organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 2| February 2009| Pages o283-o284

Bis{(E)-3-[(di­ethyl­methyl­ammonio)meth­yl]-N-[3-(N,N-di­methyl­sulfamo­yl)-1-methyl­pyridin-4-yl­­idene]-4-meth­oxy­anilinium} tetra­iodide penta­hydrate

aiMed.UL, Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal, and bEd. CACTUS, Campus Sur, Unidade de Raios X, Universidad de Santiago Compostela 15782, Spain
*Correspondence e-mail: fclopes@ff.ul.pt

(Received 12 November 2008; accepted 5 January 2009; online 10 January 2009)

The title compound, 2C21H34N4O3S2+·4I·5H2O, was prepared exclusively as the E isomer by methyl­ation of the corresponding N-phenyl­pyridin-4-amine. There are two symmetry-independent mol­ecules in the asymmetric unit with no significant differences in bond lengths and angles. The aromatic rings are not coplanar with the pyridin-4-imine groups, as indicated by the C—N—C—C torsion angles of 47.7 (7) and 132.6 (5)°.

Related literature

For background information see: Bjorkman & Bhattarai (2005[Bjorkman, A. & Bhattarai, A. (2005). Acta Trop. 94, 163-169.]); Yeates et al. (2008[Yeates, C. L., Batchelor, J. F., Capon, E. C., Cheesman, N. J., Fry, M., Hudson, A. T., Pudney, M., Trimming, H., Woolven, J., Bueno, J. M., Chicharro, J., Fernández, E., Fiandor, J. M., Gargallo-Viola, D., de las Heras, F. G., Herreros, E. & León, M. L. (2008). J. Med. Chem. 51, 2845-2852.]). For related literature structures, see: Lopes et al. (2004[Lopes, F., Capela, R., Gonçalves, J. O., Horton, P. N., Hursthouse, M. B., Iley, J., Casimiro, C. M., Bom, J. & Moreira, R. (2004). Tetrahedron Lett. 45, 7663-7666.]); Wang et al. (2008[Wang, Y., Zhang, J., Chen, H. & Luo, S. (2008). Acta Cryst. E64, o1025.]); Djedouani et al. (2008[Djedouani, A., Boufas, S., Allain, M., Bouet, G. & Khan, M. (2008). Acta Cryst. E64, o1785.]).

[Scheme 1]

Experimental

Crystal data
  • 2C21H34N4O3S2+·4I·5H2O

  • Mr = 1442.86

  • Triclinic, [P \overline 1]

  • a = 12.7930 (5) Å

  • b = 13.5539 (6) Å

  • c = 16.8386 (7) Å

  • α = 96.670 (2)°

  • β = 97.667 (2)°

  • γ = 98.224 (1)°

  • V = 2836.5 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.33 mm−1

  • T = 100 (2) K

  • 0.35 × 0.2 × 0.08 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.575, Tmax = 0.830

  • 49577 measured reflections

  • 11468 independent reflections

  • 8753 reflections with I > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.116

  • S = 1.00

  • 11468 reflections

  • 654 parameters

  • 17 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 2.07 e Å−3

  • Δρmin = −1.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1WA⋯I4 0.91 (3) 2.60 (4) 3.489 (4) 170 (3)
O1W—H1WB⋯I2 0.90 (2) 2.663 (17) 3.561 (4) 176 (4)
O2W—H2WA⋯O5wi 0.90 (4) 1.98 (5) 2.799 (7) 147 (5)
O2W—H2WB⋯I3 0.90 (4) 2.69 (4) 3.580 (5) 175 (4)
O3W—H3WA⋯O1Wi 0.90 (4) 1.91 (4) 2.781 (6) 161 (18)
O3W—H3WB⋯I1 0.90 (4) 2.64 (4) 3.544 (4) 178 (5)
O4W—H4WA⋯I4 0.90 (3) 2.75 (3) 3.613 (5) 160 (4)
O4W—H4WB⋯O3Wii 0.89 (5) 1.92 (4) 2.795 (7) 162 (2)
O5W—H5WA⋯I2 0.90 (4) 2.75 (5) 3.614 (5) 165 (4)
O5W—H5WB⋯O4wiii 0.90 (4) 1.94 (4) 2.809 (7) 161 (3)
N14—H14⋯O9 0.90 (3) 1.93 (4) 2.733 (5) 149 (4)
N54—H54⋯O49 0.90 (5) 2.08 (4) 2.767 (5) 133 (4)
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Malaria is accounted as one of the major diseases worldwide, and for which few efficient drugs are known today [Bjorkman and Bhattarai, 2005]. 4(1H)-Pyridones are currently being developed as important and potential antimalarial agents, capable of inhibiting the bc1 complex, at the oxidation site (Qo site) level in the Plasmodium falciparum mitochondrion [Yeates et al., 2008]. As part of our project towards the synthesis of 4(1H)-pyridone bioisosteric scaffolds, the (1H-pyridin-4-ylidene)amine scaffold was studied.

The title compound was prepared by reaction of the corresponding N-phenylpyridin-4-amine with methyl iodide. Interestingly, only the E isomer of the compound was obtained, as it was previously observed for amodiaquine analogues [Lopes et al., 2004]. There are two symmetry-independent molecules in the asymmetric unit with no significant differences in bond lengths and angles. The observed imine bond distances C4—N14 and C44—N54 are longer than the expected by ca 0.035 Å [Wang et al., 2008 and Djedouani et al., 2008], a consequence of the imine group being protonated. The aromatic rings are not coplanar relatively to the pyridin-4-imine moieties, as indicated by the C4—N14—C15—C16 and C44—N54—C55—C56 dihedral angles of 47.7 (7)° and 132.6 (5)°, respectively. The molecules are hydrogen-bonded through the imine nitrogen atoms at N14 and N54, acting as donors towards the sulfonyl oxygen atoms O9 and O19 of each sulfonamide moiety, respectively. The (1H-pyridin-4-ylidene)amine scaffold is nearly planar and the C5—C4—N14—C15 dihedral angle is 7.9 (7)° for one of the molecules, whereas the C43—C44—N54—C55 dihedral angle on the other molecule is -14.1 (7)°.

