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Journal List > Acta Crystallogr Sect E Struct Rep Online > v.64(Pt 10); Oct 1, 2008

Formats:
Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1986.
Published online 2008 September 24. doi: 10.1107/S160053680802970X.
PMCID: PMC2959371
Copyright © Chee et al. 2008
Pheophorbide b ethyl ester from a chlorella vulgaris dietary supplement
Chin Fei Chee,a Noorsaadah Abdul Rahman,a Sharifuddin M. Zain,a and Seik Weng Nga*
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received September 10, 2008; Accepted September 16, 2008.
This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Abstract
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[cdots, three dots, centered]N hydrogen bonds [N[cdots, three dots, centered]N = 2.713 (5)–3.033 (6) Å].
Related literature
For the crystal structure of pheophorbide a methyl ester, see: Fischer et al. (1972 [triangle]). For another example of a chlorin, see: Senge & Smith (1997 [triangle]).
Click on image to enlarge
An external file that holds a picture, illustration, etc. Object name is e-64-o1986-scheme1.jpg Object name is e-64-o1986-scheme1.jpg
Crystal data
  • C37H38N4O6
  • M r = 634.71
  • Monoclinic, An external file that holds a picture, illustration, etc. Object name is e-64-o1986-efi1.jpg
  • a = 7.0222 (2) Å
  • b = 30.5501 (7) Å
  • c = 7.8539 (2) Å
  • β = 112.300 (2)°
  • V = 1558.87 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 (2) K
  • 0.35 × 0.20 × 0.01 mm
Data collection
  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 14310 measured reflections
  • 3633 independent reflections
  • 3100 reflections with I > 2σ(I)
  • R int = 0.054
Refinement
  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.177
  • S = 1.17
  • 3633 reflections
  • 438 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.38 e Å−3
Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).
​
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802970X/cv2447sup1.cif
Click here to view.(29K, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S160053680802970X/cv2447Isup2.hkl
Click here to view.(178K, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
We thank the University of Malaya (grant No. PS149/2007B) for supporting this study.
supplementary crystallographic information
Experimental
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
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.
Figures
Fig. 1.
Fig. 1.
The molecular structure of the title compound showing the atomic numbering and 70% probability displacement ellipsoids.
Crystal data
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
Bruker SMART APEX diffractometer3100 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
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 = 1.17w = 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
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
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)
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, °)
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, °)
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)
 
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2447).
References
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fischer, M. S., Templeton, D. H., Zalkin, A. & Calvin, M. (1972). J. Am. Chem. Soc.94, 3613–3619.
  • Senge, M. O. & Smith, K. M. (1997). Acta Cryst. C53, 1314–1318.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
  • Westrip, S. P. (2008). publCIF In preparation.
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