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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1226.
Published online 2009 May 7. doi:  10.1107/S1600536809016407
PMCID: PMC2969659

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

Abstract

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.

Related literature

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

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Object name is e-65-o1226-scheme1.jpg

Experimental

Crystal data

  • C23H19NO3
  • M r = 357.39
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1226-efi1.jpg
  • a = 12.6184 (3) Å
  • b = 9.7774 (2) Å
  • c = 29.7991 (6) Å
  • V = 3676.47 (14) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.50 × 0.40 × 0.36 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.661, T max = 1.000 (expected range = 0.641–0.970)
  • 24940 measured reflections
  • 4220 independent reflections
  • 1912 reflections with I > 2σ(I)
  • R int = 0.089

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.135
  • S = 1.00
  • 4220 reflections
  • 252 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016407/bt2938sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016407/bt2938Isup2.hkl

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

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
A perspective view of the title compound.
Fig. 2.
Intermolecular hydrogen bonding in the crystal structure of (I).

Crystal data

C23H19NO3Dx = 1.291 Mg m3
Mr = 357.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 3454 reflections
a = 12.6184 (3) Åθ = 2.7–22.4°
b = 9.7774 (2) ŵ = 0.09 mm1
c = 29.7991 (6) ÅT = 296 K
V = 3676.47 (14) Å3Block, red
Z = 80.50 × 0.40 × 0.36 mm
F(000) = 1504

Data collection

Bruker SMART CCD area-detector diffractometer4220 independent reflections
Radiation source: fine-focus sealed tube1912 reflections with I > 2σ(I)
graphiteRint = 0.089
[var phi] and ω scansθmax = 27.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −15→16
Tmin = 0.661, Tmax = 1.000k = −12→12
24940 measured reflectionsl = −38→38

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0475P)2] where P = (Fo2 + 2Fc2)/3
4220 reflections(Δ/σ)max < 0.001
252 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.14 e Å3

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2938).

References

  • 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. [PubMed]
  • Pu, L. (1998). Chem. Rev.98, 2405–2494. [PubMed]
  • Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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