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Acta Cryst. (2009). E65, o1226    [ doi:10.1107/S1600536809016407 ]

3-[(2-Hydroxyethyl)iminomethyl]-1,1'-bi-2-naphthol

Y. Zhang, K. Wang, L.-Z. Zhong and R.-X. Li

Abstract top

In the title compound, C23H19NO3, there is an intramolecular O-H...N hydrogen bond, which forms a six-membered ring, and intermolecular O-H...O hydrogen bonds stabilize the crystal structure.

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 (I), as the continuation of our previous studies.

As shown in Figure 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 the synthesis of the title compound, see: Chin et al. (2004).

Experimental top

The salen ligand,

3-((2-hydroxyethylimino)methyl)-1,1'-binaphthol was prepared by condensation of 3-carboxaldehyde-1,1'-binaphthol with 2-aminoethanol. Crystals suitable for X-ray analysis were obtained by slow evaporation of a ethanol /methylene chloride (1:5) solution of the compound.

Refinement top

All H atoms except the one bonded to O1 (which was freely refined) were placed in calculated positions and refined in the riding-model approximation with O—H = 0.82Å and C—H = 0.93 or 0.97 Å) using a riding model with Uiso(H) = 1.2 Ueq(C,O).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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
[Figure 1] Fig. 1. A perspective view of the title compound.
[Figure 2] Fig. 2. Intermolecular hydrogen bonding in the crystal structure of (I).
3-[(2-Hydroxyethyl)iminomethyl]-1,1'-bi-2-naphthol top
Crystal data top
C23H19NO3Dx = 1.291 Mg m−3
Mr = 357.39Mo Kα radiation
λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 3454 reflections
a = 12.6184 (3) Åθ = 2.7–22.4º
b = 9.7774 (2) ŵ = 0.09 mm−1
c = 29.7991 (6) ÅT = 296 K
V = 3676.47 (14) Å3Block, red
Z = 80.50 × 0.40 × 0.36 mm
F000 = 1504
Data collection top
Bruker SMART CCD area-detector
diffractometer		4220 independent reflections
Radiation source: fine-focus sealed tube1912 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.089
T = 296 Kθmax = 27.6º
φ and ω scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −15→16
Tmin = 0.661, Tmax = 1.000k = −12→12
24940 measured reflectionsl = −38→38
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.135  w = 1/[σ2(Fo2) + (0.0475P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4220 reflectionsΔρmax = 0.15 e Å−3
252 parametersΔρmin = −0.14 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C23H19NO3V = 3676.47 (14) Å3
Mr = 357.39Z = 8
Orthorhombic, PbcaMo Kα
a = 12.6184 (3) ŵ = 0.09 mm−1
b = 9.7774 (2) ÅT = 296 K
c = 29.7991 (6) Å0.50 × 0.40 × 0.36 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4220 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		1912 reflections with I > 2σ(I)
Tmin = 0.661, Tmax = 1.000Rint = 0.089
