6,6'-Dihydr-oxy-2,2'-[(propane-1,3-diyl-dioxy)bis-(nitrilo-methyl-idyne)]diphenol.

The mol-ecule of the title compound, C(17)H(18)N(2)O(6), adopts a V-shaped conformation, the dihedral angle between the two halves of the mol-ecule being 81.31 (4) °. There is one half-mol-ecule in the asymmetric unit, with a crystallographic twofold rotation axis passing through the central C atom. There are strong intra-molecular O-H⋯N and O-H⋯O hydrogen bonds involving the hydr-oxy group and adjacent O and N atoms. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules, forming an infinite three-dimensional supra-molecular structure.

Related literature

For related literature, see: Akine et al. (2006 ▶); Dong & Feng (2006 ▶); Dong et al. (2008a ▶,b ▶,c ▶); Duan et al. (2007 ▶); Sharma (2002 ▶); Sun et al. (2004 ▶); Venkataramanan et al. (2005 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

C17H18N2O6

M = 346.33

Monoclinic,

a = 27.836 (3) Å

b = 4.5949 (5) Å

c = 13.8081 (10) Å

β = 109.363 (2)°

V = 1666.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.43 × 0.40 × 0.31 mm

Data collection

Brucker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.956, T max = 0.968

4032 measured reflections

1476 independent reflections

1025 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.186

S = 1.05

1476 reflections

114 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 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 2, I. DOI: 10.1107/S1600536808026731/pv2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026731/pv2099Isup2.hkl

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

C17H18N2O6	F000 = 728
Mr = 346.33	Dx = 1.381 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1493 reflections
a = 27.836 (3) Å	θ = 2.8–27.7º
b = 4.5949 (5) Å	µ = 0.11 mm−1
c = 13.8081 (10) Å	T = 298 (2) K
β = 109.363 (2)º	Prismatic, pale-brown
V = 1666.2 (3) Å3	0.43 × 0.40 × 0.31 mm
Z = 4

Brucker SMART 1000 CCD area-detector diffractometer	1476 independent reflections
Radiation source: fine-focus sealed tube	1025 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 298(2) K	θmax = 25.0º
phi and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −32→27
Tmin = 0.956, Tmax = 0.968	k = −5→5
4032 measured reflections	l = −16→16

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.186	w = 1/[σ2(Fo2) + (0.0856P)2 + 2.8739P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1476 reflections	Δρmax = 0.20 e Å−3
114 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. Yield, 59.1%, mp. 425–427 K. Anal. Calc. for C17H18N2O6: C, 59.96; H, 5.24; N, 8.09. Found: C, 60.17; H, 5.31; N, 7.92.

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)
O1	0.43592 (8)	0.2306 (5)	1.15521 (16)	0.0466 (6)
O2	0.41085 (8)	0.6412 (6)	0.88832 (17)	0.0539 (7)
H2	0.4236	0.5367	0.9385	0.081*
O3	0.36020 (10)	1.0086 (6)	0.73677 (18)	0.0671 (9)
H3	0.3855	0.9080	0.7439	0.101*
N1	0.41732 (9)	0.4035 (6)	1.06706 (18)	0.0413 (7)
C1	0.48064 (12)	0.0823 (7)	1.1531 (2)	0.0456 (8)
H1A	0.5063	0.2214	1.1500	0.055*
H1B	0.4727	−0.0431	1.0933	0.055*
C2	0.5000	−0.0961 (11)	1.2500	0.0529 (13)
H2A	0.4727	−0.2207	1.2545	0.063*	0.50
H2B	0.5273	−0.2207	1.2455	0.063*	0.50
C4	0.37794 (11)	0.5439 (7)	1.0649 (2)	0.0409 (8)
H4	0.3650	0.5210	1.1185	0.049*
C5	0.35228 (11)	0.7400 (7)	0.9813 (2)	0.0372 (7)
C6	0.36954 (11)	0.7802 (7)	0.8979 (2)	0.0387 (8)
C7	0.34391 (12)	0.9687 (7)	0.8197 (2)	0.0446 (8)
C8	0.30183 (13)	1.1161 (8)	0.8225 (3)	0.0499 (9)
H8	0.2850	1.2423	0.7695	0.060*
C9	0.28425 (12)	1.0774 (8)	0.9046 (3)	0.0490 (9)
H9	0.2555	1.1772	0.9066	0.059*
C10	0.30912 (12)	0.8929 (8)	0.9822 (2)	0.0443 (8)
H10	0.2971	0.8682	1.0369	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.0425 (12)	0.0521 (15)	0.0435 (13)	0.0042 (11)	0.0119 (10)	0.0151 (11)
O2	0.0523 (14)	0.0655 (16)	0.0510 (14)	0.0138 (12)	0.0267 (11)	0.0107 (12)
O3	0.0821 (19)	0.0788 (19)	0.0470 (15)	0.0177 (15)	0.0303 (13)	0.0176 (13)
N1	0.0411 (15)	0.0424 (16)	0.0377 (14)	−0.0041 (13)	0.0096 (11)	0.0029 (12)
C1	0.0406 (18)	0.044 (2)	0.0480 (19)	0.0026 (15)	0.0094 (15)	−0.0031 (16)
C2	0.049 (3)	0.044 (3)	0.056 (3)	0.000	0.005 (2)	0.000
C4	0.0387 (17)	0.047 (2)	0.0377 (17)	−0.0033 (15)	0.0133 (14)	−0.0002 (15)
C5	0.0364 (16)	0.0367 (18)	0.0360 (16)	−0.0084 (14)	0.0088 (13)	−0.0060 (14)
C6	0.0352 (16)	0.0391 (18)	0.0407 (17)	−0.0009 (14)	0.0110 (13)	−0.0033 (15)
C7	0.051 (2)	0.047 (2)	0.0352 (17)	−0.0083 (16)	0.0123 (15)	−0.0008 (15)
C8	0.0468 (19)	0.048 (2)	0.0446 (19)	0.0064 (17)	0.0017 (15)	0.0040 (16)
C9	0.0396 (18)	0.054 (2)	0.050 (2)	0.0042 (17)	0.0106 (15)	−0.0062 (18)
C10	0.0418 (18)	0.050 (2)	0.0429 (18)	−0.0044 (16)	0.0165 (14)	−0.0055 (16)

O1—N1	1.401 (3)	C2—H2B	0.9700
O1—C1	1.428 (4)	C4—C5	1.452 (4)
O2—C6	1.359 (4)	C4—H4	0.9300
O2—H2	0.8207	C5—C10	1.395 (4)
O3—C7	1.377 (4)	C5—C6	1.400 (4)
O3—H3	0.8195	C6—C7	1.383 (4)
N1—C4	1.264 (4)	C7—C8	1.365 (5)
C1—C2	1.508 (4)	C8—C9	1.387 (5)
C1—H1A	0.9700	C8—H8	0.9300
C1—H1B	0.9700	C9—C10	1.362 (5)
C2—C1i	1.508 (4)	C9—H9	0.9300
C2—H2A	0.9700	C10—H10	0.9300
N1—O1—C1	109.0 (2)	C10—C5—C6	118.2 (3)
C6—O2—H2	109.7	C10—C5—C4	120.2 (3)
C7—O3—H3	109.3	C6—C5—C4	121.6 (3)
C4—N1—O1	112.2 (2)	O2—C6—C7	116.9 (3)
O1—C1—C2	107.4 (2)	O2—C6—C5	123.4 (3)
O1—C1—H1A	110.2	C7—C6—C5	119.7 (3)
C2—C1—H1A	110.2	C8—C7—O3	118.7 (3)
O1—C1—H1B	110.2	C8—C7—C6	121.0 (3)
C2—C1—H1B	110.2	O3—C7—C6	120.3 (3)
H1A—C1—H1B	108.5	C7—C8—C9	119.9 (3)
C1i—C2—C1	114.2 (4)	C7—C8—H8	120.1
C1i—C2—H2A	108.7	C9—C8—H8	120.1
C1—C2—H2A	108.7	C10—C9—C8	119.9 (3)
C1i—C2—H2B	108.7	C10—C9—H9	120.1
C1—C2—H2B	108.7	C8—C9—H9	120.1
H2A—C2—H2B	107.6	C9—C10—C5	121.4 (3)
N1—C4—C5	122.0 (3)	C9—C10—H10	119.3
N1—C4—H4	119.0	C5—C10—H10	119.3
C5—C4—H4	119.0
C1—O1—N1—C4	−179.2 (3)	O2—C6—C7—C8	179.6 (3)
N1—O1—C1—C2	178.9 (3)	C5—C6—C7—C8	−0.2 (5)
O1—C1—C2—C1i	−66.8 (2)	O2—C6—C7—O3	0.3 (5)
O1—N1—C4—C5	179.3 (3)	C5—C6—C7—O3	−179.5 (3)
N1—C4—C5—C10	−179.5 (3)	O3—C7—C8—C9	179.3 (3)
N1—C4—C5—C6	0.9 (5)	C6—C7—C8—C9	0.0 (5)
C10—C5—C6—O2	−179.4 (3)	C7—C8—C9—C10	0.1 (5)
C4—C5—C6—O2	0.2 (5)	C8—C9—C10—C5	0.0 (5)
C10—C5—C6—C7	0.3 (4)	C6—C5—C10—C9	−0.2 (5)
C4—C5—C6—C7	179.9 (3)	C4—C5—C10—C9	−179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.94	2.650 (3)	144
O3—H3···O2	0.82	2.25	2.694 (4)	115
O3—H3···O1ii	0.82	2.24	2.914 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.94	2.650 (3)	144
O3—H3⋯O2	0.82	2.25	2.694 (4)	115
O3—H3⋯O1i	0.82	2.24	2.914 (4)	140

Symmetry code: (i) .