Diethyl 2,2'-bis-(hy-droxy-imino)-3,3'-(hydrazinediyl-idene)dibutano-ate.

Each mol-ecule of the title compound, C(12)H(18)N(4)O(6), is located on an inversion centre at the mid-point of the central N-N bond. The azo groups C=N of the Schiff base group have an E conformation and the azo groups in the oxime C=N-O groups have a Z conformation. O-H⋯O hydrogen bonds link neighbouring mol-ecules into infinite monolayers perpendicular to the a axis.

Related literature

For background to strobilurin A and strobilurin analogs, see: Zhao et al. (2007 ▶); Balbaa (2007 ▶); Li et al. (2010 ▶); Zakharychev et al. (1999 ▶, 2001 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H18N4O6

M = 314.30

Monoclinic,

a = 10.8587 (11) Å

b = 8.3068 (9) Å

c = 8.8465 (9) Å

β = 99.782 (2)°

V = 786.36 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.18 × 0.18 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

3779 measured reflections

1385 independent reflections

1235 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.09

1385 reflections

103 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812007398/zl2446sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007398/zl2446Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007398/zl2446Isup3.cml

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

C12H18N4O6	F(000) = 332
Mr = 314.30	Dx = 1.327 Mg m−3
Monoclinic, P21/c	Melting point = 473–475 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.8587 (11) Å	Cell parameters from 2318 reflections
b = 8.3068 (9) Å	θ = 3.1–28.2°
c = 8.8465 (9) Å	µ = 0.11 mm−1
β = 99.782 (2)°	T = 296 K
V = 786.36 (14) Å3	Block-like, yellow
Z = 2	0.18 × 0.18 × 0.10 mm

Bruker APEXII CCD diffractometer	1235 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
φ and ω scans	h = −6→12
3779 measured reflections	k = −9→9
1385 independent reflections	l = −10→10

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) = 0.110	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.202P] where P = (Fo2 + 2Fc2)/3
1385 reflections	(Δ/σ)max = 0.001
103 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.24 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
C1	0.3173 (2)	−0.3855 (3)	0.1974 (3)	0.0815 (7)
H1A	0.2823	−0.3486	0.0964	0.122*
H1B	0.2514	−0.4229	0.2485	0.122*
H1C	0.3745	−0.4720	0.1899	0.122*
C2	0.38401 (17)	−0.2522 (2)	0.2854 (2)	0.0543 (5)
H2A	0.4193	−0.2890	0.3877	0.065*
H2B	0.4520	−0.2159	0.2355	0.065*
C3	0.29765 (13)	0.00236 (17)	0.20059 (16)	0.0335 (3)
C4	0.20477 (13)	0.12983 (16)	0.22471 (16)	0.0350 (4)
C5	0.08145 (13)	0.12936 (17)	0.12596 (17)	0.0364 (4)
C6	−0.00087 (18)	0.2722 (2)	0.1254 (3)	0.0702 (6)
H6A	−0.0799	0.2511	0.0615	0.105*
H6B	0.0377	0.3636	0.0862	0.105*
H6C	−0.0137	0.2943	0.2281	0.105*
O1	0.29746 (10)	−0.11865 (13)	0.29545 (13)	0.0455 (3)
O2	0.36466 (10)	0.01499 (13)	0.10565 (12)	0.0442 (3)
O3	0.34902 (10)	0.22632 (15)	0.40794 (13)	0.0518 (4)
H3	0.3626	0.2998	0.4704	0.078*
N2	0.22952 (12)	0.24201 (15)	0.32449 (15)	0.0431 (4)
N1	0.05904 (11)	0.00033 (14)	0.04649 (14)	0.0372 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0890 (16)	0.0520 (12)	0.0992 (17)	0.0159 (11)	0.0036 (13)	−0.0098 (11)
C2	0.0521 (10)	0.0444 (10)	0.0662 (11)	0.0153 (7)	0.0097 (9)	0.0135 (8)
C3	0.0317 (7)	0.0335 (8)	0.0333 (7)	−0.0029 (6)	−0.0005 (6)	−0.0018 (5)
C4	0.0343 (8)	0.0335 (8)	0.0370 (7)	−0.0025 (6)	0.0056 (6)	−0.0020 (6)
C5	0.0333 (8)	0.0356 (8)	0.0399 (8)	0.0008 (6)	0.0051 (6)	−0.0025 (6)
C6	0.0517 (11)	0.0600 (12)	0.0899 (15)	0.0196 (9)	−0.0140 (10)	−0.0303 (11)
O1	0.0461 (7)	0.0393 (6)	0.0530 (7)	0.0064 (5)	0.0133 (5)	0.0100 (5)
O2	0.0430 (6)	0.0473 (7)	0.0441 (6)	0.0072 (5)	0.0123 (5)	0.0068 (5)
O3	0.0424 (6)	0.0549 (7)	0.0529 (7)	−0.0011 (5)	−0.0065 (5)	−0.0187 (5)
N2	0.0381 (7)	0.0438 (8)	0.0458 (7)	−0.0014 (5)	0.0026 (6)	−0.0101 (6)
N1	0.0318 (6)	0.0352 (7)	0.0420 (7)	−0.0003 (5)	−0.0012 (5)	−0.0008 (5)

