N-(1,4-Dioxo-1,4-dihydro­naphthalen-2-yl)benzamide

Brandy, Y.; Butcher, R.J.; Bakare, O.

doi:10.1107/S1600536812034150

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages o2775-o2776

doi:10.1107/S1600536812034150

Open

access

N-(1,4-Dioxo-1,4-dihydronaphthalen-2-yl)benzamide

Yakini Brandy,^a Ray J. Butcher ^a ^* and Oladapo Bakare ^a

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 2 July 2012; accepted 31 July 2012; online 25 August 2012)

The title compound, C₁₇H₁₁NO₃, was an intermediate synthesized during bisacylation of 2-amino-1,4-naphthoquinone with benzoyl chloride. A mixture of block- and needle-shaped crystals were obtained after column chromatography. The block-shaped crystals were identified as the imide and the needles were the title amide. The naphthoquinone scaffold is roughly planar (r.m.s. deviation = 0.047 Å for the C atoms). The N—H and C=O bonds of the amide group are anti to each other. A dihedral angle between the naphthoquinone ring system and the amide group of 3.56 (3)°, accompanied by a dihedral angle between the amide group and the phenyl group of 9.51 (3)°, makes the naphthoquinone ring essentially coplanar with the phenyl ring [dihedral angle = 7.12 (1)°]. In the crystal, molecules are linked by a weak N—H⋯O hydrogen bond and by two weak C—H⋯O interactions leading to the formation of zigzag chains along [010].

Related literature

For similar crystal structures, see: Brandy et al. (2009 , 2012 ); Akinboye et al. (2009a ,b ). For the pharmacological properties of related compounds, see: Bakare et al. (2003 ); Berhe et al. (2008 ); Lien et al. (1997 ); Huang, et al. (2005 ); Khraiwesh et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₁NO₃
M_r = 277.27
Monoclinic, P 2₁ /n
a = 6.9433 (3) Å
b = 12.0112 (4) Å
c = 15.2129 (5) Å
β = 94.129 (3)°
V = 1265.42 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.83 mm⁻¹
T = 123 K
0.67 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.819, T_max = 1.000
4550 measured reflections
2553 independent reflections
2123 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.148
S = 1.05
2553 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.88	2.65	3.3299 (19)	135
C4—H4A⋯O3ⁱ	0.95	2.49	3.149 (2)	127
C17—H17A⋯O2ⁱ	0.95	2.57	3.404 (2)	146
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812034150/bt5965sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034150/bt5965Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034150/bt5965Isup3.cml

checkCIF report

Comment top

Amido and imidonaphthoquinones are known for their anti-inflammatory, antiplatelet, antiallergic, antiparasitic and anticancer activities (Lien et al.(1997); Huang et al. (2005); Bakare et al. (2003), Khraiwesh et al. (2011)). During imide synthesis (2-N-bis(benzoyl)amino-1,4-naphthoquinone (Brandy et al. (2012)), we obtained the intermediate amido analog, 2-N-benzoylamino-1,4-naphthoquinone. In order to eventually perform an anticancer SAR (structure-activity relationship) study, these intermediate amido analogs were isolated, crystallized and subjected to an X-ray diffraction study.

This showed that the naphthoquinone scaffold was planar with N—H and C=O bonds anti to each other. A dihedral angle between the naphthoquinone ring and the amide group of -2.6 (3)°, accompanied with the dihedral angle between the amide group and the phenyl group of -8.8 (2)° makes the naphthoquinone ring coplanar to the phenyl group. The bond distances and angles are similar to those found in related structures (Brandy et al., 2009, 2012; Akinboye et al., 2009a, 2009b). The crystal packing pattern results from N—H···O hydrogen bonds along with two weak intermolecular C—H···O interactions.

Related literature top

For similar crystal structures, see: Brandy et al. (2009, 2012); Akinboye et al. (2009a,b). For the pharmacological properties of related compounds, see: Bakare et al. (2003); Berhe et al. (2008); Lien et al. (1997); Huang, et al. (2005); Khraiwesh et al. (2011).

