In the title compound, C
19H
12O
4, the dioxole ring adopts a flattened envelope conformation with the methylene C at the flap [deviation = 0.104 (2) Å]. The benzene ring of the benzodioxole ring system makes a dihedral angle of 76.45 (5)° with the planar [maximum deviation = 0.016 (1) Å] 3
H-benzo[
f]isobenzofuran-1-one ring system. In the crystal structure, the molecules are linked into
C(5) chains running along the
b axis by intermolecular C—H

O hydrogen bonds. In addition, C—H

π interactions are observed.
Supporting information
CCDC reference: 774324
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.046
- wR factor = 0.137
- Data-to-parameter ratio = 20.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 10
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K
PLAT793_ALERT_4_G The Model has Chirality at C12 (Verify) .... R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
NaBH4 (1.6 g, 43.75 mmol) was carefully added in small portions to a solution
of keto acid (3.5 g, 10.93 mmol) in THF-EtOH (2:5) at 273 K. The reaction
mixture was refluxed for 12 h and then poured into ice water (200 ml). The
reaction mixture was acidified using HCl (pH = 2-3) and then stirred for
0.5 h at room temperature. The solid formed was filtered and washed with
methanol to afford lactone as a colourless solid.
H atoms were positioned geometrically and allowed to ride on their parent C
atoms, with C–H distances fixed in the range 0.93–0.98 Å and Uiso(H) =
1.2Ueq(C).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
3-(1,3-Benzodioxol-5-yl)-3
H-benzo[
f]isobenzofuran-1-one
top
Crystal data top
C19H12O4 | F(000) = 632 |
Mr = 304.29 | Dx = 1.429 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4251 reflections |
a = 7.8617 (3) Å | θ = 2.2–30.4° |
b = 12.0417 (4) Å | µ = 0.10 mm−1 |
c = 15.0214 (5) Å | T = 293 K |
β = 95.848 (2)° | Block, colourless |
V = 1414.65 (9) Å3 | 0.21 × 0.19 × 0.17 mm |
Z = 4 | |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 4251 independent reflections |
Radiation source: fine-focus sealed tube | 3370 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 30.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→10 |
Tmin = 0.979, Tmax = 0.983 | k = −17→16 |
19039 measured reflections | l = −21→13 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0727P)2 + 0.2801P] where P = (Fo2 + 2Fc2)/3 |
4251 reflections | (Δ/σ)max = 0.002 |
208 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
C19H12O4 | V = 1414.65 (9) Å3 |
Mr = 304.29 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.8617 (3) Å | µ = 0.10 mm−1 |
b = 12.0417 (4) Å | T = 293 K |
c = 15.0214 (5) Å | 0.21 × 0.19 × 0.17 mm |
β = 95.848 (2)° | |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 4251 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3370 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.983 | Rint = 0.038 |
19039 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.34 e Å−3 |
4251 reflections | Δρmin = −0.22 e Å−3 |
208 parameters | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.50740 (15) | 1.28238 (9) | 0.19129 (8) | 0.0587 (3) | |
O2 | 0.58783 (11) | 1.12957 (8) | 0.26946 (6) | 0.0419 (2) | |
O3 | 1.20824 (14) | 1.15928 (9) | 0.41662 (8) | 0.0588 (3) | |
O4 | 1.29651 (13) | 0.98350 (9) | 0.46223 (8) | 0.0548 (3) | |
C1 | 0.70723 (14) | 1.07497 (10) | −0.02366 (7) | 0.0333 (2) | |
C2 | 0.71799 (18) | 1.09700 (12) | −0.11570 (9) | 0.0443 (3) | |
H2 | 0.6798 | 1.1648 | −0.1397 | 0.053* | |
C3 | 0.7832 (2) | 1.02046 (14) | −0.16932 (9) | 0.0503 (4) | |
H3 | 0.7902 | 1.0364 | −0.2294 | 0.060* | |
C4 | 0.84016 (19) | 0.91727 (13) | −0.13420 (9) | 0.0479 (3) | |
H4 | 0.8842 | 0.8652 | −0.1714 | 0.057* | |
C5 | 0.83164 (17) | 0.89258 (11) | −0.04622 (9) | 0.0401 (3) | |
H5 | 0.8700 | 0.8239 | −0.0241 | 0.048* | |
C6 | 0.76513 (14) | 0.97022 (9) | 0.01198 (7) | 0.0307 (2) | |
C7 | 0.75593 (14) | 0.94554 (9) | 0.10366 (7) | 0.0313 (2) | |
H7 | 0.7938 | 0.8775 | 0.1274 | 0.038* | |
C8 | 0.69034 (13) | 1.02365 (9) | 0.15634 (7) | 0.0289 (2) | |
C9 | 0.63280 (14) | 1.12596 (9) | 0.12091 (8) | 0.0324 (2) | |
C10 | 0.64042 (16) | 1.15336 (10) | 0.03305 (8) | 0.0369 (3) | |
H10 | 0.6023 | 1.2222 | 0.0112 | 0.044* | |
C11 | 0.56804 (15) | 1.19097 (11) | 0.19281 (9) | 0.0396 (3) | |
C12 | 0.66602 (15) | 1.02200 (10) | 0.25451 (7) | 0.0329 (2) | |
H12 | 0.5871 | 0.9622 | 0.2667 | 0.039* | |
C13 | 0.83094 (15) | 1.00982 (10) | 0.31446 (7) | 0.0310 (2) | |
C14 | 0.88263 (17) | 0.90475 (10) | 0.34263 (9) | 0.0389 (3) | |
H14 | 0.8110 | 0.8446 | 0.3280 | 0.047* | |
C15 | 1.04087 (17) | 0.88686 (11) | 0.39288 (9) | 0.0420 (3) | |
H15 | 1.0765 | 0.8161 | 0.4114 | 0.050* | |
C16 | 1.13967 (16) | 0.97803 (11) | 0.41324 (8) | 0.0364 (3) | |
C17 | 1.08753 (16) | 1.08282 (10) | 0.38590 (8) | 0.0355 (2) | |
C18 | 0.93465 (15) | 1.10207 (10) | 0.33622 (8) | 0.0351 (2) | |
H18 | 0.9013 | 1.1732 | 0.3178 | 0.042* | |
C19 | 1.34790 (18) | 1.09710 (13) | 0.45929 (10) | 0.0497 (3) | |
H19A | 1.3783 | 1.1248 | 0.5195 | 0.060* | |
H19B | 1.4468 | 1.1041 | 0.4260 | 0.060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0624 (7) | 0.0454 (6) | 0.0653 (7) | 0.0244 (5) | −0.0085 (5) | −0.0180 (5) |
O2 | 0.0383 (5) | 0.0475 (5) | 0.0398 (4) | 0.0108 (4) | 0.0030 (4) | −0.0106 (4) |
O3 | 0.0477 (6) | 0.0393 (5) | 0.0841 (8) | −0.0062 (4) | −0.0198 (5) | −0.0088 (5) |
O4 | 0.0438 (5) | 0.0521 (6) | 0.0637 (7) | 0.0030 (4) | −0.0172 (5) | 0.0006 (5) |
C1 | 0.0314 (5) | 0.0338 (6) | 0.0336 (5) | −0.0029 (4) | −0.0020 (4) | 0.0019 (4) |
C2 | 0.0467 (7) | 0.0483 (7) | 0.0367 (6) | −0.0045 (6) | −0.0013 (5) | 0.0095 (5) |
C3 | 0.0534 (8) | 0.0644 (9) | 0.0342 (6) | −0.0127 (7) | 0.0097 (5) | 0.0010 (6) |
C4 | 0.0511 (8) | 0.0527 (8) | 0.0424 (7) | −0.0085 (6) | 0.0165 (6) | −0.0114 (6) |
C5 | 0.0432 (6) | 0.0367 (6) | 0.0415 (6) | −0.0020 (5) | 0.0094 (5) | −0.0059 (5) |
C6 | 0.0292 (5) | 0.0291 (5) | 0.0335 (5) | −0.0028 (4) | 0.0014 (4) | −0.0027 (4) |
C7 | 0.0343 (5) | 0.0248 (5) | 0.0342 (5) | 0.0013 (4) | 0.0011 (4) | −0.0002 (4) |
C8 | 0.0271 (5) | 0.0266 (5) | 0.0322 (5) | −0.0010 (4) | −0.0010 (4) | −0.0023 (4) |
C9 | 0.0306 (5) | 0.0267 (5) | 0.0385 (5) | 0.0038 (4) | −0.0037 (4) | −0.0043 (4) |
C10 | 0.0391 (6) | 0.0283 (5) | 0.0412 (6) | 0.0044 (4) | −0.0056 (5) | 0.0026 (4) |
C11 | 0.0333 (6) | 0.0383 (6) | 0.0453 (6) | 0.0072 (5) | −0.0056 (5) | −0.0111 (5) |
C12 | 0.0319 (5) | 0.0336 (6) | 0.0331 (5) | 0.0005 (4) | 0.0026 (4) | −0.0039 (4) |
C13 | 0.0328 (5) | 0.0335 (5) | 0.0270 (5) | −0.0011 (4) | 0.0037 (4) | −0.0009 (4) |
C14 | 0.0402 (6) | 0.0319 (6) | 0.0440 (6) | −0.0052 (5) | 0.0016 (5) | 0.0033 (5) |
C15 | 0.0453 (7) | 0.0334 (6) | 0.0463 (7) | 0.0007 (5) | −0.0004 (5) | 0.0083 (5) |
C16 | 0.0364 (6) | 0.0401 (6) | 0.0320 (5) | 0.0031 (5) | 0.0000 (4) | 0.0004 (4) |
C17 | 0.0372 (6) | 0.0325 (6) | 0.0363 (5) | −0.0029 (4) | 0.0010 (4) | −0.0061 (4) |
C18 | 0.0385 (6) | 0.0290 (5) | 0.0373 (5) | 0.0011 (4) | 0.0005 (4) | −0.0013 (4) |
C19 | 0.0391 (7) | 0.0562 (9) | 0.0515 (8) | −0.0040 (6) | −0.0063 (6) | −0.0052 (6) |
Geometric parameters (Å, º) top
O1—C11 | 1.1988 (15) | C7—H7 | 0.93 |
O2—C11 | 1.3639 (17) | C8—C9 | 1.3988 (15) |
O2—C12 | 1.4610 (14) | C8—C12 | 1.5063 (15) |
O3—C17 | 1.3682 (15) | C9—C10 | 1.3675 (17) |
O3—C19 | 1.4260 (18) | C9—C11 | 1.4665 (16) |
O4—C16 | 1.3716 (15) | C10—H10 | 0.93 |
O4—C19 | 1.4283 (18) | C12—C13 | 1.5085 (16) |
C1—C10 | 1.4085 (17) | C12—H12 | 0.98 |
C1—C2 | 1.4188 (17) | C13—C14 | 1.3820 (17) |
C1—C6 | 1.4266 (16) | C13—C18 | 1.3969 (16) |
C2—C3 | 1.358 (2) | C14—C15 | 1.4044 (18) |
C2—H2 | 0.93 | C14—H14 | 0.93 |
C3—C4 | 1.405 (2) | C15—C16 | 1.3615 (18) |
C3—H3 | 0.93 | C15—H15 | 0.93 |
C4—C5 | 1.3628 (19) | C16—C17 | 1.3765 (17) |
C4—H4 | 0.93 | C17—C18 | 1.3684 (17) |
C5—C6 | 1.4160 (16) | C18—H18 | 0.93 |
C5—H5 | 0.93 | C19—H19A | 0.97 |
C6—C7 | 1.4178 (15) | C19—H19B | 0.97 |
C7—C8 | 1.3638 (15) | | |
| | | |
C11—O2—C12 | 111.37 (9) | O1—C11—O2 | 121.65 (12) |
C17—O3—C19 | 105.91 (11) | O1—C11—C9 | 130.04 (13) |
C16—O4—C19 | 105.73 (10) | O2—C11—C9 | 108.31 (10) |
C10—C1—C2 | 121.80 (11) | O2—C12—C8 | 103.66 (9) |
C10—C1—C6 | 119.34 (10) | O2—C12—C13 | 110.11 (9) |
C2—C1—C6 | 118.86 (11) | C8—C12—C13 | 113.49 (9) |
C3—C2—C1 | 120.96 (13) | O2—C12—H12 | 109.8 |
C3—C2—H2 | 119.5 | C8—C12—H12 | 109.8 |
C1—C2—H2 | 119.5 | C13—C12—H12 | 109.8 |
C2—C3—C4 | 120.17 (12) | C14—C13—C18 | 120.66 (11) |
C2—C3—H3 | 119.9 | C14—C13—C12 | 118.67 (10) |
C4—C3—H3 | 119.9 | C18—C13—C12 | 120.54 (10) |
C5—C4—C3 | 120.77 (13) | C13—C14—C15 | 121.45 (12) |
C5—C4—H4 | 119.6 | C13—C14—H14 | 119.3 |
C3—C4—H4 | 119.6 | C15—C14—H14 | 119.3 |
C4—C5—C6 | 120.83 (13) | C16—C15—C14 | 116.80 (11) |
C4—C5—H5 | 119.6 | C16—C15—H15 | 121.6 |
C6—C5—H5 | 119.6 | C14—C15—H15 | 121.6 |
C7—C6—C5 | 121.33 (11) | C15—C16—O4 | 128.34 (12) |
C7—C6—C1 | 120.26 (10) | C15—C16—C17 | 121.77 (11) |
C5—C6—C1 | 118.41 (11) | O4—C16—C17 | 109.88 (11) |
C8—C7—C6 | 118.60 (10) | O3—C17—C18 | 127.62 (12) |
C8—C7—H7 | 120.7 | O3—C17—C16 | 109.94 (11) |
C6—C7—H7 | 120.7 | C18—C17—C16 | 122.43 (11) |
C7—C8—C9 | 120.89 (10) | C17—C18—C13 | 116.89 (11) |
C7—C8—C12 | 130.70 (10) | C17—C18—H18 | 121.6 |
C9—C8—C12 | 108.41 (9) | C13—C18—H18 | 121.6 |
C10—C9—C8 | 122.37 (11) | O3—C19—O4 | 108.03 (11) |
C10—C9—C11 | 129.39 (11) | O3—C19—H19A | 110.1 |
C8—C9—C11 | 108.24 (10) | O4—C19—H19A | 110.1 |
C9—C10—C1 | 118.54 (11) | O3—C19—H19B | 110.1 |
C9—C10—H10 | 120.7 | O4—C19—H19B | 110.1 |
C1—C10—H10 | 120.7 | H19A—C19—H19B | 108.4 |
| | | |
C10—C1—C2—C3 | 179.83 (13) | C11—O2—C12—C8 | −0.87 (12) |
C6—C1—C2—C3 | −0.45 (19) | C11—O2—C12—C13 | 120.86 (11) |
C1—C2—C3—C4 | 0.5 (2) | C7—C8—C12—O2 | −179.21 (11) |
C2—C3—C4—C5 | −0.3 (2) | C9—C8—C12—O2 | 1.19 (12) |
C3—C4—C5—C6 | 0.0 (2) | C7—C8—C12—C13 | 61.35 (16) |
C4—C5—C6—C7 | −179.88 (12) | C9—C8—C12—C13 | −118.25 (11) |
C4—C5—C6—C1 | −0.01 (18) | O2—C12—C13—C14 | 150.18 (11) |
C10—C1—C6—C7 | −0.20 (16) | C8—C12—C13—C14 | −94.13 (13) |
C2—C1—C6—C7 | −179.92 (11) | O2—C12—C13—C18 | −33.93 (14) |
C10—C1—C6—C5 | 179.93 (11) | C8—C12—C13—C18 | 81.76 (13) |
C2—C1—C6—C5 | 0.21 (17) | C18—C13—C14—C15 | −0.74 (19) |
C5—C6—C7—C8 | −179.90 (11) | C12—C13—C14—C15 | 175.14 (11) |
C1—C6—C7—C8 | 0.23 (16) | C13—C14—C15—C16 | 0.7 (2) |
C6—C7—C8—C9 | 0.16 (16) | C14—C15—C16—O4 | 178.80 (13) |
C6—C7—C8—C12 | −179.39 (11) | C14—C15—C16—C17 | −0.1 (2) |
C7—C8—C9—C10 | −0.61 (17) | C19—O4—C16—C15 | 176.89 (14) |
C12—C8—C9—C10 | 179.03 (11) | C19—O4—C16—C17 | −4.11 (15) |
C7—C8—C9—C11 | 179.26 (10) | C19—O3—C17—C18 | −176.17 (13) |
C12—C8—C9—C11 | −1.10 (13) | C19—O3—C17—C16 | 4.60 (15) |
C8—C9—C10—C1 | 0.63 (18) | C15—C16—C17—O3 | 178.77 (12) |
C11—C9—C10—C1 | −179.21 (11) | O4—C16—C17—O3 | −0.31 (15) |
C2—C1—C10—C9 | 179.49 (12) | C15—C16—C17—C18 | −0.5 (2) |
C6—C1—C10—C9 | −0.22 (17) | O4—C16—C17—C18 | −179.59 (12) |
C12—O2—C11—O1 | −179.35 (12) | O3—C17—C18—C13 | −178.66 (12) |
C12—O2—C11—C9 | 0.24 (13) | C16—C17—C18—C13 | 0.49 (18) |
C10—C9—C11—O1 | 0.0 (2) | C14—C13—C18—C17 | 0.13 (17) |
C8—C9—C11—O1 | −179.90 (14) | C12—C13—C18—C17 | −175.68 (10) |
C10—C9—C11—O2 | −179.59 (12) | C17—O3—C19—O4 | −7.07 (15) |
C8—C9—C11—O2 | 0.56 (13) | C16—O4—C19—O3 | 6.88 (15) |
Hydrogen-bond geometry (Å, º) topCg1 is the centroid of the C13–C18 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.98 | 2.39 | 3.3277 (16) | 159 |
C3—H3···Cg1ii | 0.93 | 2.84 | 3.6021 (15) | 140 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, −y+2, −z. |
Experimental details
Crystal data |
Chemical formula | C19H12O4 |
Mr | 304.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 7.8617 (3), 12.0417 (4), 15.0214 (5) |
β (°) | 95.848 (2) |
V (Å3) | 1414.65 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.21 × 0.19 × 0.17 |
|
Data collection |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.979, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19039, 4251, 3370 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.711 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.137, 1.02 |
No. of reflections | 4251 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.22 |
Hydrogen-bond geometry (Å, º) topCg1 is the centroid of the C13–C18 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.98 | 2.39 | 3.3277 (16) | 159 |
C3—H3···Cg1ii | 0.93 | 2.84 | 3.6021 (15) | 140 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, −y+2, −z. |
Molecules containing a benzofuran ring system have attracted considerable interest in view of their biological and pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999). Furan compounds exhibit antibacterial and antifungal activities (Valerga et al., 2009). Against this background and in order to obtain detailed information on molecular conformation in the solid state, an X-ray crystallographic study of the title compound has been carried out and the results are presented here.
The 3H-benzo[f]isobenzofuran-1-one ring system is essentially planar, with a maximum deviation of 0.016 (1) Å for atom C12. In the 1,3-benzodioxole ring system, the dioxole ring adopts a flattened envelope conformation with the methylene C at the flap [deviation = 0.104 (2) Å]. The benzene ring of the benzodioxole ring system makes a dihedral angle of 76.45 (5)° with the 3H-benzo[f]isobenzofuran-1-one ring system.
In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) involving atoms C12 and O1, link the molecules into chains which run parallel to the b axis and can be described by a graph set motif of C(5). In addition, the crystal packing is stabilized by C—H···π interactions involving the C13–C18 ring.