1,10,10-Trimethyl-5-phenyl-3-oxa-4-aza-tri-cyclo-[5.2.1.0(2,6)]dec-4-en-2-ol.

The title compound, C17H21NO2, was synthesized by the reaction of (1R)-(+)-3-benzyl-camphor and hydroxyl-amine. The oxazole ring makes a dihedral angle of 23.42 (16)° with the phenyl ring. The six-membered ring of the norboryl group adopts a boat conformation, whereas each of the five-membered rings of the norboryl group displays a flattened envelope conformation, with the C atom carrying the methyl groups representing the flap for both rings. In the crystal, mol-ecules are linked into zigzag chains propagating along the b axis by O-H⋯N hydrogen bonds.

Related literature

For the functionalization of camphor, see: Jennings & Herschbach (1965 ▶); Pastrán et al., (2011 ▶). For transition metal complexes of camphor, see: Spannenberg et al. (2002 ▶); Harrad et al. (2010 ▶); Ait Ali et al. (2006 ▶); Gaudo et al. (2011 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H21NO2

M = 271.35

Monoclinic,

a = 22.1681 (18) Å

b = 6.6134 (5) Å

c = 10.7358 (8) Å

β = 108.277 (3)°

V = 1494.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.58 × 0.34 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.627, T max = 0.745

4379 measured reflections

1350 independent reflections

1220 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.106

S = 1.08

1350 reflections

186 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶)and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681302000X/bt6921sup1.cif

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

C17H21NO2	F(000) = 584
Mr = 271.35	Dx = 1.202 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2921 reflections
a = 22.1681 (18) Å	θ = 3.2–24.5°
b = 6.6134 (5) Å	µ = 0.08 mm−1
c = 10.7358 (8) Å	T = 296 K
β = 108.277 (3)°	Plaquet, colourless
V = 1494.5 (2) Å3	0.58 × 0.34 × 0.14 mm
Z = 4

Bruker APEXII CCD diffractometer	1350 independent reflections
Radiation source: fine-focus sealed tube	1220 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.3333 pixels mm-1	θmax = 24.5°, θmin = 3.2°
ω and φ scans	h = −25→25
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −6→7
Tmin = 0.627, Tmax = 0.745	l = −12→12
4379 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0701P)2 + 0.2932P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1350 reflections	Δρmax = 0.29 e Å−3
186 parameters	Δρmin = −0.24 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (5)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq
C5	0.81485 (10)	0.9730 (4)	−0.0870 (2)	0.0383 (6)
C6	0.85865 (11)	1.0215 (4)	0.0464 (2)	0.0393 (6)
H6	0.8609	1.1673	0.0637	0.047*
C7	0.92540 (11)	0.9251 (5)	0.0815 (2)	0.0527 (8)
H7	0.9569	1.0084	0.0585	0.063*
C8	0.91859 (14)	0.7103 (6)	0.0251 (3)	0.0632 (9)
H8A	0.8924	0.7088	−0.0662	0.076*
H8B	0.9597	0.6520	0.0325	0.076*
C9	0.88635 (13)	0.5975 (5)	0.1116 (3)	0.0560 (7)
H9A	0.9122	0.4844	0.1557	0.067*
H9B	0.8450	0.5473	0.0598	0.067*
C1	0.87986 (11)	0.7567 (4)	0.2119 (2)	0.0445 (7)
C2	0.82786 (10)	0.9070 (4)	0.1358 (2)	0.0387 (6)
C10	0.94087 (11)	0.8860 (5)	0.2308 (2)	0.0520 (7)
C12	1.00340 (13)	0.7670 (7)	0.2908 (3)	0.0777 (11)
H12A	1.0381	0.8412	0.2775	0.116*
H12B	1.0001	0.6374	0.2490	0.116*
H12C	1.0107	0.7487	0.3831	0.116*
C11	0.94630 (15)	1.0792 (6)	0.3124 (3)	0.0690 (9)
H11A	0.9852	1.1475	0.3175	0.104*
H11B	0.9461	1.0448	0.3991	0.104*
H11C	0.9110	1.1664	0.2716	0.104*
C13	0.82295 (11)	1.0459 (5)	−0.2104 (2)	0.0443 (6)
C18	0.79751 (13)	0.9407 (6)	−0.3273 (2)	0.0586 (8)
H18	0.7746	0.8225	−0.3287	0.070*
C17	0.80638 (16)	1.0122 (7)	−0.4421 (3)	0.0738 (12)
H17	0.7889	0.9415	−0.5201	0.089*
C16	0.83984 (16)	1.1823 (8)	−0.4422 (3)	0.0794 (12)
H16	0.8461	1.2269	−0.5193	0.095*
C15	0.86471 (18)	1.2897 (8)	−0.3279 (4)	0.0852 (12)
H15	0.8870	1.4086	−0.3283	0.102*
C14	0.85657 (16)	1.2210 (6)	−0.2119 (3)	0.0671 (9)
H14	0.8739	1.2935	−0.1347	0.080*
C19	0.86922 (15)	0.6664 (6)	0.3337 (3)	0.0625 (9)
H19A	0.8294	0.5958	0.3092	0.094*
H19B	0.8686	0.7726	0.3942	0.094*
H19C	0.9030	0.5738	0.3745	0.094*
O1	0.77279 (7)	0.8072 (3)	0.04364 (16)	0.0467 (5)
N2	0.77018 (9)	0.8524 (4)	−0.08639 (18)	0.0438 (6)
O2	0.80582 (8)	1.0188 (3)	0.22155 (14)	0.0519 (6)
H2	0.7864	1.1178	0.1833	0.078*

