organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2,6-Bis[(4R,5R)-4,5-di­phenyl-4,5-di­hydro-1,3-oxazol-2-yl]pyridine

aInstitute of Drug Synthesis and Pharmaceutical Processes, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 17 April 2011; accepted 19 April 2011; online 7 May 2011)

The mol­ecule of the title compound, C35H27N3O2, lies on a twofold rotation axis passing through the pyridine ring. The five-membered ring is approximately flat (r.m.s. deviation = 0.065 Å) and is essentially coplanar [dihedral angle = 4.2 (2)°] with the pyridine ring.

Related literature

For the synthesis of the precursor, see: Desimoni et al. (2001[Desimoni, G., Faita, G., Filippone, S., Mella, M., Zampori, M. G. & Zema, M. (2001). Tetrahedron, 57, 10203-10212.]). For the structure of 2,6-bis­(2-oxazolin­yl)pyridine, see: Sada et al. (2003[Sada, K., Sugimoto, T., Tani, T., Tateishi, Y., Yi, T., Shinkai, S., Maeda, H., Tohnai, N. & Miyata, M. (2003). Chem. Lett. 32, 758-759.]).

[Scheme 1]

Experimental

Crystal data
  • C35H27N3O2

  • Mr = 521.60

  • Monoclinic, C 2

  • a = 19.035 (2) Å

  • b = 6.5908 (7) Å

  • c = 14.3001 (15) Å

  • β = 129.454 (1)°

  • V = 1385.2 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.38 × 0.20 × 0.16 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 3266 measured reflections

  • 1299 independent reflections

  • 1190 reflections with I > 2σ(I)

  • Rint = 0.017

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.099

  • S = 1.05

  • 1299 reflections

  • 182 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.11 e Å−3

  • Absolute structure: 768 Friedel pairs merged

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

We report here the cyclization of the two side arms of (2,6-bis[(1R,2S)N,N'-2-chloro-1,2-diphenylethyl]-pyridinedicarboxamide to form a di-substituted pyridine having two 1,3-oxazoline rings. The title compound is intended for an evaluation of its phamaceutical properties. It lies on a twofold rotation axis that passes through the pyridine ring (Fig. 1). The five-membered ring is approximately flat [r.m.s. deviation 0.065 Å] and is nearly coplanar [dihedral angle 4.2 (2)°] with the pyridine ring. In the parent compound, 2,6-bis(2-oxazolinyl)pyridine, the three rings are similarly nearly coplanar (Sada et al., 2003).

Related literature top

For the synthesis of the precursor, see: Desimoni et al. (2001). For the structure of 2,6-bis(2-oxazolinyl)pyridine, see: Sada et al. (2003).

Experimental top

To a suspension of 2,6-bis[(1R,2S)N,N'-2-chloro-1,2-diphenylethyl]-pyridinedicarboxamide (Desimoni et al., 2001) (0.89 g, 1.5 mmol) in ethanol (26 ml), an equeous solution of 2 N sodium hydroxide (13 ml) was added and the mixture was refluxed 8 h. The hot suspension was filtered and the white solid was washed with water (0.73 g, yield 90%). Crystals were obtained by recrystallization from ethyl acetate; m.p. 474–474 K.

Refinement top

H atoms were placed in calculated positions (C—H 0.93–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C); 768 Friedel pairs were merged. The absolute configuration was assumed to be that of the reactant.

