organic compounds
of the enol form of mesotrione: a benzoylcyclohexanedione herbicide
aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr
The title compound [systematic name: 3-hydroxy-2-(4-methylsulfonyl-2-nitrobenzoyl)cyclohex-2-enone], C14H13NO7S, is the enol form of a benzoylcyclohexanedione herbicide. As a result of this there is intramolecular O—H⋯O hydrogen bond enclosing an S(6) ring motif. The cyclohexene ring has an with the central CH2 C atom as the flap. Its mean plane is inclined to the benzene ring by 87.46 (8)°. In the crystal, molecules are linked by a series of C—H⋯O hydrogen bonds, forming a three-dimensional framework.
CCDC reference: 1410192
1. Related literature
For information on the herbicidal properties of the title compound, see: Mitchell et al. (2001). For related crystal structures, see: Eftekhari-Sis et al. (2012); Liu & Tang (2012).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick 2008).
Supporting information
CCDC reference: 1410192
https://doi.org/10.1107/S2056989015012803/su5166sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012803/su5166Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015012803/su5166Isup3.cml
The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH3CN gave single crystals suitable for X-ray analysis.
The O-bound H atom was located in a difference Fourier map and freely refined [O—H = 0.91 (3) Å]. The C-bound H atoms were positioned geometrically and refined using a riding model: C-H = 0.95 - 0.99 \%A with Uiso(H) = 1.5Ueq(C) for methyl H atoms and
1.2Ueq(C) for other H atoms.
Mesotrione, [keto form
2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione], is a benzoylcyclohexanedione herbicide and it has been developed for the selective pre- and post-emergence control of a wide range of broad-leaved and grass weeds in maize (Mitchell et al., 2001). However, until now its has not been reported.The title compound crystallized in the enol form (Fig. 1 and Table 1), with an intramolecular O6—H6O···O5 hydrogen bond embedded in an S(6) ring. The cyclohexene ring has an
with the central CH2 C-atom, C12, as the flap. Its mean plane is inclined to the benzene ring by 87.46 (8) °.All bond lengths and bond angles are normal and comparable to those observed in the crystal structures of similar compounds (Eftekhari-Sis et al., 2012; Liu et al., 2012).
In the crystal, molecules are linked by a series of C—H···O hydrogen bonds forming a three-dimensional framework (Fig. 2 and Table 1).
For information on the herbicidal properties of the title compound, see: Mitchell et al. (2001). For related crystal structures, see: Eftekhari-Sis et al. (2012); Liu & Tang (2012).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick 2008).Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular O—H···O hydrogen bond is shown as a dashed line (see Table 1 for details). | |