	U11	U22	U33	U12	U13	U23
C5	0.0383 (11)	0.0409 (14)	0.0357 (11)	−0.0014 (11)	0.0116 (9)	−0.0065 (11)
C6	0.0455 (12)	0.0374 (14)	0.0336 (11)	−0.0048 (11)	0.0103 (9)	−0.0014 (11)
C7	0.0380 (12)	0.070 (2)	0.0502 (14)	−0.0076 (14)	0.0144 (10)	0.0066 (15)
C8	0.0559 (15)	0.075 (2)	0.0647 (17)	0.0157 (17)	0.0276 (13)	−0.0043 (17)
C9	0.0555 (14)	0.0465 (17)	0.0643 (17)	0.0097 (14)	0.0165 (12)	−0.0061 (15)
C1	0.0451 (12)	0.0443 (17)	0.0422 (13)	0.0041 (12)	0.0109 (10)	0.0047 (12)
C2	0.0386 (11)	0.0430 (16)	0.0341 (11)	0.0009 (11)	0.0107 (9)	−0.0011 (11)
C10	0.0428 (12)	0.059 (2)	0.0478 (13)	0.0021 (14)	0.0047 (10)	0.0047 (15)
C12	0.0453 (14)	0.098 (3)	0.077 (2)	0.0091 (18)	0.0011 (13)	0.015 (2)
C11	0.0690 (17)	0.068 (2)	0.0520 (16)	−0.0134 (19)	−0.0069 (12)	0.0013 (17)
C13	0.0453 (12)	0.0521 (17)	0.0358 (12)	0.0018 (13)	0.0130 (9)	−0.0030 (12)
C18	0.0577 (14)	0.078 (2)	0.0395 (13)	−0.0028 (16)	0.0148 (11)	−0.0094 (15)
C17	0.0720 (18)	0.116 (4)	0.0356 (14)	0.009 (2)	0.0197 (13)	−0.0077 (18)
C16	0.0704 (19)	0.126 (4)	0.0463 (17)	0.013 (2)	0.0247 (14)	0.024 (2)
C15	0.090 (2)	0.097 (3)	0.075 (2)	−0.017 (2)	0.0348 (18)	0.024 (2)
C14	0.0841 (19)	0.070 (2)	0.0478 (15)	−0.019 (2)	0.0218 (13)	0.0020 (16)
C19	0.0637 (16)	0.066 (2)	0.0557 (16)	0.0106 (17)	0.0162 (13)	0.0225 (17)
O1	0.0397 (8)	0.0571 (13)	0.0423 (9)	−0.0071 (9)	0.0115 (6)	0.0039 (8)
N2	0.0418 (10)	0.0513 (15)	0.0371 (10)	−0.0040 (11)	0.0107 (8)	−0.0025 (10)
O2	0.0621 (11)	0.0616 (14)	0.0337 (9)	0.0215 (10)	0.0174 (7)	0.0054 (9)