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C35H37N3O2 at the 50% probability level; H atoms are drawn as arbitrary radius.
2,6-Bis[(4R,5R)-4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridine top
Crystal data top
C35H27N3O2F(000) = 548
Mr = 521.60Dx = 1.251 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 1652 reflections
a = 19.035 (2) Åθ = 2.8–26.1°
b = 6.5908 (7) ŵ = 0.08 mm1
c = 14.3001 (15) ÅT = 293 K
β = 129.454 (1)°Prism, colourless
V = 1385.2 (3) Å30.38 × 0.20 × 0.16 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer
1190 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 25.0°, θmin = 2.9°
ϕ and ω scansh = 2222
3266 measured reflectionsk = 77
1299 independent reflectionsl = 1715
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)] = 0.034H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0722P)2 + 0.0677P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
1299 reflectionsΔρmax = 0.16 e Å3
182 parametersΔρmin = 0.11 e Å3
1 restraintAbsolute structure: 768 Friedel pairs merged
Primary atom site location: structure-invariant direct methods
Crystal data top
C35H27N3O2V = 1385.2 (3) Å3
Mr = 521.60Z = 2
Monoclinic, C2Mo Kα radiation
a = 19.035 (2) ŵ = 0.08 mm1
b = 6.5908 (7) ÅT = 293 K
c = 14.3001 (15) Å0.38 × 0.20 × 0.16 mm
β = 129.454 (1)°
Data collection top
Bruker SMART CCD
diffractometer
1190 reflections with I > 2σ(I)
3266 measured reflectionsRint = 0.017
1299 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0341 restraint
wR(F2) = 0.099H-atom parameters constrained
S = 1.05Δρmax = 0.16 e Å3
1299 reflectionsΔρmin = 0.11 e Å3
182 parametersAbsolute structure: 768 Friedel pairs merged
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.00290 (12)0.4999 (2)0.24429 (14)0.0590 (5)
N10.00000.3969 (4)0.00000.0453 (6)
N20.00872 (13)0.1951 (3)0.18302 (16)0.0503 (5)
C10.00000.8221 (5)0.00000.0582 (8)
H10.00000.96320.00000.070*
C20.00113 (15)0.7152 (4)0.0817 (2)0.0538 (6)
H20.00230.78310.13770.065*
C30.00049 (13)0.5041 (3)0.07933 (18)0.0449 (5)
C40.00168 (14)0.3864 (4)0.16940 (19)0.0472 (5)
C50.00709 (15)0.1499 (4)0.2830 (2)0.0505 (5)
H50.06040.06790.34450.061*
C60.07812 (16)0.0392 (4)0.2397 (2)0.0522 (5)
C70.16168 (18)0.0935 (5)0.1346 (2)0.0769 (8)
H70.16610.19500.08590.092*
C80.2399 (2)0.0029 (6)0.1005 (3)0.0909 (10)
H80.29640.03560.02940.109*
C90.2346 (2)0.1521 (6)0.1699 (4)0.0887 (10)
H90.28720.21540.14680.106*
C100.1519 (2)0.2093 (5)0.2738 (3)0.0833 (9)
H100.14810.31240.32120.100*
C110.07370 (18)0.1150 (4)0.3090 (2)0.0648 (7)
H110.01750.15530.38000.078*
C120.01565 (15)0.3640 (4)0.33649 (19)0.0498 (5)
H120.03140.37950.34470.060*
C130.10798 (15)0.4089 (4)0.45661 (19)0.0493 (5)
C140.14229 (19)0.2821 (5)0.5543 (2)0.0654 (7)
H140.10740.17420.54630.078*
C150.2283 (2)0.3148 (6)0.6638 (3)0.0788 (8)
H150.25150.22680.72840.095*
