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Acta Cryst. (2008). E64, o1986    [ doi:10.1107/S160053680802970X ]

Pheophorbide b ethyl ester from a chlorella vulgaris dietary supplement

C. F. Chee, N. A. Rahman, S. M. Zain and S. W. Ng

Abstract top

In the title compound, C37H38N4O6, four five-membered nitrogen-bearing rings are nearly coplanar. Two N atoms in two these five-membered rings have attached H atoms, which contribute to the formation of intramolecular N-H...N hydrogen bonds [N...N = 2.713 (5)-3.033 (6) Å].

Related literature top

For the crystal structure of pheophorbide a methyl ester, see: Fischer et al. (1972). For another example of chlorin, see: Senge & Smith (1997).

Experimental top

A sample of the dietary supplement Chlorenergy (C'est Si Bon Co., USA) (20 g) was dissolved in 100 ml e thanol and 10 ml dilute sulfuric acid (10%, v/v). The mixture was heated at 323 K for 2 h. The solution was cooled and then stirred at room temperature for 3 days under normal day light (light intensity not measured), during which the solution turned green yellowish. The solvent was evaporated to dryness at reduced pressure. The crude product was purified by HPLC on an RP18e semi-preparative column (Merck Chromolith 100–10 mm) with acetonitrile-water (90:10, v/v) as the eluent. Pheophorbide b ethyl ester was isolated as brownish plates. Single crystals were grown by slow evaporation of a mixture of acetone and chloroform solution.

Refinement top

C-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C). The amino H-atoms were located on a difference Fourier map, and were isotropically refined with a distance restraint N–H=0.88 (2) Å). In the absence of heavy scatterers, 3452 Friedel pairs were merged in the refinement.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atomic numbering and 70% probability displacement ellipsoids.
(I) top
Crystal data top
C37H38N4O6F(000) = 672
Mr = 634.71Dx = 1.352 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3714 reflections
a = 7.0222 (2) Åθ = 2.7–28.4°
b = 30.5501 (7) ŵ = 0.09 mm−1
c = 7.8539 (2) ÅT = 100 K
β = 112.300 (2)°Plate, brown
V = 1558.87 (7) Å30.35 × 0.20 × 0.01 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer		3100 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
graphiteθmax = 27.5°, θmin = 1.3°
ω scansh = −9→9
14310 measured reflectionsk = −39→39
3633 independent reflectionsl = −9→10
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.17 w = 1/[σ2(Fo2) + (0.0986P)2 + 0.882P]
where P = (Fo2 + 2Fc2)/3
3633 reflections(Δ/σ)max = 0.001
438 parametersΔρmax = 0.55 e Å−3
3 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C37H38N4O6V = 1558.87 (7) Å3
Mr = 634.71Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.0222 (2) ŵ = 0.09 mm−1
b = 30.5501 (7) ÅT = 100 K
c = 7.8539 (2) Å0.35 × 0.20 × 0.01 mm
β = 112.300 (2)°
Data collection top
Bruker SMART APEX
diffractometer		3100 reflections with I > 2σ(I)
14310 measured reflectionsRint = 0.054
3633 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.177Δρmax = 0.55 e Å−3
S = 1.17Δρmin = −0.38 e Å−3
3633 reflectionsAbsolute structure: ?