Related literature top

For background information see: Bjorkman & Bhattarai (2005); Yeates et al. (2008). For related structures, see: Lopes et al. (2004); Wang et al. (2008); Djedouani et al. (2008).

Experimental top

The title compound was prepared at room temperature by reacting 2-[(diethylamino)methyl]-4-(pyridin-4-ylamino)phenol with methyl iodide in the presence of NaH in DMF. Crystals were grown from water.

Refinement top

The hydroxy H atoms for the water solvent molecules were initially located in a difference Fourier map, but their distances were constrained with DFIX at 0.9 Å from the O atom and with DANG at 2.5 Å from the other H water atom. The hydrogen atoms linked to the charged N14 and N54 atoms were located in a difference Fourier map, but the distances N—H were constrained at 0.9 Å, in order to get the refinement stabilization. The rest of the H atoms were positioned geometrically and included as riding atoms with C—H = 0.95 or 0.98 Å and Uiso(H)= 1.2 or 1.5 times Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. An ORTEPIII (Farrugia, 1997) view of the molecular structure of the title compound, showing the labelling of all non-H atoms. Displacement ellipsoids for non-H atoms are shown at the 50% probability level. H atoms have been omitted for clarity.
Bis{(E)-3-[(Diethylmethylammonio)methyl]-N-[3-(N,N- dimethylsulfamoyl)-1-methylpyridin-4-ylidene]-4-methoxyanilinium} tetraiodide pentahydrate top
Crystal data top
2C21H34N4O3S2+·4I·5H2OZ = 2
Mr = 1442.86F(000) = 1436.0
Triclinic, P1Dx = 1.687 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 12.7930 (5) ÅCell parameters from 9916 reflections
b = 13.5539 (6) Åθ = 2.4–25.8°
c = 16.8386 (7) ŵ = 2.33 mm1
α = 96.670 (2)°T = 100 K
β = 97.667 (2)°Prism, colourless
γ = 98.224 (1)°0.35 × 0.2 × 0.08 mm
V = 2836.5 (2) Å3
Data collection top
Bruker APEXII CCD
diffractometer
8753 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
ω and ϕ scansθmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1515
Tmin = 0.575, Tmax = 0.830k = 1616
49577 measured reflectionsl = 021
11468 independent reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0655P)2]
where P = (Fo2 + 2Fc2)/3
11468 reflections(Δ/σ)max = 0.002
654 parametersΔρmax = 2.07 e Å3
17 restraintsΔρmin = 1.42 e Å3
Crystal data top
2C21H34N4O3S2+·4I·5H2Oγ = 98.224 (1)°
Mr = 1442.86V = 2836.5 (2) Å3
Triclinic, P1Z = 2
a = 12.7930 (5) ÅMo Kα radiation
b = 13.5539 (6) ŵ = 2.33 mm1
c = 16.8386 (7) ÅT = 100 K
α = 96.670 (2)°0.35 × 0.2 × 0.08 mm
β = 97.667 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
11468 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
8753 reflections with I > 2σ(I)
Tmin = 0.575, Tmax = 0.830Rint = 0.050
49577 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04317 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 2.07 e Å3
11468 reflectionsΔρmin = 1.42 e Å3
654 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1W0.4474 (3)0.1184 (3)0.6544 (2)0.0347 (10)
H1WA0.414 (3)0.172 (2)0.665 (3)0.042*
H1WB0.5190 (9)0.135 (3)0.665 (3)0.042*
O2W0.8769 (5)0.9278 (3)0.8610 (3)0.0587 (14)
H2WA0.913 (5)0.940 (4)0.820 (3)0.070*
H2WB0.836 (5)0.867 (2)0.852 (3)0.070*
O3W0.2931 (4)0.9651 (3)0.6823 (2)0.0428 (11)
H3WA0.352 (3)1.010 (3)0.681 (3)0.051*
H3WB0.299 (4)0.931 (4)0.725 (2)0.051*
O4W0.1157 (4)0.0625 (4)0.6565 (3)0.0485 (12)
H4WA0.145 (4)0.1267 (15)0.655 (4)0.058*
H4WB0.166 (3)0.026 (3)0.674 (4)0.058*
O5W0.9315 (4)0.0196 (4)0.7284 (3)0.0555 (13)
H5WA0.892 (4)0.065 (4)0.713 (4)0.067*
H5WB0.989 (3)0.018 (4)0.703 (3)0.067*
I10.32351 (3)0.83284 (3)0.85134 (2)0.02456 (10)
I20.73146 (3)0.17740 (3)0.68619 (2)0.02986 (11)
I30.71949 (3)0.68226 (3)0.811724 (17)0.01851 (10)
I40.28842 (3)0.30343 (3)0.687434 (18)0.02097 (10)
N10.0320 (3)0.6774 (3)0.7703 (2)0.0179 (9)
C20.0149 (4)0.6876 (4)0.8477 (2)0.0171 (11)