C160.27910 (19)0.4766 (5)0.6770 (3)0.0738 (8)
H160.33670.49950.75060.089*
C170.24501 (16)0.6032 (5)0.5823 (3)0.0712 (8)
H170.27940.71360.59160.085*
C180.16001 (17)0.5710 (4)0.4720 (2)0.0600 (6)
H180.13780.65920.40790.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0850 (11)0.0442 (10)0.0564 (9)0.0107 (8)0.0489 (9)0.0016 (8)
N10.0524 (14)0.0389 (14)0.0499 (14)0.0000.0350 (12)0.000
N20.0666 (11)0.0425 (12)0.0597 (11)0.0016 (9)0.0486 (10)0.0038 (9)
C10.070 (2)0.0344 (17)0.061 (2)0.0000.0377 (17)0.000
C20.0642 (14)0.0395 (13)0.0570 (13)0.0013 (11)0.0381 (12)0.0048 (11)
C30.0466 (12)0.0397 (13)0.0473 (11)0.0004 (9)0.0294 (10)0.0013 (9)
C40.0525 (12)0.0443 (13)0.0496 (12)0.0032 (10)0.0347 (10)0.0006 (10)
C50.0618 (13)0.0449 (13)0.0549 (12)0.0013 (10)0.0418 (11)0.0010 (11)
C60.0666 (13)0.0445 (12)0.0565 (12)0.0065 (11)0.0442 (12)0.0076 (10)
C70.0767 (17)0.079 (2)0.0661 (15)0.0148 (16)0.0411 (15)0.0034 (15)
C80.0714 (18)0.103 (3)0.0825 (19)0.0200 (19)0.0413 (16)0.010 (2)
C90.090 (2)0.083 (2)0.117 (2)0.0336 (19)0.078 (2)0.029 (2)
C100.106 (2)0.0622 (18)0.122 (2)0.0105 (17)0.092 (2)0.0006 (19)
C110.0817 (16)0.0521 (14)0.0830 (17)0.0032 (13)0.0629 (15)0.0058 (14)
C120.0648 (13)0.0450 (13)0.0543 (12)0.0017 (11)0.0448 (12)0.0005 (10)
C130.0642 (13)0.0468 (13)0.0546 (12)0.0019 (10)0.0460 (11)0.0041 (10)
C140.0837 (17)0.0614 (17)0.0612 (14)0.0122 (14)0.0507 (14)0.0017 (13)
C150.0943 (19)0.080 (2)0.0591 (15)0.0159 (19)0.0474 (15)0.0108 (16)
C160.0644 (15)0.078 (2)0.0718 (16)0.0007 (15)0.0399 (14)0.0115 (16)
C170.0644 (16)0.0689 (18)0.0885 (18)0.0091 (14)0.0523 (16)0.0086 (16)
C180.0687 (15)0.0554 (15)0.0696 (14)0.0040 (13)0.0504 (13)0.0000 (12)
Geometric parameters (Å, º) top
O1—C41.354 (3)C8—H80.9300
O1—C121.440 (3)C9—C101.362 (5)
N1—C31.341 (2)C9—H90.9300
N1—C3i1.341 (2)C10—C111.379 (4)
N2—C41.270 (3)C10—H100.9300
N2—C51.480 (3)C11—H110.9300
C1—C21.376 (3)C12—C131.513 (3)
C1—C2i1.376 (3)C12—H120.9800
C1—H10.9300C13—C181.376 (3)
C2—C31.392 (3)C13—C141.384 (3)
C2—H20.9300C14—C151.386 (4)
C3—C41.481 (3)C14—H140.9300
C5—C61.507 (3)C15—C161.370 (5)
C5—C121.563 (3)C15—H150.9300
C5—H50.9800C16—C171.355 (4)
C6—C71.371 (4)C16—H160.9300
C6—C111.384 (3)C17—C181.381 (4)
C7—C81.392 (4)C17—H170.9300
C7—H70.9300C18—H180.9300
C8—C91.355 (5)
C4—O1—C12106.19 (17)C10—C9—H9120.1
C3—N1—C3i116.5 (2)C9—C10—C11120.4 (3)
C4—N2—C5106.44 (19)C9—C10—H10119.8
C2—C1—C2i118.4 (3)C11—C10—H10119.8
C2—C1—H1120.8C10—C11—C6120.6 (3)
C2i—C1—H1120.8C10—C11—H11119.7
C1—C2—C3119.1 (2)C6—C11—H11119.7
C1—C2—H2120.5O1—C12—C13110.46 (18)
C3—C2—H2120.5O1—C12—C5103.00 (15)
N1—C3—C2123.5 (2)C13—C12—C5114.64 (19)
N1—C3—C4116.65 (18)O1—C12—H12109.5
C2—C3—C4119.9 (2)C13—C12—H12109.5
N2—C4—O1118.7 (2)C5—C12—H12109.5
N2—C4—C3126.5 (2)C18—C13—C14118.5 (2)
O1—C4—C3114.73 (18)C18—C13—C12122.2 (2)
N2—C5—C6112.22 (19)C14—C13—C12119.3 (2)
N2—C5—C12103.37 (18)C13—C14—C15120.5 (3)