438 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4731 (6)0.50000 (12)0.2630 (5)0.0208 (8)
O20.2600 (6)0.49420 (13)0.4146 (6)0.0291 (9)
O3−0.0879 (6)0.43359 (11)0.0419 (5)0.0197 (8)
O4−0.2243 (5)0.39650 (12)0.2153 (5)0.0194 (7)
O5−0.1704 (5)0.33907 (12)−0.1938 (4)0.0185 (7)
O60.2153 (7)0.07387 (13)0.9416 (5)0.0317 (9)
N10.3166 (7)0.25068 (14)0.8896 (6)0.0151 (8)
H1N0.236 (11)0.251 (3)0.772 (3)0.06 (3)*
N20.2567 (6)0.32123 (13)0.6242 (5)0.0144 (8)
N30.0540 (6)0.25217 (13)0.3274 (5)0.0132 (8)
H3N0.101 (8)0.2426 (19)0.441 (3)0.019 (15)*
N40.1148 (6)0.18688 (13)0.5768 (5)0.0145 (8)
C10.3315 (7)0.21173 (16)0.9824 (6)0.0136 (9)
C20.4415 (7)0.22289 (17)1.1778 (6)0.0147 (9)
C30.4902 (9)0.19315 (19)1.3358 (7)0.0270 (12)
H30.54250.20791.45080.032*
C40.4778 (11)0.1527 (2)1.3517 (8)0.0388 (16)
H4A0.42730.13481.24510.047*
H4B0.51870.13991.47040.047*
C50.4844 (7)0.26621 (16)1.1902 (6)0.0149 (9)
C60.6018 (8)0.29141 (17)1.3629 (6)0.0173 (10)
H6A0.72680.27531.43600.026*
H6B0.51550.29521.43490.026*
H6C0.63950.32021.33030.026*
C70.4064 (7)0.28444 (16)1.0051 (6)0.0135 (9)
C80.4182 (7)0.32710 (16)0.9564 (6)0.0129 (9)
H80.48040.34711.05450.016*
C90.3481 (7)0.34462 (16)0.7770 (6)0.0142 (9)
C100.3693 (7)0.39297 (15)0.7423 (6)0.0132 (9)
H100.51720.40180.80000.016*
C110.2387 (9)0.42253 (16)0.8135 (7)0.0200 (10)
H11A0.29310.42150.94820.030*
H11B0.09590.41220.76470.030*
H11C0.24390.45270.77290.030*
C120.2977 (7)0.39420 (16)0.5286 (6)0.0137 (9)
H120.18650.41650.47530.016*
C130.4771 (7)0.40329 (15)0.4667 (6)0.0151 (9)
H13A0.58840.38200.52770.018*
H13B0.42890.39830.33240.018*
C140.5668 (8)0.44977 (16)0.5091 (7)0.0187 (10)
H14A0.60300.45620.64130.022*
H14B0.69440.45140.48390.022*
C150.4162 (8)0.48372 (16)0.3950 (7)0.0180 (10)
C160.3316 (9)0.53099 (19)0.1365 (7)0.0243 (11)
H16A0.18840.52100.10610.029*
H16B0.35710.53200.02090.029*
C170.3570 (9)0.5764 (2)0.2186 (9)0.0294 (12)
H17A0.26950.59700.12620.044*
H17B0.50110.58550.25760.044*
H17C0.31670.57620.32520.044*
C180.2128 (7)0.34861 (15)0.4764 (6)0.0137 (9)
C190.1041 (7)0.33397 (15)0.3001 (6)0.0139 (9)
C200.0327 (7)0.36154 (15)0.1264 (6)0.0131 (9)
H200.15440.37370.10580.016*
C21−0.1089 (7)0.39854 (15)0.1341 (6)0.0135 (9)
C22−0.2130 (8)0.47095 (16)0.0499 (7)0.0200 (10)
H22A−0.19340.4948−0.02510.030*
H22B−0.17140.48070.17770.030*
H22C−0.35830.46240.00240.030*
