organic compounds
N′-[(E)-2-Hydroxy-5-methoxybenzylidene]-2-methoxybenzohydrazide
aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E. Malaysia, bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Malaysia, cFaculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam, 42300, Selangor, Malaysia, and dH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com
The molecule of the title compound, C16H16N2O4, adopts an E conformation about the azomethine C=N double bond. The dihedral angle formed by the benzene rings is 18.88 (9)°. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, which forms an S(6) ring. In the crystal, the molecules are linked into chains parallel to [001] by N—H⋯O hydrogen bonds. The chains are further connected into a three-dimensional network by π–π stacking interactions with centroid–centroid distances of 3.6538 (10) and 3.8995 (11) Å.
Related literature
For the applications and biological activity of et al. (2009); Khan et al. (2009); Jarahpour et al. (2007); Pandeya et al. (1999). For related structures, see: Taha et al. (2012a,b); Lu et al. (2008).
see: PanneerselvamExperimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; 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, PARST (Nardelli, 1995) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812042389/rz5014sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042389/rz5014Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812042389/rz5014Isup3.cml
The title compound was synthesized by refluxing a mixture of 2-methoxybenzohydrazide (0.332 g, 2 mmol) and 2-hydroxy-5-methoxybenzaldehyde (0.304 g, 2 mmol) in methanol along with a catalytical amount of acetic acid for 3 hrs. The progress of reaction was monitored by TLC. After completion of reaction, the solvent was evaporated by vacuum to afford the crude product which was recrystallized by dissolving in methanol at room temperature to obtained needle-like crystals (0.504 g, 84% yield). All chemicals were purchased by Sigma Aldrich Germany.
H atoms on methyl, phenyl and methine carbon atoms were positioned geometrically with C—H = 0.96 Å (CH3) and 0.93 Å (CH), and constrained to ride on their parent atoms with Uiso(H) = 1.5Ueq(CH3) or 1.2Ueq(CH). The H atoms on the nitrogen (N–H= 0.835 (17) Å) and oxygen (O–H= 0.84 (2) Å) atoms were located in a difference Fourier map and refined isotropically. A rotating group model was applied to the methyl groups.
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2009).C16H16N2O4 | F(000) = 632 |
Mr = 300.31 | Dx = 1.307 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3190 reflections |
a = 14.5775 (13) Å | θ = 2.3–25.0° |
b = 11.0798 (11) Å | µ = 0.10 mm−1 |
c = 9.5893 (9) Å | T = 273 K |
β = 99.872 (2)° | Block, colourless |
V = 1525.9 (2) Å3 | 0.59 × 0.45 × 0.39 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 2767 independent reflections |
Radiation source: fine-focus sealed tube | 2210 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scan | θmax = 25.5°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −17→16 |
Tmin = 0.946, Tmax = 0.964 | k = −13→13 |
8886 measured reflections | l = −9→11 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0648P)2 + 0.1784P] where P = (Fo2 + 2Fc2)/3 |
2767 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C16H16N2O4 | V = 1525.9 (2) Å3 |
Mr = 300.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.5775 (13) Å | µ = 0.10 mm−1 |
b = 11.0798 (11) Å | T = 273 K |
c = 9.5893 (9) Å | 0.59 × 0.45 × 0.39 mm |
β = 99.872 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 2767 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2210 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.964 | Rint = 0.016 |
8886 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.15 e Å−3 |
2767 reflections | Δρmin = −0.15 e Å−3 |
208 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. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.41411 (11) | 0.06306 (13) | 0.11043 (13) | 0.0918 (4) | |
O2 | 0.68838 (9) | 0.10138 (14) | 0.58074 (17) | 0.1009 (4) | |
O3 | 0.17476 (9) | 0.24072 (14) | 0.01591 (12) | 0.0957 (5) | |
O4 | 0.16599 (8) | 0.47356 (10) | 0.32496 (12) | 0.0767 (3) | |
N1 | 0.31001 (9) | 0.20202 (11) | 0.23724 (13) | 0.0618 (3) | |
N2 | 0.22889 (9) | 0.26092 (12) | 0.24670 (14) | 0.0634 (4) | |
C1 | 0.47885 (12) | 0.07530 (15) | 0.22962 (18) | 0.0714 (5) | |
C2 | 0.56411 (15) | 0.01986 (17) | 0.2354 (2) | 0.0881 (6) | |
H2B | 0.5758 | −0.0250 | 0.1584 | 0.106* | |
C3 | 0.63154 (14) | 0.03008 (17) | 0.3527 (2) | 0.0884 (6) | |
H3A | 0.6885 | −0.0083 | 0.3548 | 0.106* | |
C4 | 0.61614 (11) | 0.09696 (16) | 0.4685 (2) | 0.0752 (5) | |
C5 | 0.53108 (11) | 0.15170 (14) | 0.46503 (19) | 0.0692 (4) | |
H5A | 0.5198 | 0.1959 | 0.5428 | 0.083* | |
C6 | 0.46152 (10) | 0.14167 (13) | 0.34613 (16) | 0.0612 (4) | |
C7 | 0.37267 (11) | 0.19998 (13) | 0.34759 (17) | 0.0629 (4) | |
H7A | 0.3612 | 0.2364 | 0.4303 | 0.076* | |
C8 | 0.16545 (10) | 0.28010 (13) | 0.13077 (15) | 0.0585 (4) | |
C9 | 0.08121 (10) | 0.34987 (13) | 0.15057 (14) | 0.0578 (4) | |
C10 | 0.08163 (11) | 0.44261 (14) | 0.24890 (16) | 0.0631 (4) | |
C11 | −0.00098 (14) | 0.50192 (17) | 0.2600 (2) | 0.0822 (5) | |
H11A | −0.0012 | 0.5626 | 0.3270 | 0.099* | |
C12 | −0.08169 (14) | 0.47113 (19) | 0.1728 (3) | 0.0922 (6) | |
H12A | −0.1367 | 0.5106 | 0.1818 | 0.111* | |
C13 | −0.08304 (12) | 0.3835 (2) | 0.0728 (2) | 0.0883 (6) | |
H13A | −0.1383 | 0.3641 | 0.0131 | 0.106* | |
C14 | −0.00128 (12) | 0.32362 (16) | 0.06098 (18) | 0.0743 (5) | |
H14A | −0.0019 | 0.2648 | −0.0083 | 0.089* | |
C15 | 0.17013 (18) | 0.5590 (2) | 0.4353 (3) | 0.1167 (8) | |
H15A | 0.2339 | 0.5716 | 0.4783 | 0.175* | |
H15B | 0.1357 | 0.5295 | 0.5050 | 0.175* | |
H15C | 0.1437 | 0.6339 | 0.3974 | 0.175* | |
C16 | 0.67844 (15) | 0.1759 (2) | 0.6962 (3) | 0.1081 (7) | |
H16A | 0.7359 | 0.1775 | 0.7622 | 0.162* | |
H16B | 0.6299 | 0.1448 | 0.7421 | 0.162* | |
H16C | 0.6628 | 0.2563 | 0.6629 | 0.162* | |
H2A | 0.2202 (11) | 0.2826 (14) | 0.3268 (18) | 0.066 (5)* | |
H1A | 0.3662 (16) | 0.101 (2) | 0.120 (2) | 0.106 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1031 (10) | 0.1066 (10) | 0.0695 (8) | 0.0320 (8) | 0.0257 (7) | −0.0085 (7) |
O2 | 0.0627 (8) | 0.1096 (10) | 0.1274 (11) | 0.0180 (7) | 0.0077 (8) | −0.0032 (9) |
O3 | 0.1036 (10) | 0.1328 (11) | 0.0532 (7) | 0.0220 (8) | 0.0202 (6) | −0.0145 (7) |
O4 | 0.0744 (8) | 0.0750 (7) | 0.0801 (7) | 0.0077 (6) | 0.0118 (6) | −0.0138 (6) |
N1 | 0.0644 (8) | 0.0624 (7) | 0.0623 (8) | 0.0105 (6) | 0.0214 (7) | 0.0013 (6) |
N2 | 0.0642 (8) | 0.0780 (8) | 0.0509 (7) | 0.0163 (6) | 0.0180 (6) | −0.0018 (6) |
C1 | 0.0783 (11) | 0.0701 (10) | 0.0719 (10) | 0.0150 (8) | 0.0298 (9) | 0.0068 (8) |
C2 | 0.0933 (14) | 0.0870 (12) | 0.0924 (13) | 0.0288 (11) | 0.0400 (12) | −0.0002 (10) |
C3 | 0.0740 (12) | 0.0836 (12) | 0.1166 (16) | 0.0274 (10) | 0.0418 (12) | 0.0122 (11) |
C4 | 0.0571 (10) | 0.0719 (10) | 0.0989 (12) | 0.0093 (8) | 0.0204 (9) | 0.0092 (9) |
C5 | 0.0634 (10) | 0.0658 (9) | 0.0826 (11) | 0.0059 (7) | 0.0241 (9) | −0.0007 (8) |
C6 | 0.0608 (9) | 0.0569 (8) | 0.0708 (9) | 0.0071 (7) | 0.0247 (8) | 0.0039 (7) |
C7 | 0.0648 (10) | 0.0622 (8) | 0.0654 (9) | 0.0073 (7) | 0.0211 (8) | −0.0030 (7) |
C8 | 0.0666 (9) | 0.0629 (8) | 0.0488 (8) | −0.0017 (7) | 0.0180 (7) | 0.0036 (6) |
C9 | 0.0581 (9) | 0.0632 (8) | 0.0539 (8) | 0.0000 (7) | 0.0142 (7) | 0.0152 (6) |
C10 | 0.0643 (10) | 0.0622 (8) | 0.0654 (9) | 0.0052 (7) | 0.0183 (8) | 0.0104 (7) |
C11 | 0.0774 (12) | 0.0749 (11) | 0.0991 (13) | 0.0142 (9) | 0.0293 (10) | 0.0068 (9) |
C12 | 0.0663 (12) | 0.0863 (13) | 0.1271 (17) | 0.0149 (10) | 0.0258 (12) | 0.0237 (12) |
C13 | 0.0587 (11) | 0.0930 (13) | 0.1090 (15) | −0.0021 (9) | 0.0026 (10) | 0.0306 (12) |
C14 | 0.0737 (11) | 0.0744 (10) | 0.0733 (10) | −0.0056 (8) | 0.0082 (9) | 0.0145 (8) |
C15 | 0.1156 (18) | 0.1105 (17) | 0.1212 (18) | 0.0065 (13) | 0.0127 (14) | −0.0508 (14) |
C16 | 0.0801 (14) | 0.1211 (18) | 0.1162 (17) | 0.0058 (12) | −0.0030 (12) | −0.0012 (15) |
O1—C1 | 1.359 (2) | C6—C7 | 1.450 (2) |
O1—H1A | 0.84 (2) | C7—H7A | 0.9300 |
O2—C4 | 1.372 (2) | C8—C9 | 1.491 (2) |
O2—C16 | 1.408 (3) | C9—C14 | 1.384 (2) |
O3—C8 | 1.2138 (17) | C9—C10 | 1.394 (2) |
O4—C10 | 1.362 (2) | C10—C11 | 1.392 (2) |
O4—C15 | 1.413 (2) | C11—C12 | 1.365 (3) |
N1—C7 | 1.2740 (18) | C11—H11A | 0.9300 |
N1—N2 | 1.3671 (17) | C12—C13 | 1.362 (3) |
N2—C8 | 1.3356 (19) | C12—H12A | 0.9300 |
N2—H2A | 0.835 (17) | C13—C14 | 1.386 (3) |
C1—C2 | 1.379 (2) | C13—H13A | 0.9300 |
C1—C6 | 1.396 (2) | C14—H14A | 0.9300 |
C2—C3 | 1.366 (3) | C15—H15A | 0.9600 |
C2—H2B | 0.9300 | C15—H15B | 0.9600 |
C3—C4 | 1.385 (3) | C15—H15C | 0.9600 |
C3—H3A | 0.9300 | C16—H16A | 0.9600 |
C4—C5 | 1.376 (2) | C16—H16B | 0.9600 |
C5—C6 | 1.394 (2) | C16—H16C | 0.9600 |
C5—H5A | 0.9300 | ||
C1—O1—H1A | 109.1 (15) | C14—C9—C10 | 118.52 (15) |
C4—O2—C16 | 117.98 (14) | C14—C9—C8 | 117.34 (14) |
C10—O4—C15 | 119.23 (15) | C10—C9—C8 | 124.08 (14) |
C7—N1—N2 | 117.29 (12) | O4—C10—C11 | 123.63 (16) |
C8—N2—N1 | 120.27 (12) | O4—C10—C9 | 116.54 (13) |
C8—N2—H2A | 121.8 (11) | C11—C10—C9 | 119.75 (16) |
N1—N2—H2A | 117.9 (11) | C12—C11—C10 | 120.09 (19) |
O1—C1—C2 | 118.72 (16) | C12—C11—H11A | 120.0 |
O1—C1—C6 | 122.06 (14) | C10—C11—H11A | 120.0 |
C2—C1—C6 | 119.22 (17) | C13—C12—C11 | 121.09 (18) |
C3—C2—C1 | 120.82 (17) | C13—C12—H12A | 119.5 |
C3—C2—H2B | 119.6 | C11—C12—H12A | 119.5 |
C1—C2—H2B | 119.6 | C12—C13—C14 | 119.35 (18) |
C2—C3—C4 | 120.80 (16) | C12—C13—H13A | 120.3 |
C2—C3—H3A | 119.6 | C14—C13—H13A | 120.3 |
C4—C3—H3A | 119.6 | C9—C14—C13 | 121.11 (18) |
O2—C4—C5 | 124.81 (17) | C9—C14—H14A | 119.4 |
O2—C4—C3 | 116.11 (16) | C13—C14—H14A | 119.4 |
C5—C4—C3 | 119.07 (18) | O4—C15—H15A | 109.5 |
C4—C5—C6 | 120.71 (16) | O4—C15—H15B | 109.5 |
C4—C5—H5A | 119.6 | H15A—C15—H15B | 109.5 |
C6—C5—H5A | 119.6 | O4—C15—H15C | 109.5 |
C5—C6—C1 | 119.36 (14) | H15A—C15—H15C | 109.5 |
C5—C6—C7 | 118.83 (14) | H15B—C15—H15C | 109.5 |
C1—C6—C7 | 121.80 (15) | O2—C16—H16A | 109.5 |
N1—C7—C6 | 120.96 (14) | O2—C16—H16B | 109.5 |
N1—C7—H7A | 119.5 | H16A—C16—H16B | 109.5 |
C6—C7—H7A | 119.5 | O2—C16—H16C | 109.5 |
O3—C8—N2 | 121.93 (14) | H16A—C16—H16C | 109.5 |
O3—C8—C9 | 121.66 (14) | H16B—C16—H16C | 109.5 |
N2—C8—C9 | 116.39 (12) | ||
C7—N1—N2—C8 | 171.24 (14) | N1—N2—C8—O3 | 4.2 (2) |
O1—C1—C2—C3 | 179.69 (17) | N1—N2—C8—C9 | −177.33 (12) |
C6—C1—C2—C3 | −0.6 (3) | O3—C8—C9—C14 | 29.3 (2) |
C1—C2—C3—C4 | −0.4 (3) | N2—C8—C9—C14 | −149.17 (14) |
C16—O2—C4—C5 | −6.0 (3) | O3—C8—C9—C10 | −147.80 (16) |
C16—O2—C4—C3 | 175.16 (18) | N2—C8—C9—C10 | 33.75 (19) |
C2—C3—C4—O2 | 180.00 (17) | C15—O4—C10—C11 | 9.0 (2) |
C2—C3—C4—C5 | 1.1 (3) | C15—O4—C10—C9 | −174.19 (17) |
O2—C4—C5—C6 | −179.68 (15) | C14—C9—C10—O4 | −173.55 (13) |
C3—C4—C5—C6 | −0.9 (3) | C8—C9—C10—O4 | 3.5 (2) |
C4—C5—C6—C1 | 0.0 (2) | C14—C9—C10—C11 | 3.4 (2) |
C4—C5—C6—C7 | 179.48 (14) | C8—C9—C10—C11 | −179.56 (14) |
O1—C1—C6—C5 | −179.50 (15) | O4—C10—C11—C12 | 175.27 (16) |
C2—C1—C6—C5 | 0.8 (2) | C9—C10—C11—C12 | −1.4 (3) |
O1—C1—C6—C7 | 1.0 (2) | C10—C11—C12—C13 | −0.8 (3) |
C2—C1—C6—C7 | −178.75 (15) | C11—C12—C13—C14 | 0.9 (3) |
N2—N1—C7—C6 | −178.73 (13) | C10—C9—C14—C13 | −3.3 (2) |
C5—C6—C7—N1 | 173.93 (14) | C8—C9—C14—C13 | 179.48 (14) |
C1—C6—C7—N1 | −6.6 (2) | C12—C13—C14—C9 | 1.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N1 | 0.83 (2) | 1.87 (2) | 2.605 (2) | 146.0 (19) |
N2—H2A···O3i | 0.835 (17) | 2.051 (17) | 2.8258 (17) | 154.2 (15) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H16N2O4 |
Mr | 300.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 14.5775 (13), 11.0798 (11), 9.5893 (9) |
β (°) | 99.872 (2) |
V (Å3) | 1525.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.59 × 0.45 × 0.39 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.946, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8886, 2767, 2210 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.124, 1.04 |
No. of reflections | 2767 |
No. of parameters | 208 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.15 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N1 | 0.83 (2) | 1.87 (2) | 2.605 (2) | 146.0 (19) |
N2—H2A···O3i | 0.835 (17) | 2.051 (17) | 2.8258 (17) | 154.2 (15) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
References
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Applications of Schiff bases are reported in different fields of chemistry with a broad range of biological activities (Panneerselvam et al., 2009, Khan et al., 2009, Jarahpour et al., 2007, Pandeya et al., 1999). The title compound is a Schiff base synthesize as a part of our ongoing resaerch to study different biological activities of this medicinally important class of organic compounds.
The structure of title compound (Fig. 1) is similar to that of the previously published compound N'-(2-hydroxybenzylidene)-2-methoxybenzohydrazide monohydrate (Lu et al., 2008), with the difference that the 2-hydroxy benzene ring is replaced by a 2-hydroxy-5-methoxy phenyl ring (C1–C6). The phenyl rings (C1–C6 and C9–C14) form an angle of 18.88 (9)°. Bond lengths and angles are similar to those observed in structurally related benzohydrazide derivatives (Taha et al., 2012; Lu et al., 2008). The E configuration of the azomethine olefinic bond is stabilized by an intramolecular O1—H1A···N1 hydrogen bond (Table 1) forming a ring of S(6) graph set motif. The crystal structure is stabilized by an intermolecular N2—H2A···O3 interaction forming chains running parallel to the [001] direction (Fig. 2). The chains are further linked into a three-dimensional network by π···π stacking interactions with centroid–centroid distances of 3.6538 (10) and 3.8995 (11) Å.