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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 66| Part 2| February 2010| Pages o470-o471
https://doi.org/10.1107/S1600536810003107

Di­methyl­ammonium 5,5-di­methyl-3-oxo-2-(3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthen-9-yl)cyclo­hex-1-enolate 9-(2-hydr­­oxy-4,4-di­methyl-6-oxo­cyclo­hex-1-en­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione n-hexane hemisolvate monohydrate

Noorhafizah Hasanudin,a Aisyah Saad Abdul Rahim,a‡ Salizawati Muhamad Salhimi,a Jia Hao Gohb§ and Hoong-Kun Funb*

aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 17 January 2010; accepted 25 January 2010; online 30 January 2010)

The main mol­ecule of the title compound, C2H8N+·C25H31O5−·C25H32O5·0.5C6H14·H2O, exists as two crystallographically independent mol­ecules, the hydr­oxy group of one being deprotonated. The pyran rings of both independent units adopt boat conformations. One of the two cyclo­hexene rings of the xanthene unit adopts an envelope conformation whereas the other is in a half-chair conformation. The cyclo­hexene ring attached to the xanthene unit adopts an envelope conformation. The n-hexane solvent mol­ecule is disordered about a crystallographic glide plane and the symmetry-independent components are again disordered over two positions, each with an occupancy of 0.25. In the crystal structure, the xanthene derivatives are linked by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network with channels along the a axis. The dimethyl­ammonium cations and water mol­ecules lie in small channels and are linked to the framework via O—H.·O and N—H⋯O hydrogen bonds. The n-hexane solvent mol­ecules occupy large channels.

Related literature

For general background and the preparation and applications of the title compound, see: Ashry et al. (2006[Ashry, E. S. H. E., Awad, L. F., Ibrahim, E. S. I. & Bdeewy, O. K. (2006). ARKIVOC, 2, 178-186.]); Rubinov et al. (1999[Rubinov, D. B., Rubinova, I. L. & Akhrem, A. A. (1999). Chem. Rev. 99, 1047-1066.]); Saitoh et al. (2006[Saitoh, T., Suzuki, S. & Hiraide, M. (2006). J. Chromatogr. A, 1134, 38-44.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, see: Jeyakanthan et al. (1999[Jeyakanthan, J., Shanmuga Sundara Raj, S., Velmurugan, D., Fun, H.-K. & Murugan, P. (1999). Acta Cryst. C55, 1515-1517.]); Odabaşoğlu et al. (2008[Odabaşoğlu, M., Kaya, M., Yıldırır, Y. & Büyükgüngör, O. (2008). Acta Cryst. E64, o681.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C2H8N+·C25H31O5−·C25H32O5·0.5C6H14·H2O

  • Mr = 931.20

  • Orthorhombic, P n a 21

  • a = 11.2438 (2) Å

  • b = 20.1671 (3) Å

  • c = 23.6474 (3) Å

  • V = 5362.16 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.48 × 0.38 × 0.20 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.984

  • 31958 measured reflections

  • 8021 independent reflections

  • 6458 reflections with I > 2σ(I)

  • Rint = 0.040
Refinement

  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.145

  • S = 1.03

  • 8021 reflections

  • 640 parameters

  • 19 restraints

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O5B—H5OB⋯O5A 0.82 1.69 2.488 (2) 163
O1W—H2W1⋯O4Ai 0.89 2.03 2.918 (3) 175
N1—H1N1⋯O4Aii 0.88 1.94 2.755 (3) 155
N1—H2N1⋯O1W 0.87 2.01 2.860 (3) 167
C4B—H4C⋯O2Ai 0.97 2.48 3.353 (4) 150
C12A—H12B⋯O3Aiii 0.97 2.41 3.261 (3) 146
C12B—H12C⋯O3Biv 0.97 2.36 3.238 (3) 150
C18A—H18A⋯O5B 0.97 2.55 3.227 (3) 126
C26—H26C⋯O4B 0.96 2.42 3.244 (4) 144
C27—H27B⋯O3B 0.96 2.34 3.055 (4) 131
Symmetry codes: (i) [-x, -y+1, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (iv) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z].

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810003107/ci5021sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810003107/ci5021Isup2.hkl

checkCIF report


Comment top

Dimedone derivatives are useful to determine airbone aldehydes (Saitoh et al., 2006) and these compounds are useful precursors of antibiotics and anticancer agents (Rubinov et al., 1999). Dimedone can also be further elaborated by condensing with 2-formyldimedone or triethyl orthoformate to form xanthene derivatives (Ashry et al., 2006). As part of an ongoing study on such compounds, in this paper, we present the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) comprises of two crystallographically independent 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione molecules, a dimethylammonia molecule, a partially occupied n-hexane solvent molecule and a water molecule. A proton is transferred from the atom O5A of hydroxy group in molecule A to the dimethylammonia molecule resulted in the formation of ions. The n-hexane solvent molecule is disordered over two positions each with an occupancy of 0.25. Both of these disordered components are further disordered over a crystallographic glide plane [symmetry code: x-1/2, 3/2-y, z]. Each main molecule contains a fused three-ring xanthene moiety and a cyclohexene moiety attached to the xanthene moiety. In the xanthene moiety, the cyclohexene ring A (C1-C6), the 4H-pyran ring B (O1/C1/C6-C8/C13) and the cyclohexene ring C (C8-C13) are not planar, having total puckering amplitudes Q of 0.495 (3), 0.238 (2) and 0.474 (3) Å, respectively; the corresponding values for rings D, E and F in molecule B are 0.482 (3), 0.196 (2) and 0.478 (3), respectively. Rings A, B and C adopt envelope [θ = 121.4 (3)° and φ = 307.8 (4)°], boat [θ = 73.3 (5)° and φ = 180.0 (1)°] and half-chair [θ = 55.6 (4)° and φ = 161.4 (4)°] conformations, respectively. Rings D, E and F in molecule B adopt similar conformations; the θ/φ values of 53.9 (4)°/127.5 (4)°, 108.2 (6)°/0.6 (8)° and 122.9 (4)°/340.7 (4)°, respectively. The cyclohexene ring (C14-C19) attached to the xanthene moiety is in an envelope conformation with puckering parameters Q = 0.466 (3) Å, θ = 59.6 (4)° and φ = 189.8 (4)° for molecule A and Q = 0.482 (3) Å, θ = 126.9 (4)° and φ = 353.3 (4)° for molecule B. The bond lengths and angles are comparable to those observed in related structures (Jeyakanthan et al., 1999; Odabaşoğlu et al., 2008).

In the crystal structure (Fig. 2), the n-hexane solvent molecule is not involved in intermolecular hydrogen bonding. All the other molecules and ions are linked by intermolecular O5B—H5OB···O5A, O1W—H2W1···O4A, N1—H2N1···O1W, C4B—H4C···O2A, C12A—H12B···O3A, C12B—H12C···O3B, C18A—H18A···O5B, C26—H26C···O4B and C27—H27B···O3B hydrogen bonds (Table 1) into three-dimensional supramolecular network such that n-hexane molecules are surrounded by these ions and molecules.

Related literature top

For general background to and the preparation and applications of the title compound, see: Ashry et al. (2006); Rubinov et al. (1999); Saitoh et al. (2006). For ring conformations, see: Cremer & Pople (1975). For related structures, see: Jeyakanthan et al. (1999); Odabaşoğlu et al. (2008). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound (Ashry et al., 2006) was obtained as a side product by refluxing a solution of dimethylformamide dimethylacetal (10 ml, 73.0 mmol) with 5,5-dimethylcyclohexane-1,3-dione (10.0 g, 71.4 mmol) in 1,2-dimethoxyethane (70 ml) for 2 h. The solution was evaporated in vacuo to yield a crude material. Good quality single crystals were obtained by recrystallization from EtOAc/Hexane (1:1).

Refinement top

The n-hexane solvent molecule is disordered over two positions each with an occupancy of 0.25; all atoms refined isotropically. The 1-2 and 1-3 C—C distances in the disordered components were restrained to 1.52 (1) and 2.50 (1) Å, respectively. H atoms bound to O1W and N1 were located in a difference Fourier map and then constrained to ride with the parent atom with Uiso(H) = 1.5Ueq(O) and 1.2 Ueq(N). The remaining H atoms were placed in the calculated positions (C—H = 0.96–0.98 Å) and refined using a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was used for the hydroxy and non-disordered methyl groups. Reflections 011 and 020 were omitted as their intensities were affected by the beam backstop. In the absence of significant anomalous dispersion, 4774 Friedel pairs were merged for the final refinement.

Structure description top

Dimedone derivatives are useful to determine airbone aldehydes (Saitoh et al., 2006) and these compounds are useful precursors of antibiotics and anticancer agents (Rubinov et al., 1999). Dimedone can also be further elaborated by condensing with 2-formyldimedone or triethyl orthoformate to form xanthene derivatives (Ashry et al., 2006). As part of an ongoing study on such compounds, in this paper, we present the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) comprises of two crystallographically independent 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione molecules, a dimethylammonia molecule, a partially occupied n-hexane solvent molecule and a water molecule. A proton is transferred from the atom O5A of hydroxy group in molecule A to the dimethylammonia molecule resulted in the formation of ions. The n-hexane solvent molecule is disordered over two positions each with an occupancy of 0.25. Both of these disordered components are further disordered over a crystallographic glide plane [symmetry code: x-1/2, 3/2-y, z]. Each main molecule contains a fused three-ring xanthene moiety and a cyclohexene moiety attached to the xanthene moiety. In the xanthene moiety, the cyclohexene ring A (C1-C6), the 4H-pyran ring B (O1/C1/C6-C8/C13) and the cyclohexene ring C (C8-C13) are not planar, having total puckering amplitudes Q of 0.495 (3), 0.238 (2) and 0.474 (3) Å, respectively; the corresponding values for rings D, E and F in molecule B are 0.482 (3), 0.196 (2) and 0.478 (3), respectively. Rings A, B and C adopt envelope [θ = 121.4 (3)° and φ = 307.8 (4)°], boat [θ = 73.3 (5)° and φ = 180.0 (1)°] and half-chair [θ = 55.6 (4)° and φ = 161.4 (4)°] conformations, respectively. Rings D, E and F in molecule B adopt similar conformations; the θ/φ values of 53.9 (4)°/127.5 (4)°, 108.2 (6)°/0.6 (8)° and 122.9 (4)°/340.7 (4)°, respectively. The cyclohexene ring (C14-C19) attached to the xanthene moiety is in an envelope conformation with puckering parameters Q = 0.466 (3) Å, θ = 59.6 (4)° and φ = 189.8 (4)° for molecule A and Q = 0.482 (3) Å, θ = 126.9 (4)° and φ = 353.3 (4)° for molecule B. The bond lengths and angles are comparable to those observed in related structures (Jeyakanthan et al., 1999; Odabaşoğlu et al., 2008).

In the crystal structure (Fig. 2), the n-hexane solvent molecule is not involved in intermolecular hydrogen bonding. All the other molecules and ions are linked by intermolecular O5B—H5OB···O5A, O1W—H2W1···O4A, N1—H2N1···O1W, C4B—H4C···O2A, C12A—H12B···O3A, C12B—H12C···O3B, C18A—H18A···O5B, C26—H26C···O4B and C27—H27B···O3B hydrogen bonds (Table 1) into three-dimensional supramolecular network such that n-hexane molecules are surrounded by these ions and molecules.

For general background to and the preparation and applications of the title compound, see: Ashry et al. (2006); Rubinov et al. (1999); Saitoh et al. (2006). For ring conformations, see: Cremer & Pople (1975). For related structures, see: Jeyakanthan et al. (1999); Odabaşoğlu et al. (2008). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. For clarity, n-hexane and water molecule are not shown.
[Figure 2] Fig. 2. The crystal structure of the title compound, viewed along the a axis, showing a three-dimensional extended framework. Only the major component of the n-hexane solvent is shown. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.
Dimethylammonium 5,5-dimethyl-3-oxo-2-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)cyclohex-1-enolate 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione n-hexane hemisolvate monohydrate top
Crystal data top
C2H8N+·C25H31O5−·C25H32O5·0.5C6H14·H2OF(000) = 2020
Mr = 931.20Dx = 1.153 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 8018 reflections
a = 11.2438 (2) Åθ = 2.3–27.8°
b = 20.1671 (3) ŵ = 0.08 mm−1
c = 23.6474 (3) ÅT = 100 K
V = 5362.16 (14) Å3Block, green
Z = 40.48 × 0.38 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		8021 independent reflections
Radiation source: fine-focus sealed tube6458 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −15→15
Tmin = 0.963, Tmax = 0.984k = −24→28
31958 measured reflectionsl = −33→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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0895P)2 + 0.2048P]
where P = (Fo2 + 2Fc2)/3
8021 reflections(Δ/σ)max = 0.001
640 parametersΔρmax = 0.48 e Å−3
19 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C2H8N+·C25H31O5−·C25H32O5·0.5C6H14·H2OV = 5362.16 (14) Å3
Mr = 931.20Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 11.2438 (2) ŵ = 0.08 mm−1
b = 20.1671 (3) ÅT = 100 K
c = 23.6474 (3) Å0.48 × 0.38 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		8021 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		6458 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.984Rint = 0.040
31958 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05219 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.03Δρmax = 0.48 e Å−3
8021 reflectionsΔρmin = −0.28 e Å−3
640 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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)
O1A0.40532 (16)0.38960 (9)0.07400 (7)0.0230 (4)
O2A0.20587 (19)0.44391 (10)−0.09549 (8)0.0320 (5)
O3A0.07499 (18)0.25143 (9)0.03492 (8)0.0279 (4)
O4A−0.05916 (17)0.36915 (9)−0.03060 (8)0.0264 (4)
O5A0.19677 (17)0.46088 (9)0.10553 (7)0.0239 (4)
C1A0.3864 (2)0.42668 (12)0.02593 (11)0.0219 (5)
C2A0.4877 (2)0.47346 (13)0.01506 (11)0.0254 (5)
H2A0.55390.4491−0.00110.030*
H2B0.51390.49250.05060.030*
C3A0.4517 (3)0.52930 (13)−0.02534 (11)0.0254 (5)
C4A0.3920 (3)0.49699 (14)−0.07642 (11)0.0266 (5)
H4A0.36570.5316−0.10200.032*
H4B0.45050.4703−0.09630.032*
C5A0.2873 (2)0.45387 (12)−0.06170 (11)0.0232 (5)
C6A0.2893 (2)0.41933 (12)−0.00681 (10)0.0200 (5)
C7A0.1862 (2)0.37597 (12)0.00998 (10)0.0194 (5)
H7A0.15960.3519−0.02370.023*
C8A0.2320 (2)0.32568 (12)0.05230 (10)0.0211 (5)
C9A0.1683 (2)0.26346 (12)0.05998 (11)0.0218 (5)
C10A0.2249 (3)0.21248 (13)0.09860 (12)0.0296 (6)
H10A0.28290.18720.07720.035*
H10B0.16400.18190.11150.035*
C11A0.2865 (3)0.24320 (14)0.15039 (12)0.0286 (6)
C12A0.3784 (2)0.29328 (13)0.12886 (11)0.0255 (5)
H12A0.40410.32090.16020.031*
H12B0.44740.26940.11490.031*
C13A0.3317 (2)0.33670 (12)0.08282 (11)0.0217 (5)
C14A0.0810 (2)0.41625 (12)0.03236 (11)0.0202 (5)
C15A−0.0335 (2)0.41081 (11)0.00663 (10)0.0203 (5)
C16A−0.1331 (2)0.45688 (13)0.02524 (12)0.0251 (5)
H16A−0.18690.43200.04930.030*
H16B−0.17740.4703−0.00800.030*
C17A−0.0947 (2)0.51939 (12)0.05702 (11)0.0217 (5)
C18A−0.0049 (2)0.49856 (13)0.10225 (11)0.0242 (5)
H18A0.02720.53810.12000.029*
H18B−0.04600.47330.13120.029*
C19A0.0967 (2)0.45751 (12)0.07962 (10)0.0210 (5)
C20A0.3661 (3)0.57760 (14)0.00350 (13)0.0329 (6)
H20A0.34200.6110−0.02310.049*
H20B0.40530.59820.03500.049*
H20C0.29750.55390.01660.049*
C21A0.5624 (3)0.56702 (16)−0.04494 (13)0.0345 (7)
H21A0.54010.5992−0.07290.052*
H21B0.61830.5364−0.06100.052*
H21C0.59800.5891−0.01320.052*
C22A0.1961 (3)0.2771 (2)0.18799 (13)0.0423 (8)
H22A0.16090.31360.16800.063*
H22B0.23470.29330.22150.063*
H22C0.13520.24600.19840.063*
C23A0.3510 (3)0.18878 (17)0.18375 (16)0.0439 (8)
H23A0.29360.15900.19990.066*
H23B0.39720.20860.21340.066*
H23C0.40260.16460.15880.066*
C24A−0.0372 (3)0.56907 (14)0.01634 (12)0.0315 (6)
H24A0.02900.5485−0.00230.047*
H24B−0.01000.60700.03720.047*
H24C−0.09460.5829−0.01130.047*
C25A−0.2012 (3)0.55234 (16)0.08483 (13)0.0333 (6)
H25A−0.24060.52100.10890.050*
H25B−0.25540.56740.05620.050*
H25C−0.17480.58950.10690.050*
O1B−0.00738 (16)0.60448 (8)0.22261 (7)0.0212 (4)
O2B0.23071 (18)0.53361 (9)0.37642 (7)0.0266 (4)
O3B0.3163 (2)0.74774 (11)0.25737 (9)0.0367 (5)
O4B0.44844 (17)0.61828 (9)0.33352 (8)0.0272 (4)
O5B0.21200 (16)0.54438 (9)0.18264 (7)0.0230 (4)
H5OB0.21920.52020.15490.035*
C1B0.0201 (2)0.56519 (12)0.26823 (10)0.0200 (5)
C2B−0.0728 (2)0.51373 (12)0.27835 (11)0.0229 (5)
H2C−0.10480.49920.24230.027*
H2D−0.13730.53300.30000.027*
C3B−0.0228 (2)0.45368 (12)0.31038 (11)0.0242 (5)
C4B0.0443 (3)0.48012 (13)0.36252 (11)0.0254 (5)
H4C−0.01230.50090.38790.031*
H4D0.08010.44310.38240.031*
C5B0.1397 (2)0.52953 (12)0.34798 (10)0.0212 (5)
C6B0.1197 (2)0.57298 (12)0.29920 (10)0.0193 (5)
C7B0.2158 (2)0.62140 (11)0.28249 (10)0.0180 (4)
H7B0.24120.64530.31650.022*
C8B0.1635 (2)0.67112 (12)0.24145 (11)0.0202 (5)
C9B0.2234 (3)0.73471 (13)0.23309 (12)0.0260 (5)
C10B0.1621 (3)0.78421 (14)0.19539 (14)0.0331 (6)
H10C0.22030.81610.18210.040*
H10D0.10330.80810.21740.040*
C11B0.1011 (3)0.75288 (15)0.14464 (14)0.0326 (6)
C12B0.0122 (2)0.70132 (13)0.16690 (12)0.0276 (6)
H12C−0.05780.72410.18110.033*
H12D−0.01270.67300.13590.033*
C13B0.0629 (2)0.65929 (11)0.21284 (11)0.0209 (5)
C14B0.3234 (2)0.58432 (12)0.25854 (10)0.0188 (5)
C15B0.4346 (2)0.58579 (12)0.28963 (11)0.0212 (5)
C16B0.5389 (2)0.54591 (12)0.26644 (11)0.0233 (5)
H16C0.59160.53440.29740.028*
H16D0.58330.57340.24020.028*
C17B0.5006 (2)0.48219 (12)0.23613 (11)0.0234 (5)
C18B0.4128 (2)0.50197 (13)0.18981 (11)0.0245 (5)
H18C0.45530.52560.16030.029*
H18D0.37930.46220.17320.029*
C19B0.3128 (2)0.54520 (12)0.21138 (10)0.0194 (5)
C20B0.0617 (3)0.41407 (14)0.27239 (13)0.0301 (6)
H20D0.01920.39830.23990.045*
H20E0.09290.37700.29310.045*
H20F0.12600.44210.26040.045*
C21B−0.1251 (3)0.40906 (14)0.33016 (13)0.0322 (6)
H21D−0.16750.39250.29790.048*
H21E−0.17820.43420.35360.048*
H21F−0.09350.37250.35140.048*
C22B0.1928 (3)0.7193 (2)0.10600 (13)0.0420 (8)
H22D0.23490.68590.12690.063*
H22E0.24820.75180.09240.063*
H22F0.15280.69910.07450.063*
C23B0.0340 (3)0.80580 (18)0.11072 (19)0.0509 (10)
H23D0.08920.83850.09720.076*
H23E−0.02400.82670.13460.076*
H23F−0.00520.78530.07920.076*
C24B0.4438 (3)0.43408 (13)0.27822 (13)0.0297 (6)
H24D0.42150.39410.25900.045*
H24E0.37440.45420.29450.045*
H24F0.49980.42380.30760.045*
C25B0.6089 (3)0.44849 (16)0.20926 (14)0.0343 (6)
H25D0.58370.40940.18940.051*
H25E0.66450.43650.23830.051*
H25F0.64620.47850.18320.051*
O1W0.30424 (18)0.65488 (10)0.43443 (8)0.0309 (4)
H1W10.33030.61610.44100.046*
H2W10.22800.64820.44310.046*
N10.4847 (2)0.75319 (10)0.41903 (9)0.0224 (4)
H1N10.49230.78660.44240.027*
H2N10.42230.72860.42340.027*
C260.5972 (3)0.71579 (16)0.41662 (17)0.0443 (8)
H26A0.61880.70160.45400.066*
H26B0.65880.74370.40160.066*
H26C0.58740.67770.39270.066*
C270.4533 (3)0.78416 (15)0.36451 (12)0.0357 (7)
H27A0.38230.81010.36900.054*
H27B0.43990.75020.33670.054*
H27C0.51720.81230.35230.054*
C28−0.1459 (18)0.7689 (14)0.8581 (10)0.095 (7)*0.25
H28A−0.22330.75540.87080.143*0.25
H28B−0.14420.81620.85380.143*0.25
H28C−0.12890.74830.82240.143*0.25
C29−0.0513 (16)0.7452 (12)0.8987 (9)0.091 (7)*0.25
H29A−0.05670.69800.90340.110*0.25
H29B−0.07190.76500.93430.110*0.25
C300.0716 (16)0.7662 (11)0.8792 (8)0.075 (5)*0.25
H30A0.07050.81240.86930.090*0.25
H30B0.08960.74290.84480.090*0.25
C310.1606 (17)0.7533 (15)0.9274 (9)0.105 (8)*0.25
H31A0.16000.71180.94730.126*0.25
H31B0.16890.78890.95400.126*0.25
C320.2838 (17)0.773 (2)0.9061 (12)0.120 (10)*0.25
H32A0.27410.81050.88150.144*0.25
H32B0.28390.73320.88390.144*0.25
C330.375 (2)0.768 (4)0.9532 (17)0.28 (4)*0.25
H33A0.44230.76950.92830.420*0.25
H33B0.37200.80770.97540.420*0.25
H33C0.38180.73020.97780.420*0.25
C28X−0.1944 (19)0.743 (2)0.8716 (16)0.164 (18)*0.25
H28D−0.23890.73980.83710.246*0.25
H28E−0.21070.70550.89500.246*0.25
H28F−0.21690.78300.89120.246*0.25
C29X−0.0707 (19)0.7670 (16)0.8539 (10)0.116 (10)*0.25
H29C−0.06440.80330.82790.139*0.25
H29D−0.05830.72790.83160.139*0.25
C30X0.0192 (17)0.7572 (13)0.9005 (8)0.088 (7)*0.25
H30C0.01660.71770.92320.105*0.25
H30D0.00140.79260.92630.105*0.25
C31X0.1456 (17)0.7710 (14)0.8791 (8)0.098 (8)*0.25
H31C0.16190.81510.86620.117*0.25
H31D0.17310.74010.85110.117*0.25
C32X0.2331 (18)0.760 (2)0.9278 (9)0.126 (11)*0.25
H32C0.21800.71570.94140.151*0.25
H32D0.20940.79130.95590.151*0.25
C33X0.3598 (18)0.7691 (15)0.9074 (11)0.101 (8)*0.25
H33D0.40980.76230.93990.151*0.25
H33E0.38010.73750.87860.151*0.25
H33F0.37140.81320.89320.151*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0221 (9)0.0246 (8)0.0224 (9)0.0006 (7)−0.0049 (7)0.0015 (7)
O2A0.0353 (12)0.0373 (10)0.0235 (9)−0.0043 (9)−0.0110 (8)0.0036 (8)
O3A0.0297 (10)0.0314 (9)0.0226 (9)−0.0045 (8)−0.0035 (8)0.0001 (8)
O4A0.0254 (9)0.0249 (8)0.0289 (9)0.0029 (8)−0.0095 (8)−0.0076 (7)
O5A0.0224 (9)0.0292 (9)0.0202 (8)0.0056 (7)−0.0059 (7)−0.0081 (7)
C1A0.0241 (13)0.0225 (11)0.0192 (11)0.0032 (10)−0.0002 (10)−0.0007 (9)
C2A0.0228 (13)0.0299 (12)0.0235 (12)−0.0028 (10)−0.0046 (10)0.0009 (10)
C3A0.0258 (13)0.0269 (11)0.0234 (12)−0.0040 (11)−0.0018 (10)0.0022 (10)
C4A0.0295 (14)0.0301 (12)0.0203 (12)−0.0029 (11)−0.0023 (10)0.0036 (10)
C5A0.0256 (13)0.0248 (11)0.0192 (11)0.0015 (10)−0.0013 (10)−0.0012 (9)
C6A0.0208 (12)0.0208 (11)0.0184 (11)0.0019 (9)−0.0009 (9)−0.0021 (9)
C7A0.0205 (11)0.0212 (10)0.0164 (11)0.0019 (9)−0.0010 (9)−0.0025 (9)
C8A0.0217 (12)0.0228 (10)0.0189 (11)0.0054 (10)0.0011 (10)−0.0015 (9)
C9A0.0260 (13)0.0234 (11)0.0159 (10)0.0019 (10)0.0019 (10)−0.0020 (9)
C10A0.0299 (14)0.0232 (11)0.0357 (15)0.0008 (11)−0.0042 (12)0.0065 (11)
C11A0.0225 (13)0.0345 (14)0.0289 (13)−0.0012 (11)−0.0028 (11)0.0109 (11)
C12A0.0232 (13)0.0307 (12)0.0225 (12)0.0048 (11)−0.0003 (10)0.0044 (10)
C13A0.0202 (12)0.0247 (11)0.0201 (11)0.0038 (10)0.0029 (10)−0.0007 (9)
C14A0.0203 (12)0.0213 (10)0.0191 (11)0.0029 (9)−0.0032 (9)−0.0031 (9)
C15A0.0221 (12)0.0188 (10)0.0200 (11)0.0026 (9)−0.0022 (9)−0.0013 (9)
C16A0.0208 (12)0.0271 (12)0.0273 (13)0.0033 (10)−0.0036 (10)−0.0036 (10)
C17A0.0209 (12)0.0246 (11)0.0195 (11)0.0067 (10)−0.0040 (9)−0.0052 (9)
C18A0.0256 (13)0.0286 (12)0.0184 (11)0.0063 (10)−0.0028 (10)−0.0057 (10)
C19A0.0236 (12)0.0212 (11)0.0182 (11)0.0020 (10)−0.0034 (10)−0.0022 (9)
C20A0.0355 (16)0.0269 (12)0.0362 (15)−0.0031 (12)0.0002 (13)−0.0031 (11)
C21A0.0313 (15)0.0378 (14)0.0344 (15)−0.0138 (13)−0.0067 (12)0.0091 (12)
C22A0.0280 (15)0.074 (2)0.0251 (14)−0.0032 (15)0.0013 (12)0.0021 (15)
C23A0.0373 (17)0.0426 (17)0.052 (2)−0.0061 (15)−0.0141 (16)0.0247 (15)
C24A0.0419 (16)0.0257 (12)0.0267 (14)0.0034 (12)−0.0031 (12)−0.0008 (11)
C25A0.0268 (14)0.0407 (15)0.0323 (15)0.0123 (12)−0.0049 (12)−0.0111 (12)
O1B0.0205 (9)0.0234 (8)0.0196 (8)0.0017 (7)−0.0009 (7)0.0009 (7)
O2B0.0311 (10)0.0288 (9)0.0201 (9)−0.0009 (8)−0.0039 (8)0.0000 (7)
O3B0.0380 (13)0.0371 (11)0.0349 (11)−0.0134 (10)−0.0096 (10)0.0076 (9)
O4B0.0261 (10)0.0294 (9)0.0259 (9)0.0002 (8)−0.0055 (8)−0.0084 (8)
O5B0.0238 (9)0.0278 (9)0.0175 (8)0.0059 (7)−0.0060 (7)−0.0078 (7)
C1B0.0214 (12)0.0214 (10)0.0173 (11)0.0011 (10)0.0018 (9)−0.0033 (9)
C2B0.0229 (12)0.0250 (11)0.0207 (12)−0.0031 (10)0.0017 (10)−0.0026 (9)
C3B0.0256 (13)0.0252 (11)0.0217 (12)−0.0047 (10)0.0011 (10)−0.0030 (10)
C4B0.0314 (14)0.0280 (12)0.0170 (11)−0.0036 (11)0.0004 (10)0.0003 (10)
C5B0.0263 (13)0.0226 (11)0.0148 (11)0.0004 (10)0.0013 (10)−0.0038 (9)
C6B0.0218 (12)0.0188 (10)0.0173 (11)0.0028 (9)0.0019 (9)−0.0034 (8)
C7B0.0176 (11)0.0199 (10)0.0166 (10)0.0002 (9)0.0012 (9)−0.0035 (9)
C8B0.0213 (12)0.0196 (10)0.0196 (11)0.0023 (9)0.0035 (9)−0.0023 (9)
C9B0.0245 (13)0.0258 (12)0.0277 (13)0.0006 (11)0.0020 (11)0.0004 (10)
C10B0.0286 (14)0.0249 (12)0.0458 (17)−0.0026 (12)0.0006 (13)0.0093 (12)
C11B0.0238 (13)0.0351 (14)0.0389 (15)0.0014 (12)−0.0019 (12)0.0164 (13)
C12B0.0225 (13)0.0289 (12)0.0315 (14)0.0042 (11)−0.0034 (11)0.0065 (11)
C13B0.0199 (12)0.0207 (10)0.0221 (12)0.0022 (10)0.0032 (9)−0.0028 (9)
C14B0.0185 (11)0.0214 (10)0.0166 (11)0.0032 (9)0.0006 (9)−0.0015 (9)
C15B0.0229 (12)0.0203 (10)0.0203 (11)0.0006 (10)−0.0025 (10)−0.0003 (9)
C16B0.0209 (12)0.0271 (12)0.0218 (12)0.0011 (10)−0.0020 (10)−0.0035 (10)
C17B0.0212 (12)0.0270 (12)0.0222 (12)0.0067 (10)−0.0021 (10)−0.0043 (10)
C18B0.0247 (13)0.0305 (12)0.0183 (11)0.0082 (11)−0.0034 (10)−0.0079 (10)
C19B0.0200 (12)0.0228 (11)0.0155 (11)0.0026 (9)−0.0004 (9)−0.0018 (9)
C20B0.0285 (14)0.0265 (12)0.0352 (15)−0.0025 (11)0.0016 (12)−0.0066 (11)
C21B0.0368 (16)0.0292 (13)0.0305 (14)−0.0098 (12)0.0005 (12)0.0006 (11)
C22B0.0281 (15)0.071 (2)0.0272 (14)0.0002 (15)0.0029 (13)0.0176 (15)
C23B0.0319 (17)0.0468 (18)0.074 (2)−0.0052 (15)−0.0131 (17)0.0333 (19)
C24B0.0321 (14)0.0245 (12)0.0326 (14)0.0014 (11)−0.0053 (12)−0.0016 (11)
C25B0.0248 (14)0.0422 (15)0.0358 (15)0.0111 (12)−0.0024 (12)−0.0118 (13)
O1W0.0320 (10)0.0303 (9)0.0305 (10)−0.0071 (8)0.0062 (9)−0.0044 (8)
N10.0248 (11)0.0230 (9)0.0196 (10)−0.0026 (9)0.0008 (8)0.0009 (8)
C260.0393 (18)0.0306 (14)0.063 (2)0.0081 (14)−0.0194 (17)−0.0175 (15)
C270.053 (2)0.0293 (13)0.0245 (13)−0.0020 (14)−0.0030 (13)0.0025 (11)
Geometric parameters (Å, º) top
O1A—C13A1.367 (3)C10B—C11B1.520 (5)
O1A—C1A1.377 (3)C10B—H10C0.97
O2A—C5A1.232 (3)C10B—H10D0.97
O3A—C9A1.229 (3)C11B—C23B1.533 (4)
O4A—C15A1.251 (3)C11B—C22B1.535 (5)
O5A—C19A1.283 (3)C11B—C12B1.536 (4)
C1A—C6A1.346 (4)C12B—C13B1.492 (4)
C1A—C2A1.501 (4)C12B—H12C0.97
C2A—C3A1.531 (4)C12B—H12D0.97
C2A—H2A0.97C14B—C19B1.371 (3)
C2A—H2B0.97C14B—C15B1.450 (3)
C3A—C4A1.528 (4)C15B—C16B1.524 (4)
C3A—C20A1.530 (4)C16B—C17B1.533 (4)
C3A—C21A1.530 (4)C16B—H16C0.97
C4A—C5A1.504 (4)C16B—H16D0.97
C4A—H4A0.97C17B—C18B1.528 (4)
C4A—H4B0.97C17B—C24B1.530 (4)
C5A—C6A1.473 (3)C17B—C25B1.532 (4)
C6A—C7A1.505 (4)C18B—C19B1.512 (3)
C7A—C8A1.515 (3)C18B—H18C0.97
C7A—C14A1.530 (3)C18B—H18D0.97
C7A—H7A0.98C20B—H20D0.96
C8A—C13A1.352 (4)C20B—H20E0.96
C8A—C9A1.456 (4)C20B—H20F0.96
C9A—C10A1.515 (4)C21B—H21D0.96
C10A—C11A1.538 (4)C21B—H21E0.96
C10A—H10A0.97C21B—H21F0.96
C10A—H10B0.97C22B—H22D0.96
C11A—C22A1.514 (4)C22B—H22E0.96
C11A—C12A1.532 (4)C22B—H22F0.96
C11A—C23A1.534 (4)C23B—H23D0.96
C12A—C13A1.493 (4)C23B—H23E0.96
C12A—H12A0.97C23B—H23F0.96
C12A—H12B0.97C24B—H24D0.96
C14A—C19A1.404 (3)C24B—H24E0.96
C14A—C15A1.429 (3)C24B—H24F0.96
C15A—C16A1.520 (4)C25B—H25D0.96
C16A—C17A1.530 (3)C25B—H25E0.96
C16A—H16A0.97C25B—H25F0.96
C16A—H16B0.97O1W—H1W10.85
C17A—C25A1.519 (4)O1W—H2W10.89
C17A—C18A1.530 (4)N1—C261.474 (4)
C17A—C24A1.532 (4)N1—C271.476 (4)
C18A—C19A1.509 (4)N1—H1N10.88
C18A—H18A0.97N1—H2N10.86
C18A—H18B0.97C26—H26A0.96
C20A—H20A0.96C26—H26B0.96
C20A—H20B0.96C26—H26C0.96
C20A—H20C0.96C27—H27A0.96
C21A—H21A0.96C27—H27B0.96
C21A—H21B0.96C27—H27C0.96
C21A—H21C0.96C28—C291.511 (10)
C22A—H22A0.96C28—H28A0.96
C22A—H22B0.96C28—H28B0.96
C22A—H22C0.96C28—H28C0.96
C23A—H23A0.96C29—C301.518 (10)
C23A—H23B0.96C29—H29A0.96
C23A—H23C0.96C29—H29B0.96
C24A—H24A0.96C30—C311.539 (10)
C24A—H24B0.96C30—H30A0.96
C24A—H24C0.96C30—H30B0.96
C25A—H25A0.96C31—C321.526 (10)
C25A—H25B0.96C31—H31A0.96
C25A—H25C0.96C31—H31B0.96
O1B—C1B1.374 (3)C32—C331.516 (10)
O1B—C13B1.379 (3)C32—H32A0.96
O2B—C5B1.227 (3)C32—H32B0.96
O3B—C9B1.221 (3)C33—H33A0.96
O4B—C15B1.237 (3)C33—H33B0.96
O5B—C19B1.322 (3)C33—H33C0.96
O5B—H5OB0.82C28X—C29X1.529 (10)
C1B—C6B1.347 (4)C28X—H28D0.96
C1B—C2B1.492 (4)C28X—H28E0.96
C2B—C3B1.535 (4)C28X—H28F0.96
C2B—H2C0.97C29X—C30X1.508 (10)
C2B—H2D0.97C29X—H29C0.96
C3B—C20B1.532 (4)C29X—H29D0.96
C3B—C21B1.533 (4)C30X—C31X1.534 (10)
C3B—C4B1.541 (4)C30X—H30C0.96
C4B—C5B1.504 (4)C30X—H30D0.96
C4B—H4C0.97C31X—C32X1.530 (10)
C4B—H4D0.97C31X—H31C0.96
C5B—C6B1.466 (3)C31X—H31D0.96
C6B—C7B1.509 (3)C32X—C33X1.516 (10)
C7B—C8B1.514 (3)C32X—H32C0.96
C7B—C14B1.532 (3)C32X—H32D0.96
C7B—H7B0.98C33X—H33D0.96
C8B—C13B1.339 (4)C33X—H33E0.96
C8B—C9B1.462 (4)C33X—H33F0.96
C9B—C10B1.506 (4)
C13A—O1A—C1A117.2 (2)H10C—C10B—H10D107.7
C6A—C1A—O1A122.7 (2)C10B—C11B—C23B110.2 (3)
C6A—C1A—C2A125.9 (2)C10B—C11B—C22B110.5 (3)
O1A—C1A—C2A111.4 (2)C23B—C11B—C22B109.0 (3)
C1A—C2A—C3A111.6 (2)C10B—C11B—C12B107.7 (2)
C1A—C2A—H2A109.3C23B—C11B—C12B109.3 (2)
C3A—C2A—H2A109.3C22B—C11B—C12B110.1 (3)
C1A—C2A—H2B109.3C13B—C12B—C11B112.7 (2)
C3A—C2A—H2B109.3C13B—C12B—H12C109.1
H2A—C2A—H2B108.0C11B—C12B—H12C109.1
C4A—C3A—C20A110.3 (2)C13B—C12B—H12D109.1
C4A—C3A—C21A109.2 (2)C11B—C12B—H12D109.1
C20A—C3A—C21A109.3 (2)H12C—C12B—H12D107.8
C4A—C3A—C2A107.2 (2)C8B—C13B—O1B122.9 (2)
C20A—C3A—C2A110.9 (2)C8B—C13B—C12B126.1 (2)
C21A—C3A—C2A109.9 (2)O1B—C13B—C12B111.0 (2)
C5A—C4A—C3A114.0 (2)C19B—C14B—C15B120.0 (2)
C5A—C4A—H4A108.7C19B—C14B—C7B120.8 (2)
C3A—C4A—H4A108.7C15B—C14B—C7B118.9 (2)
C5A—C4A—H4B108.7O4B—C15B—C14B123.0 (2)
C3A—C4A—H4B108.7O4B—C15B—C16B119.0 (2)
H4A—C4A—H4B107.6C14B—C15B—C16B118.0 (2)
O2A—C5A—C6A120.4 (2)C15B—C16B—C17B113.2 (2)
O2A—C5A—C4A121.7 (2)C15B—C16B—H16C108.9
C6A—C5A—C4A117.7 (2)C17B—C16B—H16C108.9
C1A—C6A—C5A117.8 (2)C15B—C16B—H16D108.9
C1A—C6A—C7A122.4 (2)C17B—C16B—H16D108.9
C5A—C6A—C7A119.7 (2)H16C—C16B—H16D107.7
C6A—C7A—C8A107.6 (2)C18B—C17B—C24B111.2 (2)
C6A—C7A—C14A112.2 (2)C18B—C17B—C25B109.4 (2)
C8A—C7A—C14A112.9 (2)C24B—C17B—C25B108.7 (2)
C6A—C7A—H7A108.0C18B—C17B—C16B107.3 (2)
C8A—C7A—H7A108.0C24B—C17B—C16B110.2 (2)
C14A—C7A—H7A108.0C25B—C17B—C16B110.1 (2)
C13A—C8A—C9A118.9 (2)C19B—C18B—C17B112.9 (2)
C13A—C8A—C7A121.6 (2)C19B—C18B—H18C109.0
C9A—C8A—C7A119.5 (2)C17B—C18B—H18C109.0
O3A—C9A—C8A122.0 (2)C19B—C18B—H18D109.0
O3A—C9A—C10A121.0 (2)C17B—C18B—H18D109.0
C8A—C9A—C10A117.0 (2)H18C—C18B—H18D107.8
C9A—C10A—C11A113.3 (2)O5B—C19B—C14B120.0 (2)
C9A—C10A—H10A108.9O5B—C19B—C18B117.2 (2)
C11A—C10A—H10A108.9C14B—C19B—C18B122.8 (2)
C9A—C10A—H10B108.9C3B—C20B—H20D109.5
C11A—C10A—H10B108.9C3B—C20B—H20E109.5
H10A—C10A—H10B107.7H20D—C20B—H20E109.5
C22A—C11A—C12A110.5 (3)C3B—C20B—H20F109.5
C22A—C11A—C23A109.8 (3)H20D—C20B—H20F109.5
C12A—C11A—C23A108.9 (2)H20E—C20B—H20F109.5
C22A—C11A—C10A110.3 (2)C3B—C21B—H21D109.5
C12A—C11A—C10A107.8 (2)C3B—C21B—H21E109.5
C23A—C11A—C10A109.5 (3)H21D—C21B—H21E109.5
C13A—C12A—C11A113.0 (2)C3B—C21B—H21F109.5
C13A—C12A—H12A109.0H21D—C21B—H21F109.5
C11A—C12A—H12A109.0H21E—C21B—H21F109.5
C13A—C12A—H12B109.0C11B—C22B—H22D109.5
C11A—C12A—H12B109.0C11B—C22B—H22E109.5
H12A—C12A—H12B107.8H22D—C22B—H22E109.5
C8A—C13A—O1A123.3 (2)C11B—C22B—H22F109.5
C8A—C13A—C12A125.8 (2)H22D—C22B—H22F109.5
O1A—C13A—C12A110.8 (2)H22E—C22B—H22F109.5
C19A—C14A—C15A119.8 (2)C11B—C23B—H23D109.5
C19A—C14A—C7A119.5 (2)C11B—C23B—H23E109.5
C15A—C14A—C7A120.6 (2)H23D—C23B—H23E109.5
O4A—C15A—C14A124.0 (2)C11B—C23B—H23F109.5
O4A—C15A—C16A116.4 (2)H23D—C23B—H23F109.5
C14A—C15A—C16A119.6 (2)H23E—C23B—H23F109.5
C15A—C16A—C17A116.0 (2)C17B—C24B—H24D109.5
C15A—C16A—H16A108.3C17B—C24B—H24E109.5
C17A—C16A—H16A108.3H24D—C24B—H24E109.5
C15A—C16A—H16B108.3C17B—C24B—H24F109.5
C17A—C16A—H16B108.3H24D—C24B—H24F109.5
H16A—C16A—H16B107.4H24E—C24B—H24F109.5
C25A—C17A—C16A110.6 (2)C17B—C25B—H25D109.5
C25A—C17A—C18A109.7 (2)C17B—C25B—H25E109.5