24940 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055252 parameters
wR(F2) = 0.135H atoms treated by a mixture of
independent and constrained refinement
S = 1.00Δρmax = 0.15 e Å−3
4220 reflectionsΔρmin = −0.14 e Å−3
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
xyzUiso*/Ueq
O10.50545 (11)0.24608 (12)0.43973 (4)0.0661 (4)
H10.5349 (18)0.278 (2)0.4675 (8)0.109 (8)*
O20.31307 (9)−0.02597 (13)0.38718 (4)0.0615 (4)
H2A0.2483−0.03210.38600.092*
O30.60553 (9)0.53599 (13)0.59680 (4)0.0647 (4)
H3A0.57900.61250.59630.097*
N10.60154 (12)0.25597 (15)0.51551 (4)0.0528 (4)
C10.54441 (13)0.11749 (16)0.43397 (5)0.0423 (5)
C20.52157 (13)0.04833 (17)0.39500 (5)0.0406 (4)
C30.56310 (13)−0.08531 (17)0.38917 (5)0.0424 (5)
C40.54263 (15)−0.16310 (18)0.35028 (6)0.0572 (6)
H4A0.5016−0.12550.32750.069*
C50.58156 (16)−0.2919 (2)0.34540 (7)0.0696 (6)
H5A0.5678−0.34060.31920.083*
C60.64219 (16)−0.3519 (2)0.37943 (7)0.0710 (6)
H6A0.6673−0.44070.37610.085*
C70.66425 (15)−0.28066 (19)0.41715 (7)0.0617 (6)
H7A0.7059−0.32070.43930.074*
C80.62541 (13)−0.14683 (17)0.42360 (6)0.0445 (5)
C90.64473 (13)−0.07085 (18)0.46275 (6)0.0478 (5)
H9A0.6848−0.11040.48550.057*
C100.60711 (12)0.05847 (17)0.46872 (5)0.0392 (4)
C110.62936 (13)0.13284 (19)0.51008 (5)0.0452 (5)
H11A0.6693 (11)0.0826 (15)0.5322 (5)0.044 (4)*
C120.62678 (15)0.32605 (17)0.55768 (5)0.0530 (5)
H12A0.70290.32700.56230.064*
H12B0.59430.27830.58270.064*
C130.58577 (14)0.46884 (18)0.55525 (6)0.0549 (5)
H13A0.62070.51770.53110.066*
H13B0.51020.46770.54920.066*
C140.45087 (14)0.11281 (17)0.36073 (5)0.0432 (5)
C150.34642 (14)0.07470 (18)0.35878 (5)0.0472 (5)
C160.27531 (15)0.1368 (2)0.32883 (6)0.0590 (6)
H16A0.20460.10990.32830.071*
C170.31035 (17)0.2365 (2)0.30064 (6)0.0650 (6)
H17A0.26260.27820.28120.078*
C180.41683 (16)0.27781 (19)0.30024 (6)0.0549 (5)
C190.45588 (19)0.3789 (2)0.27067 (6)0.0702 (6)
H19A0.40920.42170.25100.084*
C200.5592 (2)0.4152 (2)0.27016 (6)0.0761 (7)
H20A0.58320.48110.25010.091*
C210.62985 (19)0.3531 (2)0.29999 (6)0.0734 (7)
H21A0.70090.37830.29970.088*
C220.59561 (16)0.25552 (19)0.32973 (6)0.0593 (6)
H22A0.64370.21600.34950.071*
C230.48854 (15)0.21437 (18)0.33073 (5)0.0478 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0975 (10)0.0520 (8)0.0489 (8)0.0232 (7)−0.0257 (8)−0.0095 (6)
O20.0562 (8)0.0747 (9)0.0536 (8)−0.0005 (7)0.0008 (6)0.0132 (7)
O30.0730 (8)0.0630 (8)0.0579 (8)0.0175 (7)−0.0196 (7)−0.0187 (7)
N10.0659 (10)0.0540 (10)0.0385 (9)0.0022 (8)−0.0086 (8)−0.0029 (7)
C10.0485 (10)0.0401 (10)0.0382 (10)0.0048 (8)0.0000 (9)0.0015 (8)
C20.0447 (10)0.0445 (10)0.0325 (9)0.0024 (8)−0.0005 (8)−0.0010 (8)
C30.0442 (10)0.0481 (11)0.0350 (10)0.0015 (8)0.0035 (8)−0.0005 (8)
C40.0661 (13)0.0612 (13)0.0442 (11)0.0094 (10)0.0003 (10)−0.0067 (10)
C50.0841 (15)0.0675 (14)0.0571 (13)0.0148 (11)0.0012 (12)−0.0223 (11)