Fig. 2. Crystal packing of the title compound viewed along the a axis. The intermolecular C—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details). |
C14H13NO7S | F(000) = 704 |
Mr = 339.31 | Dx = 1.563 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4208 (2) Å | Cell parameters from 7168 reflections |
b = 11.2525 (3) Å | θ = 2.5–27.5° |
c = 12.3550 (3) Å | µ = 0.26 mm−1 |
β = 95.370 (1)° | T = 173 K |
V = 1442.39 (6) Å3 | Block, colourless |
Z = 4 | 0.43 × 0.30 × 0.20 mm |
Bruker APEXII CCD diffractometer | 2572 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.025 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | θmax = 26.0°, θmin = 2.0° |
Tmin = 0.895, Tmax = 0.949 | h = −12→12 |
12093 measured reflections | k = −13→13 |
2828 independent reflections | l = −15→15 |
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)] = 0.036 | Hydrogen site location: mixed |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0538P)2 + 0.7458P] where P = (Fo2 + 2Fc2)/3 |
2828 reflections | (Δ/σ)max < 0.001 |
213 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C14H13NO7S | V = 1442.39 (6) Å3 |
Mr = 339.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.4208 (2) Å | µ = 0.26 mm−1 |
b = 11.2525 (3) Å | T = 173 K |
c = 12.3550 (3) Å | 0.43 × 0.30 × 0.20 mm |
β = 95.370 (1)° |
Bruker APEXII CCD diffractometer | 2828 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2572 reflections with I > 2σ(I) |
Tmin = 0.895, Tmax = 0.949 | Rint = 0.025 |
12093 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.48 e Å−3 |
2828 reflections | Δρmin = −0.40 e Å−3 |
213 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.31056 (3) | 0.24106 (4) | 1.11672 (3) | 0.02141 (13) | |
O1 | 0.24559 (11) | 0.12877 (11) | 1.11593 (11) | 0.0333 (3) | |
O2 | 0.24978 (11) | 0.33729 (12) | 1.05544 (10) | 0.0341 (3) | |
O3 | 0.78663 (13) | 0.37212 (12) | 0.87472 (13) | 0.0461 (4) | |
O4 | 0.59220 (13) | 0.44028 (12) | 0.84539 (11) | 0.0406 (3) | |
O5 | 0.92622 (11) | 0.18323 (14) | 1.03272 (11) | 0.0420 (4) | |
O6 | 1.08825 (11) | 0.11994 (14) | 0.90444 (11) | 0.0387 (3) | |
H6O | 1.057 (3) | 0.151 (2) | 0.965 (2) | 0.062 (8)* | |
O7 | 0.64741 (11) | 0.12478 (13) | 0.77772 (11) | 0.0367 (3) | |
N1 | 0.67227 (14) | 0.37175 (13) | 0.88940 (12) | 0.0280 (3) | |
C1 | 0.34825 (16) | 0.28528 (17) | 1.25212 (13) | 0.0279 (4) | |
H1A | 0.2685 | 0.2995 | 1.2863 | 0.042* | |
H1B | 0.3993 | 0.3585 | 1.2540 | 0.042* | |
H1C | 0.3981 | 0.2225 | 1.2918 | 0.042* | |
C2 | 0.46359 (14) | 0.21719 (14) | 1.06875 (12) | 0.0195 (3) | |
C3 | 0.51015 (14) | 0.30302 (14) | 1.00287 (12) | 0.0206 (3) | |
H3 | 0.4624 | 0.3733 | 0.9847 | 0.025* | |
C4 | 0.62836 (15) | 0.28346 (14) | 0.96419 (12) | 0.0213 (3) | |
C5 | 0.70348 (14) | 0.18398 (15) | 0.99181 (13) | 0.0224 (3) | |
C6 | 0.65419 (15) | 0.09958 (15) | 1.05868 (13) | 0.0247 (3) | |
H6 | 0.7035 | 0.0309 | 1.0792 | 0.030* | |
C7 | 0.53315 (15) | 0.11459 (14) | 1.09596 (13) | 0.0234 (3) | |
H7 | 0.4986 | 0.0552 | 1.1396 | 0.028* | |
C8 | 0.83866 (15) | 0.16470 (15) | 0.95976 (14) | 0.0258 (4) | |
C9 | 0.86333 (14) | 0.11938 (14) | 0.85403 (13) | 0.0221 (3) | |
C10 | 0.98924 (15) | 0.09727 (16) | 0.83365 (14) | 0.0268 (4) | |
C11 | 1.02509 (16) | 0.0464 (2) | 0.72964 (16) | 0.0378 (5) | |
H11A | 1.1048 | −0.0012 | 0.7437 | 0.045* | |
H11B | 1.0428 | 0.1117 | 0.6795 | 0.045* | |
C12 | 0.91933 (17) | −0.03099 (19) | 0.67708 (16) | 0.0368 (4) | |
H12A | 0.9099 | −0.1027 | 0.7220 | 0.044* | |
H12B | 0.9416 | −0.0569 | 0.6046 | 0.044* | |
C13 | 0.79406 (16) | 0.03715 (17) | 0.66546 (14) | 0.0312 (4) | |
H13A | 0.7239 | −0.0180 | 0.6393 | 0.037* | |
H13B | 0.7995 | 0.0992 | 0.6093 | 0.037* | |
C14 | 0.75890 (15) | 0.09568 (15) | 0.76871 (13) | 0.0238 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0139 (2) | 0.0295 (2) | 0.0211 (2) | 0.00081 (14) | 0.00345 (15) | 0.00020 (15) |
O1 | 0.0245 (6) | 0.0388 (7) | 0.0376 (7) | −0.0102 (5) | 0.0082 (5) | −0.0049 (6) |
O2 | 0.0242 (6) | 0.0461 (8) | 0.0324 (7) | 0.0129 (5) | 0.0046 (5) | 0.0085 (6) |
O3 | 0.0384 (8) | 0.0357 (8) | 0.0693 (10) | −0.0057 (6) | 0.0325 (7) | 0.0051 (7) |
O4 | 0.0450 (8) | 0.0374 (8) | 0.0395 (8) | −0.0054 (6) | 0.0042 (6) | 0.0145 (6) |
O5 | 0.0205 (6) | 0.0733 (10) | 0.0320 (7) | −0.0026 (6) | 0.0022 (5) | −0.0197 (7) |
O6 | 0.0158 (6) | 0.0656 (10) | 0.0350 (7) | −0.0005 (6) | 0.0033 (5) | −0.0182 (7) |
O7 | 0.0193 (6) | 0.0557 (9) | 0.0344 (7) | 0.0087 (5) | −0.0007 (5) | −0.0121 (6) |
N1 | 0.0321 (8) | 0.0249 (7) | 0.0286 (8) | −0.0075 (6) | 0.0116 (6) | −0.0025 (6) |
C1 | 0.0227 (8) | 0.0394 (10) | 0.0222 (8) | 0.0006 (7) | 0.0043 (6) | −0.0043 (7) |
C2 | 0.0155 (7) | 0.0250 (8) | 0.0185 (7) | −0.0002 (6) | 0.0035 (6) | −0.0027 (6) |
C3 | 0.0196 (7) | 0.0219 (8) | 0.0203 (7) | 0.0000 (6) | 0.0022 (6) | −0.0026 (6) |
C4 | 0.0220 (8) | 0.0236 (8) | 0.0190 (7) | −0.0050 (6) | 0.0054 (6) | −0.0028 (6) |
C5 | 0.0183 (7) | 0.0282 (9) | 0.0212 (8) | −0.0014 (6) | 0.0039 (6) | −0.0074 (6) |
C6 | 0.0219 (7) | 0.0267 (8) | 0.0259 (8) | 0.0047 (6) | 0.0040 (6) | 0.0005 (7) |
C7 | 0.0226 (8) | 0.0252 (8) | 0.0228 (8) | 0.0001 (6) | 0.0046 (6) | 0.0027 (6) |
C8 | 0.0183 (7) | 0.0318 (9) | 0.0276 (8) | −0.0019 (6) | 0.0042 (6) | −0.0052 (7) |
C9 | 0.0181 (7) | 0.0249 (8) | 0.0240 (8) | −0.0010 (6) | 0.0051 (6) | −0.0029 (6) |
C10 | 0.0185 (7) | 0.0340 (9) | 0.0283 (8) | −0.0013 (7) | 0.0044 (6) | −0.0047 (7) |
C11 | 0.0218 (8) | 0.0590 (13) | 0.0341 (10) | 0.0007 (8) | 0.0103 (7) | −0.0155 (9) |
C12 | 0.0304 (9) | 0.0471 (11) | 0.0338 (10) | 0.0009 (8) | 0.0082 (8) | −0.0131 (8) |
C13 | 0.0269 (8) | 0.0437 (10) | 0.0227 (8) | 0.0024 (7) | 0.0006 (6) | −0.0060 (7) |
C14 | 0.0212 (8) | 0.0268 (8) | 0.0234 (8) | 0.0011 (6) | 0.0026 (6) | −0.0005 (6) |
S1—O1 | 1.4331 (13) | C5—C6 | 1.389 (2) |
S1—O2 | 1.4343 (12) | C5—C8 | 1.514 (2) |
S1—C1 | 1.7543 (17) | C6—C7 | 1.393 (2) |
S1—C2 | 1.7730 (15) | C6—H6 | 0.9500 |
O3—N1 | 1.2222 (19) | C7—H7 | 0.9500 |
O4—N1 | 1.225 (2) | C8—C9 | 1.448 (2) |
O5—C8 | 1.239 (2) | C9—C10 | 1.382 (2) |
O6—C10 | 1.314 (2) | C9—C14 | 1.467 (2) |
O6—H6O | 0.91 (3) | C10—C11 | 1.486 (2) |
O7—C14 | 1.222 (2) | C11—C12 | 1.504 (3) |
N1—C4 | 1.459 (2) | C11—H11A | 0.9900 |
C1—H1A | 0.9800 | C11—H11B | 0.9900 |
C1—H1B | 0.9800 | C12—C13 | 1.509 (2) |
C1—H1C | 0.9800 | C12—H12A | 0.9900 |
C2—C3 | 1.380 (2) | C12—H12B | 0.9900 |
C2—C7 | 1.388 (2) | C13—C14 | 1.511 (2) |
C3—C4 | 1.380 (2) | C13—H13A | 0.9900 |
C3—H3 | 0.9500 | C13—H13B | 0.9900 |
C4—C5 | 1.390 (2) | ||
O1—S1—O2 | 118.50 (8) | C2—C7—H7 | 120.4 |
O1—S1—C1 | 108.66 (8) | C6—C7—H7 | 120.4 |
O2—S1—C1 | 109.73 (8) | O5—C8—C9 | 122.34 (14) |
O1—S1—C2 | 107.66 (7) | O5—C8—C5 | 115.18 (14) |
O2—S1—C2 | 107.73 (7) | C9—C8—C5 | 122.32 (13) |
C1—S1—C2 | 103.51 (7) | C10—C9—C8 | 118.67 (14) |
C10—O6—H6O | 107.8 (17) | C10—C9—C14 | 119.31 (14) |
O3—N1—O4 | 124.40 (15) | C8—C9—C14 | 122.01 (14) |
O3—N1—C4 | 117.66 (15) | O6—C10—C9 | 122.94 (15) |
O4—N1—C4 | 117.94 (14) | O6—C10—C11 | 113.90 (14) |
S1—C1—H1A | 109.5 | C9—C10—C11 | 123.15 (15) |
S1—C1—H1B | 109.5 | C10—C11—C12 | 111.30 (14) |
H1A—C1—H1B | 109.5 | C10—C11—H11A | 109.4 |
S1—C1—H1C | 109.5 | C12—C11—H11A | 109.4 |
H1A—C1—H1C | 109.5 | C10—C11—H11B | 109.4 |
H1B—C1—H1C | 109.5 | C12—C11—H11B | 109.4 |
C3—C2—C7 | 121.38 (14) | H11A—C11—H11B | 108.0 |
C3—C2—S1 | 117.90 (12) | C11—C12—C13 | 109.84 (16) |
C7—C2—S1 | 120.72 (12) | C11—C12—H12A | 109.7 |
C2—C3—C4 | 117.84 (14) | C13—C12—H12A | 109.7 |
C2—C3—H3 | 121.1 | C11—C12—H12B | 109.7 |
C4—C3—H3 | 121.1 | C13—C12—H12B | 109.7 |
C3—C4—C5 | 122.95 (14) | H12A—C12—H12B | 108.2 |
C3—C4—N1 | 116.98 (14) | C12—C13—C14 | 114.66 (14) |
C5—C4—N1 | 120.06 (14) | C12—C13—H13A | 108.6 |
C6—C5—C4 | 117.75 (14) | C14—C13—H13A | 108.6 |
C6—C5—C8 | 117.56 (14) | C12—C13—H13B | 108.6 |
C4—C5—C8 | 124.58 (15) | C14—C13—H13B | 108.6 |
C5—C6—C7 | 120.71 (15) | H13A—C13—H13B | 107.6 |
C5—C6—H6 | 119.6 | O7—C14—C9 | 122.24 (15) |
C7—C6—H6 | 119.6 | O7—C14—C13 | 120.09 (14) |
C2—C7—C6 | 119.30 (15) | C9—C14—C13 | 117.63 (14) |
O1—S1—C2—C3 | 141.94 (12) | C6—C5—C8—O5 | −73.6 (2) |
O2—S1—C2—C3 | 13.08 (15) | C4—C5—C8—O5 | 102.5 (2) |
C1—S1—C2—C3 | −103.11 (13) | C6—C5—C8—C9 | 101.98 (19) |
O1—S1—C2—C7 | −37.36 (15) | C4—C5—C8—C9 | −81.9 (2) |
O2—S1—C2—C7 | −166.22 (13) | O5—C8—C9—C10 | −0.7 (3) |
C1—S1—C2—C7 | 77.59 (15) | C5—C8—C9—C10 | −175.97 (15) |
C7—C2—C3—C4 | 0.3 (2) | O5—C8—C9—C14 | 178.90 (17) |
S1—C2—C3—C4 | −179.00 (11) | C5—C8—C9—C14 | 3.6 (3) |
C2—C3—C4—C5 | −2.4 (2) | C8—C9—C10—O6 | −2.8 (3) |
C2—C3—C4—N1 | 176.38 (13) | C14—C9—C10—O6 | 177.62 (16) |
O3—N1—C4—C3 | 162.96 (15) | C8—C9—C10—C11 | 177.56 (17) |
O4—N1—C4—C3 | −17.2 (2) | C14—C9—C10—C11 | −2.0 (3) |
O3—N1—C4—C5 | −18.3 (2) | O6—C10—C11—C12 | 151.87 (17) |
O4—N1—C4—C5 | 161.57 (15) | C9—C10—C11—C12 | −28.4 (3) |
C3—C4—C5—C6 | 2.0 (2) | C10—C11—C12—C13 | 53.4 (2) |
N1—C4—C5—C6 | −176.65 (14) | C11—C12—C13—C14 | −51.4 (2) |
C3—C4—C5—C8 | −174.05 (14) | C10—C9—C14—O7 | −172.27 (17) |
N1—C4—C5—C8 | 7.3 (2) | C8—C9—C14—O7 | 8.1 (3) |
C4—C5—C6—C7 | 0.3 (2) | C10—C9—C14—C13 | 5.5 (2) |
C8—C5—C6—C7 | 176.70 (14) | C8—C9—C14—C13 | −174.07 (16) |
C3—C2—C7—C6 | 2.0 (2) | C12—C13—C14—O7 | −160.12 (17) |
S1—C2—C7—C6 | −178.77 (12) | C12—C13—C14—C9 | 22.0 (2) |
C5—C6—C7—C2 | −2.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6O···O5 | 0.91 (3) | 1.71 (3) | 2.524 (2) | 148 (2) |
C1—H1B···O4i | 0.98 | 2.58 | 3.393 (2) | 140 |
C1—H1B···O7ii | 0.98 | 2.58 | 3.265 (2) | 127 |
C11—H11A···O3iii | 0.99 | 2.40 | 3.135 (2) | 131 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+1/2, z+1/2; (iii) −x+2, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6O···O5 | 0.91 (3) | 1.71 (3) | 2.524 (2) | 148 (2) |
C1—H1B···O4i | 0.98 | 2.58 | 3.393 (2) | 140 |
C1—H1B···O7ii | 0.98 | 2.58 | 3.265 (2) | 127 |
C11—H11A···O3iii | 0.99 | 2.40 | 3.135 (2) | 131 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+1/2, z+1/2; (iii) −x+2, y−1/2, −z+3/2. |
Acknowledgements
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2014R1A1A4A01009105).
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Mesotrione, [keto form systematic name: 2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione], is a benzoylcyclohexanedione herbicide and it has been developed for the selective pre- and post-emergence control of a wide range of broad-leaved and grass weeds in maize (Mitchell et al., 2001). However, until now its crystal structure has not been reported.
The title compound crystallized in the enol form (Fig. 1 and Table 1), with an intramolecular O6—H6O···O5 hydrogen bond embedded in an S(6) ring. The cyclohexene ring has an envelope conformation with the central CH2 C-atom, C12, as the flap. Its mean plane is inclined to the benzene ring by 87.46 (8) °.
All bond lengths and bond angles are normal and comparable to those observed in the crystal structures of similar compounds (Eftekhari-Sis et al., 2012; Liu et al., 2012).
In the crystal, molecules are linked by a series of C—H···O hydrogen bonds forming a three-dimensional framework (Fig. 2 and Table 1).