Crystal structure of 3-(4-meth­oxy­phen­yl)-2,3-di­hydro-1H-naphtho­[2,1-b]pyran-1-one

Vasanthi, R.; Reuben Jonathan, D.; Elizhlarasi, K.S.; Revathi, B.K.; Usha, G.

doi:10.1107/S2056989015007082

organic compounds

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Volume 71| Part 5| May 2015| Page o332

https://doi.org/10.1107/S2056989015007082

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Crystal structure of 3-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[2,1-b]pyran-1-one

R. Vasanthi,^a D. Reuben Jonathan,^b K. S. Elizhlarasi,^a B. K. Revathi ^a and G. Usha ^a ^*

^aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^bDepartment of Chemistry, Madras Christian College, Chennai-59, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 7 April 2015; accepted 9 April 2015; online 22 April 2015)

In the title compound, C₂₀H₁₆O₃, the hydropyran ring adopts a distorted half-chair conformation with the methine C atom and the ring O atom displaced by −0.554 (2) and 0.158 (1) Å, respectively, from the plane of the other four atoms (r.m.s. deviation = 0.020 Å). Its mean plane (all atoms) is inclined to the naphthalene ring system at a dihedral angle of 11.67 (1)°. The dihedral angle between the napthalene ring system and the phenyl ring is 71.84 (1)°. In the crystal, no diectional interactions beyond van der Waals contacts could be identified.

Keywords: crystal structure; hydropyran; flavone derivative.

CCDC reference: 1058707

1. Related literature

For the biological activity of flavone derivatives, see: Thomas et al. (2013 ); Kumar et al. (2014 ); Lee et al. (2014 ). For further synthetic details, see: Vasanthi et al. (2014 ).

2. Experimental

2.1. Crystal data

C₂₀H₁₆O₃
M_r = 304.33
Monoclinic, P 2₁ /n
a = 7.3612 (3) Å
b = 17.8540 (9) Å
c = 11.9465 (6) Å
β = 105.697 (2)°
V = 1511.54 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.974, T_max = 0.982
33755 measured reflections
3548 independent reflections
2297 reflections with I > 2σ(I)
R_int = 0.035

2.3. Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.171
S = 1.00
3548 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1058707

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015007082/hb7401sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007082/hb7401Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015007082/hb7401Isup3.cml

checkCIF report

Synthesis and crystallization top

The procedure (Vasanthi et al., 2014) adopted in the synthesis of the compound 3-(4-methoxyphenyl)-2,3-dihydro-1H-benzo(f)chromen-1-one is represented here. In a 250 ml round-bottomed flask 2-hydroxy-1-acetonaphthone (0.05 mol) and 4-methoxyoxybenzaldehyde (0.05mol) were placed to which about 100 ml of absolute alcohol was added and stirred at room temperature for a time span of 5 minutes. Then about 10 ml of 40% sodium hydroxide solution was added and the mixture was stirred for 6 hours. On adding ice cold water a precipitate was generated which was filtered, washed with sufficient quantity of distilled water and dried. The crude product was recrystallized twice from chloroform (yield = 86%).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H distance of 0.93-0.97Å with Uiso(H)= 1.5 Ueq(c-methyl) and Uiso(H)= 1.2Ueq(C) for other H atom.

Related literature top

For the biological activity of flavone derivatives, see: Thomas et al. (2013); Kumar et al. (2014); Lee et al. (2014). For further synthetic details, see: Vasanthi et al. (2014).

Structure description top

For the biological activity of flavone derivatives, see: Thomas et al. (2013); Kumar et al. (2014); Lee et al. (2014). For further synthetic details, see: Vasanthi et al. (2014).

Synthesis and crystallization top

Refinement details top

Computing details top

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 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of the molecules in the crystal structure. The dashed lines indicate the hydrogen bonds.

3-(4-Methoxyphenyl)-2,3-dihydro-1H-naphtho[2,1-b]pyran-1-one top

Crystal data top

C₂₀H₁₆O₃	F(000) = 640
M_r = 304.33	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 3548 reflections
a = 7.3612 (3) Å	θ = 2.1–27.7°
b = 17.8540 (9) Å	µ = 0.09 mm⁻¹
c = 11.9465 (6) Å	T = 293 K
β = 105.697 (2)°	Block, pale yellow
V = 1511.54 (12) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3548 independent reflections
Radiation source: fine-focus sealed tube	2297 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and φ scan	θ_max = 27.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
T_min = 0.974, T_max = 0.982	k = −23→23
33755 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0866P)² + 0.5483P] where P = (F_o² + 2F_c²)/3
3548 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₁₆O₃	V = 1511.54 (12) Å³
M_r = 304.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.3612 (3) Å	µ = 0.09 mm⁻¹
b = 17.8540 (9) Å	T = 293 K
c = 11.9465 (6) Å	0.30 × 0.25 × 0.20 mm
β = 105.697 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3548 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2297 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.982	R_int = 0.035
33755 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.00	Δρ_max = 0.35 e Å⁻³
3548 reflections	Δρ_min = −0.21 e Å⁻³
209 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.8210 (3)	0.31670 (11)	0.50857 (17)	0.0479 (5)
H1	0.7380	0.3483	0.4572	0.057*
C2	0.9984 (3)	0.34116 (12)	0.5627 (2)	0.0569 (6)
H2	1.0348	0.3890	0.5468	0.068*
C3	1.1261 (3)	0.29601 (14)	0.6411 (2)	0.0615 (6)
H3	1.2457	0.3139	0.6785	0.074*
C4	1.0749 (3)	0.22571 (13)	0.66264 (19)	0.0552 (5)
H4	1.1603	0.1956	0.7152	0.066*
C5	0.8940 (3)	0.19745 (11)	0.60665 (16)	0.0442 (4)
C6	0.7616 (2)	0.24405 (10)	0.52940 (15)	0.0398 (4)
C7	0.5772 (2)	0.21474 (10)	0.47367 (14)	0.0380 (4)
C8	0.5436 (2)	0.13995 (10)	0.48896 (15)	0.0404 (4)
C9	0.6770 (3)	0.09415 (11)	0.56488 (18)	0.0480 (5)
H9	0.6500	0.0440	0.5741	0.058*
C10	0.8442 (3)	0.12317 (11)	0.62434 (17)	0.0494 (5)
H10	0.9285	0.0935	0.6782	0.059*
C11	0.4166 (3)	0.26181 (11)	0.41137 (16)	0.0444 (4)
C12	0.2355 (3)	0.22029 (11)	0.3582 (2)	0.0534 (5)
H12A	0.1573	0.2214	0.4118	0.064*
H12B	0.1675	0.2456	0.2875	0.064*
C13	0.2685 (3)	0.14097 (11)	0.33062 (18)	0.0478 (5)
H13	0.3405	0.1408	0.2726	0.057*
C14	0.0947 (3)	0.09419 (11)	0.28505 (18)	0.0461 (5)
C15	−0.0210 (3)	0.07528 (12)	0.35425 (18)	0.0537 (5)
H15	0.0094	0.0918	0.4309	0.064*
C16	−0.1816 (3)	0.03216 (12)	0.31180 (18)	0.0514 (5)
H16	−0.2587	0.0201	0.3593	0.062*
C17	−0.2257 (3)	0.00744 (10)	0.19866 (17)	0.0451 (5)
C18	0.0466 (3)	0.06940 (12)	0.17210 (18)	0.0511 (5)
H18	0.1226	0.0818	0.1241	0.061*
C19	−0.1111 (3)	0.02680 (12)	0.12893 (18)	0.0521 (5)
H19	−0.1413	0.0107	0.0520	0.062*
C20	−0.5019 (3)	−0.05604 (15)	0.2142 (3)	0.0741 (7)
H20A	−0.4325	−0.0834	0.2814	0.111*
H20B	−0.6009	−0.0870	0.1684	0.111*
H20C	−0.5558	−0.0120	0.2386	0.111*
O1	0.38066 (18)	0.10428 (7)	0.43445 (12)	0.0496 (4)
O2	0.4204 (2)	0.32953 (8)	0.40683 (15)	0.0635 (5)
O3	−0.3787 (2)	−0.03475 (9)	0.14670 (14)	0.0619 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0537 (11)	0.0423 (11)	0.0461 (11)	−0.0051 (8)	0.0107 (9)	−0.0012 (8)
C2	0.0593 (13)	0.0490 (12)	0.0598 (13)	−0.0147 (10)	0.0116 (10)	−0.0031 (10)
C3	0.0483 (11)	0.0647 (14)	0.0659 (14)	−0.0137 (10)	0.0059 (10)	−0.0081 (11)
C4	0.0475 (11)	0.0594 (13)	0.0524 (12)	0.0030 (9)	0.0026 (9)	−0.0006 (10)
C5	0.0453 (10)	0.0439 (10)	0.0416 (10)	0.0005 (8)	0.0083 (8)	−0.0015 (8)
C6	0.0460 (10)	0.0382 (9)	0.0351 (9)	−0.0008 (7)	0.0110 (7)	−0.0026 (7)
C7	0.0438 (9)	0.0356 (9)	0.0336 (9)	0.0003 (7)	0.0089 (7)	−0.0012 (7)
C8	0.0424 (10)	0.0377 (10)	0.0404 (10)	−0.0021 (7)	0.0103 (7)	0.0002 (8)
C9	0.0535 (11)	0.0367 (10)	0.0514 (11)	0.0010 (8)	0.0099 (9)	0.0069 (8)
C10	0.0523 (11)	0.0460 (11)	0.0451 (11)	0.0071 (9)	0.0047 (9)	0.0066 (9)
C11	0.0499 (10)	0.0365 (10)	0.0443 (10)	0.0010 (8)	0.0084 (8)	0.0005 (8)
C12	0.0491 (11)	0.0445 (11)	0.0597 (13)	0.0020 (8)	0.0029 (9)	0.0016 (9)
C13	0.0472 (11)	0.0463 (11)	0.0473 (11)	−0.0005 (8)	0.0084 (8)	0.0003 (9)
C14	0.0424 (10)	0.0417 (10)	0.0520 (11)	0.0004 (8)	0.0091 (8)	−0.0005 (8)
C15	0.0587 (12)	0.0587 (13)	0.0419 (11)	−0.0037 (10)	0.0104 (9)	−0.0084 (9)
C16	0.0515 (11)	0.0538 (12)	0.0512 (12)	−0.0021 (9)	0.0178 (9)	−0.0032 (9)
C17	0.0414 (10)	0.0399 (10)	0.0520 (11)	0.0015 (8)	0.0093 (8)	−0.0043 (8)
C18	0.0495 (11)	0.0545 (12)	0.0518 (12)	−0.0038 (9)	0.0182 (9)	−0.0047 (9)
C19	0.0536 (11)	0.0571 (13)	0.0461 (11)	−0.0038 (9)	0.0146 (9)	−0.0103 (9)
C20	0.0521 (13)	0.0760 (17)	0.098 (2)	−0.0161 (12)	0.0263 (13)	−0.0099 (15)
O1	0.0474 (8)	0.0395 (7)	0.0554 (8)	−0.0048 (6)	0.0028 (6)	0.0053 (6)
O2	0.0619 (10)	0.0377 (8)	0.0802 (11)	0.0039 (6)	0.0008 (8)	0.0028 (7)
O3	0.0538 (9)	0.0633 (10)	0.0681 (10)	−0.0171 (7)	0.0159 (7)	−0.0162 (8)

Geometric parameters (Å, º) top

C1—C2	1.362 (3)	C12—C13	1.489 (3)
C1—C6	1.413 (3)	C12—H12A	0.9700
C1—H1	0.9300	C12—H12B	0.9700
C2—C3	1.391 (3)	C13—O1	1.448 (2)
C2—H2	0.9300	C13—C14	1.501 (3)
C3—C4	1.355 (3)	C13—H13	0.9800
C3—H3	0.9300	C14—C18	1.372 (3)
C4—C5	1.412 (3)	C14—C15	1.380 (3)
C4—H4	0.9300	C15—C16	1.387 (3)
C5—C10	1.407 (3)	C15—H15	0.9300
C5—C6	1.417 (3)	C16—C17	1.375 (3)
C6—C7	1.439 (2)	C16—H16	0.9300
C7—C8	1.379 (2)	C17—O3	1.357 (2)
C7—C11	1.477 (2)	C17—C19	1.381 (3)
C8—O1	1.359 (2)	C18—C19	1.366 (3)
C8—C9	1.405 (3)	C18—H18	0.9300
C9—C10	1.347 (3)	C19—H19	0.9300
C9—H9	0.9300	C20—O3	1.419 (3)
C10—H10	0.9300	C20—H20A	0.9600
C11—O2	1.211 (2)	C20—H20B	0.9600
C11—C12	1.507 (3)	C20—H20C	0.9600

C2—C1—C6	120.91 (19)	C13—C12—H12B	109.1
C2—C1—H1	119.5	C11—C12—H12B	109.1
C6—C1—H1	119.5	H12A—C12—H12B	107.8
C1—C2—C3	121.3 (2)	O1—C13—C12	109.26 (16)
C1—C2—H2	119.3	O1—C13—C14	106.95 (15)
C3—C2—H2	119.3	C12—C13—C14	115.83 (16)
C4—C3—C2	119.52 (19)	O1—C13—H13	108.2
C4—C3—H3	120.2	C12—C13—H13	108.2
C2—C3—H3	120.2	C14—C13—H13	108.2
C3—C4—C5	121.08 (19)	C18—C14—C15	118.26 (18)
C3—C4—H4	119.5	C18—C14—C13	120.25 (18)
C5—C4—H4	119.5	C15—C14—C13	121.49 (18)
C10—C5—C4	121.09 (18)	C14—C15—C16	121.34 (19)
C10—C5—C6	119.34 (17)	C14—C15—H15	119.3
C4—C5—C6	119.56 (18)	C16—C15—H15	119.3
C1—C6—C5	117.55 (17)	C17—C16—C15	119.26 (19)
C1—C6—C7	123.44 (17)	C17—C16—H16	120.4
C5—C6—C7	118.98 (16)	C15—C16—H16	120.4
C8—C7—C6	118.11 (16)	O3—C17—C16	125.00 (19)
C8—C7—C11	118.04 (16)	O3—C17—C19	115.47 (18)
C6—C7—C11	123.53 (16)	C16—C17—C19	119.52 (18)
O1—C8—C7	123.85 (16)	C19—C18—C14	121.16 (19)
O1—C8—C9	114.13 (16)	C19—C18—H18	119.4
C7—C8—C9	122.01 (17)	C14—C18—H18	119.4
C10—C9—C8	119.73 (18)	C18—C19—C17	120.47 (19)
C10—C9—H9	120.1	C18—C19—H19	119.8
C8—C9—H9	120.1	C17—C19—H19	119.8
C9—C10—C5	121.42 (17)	O3—C20—H20A	109.5
C9—C10—H10	119.3	O3—C20—H20B	109.5
C5—C10—H10	119.3	H20A—C20—H20B	109.5
O2—C11—C7	124.46 (17)	O3—C20—H20C	109.5
O2—C11—C12	120.04 (17)	H20A—C20—H20C	109.5
C7—C11—C12	115.37 (16)	H20B—C20—H20C	109.5
C13—C12—C11	112.50 (16)	C8—O1—C13	115.06 (14)
C13—C12—H12A	109.1	C17—O3—C20	117.87 (18)
C11—C12—H12A	109.1

C6—C1—C2—C3	−0.8 (3)	C8—C7—C11—C12	−7.0 (2)
C1—C2—C3—C4	1.3 (4)	C6—C7—C11—C12	179.61 (17)
C2—C3—C4—C5	0.1 (4)	O2—C11—C12—C13	157.9 (2)
C3—C4—C5—C10	176.6 (2)	C7—C11—C12—C13	−26.1 (2)
C3—C4—C5—C6	−2.0 (3)	C11—C12—C13—O1	55.1 (2)
C2—C1—C6—C5	−1.1 (3)	C11—C12—C13—C14	175.91 (17)
C2—C1—C6—C7	−179.08 (19)	O1—C13—C14—C18	−126.0 (2)
C10—C5—C6—C1	−176.18 (18)	C12—C13—C14—C18	112.0 (2)
C4—C5—C6—C1	2.5 (3)	O1—C13—C14—C15	54.4 (2)
C10—C5—C6—C7	1.9 (3)	C12—C13—C14—C15	−67.7 (3)
C4—C5—C6—C7	−179.48 (17)	C18—C14—C15—C16	0.2 (3)
C1—C6—C7—C8	171.55 (18)	C13—C14—C15—C16	179.89 (18)
C5—C6—C7—C8	−6.4 (3)	C14—C15—C16—C17	0.4 (3)
C1—C6—C7—C11	−15.1 (3)	C15—C16—C17—O3	−179.74 (19)
C5—C6—C7—C11	167.02 (17)	C15—C16—C17—C19	−0.9 (3)
C6—C7—C8—O1	−175.03 (16)	C15—C14—C18—C19	−0.3 (3)
C11—C7—C8—O1	11.2 (3)	C13—C14—C18—C19	−179.97 (19)
C6—C7—C8—C9	5.9 (3)	C14—C18—C19—C17	−0.2 (3)
C11—C7—C8—C9	−167.86 (18)	O3—C17—C19—C18	179.78 (18)
O1—C8—C9—C10	−179.81 (18)	C16—C17—C19—C18	0.9 (3)
C7—C8—C9—C10	−0.7 (3)	C7—C8—O1—C13	20.1 (3)
C8—C9—C10—C5	−4.2 (3)	C9—C8—O1—C13	−160.76 (17)
C4—C5—C10—C9	−175.1 (2)	C12—C13—O1—C8	−52.9 (2)
C6—C5—C10—C9	3.5 (3)	C14—C13—O1—C8	−178.94 (15)
C8—C7—C11—O2	168.8 (2)	C16—C17—O3—C20	−0.9 (3)
C6—C7—C11—O2	−4.6 (3)	C19—C17—O3—C20	−179.7 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆O₃
M_r	304.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.3612 (3), 17.8540 (9), 11.9465 (6)
β (°)	105.697 (2)
V (Å³)	1511.54 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.974, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	33755, 3548, 2297
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.655

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.171, 1.00
No. of reflections	3548
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Acknowledgements

The authors thank SAIF (IIT Madras) for collecting the intensity data.

References

Bruker (2004). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kumar, B., Kumari, B., Singh, N., Ram, B. & Balram, B. (2014). J. Appl. Chem. 3, 1468–1474. CAS Google Scholar
Lee, M. S., Yong, Y., Lee, J. M., Koh, D., Shin, S. Y. & Lee, Y. H. (2014). Biol. Chem. 57, 129–132. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomas, N. & Zachariah, S. M. (2013). Asia. J. Pharm. Clin. Res. 6 (Suppl. 2), 11–15. Google Scholar
Vasanthi, R., Reuben Jonathan, D., Ezhilarasi, K. S., Sathya, S. & Usha, G. (2014). Acta Cryst. E70, o1116–o1117. CSD CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 3-(4-meth­­oxy­phen­yl)-2,3-di­hydro-1H-naphtho­[2,1-b]pyran-1-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 3-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[2,1-b]pyran-1-one