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Acta Cryst. (2009). E65, o2443    [ doi:10.1107/S1600536809032954 ]

15-Hydroxyethyl-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-azapentacyclo[10.5.2.01,10.04,9.013,17]nonadec-18-ene-5-carboxylic acid

X. Xu, Z. Song, S. Shang, H. Wang and X. Rao

Abstract top

The title compound, C26H37NO5, which was synthesized from monoethanolamine and maleopimaric acid, consists of two fused and unbridged cyclohexane rings. They form a trans ring junction with a chair conformation. The two methyl groups are in axial positions. In the crystal, intermolecular O-H...O hydrogen bonds link adjacent molecules into a layer structure. Two C-H...O interactions are also present.

Comment top

Maleopimaric acid is a readily obtainable compound, which is made by the reaction of maleic anhydride and rosin. A number of new derivatives of maleopimaric acid have been prepared (Walter, 1967). The title compound is one of modified products of maleopimaric acid, which could be used in varnishes and surface coatings (Xiao, 2003). Although, it has been prepared by Penczek P. (Penczek, 1970), the crystal structure of it has not yet been reported. In this work, we describe the crystal structure of the title compound. The molecular structure is shown in Fig. 1 and the crystal packing in Fig.2.

Related literature top

For the synthesis of maleopimaric acid derivatives, see: Walter & Ray (1967). For the use of the title compound in varnishes and surface coatings, see: Penczek (1970); Xiao (2003).

Experimental top

Maleopimaric acid (80.0 g) and monoethanolamine (35.8 g) were slowly heated to 130 degrees centigrade and the reaction was carried out for 2 h. Subsequently, the resulting acrylic modified rosin was cooled to room temperature. Then acetone (150 ml) was added dropwise successively with constant stirring. After dropping the mixture was stirred for another 15 minutes and then filtered. The title compound was precipitated from the solution. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. The crystal data were collected on an Enraf–Nonius CAD-4 difractometer. Data collection and cell refinement were performed using Enraf–Nonius CAD-4 Software.

