Bis[4-(2-hydroxy­benzyl­amino)phen­yl] ether

Guo, Y.-N.; Ge, C.-H.; Zhang, X.-D.; Zhang, X.-Y.; Liu, Q.-T.

doi:10.1107/S1600536807061740

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o505

doi:10.1107/S1600536807061740

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Bis[4-(2-hydroxybenzylamino)phenyl] ether

Ya-Nan Guo,^a Chun-Hua Ge,^a ^* Xiang-Dong Zhang,^a Xiao-Yan Zhang ^a and Qi-Tao Liu ^a

^aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
^*Correspondence e-mail: chhge@lnu.edu.cn

(Received 12 November 2007; accepted 21 November 2007; online 23 January 2008)

The title compound, C₂₆H₂₄N₂O₃, was synthesized by reduction of the corresponding Schiff base. The molecule does not possess crystallographic or non-crystallographic symmetry. The dihedral angle between the oxygen-bridged benzene rings is 67.98 (8)°. Both hydroxyl groups are involved in O—H⋯O intramolecular hydrogen bonding. The molecules are linked into a two-dimensional network parallel to the (010) plane by N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Ge, Zhang, Zhang, Guan et al. (2003 ); Ge, Zhang, Zhang, Guo et al. (2003 ).

Experimental

Crystal data

C₂₆H₂₄N₂O₃
M_r = 412.47
Monoclinic, P 2₁ /n
a = 5.8241 (5) Å
b = 43.960 (4) Å
c = 8.2874 (7) Å
β = 92.287 (1)°
V = 2120.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 (2) K
0.30 × 0.26 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.971, T_max = 0.982
11851 measured reflections
4170 independent reflections
2737 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.095
S = 0.93
4170 reflections
296 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.90 (2)	1.80 (2)	2.628 (2)	152 (2)
O3—H3⋯N2	0.94 (3)	1.82 (3)	2.670 (2)	150 (2)
N1—H1B⋯O3ⁱ	0.88 (2)	2.00 (2)	2.876 (2)	179 (2)
N2—H2B⋯O1ⁱⁱ	0.88 (2)	2.03 (2)	2.914 (2)	176 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061740/ci2520sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807061740/ci2520Isup2.hkl

checkCIF report

Comment top

The title compound has amino and hydroxyl groups which are good donor and acceptor for hydrogen bonding (Fig. 1). There are rigid phenyl rings and flexible methylene units in the same molecule which is similar to the ligands reported by Ge, Zhang, Zhang, Guan et al. (2003) and Ge, Zhang, Zhang, Guo et al. (2003). The molecule can be used as a semi-rigid ligand for metal complex formation or as a host for small molecule.

The dihedral angles formed by the C1—C6 (A), C8—C13 (B), C14—C19 (C) and C21—C26 (D) benzene rings are: A/B 66.36 (8)°, B/C 67.98 (8)° and C/D 67.68 (8)°. Both hydroxyl groups in the title molecule are involved in O—H···O intramolecular hydrogen bonding (Table 1). The molecules are linked into a two-dimensional network parallel to the (0 1 0) plane by N—H···O hydrogen bonds (Fig. 2).

Related literature top

For related literature, see: Ge, Zhang, Zhang, Guan et al. (2003); Ge, Zhang, Zhang, Guo et al. (2003).

Experimental top

A solution of 4,4'-diaminodiphenyl ether (0.1 mol) in ethanol (50 ml) was added dropwise to a solution of salicylaldehyde (0.21 mol) in ethanol (50 ml). The mixture was stirred for 4 h. The resulting solution was filtered to obtain a Schiff base, and it was dried. The title compound was obtained by the reaction of the Schiff base (0.05 mol) with a solution of NaBH₄ (0.4 mol) in ethanol (30 ml). Removal of the solvent under vacuum gave a white solid. Single crystals of the title compound were obtained by evaporating a solution of above-mentioned solid (0.2 mmol) in ethanol-water (30 ml, 2:1 v/v).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound.

Bis[4-(2-hydroxybenzylamino)phenyl] ether top

Crystal data top

C₂₆H₂₄N₂O₃	F(000) = 872
M_r = 412.47	D_x = 1.292 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 774 reflections
a = 5.8241 (5) Å	θ = 2.5–22.7°
b = 43.960 (4) Å	µ = 0.09 mm⁻¹
c = 8.2874 (7) Å	T = 295 K
β = 92.287 (1)°	Block, colourless
V = 2120.1 (3) Å³	0.30 × 0.26 × 0.13 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4170 independent reflections
Radiation source: fine-focus sealed tube	2737 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 26.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
T_min = 0.971, T_max = 0.982	k = −49→54
11851 measured reflections	l = −9→10

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ²(F_o²) + (0.0352P)²] where P = (F_o² + 2F_c²)/3
4170 reflections	(Δ/σ)_max = 0.001
296 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₆H₂₄N₂O₃	V = 2120.1 (3) Å³
M_r = 412.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8241 (5) Å	µ = 0.09 mm⁻¹
b = 43.960 (4) Å	T = 295 K
c = 8.2874 (7) Å	0.30 × 0.26 × 0.13 mm
β = 92.287 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4170 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2737 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.982	R_int = 0.046
11851 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	Δρ_max = 0.20 e Å⁻³
4170 reflections	Δρ_min = −0.21 e Å⁻³
296 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
O1	−0.1278 (2)	0.10829 (3)	0.88351 (16)	0.0397 (3)
O2	0.5755 (2)	0.23713 (3)	0.53721 (16)	0.0457 (4)
N1	0.1605 (3)	0.12562 (3)	0.66554 (19)	0.0330 (4)
N2	0.2491 (3)	0.35409 (3)	0.65634 (19)	0.0343 (4)
C17	0.3126 (3)	0.32377 (4)	0.6221 (2)	0.0300 (4)
C19	0.5823 (3)	0.28987 (4)	0.4995 (2)	0.0336 (4)
H19	0.7096	0.2870	0.4369	0.040*
C6	0.1360 (3)	0.07358 (4)	0.7657 (2)	0.0305 (4)
C18	0.5022 (3)	0.31878 (4)	0.5268 (2)	0.0323 (4)
H18	0.5753	0.3353	0.4812	0.039*
C1	−0.0656 (3)	0.07893 (4)	0.8465 (2)	0.0313 (4)
O3	0.3648 (2)	0.39237 (3)	0.89618 (17)	0.0507 (4)
C12	0.2522 (3)	0.20261 (4)	0.5023 (2)	0.0367 (5)
H12	0.1763	0.2162	0.4325	0.044*
C16	0.2036 (3)	0.29862 (4)	0.6834 (2)	0.0401 (5)
H16	0.0741	0.3013	0.7439	0.048*
C14	0.4741 (3)	0.26513 (4)	0.5647 (2)	0.0326 (4)
C13	0.1566 (3)	0.17455 (4)	0.5332 (2)	0.0339 (4)
H13	0.0145	0.1695	0.4853	0.041*
C11	0.4610 (3)	0.21042 (4)	0.5755 (2)	0.0348 (5)
C15	0.2846 (3)	0.26944 (4)	0.6559 (2)	0.0412 (5)
H15	0.2106	0.2528	0.6994	0.049*
C10	0.5729 (3)	0.19037 (4)	0.6786 (2)	0.0376 (5)
H10	0.7122	0.1958	0.7294	0.045*
C20	0.0224 (3)	0.36069 (4)	0.7182 (2)	0.0402 (5)
H20A	0.0016	0.3493	0.8169	0.048*
H20B	−0.0964	0.3545	0.6396	0.048*
C26	0.1751 (3)	0.40877 (4)	0.8431 (2)	0.0361 (5)
C21	0.0020 (3)	0.39425 (4)	0.7514 (2)	0.0331 (4)
C2	−0.2046 (3)	0.05532 (4)	0.8928 (2)	0.0395 (5)
H2	−0.3369	0.0593	0.9483	0.047*
C8	0.2693 (3)	0.15367 (4)	0.6348 (2)	0.0300 (4)
C5	0.1885 (3)	0.04368 (4)	0.7293 (2)	0.0445 (5)
H5	0.3207	0.0395	0.6740	0.053*
C3	−0.1467 (3)	0.02578 (4)	0.8566 (2)	0.0458 (5)
H3A	−0.2396	0.0098	0.8882	0.055*
C7	0.2944 (3)	0.09951 (4)	0.7283 (2)	0.0372 (5)
H7A	0.3815	0.1054	0.8255	0.045*
H7B	0.4021	0.0931	0.6488	0.045*
C9	0.4781 (3)	0.16194 (4)	0.7071 (2)	0.0365 (5)
H9	0.5560	0.1483	0.7756	0.044*
C25	0.1609 (3)	0.43923 (4)	0.8814 (2)	0.0455 (5)
H25	0.2769	0.4486	0.9438	0.055*
C22	−0.1831 (3)	0.41142 (4)	0.6961 (2)	0.0447 (5)
H22	−0.2991	0.4022	0.6331	0.054*
C24	−0.0287 (4)	0.45572 (5)	0.8255 (2)	0.0501 (6)
H24	−0.0403	0.4762	0.8510	0.060*
C4	0.0490 (3)	0.01987 (4)	0.7735 (3)	0.0524 (6)
H4	0.0869	0.0000	0.7473	0.063*
C23	−0.1999 (4)	0.44200 (5)	0.7326 (2)	0.0513 (6)
H23	−0.3261	0.4532	0.6945	0.062*
H1	−0.051 (3)	0.1201 (5)	0.815 (2)	0.065 (7)*
H3	0.369 (4)	0.3753 (6)	0.828 (3)	0.105 (10)*
H1B	0.071 (3)	0.1200 (4)	0.583 (2)	0.037 (6)*
H2B	0.283 (3)	0.3663 (4)	0.576 (2)	0.042 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0467 (9)	0.0271 (8)	0.0462 (9)	0.0022 (6)	0.0127 (7)	−0.0026 (6)
O2	0.0470 (9)	0.0249 (8)	0.0666 (10)	−0.0008 (6)	0.0198 (7)	0.0036 (6)
N1	0.0368 (10)	0.0274 (9)	0.0341 (10)	−0.0040 (7)	−0.0070 (8)	0.0043 (7)
N2	0.0420 (10)	0.0268 (9)	0.0345 (10)	−0.0023 (7)	0.0082 (8)	0.0037 (7)
C17	0.0382 (11)	0.0248 (10)	0.0268 (10)	−0.0034 (8)	−0.0024 (8)	0.0000 (8)
C19	0.0323 (11)	0.0345 (11)	0.0343 (11)	−0.0036 (8)	0.0043 (8)	−0.0014 (8)
C6	0.0351 (11)	0.0236 (10)	0.0327 (11)	0.0013 (8)	−0.0007 (8)	0.0012 (8)
C18	0.0361 (11)	0.0268 (11)	0.0341 (11)	−0.0078 (8)	0.0019 (9)	0.0031 (8)
C1	0.0376 (11)	0.0231 (10)	0.0331 (11)	0.0011 (8)	−0.0008 (8)	−0.0004 (8)
O3	0.0562 (10)	0.0435 (9)	0.0507 (9)	0.0096 (7)	−0.0195 (7)	−0.0059 (7)
C12	0.0444 (12)	0.0294 (11)	0.0364 (11)	0.0078 (9)	0.0041 (9)	0.0043 (8)
C16	0.0479 (13)	0.0339 (12)	0.0395 (12)	−0.0022 (9)	0.0156 (9)	0.0003 (9)
C14	0.0382 (11)	0.0254 (11)	0.0343 (11)	−0.0015 (8)	0.0030 (9)	0.0004 (8)
C13	0.0355 (11)	0.0313 (11)	0.0346 (11)	0.0003 (8)	−0.0012 (9)	0.0004 (8)
C11	0.0404 (12)	0.0248 (11)	0.0400 (12)	−0.0003 (9)	0.0116 (9)	−0.0017 (8)
C15	0.0530 (13)	0.0258 (11)	0.0460 (12)	−0.0051 (9)	0.0161 (10)	0.0048 (9)
C10	0.0334 (11)	0.0362 (12)	0.0432 (12)	−0.0027 (9)	0.0013 (9)	−0.0008 (9)
C20	0.0412 (12)	0.0353 (12)	0.0444 (12)	−0.0022 (9)	0.0058 (9)	−0.0016 (9)
C26	0.0427 (12)	0.0346 (12)	0.0309 (11)	0.0040 (9)	0.0002 (9)	0.0030 (8)
C21	0.0362 (11)	0.0306 (11)	0.0328 (11)	−0.0008 (8)	0.0047 (8)	0.0014 (8)
C2	0.0366 (12)	0.0351 (12)	0.0468 (13)	−0.0008 (9)	0.0043 (9)	0.0025 (9)
C8	0.0349 (11)	0.0272 (10)	0.0280 (10)	0.0003 (8)	0.0037 (8)	−0.0019 (8)
C5	0.0472 (13)	0.0308 (12)	0.0564 (14)	0.0040 (9)	0.0138 (10)	−0.0008 (10)
C3	0.0469 (13)	0.0285 (12)	0.0620 (15)	−0.0067 (9)	0.0026 (11)	0.0034 (10)
C7	0.0389 (12)	0.0286 (11)	0.0444 (12)	0.0030 (8)	0.0070 (9)	0.0035 (9)
C9	0.0375 (12)	0.0314 (11)	0.0402 (12)	0.0003 (9)	−0.0012 (9)	0.0067 (9)
C25	0.0575 (15)	0.0345 (12)	0.0443 (13)	−0.0048 (10)	−0.0008 (10)	−0.0042 (9)
C22	0.0374 (12)	0.0460 (14)	0.0505 (13)	0.0030 (10)	−0.0001 (10)	−0.0027 (10)
C24	0.0648 (16)	0.0311 (12)	0.0552 (14)	0.0071 (11)	0.0124 (12)	−0.0003 (10)
C4	0.0619 (15)	0.0228 (11)	0.0732 (16)	0.0014 (10)	0.0101 (12)	−0.0034 (10)
C23	0.0451 (14)	0.0485 (14)	0.0605 (15)	0.0134 (11)	0.0035 (11)	0.0038 (11)

Geometric parameters (Å, º) top

O1—C1	1.3784 (19)	C13—H13	0.93
O1—H1	0.90 (2)	C11—C10	1.374 (2)
O2—C14	1.3883 (19)	C15—H15	0.93
O2—C11	1.394 (2)	C10—C9	1.390 (2)
N1—C8	1.414 (2)	C10—H10	0.93
N1—C7	1.471 (2)	C20—C21	1.506 (2)
N1—H1B	0.877 (17)	C20—H20A	0.97
N2—C17	1.415 (2)	C20—H20B	0.97
N2—C20	1.465 (2)	C26—C25	1.379 (2)
N2—H2B	0.882 (17)	C26—C21	1.393 (2)
C17—C16	1.381 (2)	C21—C22	1.379 (2)
C17—C18	1.400 (2)	C2—C3	1.378 (2)
C19—C18	1.375 (2)	C2—H2	0.93
C19—C14	1.378 (2)	C8—C9	1.383 (2)
C19—H19	0.93	C5—C4	1.383 (2)
C6—C5	1.385 (2)	C5—H5	0.93
C6—C1	1.395 (2)	C3—C4	1.380 (3)
C6—C7	1.507 (2)	C3—H3A	0.93
C18—H18	0.93	C7—H7A	0.97
C1—C2	1.380 (2)	C7—H7B	0.97
O3—C26	1.377 (2)	C9—H9	0.93
O3—H3	0.94 (3)	C25—C24	1.385 (3)
C12—C11	1.381 (2)	C25—H25	0.93
C12—C13	1.382 (2)	C22—C23	1.382 (3)
C12—H12	0.93	C22—H22	0.93
C16—C15	1.389 (2)	C24—C23	1.374 (3)
C16—H16	0.93	C24—H24	0.93
C14—C15	1.376 (2)	C4—H4	0.93
C13—C8	1.392 (2)	C23—H23	0.93

C1—O1—H1	105.1 (13)	C21—C20—H20A	109.7
C14—O2—C11	119.95 (13)	N2—C20—H20B	109.7
C8—N1—C7	120.62 (15)	C21—C20—H20B	109.7
C8—N1—H1B	111.2 (11)	H20A—C20—H20B	108.2
C7—N1—H1B	110.2 (11)	O3—C26—C25	119.30 (18)
C17—N2—C20	120.24 (15)	O3—C26—C21	119.25 (17)
C17—N2—H2B	110.8 (12)	C25—C26—C21	121.45 (18)
C20—N2—H2B	112.1 (11)	C22—C21—C26	118.01 (18)
C16—C17—C18	117.79 (16)	C22—C21—C20	122.77 (17)
C16—C17—N2	123.51 (16)	C26—C21—C20	119.21 (16)
C18—C17—N2	118.64 (15)	C3—C2—C1	119.80 (17)
C18—C19—C14	120.09 (16)	C3—C2—H2	120.1
C18—C19—H19	120.0	C1—C2—H2	120.1
C14—C19—H19	120.0	C9—C8—C13	118.32 (16)
C5—C6—C1	117.52 (16)	C9—C8—N1	122.91 (16)
C5—C6—C7	122.06 (16)	C13—C8—N1	118.70 (16)
C1—C6—C7	120.34 (15)	C4—C5—C6	121.54 (18)
C19—C18—C17	121.18 (16)	C4—C5—H5	119.2
C19—C18—H18	119.4	C6—C5—H5	119.2
C17—C18—H18	119.4	C2—C3—C4	120.01 (18)
O1—C1—C2	118.68 (16)	C2—C3—H3A	120.0
O1—C1—C6	119.93 (15)	C4—C3—H3A	120.0
C2—C1—C6	121.39 (16)	N1—C7—C6	110.04 (14)
C26—O3—H3	105.5 (15)	N1—C7—H7A	109.7
C11—C12—C13	119.65 (17)	C6—C7—H7A	109.7
C11—C12—H12	120.2	N1—C7—H7B	109.7
C13—C12—H12	120.2	C6—C7—H7B	109.7
C17—C16—C15	120.99 (17)	H7A—C7—H7B	108.2
C17—C16—H16	119.5	C8—C9—C10	120.73 (17)
C15—C16—H16	119.5	C8—C9—H9	119.6
C15—C14—C19	119.76 (16)	C10—C9—H9	119.6
C15—C14—O2	124.64 (15)	C26—C25—C24	119.02 (19)
C19—C14—O2	115.55 (15)	C26—C25—H25	120.5
C12—C13—C8	121.12 (17)	C24—C25—H25	120.5
C12—C13—H13	119.4	C21—C22—C23	121.37 (19)
C8—C13—H13	119.4	C21—C22—H22	119.3
C10—C11—C12	120.12 (17)	C23—C22—H22	119.3
C10—C11—O2	117.58 (17)	C23—C24—C25	120.6 (2)
C12—C11—O2	122.03 (17)	C23—C24—H24	119.7
C14—C15—C16	120.15 (16)	C25—C24—H24	119.7
C14—C15—H15	119.9	C3—C4—C5	119.71 (18)
C16—C15—H15	119.9	C3—C4—H4	120.1
C11—C10—C9	120.03 (18)	C5—C4—H4	120.1
C11—C10—H10	120.0	C24—C23—C22	119.54 (19)
C9—C10—H10	120.0	C24—C23—H23	120.2
N2—C20—C21	109.67 (14)	C22—C23—H23	120.2
N2—C20—H20A	109.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.90 (2)	1.80 (2)	2.628 (2)	152 (2)
O3—H3···N2	0.94 (3)	1.82 (3)	2.670 (2)	150 (2)
N1—H1B···O3ⁱ	0.88 (2)	2.00 (2)	2.876 (2)	179 (2)
N2—H2B···O1ⁱⁱ	0.88 (2)	2.03 (2)	2.914 (2)	176 (2)

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄N₂O₃
M_r	412.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	5.8241 (5), 43.960 (4), 8.2874 (7)
β (°)	92.287 (1)
V (Å³)	2120.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.26 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.971, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	11851, 4170, 2737
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.095, 0.93
No. of reflections	4170
No. of parameters	296
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.90 (2)	1.80 (2)	2.628 (2)	152 (2)
O3—H3···N2	0.94 (3)	1.82 (3)	2.670 (2)	150 (2)
N1—H1B···O3ⁱ	0.88 (2)	2.00 (2)	2.876 (2)	179 (2)
N2—H2B···O1ⁱⁱ	0.88 (2)	2.03 (2)	2.914 (2)	176 (2)

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z−1/2.

Acknowledgements

This work was supported by the Natural Science Foundation of the Education Bureau of Liaoning Province (grant No. 05 L159).

References

Bruker (2001). SMART (Version 5.624), SAINT (Version 6.04) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ge, C. H., Zhang, X. D., Zhang, P., Guan, W., Guo, F. & Liu, Q. T. (2003). Polyhedron, 22, 3493–3497. Web of Science CSD CrossRef CAS Google Scholar
Ge, C. H., Zhang, X. D., Zhang, P., Guo, F. & Liu, Q. T. (2003). Inorg. Chem. Commun. 6, 1061–1064. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar