8-Eth-oxy-3-(4-isopropyl-benzyl-idene)-6-methyl-chroman-4-one.

In the title compound, C(22)H(24)O(3), the non-fused benzene ring makes a dihedral angle of 52.56 (7)° with the benzene ring of the chromanone unit. 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. The isopropyl group is disordered over two positions, with site occupancies of 0.48/0.52.

Related literature

For related literature, see: Kang et al. (2004 ▶); Marx et al. (2007 ▶); Puviarasan et al. (1998 ▶); Tillekeratne et al. (2001 ▶); Nissa et al. (2001 ▶); Schollmeyer et al. (2005 ▶). A related compound has been reported by Marx et al. (2007 ▶).

Experimental

Crystal data

C22H24O3

M = 336.41

Monoclinic,

a = 10.3568 (9) Å

b = 16.8154 (15) Å

c = 10.8962 (10) Å

β = 99.873 (1)°

V = 1869.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 (2) K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.988

21105 measured reflections

4385 independent reflections

3220 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.158

S = 1.02

4385 reflections

256 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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/S1600536807066925/bq2050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066925/bq2050Isup2.hkl

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

C22H24O3	Z = 4
Mr = 336.41	F000 = 720
Monoclinic, P21/n	Dx = 1.195 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 10.3568 (9) Å	θ = 1.9–27.2º
b = 16.8154 (15) Å	µ = 0.08 mm−1
c = 10.8962 (10) Å	T = 295 (2) K
β = 99.873 (1)º	Block, colourless
V = 1869.5 (3) Å3	0.22 × 0.18 × 0.16 mm

Bruker SMART APEX area-detector diffractometer	4385 independent reflections
Radiation source: fine-focus sealed tube	3220 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 295(2) K	θmax = 28.0º
ω and φ scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.983, Tmax = 0.988	k = −21→21
21105 measured reflections	l = −14→14