H20.03680.72510.86230.021*
C30.0710 (4)0.6446 (4)0.9058 (2)0.0147 (10)
C40.1531 (4)0.5890 (3)0.8865 (3)0.0136 (10)
C50.1607 (4)0.5714 (4)0.8024 (3)0.0155 (10)
H50.20570.52820.78460.019*
C60.1033 (4)0.6167 (4)0.7484 (2)0.0185 (11)
H60.11260.60640.69430.022*
C70.0207 (4)0.7323 (4)0.7111 (3)0.0278 (13)
H7A0.06280.77540.73740.042*
H7B0.06620.68530.66930.042*
H7C0.03230.77220.68780.042*
S80.03896 (9)0.67067 (9)1.00503 (6)0.0135 (3)
O90.0913 (3)0.6067 (3)1.05430 (18)0.0209 (8)
O100.0746 (3)0.6639 (3)0.99700 (18)0.0204 (8)
N110.0902 (3)0.7864 (3)1.0408 (2)0.0175 (9)
C120.2061 (4)0.8092 (5)1.0648 (3)0.0321 (14)
H12A0.24010.81281.01750.048*
H12B0.22990.75731.09340.048*
H12C0.22450.87261.09930.048*
C130.0461 (5)0.8645 (4)0.9992 (3)0.0293 (13)
H13A0.07690.87100.95080.044*
H13B0.06250.92761.03430.044*
H13C0.03010.84600.98550.044*
N140.2167 (3)0.5534 (3)0.9424 (2)0.0146 (9)
H140.194 (4)0.561 (3)0.9901 (14)0.017*
C150.3067 (4)0.5053 (3)0.9282 (2)0.0134 (10)
C160.3822 (4)0.5466 (3)0.8849 (2)0.0116 (10)
H160.37530.60650.86430.014*
C170.4682 (4)0.4985 (4)0.8721 (2)0.0141 (10)
H170.51910.52620.84290.017*
C180.4789 (4)0.4094 (4)0.9026 (2)0.0134 (10)
C190.4046 (4)0.3688 (3)0.9500 (2)0.0131 (10)
C200.3190 (4)0.4191 (4)0.9622 (2)0.0135 (10)
H200.26960.39410.99360.016*
O210.5609 (3)0.3568 (2)0.89193 (18)0.0156 (7)
C220.6274 (4)0.3884 (4)0.8348 (3)0.0284 (13)
H22A0.58360.39180.78450.043*
H22B0.67510.34100.82610.043*
H22C0.66810.45360.85530.043*
C230.4197 (4)0.2776 (3)0.9912 (2)0.0140 (10)
H23A0.39600.28711.04360.017*
H23B0.49560.27451.00100.017*
N240.3617 (3)0.1764 (3)0.9456 (2)0.0142 (9)
C250.4097 (4)0.1478 (4)0.8698 (3)0.0172 (11)
H25A0.36270.09090.83690.021*
H25B0.41300.20370.83860.021*
C260.5201 (4)0.1207 (4)0.8870 (3)0.0238 (12)
H26A0.56410.17160.92670.036*
H26B0.55110.11620.83800.036*
H26C0.51540.05700.90710.036*
C270.2446 (4)0.1837 (4)0.9202 (3)0.0199 (11)
H27A0.21770.21540.96630.024*
H27B0.23990.22710.87840.024*
C280.1728 (4)0.0841 (4)0.8887 (3)0.0295 (13)
H28A0.20540.04620.84990.044*
H28B0.10490.09630.86350.044*
H28C0.16260.04680.93290.044*
C290.3720 (4)0.1004 (4)1.0034 (3)0.0193 (11)
H29A0.34950.03380.97450.029*
H29B0.32800.11161.04450.029*
H29C0.44520.10731.02830.029*
N410.9817 (3)0.3632 (3)0.7359 (2)0.0143 (9)
C420.9073 (4)0.4212 (4)0.7574 (2)0.0150 (11)
H420.89880.43300.81150.018*
C430.8464 (4)0.4612 (4)0.7019 (3)0.0140 (10)
H430.79750.50080.71850.017*
C440.8558 (4)0.4437 (3)0.6181 (2)0.0118 (10)
C450.9372 (4)0.3870 (3)0.5991 (2)0.0113 (10)
C460.9962 (4)0.3490 (3)0.6584 (3)0.0135 (10)
H461.04840.31190.64450.016*
C471.0393 (4)0.3134 (4)0.7974 (3)0.0226 (12)
H47A0.99040.26170.81360.034*
H47B1.07030.36210.84360.034*
H47C1.09480.28400.77510.034*
S480.95911 (10)0.34819 (9)0.49898 (6)0.0144 (3)
O490.9141 (3)0.4153 (2)0.44787 (17)0.0172 (7)
O501.0700 (3)0.3398 (3)0.50195 (18)0.0179 (8)
N510.8905 (3)0.2370 (3)0.4701 (2)0.0191 (9)
C520.9303 (5)0.1519 (4)0.5057 (3)0.0262 (13)
H52A0.90040.14290.55420.039*
H52B1.00680.16600.51820.039*
H52C0.90930.09150.46760.039*
C530.7730 (4)0.2294 (4)0.4602 (3)0.0265 (13)
H53A0.75160.28230.43160.040*
H53B0.75050.23560.51250.040*
H53C0.74050.16530.43010.040*
N540.7923 (3)0.4792 (3)0.5618 (2)0.0145 (9)
H540.813 (4)0.486 (3)0.5136 (14)0.017*
C550.6969 (4)0.5173 (4)0.5752 (2)0.0142 (10)
C560.6208 (4)0.4609 (4)0.6102 (2)0.0129 (10)
H560.63350.39980.62630.015*
C570.5259 (4)0.4951 (4)0.6215 (2)0.0156 (10)
H570.47510.45710.64510.019*
C580.5075 (4)0.5860 (4)0.5973 (2)0.0123 (10)
C590.5836 (4)0.6442 (3)0.5615 (2)0.0120 (10)
C600.6781 (4)0.6071 (4)0.5503 (2)0.0148 (10)
H600.72870.64380.52570.018*
O610.4154 (3)0.6249 (3)0.60549 (18)0.0172 (8)
C620.3569 (5)0.5914 (5)0.6669 (3)0.0381 (16)
H62A0.31510.52640.64730.057*
H62B0.31050.63850.68030.057*
H62C0.40600.58690.71430.057*
C630.5599 (4)0.7401 (3)0.5315 (2)0.0154 (10)
H63A0.48320.73410.51590.019*
H63B0.59250.74730.48330.019*
N640.5981 (3)0.8360 (3)0.5915 (2)0.0162 (9)
C650.5493 (4)0.8250 (4)0.6690 (3)0.0182 (11)
H65A0.47210.81080.65460.022*
H65B0.57180.76720.69120.022*
C660.5774 (4)0.9148 (4)0.7346 (3)0.0221 (12)
H66A0.65220.92360.75560.033*
H66B0.53630.90370.77740.033*
H66C0.56150.97400.71240.033*
C670.7185 (4)0.8567 (4)0.6140 (3)0.0192 (11)
H67A0.74160.79930.63660.023*
H67B0.73770.91440.65590.023*
C680.7793 (4)0.8771 (4)0.5438 (3)0.0298 (14)
H68A0.76360.81920.50300.045*
H68B0.85470.89070.56320.045*
H68C0.75780.93420.52120.045*
C690.5592 (4)0.9205 (4)0.5531 (3)0.0244 (12)
H69A0.59490.98350.58330.037*
H69B0.48350.91580.55280.037*
H69C0.57420.91670.49860.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1W0.039 (3)0.033 (3)0.037 (2)0.018 (2)0.011 (2)0.0050 (19)
O2W0.083 (4)0.032 (3)0.046 (3)0.016 (3)0.019 (3)0.008 (2)
O3W0.059 (3)0.027 (3)0.037 (2)0.000 (2)0.003 (2)0.0035 (19)
O4W0.044 (3)0.034 (3)0.061 (3)0.010 (2)0.001 (2)0.008 (2)
O5W0.034 (3)0.063 (4)0.072 (3)0.003 (2)0.006 (2)0.028 (3)
I10.0291 (2)0.0148 (2)0.03152 (18)0.00230 (15)0.01180 (15)0.00385 (14)
I20.0374 (2)0.0207 (2)0.03183 (19)0.00250 (17)0.01728 (17)0.00016 (15)
I30.02080 (19)0.0211 (2)0.01620 (15)0.00576 (15)0.00688 (13)0.00553 (13)
I40.02065 (19)0.0215 (2)0.02325 (16)0.00578 (15)0.00691 (14)0.00628 (14)
N10.021 (2)0.026 (3)0.0111 (17)0.009 (2)0.0055 (16)0.0093 (17)
C20.016 (3)0.024 (3)0.013 (2)0.005 (2)0.0072 (19)0.005 (2)
C30.020 (3)0.016 (3)0.010 (2)0.002 (2)0.0079 (19)0.0060 (19)
C40.015 (3)0.009 (3)0.017 (2)0.001 (2)0.0066 (19)0.0013 (19)
C50.013 (3)0.010 (3)0.020 (2)0.001 (2)0.001 (2)0.0069 (19)
C60.020 (3)0.028 (3)0.008 (2)0.001 (2)0.0085 (19)0.003 (2)
C70.033 (3)0.043 (4)0.014 (2)0.019 (3)0.008 (2)0.011 (2)
S80.0166 (6)0.0169 (7)0.0104 (5)0.0073 (5)0.0068 (5)0.0052 (5)
O90.027 (2)0.030 (2)0.0143 (15)0.0194 (17)0.0100 (14)0.0111 (14)
O100.0186 (19)0.029 (2)0.0169 (15)0.0085 (16)0.0073 (14)0.0054 (15)
N110.020 (2)0.016 (2)0.0162 (18)0.0019 (19)0.0064 (17)0.0004 (17)
C120.027 (3)0.045 (4)0.019 (2)0.007 (3)0.002 (2)0.000 (2)
C130.045 (4)0.017 (3)0.032 (3)0.014 (3)0.012 (3)0.007 (2)
N140.020 (2)0.017 (2)0.0110 (17)0.0109 (19)0.0099 (16)0.0027 (16)
C150.017 (3)0.010 (3)0.013 (2)0.004 (2)0.0037 (19)0.0021 (18)
C160.014 (2)0.009 (3)0.0121 (19)0.003 (2)0.0003 (18)0.0009 (18)
C170.013 (2)0.015 (3)0.013 (2)0.001 (2)0.0028 (18)0.0013 (19)
C180.017 (3)0.013 (3)0.012 (2)0.005 (2)0.0078 (19)0.0003 (18)
C190.018 (3)0.009 (3)0.012 (2)0.006 (2)0.0009 (19)0.0010 (18)
C200.018 (3)0.016 (3)0.0069 (19)0.003 (2)0.0046 (18)0.0002 (18)
O210.0182 (18)0.0119 (19)0.0200 (15)0.0068 (15)0.0084 (14)0.0044 (14)
C220.031 (3)0.033 (4)0.033 (3)0.020 (3)0.025 (3)0.013 (2)
C230.019 (3)0.013 (3)0.013 (2)0.006 (2)0.0072 (19)0.0026 (18)
N240.022 (2)0.009 (2)0.0134 (17)0.0030 (18)0.0061 (16)0.0032 (16)
C250.021 (3)0.015 (3)0.015 (2)0.006 (2)0.006 (2)0.0019 (19)
C260.026 (3)0.023 (3)0.026 (2)0.010 (2)0.010 (2)0.004 (2)
C270.017 (3)0.016 (3)0.027 (2)0.004 (2)0.003 (2)0.005 (2)
C280.027 (3)0.018 (3)0.040 (3)0.001 (3)0.002 (3)0.006 (2)
C290.027 (3)0.012 (3)0.020 (2)0.005 (2)0.005 (2)0.004 (2)
N410.015 (2)0.018 (2)0.0118 (17)0.0056 (18)0.0040 (16)0.0040 (16)
C420.018 (3)0.019 (3)0.011 (2)0.006 (2)0.0092 (19)0.0050 (19)
C430.011 (2)0.013 (3)0.019 (2)0.003 (2)0.0057 (19)0.0019 (19)
C440.016 (3)0.008 (2)0.013 (2)0.003 (2)0.0039 (19)0.0030 (18)
C450.017 (3)0.010 (3)0.0083 (19)0.003 (2)0.0049 (18)0.0022 (17)
C460.012 (2)0.013 (3)0.019 (2)0.005 (2)0.0088 (19)0.0037 (19)
C470.024 (3)0.034 (3)0.016 (2)0.014 (3)0.008 (2)0.012 (2)
S480.0197 (7)0.0166 (7)0.0100 (5)0.0068 (5)0.0079 (5)0.0029 (5)
O490.024 (2)0.017 (2)0.0133 (14)0.0087 (16)0.0059 (14)0.0050 (14)
O500.0163 (19)0.024 (2)0.0172 (15)0.0073 (16)0.0084 (14)0.0061 (14)
N510.025 (2)0.016 (2)0.0178 (19)0.0041 (19)0.0074 (18)0.0003 (17)
C520.038 (3)0.014 (3)0.029 (3)0.005 (3)0.013 (2)0.003 (2)
C530.026 (3)0.025 (3)0.026 (3)0.002 (3)0.004 (2)0.000 (2)
N540.014 (2)0.021 (2)0.0113 (17)0.0080 (18)0.0051 (16)0.0044 (16)
C550.012 (2)0.020 (3)0.011 (2)0.007 (2)0.0008 (18)0.0023 (19)
C560.019 (3)0.010 (3)0.012 (2)0.006 (2)0.0043 (19)0.0023 (18)
C570.018 (3)0.016 (3)0.012 (2)0.001 (2)0.0027 (19)0.0011 (19)
C580.014 (3)0.015 (3)0.0090 (19)0.007 (2)0.0026 (18)0.0024 (18)
C590.017 (3)0.009 (3)0.0084 (19)0.003 (2)0.0013 (18)0.0018 (17)
C600.018 (3)0.015 (3)0.014 (2)0.006 (2)0.0068 (19)0.0022 (19)
O610.0165 (18)0.023 (2)0.0173 (15)0.0080 (16)0.0107 (14)0.0070 (14)
C620.039 (4)0.050 (4)0.045 (3)0.030 (3)0.033 (3)0.032 (3)
C630.017 (3)0.014 (3)0.015 (2)0.002 (2)0.0048 (19)0.0026 (19)
N640.023 (2)0.013 (2)0.0151 (18)0.0059 (19)0.0065 (17)0.0036 (16)
C650.022 (3)0.018 (3)0.018 (2)0.007 (2)0.009 (2)0.006 (2)
C660.029 (3)0.020 (3)0.020 (2)0.005 (2)0.010 (2)0.004 (2)
C670.018 (3)0.018 (3)0.022 (2)0.001 (2)0.006 (2)0.002 (2)
C680.033 (3)0.024 (3)0.036 (3)0.001 (3)0.021 (3)0.006 (2)
C690.039 (3)0.012 (3)0.025 (2)0.010 (3)0.005 (2)0.007 (2)
Geometric parameters (Å, º) top
O1W—H1WA0.90 (6)C28—H28B0.9600
O1W—H1WB0.90 (2)C28—H28C0.9600
O2W—H2WA0.90 (6)C29—H29A0.9600
O2W—H2WB0.89 (5)C29—H29B0.9600
O3W—H3WA0.89 (4)C29—H29C0.9600
O3W—H3WB0.90 (3)N41—C461.338 (5)
O4W—H4WA0.90 (4)N41—C421.377 (6)
O4W—H4WB0.90 (3)N41—C471.473 (6)
O5W—H5WA0.89 (4)C42—C431.349 (7)
O5W—H5WB0.89 (5)C42—H420.9300
N1—C21.346 (5)C43—C441.428 (6)
N1—C61.371 (6)C43—H430.9300
N1—C71.461 (6)C44—N541.342 (6)
C2—C31.369 (6)C44—C451.427 (6)
C2—H20.9300C45—C461.365 (6)
C3—C41.428 (6)C45—S481.777 (4)
C3—S81.781 (4)C46—H460.9300
C4—N141.339 (6)C47—H47A0.9600
C4—C51.428 (6)C47—H47B0.9600
C5—C61.351 (7)C47—H47C0.9600
C5—H50.9300S48—O501.434 (3)
C6—H60.9300S48—O491.449 (3)
C7—H7A0.9600S48—N511.617 (4)
C7—H7B0.9600N51—C531.478 (6)
C7—H7C0.9600N51—C521.482 (6)
S8—O101.430 (3)C52—H52A0.9600
S8—O91.440 (3)C52—H52B0.9600
S8—N111.622 (4)C52—H52C0.9600
N11—C121.463 (6)C53—H53A0.9600
N11—C131.473 (6)C53—H53B0.9600
C12—H12A0.9600C53—H53C0.9600
C12—H12B0.9600N54—C551.426 (6)
C12—H12C0.9600N54—H540.90 (6)
C13—H13A0.9600C55—C601.375 (6)
C13—H13B0.9600C55—C561.388 (6)
C13—H13C0.9600C56—C571.387 (6)
N14—C151.436 (6)C56—H560.9300
N14—H140.89 (6)C57—C581.383 (6)
C15—C161.380 (6)C57—H570.9300
C15—C201.378 (6)C58—O611.375 (5)
C16—C171.385 (6)C58—C591.407 (6)
C16—H160.9300C59—C601.401 (6)
C17—C181.382 (6)C59—C631.504 (6)
C17—H170.9300C60—H600.9300
C18—O211.369 (5)O61—C621.433 (5)
C18—C191.414 (6)C62—H62A0.9600
C19—C201.396 (6)C62—H62B0.9600
C19—C231.509 (6)C62—H62C0.9600
C20—H200.9300C63—N641.526 (6)
O21—C221.429 (5)C63—H63A0.9700
C22—H22A0.9600C63—H63B0.9700
C22—H22B0.9600N64—C691.493 (6)
C22—H22C0.9600N64—C671.513 (6)
C23—N241.528 (6)N64—C651.534 (5)
C23—H23A0.9700C65—C661.511 (6)
C23—H23B0.9700C65—H65A0.9700
N24—C291.505 (6)C65—H65B0.9700
N24—C271.522 (6)C66—H66A0.9600
N24—C251.523 (5)C66—H66B0.9600
C25—C261.510 (7)C66—H66C0.9600
C25—H25A0.9700C67—C681.529 (6)
C25—H25B0.9700C67—H67A0.9700
C26—H26A0.9600C67—H67B0.9700
C26—H26B0.9600C68—H68A0.9600
C26—H26C0.9600C68—H68B0.9600
C27—C281.514 (7)C68—H68C0.9600
C27—H27A0.9700C69—H69A0.9600
C27—H27B0.9700C69—H69B0.9600
C28—H28A0.9600C69—H69C0.9600
H1WA—O1W—H1WB112 (4)H29A—C29—H29C109.5
H2WA—O2W—H2WB113 (5)H29B—C29—H29C109.5
H3WA—O3W—H3WB111 (4)C46—N41—C42119.0 (4)
H4WA—O4W—H4WB111 (4)C46—N41—C47121.3 (4)
H5WA—O5W—H5WB113 (5)C42—N41—C47119.6 (3)
C2—N1—C6118.4 (4)C43—C42—N41121.6 (4)
C2—N1—C7121.3 (4)C43—C42—H42119.2
C6—N1—C7120.3 (4)N41—C42—H42119.2
N1—C2—C3122.2 (4)C42—C43—C44121.0 (4)
N1—C2—H2118.9C42—C43—H43119.5
C3—C2—H2118.9C44—C43—H43119.5
C2—C3—C4120.7 (4)N54—C44—C43121.6 (4)
C2—C3—S8115.0 (3)N54—C44—C45123.0 (4)
C4—C3—S8124.2 (3)C43—C44—C45115.4 (4)