C16A—C17A—C18A107.7 (2)H25D—C25B—H25E109.5
C25A—C17A—C24A108.6 (2)C17B—C25B—H25F109.5
C16A—C17A—C24A110.5 (2)H25D—C25B—H25F109.5
C18A—C17A—C24A109.9 (2)H25E—C25B—H25F109.5
C19A—C18A—C17A113.7 (2)H1W1—O1W—H2W198.6
C19A—C18A—H18A108.8C26—N1—C27112.9 (3)
C17A—C18A—H18A108.8C26—N1—H1N1109.5
C19A—C18A—H18B108.8C27—N1—H1N1104.4
C17A—C18A—H18B108.8C26—N1—H2N1114.0
H18A—C18A—H18B107.7C27—N1—H2N198.8
O5A—C19A—C14A121.4 (2)H1N1—N1—H2N1116.4
O5A—C19A—C18A117.7 (2)N1—C26—H26A109.5
C14A—C19A—C18A120.8 (2)N1—C26—H26B109.5
C3A—C20A—H20A109.5H26A—C26—H26B109.5
C3A—C20A—H20B109.5N1—C26—H26C109.5
H20A—C20A—H20B109.5H26A—C26—H26C109.5
C3A—C20A—H20C109.5H26B—C26—H26C109.5
H20A—C20A—H20C109.5N1—C27—H27A109.5
H20B—C20A—H20C109.5N1—C27—H27B109.5
C3A—C21A—H21A109.5H27A—C27—H27B109.5
C3A—C21A—H21B109.5N1—C27—H27C109.5
H21A—C21A—H21B109.5H27A—C27—H27C109.5
C3A—C21A—H21C109.5H27B—C27—H27C109.5
H21A—C21A—H21C109.5C29—C28—H28A110.4
H21B—C21A—H21C109.5C29—C28—H28B111.6
C11A—C22A—H22A109.5H28A—C28—H28B109.5
C11A—C22A—H22B109.5C29—C28—H28C106.4
H22A—C22A—H22B109.5H28A—C28—H28C109.5
C11A—C22A—H22C109.5H28B—C28—H28C109.5
H22A—C22A—H22C109.5C28—C29—C30111.0 (10)
H22B—C22A—H22C109.5C28—C29—H29A110.0
C11A—C23A—H23A109.5C30—C29—H29A111.6
C11A—C23A—H23B109.5C28—C29—H29B104.9
H23A—C23A—H23B109.5C30—C29—H29B111.7
C11A—C23A—H23C109.5H29A—C29—H29B107.2
H23A—C23A—H23C109.5C29—C30—C31108.7 (9)
H23B—C23A—H23C109.5C29—C30—H30A109.4
C17A—C24A—H24A109.5C31—C30—H30A110.7
C17A—C24A—H24B109.5C29—C30—H30B108.2
H24A—C24A—H24B109.5C31—C30—H30B114.0
C17A—C24A—H24C109.5H30A—C30—H30B105.8
H24A—C24A—H24C109.5C32—C31—C30107.6 (9)
H24B—C24A—H24C109.5C32—C31—H31A113.3
C17A—C25A—H25A109.5C30—C31—H31A120.4
C17A—C25A—H25B109.5C32—C31—H31B86.1
H25A—C25A—H25B109.5C30—C31—H31B114.9
C17A—C25A—H25C109.5H31A—C31—H31B109.4
H25A—C25A—H25C109.5C33—C32—C31110.7 (10)
H25B—C25A—H25C109.5C33—C32—H32A125.1
C1B—O1B—C13B117.7 (2)C31—C32—H32A107.6
C19B—O5B—H5OB109.5C33—C32—H32B110.2
C6B—C1B—O1B123.1 (2)C31—C32—H32B87.9
C6B—C1B—C2B125.2 (2)H32A—C32—H32B109.1
O1B—C1B—C2B111.7 (2)C32—C33—H33A94.7
C1B—C2B—C3B111.8 (2)C32—C33—H33B108.8
C1B—C2B—H2C109.3H33A—C33—H33B109.5
C3B—C2B—H2C109.3C32—C33—H33C123.6
C1B—C2B—H2D109.3H33A—C33—H33C109.5
C3B—C2B—H2D109.3H33B—C33—H33C109.5
H2C—C2B—H2D107.9C29X—C28X—H28D105.3
C20B—C3B—C21B109.8 (2)C29X—C28X—H28E125.5
C20B—C3B—C2B110.4 (2)H28D—C28X—H28E109.5
C21B—C3B—C2B109.8 (2)C29X—C28X—H28F96.4
C20B—C3B—C4B110.2 (2)H28D—C28X—H28F109.5
C21B—C3B—C4B109.0 (2)H28E—C28X—H28F109.5
C2B—C3B—C4B107.5 (2)C30X—C29X—C28X111.7 (10)
C5B—C4B—C3B113.3 (2)C30X—C29X—H29C121.3
C5B—C4B—H4C108.9C28X—C29X—H29C118.8
C3B—C4B—H4C108.9C30X—C29X—H29D101.4
C5B—C4B—H4D108.9C28X—C29X—H29D91.5
C3B—C4B—H4D108.9H29C—C29X—H29D105.2
H4C—C4B—H4D107.7C29X—C30X—C31X110.9 (9)
O2B—C5B—C6B121.3 (2)C29X—C30X—H30C119.6
O2B—C5B—C4B120.9 (2)C31X—C30X—H30C111.3
C6B—C5B—C4B117.8 (2)C29X—C30X—H30D103.1
C1B—C6B—C5B119.1 (2)C31X—C30X—H30D105.6
C1B—C6B—C7B121.9 (2)H30C—C30X—H30D104.9
C5B—C6B—C7B118.9 (2)C32X—C31X—C30X108.7 (9)
C6B—C7B—C8B108.6 (2)C32X—C31X—H31C104.8
C6B—C7B—C14B110.29 (19)C30X—C31X—H31C116.8
C8B—C7B—C14B113.1 (2)C32X—C31X—H31D102.5
C6B—C7B—H7B108.2C30X—C31X—H31D114.1
C8B—C7B—H7B108.2H31C—C31X—H31D108.6
C14B—C7B—H7B108.2C33X—C32X—C31X110.3 (10)
C13B—C8B—C9B118.5 (2)C33X—C32X—H32C112.9
C13B—C8B—C7B122.2 (2)C31X—C32X—H32C106.1
C9B—C8B—C7B119.3 (2)C33X—C32X—H32D113.4
O3B—C9B—C8B121.3 (3)C31X—C32X—H32D104.1
O3B—C9B—C10B121.8 (3)H32C—C32X—H32D109.4
C8B—C9B—C10B116.8 (2)C32X—C33X—H33D106.2
C9B—C10B—C11B113.5 (2)C32X—C33X—H33E111.4
C9B—C10B—H10C108.9H33D—C33X—H33E109.5
C11B—C10B—H10C108.9C32X—C33X—H33F110.8
C9B—C10B—H10D108.9H33D—C33X—H33F109.5
C11B—C10B—H10D108.9H33E—C33X—H33F109.5
C13A—O1A—C1A—C6A10.7 (3)O1B—C1B—C2B—C3B155.9 (2)
C13A—O1A—C1A—C2A−167.9 (2)C1B—C2B—C3B—C20B−70.1 (3)
C6A—C1A—C2A—C3A20.0 (4)C1B—C2B—C3B—C21B168.7 (2)
O1A—C1A—C2A—C3A−161.5 (2)C1B—C2B—C3B—C4B50.2 (3)
C1A—C2A—C3A—C4A−49.6 (3)C20B—C3B—C4B—C5B64.7 (3)
C1A—C2A—C3A—C20A70.9 (3)C21B—C3B—C4B—C5B−174.7 (2)
C1A—C2A—C3A—C21A−168.2 (2)C2B—C3B—C4B—C5B−55.7 (3)
C20A—C3A—C4A—C5A−64.5 (3)C3B—C4B—C5B—O2B−147.8 (2)
C21A—C3A—C4A—C5A175.4 (2)C3B—C4B—C5B—C6B32.9 (3)
C2A—C3A—C4A—C5A56.4 (3)O1B—C1B—C6B—C5B178.5 (2)
C3A—C4A—C5A—O2A153.4 (3)C2B—C1B—C6B—C5B−1.8 (4)
C3A—C4A—C5A—C6A−31.2 (3)O1B—C1B—C6B—C7B−6.4 (4)
O1A—C1A—C6A—C5A−170.5 (2)C2B—C1B—C6B—C7B173.3 (2)
C2A—C1A—C6A—C5A7.8 (4)O2B—C5B—C6B—C1B177.9 (2)
O1A—C1A—C6A—C7A7.6 (4)C4B—C5B—C6B—C1B−2.7 (3)
C2A—C1A—C6A—C7A−174.0 (2)O2B—C5B—C6B—C7B2.7 (3)
O2A—C5A—C6A—C1A173.2 (2)C4B—C5B—C6B—C7B−178.0 (2)
C4A—C5A—C6A—C1A−2.2 (3)C1B—C6B—C7B—C8B18.8 (3)
O2A—C5A—C6A—C7A−5.0 (4)C5B—C6B—C7B—C8B−166.2 (2)
C4A—C5A—C6A—C7A179.6 (2)C1B—C6B—C7B—C14B−105.7 (3)
C1A—C6A—C7A—C8A−22.5 (3)C5B—C6B—C7B—C14B69.3 (3)
C5A—C6A—C7A—C8A155.6 (2)C6B—C7B—C8B—C13B−19.1 (3)
C1A—C6A—C7A—C14A102.3 (3)C14B—C7B—C8B—C13B103.7 (3)
C5A—C6A—C7A—C14A−79.6 (3)C6B—C7B—C8B—C9B160.0 (2)
C6A—C7A—C8A—C13A22.2 (3)C14B—C7B—C8B—C9B−77.2 (3)
C14A—C7A—C8A—C13A−102.2 (3)C13B—C8B—C9B—O3B−178.8 (3)
C6A—C7A—C8A—C9A−156.9 (2)C7B—C8B—C9B—O3B2.0 (4)
C14A—C7A—C8A—C9A78.7 (3)C13B—C8B—C9B—C10B3.9 (4)
C13A—C8A—C9A—O3A177.5 (2)C7B—C8B—C9B—C10B−175.2 (2)
C7A—C8A—C9A—O3A−3.3 (4)O3B—C9B—C10B—C11B144.8 (3)
C13A—C8A—C9A—C10A−5.0 (4)C8B—C9B—C10B—C11B−37.9 (4)
C7A—C8A—C9A—C10A174.2 (2)C9B—C10B—C11B—C23B176.2 (3)
O3A—C9A—C10A—C11A−145.0 (3)C9B—C10B—C11B—C22B−63.2 (3)
C8A—C9A—C10A—C11A37.5 (3)C9B—C10B—C11B—C12B57.0 (3)
C9A—C10A—C11A—C22A64.4 (3)C10B—C11B—C12B—C13B−44.3 (3)
C9A—C10A—C11A—C12A−56.3 (3)C23B—C11B—C12B—C13B−164.1 (3)
C9A—C10A—C11A—C23A−174.6 (3)C22B—C11B—C12B—C13B76.2 (3)
C22A—C11A—C12A—C13A−75.9 (3)C9B—C8B—C13B—O1B−172.2 (2)
C23A—C11A—C12A—C13A163.5 (3)C7B—C8B—C13B—O1B6.9 (4)
C10A—C11A—C12A—C13A44.7 (3)C9B—C8B—C13B—C12B8.4 (4)
C9A—C8A—C13A—O1A171.9 (2)C7B—C8B—C13B—C12B−172.5 (2)
C7A—C8A—C13A—O1A−7.2 (4)C1B—O1B—C13B—C8B8.1 (3)
C9A—C8A—C13A—C12A−6.3 (4)C1B—O1B—C13B—C12B−172.4 (2)
C7A—C8A—C13A—C12A174.5 (2)C11B—C12B—C13B—C8B13.5 (4)
C1A—O1A—C13A—C8A−10.8 (3)C11B—C12B—C13B—O1B−166.0 (2)
C1A—O1A—C13A—C12A167.7 (2)C6B—C7B—C14B—C19B60.2 (3)
C11A—C12A—C13A—C8A−15.4 (4)C8B—C7B—C14B—C19B−61.6 (3)
C11A—C12A—C13A—O1A166.1 (2)C6B—C7B—C14B—C15B−113.7 (2)
C6A—C7A—C14A—C19A−58.8 (3)C8B—C7B—C14B—C15B124.5 (2)
C8A—C7A—C14A—C19A63.0 (3)C19B—C14B—C15B—O4B−177.5 (2)
C6A—C7A—C14A—C15A123.0 (2)C7B—C14B—C15B—O4B−3.5 (4)
C8A—C7A—C14A—C15A−115.2 (3)C19B—C14B—C15B—C16B3.2 (3)
C19A—C14A—C15A—O4A−170.3 (2)C7B—C14B—C15B—C16B177.2 (2)
C7A—C14A—C15A—O4A7.9 (4)O4B—C15B—C16B—C17B147.8 (2)
C19A—C14A—C15A—C16A8.6 (4)C14B—C15B—C16B—C17B−32.9 (3)
C7A—C14A—C15A—C16A−173.2 (2)C15B—C16B—C17B—C18B55.7 (3)
O4A—C15A—C16A—C17A−162.9 (2)C15B—C16B—C17B—C24B−65.6 (3)
C14A—C15A—C16A—C17A18.1 (3)C15B—C16B—C17B—C25B174.6 (2)
C15A—C16A—C17A—C25A−166.8 (2)C24B—C17B—C18B—C19B69.2 (3)
C15A—C16A—C17A—C18A−46.9 (3)C25B—C17B—C18B—C19B−170.8 (2)
C15A—C16A—C17A—C24A73.0 (3)C16B—C17B—C18B—C19B−51.4 (3)
C25A—C17A—C18A—C19A172.6 (2)C15B—C14B—C19B—O5B−179.2 (2)
C16A—C17A—C18A—C19A52.2 (3)C7B—C14B—C19B—O5B6.9 (4)
C24A—C17A—C18A—C19A−68.2 (3)C15B—C14B—C19B—C18B0.6 (4)
C15A—C14A—C19A—O5A176.3 (2)C7B—C14B—C19B—C18B−173.3 (2)
C7A—C14A—C19A—O5A−1.9 (4)C17B—C18B—C19B—O5B−154.9 (2)
C15A—C14A—C19A—C18A−2.6 (4)C17B—C18B—C19B—C14B25.3 (4)
C7A—C14A—C19A—C18A179.2 (2)C28—C29—C30—C31169 (2)
C17A—C18A—C19A—O5A151.4 (2)C29—C30—C31—C32178 (2)
C17A—C18A—C19A—C14A−29.7 (3)C30—C31—C32—C33175 (4)
C13B—O1B—C1B—C6B−8.4 (3)C28X—C29X—C30X—C31X171 (3)
C13B—O1B—C1B—C2B171.9 (2)C29X—C30X—C31X—C32X−179 (3)
C6B—C1B—C2B—C3B−23.8 (3)C30X—C31X—C32X—C33X177 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5B—H5OB···O5A0.821.692.488 (2)163
O1W—H2W1···O4Ai0.892.032.918 (3)175
N1—H1N1···O4Aii0.881.942.755 (3)155
N1—H2N1···O1W0.872.012.860 (3)167
C4B—H4C···O2Ai0.972.483.353 (4)150
C12A—H12B···O3Aiii0.972.413.261 (3)146
C12B—H12C···O3Biv0.972.363.238 (3)150
C18A—H18A···O5B0.972.553.227 (3)126
C26—H26C···O4B0.962.423.244 (4)144
C27—H27B···O3B0.962.343.055 (4)131
Symmetry codes: (i) −x, −y+1, z+1/2; (ii) −x+1/2, y+1/2, z+1/2; (iii) x+1/2, −y+1/2, z; (iv) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formulaC2H8N+·C25H31O5−·C25H32O5·0.5C6H14·H2O
Mr931.20
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)100
a, b, c (Å)11.2438 (2), 20.1671 (3), 23.6474 (3)
V (Å3)5362.16 (14)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.48 × 0.38 × 0.20
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.963, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		31958, 8021, 6458
Rint0.040
(sin θ/λ)max (Å−1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.145, 1.03
No. of reflections8021
No. of parameters640
No. of restraints19
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.48, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5B—H5OB···O5A0.821.692.488 (2)163
O1W—H2W1···O4Ai0.892.032.918 (3)175
N1—H1N1···O4Aii0.881.942.755 (3)155
N1—H2N1···O1W0.872.012.860 (3)167
C4B—H4C···O2Ai0.972.483.353 (4)150
C12A—H12B···O3Aiii0.972.413.261 (3)146
C12B—H12C···O3Biv0.972.363.238 (3)150
C18A—H18A···O5B0.972.553.227 (3)126
C26—H26C···O4B0.962.423.244 (4)144
C27—H27B···O3B0.962.343.055 (4)131
Symmetry codes: (i) −x, −y+1, z+1/2; (ii) −x+1/2, y+1/2, z+1/2; (iii) x+1/2, −y+1/2, z; (iv) x−1/2, −y+3/2, z.
 

Footnotes

‡Additional corresponding author: aisyah@usm.my.

§Thomson Reuters ResearcherID: C-7576-2009.

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NH, ASAR and SMS are grateful to Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under the University Research grant (No. 1001/PFARMASI/815026). HKF and JHG thank USM for a Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

References

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ISSN: 2056-9890
Volume 66| Part 2| February 2010| Pages o470-o471
https://doi.org/10.1107/S1600536810003107
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