2,6-Bis[(S)-4-benzyl-4,5-dihydro-1,3-oxazol-2-yl]pyridine.

The commercially available title compound, C(25)H(23)N(3)O(2), has been known since 1993 [Nesper et al. (1993 ▶). Helv. Chim. Acta, 76, 2239-2249], but has not been structurally characterized until now. In the free ligand, the N atoms of both oxazoline rings point in opposite directions. The phenyl rings make dihedral angles of 30.56 (5) and 84.57 (3)° with the pyridine ring and 72.85 (3)° with each other.

Related literature

For the synthesis, see: Nesper et al. (1993 ▶; 1996 ▶); Schaus & Jacobsen (2000 ▶); Towers et al. (2003 ▶); Meng et al. (2005 ▶); Hui et al. (2006 ▶). For crystal structures showing the same ligand coordinated to Pd(BF4)2 or AgBF4, see: Nesper et al. (1996 ▶); Provent et al. (1997 ▶). For applications in asymmetric catalysis, see: Desimoni et al. (2003 ▶); Tse et al. (2006 ▶).

Experimental

Crystal data

C25H23N3O2

M = 397.46

Orthorhombic,

a = 7.0184 (2) Å

b = 13.2654 (3) Å

c = 21.5542 (8) Å

V = 2006.74 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.50 × 0.45 × 0.25 mm

Data collection

Stoe IPDS II diffractometer

38412 measured reflections

5433 independent reflections

4254 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.053

S = 0.86

5433 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.18 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014061/om2419sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014061/om2419Isup2.hkl

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

C25H23N3O2	F(000) = 840
Mr = 397.46	Dx = 1.316 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7372 reflections
a = 7.0184 (2) Å	θ = 1.8–29.6°
b = 13.2654 (3) Å	µ = 0.09 mm−1
c = 21.5542 (8) Å	T = 150 K
V = 2006.74 (10) Å3	Prism, colourless
Z = 4	0.50 × 0.45 × 0.25 mm

Stoe IPDS II diffractometer	4254 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 29.2°, θmin = 1.8°
ω scans	h = −9→9
38412 measured reflections	k = −18→18
5433 independent reflections	l = −29→29

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.053	H-atom parameters constrained
S = 0.86	w = 1/[σ2(Fo2) + (0.0277P)2] where P = (Fo2 + 2Fc2)/3
5433 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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 > σ(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.

