(5R,6S)-4-Isopropyl-5-methyl-6-phenyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one.

The title compound, C(16)H(22)N(2)O(3), was synthesized during the course of a study on (1R,2S)-norephedrine-derived 1,3,4-oxadiazinan-2-ones. The conformation adopted by the isopropyl group is pseudo-axial relative to the oxadiazinan core. The allylic strain contributes to this conformational arrangement.

Related literature

For related structures and background, see: Casper, Blackburn et al. (2002 ▶); Casper, Burgeson et al. (2002 ▶); Casper & Hitchcock (2003 ▶); Evans et al. (1981 ▶); Ferrence et al. (2003 ▶), Hitchcock et al. (2001 ▶); Trepanier et al. (1968 ▶). The synthesis of the title compound is described by Hitchcock et al. (2004 ▶). For ring puckering analysis, see: Boeyens (1978 ▶); Cremer & Pople (1975 ▶); Spek (2009 ▶). For non-classical hydrogen bonding, see: Steiner (1996 ▶).

Experimental

Crystal data

C16H22N2O3

M = 290.36

Orthorhombic,

a = 6.8644 (3) Å

b = 10.8370 (5) Å

c = 21.2348 (10) Å

V = 1579.65 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 140 K

0.45 × 0.29 × 0.2 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003 ▶) T min = 0.878, T max = 0.983

16184 measured reflections

2263 independent reflections

2231 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.099

S = 1.18

2263 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022363/zl2203sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022363/zl2203Isup2.hkl

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

Enhanced figure: interactive version of Fig. 2

C16H22N2O3	F(000) = 624
Mr = 290.36	Dx = 1.221 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7989 reflections
a = 6.8644 (3) Å	θ = 2.7–30.4°
b = 10.8370 (5) Å	µ = 0.09 mm−1
c = 21.2348 (10) Å	T = 140 K
V = 1579.65 (12) Å3	Needle, colourless
Z = 4	0.45 × 0.29 × 0.2 mm

Bruker SMART APEX CCD diffractometer	2263 independent reflections
Radiation source: sealed tube	2231 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	h = −9→9
Tmin = 0.878, Tmax = 0.983	k = −14→14
16184 measured reflections	l = −28→27

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.4577P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max < 0.001
S = 1.18	Δρmax = 0.32 e Å−3
2263 reflections	Δρmin = −0.21 e Å−3
190 parameters

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.

	x	y	z	Uiso*/Ueq
O1	0.75439 (18)	0.26491 (11)	0.44189 (6)	0.0196 (3)
C2	0.8863 (3)	0.34214 (16)	0.41773 (8)	0.0188 (3)
N3	0.8136 (2)	0.44240 (13)	0.38381 (7)	0.0178 (3)
N4	0.6120 (2)	0.47290 (13)	0.39003 (6)	0.0166 (3)
C5	0.5006 (2)	0.36039 (15)	0.37440 (7)	0.0165 (3)
H5	0.3593	0.3803	0.3796	0.020*
C6	0.5509 (2)	0.25838 (16)	0.42207 (8)	0.0163 (3)
H6	0.4683	0.2717	0.4602	0.020*
C7	0.5138 (3)	0.12801 (16)	0.39890 (8)	0.0187 (3)
C8	0.6638 (3)	0.05224 (17)	0.37881 (9)	0.0262 (4)
H8	0.7946	0.0806	0.3807	0.031*
C9	0.6234 (4)	−0.06520 (19)	0.35596 (10)	0.0326 (5)
H9	0.7270	−0.1166	0.3421	0.039*
C10	0.4342 (4)	−0.10773 (17)	0.35327 (9)	0.0320 (5)
H10	0.4073	−0.1883	0.3380	0.038*
C11	0.2841 (3)	−0.03214 (19)	0.37300 (10)	0.0315 (4)
H11	0.1535	−0.0608	0.3710	0.038*
C12	0.3230 (3)	0.08577 (17)	0.39586 (9)	0.0251 (4)
H12	0.2191	0.1373	0.4094	0.030*
C13	0.5331 (3)	0.32666 (16)	0.30550 (8)	0.0208 (3)
H13A	0.4971	0.3968	0.2788	0.031*
H13B	0.4523	0.2552	0.2946	0.031*
H13C	0.6706	0.3063	0.2988	0.031*
C14	0.5736 (3)	0.52506 (17)	0.45405 (8)	0.0225 (4)
H14	0.6017	0.4607	0.4865	0.027*
C15	0.7025 (3)	0.63686 (18)	0.46590 (10)	0.0310 (4)
H15A	0.8396	0.6123	0.4632	0.046*
H15B	0.6756	0.6700	0.5079	0.046*
H15C	0.6752	0.7002	0.4342	0.046*
C16	0.3600 (3)	0.5623 (2)	0.45843 (11)	0.0344 (5)
H16B	0.2776	0.4899	0.4511	0.052*
H16A	0.3318	0.6253	0.4266	0.052*
H16C	0.3334	0.5958	0.5004	0.052*
C17	0.9228 (2)	0.50008 (16)	0.33572 (8)	0.0195 (3)
C18	0.8239 (3)	0.60532 (17)	0.30136 (9)	0.0245 (4)
H18A	0.7224	0.5718	0.2730	0.029*
H18B	0.7594	0.6601	0.3323	0.029*
C19	0.9691 (3)	0.6793 (2)	0.26320 (11)	0.0344 (5)
H19C	0.9013	0.7465	0.2414	0.052*
H19B	1.0317	0.6254	0.2322	0.052*
H19A	1.0682	0.7139	0.2913	0.052*
O20	1.08450 (19)	0.46487 (14)	0.32269 (7)	0.0296 (3)
O21	1.05596 (18)	0.32428 (13)	0.42830 (6)	0.0266 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0168 (6)	0.0205 (6)	0.0214 (6)	−0.0011 (5)	−0.0033 (5)	0.0057 (5)
C2	0.0173 (7)	0.0213 (8)	0.0177 (7)	0.0005 (7)	−0.0004 (6)	0.0014 (6)
N3	0.0122 (6)	0.0190 (6)	0.0222 (7)	0.0004 (6)	0.0001 (5)	0.0033 (5)
N4	0.0121 (6)	0.0184 (6)	0.0194 (6)	0.0011 (5)	0.0013 (5)	−0.0003 (5)
C5	0.0144 (7)	0.0168 (7)	0.0183 (7)	0.0007 (6)	−0.0004 (6)	0.0017 (6)
C6	0.0126 (7)	0.0188 (7)	0.0174 (7)	−0.0009 (6)	0.0006 (6)	0.0014 (6)
C7	0.0216 (8)	0.0183 (7)	0.0163 (7)	−0.0009 (7)	0.0006 (6)	0.0015 (6)
C8	0.0260 (9)	0.0229 (8)	0.0297 (9)	0.0018 (8)	0.0019 (8)	−0.0018 (7)
C9	0.0420 (12)	0.0240 (9)	0.0318 (10)	0.0069 (9)	0.0038 (9)	−0.0036 (8)
C10	0.0539 (13)	0.0182 (8)	0.0239 (9)	−0.0074 (9)	−0.0026 (9)	−0.0011 (7)
C11	0.0337 (10)	0.0287 (10)	0.0322 (10)	−0.0126 (9)	−0.0017 (9)	0.0020 (8)
C12	0.0238 (9)	0.0230 (8)	0.0287 (9)	−0.0032 (8)	0.0008 (8)	0.0002 (7)
C13	0.0223 (8)	0.0226 (8)	0.0176 (7)	−0.0019 (8)	−0.0014 (6)	0.0010 (6)
C14	0.0281 (9)	0.0190 (7)	0.0203 (8)	−0.0011 (7)	0.0038 (7)	−0.0027 (6)
C15	0.0372 (11)	0.0242 (9)	0.0315 (9)	−0.0071 (8)	−0.0018 (9)	−0.0061 (8)
C16	0.0311 (10)	0.0337 (10)	0.0384 (11)	0.0030 (9)	0.0099 (9)	−0.0119 (9)
C17	0.0172 (7)	0.0208 (8)	0.0206 (7)	−0.0032 (7)	0.0000 (6)	0.0024 (6)
C18	0.0202 (8)	0.0239 (8)	0.0295 (9)	0.0003 (8)	0.0032 (7)	0.0086 (7)
C19	0.0281 (10)	0.0326 (10)	0.0424 (11)	−0.0031 (9)	0.0066 (9)	0.0167 (9)
O20	0.0183 (6)	0.0387 (8)	0.0318 (7)	0.0052 (6)	0.0061 (5)	0.0110 (6)
O21	0.0160 (6)	0.0325 (7)	0.0314 (7)	0.0020 (6)	−0.0018 (5)	0.0102 (6)

O1—C2	1.336 (2)	C11—H11	0.9500
O1—C6	1.460 (2)	C12—H12	0.9500
C2—O21	1.202 (2)	C13—H13A	0.9800
C2—N3	1.396 (2)	C13—H13B	0.9800
N3—C17	1.413 (2)	C13—H13C	0.9800
N3—N4	1.4291 (19)	C14—C15	1.521 (3)
N4—C5	1.477 (2)	C14—C16	1.523 (3)
N4—C14	1.496 (2)	C14—H14	1.0000
C5—C13	1.524 (2)	C15—H15A	0.9800
C5—C6	1.538 (2)	C15—H15B	0.9800
C5—H5	1.0000	C15—H15C	0.9800
C6—C7	1.518 (2)	C16—H16B	0.9800
C6—H6	1.0000	C16—H16A	0.9800
C7—C8	1.384 (3)	C16—H16C	0.9800
C7—C12	1.389 (3)	C17—O20	1.206 (2)
C8—C9	1.390 (3)	C17—C18	1.515 (2)
C8—H8	0.9500	C18—C19	1.514 (3)
C9—C10	1.379 (3)	C18—H18A	0.9900
C9—H9	0.9500	C18—H18B	0.9900
C10—C11	1.381 (3)	C19—H19C	0.9800
C10—H10	0.9500	C19—H19B	0.9800
C11—C12	1.393 (3)	C19—H19A	0.9800
C2—O1—C6	124.62 (13)	C5—C13—H13A	109.5
O21—C2—O1	118.98 (16)	C5—C13—H13B	109.5
O21—C2—N3	124.62 (16)	H13A—C13—H13B	109.5
O1—C2—N3	116.34 (15)	C5—C13—H13C	109.5
C2—N3—C17	121.86 (14)	H13A—C13—H13C	109.5
C2—N3—N4	118.59 (14)	H13B—C13—H13C	109.5
C17—N3—N4	118.58 (14)	N4—C14—C15	110.40 (15)
N3—N4—C5	106.83 (12)	N4—C14—C16	108.99 (15)
N3—N4—C14	110.01 (13)	C15—C14—C16	109.78 (16)
C5—N4—C14	115.14 (13)	N4—C14—H14	109.2
N4—C5—C13	109.75 (13)	C15—C14—H14	109.2
N4—C5—C6	109.23 (13)	C16—C14—H14	109.2
C13—C5—C6	115.24 (14)	C14—C15—H15A	109.5
N4—C5—H5	107.4	C14—C15—H15B	109.5
C13—C5—H5	107.4	H15A—C15—H15B	109.5
C6—C5—H5	107.4	C14—C15—H15C	109.5
O1—C6—C7	107.41 (14)	H15A—C15—H15C	109.5
O1—C6—C5	111.69 (13)	H15B—C15—H15C	109.5
C7—C6—C5	114.71 (13)	C14—C16—H16B	109.5
O1—C6—H6	107.6	C14—C16—H16A	109.5
C7—C6—H6	107.6	H16B—C16—H16A	109.5
C5—C6—H6	107.6	C14—C16—H16C	109.5
C8—C7—C12	119.44 (17)	H16B—C16—H16C	109.5
C8—C7—C6	121.81 (16)	H16A—C16—H16C	109.5
C12—C7—C6	118.71 (15)	O20—C17—N3	120.94 (16)
C7—C8—C9	120.16 (19)	O20—C17—C18	122.72 (16)
C7—C8—H8	119.9	N3—C17—C18	116.33 (15)
C9—C8—H8	119.9	C19—C18—C17	111.18 (16)
C10—C9—C8	120.54 (19)	C19—C18—H18A	109.4
C10—C9—H9	119.7	C17—C18—H18A	109.4
C8—C9—H9	119.7	C19—C18—H18B	109.4
C9—C10—C11	119.44 (18)	C17—C18—H18B	109.4
C9—C10—H10	120.3	H18A—C18—H18B	108.0
C11—C10—H10	120.3	C18—C19—H19C	109.5
C10—C11—C12	120.46 (19)	C18—C19—H19B	109.5
C10—C11—H11	119.8	H19C—C19—H19B	109.5
C12—C11—H11	119.8	C18—C19—H19A	109.5
C7—C12—C11	119.96 (18)	H19C—C19—H19A	109.5
C7—C12—H12	120.0	H19B—C19—H19A	109.5
C11—C12—H12	120.0
C6—O1—C2—O21	−165.68 (17)	O1—C6—C7—C12	160.20 (15)
C6—O1—C2—N3	17.1 (2)	C5—C6—C7—C12	−75.0 (2)
O21—C2—N3—C17	29.6 (3)	C12—C7—C8—C9	−0.2 (3)
O1—C2—N3—C17	−153.40 (15)	C6—C7—C8—C9	−177.88 (17)
O21—C2—N3—N4	−161.87 (17)	C7—C8—C9—C10	−0.3 (3)
O1—C2—N3—N4	15.2 (2)	C8—C9—C10—C11	0.6 (3)
C2—N3—N4—C5	−55.15 (18)	C9—C10—C11—C12	−0.4 (3)
C17—N3—N4—C5	113.79 (15)	C8—C7—C12—C11	0.3 (3)
C2—N3—N4—C14	70.48 (18)	C6—C7—C12—C11	178.08 (16)
C17—N3—N4—C14	−120.58 (16)	C10—C11—C12—C7	0.0 (3)
N3—N4—C5—C13	−64.81 (16)	N3—N4—C14—C15	56.73 (18)
C14—N4—C5—C13	172.72 (14)	C5—N4—C14—C15	177.48 (15)
N3—N4—C5—C6	62.43 (16)	N3—N4—C14—C16	177.38 (15)
C14—N4—C5—C6	−60.04 (17)	C5—N4—C14—C16	−61.87 (18)
C2—O1—C6—C7	120.86 (16)	C2—N3—C17—O20	−0.7 (3)
C2—O1—C6—C5	−5.7 (2)	N4—N3—C17—O20	−169.21 (16)
N4—C5—C6—O1	−34.68 (18)	C2—N3—C17—C18	178.17 (16)
C13—C5—C6—O1	89.39 (17)	N4—N3—C17—C18	9.6 (2)
N4—C5—C6—C7	−157.20 (14)	O20—C17—C18—C19	−15.4 (3)
C13—C5—C6—C7	−33.1 (2)	N3—C17—C18—C19	165.80 (17)
O1—C6—C7—C8	−22.1 (2)	O21—C2—C17—O20	23.67 (17)
C5—C6—C7—C8	102.74 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.95	2.40	2.737 (2)	101
C14—H14···O1	1.00	2.55	3.091 (2)	114
C15—H15A···N3	0.98	2.50	2.839 (2)	100
C5—H5···O20i	1.00	2.42	3.263 (2)	142
C16—H16B···O21i	0.98	2.40	3.380 (3)	175
C12—H12···O21i	0.95	2.35	3.243 (2)	156
C5—H5···O21i	1.00	2.40	3.283 (2)	147
C6—H6···O1ii	1.00	2.58	3.543 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.95	2.40	2.737 (2)	101
C14—H14⋯O1	1.00	2.55	3.091 (2)	114
C15—H15A⋯N3	0.98	2.50	2.839 (2)	100
C5—H5⋯O20i	1.00	2.42	3.263 (2)	142
C16—H16B⋯O21i	0.98	2.40	3.380 (3)	175
C12—H12⋯O21i	0.95	2.35	3.243 (2)	156
C5—H5⋯O21i	1.00	2.40	3.283 (2)	147
C6—H6⋯O1ii	1.00	2.58	3.543 (2)	163

Symmetry codes: (i) ; (ii) .