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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o81–o82.
Published online 2009 December 9. doi:  10.1107/S1600536809051885
PMCID: PMC2980031

Atalaphylline1

Abstract

The title acridone alkaloid [systematic name: 1,3,5-trihydr­oxy-2,4-bis­(3-methyl­but-2-en­yl)acridin-9(10H)-one], C23H25NO4, known as atalaphylline, was isolated from Atalantia monophylla Corrêa, a mangrove plant. The mol­ecule contains three fused planar rings with an r.m.s. deviation of 0.026 (2) Å. Both 3-methyl­but-2-enyl substituents are in a (−)anticlinal conformation. An intra­molecular N—H(...)O hydrogen bond generates an S(5) ring motif, while an intra­molecular O—H(...)O hydrogen bond generates an S(6) ring motif. In the crystal structure, the mol­ecules are linked into screw chains along [010] by inter­molecular O—H(...)O hydrogen bonds. These chains are stacked along the a axis by π–π inter­actions with centroid–centroid distances of 3.6695 (13) and 3.6696 (13) Å.

Related literature

For hydrogen-bond motifs, see Bernstein et al. (1995 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For details of acridone alkaloids and their biological activity, see: Basu & Basa (1972 [triangle]); Itoigawa et al. (2003 [triangle]); Kawaii et al. (1999a [triangle],b [triangle]). For a related structure, see: Chukaew et al. (2007 [triangle]). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 [triangle]).

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Object name is e-66-00o81-scheme1.jpg

Experimental

Crystal data

  • C23H25NO4
  • M r = 379.44
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o81-efi1.jpg
  • a = 5.0650 (1) Å
  • b = 15.0131 (4) Å
  • c = 24.5813 (5) Å
  • V = 1869.20 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.40 × 0.21 × 0.04 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.964, T max = 0.996
  • 17852 measured reflections
  • 3142 independent reflections
  • 2525 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.118
  • S = 1.03
  • 3142 reflections
  • 257 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051885/sj2692sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051885/sj2692Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. NB thanks the Development and Promotion of Science and Technology Talents Project for a fellowship. Mr Arnon Chukaew is acknowledged for supplying the authentic sample of atalaphylline. The authors also thank the Malaysian Government and Universiti Sains Malaysia for the University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Acridone alkaloids display a variety of biological activities such as antiproliferative (Kawii et al., 1999a), induction of human promyelocytic leukemia cell (HL-60) differentiation (Kawii et al., 1999b) and cancer chemopreventive activities (Itoigawa et al., 2003). The title acridone alkaloid (I) known as atalaphylline (Basu & Basa, 1972) was isolated from Atalantia monophylla Corrêa, known locally in Thai as Manao Phi, a mangrove plant which was collected from Trang province in the southern part of Thailand. We previously reported the crystal structure of N-methylataphyllinine, an acridone alkaloid which was isolated from the same plant (Chukaew et al., 2007). As part of our research on the crystal structures of natural product compounds from Thai medicinal plants, the molecular and crystal structure of the title acridone alkaloid was investigated and is reported here.

The title molecule (Fig. 1) has a three-fused planar rings with an r.m.s. deviation of 0.026 (2) Å. The pyridine ring makes the dihedral angles of 1.82 (11) and 1.14 (11)° with the C1–C3/C11–C13 and C5–C10 benzene rings, respectively. All the three hydroxyl groups are co-planar with the attached benzene rings. All C atoms of each of the 3-methylbut-2-enyl substituents lie on the same plane with r.m.s. deviations of 0.018 (2) and 0.004 (3)Å for the C14/C15/C16/C17/C18 and C19/C20/C21/C22/C23 planes, respectively. These two planes make dihedral angles of 88.55 (13) (for the 3-methylbut-2-enyl unit at atom C1) and 69.66 (13)° (for the 3-methylbut-2-enyl unit at atom C12) with the C1–C3/C11–C13 benzene ring. The torsion angles C2–C1–C19–C20 and C13–C12–C14–C15 are -103.0 (3) and -120.8 (2)°, indicating an (-)anti-clinal conformation of both the 3-methylbut-2-enyl units. An intramolecular N—H···O hydrogen bond generates an S(5) ring while an intramolecular O—H···O hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995); these help to maintain the planarity of the acridone skeleton. The bond lengths in (I) are within normal ranges (Allen et al., 1987) and comparable with those found in a related structure (Chukaew et al., 2007).

In the crystal packing (Fig. 2), the molecules are linked into screw chains along the [0 1 0] direction by O3—H1O3···O2 hydrogen bonds (Table 1). These chains are stacked along the a axis (Fig. 2) by π···π interactions with distances Cg1···Cg2 = 3.6696 (13) Å and Cg2···Cg3 = 3.6695 (13) Å (symmetry codes for the interactions: 1 + x, y, z and -1 + x, y, z respectively); Cg1, Cg2 and Cg3 are the centroids of C3–C5/C10–C11/N1, C1–C3/C11–C13 and C5–C10 rings, respectively.

Experimental

The air-dried and pulverized root of A. monophylla (6.0 kg) was exhaustively extracted with methylene chloride (2 × 20 l for one week) at room temperature. Removal of the solvent from the methylene chloride extract under reduced pressure gave a yellow viscous residue (52.5 g) which was subjected to quick column chromatography over silica gel using solvents of increasing polarity from n-hexane through EtOAc. The eluents were separated into 18 fractions (F1–F18) on the basis of TLC analysis. Fraction F12 (4.3 g) was further separated by quick column chromatography (QCC) with a gradient of acetone-hexane to afford 6 subfractions (12 A-12 F). Subfraction 12 C (385.0 mg) was further purified by QCC with a gradient of acetone-hexane to give the title compound (22.0 mg). Brown plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from CHCl3/CH3OH (9:1, v/v) after several days, m.p. 518–520 K.

Refinement

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(O—H) = 0.82 Å, d(N—H) = 0.86 Å and d(C—H) = 0.93 Å for aromatic and CH, 0.97 for CH2 and 0.96 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for hydroxy and methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.68 Å from C5 and the deepest hole is located at 1.28 Å from C10. A total of 2260 Friedel pairs were merged before final refinement as there is no large anomalous dispersion for the determination of the absolute configuration.

Figures

Fig. 1.
The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering scheme. Intramolecular hydrogen bonds are shown as dashed lines.
Fig. 2.
The crystal packing of (I) view along the a axis. Hydrogen bonds are drawn as dashed lines.

Crystal data

C23H25NO4Dx = 1.348 Mg m3
Mr = 379.44Melting point = 518–520 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3142 reflections
a = 5.0650 (1) Åθ = 1.6–30.0°
b = 15.0131 (4) ŵ = 0.09 mm1
c = 24.5813 (5) ÅT = 100 K
V = 1869.20 (7) Å3Plate, brown
Z = 40.40 × 0.21 × 0.04 mm
F(000) = 808

Data collection

Bruker APEXII CCD area-detector diffractometer3142 independent reflections
Radiation source: sealed tube2525 reflections with I > 2σ(I)
graphiteRint = 0.041
[var phi] and ω scansθmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −6→7
Tmin = 0.964, Tmax = 0.996k = −21→15
17852 measured reflectionsl = −34→34

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0588P)2 + 0.5624P] where P = (Fo2 + 2Fc2)/3
3142 reflections(Δ/σ)max < 0.001
257 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

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

xyzUiso*/Ueq
O10.3340 (3)0.33730 (11)0.16280 (7)0.0193 (4)
H1O10.45520.33070.18450.029*
O20.7218 (3)0.37946 (11)0.22404 (6)0.0183 (4)
O30.9035 (4)0.77231 (10)0.22808 (6)0.0187 (4)
H1O31.01120.80670.24150.028*
O4−0.0692 (3)0.56738 (12)0.05943 (7)0.0220 (4)
H1O4−0.15450.52440.04870.026*
N10.6177 (4)0.64068 (12)0.18267 (8)0.0150 (4)
H1N10.60020.69560.17340.018*
C10.1293 (5)0.44831 (15)0.11046 (9)0.0149 (5)
C20.3171 (5)0.42414 (15)0.14846 (9)0.0148 (5)
C30.4888 (4)0.48744 (14)0.17270 (9)0.0137 (4)
C40.6867 (5)0.46079 (15)0.21169 (9)0.0141 (4)
C50.8434 (5)0.53044 (15)0.23695 (9)0.0152 (5)
C61.0356 (5)0.51065 (15)0.27656 (9)0.0193 (5)
H6A1.06480.45190.28680.023*
C71.1794 (5)0.57750 (17)0.29992 (10)0.0226 (5)
H7A1.30610.56390.32600.027*
C81.1368 (5)0.66664 (16)0.28480 (9)0.0198 (5)
H8A1.23420.71160.30140.024*
C90.9534 (5)0.68805 (15)0.24586 (9)0.0159 (5)
C100.8024 (5)0.61953 (15)0.22133 (9)0.0147 (4)
C110.4593 (4)0.57851 (14)0.15804 (9)0.0143 (4)
C120.2707 (5)0.60543 (15)0.11958 (9)0.0149 (5)
C130.1139 (5)0.53968 (15)0.09674 (9)0.0167 (5)
C140.2242 (5)0.70302 (15)0.10646 (10)0.0176 (5)
H14A0.07470.70720.08190.021*
H14B0.17650.73360.13980.021*
C150.4547 (5)0.75103 (16)0.08107 (9)0.0185 (5)
H15A0.54470.72100.05370.022*
C160.5433 (5)0.83205 (16)0.09377 (10)0.0214 (5)
C170.7643 (6)0.87496 (19)0.06275 (13)0.0337 (7)
H17A0.82380.83530.03470.051*
H17B0.90770.88770.08710.051*
H17C0.70280.92940.04660.051*
C180.4340 (6)0.88750 (17)0.13926 (11)0.0284 (6)
H18A0.29030.85640.15620.043*
H18B0.37170.94320.12500.043*
H18C0.57000.89840.16560.043*
C19−0.0597 (5)0.38065 (15)0.08666 (9)0.0179 (5)
H19A−0.06380.32870.11010.022*
H19B−0.23580.40600.08620.022*
C200.0113 (5)0.35141 (15)0.02980 (9)0.0190 (5)
H20A0.16200.31640.02660.023*
C21−0.1154 (5)0.36960 (16)−0.01649 (10)0.0219 (5)
C22−0.0143 (7)0.3355 (2)−0.07035 (10)0.0323 (7)
H22A0.13690.2982−0.06430.049*
H22B0.03490.3850−0.09290.049*
H22C−0.15020.3017−0.08800.049*
C23−0.3584 (6)0.4259 (2)−0.02118 (12)0.0333 (6)
H23A−0.43160.43560.01430.050*
H23B−0.48590.3961−0.04360.050*
H23C−0.31340.4821−0.03730.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0209 (8)0.0137 (8)0.0235 (8)−0.0020 (7)−0.0046 (7)0.0007 (7)
O20.0205 (8)0.0100 (7)0.0243 (8)−0.0001 (7)−0.0030 (7)0.0012 (7)
O30.0236 (9)0.0098 (7)0.0227 (8)−0.0018 (7)−0.0055 (7)−0.0001 (6)
O40.0206 (8)0.0205 (8)0.0251 (9)−0.0028 (8)−0.0084 (7)0.0007 (7)
N10.0153 (9)0.0083 (9)0.0214 (9)0.0004 (8)−0.0029 (8)0.0009 (7)
C10.0155 (10)0.0137 (10)0.0155 (10)−0.0026 (9)0.0010 (9)−0.0029 (9)
C20.0167 (11)0.0107 (10)0.0169 (11)−0.0015 (9)0.0031 (9)−0.0020 (9)
C30.0143 (10)0.0110 (9)0.0158 (10)−0.0010 (9)0.0004 (9)−0.0014 (8)
C40.0147 (10)0.0133 (10)0.0141 (10)0.0009 (9)−0.0006 (9)−0.0013 (9)
C50.0169 (11)0.0121 (10)0.0164 (10)−0.0003 (9)0.0003 (9)−0.0013 (9)
C60.0255 (12)0.0112 (10)0.0213 (12)0.0022 (10)−0.0066 (10)0.0013 (9)
C70.0264 (13)0.0179 (11)0.0236 (12)0.0013 (11)−0.0108 (11)0.0011 (10)
C80.0246 (12)0.0135 (11)0.0211 (12)−0.0040 (10)−0.0063 (10)−0.0031 (9)
C90.0194 (11)0.0113 (10)0.0170 (11)−0.0017 (9)0.0008 (10)−0.0021 (9)
C100.0152 (10)0.0144 (10)0.0145 (10)0.0006 (9)0.0003 (9)−0.0003 (9)
C110.0125 (10)0.0115 (9)0.0190 (11)−0.0019 (9)0.0013 (9)−0.0006 (9)
C120.0161 (10)0.0099 (10)0.0186 (11)0.0000 (9)−0.0008 (9)0.0011 (9)
C130.0159 (11)0.0176 (11)0.0167 (10)0.0012 (10)0.0006 (9)0.0014 (9)
C140.0154 (11)0.0121 (10)0.0252 (12)−0.0004 (9)−0.0036 (10)0.0024 (9)
C150.0200 (11)0.0174 (11)0.0181 (11)0.0026 (10)−0.0021 (9)0.0023 (9)
C160.0192 (11)0.0191 (11)0.0258 (12)−0.0022 (10)−0.0084 (10)0.0073 (10)
C170.0237 (13)0.0263 (14)0.0510 (18)−0.0056 (13)−0.0017 (14)0.0111 (13)
C180.0376 (15)0.0150 (11)0.0326 (14)−0.0031 (12)−0.0083 (13)−0.0037 (11)
C190.0172 (11)0.0155 (10)0.0211 (11)−0.0045 (10)−0.0004 (9)0.0005 (9)
C200.0202 (11)0.0148 (10)0.0220 (12)−0.0034 (10)0.0012 (10)−0.0033 (9)
C210.0283 (13)0.0170 (11)0.0205 (12)−0.0085 (11)0.0017 (11)−0.0007 (10)
C220.0453 (17)0.0313 (14)0.0204 (13)−0.0074 (15)0.0010 (13)−0.0022 (11)
C230.0268 (14)0.0446 (17)0.0287 (14)−0.0006 (14)−0.0086 (12)0.0017 (13)

Geometric parameters (Å, °)

O1—C21.353 (3)C12—C141.519 (3)
O1—H1O10.8200C14—C151.508 (3)
O2—C41.271 (3)C14—H14A0.9700
O3—C91.362 (3)C14—H14B0.9700
O3—H1O30.8200C15—C161.334 (3)
O4—C131.369 (3)C15—H15A0.9300
O4—H1O40.8200C16—C171.500 (4)
N1—C101.371 (3)C16—C181.500 (4)
N1—C111.372 (3)C17—H17A0.9600
N1—H1N10.8600C17—H17B0.9600
C1—C21.381 (3)C17—H17C0.9600
C1—C131.415 (3)C18—H18A0.9600
C1—C191.514 (3)C18—H18B0.9600
C2—C31.419 (3)C18—H18C0.9600
C3—C111.422 (3)C19—C201.508 (3)
C3—C41.443 (3)C19—H19A0.9700
C4—C51.452 (3)C19—H19B0.9700
C5—C101.407 (3)C20—C211.335 (3)
C5—C61.408 (3)C20—H20A0.9300
C6—C71.366 (3)C21—C231.497 (4)
C6—H6A0.9300C21—C221.509 (3)
C7—C81.406 (3)C22—H22A0.9600
C7—H7A0.9300C22—H22B0.9600
C8—C91.372 (3)C22—H22C0.9600
C8—H8A0.9300C23—H23A0.9600
C9—C101.417 (3)C23—H23B0.9600
C11—C121.404 (3)C23—H23C0.9600
C12—C131.386 (3)
C2—O1—H1O1109.5C12—C14—H14A108.4
C9—O3—H1O3109.5C15—C14—H14B108.4
C13—O4—H1O4109.5C12—C14—H14B108.4
C10—N1—C11123.20 (19)H14A—C14—H14B107.5
C10—N1—H1N1118.4C16—C15—C14126.8 (2)
C11—N1—H1N1118.4C16—C15—H15A116.6
C2—C1—C13117.0 (2)C14—C15—H15A116.6
C2—C1—C19121.4 (2)C15—C16—C17121.6 (3)
C13—C1—C19121.6 (2)C15—C16—C18123.8 (2)
O1—C2—C1118.2 (2)C17—C16—C18114.6 (2)
O1—C2—C3119.8 (2)C16—C17—H17A109.5
C1—C2—C3122.0 (2)C16—C17—H17B109.5
C2—C3—C11118.2 (2)H17A—C17—H17B109.5
C2—C3—C4121.2 (2)C16—C17—H17C109.5
C11—C3—C4120.5 (2)H17A—C17—H17C109.5
O2—C4—C3121.5 (2)H17B—C17—H17C109.5
O2—C4—C5120.9 (2)C16—C18—H18A109.5
C3—C4—C5117.64 (19)C16—C18—H18B109.5
C10—C5—C6119.4 (2)H18A—C18—H18B109.5
C10—C5—C4119.1 (2)C16—C18—H18C109.5
C6—C5—C4121.4 (2)H18A—C18—H18C109.5
C7—C6—C5120.3 (2)H18B—C18—H18C109.5
C7—C6—H6A119.9C20—C19—C1113.73 (19)
C5—C6—H6A119.9C20—C19—H19A108.8
C6—C7—C8120.4 (2)C1—C19—H19A108.8
C6—C7—H7A119.8C20—C19—H19B108.8
C8—C7—H7A119.8C1—C19—H19B108.8
C9—C8—C7120.8 (2)H19A—C19—H19B107.7
C9—C8—H8A119.6C21—C20—C19128.0 (2)
C7—C8—H8A119.6C21—C20—H20A116.0
O3—C9—C8124.5 (2)C19—C20—H20A116.0
O3—C9—C10116.0 (2)C20—C21—C23125.2 (2)
C8—C9—C10119.5 (2)C20—C21—C22121.0 (2)
N1—C10—C5120.7 (2)C23—C21—C22113.8 (2)
N1—C10—C9119.7 (2)C21—C22—H22A109.5
C5—C10—C9119.6 (2)C21—C22—H22B109.5
N1—C11—C12119.97 (19)H22A—C22—H22B109.5
N1—C11—C3118.7 (2)C21—C22—H22C109.5
C12—C11—C3121.3 (2)H22A—C22—H22C109.5
C13—C12—C11117.3 (2)H22B—C22—H22C109.5
C13—C12—C14120.8 (2)C21—C23—H23A109.5
C11—C12—C14121.8 (2)C21—C23—H23B109.5
O4—C13—C12116.3 (2)H23A—C23—H23B109.5
O4—C13—C1119.5 (2)C21—C23—H23C109.5
C12—C13—C1124.2 (2)H23A—C23—H23C109.5
C15—C14—C12115.4 (2)H23B—C23—H23C109.5
C15—C14—H14A108.4
C13—C1—C2—O1179.2 (2)O3—C9—C10—C5179.3 (2)
C19—C1—C2—O12.1 (3)C8—C9—C10—C5−0.4 (3)
C13—C1—C2—C3−0.3 (3)C10—N1—C11—C12178.7 (2)
C19—C1—C2—C3−177.5 (2)C10—N1—C11—C3−0.6 (3)
O1—C2—C3—C11−177.9 (2)C2—C3—C11—N1177.7 (2)
C1—C2—C3—C111.7 (3)C4—C3—C11—N1−1.7 (3)
O1—C2—C3—C41.4 (3)C2—C3—C11—C12−1.7 (3)
C1—C2—C3—C4−179.0 (2)C4—C3—C11—C12179.0 (2)
C2—C3—C4—O23.0 (3)N1—C11—C12—C13−179.0 (2)
C11—C3—C4—O2−177.7 (2)C3—C11—C12—C130.3 (3)
C2—C3—C4—C5−176.4 (2)N1—C11—C12—C14−3.6 (3)
C11—C3—C4—C52.9 (3)C3—C11—C12—C14175.7 (2)
O2—C4—C5—C10178.7 (2)C11—C12—C13—O4179.85 (19)
C3—C4—C5—C10−2.0 (3)C14—C12—C13—O44.4 (3)
O2—C4—C5—C6−1.2 (3)C11—C12—C13—C11.2 (3)
C3—C4—C5—C6178.2 (2)C14—C12—C13—C1−174.3 (2)
C10—C5—C6—C70.5 (4)C2—C1—C13—O4−179.8 (2)
C4—C5—C6—C7−179.6 (2)C19—C1—C13—O4−2.7 (3)
C5—C6—C7—C80.1 (4)C2—C1—C13—C12−1.2 (3)
C6—C7—C8—C9−0.9 (4)C19—C1—C13—C12176.0 (2)
C7—C8—C9—O3−178.7 (2)C13—C12—C14—C15−120.8 (2)
C7—C8—C9—C101.0 (4)C11—C12—C14—C1564.0 (3)
C11—N1—C10—C51.6 (3)C12—C14—C15—C16−136.1 (2)
C11—N1—C10—C9−178.3 (2)C14—C15—C16—C17−175.8 (2)
C6—C5—C10—N1179.6 (2)C14—C15—C16—C184.2 (4)
C4—C5—C10—N1−0.2 (3)C2—C1—C19—C20−103.0 (3)
C6—C5—C10—C9−0.4 (3)C13—C1—C19—C2079.9 (3)
C4—C5—C10—C9179.7 (2)C1—C19—C20—C21−110.2 (3)
O3—C9—C10—N1−0.7 (3)C19—C20—C21—C231.2 (4)
C8—C9—C10—N1179.6 (2)C19—C20—C21—C22179.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O1···O20.821.822.554 (2)149
O3—H1O3···O2i0.821.932.752 (2)175
N1—H1N1···O30.862.342.692 (3)105
C14—H14A···O40.972.292.773 (3)110
C19—H19A···O10.972.402.811 (3)105

Symmetry codes: (i) −x+2, y+1/2, −z+1/2.

Footnotes

1This paper is dedicated to the late His Royal Highness Prince Mahidol of Songkla for his contributions to the development of medical education in Thailand.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2692).

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