(5R)-3-(2-Chloro-acet-yl)-4-methyl-5-phenyl-1,3,4-oxadiazinan-2-one.

The 1,3,4-oxadiazinan-2-one ring in the title compound, C(12)H(13)ClN(2)O(3), is in a distorted half-chair conformation. The phenyl and chloro-acetyl groups occupy axial and equatorial positions, respectively, and lie to the opposite side of the mol-ecule to the N-bound methyl substituent. Mol-ecules are consolidated in the crystal structure by C-H⋯O inter-actions.

Related literature

For background to 1,3,4-oxadiazin-2-ones, see: Trepanier et al. (1968 ▶); Roussi et al. (1998 ▶, 1999 ▶, 2000 ▶); Casper et al. (2002a ▶,b ▶); Bonin et al. (2006 ▶). For a related structure, see: Zukerman-Schpector et al. (2009 ▶). For the synthesis, see: Rodrigues et al. (2005 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H13ClN2O3

M = 268.69

Orthorhombic,

a = 9.4862 (2) Å

b = 9.6237 (2) Å

c = 13.2433 (3) Å

V = 1209.01 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

29813 measured reflections

2378 independent reflections

2334 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.054

S = 1.07

2378 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 993 Friedel pairs

Flack parameter: 0.01 (5)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: MarvinSketch (Chemaxon, 2010 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020356/hg5045sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020356/hg5045Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020356/hg5045Isup3.cml

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

C12H13ClN2O3	F(000) = 560
Mr = 268.69	Dx = 1.476 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2003 reflections
a = 9.4862 (2) Å	θ = 2.8–16.3°
b = 9.6237 (2) Å	µ = 0.32 mm−1
c = 13.2433 (3) Å	T = 100 K
V = 1209.01 (5) Å3	Block, colourless
Z = 4	0.35 × 0.30 × 0.25 mm

Bruker APEXII CCD diffractometer	2334 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 26.0°, θmin = 2.6°
ω scans	h = −11→11
29813 measured reflections	k = −11→11
2378 independent reflections	l = −16→16

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)] = 0.020	H-atom parameters constrained
wR(F2) = 0.054	w = 1/[σ2(Fo2) + (0.028P)2 + 0.320P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2378 reflections	Δρmax = 0.19 e Å−3
164 parameters	Δρmin = −0.20 e Å−3
0 restraints	Absolute structure: Flack (1983), 993 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (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
Cl	0.24739 (4)	−0.34782 (3)	0.91280 (2)	0.02998 (10)
O1	0.05085 (9)	0.22385 (9)	0.73203 (7)	0.0182 (2)
O2	−0.07381 (9)	0.09934 (10)	0.83862 (7)	0.0196 (2)
O3	0.09385 (10)	−0.08909 (10)	0.93619 (7)	0.0200 (2)
N1	0.13328 (11)	0.00514 (11)	0.77991 (8)	0.0146 (2)
N2	0.22794 (11)	0.00168 (11)	0.69603 (7)	0.0156 (2)
C1	0.02961 (13)	0.10834 (13)	0.78683 (9)	0.0153 (2)
C2	0.28807 (12)	0.14314 (13)	0.68462 (9)	0.0165 (2)
H2	0.3517	0.1421	0.6244	0.020*
C3	0.16885 (13)	0.24374 (14)	0.66273 (9)	0.0184 (3)
H3A	0.2041	0.3402	0.6689	0.022*
H3B	0.1359	0.2301	0.5925	0.022*
C4	0.37768 (13)	0.17604 (13)	0.77675 (9)	0.0163 (2)
C5	0.49224 (13)	0.08997 (14)	0.79745 (10)	0.0200 (3)
H5	0.5116	0.0132	0.7545	0.024*
C6	0.57847 (14)	0.11524 (15)	0.88025 (11)	0.0228 (3)
H6	0.6556	0.0553	0.8942	0.027*
C7	0.55191 (14)	0.22803 (15)	0.94258 (10)	0.0221 (3)
H7	0.6113	0.2458	0.9988	0.027*
C8	0.43859 (15)	0.31474 (13)	0.92274 (10)	0.0212 (3)
H8	0.4203	0.3921	0.9654	0.025*
C9	0.35165 (14)	0.28841 (13)	0.84028 (10)	0.0185 (3)
H9	0.2737	0.3477	0.8272	0.022*
C10	0.15311 (13)	−0.09421 (13)	0.85593 (9)	0.0157 (2)
C11	0.25837 (14)	−0.20626 (13)	0.82638 (9)	0.0194 (3)
H11A	0.3550	−0.1674	0.8271	0.023*
H11B	0.2378	−0.2394	0.7571	0.023*
C12	0.15380 (14)	−0.04923 (14)	0.60530 (9)	0.0195 (3)
H12A	0.1286	−0.1472	0.6146	0.029*
H12B	0.2155	−0.0399	0.5464	0.029*
H12C	0.0680	0.0056	0.5947	0.029*

