organic compounds
E)-1-(1-hydroxynaphthalen-2-yl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
of (aPG and Research Department of Physics, Queen Mary's College, Chennai 600 004, India, bDepartment of Chemistry, Madras Christian College, Chennai-59, India, and cPG and Research Department of Physics, Presidency College, University of Madras, Chennai 600 005, India
*Correspondence e-mail: anbu24663@yahoo.co.in
The title compound, C22H20O5, is composed of a hydroxynaphthyl ring and a trimethoxyphenyl ring [the planes of which are inclined to one another by 21.61 (10)°] bridged by an unsaturated prop-2-en-1-one group. The mean plane of the prop-2-en-1-one group [–C(=O)—C=C–] is inclined to that of the naphthyl system and benzene rings by 3.77 (14) and 18.01 (16)°, respectively. There is an intramolecular O—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, inversion-related molecules are linked by a slipped-parallel π–π interaction [intercentroid distance = 3.8942 (13) Å, interplanar distance = 3.478 (9) Å and slippage = 1.751 Å], and stack along the [101] direction. There are no other significant intermolecular interactions present.
Keywords: crystal structure; chalcones; hydroxynaphthalene; O—H⋯O hydrogen bond; S(6) ring motif; π–π slipped parallel interaction.
CCDC reference: 1414195
1. Related literature
For natural sources of ); Yadav et al. (2011). For their biological activities, see: Lin et al. (2002); Dhar (1981); Mukherjee et al. (2001); Bhat et al. (2005); Go et al. (2005); Sashidhara et al. (2011). For the synthesis by Claisen–Schmidt reaction, see: Shettigar et al. (2006); Ezhilarasi et al. (2015). For related structures, see: Wu et al. (2005); Lu et al. (2006); Harrison et al. (2007); Ezhilarasi et al. (2015).
and see: Anderson & Markham (20062. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 1414195
https://doi.org/10.1107/S2056989015013870/su5174sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013870/su5174Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015013870/su5174Isup3.cml
Chalcones have characteristic 1,3-diaryl-2-propen-1-one skeleton and occur naturally in roots, rhizomes, heartwood, leaves, petal pigments and seeds of many kinds of flora (Anderson & Markham, 2006; Yadav et al., 2011).
and chalconoid derivatives originate from the open chain flavonoid family form a wide spectrum of bioactive compounds exhibiting cytoprotective and immuno-modulatory functions (Anderson & Markham, 2006; Lin et al., 2002). The unsaturated ketone moiety, the conjugated double bonds and the radical quenching property of the phenolic group, presents versatile anti-inflammatory (Sashidhara et al., 2011), antibacterial, anti-oxidant (Mukherjee et al., 2001), antifungal (Go et al., 2005) and anticancerous properties (Dhar, 1981; Bhat et al., 2005). The type of substitutuent group and their pattern are linked closely to their pharmacological applications.The molecular structure of the title compound is illustrated in Fig. 1. The bond lengths and angles are similar to those reported for the above-mentioned compounds. Atoms O3, O4 and O5 of the methoxy groups deviate from the benzene ring by -0.032 (2), 0.026 (2) and -0.012 (2) Å, respectively. The dihedral angle between the planes of the naphthyl system and benzene ring is 21.61 (10)°, and those between the mean plane of the prop-2-en-1-one group [–C11(═O2)—C12═C13–] and those of the naphthyl system and benzene ring are 3.77 (14) and 18.01 (16)°, respectively. The C22—O5—C17—C18 , C20—O3—C19—C18 and C21—O4—C18—C19 torsion angles [164.3 (2), -73.7 (3) and -87.1 (3)°, respectively] indicate +ap, -sc and -sc orientations of the methoxy groups with respect to the benzene ring.
In the crystal (Fig. 2), the methoxy groups substituted in the 3- and 4-positions of the benzene ring allows stacking along [101], rather than close packing of the molecules. Inversion-related molecules are linked by a slipped parallel π–π interaction [Cg1···Cg1i = 3.8942 (13) Å, interplanar distance = 3.478 (9) Å and slippage = 1.751 Å; Cg1 is the centroid of C1–C3/C8–C10 ring ; symmetry code: (i) -x+1, -y+1, -z]. There are no other significant intermolecular interactions present.
In comparison to the
reported for (E)-1-(2-naphthyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Lu et al., 2006), the presence of an intramolecular O—H···O hydrogen bond (Table 1) between the hydroxy group and the propenone O atom in the title compound gives steric planar stability to the molecule in the E conformation and restricts the bending of the molecule.A series of related structures have been reported, viz. (E)-1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Wu et al., 2005), (E)-1-(2-naphthyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Lu et al., 2006), 1-(4-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Harrison et al., 2007) and (E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one (Ezhilarasi et al., 2015). The synthesis and
of a new similar chalcone analogue, namely (E)-1-(1-hydroxynaphthalen-2-yl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one, are reported here.The title compound was synthesized by Claisen–Schmidt reaction (Shettigar et al., 2006; Ezhilarasi et al., 2015). About 2 mmol of 1-(1-hydroxy-2-naphthyl)ethanone was added to 2,3,4-trimethoxybenzaldehyde (2 mmol) in a 250ml round-bottomed flask and the mixture was dissolved in 100 ml of absolute ethanol through constant stirring. A 10% sodium hydroxide solution (20 ml) was then added to this homogeneous mixture with continuous stirring for 24 h, which was initially pale-yellow but turned orange–red. The progress of the reaction was monitored by
(TLC) and upon completion of the reaction, the final mixture was quenched by pouring it into an ice-cold 10% solution of HCl (pH = 3) to precipitate the crude product. The orange precipitate was filtered off, washed with distilled water and dried at room temperature. The crude product after extraction with ethyl acetate was recrystallized with chloroform and allowed to evaporate slowly in a constant-temperature bath to give orange good-quality block-like crystals after 10 d (yield 79.8%; m.p. 394–395 K).Chalcones have characteristic 1,3-diaryl-2-propen-1-one skeleton and occur naturally in roots, rhizomes, heartwood, leaves, petal pigments and seeds of many kinds of flora (Anderson & Markham, 2006; Yadav et al., 2011).
and chalconoid derivatives originate from the open chain flavonoid family form a wide spectrum of bioactive compounds exhibiting cytoprotective and immuno-modulatory functions (Anderson & Markham, 2006; Lin et al., 2002). The unsaturated ketone moiety, the conjugated double bonds and the radical quenching property of the phenolic group, presents versatile anti-inflammatory (Sashidhara et al., 2011), antibacterial, anti-oxidant (Mukherjee et al., 2001), antifungal (Go et al., 2005) and anticancerous properties (Dhar, 1981; Bhat et al., 2005). The type of substitutuent group and their pattern are linked closely to their pharmacological applications.The molecular structure of the title compound is illustrated in Fig. 1. The bond lengths and angles are similar to those reported for the above-mentioned compounds. Atoms O3, O4 and O5 of the methoxy groups deviate from the benzene ring by -0.032 (2), 0.026 (2) and -0.012 (2) Å, respectively. The dihedral angle between the planes of the naphthyl system and benzene ring is 21.61 (10)°, and those between the mean plane of the prop-2-en-1-one group [–C11(═O2)—C12═C13–] and those of the naphthyl system and benzene ring are 3.77 (14) and 18.01 (16)°, respectively. The C22—O5—C17—C18 , C20—O3—C19—C18 and C21—O4—C18—C19 torsion angles [164.3 (2), -73.7 (3) and -87.1 (3)°, respectively] indicate +ap, -sc and -sc orientations of the methoxy groups with respect to the benzene ring.
In the crystal (Fig. 2), the methoxy groups substituted in the 3- and 4-positions of the benzene ring allows stacking along [101], rather than close packing of the molecules. Inversion-related molecules are linked by a slipped parallel π–π interaction [Cg1···Cg1i = 3.8942 (13) Å, interplanar distance = 3.478 (9) Å and slippage = 1.751 Å; Cg1 is the centroid of C1–C3/C8–C10 ring ; symmetry code: (i) -x+1, -y+1, -z]. There are no other significant intermolecular interactions present.
In comparison to the
reported for (E)-1-(2-naphthyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Lu et al., 2006), the presence of an intramolecular O—H···O hydrogen bond (Table 1) between the hydroxy group and the propenone O atom in the title compound gives steric planar stability to the molecule in the E conformation and restricts the bending of the molecule.A series of related structures have been reported, viz. (E)-1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Wu et al., 2005), (E)-1-(2-naphthyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Lu et al., 2006), 1-(4-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Harrison et al., 2007) and (E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one (Ezhilarasi et al., 2015). The synthesis and
of a new similar chalcone analogue, namely (E)-1-(1-hydroxynaphthalen-2-yl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one, are reported here.For natural sources of
and see: Anderson & Markham (2006); Yadav et al. (2011). For their biological activities, see: Lin et al. (2002); Dhar (1981); Mukherjee et al. (2001); Bhat et al. (2005); Go et al. (2005); Sashidhara et al. (2011). For the synthesis by Claisen-Schmidt reaction, see: Shettigar et al. (2006); Ezhilarasi et al. (2015). For related structures, see: Wu et al. (2005); Lu et al. (2006); Harrison et al. (2007); Ezhilarasi et al. (2015).The title compound was synthesized by Claisen–Schmidt reaction (Shettigar et al., 2006; Ezhilarasi et al., 2015). About 2 mmol of 1-(1-hydroxy-2-naphthyl)ethanone was added to 2,3,4-trimethoxybenzaldehyde (2 mmol) in a 250ml round-bottomed flask and the mixture was dissolved in 100 ml of absolute ethanol through constant stirring. A 10% sodium hydroxide solution (20 ml) was then added to this homogeneous mixture with continuous stirring for 24 h, which was initially pale-yellow but turned orange–red. The progress of the reaction was monitored by
(TLC) and upon completion of the reaction, the final mixture was quenched by pouring it into an ice-cold 10% solution of HCl (pH = 3) to precipitate the crude product. The orange precipitate was filtered off, washed with distilled water and dried at room temperature. The crude product after extraction with ethyl acetate was recrystallized with chloroform and allowed to evaporate slowly in a constant-temperature bath to give orange good-quality block-like crystals after 10 d (yield 79.8%; m.p. 394–395 K). detailsCrystal data, data collection and structure
details are summarized in Table 2. All H atoms were positioned geometrically and refined as riding atoms: O—H = 0.82 Å and C—H = 0.93–0.98 Å, with Uiso(H) = 1.5Ueq(O,C) for hydroxy and methyl H atoms, and 1.2Ueq(C) for the other H atoms.Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).C22H20O5 | F(000) = 768 |
Mr = 364.38 | Dx = 1.349 Mg m−3 |
Monoclinic, P21/c | Melting point: 394(2) K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4523 (8) Å | θ = 2.0–25.0° |
b = 14.0414 (12) Å | µ = 0.10 mm−1 |
c = 15.1672 (11) Å | T = 293 K |
β = 94.623 (3)° | Block, orange |
V = 1794.2 (3) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3151 independent reflections |
Radiation source: fine-focus sealed tube | 2143 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and φ scan | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→10 |
Tmin = 0.967, Tmax = 0.977 | k = −16→16 |
19676 measured reflections | l = −17→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.144 | w = 1/[σ2(Fo2) + (0.0626P)2 + 0.7956P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
3151 reflections | Δρmax = 0.19 e Å−3 |
245 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0031 (9) |
C22H20O5 | V = 1794.2 (3) Å3 |
Mr = 364.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.4523 (8) Å | µ = 0.10 mm−1 |
b = 14.0414 (12) Å | T = 293 K |
c = 15.1672 (11) Å | 0.35 × 0.30 × 0.25 mm |
β = 94.623 (3)° |
Bruker Kappa APEXII CCD diffractometer | 3151 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2143 reflections with I > 2σ(I) |
Tmin = 0.967, Tmax = 0.977 | Rint = 0.033 |
19676 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.19 e Å−3 |
3151 reflections | Δρmin = −0.18 e Å−3 |
245 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.3943 (2) | 0.35902 (11) | 0.13288 (11) | 0.0535 (5) | |
H7 | 0.3368 | 0.3315 | 0.0949 | 0.080* | |
O2 | 0.2007 (2) | 0.34197 (12) | 0.00026 (12) | 0.0590 (5) | |
C10 | 0.3050 (2) | 0.49116 (15) | 0.04358 (14) | 0.0363 (5) | |
O3 | −0.05999 (19) | 0.28866 (11) | −0.28956 (12) | 0.0522 (5) | |
C8 | 0.4894 (2) | 0.51062 (16) | 0.17556 (14) | 0.0384 (5) | |
O4 | −0.2147 (2) | 0.35002 (12) | −0.44607 (11) | 0.0556 (5) | |
C9 | 0.3937 (2) | 0.45260 (15) | 0.11569 (14) | 0.0374 (5) | |
C12 | 0.1103 (3) | 0.46876 (17) | −0.09075 (15) | 0.0441 (6) | |
H8 | 0.1033 | 0.5346 | −0.0966 | 0.053* | |
C18 | −0.1771 (3) | 0.41365 (16) | −0.37851 (15) | 0.0429 (6) | |
C3 | 0.4953 (3) | 0.60934 (16) | 0.15994 (15) | 0.0412 (6) | |
C14 | −0.0573 (3) | 0.44733 (16) | −0.23078 (15) | 0.0408 (6) | |
C11 | 0.2047 (3) | 0.42933 (17) | −0.01508 (15) | 0.0410 (6) | |
C13 | 0.0336 (3) | 0.41439 (17) | −0.15184 (15) | 0.0440 (6) | |
H9 | 0.0389 | 0.3489 | −0.1430 | 0.053* | |
C19 | −0.1002 (3) | 0.38331 (16) | −0.29973 (15) | 0.0422 (6) | |
C2 | 0.4064 (3) | 0.64762 (16) | 0.08524 (16) | 0.0475 (6) | |
H2 | 0.4108 | 0.7126 | 0.0740 | 0.057* | |
C15 | −0.1021 (3) | 0.54137 (17) | −0.24414 (15) | 0.0447 (6) | |
H10 | −0.0758 | 0.5853 | −0.1995 | 0.054* | |
C1 | 0.3154 (3) | 0.59125 (16) | 0.03021 (15) | 0.0439 (6) | |
H1 | 0.2575 | 0.6185 | −0.0181 | 0.053* | |
C16 | −0.1836 (3) | 0.57236 (17) | −0.32046 (16) | 0.0483 (6) | |
H11 | −0.2129 | 0.6360 | −0.3265 | 0.058* | |
C4 | 0.5891 (3) | 0.66571 (19) | 0.22005 (17) | 0.0523 (7) | |
H3 | 0.5934 | 0.7311 | 0.2111 | 0.063* | |
O5 | −0.3020 (2) | 0.53170 (13) | −0.46730 (11) | 0.0612 (5) | |
C17 | −0.2225 (3) | 0.50847 (17) | −0.38884 (15) | 0.0452 (6) | |
C6 | 0.6668 (3) | 0.5294 (2) | 0.30668 (17) | 0.0611 (7) | |
H5 | 0.7240 | 0.5033 | 0.3558 | 0.073* | |
C7 | 0.5762 (3) | 0.47234 (19) | 0.25003 (16) | 0.0510 (6) | |
H6 | 0.5718 | 0.4072 | 0.2609 | 0.061* | |
C5 | 0.6735 (3) | 0.6270 (2) | 0.29078 (18) | 0.0588 (7) | |
H4 | 0.7363 | 0.6657 | 0.3290 | 0.071* | |
C22 | −0.3846 (3) | 0.6192 (2) | −0.47248 (19) | 0.0649 (8) | |
H13 | −0.4353 | 0.6271 | −0.5310 | 0.097* | |
H14 | −0.3111 | 0.6705 | −0.4597 | 0.097* | |
H12 | −0.4633 | 0.6196 | −0.4303 | 0.097* | |
C20 | −0.1934 (3) | 0.22848 (19) | −0.2780 (2) | 0.0645 (8) | |
H19 | −0.1584 | 0.1637 | −0.2712 | 0.097* | |
H20 | −0.2684 | 0.2335 | −0.3288 | 0.097* | |
H18 | −0.2430 | 0.2479 | −0.2261 | 0.097* | |
C21 | −0.0907 (4) | 0.3367 (2) | −0.5025 (2) | 0.0822 (10) | |
H16 | −0.1239 | 0.2918 | −0.5480 | 0.123* | |
H15 | 0.0018 | 0.3129 | −0.4687 | 0.123* | |
H17 | −0.0661 | 0.3964 | −0.5290 | 0.123* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0681 (12) | 0.0373 (9) | 0.0539 (10) | 0.0006 (8) | −0.0029 (9) | 0.0036 (8) |
O2 | 0.0711 (13) | 0.0404 (11) | 0.0636 (12) | −0.0109 (9) | −0.0066 (9) | 0.0000 (8) |
C10 | 0.0351 (12) | 0.0352 (12) | 0.0392 (12) | 0.0002 (9) | 0.0064 (10) | 0.0003 (9) |
O3 | 0.0430 (10) | 0.0425 (10) | 0.0702 (12) | 0.0030 (8) | −0.0010 (8) | −0.0069 (8) |
C8 | 0.0321 (12) | 0.0452 (14) | 0.0384 (12) | 0.0042 (10) | 0.0059 (9) | −0.0026 (10) |
O4 | 0.0494 (10) | 0.0588 (11) | 0.0570 (11) | −0.0008 (8) | −0.0054 (8) | −0.0205 (9) |
C9 | 0.0405 (12) | 0.0315 (12) | 0.0413 (13) | 0.0040 (9) | 0.0100 (10) | 0.0012 (10) |
C12 | 0.0442 (13) | 0.0434 (14) | 0.0448 (14) | −0.0025 (11) | 0.0036 (11) | −0.0007 (11) |
C18 | 0.0334 (12) | 0.0464 (14) | 0.0483 (14) | −0.0037 (10) | −0.0010 (10) | −0.0130 (11) |
C3 | 0.0366 (12) | 0.0419 (13) | 0.0458 (14) | −0.0017 (10) | 0.0082 (10) | −0.0057 (11) |
C14 | 0.0333 (12) | 0.0466 (14) | 0.0426 (13) | −0.0035 (10) | 0.0037 (10) | −0.0055 (11) |
C11 | 0.0388 (13) | 0.0424 (14) | 0.0426 (13) | −0.0027 (10) | 0.0083 (10) | −0.0004 (10) |
C13 | 0.0399 (13) | 0.0453 (14) | 0.0471 (14) | −0.0021 (10) | 0.0052 (11) | −0.0023 (11) |
C19 | 0.0328 (12) | 0.0415 (13) | 0.0522 (15) | −0.0016 (10) | 0.0032 (10) | −0.0056 (11) |
C2 | 0.0502 (14) | 0.0339 (13) | 0.0576 (16) | −0.0030 (11) | 0.0006 (12) | 0.0023 (11) |
C15 | 0.0434 (13) | 0.0462 (14) | 0.0446 (14) | −0.0043 (11) | 0.0039 (11) | −0.0127 (11) |
C1 | 0.0460 (14) | 0.0411 (14) | 0.0436 (13) | 0.0008 (11) | −0.0021 (11) | 0.0057 (11) |
C16 | 0.0473 (14) | 0.0426 (14) | 0.0549 (16) | 0.0004 (11) | 0.0042 (12) | −0.0056 (12) |
C4 | 0.0461 (14) | 0.0523 (16) | 0.0586 (16) | −0.0045 (12) | 0.0044 (12) | −0.0109 (12) |
O5 | 0.0691 (12) | 0.0600 (12) | 0.0521 (11) | 0.0124 (9) | −0.0095 (9) | −0.0049 (9) |
C17 | 0.0394 (13) | 0.0512 (15) | 0.0445 (14) | 0.0007 (11) | 0.0009 (10) | −0.0041 (11) |
C6 | 0.0545 (16) | 0.082 (2) | 0.0450 (15) | 0.0108 (15) | −0.0073 (12) | −0.0051 (14) |
C7 | 0.0519 (15) | 0.0547 (16) | 0.0463 (14) | 0.0083 (12) | 0.0035 (12) | 0.0014 (12) |
C5 | 0.0469 (15) | 0.073 (2) | 0.0553 (17) | −0.0034 (14) | −0.0007 (13) | −0.0192 (14) |
C22 | 0.0716 (19) | 0.0591 (17) | 0.0624 (18) | 0.0114 (15) | −0.0036 (14) | 0.0067 (14) |
C20 | 0.0590 (17) | 0.0483 (16) | 0.087 (2) | −0.0054 (13) | 0.0098 (15) | −0.0017 (14) |
C21 | 0.079 (2) | 0.096 (2) | 0.073 (2) | −0.0078 (18) | 0.0174 (17) | −0.0383 (18) |
O1—C9 | 1.340 (3) | C2—H2 | 0.9300 |
O1—H7 | 0.8200 | C15—C16 | 1.369 (3) |
O2—C11 | 1.250 (3) | C15—H10 | 0.9300 |
C10—C9 | 1.386 (3) | C1—H1 | 0.9300 |
C10—C1 | 1.424 (3) | C16—C17 | 1.390 (3) |
C10—C11 | 1.464 (3) | C16—H11 | 0.9300 |
O3—C19 | 1.377 (3) | C4—C5 | 1.354 (4) |
O3—C20 | 1.431 (3) | C4—H3 | 0.9300 |
C8—C7 | 1.403 (3) | O5—C17 | 1.359 (3) |
C8—C3 | 1.408 (3) | O5—C22 | 1.413 (3) |
C8—C9 | 1.423 (3) | C6—C7 | 1.365 (4) |
O4—C18 | 1.377 (3) | C6—C5 | 1.392 (4) |
O4—C21 | 1.418 (3) | C6—H5 | 0.9300 |
C12—C13 | 1.328 (3) | C7—H6 | 0.9300 |
C12—C11 | 1.454 (3) | C5—H4 | 0.9300 |
C12—H8 | 0.9300 | C22—H13 | 0.9600 |
C18—C19 | 1.381 (3) | C22—H14 | 0.9600 |
C18—C17 | 1.391 (3) | C22—H12 | 0.9600 |
C3—C4 | 1.404 (3) | C20—H19 | 0.9600 |
C3—C2 | 1.414 (3) | C20—H20 | 0.9600 |
C14—C15 | 1.384 (3) | C20—H18 | 0.9600 |
C14—C19 | 1.404 (3) | C21—H16 | 0.9600 |
C14—C13 | 1.445 (3) | C21—H15 | 0.9600 |
C13—H9 | 0.9300 | C21—H17 | 0.9600 |
C2—C1 | 1.346 (3) | ||
C9—O1—H7 | 109.5 | C2—C1—H1 | 119.0 |
C9—C10—C1 | 117.5 (2) | C10—C1—H1 | 119.0 |
C9—C10—C11 | 119.9 (2) | C15—C16—C17 | 119.9 (2) |
C1—C10—C11 | 122.6 (2) | C15—C16—H11 | 120.1 |
C19—O3—C20 | 113.18 (18) | C17—C16—H11 | 120.1 |
C7—C8—C3 | 119.3 (2) | C5—C4—C3 | 121.5 (3) |
C7—C8—C9 | 121.8 (2) | C5—C4—H3 | 119.3 |
C3—C8—C9 | 118.8 (2) | C3—C4—H3 | 119.3 |
C18—O4—C21 | 113.39 (19) | C17—O5—C22 | 117.7 (2) |
O1—C9—C10 | 122.0 (2) | O5—C17—C16 | 124.7 (2) |
O1—C9—C8 | 116.40 (19) | O5—C17—C18 | 116.2 (2) |
C10—C9—C8 | 121.6 (2) | C16—C17—C18 | 119.2 (2) |
C13—C12—C11 | 122.5 (2) | C7—C6—C5 | 119.8 (2) |
C13—C12—H8 | 118.7 | C7—C6—H5 | 120.1 |
C11—C12—H8 | 118.7 | C5—C6—H5 | 120.1 |
O4—C18—C19 | 120.5 (2) | C6—C7—C8 | 120.8 (3) |
O4—C18—C17 | 119.5 (2) | C6—C7—H6 | 119.6 |
C19—C18—C17 | 119.9 (2) | C8—C7—H6 | 119.6 |
C4—C3—C8 | 118.1 (2) | C4—C5—C6 | 120.4 (2) |
C4—C3—C2 | 122.8 (2) | C4—C5—H4 | 119.8 |
C8—C3—C2 | 119.0 (2) | C6—C5—H4 | 119.8 |
C15—C14—C19 | 116.8 (2) | O5—C22—H13 | 109.5 |
C15—C14—C13 | 123.2 (2) | O5—C22—H14 | 109.5 |
C19—C14—C13 | 120.0 (2) | H13—C22—H14 | 109.5 |
O2—C11—C12 | 120.0 (2) | O5—C22—H12 | 109.5 |
O2—C11—C10 | 119.5 (2) | H13—C22—H12 | 109.5 |
C12—C11—C10 | 120.5 (2) | H14—C22—H12 | 109.5 |
C12—C13—C14 | 126.2 (2) | O3—C20—H19 | 109.5 |
C12—C13—H9 | 116.9 | O3—C20—H20 | 109.5 |
C14—C13—H9 | 116.9 | H19—C20—H20 | 109.5 |
O3—C19—C18 | 119.3 (2) | O3—C20—H18 | 109.5 |
O3—C19—C14 | 119.2 (2) | H19—C20—H18 | 109.5 |
C18—C19—C14 | 121.5 (2) | H20—C20—H18 | 109.5 |
C1—C2—C3 | 120.9 (2) | O4—C21—H16 | 109.5 |
C1—C2—H2 | 119.6 | O4—C21—H15 | 109.5 |
C3—C2—H2 | 119.6 | H16—C21—H15 | 109.5 |
C16—C15—C14 | 122.7 (2) | O4—C21—H17 | 109.5 |
C16—C15—H10 | 118.7 | H16—C21—H17 | 109.5 |
C14—C15—H10 | 118.7 | H15—C21—H17 | 109.5 |
C2—C1—C10 | 122.1 (2) | ||
C1—C10—C9—O1 | −178.69 (19) | C17—C18—C19—C14 | −4.0 (3) |
C11—C10—C9—O1 | 1.6 (3) | C15—C14—C19—O3 | −179.34 (19) |
C1—C10—C9—C8 | 1.3 (3) | C13—C14—C19—O3 | 2.5 (3) |
C11—C10—C9—C8 | −178.34 (19) | C15—C14—C19—C18 | 2.8 (3) |
C7—C8—C9—O1 | −1.8 (3) | C13—C14—C19—C18 | −175.3 (2) |
C3—C8—C9—O1 | 179.03 (18) | C4—C3—C2—C1 | −178.7 (2) |
C7—C8—C9—C10 | 178.2 (2) | C8—C3—C2—C1 | 0.9 (3) |
C3—C8—C9—C10 | −1.0 (3) | C19—C14—C15—C16 | −0.4 (3) |
C21—O4—C18—C19 | −87.1 (3) | C13—C14—C15—C16 | 177.7 (2) |
C21—O4—C18—C17 | 95.3 (3) | C3—C2—C1—C10 | −0.6 (4) |
C7—C8—C3—C4 | 0.2 (3) | C9—C10—C1—C2 | −0.6 (3) |
C9—C8—C3—C4 | 179.44 (19) | C11—C10—C1—C2 | 179.1 (2) |
C7—C8—C3—C2 | −179.4 (2) | C14—C15—C16—C17 | −0.9 (4) |
C9—C8—C3—C2 | −0.2 (3) | C8—C3—C4—C5 | 0.7 (3) |
C13—C12—C11—O2 | −8.7 (3) | C2—C3—C4—C5 | −179.7 (2) |
C13—C12—C11—C10 | 171.3 (2) | C22—O5—C17—C16 | −16.3 (4) |
C9—C10—C11—O2 | −0.3 (3) | C22—O5—C17—C18 | 164.3 (2) |
C1—C10—C11—O2 | −180.0 (2) | C15—C16—C17—O5 | −179.6 (2) |
C9—C10—C11—C12 | 179.7 (2) | C15—C16—C17—C18 | −0.2 (4) |
C1—C10—C11—C12 | 0.1 (3) | O4—C18—C17—O5 | −0.3 (3) |
C11—C12—C13—C14 | −177.3 (2) | C19—C18—C17—O5 | −177.9 (2) |
C15—C14—C13—C12 | −13.3 (4) | O4—C18—C17—C16 | −179.8 (2) |
C19—C14—C13—C12 | 164.7 (2) | C19—C18—C17—C16 | 2.6 (3) |
C20—O3—C19—C18 | −73.7 (3) | C5—C6—C7—C8 | 0.1 (4) |
C20—O3—C19—C14 | 108.4 (2) | C3—C8—C7—C6 | −0.6 (3) |
O4—C18—C19—O3 | 0.6 (3) | C9—C8—C7—C6 | −179.8 (2) |
C17—C18—C19—O3 | 178.2 (2) | C3—C4—C5—C6 | −1.2 (4) |
O4—C18—C19—C14 | 178.4 (2) | C7—C6—C5—C4 | 0.8 (4) |
Acknowledgements
The authors thank SAIF, IIT Madras, for providing the X-ray data collection facility and Central Instrumentation Facility, Queen Mary's College, Chennai-4, for providing the computing facility.
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