1-(Adamantan-1-yl)-3-(4-meth-oxy-phenyl)prop-2-en-1-one.

The title mol-ecule, C(20)H(24)O(2), is a chalconoid derivative in which the keto-enone group is slightly distorted from planarity; the O=C-C=C torsion angle is 12.24 (13)°.

Related literature

For the role of the keto-enone group in chalconoid chemistry, see: Homan et al. (1997 ▶). Many chalconoid derivatives are bioactive agents with anti­flammatory, anti­tumor, anti­viral, gastroprotective and/or mutagenic activity, see: Ravishankar et al. (2003 ▶); Sathiya Moorthi et al. (2005 ▶); Patil et al. (2006 ▶). Some adamantane derivatives have shown anti­viral activity, especially against influenza and herpes viruses, see: Mullica et al. (1999 ▶). For the synthesis, see: Kazlov et al. (1995 ▶).

Experimental

Crystal data

C20H24O2

M = 296.39

Monoclinic,

a = 6.4648 (1) Å

b = 16.4712 (3) Å

c = 14.6134 (4) Å

β = 92.612 (1)°

V = 1554.46 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 90 K

0.35 × 0.28 × 0.24 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.973, T max = 0.981

11653 measured reflections

6165 independent reflections

4860 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.123

S = 0.99

6165 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032400/ds2206sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032400/ds2206Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032400/ds2206Isup3.cml

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

C20H24O2	F(000) = 640
Mr = 296.39	Dx = 1.266 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5846 reflections
a = 6.4648 (1) Å	θ = 2.6–33.7°
b = 16.4712 (3) Å	µ = 0.08 mm−1
c = 14.6134 (4) Å	T = 90 K
β = 92.612 (1)°	Prism, colorless
V = 1554.46 (6) Å3	0.35 × 0.28 × 0.24 mm
Z = 4

Nonius KappaCCD diffractometer	6165 independent reflections
Radiation source: sealed tube	4860 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 9 pixels mm-1	θmax = 33.7°, θmin = 2.8°
CCD rotation images, thick slices scans	h = −10→10
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −25→24
Tmin = 0.973, Tmax = 0.981	l = −22→22
11653 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.485P] where P = (Fo2 + 2Fc2)/3
6165 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.29 e Å−3
0 constraints

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.

