(E,E)-1,2-Bis(2,4,5-trimeth-oxy-benzyl-idene)hydrazine.

The asymmetric unit of the title compound, C(20)H(24)N(2)O(6), contains one half-mol-ecule, the complete mol-ecule being generated by a crystallographic inversion centre. The mol-ecule is nearly planar with a dihedral angle between the two benzene rings of 0.03 (4)° and the central C/N/N/C plane making a dihedral angle of 8.59 (7)° with each of its two adjacent benzene rings. The two meth-oxy groups at the ortho and meta positions are slightly twisted [C-O-C-C torsion angles = 7.23 (12) and 5.73 (13)°], whereas the meth-oxy group at the para position is almost coplanar with the attached benzene ring [C-O-C-C torsion angle = -2.02 (13)°]. The crystal structure is stabilized by a weak C-H⋯π inter-action.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2010 ▶); Jansrisewangwong et al. (2010 ▶); Zhao et al. (2006 ▶). For background to and the bio­logical activity of hydrazones, see: Avaji et al. (2009 ▶); El-Tabl et al. (2008) ▶; Kitaev et al. (1970 ▶); 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

Monoclinic,

a = 7.5056 (1) Å

b = 7.2523 (1) Å

c = 17.4489 (2) Å

β = 90.600 (1)°

V = 949.74 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.47 × 0.29 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.954, T max = 0.990

18099 measured reflections

2778 independent reflections

2384 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.113

S = 1.04

2778 reflections

175 parameters

All H-atom parameters refined

Δρmax = 0.45 e Å−3

Δρmin = −0.22 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/S1600536811019040/is2713sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019040/is2713Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019040/is2713Isup3.cml

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

C20H24N2O6	F(000) = 412
Mr = 388.41	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Melting point = 523 decompose–523 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.5056 (1) Å	Cell parameters from 2778 reflections
b = 7.2523 (1) Å	θ = 2.3–30.0°
c = 17.4489 (2) Å	µ = 0.10 mm−1
β = 90.600 (1)°	T = 100 K
V = 949.74 (2) Å3	Needle, colorless
Z = 2	0.47 × 0.29 × 0.10 mm

Bruker APEXII CCD area-detector diffractometer	2778 independent reflections
Radiation source: sealed tube	2384 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.954, Tmax = 0.990	k = −10→10
18099 measured reflections	l = −24→24

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.2144P] where P = (Fo2 + 2Fc2)/3
2778 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.22 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 100.0 (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	0.26607 (9)	0.49751 (9)	0.57223 (4)	0.01763 (16)
O2	0.36459 (9)	0.78767 (10)	0.32476 (4)	0.02050 (17)
O3	0.19145 (9)	0.52720 (10)	0.25671 (4)	0.01952 (17)
N1	0.03148 (10)	0.06200 (11)	0.47211 (4)	0.01607 (17)
C1	0.16786 (11)	0.35906 (12)	0.45749 (5)	0.01377 (18)
C2	0.25348 (11)	0.50724 (13)	0.49415 (5)	0.01428 (18)
C3	0.32155 (11)	0.65346 (13)	0.45116 (5)	0.01573 (18)
H3	0.3849 (17)	0.7563 (18)	0.4767 (7)	0.017 (3)*
C4	0.30093 (11)	0.65370 (13)	0.37186 (5)	0.01537 (18)
C5	0.21005 (12)	0.50854 (13)	0.33441 (5)	0.01493 (18)
C6	0.14716 (11)	0.36283 (12)	0.37708 (5)	0.01463 (18)
H6	0.0847 (18)	0.261 (2)	0.3529 (8)	0.027 (3)*
C7	0.09679 (11)	0.20862 (13)	0.50302 (5)	0.01512 (18)
H7	0.0952 (17)	0.2209 (18)	0.5580 (8)	0.024 (3)*
C8	0.33469 (13)	0.65505 (14)	0.61202 (6)	0.0198 (2)
H8A	0.3252 (17)	0.6258 (19)	0.6634 (8)	0.024 (3)*
H8B	0.2642 (17)	0.767 (2)	0.5997 (8)	0.026 (3)*
H8C	0.4583 (18)	0.6749 (19)	0.5978 (7)	0.024 (3)*
C9	0.45348 (15)	0.94046 (15)	0.35983 (6)	0.0249 (2)
H9A	0.3707 (19)	1.004 (2)	0.3925 (8)	0.034 (4)*
H9B	0.5579 (18)	0.897 (2)	0.3891 (8)	0.031 (3)*
H9C	0.4852 (18)	1.010 (2)	0.3165 (8)	0.028 (3)*
C10	0.08467 (16)	0.39153 (16)	0.21898 (6)	0.0263 (2)
H10A	−0.0319 (16)	0.3831 (18)	0.2454 (7)	0.019 (3)*
H10B	0.1449 (19)	0.274 (2)	0.2202 (8)	0.032 (4)*
H10C	0.0681 (19)	0.439 (2)	0.1671 (9)	0.036 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0217 (3)	0.0191 (3)	0.0121 (3)	−0.0045 (3)	−0.0015 (2)	−0.0018 (2)
O2	0.0267 (3)	0.0158 (3)	0.0191 (3)	−0.0071 (3)	0.0024 (3)	0.0024 (3)
O3	0.0275 (3)	0.0192 (4)	0.0119 (3)	−0.0045 (3)	−0.0002 (2)	0.0015 (2)
N1	0.0200 (3)	0.0150 (4)	0.0132 (3)	−0.0027 (3)	0.0013 (3)	0.0023 (3)
C1	0.0144 (4)	0.0136 (4)	0.0133 (4)	−0.0009 (3)	0.0004 (3)	0.0001 (3)
C2	0.0145 (3)	0.0155 (4)	0.0128 (4)	−0.0004 (3)	0.0001 (3)	−0.0010 (3)
C3	0.0159 (4)	0.0136 (4)	0.0178 (4)	−0.0020 (3)	0.0005 (3)	−0.0014 (3)
C4	0.0162 (4)	0.0129 (4)	0.0171 (4)	−0.0003 (3)	0.0024 (3)	0.0013 (3)
C5	0.0172 (4)	0.0156 (4)	0.0121 (4)	−0.0005 (3)	0.0010 (3)	0.0004 (3)
C6	0.0166 (4)	0.0135 (4)	0.0138 (4)	−0.0018 (3)	0.0005 (3)	−0.0004 (3)
C7	0.0168 (4)	0.0164 (4)	0.0121 (4)	−0.0013 (3)	0.0001 (3)	0.0011 (3)
C8	0.0215 (4)	0.0204 (5)	0.0173 (4)	−0.0020 (4)	−0.0017 (3)	−0.0057 (3)
C9	0.0301 (5)	0.0182 (5)	0.0266 (5)	−0.0096 (4)	0.0038 (4)	−0.0007 (4)
C10	0.0402 (6)	0.0241 (5)	0.0145 (4)	−0.0086 (5)	−0.0043 (4)	−0.0010 (4)

O1—C2	1.3664 (10)	C4—C5	1.4112 (12)
O1—C8	1.4301 (11)	C5—C6	1.3789 (12)
O2—C4	1.3624 (11)	C6—H6	0.970 (14)
O2—C9	1.4279 (12)	C7—H7	0.964 (13)
O3—C5	1.3681 (10)	C8—H8A	0.924 (13)
O3—C10	1.4257 (12)	C8—H8B	0.991 (14)
N1—C7	1.2870 (12)	C8—H8C	0.974 (13)
N1—N1i	1.4103 (15)	C9—H9A	0.966 (15)
C1—C2	1.4031 (12)	C9—H9B	0.981 (14)
C1—C6	1.4102 (12)	C9—H9C	0.944 (14)
C1—C7	1.4544 (12)	C10—H10A	0.995 (12)
C2—C3	1.3987 (12)	C10—H10B	0.967 (16)
C3—C4	1.3906 (12)	C10—H10C	0.976 (15)
C3—H3	0.988 (13)
C2—O1—C8	117.62 (7)	N1—C7—C1	122.08 (8)
C4—O2—C9	117.39 (7)	N1—C7—H7	119.0 (8)
C5—O3—C10	116.12 (7)	C1—C7—H7	118.9 (8)
C7—N1—N1i	111.49 (9)	O1—C8—H8A	104.9 (8)
C2—C1—C6	118.95 (8)	O1—C8—H8B	111.1 (8)
C2—C1—C7	119.62 (8)	H8A—C8—H8B	110.6 (11)
C6—C1—C7	121.39 (8)	O1—C8—H8C	109.5 (8)
O1—C2—C3	123.51 (8)	H8A—C8—H8C	111.4 (11)
O1—C2—C1	116.21 (8)	H8B—C8—H8C	109.4 (11)
C3—C2—C1	120.28 (8)	O2—C9—H9A	108.9 (9)
C4—C3—C2	119.81 (8)	O2—C9—H9B	110.1 (9)
C4—C3—H3	119.7 (7)	H9A—C9—H9B	111.1 (12)
C2—C3—H3	120.5 (7)	O2—C9—H9C	101.2 (9)
O2—C4—C3	124.41 (8)	H9A—C9—H9C	112.6 (12)
O2—C4—C5	115.05 (8)	H9B—C9—H9C	112.4 (12)
C3—C4—C5	120.54 (8)	O3—C10—H10A	108.7 (7)
O3—C5—C6	125.38 (8)	O3—C10—H10B	109.8 (9)
O3—C5—C4	115.40 (8)	H10A—C10—H10B	110.4 (12)
C6—C5—C4	119.22 (8)	O3—C10—H10C	104.5 (9)
C5—C6—C1	121.15 (8)	H10A—C10—H10C	110.3 (11)
C5—C6—H6	121.1 (8)	H10B—C10—H10C	112.8 (12)
C1—C6—H6	117.8 (8)
C8—O1—C2—C3	7.23 (12)	C10—O3—C5—C4	−173.90 (8)
C8—O1—C2—C1	−173.26 (8)	O2—C4—C5—O3	−2.95 (12)
C6—C1—C2—O1	178.64 (7)	C3—C4—C5—O3	177.39 (8)
C7—C1—C2—O1	0.86 (12)	O2—C4—C5—C6	177.39 (8)
C6—C1—C2—C3	−1.84 (13)	C3—C4—C5—C6	−2.26 (13)
C7—C1—C2—C3	−179.61 (8)	O3—C5—C6—C1	−177.86 (8)
O1—C2—C3—C4	−179.16 (8)	C4—C5—C6—C1	1.76 (13)
C1—C2—C3—C4	1.34 (13)	C2—C1—C6—C5	0.27 (13)
C9—O2—C4—C3	−2.02 (13)	C7—C1—C6—C5	178.00 (8)
C9—O2—C4—C5	178.34 (8)	N1i—N1—C7—C1	−178.99 (9)
C2—C3—C4—O2	−178.90 (8)	C2—C1—C7—N1	−173.65 (8)
C2—C3—C4—C5	0.72 (13)	C6—C1—C7—N1	8.63 (13)
C10—O3—C5—C6	5.73 (13)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···Cg1ii	0.974 (13)	2.675 (14)	3.4837 (10)	140.7 (10)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8C⋯Cg1i	0.974 (13)	2.675 (14)	3.4837 (10)	140.7 (10)

Symmetry code: (i) .