1,3-Bis[(4-nitro-benzyl-idene)amino-oxy]propane.

The complete molecule of title compound, C(17)H(16)N(4)O(6), is generated by a crystallographic twofold axis. Within the mol-ecule, the two benzene units are approximately perpen-dicular, making a dihedral angle of 85.91 (4)°. In the crystal, mol-ecules are linked into a three-dimensional network by C-H⋯O hydrogen bonds and short O⋯O and N⋯O inter-actions, with distances of 2.998 (2) and 2.968 (3) Å, respectively.

Related literature

For general background to Schiff base complexes and their applications, see: Niederhoffer et al. (1984 ▶); Zhang et al. (1990 ▶); Tisato et al. (1994 ▶); Lacroix (2001 ▶); Sundari et al. (1997 ▶); Koehler et al. (1964 ▶); Cordes & Jencks (1962 ▶); Akine et al. (2006 ▶). For related structures, see: Fun et al. (2008a ▶,b ▶); Kia et al. (2009 ▶); Shi et al. (2007 ▶); Ren et al. (2008 ▶); Ding et al. (2009 ▶); Dong et al. (2008a ▶). For a related Schiff base bis­oxime compound synthesized using a similar route, see: Dong et al. (2008b ▶).

Experimental

Crystal data

C17H16N4O6

M = 372.34

Monoclinic,

a = 29.005 (3) Å

b = 4.7878 (5) Å

c = 6.3579 (7) Å

β = 99.144 (1)°

V = 871.71 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.45 × 0.17 × 0.06 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.993

2321 measured reflections

872 independent reflections

675 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.094

S = 0.96

872 reflections

123 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.19 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/S1600536809031316/fl2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031316/fl2256Isup2.hkl

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

C17H16N4O6	F(000) = 388
Mr = 372.34	Dx = 1.419 Mg m−3
Monoclinic, C2	Melting point = 427–429 K
Hall symbol: C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 29.005 (3) Å	Cell parameters from 773 reflections
b = 4.7878 (5) Å	θ = 2.9–25.3°
c = 6.3579 (7) Å	µ = 0.11 mm−1
β = 99.144 (1)°	T = 298 K
V = 871.71 (16) Å3	Needle-like, colorless
Z = 2	0.45 × 0.17 × 0.06 mm

Siemens SMART 1000 CCD area-detector diffractometer	872 independent reflections
Radiation source: fine-focus sealed tube	675 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→34
Tmin = 0.952, Tmax = 0.993	k = −5→5
2321 measured reflections	l = −7→7

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0524P)2] where P = (Fo2 + 2Fc2)/3
872 reflections	(Δ/σ)max < 0.001
123 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.19 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	Occ. (<1)
N1	0.93031 (9)	0.2933 (7)	0.6567 (4)	0.0497 (7)
N2	0.79744 (9)	1.2194 (6)	0.1169 (4)	0.0479 (7)
O1	0.94454 (7)	0.1141 (6)	0.8289 (3)	0.0560 (7)
O2	0.76377 (8)	1.3375 (6)	0.1705 (3)	0.0643 (7)
O3	0.81103 (8)	1.2669 (6)	−0.0530 (3)	0.0656 (8)
C1	0.98599 (10)	−0.0342 (8)	0.8012 (4)	0.0508 (9)
H1A	1.0106	0.0956	0.7815	0.061*
H1B	0.9799	−0.1551	0.6775	0.061*
C2	1.0000	−0.2040 (12)	1.0000	0.0511 (12)
H2A	0.9741	−0.3236	1.0203	0.061*	0.50
H2B	1.0259	−0.3236	0.9797	0.061*	0.50
C3	0.89337 (11)	0.4213 (8)	0.6853 (5)	0.0486 (9)
H3	0.8809	0.3840	0.8082	0.058*
C4	0.86975 (10)	0.6240 (8)	0.5337 (4)	0.0418 (8)
C5	0.88617 (10)	0.6955 (7)	0.3454 (4)	0.0501 (9)
H5	0.9130	0.6115	0.3120	0.060*
C6	0.86237 (10)	0.8918 (7)	0.2086 (5)	0.0481 (9)
H6	0.8733	0.9422	0.0841	0.058*
C7	0.82254 (10)	1.0105 (7)	0.2594 (4)	0.0405 (7)
C8	0.80565 (10)	0.9443 (8)	0.4438 (4)	0.0470 (9)
H8	0.7787	1.0280	0.4756	0.056*
C9	0.82958 (10)	0.7517 (8)	0.5798 (4)	0.0473 (8)
H9	0.8186	0.7061	0.7053	0.057*

	U11	U22	U33	U12	U13	U23
N1	0.0561 (17)	0.0467 (17)	0.0439 (14)	−0.0031 (16)	0.0009 (12)	0.0075 (15)
N2	0.0530 (16)	0.0421 (18)	0.0486 (14)	−0.0031 (15)	0.0076 (13)	0.0048 (14)
O1	0.0543 (14)	0.0622 (16)	0.0514 (12)	0.0090 (13)	0.0083 (10)	0.0130 (13)
O2	0.0691 (15)	0.0610 (18)	0.0650 (14)	0.0177 (15)	0.0178 (12)	0.0114 (14)
O3	0.0766 (15)	0.0688 (19)	0.0547 (12)	0.0025 (15)	0.0208 (11)	0.0196 (15)
C1	0.0476 (17)	0.047 (2)	0.0561 (19)	−0.0001 (18)	0.0044 (15)	−0.0014 (17)
C2	0.049 (3)	0.044 (3)	0.057 (3)	0.000	−0.001 (2)	0.000
C3	0.0467 (17)	0.051 (2)	0.0488 (18)	−0.002 (2)	0.0108 (15)	0.0082 (18)
C4	0.0441 (17)	0.0393 (19)	0.0408 (15)	−0.0048 (16)	0.0034 (14)	0.0022 (16)
C5	0.0471 (18)	0.056 (3)	0.0495 (17)	0.0035 (19)	0.0136 (15)	0.0007 (18)
C6	0.0535 (19)	0.052 (2)	0.0405 (16)	−0.0020 (19)	0.0125 (14)	0.0062 (16)
C7	0.0457 (16)	0.0351 (18)	0.0395 (15)	−0.0039 (15)	0.0032 (13)	0.0016 (14)
C8	0.0469 (18)	0.048 (2)	0.0486 (18)	0.0014 (18)	0.0165 (15)	0.0034 (17)
C9	0.0480 (17)	0.051 (2)	0.0448 (16)	0.0022 (18)	0.0139 (13)	0.0090 (17)

N1—C3	1.273 (4)	C3—C4	1.459 (4)
N1—O1	1.401 (3)	C3—H3	0.9300
N2—O2	1.223 (3)	C4—C9	1.388 (4)
N2—O3	1.229 (3)	C4—C5	1.399 (4)
N2—C7	1.464 (4)	C5—C6	1.387 (4)
O1—C1	1.431 (3)	C5—H5	0.9300
C1—C2	1.503 (5)	C6—C7	1.371 (4)
C1—H1A	0.9700	C6—H6	0.9300
C1—H1B	0.9700	C7—C8	1.378 (4)
C2—C1i	1.503 (5)	C8—C9	1.374 (5)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—H9	0.9300
C3—N1—O1	109.5 (2)	C4—C3—H3	118.5
O2—N2—O3	122.8 (3)	C9—C4—C5	119.0 (3)
O2—N2—C7	119.0 (2)	C9—C4—C3	118.4 (3)
O3—N2—C7	118.2 (3)	C5—C4—C3	122.7 (3)
N1—O1—C1	110.9 (2)	C6—C5—C4	119.9 (3)
O1—C1—C2	106.5 (2)	C6—C5—H5	120.0
O1—C1—H1A	110.4	C4—C5—H5	120.0
C2—C1—H1A	110.4	C7—C6—C5	119.2 (3)
O1—C1—H1B	110.4	C7—C6—H6	120.4
C2—C1—H1B	110.4	C5—C6—H6	120.4
H1A—C1—H1B	108.6	C6—C7—C8	122.1 (3)
C1i—C2—C1	114.5 (5)	C6—C7—N2	119.5 (3)
C1i—C2—H2A	108.6	C8—C7—N2	118.4 (3)
C1—C2—H2A	108.6	C9—C8—C7	118.5 (3)
C1i—C2—H2B	108.6	C9—C8—H8	120.7
C1—C2—H2B	108.6	C7—C8—H8	120.7
H2A—C2—H2B	107.6	C8—C9—C4	121.3 (3)
N1—C3—C4	122.9 (3)	C8—C9—H9	119.3
N1—C3—H3	118.5	C4—C9—H9	119.3
C3—N1—O1—C1	179.8 (3)	C5—C6—C7—N2	179.5 (3)
N1—O1—C1—C2	176.2 (3)	O2—N2—C7—C6	−175.2 (3)
O1—C1—C2—C1i	−64.9 (2)	O3—N2—C7—C6	5.4 (4)
O1—N1—C3—C4	179.9 (3)	O2—N2—C7—C8	3.4 (4)
N1—C3—C4—C9	179.9 (3)	O3—N2—C7—C8	−176.0 (3)
N1—C3—C4—C5	−0.6 (5)	C6—C7—C8—C9	−0.3 (5)
C9—C4—C5—C6	0.1 (5)	N2—C7—C8—C9	−178.9 (3)
C3—C4—C5—C6	−179.4 (3)	C7—C8—C9—C4	−0.4 (5)
C4—C5—C6—C7	−0.9 (5)	C5—C4—C9—C8	0.5 (5)
C5—C6—C7—C8	1.0 (5)	C3—C4—C9—C8	−179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ii	0.93	2.40	3.206 (4)	145
C9—H9···O3ii	0.93	2.63	3.395 (4)	139
C9—H9···O2iii	0.93	2.71	3.374 (4)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.40	3.206 (4)	145
C9—H9⋯O3i	0.93	2.63	3.395 (4)	139
C9—H9⋯O2ii	0.93	2.71	3.374 (4)	129

Symmetry codes: (i) ; (ii) .