C60.0750 (14)0.0562 (13)0.0816 (15)0.0182 (11)−0.0013 (13)−0.0155 (11)
C70.0581 (12)0.0565 (12)0.0704 (14)0.0155 (10)−0.0078 (11)−0.0059 (11)
C80.0423 (10)0.0461 (10)0.0450 (10)0.0051 (8)−0.0011 (9)−0.0022 (9)
C90.0427 (10)0.0554 (11)0.0454 (11)0.0046 (9)−0.0074 (9)0.0066 (9)
C100.0424 (9)0.0431 (10)0.0322 (9)0.0011 (8)0.0007 (8)0.0040 (8)
C110.0480 (10)0.0522 (11)0.0355 (10)0.0006 (9)−0.0055 (9)0.0067 (9)
C120.0664 (12)0.0519 (11)0.0407 (11)−0.0016 (10)−0.0094 (10)−0.0035 (9)
C130.0604 (12)0.0573 (12)0.0471 (11)0.0057 (9)−0.0105 (10)−0.0088 (9)
C140.0518 (10)0.0497 (11)0.0282 (9)0.0076 (8)−0.0024 (8)−0.0025 (8)
C150.0534 (11)0.0523 (11)0.0359 (10)0.0084 (9)0.0005 (9)0.0014 (9)
C160.0555 (12)0.0790 (14)0.0426 (10)0.0097 (10)−0.0091 (10)0.0000 (10)
C170.0763 (14)0.0760 (14)0.0425 (11)0.0176 (11)−0.0132 (11)0.0057 (10)
C180.0778 (14)0.0557 (12)0.0312 (10)0.0066 (10)−0.0039 (10)−0.0003 (9)
C190.1052 (17)0.0666 (14)0.0390 (12)0.0089 (12)−0.0046 (12)0.0044 (10)
C200.1250 (19)0.0609 (14)0.0425 (12)−0.0102 (13)0.0083 (13)0.0062 (10)
C210.0907 (16)0.0754 (15)0.0542 (13)−0.0164 (12)0.0142 (12)−0.0060 (12)
C220.0715 (13)0.0649 (13)0.0414 (11)−0.0009 (10)0.0031 (11)−0.0015 (10)
C230.0616 (12)0.0521 (11)0.0297 (10)0.0056 (9)0.0017 (9)−0.0043 (9)
Geometric parameters (Å, °) top
O1—C11.3609 (19)C10—C111.458 (2)
O1—H10.96 (2)C11—H11A0.964 (14)
O2—C151.3646 (19)C12—C131.491 (2)
O2—H2A0.8200C12—H12A0.9700
O3—C131.423 (2)C12—H12B0.9700
O3—H3A0.8200C13—H13A0.9700
N1—C111.264 (2)C13—H13B0.9700
N1—C121.466 (2)C14—C151.371 (2)
C1—C21.374 (2)C14—C231.418 (2)
C1—C101.425 (2)C15—C161.404 (2)
C2—C31.418 (2)C16—C171.361 (3)
C2—C141.495 (2)C16—H16A0.9300
C3—C41.410 (2)C17—C181.403 (3)
C3—C81.426 (2)C17—H17A0.9300
C4—C51.360 (3)C18—C191.413 (3)
C4—H4A0.9300C18—C231.425 (2)
C5—C61.399 (3)C19—C201.352 (3)
C5—H5A0.9300C19—H19A0.9300
C6—C71.351 (3)C20—C211.398 (3)
C6—H6A0.9300C20—H20A0.9300
C7—C81.410 (2)C21—C221.372 (3)
C7—H7A0.9300C21—H21A0.9300
C8—C91.404 (2)C22—C231.410 (3)
C9—C101.362 (2)C22—H22A0.9300
C9—H9A0.9300
C1—O1—H1105.5 (13)N1—C12—H12B109.9
C15—O2—H2A109.5C13—C12—H12B109.9
C13—O3—H3A109.5H12A—C12—H12B108.3
C11—N1—C12119.62 (14)O3—C13—C12109.21 (14)
O1—C1—C2119.04 (15)O3—C13—H13A109.8
O1—C1—C10118.87 (14)C12—C13—H13A109.8
C2—C1—C10122.08 (15)O3—C13—H13B109.8
C1—C2—C3118.63 (15)C12—C13—H13B109.8
C1—C2—C14119.65 (15)H13A—C13—H13B108.3
C3—C2—C14121.68 (14)C15—C14—C23119.07 (15)
C4—C3—C2121.99 (15)C15—C14—C2119.20 (15)
C4—C3—C8117.70 (15)C23—C14—C2121.71 (15)
C2—C3—C8120.29 (15)O2—C15—C14117.79 (15)
C5—C4—C3121.41 (17)O2—C15—C16120.60 (16)
C5—C4—H4A119.3C14—C15—C16121.60 (17)
C3—C4—H4A119.3C17—C16—C15119.64 (18)
C4—C5—C6120.56 (18)C17—C16—H16A120.2
C4—C5—H5A119.7C15—C16—H16A120.2
C6—C5—H5A119.7C16—C17—C18121.51 (18)
C7—C6—C5119.96 (19)C16—C17—H17A119.2
C7—C6—H6A120.0C18—C17—H17A119.2
C5—C6—H6A120.0C17—C18—C19122.73 (18)
C6—C7—C8121.33 (18)C17—C18—C23118.52 (17)
C6—C7—H7A119.3C19—C18—C23118.75 (19)
C8—C7—H7A119.3C20—C19—C18121.8 (2)
C9—C8—C7122.93 (16)C20—C19—H19A119.1
C9—C8—C3118.05 (15)C18—C19—H19A119.1
C7—C8—C3119.02 (16)C19—C20—C21119.6 (2)
C10—C9—C8122.62 (16)C19—C20—H20A120.2
C10—C9—H9A118.7C21—C20—H20A120.2
C8—C9—H9A118.7C22—C21—C20120.8 (2)
C9—C10—C1118.31 (15)C22—C21—H21A119.6
C9—C10—C11120.41 (15)C20—C21—H21A119.6
C1—C10—C11121.27 (15)C21—C22—C23120.92 (19)
N1—C11—C10121.97 (16)C21—C22—H22A119.5
N1—C11—H11A122.9 (9)C23—C22—H22A119.5
C10—C11—H11A115.1 (9)C22—C23—C14122.30 (16)
N1—C12—C13108.70 (14)C22—C23—C18118.10 (17)
N1—C12—H12A109.9C14—C23—C18119.61 (17)
C13—C12—H12A109.9
O1—C1—C2—C3179.60 (15)C11—N1—C12—C13179.82 (16)
C10—C1—C2—C3−0.8 (2)N1—C12—C13—O3177.37 (14)
O1—C1—C2—C14−2.7 (2)C1—C2—C14—C15−99.84 (19)
C10—C1—C2—C14176.94 (15)C3—C2—C14—C1577.8 (2)
C1—C2—C3—C4179.57 (16)C1—C2—C14—C2378.9 (2)
C14—C2—C3—C41.9 (2)C3—C2—C14—C23−103.43 (19)
C1—C2—C3—C81.2 (2)C23—C14—C15—O2178.20 (14)
C14—C2—C3—C8−176.48 (15)C2—C14—C15—O2−3.0 (2)
C2—C3—C4—C5−178.97 (17)C23—C14—C15—C16−2.0 (3)
C8—C3—C4—C5−0.6 (3)C2—C14—C15—C16176.74 (15)
C3—C4—C5—C60.9 (3)O2—C15—C16—C17−179.66 (16)
C4—C5—C6—C7−1.3 (3)C14—C15—C16—C170.6 (3)
C5—C6—C7—C81.4 (3)C15—C16—C17—C181.0 (3)
C6—C7—C8—C9178.55 (18)C16—C17—C18—C19178.59 (18)
C6—C7—C8—C3−1.0 (3)C16—C17—C18—C23−1.0 (3)
C4—C3—C8—C9−179.00 (15)C17—C18—C19—C20−178.56 (19)
C2—C3—C8—C9−0.6 (2)C23—C18—C19—C201.0 (3)
C4—C3—C8—C70.6 (2)C18—C19—C20—C21−1.0 (3)
C2—C3—C8—C7179.02 (16)C19—C20—C21—C220.2 (3)
C7—C8—C9—C10179.89 (17)C20—C21—C22—C230.6 (3)
C3—C8—C9—C10−0.5 (2)C21—C22—C23—C14179.33 (17)
C8—C9—C10—C11.0 (2)C21—C22—C23—C18−0.5 (3)
C8—C9—C10—C11179.91 (15)C15—C14—C23—C22−177.84 (16)
O1—C1—C10—C9179.33 (15)C2—C14—C23—C223.4 (3)
C2—C1—C10—C9−0.3 (2)C15—C14—C23—C182.0 (2)
O1—C1—C10—C110.4 (2)C2—C14—C23—C18−176.76 (15)
C2—C1—C10—C11−179.21 (15)C17—C18—C23—C22179.31 (17)
C12—N1—C11—C10−179.51 (15)C19—C18—C23—C22−0.3 (3)
C9—C10—C11—N1175.33 (16)C17—C18—C23—C14−0.5 (3)
C1—C10—C11—N1−5.7 (3)C19—C18—C23—C14179.91 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O3i0.821.872.6638 (17)161
O3—H3A···O1ii0.822.052.7724 (17)147
O1—H1···N10.96 (2)1.67 (2)2.5649 (18)153 (2)
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O3i0.821.872.6638 (17)161
O3—H3A···O1ii0.822.052.7724 (17)147
O1—H1···N10.96 (2)1.67 (2)2.5649 (18)153 (2)
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1.
Acknowledgements top

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references
References top

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Chin, J., Kim, D. C., Kim, H. J., Francis, B. P. & Kim, K. M. (2004). Org. Lett. 6, 2591–2593.

Pu, L. (1998). Chem. Rev. 98, 2405–2494.

Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.