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.0767P)2 + 0.3281P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4385 reflections	Δρmax = 0.23 e Å−3
256 parameters	Δρmin = −0.14 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	1.16222 (14)	0.18147 (9)	1.10909 (13)	0.0528 (3)
C2	1.27835 (14)	0.22634 (9)	1.13210 (14)	0.0554 (4)
C3	1.38353 (15)	0.19764 (10)	1.21563 (14)	0.0607 (4)
H3	1.4607	0.2270	1.2304	0.073*
C4	1.37726 (16)	0.12575 (10)	1.27856 (15)	0.0630 (4)
C5	1.26264 (17)	0.08359 (10)	1.25682 (15)	0.0636 (4)
H5	1.2568	0.0361	1.2992	0.076*
C6	1.15337 (15)	0.11036 (9)	1.17194 (14)	0.0555 (4)
C7	1.02883 (16)	0.06564 (9)	1.15305 (14)	0.0587 (4)
C8	0.92415 (15)	0.09672 (9)	1.05370 (14)	0.0568 (4)
C9	0.96801 (16)	0.15548 (10)	0.96569 (15)	0.0631 (4)
H9A	1.0068	0.1268	0.9039	0.076*
H9B	0.8919	0.1837	0.9224	0.076*
C10	0.80031 (16)	0.07161 (10)	1.04848 (15)	0.0621 (4)
H10	0.7877	0.0351	1.1094	0.075*
C11	0.68243 (16)	0.09345 (10)	0.96090 (16)	0.0621 (4)
C12	0.56167 (19)	0.09445 (13)	1.0015 (2)	0.0835 (6)
H12	0.5574	0.0804	1.0833	0.100*
C13	0.4489 (2)	0.11585 (16)	0.9224 (3)	0.1030 (8)
H13	0.3702	0.1166	0.9525	0.124*
C14	0.4489 (2)	0.13620 (13)	0.7997 (2)	0.0946 (7)
C15	0.5682 (2)	0.13326 (12)	0.7588 (2)	0.0844 (6)
H15	0.5714	0.1461	0.6763	0.101*
C16	0.68203 (18)	0.11198 (11)	0.83633 (17)	0.0713 (5)
H16	0.7601	0.1099	0.8050	0.086*
C17	0.3423 (5)	0.1672 (3)	0.6930 (5)	0.0724 (14)	0.520 (10)
H17	0.3805	0.1842	0.6209	0.087*	0.520 (10)
C18	0.2693 (9)	0.2337 (4)	0.7420 (8)	0.091 (2)	0.520 (10)
H18A	0.3260	0.2789	0.7596	0.136*	0.520 (10)
H18B	0.2403	0.2168	0.8169	0.136*	0.520 (10)
H18C	0.1948	0.2480	0.6807	0.136*	0.520 (10)
C19	0.2513 (8)	0.0950 (5)	0.6613 (10)	0.107 (3)	0.520 (10)
H19A	0.2994	0.0521	0.6323	0.160*	0.520 (10)
H19B	0.1792	0.1094	0.5974	0.160*	0.520 (10)
H19C	0.2184	0.0784	0.7345	0.160*	0.520 (10)
C171	0.3016 (5)	0.1501 (3)	0.7409 (6)	0.0780 (16)	0.480 (10)
H171	0.2387	0.1293	0.7905	0.094*	0.480 (10)
C181	0.2898 (16)	0.2399 (6)	0.7148 (16)	0.176 (7)	0.480 (10)
H18D	0.3035	0.2684	0.7922	0.263*	0.480 (10)
H18E	0.2039	0.2515	0.6696	0.263*	0.480 (10)
H18F	0.3545	0.2557	0.6662	0.263*	0.480 (10)
C191	0.2836 (11)	0.1179 (9)	0.6070 (8)	0.150 (5)	0.480 (10)
H19D	0.2892	0.0609	0.6090	0.225*	0.480 (10)
H19E	0.3510	0.1390	0.5658	0.225*	0.480 (10)
H19F	0.1993	0.1337	0.5626	0.225*	0.480 (10)
C20	1.4972 (2)	0.09598 (14)	1.36590 (19)	0.0858 (6)
H20A	1.4713	0.0568	1.4210	0.129*
H20B	1.5390	0.1397	1.4138	0.129*
H20C	1.5573	0.0726	1.3183	0.129*
