Ethyl (E)-3-(6-methyl-4-oxo-4H-chromen-3-yl)prop-2-enoate.

In the title compound, C(15)H(14)O(4), the chromone ring system is close to being planar [maximum deviation = 0.015 (2) Å]. The double bond of the ethyl prop-2-enoate chain adopts an E conformation and an intra-molecular C-H⋯O hydrogen bond generates an S6 ring. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(14) loops. Weak π-π inter-actions [centroid-centroid distance = 3.8493 (12) Å] also occur.

Related literature

For the biological activity of chromones, see: Patel et al. (2011 ▶); Khan et al. (2010 ▶); Gautam et al. (2010 ▶). For a related structure, see: Wang & Kong (2007 ▶).

Experimental

Crystal data

C15H14O4

M = 258.26

Monoclinic,

a = 13.8663 (12) Å

b = 12.3512 (10) Å

c = 7.6947 (6) Å

β = 96.390 (2)°

V = 1309.65 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.34 × 0.25 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.968, T max = 0.985

7621 measured reflections

2431 independent reflections

1650 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.142

S = 1.04

2431 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038585/hb6950sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038585/hb6950Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038585/hb6950Isup3.cml

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

C15H14O4	F(000) = 544
Mr = 258.26	Dx = 1.310 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.8663 (12) Å	Cell parameters from 1626 reflections
b = 12.3512 (10) Å	θ = 3.0–23.3°
c = 7.6947 (6) Å	µ = 0.10 mm−1
β = 96.390 (2)°	T = 298 K
V = 1309.65 (19) Å3	Block, colourless
Z = 4	0.34 × 0.25 × 0.16 mm

Bruker SMART APEX CCD diffractometer	2431 independent reflections
Radiation source: fine-focus sealed tube	1650 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scan	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
Tmin = 0.968, Tmax = 0.985	k = −14→14
7621 measured reflections	l = −9→9

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0754P)2 + 0.0649P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2431 reflections	Δρmax = 0.17 e Å−3
175 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (16)

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
O1	0.74141 (9)	0.20992 (10)	0.17694 (19)	0.0713 (4)
O2	0.85161 (10)	0.49847 (11)	0.3624 (2)	0.0786 (5)
O3	0.51893 (10)	0.66244 (12)	0.0798 (2)	0.0880 (5)
O4	0.63447 (9)	0.77677 (10)	0.18750 (18)	0.0677 (4)
C1	0.83451 (14)	0.21480 (15)	0.2624 (3)	0.0597 (5)
C2	0.88511 (15)	0.11889 (17)	0.2813 (3)	0.0715 (6)
H2A	0.8566	0.0542	0.2405	0.086*
C3	0.97837 (16)	0.12068 (19)	0.3615 (3)	0.0731 (6)
H3A	1.0133	0.0563	0.3724	0.088*
C4	1.02265 (14)	0.21586 (18)	0.4273 (3)	0.0653 (6)
C5	0.97015 (13)	0.31040 (17)	0.4062 (2)	0.0614 (5)
H5A	0.9987	0.3749	0.4476	0.074*
C6	0.87513 (12)	0.31198 (15)	0.3241 (2)	0.0540 (5)
C7	0.81876 (12)	0.41241 (16)	0.3029 (2)	0.0570 (5)
C8	0.72174 (12)	0.40105 (15)	0.2076 (2)	0.0537 (5)
C9	0.69141 (14)	0.30212 (16)	0.1524 (3)	0.0637 (5)
H9A	0.6298	0.2975	0.0913	0.076*
C10	0.65611 (13)	0.49171 (15)	0.1662 (2)	0.0571 (5)
H10A	0.5964	0.4750	0.1047	0.069*
C11	0.67129 (13)	0.59483 (16)	0.2054 (3)	0.0594 (5)
H11A	0.7292	0.6151	0.2697	0.071*
C12	0.59924 (13)	0.67789 (15)	0.1500 (3)	0.0595 (5)
C13	0.57176 (15)	0.86723 (17)	0.1372 (3)	0.0764 (6)
H13A	0.5168	0.8677	0.2049	0.092*
H13B	0.5476	0.8624	0.0142	0.092*
C14	0.63063 (19)	0.96782 (18)	0.1716 (3)	0.0915 (8)
H14A	0.5895	1.0300	0.1511	0.137*
H14B	0.6807	0.9700	0.0950	0.137*
H14C	0.6596	0.9680	0.2909	0.137*
C15	1.12484 (15)	0.2147 (2)	0.5173 (3)	0.0877 (7)
H15A	1.1556	0.2827	0.4985	0.132*
H15B	1.1606	0.1572	0.4703	0.132*
H15C	1.1234	0.2035	0.6404	0.132*

