5,5′-Bis(diethyl­amino)-2,2′-[butane-1,4-diyldioxy­bis(nitrilo­methyl­idyne)]­diphenol

Liu, G.-L.; Chen, X.; He, X.-N.; Dong, W.-K.

doi:10.1107/S1600536808004352

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o659

doi:10.1107/S1600536808004352

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5,5′-Bis(diethylamino)-2,2′-[butane-1,4-diyldioxybis(nitrilomethylidyne)]diphenol

Gai-Lan Liu,^a Xiao Chen,^a Xue-Ni He ^a and Wen-Kui Dong ^a ^*

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 29 November 2007; accepted 13 February 2008; online 5 March 2008)

The title complex, C₂₆H₃₈N₄O₄, was synthesized by the reaction of 4-diethylamino-2-hydroxybenzaldehyde with 1,4-bis(aminooxy)butane in ethanol. It crystallizes as discrete centrosymmetric molecules adopting an extended conformation where the two salicylaldoxime groups are separated from each other. Intramolecular O—H⋯N hydrogen bonding is observed between the hydroxy groups and oxime N atoms. Intermolecular π–π stacking interactions [3.979 (2) Å] between aromatic rings are apparent in the crystal structure. Each ethyl group is disordered over two positions; in one the site occupancy factors are 0.55 and 0.45, in the other 0.53 and 0.47.

Related literature

For related literature, see: Abu-Surrah et al. (1999 ); Boghaei et al. (2006 ); Costes et al. (2000 ); Dong, Duan et al. (2007 ); Dong, He et al. (2007 ); Lacroix (2001 ); Zhang et al. (2007 ).

Experimental

Crystal data

C₂₆H₃₈N₄O₄
M_r = 470.60
Monoclinic, P 2₁ /c
a = 7.6888 (9) Å
b = 13.777 (2) Å
c = 12.6547 (19) Å
β = 101.627 (2)°
V = 1313.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.45 × 0.43 × 0.37 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.971
6450 measured reflections
2303 independent reflections
1176 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.152
S = 1.06
2303 reflections
196 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.91	2.639 (2)	147

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004352/hg2359sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004352/hg2359Isup2.hkl

checkCIF report

Comment top

A great deal of attention has recently been attracted to the study of salen and its derivatives (Boghaei et al., 2006; Abu-Surrah et al., 1999) due to the ease of formation of metal complexes which model reaction centers of metalloenzymes. These compounds also have excellent magnetic properties (Costes et al., 2000) and form nonlinear optical materials (Lacroix, 2001). Recently, we have reported some salen-type bisoxime derivatives (Dong, Duan et al., 2007; Dong, He et al., 2007; Zhang et al., 2007), Now, the title compound, (I) was synthesized and its crystal structure determined. (Fig. 1). The molecule of (I) is disposed about a crystallographic centre of symmetry, and adopts an extended conformation with the two salicylaldoxime groups separated from each other.

The oxime groups and phenolic groups adopt a trans conformation about the C?N bond, and there is a strong O—H···N intramolecular hydrogen bond, O2—H2···N1 (d(O2—H2) = 0.820 Å, d(H2···N1) = 1.913 Å, d(O2···N1) = 2.639 (2) Å, <O2—H2···N1 = 147.01°). The carbon atoms of N,N'-diethylamino of the ligands (C10, C11, C12, C13 and C10', C11', C12', C13') are disordered over two different positions, which were allowed for during refinement.

Related literature top

For related literature, see: Abu-Surrah et al. (1999); Boghaei et al. (2006); Costes et al. (2000); Dong, Duan et al. (2007); Dong, He et al. (2007); Lacroix (2001); Zhang et al. (2007).

Experimental top

5,5'-di(N,N'-diethylamino)-2,2'-[(1,4-butylene) dioxybis(nitrilomethylidyne)]diphenol was synthesized according to an method reported earlier (Zhang et al., 2007). To an ethanol solution (5 ml) of 4-(N,N-diethylamino)-2-hydroxybenzaldehyde (398.07 mg, 2.06 mmol) was added an ethanol (3 ml) solution of 1,4-bis(aminooxy)butane (121.66 mg, 1.03 mmol). The solution was stirred at 328 K for 4 h. then concentrated to about 2 ml under reduced pressure, and washed successively with ethanol and hexane, respectively. The product was dried under vacuum and purified with recrystallization from ethanol to yield 436.26 mg of the title compound. Yield, 45%. mp. 397–398 K. Anal. Calc. for C₂₆H₃₈N₄O₄: C, 66.36; H, 8.14; N, 11.91%. Found: C, 66.25; H, 8.08; N, 12.07%. Colorless prismatic single crystals suitable for X-ray diffraction studies were obtained after about two weeks by slow evaporation of (I) at room temperature from an acetone/chloroform solution

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecule structure of (I) with atom labelling and displacement ellipsoids at the 30% probability level for non-hydrogen atoms.

5,5'-Bis(diethylamino)-2,2'-[butane-1,4- diyldioxybis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₆H₃₈N₄O₄	F(000) = 508
M_r = 470.60	D_x = 1.190 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1484 reflections
a = 7.6888 (9) Å	θ = 3.0–23.4°
b = 13.777 (2) Å	µ = 0.08 mm⁻¹
c = 12.6547 (19) Å	T = 298 K
β = 101.627 (2)°	Block, colourless
V = 1313.0 (3) Å³	0.45 × 0.43 × 0.37 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2303 independent reflections
Radiation source: fine-focus sealed tube	1176 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.965, T_max = 0.971	k = −16→16
6450 measured reflections	l = −15→14

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0421P)² + 0.5356P] where P = (F_o² + 2F_c²)/3
2303 reflections	(Δ/σ)_max = 0.001
196 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₆H₃₈N₄O₄	V = 1313.0 (3) Å³
M_r = 470.60	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6888 (9) Å	µ = 0.08 mm⁻¹
b = 13.777 (2) Å	T = 298 K
c = 12.6547 (19) Å	0.45 × 0.43 × 0.37 mm
β = 101.627 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2303 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1176 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.971	R_int = 0.034
6450 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.06	Δρ_max = 0.12 e Å⁻³
2303 reflections	Δρ_min = −0.15 e Å⁻³
196 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.4824 (3)	0.15042 (16)	0.05037 (19)	0.0661 (6)
N2	1.2014 (4)	0.3925 (2)	0.0621 (2)	0.1031 (10)
O1	0.3420 (3)	0.10682 (14)	0.08908 (15)	0.0762 (6)
O2	0.6803 (3)	0.21500 (17)	−0.08246 (16)	0.1077 (9)
H2	0.5962	0.1874	−0.0647	0.162*
C1	0.2185 (4)	0.0666 (2)	0.0010 (2)	0.0731 (8)
H1A	0.2763	0.0180	−0.0354	0.088*
H1B	0.1725	0.1171	−0.0505	0.088*
C2	0.0702 (3)	0.0215 (2)	0.0445 (2)	0.0721 (8)
H2A	0.0162	0.0703	0.0828	0.086*
H2B	0.1178	−0.0291	0.0954	0.086*
C3	0.5929 (4)	0.1909 (2)	0.1266 (2)	0.0640 (8)
H3	0.5727	0.1877	0.1965	0.077*
C4	0.7474 (3)	0.24132 (19)	0.1074 (2)	0.0578 (7)
C5	0.7878 (4)	0.2523 (2)	0.0062 (2)	0.0638 (7)
C6	0.9367 (4)	0.3015 (2)	−0.0082 (2)	0.0736 (9)
H6	0.9585	0.3077	−0.0776	0.088*
C7	1.0547 (4)	0.3419 (2)	0.0766 (2)	0.0765 (9)
C8	1.0136 (4)	0.3313 (3)	0.1787 (2)	0.1091 (14)
H8	1.0893	0.3572	0.2387	0.131*
C9	0.8640 (4)	0.2835 (3)	0.1913 (2)	0.0949 (11)
H9	0.8397	0.2792	0.2602	0.114*
C10	1.2063 (14)	0.4298 (8)	−0.0475 (9)	0.086 (3)	0.546 (16)
H10A	1.2705	0.4908	−0.0404	0.104*	0.546 (16)
H10B	1.0857	0.4428	−0.0852	0.104*	0.546 (16)
C11	1.2923 (12)	0.3612 (8)	−0.1148 (11)	0.117 (4)	0.546 (16)
H11A	1.4115	0.3474	−0.0779	0.175*	0.546 (16)
H11B	1.2946	0.3908	−0.1832	0.175*	0.546 (16)
H11C	1.2254	0.3020	−0.1261	0.175*	0.546 (16)
C12	1.3562 (12)	0.3955 (8)	0.1481 (10)	0.094 (4)	0.525 (13)
H12A	1.4652	0.3943	0.1205	0.112*	0.525 (13)
H12B	1.3569	0.3425	0.1986	0.112*	0.525 (13)
C13	1.3294 (17)	0.4919 (10)	0.1982 (10)	0.094 (4)	0.525 (13)
H13A	1.3161	0.5417	0.1441	0.141*	0.525 (13)
H13B	1.4304	0.5063	0.2542	0.141*	0.525 (13)
H13C	1.2245	0.4894	0.2284	0.141*	0.525 (13)
C10'	1.2900 (15)	0.3771 (9)	−0.0279 (11)	0.086 (4)	0.454 (16)
H10C	1.2714	0.3111	−0.0542	0.104*	0.454 (16)
H10D	1.4167	0.3880	−0.0051	0.104*	0.454 (16)
C11'	1.2124 (14)	0.4477 (10)	−0.1155 (12)	0.105 (4)	0.454 (16)
H11D	1.0856	0.4408	−0.1322	0.158*	0.454 (16)
H11E	1.2594	0.4346	−0.1788	0.158*	0.454 (16)
H11F	1.2427	0.5127	−0.0913	0.158*	0.454 (16)
C12'	1.298 (2)	0.4652 (12)	0.1485 (10)	0.083 (4)	0.475 (13)
H12C	1.3526	0.5158	0.1128	0.100*	0.475 (13)
H12D	1.2113	0.4956	0.1838	0.100*	0.475 (13)
C13'	1.4401 (12)	0.4176 (7)	0.2334 (9)	0.091 (4)	0.475 (13)
H13D	1.3899	0.3632	0.2640	0.136*	0.475 (13)
H13E	1.4846	0.4637	0.2891	0.136*	0.475 (13)
H13F	1.5355	0.3957	0.2007	0.136*	0.475 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0676 (15)	0.0703 (15)	0.0680 (15)	0.0002 (13)	0.0315 (13)	0.0105 (13)
N2	0.080 (2)	0.156 (3)	0.0764 (19)	−0.036 (2)	0.0222 (17)	0.008 (2)
O1	0.0714 (13)	0.0932 (15)	0.0707 (13)	−0.0087 (11)	0.0302 (11)	0.0124 (11)
O2	0.135 (2)	0.137 (2)	0.0643 (14)	−0.0630 (17)	0.0500 (13)	−0.0323 (13)
C1	0.070 (2)	0.082 (2)	0.0717 (19)	−0.0014 (17)	0.0248 (16)	0.0077 (16)
C2	0.0660 (19)	0.081 (2)	0.0742 (19)	0.0035 (16)	0.0250 (14)	0.0138 (16)
C3	0.0654 (19)	0.077 (2)	0.0546 (16)	0.0103 (16)	0.0241 (15)	0.0148 (15)
C4	0.0542 (16)	0.0727 (18)	0.0495 (15)	0.0095 (14)	0.0179 (13)	0.0136 (13)
C5	0.0772 (19)	0.0689 (18)	0.0508 (16)	−0.0059 (16)	0.0262 (15)	−0.0074 (14)
C6	0.087 (2)	0.086 (2)	0.0577 (17)	−0.0134 (18)	0.0392 (17)	−0.0018 (15)
C7	0.064 (2)	0.105 (2)	0.0617 (19)	−0.0059 (18)	0.0168 (16)	0.0116 (17)
C8	0.069 (2)	0.203 (4)	0.0511 (18)	−0.034 (2)	0.0026 (15)	0.017 (2)
C9	0.069 (2)	0.172 (3)	0.0444 (17)	−0.015 (2)	0.0130 (15)	0.0235 (19)
C10	0.078 (6)	0.103 (7)	0.082 (7)	−0.016 (5)	0.024 (5)	0.006 (6)
C11	0.118 (6)	0.125 (8)	0.124 (10)	0.000 (6)	0.063 (6)	0.014 (6)
C12	0.074 (6)	0.095 (7)	0.115 (10)	0.007 (5)	0.027 (7)	−0.001 (6)
C13	0.083 (7)	0.086 (7)	0.106 (9)	−0.006 (6)	0.003 (7)	−0.012 (7)
C10'	0.067 (6)	0.105 (8)	0.089 (9)	−0.004 (5)	0.020 (5)	0.012 (6)
C11'	0.099 (7)	0.119 (10)	0.096 (8)	0.006 (6)	0.016 (6)	0.022 (7)
C12'	0.068 (7)	0.102 (11)	0.079 (8)	−0.021 (7)	0.011 (7)	0.002 (7)
C13'	0.070 (6)	0.111 (7)	0.083 (7)	0.003 (5)	−0.004 (5)	−0.016 (5)

Geometric parameters (Å, º) top

N1—C3	1.278 (3)	C9—H9	0.9300
N1—O1	1.407 (2)	C10—C11	1.51 (2)
N2—C7	1.370 (4)	C10—H10A	0.9700
N2—C12	1.442 (12)	C10—H10B	0.9700
N2—C10'	1.456 (14)	C11—H11A	0.9600
N2—C10	1.486 (12)	C11—H11B	0.9600
N2—C12'	1.557 (13)	C11—H11C	0.9600
O1—C1	1.422 (3)	C12—C13	1.50 (2)
O2—C5	1.353 (3)	C12—H12A	0.9700
O2—H2	0.8200	C12—H12B	0.9700
C1—C2	1.497 (3)	C13—H13A	0.9600
C1—H1A	0.9700	C13—H13B	0.9600
C1—H1B	0.9700	C13—H13C	0.9600
C2—C2ⁱ	1.515 (5)	C10'—C11'	1.50 (3)
C2—H2A	0.9700	C10'—H10C	0.9700
C2—H2B	0.9700	C10'—H10D	0.9700
C3—C4	1.438 (3)	C11'—H11D	0.9600
C3—H3	0.9300	C11'—H11E	0.9600
C4—C9	1.372 (4)	C11'—H11F	0.9600
C4—C5	1.386 (3)	C12'—C13'	1.52 (2)
C5—C6	1.374 (4)	C12'—H12C	0.9700
C6—C7	1.376 (4)	C12'—H12D	0.9700
C6—H6	0.9300	C13'—H13D	0.9600
C7—C8	1.398 (4)	C13'—H13E	0.9600
C8—C9	1.363 (4)	C13'—H13F	0.9600
C8—H8	0.9300

C3—N1—O1	111.3 (2)	C9—C8—H8	119.6
C7—N2—C12	119.3 (4)	C7—C8—H8	119.6
C7—N2—C10'	124.0 (5)	C8—C9—C4	123.4 (3)
C12—N2—C10'	98.6 (6)	C8—C9—H9	118.3
C7—N2—C10	118.5 (4)	C4—C9—H9	118.3
C12—N2—C10	121.4 (5)	N2—C10—C11	114.0 (12)
C10'—N2—C10	38.4 (4)	N2—C10—H10A	108.7
C7—N2—C12'	121.5 (5)	C11—C10—H10A	108.7
C12—N2—C12'	41.1 (6)	N2—C10—H10B	108.7
C10'—N2—C12'	114.2 (6)	C11—C10—H10B	108.7
C10—N2—C12'	109.6 (6)	H10A—C10—H10B	107.6
N1—O1—C1	109.36 (19)	N2—C12—C13	100.4 (9)
C5—O2—H2	109.5	N2—C12—H12A	111.7
O1—C1—C2	108.2 (2)	C13—C12—H12A	111.7
O1—C1—H1A	110.1	N2—C12—H12B	111.7
C2—C1—H1A	110.1	C13—C12—H12B	111.7
O1—C1—H1B	110.1	H12A—C12—H12B	109.5
C2—C1—H1B	110.1	N2—C10'—C11'	107.7 (13)
H1A—C1—H1B	108.4	N2—C10'—H10C	110.2
C1—C2—C2ⁱ	111.8 (3)	C11'—C10'—H10C	110.2
C1—C2—H2A	109.3	N2—C10'—H10D	110.2
C2ⁱ—C2—H2A	109.3	C11'—C10'—H10D	110.2
C1—C2—H2B	109.3	H10C—C10'—H10D	108.5
C2ⁱ—C2—H2B	109.3	C10'—C11'—H11D	109.5
H2A—C2—H2B	107.9	C10'—C11'—H11E	109.5
N1—C3—C4	122.0 (2)	H11D—C11'—H11E	109.5
N1—C3—H3	119.0	C10'—C11'—H11F	109.5
C4—C3—H3	119.0	H11D—C11'—H11F	109.5
C9—C4—C5	115.8 (2)	H11E—C11'—H11F	109.5
C9—C4—C3	120.5 (2)	C13'—C12'—N2	113.2 (13)
C5—C4—C3	123.7 (3)	C13'—C12'—H12C	108.9
O2—C5—C6	117.6 (2)	N2—C12'—H12C	108.9
O2—C5—C4	120.8 (2)	C13'—C12'—H12D	108.9
C6—C5—C4	121.6 (3)	N2—C12'—H12D	108.9
C5—C6—C7	122.1 (3)	H12C—C12'—H12D	107.8
C5—C6—H6	118.9	C12'—C13'—H13D	109.5
C7—C6—H6	118.9	C12'—C13'—H13E	109.5
N2—C7—C6	122.1 (3)	H13D—C13'—H13E	109.5
N2—C7—C8	121.5 (3)	C12'—C13'—H13F	109.5
C6—C7—C8	116.3 (3)	H13D—C13'—H13F	109.5
C9—C8—C7	120.8 (3)	H13E—C13'—H13F	109.5

C3—N1—O1—C1	177.3 (2)	N2—C7—C8—C9	177.8 (4)
N1—O1—C1—C2	−179.6 (2)	C6—C7—C8—C9	−0.1 (5)
O1—C1—C2—C2ⁱ	178.8 (3)	C7—C8—C9—C4	1.4 (6)
O1—N1—C3—C4	−179.4 (2)	C5—C4—C9—C8	−1.7 (5)
N1—C3—C4—C9	−179.6 (3)	C3—C4—C9—C8	179.3 (3)
N1—C3—C4—C5	1.5 (4)	C7—N2—C10—C11	−92.1 (8)
C9—C4—C5—O2	−178.9 (3)	C12—N2—C10—C11	78.4 (9)
C3—C4—C5—O2	0.1 (4)	C10'—N2—C10—C11	17.7 (8)
C9—C4—C5—C6	0.7 (4)	C12'—N2—C10—C11	122.3 (9)
C3—C4—C5—C6	179.7 (3)	C7—N2—C12—C13	−97.9 (8)
O2—C5—C6—C7	−179.8 (3)	C10'—N2—C12—C13	125.0 (8)
C4—C5—C6—C7	0.6 (5)	C10—N2—C12—C13	91.8 (9)
C12—N2—C7—C6	−152.3 (6)	C12'—N2—C12—C13	7.7 (11)
C10'—N2—C7—C6	−26.5 (8)	C7—N2—C10'—C11'	93.2 (9)
C10—N2—C7—C6	18.3 (7)	C12—N2—C10'—C11'	−132.5 (8)
C12'—N2—C7—C6	159.7 (8)	C10—N2—C10'—C11'	−1.3 (8)
C12—N2—C7—C8	29.9 (7)	C12'—N2—C10'—C11'	−92.7 (10)
C10'—N2—C7—C8	155.7 (7)	C7—N2—C12'—C13'	88.0 (10)
C10—N2—C7—C8	−159.5 (6)	C12—N2—C12'—C13'	−11.8 (7)
C12'—N2—C7—C8	−18.1 (9)	C10'—N2—C12'—C13'	−86.3 (10)
C5—C6—C7—N2	−178.7 (3)	C10—N2—C12'—C13'	−127.6 (9)
C5—C6—C7—C8	−0.8 (5)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.91	2.639 (2)	147

Experimental details

Crystal data
Chemical formula	C₂₆H₃₈N₄O₄
M_r	470.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.6888 (9), 13.777 (2), 12.6547 (19)
β (°)	101.627 (2)
V (Å³)	1313.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.43 × 0.37

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	6450, 2303, 1176
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.152, 1.06
No. of reflections	2303
No. of parameters	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.15

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.913	2.639 (2)	147.01

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (grant No. 0604-01) and the Qing Lan Talent Engineering Fund of Lanzhou Jiaotong University (grant No. QL-03-01A), which are gratefully acknowledged.

References

Abu-Surrah, A. S., Thewalt, U. & Rieger, B. (1999). J. Organomet. Chem. 587, 58–66. Web of Science CSD CrossRef CAS Google Scholar
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Dong, W. K., Duan, J. G., Dong, C. M., Ren, Z. L. & Shi, J. Y. (2007). Z. Kristallogr. New Cryst. Struct. 222, 327–328. CAS Google Scholar
Dong, W. K., He, X. N., Dong, C. M., Wang, L., Zhong, J. K., Chen, X. & Yu, T. Z. (2007). Z. Kristallogr. New Cryst. Struct. 222, 289–290. CAS Google Scholar
Lacroix, P. G. (2001). Eur. J. Inorg. Chem. pp. 339–348. CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Zhang, Y.-P., Chen, X., Shi, J.-Y., Xu, L. & Dong, W.-K. (2007). Acta Cryst. E63, o3852. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 4| April 2008| Page o659

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5,5′-Bis(di­ethyl­amino)-2,2′-[butane-1,4-diyldi­oxy­bis­(nitrilo­methyl­­idyne)]­diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5,5′-Bis(diethylamino)-2,2′-[butane-1,4-diyldioxybis(nitrilomethylidyne)]diphenol