Literature DB >> 23634037

1-(5-Hy-droxy-2,2,8,8-tetra-methyl-2H,8H-pyrano[2,3-f]chromen-6-yl)-3-(4-meth-oxy-phen-yl)prop-2-en-1-one.

Sunayna Pawar1, Kaalin Gopaul, Thrineshan Moodley, Bernard Omondi, Neil Koorbanally.   

Abstract

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 benzopyran-one moiety is 31.54 (4)°. The mol-ecular structure is stabilized by an intra-molecular C=O⋯H-O hydrogen bond.

Entities:  

Year:  2013        PMID： 23634037      PMCID： PMC3629519          DOI： 10.1107/S1600536813005734

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 418.47 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.104 S = 1.01 5126 reflections 286 parameters H-atom parameters constrained Δρmax = 0.38 e Å−3 Δρmin = −0.23 e Å−3 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 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005734/ff2099sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005734/ff2099Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813005734/ff2099Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H26O5F(000) = 888
Mr = 418.47Dx = 1.309 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 71516 reflections
a = 9.6422 (2) Åθ = 2.0–28°
b = 12.0871 (3) ŵ = 0.09 mm−1
c = 18.4517 (4) ÅT = 446 K
β = 99.228 (1)°Block, brown
V = 2122.64 (8) Å30.37 × 0.33 × 0.21 mm
Z = 4
Bruker SMART APEXII CCD diffractometer4677 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 28°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −12→12
Tmin = 0.968, Tmax = 0.981k = −15→15
68753 measured reflectionsl = −24→24
5126 independent reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0564P)2 + 0.9316P] where P = (Fo2 + 2Fc2)/3
5126 reflections(Δ/σ)max = 0.003
286 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
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; Uiso(H) = 1.2Ueq(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 (Uiso(H) = 1.2Ueq(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:
xyzUiso*/Ueq
C10.14616 (10)0.12942 (8)0.45580 (6)0.0187 (2)
C20.12410 (11)0.11703 (8)0.52813 (6)0.0207 (2)
H20.11440.04680.54730.025*
C30.11675 (11)0.20968 (9)0.57126 (6)0.0192 (2)
H30.10070.2010.61930.023*
C40.13298 (10)0.31683 (8)0.54411 (5)0.01655 (19)
C50.15481 (10)0.32699 (8)0.47122 (6)0.0179 (2)
H50.16550.3970.4520.022*
C60.16087 (11)0.23495 (9)0.42712 (6)0.0190 (2)
H60.17470.24340.37870.023*
C70.17381 (13)0.04268 (10)0.34274 (6)0.0282 (2)
H7A0.09980.08620.31560.042*
H7B0.1735−0.02980.32150.042*
H7C0.26260.07770.3410.042*
C80.12434 (10)0.41146 (8)0.59236 (5)0.01725 (19)
H80.0960.39650.63720.021*
C90.15272 (10)0.51777 (8)0.57928 (5)0.01690 (19)
H90.18210.5380.53550.02*
C100.13665 (10)0.60171 (8)0.63516 (5)0.01499 (18)
C110.20284 (9)0.71156 (8)0.63883 (5)0.01365 (18)
C120.17283 (10)0.78670 (8)0.69429 (5)0.01453 (18)
C130.23344 (10)0.89200 (8)0.70296 (5)0.01503 (19)
C140.19923 (10)0.97192 (8)0.75649 (6)0.0185 (2)
H140.12280.96030.78060.022*
C150.27897 (11)1.06184 (9)0.77042 (6)0.0200 (2)
H150.25371.11630.80140.024*
C160.40971 (10)1.07586 (8)0.73628 (5)0.01676 (19)
C170.53457 (11)1.01888 (9)0.78265 (6)0.0195 (2)
H17A0.51590.94110.78530.029*
H17B0.54921.04970.83120.029*
H17C0.61721.030.76060.029*
C180.44156 (12)1.19660 (9)0.72296 (6)0.0227 (2)
H18A0.52281.20140.69910.034*
H18B0.45951.2350.76910.034*
H18C0.36251.22970.69230.034*
C190.32725 (10)0.92351 (8)0.65633 (5)0.01412 (18)
C200.35864 (10)0.85484 (8)0.60002 (5)0.01394 (18)
C210.29703 (10)0.74988 (8)0.59257 (5)0.01330 (18)
C220.38220 (10)0.72295 (8)0.47666 (5)0.01553 (19)
C230.47626 (10)0.82157 (8)0.49591 (5)0.01718 (19)
H230.54480.83860.46750.021*
C240.46159 (10)0.88436 (8)0.55330 (5)0.01615 (19)
H240.5170.94710.56370.019*
C250.45997 (12)0.62799 (9)0.44730 (6)0.0212 (2)
H25A0.53820.60660.48360.032*
H25B0.49350.65110.40340.032*
H25C0.39750.56630.43640.032*
C260.25010 (12)0.75443 (9)0.42370 (6)0.0224 (2)
H26A0.19050.69080.4140.034*
H26B0.27580.78080.37860.034*
H26C0.20080.81160.44520.034*
O10.15230 (9)0.03378 (6)0.41723 (5)0.02628 (18)
O20.06220 (8)0.57627 (6)0.68277 (4)0.02028 (16)
O30.08410 (8)0.75943 (6)0.74064 (4)0.01852 (16)
H3A0.05690.69570.73260.028*
O40.38941 (7)1.02473 (6)0.66293 (4)0.01655 (15)
O50.33812 (7)0.67778 (6)0.54356 (4)0.01567 (15)
U11U22U33U12U13U23
C10.0172 (4)0.0153 (5)0.0231 (5)0.0006 (3)0.0014 (4)−0.0037 (4)
C20.0228 (5)0.0137 (4)0.0249 (5)−0.0015 (4)0.0021 (4)0.0022 (4)
C30.0206 (5)0.0182 (5)0.0186 (5)−0.0020 (4)0.0025 (4)0.0018 (4)
C40.0138 (4)0.0148 (4)0.0204 (5)−0.0014 (3)0.0009 (3)−0.0007 (4)
C50.0176 (4)0.0145 (4)0.0213 (5)−0.0017 (3)0.0022 (4)0.0014 (4)
C60.0192 (5)0.0191 (5)0.0186 (5)−0.0006 (4)0.0027 (4)−0.0001 (4)
C70.0337 (6)0.0257 (6)0.0239 (5)0.0054 (5)0.0010 (4)−0.0075 (4)
C80.0166 (4)0.0175 (5)0.0175 (4)−0.0014 (3)0.0022 (3)−0.0001 (4)
C90.0166 (4)0.0170 (5)0.0173 (4)−0.0031 (3)0.0035 (3)−0.0013 (4)
C100.0144 (4)0.0145 (4)0.0158 (4)−0.0011 (3)0.0018 (3)0.0015 (3)
C110.0140 (4)0.0131 (4)0.0139 (4)−0.0006 (3)0.0022 (3)0.0000 (3)
C120.0134 (4)0.0162 (4)0.0142 (4)0.0003 (3)0.0029 (3)0.0007 (3)
C130.0150 (4)0.0147 (4)0.0155 (4)0.0002 (3)0.0025 (3)−0.0017 (3)
C140.0177 (4)0.0188 (5)0.0200 (5)0.0013 (4)0.0062 (4)−0.0030 (4)
C150.0224 (5)0.0173 (5)0.0213 (5)0.0013 (4)0.0064 (4)−0.0056 (4)
C160.0215 (5)0.0131 (4)0.0157 (4)−0.0023 (3)0.0030 (3)−0.0033 (3)
C170.0214 (5)0.0187 (5)0.0181 (5)−0.0015 (4)0.0021 (4)−0.0009 (4)
C180.0303 (5)0.0136 (5)0.0239 (5)−0.0037 (4)0.0029 (4)−0.0018 (4)
C190.0154 (4)0.0117 (4)0.0147 (4)−0.0003 (3)0.0006 (3)0.0006 (3)
C200.0152 (4)0.0136 (4)0.0131 (4)−0.0008 (3)0.0024 (3)0.0008 (3)
C210.0144 (4)0.0131 (4)0.0123 (4)0.0008 (3)0.0018 (3)−0.0002 (3)
C220.0191 (4)0.0150 (4)0.0135 (4)−0.0009 (3)0.0057 (3)0.0002 (3)
C230.0183 (4)0.0166 (4)0.0177 (4)−0.0022 (3)0.0062 (3)0.0018 (4)
C240.0175 (4)0.0144 (4)0.0168 (4)−0.0031 (3)0.0035 (3)0.0017 (3)
C250.0270 (5)0.0171 (5)0.0220 (5)0.0009 (4)0.0112 (4)−0.0011 (4)
C260.0233 (5)0.0236 (5)0.0193 (5)0.0004 (4)0.0000 (4)0.0003 (4)
O10.0366 (4)0.0160 (4)0.0266 (4)0.0009 (3)0.0062 (3)−0.0054 (3)
O20.0237 (4)0.0179 (4)0.0213 (4)−0.0052 (3)0.0097 (3)−0.0003 (3)
O30.0199 (3)0.0182 (3)0.0192 (3)−0.0042 (3)0.0087 (3)−0.0021 (3)
O40.0223 (3)0.0123 (3)0.0153 (3)−0.0039 (3)0.0036 (3)−0.0020 (2)
O50.0206 (3)0.0128 (3)0.0152 (3)−0.0019 (2)0.0076 (3)−0.0010 (2)
C1—O11.3638 (12)C15—C161.5064 (14)
C1—C21.3927 (15)C15—H150.93
C1—C61.3969 (14)C16—O41.4722 (11)
C2—C31.3823 (15)C16—C181.5194 (14)
C2—H20.93C16—C171.5249 (14)
C3—C41.4063 (14)C17—H17A0.96
C3—H30.93C17—H17B0.96
C4—C51.3997 (14)C17—H17C0.96
C4—C81.4601 (14)C18—H18A0.96
C5—C61.3851 (14)C18—H18B0.96
C5—H50.93C18—H18C0.96
C6—H60.93C19—O41.3593 (11)
C7—O11.4266 (14)C19—C201.4004 (13)
C7—H7A0.96C20—C211.3983 (13)
C7—H7B0.96C20—C241.4595 (13)
C7—H7C0.96C21—O51.3599 (11)
C8—C91.3438 (14)C22—O51.4733 (11)
C8—H80.93C22—C231.5054 (13)
C9—C101.4725 (13)C22—C251.5177 (14)
C9—H90.93C22—C261.5241 (14)
C10—O21.2585 (12)C23—C241.3288 (14)
C10—C111.4699 (13)C23—H230.93
C11—C211.4201 (13)C24—H240.93
C11—C121.4321 (13)C25—H25A0.96
C12—O31.3441 (11)C25—H25B0.96
C12—C131.3990 (13)C25—H25C0.96
C13—C191.3975 (13)C26—H26A0.96
C13—C141.4568 (13)C26—H26B0.96
C14—C151.3323 (14)C26—H26C0.96
C14—H140.93O3—H3A0.82
O1—C1—C2115.78 (9)C15—C16—C17110.67 (8)
O1—C1—C6124.11 (9)C18—C16—C17111.27 (8)
C2—C1—C6120.11 (9)C16—C17—H17A109.5
C3—C2—C1119.63 (9)C16—C17—H17B109.5
C3—C2—H2120.2H17A—C17—H17B109.5
C1—C2—H2120.2C16—C17—H17C109.5
C2—C3—C4121.47 (9)H17A—C17—H17C109.5
C2—C3—H3119.3H17B—C17—H17C109.5
C4—C3—H3119.3C16—C18—H18A109.5
C5—C4—C3117.75 (9)C16—C18—H18B109.5
C5—C4—C8123.32 (9)H18A—C18—H18B109.5
C3—C4—C8118.93 (9)C16—C18—H18C109.5
C6—C5—C4121.40 (9)H18A—C18—H18C109.5
C6—C5—H5119.3H18B—C18—H18C109.5
C4—C5—H5119.3O4—C19—C13120.65 (8)
C5—C6—C1119.64 (9)O4—C19—C20117.08 (8)
C5—C6—H6120.2C13—C19—C20122.25 (9)
C1—C6—H6120.2C21—C20—C19118.14 (8)
O1—C7—H7A109.5C21—C20—C24118.84 (8)
O1—C7—H7B109.5C19—C20—C24122.80 (9)
H7A—C7—H7B109.5O5—C21—C20118.84 (8)
O1—C7—H7C109.5O5—C21—C11118.25 (8)
H7A—C7—H7C109.5C20—C21—C11122.65 (8)
H7B—C7—H7C109.5O5—C22—C23109.86 (7)
C9—C8—C4127.33 (9)O5—C22—C25104.14 (7)
C9—C8—H8116.3C23—C22—C25111.69 (8)
C4—C8—H8116.3O5—C22—C26107.81 (8)
C8—C9—C10119.06 (9)C23—C22—C26111.31 (8)
C8—C9—H9120.5C25—C22—C26111.71 (8)
C10—C9—H9120.5C24—C23—C22120.21 (9)
O2—C10—C11118.73 (9)C24—C23—H23119.9
O2—C10—C9117.15 (9)C22—C23—H23119.9
C11—C10—C9124.12 (8)C23—C24—C20120.03 (9)
C21—C11—C12116.40 (8)C23—C24—H24120
C21—C11—C10125.57 (8)C20—C24—H24120
C12—C11—C10118.02 (8)C22—C25—H25A109.5
O3—C12—C13116.57 (8)C22—C25—H25B109.5
O3—C12—C11121.42 (9)H25A—C25—H25B109.5
C13—C12—C11122.01 (9)C22—C25—H25C109.5
C19—C13—C12118.51 (9)H25A—C25—H25C109.5
C19—C13—C14118.43 (9)H25B—C25—H25C109.5
C12—C13—C14123.02 (9)C22—C26—H26A109.5
C15—C14—C13119.03 (9)C22—C26—H26B109.5
C15—C14—H14120.5H26A—C26—H26B109.5
C13—C14—H14120.5C22—C26—H26C109.5
C14—C15—C16120.46 (9)H26A—C26—H26C109.5
C14—C15—H15119.8H26B—C26—H26C109.5
C16—C15—H15119.8C1—O1—C7117.64 (9)
O4—C16—C15109.90 (8)C12—O3—H3A109.5
O4—C16—C18104.77 (8)C19—O4—C16116.87 (7)
C15—C16—C18112.34 (8)C21—O5—C22118.27 (7)
O4—C16—C17107.63 (8)
O1—C1—C2—C3179.87 (9)C14—C13—C19—O42.68 (14)
C6—C1—C2—C30.06 (15)C12—C13—C19—C202.16 (14)
C1—C2—C3—C4−0.88 (15)C14—C13—C19—C20−175.54 (9)
C2—C3—C4—C50.96 (15)O4—C19—C20—C21179.39 (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—C244.86 (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—O51.87 (13)
C2—C1—C6—C50.65 (15)C19—C20—C21—C111.10 (14)
C5—C4—C8—C9−9.13 (16)C24—C20—C21—C11175.85 (9)
C3—C4—C8—C9171.79 (10)C12—C11—C21—O5174.23 (8)
C4—C8—C9—C10179.61 (9)C10—C11—C21—O5−4.63 (14)
C8—C9—C10—O2−18.82 (14)C12—C11—C21—C200.21 (14)
C8—C9—C10—C11160.57 (9)C10—C11—C21—C20−178.65 (9)
O2—C10—C11—C21175.47 (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—C2490.05 (11)
C9—C10—C11—C12177.24 (9)C22—C23—C24—C202.94 (15)
C21—C11—C12—O3179.36 (8)C21—C20—C24—C2312.64 (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—C7179.59 (9)
C10—C11—C12—C13178.56 (8)C6—C1—O1—C7−0.61 (15)
O3—C12—C13—C19179.49 (8)C13—C19—O4—C1627.90 (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—C14176.84 (9)C18—C16—O4—C19−164.82 (8)
C19—C13—C14—C15−14.31 (14)C17—C16—O4—C1976.67 (10)
C12—C13—C14—C15168.10 (10)C20—C21—O5—C22−31.54 (12)
C13—C14—C15—C16−5.24 (15)C11—C21—O5—C22154.21 (8)
C14—C15—C16—O433.00 (13)C23—C22—O5—C2143.94 (11)
C14—C15—C16—C18149.22 (10)C25—C22—O5—C21163.69 (8)
C14—C15—C16—C17−85.74 (12)C26—C22—O5—C21−77.52 (10)
C12—C13—C19—O4−179.62 (8)
D—H···AD—HH···AD···AD—H···A
O3—H3A···O20.821.722.4523 (10)148
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O3—H3A⋯O20.821.722.4523 (10)148
  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis of chromenochalcones and evaluation of their in vitro antileishmanial activity.

Authors:  Tadigoppula Narender; Tanvir Khaliq; Neena Goyal; Suman Gupta
Journal:  Bioorg Med Chem       Date:  2005-09-26       Impact factor: 3.641

3.  1-(5-Hy-droxy-2,2,8,8-tetra-methyl-2H,8H-pyrano[2,3-f]chromen-6-yl)ethanone.

Authors:  Sunayna Pawar; Adele Cheddie; Bernard Omondi; Neil Anthony Koorbanally
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-29
  3 in total

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