Experimental top

2-Amino-1,4-naphthoquinone (318 mg, 1.83 mmol) was dissolved in freshly distilled THF (15 ml). NaH (115 mg, 4.78 mmol) was added and the mixture was stirred at room temperature for 15 min. The appropriate benzoyl chloride (0.55 ml, 4.74 mmol) was added, drop wise, and the mixture was stirred for 24 h. THF was evaporated under vacuum and the mixture was washed with ice-water (10 g ice in 10 ml water). The ice-water mixture was extracted with CH₂Cl₂ (30 ml, 20 ml consecutively) and the combined organic phase washed with water (3 x 20 ml), saturated NaCl solution (20 ml), then dried over anhydrous MgSO₄. The crude was purified via triturating in ethanol (2 ml) and column chromatography with an eluent mixture of ethyl acetate and hexane to furnish the amide (39 mg, 7.7%). A mixure of block and needle crystals were obtained from column chromatography. The block crystals were identified as the imide (Brandy et al., 2012) and the needles were identified as the amide. The needle crystals were hand-picked from the mixture and analyzed by X-ray diffraction.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Diagram of C₁₇H₁₁NO₃ showing the atom labeling. Displacement ellipsoids are at the 30% probability level.

Fig. 2. The molecular packing for C₁₇H₁₁NO₃ viewed along the a axis.

N-(1,4-Dioxo-1,4-dihydronaphthalen-2-yl)benzamide top

Crystal data top

C₁₇H₁₁NO₃	F(000) = 576
M_r = 277.27	D_x = 1.455 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 6.9433 (3) Å	Cell parameters from 1585 reflections
b = 12.0112 (4) Å	θ = 2.9–75.6°
c = 15.2129 (5) Å	µ = 0.83 mm⁻¹
β = 94.129 (3)°	T = 123 K
V = 1265.42 (8) Å³	Needle, pale yellow orange
Z = 4	0.67 × 0.12 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2553 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2123 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 10.5081 pixels mm^-1	θ_max = 75.7°, θ_min = 4.7°
ω scans	h = −7→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −14→14
T_min = 0.819, T_max = 1.000	l = −18→18
4550 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0937P)²] where P = (F_o² + 2F_c²)/3
2553 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₁₁NO₃	V = 1265.42 (8) Å³
M_r = 277.27	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 6.9433 (3) Å	µ = 0.83 mm⁻¹
b = 12.0112 (4) Å	T = 123 K
c = 15.2129 (5) Å	0.67 × 0.12 × 0.08 mm
β = 94.129 (3)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2553 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	2123 reflections with I > 2σ(I)
T_min = 0.819, T_max = 1.000	R_int = 0.037
4550 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.05	Δρ_max = 0.25 e Å⁻³
2553 reflections	Δρ_min = −0.25 e Å⁻³
190 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.

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
O1	0.4411 (2)	0.09807 (11)	0.24463 (8)	0.0373 (3)
O2	0.3847 (2)	0.51857 (10)	0.13486 (8)	0.0348 (3)
O3	0.3674 (2)	0.41588 (11)	0.43416 (8)	0.0354 (3)
N1	0.3825 (2)	0.24883 (12)	0.36581 (9)	0.0273 (3)
H1A	0.3821	0.1763	0.3741	0.033*
C1	0.3905 (2)	0.28621 (14)	0.27989 (10)	0.0253 (4)
C2	0.4119 (2)	0.19196 (14)	0.21661 (10)	0.0269 (4)
C3	0.3957 (2)	0.21822 (14)	0.12102 (10)	0.0252 (4)
C4	0.3886 (2)	0.13177 (15)	0.05992 (11)	0.0299 (4)
H4A	0.3960	0.0566	0.0793	0.036*
C5	0.3707 (2)	0.15588 (15)	−0.02938 (11)	0.0314 (4)
H5A	0.3629	0.0971	−0.0713	0.038*
C6	0.3641 (2)	0.26586 (16)	−0.05777 (11)	0.0320 (4)
H6A	0.3547	0.2820	−0.1191	0.038*
C7	0.3713 (2)	0.35219 (15)	0.00297 (11)	0.0290 (4)
H7A	0.3670	0.4272	−0.0168	0.035*
C8	0.3848 (2)	0.32888 (14)	0.09291 (10)	0.0251 (4)
C9	0.3872 (2)	0.42102 (14)	0.15843 (10)	0.0266 (4)
C10	0.3855 (2)	0.39248 (14)	0.25204 (10)	0.0270 (4)
H10A	0.3807	0.4506	0.2942	0.032*
C11	0.3750 (2)	0.31531 (14)	0.43956 (10)	0.0261 (3)
C12	0.3814 (2)	0.25771 (14)	0.52731 (10)	0.0252 (4)
C13	0.4058 (2)	0.32638 (15)	0.60106 (11)	0.0294 (4)
H13A	0.4142	0.4047	0.5938	0.035*
C14	0.4181 (3)	0.28079 (16)	0.68528 (11)	0.0324 (4)
H14A	0.4353	0.3279	0.7354	0.039*
C15	0.4050 (2)	0.16642 (16)	0.69612 (11)	0.0316 (4)
H15A	0.4137	0.1352	0.7536	0.038*
C16	0.3794 (2)	0.09777 (15)	0.62296 (11)	0.0308 (4)
H16A	0.3694	0.0195	0.6306	0.037*
C17	0.3681 (2)	0.14279 (15)	0.53839 (11)	0.0286 (4)
H17A	0.3514	0.0954	0.4884	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0618 (8)	0.0246 (7)	0.0265 (6)	0.0064 (6)	0.0101 (5)	0.0045 (5)
O2	0.0576 (7)	0.0236 (6)	0.0238 (6)	−0.0019 (5)	0.0080 (5)	0.0045 (5)
O3	0.0604 (8)	0.0235 (6)	0.0221 (6)	0.0007 (5)	0.0030 (5)	0.0025 (5)
N1	0.0412 (7)	0.0216 (7)	0.0196 (7)	0.0017 (5)	0.0047 (5)	0.0045 (5)
C1	0.0299 (7)	0.0271 (8)	0.0192 (7)	0.0005 (6)	0.0037 (5)	0.0022 (6)
C2	0.0352 (7)	0.0234 (8)	0.0226 (8)	0.0011 (6)	0.0057 (6)	0.0038 (6)
C3	0.0302 (7)	0.0258 (8)	0.0202 (7)	−0.0002 (6)	0.0059 (5)	0.0011 (6)
C4	0.0380 (8)	0.0253 (8)	0.0271 (8)	−0.0008 (6)	0.0084 (6)	−0.0007 (6)
C5	0.0392 (8)	0.0315 (9)	0.0241 (8)	0.0001 (7)	0.0060 (6)	−0.0057 (7)
C6	0.0365 (8)	0.0393 (10)	0.0208 (7)	0.0005 (7)	0.0057 (6)	0.0008 (7)
C7	0.0369 (8)	0.0294 (9)	0.0211 (8)	0.0007 (7)	0.0054 (6)	0.0035 (6)
C8	0.0288 (7)	0.0260 (9)	0.0208 (7)	0.0001 (6)	0.0042 (5)	0.0025 (6)
C9	0.0349 (7)	0.0239 (8)	0.0214 (7)	−0.0006 (6)	0.0043 (6)	0.0037 (6)
C10	0.0378 (8)	0.0250 (8)	0.0184 (7)	−0.0014 (6)	0.0041 (6)	0.0010 (6)
C11	0.0325 (7)	0.0265 (8)	0.0195 (7)	0.0004 (6)	0.0027 (6)	0.0029 (6)
C12	0.0289 (7)	0.0270 (8)	0.0201 (8)	0.0007 (6)	0.0037 (6)	0.0046 (6)
C13	0.0373 (8)	0.0286 (9)	0.0227 (8)	0.0001 (6)	0.0045 (6)	0.0017 (6)
C14	0.0403 (9)	0.0382 (10)	0.0191 (7)	−0.0006 (7)	0.0048 (6)	−0.0015 (6)
C15	0.0351 (8)	0.0412 (10)	0.0187 (7)	0.0001 (7)	0.0032 (6)	0.0077 (7)
C16	0.0390 (8)	0.0287 (9)	0.0247 (8)	−0.0003 (7)	0.0034 (6)	0.0070 (7)
C17	0.0373 (8)	0.0282 (9)	0.0202 (7)	0.0002 (6)	0.0024 (6)	0.0017 (6)

Geometric parameters (Å, º) top

O1—C2	1.217 (2)	C7—C8	1.393 (2)
O2—C9	1.225 (2)	C7—H7A	0.9500
O3—C11	1.212 (2)	C8—C9	1.489 (2)
N1—C11	1.381 (2)	C9—C10	1.466 (2)
N1—C1	1.3869 (19)	C10—H10A	0.9500
N1—H1A	0.8800	C11—C12	1.501 (2)
C1—C10	1.345 (2)	C12—C13	1.393 (2)
C1—C2	1.500 (2)	C12—C17	1.394 (2)
C2—C3	1.484 (2)	C13—C14	1.390 (2)
C3—C4	1.392 (2)	C13—H13A	0.9500
C3—C8	1.397 (2)	C14—C15	1.387 (3)
C4—C5	1.386 (2)	C14—H14A	0.9500
C4—H4A	0.9500	C15—C16	1.386 (3)
C5—C6	1.390 (3)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C17	1.393 (2)
C6—C7	1.387 (2)	C16—H16A	0.9500
C6—H6A	0.9500	C17—H17A	0.9500

C11—N1—C1	125.79 (14)	O2—C9—C10	120.48 (15)
C11—N1—H1A	117.1	O2—C9—C8	121.05 (14)
C1—N1—H1A	117.1	C10—C9—C8	118.44 (14)
C10—C1—N1	127.04 (15)	C1—C10—C9	121.76 (15)
C10—C1—C2	121.04 (14)	C1—C10—H10A	119.1
N1—C1—C2	111.90 (14)	C9—C10—H10A	119.1
O1—C2—C3	122.60 (16)	O3—C11—N1	121.69 (14)
O1—C2—C1	119.73 (14)	O3—C11—C12	121.20 (15)
C3—C2—C1	117.67 (14)	N1—C11—C12	117.10 (15)
C4—C3—C8	120.45 (15)	C13—C12—C17	119.61 (14)
C4—C3—C2	119.49 (15)	C13—C12—C11	115.94 (15)
C8—C3—C2	120.05 (15)	C17—C12—C11	124.45 (15)
C5—C4—C3	119.67 (16)	C14—C13—C12	120.32 (16)
C5—C4—H4A	120.2	C14—C13—H13A	119.8
C3—C4—H4A	120.2	C12—C13—H13A	119.8
C4—C5—C6	120.13 (16)	C15—C14—C13	119.96 (16)
C4—C5—H5A	119.9	C15—C14—H14A	120.0
C6—C5—H5A	119.9	C13—C14—H14A	120.0
C7—C6—C5	120.31 (15)	C16—C15—C14	119.95 (15)
C7—C6—H6A	119.8	C16—C15—H15A	120.0
C5—C6—H6A	119.8	C14—C15—H15A	120.0
C6—C7—C8	120.04 (16)	C15—C16—C17	120.41 (17)
C6—C7—H7A	120.0	C15—C16—H16A	119.8
C8—C7—H7A	120.0	C17—C16—H16A	119.8
C7—C8—C3	119.36 (16)	C16—C17—C12	119.75 (16)
C7—C8—C9	120.32 (15)	C16—C17—H17A	120.1
C3—C8—C9	120.32 (14)	C12—C17—H17A	120.1

C11—N1—C1—C10	−2.6 (3)	C3—C8—C9—O2	177.33 (15)
C11—N1—C1—C2	175.82 (14)	C7—C8—C9—C10	175.06 (14)
C10—C1—C2—O1	170.53 (16)	C3—C8—C9—C10	−4.8 (2)
N1—C1—C2—O1	−8.0 (2)	N1—C1—C10—C9	−177.44 (15)
C10—C1—C2—C3	−9.6 (2)	C2—C1—C10—C9	4.3 (2)
N1—C1—C2—C3	171.88 (13)	O2—C9—C10—C1	−179.15 (15)
O1—C2—C3—C4	8.5 (2)	C8—C9—C10—C1	3.0 (2)
C1—C2—C3—C4	−171.42 (14)	C1—N1—C11—O3	2.9 (3)
O1—C2—C3—C8	−172.50 (15)	C1—N1—C11—C12	−175.70 (14)
C1—C2—C3—C8	7.6 (2)	O3—C11—C12—C13	−8.8 (2)
C8—C3—C4—C5	0.1 (2)	N1—C11—C12—C13	169.78 (14)
C2—C3—C4—C5	179.07 (15)	O3—C11—C12—C17	172.36 (16)
C3—C4—C5—C6	1.4 (3)	N1—C11—C12—C17	−9.0 (2)
C4—C5—C6—C7	−1.4 (2)	C17—C12—C13—C14	0.4 (2)
C5—C6—C7—C8	−0.1 (2)	C11—C12—C13—C14	−178.52 (15)
C6—C7—C8—C3	1.6 (2)	C12—C13—C14—C15	−0.3 (2)
C6—C7—C8—C9	−178.34 (14)	C13—C14—C15—C16	−0.2 (3)
C4—C3—C8—C7	−1.5 (2)	C14—C15—C16—C17	0.5 (3)
C2—C3—C8—C7	179.46 (14)	C15—C16—C17—C12	−0.5 (2)
C4—C3—C8—C9	178.37 (14)	C13—C12—C17—C16	0.0 (2)
C2—C3—C8—C9	−0.6 (2)	C11—C12—C17—C16	178.79 (15)
C7—C8—C9—O2	−2.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.88	2.65	3.3299 (19)	135
C4—H4A···O3ⁱ	0.95	2.49	3.149 (2)	127
C17—H17A···O2ⁱ	0.95	2.57	3.404 (2)	146

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁NO₃
M_r	277.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	6.9433 (3), 12.0112 (4), 15.2129 (5)
β (°)	94.129 (3)
V (Å³)	1265.42 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.67 × 0.12 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.819, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4550, 2553, 2123
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.148, 1.05
No. of reflections	2553
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.25

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.88	2.65	3.3299 (19)	135.3
C4—H4A···O3ⁱ	0.95	2.49	3.149 (2)	126.7
C17—H17A···O2ⁱ	0.95	2.57	3.404 (2)	146.4

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer. We also acknowledge MRI grant No. CHE-1126533 from the National Science Foundation for the purchase of a TOF LC/MS system used in this study and also funded in part by grant No. 5-U54—CA914–31 (Howard University/Johns Hopkins Cancer Center Partnership).

References

Akinboye, E. S., Butcher, R. J., Brandy, Y., Adesiyun, T. A. & Bakare, O. (2009a). Acta Cryst. E65, o24. Web of Science CSD CrossRef IUCr Journals Google Scholar
Akinboye, E. S., Butcher, R. J., Wright, D. A., Brandy, Y. & Bakare, O. (2009b). Acta Cryst. E65, o277. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bakare, O., Ashendel, C. L., Peng, H., Zalkow, L. H. & Burgess, E. M. (2003). Bioorg. Med. Chem. 11, 3165–3170. Web of Science CrossRef PubMed CAS Google Scholar
Berhe, S., Kanaan, Y., Copeland, R. L., Wright, D. A., Zalkow, L. H. & Bakare, O. (2008). Lett. Drug. Des. Discov. 5, 485–488. CrossRef CAS Google Scholar
Brandy, Y., Butcher, R. J., Adesiyun, T. A., Berhe, S. & Bakare, O. (2009). Acta Cryst. E65, o64. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandy, Y., Butcher, R. J. & Bakare, O. (2012). Acta Cryst. E68, o2379. CSD CrossRef IUCr Journals Google Scholar
Huang, L., Chang, F., Lee, K., Wang, J., Teng, C. & Kuo, S. (2005). Bioorg. Med. Chem. 6, 2261–2269. Web of Science CrossRef Google Scholar
Khraiwesh, H. M., Lee, C. M., Brandy, Y., Akinboye, E. S., Berhe, S., Gittens, G., Abbas, M. M., Ampy, F. R., Ashraf, M. & Bakare, O. (2011). Arch. Pharm. Res. 35, 27–33. Web of Science CrossRef Google Scholar
Lien, J., Huang, L., Wang, J., Teng, C., Lee, K. & Kuo, S. (1997). Bioorg. Med. Chem. 5, 2111–2120. Web of Science CrossRef CAS PubMed Google Scholar
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar