tert-Butyl 4-isopropyl-2-oxo-6-phenyl-3,4-dihydro-2H-pyran-3-carboxyl-ate.

In the title compound, C(19)H(24)O(4), the six-membered lactone ring adopts an envelope conformation with the tert-butoxy-carbonyl and isopropyl substituents in axial positions, and the phenyl group in an equatorial position. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For the applications and synthesis of endocyclic enol lactones, see: Davies & Jin (2004 ▶); Evans et al. (2005 ▶); Krafft & Katzenellenbogen (1981 ▶); Li et al. (2007 ▶); Zeni et al. (2004 ▶); Zhao et al. (1997 ▶); Jimenez-Tenorio et al. (2001 ▶). For the synthesis, see: Li et al. (2009 ▶).

Experimental

Crystal data

C19H24O4

M = 316.38

Triclinic,

a = 8.6163 (9) Å

b = 10.888 (1) Å

c = 11.261 (1) Å

α = 68.393 (2)°

β = 79.118 (2)°

γ = 67.998 (2)°

V = 909.09 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.48 × 0.46 × 0.42 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.760, T max = 1.000

4986 measured reflections

3510 independent reflections

2759 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.158

S = 1.04

3510 reflections

213 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001367X/lx2139sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001367X/lx2139Isup2.hkl

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

C19H24O4	Z = 2
Mr = 316.38	F(000) = 340
Triclinic, P1	Dx = 1.156 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6163 (9) Å	Cell parameters from 2216 reflections
b = 10.888 (1) Å	θ = 4.8–55.3°
c = 11.261 (1) Å	µ = 0.08 mm−1
α = 68.393 (2)°	T = 293 K
β = 79.118 (2)°	Prismatic, colorless
γ = 67.998 (2)°	0.48 × 0.46 × 0.42 mm
V = 909.09 (15) Å3