N14—C4—C5122.1 (4)C46—C45—C44120.4 (4)
N14—C4—C3123.0 (4)C46—C45—S48115.1 (3)
C5—C4—C3114.9 (4)C44—C45—S48124.1 (3)
C6—C5—C4120.7 (4)N41—C46—C45122.4 (4)
C6—C5—H5119.7N41—C46—H46118.8
C4—C5—H5119.7C45—C46—H46118.8
C5—C6—N1122.4 (4)N41—C47—H47A109.5
C5—C6—H6118.8N41—C47—H47B109.5
N1—C6—H6118.8H47A—C47—H47B109.5
N1—C7—H7A109.5N41—C47—H47C109.5
N1—C7—H7B109.5H47A—C47—H47C109.5
H7A—C7—H7B109.5H47B—C47—H47C109.5
N1—C7—H7C109.5O50—S48—O49119.00 (19)
H7A—C7—H7C109.5O50—S48—N51107.7 (2)
H7B—C7—H7C109.5O49—S48—N51107.2 (2)
O10—S8—O9119.4 (2)O50—S48—C45107.9 (2)
O10—S8—N11107.1 (2)O49—S48—C45107.1 (2)
O9—S8—N11107.6 (2)N51—S48—C45107.4 (2)
O10—S8—C3107.0 (2)C53—N51—C52113.4 (4)
O9—S8—C3107.0 (2)C53—N51—S48116.5 (3)
N11—S8—C3108.3 (2)C52—N51—S48117.6 (3)
C12—N11—C13113.2 (4)N51—C52—H52A109.5
C12—N11—S8117.3 (4)N51—C52—H52B109.5
C13—N11—S8116.3 (3)H52A—C52—H52B109.5
N11—C12—H12A109.5N51—C52—H52C109.5
N11—C12—H12B109.5H52A—C52—H52C109.5
H12A—C12—H12B109.5H52B—C52—H52C109.5
N11—C12—H12C109.5N51—C53—H53A109.5
H12A—C12—H12C109.5N51—C53—H53B109.5
H12B—C12—H12C109.5H53A—C53—H53B109.5
N11—C13—H13A109.5N51—C53—H53C109.5
N11—C13—H13B109.5H53A—C53—H53C109.5
H13A—C13—H13B109.5H53B—C53—H53C109.5
N11—C13—H13C109.5C44—N54—C55124.6 (4)
H13A—C13—H13C109.5C44—N54—H54119 (3)
H13B—C13—H13C109.5C55—N54—H54116 (3)
C4—N14—C15125.7 (4)C60—C55—C56120.1 (4)
C4—N14—H14110 (3)C60—C55—N54120.4 (4)
C15—N14—H14124 (3)C56—C55—N54119.5 (4)
C16—C15—C20120.5 (4)C55—C56—C57120.5 (4)
C16—C15—N14121.1 (4)C55—C56—H56119.8
C20—C15—N14118.4 (4)C57—C56—H56119.8
C15—C16—C17119.8 (4)C58—C57—C56119.4 (4)
C15—C16—H16120.1C58—C57—H57120.3
C17—C16—H16120.1C56—C57—H57120.3
C16—C17—C18120.3 (4)O61—C58—C57123.2 (4)
C16—C17—H17119.8O61—C58—C59115.8 (4)
C18—C17—H17119.8C57—C58—C59120.9 (4)
O21—C18—C17123.9 (4)C60—C59—C58118.2 (4)
O21—C18—C19115.8 (4)C60—C59—C63121.4 (4)
C17—C18—C19120.3 (4)C58—C59—C63120.3 (4)
C20—C19—C18118.0 (4)C55—C60—C59120.9 (4)
C20—C19—C23120.0 (4)C55—C60—H60119.6
C18—C19—C23121.8 (4)C59—C60—H60119.6
C15—C20—C19120.9 (4)C58—O61—C62116.7 (4)
C15—C20—H20119.5O61—C62—H62A109.5
C19—C20—H20119.5O61—C62—H62B109.5
C18—O21—C22116.3 (4)H62A—C62—H62B109.5
O21—C22—H22A109.5O61—C62—H62C109.5
O21—C22—H22B109.5H62A—C62—H62C109.5
H22A—C22—H22B109.5H62B—C62—H62C109.5
O21—C22—H22C109.5C59—C63—N64115.6 (4)
H22A—C22—H22C109.5C59—C63—H63A108.4
H22B—C22—H22C109.5N64—C63—H63A108.4
C19—C23—N24116.0 (4)C59—C63—H63B108.4
C19—C23—H23A108.3N64—C63—H63B108.4
N24—C23—H23A108.3H63A—C63—H63B107.4
C19—C23—H23B108.3C69—N64—C67110.6 (4)
N24—C23—H23B108.3C69—N64—C63107.3 (4)
H23A—C23—H23B107.4C67—N64—C63112.2 (3)
C29—N24—C27110.4 (4)C69—N64—C65109.5 (4)
C29—N24—C25111.2 (4)C67—N64—C65108.2 (3)
C27—N24—C25108.3 (3)C63—N64—C65109.1 (3)
C29—N24—C23106.6 (3)C66—C65—N64116.0 (4)
C27—N24—C23109.3 (3)C66—C65—H65A108.3
C25—N24—C23111.0 (3)N64—C65—H65A108.3
C26—C25—N24113.8 (4)C66—C65—H65B108.3
C26—C25—H25A108.8N64—C65—H65B108.3
N24—C25—H25A108.8H65A—C65—H65B107.4
C26—C25—H25B108.8C65—C66—H66A109.5
N24—C25—H25B108.8C65—C66—H66B109.5
H25A—C25—H25B107.7H66A—C66—H66B109.5
C25—C26—H26A109.5C65—C66—H66C109.5
C25—C26—H26B109.5H66A—C66—H66C109.5
H26A—C26—H26B109.5H66B—C66—H66C109.5
C25—C26—H26C109.5N64—C67—C68114.7 (4)
H26A—C26—H26C109.5N64—C67—H67A108.6
H26B—C26—H26C109.5C68—C67—H67A108.6
C28—C27—N24115.0 (4)N64—C67—H67B108.6
C28—C27—H27A108.5C68—C67—H67B108.6
N24—C27—H27A108.5H67A—C67—H67B107.6
C28—C27—H27B108.5C67—C68—H68A109.5
N24—C27—H27B108.5C67—C68—H68B109.5
H27A—C27—H27B107.5H68A—C68—H68B109.5
C27—C28—H28A109.5C67—C68—H68C109.5
C27—C28—H28B109.5H68A—C68—H68C109.5
H28A—C28—H28B109.5H68B—C68—H68C109.5
C27—C28—H28C109.5N64—C69—H69A109.5
H28A—C28—H28C109.5N64—C69—H69B109.5
H28B—C28—H28C109.5H69A—C69—H69B109.5
N24—C29—H29A109.5N64—C69—H69C109.5
N24—C29—H29B109.5H69A—C69—H69C109.5
H29A—C29—H29B109.5H69B—C69—H69C109.5
