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

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ISSN: 2056-9890

(3E)-11,16-Dioxatri­cyclo­[15.4.0.05,10]henicosa-1(21),3,5,7,9,17,19-heptaen-2-one

aDepartment of Physics, SMK Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
*Correspondence e-mail: a_sp59@yahoo.in

(Received 22 December 2012; accepted 3 January 2013; online 23 February 2013)

The title compound, C19H18O3, crystallizes with three mol­ecules (A, B and C) in the asymmetric unit. The carbonyl O atom shows positional disorder over two sites in mol­ecules A and B; the site-occupancy ratios are 0.76 (3):0.24 (3) and 0.86 (3):0.14 (3), respectively. The ethyl­ene fragments in each mol­ecule have an E conformation, while the C—O—C—C torsion angles indicate near planarity. The dihedral angles formed by the aromatic rings are 20.0 (1), 23.7 (1) and 16.1 (1)° for mol­ecules A, B and C, respectively. Intra­molecular C—H⋯O hydrogen bonds occur in each mol­ecule.

Related literature

For the biological activities of chalcones, see: Xue et al. (2004[Xue, C. X., Cui, S. Y., Liu, M. C., Hu, Z. D. & Fan, B. T. (2004). Eur. J. Med. Chem. 39, 745-753.]); Lee et al. (2006[Lee, Y. S., Lim, S. S., Shin, K. H., Kim, Y. S., Ohuchi, K. & Jung, S. H. (2006). Biol. Pharm. Bull. 29, 1028-1031.]); Bhat et al. (2005[Bhat, B. A., Dhar, K. L., Puri, S. C., Saxena, A. K., Shanmugavel, M. & Qazi, G. N. (2005). Bioorg. Med. Chem. Lett. 15, 3177-3180.]); Satyanarayana et al. (2004[Satyanarayana, M., Tiwari, P., Tripathi, B. K., Srivastava, A. K. & Pratap, R. (2004). Bioorg. Med. Chem. Lett. 12, 883-889.]). For a related crown ether structure, see: Anh et al. (2011[Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Soldatova, S. A. & Khrustalev, V. N. (2011). Acta Cryst. E67, o1128-o1129.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18O3

  • Mr = 294.34

  • Triclinic, [P \overline 1]

  • a = 9.0976 (6) Å

  • b = 16.9797 (11) Å

  • c = 17.2713 (9) Å

  • α = 62.590 (2)°

  • β = 88.440 (2)°

  • γ = 78.092 (2)°

  • V = 2310.4 (2) Å3

  • Z = 6

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.40 × 0.30 × 0.25 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker. (2008). APEX2 and SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.979

  • 44770 measured reflections

  • 9919 independent reflections

  • 5862 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.143

  • S = 1.04

  • 9919 reflections

  • 629 parameters

  • 15 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C18—H18⋯O2 0.93 2.15 2.746 (2) 121
C18—H18⋯O3 0.93 2.12 2.763 (2) 126
C38—H38⋯O5 0.93 2.24 2.753 (2) 114
C38—H38⋯O6 0.93 2.13 2.753 (3) 123
C56—H56⋯O8 0.93 2.23 2.766 (2) 116
C56—H56⋯O9 0.93 2.15 2.764 (2) 122

Data collection: APEX2 (Bruker, 2008[Bruker. (2008). APEX2 and SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker. (2008). APEX2 and SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Chalcone derivatives possess a wide range of biological properties such as antimalarial (Xue et al., 2004), antiangiogenic and antitumour (Lee et al., 2006), anticancer (Bhat et al., 2005) and antihyperglycemic (Satyanarayana et al., 2004) activities. Chalcones have been widely studied and developed as one of the pharmaceutically important molecules. Herein we report the crystal structure of the title compound.

The macomolecular structure of the title compound, C57H52O9, includes 14-crown-2-ether skeletal moiety (Fig. 1). The bond lengths and bond angles are comparable with the related crown ether structure (Anh et al., 2011). The compound crystallizes with three independent molecules (A, B and C) per asymmetric unit. Out of three molecules, two molecules are disordered with two alternate positions for the O atoms [atom O1/O1' in molecule A, and O4/O4' in molecule B] with site occupancies are 0.76/0.24 and 0.86/0.14. The ethylene fragments in all the three molecules have E configuration, while the C—O—C—C torsion angles indicate planarity of the segments. The dihedral angles between the aromatic rings are 20.0 (1), 23.7 (1) and 16.1 (1)° for molecules A, B and C, respectively.

Each molecule of the asymmetric unit exhibits intramolecular C—H···O hydrogen bonds [Table 1].

Related literature top

For the biological activities of chalcone, see: Xue et al. (2004); Lee et al. (2006); Bhat et al. (2005); Satyanarayana et al. (2004). For related crown ether structure, see: Anh et al. (2011).

Experimental top

To a solution of 2 g (5.08 mmol) of 2-(4-(4-((2-acetylphenoxy) methyl)-1H-1,2,3-triazol-1-yl) butoxy)benzaldehyde in 30 ml of methanol, 0.30 g (7.63 mmol) of NaOH in 30 ml of methanol was added drop wise and the mixture was stirred vigorously at room temperature for about 8 h. After the completion of the reaction, as evidenced by TLC analysis, the solvent was removed under vacuum. The crude product was then subjected to column chromatography using petroleum ether/ethylacetate (1:1) as eluent. The single crystal suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

Refinement top

All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C—H distances fixed in the range 0.93–0.97 Å with Uiso(H) = 1.2Ueq(C) for other H atoms. The carbonyl group O atoms of two molecules shows positional disorder and were refined split into two positions with occupancies of 0.76 (3)/0.24 (3) and 0.86 (3)/0.14 (3).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.
(3E)-11,16-Dioxatricyclo[15.4.0.05,10]henicosa-1(21),3,5,7,9,17,19- heptaen-2-one top
Crystal data top
C19H18O3Z = 6
Mr = 294.34F(000) = 936
Triclinic, P1Dx = 1.269 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0976 (6) ÅCell parameters from 9919 reflections
b = 16.9797 (11) Åθ = 2.0–26.9°
c = 17.2713 (9) ŵ = 0.09 mm1
α = 62.590 (2)°T = 293 K
β = 88.440 (2)°Block, white crystalline
γ = 78.092 (2)°0.40 × 0.30 × 0.25 mm
V = 2310.4 (2) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
9919 independent reflections
Radiation source: fine-focus sealed tube5862 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω and ϕ scansθmax = 26.9°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1111
Tmin = 0.967, Tmax = 0.979k = 2121
44770 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.063P)2 + 0.2901P]
where P = (Fo2 + 2Fc2)/3
9919 reflections(Δ/σ)max < 0.001
629 parametersΔρmax = 0.19 e Å3
15 restraintsΔρmin = 0.16 e Å3
Crystal data top
C19H18O3γ = 78.092 (2)°
Mr = 294.34V = 2310.4 (2) Å3
Triclinic, P1Z = 6
a = 9.0976 (6) ÅMo Kα radiation
b = 16.9797 (11) ŵ = 0.09 mm1
c = 17.2713 (9) ÅT = 293 K
α = 62.590 (2)°0.40 × 0.30 × 0.25 mm
β = 88.440 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
9919 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
5862 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.979Rint = 0.032
44770 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04515 restraints
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.19 e Å3
9919 reflectionsΔρmin = 0.16 e Å3
629 parameters
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.

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 > 2sigma(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
xyzUiso*/UeqOcc. (<1)
C10.2486 (2)0.55742 (11)0.08728 (12)0.0588 (5)
C20.3295 (3)0.56983 (13)0.01475 (14)0.0739 (6)
H20.43390.55920.02120.089*
C30.2613 (3)0.59712 (15)0.06609 (15)0.0862 (7)
H30.31890.60370.11320.103*
C40.1071 (3)0.61454 (15)0.07661 (15)0.0819 (6)
H40.05990.63410.13140.098*
C50.0222 (3)0.60341 (13)0.00704 (13)0.0705 (5)
H50.08220.61510.01490.085*
C60.0908 (2)0.57491 (12)0.07496 (12)0.0604 (5)
C70.1490 (2)0.58850 (16)0.13795 (14)0.0746 (6)
H7A0.19100.55760.11150.089*
H7B0.18400.65360.10230.089*
C80.1943 (2)0.55946 (15)0.22954 (14)0.0751 (6)
H8A0.30070.58530.22720.090*
H8B0.13890.58400.25730.090*
C90.1666 (2)0.45690 (16)0.28566 (15)0.0799 (6)
H9A0.26190.43860.29000.096*
H9B0.10120.42810.25630.096*
C100.0971 (2)0.42235 (16)0.37628 (14)0.0788 (6)
H10A0.15560.45360.40570.095*
H10B0.09190.35770.41050.095*
C110.1433 (2)0.42178 (13)0.43431 (13)0.0630 (5)
C120.1029 (2)0.38431 (14)0.51991 (13)0.0713 (5)
H120.00780.37140.53160.086*
C130.2019 (3)0.36627 (15)0.58727 (14)0.0776 (6)
H130.17430.34020.64450.093*
C140.3413 (3)0.38636 (16)0.57095 (15)0.0823 (6)
H140.40800.37490.61670.099*
C150.3817 (2)0.42369 (13)0.48619 (14)0.0720 (5)
H150.47650.43720.47570.086*
C160.2861 (2)0.44200 (12)0.41563 (12)0.0601 (5)
C170.3411 (2)0.47976 (13)0.32785 (14)0.0654 (5)
C180.2732 (2)0.49489 (13)0.25304 (13)0.0716 (6)
H180.17810.48230.25490.086*
C190.3368 (2)0.52898 (12)0.17062 (13)0.0663 (5)
C200.7253 (2)0.13378 (14)0.66919 (13)0.0646 (5)
C210.6521 (2)0.17445 (13)0.75325 (13)0.0626 (5)
C220.6970 (3)0.26840 (16)0.80557 (16)0.0811 (6)
H220.76590.30220.78550.097*
C230.6422 (3)0.31261 (17)0.88618 (18)0.0928 (7)
H230.67190.37540.91900.111*
C240.5441 (3)0.26358 (19)0.91737 (18)0.0963 (7)
H240.51000.29300.97260.116*
C250.4957 (3)0.17205 (16)0.86847 (15)0.0809 (6)
H250.42800.13950.89030.097*
C260.5470 (2)0.12669 (14)0.78589 (13)0.0644 (5)
C270.3856 (2)0.01519 (14)0.76303 (13)0.0705 (5)
H27A0.42060.01440.81600.085*
H27B0.29710.01080.77460.085*
C280.3489 (2)0.11039 (14)0.69007 (12)0.0674 (5)
H28A0.44230.13040.67210.081*
H28B0.29090.14950.71210.081*
C290.2608 (2)0.12287 (15)0.60977 (13)0.0698 (5)
H29A0.26170.06350.61480.084*
H29B0.15690.15200.60900.084*
C300.3217 (2)0.17845 (14)0.52471 (12)0.0666 (5)
H30A0.25390.19200.47570.080*
H30B0.33490.23520.52130.080*
C310.5525 (2)0.15677 (13)0.45736 (12)0.0564 (4)
C320.5141 (2)0.24309 (14)0.38767 (12)0.0672 (5)
H320.42240.28120.38440.081*
C330.6110 (3)0.27270 (17)0.32327 (15)0.0850 (6)
H330.58430.33070.27630.102*
C340.7463 (3)0.2176 (2)0.32775 (18)0.1040 (8)
H340.81250.23820.28450.125*
C350.7843 (3)0.13101 (18)0.39687 (16)0.0888 (7)
H350.87690.09400.39940.107*
C360.6886 (2)0.09715 (14)0.46310 (12)0.0611 (5)
C370.7366 (2)0.00422 (16)0.53391 (14)0.0654 (5)
C380.6604 (2)0.04329 (13)0.60039 (12)0.0615 (5)
H380.56100.01710.60270.074*
C390.93750 (19)0.19043 (12)0.74456 (11)0.0533 (4)
C400.8673 (2)0.28237 (13)0.69700 (13)0.0678 (5)
H400.89080.32360.71340.081*
C410.7645 (2)0.31371 (15)0.62675 (15)0.0797 (6)
H410.71840.37510.59690.096*
C420.7305 (2)0.25418 (16)0.60102 (15)0.0810 (6)
H420.66230.27540.55290.097*
C430.7958 (2)0.16383 (14)0.64527 (13)0.0697 (5)
H430.77170.12400.62700.084*
C440.89803 (19)0.13060 (12)0.71742 (11)0.0546 (4)
C450.9246 (2)0.02235 (13)0.73831 (13)0.0680 (5)
H45A0.95650.01160.68090.082*
H45B0.81620.01590.73690.082*
C461.0010 (2)0.11563 (13)0.80595 (13)0.0671 (5)
H46A1.10710.11720.81300.081*
H46B0.99330.15870.78480.081*
C470.9366 (2)0.14613 (13)0.89507 (13)0.0699 (5)
H47A0.86980.09410.89600.084*
H47B0.87690.19010.90300.084*
C481.0545 (2)0.18769 (13)0.97021 (13)0.0692 (5)
H48A1.00960.21391.02560.083*
H48B1.13070.23490.96660.083*
C491.2255 (2)0.12862 (13)1.02307 (11)0.0564 (4)
C501.2922 (2)0.21385 (14)1.08800 (13)0.0709 (5)
H501.26280.26491.09210.085*
C511.4023 (3)0.22336 (17)1.14669 (14)0.0836 (6)
H511.44750.28101.19020.100*
C521.4454 (3)0.14910 (19)1.14138 (15)0.0945 (7)
H521.51920.15581.18140.113*
C531.3792 (2)0.06407 (17)1.07647 (14)0.0808 (6)
H531.40990.01391.07350.097*
C541.26825 (19)0.05043 (13)1.01523 (11)0.0557 (4)
C551.2065 (2)0.04182 (13)0.94696 (12)0.0569 (4)
H551.25420.08610.94490.068*
C561.09217 (19)0.07140 (12)0.88751 (11)0.0534 (4)
H561.03630.03030.88980.064*
C571.0495 (2)0.16541 (12)0.81842 (12)0.0554 (4)
O10.4695 (2)0.54064 (15)0.16521 (13)0.1011 (9)0.797 (4)
O1'0.4746 (8)0.4998 (7)0.3293 (9)0.100 (3)0.204 (4)
O20.01235 (14)0.56378 (11)0.14559 (9)0.0789 (4)
O30.05022 (15)0.44048 (11)0.36520 (9)0.0831 (4)
O40.84438 (19)0.17918 (15)0.66161 (14)0.0896 (7)0.907 (4)
O4'0.8606 (10)0.036 (2)0.519 (2)0.121 (9)0.095 (4)
O50.50151 (15)0.03546 (9)0.73550 (8)0.0712 (4)
O60.46332 (14)0.12368 (9)0.52412 (8)0.0669 (4)
O71.10487 (18)0.22515 (9)0.81922 (10)0.0826 (4)
O80.96687 (14)0.04133 (8)0.76207 (8)0.0635 (3)
O91.11850 (16)0.11450 (8)0.96222 (8)0.0692 (4)
H170.4431 (7)0.4810 (13)0.327 (3)0.083*0.797 (4)
H190.4298 (5)0.5422 (5)0.1523 (6)0.083*0.204 (4)
H370.8275 (6)0.024 (3)0.522 (3)0.083*0.907 (4)
H200.815 (2)0.166 (11)0.662 (11)0.083*0.095 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0621 (12)0.0419 (10)0.0679 (12)0.0111 (8)0.0108 (9)0.0222 (9)
C20.0787 (14)0.0573 (12)0.0780 (14)0.0147 (10)0.0209 (12)0.0257 (11)
C30.108 (2)0.0759 (15)0.0725 (15)0.0216 (13)0.0268 (14)0.0332 (12)
C40.114 (2)0.0695 (14)0.0671 (14)0.0258 (13)0.0062 (13)0.0332 (11)
C50.0821 (14)0.0606 (12)0.0723 (13)0.0221 (10)0.0007 (11)0.0308 (11)
C60.0680 (13)0.0512 (11)0.0638 (12)0.0162 (9)0.0098 (10)0.0271 (9)
C70.0511 (11)0.0862 (15)0.0838 (14)0.0082 (10)0.0030 (10)0.0397 (12)
C80.0482 (11)0.0897 (16)0.0924 (15)0.0108 (10)0.0067 (10)0.0482 (13)
C90.0614 (13)0.0990 (18)0.0937 (16)0.0342 (12)0.0097 (11)0.0503 (14)
C100.0625 (13)0.0915 (16)0.0852 (15)0.0322 (11)0.0170 (11)0.0378 (13)
C110.0589 (12)0.0605 (12)0.0649 (12)0.0069 (9)0.0030 (9)0.0277 (10)
C120.0671 (13)0.0722 (14)0.0730 (13)0.0095 (10)0.0118 (11)0.0352 (11)
C130.0893 (17)0.0758 (15)0.0682 (13)0.0053 (12)0.0098 (12)0.0394 (11)
C140.0887 (17)0.0839 (16)0.0762 (15)0.0056 (13)0.0079 (12)0.0434 (13)
C150.0661 (13)0.0657 (13)0.0821 (15)0.0076 (10)0.0037 (11)0.0349 (11)
C160.0546 (11)0.0507 (11)0.0690 (12)0.0038 (8)0.0004 (9)0.0257 (9)
C170.0504 (11)0.0567 (12)0.0773 (14)0.0054 (9)0.0035 (11)0.0239 (10)
C180.0493 (11)0.0829 (15)0.0690 (13)0.0173 (10)0.0036 (10)0.0227 (11)
C190.0566 (12)0.0562 (12)0.0761 (13)0.0092 (9)0.0065 (10)0.0239 (10)
C200.0573 (12)0.0747 (14)0.0786 (13)0.0071 (10)0.0052 (10)0.0521 (12)
C210.0588 (11)0.0622 (12)0.0732 (12)0.0139 (9)0.0088 (9)0.0358 (10)
C220.0760 (14)0.0733 (15)0.0978 (17)0.0102 (12)0.0179 (13)0.0440 (14)
C230.0973 (19)0.0671 (15)0.0985 (19)0.0282 (14)0.0157 (15)0.0203 (14)
C240.0984 (19)0.0875 (19)0.0934 (18)0.0382 (15)0.0097 (15)0.0268 (16)
C250.0810 (15)0.0785 (16)0.0796 (15)0.0282 (12)0.0141 (12)0.0299 (13)
C260.0610 (12)0.0670 (13)0.0699 (12)0.0207 (10)0.0024 (10)0.0328 (11)
C270.0714 (13)0.0829 (15)0.0701 (12)0.0177 (11)0.0212 (10)0.0469 (12)
C280.0715 (13)0.0739 (14)0.0701 (12)0.0128 (10)0.0194 (10)0.0466 (11)
C290.0526 (11)0.0845 (14)0.0787 (13)0.0106 (10)0.0152 (10)0.0457 (12)
C300.0570 (11)0.0759 (13)0.0704 (12)0.0012 (10)0.0084 (9)0.0426 (11)
C310.0556 (11)0.0716 (13)0.0587 (11)0.0166 (9)0.0090 (8)0.0433 (10)
C320.0712 (13)0.0709 (14)0.0661 (12)0.0156 (10)0.0090 (10)0.0375 (11)
C330.0911 (17)0.0847 (16)0.0788 (15)0.0267 (14)0.0202 (13)0.0353 (13)
C340.100 (2)0.105 (2)0.0972 (19)0.0329 (17)0.0438 (15)0.0366 (17)
C350.0691 (14)0.1033 (19)0.0983 (17)0.0151 (13)0.0281 (13)0.0532 (16)
C360.0560 (11)0.0763 (14)0.0653 (12)0.0148 (10)0.0089 (9)0.0450 (11)
C370.0502 (11)0.0862 (15)0.0769 (13)0.0054 (11)0.0042 (11)0.0561 (12)
C380.0540 (11)0.0717 (13)0.0677 (12)0.0020 (10)0.0015 (9)0.0445 (11)
C390.0499 (10)0.0532 (11)0.0595 (10)0.0126 (8)0.0129 (8)0.0282 (9)
C400.0667 (12)0.0571 (12)0.0801 (13)0.0163 (10)0.0156 (11)0.0317 (11)
C410.0701 (14)0.0611 (13)0.0848 (15)0.0014 (11)0.0053 (12)0.0192 (12)
C420.0704 (14)0.0776 (16)0.0792 (14)0.0040 (12)0.0134 (11)0.0272 (13)
C430.0657 (12)0.0718 (14)0.0712 (13)0.0082 (10)0.0069 (10)0.0351 (11)
C440.0491 (10)0.0569 (11)0.0592 (11)0.0095 (8)0.0053 (8)0.0290 (9)
C450.0749 (13)0.0705 (13)0.0748 (13)0.0138 (10)0.0067 (10)0.0474 (11)
C460.0723 (13)0.0632 (12)0.0829 (14)0.0085 (10)0.0070 (10)0.0501 (11)
C470.0722 (13)0.0606 (12)0.0876 (14)0.0209 (10)0.0005 (11)0.0406 (11)
C480.0858 (14)0.0536 (12)0.0744 (13)0.0209 (10)0.0016 (11)0.0321 (10)
C490.0562 (11)0.0631 (12)0.0539 (10)0.0095 (9)0.0047 (8)0.0321 (9)
C500.0760 (14)0.0668 (13)0.0653 (12)0.0101 (11)0.0009 (11)0.0289 (11)
C510.0762 (15)0.0821 (16)0.0709 (14)0.0058 (12)0.0059 (11)0.0218 (12)
C520.0787 (16)0.112 (2)0.0822 (16)0.0230 (15)0.0214 (13)0.0337 (16)
C530.0742 (14)0.0912 (17)0.0804 (14)0.0287 (12)0.0087 (12)0.0376 (13)
C540.0499 (10)0.0691 (12)0.0569 (10)0.0167 (9)0.0062 (8)0.0352 (10)
C550.0574 (11)0.0632 (12)0.0663 (11)0.0226 (9)0.0090 (9)0.0399 (10)
C560.0574 (11)0.0568 (11)0.0588 (10)0.0195 (8)0.0089 (9)0.0349 (9)
C570.0579 (11)0.0554 (11)0.0649 (11)0.0177 (9)0.0146 (9)0.0362 (10)
O10.0545 (12)0.139 (2)0.0884 (14)0.0309 (12)0.0096 (10)0.0315 (13)
O1'0.079 (6)0.142 (8)0.090 (6)0.063 (5)0.018 (4)0.047 (6)
O20.0511 (8)0.1105 (12)0.0688 (9)0.0109 (7)0.0041 (6)0.0391 (8)
O30.0572 (8)0.1169 (12)0.0693 (9)0.0312 (8)0.0090 (7)0.0337 (8)
O40.0751 (12)0.0944 (13)0.0961 (13)0.0129 (9)0.0005 (9)0.0541 (10)
O4'0.052 (10)0.097 (15)0.162 (19)0.027 (10)0.005 (12)0.034 (13)
O50.0779 (9)0.0655 (9)0.0703 (8)0.0123 (7)0.0215 (7)0.0338 (7)
O60.0605 (8)0.0707 (9)0.0639 (8)0.0012 (6)0.0161 (6)0.0324 (7)
O70.1009 (11)0.0641 (9)0.0927 (10)0.0327 (8)0.0031 (8)0.0382 (8)
O80.0721 (8)0.0557 (8)0.0694 (8)0.0076 (6)0.0115 (6)0.0363 (7)
O90.0904 (10)0.0537 (8)0.0676 (8)0.0195 (7)0.0140 (7)0.0289 (6)
Geometric parameters (Å, º) top
C1—C21.388 (3)C29—H29A0.9700
C1—C61.406 (3)C29—H29B0.9700
C1—C191.487 (3)C30—O61.428 (2)
C2—C31.372 (3)C30—H30A0.9700
C2—H20.9300C30—H30B0.9700
C3—C41.371 (3)C31—O61.358 (2)
C3—H30.9300C31—C321.381 (3)
C4—C51.370 (3)C31—C361.402 (2)
C4—H40.9300C32—C331.372 (3)
C5—C61.386 (3)C32—H320.9300
C5—H50.9300C33—C341.364 (3)
C6—O21.353 (2)C33—H330.9300
C7—O21.433 (2)C34—C351.379 (3)
C7—C81.499 (3)C34—H340.9300
C7—H7A0.9700C35—C361.394 (3)
C7—H7B0.9700C35—H350.9300
C8—C91.521 (3)C36—C371.464 (3)
C8—H8A0.9700C37—O4'1.276 (9)
C8—H8B0.9700C37—C381.336 (3)
C9—C101.500 (3)C37—H370.935 (5)
C9—H9A0.9700C38—H380.9300
C9—H9B0.9700C39—C401.399 (3)
C10—O31.425 (2)C39—C441.407 (2)
C10—H10A0.9700C39—C571.496 (2)
C10—H10B0.9700C40—C411.375 (3)
C11—O31.355 (2)C40—H400.9300
C11—C121.388 (3)C41—C421.366 (3)
C11—C161.404 (3)C41—H410.9300
C12—C131.369 (3)C42—C431.364 (3)
C12—H120.9300C42—H420.9300
C13—C141.370 (3)C43—C441.391 (3)
C13—H130.9300C43—H430.9300
C14—C151.376 (3)C44—O81.358 (2)
C14—H140.9300C45—O81.440 (2)
C15—C161.391 (3)C45—C461.497 (3)
C15—H150.9300C45—H45A0.9700
C16—C171.468 (3)C45—H45B0.9700
C17—O1'1.331 (6)C46—C471.524 (3)
C17—C181.337 (3)C46—H46A0.9700
C17—H170.933 (5)C46—H46B0.9700
C18—C191.425 (3)C47—C481.501 (3)
C18—H180.9300C47—H47A0.9700
C19—O11.258 (2)C47—H47B0.9700
C19—H190.930 (5)C48—O91.428 (2)
C20—O41.235 (2)C48—H48A0.9700
C20—C381.451 (3)C48—H48B0.9700
C20—C211.497 (3)C49—O91.355 (2)
C20—H200.930 (5)C49—C501.379 (3)
C21—C221.397 (3)C49—C541.406 (2)
C21—C261.400 (3)C50—C511.377 (3)
C22—C231.380 (3)C50—H500.9300
C22—H220.9300C51—C521.359 (3)
C23—C241.364 (4)C51—H510.9300
C23—H230.9300C52—C531.375 (3)
C24—C251.361 (3)C52—H520.9300
C24—H240.9300C53—C541.388 (3)
C25—C261.395 (3)C53—H530.9300
C25—H250.9300C54—C551.460 (3)
C26—O51.357 (2)C55—C561.325 (2)
C27—O51.433 (2)C55—H550.9300
C27—C281.496 (3)C56—C571.462 (2)
C27—H27A0.9700C56—H560.9300
C27—H27B0.9700C57—O71.228 (2)
C28—C291.527 (3)O1—H190.420 (5)
C28—H28A0.9700O1'—H170.484 (15)
C28—H28B0.9700O4—H200.31 (3)
C29—C301.500 (3)O4'—H370.342 (12)
C2—C1—C6117.19 (18)C28—C29—H29B108.8
C2—C1—C19116.88 (18)H29A—C29—H29B107.7
C6—C1—C19125.91 (17)O6—C30—C29105.39 (16)
C3—C2—C1122.5 (2)O6—C30—H30A110.7
C3—C2—H2118.7C29—C30—H30A110.7
C1—C2—H2118.7O6—C30—H30B110.7
C4—C3—C2119.1 (2)C29—C30—H30B110.7
C4—C3—H3120.4H30A—C30—H30B108.8
C2—C3—H3120.4O6—C31—C32123.27 (17)
C5—C4—C3120.5 (2)O6—C31—C36115.58 (17)
C5—C4—H4119.7C32—C31—C36121.15 (17)
C3—C4—H4119.7C33—C32—C31120.1 (2)
C4—C5—C6120.5 (2)C33—C32—H32119.9
C4—C5—H5119.8C31—C32—H32119.9
C6—C5—H5119.8C34—C33—C32120.4 (2)
O2—C6—C5122.91 (18)C34—C33—H33119.8
O2—C6—C1116.99 (17)C32—C33—H33119.8
C5—C6—C1120.09 (18)C33—C34—C35119.5 (2)
O2—C7—C8105.59 (16)C33—C34—H34120.2
O2—C7—H7A110.6C35—C34—H34120.2
C8—C7—H7A110.6C34—C35—C36122.2 (2)
O2—C7—H7B110.6C34—C35—H35118.9
C8—C7—H7B110.6C36—C35—H35118.9
H7A—C7—H7B108.8C35—C36—C31116.46 (19)
C7—C8—C9113.87 (18)C35—C36—C37118.94 (18)
C7—C8—H8A108.8C31—C36—C37124.58 (17)
C9—C8—H8A108.8O4'—C37—C38119.5 (18)
C7—C8—H8B108.8O4'—C37—C36110.8 (18)
C9—C8—H8B108.8C38—C37—C36128.95 (17)
H8A—C8—H8B107.7O4'—C37—H371 (5)
C10—C9—C8114.65 (18)C38—C37—H37121 (3)
C10—C9—H9A108.6C36—C37—H37109 (3)
C8—C9—H9A108.6C37—C38—C20123.12 (18)
C10—C9—H9B108.6C37—C38—H38118.4
C8—C9—H9B108.6C20—C38—H38118.4
H9A—C9—H9B107.6C40—C39—C44116.89 (17)
O3—C10—C9105.56 (16)C40—C39—C57116.85 (16)
O3—C10—H10A110.6C44—C39—C57126.25 (16)
C9—C10—H10A110.6C41—C40—C39122.10 (19)
O3—C10—H10B110.6C41—C40—H40119.0
C9—C10—H10B110.6C39—C40—H40119.0
H10A—C10—H10B108.8C42—C41—C40119.6 (2)
O3—C11—C12123.02 (18)C42—C41—H41120.2
O3—C11—C16116.58 (17)C40—C41—H41120.2
C12—C11—C16120.39 (19)C43—C42—C41120.6 (2)
C13—C12—C11120.5 (2)C43—C42—H42119.7
C13—C12—H12119.7C41—C42—H42119.7
C11—C12—H12119.7C42—C43—C44120.7 (2)
C12—C13—C14120.4 (2)C42—C43—H43119.7
C12—C13—H13119.8C44—C43—H43119.7
C14—C13—H13119.8O8—C44—C43122.17 (16)
C13—C14—C15119.3 (2)O8—C44—C39117.63 (15)
C13—C14—H14120.4C43—C44—C39120.16 (17)
C15—C14—H14120.4O8—C45—C46107.12 (14)
C14—C15—C16122.5 (2)O8—C45—H45A110.3
C14—C15—H15118.7C46—C45—H45A110.3
C16—C15—H15118.7O8—C45—H45B110.3
C15—C16—C11116.87 (18)C46—C45—H45B110.3
C15—C16—C17118.42 (18)H45A—C45—H45B108.5
C11—C16—C17124.71 (18)C45—C46—C47114.28 (16)
O1'—C17—C18121.0 (6)C45—C46—H46A108.7
O1'—C17—C16111.1 (6)C47—C46—H46A108.7
C18—C17—C16127.94 (18)C45—C46—H46B108.7
O1'—C17—H1714.2 (12)C47—C46—H46B108.7
C18—C17—H17116 (3)H46A—C46—H46B107.6
C16—C17—H17114 (3)C48—C47—C46113.72 (17)
C17—C18—C19124.49 (19)C48—C47—H47A108.8
C17—C18—H18117.8C46—C47—H47A108.8
C19—C18—H18117.8C48—C47—H47B108.8
O1—C19—C18120.5 (2)C46—C47—H47B108.8
O1—C19—C1116.98 (19)H47A—C47—H47B107.7
C18—C19—C1122.37 (18)O9—C48—C47105.23 (15)
O1—C19—H1913.9 (6)O9—C48—H48A110.7
C18—C19—H19134.5 (6)C47—C48—H48A110.7
C1—C19—H19103.1 (6)O9—C48—H48B110.7
O4—C20—C38121.5 (2)C47—C48—H48B110.7
O4—C20—C21117.6 (2)H48A—C48—H48B108.8
C38—C20—C21120.96 (17)O9—C49—C50123.04 (17)
O4—C20—H202 (10)O9—C49—C54115.83 (16)
C38—C20—H20120 (10)C50—C49—C54121.12 (17)
C21—C20—H20119 (10)C51—C50—C49120.0 (2)
C22—C21—C26116.9 (2)C51—C50—H50120.0
C22—C21—C20116.97 (19)C49—C50—H50120.0
C26—C21—C20126.07 (18)C52—C51—C50120.4 (2)
C23—C22—C21122.0 (2)C52—C51—H51119.8
C23—C22—H22119.0C50—C51—H51119.8
C21—C22—H22119.0C51—C52—C53119.7 (2)
C24—C23—C22119.6 (2)C51—C52—H52120.2
C24—C23—H23120.2C53—C52—H52120.2
C22—C23—H23120.2C52—C53—C54122.4 (2)
C25—C24—C23120.6 (2)C52—C53—H53118.8
C25—C24—H24119.7C54—C53—H53118.8
C23—C24—H24119.7C53—C54—C49116.41 (18)
C24—C25—C26120.5 (2)C53—C54—C55119.04 (17)
C24—C25—H25119.8C49—C54—C55124.54 (16)
C26—C25—H25119.8C56—C55—C54129.21 (17)
O5—C26—C25122.03 (19)C56—C55—H55115.4
O5—C26—C21117.57 (17)C54—C55—H55115.4
C25—C26—C21120.4 (2)C55—C56—C57123.24 (16)
O5—C27—C28106.78 (15)C55—C56—H56118.4
O5—C27—H27A110.4C57—C56—H56118.4
C28—C27—H27A110.4O7—C57—C56121.13 (17)
O5—C27—H27B110.4O7—C57—C39118.62 (16)
C28—C27—H27B110.4C56—C57—C39120.25 (15)
H27A—C27—H27B108.6C19—O1—H1932.3 (13)
C27—C28—C29114.89 (17)C17—O1'—H1728.3 (18)
C27—C28—H28A108.5C6—O2—C7121.20 (15)
C29—C28—H28A108.5C11—O3—C10121.56 (16)
C27—C28—H28B108.5C20—O4—H205 (10)
C29—C28—H28B108.5C37—O4'—H374 (10)
H28A—C28—H28B107.5C26—O5—C27119.54 (15)
C30—C29—C28113.87 (17)C31—O6—C30120.30 (15)
C30—C29—H29A108.8C44—O8—C45119.07 (14)
C28—C29—H29A108.8C49—O9—C48120.23 (14)
C30—C29—H29B108.8
C6—C1—C2—C30.6 (3)C32—C31—C36—C352.4 (3)
C19—C1—C2—C3179.13 (19)O6—C31—C36—C371.0 (3)
C1—C2—C3—C41.2 (3)C32—C31—C36—C37178.98 (17)
C2—C3—C4—C51.1 (3)C35—C36—C37—O4'5.5 (3)
C3—C4—C5—C60.4 (3)C31—C36—C37—O4'175.9 (3)
C4—C5—C6—O2179.27 (18)C35—C36—C37—C38175.71 (19)
C4—C5—C6—C10.2 (3)C31—C36—C37—C385.7 (3)
C2—C1—C6—O2179.23 (16)O4'—C37—C38—C2014.1 (4)
C19—C1—C6—O20.9 (3)C36—C37—C38—C20176.43 (17)
C2—C1—C6—C50.1 (3)O4—C20—C38—C3714.3 (3)
C19—C1—C6—C5178.27 (17)C21—C20—C38—C37163.96 (17)
O2—C7—C8—C969.8 (2)C44—C39—C40—C410.1 (3)
C7—C8—C9—C10135.73 (19)C57—C39—C40—C41178.80 (17)
C8—C9—C10—O366.2 (2)C39—C40—C41—C421.0 (3)
O3—C11—C12—C13179.56 (19)C40—C41—C42—C431.1 (3)
C16—C11—C12—C130.2 (3)C41—C42—C43—C440.0 (3)
C11—C12—C13—C141.1 (3)C42—C43—C44—O8178.90 (18)
C12—C13—C14—C150.9 (3)C42—C43—C44—C391.2 (3)
C13—C14—C15—C160.1 (3)C40—C39—C44—O8179.03 (15)
C14—C15—C16—C110.9 (3)C57—C39—C44—O80.2 (3)
C14—C15—C16—C17178.48 (18)C40—C39—C44—C431.2 (2)
O3—C11—C16—C15179.47 (17)C57—C39—C44—C43177.58 (17)
C12—C11—C16—C150.7 (3)O8—C45—C46—C4771.1 (2)
O3—C11—C16—C171.2 (3)C45—C46—C47—C48133.37 (17)
C12—C11—C16—C17178.60 (18)C46—C47—C48—O968.7 (2)
C15—C16—C17—O1'6.6 (5)O9—C49—C50—C51178.75 (18)
C11—C16—C17—O1'174.1 (5)C54—C49—C50—C510.2 (3)
C15—C16—C17—C18173.84 (18)C49—C50—C51—C520.3 (3)
C11—C16—C17—C185.5 (3)C50—C51—C52—C530.5 (4)
O1'—C17—C18—C192.8 (5)C51—C52—C53—C540.2 (4)
C16—C17—C18—C19177.69 (17)C52—C53—C54—C490.3 (3)
C17—C18—C19—O15.5 (2)C52—C53—C54—C55178.4 (2)
C17—C18—C19—C1170.82 (18)O9—C49—C54—C53179.17 (16)
C2—C1—C19—O117.7 (3)C50—C49—C54—C530.5 (3)
C6—C1—C19—O1160.68 (19)O9—C49—C54—C550.5 (2)
C2—C1—C19—C18165.91 (16)C50—C49—C54—C55178.11 (17)
C6—C1—C19—C1815.7 (3)C53—C54—C55—C56173.20 (19)
O4—C20—C21—C2218.2 (3)C49—C54—C55—C568.2 (3)
C38—C20—C21—C22163.50 (17)C54—C55—C56—C57175.25 (16)
O4—C20—C21—C26159.25 (18)C55—C56—C57—O710.3 (3)
C38—C20—C21—C2619.0 (3)C55—C56—C57—C39169.22 (16)
C26—C21—C22—C230.7 (3)C40—C39—C57—O719.8 (2)
C20—C21—C22—C23177.04 (18)C44—C39—C57—O7159.01 (17)
C21—C22—C23—C241.7 (3)C40—C39—C57—C56160.68 (15)
C22—C23—C24—C252.4 (4)C44—C39—C57—C5620.5 (3)
C23—C24—C25—C260.7 (4)C5—C6—O2—C75.4 (3)
C24—C25—C26—O5179.8 (2)C1—C6—O2—C7173.73 (17)
C24—C25—C26—C211.7 (3)C8—C7—O2—C6175.49 (17)
C22—C21—C26—O5179.53 (17)C12—C11—O3—C100.2 (3)
C20—C21—C26—O53.0 (3)C16—C11—O3—C10179.64 (18)
C22—C21—C26—C252.3 (3)C9—C10—O3—C11176.79 (18)
C20—C21—C26—C25175.11 (18)C25—C26—O5—C276.7 (3)
O5—C27—C28—C2972.9 (2)C21—C26—O5—C27175.18 (16)
C27—C28—C29—C30133.58 (18)C28—C27—O5—C26173.76 (16)
C28—C29—C30—O668.8 (2)C32—C31—O6—C300.3 (3)
O6—C31—C32—C33178.75 (17)C36—C31—O6—C30179.69 (16)
C36—C31—C32—C331.3 (3)C29—C30—O6—C31176.31 (15)
C31—C32—C33—C340.5 (3)C43—C44—O8—C454.8 (3)
C32—C33—C34—C351.1 (4)C39—C44—O8—C45177.49 (16)
C33—C34—C35—C360.1 (4)C46—C45—O8—C44171.89 (15)
C34—C35—C36—C311.8 (3)C50—C49—O9—C488.7 (3)
C34—C35—C36—C37179.5 (2)C54—C49—O9—C48172.64 (16)
O6—C31—C36—C35177.69 (17)C47—C48—O9—C49177.11 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.372.712 (3)101
C18—H18···O20.932.152.746 (2)121
C18—H18···O30.932.122.763 (2)126
C38—H38···O50.932.242.753 (2)114
C38—H38···O60.932.132.753 (3)123
C55—H55···O70.932.502.829 (2)101
C56—H56···O80.932.232.766 (2)116
C56—H56···O90.932.152.764 (2)122

Experimental details

Crystal data
Chemical formulaC19H18O3
Mr294.34
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.0976 (6), 16.9797 (11), 17.2713 (9)
α, β, γ (°)62.590 (2), 88.440 (2), 78.092 (2)
V3)2310.4 (2)
Z6
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.30 × 0.25
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.967, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
44770, 9919, 5862
Rint0.032
(sin θ/λ)max1)0.637
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.143, 1.04
No. of reflections9919
No. of parameters629
No. of restraints15
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.16

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.372.712 (3)101
C18—H18···O20.932.152.746 (2)121
C18—H18···O30.932.122.763 (2)126
C38—H38···O50.932.242.753 (2)114
C38—H38···O60.932.132.753 (3)123
C55—H55···O70.932.502.829 (2)101
C56—H56···O80.932.232.766 (2)116
C56—H56···O90.932.152.764 (2)122
 

Acknowledgements

The authors thank Dr Babu Varghese and SAIF, IIT, Chennai, India, for the data collection.

References

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