	U11	U22	U33	U12	U13	U23
Cl	0.0483 (2)	0.01763 (15)	0.02398 (16)	0.00875 (16)	−0.00658 (16)	0.00243 (12)
O1	0.0178 (4)	0.0164 (4)	0.0205 (4)	0.0022 (4)	0.0018 (4)	0.0041 (4)
O2	0.0179 (4)	0.0206 (5)	0.0202 (4)	0.0031 (4)	0.0031 (4)	0.0011 (4)
O3	0.0249 (5)	0.0204 (4)	0.0148 (4)	0.0010 (4)	−0.0004 (4)	−0.0004 (4)
N1	0.0149 (5)	0.0139 (5)	0.0150 (5)	−0.0001 (4)	0.0019 (4)	−0.0008 (4)
N2	0.0170 (5)	0.0159 (5)	0.0138 (5)	−0.0026 (4)	0.0035 (4)	−0.0031 (4)
C1	0.0170 (6)	0.0150 (6)	0.0137 (5)	0.0002 (5)	−0.0030 (5)	−0.0017 (5)
C2	0.0177 (6)	0.0157 (6)	0.0162 (5)	−0.0024 (5)	0.0035 (4)	0.0002 (5)
C3	0.0196 (6)	0.0191 (6)	0.0164 (6)	−0.0026 (5)	0.0014 (5)	0.0025 (5)
C4	0.0157 (6)	0.0163 (6)	0.0170 (5)	−0.0050 (5)	0.0035 (5)	0.0016 (5)
C5	0.0160 (6)	0.0195 (6)	0.0245 (7)	−0.0014 (5)	0.0050 (5)	−0.0024 (5)
C6	0.0142 (6)	0.0263 (7)	0.0280 (7)	−0.0014 (5)	0.0016 (5)	0.0039 (6)
C7	0.0200 (6)	0.0271 (7)	0.0193 (6)	−0.0099 (5)	−0.0015 (5)	0.0034 (5)
C8	0.0270 (7)	0.0181 (6)	0.0186 (6)	−0.0052 (5)	0.0019 (5)	−0.0011 (5)
C9	0.0210 (6)	0.0153 (6)	0.0192 (6)	−0.0001 (5)	0.0029 (5)	0.0012 (5)
C10	0.0169 (6)	0.0141 (6)	0.0160 (6)	−0.0031 (5)	−0.0046 (5)	−0.0024 (5)
C11	0.0210 (6)	0.0156 (6)	0.0218 (6)	0.0012 (5)	−0.0027 (5)	0.0017 (5)
C12	0.0233 (7)	0.0199 (6)	0.0154 (6)	−0.0024 (5)	−0.0006 (5)	−0.0034 (5)

