3-(2-Meth­oxy­phen­yl)-2,3-di­hydro-1H-benzo[f]chromen-1-one

Sung, J.

doi:10.1107/S2414314620012092

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 9| September 2020| x201209

https://doi.org/10.1107/S2414314620012092

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access

3-(2-Methoxyphenyl)-2,3-dihydro-1H-benzo[f]chromen-1-one

Jiha Sung ^a ^*

^aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
^*Correspondence e-mail: dddklab@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 August 2020; accepted 1 September 2020; online 8 September 2020)

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 envelope conformation 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 crystal structure 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 envelope conformation 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 racemic mixture. 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.

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

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.

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Part of the crystal structure of the title compound, showing the weak C—H⋯O hydrogen bonds as blue lines. H atoms not involved in these interactions have been omitted for clarity.

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.

Figure 3
A synthetic scheme for the preparation of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₆O₃
M_r	304.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	223
a, b, c (Å)	12.4519 (5), 7.8785 (3), 15.6680 (7)
β (°)	105.2534 (16)
V (Å³)	1482.92 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.21 × 0.14 × 0.10

Data collection
Diffractometer	PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2012 )
T_min, T_max	0.691, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	40884, 3704, 2879
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.113, 1.03
No. of reflections	3704
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.20
Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXS and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 )and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2026731

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314620012092/hb4362sup1.cif

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

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: 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).

3-(2-Methoxyphenyl)-2,3-dihydro-1H-benzo[f]chromen-1-one top

Crystal data top

C₂₀H₁₆O₃	F(000) = 640
M_r = 304.33	D_x = 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

Data collection top

PHOTON 100 CMOS diffractometer	2879 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.049
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θ_max = 28.4°, θ_min = 2.7°
T_min = 0.691, T_max = 0.746	h = −16→16
40884 measured reflections	k = −10→10
3704 independent reflections	l = −20→20

Refinement top

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(F_o²) + (0.0466P)² + 0.6269P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3704 reflections	Δρ_max = 0.32 e Å⁻³
209 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

References

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