organic compounds
4-(4-Iodoanilino)-2-methylene-4-oxobutanoic acid
aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India, bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
*Correspondence e-mail: richard.betz@webmail.co.za
In the title compound, C11H10INO3, an addition product of itaconic acid anhydride and 4-iodoaniline, the least-squares planes defined by the atoms of the aromatic moiety and the non-H atoms of the carboxylic acid group enclose an angle of 74.82 (11)°. In the crystal, classical O—H⋯O hydrogen bonds formed by carboxylic groups, as well as N—H⋯O hydrogen bonds formed by amide groups, are present along with C—H⋯O contacts. Together, these connect the molecules into dimeric chains along the b-axis direction.
Related literature
For applications of itaconic acid anhydride, see: Oishi (1980); Urzua et al. (1998); Shetgiri & Nayak (2005); Katla et al. (2011); Hanoon (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2010); cell SAINT (Bruker, 2010); 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, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S160053681205012X/gk2533sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: https://doi.org/10.1107/S160053681205012X/gk2533Isup2.cdx
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681205012X/gk2533Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681205012X/gk2533Isup4.cml
Itaconic anhydride (0.112 g, 1 mmol) was dissolved in acetone (30 ml) and 4-iodoaniline (0.219 g, 1 mmol) was added in small portions under stirring at room temperature over a timespan of 30 minutes. The mixture turned into a yellow slurry. Stirring was continued for 1.5 h after which the slurry was filtered and the solid obtained was washed with acetone and dried to yield the title compound. Single crystals suitable for the X-ray diffraction study were grown from methanol by slow evaporation at room temperature.
Carbon-bound H atoms were placed in calculated positions (C–H 0.95 Å for aromatic and vinylic carbon atoms, C–H 0.99 Å for methylene groups) and were included in the
in the riding model approximation, with U(H) set to 1.2Ueq(C). The H atom of the hydroxyl group was allowed to rotate with a fixed angle around the C–O bond to best fit the experimental electron density (HFIX 147 in the SHELX program suite (Sheldrick, 2008)), with U(H) set to 1.5Ueq(O). The nitrogen-bound H atom was located on a difference Fourier map and refined freely.Itaconic acid anhydride is a monomeric building block obtained from renewable sources. Copolymers containing both hydrophilic and hydrophobic segments are drawing considerable attention because of their possible use in biological systems. In this aspect, N-substituted itaconamic acid derivatives have attracted attention due to their
properties. Being more reactive than maleic anhydride, itaconic anhydride has already been applied for introducing polar functional groups into polymers (Oishi, 1980; Urzua et al.,1998). In addition, the basic skeleton of itaconic anhydride is useful for the synthesis of cyclic derivatives of (Shetgiri & Nayak, 2005), pyridazines (Katla et al., 2011), oxazepines and diazepines (Hanoon, 2011) which show pharmacological activity. In continuation of our studies of pharmacologically active compounds, the of the title compound was determined.The C=C bond is present as its anti-Saytzeff tautomer. The N–C(=O) bond length of 1.351 (2) Å is indicative of amide-type resonance. The least-squares plane defined by the atoms of the aromatic moiety on the one hand and the non-hydrogen atoms of the carboxylic acid group on the other hand enclose an angle of 74.82 (11) ° (Fig. 1).
In the crystal, C–H···O contatcs whose range falls by more than 0.1 Å below the sum of van-der-Waals radii are observed next to classical hydrogen bonds of the N–H···O and C–H···O type. The N–H···O hydrogen bonds are supported by the carbonyl oxygen atom of the amide functionality as acceptor. Simultaneously, one of the hydrogen atoms of the methylene group forms a C–H···O contact to the same oxygen atom which, therefore, acts as twofold acceptor. The carboxylic acid groups engage in the common dimeric hydrogen bonding pattern frequently encountered for many
In total, the molecules are connected to dimeric chains along the crystallographic b axis. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is C11(4)C11(4)R22(8) on the unary level. The shortest intercentroid distance between two aromatic systems was found at 4.7863 (11) Å which is about the length of axis b (Fig. 2).The packing of the title compound in the
is shown in Figure 3.For applications of itaconic acid anhydride, see: Oishi (1980); Urzua et al. (1998); Shetgiri & Nayak (2005); Katla et al. (2011); Hanoon (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C11H10INO3 | F(000) = 640 |
Mr = 331.10 | Dx = 1.921 Mg m−3 |
Monoclinic, P21/c | Melting point = 447–445 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 23.1111 (6) Å | Cell parameters from 9343 reflections |
b = 4.7863 (1) Å | θ = 2.7–28.3° |
c = 10.4262 (2) Å | µ = 2.79 mm−1 |
β = 97.071 (1)° | T = 200 K |
V = 1144.54 (4) Å3 | Rectangular, colourless |
Z = 4 | 0.29 × 0.16 × 0.10 mm |
Bruker APEXII CCD diffractometer | 2839 independent reflections |
Radiation source: fine-focus sealed tube | 2612 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
φ and ω scans | θmax = 28.3°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −30→30 |
Tmin = 0.503, Tmax = 0.776 | k = −6→6 |
12435 measured reflections | l = −8→13 |
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)] = 0.018 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0202P)2 + 0.979P] where P = (Fo2 + 2Fc2)/3 |
2839 reflections | (Δ/σ)max = 0.002 |
150 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.61 e Å−3 |
C11H10INO3 | V = 1144.54 (4) Å3 |
Mr = 331.10 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 23.1111 (6) Å | µ = 2.79 mm−1 |
b = 4.7863 (1) Å | T = 200 K |
c = 10.4262 (2) Å | 0.29 × 0.16 × 0.10 mm |
β = 97.071 (1)° |
Bruker APEXII CCD diffractometer | 2839 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2612 reflections with I > 2σ(I) |
Tmin = 0.503, Tmax = 0.776 | Rint = 0.015 |
12435 measured reflections |
R[F2 > 2σ(F2)] = 0.018 | 0 restraints |
wR(F2) = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.73 e Å−3 |
2839 reflections | Δρmin = −0.61 e Å−3 |
150 parameters |
x | y | z | Uiso*/Ueq | ||
I1 | 0.056006 (5) | −0.19408 (3) | 0.680940 (13) | 0.03784 (5) | |
O1 | 0.48205 (6) | −0.1867 (3) | 0.34828 (13) | 0.0334 (3) | |
H1 | 0.5045 | −0.1852 | 0.4180 | 0.050* | |
O2 | 0.43726 (6) | 0.1500 (3) | 0.44728 (13) | 0.0335 (3) | |
O3 | 0.30129 (6) | −0.2166 (2) | 0.35760 (14) | 0.0301 (3) | |
N1 | 0.26626 (6) | 0.2123 (3) | 0.39810 (15) | 0.0238 (3) | |
H71 | 0.2679 (10) | 0.382 (5) | 0.380 (2) | 0.031 (6)* | |
C1 | 0.43994 (7) | −0.0058 (4) | 0.35485 (16) | 0.0232 (3) | |
C2 | 0.39444 (7) | 0.0026 (3) | 0.24115 (16) | 0.0225 (3) | |
C3 | 0.34191 (7) | 0.1767 (3) | 0.25648 (16) | 0.0232 (3) | |
H3A | 0.3198 | 0.2104 | 0.1703 | 0.028* | |
H3B | 0.3547 | 0.3601 | 0.2937 | 0.028* | |
C4 | 0.30202 (7) | 0.0375 (3) | 0.34331 (15) | 0.0202 (3) | |
C5 | 0.40223 (8) | −0.1299 (4) | 0.13366 (18) | 0.0330 (4) | |
H5A | 0.4371 | −0.2318 | 0.1286 | 0.040* | |
H5B | 0.3729 | −0.1235 | 0.0614 | 0.040* | |
C11 | 0.21964 (7) | 0.1204 (3) | 0.46527 (16) | 0.0218 (3) | |
C12 | 0.22773 (7) | −0.0842 (4) | 0.55994 (17) | 0.0263 (3) | |
H12 | 0.2652 | −0.1644 | 0.5823 | 0.032* | |
C13 | 0.18104 (8) | −0.1721 (4) | 0.62227 (18) | 0.0284 (4) | |
H13 | 0.1864 | −0.3137 | 0.6865 | 0.034* | |
C14 | 0.12659 (7) | −0.0515 (4) | 0.58994 (16) | 0.0265 (3) | |
C15 | 0.11850 (8) | 0.1576 (4) | 0.49805 (19) | 0.0308 (4) | |