Cl—C11	1.7823 (13)	C4—C5	1.3937 (18)
O1—C1	1.3428 (15)	C5—C6	1.3895 (19)
O1—C3	1.4601 (15)	C5—H5	0.9500
O2—C1	1.2001 (15)	C6—C7	1.387 (2)
O3—C10	1.2034 (16)	C6—H6	0.9500
N1—C1	1.4006 (16)	C7—C8	1.386 (2)
N1—C10	1.4012 (16)	C7—H7	0.9500
N1—N2	1.4287 (14)	C8—C9	1.3917 (19)
N2—C12	1.4760 (15)	C8—H8	0.9500
N2—C2	1.4838 (16)	C9—H9	0.9500
C2—C3	1.5167 (18)	C10—C11	1.5209 (17)
C2—C4	1.5203 (17)	C11—H11A	0.9900
C2—H2	1.0000	C11—H11B	0.9900
C3—H3A	0.9900	C12—H12A	0.9800
C3—H3B	0.9900	C12—H12B	0.9800
C4—C9	1.3923 (18)	C12—H12C	0.9800
C1—O1—C3	124.28 (10)	C7—C6—C5	119.99 (12)
C1—N1—C10	122.08 (11)	C7—C6—H6	120.0
C1—N1—N2	120.58 (10)	C5—C6—H6	120.0
C10—N1—N2	117.28 (10)	C8—C7—C6	119.96 (12)
N1—N2—C12	109.95 (9)	C8—C7—H7	120.0
N1—N2—C2	107.42 (9)	C6—C7—H7	120.0
C12—N2—C2	113.88 (10)	C7—C8—C9	119.92 (13)
O2—C1—O1	119.42 (11)	C7—C8—H8	120.0
O2—C1—N1	124.07 (12)	C9—C8—H8	120.0
O1—C1—N1	116.50 (10)	C8—C9—C4	120.70 (12)
N2—C2—C3	108.57 (10)	C8—C9—H9	119.7
N2—C2—C4	108.92 (10)	C4—C9—H9	119.7
C3—C2—C4	115.94 (11)	O3—C10—N1	122.96 (12)
N2—C2—H2	107.7	O3—C10—C11	124.27 (12)
C3—C2—H2	107.7	N1—C10—C11	112.77 (11)
C4—C2—H2	107.7	C10—C11—Cl	109.77 (9)
O1—C3—C2	111.58 (10)	C10—C11—H11A	109.7
O1—C3—H3A	109.3	Cl—C11—H11A	109.7
C2—C3—H3A	109.3	C10—C11—H11B	109.7
O1—C3—H3B	109.3	Cl—C11—H11B	109.7
C2—C3—H3B	109.3	H11A—C11—H11B	108.2
H3A—C3—H3B	108.0	N2—C12—H12A	109.5
C9—C4—C5	118.75 (12)	N2—C12—H12B	109.5
C9—C4—C2	123.20 (12)	H12A—C12—H12B	109.5
C5—C4—C2	118.04 (12)	N2—C12—H12C	109.5
C6—C5—C4	120.68 (12)	H12A—C12—H12C	109.5
C6—C5—H5	119.7	H12B—C12—H12C	109.5
C4—C5—H5	119.7
C1—N1—N2—C12	−74.26 (13)	C3—C2—C4—C9	1.96 (17)
C10—N1—N2—C12	108.57 (12)	N2—C2—C4—C5	59.96 (14)
C1—N1—N2—C2	50.16 (13)	C3—C2—C4—C5	−177.28 (11)
C10—N1—N2—C2	−127.01 (11)	C9—C4—C5—C6	0.36 (19)
C3—O1—C1—O2	−176.89 (11)	C2—C4—C5—C6	179.64 (11)
C3—O1—C1—N1	3.76 (17)	C4—C5—C6—C7	−0.77 (19)
C10—N1—C1—O2	−22.68 (18)	C5—C6—C7—C8	0.57 (19)
N2—N1—C1—O2	160.29 (11)	C6—C7—C8—C9	0.02 (19)
C10—N1—C1—O1	156.64 (11)	C7—C8—C9—C4	−0.42 (19)
N2—N1—C1—O1	−20.39 (16)	C5—C4—C9—C8	0.23 (19)
N1—N2—C2—C3	−61.59 (12)	C2—C4—C9—C8	−179.00 (11)
C12—N2—C2—C3	60.42 (12)	C1—N1—C10—O3	−8.18 (18)
N1—N2—C2—C4	65.49 (12)	N2—N1—C10—O3	168.94 (11)
C12—N2—C2—C4	−172.50 (10)	C1—N1—C10—C11	172.73 (11)
C1—O1—C3—C2	−18.86 (16)	N2—N1—C10—C11	−10.15 (15)
N2—C2—C3—O1	47.44 (13)	O3—C10—C11—Cl	14.29 (16)
C4—C2—C3—O1	−75.51 (14)	N1—C10—C11—Cl	−166.64 (8)
N2—C2—C4—C9	−120.81 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	1.00	2.60	3.5142 (15)	153
C8—H8···O2ii	0.95	2.60	3.2689 (16)	128
C11—H11b···O2iii	0.99	2.54	3.3675 (16)	141
C12—H12a···O2iii	0.98	2.57	3.5448 (16)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	1.00	2.60	3.5142 (15)	153
C8—H8⋯O2ii	0.95	2.60	3.2689 (16)	128
C11—H11b⋯O2iii	0.99	2.54	3.3675 (16)	141
C12—H12a⋯O2iii	0.98	2.57	3.5448 (16)	173

Symmetry codes: (i) ; (ii) ; (iii) .