	U11	U22	U33	U12	U13	U23
O1	0.0564 (9)	0.0616 (9)	0.0918 (11)	−0.0011 (6)	−0.0101 (7)	−0.0061 (7)
O2	0.0551 (8)	0.0610 (9)	0.1124 (12)	−0.0051 (6)	−0.0225 (8)	−0.0025 (8)
O3	0.0525 (9)	0.0756 (10)	0.1274 (14)	−0.0032 (7)	−0.0270 (9)	0.0082 (9)
O4	0.0541 (8)	0.0600 (9)	0.0857 (10)	0.0022 (6)	−0.0068 (7)	0.0026 (7)
C1	0.0510 (11)	0.0680 (13)	0.0589 (12)	0.0022 (9)	0.0009 (9)	0.0014 (10)
C2	0.0715 (14)	0.0655 (13)	0.0760 (14)	0.0070 (10)	0.0019 (11)	−0.0045 (11)
C3	0.0705 (14)	0.0801 (15)	0.0680 (14)	0.0231 (11)	0.0049 (11)	0.0014 (11)
C4	0.0547 (12)	0.0860 (15)	0.0544 (12)	0.0135 (10)	0.0027 (9)	−0.0025 (10)
C5	0.0481 (11)	0.0766 (14)	0.0585 (12)	0.0038 (9)	0.0016 (9)	−0.0031 (10)
C6	0.0450 (10)	0.0643 (12)	0.0521 (11)	0.0008 (8)	0.0023 (8)	0.0018 (9)
C7	0.0440 (10)	0.0626 (12)	0.0628 (12)	−0.0046 (9)	−0.0012 (9)	0.0042 (10)
C8	0.0434 (10)	0.0589 (11)	0.0573 (11)	−0.0043 (8)	−0.0004 (8)	0.0041 (9)
C9	0.0471 (11)	0.0678 (13)	0.0732 (14)	−0.0010 (9)	−0.0067 (10)	0.0017 (10)
C10	0.0416 (10)	0.0668 (13)	0.0611 (12)	−0.0055 (8)	−0.0028 (8)	0.0088 (9)
C11	0.0452 (10)	0.0651 (13)	0.0651 (12)	−0.0041 (9)	−0.0057 (9)	0.0069 (10)
C12	0.0444 (11)	0.0650 (13)	0.0669 (13)	−0.0038 (9)	−0.0036 (9)	0.0065 (10)
C13	0.0689 (14)	0.0685 (14)	0.0901 (16)	0.0141 (10)	0.0014 (12)	0.0090 (11)
C14	0.117 (2)	0.0648 (14)	0.0893 (17)	0.0040 (13)	−0.0039 (15)	−0.0030 (12)
C15	0.0587 (13)	0.118 (2)	0.0827 (16)	0.0251 (13)	−0.0066 (11)	−0.0078 (14)

O1—C9	1.336 (2)	C7—C8	1.465 (2)
O1—C1	1.383 (2)	C8—C9	1.346 (3)
O2—C7	1.225 (2)	C8—C10	1.456 (2)
O3—C12	1.198 (2)	C9—H9A	0.9300
O4—C12	1.335 (2)	C10—C11	1.320 (3)
O4—C13	1.442 (2)	C10—H10A	0.9300
C1—C2	1.376 (3)	C11—C12	1.462 (3)
C1—C6	1.387 (3)	C11—H11A	0.9300
C2—C3	1.370 (3)	C13—C14	1.494 (3)
C2—H2A	0.9300	C13—H13A	0.9700
C3—C4	1.395 (3)	C13—H13B	0.9700
C3—H3A	0.9300	C14—H14A	0.9600
C4—C5	1.376 (3)	C14—H14B	0.9600
C4—C15	1.506 (3)	C14—H14C	0.9600
C5—C6	1.396 (3)	C15—H15A	0.9600
C5—H5A	0.9300	C15—H15B	0.9600
C6—C7	1.466 (3)	C15—H15C	0.9600
C9—O1—C1	118.19 (15)	C8—C9—H9A	116.9
C12—O4—C13	117.10 (15)	C11—C10—C8	127.74 (18)
C2—C1—O1	116.79 (18)	C11—C10—H10A	116.1
C2—C1—C6	121.72 (19)	C8—C10—H10A	116.1
O1—C1—C6	121.49 (16)	C10—C11—C12	121.59 (18)
C3—C2—C1	118.6 (2)	C10—C11—H11A	119.2
C3—C2—H2A	120.7	C12—C11—H11A	119.2
C1—C2—H2A	120.7	O3—C12—O4	122.87 (18)
C2—C3—C4	122.18 (19)	O3—C12—C11	126.20 (18)
C2—C3—H3A	118.9	O4—C12—C11	110.92 (16)
C4—C3—H3A	118.9	O4—C13—C14	107.19 (18)
C5—C4—C3	117.80 (19)	O4—C13—H13A	110.3
C5—C4—C15	121.4 (2)	C14—C13—H13A	110.3
C3—C4—C15	120.81 (19)	O4—C13—H13B	110.3
C4—C5—C6	121.70 (19)	C14—C13—H13B	110.3
C4—C5—H5A	119.1	H13A—C13—H13B	108.5
C6—C5—H5A	119.1	C13—C14—H14A	109.5
C1—C6—C5	118.00 (17)	C13—C14—H14B	109.5
C1—C6—C7	120.19 (17)	H14A—C14—H14B	109.5
C5—C6—C7	121.81 (17)	C13—C14—H14C	109.5
O2—C7—C8	123.54 (17)	H14A—C14—H14C	109.5
O2—C7—C6	121.42 (16)	H14B—C14—H14C	109.5
C8—C7—C6	115.04 (17)	C4—C15—H15A	109.5
C9—C8—C10	117.61 (16)	C4—C15—H15B	109.5
C9—C8—C7	118.83 (17)	H15A—C15—H15B	109.5
C10—C8—C7	123.55 (16)	C4—C15—H15C	109.5
O1—C9—C8	126.19 (18)	H15A—C15—H15C	109.5
O1—C9—H9A	116.9	H15B—C15—H15C	109.5
C9—O1—C1—C2	−178.25 (17)	C1—C6—C7—C8	−2.5 (3)
C9—O1—C1—C6	1.1 (3)	C5—C6—C7—C8	177.57 (16)
O1—C1—C2—C3	178.48 (17)	O2—C7—C8—C9	−177.91 (19)
C6—C1—C2—C3	−0.8 (3)	C6—C7—C8—C9	1.7 (2)
C1—C2—C3—C4	1.3 (3)	O2—C7—C8—C10	3.2 (3)
C2—C3—C4—C5	−1.4 (3)	C6—C7—C8—C10	−177.23 (16)
C2—C3—C4—C15	179.04 (19)	C1—O1—C9—C8	−2.1 (3)
C3—C4—C5—C6	0.9 (3)	C10—C8—C9—O1	179.58 (17)
C15—C4—C5—C6	−179.49 (19)	C7—C8—C9—O1	0.6 (3)
C2—C1—C6—C5	0.4 (3)	C9—C8—C10—C11	−179.17 (19)
O1—C1—C6—C5	−178.87 (16)	C7—C8—C10—C11	−0.2 (3)
C2—C1—C6—C7	−179.49 (17)	C8—C10—C11—C12	178.09 (17)
O1—C1—C6—C7	1.2 (3)	C13—O4—C12—O3	−1.0 (3)
C4—C5—C6—C1	−0.5 (3)	C13—O4—C12—C11	178.89 (16)
C4—C5—C6—C7	179.43 (17)	C10—C11—C12—O3	6.7 (3)
C1—C6—C7—O2	177.08 (18)	C10—C11—C12—O4	−173.18 (17)
C5—C6—C7—O2	−2.8 (3)	C12—O4—C13—C14	−172.99 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2	0.93	2.28	2.908 (2)	124
C9—H9A···O3i	0.93	2.37	3.276 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2	0.93	2.28	2.908 (2)	124
C9—H9A⋯O3i	0.93	2.37	3.276 (3)	164

Symmetry code: (i) .