	x	y	z	Uiso*/Ueq
C1	0.08221 (18)	0.78242 (8)	0.86378 (6)	0.0391 (3)
H1A	0.0477	0.8470	0.8436	0.047*
H1B	0.1124	0.7953	0.9079	0.047*
C2	−0.07905 (16)	0.70557 (7)	0.85760 (5)	0.0307 (2)
H2	−0.1664	0.7274	0.8235	0.037*
C3	0.18890 (16)	0.63775 (7)	0.82495 (5)	0.0271 (2)
C4	0.33449 (15)	0.56927 (7)	0.79877 (5)	0.0271 (2)
C5	0.30631 (16)	0.46567 (7)	0.80236 (5)	0.0320 (2)
H5	0.1993	0.4390	0.8238	0.038*
C6	0.43561 (16)	0.40269 (8)	0.77450 (5)	0.0330 (3)
H6	0.4199	0.3316	0.7762	0.040*
C7	0.58872 (16)	0.44469 (7)	0.74402 (5)	0.0302 (2)
H7	0.6801	0.4029	0.7241	0.036*
C8	0.60768 (16)	0.54896 (7)	0.74277 (5)	0.0261 (2)
C9	0.76549 (16)	0.59535 (7)	0.70744 (4)	0.0274 (2)
C10	1.02808 (19)	0.58556 (8)	0.64867 (6)	0.0410 (3)
H10A	1.0471	0.5688	0.6044	0.049*
H10B	1.1483	0.5731	0.6715	0.049*
C11	0.96205 (16)	0.69563 (8)	0.65652 (5)	0.0307 (2)
H11	0.9089	0.7199	0.6161	0.037*
C12	1.11831 (16)	0.76752 (8)	0.67706 (5)	0.0308 (2)
H12A	1.0595	0.8305	0.6927	0.037*
H12B	1.1903	0.7366	0.7116	0.037*
C13	1.25418 (16)	0.79284 (7)	0.62524 (5)	0.0287 (2)
C14	1.23770 (17)	0.88259 (8)	0.59240 (5)	0.0341 (2)
H14	1.1407	0.9293	0.6032	0.041*
C15	1.36016 (18)	0.90471 (10)	0.54433 (6)	0.0422 (3)
H15	1.3472	0.9665	0.5225	0.051*
C16	1.50168 (19)	0.83760 (9)	0.52768 (6)	0.0415 (3)
H16	1.5855	0.8528	0.4944	0.050*
C17	1.52003 (17)	0.74822 (9)	0.55991 (6)	0.0403 (3)
H17	1.6169	0.7016	0.5488	0.048*
C18	1.39795 (17)	0.72647 (8)	0.60832 (5)	0.0352 (3)
H18	1.4126	0.6650	0.6304	0.042*
C19	−0.19380 (17)	0.69334 (8)	0.91699 (5)	0.0338 (2)
H19A	−0.3029	0.6477	0.9093	0.041*
H19B	−0.1127	0.6623	0.9494	0.041*
C20	−0.26647 (15)	0.79374 (7)	0.93971 (5)	0.0284 (2)
C21	−0.19421 (16)	0.83776 (8)	0.99302 (5)	0.0331 (3)
H21	−0.0999	0.8031	1.0164	0.040*
C22	−0.25669 (18)	0.93129 (8)	1.01295 (5)	0.0369 (3)
H22	−0.2051	0.9603	1.0496	0.044*
C23	−0.39392 (18)	0.98226 (8)	0.97955 (6)	0.0385 (3)
H23	−0.4370	1.0466	0.9930	0.046*
C24	−0.46803 (17)	0.93922 (9)	0.92658 (6)	0.0380 (3)
H24	−0.5632	0.9739	0.9037	0.046*
C25	−0.40519 (17)	0.84613 (8)	0.90655 (5)	0.0329 (2)
H25	−0.4570	0.8175	0.8698	0.040*
N1	0.48293 (13)	0.61177 (6)	0.76977 (4)	0.02706 (19)
N2	0.02005 (14)	0.61231 (6)	0.83845 (4)	0.0311 (2)
N3	0.80484 (13)	0.68788 (6)	0.70200 (4)	0.0307 (2)
O1	0.24182 (12)	0.73528 (5)	0.83241 (3)	0.03401 (18)
O2	0.87275 (12)	0.52786 (5)	0.67492 (4)	0.0402 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0401 (7)	0.0291 (5)	0.0482 (7)	−0.0040 (5)	0.0204 (6)	−0.0039 (5)
C2	0.0318 (6)	0.0266 (5)	0.0337 (6)	−0.0005 (4)	0.0013 (5)	0.0007 (4)
C3	0.0318 (6)	0.0241 (5)	0.0255 (5)	−0.0043 (4)	0.0004 (5)	0.0029 (4)
C4	0.0289 (6)	0.0273 (5)	0.0251 (5)	−0.0027 (4)	−0.0007 (4)	0.0015 (4)
C5	0.0320 (6)	0.0283 (5)	0.0357 (6)	−0.0042 (5)	0.0018 (5)	0.0048 (4)
C6	0.0398 (7)	0.0218 (5)	0.0375 (6)	−0.0016 (5)	−0.0023 (5)	0.0023 (4)
C7	0.0332 (6)	0.0264 (5)	0.0310 (6)	0.0034 (4)	0.0003 (5)	−0.0002 (4)
C8	0.0289 (6)	0.0249 (5)	0.0245 (5)	−0.0005 (4)	−0.0013 (4)	0.0006 (4)
C9	0.0293 (6)	0.0266 (5)	0.0262 (5)	0.0016 (5)	0.0004 (5)	−0.0035 (4)
C10	0.0403 (7)	0.0347 (6)	0.0480 (7)	−0.0067 (5)	0.0162 (6)	−0.0078 (5)
C11	0.0302 (6)	0.0337 (5)	0.0282 (5)	−0.0001 (5)	0.0037 (5)	0.0020 (4)
C12	0.0330 (6)	0.0295 (5)	0.0299 (5)	0.0017 (5)	0.0008 (5)	0.0009 (4)
C13	0.0255 (6)	0.0297 (5)	0.0310 (5)	−0.0031 (4)	−0.0036 (5)	−0.0033 (4)
C14	0.0294 (6)	0.0325 (5)	0.0404 (6)	−0.0010 (5)	−0.0008 (5)	0.0025 (4)
C15	0.0402 (7)	0.0439 (7)	0.0424 (7)	−0.0079 (6)	−0.0013 (6)	0.0104 (5)
C16	0.0349 (7)	0.0544 (7)	0.0351 (6)	−0.0136 (6)	0.0054 (6)	−0.0025 (5)
C17	0.0264 (6)	0.0450 (7)	0.0494 (7)	−0.0017 (5)	0.0039 (6)	−0.0128 (5)
C18	0.0297 (6)	0.0315 (6)	0.0444 (7)	−0.0004 (5)	−0.0007 (5)	−0.0013 (5)
C19	0.0294 (6)	0.0292 (5)	0.0429 (6)	−0.0006 (5)	0.0083 (5)	0.0054 (5)
C20	0.0228 (5)	0.0304 (5)	0.0320 (5)	−0.0024 (5)	0.0068 (5)	0.0071 (4)
C21	0.0263 (6)	0.0406 (6)	0.0323 (6)	0.0000 (5)	0.0018 (5)	0.0084 (4)
C22	0.0376 (7)	0.0416 (6)	0.0314 (5)	−0.0076 (5)	0.0043 (5)	−0.0013 (5)
C23	0.0416 (7)	0.0297 (6)	0.0443 (7)	0.0022 (5)	0.0132 (6)	0.0028 (5)
C24	0.0311 (6)	0.0396 (6)	0.0433 (7)	0.0069 (5)	0.0001 (5)	0.0101 (5)
C25	0.0289 (6)	0.0364 (6)	0.0335 (6)	−0.0028 (5)	−0.0015 (5)	0.0031 (5)
N1	0.0295 (5)	0.0247 (4)	0.0270 (4)	−0.0009 (4)	0.0019 (4)	−0.0001 (3)
N2	0.0297 (5)	0.0268 (4)	0.0370 (5)	−0.0031 (4)	0.0034 (4)	−0.0014 (4)
N3	0.0300 (5)	0.0277 (4)	0.0345 (5)	0.0021 (4)	0.0052 (4)	0.0030 (4)
O1	0.0351 (4)	0.0253 (3)	0.0416 (4)	−0.0049 (3)	0.0136 (4)	−0.0037 (3)
O2	0.0407 (5)	0.0283 (4)	0.0515 (5)	−0.0052 (4)	0.0187 (4)	−0.0111 (3)