H15 | 0.0813 | 0.2421 | 0.4777 | 0.037* | |
C16 | 0.16521 (8) | 0.2432 (4) | 0.43571 (18) | 0.0290 (4) | |
H16 | 0.1599 | 0.3867 | 0.3724 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02465 (7) | 0.04793 (9) | 0.04370 (9) | −0.00628 (5) | 0.01530 (5) | −0.00051 (6) |
O1 | 0.0276 (6) | 0.0373 (7) | 0.0342 (7) | 0.0105 (5) | −0.0003 (5) | −0.0044 (6) |
O2 | 0.0336 (7) | 0.0386 (8) | 0.0276 (6) | 0.0087 (6) | 0.0003 (5) | −0.0064 (5) |
O3 | 0.0333 (7) | 0.0172 (5) | 0.0428 (7) | 0.0000 (5) | 0.0167 (6) | 0.0006 (5) |
N1 | 0.0239 (7) | 0.0160 (6) | 0.0331 (7) | 0.0002 (5) | 0.0096 (6) | 0.0033 (6) |
C1 | 0.0217 (7) | 0.0230 (7) | 0.0258 (7) | 0.0002 (6) | 0.0066 (6) | 0.0026 (6) |
C2 | 0.0204 (7) | 0.0216 (7) | 0.0262 (7) | −0.0017 (6) | 0.0060 (6) | 0.0036 (6) |
C3 | 0.0205 (7) | 0.0223 (8) | 0.0274 (8) | 0.0007 (6) | 0.0050 (6) | 0.0052 (6) |
C4 | 0.0179 (7) | 0.0194 (7) | 0.0230 (7) | −0.0010 (5) | 0.0011 (5) | 0.0009 (6) |
C5 | 0.0271 (9) | 0.0400 (10) | 0.0320 (9) | 0.0016 (7) | 0.0040 (7) | −0.0066 (8) |
C11 | 0.0201 (7) | 0.0201 (7) | 0.0261 (7) | −0.0020 (6) | 0.0064 (6) | −0.0024 (6) |
C12 | 0.0194 (7) | 0.0279 (8) | 0.0318 (8) | 0.0017 (6) | 0.0046 (6) | 0.0035 (7) |
C13 | 0.0251 (8) | 0.0316 (9) | 0.0294 (8) | −0.0007 (7) | 0.0072 (7) | 0.0045 (7) |
C14 | 0.0194 (7) | 0.0323 (9) | 0.0291 (8) | −0.0046 (6) | 0.0083 (6) | −0.0042 (7) |
C15 | 0.0182 (7) | 0.0390 (10) | 0.0356 (9) | 0.0038 (7) | 0.0055 (7) | 0.0012 (8) |
C16 | 0.0246 (8) | 0.0306 (9) | 0.0324 (9) | 0.0044 (7) | 0.0060 (7) | 0.0070 (7) |
I1—C14 | 2.0994 (16) | C3—H3B | 0.9900 |
O1—C1 | 1.311 (2) | C5—H5A | 0.9500 |
O1—H1 | 0.8400 | C5—H5B | 0.9500 |
O2—C1 | 1.226 (2) | C11—C12 | 1.387 (2) |
O3—C4 | 1.2258 (19) | C11—C16 | 1.388 (2) |
N1—C4 | 1.351 (2) | C12—C13 | 1.392 (2) |
N1—C11 | 1.425 (2) | C12—H12 | 0.9500 |
N1—H71 | 0.83 (2) | C13—C14 | 1.388 (2) |
C1—C2 | 1.485 (2) | C13—H13 | 0.9500 |
C2—C5 | 1.319 (2) | C14—C15 | 1.382 (3) |
C2—C3 | 1.497 (2) | C15—C16 | 1.389 (3) |
C3—C4 | 1.523 (2) | C15—H15 | 0.9500 |
C3—H3A | 0.9900 | C16—H16 | 0.9500 |
C1—O1—H1 | 109.5 | C2—C5—H5B | 120.0 |
C4—N1—C11 | 123.75 (14) | H5A—C5—H5B | 120.0 |
C4—N1—H71 | 117.5 (16) | C12—C11—C16 | 119.74 (15) |
C11—N1—H71 | 117.8 (16) | C12—C11—N1 | 121.60 (15) |
O2—C1—O1 | 123.55 (16) | C16—C11—N1 | 118.65 (15) |
O2—C1—C2 | 120.76 (15) | C11—C12—C13 | 120.12 (16) |
O1—C1—C2 | 115.69 (15) | C11—C12—H12 | 119.9 |
C5—C2—C1 | 120.52 (16) | C13—C12—H12 | 119.9 |
C5—C2—C3 | 123.74 (16) | C14—C13—C12 | 119.52 (16) |
C1—C2—C3 | 115.70 (14) | C14—C13—H13 | 120.2 |
C2—C3—C4 | 112.22 (13) | C12—C13—H13 | 120.2 |
C2—C3—H3A | 109.2 | C15—C14—C13 | 120.72 (16) |
C4—C3—H3A | 109.2 | C15—C14—I1 | 120.15 (13) |
C2—C3—H3B | 109.2 | C13—C14—I1 | 119.13 (13) |
C4—C3—H3B | 109.2 | C14—C15—C16 | 119.43 (16) |
H3A—C3—H3B | 107.9 | C14—C15—H15 | 120.3 |
O3—C4—N1 | 123.00 (15) | C16—C15—H15 | 120.3 |
O3—C4—C3 | 121.66 (15) | C11—C16—C15 | 120.43 (17) |
N1—C4—C3 | 115.28 (14) | C11—C16—H16 | 119.8 |
C2—C5—H5A | 120.0 | C15—C16—H16 | 119.8 |
O2—C1—C2—C5 | 168.65 (18) | C4—N1—C11—C16 | −131.82 (18) |
O1—C1—C2—C5 | −11.0 (2) | C16—C11—C12—C13 | 2.0 (3) |
O2—C1—C2—C3 | −9.2 (2) | N1—C11—C12—C13 | −179.01 (16) |
O1—C1—C2—C3 | 171.13 (14) | C11—C12—C13—C14 | −0.7 (3) |
C5—C2—C3—C4 | 108.2 (2) | C12—C13—C14—C15 | −1.0 (3) |
C1—C2—C3—C4 | −74.03 (18) | C12—C13—C14—I1 | 178.29 (14) |
C11—N1—C4—O3 | −7.6 (3) | C13—C14—C15—C16 | 1.4 (3) |
C11—N1—C4—C3 | 169.68 (15) | I1—C14—C15—C16 | −177.91 (14) |
C2—C3—C4—O3 | −25.0 (2) | C12—C11—C16—C15 | −1.6 (3) |
C2—C3—C4—N1 | 157.71 (14) | N1—C11—C16—C15 | 179.35 (17) |
C4—N1—C11—C12 | 49.1 (2) | C14—C15—C16—C11 | −0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.83 | 2.6597 (19) | 170 |
N1—H71···O3ii | 0.83 (2) | 2.10 (2) | 2.8963 (18) | 161 (2) |