C23−0.0867 (7)0.32839 (16)−0.0327 (7)0.0158 (9)
C24−0.0692 (7)0.28555 (15)0.0547 (6)0.0128 (9)
C250.0404 (7)0.29118 (16)0.2478 (7)0.0147 (9)
C26−0.1222 (7)0.24197 (16)0.0190 (6)0.0139 (9)
C27−0.2368 (8)0.22101 (17)−0.1630 (7)0.0191 (10)
H27A−0.33050.2424−0.24610.029*
H27B−0.31630.1961−0.14650.029*
H27C−0.13890.2107−0.21580.029*
C28−0.0448 (7)0.22063 (16)0.1955 (6)0.0145 (9)
C29−0.0575 (7)0.17779 (16)0.2429 (7)0.0143 (9)
H29−0.12210.15770.14580.017*
C300.0173 (7)0.16128 (16)0.4234 (7)0.0157 (9)
C310.0040 (7)0.11672 (16)0.4739 (7)0.0180 (10)
C32−0.0871 (8)0.07875 (17)0.3481 (7)0.0217 (10)
H32A−0.18300.08990.22780.026*
H32B−0.16720.06050.40110.026*
C330.0764 (9)0.0507 (2)0.3185 (9)0.0298 (12)
H33A0.01270.02400.25190.045*
H33B0.18210.04280.43800.045*
H33C0.13970.06710.24650.045*
C340.0948 (8)0.11562 (17)0.6626 (7)0.0207 (11)
C350.1192 (9)0.07653 (17)0.7743 (7)0.0216 (10)
H350.05500.05060.71240.026*
C360.1628 (8)0.15993 (17)0.7220 (7)0.0177 (10)
C370.2647 (8)0.17179 (16)0.9098 (7)0.0194 (10)
H370.28930.14860.99600.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0238 (18)0.0243 (19)0.0161 (17)0.0037 (15)0.0096 (14)0.0056 (14)
O20.027 (2)0.025 (2)0.041 (2)0.0052 (16)0.0194 (18)0.0084 (17)
O30.0251 (19)0.0137 (17)0.0232 (19)0.0047 (14)0.0125 (15)0.0038 (14)
O40.0182 (16)0.0191 (18)0.0251 (18)0.0012 (14)0.0130 (14)0.0029 (14)
O50.0202 (17)0.0240 (19)0.0094 (16)0.0010 (14)0.0034 (13)0.0023 (13)
O60.052 (3)0.021 (2)0.023 (2)−0.0026 (18)0.0138 (18)0.0042 (16)
N10.0177 (19)0.0155 (19)0.0128 (19)0.0002 (15)0.0068 (16)0.0017 (15)
N20.017 (2)0.012 (2)0.014 (2)−0.0004 (15)0.0055 (16)0.0021 (15)
N30.0161 (19)0.0112 (19)0.0125 (19)0.0002 (15)0.0058 (16)0.0006 (15)
N40.0158 (19)0.016 (2)0.0136 (19)−0.0003 (15)0.0080 (16)0.0009 (15)
C10.014 (2)0.018 (2)0.012 (2)0.0036 (18)0.0081 (17)0.0018 (17)
C20.014 (2)0.021 (2)0.012 (2)0.0024 (18)0.0078 (18)0.0013 (18)
C30.041 (3)0.024 (3)0.012 (2)0.000 (2)0.006 (2)0.002 (2)
C40.053 (4)0.032 (3)0.018 (3)−0.008 (3)−0.002 (3)0.006 (2)
C50.015 (2)0.020 (2)0.010 (2)0.0031 (18)0.0055 (18)0.0038 (17)
C60.016 (2)0.026 (3)0.010 (2)0.0034 (19)0.0058 (18)−0.0005 (18)
C70.011 (2)0.016 (2)0.014 (2)0.0004 (17)0.0057 (17)−0.0003 (17)
C80.011 (2)0.018 (2)0.009 (2)−0.0013 (17)0.0034 (16)0.0002 (17)
C90.013 (2)0.018 (2)0.011 (2)0.0022 (18)0.0044 (17)0.0031 (17)
C100.017 (2)0.013 (2)0.009 (2)−0.0014 (18)0.0048 (17)−0.0019 (17)
C110.032 (3)0.014 (2)0.018 (2)0.002 (2)0.014 (2)0.0001 (18)
C120.016 (2)0.013 (2)0.014 (2)0.0024 (17)0.0089 (17)0.0027 (17)
C130.017 (2)0.015 (2)0.016 (2)0.0011 (18)0.0088 (18)0.0022 (17)
C140.023 (3)0.018 (2)0.013 (2)−0.0040 (19)0.0049 (19)0.0009 (18)
C150.018 (2)0.015 (2)0.023 (2)−0.0048 (18)0.0096 (19)−0.0008 (19)
C160.024 (3)0.027 (3)0.020 (3)0.007 (2)0.007 (2)0.007 (2)
C170.027 (3)0.026 (3)0.037 (3)0.004 (2)0.015 (2)0.003 (2)
C180.014 (2)0.014 (2)0.014 (2)0.0047 (17)0.0060 (18)0.0012 (17)
C190.015 (2)0.015 (2)0.013 (2)0.0012 (17)0.0065 (17)0.0039 (17)
C200.015 (2)0.015 (2)0.010 (2)0.0020 (18)0.0054 (17)0.0009 (16)
C210.016 (2)0.009 (2)0.016 (2)−0.0018 (17)0.0053 (17)−0.0015 (17)
C220.022 (2)0.010 (2)0.028 (3)0.0020 (18)0.010 (2)−0.0006 (19)
C230.014 (2)0.018 (2)0.016 (2)0.0022 (18)0.0062 (18)−0.0001 (18)
C240.009 (2)0.019 (2)0.012 (2)0.0030 (17)0.0056 (17)0.0004 (17)
C250.009 (2)0.021 (2)0.015 (2)0.0041 (18)0.0054 (17)0.0026 (18)
C260.011 (2)0.019 (2)0.013 (2)0.0066 (18)0.0072 (18)0.0017 (18)
C270.019 (2)0.021 (3)0.016 (2)−0.002 (2)0.0052 (19)−0.0046 (19)
C280.009 (2)0.019 (2)0.015 (2)0.0037 (17)0.0051 (17)−0.0012 (18)
C290.013 (2)0.013 (2)0.018 (2)−0.0019 (17)0.0075 (18)−0.0042 (18)
C300.014 (2)0.014 (2)0.022 (2)−0.0014 (17)0.0100 (19)−0.0038 (18)
C310.012 (2)0.019 (2)0.024 (3)−0.0003 (18)0.0080 (19)0.001 (2)
C320.021 (2)0.018 (3)0.022 (3)−0.001 (2)0.004 (2)0.000 (2)
C330.032 (3)0.026 (3)0.031 (3)0.002 (2)0.011 (2)−0.007 (2)
C340.027 (3)0.017 (3)0.021 (2)0.000 (2)0.011 (2)0.0016 (19)
C350.033 (3)0.014 (2)0.022 (2)−0.005 (2)0.015 (2)0.0004 (19)
C360.016 (2)0.016 (2)0.023 (2)0.0008 (18)0.0107 (19)−0.0003 (19)
C370.030 (3)0.012 (2)0.018 (2)0.003 (2)0.011 (2)0.0032 (18)
Geometric parameters (Å, °) top
O1—C151.340 (6)C13—H13A0.9900
O1—C161.456 (6)C13—H13B0.9900
O2—C151.207 (6)C14—C151.509 (7)
O3—C211.332 (6)C14—H14A0.9900
O3—C221.456 (6)C14—H14B0.9900
O4—C211.208 (6)C16—C171.511 (8)
O5—C231.220 (6)C16—H16A0.9900
O6—C351.231 (7)C16—H16B0.9900
N1—C71.360 (6)C17—H17A0.9800
N1—C11.379 (6)C17—H17B0.9800
N1—H1N0.88 (3)C17—H17C0.9800
N2—C91.333 (6)C18—C191.378 (6)
N2—C181.368 (6)C19—C251.392 (7)
N3—C251.332 (6)C19—C201.518 (6)
N3—C281.392 (6)C20—C211.522 (6)
N3—H3N0.88 (3)C20—C231.579 (6)
