3-(n-Propyl­imino­meth­yl)-1,1′-bi-2-naphthol ethanol solvate

Zhong, L.-Z.; Wang, K.; Ma, X.-Y.; Li, R.-X.

doi:10.1107/S1600536808020436

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1438

doi:10.1107/S1600536808020436

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3-(n-Propyliminomethyl)-1,1′-bi-2-naphthol ethanol solvate

Ling-Zhi Zhong,^a Kun Wang,^a Xiao-Yan Ma ^a and Rui-Xiang Li ^a ^*

^aInstitute of Homogeneous Catalysis, Department of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: sculiruixiang@163.com

(Received 28 June 2008; accepted 3 July 2008; online 9 July 2008)

In the title compound, C₂₄H₂₁NO₂·C₂H₆O, the dihedral angle between the two aromatic ring systems is 87.00 (6)°. There is an intramolecular O—H⋯N hydrogen bond, which forms a six-membered ring. Intermolecular O—H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For background on the application of salen complexes to asymmetric catalysis, see: Pu (1998 ). For synthesis, see: Chin et al. (2004 ).

Experimental

Crystal data

C₂₄H₂₁NO₂·C₂H₆O
M_r = 401.49
Triclinic, $[P \overline 1]$
a = 10.356 (5) Å
b = 10.702 (4) Å
c = 11.681 (6) Å
α = 94.74 (3)°
β = 113.53 (4)°
γ = 110.21 (3)°
V = 1076.7 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 292 (2) K
0.42 × 0.40 × 0.38 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3981 measured reflections
3973 independent reflections
1867 reflections with I > 2σ(I)
R_int = 0.002
3 standard reflections every 300 reflections intensity decay: 2.1%

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.120
S = 0.94
3973 reflections
276 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.82	1.92	2.738 (2)	175
O2—H2⋯N1	0.82	1.85	2.590 (3)	149
O3—H3⋯O2	0.82	2.19	2.939 (3)	151
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); 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 I, global. DOI: 10.1107/S1600536808020436/bt2737sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020436/bt2737Isup2.hkl

checkCIF report

Comment top

Binol and its derivatives have been largely used in asymmetric catalysis and chiral recognition (Pu, 1998). In this paper we present X-ray crystallographic analysis of the title compound .

As shown in Fig. 1, an intramolecular O—H···N hydrogen bond between the hydroxy and the imino moieties forms a ring.

In the crystal, the molecules are connected by O—H···O hydrogen bonds (Fig. 2).

Related literature top

For background on the application of salen complexes to asymmetric catalysis, see: Pu (1998). For synthesis, see: Chin et al. (2004).

Experimental top

The salen ligand, 3-(n-propyliminomethyl)-1,1'-binaphthol was prepared by condensation of 3-carboxaldehyde-1,1'-binaphthol with n-propyamine, which was prepared by reported methods (Chin et al., 2004). Crystals suitable for X-ray analysis were obtained by slow evaporation of a ethanol /methylene chloride (1:5) solution of the compound.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); 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. A perspective view of the title compound.
	Fig. 2. Hydrogen bonding in the crystal structure of the title compound.

3-(n-Propyliminomethyl)-1,1'-bi-2-naphthol ethanol solvate top

Crystal data top

C₂₄H₂₁NO₂·C₂H₆O	Z = 2
M_r = 401.49	F(000) = 428
Triclinic, P1	D_x = 1.239 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.356 (5) Å	Cell parameters from 37 reflections
b = 10.702 (4) Å	θ = 4.6–9.7°
c = 11.681 (6) Å	µ = 0.08 mm⁻¹
α = 94.74 (3)°	T = 292 K
β = 113.53 (4)°	Block, red
γ = 110.21 (3)°	0.42 × 0.40 × 0.38 mm
V = 1076.7 (10) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.002
Radiation source: fine-focus sealed tube	θ_max = 25.4°, θ_min = 2.0°
Graphite monochromator	h = −12→11
ω/2–θ scans	k = −4→12
3981 measured reflections	l = −14→14
3973 independent reflections	3 standard reflections every 300 reflections
1867 reflections with I > 2σ(I)	intensity decay: 2.1%