Refinement top

All H atoms bonded to the C atoms were placed geometrically at the distances of 0.93–0.98 Å and included in the refinement in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, showing displacement ellipsoids at the 15% probability level.
[Figure 2] Fig. 2. A view of the packing of the title compound.
15-Hydroxyethyl-19-isopropyl-5,9-dimethyl-14,16-dioxo-15- azapentacyclo[10.5.2.01,10.04,9.013,17]nonadec-18-ene-5-carboxylic acid top
Crystal data top
C26H37NO5F(000) = 480
Mr = 443.57Dx = 1.222 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 12.274 (3) Åθ = 9–12°
b = 6.9550 (14) ŵ = 0.08 mm−1
c = 14.445 (3) ÅT = 293 K
β = 102.22 (3)°Block, colorless
V = 1205.2 (4) Å30.30 × 0.20 × 0.10 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer		1744 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 25.2°, θmin = 1.4°
ω/2θ scansh = 0→14
Absorption correction: ψ scan
(North et al., 1968)		k = 0→8
Tmin = 0.975, Tmax = 0.992l = −17→16
2487 measured reflections3 standard reflections every 200 reflections
2373 independent reflections intensity decay: 1%
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.09P)2 + P]
where P = (Fo2 + 2Fc2)/3
2373 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.44 e Å−3
22 restraintsΔρmin = −0.33 e Å−3
Crystal data top
C26H37NO5V = 1205.2 (4) Å3
Mr = 443.57Z = 2
Monoclinic, P21Mo Kα radiation
a = 12.274 (3) ŵ = 0.08 mm−1
b = 6.9550 (14) ÅT = 293 K
c = 14.445 (3) Å0.30 × 0.20 × 0.10 mm
β = 102.22 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		1744 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.024
Tmin = 0.975, Tmax = 0.992θmax = 25.2°
2487 measured reflections3 standard reflections every 200 reflections
2373 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.189Δρmax = 0.44 e Å−3
S = 1.00Δρmin = −0.33 e Å−3
2373 reflectionsAbsolute structure: ?
271 parametersFlack parameter: ?
22 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N0.7569 (3)0.2774 (8)0.9683 (3)0.0527 (12)
C10.4892 (4)0.2559 (8)0.8217 (3)0.0363 (11)
O10.0325 (6)−0.1069 (12)0.7369 (5)0.123 (2)
C20.4169 (4)0.1064 (8)0.8588 (3)0.0423 (12)
H2A0.39180.16020.91260.051*
H2B0.4622−0.00550.88070.051*
O20.0550 (5)0.1493 (10)0.8226 (4)0.108
H2C0.00390.09290.84390.162*
O30.6287 (3)0.0996 (9)1.0198 (3)0.0839 (18)
C30.3148 (4)0.0426 (9)0.7842 (4)0.0532 (14)
H3A0.3390−0.02420.73310.064*
H3B0.2700−0.04530.81260.064*
C40.2447 (4)0.2185 (7)0.7446 (4)0.0459 (13)
H4A0.23420.29100.80030.055*
O40.8467 (4)0.5151 (11)0.8999 (4)0.110 (2)
C50.1243 (5)0.1684 (10)0.6886 (5)0.0681 (17)
O50.8772 (5)−0.0458 (10)0.9037 (4)0.105
H5A0.8826−0.15840.88220.126*
C60.0641 (5)0.3588 (11)0.6566 (6)0.077 (2)
H6A−0.00870.33020.61760.093*
H6B0.05250.42780.71210.093*
C70.1256 (6)0.4859 (10)0.6020 (5)0.074 (2)
H7A0.08420.60430.58560.089*
H7B0.13220.42240.54370.089*
C80.2398 (5)0.5316 (9)0.6592 (4)0.0623 (17)
H8A0.23180.60510.71450.075*
H8B0.27800.61230.62150.075*
C90.3132 (5)0.3529 (8)0.6926 (3)0.0448 (13)
C100.4166 (4)0.4214 (7)0.7671 (3)0.0381 (11)
H10A0.38710.49270.81500.046*
C110.4956 (5)0.5621 (8)0.7305 (4)0.0577 (15)
H11A0.47490.56890.66200.069*
H11B0.48770.68970.75540.069*
C120.6177 (5)0.4975 (9)0.7605 (4)0.0587 (16)
H12A0.66690.58340.73440.070*
C130.6456 (5)0.5035 (10)0.8703 (4)0.0613 (16)
H13A0.63250.63310.89240.074*
C140.5700 (4)0.3595 (8)0.9058 (3)0.0413 (12)
H14A0.52490.42920.94320.050*
C150.5630 (4)0.1723 (7)0.7609 (3)0.0374 (11)
H15A0.56160.04240.74550.045*
C160.6300 (5)0.2951 (10)0.7306 (4)0.0539 (15)
C170.7128 (7)0.2472 (14)0.6679 (5)0.083 (2)
H17A0.78660.28920.70190.099*
C180.6885 (7)0.3491 (16)0.5733 (6)0.098
H18A0.68110.48450.58310.148*
H18B0.62050.30020.53520.148*
H18C0.74870.32710.54150.148*
C190.7198 (7)0.0228 (16)0.6504 (6)0.103 (3)
H19A0.7720−0.00130.61070.155*
H19B0.6477−0.02430.61980.155*
H19C0.7441−0.04160.70990.155*
C200.1193 (7)0.0313 (11)0.6079 (6)0.096 (3)
H20A0.1590−0.08410.63060.144*
H20B0.15270.08960.56050.144*
H20C0.04290.00050.58100.144*
C210.0670 (7)0.0619 (15)0.7521 (6)0.088 (2)
C220.3508 (5)0.2610 (10)0.6074 (3)0.0609 (16)
H22A0.39270.35300.57970.091*
H22B0.28650.22180.56110.091*
H22C0.39660.15090.62840.091*
C230.6475 (4)0.2278 (10)0.9707 (3)0.0520 (15)
C240.7590 (5)0.4422 (11)0.9121 (4)0.0631 (17)
C250.8560 (5)0.1800 (12)1.0236 (5)0.070 (2)
H25A0.85280.18271.09010.084*
H25B0.92220.24981.01660.084*
C260.8656 (7)−0.0272 (14)0.9932 (5)0.090 (3)
H26A0.9292−0.08601.03490.109*
H26B0.7995−0.09661.00070.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.037 (2)0.070 (3)0.049 (2)−0.010 (2)0.0038 (17)0.004 (3)
C10.046 (3)0.034 (3)0.028 (2)0.002 (2)0.0057 (18)0.004 (2)
O10.124 (5)0.110 (6)0.137 (6)−0.016 (5)0.033 (4)−0.014 (5)
C20.041 (2)0.044 (3)0.039 (2)0.002 (2)0.002 (2)0.011 (2)
O20.1160.1140.114−0.0340.071−0.018
O30.046 (2)0.133 (5)0.067 (3)−0.014 (3)0.0006 (18)0.062 (3)
C30.050 (3)0.044 (3)0.060 (3)0.004 (3)−0.002 (2)0.006 (3)
C40.051 (3)0.028 (3)0.053 (3)0.005 (2)−0.003 (2)−0.001 (2)
O40.063 (3)0.124 (5)0.133 (5)−0.031 (3)0.000 (3)0.052 (4)
C50.060 (3)0.058 (4)0.080 (4)0.005 (3)0.000 (3)−0.004 (3)
O50.1050.1050.1050.0000.0220.000
C60.058 (4)0.058 (4)0.100 (5)0.014 (3)−0.023 (4)0.006 (4)
C70.078 (4)0.047 (4)0.076 (4)0.018 (4)−0.031 (4)0.007 (4)
C80.084 (4)0.033 (3)0.059 (3)0.018 (3)−0.009 (3)0.001 (3)
C90.060 (3)0.031 (3)0.038 (3)0.010 (3)−0.002 (2)−0.003 (2)
C100.056 (3)0.029 (2)0.029 (2)0.007 (2)0.007 (2)−0.003 (2)
C110.072 (4)0.035 (3)0.060 (3)−0.002 (3)0.001 (3)0.010 (3)
C120.066 (4)0.047 (3)0.061 (4)−0.018 (3)0.011 (3)0.011 (3)
C130.067 (4)0.042 (3)0.070 (4)−0.002 (3)0.002 (3)−0.010 (3)
C140.044 (3)0.053 (3)0.027 (2)0.002 (2)0.0063 (19)−0.009 (2)
C150.053 (3)0.029 (2)0.033 (2)0.001 (2)0.015 (2)−0.003 (2)
C160.058 (3)0.067 (4)0.040 (3)0.007 (3)0.017 (2)0.007 (3)
C170.088 (5)0.108 (7)0.067 (4)0.010 (5)0.051 (4)0.005 (5)
C180.0980.0980.0980.0000.0210.000
C190.095 (6)0.130 (8)0.096 (6)0.024 (6)0.044 (5)−0.034 (6)
C200.081 (5)0.049 (4)0.136 (7)0.003 (4)−0.029 (5)−0.017 (5)
C210.071 (4)0.090 (6)0.098 (5)0.009 (4)0.011 (4)0.005 (4)
C220.087 (4)0.058 (4)0.030 (2)0.014 (4)−0.006 (2)−0.007 (3)
C230.038 (3)0.079 (5)0.038 (3)0.001 (3)0.005 (2)0.000 (3)
C240.055 (3)0.069 (4)0.063 (4)−0.018 (3)0.007 (3)0.003 (3)
C250.038 (3)0.100 (6)0.064 (4)−0.005 (3)−0.004 (3)0.012 (4)
C260.089 (5)0.107 (7)0.078 (5)0.039 (5)0.022 (4)0.030 (5)
Geometric parameters (Å, °) top
N—C231.395 (6)C10—C111.548 (7)
N—C241.407 (8)C10—H10A0.9800
N—C251.472 (7)C11—C121.536 (8)
C1—C151.506 (6)C11—H11A0.9700
C1—C21.535 (7)C11—H11B0.9700
C1—C101.563 (7)C12—C161.489 (9)
C1—C141.571 (6)C12—C131.551 (8)
O1—C211.251 (12)C12—H12A0.9800
C2—C31.535 (7)C13—C241.459 (9)
C2—H2A0.9700C13—C141.526 (8)
C2—H2B0.9700C13—H13A0.9800
O2—C211.222 (10)C14—C231.498 (8)
O2—H2C0.8500C14—H14A0.9800
O3—C231.192 (8)C15—C161.322 (8)
C3—C41.535 (7)C15—H15A0.9300
C3—H3A0.9700C16—C171.534 (8)
C3—H3B0.9700C17—C181.512 (11)
C4—C91.554 (8)C17—C191.586 (14)
C4—C51.567 (8)C17—H17A0.9800
C4—H4A0.9800C18—H18A0.9600
O4—C241.236 (7)C18—H18B0.9600
C5—C211.470 (11)C18—H18C0.9600
C5—C201.497 (10)C19—H19A0.9600
C5—C61.539 (9)C19—H19B0.9600
O5—C261.337 (9)C19—H19C0.9600
O5—H5A0.8500C20—H20A0.9600
C6—C71.491 (10)C20—H20B0.9600
C6—H6A0.9700C20—H20C0.9600
C6—H6B0.9700C22—H22A0.9600
C7—C81.503 (8)C22—H22B0.9600
C7—H7A0.9700C22—H22C0.9600
C7—H7B0.9700C25—C261.518 (13)
C8—C91.550 (7)C25—H25A0.9700
C8—H8A0.9700C25—H25B0.9700
C8—H8B0.9700C26—H26A0.9700
C9—C221.541 (7)C26—H26B0.9700
C9—C101.556 (7)
C23—N—C24110.5 (5)C11—C12—C13105.8 (5)
C23—N—C25124.2 (5)C16—C12—H12A110.9
C24—N—C25125.1 (5)C11—C12—H12A110.9
C15—C1—C2113.9 (4)C13—C12—H12A110.9
C15—C1—C10109.8 (3)C24—C13—C14105.3 (5)
C2—C1—C10111.4 (4)C24—C13—C12113.6 (5)
