organic papers
o974
Liuet al. C30H28N6O6S4CHCl3 doi:10.1107/S1600536806004284 Acta Cryst.(2006). E62, o974–o976
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Verticillin chloroform solvate
Feiyan Liu, Shihua Wu, Yunlong Chen, Lu Yang and Ping Wu*
Research Centre of Siyuan Natural Pharmacy and Biotoxicology, College of Life Science, Zijinggang Campus, Zhejiang University, Hangzhou 310058, People’s Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 286 K
Mean(C–C) = 0.007 A˚
Rfactor = 0.054
wRfactor = 0.119
Data-to-parameter ratio = 14.8
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 4 January 2006 Accepted 3 February 2006
#2006 International Union of Crystallography All rights reserved
The title compound, C30H28N6O6S4CHCl3, is a cytotoxic and
antibacterial compound which was isolated from ethyl acetate extracts of Amanita flavorubescens Alk. affected by Verticil-lium sp. The molecule is a dimer with two epidithio-dioxopiperazine nuclei, the two halves being related by an approximate twofold axis. The two five-membered rings are
cis-fused. The crystal structure is stablized by a hydrogen-bond network involving both OH groups and the carbonyl group.
Comment
[image:1.610.242.425.508.719.2]In the course of our screening for compounds with antitumour activity based on cytotoxic assays, verticillin A was isolated from ethyl acetate extracts of Amanita flavorubescens Alk. affected byVerticilliumsp. It shows strong cytotoxicity against HeLa cells at the 0.2mg ml1 level and can inhibit Ehrlich ascitescarcinoma in the range 0.25–1.0mg ml1, but at 2.5 or 5 mg per kg per day it was toxic to the host (Katagiri et al., 1970). Verticillin A is a compound of the novel epidithio-dioxopiprazine structural class, which was first isolated from a species of Verticillium, an imperfect fungus isolated from a basidiocarp ofColtricia cinnomea(Polystictus cinnamomeus). On the basis of its spectroscopic data and chemical reactions, its structure was assigned and its absolute configuration was proposed (Minatoet al., 1973). However, no details were given to support these results further. We report here the crystal structure of the title compound, (I).
imate twofold axis perpendicular to the C11—C26 bond. The two five-memembered rings arecis-fused. As shown in Table 1, the bond lengths and angles of the two epidithio-diketo-piperazine systems in verticillin A are quite similar within the limits of error. However, some differences between chemically equivalent torsion angles are significant (Table 1).
The structure of (I) is stabilized by O—H O interactions (Table 2). The packing of the molecules is shown in Fig. 2.
Experimental
The title compound was isolated from ethyl acetate extracts of Amanita flavorubescensAlk. affected by Verticilliumsp. which was collected from Lijiang in Yunnan Province, China, and authenticated by Professor Yongchang Zhao. The fresh bodies of the fungus (1500 g) were first lyophilized and then extracted successively by light petroleum (1 l) and ethyl acetate (2 l). The ethyl acetate extract (1.2 g) was then fractionated by countercurrent chromatography using a two-phase solvent system composed of light petroleum, chloroform and acetonitrile with a volume ratio of 6:1:3, yielding cytotoxic fraction 2. Fraction 2 was subjected to semi-preparative chromatography on a reverse-phase C8 coloumn (Hypersil ODS 20
250 mm), eluted by acetonitrile and water with a gradient from 10 to 100% for 120 min and a flow rate of 10 ml min1; this afforded 10 mg
pure verticillin A. Single crystals suitable for X-ray structure analysis were obtained by slow evaporation of a chlorofom and ethanol solution (2:1v/v) at room temperature.
Crystal data
C30H28N6O6S4CHCl3 Mr= 816.19
Orthorhombic,P212121
a= 10.901 (2) A˚
b= 14.493 (3) A˚
c= 21.355 (3) A˚
V= 3373.7 (9) A˚3 Z= 4
Dx= 1.607 Mg m3
MoKradiation Cell parameters from 28
reflections
= 2.7–11.6
= 0.57 mm1 T= 286 (2) K Block, colourless 0.440.400.36 mm
Data collection
SiemensP4 diffractometer
!scans
Absorption correction: scan (XSCANS; Siemens, 1994)
Tmin= 0.766,Tmax= 0.813
8144 measured reflections 6863 independent reflections 3792 reflections withI> 2(I)
Rint= 0.029
max= 27.0
h=13!13
k=17!18
l=25!27 3 standard reflections
every 97 reflections intensity decay: 5.8%
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.054 wR(F2) = 0.119 S= 0.86 6863 reflections 463 parameters
H atoms treated by a mixture of independent and constrained
w= 1/[2
(Fo2) + (0.049P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001 max= 0.39 e A˚
3
min=0.60 e A˚3
Extinction correction:SHELXL97
[image:2.610.46.298.67.322.2]Extinction coefficient: 0.0069 (5) Absolute structure: Flack (1983),
Figure 1
A view of (1), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted.
Figure 2
[image:2.610.55.287.382.667.2]Table 1
Selected geometric parameters (A˚ ,).
S1—C2 1.890 (5) S1—S2 2.068 (2) S2—C13 1.891 (5) O1—C1 1.213 (6) O2—C3 1.217 (6) O3—C12 1.411 (6) N1—C14 1.460 (6) C4—C11 1.566 (6)
S3—C17 1.885 (5) S3—S4 2.073 (2) S4—C28 1.893 (4) O4—C16 1.241 (5) O5—C18 1.216 (6) O6—C27 1.416 (5) N4—C29 1.448 (6) C19—C26 1.558 (6) C2—S1—S2 99.28 (16)
C13—S2—S1 97.14 (16) C1—N1—C14 117.6 (5) O1—C1—N1 123.4 (5) N1—C2—C15 114.2 (5) N1—C2—S1 110.1 (4) O2—C3—N2 124.9 (5) C4—C11—C26 112.2 (4)
C17—S3—S4 99.04 (17) C28—S4—S3 97.15 (16) C16—N4—C29 119.2 (4) O4—C16—N4 123.3 (5) N4—C17—C30 114.3 (4) N4—C17—S3 110.4 (3) O5—C18—N5 122.8 (5) C19—C26—C11 111.3 (3) C5—N3—C4—C11 17.2 (5)
C4—N3—C5—C10 6.8 (5) N3—C5—C10—C11 6.7 (5)
[image:3.610.42.295.369.415.2]C20—N6—C19—C26 20.8 (5) C19—N6—C20—C25 11.2 (6) N6—C20—C25—C26 3.4 (5)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O3—H3O O1 0.73 (5) 2.31 (5) 2.785 (5) 124 (5) O3—H3O O4i
0.73 (5) 2.20 (5) 2.861 (5) 152 (6) O6—H6O O4 0.83 (5) 1.98 (5) 2.709 (5) 145 (4)
Symmetry code: (i)x1 2;yþ
1 2;zþ1.
The H atoms of the hydroxyl groups were located in a difference Fourier map and refined isotropically. The remaining H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.93–0.98 A˚ and N—H = 0.86 A˚ , and with Uiso(H) =
1.2Ueq(carrier atom).
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL/PC (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:SHELXTL/PC; software used to prepare mate-rial for publication:SHELXTL/PC.
This work was supported by the National High Technology Research and Development Program (863 Programme) of China (grant No. 2003 A A223071) and the Natural Science Foundation of Zhejiang Province (grant No. Y304118). The authors thank Professor Yongchang Zhao for collecting and authenticating the fungal material.
References
Flack, H. D. (1983).Acta Cryst.A39, 876–881.
Katagiri, K., Sato, K., Hayakawa, S., Matsushima, T. & Minato, H. (1970).J. Antibiot.23, 402–422.
Minato, H., Matsumoto, M. & Katayam, T. (1973).J. Chem. Soc. Perkin Trans. 1, pp. 1819–1825.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Siemens (1991). SHELXTL/PC. Version 4.2. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Siemens (1994).XSCANS. Version 2.10b. Siemens Analytical X-ray Instru-ments Inc., Madison, Wisconsin, USA.
Weber, H. P. (1972).Acta Cryst.B28, 2945–2951.
organic papers
o976
Liuet al. Csupporting information
Acta Cryst. (2006). E62, o974–o976 [https://doi.org/10.1107/S1600536806004284]
Verticillin chloroform solvate
Feiyan Liu, Shihua Wu, Yunlong Chen, Lu Yang and Ping Wu
Verticillin chloroform solvate
Crystal data
C30H28N6O6S4·CHCl3
Mr = 816.19
Orthorhombic, P212121
a = 10.901 (2) Å b = 14.493 (3) Å c = 21.355 (3) Å V = 3373.7 (9) Å3
Z = 4
F(000) = 1680
Dx = 1.607 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 28 reflections θ = 2.7–11.6°
µ = 0.58 mm−1
T = 286 K Block, colorless 0.44 × 0.40 × 0.36 mm
Data collection
Siemens P4 diffractometer
Radiation source: normal-focus sealed tube Graphite monochromator
ω scans
Absorption correction: ψ scan Tmin = 0.766, Tmax = 0.813
8144 measured reflections 6863 independent reflections
3792 reflections with I > 2σ(I) Rint = 0.029
θmax = 27.0°, θmin = 1.7°
h = −13→13 k = −17→18 l = −25→27
3 standard reflections every 97 reflections intensity decay: 5.8%
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.054
wR(F2) = 0.119
S = 0.86 6863 reflections 463 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.049P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.39 e Å−3
Δρmin = −0.60 e Å−3
Extinction correction: SHELXL97 Extinction coefficient: 0.0069 (5)
Absolute structure: Flack (1983), 2981 Friedel pairs
supporting information
sup-2 Acta Cryst. (2006). E62, o974–o976
Special details
Experimental. Reference?
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)
x y z Uiso*/Ueq
S1 0.26342 (14) 0.47830 (11) 0.72405 (7) 0.0490 (4)
S2 0.43132 (13) 0.42059 (11) 0.70180 (6) 0.0419 (4)
S3 1.00005 (14) 0.55228 (12) 0.35811 (6) 0.0528 (4)
S4 0.86333 (13) 0.45765 (11) 0.37873 (6) 0.0426 (4)
O1 0.3370 (3) 0.2667 (3) 0.59293 (19) 0.0514 (11)
O2 0.2172 (4) 0.6127 (3) 0.58789 (19) 0.0529 (11)
O3 0.5135 (4) 0.3591 (3) 0.52256 (17) 0.0345 (9)
H3O 0.490 (5) 0.312 (3) 0.524 (3) 0.038 (18)*
O4 1.0015 (3) 0.3362 (2) 0.49598 (15) 0.0350 (8)
O5 0.9814 (3) 0.6945 (2) 0.48748 (18) 0.0454 (10)
O6 0.7929 (3) 0.3842 (2) 0.55667 (16) 0.0364 (9)
H6O 0.858 (4) 0.356 (3) 0.552 (2) 0.030 (15)*
N1 0.1979 (4) 0.3763 (3) 0.6207 (2) 0.0384 (11)
N2 0.3713 (3) 0.5076 (3) 0.59036 (18) 0.0270 (10)
N3 0.4941 (4) 0.6452 (3) 0.60078 (19) 0.0363 (10)
H3N 0.4554 0.6968 0.5983 0.044*
N4 1.0948 (3) 0.4693 (3) 0.46379 (18) 0.0287 (10)
N5 0.8774 (3) 0.5594 (3) 0.48861 (17) 0.0265 (9)
N6 0.7050 (4) 0.6653 (3) 0.4775 (2) 0.0376 (11)
H6N 0.7191 0.7234 0.4812 0.045*
C1 0.3138 (5) 0.3459 (4) 0.6070 (2) 0.0350 (13)
C2 0.1862 (4) 0.4693 (4) 0.6450 (2) 0.0378 (13)
C3 0.2587 (5) 0.5385 (4) 0.6042 (2) 0.0335 (12)
C4 0.4708 (4) 0.5648 (3) 0.5630 (2) 0.0270 (11)
H4 0.4536 0.5812 0.5193 0.032*
C5 0.5895 (5) 0.6256 (3) 0.6419 (2) 0.0346 (13)
C6 0.6276 (6) 0.6783 (4) 0.6924 (3) 0.0468 (15)
H6 0.5937 0.7361 0.7002 0.056*
C7 0.7172 (6) 0.6425 (5) 0.7306 (3) 0.0604 (19)
H7 0.7441 0.6772 0.7646 0.073*
C8 0.7672 (5) 0.5590 (5) 0.7206 (2) 0.0530 (17)
H8 0.8252 0.5359 0.7484 0.064*
C9 0.7322 (4) 0.5067 (4) 0.6685 (2) 0.0352 (13)
C10 0.6419 (4) 0.5402 (3) 0.6296 (2) 0.0273 (11)
C11 0.5857 (4) 0.5006 (3) 0.5687 (2) 0.0249 (11)
C12 0.5343 (4) 0.4021 (3) 0.5809 (2) 0.0263 (11)
H12 0.5897 0.3657 0.6072 0.032*
C13 0.4109 (4) 0.4204 (3) 0.6139 (2) 0.0286 (11)
C14 0.1050 (5) 0.3070 (4) 0.6351 (3) 0.0551 (17)
H14A 0.1243 0.2506 0.6137 0.066*
H14B 0.0260 0.3286 0.6217 0.066*
H14C 0.1034 0.2960 0.6795 0.066*
C15 0.0561 (4) 0.5004 (4) 0.6546 (3) 0.0562 (18)
H15A 0.0144 0.5018 0.6150 0.067*
H15B 0.0557 0.5610 0.6727 0.067*
H15C 0.0149 0.4582 0.6822 0.067*
C16 0.9950 (5) 0.4174 (4) 0.4779 (2) 0.0292 (11)
C17 1.0732 (5) 0.5611 (4) 0.4379 (2) 0.0378 (13)
C18 0.9760 (5) 0.6130 (4) 0.4744 (2) 0.0318 (12)
C19 0.7606 (4) 0.5940 (3) 0.5149 (2) 0.0268 (11)
H19 0.7702 0.6136 0.5585 0.032*
C20 0.6256 (5) 0.6262 (4) 0.4347 (2) 0.0335 (13)
C21 0.5672 (5) 0.6670 (4) 0.3839 (3) 0.0468 (15)
H21 0.5771 0.7295 0.3757 0.056*
C22 0.4947 (5) 0.6133 (4) 0.3460 (3) 0.0514 (16)
H22 0.4556 0.6398 0.3117 0.062*
C23 0.4793 (5) 0.5206 (4) 0.3581 (2) 0.0450 (15)
H23 0.4318 0.4850 0.3312 0.054*
C24 0.5339 (4) 0.4796 (4) 0.4101 (2) 0.0351 (13)
H24 0.5217 0.4173 0.4185 0.042*
C25 0.6062 (4) 0.5326 (3) 0.4488 (2) 0.0247 (11)
C26 0.6744 (4) 0.5086 (3) 0.5094 (2) 0.0225 (11)
C27 0.7599 (4) 0.4244 (3) 0.4986 (2) 0.0271 (11)
H27 0.7207 0.3788 0.4713 0.033*
C28 0.8740 (4) 0.4661 (3) 0.4670 (2) 0.0254 (11)
C29 1.2123 (4) 0.4245 (4) 0.4554 (2) 0.0416 (14)
H29A 1.2098 0.3640 0.4737 0.050*
H29B 1.2752 0.4603 0.4753 0.050*
H29C 1.2299 0.4192 0.4114 0.050*
C30 1.1887 (5) 0.6189 (4) 0.4295 (3) 0.0472 (16)
H30A 1.2270 0.6283 0.4695 0.057*
H30B 1.1674 0.6776 0.4117 0.057*
H30C 1.2446 0.5874 0.4021 0.057*
C31 0.2123 (7) 0.2837 (5) 0.2576 (4) 0.087 (3)
H31 0.2037 0.3324 0.2261 0.104*
Cl1 0.1028 (2) 0.30660 (16) 0.31514 (12) 0.1085 (8)
Cl2 0.1912 (3) 0.1858 (2) 0.22083 (14) 0.1488 (12)
supporting information
sup-4 Acta Cryst. (2006). E62, o974–o976
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
S1 0.0424 (8) 0.0710 (11) 0.0336 (8) 0.0049 (8) 0.0076 (7) −0.0089 (8) S2 0.0363 (8) 0.0633 (10) 0.0259 (7) 0.0079 (7) 0.0016 (6) 0.0064 (7) S3 0.0518 (9) 0.0761 (11) 0.0303 (7) −0.0052 (9) 0.0076 (7) 0.0163 (8) S4 0.0442 (8) 0.0592 (10) 0.0244 (7) −0.0031 (8) −0.0006 (6) −0.0035 (7) O1 0.055 (3) 0.031 (2) 0.068 (3) −0.0038 (19) 0.016 (2) −0.001 (2)
O2 0.046 (2) 0.051 (3) 0.062 (3) 0.023 (2) 0.007 (2) 0.014 (2)
O3 0.043 (2) 0.025 (2) 0.036 (2) −0.005 (2) 0.0099 (18) −0.0040 (18) O4 0.040 (2) 0.0251 (19) 0.040 (2) 0.0075 (18) 0.0017 (18) 0.0026 (16) O5 0.045 (2) 0.027 (2) 0.065 (3) −0.0068 (19) 0.008 (2) 0.0022 (19) O6 0.031 (2) 0.040 (2) 0.038 (2) 0.0125 (19) 0.0075 (18) 0.0132 (17) N1 0.033 (3) 0.047 (3) 0.036 (3) −0.014 (2) 0.003 (2) 0.001 (2) N2 0.020 (2) 0.027 (2) 0.034 (2) −0.0005 (19) −0.0001 (19) 0.0014 (19) N3 0.041 (3) 0.019 (2) 0.049 (3) 0.009 (2) −0.006 (2) −0.005 (2) N4 0.023 (2) 0.030 (2) 0.034 (2) 0.002 (2) 0.0010 (18) 0.001 (2) N5 0.025 (2) 0.025 (2) 0.030 (2) −0.001 (2) 0.0046 (18) 0.0025 (19) N6 0.034 (2) 0.025 (2) 0.054 (3) 0.004 (2) −0.005 (2) −0.002 (2)
C1 0.034 (3) 0.038 (3) 0.033 (3) 0.000 (3) 0.006 (3) 0.002 (3)
C2 0.029 (3) 0.050 (4) 0.034 (3) 0.005 (3) 0.007 (2) 0.000 (3)
C3 0.028 (3) 0.037 (3) 0.035 (3) 0.002 (3) −0.001 (2) 0.002 (3) C4 0.028 (3) 0.027 (3) 0.025 (2) −0.002 (2) 0.004 (2) 0.000 (2) C5 0.042 (3) 0.032 (3) 0.030 (3) −0.007 (3) 0.013 (3) −0.001 (2) C6 0.065 (4) 0.033 (3) 0.043 (3) −0.005 (3) 0.008 (3) −0.014 (3) C7 0.064 (5) 0.079 (5) 0.038 (4) −0.017 (4) 0.000 (3) −0.024 (4) C8 0.039 (3) 0.091 (5) 0.029 (3) 0.000 (4) −0.004 (3) 0.000 (3)
C9 0.029 (3) 0.050 (3) 0.027 (3) 0.006 (3) 0.001 (2) 0.001 (2)
C30 0.031 (3) 0.048 (4) 0.062 (4) −0.009 (3) 0.009 (3) 0.013 (3) C31 0.071 (5) 0.062 (5) 0.127 (7) 0.004 (4) −0.008 (5) −0.015 (5) Cl1 0.129 (2) 0.0945 (16) 0.1025 (17) 0.0085 (15) −0.0161 (16) −0.0266 (13) Cl2 0.152 (2) 0.144 (2) 0.150 (2) −0.056 (2) 0.063 (2) −0.063 (2) Cl3 0.101 (2) 0.145 (2) 0.286 (4) 0.0228 (18) −0.086 (3) −0.048 (3)
Geometric parameters (Å, º)
S1—C2 1.890 (5) O4—C16 1.241 (5)
S1—S2 2.068 (2) O5—C18 1.216 (6)
S2—C13 1.891 (5) O6—C27 1.416 (5)
O1—C1 1.213 (6) O6—H6O 0.83 (5)
O2—C3 1.217 (6) N4—C16 1.357 (6)
O3—C12 1.411 (6) N4—C29 1.448 (6)
O3—H3O 0.73 (5) N4—C17 1.459 (6)
N1—C1 1.369 (6) N5—C18 1.361 (6)
N1—C2 1.450 (6) N5—C28 1.429 (6)
N1—C14 1.460 (6) N5—C19 1.479 (5)
N2—C3 1.340 (6) N6—C20 1.379 (6)
N2—C13 1.426 (6) N6—C19 1.439 (6)
N2—C4 1.485 (6) N6—H6N 0.8600
N3—C5 1.390 (6) C16—C28 1.514 (6)
N3—C4 1.440 (6) C17—C18 1.515 (7)
N3—H3N 0.8600 C17—C30 1.523 (7)
C1—C13 1.520 (7) C19—C26 1.558 (6)
C2—C15 1.502 (7) C19—H19 0.9800
C2—C3 1.546 (7) C20—C21 1.390 (7)
C4—C11 1.566 (6) C20—C25 1.406 (7)
C4—H4 0.9800 C21—C22 1.372 (8)
C5—C6 1.387 (7) C21—H21 0.9300
C5—C10 1.388 (6) C22—C23 1.379 (8)
C6—C7 1.374 (8) C22—H22 0.9300
C6—H6 0.9300 C23—C24 1.391 (7)
C7—C8 1.345 (8) C23—H23 0.9300
C7—H7 0.9300 C24—C25 1.377 (6)
C8—C9 1.399 (7) C24—H24 0.9300
C8—H8 0.9300 C25—C26 1.532 (6)
C9—C10 1.376 (6) C26—C27 1.553 (6)
C9—H9 0.9300 C27—C28 1.539 (6)
C10—C11 1.546 (6) C27—H27 0.9800
C11—C12 1.555 (6) C29—H29A 0.9600
C12—C13 1.542 (6) C29—H29B 0.9600
C12—H12 0.9800 C29—H29C 0.9600
C14—H14A 0.9600 C30—H30A 0.9600
C14—H14B 0.9600 C30—H30B 0.9600
C14—H14C 0.9600 C30—H30C 0.9600
C15—H15A 0.9600 C11—C26 1.598 (6)
supporting information
sup-6 Acta Cryst. (2006). E62, o974–o976
C15—H15C 0.9600 C31—Cl1 1.744 (8)
S3—C17 1.885 (5) C31—Cl3 1.745 (8)
S3—S4 2.073 (2) C31—H31 0.9800
S4—C28 1.893 (4)
C2—S1—S2 99.28 (16) C16—N4—C29 119.2 (4)
C13—S2—S1 97.14 (16) C16—N4—C17 117.4 (4)
C12—O3—H3O 115 (4) C29—N4—C17 120.3 (4)
C1—N1—C2 117.2 (4) C18—N5—C28 119.2 (4)
C1—N1—C14 117.6 (5) C18—N5—C19 124.9 (4)
