Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
cross.png
share
Previous article cross.png
Next article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
cross.png
share
Next article cross.png

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 61| Part 8| August 2005| Pages m1509-m1511
https://doi.org/10.1107/S1600536805021628

N—H⋯S and N—H⋯O hydrogen bonding in tetra-n-butyl­ammonium (imidazolidine-2-thione-2κS)dioxo-1κ2O-di-μ-sulfido-1:2κ4S:S-copper(I)tungstate(VI)

CROSSMARK_Color_square_no_text.svg
Azizolla Beheshti,a* William Clegg,b* Sophie H. Daleb and Ahmad Solimankhania

aDepartment of Chemistry, Faculty of Science, Shahid Chamran University, Ahvaz, Iran, and bSchool of Natural Sciences (Chemistry), University of Newcastle upon Tyne, Newcastle upon Tyne NE1 7RU, England
*Correspondence e-mail: beheshti_a@hotmail.com, w.clegg@ncl.ac.uk

(Received 5 July 2005; accepted 6 July 2005; online 9 July 2005)

In the title complex, (C16H36N)[WCuO2S2(C3H6N2S)], the W and Cu atoms have tetra­hedral and trigonal-planar coordination, respectively. Two sulfide ligands bridge the two metal centres; tungsten is additionally coordinated by two terminal oxo ligands and copper by the exocyclic S atom of imidazolidine-2-thione. There is an intra­molecular N—H⋯S hydrogen bond in the anion, and anions are linked into chains by N—H⋯O inter­molecular hydrogen bonds. The more loosely held cation is disordered.

Comment

The formation of hydrogen bonds, including intra­molecular N—H⋯S hydrogen bonds, in many biological macromolecules such as azurin and rubredoxin, has been confirmed by X-ray crystallography, vibrational and NMR spectroscopic studies (Houseman et al., 1992[Houseman, A. L. P., Oh, B. H., Kennedy, M. C., Fan, C., Werst, M. M., Beinert, H., Markley, J. L. & Hoffman, B. M. (1992). Biochemistry, 31, 2073-2080.]; Adman, 1991[Adman, E. T. (1991). Adv. Protein Chem. 42, 145-197.]; Backes et al., 1991[Backes, G., Mino, Y., Loehr, T. M., Meyer, T. E., Cusanovich, M. A., Sweeney, W. V., Adman, E. T. & Sanders-Loehr, J. (1991). J. Am. Chem. Soc. 113, 2055-2064.]; Blake et al., 1992[Blake, P. R., Park, J. B., Adams, M. W. W. & Summers, M. F. (1992). J. Am. Chem. Soc. 114, 4931-4933.]; Watenpaugh et al., 1979[Watenpaugh, K. D., Sieker, L. C. & Jensen, L. H. (1979). J. Mol. Biol. 131, 509-522.]; Tsukihara et al., 1981[Tsukihara, T., Fukuyama, K., Nakamura, M., Katsube, Y., Tanaka, N., Kakudo, M., Wada, K., Hase, T. & Matsubara, H. (1981). J. Biochem. 90, 1763-1773.]; Adman et al., 1975[Adman, E., Watenpaugh, K. D. & Jensen, L. H. (1975). Proc. Natl Acad. Sci. USA, 72, 4854-4858.]; Baker, 1988[Baker, E. N. (1988). J. Mol. Biol. 203, 1071-1095.]). We present here a copper(I) complex, (I)[link], with two kinds of hydrogen bonds, namely intra­molecular N—H⋯S and inter­molecular N—H⋯O.

[Scheme 1]

The structure of the bimetallic anion is shown in Fig. 1[link] and selected geometric parameters are given in Table 1[link]. The disordered cation is geometrically unexceptional. In the [O2WS2Cu(Imt)]− anion (Imt is imidazolidine-2-thione), the coordination environments of tungsten(VI) and copper(I) are slightly distorted tetra­hedral and rather more strongly distorted trigonal planar, respectively. The angular deviations around the Cu atom may be attributed to steric effects and the constraints of the WS2Cu four-membered ring. Copper is coordinated by two bridging S and a terminal, monodentate S-donating Imt ligand. The bridging angles at S are the smallest angles in the complex and are only slightly larger than the value required for regular edge-sharing tetra­hedra (70.5°; Summerville & Hoffman, 1976[Summerville, R. H. & Hoffman, R. (1976). J. Am. Chem. Soc. 98, 7240-7254.]). Narrowing of the bridging angle is inevitably accompanied by a reduction in the W⋯Cu separation distance, which is not, however, considered as indicating a direct metal-metal bond. The Cu—S1 distance and Cu—S—C angle are typical of terminal monodentate S-donating thio­nes attached to trigonal planar Cu(I) (Beheshti et al., 2004[Beheshti, A., Brooks, N. R., Clegg, W. & Khorrmdin, R. (2004). Acta Cryst. E60, m1923-m1926.]). In common with other thione complexes, a slight lengthening of the S—C distance occurs, relative to that of the C=S bond length in the free Imt ligand, due to a reduction in the π-bond character of the thione linkage accompanying metal-thione coordination. The Cu—S2 and Cu—S3 distances are in the range [2.168 (9)–2.340 (9) Å] reported for (Et4N)[WO2S2Cu(Hmimt)], where Hmimt is the closely related ligand 1-methyl­imidazole-2(3H)-thione (Beheshti et al., 2004[Beheshti, A., Brooks, N. R., Clegg, W. & Khorrmdin, R. (2004). Acta Cryst. E60, m1923-m1926.]).