N4—C361.342 (6)C20—H201.0000
N4—C301.380 (6)C22—H22A0.9800
C1—C371.353 (7)C22—H22B0.9800
C1—C21.472 (6)C22—H22C0.9800
C2—C51.352 (7)C23—C241.461 (7)
C2—C31.470 (7)C24—C261.382 (7)
C3—C41.248 (9)C24—C251.427 (6)
C3—H30.9500C26—C281.439 (6)
C4—H4A0.9500C26—C271.493 (7)
C4—H4B0.9500C27—H27A0.9800
C5—C71.456 (6)C27—H27B0.9800
C5—C61.505 (7)C27—H27C0.9800
C6—H6A0.9800C28—C291.373 (7)
C6—H6B0.9800C29—C301.405 (7)
C6—H6C0.9800C29—H290.9500
C7—C81.370 (7)C30—C311.431 (7)
C8—C91.410 (6)C31—C341.373 (7)
C8—H80.9500C31—C321.500 (7)
C9—C101.519 (7)C32—C331.520 (8)
C10—C111.535 (7)C32—H32A0.9900
C10—C121.559 (6)C32—H32B0.9900
C10—H101.0000C33—H33A0.9800
C11—H11A0.9800C33—H33B0.9800
C11—H11B0.9800C33—H33C0.9800
C11—H11C0.9800C34—C361.452 (7)
C12—C181.509 (7)C34—C351.453 (7)
C12—C131.538 (6)C35—H350.9500
C12—H121.0000C36—C371.420 (7)
C13—C141.538 (7)C37—H370.9500
C15—O1—C16116.3 (4)C16—C17—H17B109.5
C21—O3—C22114.4 (4)H17A—C17—H17B109.5
C7—N1—C1112.2 (4)C16—C17—H17C109.5
C7—N1—H1N131 (6)H17A—C17—H17C109.5
C1—N1—H1N116 (6)H17B—C17—H17C109.5
C9—N2—C18108.2 (4)N2—C18—C19121.0 (4)
C25—N3—C28110.1 (4)N2—C18—C12113.3 (4)
C25—N3—H3N135 (4)C19—C18—C12125.7 (4)
C28—N3—H3N115 (4)C18—C19—C25126.5 (4)
C36—N4—C30106.0 (4)C18—C19—C20126.3 (4)
C37—C1—N1127.6 (4)C25—C19—C20107.2 (4)
C37—C1—C2127.5 (4)C19—C20—C21112.0 (4)
N1—C1—C2104.8 (4)C19—C20—C23104.5 (4)
C5—C2—C3124.8 (5)C21—C20—C23110.4 (4)
C5—C2—C1108.4 (4)C19—C20—H20109.9
C3—C2—C1126.8 (5)C21—C20—H20109.9
C4—C3—C2133.9 (5)C23—C20—H20109.9
C4—C3—H3113.0O4—C21—O3124.3 (4)
C2—C3—H3113.0O4—C21—C20124.2 (4)
C3—C4—H4A120.0O3—C21—C20111.5 (4)
C3—C4—H4B120.0O3—C22—H22A109.5
H4A—C4—H4B120.0O3—C22—H22B109.5
C2—C5—C7108.3 (4)H22A—C22—H22B109.5
C2—C5—C6126.6 (4)O3—C22—H22C109.5
C7—C5—C6125.1 (4)H22A—C22—H22C109.5
C5—C6—H6A109.5H22B—C22—H22C109.5
C5—C6—H6B109.5O5—C23—C24130.4 (5)
H6A—C6—H6B109.5O5—C23—C20123.4 (4)
C5—C6—H6C109.5C24—C23—C20106.1 (4)
H6A—C6—H6C109.5C26—C24—C25109.1 (4)
H6B—C6—H6C109.5C26—C24—C23143.1 (4)
N1—C7—C8126.7 (4)C25—C24—C23107.8 (4)
N1—C7—C5106.2 (4)N3—C25—C19138.0 (5)
C8—C7—C5127.1 (4)N3—C25—C24107.7 (4)
C7—C8—C9127.2 (4)C19—C25—C24114.2 (4)
C7—C8—H8116.4C24—C26—C28105.5 (4)
C9—C8—H8116.4C24—C26—C27127.8 (4)
N2—C9—C8124.2 (4)C28—C26—C27126.7 (4)
N2—C9—C10114.0 (4)C26—C27—H27A109.5
C8—C9—C10121.8 (4)C26—C27—H27B109.5
C9—C10—C11113.2 (4)H27A—C27—H27B109.5
C9—C10—C12101.7 (4)C26—C27—H27C109.5
C11—C10—C12112.6 (4)H27A—C27—H27C109.5
C9—C10—H10109.7H27B—C27—H27C109.5
C11—C10—H10109.7C29—C28—N3121.6 (4)
C12—C10—H10109.7C29—C28—C26130.8 (4)
C10—C11—H11A109.5N3—C28—C26107.6 (4)
C10—C11—H11B109.5C28—C29—C30125.3 (4)
H11A—C11—H11B109.5C28—C29—H29117.3
C10—C11—H11C109.5C30—C29—H29117.3
H11A—C11—H11C109.5N4—C30—C29123.3 (4)
H11B—C11—H11C109.5N4—C30—C31111.1 (4)
C18—C12—C13111.6 (4)C29—C30—C31125.6 (4)
C18—C12—C10101.7 (4)C34—C31—C30105.7 (4)
C13—C12—C10112.1 (4)C34—C31—C32126.8 (5)
C18—C12—H12110.4C30—C31—C32127.5 (5)
C13—C12—H12110.4C31—C32—C33112.3 (4)
C10—C12—H12110.4C31—C32—H32A109.1
C14—C13—C12114.6 (4)C33—C32—H32A109.1
C14—C13—H13A108.6C31—C32—H32B109.1
C12—C13—H13A108.6C33—C32—H32B109.1
C14—C13—H13B108.6H32A—C32—H32B107.9
C12—C13—H13B108.6C32—C33—H33A109.5
H13A—C13—H13B107.6C32—C33—H33B109.5
C15—C14—C13111.7 (4)H33A—C33—H33B109.5
C15—C14—H14A109.3C32—C33—H33C109.5
C13—C14—H14A109.3H33A—C33—H33C109.5
C15—C14—H14B109.3H33B—C33—H33C109.5
C13—C14—H14B109.3C31—C34—C36106.6 (4)
H14A—C14—H14B107.9C31—C34—C35124.9 (5)
O2—C15—O1123.5 (5)C36—C34—C35128.5 (5)
O2—C15—C14124.9 (5)O6—C35—C34126.2 (5)
O1—C15—C14111.5 (4)O6—C35—H35116.9
O1—C16—C17111.5 (5)C34—C35—H35116.9
O1—C16—H16A109.3N4—C36—C37126.2 (5)
C17—C16—H16A109.3N4—C36—C34110.6 (4)
O1—C16—H16B109.3C37—C36—C34123.1 (5)
C17—C16—H16B109.3C1—C37—C36128.7 (5)
H16A—C16—H16B108.0C1—C37—H37115.7
C16—C17—H17A109.5C36—C37—H37115.7
C7—N1—C1—C37−177.9 (5)C19—C20—C21—O3147.9 (4)
C7—N1—C1—C20.6 (5)C23—C20—C21—O3−96.1 (4)
C37—C1—C2—C5178.4 (5)C19—C20—C23—O5178.5 (4)
N1—C1—C2—C50.0 (5)C21—C20—C23—O558.0 (6)
C37—C1—C2—C3−4.1 (8)C19—C20—C23—C24−2.4 (4)
N1—C1—C2—C3177.5 (5)C21—C20—C23—C24−122.9 (4)
C5—C2—C3—C4−173.5 (7)O5—C23—C24—C260.1 (10)
C1—C2—C3—C49.4 (11)C20—C23—C24—C26−178.9 (6)
C3—C2—C5—C7−178.1 (4)O5—C23—C24—C25−178.6 (5)
C1—C2—C5—C7−0.5 (5)C20—C23—C24—C252.3 (5)
C3—C2—C5—C64.8 (8)C28—N3—C25—C19−179.8 (5)
C1—C2—C5—C6−177.7 (4)C28—N3—C25—C24−0.9 (5)
C1—N1—C7—C8179.9 (4)C18—C19—C25—N3−0.8 (9)
C1—N1—C7—C5−0.9 (5)C20—C19—C25—N3178.8 (5)
C2—C5—C7—N10.9 (5)C18—C19—C25—C24−179.7 (4)
C6—C5—C7—N1178.1 (4)C20—C19—C25—C24−0.1 (5)
C2—C5—C7—C8−179.9 (4)C26—C24—C25—N30.1 (5)
C6—C5—C7—C8−2.7 (8)C23—C24—C25—N3179.3 (4)
N1—C7—C8—C9−3.0 (8)C26—C24—C25—C19179.3 (4)
C5—C7—C8—C9178.0 (4)C23—C24—C25—C19−1.5 (5)
C18—N2—C9—C8−179.1 (4)C25—C24—C26—C280.7 (5)
C18—N2—C9—C101.7 (5)C23—C24—C26—C28−178.1 (6)
C7—C8—C9—N20.3 (8)C25—C24—C26—C27−179.8 (4)
C7—C8—C9—C10179.4 (4)C23—C24—C26—C271.5 (9)
N2—C9—C10—C11113.3 (4)C25—N3—C28—C29−178.2 (4)
C8—C9—C10—C11−65.9 (6)C25—N3—C28—C261.3 (5)
N2—C9—C10—C12−7.8 (5)C24—C26—C28—C29178.3 (5)
C8—C9—C10—C12173.0 (4)C27—C26—C28—C29−1.3 (8)
C9—C10—C12—C189.8 (4)C24—C26—C28—N3−1.2 (5)
C11—C10—C12—C18−111.7 (4)C27—C26—C28—N3179.2 (4)
C9—C10—C12—C13−109.5 (4)N3—C28—C29—C302.5 (7)
C11—C10—C12—C13129.0 (4)C26—C28—C29—C30−176.9 (4)
C18—C12—C13—C14177.9 (4)C36—N4—C30—C29179.8 (4)
C10—C12—C13—C14−68.7 (5)C36—N4—C30—C31−0.2 (5)
C12—C13—C14—C15−68.1 (5)C28—C29—C30—N4−0.2 (7)
C16—O1—C15—O2−1.7 (7)C28—C29—C30—C31179.8 (5)
C16—O1—C15—C14176.1 (4)N4—C30—C31—C340.4 (6)
C13—C14—C15—O270.4 (7)C29—C30—C31—C34−179.6 (5)
C13—C14—C15—O1−107.3 (5)N4—C30—C31—C32−178.9 (5)
C15—O1—C16—C1781.0 (6)C29—C30—C31—C321.1 (8)
C9—N2—C18—C19−175.3 (4)C34—C31—C32—C33−78.8 (7)
C9—N2—C18—C125.7 (5)C30—C31—C32—C33100.3 (6)
C13—C12—C18—N2109.5 (4)C30—C31—C34—C36−0.4 (5)
C10—C12—C18—N2−10.2 (5)C32—C31—C34—C36178.8 (5)
C13—C12—C18—C19−69.4 (6)C30—C31—C34—C35−178.9 (5)
C10—C12—C18—C19170.9 (4)C32—C31—C34—C350.3 (9)
N2—C18—C19—C25−5.0 (7)C31—C34—C35—O6173.3 (6)
C12—C18—C19—C25173.9 (4)C36—C34—C35—O6−4.9 (9)
N2—C18—C19—C20175.5 (4)C30—N4—C36—C37−179.8 (5)
C12—C18—C19—C20−5.6 (7)C30—N4—C36—C34−0.1 (5)
C18—C19—C20—C21−59.4 (6)C31—C34—C36—N40.3 (6)
C25—C19—C20—C21121.0 (4)C35—C34—C36—N4178.8 (5)
C18—C19—C20—C23−178.9 (4)C31—C34—C36—C37−180.0 (5)
C25—C19—C20—C231.5 (5)C35—C34—C36—C37−1.5 (8)
C22—O3—C21—O41.7 (7)N1—C1—C37—C36−0.3 (9)
C22—O3—C21—C20−177.6 (4)C2—C1—C37—C36−178.4 (5)
C19—C20—C21—O4−31.4 (6)N4—C36—C37—C11.1 (9)
C23—C20—C21—O484.6 (5)C34—C36—C37—C1−178.6 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.88 (3)2.48 (9)2.915 (6)111 (7)
N1—H1N···N40.88 (3)2.42 (8)3.033 (6)127 (8)
N3—H3N···N40.88 (3)1.99 (4)2.713 (5)139 (5)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.88 (3)2.48 (9)2.915 (6)111 (7)
N1—H1N···N40.88 (3)2.42 (8)3.033 (6)127 (8)
N3—H3N···N40.88 (3)1.99 (4)2.713 (5)139 (5)
Acknowledgements top

We thank the University of Malaya (grant No. PS149/2007B) for supporting this study.

references
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