N24—C29—H29C109.5
C6—N1—C2—C34.1 (7)C46—N41—C42—C432.2 (7)
C7—N1—C2—C3173.6 (5)C47—N41—C42—C43174.4 (5)
N1—C2—C3—C41.9 (8)N41—C42—C43—C440.9 (7)
N1—C2—C3—S8178.1 (4)C42—C43—C44—N54176.9 (5)
C2—C3—C4—N14173.7 (5)C42—C43—C44—C453.6 (7)
S8—C3—C4—N142.2 (7)N54—C44—C45—C46177.1 (4)
C2—C3—C4—C58.0 (7)C43—C44—C45—C463.4 (7)
S8—C3—C4—C5176.2 (4)N54—C44—C45—S484.7 (7)
N14—C4—C5—C6173.1 (5)C43—C44—C45—S48175.7 (3)
C3—C4—C5—C68.5 (7)C42—N41—C46—C452.4 (7)
C4—C5—C6—N13.1 (8)C47—N41—C46—C45174.2 (5)
C2—N1—C6—C53.5 (7)C44—C45—C46—N410.5 (7)
C7—N1—C6—C5174.2 (5)S48—C45—C46—N41173.5 (4)
C2—C3—S8—O1041.5 (4)C46—C45—S48—O5035.4 (4)
C4—C3—S8—O10142.5 (4)C44—C45—S48—O50151.9 (4)
C2—C3—S8—O9170.5 (4)C46—C45—S48—O49164.7 (4)
C4—C3—S8—O913.4 (5)C44—C45—S48—O4922.6 (5)
C2—C3—S8—N1173.7 (4)C46—C45—S48—N5180.4 (4)
C4—C3—S8—N11102.4 (4)C44—C45—S48—N5192.3 (4)
O10—S8—N11—C12171.9 (3)O50—S48—N51—C53177.9 (3)
O9—S8—N11—C1242.4 (4)O49—S48—N51—C5348.7 (4)
C3—S8—N11—C1273.1 (4)C45—S48—N51—C5366.1 (4)
O10—S8—N11—C1349.7 (4)O50—S48—N51—C5242.5 (4)
O9—S8—N11—C13179.2 (3)O49—S48—N51—C52171.7 (3)
C3—S8—N11—C1365.4 (4)C45—S48—N51—C5273.4 (4)
C5—C4—N14—C157.9 (7)C43—C44—N54—C5514.1 (7)
C3—C4—N14—C15173.8 (4)C45—C44—N54—C55166.3 (4)
C4—N14—C15—C1647.5 (7)C44—N54—C55—C60132.6 (5)
C4—N14—C15—C20135.6 (5)C44—N54—C55—C5650.3 (6)
C20—C15—C16—C173.1 (7)C60—C55—C56—C570.9 (7)
N14—C15—C16—C17180.0 (4)N54—C55—C56—C57178.0 (4)
C15—C16—C17—C180.1 (7)C55—C56—C57—C580.1 (6)
C16—C17—C18—O21179.3 (4)C56—C57—C58—O61179.3 (4)
C16—C17—C18—C192.7 (7)C56—C57—C58—C590.0 (6)
O21—C18—C19—C20179.5 (4)O61—C58—C59—C60178.8 (4)
C17—C18—C19—C202.4 (7)C57—C58—C59—C600.6 (6)
O21—C18—C19—C234.4 (6)O61—C58—C59—C632.7 (6)
C17—C18—C19—C23173.7 (4)C57—C58—C59—C63176.7 (4)
C16—C15—C20—C193.4 (7)C56—C55—C60—C591.5 (7)
N14—C15—C20—C19179.6 (4)N54—C55—C60—C59178.6 (4)
C18—C19—C20—C150.7 (7)C58—C59—C60—C551.3 (6)
C23—C19—C20—C15176.8 (4)C63—C59—C60—C55177.4 (4)
C17—C18—O21—C2210.8 (6)C57—C58—O61—C6224.1 (6)
C19—C18—O21—C22171.1 (4)C59—C58—O61—C62156.6 (4)
C20—C19—C23—N2488.3 (5)C60—C59—C63—N6490.8 (5)
C18—C19—C23—N2495.7 (5)C58—C59—C63—N6493.3 (5)
C19—C23—N24—C29170.2 (4)C59—C63—N64—C69175.4 (4)
C19—C23—N24—C2750.9 (5)C59—C63—N64—C6763.0 (5)
C19—C23—N24—C2568.5 (5)C59—C63—N64—C6556.9 (5)
C29—N24—C25—C2648.6 (5)C69—N64—C65—C6661.7 (5)
C27—N24—C25—C26170.1 (4)C67—N64—C65—C6658.9 (5)
C23—N24—C25—C2669.9 (5)C63—N64—C65—C66178.8 (4)
C29—N24—C27—C2851.8 (5)C69—N64—C67—C6856.0 (5)
C25—N24—C27—C2870.2 (5)C63—N64—C67—C6863.7 (5)
C23—N24—C27—C28168.7 (4)C65—N64—C67—C68175.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···I40.91 (3)2.60 (4)3.489 (4)170 (3)
O1W—H1WB···I20.90 (2)2.66 (2)3.561 (4)176 (4)
O2W—H2WA···O5wi0.90 (4)1.98 (5)2.799 (7)147 (5)
O2W—H2WB···I30.90 (4)2.69 (4)3.580 (5)175 (4)
O3W—H3WA···O1Wi0.90 (4)1.91 (4)2.781 (6)161 (18)
O3W—H3WB···I10.90 (4)2.64 (4)3.544 (4)178 (5)
O4W—H4WA···I40.90 (3)2.75 (3)3.613 (5)160 (4)
O4W—H4WB···O3Wii0.89 (5)1.92 (4)2.795 (7)162 (2)
O5W—H5WA···I20.90 (4)2.75 (5)3.614 (5)165 (4)
O5W—H5WB···O4wiii0.90 (4)1.94 (4)2.809 (7)161 (3)
N14—H14···O90.90 (3)1.93 (4)2.733 (5)149 (4)
N54—H54···O490.90 (5)2.08 (4)2.767 (5)133 (4)
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula2C21H34N4O3S2+·4I·5H2O
Mr1442.86
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)12.7930 (5), 13.5539 (6), 16.8386 (7)
α, β, γ (°)96.670 (2), 97.667 (2), 98.224 (1)
V3)2836.5 (2)
Z2
Radiation typeMo Kα
µ (mm1)2.33
Crystal size (mm)0.35 × 0.2 × 0.08
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.575, 0.830
No. of measured, independent and
observed [I > 2σ(I)] reflections
49577, 11468, 8753
Rint0.050
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.116, 1.00
No. of reflections11468
No. of parameters654
No. of restraints17
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)2.07, 1.42

