organic compounds
3-(2-Methoxyphenyl)-2,3-dihydro-1H-benzo[f]chromen-1-one
aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
*Correspondence e-mail: dddklab@gmail.com
In the title compound, C20H16O3, the 2-methoxyphenyl ring is tilted by 50.67 (3)° with respect to the naphthyl ring system. The central pyran ring has an with the C atom bearing the pendant ring system as the flap. The methoxy group attached to the benzene ring is slightly twisted [C—C—O—C = −15.2 (1)°] from the ring. In the crystal, weak C—H⋯O interactions link the molecules into C(7) chains propagating along [101].
Keywords: crystal structure; flavanone; C—H⋯O hydrogen bonds.
CCDC reference: 2026731
Structure description
Flavanones are widely used as health-care products because they are found at high concentrations in natural sources (Lichota et al., 2019). Flavanones possess a chromane ring as a common structural feature, but they show a broad spectrum of biological activities depending on the placement of the hydroxyl or methoxy group substituents at different positions of the flavanone skeleton (Lee et al., 2016; Singh et al., 2014). Compounds in which the phenyl group in the chromane ring system is replaced by a naphthyl ring system have shown versatile biological activities and physiochemical properties (Kumar et al., 2017; Shin et al., 2014). Therefore, the naphthyl ring system-containing title flavanone compound, C20H16O3, was synthesized and its was determined.
The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the C2–C11 naphthyl ring system (r.m.s. deviation = 0.026 Å) and the C14–C19 2-methoxyphenyl ring is 50.67 (3)°. The central pyran ring (C1/C2/C11/O2/C12/C13) has an with atom C12 as the flap, which is displaced by 0.691 (2) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.023 Å). In the arbitrarily chosen asymmetric molecule, C12 has an R configuration but crystal symmetry generates a The hydrogen atom H12 attached to C12 forms a trans diaxial conformation with one of H atoms of the C13 methylene group (H12—C12—C13—H13A = 179°] and a gauche conformation with the other methylene H atom H13B (H12—C12—C13—H13B = 61°). The methoxy group in the benzene ring is slightly tilted [C16—C15—O3—C20 = −15.2 (2)°] from the ring.
In the crystal, weak C—H⋯O interactions link the molecules into C(7) chains propagating along [101] (Table 1, Fig. 2) with adjacent molecules in the chain related by n-glide symmetry.
Synthesis and crystallization
The synthetic scheme for the preparation of the title compound is shown in Fig. 3: 2-hydroxy-1-acetonaphthone (I, 372 mg, 2 mmol) and 2-methoxybenzaldehyde (II, 272 mg, 2 mmol) were dissolved in ethanol (20 ml) and the temperature was adjusted to around 276–277 K in an ice-bath. To the cooled reaction mixture was added 1.5 ml of 50% aqueous KOH solution, and the reaction mixture was stirred at room temperature for 24 h. The mixture was poured into iced water (80 ml) and was acidified with 6 N HCl solution. The mixture was extracted with ethyl acetate (3 × 40 ml) and the combined organic layers were dried with MgSO4. Filtration and evaporation of the filtrate gave a solid product of chalcone (III), which was used for next reaction: the solid was dissolved in DMSO and a catalytic amount of conc. HCl was added. After stirring for 10 h, the reaction mixture was poured into iced water to give a solid product of the title flavanone and yellow blocks were recovered by recrystallization from ethanol solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2026731
https://doi.org/10.1107/S2414314620012092/hb4362sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620012092/hb4362Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620012092/hb4362Isup3.cml
Data collection: APEX2 (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).C20H16O3 | F(000) = 640 |
Mr = 304.33 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.4519 (5) Å | Cell parameters from 9975 reflections |
b = 7.8785 (3) Å | θ = 2.7–28.3° |
c = 15.6680 (7) Å | µ = 0.09 mm−1 |
β = 105.2534 (16)° | T = 223 K |
V = 1482.92 (11) Å3 | Block, yellow |
Z = 4 | 0.21 × 0.14 × 0.10 mm |
PHOTON 100 CMOS diffractometer | 2879 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.049 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | θmax = 28.4°, θmin = 2.7° |
Tmin = 0.691, Tmax = 0.746 | h = −16→16 |
40884 measured reflections | k = −10→10 |
3704 independent reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0466P)2 + 0.6269P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3704 reflections | Δρmax = 0.32 e Å−3 |
209 parameters | Δρmin = −0.20 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.02968 (9) | 0.67451 (14) | 0.13018 (7) | 0.0408 (3) | |
C1 | 0.96744 (11) | 0.55251 (17) | 0.11882 (8) | 0.0277 (3) | |
C2 | 0.87200 (10) | 0.52818 (17) | 0.04044 (8) | 0.0254 (3) | |
C3 | 0.83775 (10) | 0.65224 (17) | −0.02963 (8) | 0.0256 (3) | |
C4 | 0.88498 (11) | 0.81647 (18) | −0.02699 (9) | 0.0319 (3) | |
H4 | 0.9442 | 0.8475 | 0.0214 | 0.038* | |
C5 | 0.84549 (12) | 0.93097 (19) | −0.09406 (10) | 0.0373 (3) | |
H5 | 0.8778 | 1.0394 | −0.0906 | 0.045* | |
C6 | 0.75818 (12) | 0.8889 (2) | −0.16720 (10) | 0.0383 (3) | |
H6 | 0.7318 | 0.9687 | −0.2125 | 0.046* | |
C7 | 0.71140 (12) | 0.7314 (2) | −0.17257 (9) | 0.0344 (3) | |
H7 | 0.6531 | 0.7029 | −0.2221 | 0.041* | |
C8 | 0.74920 (11) | 0.61053 (18) | −0.10475 (8) | 0.0279 (3) | |
C9 | 0.69968 (11) | 0.44738 (19) | −0.11078 (9) | 0.0312 (3) | |
H9 | 0.6434 | 0.4186 | −0.1616 | 0.037* | |
C10 | 0.73167 (11) | 0.33232 (18) | −0.04500 (9) | 0.0308 (3) | |
H10 | 0.6983 | 0.2245 | −0.0504 | 0.037* | |
C11 | 0.81568 (11) | 0.37503 (17) | 0.03210 (8) | 0.0268 (3) | |
O2 | 0.83415 (8) | 0.25362 (12) | 0.09597 (6) | 0.0327 (2) | |
C12 | 0.88068 (11) | 0.31806 (18) | 0.18418 (8) | 0.0284 (3) | |
H12 | 0.8275 | 0.4002 | 0.1981 | 0.034* | |
C13 | 0.98756 (11) | 0.41041 (18) | 0.18597 (9) | 0.0301 (3) | |
H13A | 1.0414 | 0.3302 | 0.1732 | 0.036* | |
H13B | 1.0193 | 0.4572 | 0.2452 | 0.036* | |
C14 | 0.89365 (11) | 0.17138 (18) | 0.24762 (9) | 0.0290 (3) | |
C15 | 0.89304 (11) | 0.20426 (18) | 0.33543 (9) | 0.0301 (3) | |
C16 | 0.90122 (12) | 0.0723 (2) | 0.39537 (10) | 0.0352 (3) | |
H16 | 0.9000 | 0.0947 | 0.4540 | 0.042* | |
C17 | 0.91114 (12) | −0.0927 (2) | 0.36806 (10) | 0.0381 (3) | |
H17 | 0.9166 | −0.1824 | 0.4086 | 0.046* | |
C18 | 0.91317 (13) | −0.1273 (2) | 0.28268 (11) | 0.0398 (3) | |
H18 | 0.9203 | −0.2397 | 0.2649 | 0.048* | |
C19 | 0.90462 (12) | 0.00531 (19) | 0.22271 (10) | 0.0358 (3) | |
H19 | 0.9063 | −0.0184 | 0.1643 | 0.043* | |
O3 | 0.88502 (9) | 0.37221 (13) | 0.35620 (7) | 0.0398 (3) | |
C20 | 0.85783 (17) | 0.4093 (2) | 0.43593 (11) | 0.0520 (5) | |
H20A | 0.7929 | 0.3441 | 0.4391 | 0.078* | |
H20B | 0.8418 | 0.5295 | 0.4381 | 0.078* | |
H20C | 0.9200 | 0.3799 | 0.4855 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0417 (6) | 0.0414 (6) | 0.0332 (6) | −0.0146 (5) | −0.0011 (4) | 0.0012 (5) |
C1 | 0.0279 (6) | 0.0315 (7) | 0.0237 (6) | −0.0012 (5) | 0.0070 (5) | −0.0024 (5) |
C2 | 0.0248 (6) | 0.0290 (7) | 0.0224 (6) | −0.0004 (5) | 0.0063 (5) | −0.0012 (5) |
C3 | 0.0255 (6) | 0.0289 (7) | 0.0237 (6) | 0.0009 (5) | 0.0086 (5) | −0.0009 (5) |
C4 | 0.0314 (7) | 0.0320 (7) | 0.0317 (7) | −0.0033 (6) | 0.0072 (5) | −0.0011 (6) |
C5 | 0.0384 (8) | 0.0297 (7) | 0.0447 (8) | −0.0017 (6) | 0.0124 (6) | 0.0056 (6) |
C6 | 0.0364 (8) | 0.0393 (8) | 0.0391 (8) | 0.0066 (6) | 0.0094 (6) | 0.0141 (7) |
C7 | 0.0299 (7) | 0.0422 (8) | 0.0289 (7) | 0.0034 (6) | 0.0036 (5) | 0.0060 (6) |
C8 | 0.0258 (6) | 0.0338 (7) | 0.0242 (6) | 0.0011 (5) | 0.0066 (5) | 0.0008 (5) |
C9 | 0.0289 (7) | 0.0384 (8) | 0.0235 (6) | −0.0041 (6) | 0.0022 (5) | −0.0024 (6) |
C10 | 0.0317 (7) | 0.0315 (7) | 0.0280 (7) | −0.0075 (5) | 0.0059 (5) | −0.0031 (6) |
C11 | 0.0287 (6) | 0.0288 (6) | 0.0233 (6) | 0.0001 (5) | 0.0078 (5) | 0.0012 (5) |
O2 | 0.0403 (5) | 0.0299 (5) | 0.0248 (5) | −0.0056 (4) | 0.0033 (4) | 0.0037 (4) |
C12 | 0.0297 (6) | 0.0319 (7) | 0.0228 (6) | 0.0005 (5) | 0.0054 (5) | 0.0019 (5) |
C13 | 0.0273 (6) | 0.0369 (7) | 0.0248 (6) | 0.0000 (6) | 0.0044 (5) | 0.0019 (5) |
C14 | 0.0257 (6) | 0.0322 (7) | 0.0286 (7) | 0.0021 (5) | 0.0064 (5) | 0.0051 (6) |
C15 | 0.0274 (6) | 0.0326 (7) | 0.0305 (7) | 0.0004 (5) | 0.0083 (5) | 0.0036 (6) |
C16 | 0.0352 (7) | 0.0413 (8) | 0.0285 (7) | −0.0005 (6) | 0.0073 (6) | 0.0078 (6) |
C17 | 0.0354 (7) | 0.0359 (8) | 0.0419 (8) | 0.0025 (6) | 0.0083 (6) | 0.0143 (7) |
C18 | 0.0409 (8) | 0.0316 (7) | 0.0465 (9) | 0.0056 (6) | 0.0110 (7) | 0.0039 (7) |
C19 | 0.0380 (8) | 0.0365 (8) | 0.0329 (7) | 0.0045 (6) | 0.0095 (6) | 0.0019 (6) |
O3 | 0.0562 (7) | 0.0342 (6) | 0.0333 (6) | 0.0010 (5) | 0.0192 (5) | 0.0029 (4) |
C20 | 0.0748 (12) | 0.0454 (10) | 0.0433 (9) | 0.0065 (9) | 0.0290 (9) | −0.0019 (8) |
O1—C1 | 1.2180 (16) | O2—C12 | 1.4430 (16) |
C1—C2 | 1.4796 (17) | C12—C14 | 1.5050 (18) |
C1—C13 | 1.5114 (18) | C12—C13 | 1.5105 (18) |
C2—C11 | 1.3844 (18) | C12—H12 | 0.9900 |
C2—C3 | 1.4478 (18) | C13—H13A | 0.9800 |
C3—C4 | 1.4173 (19) | C13—H13B | 0.9800 |
C3—C8 | 1.4235 (18) | C14—C19 | 1.382 (2) |
C4—C5 | 1.374 (2) | C14—C15 | 1.4020 (19) |
C4—H4 | 0.9400 | C15—O3 | 1.3725 (17) |
C5—C6 | 1.396 (2) | C15—C16 | 1.3869 (19) |
C5—H5 | 0.9400 | C16—C17 | 1.384 (2) |
C6—C7 | 1.364 (2) | C16—H16 | 0.9400 |
C6—H6 | 0.9400 | C17—C18 | 1.372 (2) |
C7—C8 | 1.4123 (19) | C17—H17 | 0.9400 |
C7—H7 | 0.9400 | C18—C19 | 1.390 (2) |
C8—C9 | 1.4179 (19) | C18—H18 | 0.9400 |
C9—C10 | 1.3515 (19) | C19—H19 | 0.9400 |
C9—H9 | 0.9400 | O3—C20 | 1.4083 (18) |
C10—C11 | 1.4149 (18) | C20—H20A | 0.9700 |
C10—H10 | 0.9400 | C20—H20B | 0.9700 |
C11—O2 | 1.3595 (15) | C20—H20C | 0.9700 |
O1—C1—C2 | 124.39 (12) | C14—C12—C13 | 114.63 (11) |
O1—C1—C13 | 120.01 (12) | O2—C12—H12 | 108.5 |
C2—C1—C13 | 115.57 (11) | C14—C12—H12 | 108.5 |
C11—C2—C3 | 118.42 (11) | C13—C12—H12 | 108.5 |
C11—C2—C1 | 117.88 (12) | C12—C13—C1 | 111.10 (11) |
C3—C2—C1 | 123.64 (12) | C12—C13—H13A | 109.4 |
C4—C3—C8 | 117.39 (12) | C1—C13—H13A | 109.4 |
C4—C3—C2 | 123.84 (12) | C12—C13—H13B | 109.4 |
C8—C3—C2 | 118.73 (12) | C1—C13—H13B | 109.4 |
C5—C4—C3 | 120.98 (13) | H13A—C13—H13B | 108.0 |
C5—C4—H4 | 119.5 | C19—C14—C15 | 118.58 (13) |
C3—C4—H4 | 119.5 | C19—C14—C12 | 122.80 (12) |
C4—C5—C6 | 121.10 (14) | C15—C14—C12 | 118.61 (12) |
C4—C5—H5 | 119.4 | O3—C15—C16 | 124.01 (13) |
C6—C5—H5 | 119.4 | O3—C15—C14 | 115.49 (12) |
C7—C6—C5 | 119.62 (14) | C16—C15—C14 | 120.50 (13) |
C7—C6—H6 | 120.2 | C17—C16—C15 | 119.44 (14) |
C5—C6—H6 | 120.2 | C17—C16—H16 | 120.3 |
C6—C7—C8 | 120.98 (13) | C15—C16—H16 | 120.3 |
C6—C7—H7 | 119.5 | C18—C17—C16 | 120.90 (14) |
C8—C7—H7 | 119.5 | C18—C17—H17 | 119.5 |
C7—C8—C9 | 120.54 (12) | C16—C17—H17 | 119.5 |
C7—C8—C3 | 119.91 (13) | C17—C18—C19 | 119.50 (15) |
C9—C8—C3 | 119.54 (12) | C17—C18—H18 | 120.2 |
C10—C9—C8 | 121.43 (12) | C19—C18—H18 | 120.2 |
C10—C9—H9 | 119.3 | C14—C19—C18 | 121.06 (14) |
C8—C9—H9 | 119.3 | C14—C19—H19 | 119.5 |
C9—C10—C11 | 119.67 (13) | C18—C19—H19 | 119.5 |
C9—C10—H10 | 120.2 | C15—O3—C20 | 117.37 (12) |
C11—C10—H10 | 120.2 | O3—C20—H20A | 109.5 |
O2—C11—C2 | 124.08 (12) | O3—C20—H20B | 109.5 |
O2—C11—C10 | 113.89 (12) | H20A—C20—H20B | 109.5 |
C2—C11—C10 | 122.02 (12) | O3—C20—H20C | 109.5 |
C11—O2—C12 | 113.89 (10) | H20A—C20—H20C | 109.5 |
O2—C12—C14 | 107.98 (11) | H20B—C20—H20C | 109.5 |
O2—C12—C13 | 108.49 (10) | ||
O1—C1—C2—C11 | 173.33 (13) | C9—C10—C11—C2 | −4.2 (2) |
C13—C1—C2—C11 | −4.76 (17) | C2—C11—O2—C12 | 24.36 (17) |
O1—C1—C2—C3 | −3.7 (2) | C10—C11—O2—C12 | −155.02 (11) |
C13—C1—C2—C3 | 178.17 (11) | C11—O2—C12—C14 | 178.52 (10) |
C11—C2—C3—C4 | 176.81 (12) | C11—O2—C12—C13 | −56.70 (14) |
C1—C2—C3—C4 | −6.14 (19) | O2—C12—C13—C1 | 57.80 (14) |
C11—C2—C3—C8 | −1.15 (18) | C14—C12—C13—C1 | 178.55 (11) |
C1—C2—C3—C8 | 175.91 (12) | O1—C1—C13—C12 | 154.04 (13) |
C8—C3—C4—C5 | 0.76 (19) | C2—C1—C13—C12 | −27.78 (16) |
C2—C3—C4—C5 | −177.22 (13) | O2—C12—C14—C19 | 24.76 (17) |
C3—C4—C5—C6 | −0.4 (2) | C13—C12—C14—C19 | −96.26 (16) |
C4—C5—C6—C7 | −0.3 (2) | O2—C12—C14—C15 | −154.33 (12) |
C5—C6—C7—C8 | 0.6 (2) | C13—C12—C14—C15 | 84.64 (15) |
C6—C7—C8—C9 | 179.72 (14) | C19—C14—C15—O3 | 178.25 (12) |
C6—C7—C8—C3 | −0.3 (2) | C12—C14—C15—O3 | −2.62 (18) |
C4—C3—C8—C7 | −0.40 (18) | C19—C14—C15—C16 | −1.2 (2) |
C2—C3—C8—C7 | 177.69 (12) | C12—C14—C15—C16 | 177.95 (12) |
C4—C3—C8—C9 | 179.58 (12) | O3—C15—C16—C17 | −178.74 (13) |
C2—C3—C8—C9 | −2.33 (18) | C14—C15—C16—C17 | 0.6 (2) |
C7—C8—C9—C10 | −177.34 (13) | C15—C16—C17—C18 | 0.1 (2) |
C3—C8—C9—C10 | 2.7 (2) | C16—C17—C18—C19 | −0.3 (2) |
C8—C9—C10—C11 | 0.5 (2) | C15—C14—C19—C18 | 1.0 (2) |
C3—C2—C11—O2 | −174.87 (11) | C12—C14—C19—C18 | −178.10 (13) |
C1—C2—C11—O2 | 7.90 (19) | C17—C18—C19—C14 | −0.3 (2) |
C3—C2—C11—C10 | 4.46 (19) | C16—C15—O3—C20 | −15.2 (2) |
C1—C2—C11—C10 | −172.76 (12) | C14—C15—O3—C20 | 165.38 (14) |
C9—C10—C11—O2 | 175.16 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1i | 0.94 | 2.60 | 3.3973 (17) | 142 |
Symmetry code: (i) x−1/2, −y+3/2, z−1/2. |
Funding information
This work was supported by a Dongduk Women's University grant.
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