Refinement top

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0567P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max < 0.001
3973 reflections	Δρ_max = 0.20 e Å⁻³
276 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (3)

Crystal data top

C₂₄H₂₁NO₂·C₂H₆O	γ = 110.21 (3)°
M_r = 401.49	V = 1076.7 (10) Å³
Triclinic, P1	Z = 2
a = 10.356 (5) Å	Mo Kα radiation
b = 10.702 (4) Å	µ = 0.08 mm⁻¹
c = 11.681 (6) Å	T = 292 K
α = 94.74 (3)°	0.42 × 0.40 × 0.38 mm
β = 113.53 (4)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.002
3981 measured reflections	3 standard reflections every 300 reflections
3973 independent reflections	intensity decay: 2.1%
1867 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 0.94	Δρ_max = 0.20 e Å⁻³
3973 reflections	Δρ_min = −0.16 e Å⁻³
276 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 > 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.

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

	x	y	z	U_iso*/U_eq
O1	1.05783 (17)	0.49721 (14)	0.36028 (17)	0.0594 (5)
H1	1.0117	0.5411	0.3732	0.071*
O2	1.23674 (17)	0.25319 (17)	0.46653 (16)	0.0542 (5)
H2	1.3092	0.2426	0.5213	0.065*
O3	1.0938 (2)	0.34869 (17)	0.60697 (19)	0.0706 (6)
H3	1.1196	0.3381	0.5503	0.085*
N1	1.5128 (2)	0.2638 (2)	0.5883 (2)	0.0577 (6)
C1	0.9549 (2)	0.3634 (2)	0.2954 (2)	0.0422 (6)
C2	0.8018 (3)	0.3178 (2)	0.2763 (2)	0.0499 (6)
H2A	0.7694	0.3791	0.3055	0.060*
C3	0.7007 (3)	0.1847 (2)	0.2154 (2)	0.0530 (7)
H3A	0.5997	0.1553	0.2039	0.064*
C4	0.7464 (2)	0.0903 (2)	0.1693 (2)	0.0438 (6)
C5	0.6427 (3)	−0.0497 (2)	0.1053 (2)	0.0574 (7)
H5	0.5418	−0.0811	0.0946	0.069*
C6	0.6889 (3)	−0.1383 (2)	0.0595 (2)	0.0631 (8)
H6	0.6194	−0.2294	0.0169	0.076*
C7	0.8399 (3)	−0.0930 (2)	0.0762 (2)	0.0571 (7)
H7	0.8705	−0.1542	0.0444	0.069*
C8	0.9434 (3)	0.0399 (2)	0.1384 (2)	0.0470 (6)
H8	1.0439	0.0681	0.1488	0.056*
C9	0.9004 (2)	0.1357 (2)	0.1875 (2)	0.0379 (5)
C10	1.0073 (2)	0.2762 (2)	0.25333 (19)	0.0365 (5)
C11	1.1704 (2)	0.3247 (2)	0.2740 (2)	0.0375 (5)
C12	1.2792 (2)	0.3084 (2)	0.3796 (2)	0.0408 (6)
C13	1.4355 (2)	0.3485 (2)	0.4005 (2)	0.0445 (6)
C14	1.4773 (3)	0.4108 (2)	0.3151 (2)	0.0511 (7)
H14	1.5796	0.4407	0.3302	0.061*
C15	1.3714 (3)	0.4312 (2)	0.2059 (2)	0.0461 (6)
C16	1.4142 (3)	0.4958 (2)	0.1180 (3)	0.0625 (7)
H16	1.5173	0.5310	0.1345	0.075*
C17	1.3077 (4)	0.5073 (3)	0.0103 (3)	0.0691 (8)
H17	1.3382	0.5510	−0.0460	0.083*
C18	1.1518 (3)	0.4538 (3)	−0.0169 (3)	0.0625 (7)
H18	1.0785	0.4583	−0.0933	0.075*
C19	1.1064 (3)	0.3949 (2)	0.0678 (2)	0.0490 (6)
H19	1.0027	0.3619	0.0493	0.059*
C20	1.2138 (2)	0.3833 (2)	0.1827 (2)	0.0418 (6)
C21	1.5484 (3)	0.3257 (2)	0.5097 (3)	0.0539 (7)
H21	1.6501	0.3574	0.5226	0.065*
C22	1.6320 (3)	0.2426 (2)	0.6952 (2)	0.0657 (8)
H22A	1.6428	0.2869	0.7764	0.079*
H22B	1.7303	0.2855	0.6937	0.079*
