(Z)-5-Benzyl-idene-3-butyl-4-phenyl-1,3-oxazolidin-2-one.

In the title compound, C(20)H(21)NO(2), the benzyl group and the oxazolidin-2-one unit are each essentially planar, with maximum deviations of 0.026 (2) and 0.031 (2) Å, respectively. The dihedral angle between the phenyl ring and the oxazolidin-2-one unit is 69.25 (2)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For general background to 2-oxazolidinone derivatives and for heterocyclic systems of anti­bacterial inter­est, see: Mukhtar & Wright (2005 ▶); Ager et al. (1996 ▶); Renslo et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the chemical structure of the title compound established from NMR data, see: Yoo & Li (2008 ▶).

Experimental

Crystal data

C20H21NO2

M = 307.38

Monoclinic,

a = 10.029 (2) Å

b = 9.1941 (18) Å

c = 18.389 (4) Å

β = 100.51 (3)°

V = 1667.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.31 × 0.25 × 0.18 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.989, T max = 0.997

12969 measured reflections

2994 independent reflections

1803 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.03

2994 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008762/bg2393sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008762/bg2393Isup2.hkl

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

C20H21NO2	F(000) = 656
Mr = 307.38	Dx = 1.225 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5837 reflections
a = 10.029 (2) Å	θ = 2.8–27.9°
b = 9.1941 (18) Å	µ = 0.08 mm−1
c = 18.389 (4) Å	T = 293 K
β = 100.51 (3)°	Block, colorless
V = 1667.1 (6) Å3	0.31 × 0.25 × 0.18 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	2994 independent reflections
Radiation source: fine-focus sealed tube	1803 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scans	θmax = 25.2°, θmin = 3.0°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −12→12
Tmin = 0.989, Tmax = 0.997	k = −11→11
12969 measured reflections	l = −22→21