C1—C2	1.472 (3)	C4—N2	1.2803 (19)
C1—H1A	0.9600	C4—C5	1.469 (2)
C1—H1B	0.9600	C5—N1	1.2822 (19)
C1—H1C	0.9600	C5—C6	1.485 (2)
C2—O1	1.4663 (19)	C6—H6A	0.9600
C2—H2A	0.9700	C6—H6B	0.9600
C2—H2B	0.9700	C6—H6C	0.9600
C3—O2	1.2056 (17)	O3—N2	1.3857 (17)
C3—O1	1.3097 (18)	O3—H3	0.8200
C3—C4	1.5024 (19)	N1—N1i	1.401 (2)
C2—C1—H1A	109.5	N2—C4—C3	122.92 (13)
C2—C1—H1B	109.5	C5—C4—C3	118.66 (12)
H1A—C1—H1B	109.5	N1—C5—C4	113.40 (12)
C2—C1—H1C	109.5	N1—C5—C6	127.44 (14)
H1A—C1—H1C	109.5	C4—C5—C6	119.15 (13)
H1B—C1—H1C	109.5	C5—C6—H6A	109.5
O1—C2—C1	109.77 (16)	C5—C6—H6B	109.5
O1—C2—H2A	109.7	H6A—C6—H6B	109.5
C1—C2—H2A	109.7	C5—C6—H6C	109.5
O1—C2—H2B	109.7	H6A—C6—H6C	109.5
C1—C2—H2B	109.7	H6B—C6—H6C	109.5
H2A—C2—H2B	108.2	C3—O1—C2	118.11 (12)
O2—C3—O1	125.45 (13)	N2—O3—H3	109.5
O2—C3—C4	122.47 (13)	C4—N2—O3	111.52 (12)
O1—C3—C4	112.07 (12)	C5—N1—N1i	113.25 (14)
N2—C4—C5	118.38 (13)
O2—C3—C4—N2	−93.59 (18)	O2—C3—O1—C2	−1.0 (2)
O1—C3—C4—N2	85.26 (17)	C4—C3—O1—C2	−179.80 (13)
O2—C3—C4—C5	84.22 (17)	C1—C2—O1—C3	−99.25 (19)
O1—C3—C4—C5	−96.93 (15)	C5—C4—N2—O3	−179.79 (12)
N2—C4—C5—N1	−170.22 (14)	C3—C4—N2—O3	−2.0 (2)
C3—C4—C5—N1	11.88 (19)	C4—C5—N1—N1i	179.46 (13)
N2—C4—C5—C6	10.7 (2)	C6—C5—N1—N1i	−1.6 (3)
C3—C4—C5—C6	−167.18 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ii	0.82	1.95	2.7577 (15)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.82	1.95	2.7577 (15)	170

Symmetry code: (i) .