Bruker SMART CCD area-detector diffractometer	3510 independent reflections
Radiation source: fine-focus sealed tube	2759 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 10.0 pixels mm-1	θmax = 26.0°, θmin = 2.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −10→13
Tmin = 0.760, Tmax = 1.000	l = −13→12
4986 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0925P)2 + 0.0377P] where P = (Fo2 + 2Fc2)/3
3510 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	−0.04144 (14)	0.87317 (11)	0.66284 (11)	0.0535 (3)
O2	0.07228 (13)	0.64576 (11)	0.71597 (10)	0.0461 (3)
O3	0.48770 (16)	0.75686 (16)	0.51105 (14)	0.0721 (4)
O4	0.33639 (14)	0.77581 (13)	0.69310 (12)	0.0554 (3)
C1	0.06511 (19)	0.77682 (15)	0.63769 (14)	0.0408 (4)
C2	0.19583 (19)	0.78720 (16)	0.52821 (14)	0.0425 (4)
H2	0.1560	0.8805	0.4644	0.051*
C3	0.2282 (2)	0.67697 (16)	0.46303 (15)	0.0441 (4)
H3	0.3364	0.6694	0.4143	0.053*
C4	0.2483 (2)	0.53947 (16)	0.56580 (15)	0.0450 (4)
H4	0.3113	0.4581	0.5464	0.054*
C5	0.18081 (19)	0.52752 (15)	0.68321 (15)	0.0412 (4)
C6	0.3589 (2)	0.77079 (16)	0.57572 (16)	0.0470 (4)
C7	0.4744 (3)	0.7625 (3)	0.7630 (2)	0.0739 (6)
C8	0.5394 (3)	0.8833 (3)	0.6928 (3)	0.0982 (9)
H8A	0.5896	0.8764	0.6108	0.147*
H8B	0.6216	0.8799	0.7418	0.147*
H8C	0.4481	0.9703	0.6812	0.147*
C9	0.3851 (4)	0.7727 (4)	0.8901 (2)	0.1092 (10)
H9A	0.2958	0.8610	0.8764	0.164*
H9B	0.4630	0.7658	0.9448	0.164*
H9C	0.3398	0.6978	0.9296	0.164*
C10	0.6078 (4)	0.6211 (3)	0.7773 (4)	0.1282 (12)
H10A	0.5556	0.5509	0.8000	0.192*
H10B	0.6796	0.5992	0.8432	0.192*
H10C	0.6730	0.6233	0.6979	0.192*
C11	0.0973 (2)	0.7132 (2)	0.36787 (17)	0.0589 (5)
H11	0.1194	0.6283	0.3467	0.071*
C12	0.1187 (4)	0.8256 (3)	0.2436 (2)	0.0887 (8)
H12A	0.0410	0.8410	0.1845	0.133*
H12B	0.2312	0.7957	0.2076	0.133*
H12C	0.0976	0.9111	0.2601	0.133*
C13	−0.0809 (3)	0.7518 (3)	0.4235 (2)	0.0799 (6)
H13A	−0.1104	0.8386	0.4398	0.120*
H13B	−0.0909	0.6793	0.5021	0.120*
H13C	−0.1549	0.7622	0.3639	0.120*
C14	0.1969 (2)	0.39882 (16)	0.79280 (14)	0.0423 (4)
C15	0.0804 (2)	0.39429 (19)	0.89627 (17)	0.0575 (5)
H15	−0.0092	0.4750	0.8975	0.069*