Although there are many crystallographically characterized examples of complexes in which CuI is bonded across S⋯S edges of [WS4]2− and [OWS3]2− tetra­hedra, the title complex appears to be only the third case for [O2WS2]2−, the others being the closely related Cu(Hmimt) complex mentioned above (Beheshti et al., 2004[Beheshti, A., Brooks, N. R., Clegg, W. & Khorrmdin, R. (2004). Acta Cryst. E60, m1923-m1926.]) and a CuPPh3 complex (Beheshti et al., 2001[Beheshti, A., Clegg, W. & Fallah, H. (2001). Inorg. Chim. Acta, 322, 1-6.]).

The striking feature of the structure of the anion is the orientation of the thione ligand; this brings one NH group of the heterocyclic ligand into a position close to one bridging sulfur atom of the WO2S2 group, with the formation of an intra­molecular N—H⋯S hydrogen bond (Fig.1 and Table 2[link]). In addition to the intra­molecular N—H⋯S hydrogen bond, the second NH group of Imt forms an inter­molecular hydrogen bond with an oxo ligand attached to tungsten in a neighbouring anion (Fig. 2[link] and Table 2[link]). This hydrogen bond generates a chain of anions. Such hydrogen bonds have been found to play important roles in regulating the properties of metal-sulfur proteins as well as their model complexes (Houseman et al., 1992[Houseman, A. L. P., Oh, B. H., Kennedy, M. C., Fan, C., Werst, M. M., Beinert, H., Markley, J. L. & Hoffman, B. M. (1992). Biochemistry, 31, 2073-2080.]; Sun et al., 1993[Sun, W.-Y., Ueyama, N. & Nakamura, A. (1993). Inorg. Chem. 32, 1095-1100.]).

In the solid state, infrared spectroscopy may also be used to probe the mode of coordination of Imt and [WO2S2]2− ligands. Uncoordinated Imt exhibits N—H stretching and C=S bands at 3200 and 510 cm−1, respectively. The corresponding N—H and C=S vibration bands were observed at 3308 and 500 cm−1 for the complex. The shifts of ν(N—H) (108 cm−1 upwards) and ν(C=S) (10 cm−1 downwards) and the absence of a ν(S—H) band at 2500 cm−1 clearly indicate that the Imt ligand is coordinated only via the thione sulfur in the complex. The W=O stretching frequencies of the [WO2S2]2− ligand in the complex (918 and 867 cm−1) are shifted to higher values than for the free [WO2S2]2− anion (850 and 795 cm−1 in the ammonium salt; McDonald et al., 1983[McDonald, J. W., Friesen, G. D., Rosenhein, L. D. & Newton, W. E. (1983). Inorg. Chim. Acta, 72, 205-210.]); this indicates that the [WO2S2]2− ligand is coordinated through its sulfur atoms. The band at 437 cm−1 is assigned to the bridging W—S bonds. Thus, the infrared spectroscopic results are consistent with the X-ray structural analysis.

[Figure 1]
Figure 1
The structure of the anion with atom labels and 50% probability displacement ellipsoids for non-H atoms. The intra­molecular hydrogen bond is shown as a dashed line.
[Figure 2]
Figure 2
A section of the packing, viewed along the a axis. Hydrogen bonds are shown as dashed lines, and other H atoms have been omitted, together with minor disorder components.

Experimental

(NH4)2[WO2S2] (0.316 g, 1.0 mmol) was dissolved in acetone (40 ml) and solid (n-Bu4N)Br (0.676 g, 2.1 mmol) was added. The mixture was stirred at room temperature for 5 min. CuCl (0.099 g, 1 mmol) was added and the mixture was stirred for 1 h. Imt (0.112 g, 1.1 mmol) was added and the mixture was stirred at room temperature for 4 h and then filtered. The filtrate was evaporated under vacuum. The oily residue was dissolved in dichloro­methane (25 ml) and the solution filtered to remove any insoluble material. The filtrate was evaporated to dryness under vacuum. The residue was washed with distilled water (2 × 2 ml), 2-propanol (2 × 2 ml) and dieth­yl ether (2 × 5 ml) and dried in vacuo to give a pale-brown powder. The yield at this stage was 0.43 g (46%). Crystals were obtained by diffusing dieth­yl ether into a saturated solution in acetone. On leaving the solution to stand in a refrigerator overnight, air-stable orange crystals were deposited, which are soluble in common organic solvents. 1H NMR (DMSO-d6, 300 K): δ 8.38 (s, N—H), 3.68 (s, CH2); 13C NMR (DMSO-d6, 300 K): δ 180.23 (C1), 45.41 (C2 and C3) (using the atom numbering of Fig. 1[link]). In the 1H NMR spectrum of the complex, the ligand signals are shifted down-field from their positions in the spectrum of the free ligand (N—H,7.94 and CH2 3.505 p.p.m.), but in the 13C NMR spectrum of the complex, the C=S signal is shifted up-field from its position in the spectrum of the free ligand (183.35 p.p.m.), due to the reduction of the C=S bond order upon coord­ination and a shift of electron density producing partial double bond character in the C—N bond. These observations indicate that, in DMSO-d6, the ligand remains coordinated to the metal.

Crystal data

  • (C16H36N)[WCuO2S2(C3H6N2S)]

  • Mr = 688.13

  • Monoclinic, P 21 /c

  • a = 10.6925 (16) Å

  • b = 14.875 (2) Å

  • c = 17.2342 (8) Å

  • β = 94.742 (7)°

  • V = 2731.7 (6) Å3

  • Z = 4

  • Dx = 1.673 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 227 reflections

  • θ = 2.5–27.5°

  • μ = 5.23 mm−1

  • T = 150 (2) K

  • Block, orange

  • 0.77 × 0.43 × 0.31 mm
Data collection

  • Nonius KappaCCD diffractometer

  • φ and ω scans

  • Absorption correction: numerical(SHELXTL; Sheldrick, 2001[Sheldrick, G. M. (2001). SHELXTL. Version 5. Bruker AXS Inc., Madison, Wisconsin, USA.])Tmin = 0.100, Tmax = 0.239

  • 28801 measured reflections

  • 6215 independent reflections

  • 4881 reflections with I > 2σ(I)

  • Rint = 0.055

  • θmax = 27.5°

  • h = −13 → 13

  • k = −19 → 18

  • l = −22 → 18
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.074

  • S = 1.07

  • 6215 reflections

  • 378 parameters

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

  • w = 1/[σ2(Fo2) + (0.0159P)2 + 6.5317P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.029

  • Δρmax = 0.94 e Å−3

  • Δρmin = −0.96 e Å−3

  • Extinction correction: SHELXTL

  • Extinction coefficient: 0.00053 (11)

Table 1
Selected geometric parameters (Å, °)[link]

W—Cu 2.6755 (6)
W—O1 1.731 (4)
W—O2 1.750 (3)
W—S2 2.2652 (13)
W—S3 2.2670 (13)
Cu—S1 2.2047 (13)
Cu—S2 2.2385 (14)
Cu—S3 2.2459 (14)
S1—C1 1.711 (5)
C1—N1 1.338 (6)
C1—N2 1.326 (6)
N1—C2 1.471 (6)
C2—C3 1.543 (7)
C3—N2 1.453 (6)
O1—W—O2 109.42 (18)
O1—W—S2 109.53 (14)
O1—W—S3 109.63 (15)
O2—W—S2 110.36 (13)
O2—W—S3 111.47 (13)
S2—W—S3 106.37 (5)
S1—Cu—S2 123.40 (5)
S1—Cu—S3 128.57 (5)
S2—Cu—S3 108.02 (5)
Cu—S1—C1 106.99 (16)
S1—C1—N1 126.8 (4)
S1—C1—N2 123.3 (3)
N1—C1—N2 109.9 (4)
C1—N1—C2 111.5 (4)
N1—C2—C3 101.2 (4)
C2—C3—N2 102.5 (4)
C1—N2—C3 112.0 (4)
W—S2—Cu 72.89 (4)
W—S3—Cu 72.72 (4)

Table 2
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯S3 0.87 (1) 2.66 (2) 3.490 (4) 160 (5)
N2—H2⋯O2i 0.87 (1) 1.87 (1) 2.729 (5) 174 (5)
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

The cation is disordered. Most C atoms could be resolved into two components with sensible connectivities. Separate occupancy factors were refined for the components of each n-but­yl group, giving values of 0.747 (9), 0.660 (12), 0.690 (9) and 0.817 (10) for the major sites; similarity restraints were applied to the displacement parameters and bond lengths. The remaining C atoms may also be disordered, to a smaller extent, but this could not be resolved. H atoms bonded to N were located in a difference map and refined with a restrained N—H distance of 0.87 (2) Å, and with Uiso(H) = 1.2Ueq(N). Other H atoms were positioned geometrically and refined with a riding model, with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.2 (1.5 for meth­yl groups) times Ueq(C).

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX (Duisenberg, 1992[Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2001[Sheldrick, G. M. (2001). SHELXTL. Version 5. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536805021628/bt6695sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805021628/bt6695Isup2.hkl


Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

tetra-n-butylammonium (imidazolidine-2-thione-2κS)dioxo-1κ2O-di-µ-sulfido-1:2κ4S:S- copper(I)tungstate(VI) top
Crystal data top
(C16H36N)[WCuO2S2(C3H6N2S)]F(000) = 1376
Mr = 688.13Dx = 1.673 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.6925 (16) ÅCell parameters from 227 reflections
b = 14.875 (2) Åθ = 2.5–27.5°
c = 17.2342 (8) ŵ = 5.23 mm−1
β = 94.742 (7)°T = 150 K
V = 2731.7 (6) Å3Block, orange
Z = 40.77 × 0.43 × 0.31 mm
Data collection top
Nonius KappaCCD
diffractometer		6215 independent reflections
Radiation source: sealed tube4881 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
φ and ω scansθmax = 27.5°, θmin = 4.0°
Absorption correction: numerical
(SHELXTL; Sheldrick, 2001)		h = −13→13
Tmin = 0.100, Tmax = 0.239k = −19→18
28801 measured reflectionsl = −22→18
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.0159P)2 + 6.5317P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.029
6215 reflectionsΔρmax = 0.94 e Å−3
378 parametersΔρmin = −0.96 e Å−3
623 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00053 (11)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
W0.713367 (17)0.642794 (12)0.184549 (11)0.03394 (7)
Cu0.85205 (5)0.50990 (4)0.25158 (3)0.03535 (14)
S10.96624 (11)0.39730 (8)0.30142 (7)0.0405 (3)
C11.0637 (4)0.4403 (3)0.3761 (3)0.0342 (10)
N11.0582 (4)0.5224 (3)0.4072 (2)0.0439 (10)
H11.016 (4)0.563 (3)0.380 (3)0.053*
C21.1657 (5)0.5394 (3)0.4642 (3)0.0469 (12)
H2A1.13880.56650.51260.056*
H2B1.22870.57890.44240.056*
C31.2168 (5)0.4433 (3)0.4784 (3)0.0458 (12)
H3A1.30930.44160.47800.055*
H3B1.19280.41900.52860.055*
N21.1563 (4)0.3938 (3)0.4130 (2)0.0416 (9)
H21.176 (5)0.3388 (14)0.402 (3)0.050*
O10.5557 (4)0.6585 (3)0.1964 (3)0.0608 (11)
O20.7641 (4)0.7254 (2)0.1219 (2)0.0548 (9)
S20.74285 (13)0.50400 (9)0.13514 (8)0.0479 (3)
S30.82482 (15)0.64692 (9)0.30226 (8)0.0535 (3)
N30.2927 (3)0.4345 (2)0.1444 (2)0.0425 (8)
C40.3881 (5)0.4170 (4)0.0858 (3)0.0557 (12)
H4A0.35390.44040.03460.067*
H4B0.46500.45170.10170.067*
C50.4243 (6)0.3196 (4)0.0759 (4)0.0765 (17)
H5A0.35230.28380.05310.092*0.747 (9)
H5B0.45590.29260.12630.092*0.747 (9)
H5C0.34520.28810.08490.092*0.253 (9)
H5D0.47990.30870.12380.092*0.253 (9)
C60.5292 (7)0.3255 (6)0.0195 (5)0.067 (2)0.747 (9)
H6A0.49760.3566−0.02900.081*0.747 (9)
H6B0.60130.36000.04390.081*0.747 (9)
C70.5704 (10)0.2307 (7)0.0010 (6)0.093 (3)0.747 (9)
H7A0.61260.20340.04790.139*0.747 (9)
H7B0.62840.2328−0.04010.139*0.747 (9)
H7C0.49670.1947−0.01670.139*0.747 (9)
C6X0.4808 (19)0.2572 (16)0.0178 (14)0.073 (3)0.253 (9)
H6C0.49200.19550.03880.088*0.253 (9)
H6D0.42830.2550−0.03230.088*0.253 (9)
C7X0.606 (2)0.302 (2)0.0086 (18)0.083 (5)0.253 (9)
H7D0.59260.3656−0.00500.124*0.253 (9)
H7E0.64800.2721−0.03280.124*0.253 (9)
H7F0.65920.29790.05760.124*0.253 (9)
C80.3408 (5)0.4008 (4)0.2244 (3)0.0495 (11)
H8A0.27170.40480.25910.059*0.660 (12)
H8B0.36310.33650.22010.059*0.660 (12)
H8C0.32870.33490.22630.059*0.340 (12)
H8D0.28970.42810.26360.059*0.340 (12)
C90.4529 (10)0.4502 (7)0.2623 (5)0.065 (2)0.660 (12)
H9A0.43240.51430.26990.078*0.660 (12)
H9B0.52450.44640.22950.078*0.660 (12)
C100.4848 (10)0.4045 (7)0.3401 (5)0.062 (2)0.660 (12)
H10A0.41090.40630.37110.075*0.660 (12)
H10B0.50610.34070.33150.075*0.660 (12)
C110.5946 (11)0.4507 (9)0.3848 (6)0.086 (4)0.660 (12)
H11A0.67330.42520.36930.129*0.660 (12)
H11B0.58950.44160.44070.129*0.660 (12)
H11C0.59200.51520.37320.129*0.660 (12)
C9X0.4797 (10)0.4220 (17)0.2469 (11)0.064 (3)0.340 (12)
H9C0.52910.38350.21380.076*0.340 (12)
H9D0.49360.48490.23080.076*0.340 (12)
C10X0.539 (2)0.4127 (14)0.3300 (9)0.069 (3)0.340 (12)
H10C0.51050.35610.35280.083*0.340 (12)
H10D0.63160.40950.32920.083*0.340 (12)
C11X0.505 (3)0.4914 (14)0.3806 (11)0.080 (5)0.340 (12)
H11D0.54480.54640.36280.120*0.340 (12)
H11E0.53530.47950.43490.120*0.340 (12)
H11F0.41400.49910.37660.120*0.340 (12)
C120.1712 (4)0.3831 (3)0.1232 (3)0.0477 (11)
H12A0.10890.40100.15970.057*0.690 (9)
H12B0.18780.31810.13080.057*0.690 (9)
H12C0.12140.38500.16910.057*0.310 (9)
H12D0.19400.31940.11540.057*0.310 (9)
C130.1135 (7)0.3978 (8)0.0399 (5)0.063 (2)0.690 (9)
H13A0.16450.36660.00280.076*0.690 (9)
H13B0.11280.46280.02740.076*0.690 (9)
C14−0.0226 (7)0.3607 (5)0.0317 (7)0.068 (2)0.690 (9)
H14A−0.06640.37670.07830.081*0.690 (9)
H14B−0.06980.3870−0.01470.081*0.690 (9)
C15−0.0157 (10)0.2602 (5)0.0237 (7)0.077 (3)0.690 (9)
H15A0.04870.2447−0.01140.116*0.690 (9)
H15B−0.09720.23710.00230.116*0.690 (9)
H15C0.00610.23320.07490.116*0.690 (9)
C13X0.085 (2)0.4117 (13)0.0527 (11)0.065 (3)0.310 (9)
H13C0.13260.44420.01480.077*0.310 (9)
H13D0.01760.45170.06890.077*0.310 (9)
C14X0.0277 (18)0.3248 (14)0.0162 (12)0.069 (3)0.310 (9)
H14C−0.00660.3355−0.03820.082*0.310 (9)
H14D0.09170.27670.01650.082*0.310 (9)
C15X−0.0763 (18)0.2993 (16)0.0669 (13)0.076 (5)0.310 (9)
H15D−0.04100.29160.12080.114*0.310 (9)
H15E−0.11500.24280.04810.114*0.310 (9)
H15F−0.13980.34690.06460.114*0.310 (9)
C160.2708 (5)0.5361 (3)0.1449 (4)0.0576 (12)
H16A0.25420.55650.09030.069*0.817 (10)
H16B0.34920.56560.16630.069*0.817 (10)
H16C0.34960.56690.13410.069*0.183 (10)
H16D0.20650.55150.10230.069*0.183 (10)
C170.1630 (7)0.5687 (4)0.1912 (6)0.0682 (19)0.817 (10)
H17A0.08230.54880.16440.082*0.817 (10)
H17B0.17110.54040.24340.082*0.817 (10)
C180.1602 (8)0.6708 (4)0.2010 (5)0.070 (2)0.817 (10)
H18A0.17020.69900.14980.084*0.817 (10)
H18B0.07680.68840.21690.084*0.817 (10)
C190.2605 (7)0.7082 (6)0.2600 (5)0.064 (2)0.817 (10)
H19A0.24200.69020.31250.097*0.817 (10)
H19B0.26140.77390.25640.097*0.817 (10)
H19C0.34270.68440.24900.097*0.817 (10)
C17X0.228 (4)0.5713 (16)0.2212 (12)0.065 (3)0.183 (10)
H17C0.28420.55170.26680.078*0.183 (10)
H17D0.14040.55470.22860.078*0.183 (10)
C18X0.243 (4)0.6711 (17)0.203 (2)0.066 (3)0.183 (10)
H18C0.32970.68540.19200.079*0.183 (10)
H18D0.18430.68970.15870.079*0.183 (10)
C19X0.210 (4)0.716 (3)0.278 (2)0.069 (5)0.183 (10)
H19D0.13690.68600.29770.104*0.183 (10)
H19E0.18960.77950.26810.104*0.183 (10)
H19F0.28130.71190.31750.104*0.183 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
W0.03594 (11)0.02814 (10)0.03732 (12)−0.00322 (8)0.00050 (7)0.00084 (8)
Cu0.0374 (3)0.0294 (3)0.0387 (3)−0.0017 (2)−0.0002 (2)−0.0011 (2)
S10.0453 (7)0.0279 (6)0.0470 (7)−0.0012 (5)−0.0032 (5)−0.0037 (5)
C10.039 (2)0.029 (2)0.035 (2)0.0003 (18)0.0072 (19)0.0018 (19)
N10.050 (2)0.035 (2)0.044 (2)0.0071 (18)−0.0077 (19)−0.0027 (19)
C20.053 (3)0.040 (3)0.046 (3)−0.001 (2)−0.004 (2)−0.006 (2)
C30.049 (3)0.046 (3)0.042 (3)0.008 (2)−0.002 (2)−0.005 (2)
N20.046 (2)0.033 (2)0.044 (2)0.0052 (18)−0.0031 (19)−0.0035 (19)
O10.046 (2)0.051 (2)0.086 (3)0.0042 (17)0.009 (2)0.009 (2)
O20.067 (2)0.042 (2)0.056 (2)−0.0083 (18)0.0093 (18)0.0126 (18)
S20.0622 (8)0.0368 (7)0.0424 (7)0.0020 (6)−0.0098 (6)−0.0093 (6)
S30.0791 (9)0.0342 (6)0.0439 (7)0.0075 (6)−0.0151 (6)−0.0121 (6)
N30.0447 (19)0.0399 (19)0.044 (2)−0.0052 (16)0.0082 (14)0.0101 (17)
C40.044 (2)0.085 (3)0.039 (2)0.000 (2)0.007 (2)0.005 (3)
C50.063 (3)0.102 (4)0.065 (3)0.011 (3)0.007 (3)−0.028 (3)
C60.048 (4)0.086 (5)0.067 (4)0.002 (3)−0.002 (3)−0.030 (4)
C70.088 (6)0.101 (6)0.089 (6)0.020 (5)0.011 (5)−0.042 (6)
C6X0.056 (6)0.095 (6)0.068 (6)−0.001 (6)0.004 (6)−0.029 (6)
C7X0.073 (9)0.093 (11)0.086 (10)−0.015 (8)0.025 (8)−0.033 (10)
C80.072 (3)0.041 (3)0.037 (2)−0.010 (2)0.0070 (19)0.006 (2)
C90.090 (5)0.060 (5)0.042 (4)−0.023 (4)−0.007 (3)0.002 (3)
C100.075 (5)0.067 (5)0.043 (4)−0.028 (4)−0.004 (4)0.003 (3)
C110.085 (7)0.109 (8)0.060 (5)−0.041 (6)−0.020 (5)0.011 (6)
C9X0.087 (5)0.054 (6)0.047 (5)−0.019 (5)−0.014 (4)0.003 (5)
C10X0.091 (6)0.069 (6)0.046 (5)−0.025 (6)−0.009 (5)0.010 (5)
C11X0.099 (10)0.094 (9)0.047 (7)−0.025 (9)0.007 (8)0.000 (7)
C120.043 (2)0.033 (2)0.067 (3)−0.0051 (18)0.0109 (19)0.008 (2)
C130.044 (4)0.051 (4)0.090 (4)−0.003 (3)−0.015 (3)0.015 (4)
C140.045 (4)0.045 (4)0.110 (5)0.004 (3)−0.011 (4)0.003 (4)
C150.082 (6)0.046 (4)0.098 (7)0.001 (4)−0.031 (5)0.000 (5)
C13X0.048 (5)0.046 (5)0.096 (5)−0.004 (4)−0.012 (4)0.013 (5)
C14X0.051 (6)0.052 (6)0.101 (6)−0.001 (5)−0.013 (5)0.005 (5)
C15X0.060 (8)0.059 (9)0.107 (10)−0.013 (7)−0.010 (7)0.004 (9)
C160.055 (3)0.037 (2)0.082 (3)−0.008 (2)0.009 (2)0.014 (2)
C170.055 (4)0.039 (3)0.112 (5)−0.002 (3)0.017 (3)0.005 (3)
C180.055 (4)0.037 (3)0.119 (5)0.003 (3)0.010 (4)0.001 (3)
C190.064 (5)0.052 (4)0.079 (5)0.013 (4)0.017 (4)−0.003 (4)
C17X0.056 (6)0.039 (4)0.101 (6)0.001 (5)0.010 (5)0.001 (5)
C18X0.052 (7)0.041 (5)0.106 (7)−0.001 (7)0.012 (7)0.003 (5)
C19X0.062 (12)0.043 (8)0.102 (10)0.003 (11)0.006 (10)0.001 (8)
Geometric parameters (Å, º) top
W—Cu2.6755 (6)C11—H11C0.980
W—O11.731 (4)C9X—H9C0.990
W—O21.750 (3)C9X—H9D0.990
W—S22.2652 (13)C9X—C10X1.525 (8)
W—S32.2670 (13)C10X—H10C0.990
Cu—S12.2047 (13)C10X—H10D0.990
Cu—S22.2385 (14)C10X—C11X1.522 (8)
Cu—S32.2459 (14)C11X—H11D0.980
S1—C11.711 (5)C11X—H11E0.980
C1—N11.338 (6)C11X—H11F0.980
C1—N21.326 (6)C12—H12A0.990
N1—H10.868 (10)C12—H12B0.990
N1—C21.471 (6)C12—H12C0.990
C2—H2A0.990C12—H12D0.990
C2—H2B0.990C12—C131.531 (7)
C2—C31.543 (7)C12—C13X1.525 (8)
C3—H3A0.990C13—H13A0.990
C3—H3B0.990C13—H13B0.990
C3—N21.453 (6)C13—C141.552 (7)
N2—H20.867 (10)C14—H14A0.990
N3—C41.517 (5)C14—H14B0.990
N3—C81.516 (5)C14—C151.504 (7)
N3—C121.525 (5)C15—H15A0.980
N3—C161.530 (5)C15—H15B0.980
C4—H4A0.990C15—H15C0.980
C4—H4B0.990C13X—H13C0.990
C4—C51.513 (6)C13X—H13D0.990
C5—H5A0.990C13X—C14X1.541 (8)
C5—H5B0.990C14X—H14C0.990
C5—H5C0.990C14X—H14D0.990
C5—H5D0.990C14X—C15X1.518 (8)
C5—C61.547 (7)C15X—H15D0.980
C5—C6X1.527 (8)C15X—H15E0.980
C6—H6A0.990C15X—H15F0.980
C6—H6B0.990C16—H16A0.990
C6—C71.518 (7)C16—H16B0.990
C7—H7A0.980C16—H16C0.990
C7—H7B0.980C16—H16D0.990
C7—H7C0.980C16—C171.535 (6)
C6X—H6C0.990C16—C17X1.520 (8)
C6X—H6D0.990C17—H17A0.990
C6X—C7X1.519 (8)C17—H17B0.990
C7X—H7D0.980C17—C181.528 (6)
C7X—H7E0.980C18—H18A0.990
C7X—H7F0.980C18—H18B0.990
C8—H8A0.990C18—C191.521 (7)
C8—H8B0.990C19—H19A0.980
C8—H8C0.990C19—H19B0.980
C8—H8D0.990C19—H19C0.980
C8—C91.507 (7)C17X—H17C0.990
C8—C9X1.536 (8)C17X—H17D0.990
C9—H9A0.990C17X—C18X1.526 (8)
C9—H9B0.990C18X—H18C0.990
C9—C101.518 (7)C18X—H18D0.990
C10—H10A0.990C18X—C19X1.523 (8)
C10—H10B0.990C19X—H19D0.980
C10—C111.514 (7)C19X—H19E0.980
C11—H11A0.980C19X—H19F0.980
C11—H11B0.980
Cu—W—O1124.00 (13)C8—C9X—H9D106.7
Cu—W—O2126.57 (13)C8—C9X—C10X122.5 (15)
Cu—W—S253.09 (4)H9C—C9X—H9D106.6
Cu—W—S353.28 (4)H9C—C9X—C10X106.7
O1—W—O2109.42 (18)H9D—C9X—C10X106.7
O1—W—S2109.53 (14)C9X—C10X—H10C109.3
O1—W—S3109.63 (15)C9X—C10X—H10D109.3
O2—W—S2110.36 (13)C9X—C10X—C11X111.6 (17)
O2—W—S3111.47 (13)H10C—C10X—H10D108.0
S2—W—S3106.37 (5)H10C—C10X—C11X109.3
W—Cu—S1177.30 (4)H10D—C10X—C11X109.3
W—Cu—S254.02 (4)C10X—C11X—H11D109.5
W—Cu—S354.01 (4)C10X—C11X—H11E109.5
S1—Cu—S2123.40 (5)C10X—C11X—H11F109.5
S1—Cu—S3128.57 (5)H11D—C11X—H11E109.5
S2—Cu—S3108.02 (5)H11D—C11X—H11F109.5
Cu—S1—C1106.99 (16)H11E—C11X—H11F109.5
S1—C1—N1126.8 (4)N3—C12—H12A108.5
S1—C1—N2123.3 (3)N3—C12—H12B108.5
N1—C1—N2109.9 (4)N3—C12—H12C107.3
C1—N1—H1118 (4)N3—C12—H12D107.3
C1—N1—C2111.5 (4)N3—C12—C13115.0 (5)
H1—N1—C2125 (4)N3—C12—C13X120.0 (9)
N1—C2—H2A111.5H12A—C12—H12B107.5
N1—C2—H2B111.5H12A—C12—C13108.5
N1—C2—C3101.2 (4)H12B—C12—C13108.5
H2A—C2—H2B109.4H12C—C12—H12D106.9
H2A—C2—C3111.5H12C—C12—C13X107.4
H2B—C2—C3111.5H12D—C12—C13X107.3
C2—C3—H3A111.3C12—C13—H13A109.7
C2—C3—H3B111.3C12—C13—H13B109.8
C2—C3—N2102.5 (4)C12—C13—C14109.6 (7)
H3A—C3—H3B109.2H13A—C13—H13B108.2
H3A—C3—N2111.3H13A—C13—C14109.7
H3B—C3—N2111.3H13B—C13—C14109.8
C1—N2—C3112.0 (4)C13—C14—H14A110.1
C1—N2—H2125 (4)C13—C14—H14B110.1
C3—N2—H2123 (4)C13—C14—C15108.0 (9)
W—S2—Cu72.89 (4)H14A—C14—H14B108.4
W—S3—Cu72.72 (4)H14A—C14—C15110.1
C4—N3—C8110.7 (4)H14B—C14—C15110.1
C4—N3—C12111.1 (4)C12—C13X—H13C110.4
C4—N3—C16106.5 (4)C12—C13X—H13D110.4