C23	1.5938 (3)	0.0939 (3)	0.6875 (2)	0.0654 (8)
H23A	1.5885	0.0510	0.6083	0.078*
H23B	1.4925	0.0502	0.6837	0.078*
C24	1.7112 (3)	0.0693 (3)	0.8015 (3)	0.0837 (9)
H24A	1.8123	0.1147	0.8074	0.126*
H24B	1.6842	−0.0278	0.7895	0.126*
H24C	1.7115	0.1055	0.8796	0.126*
C25	1.0527 (4)	0.2247 (3)	0.6459 (3)	0.0819 (9)
H25A	1.0438	0.2428	0.7246	0.098*
H25B	1.1341	0.1927	0.6647	0.098*
C26	0.9048 (4)	0.1156 (3)	0.5454 (3)	0.1148 (13)
H26A	0.8227	0.1446	0.5305	0.172*
H26B	0.8834	0.0325	0.5739	0.172*
H26C	0.9123	0.0988	0.4668	0.172*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0426 (10)	0.0422 (9)	0.0837 (13)	0.0137 (8)	0.0270 (9)	−0.0041 (9)
O2	0.0418 (10)	0.0671 (10)	0.0566 (12)	0.0264 (9)	0.0201 (9)	0.0260 (9)
O3	0.0925 (15)	0.0585 (11)	0.0825 (15)	0.0393 (11)	0.0532 (12)	0.0186 (10)
N1	0.0453 (13)	0.0549 (13)	0.0607 (15)	0.0258 (11)	0.0092 (11)	0.0122 (11)
C1	0.0345 (13)	0.0363 (12)	0.0501 (15)	0.0130 (11)	0.0161 (11)	0.0073 (11)
C2	0.0412 (14)	0.0496 (15)	0.0622 (17)	0.0217 (12)	0.0250 (12)	0.0099 (12)
C3	0.0330 (13)	0.0586 (16)	0.0629 (17)	0.0177 (12)	0.0194 (12)	0.0116 (13)
C4	0.0338 (13)	0.0431 (13)	0.0457 (15)	0.0125 (11)	0.0132 (11)	0.0096 (11)
C5	0.0389 (14)	0.0526 (15)	0.0619 (17)	0.0091 (13)	0.0153 (13)	0.0083 (13)
C6	0.0558 (18)	0.0429 (15)	0.0629 (19)	0.0072 (14)	0.0147 (14)	0.0022 (13)
C7	0.0617 (18)	0.0452 (15)	0.0572 (17)	0.0232 (13)	0.0211 (14)	0.0044 (12)
C8	0.0443 (14)	0.0472 (14)	0.0486 (15)	0.0222 (12)	0.0182 (12)	0.0090 (12)
C9	0.0346 (13)	0.0406 (12)	0.0358 (13)	0.0162 (10)	0.0128 (10)	0.0107 (10)
C10	0.0290 (12)	0.0390 (12)	0.0369 (13)	0.0137 (10)	0.0112 (10)	0.0090 (10)
C11	0.0322 (12)	0.0351 (12)	0.0433 (14)	0.0149 (10)	0.0157 (11)	0.0056 (10)
C12	0.0390 (13)	0.0346 (12)	0.0485 (15)	0.0140 (10)	0.0213 (12)	0.0085 (11)
C13	0.0343 (13)	0.0403 (13)	0.0551 (16)	0.0180 (11)	0.0162 (12)	0.0054 (11)
C14	0.0366 (14)	0.0458 (14)	0.0752 (19)	0.0181 (12)	0.0298 (14)	0.0092 (13)
C15	0.0461 (15)	0.0442 (13)	0.0601 (17)	0.0235 (12)	0.0313 (13)	0.0133 (12)
C16	0.0649 (18)	0.0616 (17)	0.086 (2)	0.0319 (15)	0.0522 (17)	0.0241 (15)
C17	0.092 (2)	0.0770 (19)	0.080 (2)	0.0509 (18)	0.0620 (19)	0.0361 (16)
C18	0.085 (2)	0.0717 (18)	0.0572 (18)	0.0507 (17)	0.0407 (16)	0.0227 (15)
C19	0.0524 (15)	0.0507 (14)	0.0504 (16)	0.0271 (12)	0.0246 (13)	0.0130 (12)
C20	0.0439 (14)	0.0368 (12)	0.0488 (15)	0.0199 (11)	0.0232 (12)	0.0060 (11)
C21	0.0342 (14)	0.0452 (15)	0.0705 (19)	0.0178 (12)	0.0133 (13)	0.0060 (13)
C22	0.0535 (16)	0.0645 (17)	0.0633 (18)	0.0300 (14)	0.0085 (14)	0.0109 (14)
C23	0.0583 (17)	0.0684 (17)	0.0583 (17)	0.0280 (14)	0.0137 (14)	0.0221 (13)
C24	0.0665 (19)	0.096 (2)	0.088 (2)	0.0434 (17)	0.0230 (17)	0.0439 (18)
C25	0.123 (3)	0.077 (2)	0.074 (2)	0.056 (2)	0.056 (2)	0.0300 (17)
C26	0.122 (3)	0.078 (2)	0.123 (3)	0.015 (2)	0.059 (3)	0.025 (2)

