1-(Anthracen-1-yl)pyrrolidine-2,5-dione

Khorasani, S.; Fernandes, M.A.

doi:10.1107/S160053681201536X

organic compounds

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Volume 68| Part 5| May 2012| Page o1503

doi:10.1107/S160053681201536X

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1-(Anthracen-1-yl)pyrrolidine-2,5-dione

Sanaz Khorasani ^a and Manuel A. Fernandes ^a ^*

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
^*Correspondence e-mail: manuel.fernandes@wits.ac.za

(Received 2 March 2012; accepted 8 April 2012; online 21 April 2012)

In the molecular structure of title compound, C₁₈H₁₃NO₂, the succinimide ring is orientated away from the plane of the anthracene moiety by 71.94 (4)°. The crystal structure features three different types of intermolecular interactions, viz. C—H⋯O, C—H⋯π and π–π bonds. Molecules along the b axis stack on each other as a result of π–π interactions which have a centroid–centroid distance of 3.6780 (15) Å, while C—H⋯π interactions are present between neigbouring stacks. Also, acting between the stacks are the C—H⋯O interactions between the aromatic H atoms of the anthracene and the O atoms of the succinimide.

Related literature

For studies of regio- and sterio-selectivity of substituted anthracenes in Diels–Alder reactions, see: Singh & Ningombom (2010 ); Alston et al. (1979 ); Meek et al. (1960 ); Kaplan & Conroy (1963 ); Verma & Singh (1977 ). For a study involving NMR experiments, see: Hubbard et al. (1992 ).

Experimental

Crystal data

C₁₈H₁₃NO₂
M_r = 275.29
Orthorhombic, P n a 2₁
a = 18.4179 (9) Å
b = 5.7697 (4) Å
c = 12.4403 (6) Å
V = 1321.98 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.49 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
10655 measured reflections
1667 independent reflections
1258 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.088
S = 0.95
1667 reflections
190 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.95	2.38	3.234 (3)	149
C6—H6⋯O1ⁱⁱ	0.95	2.49	3.357 (3)	152
C9—H9⋯O2ⁱⁱⁱ	0.95	2.53	3.465 (3)	167
C13—H13⋯O1^iv	0.95	2.70	3.471 (3)	139
C17—H17A⋯Cg2^v	0.99	2.92	3.709 (3)	138
Symmetry codes: (i) x, y+1, z; (ii) $[-x, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iv) x, y-1, z; (v) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

Data collection: APEX2 (Bruker 2005 ); cell refinement: SAINT (Bruker 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and SCHAKAL99 (Keller, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201536X/rk2341sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201536X/rk2341Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201536X/rk2341Isup3.cml

checkCIF report

Comment top

The compound anthracene has been known for a long time and its properties have been extensively studied. The regio- and sterio-selectivity of substituted anthracenes in Diels-Alder reactions have been investigated and reported (Alston et al., 1979; Meek et al., 1960; Kaplan & Conroy, 1963; Verma & Singh, 1977; Singh & Ningombom, 2010). A study of the title compound and 1-succinimidonaphthalene involving synthesis, NMR experiments and molecular mechanics has been reported by Hubbard et al. (1992).

Both the anthracene and succinimide moeities are planar but are tilted with respect to each other at an angle of 71.94 (4)° (Fig. 1). Two anthracene bond lengths – C1—C14 [1.430 (3)Å] and C5—C14 [1.443 (3)Å] – are significantly longer than the 1.39Å typical of aromatic rings. As a consequence the rings containing these have been flagged as having larger than average C6-ring C—C bond lengths by PLATON (Spek, 2009), suggesting that the succinimide group has a significant effect on the charge distribution within the anthracene ring. The crystal structure contains three different types of intermolecular interactions, these include C–H···O, C–H···π and π–π interactions (Fig. 2). The π–π interaction occurs over a Cg1···Cg2 distance of 3.678 (2)Å between the rings defined by C1-C5/C14 (Cg1) and C7-C12 (Cg2). This leads to the stacking of molecules along b axis. Geometrical details of the C–H···π and C–H···O interactions are given in the Table 1.

Related literature top

For studies involving Diels–Alder reactions with anthracene, see: Singh & Ningombom (2010); Alston et al. (1979); Meek et al. (1960); Kaplan & Conroy (1963); Verma & Singh (1977). For a study involving NMR experiments, see: Hubbard et al. (1992).

Experimental top

The title compound was synthesized with very low yield (a few crystals) by reaction of 1-aminoanthracene (0.200 g, 1 mmol) with succinic anhydride (0.107 g, 1 mmol) in the presence of dioxane as a solvent (3 ml) by strirring at room temperature for a few hours. Thionyl chloride (3 ml) in dioxane (2 ml) was then slowly added to the reaction mixture at room temperature. The mixture was then kept at 323 K for 12 h, followed by neutralization of excess thionyl chloride by pouring the mixture into a beaker containing ice. This mixture was then filtered yielding a dark brown material, which after recrystallization by slow evaporation from chloroform yielded a few crystals suitable for analysis by X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker 2005); cell refinement: SAINT (Bruker 2005); data reduction: SAINT (Bruker 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. C–H···O, C–H···π and π–π interactions in the structure of the title compound. The C–H···π and π–π interactions are respectively indicated by dollar ($) or hash (#) symbols.

1-(Anthracen-1-yl)pyrrolidine-2,5-dione top

Crystal data top

C₁₈H₁₃NO₂	F(000) = 576
M_r = 275.29	D_x = 1.383 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2466 reflections
a = 18.4179 (9) Å	θ = 2.8–26.7°
b = 5.7697 (4) Å	µ = 0.09 mm⁻¹
c = 12.4403 (6) Å	T = 173 K
V = 1321.98 (13) Å³	Plate, brown
Z = 4	0.49 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	1258 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.081
Graphite monochromator	θ_max = 28.0°, θ_min = 2.2°
ϕ– and ω–scans	h = −24→24
10655 measured reflections	k = −7→7
1667 independent reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0468P)²] where P = (F_o² + 2F_c²)/3
1667 reflections	(Δ/σ)_max = 0.002
190 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₁₃NO₂	V = 1321.98 (13) Å³
M_r = 275.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 18.4179 (9) Å	µ = 0.09 mm⁻¹
b = 5.7697 (4) Å	T = 173 K
c = 12.4403 (6) Å	0.49 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	1258 reflections with I > 2σ(I)
10655 measured reflections	R_int = 0.081
1667 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.088	H-atom parameters constrained
S = 0.95	Δρ_max = 0.17 e Å⁻³
1667 reflections	Δρ_min = −0.19 e Å⁻³
190 parameters

Special details top

Geometry. All s.u.'s (except s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.12512 (12)	1.0166 (5)	0.33781 (19)	0.0300 (6)
C2	−0.13405 (14)	1.2022 (5)	0.40282 (19)	0.0348 (7)
H2	−0.1762	1.2958	0.3959	0.042*
C3	−0.08086 (14)	1.2588 (5)	0.4816 (2)	0.0369 (7)
H3	−0.0870	1.3914	0.5259	0.044*
C4	−0.02145 (13)	1.1223 (5)	0.4929 (2)	0.0373 (7)
H4	0.0131	1.1585	0.5471	0.045*
C5	−0.00952 (13)	0.9262 (5)	0.42571 (18)	0.0313 (6)
C6	0.05236 (13)	0.7881 (5)	0.43475 (19)	0.0340 (7)
H6	0.0869	0.8231	0.4891	0.041*
C7	0.06517 (13)	0.6010 (5)	0.3669 (2)	0.0331 (6)
C8	0.12738 (13)	0.4548 (5)	0.3779 (2)	0.0393 (7)
H8	0.1618	0.4860	0.4329	0.047*
C9	0.13797 (14)	0.2722 (6)	0.3111 (2)	0.0420 (7)
H9	0.1795	0.1764	0.3200	0.050*
C10	0.08711 (14)	0.2228 (6)	0.2274 (2)	0.0429 (7)
H10	0.0952	0.0961	0.1801	0.051*
C11	0.02709 (13)	0.3575 (5)	0.2156 (2)	0.0351 (7)
H11	−0.0065	0.3229	0.1599	0.042*
C12	0.01350 (12)	0.5483 (5)	0.28448 (18)	0.0300 (6)
C13	−0.04932 (12)	0.6848 (5)	0.27515 (19)	0.0298 (6)
H13	−0.0837	0.6496	0.2206	0.036*
C14	−0.06241 (12)	0.8710 (5)	0.34406 (18)	0.0280 (6)
C15	−0.19237 (13)	1.1049 (5)	0.16742 (19)	0.0324 (6)
C16	−0.24985 (14)	0.9892 (5)	0.1008 (2)	0.0409 (7)
H16A	−0.2302	0.9440	0.0298	0.049*
H16B	−0.2917	1.0943	0.0898	0.049*
C17	−0.27266 (14)	0.7749 (5)	0.1650 (2)	0.0394 (7)
H17A	−0.3250	0.7813	0.1828	0.047*
H17B	−0.2630	0.6316	0.1236	0.047*
C18	−0.22734 (12)	0.7812 (5)	0.2656 (2)	0.0328 (6)
N1	−0.17925 (10)	0.9652 (4)	0.25776 (16)	0.0301 (5)
O1	−0.16111 (10)	1.2847 (4)	0.14866 (14)	0.0409 (5)
O2	−0.23048 (9)	0.6519 (4)	0.34224 (15)	0.0415 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0272 (12)	0.0376 (16)	0.0252 (11)	−0.0043 (11)	0.0015 (9)	0.0022 (13)
C2	0.0324 (13)	0.0423 (18)	0.0298 (13)	0.0020 (12)	0.0038 (10)	0.0024 (14)
C3	0.0414 (15)	0.0417 (18)	0.0278 (12)	−0.0020 (13)	0.0027 (11)	−0.0064 (13)
C4	0.0360 (14)	0.051 (2)	0.0253 (12)	−0.0075 (13)	0.0000 (11)	−0.0014 (14)
C5	0.0294 (12)	0.0421 (17)	0.0223 (11)	−0.0043 (12)	0.0000 (10)	0.0022 (12)
C6	0.0275 (12)	0.0484 (19)	0.0260 (12)	−0.0051 (12)	−0.0050 (10)	0.0036 (14)
C7	0.0280 (12)	0.0402 (18)	0.0312 (13)	−0.0038 (12)	0.0001 (10)	0.0069 (13)
C8	0.0262 (12)	0.050 (2)	0.0419 (14)	−0.0011 (13)	−0.0026 (11)	0.0111 (15)
C9	0.0290 (13)	0.0429 (19)	0.0541 (17)	0.0058 (13)	0.0047 (13)	0.0080 (16)
C10	0.0365 (15)	0.0420 (19)	0.0503 (17)	0.0007 (14)	0.0099 (13)	−0.0003 (17)
C11	0.0320 (14)	0.0402 (18)	0.0333 (13)	−0.0010 (13)	0.0013 (10)	−0.0016 (13)
C12	0.0260 (12)	0.0353 (17)	0.0287 (12)	−0.0020 (11)	0.0030 (9)	0.0051 (13)
C13	0.0258 (11)	0.0403 (18)	0.0235 (11)	−0.0061 (11)	0.0000 (9)	0.0032 (13)
C14	0.0261 (11)	0.0361 (16)	0.0217 (11)	−0.0054 (11)	0.0019 (9)	0.0022 (12)
C15	0.0279 (12)	0.0426 (17)	0.0267 (12)	0.0034 (12)	0.0039 (9)	0.0004 (13)
C16	0.0381 (13)	0.052 (2)	0.0326 (12)	−0.0054 (14)	−0.0045 (10)	0.0022 (14)
C17	0.0344 (13)	0.0445 (18)	0.0393 (14)	−0.0035 (12)	−0.0058 (11)	0.0011 (14)
C18	0.0260 (12)	0.0367 (16)	0.0357 (13)	0.0043 (11)	0.0009 (10)	0.0031 (14)
N1	0.0257 (9)	0.0377 (13)	0.0269 (9)	0.0010 (9)	−0.0007 (8)	0.0015 (10)
O1	0.0431 (10)	0.0482 (13)	0.0313 (9)	−0.0103 (10)	0.0025 (8)	0.0046 (9)
O2	0.0349 (9)	0.0453 (12)	0.0443 (11)	−0.0037 (9)	−0.0026 (8)	0.0134 (10)

Geometric parameters (Å, º) top

C1—C2	1.352 (4)	C10—C11	1.359 (4)
C1—C14	1.430 (3)	C10—H10	0.9500
C1—N1	1.440 (3)	C11—C12	1.418 (4)
C2—C3	1.423 (4)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.405 (3)
C3—C4	1.355 (4)	C13—C14	1.395 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.424 (4)	C15—O1	1.209 (3)
C4—H4	0.9500	C15—N1	1.404 (3)
C5—C6	1.395 (4)	C15—C16	1.501 (4)
C5—C14	1.443 (3)	C16—C17	1.531 (4)
C6—C7	1.390 (4)	C16—H16A	0.9900
C6—H6	0.9500	C16—H16B	0.9900
C7—C8	1.429 (4)	C17—C18	1.505 (3)
C7—C12	1.432 (3)	C17—H17A	0.9900
C8—C9	1.357 (4)	C17—H17B	0.9900
C8—H8	0.9500	C18—O2	1.211 (3)
C9—C10	1.430 (4)	C18—N1	1.386 (3)
C9—H9	0.9500

C2—C1—C14	122.1 (2)	C12—C11—H11	119.3
C2—C1—N1	119.5 (2)	C13—C12—C11	122.1 (2)
C14—C1—N1	118.4 (2)	C13—C12—C7	119.2 (2)
C1—C2—C3	120.6 (3)	C11—C12—C7	118.7 (2)
C1—C2—H2	119.7	C14—C13—C12	121.6 (2)
C3—C2—H2	119.7	C14—C13—H13	119.2
C4—C3—C2	119.6 (3)	C12—C13—H13	119.2
C4—C3—H3	120.2	C13—C14—C1	123.9 (2)
C2—C3—H3	120.2	C13—C14—C5	119.1 (2)
C3—C4—C5	121.7 (2)	C1—C14—C5	117.0 (2)
C3—C4—H4	119.2	O1—C15—N1	124.4 (2)
C5—C4—H4	119.2	O1—C15—C16	127.7 (2)
C6—C5—C4	122.2 (2)	N1—C15—C16	107.9 (2)
C6—C5—C14	118.8 (2)	C15—C16—C17	105.4 (2)
C4—C5—C14	119.0 (2)	C15—C16—H16A	110.7
C7—C6—C5	122.2 (2)	C17—C16—H16A	110.7
C7—C6—H6	118.9	C15—C16—H16B	110.7
C5—C6—H6	118.9	C17—C16—H16B	110.7
C6—C7—C8	122.4 (2)	H16A—C16—H16B	108.8
C6—C7—C12	119.1 (2)	C18—C17—C16	105.2 (2)
C8—C7—C12	118.4 (3)	C18—C17—H17A	110.7
C9—C8—C7	121.0 (3)	C16—C17—H17A	110.7
C9—C8—H8	119.5	C18—C17—H17B	110.7
C7—C8—H8	119.5	C16—C17—H17B	110.7
C8—C9—C10	120.5 (3)	H17A—C17—H17B	108.8
C8—C9—H9	119.8	O2—C18—N1	123.9 (2)
C10—C9—H9	119.8	O2—C18—C17	127.8 (2)
C11—C10—C9	119.8 (3)	N1—C18—C17	108.3 (2)
C11—C10—H10	120.1	C18—N1—C15	112.7 (2)
C9—C10—H10	120.1	C18—N1—C1	123.5 (2)
C10—C11—C12	121.5 (3)	C15—N1—C1	123.7 (2)
C10—C11—H11	119.3

C14—C1—C2—C3	−0.6 (4)	C2—C1—C14—C13	−176.7 (2)
N1—C1—C2—C3	−179.1 (2)	N1—C1—C14—C13	1.8 (3)
C1—C2—C3—C4	−1.4 (4)	C2—C1—C14—C5	1.9 (3)
C2—C3—C4—C5	1.9 (4)	N1—C1—C14—C5	−179.5 (2)
C3—C4—C5—C6	178.3 (3)	C6—C5—C14—C13	−1.4 (3)
C3—C4—C5—C14	−0.4 (4)	C4—C5—C14—C13	177.3 (2)
C4—C5—C6—C7	−177.9 (2)	C6—C5—C14—C1	179.8 (2)
C14—C5—C6—C7	0.8 (4)	C4—C5—C14—C1	−1.4 (3)
C5—C6—C7—C8	−178.1 (3)	O1—C15—C16—C17	−177.3 (2)
C5—C6—C7—C12	0.4 (4)	N1—C15—C16—C17	3.5 (3)
C6—C7—C8—C9	179.4 (3)	C15—C16—C17—C18	0.6 (3)
C12—C7—C8—C9	0.9 (4)	C16—C17—C18—O2	175.4 (3)
C7—C8—C9—C10	0.4 (4)	C16—C17—C18—N1	−4.5 (3)
C8—C9—C10—C11	−1.0 (4)	O2—C18—N1—C15	−172.7 (2)
C9—C10—C11—C12	0.3 (4)	C17—C18—N1—C15	7.2 (3)
C10—C11—C12—C13	−178.2 (3)	O2—C18—N1—C1	3.1 (4)
C10—C11—C12—C7	1.1 (4)	C17—C18—N1—C1	−177.0 (2)
C6—C7—C12—C13	−0.9 (3)	O1—C15—N1—C18	173.9 (2)
C8—C7—C12—C13	177.6 (2)	C16—C15—N1—C18	−6.9 (3)
C6—C7—C12—C11	179.9 (2)	O1—C15—N1—C1	−1.8 (4)
C8—C7—C12—C11	−1.6 (4)	C16—C15—N1—C1	177.4 (2)
C11—C12—C13—C14	179.4 (2)	C2—C1—N1—C18	−107.2 (3)
C7—C12—C13—C14	0.2 (3)	C14—C1—N1—C18	74.2 (3)
C12—C13—C14—C1	179.6 (2)	C2—C1—N1—C15	68.1 (3)
C12—C13—C14—C5	0.9 (3)	C14—C1—N1—C15	−110.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.95	2.38	3.234 (3)	149
C6—H6···O1ⁱⁱ	0.95	2.49	3.357 (3)	152
C9—H9···O2ⁱⁱⁱ	0.95	2.53	3.465 (3)	167
C13—H13···O1^iv	0.95	2.70	3.471 (3)	139
C17—H17A···Cg2^v	0.99	2.92	3.709 (3)	138

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, z+1/2; (iii) x+1/2, −y+1/2, z; (iv) x, y−1, z; (v) x+1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃NO₂
M_r	275.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	18.4179 (9), 5.7697 (4), 12.4403 (6)
V (Å³)	1321.98 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.49 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10655, 1667, 1258
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.088, 0.95
No. of reflections	1667
No. of parameters	190
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: APEX2 (Bruker 2005), SAINT (Bruker 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and SCHAKAL99 (Keller, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.95	2.38	3.234 (3)	149
C6—H6···O1ⁱⁱ	0.95	2.49	3.357 (3)	152
C9—H9···O2ⁱⁱⁱ	0.95	2.53	3.465 (3)	167
C13—H13···O1^iv	0.95	2.70	3.471 (3)	139
C17—H17A···Cg2^v	0.99	2.92	3.709 (3)	138

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, z+1/2; (iii) x+1/2, −y+1/2, z; (iv) x, y−1, z; (v) x+1/2, −y+3/2, z.

Acknowledgements

This work was supported by the National Research Foundation, Pretoria (NRF, GUN 77122) and the University of the Witwatersrand.

References

Alston, P. V., Ottenbrite, R. M. & Newby, J. (1979). J. Org. Chem. 44, 4939–4943. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hubbard, J. L., Carl, J. M. III, Anderson, G. D. & Rankin, G. O. (1992). J. Heterocycl. Chem. 29, 719–721. CrossRef CAS Google Scholar
Kaplan, F. & Conroy, H. (1963). J. Org. Chem. 28, 1593–1596. CrossRef CAS Web of Science Google Scholar
Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany. Google Scholar
Meek, J. S., Wilgus, D. R. & Dann, J. R. (1960). J. Am. Chem. Soc. 82, 2566–2569. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, M. D. & Ningombom, A. (2010). Indian J. Chem. Sect. B, 49, 789–794. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Verma, S. M. & Singh, M. D. (1977). J. Org. Chem. 42, 3736–3740. CrossRef CAS Web of Science Google Scholar

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