C6—C5—C12112.88 (18)C13—C14—H14119.7
N2—C5—H5109.4C15—C14—H14119.7
C6—C5—H5109.4C16—C15—C14120.0 (3)
C12—C5—H5109.4C16—C15—H15120.0
C7—C6—C11118.5 (2)C14—C15—H15120.0
C7—C6—C5121.4 (2)C17—C16—C15119.6 (3)
C11—C6—C5120.1 (2)C17—C16—H16120.2
C6—C7—C8120.2 (3)C15—C16—H16120.2
C6—C7—H7119.9C16—C17—C18121.1 (3)
C8—C7—H7119.9C16—C17—H17119.5
C9—C8—C7120.6 (3)C18—C17—H17119.5
C9—C8—H8119.7C13—C18—C17120.3 (3)
C7—C8—H8119.7C13—C18—H18119.9
C8—C9—C10119.7 (3)C17—C18—H18119.9
C8—C9—H9120.1
C2i—C1—C2—C30.42 (15)C8—C9—C10—C110.5 (5)
C3i—N1—C3—C20.45 (17)C9—C10—C11—C60.1 (5)
C3i—N1—C3—C4178.3 (2)C7—C6—C11—C101.0 (4)
C1—C2—C3—N10.9 (3)C5—C6—C11—C10176.2 (3)
C1—C2—C3—C4177.79 (15)C4—O1—C12—C13109.2 (2)
C5—N2—C4—O11.7 (3)C4—O1—C12—C513.6 (2)
C5—N2—C4—C3179.57 (19)N2—C5—C12—O114.4 (2)
C12—O1—C4—N28.5 (3)C6—C5—C12—O1107.09 (19)
C12—O1—C4—C3170.44 (17)N2—C5—C12—C13105.65 (19)
N1—C3—C4—N23.9 (3)C6—C5—C12—C13132.9 (2)
C2—C3—C4—N2174.8 (2)O1—C12—C13—C185.3 (3)
N1—C3—C4—O1177.25 (15)C5—C12—C13—C18121.1 (2)
C2—C3—C4—O14.0 (3)O1—C12—C13—C14173.81 (18)
C4—N2—C5—C6111.8 (2)C5—C12—C13—C1458.0 (3)
C4—N2—C5—C1210.1 (3)C18—C13—C14—C151.9 (4)
N2—C5—C6—C742.1 (3)C12—C13—C14—C15177.2 (2)
C12—C5—C6—C774.2 (3)C13—C14—C15—C161.7 (4)
N2—C5—C6—C11140.8 (2)C14—C15—C16—C170.4 (4)
C12—C5—C6—C11102.8 (2)C15—C16—C17—C180.5 (4)
C11—C6—C7—C81.1 (4)C14—C13—C18—C171.0 (3)
C5—C6—C7—C8176.0 (3)C12—C13—C18—C17178.2 (2)
C6—C7—C8—C90.5 (5)C16—C17—C18—C130.3 (4)
C7—C8—C9—C100.3 (5)
Symmetry code: (i) x, y, z.

Experimental details

Crystal data
Chemical formulaC35H27N3O2
Mr521.60
Crystal system, space groupMonoclinic, C2
Temperature (K)293
a, b, c (Å)19.035 (2), 6.5908 (7), 14.3001 (15)
β (°) 129.454 (1)
V3)1385.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.38 × 0.20 × 0.16
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3266, 1299, 1190
Rint0.017
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.099, 1.05
No. of reflections1299
No. of parameters182
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.11
Absolute structure768 Friedel pairs merged

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

The authors thank the Scientific Research Foundation for Returned Overseas Chinese Scholars and the Programme for New Century Excellent Talents (both from the State Education Ministry of China), the Project of Inter­national Science and Technology Cooperation (from the Ministry of Science and Technology of China) and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDesimoni, G., Faita, G., Filippone, S., Mella, M., Zampori, M. G. & Zema, M. (2001). Tetrahedron, 57, 10203–10212.  CrossRef CAS
First citationSada, K., Sugimoto, T., Tani, T., Tateishi, Y., Yi, T., Shinkai, S., Maeda, H., Tohnai, N. & Miyata, M. (2003). Chem. Lett. 32, 758–759.  CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds