1-(5-Hy­droxy-2,2,8,8-tetra­methyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one

Pawar, S.; Gopaul, K.; Moodley, T.; Omondi, B.; Koorbanally, N.

doi:10.1107/S1600536813005734

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o484

doi:10.1107/S1600536813005734

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1-(5-Hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one

Sunayna Pawar,^a Kaalin Gopaul,^a Thrineshan Moodley,^a Bernard Omondi ^a and Neil Koorbanally ^a ^*

^aSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: koorbanally@ukzn.ac.za

(Received 18 February 2013; accepted 27 February 2013; online 2 March 2013)

In the biologically active title compound, C₂₆H₂₆O₅, the pyran ring of the chromene unit adopts a half-chair conformation. The C=C double bond of the propenone unit exhibits a trans conformation and the carbonyl group is syn conformation to the double bond. The dihedral angle between the benzene ring and the benzopyranone moiety is 31.54 (4)°. The molecular structure is stabilized by an intramolecular C=O⋯H—O hydrogen bond.

Related literature

For related structures, see: Bhattacharyya et al. (1999 ); Lee & Li (2007 ); Lin et al. (1992 ); Narender et al. (2005 ); Liu et al. (2005 ). For the biological activity of similar molecules, see: Nicolaou et al. (2000 ); Dhar (1981 ). For bond lengths and angles in related structures, see: Bhattacharyya et al. (1999); Pawar et al. (2012 ).

Experimental

Crystal data

C₂₆H₂₆O₅
M_r = 418.47
Monoclinic, P 2₁ /c
a = 9.6422 (2) Å
b = 12.0871 (3) Å
c = 18.4517 (4) Å
β = 99.228 (1)°
V = 2122.64 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 446 K
0.37 × 0.33 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.968, T_max = 0.981
68753 measured reflections
5126 independent reflections
4677 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.01
5126 reflections
286 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82	1.72	2.4523 (10)	148

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); 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: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813005734/ff2099sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005734/ff2099Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813005734/ff2099Isup3.cml

checkCIF report

Comment top

Chalcones are considered to be the primary precursors and constitute important intermediates in the synthesis of flavonoids. Pyranochromenechalcone is a core structure in various naturally active compounds (Nicolaou et al., 2000). Chalcones are synthesized by the Claisen-Schmidt condensation of an aldehyde and ketone using a base as a catalyst, which is followed by dehydration. Chalcones possess antifungal, antioxidant,anti-inflammatory, antimalarial and antileishmanial activity amongst others (Dhar, 1981). With this in mind, a series of chalcones have been synthesized in our laboratory and their biological activity is currently under investigation.

The title compound is a 2-hydroxychalcone, with a central tricyclic core and a peripheral aromatic ring (Lee & Li 2007). The middle ring of the tricyclic core is fully substituted while the pyran rings have two unsubstituted sites. The pyran rings of the chromene unit forms a half chair conformation [Q = 0.3750 (10) Å, θ = 66.86 (15)° and ψ = 39.54 (17) °]. The C8— C9—C10—C11 torsion angle is 160.57 (9) Å, indicating a trans configuration of the double bond. This is supported by ¹H NMR spectroscopy where a trans arrangement of the H atoms in the —CH = CH— group is evident by the coupling constant of J = 15.6 Hz. The carbonyl group is in a cis configuration with respect to the double bond (Liu et al. 2005). The dihedral angle between the phenyl ring and the benzopyranone moiety is 31.54 (4)°. Bond angles and lenghs are within normal ranges relative to reported compounds (Bhattacharyya et al.,1999; Pawar et al., 2012).

Related literature top

For related structures, see: Bhattacharyya et al. (1999); Lee & Li (2007); Lin et al. (1992); Narender et al. (2005); Liu et al. (2005). For the biological activity of similar molecules, see: Nicolaou et al. (2000); Dhar (1981). For bond lengths and angles in related structures, see: Bhattacharyya et al. (1999); Pawar et al. (2012).

Experimental top

Potassium hydroxide (112 mg, 0.7 mmol) and 4-methoxybenzaldehyde (95 mg, 0.7 mmol) was added to a solution of octandrenolone (150 mg, 0.5 mmol) in ethanol (10 ml) and water (2 ml) at room temperature. The reaction mixture was stirred for 48 h at room temperature. The solvent was then distilled off under reduced pressure and the residue dissolved in water (20 ml). The solution was then acidified with 2 N-HCl (20 ml) and the mixture extracted with ethyl acetate (3 × 30 ml), washed with water, and dried over anhydrous MgSO₄. Removal of the solvent followed by flash column chromatography on silica gel gave the pure compound (178 mg, 85%) as a brown solid with a m.p. of 125 - 126 ^oC.

¹HNMR (400 MHz, CDCl₃): 14.49 (1H, s), 8.00 (1H, d, J = 15.56 Hz), 7.76 (1H, d, J = 15.56 Hz), 7.55 (2H, d, J = 8.32 Hz), 6.93 (2H, d, J = 8.32 Hz), 6.69 (1H, d, J = 10.0 Hz), 6.61 (1H,d, J = 10.0 Hz), 5.47 (2H, d, J= 10.0 Hz), 3.85 (3H, s), 1.55 (6H, s), 1.45 (6H, s)

¹³C NMR (100 MHz, CDCl₃): 193.0, 161.7, 161.5, 156.3, 155.3, 142.4, 130.1, 128.6, 125.5, 125.4, 124.9, 116.8, 116.5, 114.5, 106.1, 102.8, 102.7, 78.3, 78.4, 55.6, 28.3, 28.6

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); 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: WinGX (Farrugia, 2012).

Figures top

Fig. 1. ORTEP diagram showing the molecular structure of the titled compound with atomic labelling scheme. Non-H atoms are drawn with 50% probability displacement ellipsoids and H atoms are shown as open circles.

1-(5-Hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₂₆H₂₆O₅	F(000) = 888
M_r = 418.47	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 71516 reflections
a = 9.6422 (2) Å	θ = 2.0–28°
b = 12.0871 (3) Å	µ = 0.09 mm⁻¹
c = 18.4517 (4) Å	T = 446 K
β = 99.228 (1)°	Block, brown
V = 2122.64 (8) Å³	0.37 × 0.33 × 0.21 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4677 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 28°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
T_min = 0.968, T_max = 0.981	k = −15→15
68753 measured reflections	l = −24→24
5126 independent reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0564P)² + 0.9316P] where P = (F_o² + 2F_c²)/3
5126 reflections	(Δ/σ)_max = 0.003
286 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₆H₂₆O₅	V = 2122.64 (8) Å³
M_r = 418.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6422 (2) Å	µ = 0.09 mm⁻¹
b = 12.0871 (3) Å	T = 446 K
c = 18.4517 (4) Å	0.37 × 0.33 × 0.21 mm
β = 99.228 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5126 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4677 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.981	R_int = 0.020
68753 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	Δρ_max = 0.38 e Å⁻³
5126 reflections	Δρ_min = −0.23 e Å⁻³
286 parameters

Special details top

Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.96 Å for Me H atoms and 0.93 Å for aromatic H atoms; U_iso(H) = 1.2U_eq(C) (1.5 for Me groups)] and were included in the refinement in the riding model approximation. The O—H H-atom was located in a difference map and also placed in calculated position O—H = 0.84 Å (U_iso(H) = 1.2U_eq(O).

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. >>> The Following Model ALERT was generated - (Acta-Mode) <<< Format: alert-number_ALERT_alert-type_alert-level text 918_ALERT_3_C Reflection(s) # with I(obs) much smaller I(calc) 1 NOTED:

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

	x	y	z	U_iso*/U_eq
C1	0.14616 (10)	0.12942 (8)	0.45580 (6)	0.0187 (2)
C2	0.12410 (11)	0.11703 (8)	0.52813 (6)	0.0207 (2)
H2	0.1144	0.0468	0.5473	0.025*
C3	0.11675 (11)	0.20968 (9)	0.57126 (6)	0.0192 (2)
H3	0.1007	0.201	0.6193	0.023*
C4	0.13298 (10)	0.31683 (8)	0.54411 (5)	0.01655 (19)
C5	0.15481 (10)	0.32699 (8)	0.47122 (6)	0.0179 (2)
H5	0.1655	0.397	0.452	0.022*
C6	0.16087 (11)	0.23495 (9)	0.42712 (6)	0.0190 (2)
H6	0.1747	0.2434	0.3787	0.023*
C7	0.17381 (13)	0.04268 (10)	0.34274 (6)	0.0282 (2)
H7A	0.0998	0.0862	0.3156	0.042*
H7B	0.1735	−0.0298	0.3215	0.042*
H7C	0.2626	0.0777	0.341	0.042*
C8	0.12434 (10)	0.41146 (8)	0.59236 (5)	0.01725 (19)
H8	0.096	0.3965	0.6372	0.021*
C9	0.15272 (10)	0.51777 (8)	0.57928 (5)	0.01690 (19)
H9	0.1821	0.538	0.5355	0.02*
C10	0.13665 (10)	0.60171 (8)	0.63516 (5)	0.01499 (18)
C11	0.20284 (9)	0.71156 (8)	0.63883 (5)	0.01365 (18)
C12	0.17283 (10)	0.78670 (8)	0.69429 (5)	0.01453 (18)
C13	0.23344 (10)	0.89200 (8)	0.70296 (5)	0.01503 (19)
C14	0.19923 (10)	0.97192 (8)	0.75649 (6)	0.0185 (2)
H14	0.1228	0.9603	0.7806	0.022*
C15	0.27897 (11)	1.06184 (9)	0.77042 (6)	0.0200 (2)
H15	0.2537	1.1163	0.8014	0.024*
C16	0.40971 (10)	1.07586 (8)	0.73628 (5)	0.01676 (19)
C17	0.53457 (11)	1.01888 (9)	0.78265 (6)	0.0195 (2)
H17A	0.5159	0.9411	0.7853	0.029*
H17B	0.5492	1.0497	0.8312	0.029*
H17C	0.6172	1.03	0.7606	0.029*
C18	0.44156 (12)	1.19660 (9)	0.72296 (6)	0.0227 (2)
H18A	0.5228	1.2014	0.6991	0.034*
H18B	0.4595	1.235	0.7691	0.034*
H18C	0.3625	1.2297	0.6923	0.034*
C19	0.32725 (10)	0.92351 (8)	0.65633 (5)	0.01412 (18)
C20	0.35864 (10)	0.85484 (8)	0.60002 (5)	0.01394 (18)
C21	0.29703 (10)	0.74988 (8)	0.59257 (5)	0.01330 (18)
C22	0.38220 (10)	0.72295 (8)	0.47666 (5)	0.01553 (19)
C23	0.47626 (10)	0.82157 (8)	0.49591 (5)	0.01718 (19)
H23	0.5448	0.8386	0.4675	0.021*
C24	0.46159 (10)	0.88436 (8)	0.55330 (5)	0.01615 (19)
H24	0.517	0.9471	0.5637	0.019*
C25	0.45997 (12)	0.62799 (9)	0.44730 (6)	0.0212 (2)
H25A	0.5382	0.6066	0.4836	0.032*
H25B	0.4935	0.6511	0.4034	0.032*
H25C	0.3975	0.5663	0.4364	0.032*
C26	0.25010 (12)	0.75443 (9)	0.42370 (6)	0.0224 (2)
H26A	0.1905	0.6908	0.414	0.034*
H26B	0.2758	0.7808	0.3786	0.034*
H26C	0.2008	0.8116	0.4452	0.034*
O1	0.15230 (9)	0.03378 (6)	0.41723 (5)	0.02628 (18)
O2	0.06220 (8)	0.57627 (6)	0.68277 (4)	0.02028 (16)
O3	0.08410 (8)	0.75943 (6)	0.74064 (4)	0.01852 (16)
H3A	0.0569	0.6957	0.7326	0.028*
O4	0.38941 (7)	1.02473 (6)	0.66293 (4)	0.01655 (15)
O5	0.33812 (7)	0.67778 (6)	0.54356 (4)	0.01567 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0172 (4)	0.0153 (5)	0.0231 (5)	0.0006 (3)	0.0014 (4)	−0.0037 (4)
C2	0.0228 (5)	0.0137 (4)	0.0249 (5)	−0.0015 (4)	0.0021 (4)	0.0022 (4)
C3	0.0206 (5)	0.0182 (5)	0.0186 (5)	−0.0020 (4)	0.0025 (4)	0.0018 (4)
C4	0.0138 (4)	0.0148 (4)	0.0204 (5)	−0.0014 (3)	0.0009 (3)	−0.0007 (4)
C5	0.0176 (4)	0.0145 (4)	0.0213 (5)	−0.0017 (3)	0.0022 (4)	0.0014 (4)
C6	0.0192 (5)	0.0191 (5)	0.0186 (5)	−0.0006 (4)	0.0027 (4)	−0.0001 (4)
C7	0.0337 (6)	0.0257 (6)	0.0239 (5)	0.0054 (5)	0.0010 (4)	−0.0075 (4)
C8	0.0166 (4)	0.0175 (5)	0.0175 (4)	−0.0014 (3)	0.0022 (3)	−0.0001 (4)
C9	0.0166 (4)	0.0170 (5)	0.0173 (4)	−0.0031 (3)	0.0035 (3)	−0.0013 (4)
C10	0.0144 (4)	0.0145 (4)	0.0158 (4)	−0.0011 (3)	0.0018 (3)	0.0015 (3)
C11	0.0140 (4)	0.0131 (4)	0.0139 (4)	−0.0006 (3)	0.0022 (3)	0.0000 (3)
C12	0.0134 (4)	0.0162 (4)	0.0142 (4)	0.0003 (3)	0.0029 (3)	0.0007 (3)
C13	0.0150 (4)	0.0147 (4)	0.0155 (4)	0.0002 (3)	0.0025 (3)	−0.0017 (3)
C14	0.0177 (4)	0.0188 (5)	0.0200 (5)	0.0013 (4)	0.0062 (4)	−0.0030 (4)
C15	0.0224 (5)	0.0173 (5)	0.0213 (5)	0.0013 (4)	0.0064 (4)	−0.0056 (4)
C16	0.0215 (5)	0.0131 (4)	0.0157 (4)	−0.0023 (3)	0.0030 (3)	−0.0033 (3)
C17	0.0214 (5)	0.0187 (5)	0.0181 (5)	−0.0015 (4)	0.0021 (4)	−0.0009 (4)
C18	0.0303 (5)	0.0136 (5)	0.0239 (5)	−0.0037 (4)	0.0029 (4)	−0.0018 (4)
C19	0.0154 (4)	0.0117 (4)	0.0147 (4)	−0.0003 (3)	0.0006 (3)	0.0006 (3)
C20	0.0152 (4)	0.0136 (4)	0.0131 (4)	−0.0008 (3)	0.0024 (3)	0.0008 (3)
C21	0.0144 (4)	0.0131 (4)	0.0123 (4)	0.0008 (3)	0.0018 (3)	−0.0002 (3)
C22	0.0191 (4)	0.0150 (4)	0.0135 (4)	−0.0009 (3)	0.0057 (3)	0.0002 (3)
C23	0.0183 (4)	0.0166 (4)	0.0177 (4)	−0.0022 (3)	0.0062 (3)	0.0018 (4)
C24	0.0175 (4)	0.0144 (4)	0.0168 (4)	−0.0031 (3)	0.0035 (3)	0.0017 (3)
C25	0.0270 (5)	0.0171 (5)	0.0220 (5)	0.0009 (4)	0.0112 (4)	−0.0011 (4)
C26	0.0233 (5)	0.0236 (5)	0.0193 (5)	0.0004 (4)	0.0000 (4)	0.0003 (4)
O1	0.0366 (4)	0.0160 (4)	0.0266 (4)	0.0009 (3)	0.0062 (3)	−0.0054 (3)
O2	0.0237 (4)	0.0179 (4)	0.0213 (4)	−0.0052 (3)	0.0097 (3)	−0.0003 (3)
O3	0.0199 (3)	0.0182 (3)	0.0192 (3)	−0.0042 (3)	0.0087 (3)	−0.0021 (3)
O4	0.0223 (3)	0.0123 (3)	0.0153 (3)	−0.0039 (3)	0.0036 (3)	−0.0020 (2)
O5	0.0206 (3)	0.0128 (3)	0.0152 (3)	−0.0019 (2)	0.0076 (3)	−0.0010 (2)

Geometric parameters (Å, º) top

C1—O1	1.3638 (12)	C15—C16	1.5064 (14)
C1—C2	1.3927 (15)	C15—H15	0.93
C1—C6	1.3969 (14)	C16—O4	1.4722 (11)
C2—C3	1.3823 (15)	C16—C18	1.5194 (14)
C2—H2	0.93	C16—C17	1.5249 (14)
C3—C4	1.4063 (14)	C17—H17A	0.96
C3—H3	0.93	C17—H17B	0.96
C4—C5	1.3997 (14)	C17—H17C	0.96
C4—C8	1.4601 (14)	C18—H18A	0.96
C5—C6	1.3851 (14)	C18—H18B	0.96
C5—H5	0.93	C18—H18C	0.96
C6—H6	0.93	C19—O4	1.3593 (11)
C7—O1	1.4266 (14)	C19—C20	1.4004 (13)
C7—H7A	0.96	C20—C21	1.3983 (13)
C7—H7B	0.96	C20—C24	1.4595 (13)
C7—H7C	0.96	C21—O5	1.3599 (11)
C8—C9	1.3438 (14)	C22—O5	1.4733 (11)
C8—H8	0.93	C22—C23	1.5054 (13)
C9—C10	1.4725 (13)	C22—C25	1.5177 (14)
C9—H9	0.93	C22—C26	1.5241 (14)
C10—O2	1.2585 (12)	C23—C24	1.3288 (14)
C10—C11	1.4699 (13)	C23—H23	0.93
C11—C21	1.4201 (13)	C24—H24	0.93
C11—C12	1.4321 (13)	C25—H25A	0.96
C12—O3	1.3441 (11)	C25—H25B	0.96
C12—C13	1.3990 (13)	C25—H25C	0.96
C13—C19	1.3975 (13)	C26—H26A	0.96
C13—C14	1.4568 (13)	C26—H26B	0.96
C14—C15	1.3323 (14)	C26—H26C	0.96
C14—H14	0.93	O3—H3A	0.82

O1—C1—C2	115.78 (9)	C15—C16—C17	110.67 (8)
O1—C1—C6	124.11 (9)	C18—C16—C17	111.27 (8)
C2—C1—C6	120.11 (9)	C16—C17—H17A	109.5
C3—C2—C1	119.63 (9)	C16—C17—H17B	109.5
C3—C2—H2	120.2	H17A—C17—H17B	109.5
C1—C2—H2	120.2	C16—C17—H17C	109.5
C2—C3—C4	121.47 (9)	H17A—C17—H17C	109.5
C2—C3—H3	119.3	H17B—C17—H17C	109.5
C4—C3—H3	119.3	C16—C18—H18A	109.5
C5—C4—C3	117.75 (9)	C16—C18—H18B	109.5
C5—C4—C8	123.32 (9)	H18A—C18—H18B	109.5
C3—C4—C8	118.93 (9)	C16—C18—H18C	109.5
C6—C5—C4	121.40 (9)	H18A—C18—H18C	109.5
C6—C5—H5	119.3	H18B—C18—H18C	109.5
C4—C5—H5	119.3	O4—C19—C13	120.65 (8)
C5—C6—C1	119.64 (9)	O4—C19—C20	117.08 (8)
C5—C6—H6	120.2	C13—C19—C20	122.25 (9)
C1—C6—H6	120.2	C21—C20—C19	118.14 (8)
O1—C7—H7A	109.5	C21—C20—C24	118.84 (8)
O1—C7—H7B	109.5	C19—C20—C24	122.80 (9)
H7A—C7—H7B	109.5	O5—C21—C20	118.84 (8)
O1—C7—H7C	109.5	O5—C21—C11	118.25 (8)
H7A—C7—H7C	109.5	C20—C21—C11	122.65 (8)
H7B—C7—H7C	109.5	O5—C22—C23	109.86 (7)
C9—C8—C4	127.33 (9)	O5—C22—C25	104.14 (7)
C9—C8—H8	116.3	C23—C22—C25	111.69 (8)
C4—C8—H8	116.3	O5—C22—C26	107.81 (8)
C8—C9—C10	119.06 (9)	C23—C22—C26	111.31 (8)
C8—C9—H9	120.5	C25—C22—C26	111.71 (8)
C10—C9—H9	120.5	C24—C23—C22	120.21 (9)
O2—C10—C11	118.73 (9)	C24—C23—H23	119.9
O2—C10—C9	117.15 (9)	C22—C23—H23	119.9
C11—C10—C9	124.12 (8)	C23—C24—C20	120.03 (9)
C21—C11—C12	116.40 (8)	C23—C24—H24	120
C21—C11—C10	125.57 (8)	C20—C24—H24	120
C12—C11—C10	118.02 (8)	C22—C25—H25A	109.5
O3—C12—C13	116.57 (8)	C22—C25—H25B	109.5
O3—C12—C11	121.42 (9)	H25A—C25—H25B	109.5
C13—C12—C11	122.01 (9)	C22—C25—H25C	109.5
C19—C13—C12	118.51 (9)	H25A—C25—H25C	109.5
C19—C13—C14	118.43 (9)	H25B—C25—H25C	109.5
C12—C13—C14	123.02 (9)	C22—C26—H26A	109.5
C15—C14—C13	119.03 (9)	C22—C26—H26B	109.5
C15—C14—H14	120.5	H26A—C26—H26B	109.5
C13—C14—H14	120.5	C22—C26—H26C	109.5
C14—C15—C16	120.46 (9)	H26A—C26—H26C	109.5
C14—C15—H15	119.8	H26B—C26—H26C	109.5
C16—C15—H15	119.8	C1—O1—C7	117.64 (9)
O4—C16—C15	109.90 (8)	C12—O3—H3A	109.5
O4—C16—C18	104.77 (8)	C19—O4—C16	116.87 (7)
C15—C16—C18	112.34 (8)	C21—O5—C22	118.27 (7)
O4—C16—C17	107.63 (8)

O1—C1—C2—C3	179.87 (9)	C14—C13—C19—O4	2.68 (14)
C6—C1—C2—C3	0.06 (15)	C12—C13—C19—C20	2.16 (14)
C1—C2—C3—C4	−0.88 (15)	C14—C13—C19—C20	−175.54 (9)
C2—C3—C4—C5	0.96 (15)	O4—C19—C20—C21	179.39 (8)
C2—C3—C4—C8	−179.91 (9)	C13—C19—C20—C21	−2.33 (14)
C3—C4—C5—C6	−0.24 (14)	O4—C19—C20—C24	4.86 (14)
C8—C4—C5—C6	−179.33 (9)	C13—C19—C20—C24	−176.85 (9)
C4—C5—C6—C1	−0.55 (15)	C19—C20—C21—O5	−172.89 (8)
O1—C1—C6—C5	−179.15 (9)	C24—C20—C21—O5	1.87 (13)
C2—C1—C6—C5	0.65 (15)	C19—C20—C21—C11	1.10 (14)
C5—C4—C8—C9	−9.13 (16)	C24—C20—C21—C11	175.85 (9)
C3—C4—C8—C9	171.79 (10)	C12—C11—C21—O5	174.23 (8)
C4—C8—C9—C10	179.61 (9)	C10—C11—C21—O5	−4.63 (14)
C8—C9—C10—O2	−18.82 (14)	C12—C11—C21—C20	0.21 (14)
C8—C9—C10—C11	160.57 (9)	C10—C11—C21—C20	−178.65 (9)
O2—C10—C11—C21	175.47 (9)	O5—C22—C23—C24	−29.29 (12)
C9—C10—C11—C21	−3.91 (15)	C25—C22—C23—C24	−144.33 (10)
O2—C10—C11—C12	−3.37 (13)	C26—C22—C23—C24	90.05 (11)
C9—C10—C11—C12	177.24 (9)	C22—C23—C24—C20	2.94 (15)
C21—C11—C12—O3	179.36 (8)	C21—C20—C24—C23	12.64 (14)
C10—C11—C12—O3	−1.69 (14)	C19—C20—C24—C23	−172.87 (9)
C21—C11—C12—C13	−0.39 (14)	C2—C1—O1—C7	179.59 (9)
C10—C11—C12—C13	178.56 (8)	C6—C1—O1—C7	−0.61 (15)
O3—C12—C13—C19	179.49 (8)	C13—C19—O4—C16	27.90 (12)
C11—C12—C13—C19	−0.75 (14)	C20—C19—O4—C16	−153.79 (8)
O3—C12—C13—C14	−2.92 (14)	C15—C16—O4—C19	−43.92 (11)
C11—C12—C13—C14	176.84 (9)	C18—C16—O4—C19	−164.82 (8)
C19—C13—C14—C15	−14.31 (14)	C17—C16—O4—C19	76.67 (10)
C12—C13—C14—C15	168.10 (10)	C20—C21—O5—C22	−31.54 (12)
C13—C14—C15—C16	−5.24 (15)	C11—C21—O5—C22	154.21 (8)
C14—C15—C16—O4	33.00 (13)	C23—C22—O5—C21	43.94 (11)
C14—C15—C16—C18	149.22 (10)	C25—C22—O5—C21	163.69 (8)
C14—C15—C16—C17	−85.74 (12)	C26—C22—O5—C21	−77.52 (10)
C12—C13—C19—O4	−179.62 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	1.72	2.4523 (10)	148

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆O₅
M_r	418.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	446
a, b, c (Å)	9.6422 (2), 12.0871 (3), 18.4517 (4)
β (°)	99.228 (1)
V (Å³)	2122.64 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.37 × 0.33 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.968, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	68753, 5126, 4677
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.01
No. of reflections	5126
No. of parameters	286
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.23

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	1.72	2.4523 (10)	148.3

Acknowledgements

SP thanks the College of Agriculture, Engineering and Science of the University of KwaZulu-Natal for a doctoral bursary.

References

Bhattacharyya, K., Mazumdar, S. K., Bocelli, G., Cantoni, A., Ray, A. B., Neogi, P. & Mazumdar, G. (1999). Acta Cryst. C55, 215–217. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds, pp. 1–32. New York: John Wiley and Sons. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Lee, Y. R. & Li, X. (2007). Bull. Korean Chem. Soc. 28, 1739–1745. CAS Google Scholar
Lin, Y.-L., Chen, Y.-L. & Kuo, Y.-H. (1992). Chem. Pharm. Bull. 40, 2295–2299. CrossRef CAS Google Scholar
Liu, T., Xu, Z.-M. & Hu, Y.-Z. (2005). Acta Cryst. E61, o3389–o3390. Web of Science CSD CrossRef IUCr Journals Google Scholar
Narender, T., Khaliq, T., Shweta, Nishi, Goyal, N. & Gupta, S. (2005). Bioorg. Med. Chem. 13, 6543–6550. Web of Science CrossRef PubMed CAS Google Scholar
Nicolaou, K. C., Pfefferkorn, J. A., Roecker, A. J., Cao, G.-Q., Barluenga, S. & Mitchell, H. J. (2000). J. Am. Chem. Soc. 122, 9939–9953. Web of Science CrossRef CAS Google Scholar
Pawar, S., Cheddie, A., Omondi, B. & Koorbanally, N. A. (2012). Acta Cryst. E68, o3048. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

1-(5-Hy­dr­oxy-2,2,8,8-tetra­methyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-3-(4-meth­­oxy­phen­yl)prop-2-en-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(5-Hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one