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···I40.91 (3)2.60 (4)3.489 (4)170 (3)
O1W—H1WB···I20.90 (2)2.663 (17)3.561 (4)176 (4)
O2W—H2WA···O5wi0.90 (4)1.98 (5)2.799 (7)147 (5)
O2W—H2WB···I30.90 (4)2.69 (4)3.580 (5)175 (4)
O3W—H3WA···O1Wi0.90 (4)1.91 (4)2.781 (6)161 (18)
O3W—H3WB···I10.90 (4)2.64 (4)3.544 (4)178 (5)
O4W—H4WA···I40.90 (3)2.75 (3)3.613 (5)160 (4)
O4W—H4WB···O3Wii0.89 (5)1.92 (4)2.795 (7)162 (2)
O5W—H5WA···I20.90 (4)2.75 (5)3.614 (5)165 (4)
O5W—H5WB···O4wiii0.90 (4)1.94 (4)2.809 (7)161 (3)
N14—H14···O90.90 (3)1.93 (4)2.733 (5)149 (4)
N54—H54···O490.90 (5)2.08 (4)2.767 (5)133 (4)
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y, z.
 

Acknowledgements

Intensity measurements were performed at the Unidade de Raios X, RIAIDT, University of Santiago de Compostela, SPAIN. This work was supported by Fundação para a Ciência e Tecnologia (FCT, Portugal); TR acknowledges the FCT for the PhD grant SFRH/BD/30689/2006.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals
First citationBjorkman, A. & Bhattarai, A. (2005). Acta Trop. 94, 163–169.  Web of Science PubMed
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDjedouani, A., Boufas, S., Allain, M., Bouet, G. & Khan, M. (2008). Acta Cryst. E64, o1785.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals
First citationLopes, F., Capela, R., Gonçalves, J. O., Horton, P. N., Hursthouse, M. B., Iley, J., Casimiro, C. M., Bom, J. & Moreira, R. (2004). Tetrahedron Lett. 45, 7663–7666.  Web of Science CSD CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWang, Y., Zhang, J., Chen, H. & Luo, S. (2008). Acta Cryst. E64, o1025.  Web of Science CSD CrossRef IUCr Journals
First citationYeates, C. L., Batchelor, J. F., Capon, E. C., Cheesman, N. J., Fry, M., Hudson, A. T., Pudney, M., Trimming, H., Woolven, J., Bueno, J. M., Chicharro, J., Fernández, E., Fiandor, J. M., Gargallo-Viola, D., de las Heras, F. G., Herreros, E. & León, M. L. (2008). J. Med. Chem. 51, 2845–2852.  Web of Science CrossRef PubMed CAS

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 2| February 2009| Pages o283-o284
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds