(E,E)-1,2-Bis(2,4,6-trimeth-oxy-benzyl-idene)hydrazine.

The title mol-ecule, C(20)H(24)N(2)O(6), lies on an inversion centre. All non-H atoms are essentially coplanar, with an r.m.s. deviation of 0.0415 (1) Å and a maximum deviation of 0.1476 (1) Å for the meth-oxy C atom at the 4-position of the benzene ring. The crystal structure is stabilized by weak C-H⋯N and C-H⋯π inter-actions.

Related literature

For standard bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Jansrisewangwong et al. (2010 ▶); Zhao et al. (2006 ▶). For background and the biological activity of hydro­zones, see: El-Tabl et al. (2008 ▶); Qin et al. (2009 ▶); Ramamohan et al. (1995 ▶); Rollas & Küçükgüzel (2007 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C20H24N2O6

M = 388.41

Triclinic,

a = 7.3851 (2) Å

b = 7.4043 (2) Å

c = 9.5440 (2) Å

α = 71.412 (1)°

β = 78.095 (1)°

γ = 79.449 (1)°

V = 480.13 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.29 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.972, T max = 0.992

11100 measured reflections

2791 independent reflections

2244 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.03

2791 reflections

134 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033684/lh5117sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033684/lh5117Isup2.hkl

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

C20H24N2O6	Z = 1
Mr = 388.41	F(000) = 206
Triclinic, P1	Dx = 1.343 Mg m−3
Hall symbol: -P 1	Melting point = 484–486 K
a = 7.3851 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4043 (2) Å	Cell parameters from 2791 reflections
c = 9.5440 (2) Å	θ = 2.3–30.0°
α = 71.412 (1)°	µ = 0.10 mm−1
β = 78.095 (1)°	T = 100 K
γ = 79.449 (1)°	Block, yellow
V = 480.13 (2) Å3	0.29 × 0.14 × 0.08 mm

Bruker APEXII CCD area-detector diffractometer	2791 independent reflections
Radiation source: sealed tube	2244 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.972, Tmax = 0.992	k = −10→10
11100 measured reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.1087P] where P = (Fo2 + 2Fc2)/3
2791 reflections	(Δ/σ)max = 0.001
134 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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
O1	0.20858 (11)	0.87907 (11)	0.08848 (8)	0.01756 (18)
O2	0.82788 (11)	0.57545 (11)	0.12544 (8)	0.01906 (19)
O3	0.44058 (10)	0.78425 (11)	0.53298 (8)	0.01517 (17)
N1	0.09376 (12)	0.95751 (13)	0.49155 (10)	0.0163 (2)
C1	0.35619 (14)	0.81164 (14)	0.16438 (11)	0.0142 (2)
C2	0.52565 (15)	0.72803 (15)	0.10450 (11)	0.0158 (2)
H2A	0.5443	0.7178	0.0078	0.019*
C3	0.66759 (14)	0.65957 (15)	0.19168 (11)	0.0148 (2)
C4	0.64415 (14)	0.67699 (14)	0.33540 (11)	0.0143 (2)
H4A	0.7406	0.6318	0.3917	0.017*
C5	0.47341 (14)	0.76345 (14)	0.39383 (10)	0.0133 (2)
C6	0.32381 (14)	0.83151 (14)	0.31125 (11)	0.0134 (2)
C7	0.14037 (15)	0.91807 (15)	0.36584 (11)	0.0147 (2)
C8	0.22823 (17)	0.85390 (17)	−0.05710 (12)	0.0205 (2)
H8A	0.1127	0.9008	−0.0954	0.031*
H8B	0.2601	0.7199	−0.0499	0.031*
H8C	0.3251	0.9241	−0.1234	0.031*
C9	0.96932 (16)	0.47848 (17)	0.21582 (12)	0.0212 (2)
H9A	1.0697	0.4173	0.1585	0.032*
H9B	0.9173	0.3834	0.3022	0.032*
H9C	1.0157	0.5698	0.2473	0.032*
C10	0.59168 (15)	0.72427 (16)	0.61730 (11)	0.0167 (2)
H10A	0.5516	0.7495	0.7123	0.025*
H10B	0.6945	0.7939	0.5631	0.025*
H10C	0.6302	0.5892	0.6330	0.025*
H7	0.0407 (19)	0.9430 (19)	0.3064 (15)	0.022 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0168 (4)	0.0235 (4)	0.0134 (3)	0.0022 (3)	−0.0047 (3)	−0.0080 (3)
O2	0.0149 (4)	0.0236 (4)	0.0163 (4)	0.0049 (3)	0.0002 (3)	−0.0082 (3)
O3	0.0145 (4)	0.0196 (4)	0.0124 (3)	0.0013 (3)	−0.0034 (3)	−0.0073 (3)
N1	0.0125 (4)	0.0186 (4)	0.0173 (4)	−0.0003 (3)	−0.0004 (3)	−0.0069 (3)
C1	0.0156 (5)	0.0131 (4)	0.0133 (4)	−0.0010 (4)	−0.0031 (4)	−0.0032 (4)
C2	0.0175 (5)	0.0173 (5)	0.0122 (4)	−0.0009 (4)	−0.0001 (4)	−0.0058 (4)
C3	0.0134 (5)	0.0145 (5)	0.0150 (4)	−0.0007 (4)	0.0012 (4)	−0.0049 (4)
C4	0.0133 (5)	0.0149 (5)	0.0144 (4)	−0.0008 (4)	−0.0028 (4)	−0.0043 (4)
C5	0.0153 (5)	0.0120 (4)	0.0123 (4)	−0.0028 (4)	−0.0003 (4)	−0.0040 (3)
C6	0.0140 (5)	0.0134 (4)	0.0126 (4)	−0.0010 (4)	−0.0014 (3)	−0.0046 (4)
C7	0.0137 (5)	0.0151 (5)	0.0151 (4)	−0.0006 (4)	−0.0027 (4)	−0.0049 (4)
C8	0.0240 (6)	0.0251 (6)	0.0143 (5)	0.0020 (4)	−0.0061 (4)	−0.0093 (4)
C9	0.0159 (5)	0.0242 (5)	0.0198 (5)	0.0043 (4)	−0.0014 (4)	−0.0061 (4)
C10	0.0157 (5)	0.0207 (5)	0.0157 (4)	−0.0010 (4)	−0.0051 (4)	−0.0071 (4)

O1—C1	1.3632 (12)	C4—H4A	0.9300
O1—C8	1.4347 (12)	C5—C6	1.4135 (14)
O2—C3	1.3642 (12)	C6—C7	1.4564 (14)
O2—C9	1.4328 (13)	C7—H7	0.976 (14)
O3—C5	1.3528 (11)	C8—H8A	0.9600
O3—C10	1.4322 (12)	C8—H8B	0.9600
N1—C7	1.2882 (13)	C8—H8C	0.9600
N1—N1i	1.4117 (18)	C9—H9A	0.9600
C1—C2	1.3866 (14)	C9—H9B	0.9600
C1—C6	1.4226 (13)	C9—H9C	0.9600
C2—C3	1.3944 (15)	C10—H10A	0.9600
C2—H2A	0.9300	C10—H10B	0.9600
C3—C4	1.3909 (13)	C10—H10C	0.9600
C4—C5	1.3974 (14)
C1—O1—C8	118.01 (8)	N1—C7—C6	125.41 (9)
C3—O2—C9	117.79 (8)	N1—C7—H7	115.8 (8)
C5—O3—C10	117.61 (8)	C6—C7—H7	118.7 (8)
C7—N1—N1i	110.66 (11)	O1—C8—H8A	109.5
O1—C1—C2	122.94 (9)	O1—C8—H8B	109.5
O1—C1—C6	115.10 (9)	H8A—C8—H8B	109.5
C2—C1—C6	121.95 (9)	O1—C8—H8C	109.5
C1—C2—C3	118.90 (9)	H8A—C8—H8C	109.5
C1—C2—H2A	120.5	H8B—C8—H8C	109.5
C3—C2—H2A	120.5	O2—C9—H9A	109.5
O2—C3—C4	123.44 (9)	O2—C9—H9B	109.5
O2—C3—C2	115.02 (9)	H9A—C9—H9B	109.5
C4—C3—C2	121.55 (9)	O2—C9—H9C	109.5
C3—C4—C5	118.99 (9)	H9A—C9—H9C	109.5
C3—C4—H4A	120.5	H9B—C9—H9C	109.5
C5—C4—H4A	120.5	O3—C10—H10A	109.5
O3—C5—C4	122.15 (9)	O3—C10—H10B	109.5
O3—C5—C6	116.17 (9)	H10A—C10—H10B	109.5
C4—C5—C6	121.67 (9)	O3—C10—H10C	109.5
C5—C6—C1	116.93 (9)	H10A—C10—H10C	109.5
C5—C6—C7	124.92 (9)	H10B—C10—H10C	109.5
C1—C6—C7	118.15 (9)
C8—O1—C1—C2	2.86 (15)	C3—C4—C5—C6	0.69 (15)
C8—O1—C1—C6	−176.61 (9)	O3—C5—C6—C1	179.70 (8)
O1—C1—C2—C3	−178.70 (9)	C4—C5—C6—C1	−1.27 (15)
C6—C1—C2—C3	0.74 (16)	O3—C5—C6—C7	−0.86 (15)
C9—O2—C3—C4	8.39 (15)	C4—C5—C6—C7	178.16 (9)
C9—O2—C3—C2	−171.46 (9)	O1—C1—C6—C5	−179.97 (8)
C1—C2—C3—O2	178.49 (9)	C2—C1—C6—C5	0.55 (15)
C1—C2—C3—C4	−1.37 (16)	O1—C1—C6—C7	0.55 (14)
O2—C3—C4—C5	−179.18 (9)	C2—C1—C6—C7	−178.93 (9)
C2—C3—C4—C5	0.67 (16)	N1i—N1—C7—C6	179.28 (10)
C10—O3—C5—C4	3.58 (14)	C5—C6—C7—N1	5.52 (17)
C10—O3—C5—C6	−177.40 (8)	C1—C6—C7—N1	−175.05 (10)
C3—C4—C5—O3	179.66 (9)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.977 (14)	2.332 (14)	2.6886 (12)	100.6 (10)
C10—H10B···N1ii	0.96	2.49	3.3876 (15)	155
C8—H8C···Cgiii	0.97	2.79	3.6678 (13)	152
C10—H10C···Cgiv	0.97	2.63	3.4385 (13)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯N1i	0.96	2.49	3.3876 (15)	155
C8—H8C⋯Cgii	0.97	2.79	3.6678 (13)	152
C10—H10C⋯Cgiii	0.97	2.63	3.4385 (13)	142

Symmetry codes: (i) ; (ii) ; (iii) .