C2—N1—C14 120.2 (4) C28—N5—C19 114.9 (4)
C3—N2—C13 119.7 (4) C20—N6—C19 109.7 (4)
C3—N2—C4 124.7 (4) C20—N6—H6N 125.1
C13—N2—C4 114.4 (4) C19—N6—H6N 125.1
C5—N3—C4 108.7 (4) O4—C16—N4 123.3 (5)
C5—N3—H3N 125.6 O4—C16—C28 122.7 (5)
C4—N3—H3N 125.6 N4—C16—C28 113.9 (4)
O1—C1—N1 123.4 (5) N4—C17—C18 111.7 (4)
O1—C1—C13 123.4 (5) N4—C17—C30 114.3 (4)
N1—C1—C13 113.1 (5) C18—C17—C30 111.4 (4)
N1—C2—C15 114.2 (5) N4—C17—S3 110.4 (3)
N1—C2—C3 110.9 (4) C18—C17—S3 101.7 (3)
C15—C2—C3 111.4 (5) C30—C17—S3 106.3 (4)
N1—C2—S1 110.1 (4) O5—C18—N5 122.8 (5)
C15—C2—S1 106.2 (4) O5—C18—C17 124.6 (5)
C3—C2—S1 103.4 (3) N5—C18—C17 112.6 (4)
O2—C3—N2 124.9 (5) N6—C19—N5 113.3 (4)
O2—C3—C2 123.0 (5) N6—C19—C26 105.9 (4)
N2—C3—C2 112.1 (4) N5—C19—C26 102.8 (3)
N3—C4—N2 111.1 (4) N6—C19—H19 111.5
N3—C4—C11 107.2 (4) N5—C19—H19 111.5
N2—C4—C11 102.8 (4) C26—C19—H19 111.5
N3—C4—H4 111.8 N6—C20—C21 129.0 (5)
N2—C4—H4 111.8 N6—C20—C25 110.4 (4)
C11—C4—H4 111.8 C21—C20—C25 120.5 (5)
C6—C5—C10 121.0 (5) C22—C21—C20 118.9 (5)
C6—C5—N3 127.1 (5) C22—C21—H21 120.5
C10—C5—N3 111.8 (4) C20—C21—H21 120.5
C7—C6—C5 117.9 (5) C21—C22—C23 120.7 (5)
C7—C6—H6 121.1 C21—C22—H22 119.6
C5—C6—H6 121.1 C23—C22—H22 119.6
C8—C7—C6 122.2 (6) C22—C23—C24 120.9 (5)
C8—C7—H7 118.9 C22—C23—H23 119.5
C6—C7—H7 118.9 C24—C23—H23 119.5
C7—C8—C9 120.2 (5) C25—C24—C23 119.1 (5)
C7—C8—H8 119.9 C25—C24—H24 120.5
C9—C8—H8 119.9 C23—C24—H24 120.5
C10—C9—H9 120.5 C24—C25—C26 131.2 (4)
C8—C9—H9 120.5 C20—C25—C26 109.1 (4)
C9—C10—C5 119.6 (5) C25—C26—C27 110.2 (3)
C9—C10—C11 131.3 (5) C25—C26—C19 100.1 (3)
C5—C10—C11 109.1 (4) C27—C26—C19 105.9 (3)
C10—C11—C12 110.1 (4) C25—C26—C11 113.1 (4)
C10—C11—C4 99.3 (4) C27—C26—C11 115.0 (4)
C12—C11—C4 105.7 (4) C19—C26—C11 111.3 (3)
C10—C11—C26 113.5 (4) O6—C27—C28 109.9 (4)
C12—C11—C26 114.7 (3) O6—C27—C26 110.2 (4)
C4—C11—C26 112.2 (4) C28—C27—C26 103.9 (4)
O3—C12—C13 109.8 (4) O6—C27—H27 110.9
O3—C12—C11 108.4 (4) C28—C27—H27 110.9
C13—C12—C11 103.5 (4) C26—C27—H27 110.9
O3—C12—H12 111.6 N5—C28—C16 111.7 (4)
C13—C12—H12 111.6 N5—C28—C27 104.5 (4)
C11—C12—H12 111.6 C16—C28—C27 117.0 (4)
N2—C13—C1 112.7 (4) N5—C28—S4 112.6 (3)
N2—C13—C12 104.8 (4) C16—C28—S4 100.1 (3)
C1—C13—C12 116.2 (4) C27—C28—S4 111.2 (3)
N2—C13—S2 112.6 (3) N4—C29—H29A 109.5
C1—C13—S2 100.3 (3) N4—C29—H29B 109.5
C12—C13—S2 110.5 (3) H29A—C29—H29B 109.5
N1—C14—H14A 109.5 N4—C29—H29C 109.5
N1—C14—H14B 109.5 H29A—C29—H29C 109.5
H14A—C14—H14B 109.5 H29B—C29—H29C 109.5
N1—C14—H14C 109.5 C17—C30—H30A 109.5
H14A—C14—H14C 109.5 C17—C30—H30B 109.5
H14B—C14—H14C 109.5 H30A—C30—H30B 109.5
C2—C15—H15A 109.5 C17—C30—H30C 109.5
C2—C15—H15B 109.5 H30A—C30—H30C 109.5
H15A—C15—H15B 109.5 H30B—C30—H30C 109.5
C2—C15—H15C 109.5 Cl2—C31—Cl1 114.0 (4)
H15A—C15—H15C 109.5 Cl2—C31—Cl3 112.1 (4)
H15B—C15—H15C 109.5 Cl1—C31—Cl3 111.2 (5)
C17—S3—S4 99.04 (17) Cl2—C31—H31 106.3
C28—S4—S3 97.15 (16) Cl1—C31—H31 106.3
C27—O6—H6O 108 (3) Cl3—C31—H31 106.3
C2—S1—S2—C13 11.7 (2) C16—N4—C17—C18 46.4 (6)
C17—S3—S4—C28 14.2 (2) C29—N4—C17—C18 −153.7 (4)
C2—N1—C1—O1 171.8 (5) C16—N4—C17—C30 174.0 (4)
C14—N1—C1—O1 16.6 (8) C29—N4—C17—C30 −26.0 (6)
C2—N1—C1—C13 −5.8 (6) C16—N4—C17—S3 −66.1 (5)
C14—N1—C1—C13 −161.0 (4) C29—N4—C17—S3 93.9 (4)
C1—N1—C2—C15 175.8 (5) S4—S3—C17—N4 47.8 (3)
C14—N1—C2—C15 −29.7 (7) S4—S3—C17—C18 −71.0 (3)
supporting information
sup-8 Acta Cryst. (2006). E62, o974–o976
C14—N1—C2—C3 −156.5 (4) C28—N5—C18—O5 174.8 (5)
C1—N1—C2—S1 −64.8 (5) C19—N5—C18—O5 7.0 (7)
C14—N1—C2—S1 89.7 (5) C28—N5—C18—C17 −2.0 (6)
S2—S1—C2—N1 50.3 (3) C19—N5—C18—C17 −169.9 (4)
S2—S1—C2—C15 174.5 (4) N4—C17—C18—O5 139.4 (5)
S2—S1—C2—C3 −68.2 (3) C30—C17—C18—O5 10.2 (7)
C13—N2—C3—O2 178.0 (5) S3—C17—C18—O5 −102.8 (5)
C4—N2—C3—O2 11.5 (8) N4—C17—C18—N5 −43.8 (6)
C13—N2—C3—C2 −0.8 (6) C30—C17—C18—N5 −173.1 (4)
C4—N2—C3—C2 −167.4 (4) S3—C17—C18—N5 74.0 (4)
N1—C2—C3—O2 135.4 (5) C20—N6—C19—N5 91.1 (5)
C15—C2—C3—O2 7.0 (7) C20—N6—C19—C26 −20.8 (5)
S1—C2—C3—O2 −106.7 (5) C18—N5—C19—N6 55.6 (6)
N1—C2—C3—N2 −45.8 (6) C28—N5—C19—N6 −112.8 (4)
C15—C2—C3—N2 −174.2 (4) C18—N5—C19—C26 169.4 (4)
S1—C2—C3—N2 72.2 (4) C28—N5—C19—C26 1.0 (5)
C5—N3—C4—N2 94.4 (5) C19—N6—C20—C21 −169.4 (5)
C5—N3—C4—C11 −17.2 (5) C19—N6—C20—C25 11.2 (6)
C3—N2—C4—N3 55.3 (6) N6—C20—C21—C22 177.7 (5)
C13—N2—C4—N3 −111.9 (4) C25—C20—C21—C22 −3.0 (8)
C3—N2—C4—C11 169.6 (4) C20—C21—C22—C23 0.3 (9)
C13—N2—C4—C11 2.4 (5) C21—C22—C23—C24 1.9 (9)
C4—N3—C5—C6 −169.2 (5) C22—C23—C24—C25 −1.4 (8)
C4—N3—C5—C10 6.8 (5) C23—C24—C25—C20 −1.3 (7)
C10—C5—C6—C7 −1.3 (8) C23—C24—C25—C26 178.1 (4)
N3—C5—C6—C7 174.3 (5) N6—C20—C25—C24 −177.1 (4)
C5—C6—C7—C8 −0.4 (9) C21—C20—C25—C24 3.5 (7)
C6—C7—C8—C9 2.6 (9) N6—C20—C25—C26 3.4 (5)
C7—C8—C9—C10 −3.1 (8) C21—C20—C25—C26 −176.0 (4)
C8—C9—C10—C5 1.4 (7) C24—C25—C26—C27 54.4 (6)
C8—C9—C10—C11 178.6 (5) C20—C25—C26—C27 −126.2 (4)
C6—C5—C10—C9 0.7 (7) C24—C25—C26—C19 165.6 (5)
N3—C5—C10—C9 −175.5 (4) C20—C25—C26—C19 −14.9 (5)
C6—C5—C10—C11 −177.1 (5) C24—C25—C26—C11 −75.9 (6)
N3—C5—C10—C11 6.7 (5) C20—C25—C26—C11 103.5 (4)
C9—C10—C11—C12 56.2 (6) N6—C19—C26—C25 20.9 (4)
C5—C10—C11—C12 −126.3 (4) N5—C19—C26—C25 −98.2 (4)
C9—C10—C11—C4 166.8 (5) N6—C19—C26—C27 135.4 (4)
C5—C10—C11—C4 −15.8 (5) N5—C19—C26—C27 16.4 (4)
C9—C10—C11—C26 −73.8 (6) N6—C19—C26—C11 −98.9 (4)
C5—C10—C11—C26 103.6 (4) N5—C19—C26—C11 142.1 (4)
N3—C4—C11—C10 19.4 (4) C10—C11—C26—C25 −141.5 (4)
N2—C4—C11—C10 −97.7 (4) C12—C11—C26—C25 90.7 (5)
N3—C4—C11—C12 133.5 (4) C4—C11—C26—C25 −29.9 (5)
N2—C4—C11—C12 16.3 (4) C10—C11—C26—C27 90.7 (5)
N3—C4—C11—C26 −100.9 (4) C12—C11—C26—C27 −37.1 (5)
N2—C4—C11—C26 142.0 (3) C4—C11—C26—C27 −157.6 (4)
C4—C11—C12—O3 88.7 (4) C12—C11—C26—C19 −157.5 (4)
C26—C11—C12—O3 −35.4 (5) C4—C11—C26—C19 81.9 (4)
C10—C11—C12—C13 78.5 (4) C25—C26—C27—O6 −161.8 (4)
C4—C11—C12—C13 −27.9 (4) C19—C26—C27—O6 90.8 (4)
C26—C11—C12—C13 −152.0 (4) C11—C26—C27—O6 −32.6 (5)
C3—N2—C13—C1 44.6 (6) C25—C26—C27—C28 80.5 (4)
C4—N2—C13—C1 −147.5 (4) C19—C26—C27—C28 −26.9 (4)
C3—N2—C13—C12 171.9 (4) C11—C26—C27—C28 −150.2 (4)
C4—N2—C13—C12 −20.2 (5) C18—N5—C28—C16 45.5 (5)
C3—N2—C13—S2 −67.9 (5) C19—N5—C28—C16 −145.5 (4)
C4—N2—C13—S2 100.0 (4) C18—N5—C28—C27 172.9 (4)
O1—C1—C13—N2 141.3 (5) C19—N5—C28—C27 −18.1 (5)
N1—C1—C13—N2 −41.0 (6) C18—N5—C28—S4 −66.3 (5)
O1—C1—C13—C12 20.4 (7) C19—N5—C28—S4 102.8 (4)
N1—C1—C13—C12 −162.0 (4) O4—C16—C28—N5 139.6 (4)
O1—C1—C13—S2 −98.7 (5) N4—C16—C28—N5 −42.7 (5)
N1—C1—C13—S2 78.9 (4) O4—C16—C28—C27 19.2 (6)
O3—C12—C13—N2 −86.6 (4) N4—C16—C28—C27 −163.1 (4)
C11—C12—C13—N2 29.0 (4) O4—C16—C28—S4 −101.0 (4)
O3—C12—C13—C1 38.5 (5) N4—C16—C28—S4 76.7 (4)
C11—C12—C13—C1 154.1 (4) O6—C27—C28—N5 −90.9 (4)
O3—C12—C13—S2 151.9 (3) C26—C27—C28—N5 27.0 (4)
C11—C12—C13—S2 −92.5 (4) O6—C27—C28—C16 33.2 (5)
S1—S2—C13—N2 49.7 (3) C26—C27—C28—C16 151.1 (4)
S1—S2—C13—C1 −70.3 (3) O6—C27—C28—S4 147.3 (3)
S1—S2—C13—C12 166.5 (3) C26—C27—C28—S4 −94.7 (4)
C29—N4—C16—O4 14.6 (7) S3—S4—C28—N5 47.1 (3)
C17—N4—C16—O4 174.8 (4) S3—S4—C28—C16 −71.7 (3)
C29—N4—C16—C28 −163.1 (4) S3—S4—C28—C27 164.0 (3)
C17—N4—C16—C28 −2.9 (6)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O3—H3O···O1 0.73 (5) 2.31 (5) 2.785 (5) 124 (5)
O3—H3O···O4i 0.73 (5) 2.20 (5) 2.861 (5) 152 (6)
O6—H6O···O4 0.83 (5) 1.98 (5) 2.709 (5) 145 (4)