C3—H3B···O3ii | 0.99 | 2.51 | 3.266 (2) | 134 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C11H10INO3 |
Mr | 331.10 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 23.1111 (6), 4.7863 (1), 10.4262 (2) |
β (°) | 97.071 (1) |
V (Å3) | 1144.54 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.79 |
Crystal size (mm) | 0.29 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.503, 0.776 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12435, 2839, 2612 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.018, 0.047, 1.06 |
No. of reflections | 2839 |
No. of parameters | 150 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.73, −0.61 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.83 | 2.6597 (19) | 170 |
N1—H71···O3ii | 0.83 (2) | 2.10 (2) | 2.8963 (18) | 161 (2) |
C3—H3B···O3ii | 0.99 | 2.51 | 3.266 (2) | 134 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z. |
Acknowledgements
BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST–PURSE for financial assistance.
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA. Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hanoon, H. D. (2011). Nat. J. Chem. 41, 77–89. Google Scholar
Katla, S., Pothana, P., Gubba, B. & Manda, S. (2011). Der Chem. Sin. 2, 47–53. CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Oishi, T. (1980). Polym. J. 12, 719–727. 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
Shetgiri, N. P. & Nayak, B. K. (2005). Indian J. Chem. Sect. B, 44, 1933–1936. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Urzua, M., Opazo, A., Gargallo, L. & Radic, D. (1998). Polym. Bull. 40, 63–67. CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Itaconic acid anhydride is a monomeric building block obtained from renewable sources. Copolymers containing both hydrophilic and hydrophobic segments are drawing considerable attention because of their possible use in biological systems. In this aspect, N-substituted itaconamic acid derivatives have attracted attention due to their amphiphilic properties. Being more reactive than maleic anhydride, itaconic anhydride has already been applied for introducing polar functional groups into polymers (Oishi, 1980; Urzua et al.,1998). In addition, the basic skeleton of itaconic anhydride is useful for the synthesis of cyclic derivatives of imides (Shetgiri & Nayak, 2005), pyridazines (Katla et al., 2011), oxazepines and diazepines (Hanoon, 2011) which show pharmacological activity. In continuation of our studies of pharmacologically active compounds, the crystal structure of the title compound was determined.
The C=C bond is present as its anti-Saytzeff tautomer. The N–C(=O) bond length of 1.351 (2) Å is indicative of amide-type resonance. The least-squares plane defined by the atoms of the aromatic moiety on the one hand and the non-hydrogen atoms of the carboxylic acid group on the other hand enclose an angle of 74.82 (11) ° (Fig. 1).
In the crystal, C–H···O contatcs whose range falls by more than 0.1 Å below the sum of van-der-Waals radii are observed next to classical hydrogen bonds of the N–H···O and C–H···O type. The N–H···O hydrogen bonds are supported by the carbonyl oxygen atom of the amide functionality as acceptor. Simultaneously, one of the hydrogen atoms of the methylene group forms a C–H···O contact to the same oxygen atom which, therefore, acts as twofold acceptor. The carboxylic acid groups engage in the common dimeric hydrogen bonding pattern frequently encountered for many carboxylic acids. In total, the molecules are connected to dimeric chains along the crystallographic b axis. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is C11(4)C11(4)R22(8) on the unary level. The shortest intercentroid distance between two aromatic systems was found at 4.7863 (11) Å which is about the length of axis b (Fig. 2).
The packing of the title compound in the crystal structure is shown in Figure 3.