C5—N2	1.273 (3)	C12—H12A	0.9600
C5—C13	1.473 (3)	C12—H12B	0.9600
C5—C6	1.492 (3)	C12—H12C	0.9600
C6—C2	1.540 (3)	C11—H11A	0.9600
C6—C7	1.545 (4)	C11—H11B	0.9600
C6—H6	0.9800	C11—H11C	0.9600
C7—C8	1.534 (5)	C13—C14	1.380 (5)
C7—C10	1.552 (4)	C13—C18	1.390 (4)
C7—H7	0.9800	C18—C17	1.391 (4)
C8—C9	1.532 (4)	C18—H18	0.9300
C8—H8A	0.9700	C17—C16	1.348 (6)
C8—H8B	0.9700	C17—H17	0.9300
C9—C1	1.545 (4)	C16—C15	1.374 (6)
C9—H9A	0.9700	C16—H16	0.9300
C9—H9B	0.9700	C15—C14	1.390 (4)
C1—C19	1.522 (4)	C15—H15	0.9300
C1—C2	1.547 (3)	C14—H14	0.9300
C1—C10	1.558 (4)	C19—H19A	0.9600
C2—O2	1.384 (3)	C19—H19B	0.9600
C2—O1	1.465 (3)	C19—H19C	0.9600
C10—C11	1.532 (5)	O1—N2	1.411 (3)
C10—C12	1.548 (4)	O2—H2	0.8200
N2—C5—C13	121.6 (2)	C11—C10—C1	116.2 (2)
N2—C5—C6	113.7 (2)	C12—C10—C1	113.8 (3)
C13—C5—C6	124.6 (2)	C7—C10—C1	93.18 (19)
C5—C6—C2	102.15 (19)	C10—C12—H12A	109.5
C5—C6—C7	115.5 (2)	C10—C12—H12B	109.5
C2—C6—C7	102.88 (19)	H12A—C12—H12B	109.5
C5—C6—H6	111.8	C10—C12—H12C	109.5
C2—C6—H6	111.8	H12A—C12—H12C	109.5
C7—C6—H6	111.8	H12B—C12—H12C	109.5
C8—C7—C6	108.5 (2)	C10—C11—H11A	109.5
C8—C7—C10	102.5 (3)	C10—C11—H11B	109.5
C6—C7—C10	101.8 (2)	H11A—C11—H11B	109.5
C8—C7—H7	114.2	C10—C11—H11C	109.5
C6—C7—H7	114.2	H11A—C11—H11C	109.5
C10—C7—H7	114.2	H11B—C11—H11C	109.5
C9—C8—C7	102.6 (2)	C14—C13—C18	118.5 (3)
C9—C8—H8A	111.2	C14—C13—C5	120.2 (2)
C7—C8—H8A	111.2	C18—C13—C5	121.3 (3)
C9—C8—H8B	111.2	C17—C18—C13	120.0 (3)
C7—C8—H8B	111.2	C17—C18—H18	120.0
H8A—C8—H8B	109.2	C13—C18—H18	120.0
C8—C9—C1	104.7 (3)	C16—C17—C18	121.0 (3)
C8—C9—H9A	110.8	C16—C17—H17	119.5
C1—C9—H9A	110.8	C18—C17—H17	119.5
C8—C9—H9B	110.8	C17—C16—C15	119.9 (3)
C1—C9—H9B	110.8	C17—C16—H16	120.1
H9A—C9—H9B	108.9	C15—C16—H16	120.1
C19—C1—C9	113.9 (3)	C16—C15—C14	120.2 (4)
C19—C1—C2	114.5 (2)	C16—C15—H15	119.9
C9—C1—C2	106.7 (2)	C14—C15—H15	119.9
C19—C1—C10	117.8 (2)	C13—C14—C15	120.4 (3)
C9—C1—C10	101.4 (2)	C13—C14—H14	119.8
C2—C1—C10	100.9 (2)	C15—C14—H14	119.8
O2—C2—O1	107.27 (17)	C1—C19—H19A	109.5
O2—C2—C6	118.0 (2)	C1—C19—H19B	109.5
O1—C2—C6	103.82 (17)	H19A—C19—H19B	109.5
O2—C2—C1	110.61 (19)	C1—C19—H19C	109.5
O1—C2—C1	113.1 (2)	H19A—C19—H19C	109.5
C6—C2—C1	104.03 (18)	H19B—C19—H19C	109.5
C11—C10—C12	106.6 (3)	N2—O1—C2	109.86 (17)
C11—C10—C7	113.8 (3)	C5—N2—O1	110.33 (18)
C12—C10—C7	113.2 (2)	C2—O2—H2	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2i	0.82	2.06	2.877 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2i	0.82	2.06	2.877 (3)	174

Symmetry code: (i) .