C16	0.0954 (3)	0.2717 (2)	0.99749 (19)	0.0686 (6)
H16	0.0167	0.2701	1.0665	0.082*
C17	0.2272 (3)	0.1519 (2)	0.99593 (19)	0.0678 (6)
H17	0.2381	0.0692	1.0643	0.081*
C18	0.3423 (3)	0.15430 (19)	0.89392 (19)	0.0637 (5)
H18	0.4300	0.0726	0.8925	0.076*
C19	0.3295 (2)	0.27597 (18)	0.79372 (17)	0.0531 (4)
H19	0.4099	0.2766	0.7258	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.0522 (7)	0.0401 (7)	0.0579 (7)	−0.0079 (5)	0.0052 (5)	−0.0165 (5)
O2	0.0517 (6)	0.0357 (6)	0.0438 (6)	−0.0129 (5)	0.0106 (5)	−0.0134 (5)
O3	0.0540 (8)	0.0982 (11)	0.0823 (10)	−0.0365 (7)	0.0214 (7)	−0.0508 (9)
O4	0.0482 (7)	0.0722 (9)	0.0523 (7)	−0.0250 (6)	0.0004 (5)	−0.0241 (6)
C1	0.0431 (8)	0.0347 (8)	0.0416 (8)	−0.0115 (7)	−0.0013 (6)	−0.0111 (6)
C2	0.0481 (9)	0.0342 (8)	0.0390 (8)	−0.0142 (7)	0.0015 (7)	−0.0068 (6)
C3	0.0499 (9)	0.0437 (9)	0.0368 (8)	−0.0174 (7)	0.0050 (7)	−0.0129 (7)
C4	0.0528 (9)	0.0372 (8)	0.0431 (9)	−0.0126 (7)	0.0014 (7)	−0.0156 (7)
C5	0.0432 (8)	0.0351 (8)	0.0437 (9)	−0.0113 (6)	0.0007 (6)	−0.0145 (7)
C6	0.0498 (9)	0.0401 (9)	0.0508 (10)	−0.0178 (7)	0.0057 (7)	−0.0159 (7)
C7	0.0590 (12)	0.1008 (17)	0.0697 (13)	−0.0321 (12)	−0.0105 (10)	−0.0277 (12)
C8	0.0908 (18)	0.139 (2)	0.108 (2)	−0.0700 (17)	0.0064 (15)	−0.0615 (18)
C9	0.110 (2)	0.184 (3)	0.0641 (15)	−0.076 (2)	−0.0044 (14)	−0.0459 (18)
C10	0.094 (2)	0.116 (3)	0.146 (3)	0.0030 (18)	−0.057 (2)	−0.026 (2)
C11	0.0786 (13)	0.0560 (11)	0.0459 (10)	−0.0254 (9)	−0.0091 (9)	−0.0156 (8)
C12	0.133 (2)	0.0810 (16)	0.0502 (12)	−0.0445 (15)	−0.0187 (13)	−0.0041 (11)
C13	0.0670 (13)	0.1032 (18)	0.0811 (15)	−0.0288 (12)	−0.0189 (11)	−0.0356 (13)
C14	0.0498 (9)	0.0409 (9)	0.0378 (8)	−0.0173 (7)	−0.0034 (7)	−0.0123 (7)
C15	0.0672 (11)	0.0478 (10)	0.0471 (10)	−0.0165 (8)	0.0072 (8)	−0.0120 (8)
C16	0.0870 (14)	0.0654 (13)	0.0459 (10)	−0.0332 (11)	0.0097 (10)	−0.0086 (9)
C17	0.0943 (15)	0.0496 (11)	0.0497 (11)	−0.0275 (11)	−0.0122 (10)	0.0020 (8)
C18	0.0752 (13)	0.0427 (10)	0.0580 (12)	−0.0073 (9)	−0.0148 (10)	−0.0071 (8)
C19	0.0539 (10)	0.0487 (10)	0.0482 (10)	−0.0123 (8)	−0.0030 (8)	−0.0112 (8)

