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

Nguyen, T.M.; Fronczek, F.R.; Watkins, S.F.

doi:10.1107/S1600536812032400

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2537

https://doi.org/10.1107/S1600536812032400

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1-(Adamantan-1-yl)-3-(4-methoxyphenyl)prop-2-en-1-one¹

Thy M. Nguyen,^a Frank R. Fronczek ^a ^* and Steven F. Watkins ^a

^aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
^*Correspondence e-mail: ffroncz@lsu.edu

(Received 13 July 2012; accepted 16 July 2012; online 25 July 2012)

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)°.

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_r = 296.39
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.123
S = 0.99
6165 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812032400/ds2206sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032400/ds2206Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812032400/ds2206Isup3.cml

checkCIF report

Comment top

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 top

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 top

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.

Structure description top

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).

Computing details top

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 top

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

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

Crystal data top

C₂₀H₂₄O₂	F(000) = 640
M_r = 296.39	D_x = 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

Data collection top

Nonius KappaCCD diffractometer	6165 independent reflections
Radiation source: sealed tube	4860 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 9 pixels mm^-1	θ_max = 33.7°, θ_min = 2.8°
CCD rotation images, thick slices scans	h = −10→10
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −25→24
T_min = 0.973, T_max = 0.981	l = −22→22
11653 measured reflections

Refinement top

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(F_o²) + (0.0625P)² + 0.485P] where P = (F_o² + 2F_c²)/3
6165 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³
0 constraints

Crystal data top

C₂₀H₂₄O₂	V = 1554.46 (6) Å³
M_r = 296.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.4648 (1) Å	µ = 0.08 mm⁻¹
b = 16.4712 (3) Å	T = 90 K
c = 14.6134 (4) Å	0.35 × 0.28 × 0.24 mm
β = 92.612 (1)°

Data collection top

Nonius KappaCCD diffractometer	6165 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	4860 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.981	R_int = 0.026
11653 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 0.99	Δρ_max = 0.47 e Å⁻³
6165 reflections	Δρ_min = −0.29 e Å⁻³
200 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄O₂
M_r	296.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	90
a, b, c (Å)	6.4648 (1), 16.4712 (3), 14.6134 (4)
β (°)	92.612 (1)
V (Å³)	1554.46 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.28 × 0.24

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.973, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	11653, 6165, 4860
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.781

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.123, 0.99
No. of reflections	6165
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.29

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Footnotes

¹CAS 174315-56-1.

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF (1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents. We thank Dr Gabriel Garcia for providing the sample.

References

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