C1—O1	1.4503 (14)	C12—C13	1.5065 (15)
C1—C2	1.5290 (17)	C12—H12A	0.9900
C1—H1A	0.9900	C12—H12B	0.9900
C1—H1B	0.9900	C13—C18	1.3879 (15)
C2—N2	1.4781 (14)	C13—C14	1.3899 (14)
C2—C19	1.5211 (15)	C14—C15	1.3778 (16)
C2—H2	1.0000	C14—H14	0.9500
C3—N2	1.2660 (14)	C15—C16	1.3813 (18)
C3—O1	1.3556 (11)	C15—H15	0.9500
C3—C4	1.4790 (14)	C16—C17	1.3801 (17)
C4—N1	1.3394 (13)	C16—H16	0.9500
C4—C5	1.3905 (14)	C17—C18	1.3808 (16)
C5—C6	1.3719 (15)	C17—H17	0.9500
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.3773 (15)	C19—C20	1.5078 (14)
C6—H6	0.9500	C19—H19A	0.9900
C7—C8	1.3898 (13)	C19—H19B	0.9900
C7—H7	0.9500	C20—C21	1.3852 (15)
C8—N1	1.3415 (13)	C20—C25	1.3934 (15)
C8—C9	1.4784 (15)	C21—C22	1.3843 (16)
C9—N3	1.2636 (13)	C21—H21	0.9500
C9—O2	1.3636 (12)	C22—C23	1.3796 (17)
C10—O2	1.4472 (14)	C22—H22	0.9500
C10—C11	1.5413 (15)	C23—C24	1.3784 (17)
C10—H10A	0.9900	C23—H23	0.9500
C10—H10B	0.9900	C24—C25	1.3806 (15)
C11—N3	1.4796 (14)	C24—H24	0.9500
C11—C12	1.5193 (16)	C25—H25	0.9500
C11—H11	1.0000
O1—C1—C2	104.10 (8)	C11—C12—H12B	109.1
O1—C1—H1A	110.9	H12A—C12—H12B	107.9
C2—C1—H1A	110.9	C18—C13—C14	118.04 (10)
O1—C1—H1B	110.9	C18—C13—C12	120.90 (9)
C2—C1—H1B	110.9	C14—C13—C12	121.05 (10)
H1A—C1—H1B	109.0	C15—C14—C13	120.90 (11)
N2—C2—C19	113.26 (8)	C15—C14—H14	119.6
N2—C2—C1	103.54 (9)	C13—C14—H14	119.6
C19—C2—C1	112.94 (9)	C14—C15—C16	120.44 (11)
N2—C2—H2	109.0	C14—C15—H15	119.8
C19—C2—H2	109.0	C16—C15—H15	119.8
C1—C2—H2	109.0	C17—C16—C15	119.34 (11)
N2—C3—O1	118.92 (10)	C17—C16—H16	120.3
N2—C3—C4	124.80 (9)	C15—C16—H16	120.3
O1—C3—C4	116.24 (9)	C16—C17—C18	120.13 (11)
N1—C4—C5	123.55 (10)	C16—C17—H17	119.9
N1—C4—C3	117.18 (8)	C18—C17—H17	119.9
C5—C4—C3	119.17 (10)	C17—C18—C13	121.14 (10)
C6—C5—C4	118.91 (10)	C17—C18—H18	119.4
C6—C5—H5	120.5	C13—C18—H18	119.4
C4—C5—H5	120.5	C20—C19—C2	110.99 (8)
C5—C6—C7	118.60 (9)	C20—C19—H19A	109.4
C5—C6—H6	120.7	C2—C19—H19A	109.4
C7—C6—H6	120.7	C20—C19—H19B	109.4
C6—C7—C8	119.11 (10)	C2—C19—H19B	109.4
C6—C7—H7	120.4	H19A—C19—H19B	108.0
C8—C7—H7	120.4	C21—C20—C25	118.10 (10)
N1—C8—C7	123.18 (10)	C21—C20—C19	121.19 (10)
N1—C8—C9	116.99 (8)	C25—C20—C19	120.69 (10)
C7—C8—C9	119.74 (9)	C22—C21—C20	121.29 (11)
N3—C9—O2	118.00 (9)	C22—C21—H21	119.4
N3—C9—C8	128.02 (9)	C20—C21—H21	119.4
O2—C9—C8	113.89 (8)	C23—C22—C21	119.90 (11)
O2—C10—C11	103.39 (9)	C23—C22—H22	120.1
O2—C10—H10A	111.1	C21—C22—H22	120.1
C11—C10—H10A	111.1	C24—C23—C22	119.52 (11)
O2—C10—H10B	111.1	C24—C23—H23	120.2
C11—C10—H10B	111.1	C22—C23—H23	120.2
H10A—C10—H10B	109.0	C23—C24—C25	120.59 (11)
N3—C11—C12	112.88 (9)	C23—C24—H24	119.7
N3—C11—C10	103.36 (8)	C25—C24—H24	119.7
C12—C11—C10	114.18 (10)	C24—C25—C20	120.60 (11)
N3—C11—H11	108.7	C24—C25—H25	119.7
C12—C11—H11	108.7	C20—C25—H25	119.7
C10—C11—H11	108.7	C4—N1—C8	116.66 (8)
C13—C12—C11	112.38 (9)	C3—N2—C2	106.35 (8)
C13—C12—H12A	109.1	C9—N3—C11	106.97 (8)
C11—C12—H12A	109.1	C3—O1—C1	104.79 (8)
C13—C12—H12B	109.1	C9—O2—C10	105.64 (8)