1-(Adamantan-1-yl)-3-(4-meth­oxy­phenyl)prop-2-en-1-one

The title mol­ecule, C₂₀H₂₄O₂, 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)°.

Key indicators

• Single-crystal X-ray study
• T = 90 K, P = 0.0 kPa
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.045
• wR factor = 0.123
• Data-to-parameter ratio = 30.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.425
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n
PLAT793_ALERT_4_G The Model has Chirality at C7      (Verify) ....          S
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         35

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Many chalconoid derivatives are bioactive agents with antiflammatory, antitumor, antiviral, gastroprotective and/or mutagenic activity (Ravishankar et al., 2003; Sathiya Moorthi et al., 2005; Patil et al., 2006). Title compound I is a chalconoid derivative with an adamantyl group in place of an aromatic system. Some adamantane derivatives have shown antiviral activity, specially against influenza and herpes viruses (Mullica et al., 1999).

The keto-enone group in particular plays a significant role in chalconoid chemistry since it is susceptible to a number of transformations (Homan et al., 1997). In I, this group is not planar: the O=C—C=C torsion is 12.24 (13)°. All other bond lengths and bond angles are within expected norms.

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).

S2. Experimental

The title compound was synthesized by Dr. Gabriel Garcia following the procedure of Kazlov et al. (1995). A suitable crystal was obtained by recrystallization from ethanol.

S3. Refinement

All H atoms were placed in calculated positions, guided by difference maps, with C—H bond distances constrained to the range 0.95–1.00 Å, and U_iso=1.2U_eq (1.5 for the methyl group), thereafter refined as riding. A torsional parameter was also refined for the methyl group.

Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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).

Figures

Fig. 1. View of (I) (50% probability displacement ellipsoids)

1-(Adamantan-1-yl)-3-(4-methoxyphenyl)prop-2-en-1-one

Crystal data

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) Å^3	0.35 × 0.28 × 0.24 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0625P)^2 + 0.485P] where P = (Fo^2 + 2Fc^2)/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

Special details

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.

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

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)