Geometric parameters (Å, º) top

O1—C1	1.372 (2)	C13—C21	1.453 (3)
O1—H1	0.8200	C14—C15	1.404 (3)
O2—C12	1.360 (3)	C14—H14	0.9300
O2—H2	0.8200	C15—C16	1.414 (3)
O3—C25	1.419 (3)	C15—C20	1.430 (3)
O3—H3	0.8200	C16—C17	1.350 (4)
N1—C21	1.272 (3)	C16—H16	0.9300
N1—C22	1.464 (3)	C17—C18	1.399 (4)
C1—C10	1.376 (3)	C17—H17	0.9300
C1—C2	1.403 (3)	C18—C19	1.367 (3)
C2—C3	1.356 (3)	C18—H18	0.9300
C2—H2A	0.9300	C19—C20	1.409 (3)
C3—C4	1.406 (3)	C19—H19	0.9300
C3—H3A	0.9300	C21—H21	0.9300
C4—C9	1.415 (3)	C22—C23	1.486 (3)
C4—C5	1.421 (3)	C22—H22A	0.9700
C5—C6	1.359 (3)	C22—H22B	0.9700
C5—H5	0.9300	C23—C24	1.519 (3)
C6—C7	1.391 (3)	C23—H23A	0.9700
C6—H6	0.9300	C23—H23B	0.9700
C7—C8	1.362 (3)	C24—H24A	0.9600
C7—H7	0.9300	C24—H24B	0.9600
C8—C9	1.413 (3)	C24—H24C	0.9600
C8—H8	0.9300	C25—C26	1.480 (4)
C9—C10	1.435 (3)	C25—H25A	0.9700
C10—C11	1.493 (3)	C25—H25B	0.9700
C11—C12	1.372 (3)	C26—H26A	0.9600
C11—C20	1.424 (3)	C26—H26B	0.9600
C12—C13	1.433 (3)	C26—H26C	0.9600
C13—C14	1.371 (3)

C1—O1—H1	109.5	C17—C16—C15	121.1 (3)
C12—O2—H2	109.5	C17—C16—H16	119.5
C25—O3—H3	109.5	C15—C16—H16	119.5
C21—N1—C22	119.3 (2)	C16—C17—C18	120.3 (3)
O1—C1—C10	118.24 (19)	C16—C17—H17	119.9
O1—C1—C2	119.98 (19)	C18—C17—H17	119.9
C10—C1—C2	121.76 (19)	C19—C18—C17	120.5 (3)
C3—C2—C1	120.2 (2)	C19—C18—H18	119.8
C3—C2—H2A	119.9	C17—C18—H18	119.8
C1—C2—H2A	119.9	C18—C19—C20	121.2 (2)
C2—C3—C4	121.0 (2)	C18—C19—H19	119.4
C2—C3—H3A	119.5	C20—C19—H19	119.4
C4—C3—H3A	119.5	C19—C20—C11	122.5 (2)
C3—C4—C9	119.16 (19)	C19—C20—C15	117.8 (2)
C3—C4—C5	122.0 (2)	C11—C20—C15	119.7 (2)
C9—C4—C5	118.9 (2)	N1—C21—C13	122.2 (2)
C6—C5—C4	120.8 (2)	N1—C21—H21	118.9
C6—C5—H5	119.6	C13—C21—H21	118.9
C4—C5—H5	119.6	N1—C22—C23	111.9 (2)
C5—C6—C7	120.2 (2)	N1—C22—H22A	109.2
C5—C6—H6	119.9	C23—C22—H22A	109.2
C7—C6—H6	119.9	N1—C22—H22B	109.2
C8—C7—C6	120.8 (2)	C23—C22—H22B	109.2
C8—C7—H7	119.6	H22A—C22—H22B	107.9
C6—C7—H7	119.6	C22—C23—C24	112.9 (2)
C7—C8—C9	121.0 (2)	C22—C23—H23A	109.0
C7—C8—H8	119.5	C24—C23—H23A	109.0
C9—C8—H8	119.5	C22—C23—H23B	109.0
C8—C9—C4	118.3 (2)	C24—C23—H23B	109.0
C8—C9—C10	122.0 (2)	H23A—C23—H23B	107.8
C4—C9—C10	119.63 (19)	C23—C24—H24A	109.5
C1—C10—C9	118.25 (19)	C23—C24—H24B	109.5
C1—C10—C11	121.72 (18)	H24A—C24—H24B	109.5
C9—C10—C11	120.02 (18)	C23—C24—H24C	109.5
C12—C11—C20	119.3 (2)	H24A—C24—H24C	109.5
C12—C11—C10	119.8 (2)	H24B—C24—H24C	109.5
C20—C11—C10	120.84 (19)	O3—C25—C26	112.0 (3)
O2—C12—C11	118.8 (2)	O3—C25—H25A	109.2
O2—C12—C13	119.5 (2)	C26—C25—H25A	109.2
C11—C12—C13	121.7 (2)	O3—C25—H25B	109.2
C14—C13—C12	118.3 (2)	C26—C25—H25B	109.2
C14—C13—C21	120.4 (2)	H25A—C25—H25B	107.9
C12—C13—C21	121.4 (2)	C25—C26—H26A	109.5
C13—C14—C15	122.5 (2)	C25—C26—H26B	109.5
C13—C14—H14	118.7	H26A—C26—H26B	109.5
C15—C14—H14	118.7	C25—C26—H26C	109.5
C14—C15—C16	122.7 (2)	H26A—C26—H26C	109.5
C14—C15—C20	118.3 (2)	H26B—C26—H26C	109.5
C16—C15—C20	119.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.82	1.92	2.738 (2)	175
O2—H2···N1	0.82	1.85	2.590 (3)	149
O3—H3···O2	0.82	2.19	2.939 (3)	151

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁NO₂·C₂H₆O
M_r	401.49
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	10.356 (5), 10.702 (4), 11.681 (6)
α, β, γ (°)	94.74 (3), 113.53 (4), 110.21 (3)
V (Å³)	1076.7 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.40 × 0.38

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3981, 3973, 1867
R_int	0.002
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.120, 0.94
No. of reflections	3973
No. of parameters	276
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.16

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), 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
O1—H1···O3ⁱ	0.82	1.92	2.738 (2)	175.3
O2—H2···N1	0.82	1.85	2.590 (3)	149.1
O3—H3···O2	0.82	2.19	2.939 (3)	150.9

Symmetry code: (i) −x+2, −y+1, −z+1.

References

Chin, J., Kim, D. C., Kim, H. J., Francis, B. P. & Kim, K. M. (2004). Org. Lett. 6, 2591–2593. Web of Science CrossRef PubMed CAS Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association Pittsburgh Meeting. Abstract PA104. Google Scholar
Pu, L. (1998). Chem. Rev. 98, 2405–2494. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 8| August 2008| Page o1438

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