Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Feb 17;68(Pt 3):o731. doi: 10.1107/S1600536812005831

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

Narsimha Reddy Penthala a, Sean Parkin b, Peter A Crooks a,*
PMCID: PMC3295502  PMID: 22412613

Abstract

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 ▶).graphic file with name e-68-0o731-scheme1.jpg

Experimental  

Crystal data  

  • C20H17NO4

  • M r = 335.35

  • Monoclinic, Inline graphic

  • 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[F 2 > 2σ(F 2)] = 0.064

  • wR(F 2) = 0.186

  • S = 1.02

  • 3790 reflections

  • 229 parameters

  • H-atom parameters constrained

  • Δρmax = 0.51 e Å−3

  • Δρmin = −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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005831/hg5136sup1.cif

e-68-0o731-sup1.cif (19.3KB, cif)

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

e-68-0o731-Isup2.hkl (185.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812005831/hg5136Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

H atoms were found in difference Fourier maps and subsequently placed in idealized positions with constrained distances of 0.98 Å (RCH3), 0.95 Å (Csp2H) and with Uiso(H) values set to either 1.2Ueq or 1.5Ueq (RCH3) of the attached atom.

Figures

Fig. 1.

Fig. 1.

Open in a new tab

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.

Crystal data

C20H17NO4 F(000) = 1408
Mr = 335.35 Dx = 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
Open in a new tab

Data collection

Nonius KappaCCD diffractometer 2183 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.085
Graphite monochromator θmax = 27.5°, θmin = 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
Open in a new tab

Refinement

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(Fo2) + (0.1061P)2] where P = (Fo2 + 2Fc2)/3
3790 reflections (Δ/σ)max < 0.001
229 parameters Δρmax = 0.51 e Å−3
0 restraints Δρmin = −0.35 e Å−3
Open in a new tab

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.
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.
Open in a new tab

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

x y z Uiso*/Ueq
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*
Open in a new tab

Atomic displacement parameters (Å2)

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)
Open in a new tab

Geometric parameters (Å, º)

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)
Open in a new tab

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5136).

References

  1. Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o521–o522.
  2. Naruto, S., Mizuta, H., Yoshida, T. & Uno, H. (1983). Chem. Pharm. Bull. 31, 3022–3032. [DOI] [PubMed]
  3. Nonius (1998). COLLECT Nonius BV, Delft, The Netherlands.
  4. Ohsumi, K., Nakagawa, R., Fukuda, Y. & Hatanaka, T. (1998). J. Med. Chem. 41, 3022–3032. [DOI] [PubMed]
  5. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  6. Parmar, V. S., Kumar, A., Prasad, A. K. & Singh, S. K. (1988). Bioorg. Med. Chem. 25, 911–914.
  7. Saczewski, F., Reszka, P., Gdaniec, M., Grunert, R. & Bednarski, P. I. (2004). J. Med. Chem. 47, 3438–3449. [DOI] [PubMed]
  8. Sanna, P., Carta, A. & Nikookar, M. E. R. (2000). Eur. J. Med. Chem. 35, 535–543. [DOI] [PubMed]
  9. Sanna, P., Carta, A. & Paglietti, G. (1999). Heterocycles, 51, 2171–2181.
  10. Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2302. [DOI] [PMC free article] [PubMed]
  11. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  12. Shiba, S. A. (1996). Phosphorus Sulfur Silicon Relat. Elem. 114, 29–37.
  13. Sonar, V. N., Parkin, S. & Crooks, P. A. (2007). Acta Cryst. C63, o743–o745. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005831/hg5136sup1.cif

e-68-0o731-sup1.cif (19.3KB, cif)

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

e-68-0o731-Isup2.hkl (185.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812005831/hg5136Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES