(E,E)-1,2-Bis[3-meth-oxy-4-(prop-2-yn-1-yl-oxy)benzyl-idene]hydrazine.

The complete mol-ecule in the title compound, C(22)H(20)N(2)O(4), is generated by the application of an inversion centre. With the exception of the terminal acetyl-ene groups [C-O-C-C = -78.02 (17)°], the remaining atoms constituting the mol-ecule are essentially coplanar. The configuration around the C=N bond [1.282 (2) Å] is E. The formation of supra-molecular chains mediated by C-H⋯O inter-actions, occurring between methyl-ene H and meth-oxy O atoms, is the most notable feature of the crystal packing.

Related literature

For background to the study see: Xu et al. (1997 ▶); Zheng et al. (2005 ▶); Kundu et al. (2005 ▶). For additional analysis, see: Spek (2009 ▶).

Experimental

Crystal data

C22H20N2O4

M = 376.40

Monoclinic,

a = 4.4840 (3) Å

b = 14.4636 (8) Å

c = 14.3939 (9) Å

β = 91.674 (4)°

V = 933.11 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.25 × 0.11 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.368, T max = 0.746

8574 measured reflections

2138 independent reflections

1625 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.124

S = 1.05

2138 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022410/hb5907sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022410/hb5907Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022410/hb5907Isup3.cml

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

C22H20N2O4	F(000) = 396
Mr = 376.40	Dx = 1.340 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1658 reflections
a = 4.4840 (3) Å	θ = 2.8–29.5°
b = 14.4636 (8) Å	µ = 0.09 mm−1
c = 14.3939 (9) Å	T = 100 K
β = 91.674 (4)°	Needle, yellow
V = 933.11 (10) Å3	0.25 × 0.11 × 0.07 mm
Z = 2

Bruker SMART APEX CCD diffractometer	2138 independent reflections
Radiation source: fine-focus sealed tube	1625 reflections with I > 2σ(I)
graphite	Rint = 0.069
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.368, Tmax = 0.746	k = −18→18
8574 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.2035P] where P = (Fo2 + 2Fc2)/3
2138 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	1.2641 (2)	0.54779 (7)	0.43315 (7)	0.0201 (3)
O2	1.3374 (2)	0.41802 (7)	0.31509 (8)	0.0218 (3)
N1	0.5998 (3)	0.49139 (8)	0.03789 (9)	0.0204 (3)
C1	0.5930 (3)	0.55648 (10)	0.09829 (11)	0.0195 (4)
H1	0.4638	0.6075	0.0867	0.023*
C2	0.7742 (3)	0.55572 (10)	0.18375 (11)	0.0187 (3)
C3	0.7351 (3)	0.62536 (10)	0.24843 (11)	0.0201 (4)
H3	0.5955	0.6733	0.2351	0.024*
C4	0.8968 (3)	0.62633 (10)	0.33254 (11)	0.0192 (3)
H4	0.8694	0.6750	0.3758	0.023*
C5	1.0972 (3)	0.55612 (9)	0.35270 (10)	0.0170 (3)
C6	1.1383 (3)	0.48469 (9)	0.28727 (11)	0.0178 (3)
C7	0.9810 (3)	0.48486 (9)	0.20414 (11)	0.0182 (3)
H7	1.0117	0.4370	0.1602	0.022*
C8	1.2080 (4)	0.61172 (10)	0.50702 (11)	0.0209 (4)
H8A	1.2888	0.5857	0.5662	0.025*
H8B	0.9898	0.6189	0.5128	0.025*
C9	1.3423 (4)	0.70363 (10)	0.49229 (11)	0.0214 (4)
C10	1.4542 (4)	0.77718 (11)	0.48483 (12)	0.0262 (4)
H10	1.5441	0.8363	0.4788	0.031*
C11	1.3762 (4)	0.34187 (10)	0.25333 (12)	0.0255 (4)
H11A	1.1830	0.3121	0.2405	0.038*
H11B	1.5142	0.2971	0.2821	0.038*
H11C	1.4578	0.3642	0.1950	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0245 (6)	0.0180 (5)	0.0174 (6)	0.0022 (4)	−0.0053 (5)	−0.0022 (4)
O2	0.0261 (6)	0.0161 (5)	0.0228 (6)	0.0055 (4)	−0.0061 (5)	−0.0030 (4)
N1	0.0202 (7)	0.0225 (6)	0.0182 (7)	−0.0017 (5)	−0.0047 (6)	0.0031 (5)
C1	0.0185 (8)	0.0176 (7)	0.0223 (8)	−0.0017 (6)	−0.0020 (7)	0.0035 (6)
C2	0.0180 (8)	0.0171 (7)	0.0209 (8)	−0.0036 (6)	−0.0014 (7)	0.0025 (6)
C3	0.0184 (8)	0.0160 (7)	0.0260 (9)	0.0001 (6)	−0.0019 (7)	0.0029 (6)
C4	0.0221 (8)	0.0150 (7)	0.0207 (8)	−0.0009 (6)	0.0004 (7)	−0.0012 (6)
C5	0.0176 (8)	0.0162 (7)	0.0171 (8)	−0.0029 (6)	−0.0013 (6)	0.0016 (5)
C6	0.0172 (8)	0.0132 (7)	0.0230 (8)	−0.0006 (6)	−0.0007 (6)	0.0023 (6)
C7	0.0195 (8)	0.0148 (7)	0.0202 (8)	−0.0019 (6)	−0.0002 (6)	−0.0013 (5)
C8	0.0259 (9)	0.0211 (7)	0.0154 (8)	0.0006 (6)	−0.0024 (7)	−0.0026 (6)
C9	0.0245 (9)	0.0227 (8)	0.0169 (8)	0.0031 (6)	−0.0020 (7)	−0.0032 (6)
C10	0.0325 (10)	0.0215 (8)	0.0244 (9)	0.0001 (7)	−0.0031 (8)	−0.0031 (6)
C11	0.0293 (9)	0.0176 (7)	0.0293 (9)	0.0034 (6)	−0.0056 (8)	−0.0055 (6)

O1—C5	1.3655 (17)	C4—H4	0.9500
O1—C8	1.4368 (18)	C5—C6	1.414 (2)
O2—C6	1.3664 (16)	C6—C7	1.371 (2)
O2—C11	1.4292 (18)	C7—H7	0.9500
N1—C1	1.282 (2)	C8—C9	1.477 (2)
N1—N1i	1.413 (2)	C8—H8A	0.9900
C1—C2	1.454 (2)	C8—H8B	0.9900
C1—H1	0.9500	C9—C10	1.182 (2)
C2—C3	1.386 (2)	C10—H10	0.9500
C2—C7	1.407 (2)	C11—H11A	0.9800
C3—C4	1.393 (2)	C11—H11B	0.9800
C3—H3	0.9500	C11—H11C	0.9800
C4—C5	1.381 (2)
C5—O1—C8	117.87 (11)	O2—C6—C5	114.66 (13)
C6—O2—C11	116.87 (11)	C7—C6—C5	120.43 (13)
C1—N1—N1i	111.53 (15)	C6—C7—C2	120.15 (14)
N1—C1—C2	122.96 (14)	C6—C7—H7	119.9
N1—C1—H1	118.5	C2—C7—H7	119.9
C2—C1—H1	118.5	O1—C8—C9	113.08 (13)
C3—C2—C7	118.98 (14)	O1—C8—H8A	109.0
C3—C2—C1	118.95 (13)	C9—C8—H8A	109.0
C7—C2—C1	122.03 (14)	O1—C8—H8B	109.0
C2—C3—C4	121.22 (14)	C9—C8—H8B	109.0
C2—C3—H3	119.4	H8A—C8—H8B	107.8
C4—C3—H3	119.4	C10—C9—C8	176.86 (17)
C5—C4—C3	119.61 (14)	C9—C10—H10	180.0
C5—C4—H4	120.2	O2—C11—H11A	109.5
C3—C4—H4	120.2	O2—C11—H11B	109.5
O1—C5—C4	125.46 (13)	H11A—C11—H11B	109.5
O1—C5—C6	114.94 (12)	O2—C11—H11C	109.5
C4—C5—C6	119.60 (13)	H11A—C11—H11C	109.5
O2—C6—C7	124.90 (13)	H11B—C11—H11C	109.5
N1i—N1—C1—C2	179.28 (15)	C11—O2—C6—C5	177.04 (14)
N1—C1—C2—C3	−174.95 (15)	O1—C5—C6—O2	0.4 (2)
N1—C1—C2—C7	2.9 (2)	C4—C5—C6—O2	−178.85 (13)
C7—C2—C3—C4	0.2 (2)	O1—C5—C6—C7	179.38 (13)
C1—C2—C3—C4	178.11 (14)	C4—C5—C6—C7	0.1 (2)
C2—C3—C4—C5	−0.9 (2)	O2—C6—C7—C2	178.03 (14)
C8—O1—C5—C4	6.4 (2)	C5—C6—C7—C2	−0.8 (2)
C8—O1—C5—C6	−172.80 (13)	C3—C2—C7—C6	0.7 (2)
C3—C4—C5—O1	−178.48 (15)	C1—C2—C7—C6	−177.22 (15)
C3—C4—C5—C6	0.7 (2)	C5—O1—C8—C9	−78.02 (17)
C11—O2—C6—C7	−1.8 (2)	O1—C8—C9—C10	−136 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8a···O2ii	0.99	2.36	3.255 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8a⋯O2i	0.99	2.36	3.255 (2)	150

Symmetry code: (i) .