C22	1.39808 (17)	0.33615 (11)	1.06840 (18)	0.0725 (5)
H22A	1.4609	0.3015	1.0385	0.087*
H22B	1.4340	0.3525	1.1527	0.087*
C23	1.3708 (2)	0.40699 (12)	0.9860 (2)	0.0940 (7)
H23A	1.3325	0.3902	0.9036	0.141*
H23B	1.4512	0.4348	0.9830	0.141*
H23C	1.3111	0.4417	1.0183	0.141*
O1	1.06117 (10)	0.21232 (6)	1.02605 (10)	0.0640 (3)
O2	1.01289 (13)	0.00744 (8)	1.21616 (12)	0.0782 (4)
O3	1.27649 (10)	0.29549 (7)	1.06605 (11)	0.0669 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0486 (8)	0.0529 (8)	0.0538 (8)	0.0013 (6)	−0.0002 (6)	−0.0003 (6)
C2	0.0514 (8)	0.0528 (8)	0.0596 (8)	−0.0002 (6)	0.0030 (6)	−0.0019 (6)
C3	0.0490 (8)	0.0660 (9)	0.0636 (9)	−0.0004 (7)	−0.0003 (7)	−0.0083 (7)
C4	0.0599 (9)	0.0664 (9)	0.0580 (9)	0.0099 (7)	−0.0029 (7)	−0.0024 (7)
C5	0.0696 (10)	0.0583 (9)	0.0588 (9)	0.0072 (7)	−0.0005 (7)	0.0059 (7)
C6	0.0576 (8)	0.0535 (8)	0.0535 (8)	0.0008 (6)	0.0037 (6)	0.0002 (6)
C7	0.0636 (9)	0.0543 (8)	0.0570 (8)	−0.0022 (7)	0.0067 (7)	0.0036 (7)
C8	0.0577 (9)	0.0546 (8)	0.0557 (8)	−0.0063 (6)	0.0028 (6)	−0.0002 (6)
C9	0.0585 (9)	0.0649 (9)	0.0605 (9)	−0.0138 (7)	−0.0053 (7)	0.0080 (7)
C10	0.0630 (9)	0.0598 (9)	0.0626 (9)	−0.0092 (7)	0.0081 (7)	0.0016 (7)
C11	0.0571 (9)	0.0582 (9)	0.0687 (10)	−0.0089 (7)	0.0041 (7)	−0.0073 (7)
C12	0.0677 (11)	0.1012 (15)	0.0823 (12)	−0.0061 (10)	0.0152 (9)	−0.0173 (11)
C13	0.0573 (11)	0.1235 (19)	0.125 (2)	0.0081 (11)	0.0063 (12)	−0.0504 (16)
C14	0.0822 (14)	0.0752 (13)	0.1122 (17)	0.0145 (10)	−0.0234 (12)	−0.0352 (12)
C15	0.0834 (14)	0.0780 (12)	0.0816 (12)	−0.0117 (10)	−0.0150 (10)	−0.0032 (10)
C16	0.0630 (10)	0.0764 (11)	0.0705 (10)	−0.0161 (8)	0.0004 (8)	−0.0039 (8)
C17	0.050 (2)	0.086 (3)	0.079 (3)	−0.0014 (19)	0.0047 (18)	0.002 (2)
C18	0.088 (4)	0.084 (4)	0.091 (3)	0.033 (3)	−0.011 (3)	−0.017 (3)
C19	0.069 (3)	0.087 (3)	0.150 (8)	−0.011 (2)	−0.024 (4)	−0.006 (4)
C171	0.052 (2)	0.082 (3)	0.103 (4)	−0.003 (2)	0.020 (2)	0.000 (3)
C181	0.164 (10)	0.089 (6)	0.253 (16)	−0.004 (6)	−0.023 (9)	0.054 (7)
C191	0.100 (7)	0.194 (13)	0.133 (7)	0.046 (7)	−0.045 (5)	−0.088 (8)
C20	0.0715 (12)	0.0963 (14)	0.0802 (12)	0.0151 (10)	−0.0134 (9)	0.0089 (10)
C22	0.0577 (9)	0.0707 (11)	0.0840 (11)	−0.0181 (8)	−0.0025 (8)	0.0016 (9)
C23	0.0835 (14)	0.0758 (12)	0.1151 (17)	−0.0291 (10)	−0.0043 (12)	0.0166 (11)
O1	0.0531 (6)	0.0561 (6)	0.0748 (7)	−0.0085 (4)	−0.0115 (5)	0.0130 (5)
O2	0.0812 (8)	0.0705 (8)	0.0798 (8)	−0.0099 (6)	0.0050 (6)	0.0233 (6)
O3	0.0513 (6)	0.0614 (6)	0.0832 (8)	−0.0095 (5)	−0.0023 (5)	0.0121 (5)

