Ethyl 2,2-dimethyl-4-oxo-6-phenyl-3,4-di­hydro-2H-pyran-5-carboxyl­ate

The title compound, C₁₆H₁₈O₄, is a derivative of 3,4-di­hydro-2H-pyran-4-one. The plane of the pyranone ring system forms a dihedral angle of 42.76 (10)° with that of the phenyl group. The crystal structure is stabilized by C—H...O inter­actions that enclose an R₂¹(6) ring motif and link the molecules into chains along the c axis. A short intra­molecular O...O contact [2.942 (3) Å] gives rise to an S(5) motif.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.122
• Data-to-parameter ratio = 22.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond   C13    -   C14    ..       1.42 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         67 %

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.400 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         99 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: QMOL (Gans & Shalloway, 2001), Mercury (Macrae et al., 2008), ORTEPIII (Burnett & Johnson, 1996) and MOPAC (Stewart, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Ethyl 2,2-dimethyl-4-oxo-6-phenyl-3,4-dihydro-2H-pyran-5-carboxylate

Crystal data

C16H18O4	Dx = 1.204 Mg m^−3
Mr = 274.30	Melting point: 353 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.4566 (2) Å	Cell parameters from 4503 reflections
b = 5.9821 (1) Å	θ = 2.8–27.1°
c = 12.2040 (3) Å	µ = 0.09 mm^−1
β = 97.460 (1)°	T = 296 K
V = 756.93 (3) Å^3	Prism, colourless
Z = 2	0.18 × 0.16 × 0.10 mm
F(000) = 292

Data collection

Bruker SMART CCD area detector diffractometer	2956 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 31.3°, θmin = 1.7°
φ and ω scans	h = −14→13
9344 measured reflections	k = −8→8
4067 independent reflections	l = −17→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.0653P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4067 reflections	Δρmax = 0.17 e Å^−3
181 parameters	Δρmin = −0.18 e Å^−3
1 restraint	Absolute structure: Flack x determined using 1007 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.3 (4)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.12555 (13)	0.2273 (3)	0.39523 (11)	0.0489 (4)
O2	0.50752 (14)	0.2713 (4)	0.37581 (15)	0.0755 (6)
O3	0.3243 (2)	0.3359 (4)	0.10399 (14)	0.0881 (8)
O4	0.40770 (18)	0.6100 (4)	0.21193 (13)	0.0752 (6)
C1	−0.0461 (2)	0.2348 (5)	0.20244 (19)	0.0561 (5)
H1	−0.0462	0.1011	0.2413	0.067*
C2	−0.1503 (2)	0.2900 (6)	0.1253 (2)	0.0729 (8)
H2	−0.2191	0.1912	0.1111	0.087*
C3	−0.1528 (3)	0.4892 (5)	0.0698 (2)	0.0674 (7)
H3	−0.2235	0.5261	0.0187	0.081*
C4	−0.0512 (3)	0.6335 (5)	0.08947 (19)	0.0627 (6)
H4	−0.0532	0.7691	0.0520	0.075*
C5	0.0551 (2)	0.5787 (4)	0.16510 (18)	0.0541 (5)
H5	0.1244	0.6769	0.1777	0.065*
C6	0.05799 (18)	0.3777 (4)	0.22179 (15)	0.0424 (4)
C7	0.16819 (18)	0.3149 (4)	0.30515 (15)	0.0423 (4)
C8	0.2174 (2)	0.1069 (4)	0.47652 (17)	0.0530 (5)
C9	0.3435 (2)	0.2362 (4)	0.49400 (17)	0.0528 (5)
H9A	0.3300	0.3770	0.5302	0.063*
H9B	0.4070	0.1512	0.5420	0.063*
C10	0.3938 (2)	0.2810 (4)	0.38704 (18)	0.0521 (5)
C11	0.29465 (19)	0.3414 (4)	0.29526 (16)	0.0459 (5)
C12	0.3405 (2)	0.4251 (5)	0.19222 (17)	0.0547 (6)
C13	0.4738 (3)	0.6981 (8)	0.1238 (2)	0.0963 (13)
H13A	0.5113	0.5760	0.0865	0.116*
H13B	0.4125	0.7746	0.0701	0.116*
C14	0.5723 (3)	0.8489 (8)	0.1667 (3)	0.1034 (13)
H14A	0.6150	0.9056	0.1075	0.155*
H14B	0.5349	0.9707	0.2027	0.155*
H14C	0.6336	0.7725	0.2191	0.155*
C15	0.2348 (3)	−0.1253 (5)	0.4300 (3)	0.0783 (9)
H15A	0.2942	−0.2090	0.4808	0.117*
H15B	0.1531	−0.2007	0.4192	0.117*
H15C	0.2681	−0.1128	0.3605	0.117*
C16	0.1518 (3)	0.1011 (8)	0.5791 (2)	0.0875 (10)
H16A	0.2058	0.0246	0.6369	0.131*
H16B	0.1367	0.2511	0.6023	0.131*
H16C	0.0710	0.0239	0.5638	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0441 (7)	0.0547 (9)	0.0467 (7)	0.0023 (7)	0.0011 (6)	0.0116 (7)
O2	0.0423 (8)	0.1023 (16)	0.0785 (11)	−0.0052 (10)	−0.0048 (7)	−0.0141 (11)
O3	0.0995 (14)	0.115 (2)	0.0519 (9)	−0.0407 (14)	0.0162 (9)	−0.0276 (11)
O4	0.0920 (13)	0.0859 (14)	0.0504 (8)	−0.0423 (12)	0.0197 (8)	−0.0099 (9)
C1	0.0504 (11)	0.0567 (14)	0.0589 (12)	−0.0055 (11)	−0.0020 (9)	0.0120 (11)
C2	0.0513 (12)	0.080 (2)	0.0815 (17)	−0.0104 (13)	−0.0140 (11)	0.0144 (16)
C3	0.0580 (13)	0.0758 (19)	0.0637 (14)	0.0122 (13)	−0.0104 (11)	0.0126 (13)
C4	0.0772 (16)	0.0557 (15)	0.0529 (12)	0.0123 (13)	−0.0002 (11)	0.0138 (11)
C5	0.0625 (12)	0.0468 (13)	0.0516 (11)	−0.0038 (11)	0.0021 (9)	0.0065 (10)
C6	0.0434 (10)	0.0437 (11)	0.0397 (9)	0.0029 (9)	0.0035 (7)	0.0003 (8)
C7	0.0465 (10)	0.0401 (11)	0.0396 (9)	−0.0008 (9)	0.0027 (7)	−0.0020 (8)
C8	0.0549 (11)	0.0503 (13)	0.0498 (10)	−0.0030 (11)	−0.0086 (9)	0.0126 (10)
C9	0.0562 (11)	0.0478 (12)	0.0495 (11)	−0.0008 (11)	−0.0115 (9)	−0.0011 (10)
C10	0.0460 (10)	0.0511 (14)	0.0565 (11)	−0.0084 (10)	−0.0042 (9)	−0.0112 (11)
C11	0.0448 (10)	0.0484 (13)	0.0437 (9)	−0.0061 (9)	0.0024 (8)	−0.0055 (9)
C12	0.0472 (11)	0.0685 (17)	0.0479 (11)	−0.0093 (11)	0.0042 (9)	−0.0089 (11)
C13	0.097 (2)	0.142 (4)	0.0517 (13)	−0.052 (2)	0.0141 (13)	0.0076 (17)
C14	0.106 (2)	0.127 (3)	0.0813 (19)	−0.042 (2)	0.0285 (18)	0.006 (2)
C15	0.0798 (17)	0.0445 (14)	0.100 (2)	−0.0041 (13)	−0.0282 (16)	0.0054 (14)
C16	0.0816 (17)	0.122 (3)	0.0569 (14)	−0.016 (2)	0.0003 (12)	0.0320 (17)

Geometric parameters (Å, º)

O1—C7	1.345 (2)	C8—C9	1.519 (3)
O1—C8	1.476 (2)	C8—C15	1.521 (4)
O2—C10	1.216 (2)	C9—C10	1.493 (3)
O3—C12	1.194 (3)	C9—H9A	0.9700
O4—C12	1.316 (3)	C9—H9B	0.9700
O4—C13	1.452 (3)	C10—C11	1.469 (3)
C1—C6	1.380 (3)	C11—C12	1.489 (3)
C1—C2	1.384 (3)	C13—C14	1.417 (5)
C1—H1	0.9300	C13—H13A	0.9700
C2—C3	1.369 (4)	C13—H13B	0.9700
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.366 (4)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.389 (3)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.386 (3)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.483 (3)	C16—H16B	0.9600
C7—C11	1.353 (3)	C16—H16C	0.9600
C8—C16	1.505 (3)
C7—O1—C8	118.91 (15)	H9A—C9—H9B	108.0
C12—O4—C13	117.7 (2)	O2—C10—C11	122.0 (2)
C6—C1—C2	120.2 (2)	O2—C10—C9	123.4 (2)
C6—C1—H1	119.9	C11—C10—C9	114.65 (17)
C2—C1—H1	119.9	C7—C11—C10	120.29 (18)
C3—C2—C1	120.4 (3)	C7—C11—C12	122.69 (18)
C3—C2—H2	119.8	C10—C11—C12	117.00 (17)
C1—C2—H2	119.8	O3—C12—O4	123.4 (2)
C4—C3—C2	119.9 (2)	O3—C12—C11	126.0 (2)
C4—C3—H3	120.0	O4—C12—C11	110.56 (18)
C2—C3—H3	120.0	C14—C13—O4	110.5 (2)
C3—C4—C5	120.3 (2)	C14—C13—H13A	109.6
C3—C4—H4	119.8	O4—C13—H13A	109.6
C5—C4—H4	119.8	C14—C13—H13B	109.6
C6—C5—C4	120.0 (2)	O4—C13—H13B	109.6
C6—C5—H5	120.0	H13A—C13—H13B	108.1
C4—C5—H5	120.0	C13—C14—H14A	109.5
C1—C6—C5	119.12 (19)	C13—C14—H14B	109.5
C1—C6—C7	119.06 (19)	H14A—C14—H14B	109.5
C5—C6—C7	121.8 (2)	C13—C14—H14C	109.5
O1—C7—C11	123.38 (17)	H14A—C14—H14C	109.5
O1—C7—C6	110.42 (15)	H14B—C14—H14C	109.5
C11—C7—C6	126.20 (17)	C8—C15—H15A	109.5
O1—C8—C16	104.07 (19)	C8—C15—H15B	109.5
O1—C8—C9	108.85 (18)	H15A—C15—H15B	109.5
C16—C8—C9	112.1 (2)	C8—C15—H15C	109.5
O1—C8—C15	107.07 (18)	H15A—C15—H15C	109.5
C16—C8—C15	112.3 (3)	H15B—C15—H15C	109.5
C9—C8—C15	112.0 (2)	C8—C16—H16A	109.5
C10—C9—C8	111.47 (17)	C8—C16—H16B	109.5
C10—C9—H9A	109.3	H16A—C16—H16B	109.5
C8—C9—H9A	109.3	C8—C16—H16C	109.5
C10—C9—H9B	109.3	H16A—C16—H16C	109.5
C8—C9—H9B	109.3	H16B—C16—H16C	109.5
C6—C1—C2—C3	−1.8 (4)	C15—C8—C9—C10	64.4 (3)
C1—C2—C3—C4	0.8 (4)	C8—C9—C10—O2	−140.8 (3)
C2—C3—C4—C5	0.4 (4)	C8—C9—C10—C11	40.0 (3)
C3—C4—C5—C6	−0.6 (4)	O1—C7—C11—C10	−2.2 (3)
C2—C1—C6—C5	1.6 (4)	C6—C7—C11—C10	177.1 (2)
C2—C1—C6—C7	179.8 (2)	O1—C7—C11—C12	176.0 (2)
C4—C5—C6—C1	−0.4 (3)	C6—C7—C11—C12	−4.7 (3)
C4—C5—C6—C7	−178.6 (2)	O2—C10—C11—C7	169.0 (2)
C8—O1—C7—C11	−14.6 (3)	C9—C10—C11—C7	−11.7 (3)
C8—O1—C7—C6	165.99 (18)	O2—C10—C11—C12	−9.3 (4)
C1—C6—C7—O1	−42.0 (3)	C9—C10—C11—C12	169.9 (2)
C5—C6—C7—O1	136.1 (2)	C13—O4—C12—O3	−5.2 (4)
C1—C6—C7—C11	138.6 (2)	C13—O4—C12—C11	172.1 (3)
C5—C6—C7—C11	−43.3 (3)	C7—C11—C12—O3	−62.4 (4)
C7—O1—C8—C16	161.9 (2)	C10—C11—C12—O3	115.9 (3)
C7—O1—C8—C9	42.2 (3)	C7—C11—C12—O4	120.3 (2)
C7—O1—C8—C15	−79.0 (2)	C10—C11—C12—O4	−61.4 (3)
O1—C8—C9—C10	−53.7 (3)	C12—O4—C13—C14	−161.2 (3)
C16—C8—C9—C10	−168.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2^i	0.97	2.60	3.470 (3)	150
C15—H15A···O2^i	0.96	2.54	3.406 (3)	151

Symmetry code: (i) −x+1, y−1/2, −z+1.