	x	y	z	Uiso*/Ueq
C1	1.17484 (12)	0.49689 (5)	0.77117 (6)	0.01203 (14)
C2	1.39267 (13)	0.50311 (5)	0.81790 (6)	0.01455 (15)
H2A	1.4965	0.5105	0.7709	0.017*
H2B	1.3994	0.5509	0.859	0.017*
C3	1.44258 (12)	0.42587 (5)	0.87340 (6)	0.01529 (16)
H3	1.585	0.4303	0.9027	0.018*
C4	1.43213 (13)	0.35203 (5)	0.80922 (7)	0.01668 (16)
H4A	1.4671	0.3021	0.8444	0.02*
H4B	1.534	0.3584	0.7611	0.02*
C5	1.21310 (13)	0.34455 (5)	0.76470 (6)	0.01470 (15)
H5	1.2062	0.296	0.7236	0.018*
C6	1.05468 (13)	0.33524 (5)	0.83940 (6)	0.01542 (15)
H6A	0.9136	0.3304	0.8107	0.019*
H6B	1.0848	0.2853	0.8753	0.019*
C7	1.06570 (13)	0.40947 (5)	0.90296 (6)	0.01396 (15)
H7	0.9626	0.4032	0.9515	0.017*
C8	1.01594 (12)	0.48667 (5)	0.84674 (6)	0.01350 (15)
H8A	1.0212	0.5346	0.8876	0.016*
H8B	0.8744	0.4827	0.8182	0.016*
C9	1.16385 (13)	0.42133 (5)	0.70825 (6)	0.01387 (15)
H9A	1.0236	0.4168	0.6786	0.017*
H9B	1.2645	0.427	0.6596	0.017*
C10	1.28430 (13)	0.41594 (6)	0.94802 (6)	0.01611 (16)
H10A	1.3163	0.3664	0.9844	0.019*
H10B	1.2919	0.4632	0.9899	0.019*
C11	1.12481 (13)	0.57368 (5)	0.71656 (6)	0.01414 (15)
C12	0.93169 (13)	0.57598 (5)	0.65717 (6)	0.01481 (15)
H12	0.8298	0.5348	0.6616	0.018*
C13	0.90363 (13)	0.63728 (5)	0.59715 (6)	0.01471 (15)
H13	1.0173	0.6735	0.5934	0.018*
C14	0.72429 (13)	0.65630 (5)	0.53694 (6)	0.01366 (15)
C15	0.53920 (13)	0.61095 (5)	0.53374 (6)	0.01574 (16)
H15	0.5296	0.5635	0.5703	0.019*
C16	0.37129 (13)	0.63471 (5)	0.47793 (6)	0.01635 (16)
H16	0.2482	0.6032	0.4758	0.02*
C17	0.38227 (13)	0.70527 (5)	0.42450 (6)	0.01399 (15)
C18	0.56503 (13)	0.75027 (5)	0.42526 (6)	0.01432 (15)
H18	0.5747	0.7973	0.3881	0.017*
C19	0.73332 (13)	0.72522 (5)	0.48129 (6)	0.01446 (15)
H19	0.8579	0.7559	0.4817	0.017*
C20	0.21429 (14)	0.79562 (5)	0.31728 (6)	0.01815 (17)
H20A	0.2512	0.8432	0.3549	0.027*
H20B	0.0786	0.8043	0.2861	0.027*
H20C	0.3187	0.7875	0.2716	0.027*
O1	1.23918 (11)	0.63302 (4)	0.72203 (5)	0.02329 (16)
O2	0.20598 (10)	0.72512 (4)	0.37467 (5)	0.01787 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0108 (3)	0.0126 (3)	0.0126 (3)	0.0000 (2)	0.0000 (2)	−0.0001 (3)
C2	0.0118 (3)	0.0153 (4)	0.0165 (4)	−0.0015 (3)	−0.0007 (3)	0.0012 (3)
C3	0.0114 (3)	0.0175 (4)	0.0168 (4)	0.0001 (3)	−0.0013 (3)	0.0023 (3)
C4	0.0146 (3)	0.0163 (4)	0.0193 (4)	0.0042 (3)	0.0033 (3)	0.0022 (3)
C5	0.0169 (3)	0.0122 (3)	0.0151 (4)	0.0011 (3)	0.0019 (3)	−0.0010 (3)
C6	0.0159 (3)	0.0142 (4)	0.0162 (4)	−0.0018 (3)	0.0019 (3)	0.0005 (3)
C7	0.0133 (3)	0.0164 (4)	0.0123 (4)	−0.0003 (3)	0.0025 (3)	0.0003 (3)
C8	0.0119 (3)	0.0151 (4)	0.0137 (4)	0.0017 (3)	0.0020 (3)	−0.0011 (3)
C9	0.0154 (3)	0.0138 (4)	0.0125 (4)	0.0006 (3)	0.0016 (3)	−0.0011 (3)
C10	0.0163 (3)	0.0187 (4)	0.0132 (4)	0.0002 (3)	−0.0010 (3)	0.0008 (3)
C11	0.0144 (3)	0.0136 (4)	0.0143 (4)	0.0008 (3)	−0.0005 (3)	0.0002 (3)
C12	0.0141 (3)	0.0148 (4)	0.0154 (4)	0.0006 (3)	−0.0007 (3)	0.0006 (3)
C13	0.0157 (3)	0.0139 (4)	0.0144 (4)	0.0017 (3)	−0.0005 (3)	−0.0010 (3)
C14	0.0150 (3)	0.0134 (3)	0.0126 (4)	0.0015 (3)	0.0005 (3)	−0.0002 (3)
C15	0.0179 (4)	0.0143 (4)	0.0150 (4)	0.0000 (3)	0.0008 (3)	0.0026 (3)
C16	0.0153 (3)	0.0168 (4)	0.0169 (4)	−0.0018 (3)	0.0008 (3)	0.0020 (3)
C17	0.0139 (3)	0.0151 (4)	0.0129 (3)	0.0012 (3)	0.0000 (3)	−0.0002 (3)
C18	0.0160 (3)	0.0135 (3)	0.0135 (4)	0.0005 (3)	0.0008 (3)	0.0013 (3)
C19	0.0147 (3)	0.0140 (4)	0.0147 (4)	−0.0005 (3)	0.0004 (3)	0.0004 (3)
C20	0.0208 (4)	0.0154 (4)	0.0179 (4)	0.0016 (3)	−0.0032 (3)	0.0016 (3)
O1	0.0247 (3)	0.0153 (3)	0.0289 (4)	−0.0052 (2)	−0.0089 (3)	0.0040 (3)
O2	0.0146 (3)	0.0193 (3)	0.0194 (3)	−0.0003 (2)	−0.0026 (2)	0.0047 (2)

C1—C11	1.5223 (12)	C9—H9B	0.99
C1—C2	1.5402 (11)	C10—H10A	0.99
C1—C9	1.5471 (12)	C10—H10B	0.99
C1—C8	1.5513 (12)	C11—O1	1.2260 (11)
C2—C3	1.5351 (12)	C11—C12	1.4882 (12)
C2—H2A	0.99	C12—C13	1.3443 (12)
C2—H2B	0.99	C12—H12	0.95
C3—C4	1.5355 (13)	C13—C14	1.4572 (12)
C3—C10	1.5378 (13)	C13—H13	0.95
C3—H3	1	C14—C19	1.3992 (12)
C4—C5	1.5361 (12)	C14—C15	1.4095 (12)
C4—H4A	0.99	C15—C16	1.3842 (12)
C4—H4B	0.99	C15—H15	0.95
C5—C9	1.5354 (12)	C16—C17	1.4037 (12)
C5—C6	1.5382 (12)	C16—H16	0.95
C5—H5	1	C17—O2	1.3639 (10)
C6—C7	1.5351 (12)	C17—C18	1.3943 (12)
C6—H6A	0.99	C18—C19	1.3939 (12)
C6—H6B	0.99	C18—H18	0.95
C7—C10	1.5354 (12)	C19—H19	0.95
C7—C8	1.5398 (12)	C20—O2	1.4348 (11)
C7—H7	1	C20—H20A	0.98
C8—H8A	0.99	C20—H20B	0.98
C8—H8B	0.99	C20—H20C	0.98
C9—H9A	0.99
C11—C1—C2	110.20 (7)	H8A—C8—H8B	108.2
C11—C1—C9	110.73 (7)	C5—C9—C1	109.91 (7)
C2—C1—C9	109.47 (7)	C5—C9—H9A	109.7
C11—C1—C8	109.37 (7)	C1—C9—H9A	109.7
C2—C1—C8	108.26 (7)	C5—C9—H9B	109.7
C9—C1—C8	108.77 (6)	C1—C9—H9B	109.7
C3—C2—C1	110.19 (7)	H9A—C9—H9B	108.2
C3—C2—H2A	109.6	C7—C10—C3	109.42 (7)
C1—C2—H2A	109.6	C7—C10—H10A	109.8
C3—C2—H2B	109.6	C3—C10—H10A	109.8
C1—C2—H2B	109.6	C7—C10—H10B	109.8
H2A—C2—H2B	108.1	C3—C10—H10B	109.8
C2—C3—C4	109.35 (7)	H10A—C10—H10B	108.2
C2—C3—C10	109.40 (7)	O1—C11—C12	120.34 (8)
C4—C3—C10	109.68 (7)	O1—C11—C1	121.00 (7)
C2—C3—H3	109.5	C12—C11—C1	118.65 (7)
C4—C3—H3	109.5	C13—C12—C11	118.97 (8)
C10—C3—H3	109.5	C13—C12—H12	120.5
C3—C4—C5	109.65 (7)	C11—C12—H12	120.5
C3—C4—H4A	109.7	C12—C13—C14	129.45 (8)
C5—C4—H4A	109.7	C12—C13—H13	115.3
C3—C4—H4B	109.7	C14—C13—H13	115.3
C5—C4—H4B	109.7	C19—C14—C15	117.94 (7)
H4A—C4—H4B	108.2	C19—C14—C13	118.18 (7)
C9—C5—C4	109.03 (7)	C15—C14—C13	123.84 (8)
C9—C5—C6	109.56 (7)	C16—C15—C14	120.76 (8)
C4—C5—C6	109.76 (7)	C16—C15—H15	119.6
C9—C5—H5	109.5	C14—C15—H15	119.6
C4—C5—H5	109.5	C15—C16—C17	120.24 (8)
