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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1438.
Published online 2008 July 9. doi:  10.1107/S1600536808020436
PMCID: PMC2962069

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

Abstract

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 [triangle]). For synthesis, see: Chin et al. (2004 [triangle]).

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Object name is e-64-o1438-scheme1.jpg

Experimental

Crystal data

  • C24H21NO2·C2H6O
  • M r = 401.49
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1438-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.120
  • S = 0.94
  • 3973 reflections
  • 276 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 [triangle]); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 [triangle]); 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/S1600536808020436/bt2737sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020436/bt2737Isup2.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 .

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).

Experimental

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.

Refinement

All H atoms were placed in calculated positions and refined using a riding-model with C-H ranging from 0.93 to 0.97Å and O-H = 0.82Å and U(H)= 1.2Ueq(C,O) or U(H)= 1.5Ueq(Cmethyl). The methyl and hydroxyl groups were allowed to rotate but not to tip.

Figures

Fig. 1.
A perspective view of the title compound.
Fig. 2.
Hydrogen bonding in the crystal structure of the title compound.

Crystal data

C24H21NO2·C2H6OZ = 2
Mr = 401.49F000 = 428
Triclinic, P1Dx = 1.239 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.356 (5) ÅCell parameters from 37 reflections
b = 10.702 (4) Åθ = 4.6–9.7º
c = 11.681 (6) ŵ = 0.08 mm1
α = 94.74 (3)ºT = 292 (2) K
β = 113.53 (4)ºBlock, red
γ = 110.21 (3)º0.42 × 0.40 × 0.38 mm
V = 1076.7 (10) Å3

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.002
Radiation source: fine-focus sealed tubeθmax = 25.4º
Monochromator: graphiteθmin = 2.0º
T = 291(2) Kh = −12→11
ω/2–θ scansk = −4→12
Absorption correction: nonel = −14→14
3981 measured reflections3 standard reflections
3973 independent reflections every 300 reflections
1867 reflections with I > 2σ(I) intensity decay: 2.1%

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045  w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120(Δ/σ)max < 0.001
S = 0.94Δρmax = 0.20 e Å3
3973 reflectionsΔρmin = −0.16 e Å3
276 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.039 (3)
Secondary atom site location: difference Fourier map

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 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)

xyzUiso*/Ueq
O11.05783 (17)0.49721 (14)0.36028 (17)0.0594 (5)
H11.01170.54110.37320.071*
O21.23674 (17)0.25319 (17)0.46653 (16)0.0542 (5)
H21.30920.24260.52130.065*
O31.0938 (2)0.34869 (17)0.60697 (19)0.0706 (6)
H31.11960.33810.55030.085*
N11.5128 (2)0.2638 (2)0.5883 (2)0.0577 (6)
C10.9549 (2)0.3634 (2)0.2954 (2)0.0422 (6)
C20.8018 (3)0.3178 (2)0.2763 (2)0.0499 (6)
H2A0.76940.37910.30550.060*
C30.7007 (3)0.1847 (2)0.2154 (2)0.0530 (7)
H3A0.59970.15530.20390.064*
C40.7464 (2)0.0903 (2)0.1693 (2)0.0438 (6)
C50.6427 (3)−0.0497 (2)0.1053 (2)0.0574 (7)
H50.5418−0.08110.09460.069*
C60.6889 (3)−0.1383 (2)0.0595 (2)0.0631 (8)
H60.6194−0.22940.01690.076*
C70.8399 (3)−0.0930 (2)0.0762 (2)0.0571 (7)
H70.8705−0.15420.04440.069*
C80.9434 (3)0.0399 (2)0.1384 (2)0.0470 (6)
H81.04390.06810.14880.056*
C90.9004 (2)0.1357 (2)0.1875 (2)0.0379 (5)
C101.0073 (2)0.2762 (2)0.25333 (19)0.0365 (5)
C111.1704 (2)0.3247 (2)0.2740 (2)0.0375 (5)
C121.2792 (2)0.3084 (2)0.3796 (2)0.0408 (6)
C131.4355 (2)0.3485 (2)0.4005 (2)0.0445 (6)
C141.4773 (3)0.4108 (2)0.3151 (2)0.0511 (7)
H141.57960.44070.33020.061*
C151.3714 (3)0.4312 (2)0.2059 (2)0.0461 (6)
C161.4142 (3)0.4958 (2)0.1180 (3)0.0625 (7)
H161.51730.53100.13450.075*
C171.3077 (4)0.5073 (3)0.0103 (3)0.0691 (8)
H171.33820.5510−0.04600.083*
C181.1518 (3)0.4538 (3)−0.0169 (3)0.0625 (7)
H181.07850.4583−0.09330.075*
C191.1064 (3)0.3949 (2)0.0678 (2)0.0490 (6)
H191.00270.36190.04930.059*
C201.2138 (2)0.3833 (2)0.1827 (2)0.0418 (6)
C211.5484 (3)0.3257 (2)0.5097 (3)0.0539 (7)
H211.65010.35740.52260.065*
C221.6320 (3)0.2426 (2)0.6952 (2)0.0657 (8)
H22A1.64280.28690.77640.079*
H22B1.73030.28550.69370.079*
C231.5938 (3)0.0939 (3)0.6875 (2)0.0654 (8)
H23A1.58850.05100.60830.078*
H23B1.49250.05020.68370.078*
C241.7112 (3)0.0693 (3)0.8015 (3)0.0837 (9)
H24A1.81230.11470.80740.126*
H24B1.6842−0.02780.78950.126*
H24C1.71150.10550.87960.126*
C251.0527 (4)0.2247 (3)0.6459 (3)0.0819 (9)
H25A1.04380.24280.72460.098*
H25B1.13410.19270.66470.098*
C260.9048 (4)0.1156 (3)0.5454 (3)0.1148 (13)
H26A0.82270.14460.53050.172*
H26B0.88340.03250.57390.172*
H26C0.91230.09880.46680.172*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0426 (10)0.0422 (9)0.0837 (13)0.0137 (8)0.0270 (9)−0.0041 (9)
O20.0418 (10)0.0671 (10)0.0566 (12)0.0264 (9)0.0201 (9)0.0260 (9)
O30.0925 (15)0.0585 (11)0.0825 (15)0.0393 (11)0.0532 (12)0.0186 (10)
N10.0453 (13)0.0549 (13)0.0607 (15)0.0258 (11)0.0092 (11)0.0122 (11)
C10.0345 (13)0.0363 (12)0.0501 (15)0.0130 (11)0.0161 (11)0.0073 (11)
C20.0412 (14)0.0496 (15)0.0622 (17)0.0217 (12)0.0250 (12)0.0099 (12)
C30.0330 (13)0.0586 (16)0.0629 (17)0.0177 (12)0.0194 (12)0.0116 (13)
C40.0338 (13)0.0431 (13)0.0457 (15)0.0125 (11)0.0132 (11)0.0096 (11)
C50.0389 (14)0.0526 (15)0.0619 (17)0.0091 (13)0.0153 (13)0.0083 (13)
C60.0558 (18)0.0429 (15)0.0629 (19)0.0072 (14)0.0147 (14)0.0022 (13)
C70.0617 (18)0.0452 (15)0.0572 (17)0.0232 (13)0.0211 (14)0.0044 (12)
C80.0443 (14)0.0472 (14)0.0486 (15)0.0222 (12)0.0182 (12)0.0090 (12)
C90.0346 (13)0.0406 (12)0.0358 (13)0.0162 (10)0.0128 (10)0.0107 (10)
C100.0290 (12)0.0390 (12)0.0369 (13)0.0137 (10)0.0112 (10)0.0090 (10)
C110.0322 (12)0.0351 (12)0.0433 (14)0.0149 (10)0.0157 (11)0.0056 (10)
C120.0390 (13)0.0346 (12)0.0485 (15)0.0140 (10)0.0213 (12)0.0085 (11)
C130.0343 (13)0.0403 (13)0.0551 (16)0.0180 (11)0.0162 (12)0.0054 (11)
C140.0366 (14)0.0458 (14)0.0752 (19)0.0181 (12)0.0298 (14)0.0092 (13)
C150.0461 (15)0.0442 (13)0.0601 (17)0.0235 (12)0.0313 (13)0.0133 (12)
C160.0649 (18)0.0616 (17)0.086 (2)0.0319 (15)0.0522 (17)0.0241 (15)
C170.092 (2)0.0770 (19)0.080 (2)0.0509 (18)0.0620 (19)0.0361 (16)
C180.085 (2)0.0717 (18)0.0572 (18)0.0507 (17)0.0407 (16)0.0227 (15)
C190.0524 (15)0.0507 (14)0.0504 (16)0.0271 (12)0.0246 (13)0.0130 (12)
C200.0439 (14)0.0368 (12)0.0488 (15)0.0199 (11)0.0232 (12)0.0060 (11)
C210.0342 (14)0.0452 (15)0.0705 (19)0.0178 (12)0.0133 (13)0.0060 (13)
C220.0535 (16)0.0645 (17)0.0633 (18)0.0300 (14)0.0085 (14)0.0109 (14)
C230.0583 (17)0.0684 (17)0.0583 (17)0.0280 (14)0.0137 (14)0.0221 (13)
C240.0665 (19)0.096 (2)0.088 (2)0.0434 (17)0.0230 (17)0.0439 (18)
C250.123 (3)0.077 (2)0.074 (2)0.056 (2)0.056 (2)0.0300 (17)
C260.122 (3)0.078 (2)0.123 (3)0.015 (2)0.059 (3)0.025 (2)

Geometric parameters (Å, °)