C15—C1—C14105.6 (4)C14—C13—C12107.9 (5)
C2—C1—C14111.0 (4)C24—C13—H13A110.0
C10—C1—C14104.6 (4)C14—C13—H13A110.0
C1—C2—C3113.4 (4)C12—C13—H13A110.0
C1—C2—H2A108.9C23—C14—C13105.1 (4)
C3—C2—H2A108.9C23—C14—C1114.6 (5)
C1—C2—H2B108.9C13—C14—C1111.8 (4)
C3—C2—H2B108.9C23—C14—H14A108.4
H2A—C2—H2B107.7C13—C14—H14A108.4
C21—O2—H2C107.4C1—C14—H14A108.4
C4—C3—C2109.9 (5)C16—C15—C1115.9 (5)
C4—C3—H3A109.7C16—C15—H15A122.1
C2—C3—H3A109.7C1—C15—H15A122.1
C4—C3—H3B109.7C15—C16—C12113.9 (5)
C2—C3—H3B109.7C15—C16—C17126.2 (7)
H3A—C3—H3B108.2C12—C16—C17119.8 (6)
C3—C4—C9110.0 (4)C18—C17—C16113.8 (7)
C3—C4—C5114.1 (5)C18—C17—C19108.9 (7)
C9—C4—C5115.5 (4)C16—C17—C19112.0 (7)
C3—C4—H4A105.4C18—C17—H17A107.3
C9—C4—H4A105.4C16—C17—H17A107.3
C5—C4—H4A105.4C19—C17—H17A107.3
C21—C5—C20102.6 (7)C17—C18—H18A109.5
C21—C5—C6111.0 (6)C17—C18—H18B109.5
C20—C5—C6112.1 (6)H18A—C18—H18B109.5
C21—C5—C4108.2 (5)C17—C18—H18C109.5
C20—C5—C4115.0 (6)H18A—C18—H18C109.5
C6—C5—C4107.7 (5)H18B—C18—H18C109.5
C26—O5—H5A118.4C17—C19—H19A109.5
C7—C6—C5113.8 (6)C17—C19—H19B109.5
C7—C6—H6A108.8H19A—C19—H19B109.5
C5—C6—H6A108.8C17—C19—H19C109.5
C7—C6—H6B108.8H19A—C19—H19C109.5
C5—C6—H6B108.8H19B—C19—H19C109.5
H6A—C6—H6B107.7C5—C20—H20A109.5
C6—C7—C8110.6 (5)C5—C20—H20B109.5
C6—C7—H7A109.5H20A—C20—H20B109.5
C8—C7—H7A109.5C5—C20—H20C109.5
C6—C7—H7B109.5H20A—C20—H20C109.5
C8—C7—H7B109.5H20B—C20—H20C109.5
H7A—C7—H7B108.1O2—C21—O1121.1 (9)
C7—C8—C9114.5 (5)O2—C21—C5115.3 (9)
C7—C8—H8A108.6O1—C21—C5123.6 (9)
C9—C8—H8A108.6C9—C22—H22A109.5
C7—C8—H8B108.6C9—C22—H22B109.5
C9—C8—H8B108.6H22A—C22—H22B109.5
H8A—C8—H8B107.6C9—C22—H22C109.5
C22—C9—C8109.7 (4)H22A—C22—H22C109.5
C22—C9—C4114.9 (5)H22B—C22—H22C109.5
C8—C9—C4107.1 (4)O3—C23—N120.6 (5)
C22—C9—C10109.9 (4)O3—C23—C14130.7 (5)
C8—C9—C10107.8 (4)N—C23—C14108.7 (5)
C4—C9—C10107.1 (4)O4—C24—N122.6 (6)
C11—C10—C9115.8 (4)O4—C24—C13127.2 (7)
C11—C10—C1107.8 (4)N—C24—C13110.2 (5)
C9—C10—C1114.8 (4)N—C25—C26112.7 (6)
C11—C10—H10A105.9N—C25—H25A109.1
C9—C10—H10A105.9C26—C25—H25A109.1
C1—C10—H10A105.9N—C25—H25B109.1
C12—C11—C10111.3 (4)C26—C25—H25B109.1
C12—C11—H11A109.4H25A—C25—H25B107.8
C10—C11—H11A109.4O5—C26—C25113.7 (7)
C12—C11—H11B109.4O5—C26—H26A108.8
C10—C11—H11B109.4C25—C26—H26A108.8
H11A—C11—H11B108.0O5—C26—H26B108.8
C16—C12—C11110.3 (5)C25—C26—H26B108.8
C16—C12—C13108.0 (5)H26A—C26—H26B107.7
C15—C1—C2—C3−77.6 (5)C12—C13—C14—C23124.2 (5)
C10—C1—C2—C347.3 (6)C24—C13—C14—C1−122.3 (5)
C14—C1—C2—C3163.3 (4)C12—C13—C14—C1−0.7 (6)
C1—C2—C3—C4−55.8 (6)C15—C1—C14—C23−65.5 (5)
C2—C3—C4—C963.4 (6)C2—C1—C14—C2358.4 (5)
C2—C3—C4—C5−164.9 (5)C10—C1—C14—C23178.7 (4)
C3—C4—C5—C2158.1 (7)C15—C1—C14—C1354.0 (5)
C9—C4—C5—C21−172.9 (6)C2—C1—C14—C13177.9 (5)
C3—C4—C5—C20−55.9 (8)C10—C1—C14—C13−61.9 (5)
C9—C4—C5—C2073.1 (7)C2—C1—C15—C16−177.4 (4)
C3—C4—C5—C6178.3 (6)C10—C1—C15—C1656.9 (6)
C9—C4—C5—C6−52.8 (7)C14—C1—C15—C16−55.3 (5)
C21—C5—C6—C7172.6 (6)C1—C15—C16—C12−1.6 (7)
C20—C5—C6—C7−73.3 (8)C1—C15—C16—C17−179.9 (5)
C4—C5—C6—C754.2 (8)C11—C12—C16—C15−54.7 (6)
C5—C6—C7—C8−57.6 (8)C13—C12—C16—C1560.5 (7)
C6—C7—C8—C957.4 (8)C11—C12—C16—C17123.8 (6)
C7—C8—C9—C2272.0 (7)C13—C12—C16—C17−121.0 (6)
C7—C8—C9—C4−53.3 (7)C15—C16—C17—C18118.0 (8)
C7—C8—C9—C10−168.3 (5)C12—C16—C17—C18−60.3 (9)
C3—C4—C9—C2260.7 (6)C15—C16—C17—C19−6.0 (10)
C5—C4—C9—C22−70.2 (6)C12—C16—C17—C19175.7 (7)
C3—C4—C9—C8−177.1 (4)C20—C5—C21—O2−176.4 (7)
C5—C4—C9—C851.9 (6)C6—C5—C21—O2−56.5 (9)
C3—C4—C9—C10−61.7 (5)C4—C5—C21—O261.5 (9)
C5—C4—C9—C10167.3 (5)C20—C5—C21—O13.9 (10)
C22—C9—C10—C1155.9 (6)C6—C5—C21—O1123.8 (9)
C8—C9—C10—C11−63.6 (6)C4—C5—C21—O1−118.1 (9)
C4—C9—C10—C11−178.6 (4)C24—N—C23—O3−174.9 (6)
C22—C9—C10—C1−70.8 (5)C25—N—C23—O30.2 (9)
C8—C9—C10—C1169.7 (4)C24—N—C23—C144.6 (6)
C4—C9—C10—C154.7 (5)C25—N—C23—C14179.6 (5)
C15—C1—C10—C11−51.5 (5)C13—C14—C23—O3175.0 (7)
C2—C1—C10—C11−178.7 (4)C1—C14—C23—O3−61.9 (8)
C14—C1—C10—C1161.4 (5)C13—C14—C23—N−4.4 (6)
C15—C1—C10—C979.2 (5)C1—C14—C23—N118.7 (5)
C2—C1—C10—C9−48.0 (5)C23—N—C24—O4179.3 (7)
C14—C1—C10—C9−167.9 (4)C25—N—C24—O44.3 (10)
C9—C10—C11—C12−131.2 (5)C23—N—C24—C13−2.9 (7)
C1—C10—C11—C12−1.1 (6)C25—N—C24—C13−177.9 (6)
C10—C11—C12—C1653.9 (6)C14—C13—C24—O4177.7 (7)
C10—C11—C12—C13−62.6 (6)C12—C13—C24—O459.9 (10)
C16—C12—C13—C2460.7 (7)C14—C13—C24—N0.0 (7)
C11—C12—C13—C24178.9 (5)C12—C13—C24—N−117.9 (6)
C16—C12—C13—C14−55.6 (6)C23—N—C25—C2666.0 (8)
C11—C12—C13—C1462.5 (6)C24—N—C25—C26−119.6 (7)
C24—C13—C14—C232.6 (6)N—C25—C26—O562.4 (9)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2c···O5i0.852.163.010 (9)178
O5—H5a···O4ii0.852.343.076 (10)145
C10—H10A···O3iii0.982.553.470 (6)157
C14—H14A···O3iii0.982.383.316 (7)159
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2c···O5i0.852.163.010 (9)178
O5—H5a···O4ii0.852.343.076 (10)145
C10—H10A···O3iii0.982.553.470 (6)157
C14—H14A···O3iii0.982.383.316 (7)159
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+2.
Acknowledgements top

This work was supported by the 948 program of the State Forestry Administration (grant No. 2006–4-C03).

references
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