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0472P)2 + 0.3223P] where P = (Fo2 + 2Fc2)/3
2994 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.17 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	0.59314 (19)	0.3280 (2)	0.36032 (11)	0.0590 (5)
H1	0.5441	0.3603	0.3154	0.071*
C2	0.5426 (2)	0.3511 (3)	0.42412 (12)	0.0675 (6)
H2	0.4609	0.4003	0.4218	0.081*
C3	0.6115 (2)	0.3023 (3)	0.49109 (12)	0.0680 (6)
H3	0.5764	0.3174	0.5339	0.082*
C4	0.7330 (2)	0.2308 (2)	0.49425 (11)	0.0636 (6)
H4	0.7798	0.1966	0.5393	0.076*
C5	0.78512 (19)	0.2099 (2)	0.43106 (10)	0.0532 (5)
H5	0.8682	0.1630	0.4342	0.064*
C6	0.71618 (17)	0.2574 (2)	0.36199 (10)	0.0477 (5)
C7	0.77658 (18)	0.2274 (2)	0.29672 (10)	0.0517 (5)
H7	0.8565	0.1737	0.3059	0.062*
C8	0.73519 (17)	0.2650 (2)	0.22699 (10)	0.0477 (5)
C9	0.6003 (2)	0.3656 (2)	0.12780 (11)	0.0560 (5)
C10	0.79952 (18)	0.2321 (2)	0.16033 (10)	0.0509 (5)
H10	0.7967	0.1270	0.1512	0.061*
C11	0.94436 (17)	0.2858 (2)	0.16712 (9)	0.0471 (5)
C12	0.9744 (2)	0.4219 (2)	0.14300 (11)	0.0569 (5)
H12	0.9047	0.4837	0.1217	0.068*
C13	1.1078 (2)	0.4670 (3)	0.15040 (12)	0.0669 (6)
H13	1.1271	0.5584	0.1333	0.080*
C14	1.2119 (2)	0.3782 (3)	0.18269 (12)	0.0688 (6)
H14	1.3013	0.4090	0.1874	0.083*
C15	1.1831 (2)	0.2442 (3)	0.20790 (12)	0.0678 (6)
H15	1.2532	0.1842	0.2306	0.081*
C16	1.05059 (19)	0.1974 (2)	0.19989 (11)	0.0585 (5)
H16	1.0322	0.1054	0.2167	0.070*
C17	0.7052 (2)	0.2948 (3)	0.02324 (10)	0.0651 (6)
H17A	0.7983	0.3011	0.0159	0.078*
H17B	0.6563	0.3771	−0.0016	0.078*
C18	0.6430 (2)	0.1560 (2)	−0.01191 (10)	0.0643 (6)
H18A	0.5527	0.1447	−0.0008	0.077*
H18B	0.6971	0.0738	0.0094	0.077*
C19	0.6343 (2)	0.1550 (3)	−0.09517 (10)	0.0707 (6)
H19A	0.7254	0.1578	−0.1060	0.085*
H19B	0.5875	0.2421	−0.1158	0.085*
C20	0.5609 (3)	0.0224 (3)	−0.13268 (12)	0.0880 (8)
H20A	0.6069	−0.0643	−0.1128	0.132*
H20B	0.5600	0.0270	−0.1849	0.132*
H20C	0.4694	0.0210	−0.1240	0.132*
N1	0.70329 (15)	0.30487 (19)	0.10237 (8)	0.0570 (5)
O1	0.61860 (12)	0.34597 (15)	0.20363 (7)	0.0572 (4)
O2	0.50276 (13)	0.43149 (18)	0.09551 (8)	0.0707 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0542 (12)	0.0656 (14)	0.0581 (12)	0.0036 (10)	0.0127 (10)	0.0080 (10)
C2	0.0576 (12)	0.0786 (16)	0.0709 (14)	0.0087 (12)	0.0242 (11)	0.0050 (12)
C3	0.0719 (14)	0.0809 (17)	0.0569 (13)	−0.0049 (13)	0.0272 (11)	−0.0012 (11)
C4	0.0655 (13)	0.0775 (16)	0.0483 (12)	−0.0063 (12)	0.0121 (10)	0.0030 (10)
C5	0.0486 (10)	0.0606 (13)	0.0501 (11)	−0.0024 (9)	0.0079 (9)	0.0028 (9)
C6	0.0439 (10)	0.0522 (12)	0.0478 (11)	−0.0035 (9)	0.0103 (8)	0.0021 (9)
C7	0.0475 (10)	0.0575 (13)	0.0496 (11)	0.0031 (9)	0.0079 (9)	0.0033 (9)
C8	0.0403 (9)	0.0536 (12)	0.0484 (11)	0.0000 (9)	0.0061 (8)	0.0021 (9)
C9	0.0478 (11)	0.0695 (14)	0.0498 (11)	−0.0064 (11)	0.0066 (9)	0.0065 (10)
C10	0.0509 (10)	0.0564 (12)	0.0440 (10)	0.0004 (9)	0.0050 (8)	−0.0012 (9)
C11	0.0451 (10)	0.0569 (13)	0.0397 (10)	0.0054 (9)	0.0090 (8)	−0.0048 (9)
C12	0.0545 (12)	0.0586 (14)	0.0572 (12)	0.0060 (10)	0.0087 (9)	0.0024 (10)
C13	0.0655 (13)	0.0702 (15)	0.0667 (14)	−0.0091 (12)	0.0163 (11)	−0.0021 (11)
C14	0.0495 (12)	0.0943 (19)	0.0639 (13)	−0.0051 (13)	0.0134 (10)	−0.0137 (13)
C15	0.0531 (12)	0.0852 (18)	0.0638 (14)	0.0157 (12)	0.0074 (10)	−0.0040 (12)
C16	0.0573 (12)	0.0622 (14)	0.0551 (12)	0.0092 (11)	0.0074 (10)	0.0002 (10)
C17	0.0596 (12)	0.0931 (17)	0.0412 (11)	−0.0056 (12)	0.0060 (9)	0.0018 (11)
C18	0.0695 (13)	0.0788 (16)	0.0429 (11)	0.0114 (12)	0.0061 (9)	0.0005 (10)
C19	0.0640 (13)	0.1041 (19)	0.0441 (11)	0.0091 (13)	0.0105 (10)	−0.0017 (12)
C20	0.122 (2)	0.091 (2)	0.0481 (13)	0.0186 (16)	0.0078 (13)	−0.0100 (12)
N1	0.0505 (9)	0.0798 (13)	0.0386 (9)	0.0037 (9)	0.0026 (7)	0.0022 (8)
O1	0.0494 (8)	0.0730 (10)	0.0493 (8)	0.0095 (7)	0.0088 (6)	0.0084 (7)
O2	0.0487 (8)	0.0929 (12)	0.0676 (9)	0.0062 (8)	0.0029 (7)	0.0216 (8)

C1—C2	1.376 (3)	C11—C16	1.387 (3)
C1—C6	1.390 (3)	C12—C13	1.383 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.373 (3)	C13—C14	1.372 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.376 (3)	C14—C15	1.365 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.372 (3)	C15—C16	1.379 (3)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.401 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—N1	1.461 (2)
C6—C7	1.466 (3)	C17—C18	1.513 (3)
C7—C8	1.320 (2)	C17—H17A	0.9700
C7—H7	0.9300	C17—H17B	0.9700
C8—O1	1.387 (2)	C18—C19	1.518 (3)
C8—C10	1.516 (3)	C18—H18A	0.9700
C9—O2	1.210 (2)	C18—H18B	0.9700
C9—N1	1.332 (2)	C19—C20	1.523 (3)
C9—O1	1.385 (2)	C19—H19A	0.9700
C10—N1	1.463 (2)	C19—H19B	0.9700
C10—C11	1.518 (2)	C20—H20A	0.9600
C10—H10	0.9800	C20—H20B	0.9600
C11—C12	1.380 (3)	C20—H20C	0.9600
C2—C1—C6	121.09 (19)	C14—C13—H13	119.7
C2—C1—H1	119.5	C12—C13—H13	119.7
C6—C1—H1	119.5	C15—C14—C13	119.5 (2)
C1—C2—C3	120.7 (2)	C15—C14—H14	120.2
C1—C2—H2	119.6	C13—C14—H14	120.2
C3—C2—H2	119.6	C14—C15—C16	120.3 (2)
C4—C3—C2	119.4 (2)	C14—C15—H15	119.9
C4—C3—H3	120.3	C16—C15—H15	119.9
C2—C3—H3	120.3	C15—C16—C11	120.8 (2)
C5—C4—C3	120.2 (2)	C15—C16—H16	119.6
C5—C4—H4	119.9	C11—C16—H16	119.6
C3—C4—H4	119.9	N1—C17—C18	113.57 (17)
C4—C5—C6	121.53 (19)	N1—C17—H17A	108.9
C4—C5—H5	119.2	C18—C17—H17A	108.9
C6—C5—H5	119.2	N1—C17—H17B	108.9
C1—C6—C5	117.08 (18)	C18—C17—H17B	108.9
C1—C6—C7	124.57 (17)	H17A—C17—H17B	107.7
C5—C6—C7	118.34 (17)	C17—C18—C19	112.31 (18)
C8—C7—C6	130.01 (18)	C17—C18—H18A	109.1
C8—C7—H7	115.0	C19—C18—H18A	109.1
C6—C7—H7	115.0	C17—C18—H18B	109.1
C7—C8—O1	122.65 (17)	C19—C18—H18B	109.1
C7—C8—C10	128.95 (17)	H18A—C18—H18B	107.9
O1—C8—C10	108.40 (15)	C18—C19—C20	113.3 (2)
O2—C9—N1	130.30 (19)	C18—C19—H19A	108.9
O2—C9—O1	120.42 (19)	C20—C19—H19A	108.9
N1—C9—O1	109.27 (17)	C18—C19—H19B	108.9
N1—C10—C8	100.16 (15)	C20—C19—H19B	108.9
N1—C10—C11	113.93 (16)	H19A—C19—H19B	107.7
C8—C10—C11	114.25 (15)	C19—C20—H20A	109.5
N1—C10—H10	109.4	C19—C20—H20B	109.5
C8—C10—H10	109.4	H20A—C20—H20B	109.5
C11—C10—H10	109.4	C19—C20—H20C	109.5
C12—C11—C16	118.39 (18)	H20A—C20—H20C	109.5
C12—C11—C10	122.06 (17)	H20B—C20—H20C	109.5
C16—C11—C10	119.54 (19)	C9—N1—C10	112.76 (15)
C13—C12—C11	120.3 (2)	C9—N1—C17	121.86 (16)
C13—C12—H12	119.8	C10—N1—C17	124.73 (16)
C11—C12—H12	119.8	C9—O1—C8	109.36 (15)
C14—C13—C12	120.6 (2)

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.93	2.58	3.343 (3)	141
C3—H3···Cg2ii	0.93	2.93	3.674 (2)	138
C12—H12···Cg1iii	0.93	2.91	3.706 (3)	145
C20—H20B···Cg2iv	0.96	2.92	3.812 (1)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.93	2.58	3.343 (3)	141
C3—H3⋯Cg2ii	0.93	2.93	3.674 (2)	138
C12—H12⋯Cg1iii	0.93	2.91	3.706 (3)	145
C20—H20B⋯Cg2iv	0.96	2.92	3.812 (1)	156

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