C6—C5—H5	109.5	C15—C16—H16	119.9
C7—C6—C5	109.64 (7)	C17—C16—H16	119.9
C7—C6—H6A	109.7	O2—C17—C18	124.33 (8)
C5—C6—H6A	109.7	O2—C17—C16	115.67 (7)
C7—C6—H6B	109.7	C18—C17—C16	120.00 (8)
C5—C6—H6B	109.7	C19—C18—C17	119.06 (8)
H6A—C6—H6B	108.2	C19—C18—H18	120.5
C10—C7—C6	109.34 (7)	C17—C18—H18	120.5
C10—C7—C8	109.71 (7)	C18—C19—C14	121.97 (8)
C6—C7—C8	109.39 (7)	C18—C19—H19	119
C10—C7—H7	109.5	C14—C19—H19	119
C6—C7—H7	109.5	O2—C20—H20A	109.5
C8—C7—H7	109.5	O2—C20—H20B	109.5
C7—C8—C1	109.90 (6)	H20A—C20—H20B	109.5
C7—C8—H8A	109.7	O2—C20—H20C	109.5
C1—C8—H8A	109.7	H20A—C20—H20C	109.5
C7—C8—H8B	109.7	H20B—C20—H20C	109.5
C1—C8—H8B	109.7	C17—O2—C20	116.96 (7)
C11—C1—C2—C3	179.68 (7)	C2—C3—C10—C7	59.86 (9)
C9—C1—C2—C3	−58.31 (9)	C4—C3—C10—C7	−60.08 (9)
C8—C1—C2—C3	60.12 (9)	C2—C1—C11—O1	−8.16 (12)
C1—C2—C3—C4	59.33 (9)	C9—C1—C11—O1	−129.42 (9)
C1—C2—C3—C10	−60.81 (9)	C8—C1—C11—O1	110.73 (9)
C2—C3—C4—C5	−60.59 (9)	C2—C1—C11—C12	172.81 (7)
C10—C3—C4—C5	59.37 (9)	C9—C1—C11—C12	51.55 (10)
C3—C4—C5—C9	60.99 (9)	C8—C1—C11—C12	−68.30 (9)
C3—C4—C5—C6	−59.03 (9)	O1—C11—C12—C13	12.24 (13)
C9—C5—C6—C7	−60.23 (9)	C1—C11—C12—C13	−168.72 (8)
C4—C5—C6—C7	59.47 (9)	C11—C12—C13—C14	−175.10 (8)
C5—C6—C7—C10	−60.07 (9)	C12—C13—C14—C19	179.04 (9)
C5—C6—C7—C8	60.10 (9)	C12—C13—C14—C15	1.35 (15)
C10—C7—C8—C1	59.94 (9)	C19—C14—C15—C16	−0.75 (13)
C6—C7—C8—C1	−60.01 (8)	C13—C14—C15—C16	176.95 (8)
C11—C1—C8—C7	−179.62 (6)	C14—C15—C16—C17	−0.90 (14)
C2—C1—C8—C7	−59.53 (8)	C15—C16—C17—O2	−177.53 (8)
C9—C1—C8—C7	59.34 (8)	C15—C16—C17—C18	2.08 (14)
C4—C5—C9—C1	−60.05 (9)	O2—C17—C18—C19	178.00 (8)
C6—C5—C9—C1	60.10 (9)	C16—C17—C18—C19	−1.57 (13)
C11—C1—C9—C5	−179.57 (7)	C17—C18—C19—C14	−0.10 (13)
C2—C1—C9—C5	58.74 (9)	C15—C14—C19—C18	1.25 (13)
C8—C1—C9—C5	−59.36 (8)	C13—C14—C19—C18	−176.58 (8)
C6—C7—C10—C3	60.33 (9)	C18—C17—O2—C20	2.20 (13)
C8—C7—C10—C3	−59.64 (9)	C16—C17—O2—C20	−178.21 (8)