O1—C1	1.1927 (18)	C9—H9C	0.9600
O2—C1	1.3584 (18)	C10—H10A	0.9600
O2—C5	1.4091 (17)	C10—H10B	0.9600
O3—C6	1.198 (2)	C10—H10C	0.9600
O4—C6	1.318 (2)	C11—C13	1.508 (3)
O4—C7	1.482 (2)	C11—C12	1.517 (3)
C1—C2	1.507 (2)	C11—H11	0.9800
C2—C6	1.523 (2)	C12—H12A	0.9600
C2—C3	1.542 (2)	C12—H12B	0.9600
C2—H2	0.9800	C12—H12C	0.9600
C3—C4	1.489 (2)	C13—H13A	0.9600
C3—C11	1.545 (2)	C13—H13B	0.9600
C3—H3	0.9800	C13—H13C	0.9600
C4—C5	1.320 (2)	C14—C15	1.386 (2)
C4—H4	0.9300	C14—C19	1.394 (2)
C5—C14	1.467 (2)	C15—C16	1.380 (3)
C7—C10	1.510 (4)	C15—H15	0.9300
C7—C8	1.512 (4)	C16—C17	1.375 (3)
C7—C9	1.513 (3)	C16—H16	0.9300
C8—H8A	0.9600	C17—C18	1.368 (3)
C8—H8B	0.9600	C17—H17	0.9300
C8—H8C	0.9600	C18—C19	1.370 (2)
C9—H9A	0.9600	C18—H18	0.9300
C9—H9B	0.9600	C19—H19	0.9300
C1—O2—C5	120.35 (11)	H9B—C9—H9C	109.5
C6—O4—C7	122.54 (14)	C7—C10—H10A	109.5
O1—C1—O2	117.45 (14)	C7—C10—H10B	109.5
O1—C1—C2	125.81 (14)	H10A—C10—H10B	109.5
O2—C1—C2	116.73 (12)	C7—C10—H10C	109.5
C1—C2—C6	109.81 (13)	H10A—C10—H10C	109.5
C1—C2—C3	112.32 (12)	H10B—C10—H10C	109.5
C6—C2—C3	109.70 (13)	C13—C11—C12	111.18 (19)
C1—C2—H2	108.3	C13—C11—C3	113.38 (15)
C6—C2—H2	108.3	C12—C11—C3	111.50 (16)
C3—C2—H2	108.3	C13—C11—H11	106.8
C4—C3—C2	107.53 (12)	C12—C11—H11	106.8
C4—C3—C11	112.76 (13)	C3—C11—H11	106.8
C2—C3—C11	115.19 (14)	C11—C12—H12A	109.5
C4—C3—H3	107.0	C11—C12—H12B	109.5
C2—C3—H3	107.0	H12A—C12—H12B	109.5
C11—C3—H3	107.0	C11—C12—H12C	109.5
C5—C4—C3	123.13 (14)	H12A—C12—H12C	109.5
C5—C4—H4	118.4	H12B—C12—H12C	109.5
C3—C4—H4	118.4	C11—C13—H13A	109.5
C4—C5—O2	121.22 (13)	C11—C13—H13B	109.5
C4—C5—C14	127.91 (14)	H13A—C13—H13B	109.5
O2—C5—C14	110.81 (12)	C11—C13—H13C	109.5
O3—C6—O4	126.45 (17)	H13A—C13—H13C	109.5
O3—C6—C2	122.48 (16)	H13B—C13—H13C	109.5
O4—C6—C2	111.06 (13)	C15—C14—C19	118.15 (15)
O4—C7—C10	108.8 (2)	C15—C14—C5	121.59 (15)
O4—C7—C8	109.19 (19)	C19—C14—C5	120.24 (14)
C10—C7—C8	113.0 (2)	C16—C15—C14	120.91 (17)
O4—C7—C9	101.57 (16)	C16—C15—H15	119.5
C10—C7—C9	111.9 (2)	C14—C15—H15	119.5
C8—C7—C9	111.7 (2)	C17—C16—C15	119.78 (19)
C7—C8—H8A	109.5	C17—C16—H16	120.1
C7—C8—H8B	109.5	C15—C16—H16	120.1
H8A—C8—H8B	109.5	C18—C17—C16	120.00 (17)
C7—C8—H8C	109.5	C18—C17—H17	120.0
H8A—C8—H8C	109.5	C16—C17—H17	120.0
H8B—C8—H8C	109.5	C17—C18—C19	120.62 (18)
C7—C9—H9A	109.5	C17—C18—H18	119.7
C7—C9—H9B	109.5	C19—C18—H18	119.7
H9A—C9—H9B	109.5	C18—C19—C14	120.52 (17)
C7—C9—H9C	109.5	C18—C19—H19	119.7
H9A—C9—H9C	109.5	C14—C19—H19	119.7
C5—O2—C1—O1	172.04 (14)	C3—C2—C6—O4	−134.60 (13)
C5—O2—C1—C2	−9.4 (2)	C6—O4—C7—C10	−61.0 (3)
O1—C1—C2—C6	97.55 (18)	C6—O4—C7—C8	62.8 (2)
O2—C1—C2—C6	−80.92 (16)	C6—O4—C7—C9	−179.16 (19)
O1—C1—C2—C3	−140.10 (16)	C4—C3—C11—C13	72.2 (2)
O2—C1—C2—C3	41.43 (19)	C2—C3—C11—C13	−51.7 (2)
C1—C2—C3—C4	−47.02 (17)	C4—C3—C11—C12	−161.41 (17)
C6—C2—C3—C4	75.39 (15)	C2—C3—C11—C12	74.6 (2)
C1—C2—C3—C11	79.62 (17)	C4—C5—C14—C15	−158.33 (18)
C6—C2—C3—C11	−157.96 (13)	O2—C5—C14—C15	18.9 (2)
C2—C3—C4—C5	25.9 (2)	C4—C5—C14—C19	20.1 (3)
C11—C3—C4—C5	−102.21 (19)	O2—C5—C14—C19	−162.68 (14)
C3—C4—C5—O2	5.5 (2)	C19—C14—C15—C16	0.2 (3)
C3—C4—C5—C14	−177.58 (15)	C5—C14—C15—C16	178.69 (17)
C1—O2—C5—C4	−15.6 (2)	C14—C15—C16—C17	−0.3 (3)
C1—O2—C5—C14	166.99 (13)	C15—C16—C17—C18	−0.4 (3)
C7—O4—C6—O3	−0.8 (3)	C16—C17—C18—C19	1.2 (3)
C7—O4—C6—C2	179.96 (15)	C17—C18—C19—C14	−1.3 (3)
C1—C2—C6—O3	170.02 (16)	C15—C14—C19—C18	0.6 (3)
C3—C2—C6—O3	46.1 (2)	C5—C14—C19—C18	−177.89 (16)
C1—C2—C6—O4	−10.70 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.98	2.44	3.407 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.98	2.44	3.407 (2)	170

Symmetry code: (i) .