5,5'-Bis(diethyl-amino)-2,2'-[butane-1,4-diyldioxy-bis(nitrilo-methyl-idyne)]-diphenol.

The title complex, C(26)H(38)N(4)O(4), was synthesized by the reaction of 4-diethyl-amino-2-hydroxy-benzaldehyde with 1,4-bis-(amino-oxy)butane in ethanol. It crystallizes as discrete centrosymmetric molecules adopting an extended conformation where the two salicylaldoxime groups are separated from each other. Intra-molecular O-H⋯N hydrogen bonding is observed between the hydr-oxy groups and oxime N atoms. Inter-molecular π-π stacking inter-actions [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 = 470.60

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.06

2303 reflections

196 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAIn class="Chemical">NT; 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 datablocks global, I. DOI: 10.1107/S1600536808004352/hg2359sup1.cif

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

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

C26H38N4O4	F000 = 508
Mr = 470.60	Dx = 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 = 3.0–23.4º
b = 13.777 (2) Å	µ = 0.08 mm−1
c = 12.6547 (19) Å	T = 298 (2) K
β = 101.627 (2)º	Block, colourless
V = 1313.0 (3) Å3	0.45 × 0.43 × 0.37 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2303 independent reflections
Radiation source: fine-focus sealed tube	1176 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.965, Tmax = 0.971	k = −16→16
6450 measured reflections	l = −15→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.5356P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2303 reflections	Δρmax = 0.12 e Å−3
196 parameters	Δρmin = −0.15 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	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)

	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)

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)

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

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