(Z)-3-(1-Benzofuran-2-yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylonitrile

Penthala, N.R.; Parkin, S.; Crooks, P.A.

doi:10.1107/S1600536812005831

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o731

doi:10.1107/S1600536812005831

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(Z)-3-(1-Benzofuran-2-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile

Narsimha Reddy Penthala,^a Sean Parkin ^b and Peter A. Crooks ^a ^*

^aDepartment of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA, and ^bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506, USA
^*Correspondence e-mail: pacrooks@uams.edu

(Received 4 November 2011; accepted 9 February 2012; online 17 February 2012)

In the title compound, C₂₀H₁₇NO₄, the double bond of the acrylonitrile group separating the 1-benzofuran moiety from the 3,4,5-trimethoxyphenyl ring has Z geometry. The 1-benzofuran groups are π–π stacked with inversion-related counterparts such that the furan ring centroid–centroid distance is 3.804 (5) Å. The dihedral angle between the planes of the trimethoxyphenyl ring and the acrylonitrile group is 24.2 (2)°.

Related literature

For the biological activity, see: Naruto et al. (1983 ); Parmar et al. (1988 ); Shiba (1996 ); Sanna et al. (1999 , 2000 ); Ohsumi et al. (1998 ); Saczewski et al. (2004 ). For similar structures, see: Choi et al. (2007 ); Seo et al. (2009 ); Sonar et al. (2007 ).

Experimental

Crystal data

C₂₀H₁₇NO₄
M_r = 335.35
Monoclinic, C 2/c
a = 28.0892 (5) Å
b = 6.9555 (1) Å
c = 20.0908 (4) Å
β = 122.678 (1)°
V = 3303.93 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 90 K
0.24 × 0.20 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer
26416 measured reflections
3790 independent reflections
2183 reflections with I > 2σ(I)
R_int = 0.085

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.186
S = 1.02
3790 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and local procedures.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005831/hg5136sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005831/hg5136Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005831/hg5136Isup3.cml

checkCIF report

Comment top

Acrylonitrile analogs that incorporate 1,2,4-triazole, benzimidazole, or 1,3,5-triazine heterocyclic groups have been found to possess interesting biological properties such as spasmolytic (Naruto et al., 1983), antioxidative (Parmar et al., 1988), insecticidal (Shiba, 1996), antitubercular (Sanna et al., 1999, 2000) and cytotoxic (Ohsumi et al., 1998; Saczewski et al., 2004) activities. From our previous studies, we reported the X-ray crystallographic data of two benzothiophene acrylonitrile analogs (Sonar et al., 2007). Based on this, and to compare the structure–activity relationships of different substituted acrylonitrile analogs, we have now prepared the title compound, (I), by the reaction of benzofuran-2-carbaldehyde with 2-(3,4,5-trimethoxyphenyl)acetonitrile in methanolic and sodium methoxide under reflux. The title compound was crystallized from the methanol. The molecular structure is shown in Fig.1. The 1-benzofuran ring is planar, with bond distances and angles comparable with those previously reported for other 1-benzofuran derivatives (Choi et al., 2007; Seo et al., 2009). The X-ray crystallographic studies revealed that the title compound is the Z isomer, since the 1-benzofuran ring is trans relative to the bulky 3,4,5-trimethoxy phenyl group. The 1-benzofuran groups are π—π stacked with inversion-related (1 - x, 1 - y, 1 - z) counterparts with a furan ring centroid—centroid distance of 3.804 (5) Å. Since the stacked benzofurans are inversion related, they are exactly parallel with perpendicular spacing of 3.409 (3) Å. The dihedral angle between the planes of the trimethoxy phenyl ring and the acrylonitrile group is 24.2 (2) Å.

Related literature top

For the biological activity, see: Naruto et al. (1983); Parmar et al. (1988); Shiba (1996); Sanna et al. (1999, 2000); Ohsumi et al. (1998); Saczewski et al. (2004). For similar structures, see: Choi et al. (2007); Seo et al. (2009); Sonar et al. (2007).

Experimental top

A mixture of benzofuran-2-carbaldehyde (0.3 g, 2.05 mmol), and 2-(3,4,5-trimethoxyphenyl)acetonitrile (0.45 g, 2.17 mmol) was refluxed in 5% methanolic sodium methoxide solution for 4 hrs. The reaction mixture was cooled to room temperature and added to ice cold water to afford a yellow crude solid, which was collected by filtration, washed with a 1:1 mixture of cold water and methanol, and suction–dried to afford the desired product. Crystallization from methanol gave a yellow crystalline product of (Z)-3-(benzofuran-2-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile that was suitable for X-ray crystallographic analysis. ¹H NMR (CDCl₃): δ 3.90 (s, 3H), 3.91 (s, 6H), 6.89 (s, 2H), 7.26–7.31 (dd, 1H), 7.36–7.40 (m, 1H), 7.41 (s, 1H), 7.50 (s, 1H),7.53–7.56(dd, 1H), 7.63–7. 65 (m, 1H); ¹³C NMR (CDCl₃): δ 56.53, 61.25, 103.30, 110.89, 111.10, 111.71, 117.60, 122.16, 123.81, 126.94, 127.66, 128.29, 129.17, 139.50, 151.21, 153.68, 155.20.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and local procedures.

Figures top

Fig. 1. A view of the molecular structure with displacement ellipsoids drawn at the 50% probability level and H atoms shown as small spheres of arbitrary radius.

(Z)-3-(1-Benzofuran-2-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile top

Crystal data top

C₂₀H₁₇NO₄	F(000) = 1408
M_r = 335.35	D_x = 1.348 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4101 reflections
a = 28.0892 (5) Å	θ = 1.0–27.5°
b = 6.9555 (1) Å	µ = 0.09 mm⁻¹
c = 20.0908 (4) Å	T = 90 K
β = 122.678 (1)°	Block, yellow
V = 3303.93 (10) Å³	0.24 × 0.20 × 0.14 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	2183 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.085
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
Detector resolution: 9.1 pixels mm^-1	h = −35→36
ω scans at fixed χ = 55°	k = −8→9
26416 measured reflections	l = −26→25
3790 independent 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1061P)²] where P = (F_o² + 2F_c²)/3
3790 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₁₇NO₄	V = 3303.93 (10) Å³
M_r = 335.35	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.0892 (5) Å	µ = 0.09 mm⁻¹
b = 6.9555 (1) Å	T = 90 K
c = 20.0908 (4) Å	0.24 × 0.20 × 0.14 mm
β = 122.678 (1)°

Data collection top

Nonius KappaCCD diffractometer	2183 reflections with I > 2σ(I)
26416 measured reflections	R_int = 0.085
3790 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.02	Δρ_max = 0.51 e Å⁻³
3790 reflections	Δρ_min = −0.35 e Å⁻³
229 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-value wR and goodness of fit S are based on F². Conventional R-values R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-values based on F² are statistically about twice as large as those based on F, and R-values 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
N1	0.48054 (9)	0.1350 (3)	0.63530 (12)	0.0314 (5)
O1	0.54675 (6)	0.4633 (2)	0.60175 (9)	0.0235 (4)
O2	0.28706 (6)	0.8492 (2)	0.58677 (9)	0.0236 (4)
O3	0.26167 (6)	0.5664 (2)	0.65217 (9)	0.0241 (4)
O4	0.33056 (7)	0.2610 (2)	0.71961 (10)	0.0267 (4)
C1	0.52309 (9)	0.6378 (3)	0.60312 (13)	0.0209 (5)
C2	0.58856 (9)	0.5094 (3)	0.58841 (12)	0.0205 (5)
C3	0.62441 (10)	0.3797 (3)	0.58480 (13)	0.0246 (6)
H3	0.6209	0.2451	0.5890	0.030*
C4	0.66571 (10)	0.4553 (3)	0.57475 (13)	0.0251 (6)
H4	0.6916	0.3717	0.5727	0.030*
C5	0.66959 (10)	0.6539 (4)	0.56754 (13)	0.0261 (6)
H5	0.6984	0.7025	0.5610	0.031*
C6	0.63306 (10)	0.7803 (4)	0.56964 (14)	0.0275 (6)
H6	0.6360	0.9145	0.5637	0.033*
C7	0.59119 (9)	0.7082 (3)	0.58073 (13)	0.0223 (5)
C8	0.54814 (10)	0.7870 (3)	0.59013 (13)	0.0238 (6)
H8	0.5388	0.9192	0.5877	0.029*
C9	0.47910 (9)	0.6394 (3)	0.61858 (13)	0.0224 (5)
H9	0.4655	0.7636	0.6198	0.027*
C10	0.45380 (9)	0.4932 (3)	0.63175 (12)	0.0195 (5)
C11	0.47002 (10)	0.2961 (3)	0.63316 (13)	0.0227 (5)
C12	0.40551 (9)	0.5193 (3)	0.64184 (12)	0.0192 (5)
C13	0.37106 (9)	0.6807 (3)	0.61109 (13)	0.0212 (5)
H13	0.3796	0.7790	0.5863	0.025*
C14	0.32409 (9)	0.6977 (3)	0.61670 (12)	0.0194 (5)
C15	0.31095 (9)	0.5540 (3)	0.65306 (12)	0.0203 (5)
C16	0.34635 (9)	0.3953 (3)	0.68529 (12)	0.0208 (5)
C17	0.39355 (9)	0.3767 (3)	0.68009 (13)	0.0217 (5)
H17	0.4176	0.2678	0.7024	0.026*
C18	0.29675 (10)	0.9924 (3)	0.54421 (13)	0.0260 (6)
H18A	0.3342	1.0497	0.5790	0.039*
H18B	0.2678	1.0926	0.5258	0.039*
H18C	0.2949	0.9330	0.4986	0.039*
C19	0.26949 (10)	0.6446 (4)	0.72368 (14)	0.0314 (6)
H19A	0.2982	0.5697	0.7691	0.047*
H19B	0.2337	0.6388	0.7211	0.047*
H19C	0.2819	0.7787	0.7296	0.047*
C20	0.36866 (10)	0.1064 (3)	0.75978 (14)	0.0260 (6)
H20A	0.3713	0.0270	0.7216	0.039*
H20B	0.3549	0.0278	0.7865	0.039*
H20C	0.4061	0.1578	0.7990	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0334 (13)	0.0259 (13)	0.0429 (13)	0.0016 (10)	0.0257 (11)	−0.0004 (10)
O1	0.0229 (9)	0.0234 (9)	0.0289 (9)	0.0020 (7)	0.0170 (8)	−0.0005 (7)
O2	0.0240 (9)	0.0228 (9)	0.0273 (9)	0.0060 (7)	0.0161 (8)	0.0043 (7)
O3	0.0194 (9)	0.0304 (10)	0.0251 (9)	0.0007 (7)	0.0136 (7)	−0.0019 (7)
O4	0.0247 (9)	0.0252 (10)	0.0334 (9)	0.0018 (7)	0.0178 (8)	0.0077 (7)
C1	0.0202 (12)	0.0174 (12)	0.0225 (12)	0.0031 (10)	0.0100 (10)	−0.0011 (10)
C2	0.0174 (12)	0.0239 (13)	0.0198 (12)	−0.0016 (10)	0.0097 (10)	−0.0023 (10)
C3	0.0281 (14)	0.0211 (13)	0.0274 (13)	0.0042 (11)	0.0168 (12)	−0.0002 (10)
C4	0.0224 (13)	0.0326 (15)	0.0208 (12)	0.0045 (11)	0.0121 (11)	0.0009 (11)
C5	0.0229 (13)	0.0344 (15)	0.0248 (13)	0.0004 (11)	0.0155 (11)	0.0016 (11)
C6	0.0293 (14)	0.0260 (14)	0.0326 (14)	−0.0035 (11)	0.0203 (12)	−0.0019 (11)
C7	0.0207 (12)	0.0231 (13)	0.0229 (12)	0.0009 (10)	0.0118 (10)	−0.0008 (10)
C8	0.0234 (13)	0.0187 (13)	0.0285 (13)	0.0028 (10)	0.0136 (11)	0.0001 (10)
C9	0.0206 (12)	0.0205 (13)	0.0258 (13)	0.0027 (10)	0.0123 (11)	−0.0033 (10)
C10	0.0204 (12)	0.0186 (12)	0.0193 (11)	0.0021 (10)	0.0107 (10)	−0.0001 (10)
C11	0.0218 (13)	0.0237 (14)	0.0273 (13)	0.0000 (11)	0.0163 (11)	−0.0001 (11)
C12	0.0180 (12)	0.0195 (12)	0.0184 (11)	−0.0021 (10)	0.0086 (10)	−0.0035 (10)
C13	0.0247 (13)	0.0192 (13)	0.0224 (12)	−0.0006 (10)	0.0144 (11)	0.0004 (10)
C14	0.0200 (12)	0.0184 (12)	0.0181 (11)	0.0013 (10)	0.0092 (10)	−0.0016 (9)
C15	0.0183 (12)	0.0229 (13)	0.0193 (12)	−0.0008 (10)	0.0100 (10)	−0.0024 (10)
C16	0.0229 (13)	0.0195 (13)	0.0193 (12)	−0.0038 (10)	0.0109 (11)	0.0001 (10)
C17	0.0215 (12)	0.0190 (13)	0.0204 (12)	0.0029 (10)	0.0086 (10)	0.0027 (10)
C18	0.0267 (13)	0.0260 (14)	0.0256 (13)	0.0037 (11)	0.0142 (11)	0.0023 (11)
C19	0.0293 (14)	0.0412 (16)	0.0279 (14)	0.0019 (12)	0.0181 (12)	−0.0012 (12)
C20	0.0320 (14)	0.0211 (13)	0.0271 (13)	0.0000 (11)	0.0173 (12)	0.0045 (10)

Geometric parameters (Å, º) top

N1—C11	1.154 (3)	C8—H8	0.9500
O1—C2	1.376 (3)	C9—C10	1.346 (3)
O1—C1	1.391 (3)	C9—H9	0.9500
O2—C14	1.371 (3)	C10—C11	1.440 (3)
O2—C18	1.431 (3)	C10—C12	1.487 (3)
O3—C15	1.377 (3)	C12—C13	1.390 (3)
O3—C19	1.438 (3)	C12—C17	1.402 (3)
O4—C16	1.370 (3)	C13—C14	1.388 (3)
O4—C20	1.421 (3)	C13—H13	0.9500
C1—C8	1.356 (3)	C14—C15	1.400 (3)
C1—C9	1.428 (3)	C15—C16	1.390 (3)
C2—C3	1.383 (3)	C16—C17	1.391 (3)
C2—C7	1.397 (3)	C17—H17	0.9500
C3—C4	1.384 (3)	C18—H18A	0.9800
C3—H3	0.9500	C18—H18B	0.9800
C4—C5	1.400 (3)	C18—H18C	0.9800
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.369 (3)	C19—H19B	0.9800
C5—H5	0.9500	C19—H19C	0.9800
C6—C7	1.403 (3)	C20—H20A	0.9800
C6—H6	0.9500	C20—H20B	0.9800
C7—C8	1.430 (3)	C20—H20C	0.9800

C2—O1—C1	105.54 (17)	C13—C12—C10	120.4 (2)
C14—O2—C18	116.95 (17)	C17—C12—C10	119.6 (2)
C15—O3—C19	113.60 (17)	C14—C13—C12	119.8 (2)
C16—O4—C20	116.92 (17)	C14—C13—H13	120.1
C8—C1—O1	111.17 (19)	C12—C13—H13	120.1
C8—C1—C9	129.5 (2)	O2—C14—C13	124.0 (2)
O1—C1—C9	119.36 (19)	O2—C14—C15	115.23 (19)
O1—C2—C3	125.5 (2)	C13—C14—C15	120.8 (2)
O1—C2—C7	110.68 (19)	O3—C15—C16	121.12 (19)
C3—C2—C7	123.8 (2)	O3—C15—C14	119.68 (19)
C2—C3—C4	116.8 (2)	C16—C15—C14	119.1 (2)
C2—C3—H3	121.6	O4—C16—C15	115.57 (19)
C4—C3—H3	121.6	O4—C16—C17	123.7 (2)
C3—C4—C5	120.6 (2)	C15—C16—C17	120.7 (2)
C3—C4—H4	119.7	C16—C17—C12	119.7 (2)
C5—C4—H4	119.7	C16—C17—H17	120.2
C6—C5—C4	122.0 (2)	C12—C17—H17	120.2
C6—C5—H5	119.0	O2—C18—H18A	109.5
C4—C5—H5	119.0	O2—C18—H18B	109.5
C5—C6—C7	118.8 (2)	H18A—C18—H18B	109.5
C5—C6—H6	120.6	O2—C18—H18C	109.5
C7—C6—H6	120.6	H18A—C18—H18C	109.5
C2—C7—C6	118.1 (2)	H18B—C18—H18C	109.5
C2—C7—C8	105.4 (2)	O3—C19—H19A	109.5
C6—C7—C8	136.5 (2)	O3—C19—H19B	109.5
C1—C8—C7	107.2 (2)	H19A—C19—H19B	109.5
C1—C8—H8	126.4	O3—C19—H19C	109.5
C7—C8—H8	126.4	H19A—C19—H19C	109.5
C10—C9—C1	130.3 (2)	H19B—C19—H19C	109.5
C10—C9—H9	114.8	O4—C20—H20A	109.5
C1—C9—H9	114.8	O4—C20—H20B	109.5
C9—C10—C11	121.9 (2)	H20A—C20—H20B	109.5
C9—C10—C12	123.5 (2)	O4—C20—H20C	109.5
C11—C10—C12	114.56 (19)	H20A—C20—H20C	109.5
N1—C11—C10	175.8 (2)	H20B—C20—H20C	109.5
C13—C12—C17	120.0 (2)

C2—O1—C1—C8	0.8 (2)	C9—C10—C12—C17	−159.1 (2)
C2—O1—C1—C9	−177.95 (18)	C11—C10—C12—C17	23.9 (3)
C1—O1—C2—C3	178.0 (2)	C17—C12—C13—C14	−1.6 (3)
C1—O1—C2—C7	−0.5 (2)	C10—C12—C13—C14	176.09 (19)
O1—C2—C3—C4	−176.8 (2)	C18—O2—C14—C13	3.0 (3)
C7—C2—C3—C4	1.5 (3)	C18—O2—C14—C15	−175.70 (18)
C2—C3—C4—C5	−0.9 (3)	C12—C13—C14—O2	−178.6 (2)
C3—C4—C5—C6	−0.4 (4)	C12—C13—C14—C15	0.0 (3)
C4—C5—C6—C7	1.1 (4)	C19—O3—C15—C16	85.9 (2)
O1—C2—C7—C6	177.78 (19)	C19—O3—C15—C14	−98.1 (2)
C3—C2—C7—C6	−0.8 (3)	O2—C14—C15—O3	4.1 (3)
O1—C2—C7—C8	0.0 (2)	C13—C14—C15—O3	−174.67 (19)
C3—C2—C7—C8	−178.5 (2)	O2—C14—C15—C16	−179.78 (19)
C5—C6—C7—C2	−0.6 (3)	C13—C14—C15—C16	1.5 (3)
C5—C6—C7—C8	176.3 (3)	C20—O4—C16—C15	−174.09 (19)
O1—C1—C8—C7	−0.8 (3)	C20—O4—C16—C17	7.6 (3)
C9—C1—C8—C7	177.8 (2)	O3—C15—C16—O4	−3.8 (3)
C2—C7—C8—C1	0.5 (3)	C14—C15—C16—O4	−179.84 (19)
C6—C7—C8—C1	−176.6 (3)	O3—C15—C16—C17	174.64 (19)
C8—C1—C9—C10	−179.9 (2)	C14—C15—C16—C17	−1.4 (3)
O1—C1—C9—C10	−1.3 (4)	O4—C16—C17—C12	178.18 (19)
C1—C9—C10—C11	0.9 (4)	C15—C16—C17—C12	−0.1 (3)
C1—C9—C10—C12	−175.8 (2)	C13—C12—C17—C16	1.6 (3)
C9—C10—C12—C13	23.2 (3)	C10—C12—C17—C16	−176.07 (19)
C11—C10—C12—C13	−153.8 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇NO₄
M_r	335.35
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	90
a, b, c (Å)	28.0892 (5), 6.9555 (1), 20.0908 (4)
β (°)	122.678 (1)
V (Å³)	3303.93 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.20 × 0.14

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26416, 3790, 2183
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.186, 1.02
No. of reflections	3790
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.35

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and local procedures.

Acknowledgements

This investigation was supported by NIH/National Cancer Institute grant No. RO1 CA140409.

References

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