(5S,6S)-4,5-Dimethyl-3-methyl-acryloyl-6-phenyl-1,3,4-oxadiazinan-2-one.

The title compound, C(15)H(18)N(2)O(3), is an example of an oxadiazinan-2-one with significant inter-action between the N(3)-acyl and N(4)-methyl groups. These steric inter-actions result in a large torsion angle between the two carbonyl groups, not present with acyl substituents with less steric demand.

Related literature

For related literature, see: Bruno et al. 2004 ▶; Burgeson et al. (2004 ▶); Casper et al. (2002a ▶,b ▶); Ferrence et al. (2003 ▶); Hitchcock et al. (2001 ▶, 2004 ▶); Szczepura et al. (2004 ▶); Trepanier et al. (1968 ▶).

Experimental

Crystal data

C15H18N2O3

M = 274.31

Orthorhombic,

a = 8.7962 (6) Å

b = 9.7797 (6) Å

c = 16.6782 (11) Å

V = 1434.73 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 193 (2) K

0.46 × 0.38 × 0.21 mm

Data collection

Bruker P4/R4/SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003 ▶) T min = 0.865, T max = 0.982

9610 measured reflections

1702 independent reflections

1593 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.080

S = 1.07

1702 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 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, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013986/zl2116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013986/zl2116Isup2.hkl

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

Enhanced figure: interactive version of Fig. 2

C15H18N2O3	F000 = 584
Mr = 274.31	Dx = 1.27 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7730 reflections
a = 8.7962 (6) Å	θ = 3.3–26.4º
b = 9.7797 (6) Å	µ = 0.09 mm−1
c = 16.6782 (11) Å	T = 193 (2) K
V = 1434.73 (16) Å3	Prism, colourless
Z = 4	0.46 × 0.38 × 0.21 mm

Bruker P4/R4/SMART 1000 CCD diffractometer	1702 independent reflections
Radiation source: sealed tube	1593 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
T = 193(2) K	θmax = 26.4º
/w scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS in SAINT-Plus; Bruker, 2003)	h = −10→11
Tmin = 0.865, Tmax = 0.982	k = −11→12
9610 measured reflections	l = −20→20

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.039P)2 + 0.2942P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.032	(Δ/σ)max < 0.001
wR(F2) = 0.080	Δρmax = 0.15 e Å−3
S = 1.07	Δρmin = −0.12 e Å−3
1702 reflections	Extinction correction: none
181 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	Occ. (<1)
O1	0.56811 (14)	0.91142 (13)	0.46559 (7)	0.0296 (3)
C2	0.6459 (2)	0.85642 (18)	0.40478 (10)	0.0255 (4)
N3	0.56076 (17)	0.80251 (16)	0.34127 (8)	0.0270 (3)
N4	0.40508 (18)	0.76608 (16)	0.35333 (9)	0.0281 (3)
C5	0.3312 (2)	0.8846 (2)	0.39098 (11)	0.0275 (4)
H5	0.3518	0.9668	0.357	0.033*
C6	0.4005 (2)	0.90915 (19)	0.47323 (10)	0.0266 (4)
H6	0.3726	0.8301	0.5083	0.032*
C7	0.3531 (2)	1.0377 (2)	0.51526 (11)	0.0293 (4)
C8	0.2870 (2)	1.0285 (2)	0.59025 (12)	0.0382 (5)
H8	0.2767	0.9415	0.615	0.046*
C9	0.2356 (3)	1.1443 (3)	0.63006 (14)	0.0501 (6)
H9	0.1901	1.1364	0.6815	0.06*
C10	0.2509 (3)	1.2699 (3)	0.59454 (16)	0.0548 (7)
H10	0.2146	1.3495	0.6211	0.066*
C11	0.3186 (3)	1.2809 (3)	0.52055 (17)	0.0581 (7)
H11	0.3305	1.3685	0.4967	0.07*
C12	0.3698 (3)	1.1662 (2)	0.48046 (14)	0.0432 (5)
H12	0.4163	1.1749	0.4293	0.052*
C13	0.1593 (2)	0.8641 (2)	0.39546 (12)	0.0368 (5)
H13A	0.119	0.8483	0.3415	0.055*
H13B	0.1119	0.9459	0.4184	0.055*
H13C	0.1366	0.7849	0.4294	0.055*
C14	0.3987 (2)	0.63742 (19)	0.39932 (11)	0.0345 (4)
H14A	0.4509	0.5651	0.3694	0.052*
H14B	0.2923	0.6114	0.4078	0.052*
H14C	0.4486	0.6503	0.4513	0.052*
C15	0.6276 (2)	0.7502 (2)	0.27061 (11)	0.0302 (4)
O16	0.56288 (17)	0.66036 (17)	0.23419 (8)	0.0436 (4)
C17	0.7710 (2)	0.8135 (3)	0.24081 (11)	0.0395 (5)
C18	0.7866 (3)	0.9514 (3)	0.23698 (14)	0.0552 (7)
H18A	0.8742	0.9903	0.2127	0.066*
H18B	0.7099	1.009	0.2586	0.066*
C19	0.8816 (3)	0.7179 (3)	0.20957 (19)	0.0697 (9)
H19A	0.8464	0.6242	0.2191	0.105*	0.5
H19B	0.9793	0.7319	0.2366	0.105*	0.5
H19C	0.8941	0.7327	0.1518	0.105*	0.5
H19D	0.9668	0.7684	0.1859	0.105*	0.5
H19E	0.8339	0.6606	0.1684	0.105*	0.5
H19F	0.9191	0.6599	0.2532	0.105*	0.5
O20	0.78185 (15)	0.85606 (15)	0.40662 (8)	0.0334 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0264 (7)	0.0361 (7)	0.0264 (6)	0.0026 (6)	−0.0026 (5)	−0.0042 (5)
C2	0.0276 (9)	0.0240 (9)	0.0249 (8)	0.0016 (7)	−0.0016 (7)	0.0032 (7)
N3	0.0232 (8)	0.0327 (8)	0.0250 (7)	−0.0007 (7)	0.0007 (6)	−0.0016 (6)
N4	0.0239 (8)	0.0330 (8)	0.0273 (7)	−0.0043 (7)	0.0012 (6)	−0.0013 (6)
C5	0.0253 (9)	0.0304 (10)	0.0267 (8)	−0.0014 (8)	0.0024 (7)	0.0034 (7)
C6	0.0255 (9)	0.0277 (9)	0.0266 (8)	−0.0010 (8)	0.0024 (8)	0.0026 (7)
C7	0.0252 (9)	0.0312 (10)	0.0315 (9)	−0.0004 (8)	−0.0011 (8)	−0.0018 (8)
C8	0.0376 (11)	0.0409 (12)	0.0360 (10)	−0.0041 (10)	0.0027 (9)	−0.0055 (9)
C9	0.0417 (12)	0.0642 (16)	0.0445 (11)	0.0043 (12)	0.0035 (10)	−0.0207 (12)
C10	0.0533 (15)	0.0482 (14)	0.0628 (15)	0.0179 (12)	−0.0107 (13)	−0.0232 (12)
C11	0.0741 (18)	0.0294 (12)	0.0707 (17)	0.0106 (12)	−0.0103 (15)	−0.0008 (12)
C12	0.0514 (13)	0.0342 (11)	0.0442 (11)	0.0028 (10)	0.0044 (10)	0.0044 (10)
C13	0.0248 (9)	0.0471 (12)	0.0384 (10)	−0.0031 (9)	0.0016 (8)	0.0015 (10)
C14	0.0386 (10)	0.0299 (10)	0.0349 (9)	−0.0052 (9)	0.0028 (9)	−0.0033 (8)
C15	0.0278 (10)	0.0379 (11)	0.0249 (8)	0.0029 (8)	−0.0018 (7)	−0.0026 (8)
O16	0.0390 (8)	0.0533 (9)	0.0385 (7)	−0.0053 (8)	0.0051 (6)	−0.0169 (7)
C17	0.0302 (10)	0.0612 (14)	0.0272 (9)	−0.0053 (10)	0.0019 (8)	−0.0060 (9)
C18	0.0665 (17)	0.0539 (15)	0.0453 (12)	−0.0102 (14)	0.0131 (12)	0.0109 (11)
C19	0.0401 (14)	0.089 (2)	0.0800 (18)	−0.0012 (15)	0.0159 (14)	−0.0317 (17)
O20	0.0253 (7)	0.0426 (8)	0.0324 (6)	0.0028 (6)	−0.0047 (5)	−0.0008 (6)

O1—C2	1.336 (2)	C11—C12	1.382 (3)
O1—C6	1.480 (2)	C11—H11	0.95
C2—O20	1.196 (2)	C12—H12	0.95
C2—N3	1.400 (2)	C13—H13A	0.98
N3—C15	1.413 (2)	C13—H13B	0.98
N3—N4	1.429 (2)	C13—H13C	0.98
N4—C5	1.470 (2)	C14—H14A	0.98
N4—C14	1.475 (2)	C14—H14B	0.98
C5—C6	1.520 (2)	C14—H14C	0.98
C5—C13	1.528 (3)	C15—O16	1.210 (2)
C5—H5	1	C15—C17	1.491 (3)
C6—C7	1.499 (3)	C17—C18	1.357 (4)
C6—H6	1	C17—C19	1.447 (3)
C7—C8	1.382 (3)	C18—H18A	0.95
C7—C12	1.392 (3)	C18—H18B	0.95
C8—C9	1.388 (3)	C19—H19A	0.98
C8—H8	0.95	C19—H19B	0.98
C9—C10	1.371 (4)	C19—H19C	0.98
C9—H9	0.95	C19—H19D	0.98
C10—C11	1.375 (4)	C19—H19E	0.98
C10—H10	0.95	C19—H19F	0.98
C2—O1—C6	124.71 (14)	C5—C13—H13B	109.5
O20—C2—O1	119.58 (17)	H13A—C13—H13B	109.5
O20—C2—N3	123.57 (17)	C5—C13—H13C	109.5
O1—C2—N3	116.85 (15)	H13A—C13—H13C	109.5
C2—N3—C15	123.02 (15)	H13B—C13—H13C	109.5
C2—N3—N4	119.99 (14)	N4—C14—H14A	109.5
C15—N3—N4	115.19 (14)	N4—C14—H14B	109.5
N3—N4—C5	106.68 (14)	H14A—C14—H14B	109.5
N3—N4—C14	108.80 (14)	N4—C14—H14C	109.5
C5—N4—C14	115.71 (14)	H14A—C14—H14C	109.5
N4—C5—C6	109.45 (14)	H14B—C14—H14C	109.5
N4—C5—C13	110.80 (16)	O16—C15—N3	119.08 (18)
C6—C5—C13	111.93 (15)	O16—C15—C17	122.15 (18)
N4—C5—H5	108.2	N3—C15—C17	118.67 (17)
C6—C5—H5	108.2	C18—C17—C19	123.9 (3)
C13—C5—H5	108.2	C18—C17—C15	120.9 (2)
O1—C6—C7	107.77 (14)	C19—C17—C15	114.9 (2)
O1—C6—C5	108.91 (14)	C17—C18—H18A	120
C7—C6—C5	116.28 (15)	C17—C18—H18B	120
O1—C6—H6	107.9	H18A—C18—H18B	120
C7—C6—H6	107.9	C17—C19—H19A	109.5
C5—C6—H6	107.9	C17—C19—H19B	109.5
C8—C7—C12	118.74 (19)	H19A—C19—H19B	109.5
C8—C7—C6	119.06 (18)	C17—C19—H19C	109.5
C12—C7—C6	122.18 (17)	H19A—C19—H19C	109.5
C7—C8—C9	121.1 (2)	H19B—C19—H19C	109.5
C7—C8—H8	119.4	C17—C19—H19D	109.5
C9—C8—H8	119.4	H19A—C19—H19D	141.1
C10—C9—C8	119.5 (2)	H19B—C19—H19D	56.3
C10—C9—H9	120.3	H19C—C19—H19D	56.3
C8—C9—H9	120.3	C17—C19—H19E	109.5
C9—C10—C11	120.0 (2)	H19A—C19—H19E	56.3
C9—C10—H10	120	H19B—C19—H19E	141.1
C11—C10—H10	120	H19C—C19—H19E	56.3
C10—C11—C12	120.8 (2)	H19D—C19—H19E	109.5
C10—C11—H11	119.6	C17—C19—H19F	109.5
C12—C11—H11	119.6	H19A—C19—H19F	56.3
C11—C12—C7	119.8 (2)	H19B—C19—H19F	56.3
C11—C12—H12	120.1	H19C—C19—H19F	141.1
C7—C12—H12	120.1	H19D—C19—H19F	109.5
C5—C13—H13A	109.5	H19E—C19—H19F	109.5
C6—O1—C2—O20	−175.30 (16)	C5—C6—C7—C8	122.65 (19)
C6—O1—C2—N3	5.1 (3)	O1—C6—C7—C12	66.8 (2)
O20—C2—N3—C15	−4.2 (3)	C5—C6—C7—C12	−55.7 (2)
O1—C2—N3—C15	175.31 (16)	C12—C7—C8—C9	1.1 (3)
O20—C2—N3—N4	159.76 (17)	C6—C7—C8—C9	−177.33 (19)
O1—C2—N3—N4	−20.7 (2)	C7—C8—C9—C10	−0.2 (3)
C2—N3—N4—C5	50.5 (2)	C8—C9—C10—C11	−0.9 (4)
C15—N3—N4—C5	−144.27 (15)	C9—C10—C11—C12	1.1 (4)
C2—N3—N4—C14	−74.94 (19)	C10—C11—C12—C7	−0.2 (4)
C15—N3—N4—C14	90.25 (17)	C8—C7—C12—C11	−0.9 (3)
N3—N4—C5—C6	−64.27 (17)	C6—C7—C12—C11	177.5 (2)
C14—N4—C5—C6	56.91 (19)	C2—N3—C15—O16	150.77 (18)
N3—N4—C5—C13	171.82 (15)	N4—N3—C15—O16	−13.9 (3)
C14—N4—C5—C13	−67.0 (2)	C2—N3—C15—C17	−32.8 (3)
C2—O1—C6—C7	−147.65 (16)	N4—N3—C15—C17	162.50 (16)
C2—O1—C6—C5	−20.7 (2)	O16—C15—C17—C18	130.5 (2)
N4—C5—C6—O1	50.02 (18)	N3—C15—C17—C18	−45.8 (3)
C13—C5—C6—O1	173.25 (16)	O16—C15—C17—C19	−43.4 (3)
N4—C5—C6—C7	171.95 (15)	N3—C15—C17—C19	140.3 (2)
C13—C5—C6—C7	−64.8 (2)	O20—C2—C15—O16	132.4 (3)
O1—C6—C7—C8	−114.81 (19)