C1—O1	1.3632 (17)	C15—H15	0.9300
C1—C6	1.389 (2)	C16—H16	0.9300
C1—C2	1.405 (2)	C17—C18	1.499 (6)
C2—O3	1.3659 (18)	C17—C19	1.540 (6)
C2—C3	1.381 (2)	C17—H17	0.9800
C3—C4	1.397 (2)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C5	1.368 (2)	C18—H18C	0.9600
C4—C20	1.514 (2)	C19—H19A	0.9600
C5—C6	1.407 (2)	C19—H19B	0.9600
C5—H5	0.9300	C19—H19C	0.9600
C6—C7	1.477 (2)	C171—C181	1.536 (9)
C7—O2	1.2234 (19)	C171—C191	1.538 (8)
C7—C8	1.489 (2)	C171—H171	0.9800
C8—C10	1.342 (2)	C181—H18D	0.9600
C8—C9	1.501 (2)	C181—H18E	0.9600
C9—O1	1.4351 (18)	C181—H18F	0.9600
C9—H9A	0.9700	C191—H19D	0.9600
C9—H9B	0.9700	C191—H19E	0.9600
C10—C11	1.462 (2)	C191—H19F	0.9600
C10—H10	0.9300	C20—H20A	0.9600
C11—C16	1.392 (2)	C20—H20B	0.9600
C11—C12	1.396 (3)	C20—H20C	0.9600
C12—C13	1.375 (3)	C22—O3	1.4294 (19)
C12—H12	0.9300	C22—C23	1.489 (3)
C13—C14	1.379 (4)	C22—H22A	0.9700
C13—H13	0.9300	C22—H22B	0.9700
C14—C15	1.384 (3)	C23—H23A	0.9600
C14—C17	1.550 (5)	C23—H23B	0.9600
C14—C171	1.568 (5)	C23—H23C	0.9600
C15—C16	1.375 (3)
O1—C1—C6	123.15 (13)	C19—C17—C14	103.5 (5)
O1—C1—C2	116.76 (13)	C18—C17—H17	111.5
C6—C1—C2	120.07 (13)	C19—C17—H17	111.5
O3—C2—C3	125.65 (14)	C14—C17—H17	111.5
O3—C2—C1	115.38 (13)	C17—C18—H18A	109.5
C3—C2—C1	118.96 (14)	C17—C18—H18B	109.5
C2—C3—C4	121.87 (15)	H18A—C18—H18B	109.5
C2—C3—H3	119.1	C17—C18—H18C	109.5
C4—C3—H3	119.1	H18A—C18—H18C	109.5
C5—C4—C3	118.40 (14)	H18B—C18—H18C	109.5
C5—C4—C20	122.08 (17)	C17—C19—H19A	109.5
C3—C4—C20	119.50 (16)	C17—C19—H19B	109.5
C4—C5—C6	121.61 (15)	H19A—C19—H19B	109.5
C4—C5—H5	119.2	C17—C19—H19C	109.5
C6—C5—H5	119.2	H19A—C19—H19C	109.5
C1—C6—C5	119.07 (14)	H19B—C19—H19C	109.5
C1—C6—C7	119.98 (13)	C181—C171—C191	100.2 (12)
C5—C6—C7	120.90 (14)	C181—C171—C14	105.3 (7)
O2—C7—C6	121.86 (15)	C191—C171—C14	106.7 (6)
O2—C7—C8	122.52 (15)	C181—C171—H171	114.4
C6—C7—C8	115.61 (13)	C191—C171—H171	114.4
C10—C8—C7	119.45 (14)	C14—C171—H171	114.4
C10—C8—C9	124.88 (14)	C171—C181—H18D	109.5
C7—C8—C9	115.66 (13)	C171—C181—H18E	109.5
O1—C9—C8	113.53 (12)	H18D—C181—H18E	109.5
O1—C9—H9A	108.9	C171—C181—H18F	109.5
C8—C9—H9A	108.9	H18D—C181—H18F	109.5
O1—C9—H9B	108.9	H18E—C181—H18F	109.5
C8—C9—H9B	108.9	C171—C191—H19D	109.5
H9A—C9—H9B	107.7	C171—C191—H19E	109.5
C8—C10—C11	129.32 (15)	H19D—C191—H19E	109.5
C8—C10—H10	115.3	C171—C191—H19F	109.5
C11—C10—H10	115.3	H19D—C191—H19F	109.5
C16—C11—C12	116.94 (17)	H19E—C191—H19F	109.5
C16—C11—C10	123.74 (15)	C4—C20—H20A	109.5
C12—C11—C10	119.30 (16)	C4—C20—H20B	109.5
C13—C12—C11	121.0 (2)	H20A—C20—H20B	109.5
C13—C12—H12	119.5	C4—C20—H20C	109.5
C11—C12—H12	119.5	H20A—C20—H20C	109.5
C12—C13—C14	122.1 (2)	H20B—C20—H20C	109.5
C12—C13—H13	119.0	O3—C22—C23	107.23 (15)
C14—C13—H13	119.0	O3—C22—H22A	110.3
C13—C14—C15	116.85 (19)	C23—C22—H22A	110.3
C13—C14—C17	133.8 (3)	O3—C22—H22B	110.3
C15—C14—C17	109.3 (3)	C23—C22—H22B	110.3
C13—C14—C171	105.8 (4)	H22A—C22—H22B	108.5
C15—C14—C171	137.1 (4)	C22—C23—H23A	109.5
C16—C15—C14	122.0 (2)	C22—C23—H23B	109.5
C16—C15—H15	119.0	H23A—C23—H23B	109.5
C14—C15—H15	119.0	C22—C23—H23C	109.5
C15—C16—C11	121.08 (18)	H23A—C23—H23C	109.5
C15—C16—H16	119.5	H23B—C23—H23C	109.5
C11—C16—H16	119.5	C1—O1—C9	115.47 (12)
C18—C17—C19	109.9 (8)	C2—O3—C22	117.71 (12)
C18—C17—C14	108.7 (5)
O1—C1—C2—O3	−1.1 (2)	C16—C11—C12—C13	−2.4 (3)
C6—C1—C2—O3	−179.60 (13)	C10—C11—C12—C13	179.00 (19)
O1—C1—C2—C3	179.92 (13)	C11—C12—C13—C14	0.9 (3)
C6—C1—C2—C3	1.4 (2)	C12—C13—C14—C15	0.7 (3)
O3—C2—C3—C4	−179.43 (15)	C12—C13—C14—C17	−175.5 (3)
C1—C2—C3—C4	−0.6 (2)	C12—C13—C14—C171	175.9 (3)
C2—C3—C4—C5	−0.6 (2)	C13—C14—C15—C16	−0.7 (3)
C2—C3—C4—C20	178.01 (16)	C17—C14—C15—C16	176.4 (2)
C3—C4—C5—C6	1.0 (3)	C171—C14—C15—C16	−173.9 (3)
C20—C4—C5—C6	−177.59 (16)	C14—C15—C16—C11	−0.9 (3)
O1—C1—C6—C5	−179.45 (14)	C12—C11—C16—C15	2.5 (3)
C2—C1—C6—C5	−1.1 (2)	C10—C11—C16—C15	−179.04 (17)
O1—C1—C6—C7	−1.9 (2)	C13—C14—C17—C18	47.0 (8)
C2—C1—C6—C7	176.48 (14)	C15—C14—C17—C18	−129.5 (6)
C4—C5—C6—C1	−0.2 (2)	C171—C14—C17—C18	64.2 (8)
C4—C5—C6—C7	−177.71 (15)	C13—C14—C17—C19	−69.9 (7)
C1—C6—C7—O2	−172.15 (15)	C15—C14—C17—C19	113.7 (7)
C5—C6—C7—O2	5.3 (3)	C171—C14—C17—C19	−52.7 (8)
C1—C6—C7—C8	7.1 (2)	C13—C14—C171—C181	111.4 (9)
C5—C6—C7—C8	−175.42 (14)	C15—C14—C171—C181	−74.9 (9)
O2—C7—C8—C10	14.1 (2)	C17—C14—C171—C181	−55.8 (9)
C6—C7—C8—C10	−165.17 (15)	C13—C14—C171—C191	−142.7 (9)
O2—C7—C8—C9	−166.14 (16)	C15—C14—C171—C191	31.0 (10)
C6—C7—C8—C9	14.6 (2)	C17—C14—C171—C191	50.1 (9)
C10—C8—C9—O1	138.48 (17)	C6—C1—O1—C9	−26.1 (2)
C7—C8—C9—O1	−41.3 (2)	C2—C1—O1—C9	155.44 (14)
C7—C8—C10—C11	179.85 (15)	C8—C9—O1—C1	47.03 (19)
C9—C8—C10—C11	0.1 (3)	C3—C2—O3—C22	9.9 (2)
C8—C10—C11—C16	33.2 (3)	C1—C2—O3—C22	−168.97 (14)
C8—C10—C11—C12	−148.30 (19)	C23—C22—O3—C2	177.70 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2i	0.97	2.60	3.407 (2)	141
C10—H10···O2	0.93	2.47	2.823 (2)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2i	0.97	2.60	3.407 (2)	141
C10—H10⋯O2	0.93	2.47	2.823 (2)	103

Symmetry code: (i) .