C8—N3—C12105.7 (3)C12—C13X—C14X106.6 (13)
C8—N3—C16111.2 (4)H13C—C13X—H13D108.6
C12—N3—C16111.6 (4)H13C—C13X—C14X110.4
N3—C4—H4A108.4H13D—C13X—C14X110.4
N3—C4—H4B108.4C13X—C14X—H14C110.8
N3—C4—C5115.6 (4)C13X—C14X—H14D110.7
H4A—C4—H4B107.4C13X—C14X—C15X104.9 (19)
H4A—C4—C5108.4H14C—C14X—H14D108.8
H4B—C4—C5108.4H14C—C14X—C15X110.8
C4—C5—H5A111.2H14D—C14X—C15X110.8
C4—C5—H5B111.2C14X—C15X—H15D109.5
C4—C5—H5C101.8C14X—C15X—H15E109.5
C4—C5—H5D101.8C14X—C15X—H15F109.5
C4—C5—C6102.9 (5)H15D—C15X—H15E109.5
C4—C5—C6X140.8 (12)H15D—C15X—H15F109.5
H5A—C5—H5B109.1H15E—C15X—H15F109.5
H5A—C5—C6111.2N3—C16—H16A108.3
H5B—C5—C6111.2N3—C16—H16B108.3
H5C—C5—H5D104.7N3—C16—H16C108.8
H5C—C5—C6X101.8N3—C16—H16D108.8
H5D—C5—C6X101.8N3—C16—C17115.9 (4)
C5—C6—H6A110.0N3—C16—C17X113.7 (10)
C5—C6—H6B110.0H16A—C16—H16B107.4
C5—C6—C7108.5 (7)H16A—C16—C17108.3
H6A—C6—H6B108.4H16B—C16—C17108.3
H6A—C6—C7110.0H16C—C16—H16D107.7
H6B—C6—C7110.0H16C—C16—C17X108.8
C5—C6X—H6C111.4H16D—C16—C17X108.8
C5—C6X—H6D111.4C16—C17—H17A108.9
C5—C6X—C7X101.6 (15)C16—C17—H17B108.9
H6C—C6X—H6D109.3C16—C17—C18113.2 (6)
H6C—C6X—C7X111.4H17A—C17—H17B107.8
H6D—C6X—C7X111.5H17A—C17—C18108.9
C6X—C7X—H7D109.5H17B—C17—C18108.9
C6X—C7X—H7E109.5C17—C18—H18A108.6
C6X—C7X—H7F109.5C17—C18—H18B108.6
H7D—C7X—H7E109.5C17—C18—C19114.7 (7)
H7D—C7X—H7F109.5H18A—C18—H18B107.6
H7E—C7X—H7F109.5H18A—C18—C19108.6
N3—C8—H8A108.4H18B—C18—C19108.6
N3—C8—H8B108.4C18—C19—H19A109.5
N3—C8—H8C108.7C18—C19—H19B109.5
N3—C8—H8D108.7C18—C19—H19C109.5
N3—C8—C9115.5 (5)H19A—C19—H19B109.5
N3—C8—C9X114.2 (8)H19A—C19—H19C109.5
H8A—C8—H8B107.5H19B—C19—H19C109.5
H8A—C8—C9108.4C16—C17X—H17C112.4
H8B—C8—C9108.4C16—C17X—H17D112.4
H8C—C8—H8D107.6C16—C17X—C18X96.8 (17)
H8C—C8—C9X108.7H17C—C17X—H17D110.0
H8D—C8—C9X108.7H17C—C17X—C18X112.4
C8—C9—H9A110.5H17D—C17X—C18X112.4
C8—C9—H9B110.5C17X—C18X—H18C111.2
C8—C9—C10106.1 (6)C17X—C18X—H18D111.2
H9A—C9—H9B108.7C17X—C18X—C19X103 (2)
H9A—C9—C10110.5H18C—C18X—H18D109.1
H9B—C9—C10110.5H18C—C18X—C19X111.2
C9—C10—H10A109.5H18D—C18X—C19X111.2
C9—C10—H10B109.5C18X—C19X—H19D109.5
C9—C10—C11110.8 (7)C18X—C19X—H19E109.5
H10A—C10—H10B108.1C18X—C19X—H19F109.5
H10A—C10—C11109.5H19D—C19X—H19E109.5
H10B—C10—C11109.5H19D—C19X—H19F109.5
C8—C9X—H9C106.7H19E—C19X—H19F109.5
O1—W—Cu—S1107.0 (9)N3—C4—C5—C6−175.0 (5)
O1—W—Cu—S289.88 (18)N3—C4—C5—C6X158.8 (14)
O1—W—Cu—S3−90.14 (18)C4—C5—C6—C7−177.1 (7)
O2—W—Cu—S1−72.0 (9)C4—C5—C6X—C7X58 (3)
O2—W—Cu—S2−89.12 (16)C4—N3—C8—C966.7 (8)
O2—W—Cu—S390.86 (17)C4—N3—C8—C9X42.3 (12)
S2—W—Cu—S117.1 (9)C12—N3—C8—C9−172.9 (7)
S2—W—Cu—S3179.99 (7)C12—N3—C8—C9X162.7 (11)
S3—W—Cu—S1−162.9 (9)C16—N3—C8—C9−51.6 (8)
S3—W—Cu—S2−179.99 (7)C16—N3—C8—C9X−75.9 (11)
W—Cu—S1—C1147.5 (9)N3—C8—C9—C10−179.2 (7)
S2—Cu—S1—C1164.09 (16)C8—C9—C10—C11−178.3 (12)
S3—Cu—S1—C1−14.74 (18)N3—C8—C9X—C10X166.5 (17)
Cu—S1—C1—N110.3 (5)C8—C9X—C10X—C11X−78 (3)
Cu—S1—C1—N2−171.4 (4)C4—N3—C12—C13−52.7 (7)
S1—C1—N1—C2−173.5 (4)C4—N3—C12—C13X−70.8 (13)
N2—C1—N1—C27.9 (6)C8—N3—C12—C13−172.9 (6)
C1—N1—C2—C3−15.3 (5)C8—N3—C12—C13X169.1 (13)
N1—C2—C3—N216.0 (5)C16—N3—C12—C1366.0 (7)
S1—C1—N2—C3−174.6 (4)C16—N3—C12—C13X48.0 (13)
N1—C1—N2—C34.0 (6)N3—C12—C13—C14−166.9 (7)
C2—C3—N2—C1−13.1 (6)C12—C13—C14—C15−78.5 (12)
S1—Cu—S2—W−179.05 (5)N3—C12—C13X—C14X144.5 (14)
S3—Cu—S2—W−0.01 (6)C12—C13X—C14X—C15X79 (2)
O1—W—S2—Cu−118.40 (15)C4—N3—C16—C17171.3 (6)
O2—W—S2—Cu121.07 (14)C4—N3—C16—C17X−153.7 (18)
S3—W—S2—Cu0.01 (6)C8—N3—C16—C17−68.0 (7)
S1—Cu—S3—W178.99 (5)C8—N3—C16—C17X−33.1 (18)
S2—Cu—S3—W0.01 (6)C12—N3—C16—C1749.9 (7)
O1—W—S3—Cu118.33 (14)C12—N3—C16—C17X84.8 (18)
O2—W—S3—Cu−120.36 (14)N3—C16—C17—C18170.2 (6)
S2—W—S3—Cu−0.01 (6)C16—C17—C18—C19−74.8 (11)
C8—N3—C4—C558.8 (6)N3—C16—C17X—C18X169.6 (18)
C12—N3—C4—C5−58.3 (6)C16—C17X—C18X—C19X−177 (3)
C16—N3—C4—C5179.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S30.87 (1)2.66 (2)3.490 (4)160 (5)
N2—H2···O2i0.87 (1)1.87 (1)2.729 (5)174 (5)
Symmetry code: (i) −x+2, y−1/2, −z+1/2.
 

Acknowledgements

We thank the EPSRC (UK) and Shahid Chamran University for financial support.

References

First citationAdman, E. T. (1991). Adv. Protein Chem. 42, 145–197.  CrossRef PubMed CAS Google Scholar
 First citationAdman, E., Watenpaugh, K. D. & Jensen, L. H. (1975). Proc. Natl Acad. Sci. USA, 72, 4854–4858.  CrossRef PubMed CAS Web of Science Google Scholar
 First citationBackes, G., Mino, Y., Loehr, T. M., Meyer, T. E., Cusanovich, M. A., Sweeney, W. V., Adman, E. T. & Sanders-Loehr, J. (1991). J. Am. Chem. Soc. 113, 2055–2064.  CrossRef CAS Web of Science Google Scholar
 First citationBaker, E. N. (1988). J. Mol. Biol. 203, 1071–1095.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationBeheshti, A., Brooks, N. R., Clegg, W. & Khorrmdin, R. (2004). Acta Cryst. E60, m1923–m1926.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationBeheshti, A., Clegg, W. & Fallah, H. (2001). Inorg. Chim. Acta, 322, 1–6.  Web of Science CSD CrossRef CAS Google Scholar
 First citationBlake, P. R., Park, J. B., Adams, M. W. W. & Summers, M. F. (1992). J. Am. Chem. Soc. 114, 4931–4933.  CrossRef CAS Web of Science Google Scholar
 First citationDuisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92–96.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationDuisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220–229.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationHouseman, A. L. P., Oh, B. H., Kennedy, M. C., Fan, C., Werst, M. M., Beinert, H., Markley, J. L. & Hoffman, B. M. (1992). Biochemistry, 31, 2073–2080.  CrossRef PubMed CAS Web of Science Google Scholar
 First citationMcDonald, J. W., Friesen, G. D., Rosenhein, L. D. & Newton, W. E. (1983). Inorg. Chim. Acta, 72, 205–210.  CrossRef CAS Web of Science Google Scholar
 First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationSheldrick, G. M. (2001). SHELXTL. Version 5. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSummerville, R. H. & Hoffman, R. (1976). J. Am. Chem. Soc. 98, 7240–7254.  CrossRef CAS Web of Science Google Scholar
 First citationSun, W.-Y., Ueyama, N. & Nakamura, A. (1993). Inorg. Chem. 32, 1095–1100.  CrossRef CAS Web of Science Google Scholar
 First citationTsukihara, T., Fukuyama, K., Nakamura, M., Katsube, Y., Tanaka, N., Kakudo, M., Wada, K., Hase, T. & Matsubara, H. (1981). J. Biochem. 90, 1763–1773.  CAS PubMed Web of Science Google Scholar
 First citationWatenpaugh, K. D., Sieker, L. C. & Jensen, L. H. (1979). J. Mol. Biol. 131, 509–522.  CrossRef CAS PubMed Web of Science Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 61| Part 8| August 2005| Pages m1509-m1511
https://doi.org/10.1107/S1600536805021628
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS