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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o842-o843
https://doi.org/10.1107/S2056989015018861

Crystal structure of 2-(2,3-di­meth­­oxy­naphthalen-1-yl)-3-hy­dr­oxy-6-meth­­oxy-4H-chromen-4-one

Seunghyun Ahn,a Yoongho Lima and Dongsoo Kohb*

aDivision of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul 143-701, Republic of Korea, and bDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
*Correspondence e-mail: dskoh@dongduk.ac.kr

Edited by K. Fejfarova, Institute of Macromolecular Chemistry, AS CR, v.v.i, Czech Republic (Received 29 September 2015; accepted 7 October 2015; online 14 October 2015)

In the title compound, C22H18O6, the dimeth­oxy-substituted naphthalene ring system is twisted relative to the 4H-chromenon skeleton by 88.96 (3)°. The two meth­oxy substituents are tilted from the naphthalene ring system by 1.4 (4) and 113.0 (2)°, respectively. An intra­molecular O—H⋯O hydrogen bond closes an S(5) ring motif. In the crystal, pairs of O—H⋯O hydrogen bonds form inversion dimers with R22(10) loops and C—H⋯O inter­actions connect the dimers into [010] chains.

CCDC reference: 1430031

Similar articles

1. Related literature

For the synthesis and biological properties of flavonols, see: Burmistrova et al. (2014[Burmistrova, O., Marrero, M., Estévez, S., Welsch, I., Brouard, I., Quintana, J. & Estévez, F. (2014). Eur. J. Med. Chem. 84, 30-41.]); Lee et al. (2014[Lee, M. S., Yong, Y., Lee, J. M., Koh, D., Shin, S. Y. & Lee, Y. H. (2014). J. Korean Soc. Appl. Biol. Chem. 57, 129-132.]); Dias et al. (2013[Dias, T. A., Duarte, C. L., Lima, C. F., Proença, F. & Pereira-Wilson, C. (2013). Eur. J. Med. Chem. 65, 500-510.]); Yong et al. (2013[Yong, Y., Ahn, S., Hwang, D., Yoon, H., Jo, G., Kim, Y. H., Kim, S. H., Koh, D. & Lim, Y. (2013). Magn. Reson. Chem. 51, 364-370.]); Klymchenko et al. (2003[Klymchenko, A. S., Pivovarenko, V. G. & Demchenko, A. P. (2003). Spectrochim. Acta Part A, 59, 787-792.]). For flavonols in natural products, see: Bendaikha et al. (2014[Bendaikha, S., Gadaut, M., Harakat, D. & Magid, A. (2014). Phytochemistry, 103, 129-136.]); Prescott et al. (2013[Prescott, T. A. K., Kite, G. C., Porter, E. A. & Veitch, N. C. (2013). Phytochemistry, 88, 85-91.]). For related structures, see: Narita et al. (2015[Narita, F., Takura, A. & Fujihara, T. (2015). Acta Cryst. E71, 824-826.]); Yoo et al. (2014[Yoo, J. S., Lim, Y. & Koh, D. (2014). Acta Cryst. E70, o999-o1000.]); Serdiuk et al. (2013[Serdiuk, I. E., Wera, M., Roshal, A. D. & Błażejowski, J. (2013). Acta Cryst. E69, o895.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C22H18O6

  • Mr = 378.36

  • Monoclinic, P 21 /c

  • a = 11.8571 (12) Å

  • b = 9.0888 (9) Å

  • c = 17.3977 (17) Å

  • β = 95.253 (2)°

  • V = 1867.0 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 200 K

  • 0.19 × 0.11 × 0.05 mm

2.2. Data collection

  • Bruker SMART CCD area-detector diffractometer

  • 13406 measured reflections

  • 4625 independent reflections

  • 2786 reflections with I > 2σ(I)

  • Rint = 0.036

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.184

  • S = 1.11

  • 4625 reflections

  • 257 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯O1 0.84 2.32 2.750 (2) 112
O2—H2⋯O1i 0.84 2.02 2.761 (2) 146
C14—H14⋯O1ii 0.95 2.60 3.502 (3) 158
C17—H17⋯O5iii 0.95 2.60 3.342 (3) 136
C22—H22A⋯O1iv 0.98 2.58 3.509 (4) 159
Symmetry codes: (i) -x, -y+1, -z; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) x, y-1, z; (iv) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1430031

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015018861/ff2142sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015018861/ff2142Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015018861/ff2142Isup3.cml

checkCIF report


Introduction top

Flavonols, such as Quercetin, Aza­leatin and Kaempferol, are a class of flavonoids that have a 3-hy­droxy­flavone backbone. Because of their wide spectrum of biological activities (Burmistrova et al. 2014, Dias et al. 2013), variety of flanonols have been isolated from natural sources and synthesized (Bendaikha et al. 2014; Prescott et al. 2013). In addition, they have been used as fluorescent probes for sensing and imaging due to their dual fluorescence. The fluorescence of flavonols has been shown to be related to the angle between the 4H-chromene-4-one moiety and the attached aromatic ring (Klymchenko et al. 2003). Our research project has been focused on development of novel flavonols which show broad range of biological activities (Lee et al. 2014), therefore the title compound was synthesized and its crystal structure was determined. A starting material, chalcone (III), was prepared by the previously reported methods (Yong et al. 2013). Flavonol was obtained by oxidative cyclization of the chalcone (III) with H2O2 in alkaline methanol medium (Fig. 3). In the title compound, C22H18O6, angle between the di­meth­oxy-substituted naphthalene ring and the 4H-chromenon skeleton is 88.96 (3)°, which shows they are almost orthogonal each other. In our previous report on flavonol (Yoo et al., 2014), the angle between 4H-chromenon and benzene ring is 5.2 (4)°. The meth­oxy groups in naphthalene ring at C12 and C13 are tilted from naphthalene ring by 1.4 (4)° and 113.0 (2)°, respectively. Meth­oxy group at C12 (meta position) lies almost in the same plane of naphthalene ring. Meth­oxy group at C13 (ortho position), however, is twisted away from the plane of naphthalene ring. An intra­molecular O—H···O hydrogen bond closes S(5) ring motif. In the crystal, pairs of O—H···O hydrogen bonds form inversion dimer with graph-set notation R22(10) and C—H···O inter­actions connect the dimers into [010] chains. Examples of structures of flavonols have been published (Narita et al., 2015; Serdiuk et al., 2013).

Experimental top

Equivalent amount of 2-hy­droxy-5-meth­oxy­aceto­phenone (I, 10 mmol, 1.66 g) and 2,3-di-meth­oxy­naphthaldehyde (II, 10mmol, 2.16 g) were dissolved in 20 mL of methanol and the temperature was adjusted to around 2-4 °C in an ice-bath. To a cooled reaction mixture was added 2 mL of 50% (w/v) aq. KOH solution and stirred at room temperature for 20h. At the end of the reaction, ice-water was added to the mixture and acidified with 3N HCl (pH = 3-4). The precipitation was filtered under vacuum and washed with methanol to give chalcone compound III (yield : 48 % , m.p : 407-408K). The chalcone compound (III, 1 mmol, 364 mg) was dissolved in 6 mL of methanol and 4 mL of THF. The reaction was cooled in a water-ice bath (2-4 °C) and a cold solution of 16% sodium hydroxide (1 mL ) was added with stirring. After 10 min, to the reaction mixture was added 2 mL of 35% H2O2. The end point of reaction was monitored by TLC. After completion of reaction, the reaction mixture was acidified with 3N HCl (pH = 4-5). The pale yellow precipitate obtained was filtered and washed with ethanol to give the titled compound (66%). Recrystallization in the ethanol solvent gave crystals (mp: 573-574K)

Refinement top

The H atoms were placed at calculated positions and refined as riding with C–H = 0.95 A [Uiso(H) = 1.2 Ueq(C)].

Related literature top

For the synthesis and biological properties of flavonols, see: Burmistrova et al. (2014); Lee et al. (2014); Dias et al. (2013); Yong et al. (2013); Klymchenko et al. (2003). For flavonols in natural products, see: Bendaikha et al. (2014); Prescott et al. (2013). For related structures, see: Narita et al. (2015); Yoo et al. (2014); Serdiuk et al. (2013).

Structure description top

Flavonols, such as Quercetin, Aza­leatin and Kaempferol, are a class of flavonoids that have a 3-hy­droxy­flavone backbone. Because of their wide spectrum of biological activities (Burmistrova et al. 2014, Dias et al. 2013), variety of flanonols have been isolated from natural sources and synthesized (Bendaikha et al. 2014; Prescott et al. 2013). In addition, they have been used as fluorescent probes for sensing and imaging due to their dual fluorescence. The fluorescence of flavonols has been shown to be related to the angle between the 4H-chromene-4-one moiety and the attached aromatic ring (Klymchenko et al. 2003). Our research project has been focused on development of novel flavonols which show broad range of biological activities (Lee et al. 2014), therefore the title compound was synthesized and its crystal structure was determined. A starting material, chalcone (III), was prepared by the previously reported methods (Yong et al. 2013). Flavonol was obtained by oxidative cyclization of the chalcone (III) with H2O2 in alkaline methanol medium (Fig. 3). In the title compound, C22H18O6, angle between the di­meth­oxy-substituted naphthalene ring and the 4H-chromenon skeleton is 88.96 (3)°, which shows they are almost orthogonal each other. In our previous report on flavonol (Yoo et al., 2014), the angle between 4H-chromenon and benzene ring is 5.2 (4)°. The meth­oxy groups in naphthalene ring at C12 and C13 are tilted from naphthalene ring by 1.4 (4)° and 113.0 (2)°, respectively. Meth­oxy group at C12 (meta position) lies almost in the same plane of naphthalene ring. Meth­oxy group at C13 (ortho position), however, is twisted away from the plane of naphthalene ring. An intra­molecular O—H···O hydrogen bond closes S(5) ring motif. In the crystal, pairs of O—H···O hydrogen bonds form inversion dimer with graph-set notation R22(10) and C—H···O inter­actions connect the dimers into [010] chains. Examples of structures of flavonols have been published (Narita et al., 2015; Serdiuk et al., 2013).

Equivalent amount of 2-hy­droxy-5-meth­oxy­aceto­phenone (I, 10 mmol, 1.66 g) and 2,3-di-meth­oxy­naphthaldehyde (II, 10mmol, 2.16 g) were dissolved in 20 mL of methanol and the temperature was adjusted to around 2-4 °C in an ice-bath. To a cooled reaction mixture was added 2 mL of 50% (w/v) aq. KOH solution and stirred at room temperature for 20h. At the end of the reaction, ice-water was added to the mixture and acidified with 3N HCl (pH = 3-4). The precipitation was filtered under vacuum and washed with methanol to give chalcone compound III (yield : 48 % , m.p : 407-408K). The chalcone compound (III, 1 mmol, 364 mg) was dissolved in 6 mL of methanol and 4 mL of THF. The reaction was cooled in a water-ice bath (2-4 °C) and a cold solution of 16% sodium hydroxide (1 mL ) was added with stirring. After 10 min, to the reaction mixture was added 2 mL of 35% H2O2. The end point of reaction was monitored by TLC. After completion of reaction, the reaction mixture was acidified with 3N HCl (pH = 4-5). The pale yellow precipitate obtained was filtered and washed with ethanol to give the titled compound (66%). Recrystallization in the ethanol solvent gave crystals (mp: 573-574K)

For the synthesis and biological properties of flavonols, see: Burmistrova et al. (2014); Lee et al. (2014); Dias et al. (2013); Yong et al. (2013); Klymchenko et al. (2003). For flavonols in natural products, see: Bendaikha et al. (2014); Prescott et al. (2013). For related structures, see: Narita et al. (2015); Yoo et al. (2014); Serdiuk et al. (2013).

Refinement details top

The H atoms were placed at calculated positions and refined as riding with C–H = 0.95 A [Uiso(H) = 1.2 Ueq(C)].

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom-labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of the crystal structure with intermolecular O—H···O hydrogen bonds shown as brown dashed lines and C—H···O interactions shown as blue dashed lines.
[Figure 3] Fig. 3. Synthetic scheme for the title compound.
2-(2,3-Dimethoxynaphthalen-1-yl)-3-hydroxy-6-methoxy-4H-chromen-4-one top
Crystal data top
C22H18O6F(000) = 792
Mr = 378.36Dx = 1.346 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4844 reflections
a = 11.8571 (12) Åθ = 2.4–28.2°
b = 9.0888 (9) ŵ = 0.10 mm−1
c = 17.3977 (17) ÅT = 200 K
β = 95.253 (2)°Block, yellow
V = 1867.0 (3) Å30.19 × 0.11 × 0.05 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2786 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 28.3°, θmin = 1.7°
phi and ω scansh = −15→10
13406 measured reflectionsk = −11→12
4625 independent reflectionsl = −22→23
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0751P)2 + 0.4684P]
where P = (Fo2 + 2Fc2)/3
4625 reflections(Δ/σ)max < 0.001
257 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
C22H18O6V = 1867.0 (3) Å3
Mr = 378.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.8571 (12) ŵ = 0.10 mm−1
b = 9.0888 (9) ÅT = 200 K
c = 17.3977 (17) Å0.19 × 0.11 × 0.05 mm
β = 95.253 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2786 reflections with I > 2σ(I)
13406 measured reflectionsRint = 0.036
4625 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.184H-atom parameters constrained
S = 1.11Δρmax = 0.28 e Å−3
4625 reflectionsΔρmin = −0.30 e Å−3
257 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*/Ueq
C10.19294 (16)0.5697 (2)0.04954 (11)0.0324 (4)
O10.12049 (12)0.59265 (17)−0.00540 (8)0.0419 (4)
C20.16533 (16)0.4835 (2)0.11528 (11)0.0334 (4)
O20.05942 (12)0.42964 (18)0.11735 (9)0.0444 (4)
H20.02020.45190.07630.067*
C30.24396 (16)0.4529 (2)0.17434 (12)0.0346 (5)
O30.35228 (12)0.50146 (17)0.17607 (8)0.0430 (4)
C40.38419 (18)0.5844 (2)0.11559 (13)0.0425 (5)
C50.4958 (2)0.6288 (3)0.11996 (15)0.0592 (7)
H50.54670.60230.16310.071*
C60.5324 (2)0.7113 (3)0.06168 (16)0.0659 (8)
H60.60960.74020.06380.079*
C70.45694 (19)0.7541 (3)−0.00160 (15)0.0533 (7)
C80.34661 (18)0.7105 (3)−0.00567 (13)0.0434 (5)
H80.29580.7393−0.04840.052*
C90.30769 (17)0.6229 (2)0.05332 (12)0.0358 (5)
O40.50460 (14)0.8384 (3)−0.05520 (11)0.0737 (6)
C100.4292 (3)0.8899 (4)−0.11779 (19)0.0901 (12)
H10A0.39530.8057−0.14650.135*
H10B0.47110.9502−0.15220.135*
H10C0.36940.9491−0.09780.135*
C110.22233 (16)0.3626 (2)0.24206 (12)0.0353 (5)
C120.18157 (18)0.4294 (2)0.30418 (12)0.0395 (5)
C130.15722 (19)0.3451 (3)0.36980 (12)0.0437 (5)
C140.16900 (19)0.1962 (3)0.36856 (13)0.0457 (6)
H140.14940.13990.41140.055*
C150.20979 (18)0.1235 (3)0.30471 (13)0.0429 (5)
C160.2199 (2)−0.0312 (3)0.30177 (16)0.0541 (6)
H160.1991−0.08870.34380.065*
C170.2589 (2)−0.0992 (3)0.23987 (17)0.0620 (7)
H170.2643−0.20350.23880.074*
C180.2910 (2)−0.0160 (3)0.17768 (17)0.0600 (7)
H180.3193−0.06410.13490.072*
C190.2818 (2)0.1338 (3)0.17818 (14)0.0480 (6)
H190.30420.18910.13580.058*
C200.23973 (17)0.2073 (2)0.24075 (12)0.0394 (5)
O50.16815 (13)0.57945 (17)0.30440 (9)0.0469 (4)
C210.0524 (2)0.6294 (3)0.30143 (18)0.0666 (8)
H21A0.00140.54430.29720.100*
H21B0.03610.69350.25650.100*
H21C0.04110.68420.34860.100*
O60.12322 (16)0.4267 (2)0.42964 (9)0.0579 (5)
C220.1006 (3)0.3472 (4)0.49711 (16)0.0753 (9)
H22A0.03460.28350.48530.113*
H22B0.08510.41660.53800.113*
H22C0.16650.28690.51450.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0330 (10)0.0339 (10)0.0302 (10)−0.0019 (8)0.0018 (8)−0.0013 (8)
O10.0368 (8)0.0538 (9)0.0339 (8)−0.0092 (7)−0.0029 (6)0.0068 (7)
C20.0314 (10)0.0361 (11)0.0329 (10)−0.0056 (8)0.0047 (8)0.0003 (8)
O20.0315 (8)0.0612 (10)0.0395 (8)−0.0139 (7)−0.0020 (6)0.0109 (7)
C30.0322 (10)0.0345 (10)0.0369 (10)−0.0035 (8)0.0018 (8)0.0025 (8)
O30.0312 (8)0.0541 (10)0.0426 (8)−0.0087 (6)−0.0025 (6)0.0135 (7)
C40.0367 (12)0.0464 (13)0.0439 (12)−0.0070 (9)0.0018 (9)0.0111 (10)
C50.0349 (12)0.0815 (19)0.0585 (15)−0.0148 (12)−0.0095 (11)0.0268 (14)
C60.0351 (13)0.091 (2)0.0703 (18)−0.0192 (13)−0.0024 (12)0.0313 (16)
C70.0389 (13)0.0680 (17)0.0532 (14)−0.0144 (11)0.0047 (10)0.0190 (12)
C80.0355 (12)0.0540 (14)0.0404 (12)−0.0096 (10)0.0017 (9)0.0095 (10)
C90.0333 (11)0.0369 (11)0.0371 (11)−0.0054 (8)0.0024 (8)0.0000 (9)
O40.0433 (10)0.1098 (17)0.0676 (12)−0.0240 (10)0.0024 (8)0.0421 (12)
C100.0637 (19)0.128 (3)0.076 (2)−0.0287 (19)−0.0054 (16)0.059 (2)
C110.0290 (10)0.0396 (11)0.0366 (11)−0.0044 (8)−0.0010 (8)0.0072 (9)
C120.0365 (11)0.0424 (12)0.0388 (11)−0.0050 (9)−0.0014 (9)0.0044 (9)
C130.0448 (13)0.0507 (14)0.0353 (11)−0.0063 (10)0.0018 (9)0.0038 (10)
C140.0436 (13)0.0549 (14)0.0378 (12)−0.0068 (10)0.0001 (9)0.0126 (10)
C150.0370 (12)0.0431 (12)0.0476 (13)−0.0033 (9)−0.0026 (9)0.0113 (10)
C160.0561 (15)0.0451 (14)0.0611 (16)−0.0010 (11)0.0048 (12)0.0147 (12)
C170.0683 (18)0.0414 (14)0.0770 (19)0.0033 (12)0.0113 (15)0.0110 (13)
C180.0646 (17)0.0470 (15)0.0698 (18)0.0048 (12)0.0144 (13)−0.0025 (13)
C190.0478 (13)0.0444 (13)0.0521 (14)0.0010 (10)0.0065 (10)0.0069 (11)
C200.0333 (11)0.0415 (12)0.0425 (12)−0.0022 (9)−0.0014 (9)0.0061 (10)
O50.0501 (10)0.0394 (9)0.0511 (9)−0.0035 (7)0.0040 (7)0.0007 (7)
C210.0572 (17)0.0562 (16)0.088 (2)0.0128 (13)0.0158 (14)0.0053 (15)
O60.0759 (12)0.0630 (12)0.0363 (9)−0.0054 (9)0.0126 (8)0.0012 (8)
C220.099 (2)0.087 (2)0.0412 (14)0.0023 (18)0.0173 (14)0.0098 (15)
Geometric parameters (Å, º) top
C1—O11.243 (2)C12—O51.373 (3)
C1—C91.440 (3)C12—C131.426 (3)
C1—C21.448 (3)C13—C141.361 (3)
C2—O21.351 (2)C13—O61.369 (3)
C2—C31.352 (3)C14—C151.415 (3)
O2—H20.8400C14—H140.9500
C3—O31.356 (2)C15—C161.413 (3)
C3—C111.477 (3)C15—C201.420 (3)
O3—C41.375 (2)C16—C171.359 (4)
C4—C51.379 (3)C16—H160.9500
C4—C91.392 (3)C17—C181.401 (4)
C5—C61.363 (3)C17—H170.9500
C5—H50.9500C18—C191.366 (3)
C6—C71.409 (3)C18—H180.9500
C6—H60.9500C19—C201.407 (3)
C7—C81.362 (3)C19—H190.9500
C7—O41.368 (3)O5—C211.442 (3)
C8—C91.410 (3)C21—H21A0.9800
C8—H80.9500C21—H21B0.9800
O4—C101.423 (3)C21—H21C0.9800
C10—H10A0.9800O6—C221.425 (3)
C10—H10B0.9800C22—H22A0.9800
C10—H10C0.9800C22—H22B0.9800
C11—C121.366 (3)C22—H22C0.9800
C11—C201.427 (3)
O1—C1—C9124.23 (18)C11—C12—C13120.4 (2)
O1—C1—C2120.52 (18)O5—C12—C13120.0 (2)
C9—C1—C2115.25 (16)C14—C13—O6126.1 (2)
O2—C2—C3118.88 (18)C14—C13—C12119.5 (2)
O2—C2—C1119.66 (16)O6—C13—C12114.4 (2)
C3—C2—C1121.45 (18)C13—C14—C15121.3 (2)
C2—O2—H2109.5C13—C14—H14119.3
C2—C3—O3122.40 (18)C15—C14—H14119.3
C2—C3—C11124.24 (18)C16—C15—C14122.0 (2)
O3—C3—C11113.35 (16)C16—C15—C20118.5 (2)
C3—O3—C4119.20 (15)C14—C15—C20119.5 (2)
O3—C4—C5116.63 (19)C17—C16—C15121.2 (2)
O3—C4—C9121.86 (18)C17—C16—H16119.4
C5—C4—C9121.5 (2)C15—C16—H16119.4
C6—C5—C4119.3 (2)C16—C17—C18120.2 (2)
C6—C5—H5120.4C16—C17—H17119.9
C4—C5—H5120.4C18—C17—H17119.9
C5—C6—C7120.7 (2)C19—C18—C17120.4 (3)
C5—C6—H6119.7C19—C18—H18119.8
C7—C6—H6119.7C17—C18—H18119.8
C8—C7—O4125.6 (2)C18—C19—C20120.8 (2)
C8—C7—C6119.9 (2)C18—C19—H19119.6
O4—C7—C6114.5 (2)C20—C19—H19119.6
C7—C8—C9120.2 (2)C19—C20—C15118.9 (2)
C7—C8—H8119.9C19—C20—C11122.9 (2)
C9—C8—H8119.9C15—C20—C11118.1 (2)
C4—C9—C8118.37 (18)C12—O5—C21115.00 (18)
C4—C9—C1119.78 (19)O5—C21—H21A109.5
C8—C9—C1121.83 (18)O5—C21—H21B109.5
C7—O4—C10115.85 (19)H21A—C21—H21B109.5
O4—C10—H10A109.5O5—C21—H21C109.5
O4—C10—H10B109.5H21A—C21—H21C109.5
H10A—C10—H10B109.5H21B—C21—H21C109.5
O4—C10—H10C109.5C13—O6—C22116.3 (2)
H10A—C10—H10C109.5O6—C22—H22A109.5
H10B—C10—H10C109.5O6—C22—H22B109.5
C12—C11—C20120.96 (19)H22A—C22—H22B109.5
C12—C11—C3118.94 (19)O6—C22—H22C109.5
C20—C11—C3120.05 (19)H22A—C22—H22C109.5
C11—C12—O5119.55 (19)H22B—C22—H22C109.5
O1—C1—C2—O2−1.1 (3)C2—C3—C11—C2090.0 (3)
C9—C1—C2—O2179.49 (18)O3—C3—C11—C20−89.0 (2)
O1—C1—C2—C3177.6 (2)C20—C11—C12—O5178.55 (17)
C9—C1—C2—C3−1.8 (3)C3—C11—C12—O5−4.0 (3)
O2—C2—C3—O3179.25 (18)C20—C11—C12—C131.0 (3)
C1—C2—C3—O30.6 (3)C3—C11—C12—C13178.53 (18)
O2—C2—C3—C110.3 (3)C11—C12—C13—C14−3.6 (3)
C1—C2—C3—C11−178.38 (19)O5—C12—C13—C14178.93 (19)
C2—C3—O3—C4−0.3 (3)C11—C12—C13—O6176.38 (19)
C11—C3—O3—C4178.71 (19)O5—C12—C13—O6−1.1 (3)
C3—O3—C4—C5−179.0 (2)O6—C13—C14—C15−177.1 (2)
C3—O3—C4—C91.5 (3)C12—C13—C14—C152.8 (3)
O3—C4—C5—C6180.0 (3)C13—C14—C15—C16−178.5 (2)
C9—C4—C5—C6−0.6 (4)C13—C14—C15—C200.4 (3)
C4—C5—C6—C71.5 (5)C14—C15—C16—C17179.8 (2)
C5—C6—C7—C8−1.3 (5)C20—C15—C16—C170.9 (4)
C5—C6—C7—O4179.1 (3)C15—C16—C17—C180.7 (4)
O4—C7—C8—C9179.7 (3)C16—C17—C18—C19−1.0 (4)
C6—C7—C8—C90.1 (4)C17—C18—C19—C20−0.2 (4)
O3—C4—C9—C8178.8 (2)C18—C19—C20—C151.8 (3)
C5—C4—C9—C8−0.6 (4)C18—C19—C20—C11−176.3 (2)
O3—C4—C9—C1−2.9 (3)C16—C15—C20—C19−2.1 (3)
C5—C4—C9—C1177.7 (2)C14—C15—C20—C19179.0 (2)
C7—C8—C9—C40.8 (4)C16—C15—C20—C11176.02 (19)
C7—C8—C9—C1−177.4 (2)C14—C15—C20—C11−2.8 (3)
O1—C1—C9—C4−176.5 (2)C12—C11—C20—C19−179.8 (2)
C2—C1—C9—C42.9 (3)C3—C11—C20—C192.7 (3)
O1—C1—C9—C81.7 (3)C12—C11—C20—C152.1 (3)
C2—C1—C9—C8−178.8 (2)C3—C11—C20—C15−175.34 (18)
C8—C7—O4—C103.5 (5)C11—C12—O5—C21113.0 (2)
C6—C7—O4—C10−176.8 (3)C13—C12—O5—C21−69.5 (3)
C2—C3—C11—C12−87.5 (3)C14—C13—O6—C221.4 (3)
O3—C3—C11—C1293.5 (2)C12—C13—O6—C22−178.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.842.322.750 (2)112
O2—H2···O1i0.842.022.7613 (19)146
C14—H14···O1ii0.952.603.502 (3)158
C17—H17···O5iii0.952.603.342 (3)136
C22—H22A···O1iv0.982.583.509 (4)159
Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+1/2, z+1/2; (iii) x, y−1, z; (iv) −x, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.842.322.750 (2)112
O2—H2···O1i0.842.022.7613 (19)146.2
C14—H14···O1ii0.952.603.502 (3)158.1
C17—H17···O5iii0.952.603.342 (3)135.7
C22—H22A···O1iv0.982.583.509 (4)159.4
Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+1/2, z+1/2; (iii) x, y−1, z; (iv) −x, y−1/2, −z+1/2.
 

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ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o842-o843
https://doi.org/10.1107/S2056989015018861
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