O1—C11.372 (2)C13—C211.453 (3)
O1—H10.8200C14—C151.404 (3)
O2—C121.360 (3)C14—H140.9300
O2—H20.8200C15—C161.414 (3)
O3—C251.419 (3)C15—C201.430 (3)
O3—H30.8200C16—C171.350 (4)
N1—C211.272 (3)C16—H160.9300
N1—C221.464 (3)C17—C181.399 (4)
C1—C101.376 (3)C17—H170.9300
C1—C21.403 (3)C18—C191.367 (3)
C2—C31.356 (3)C18—H180.9300
C2—H2A0.9300C19—C201.409 (3)
C3—C41.406 (3)C19—H190.9300
C3—H3A0.9300C21—H210.9300
C4—C91.415 (3)C22—C231.486 (3)
C4—C51.421 (3)C22—H22A0.9700
C5—C61.359 (3)C22—H22B0.9700
C5—H50.9300C23—C241.519 (3)
C6—C71.391 (3)C23—H23A0.9700
C6—H60.9300C23—H23B0.9700
C7—C81.362 (3)C24—H24A0.9600
C7—H70.9300C24—H24B0.9600
C8—C91.413 (3)C24—H24C0.9600
C8—H80.9300C25—C261.480 (4)
C9—C101.435 (3)C25—H25A0.9700
C10—C111.493 (3)C25—H25B0.9700
C11—C121.372 (3)C26—H26A0.9600
C11—C201.424 (3)C26—H26B0.9600
C12—C131.433 (3)C26—H26C0.9600
C13—C141.371 (3)
C1—O1—H1109.5C17—C16—C15121.1 (3)
C12—O2—H2109.5C17—C16—H16119.5
C25—O3—H3109.5C15—C16—H16119.5
C21—N1—C22119.3 (2)C16—C17—C18120.3 (3)
O1—C1—C10118.24 (19)C16—C17—H17119.9
O1—C1—C2119.98 (19)C18—C17—H17119.9
C10—C1—C2121.76 (19)C19—C18—C17120.5 (3)
C3—C2—C1120.2 (2)C19—C18—H18119.8
C3—C2—H2A119.9C17—C18—H18119.8
C1—C2—H2A119.9C18—C19—C20121.2 (2)
C2—C3—C4121.0 (2)C18—C19—H19119.4
C2—C3—H3A119.5C20—C19—H19119.4
C4—C3—H3A119.5C19—C20—C11122.5 (2)
C3—C4—C9119.16 (19)C19—C20—C15117.8 (2)
C3—C4—C5122.0 (2)C11—C20—C15119.7 (2)
C9—C4—C5118.9 (2)N1—C21—C13122.2 (2)
C6—C5—C4120.8 (2)N1—C21—H21118.9
C6—C5—H5119.6C13—C21—H21118.9
C4—C5—H5119.6N1—C22—C23111.9 (2)
C5—C6—C7120.2 (2)N1—C22—H22A109.2
C5—C6—H6119.9C23—C22—H22A109.2
C7—C6—H6119.9N1—C22—H22B109.2
C8—C7—C6120.8 (2)C23—C22—H22B109.2
C8—C7—H7119.6H22A—C22—H22B107.9
C6—C7—H7119.6C22—C23—C24112.9 (2)
C7—C8—C9121.0 (2)C22—C23—H23A109.0
C7—C8—H8119.5C24—C23—H23A109.0
C9—C8—H8119.5C22—C23—H23B109.0
C8—C9—C4118.3 (2)C24—C23—H23B109.0
C8—C9—C10122.0 (2)H23A—C23—H23B107.8
C4—C9—C10119.63 (19)C23—C24—H24A109.5
C1—C10—C9118.25 (19)C23—C24—H24B109.5
C1—C10—C11121.72 (18)H24A—C24—H24B109.5
C9—C10—C11120.02 (18)C23—C24—H24C109.5
C12—C11—C20119.3 (2)H24A—C24—H24C109.5
C12—C11—C10119.8 (2)H24B—C24—H24C109.5
C20—C11—C10120.84 (19)O3—C25—C26112.0 (3)
O2—C12—C11118.8 (2)O3—C25—H25A109.2
O2—C12—C13119.5 (2)C26—C25—H25A109.2
C11—C12—C13121.7 (2)O3—C25—H25B109.2
C14—C13—C12118.3 (2)C26—C25—H25B109.2
C14—C13—C21120.4 (2)H25A—C25—H25B107.9
C12—C13—C21121.4 (2)C25—C26—H26A109.5
C13—C14—C15122.5 (2)C25—C26—H26B109.5
C13—C14—H14118.7H26A—C26—H26B109.5
C15—C14—H14118.7C25—C26—H26C109.5
C14—C15—C16122.7 (2)H26A—C26—H26C109.5
C14—C15—C20118.3 (2)H26B—C26—H26C109.5
C16—C15—C20119.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.821.922.738 (2)175
O2—H2···N10.821.852.590 (3)149
O3—H3···O20.822.192.939 (3)151

Symmetry codes: (i) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2737).

References

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

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