8-Meth-oxy-3-(4-methyl-benzyl-idene)-6-(prop-1-en-yl)chroman-4-one.

In the title compound, C(21)H(20)O(3), the tolyl ring makes a dihedral angle of 31.11 (6)° with the benzene ring of the chromanone unit. The pyrone ring adopts a half-chair conformation. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O inter-action and the crystal packing is stabilized by weak inter-molecular C-H⋯O inter-actions and a C-H⋯π inter-action.

Related literature

For related lituerature, see: Puviarasan et al. (1998 ▶); Tillekeratne et al. (2001 ▶); Nissa et al. (2001 ▶); Kang et al. (2004 ▶); Wu, Xu, Wan et al. (2005 ▶); Wu, Xu, Zhou et al. (2005 ▶); Schollmeyer et al. (2005 ▶); Suresh et al. (2007 ▶).

Experimental

Crystal data

C21H20O3

M = 320.37

Monoclinic,

a = 6.8550 (5) Å

b = 11.6264 (8) Å

c = 20.9669 (14) Å

β = 96.947 (1)°

V = 1658.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.18 × 0.11 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.995

17310 measured reflections

2941 independent reflections

2054 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.05

2941 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807060989/is2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060989/is2242Isup2.hkl

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

C21H20O3	Z = 4
Mr = 320.37	F000 = 680
Monoclinic, P21/n	Dx = 1.283 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 6.8550 (5) Å	θ = 1.9–27.2º
b = 11.6264 (8) Å	µ = 0.09 mm−1
c = 20.9669 (14) Å	T = 293 (2) K
β = 96.947 (1)º	Prism, yellow
V = 1658.8 (2) Å3	0.18 × 0.11 × 0.06 mm

Bruker APEXII CCD diffractometer	2941 independent reflections
Radiation source: fine-focus sealed tube	2054 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 293(2) K	θmax = 25.1º
ω scan	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.984, Tmax = 0.995	k = −13→13
17310 measured reflections	l = −24→24

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.331P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.006
2941 reflections	Δρmax = 0.17 e Å−3
220 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.72176 (17)	0.14365 (10)	0.15211 (6)	0.0560 (4)
C11	0.5481 (2)	0.19760 (14)	0.13450 (8)	0.0431 (4)
O3	0.45043 (19)	0.02250 (10)	0.08579 (7)	0.0622 (4)
O2	0.66403 (19)	0.48556 (10)	0.18481 (7)	0.0616 (4)
C17	0.3351 (3)	0.36251 (16)	0.12538 (8)	0.0484 (5)
H17	0.3131	0.4391	0.1352	0.058*
C12	0.5149 (2)	0.31169 (14)	0.14850 (8)	0.0431 (4)
C14	0.4016 (3)	0.13375 (14)	0.09710 (9)	0.0467 (4)
C13	0.6739 (2)	0.38058 (14)	0.18298 (8)	0.0439 (4)
C9	0.8458 (2)	0.31532 (14)	0.21405 (8)	0.0429 (4)
C15	0.2262 (3)	0.18653 (16)	0.07531 (9)	0.0519 (5)
H15	0.1286	0.1442	0.0511	0.062*
C16	0.1906 (3)	0.30248 (16)	0.08862 (9)	0.0498 (5)
C8	0.9929 (2)	0.37410 (15)	0.24703 (8)	0.0461 (4)
H8	0.9749	0.4534	0.2468	0.055*
C19	0.0062 (3)	0.36065 (18)	0.06302 (10)	0.0593 (5)
H19	−0.0081	0.4355	0.0774	0.071*
C1	1.1769 (2)	0.33551 (15)	0.28342 (8)	0.0436 (4)
C20	−0.1372 (3)	0.32230 (19)	0.02369 (10)	0.0652 (6)
H20	−0.1260	0.2473	0.0092	0.078*
C10	0.8380 (3)	0.18735 (15)	0.20825 (10)	0.0562 (5)
H10A	0.9711	0.1588	0.2087	0.067*
H10B	0.7866	0.1565	0.2458	0.067*
C2	1.3272 (3)	0.41550 (16)	0.29596 (9)	0.0545 (5)
H2	1.3065	0.4906	0.2814	0.065*
C4	1.5439 (3)	0.27688 (17)	0.35240 (9)	0.0506 (5)
C3	1.5067 (3)	0.38657 (17)	0.32947 (9)	0.0568 (5)
H3	1.6042	0.4423	0.3366	0.068*
C6	1.2140 (3)	0.22494 (16)	0.30760 (9)	0.0532 (5)
H6	1.1164	0.1691	0.3012	0.064*
C5	1.3935 (3)	0.19739 (17)	0.34087 (10)	0.0575 (5)
H5	1.4144	0.1227	0.3561	0.069*
C21	−0.3191 (3)	0.3854 (2)	−0.00093 (11)	0.0740 (7)
H21A	−0.3129	0.4622	0.0160	0.111*
H21B	−0.4310	0.3464	0.0122	0.111*
H21C	−0.3309	0.3884	−0.0470	0.111*
C7	1.7370 (3)	0.2454 (2)	0.39040 (10)	0.0685 (6)
H7A	1.7215	0.2423	0.4353	0.103*
H7B	1.8339	0.3022	0.3835	0.103*
H7C	1.7788	0.1716	0.3766	0.103*
C18	0.3117 (3)	−0.04441 (18)	0.04568 (11)	0.0714 (6)
H18A	0.1910	−0.0487	0.0645	0.107*
H18B	0.3629	−0.1205	0.0414	0.107*
H18C	0.2875	−0.0092	0.0041	0.107*

	U11	U22	U33	U12	U13	U23
O1	0.0484 (7)	0.0417 (7)	0.0717 (9)	0.0082 (6)	−0.0177 (6)	−0.0105 (6)
C11	0.0403 (9)	0.0413 (10)	0.0459 (10)	0.0016 (7)	−0.0016 (8)	0.0025 (7)
O3	0.0573 (8)	0.0466 (8)	0.0776 (10)	−0.0033 (6)	−0.0127 (7)	−0.0133 (7)
O2	0.0621 (8)	0.0375 (7)	0.0800 (10)	0.0054 (6)	−0.0125 (7)	−0.0039 (6)
C17	0.0456 (10)	0.0472 (10)	0.0509 (11)	0.0076 (8)	−0.0001 (9)	−0.0037 (8)
C12	0.0412 (9)	0.0423 (10)	0.0445 (10)	0.0036 (7)	−0.0003 (8)	0.0010 (7)
C14	0.0478 (10)	0.0407 (10)	0.0503 (10)	−0.0017 (8)	0.0006 (8)	−0.0019 (8)
C13	0.0445 (10)	0.0387 (10)	0.0474 (10)	0.0027 (7)	0.0010 (8)	−0.0017 (8)
C9	0.0424 (10)	0.0386 (9)	0.0462 (10)	0.0010 (7)	−0.0005 (8)	0.0009 (7)
C15	0.0420 (10)	0.0592 (12)	0.0517 (11)	−0.0058 (9)	−0.0056 (8)	−0.0034 (9)
C16	0.0427 (10)	0.0560 (11)	0.0494 (10)	0.0043 (8)	0.0005 (8)	−0.0014 (8)
C8	0.0466 (11)	0.0395 (9)	0.0512 (10)	−0.0006 (8)	0.0015 (8)	0.0011 (8)
C19	0.0462 (11)	0.0651 (13)	0.0639 (13)	0.0047 (9)	−0.0046 (10)	−0.0083 (10)
C1	0.0400 (9)	0.0448 (10)	0.0447 (10)	−0.0033 (8)	−0.0004 (8)	−0.0017 (8)
C20	0.0523 (12)	0.0696 (13)	0.0702 (14)	0.0056 (10)	−0.0074 (10)	−0.0053 (11)
C10	0.0514 (11)	0.0419 (10)	0.0685 (13)	0.0005 (8)	−0.0197 (10)	−0.0022 (9)
C2	0.0533 (11)	0.0458 (10)	0.0620 (12)	−0.0098 (9)	−0.0036 (9)	0.0048 (9)
C4	0.0388 (10)	0.0624 (12)	0.0496 (11)	−0.0015 (9)	0.0014 (8)	−0.0043 (9)
C3	0.0450 (11)	0.0589 (12)	0.0643 (12)	−0.0164 (9)	−0.0016 (9)	0.0006 (10)
C6	0.0446 (10)	0.0469 (10)	0.0643 (12)	−0.0085 (8)	−0.0086 (9)	0.0046 (9)
C5	0.0515 (11)	0.0480 (11)	0.0688 (13)	−0.0012 (9)	−0.0091 (10)	0.0063 (9)
C21	0.0482 (12)	0.0975 (17)	0.0734 (15)	0.0099 (11)	−0.0044 (11)	0.0110 (13)
C7	0.0460 (11)	0.0862 (16)	0.0692 (14)	0.0021 (10)	−0.0093 (10)	−0.0048 (12)
C18	0.0684 (14)	0.0598 (13)	0.0821 (16)	−0.0118 (11)	−0.0073 (12)	−0.0215 (11)

O1—C11	1.3567 (19)	C1—C6	1.394 (2)
O1—C10	1.432 (2)	C20—C21	1.484 (3)
C11—C12	1.383 (2)	C20—H20	0.9300
C11—C14	1.408 (2)	C10—H10A	0.9700
O3—C14	1.364 (2)	C10—H10B	0.9700
O3—C18	1.422 (2)	C2—C3	1.383 (3)
O2—C13	1.2232 (19)	C2—H2	0.9300
C17—C16	1.370 (2)	C4—C3	1.376 (3)
C17—C12	1.400 (2)	C4—C5	1.384 (3)
C17—H17	0.9300	C4—C7	1.505 (2)
C12—C13	1.470 (2)	C3—H3	0.9300
C14—C15	1.378 (2)	C6—C5	1.377 (2)
C13—C9	1.484 (2)	C6—H6	0.9300
C9—C8	1.339 (2)	C5—H5	0.9300
C9—C10	1.493 (2)	C21—H21A	0.9600
C15—C16	1.404 (3)	C21—H21B	0.9600
C15—H15	0.9300	C21—H21C	0.9600
C16—C19	1.476 (2)	C7—H7A	0.9600
C8—C1	1.464 (2)	C7—H7B	0.9600
C8—H8	0.9300	C7—H7C	0.9600
C19—C20	1.284 (3)	C18—H18A	0.9600
C19—H19	0.9300	C18—H18B	0.9600
C1—C2	1.389 (2)	C18—H18C	0.9600
C11—O1—C10	116.25 (14)	O1—C10—H10A	108.4
O1—C11—C12	123.15 (15)	C9—C10—H10A	108.4
O1—C11—C14	116.80 (15)	O1—C10—H10B	108.4
C12—C11—C14	119.95 (15)	C9—C10—H10B	108.4
C14—O3—C18	117.44 (14)	H10A—C10—H10B	107.5
C16—C17—C12	121.75 (17)	C3—C2—C1	121.84 (17)
C16—C17—H17	119.1	C3—C2—H2	119.1
C12—C17—H17	119.1	C1—C2—H2	119.1
C11—C12—C17	119.46 (15)	C3—C4—C5	117.07 (17)
C11—C12—C13	119.72 (15)	C3—C4—C7	121.62 (17)
C17—C12—C13	120.65 (15)	C5—C4—C7	121.27 (18)
O3—C14—C15	125.96 (16)	C4—C3—C2	121.27 (17)
O3—C14—C11	115.04 (15)	C4—C3—H3	119.4
C15—C14—C11	119.00 (16)	C2—C3—H3	119.4
O2—C13—C12	121.22 (15)	C5—C6—C1	120.76 (17)
O2—C13—C9	122.71 (15)	C5—C6—H6	119.6
C12—C13—C9	116.06 (14)	C1—C6—H6	119.6
C8—C9—C13	118.29 (15)	C6—C5—C4	122.31 (18)
C8—C9—C10	124.61 (15)	C6—C5—H5	118.8
C13—C9—C10	117.05 (14)	C4—C5—H5	118.8
C14—C15—C16	121.81 (16)	C20—C21—H21A	109.5
C14—C15—H15	119.1	C20—C21—H21B	109.5
C16—C15—H15	119.1	H21A—C21—H21B	109.5
C17—C16—C15	118.03 (16)	C20—C21—H21C	109.5
C17—C16—C19	120.01 (17)	H21A—C21—H21C	109.5
C15—C16—C19	121.95 (16)	H21B—C21—H21C	109.5
C9—C8—C1	131.33 (16)	C4—C7—H7A	109.5
C9—C8—H8	114.3	C4—C7—H7B	109.5
C1—C8—H8	114.3	H7A—C7—H7B	109.5
C20—C19—C16	129.0 (2)	C4—C7—H7C	109.5
C20—C19—H19	115.5	H7A—C7—H7C	109.5
C16—C19—H19	115.5	H7B—C7—H7C	109.5
C2—C1—C6	116.74 (16)	O3—C18—H18A	109.5
C2—C1—C8	117.80 (16)	O3—C18—H18B	109.5
C6—C1—C8	125.46 (15)	H18A—C18—H18B	109.5
C19—C20—C21	126.7 (2)	O3—C18—H18C	109.5
C19—C20—H20	116.7	H18A—C18—H18C	109.5
C21—C20—H20	116.7	H18B—C18—H18C	109.5
O1—C10—C9	115.55 (14)
C10—O1—C11—C12	27.3 (2)	C12—C17—C16—C15	1.0 (3)
C10—O1—C11—C14	−156.35 (16)	C12—C17—C16—C19	−177.52 (17)
O1—C11—C12—C17	176.39 (16)	C14—C15—C16—C17	−1.2 (3)
C14—C11—C12—C17	0.2 (3)	C14—C15—C16—C19	177.31 (18)
O1—C11—C12—C13	1.2 (3)	C13—C9—C8—C1	178.65 (17)
C14—C11—C12—C13	−174.98 (16)	C10—C9—C8—C1	1.2 (3)
C16—C17—C12—C11	−0.6 (3)	C17—C16—C19—C20	173.4 (2)
C16—C17—C12—C13	174.58 (17)	C15—C16—C19—C20	−5.1 (3)
C18—O3—C14—C15	2.8 (3)	C9—C8—C1—C2	160.54 (19)
C18—O3—C14—C11	−177.03 (17)	C9—C8—C1—C6	−20.4 (3)
O1—C11—C14—O3	3.0 (2)	C16—C19—C20—C21	−179.4 (2)
C12—C11—C14—O3	179.47 (16)	C11—O1—C10—C9	−41.3 (2)
O1—C11—C14—C15	−176.79 (16)	C8—C9—C10—O1	−154.41 (17)
C12—C11—C14—C15	−0.4 (3)	C13—C9—C10—O1	28.1 (2)
C11—C12—C13—O2	165.08 (18)	C6—C1—C2—C3	1.5 (3)
C17—C12—C13—O2	−10.0 (3)	C8—C1—C2—C3	−179.40 (17)
C11—C12—C13—C9	−14.0 (2)	C5—C4—C3—C2	−0.5 (3)
C17—C12—C13—C9	170.86 (16)	C7—C4—C3—C2	−178.38 (18)
O2—C13—C9—C8	2.1 (3)	C1—C2—C3—C4	−0.5 (3)
C12—C13—C9—C8	−178.81 (16)	C2—C1—C6—C5	−1.5 (3)
O2—C13—C9—C10	179.76 (18)	C8—C1—C6—C5	179.48 (18)
C12—C13—C9—C10	−1.2 (2)	C1—C6—C5—C4	0.5 (3)
O3—C14—C15—C16	−178.93 (18)	C3—C4—C5—C6	0.5 (3)
C11—C14—C15—C16	0.9 (3)	C7—C4—C5—C6	178.39 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2	0.93	2.39	2.784 (2)	106
C7—H7C···O2i	0.96	2.57	3.512 (4)	166
C10—H10B···O2ii	0.97	2.46	3.246 (4)	138
C21—H21B···Cgiii	0.96	2.86	3.722 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11/C14–C17/C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2	0.93	2.39	2.784 (2)	106
C7—H7C⋯O2i	0.96	2.57	3.512 (4)	166
C10—H10B⋯O2ii	0.97	2.46	3.246 (4)	138
C21—H21B⋯Cgiii	0.96	2.86	3.722 (2)	150

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