O1—C1	1.432 (5)	C4—C5	1.464 (6)
O2—C6	1.359 (5)	C5—C10	1.383 (6)
O2—H2	0.8200	C5—C6	1.410 (6)
C1—C2	1.505 (6)	C6—C7	1.370 (7)
C1—H1A	0.9700	C7—C8	1.366 (7)
C1—H1B	0.9700	C7—H7	0.9300
C2—C1i	1.505 (6)	C8—C9	1.374 (7)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—C10	1.358 (8)
C3—C4	1.505 (6)	C9—H9	0.9300
C3—H3A	0.9600	C10—H10	0.9300
C4—N1—O1	112.4 (3)	N1—C4—C5	117.1 (4)
N1—O1—C1	109.5 (3)	N1—C4—C3	121.8 (4)
C6—O2—H2	109.5	C5—C4—C3	121.1 (4)
O1—C1—C2	106.5 (3)	C10—C5—C6	116.2 (4)
O1—C1—H1A	110.4	C10—C5—C4	120.9 (4)
C2—C1—H1A	110.4	C6—C5—C4	122.8 (4)
O1—C1—H1B	110.4	O2—C6—C7	117.6 (4)
C2—C1—H1B	110.4	O2—C6—C5	121.7 (4)
H1A—C1—H1B	108.6	C7—C6—C5	120.7 (4)
C1—C2—C1i	114.3 (6)	C8—C7—C6	120.8 (5)
C1—C2—H2A	108.7	C8—C7—H7	119.6
C1i—C2—H2A	108.7	C6—C7—H7	119.6
C1—C2—H2B	108.7	C7—C8—C9	119.6 (5)
C1i—C2—H2B	108.7	C7—C8—H8	120.2
H2A—C2—H2B	107.6	C9—C8—H8	120.2
C4—C3—H3A	109.5	C10—C9—C8	119.7 (5)
C4—C3—H3B	109.5	C10—C9—H9	120.1
H3A—C3—H3B	109.5	C8—C9—H9	120.1
C4—C3—H3C	109.5	C9—C10—C5	122.9 (5)
H3A—C3—H3C	109.5	C9—C10—H10	118.5
H3B—C3—H3C	109.5	C5—C10—H10	118.5
C4—N1—O1—C1	−179.4 (4)	C4—C5—C6—O2	3.6 (7)
N1—O1—C1—C2	177.5 (4)	C10—C5—C6—C7	1.7 (7)
O1—C1—C2—C1i	−70.3 (3)	C4—C5—C6—C7	−176.2 (4)
O1—N1—C4—C5	180.0 (3)	O2—C6—C7—C8	178.9 (5)
O1—N1—C4—C3	−0.3 (7)	C5—C6—C7—C8	−1.3 (8)
N1—C4—C5—C10	177.4 (5)	C6—C7—C8—C9	−0.1 (9)
C3—C4—C5—C10	−2.3 (7)	C7—C8—C9—C10	1.1 (10)
N1—C4—C5—C6	−4.9 (6)	C8—C9—C10—C5	−0.7 (9)
C3—C4—C5—C6	175.4 (5)	C6—C5—C10—C9	−0.7 (8)
C10—C5—C6—O2	−178.6 (4)	C4—C5—C10—C9	177.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.85	2.570 (5)	146
C3—H3A···O1	0.96	2.17	2.603 (6)	106

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.85	2.570 (5)	146
C3—H3A⋯O1	0.96	2.17	2.603 (6)	106