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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2195
https://doi.org/10.1107/S160053681002996X

2,2′-Bi-1,3,4-thia­diazole-5,5′-di­amine tetra­hydrate

Chaveng Pakawatchaia and Saowanit Saithonga*

aDepartment of Chemistry and Centre for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
*Correspondence e-mail: saowanit.sa@psu.ac.th

(Received 26 July 2010; accepted 28 July 2010; online 4 August 2010)

In the title compound, C4H4N6S2·4H2O, the complete organic mol­ecule is generated by crystallographic twofold symmetry and the dihedral angle between the aromatic rings is 10.24 (3)°. In the crystal, inter­molecular N—H⋯N, N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds and aromatic π–π stacking inter­actions [centroid–centroid separations = 3.530 (3) and 3.600 (3) Å] are observed.

Related literature

For background to the pharmacutical properties of thia­dia­zo­les, see: Chapleo et al. (1986[Chapleo, C. B., Myers, M., Myers, P. L., Saville, J. F., Smith, A. C. B., Stillings, M. R., Tulloch, I. F., Walter, D. S. & Welbourn, A. P. (1986). J. Med. Chem. 29, 2273-2280.]; 1987[Chapleo, C. B., Myers, P. L., Smith, A. C. B., Tulloch, I. F. & Walter, D. S. (1987). J. Med. Chem. 30, 951-954.]); Stillings et al. (1986[Stillings, M. R., Welbourn, A. P. & Walter, D. S. (1986). J. Med. Chem. 29, 2280-2284.]); Clerici et al. (2001[Clerici, F., Pocar, D., Guido, M., Loche, A., Perlini, V. & Brufani, M. (2001). J. Med. Chem. 44, 931-936.]). For their tribological behavior, see: Zhu et al. (2009[Zhu, F., Fan, W., Wang, A. & Zhu, Y. (2009). Wear, 266, 233-238.]) and for their pesticidal activity, see: Fan et al. (2010[Fan, Z., Yang, Z., Zhang, H., Mi, N., Wang, H., Cai, F., Zuo, X., Zheng, Q. & Song, H. (2010). J. Agric. Food Chem. 58, 2630-2636.]).

[Scheme 1]

Experimental

Crystal data

  • C4H4N6S2·4H2O

  • Mr = 272.32

  • Monoclinic, C 2/c

  • a = 19.977 (6) Å

  • b = 6.678 (2) Å

  • c = 9.328 (3) Å

  • β = 112.514 (6)°

  • V = 1149.7 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.48 mm−1

  • T = 293 K

  • 0.29 × 0.06 × 0.03 mm
Data collection

  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.659, Tmax = 1.000

  • 5047 measured reflections

  • 1015 independent reflections

  • 902 reflections with I > 2σ(I)

  • Rint = 0.040
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.091

  • S = 1.12

  • 1015 reflections

  • 91 parameters

  • 6 restraints

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

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H3A⋯O2i 0.88 (2) 2.11 (2) 2.953 (3) 161 (2)
N3—H3B⋯N2ii 0.88 (2) 2.12 (2) 2.981 (3) 170 (3)
O1—H1A⋯N1iii 0.83 (2) 2.05 (2) 2.872 (3) 171 (3)
O1—H1B⋯O2iv 0.83 (2) 1.96 (2) 2.780 (3) 168 (3)
O2—H2A⋯O1v 0.82 (2) 2.07 (2) 2.867 (3) 167 (3)
O2—H2B⋯O1vi 0.83 (2) 1.97 (2) 2.806 (3) 178 (3)
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, y, -z+{\script{5\over 2}}]; (iii) [-x+1, y, -z+{\script{3\over 2}}]; (iv) [x, -y+1, z-{\script{1\over 2}}]; (v) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (vi) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: Mercury.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681002996X/hb5580sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681002996X/hb5580Isup2.hkl

checkCIF report


Comment top

Most of Shift bases, five membered heterocyclic thiadiazole derivatives containg N and S atoms were studied and reported due to the various applications. Different classes of thiadiazole compounds were found to be pharmacologically active using antihypertensive, anticonvulsant (Chapleo et al., 1986; 1987; Stillings et al., 1986), anti-depressant and anxiolytic activities (Clerici et al., 2001). Recently, the friction and wear properties of 1,3,4-thiadiazole-2-thione derivatives have attracted a considerable amount of research effort. The compounds were synthesized and tested their tribological behavior as additive in rapeseed oil (ROS) to possess good thermal stabilities and anti-corrosive abilities and excellent load-carrying capacities. Moreover, they have good anti-wear and friction-reducing properties (Zhu et al., 2009). In the agriculture, these compounds are widely use as pesticides activities and they have been comercialed as agrochemicals (Fan et al., 2010)

In the present work, the title compound is the by-product of the reaction between copper(I) thiocyanate and 5-amino-1,3,4-thiadiazole-2-thiol ligand. Its crystal structure is reported here. The compound crystallizes in monoclinic system, space group C2/c. The asymetric unit contains half the molecules of the title compound. The crystal structure consists of discrete molecules (Fig. 1) and 5,5'-amine-(2,2'-1,3,4-thiadiazole) molecules arrange as alternated sheets lying parallel to [010]. In addition, each set of sheets are separated by the layer of water molecules runing in same direction. The dihedral angle between mean plane of two thiadiazole rings is 10.24 (3)°. It could be indicated the effect of centroid-centroid interactions with the distances of 3.530 (3) and 3.600 (3)Å between the adjacent thidiazole rings in the same layer as depicted in Fig. 2. In the crystal lattice, amide nitrogen protons form N3—H3A···O2ii [N3···O2ii = 2.953 (3) Å] and N3—H3B···N2iii [N3···N2iii = 2.981 (3) Å] intermolecular hydrogen bonds with oxygen atoms of water molecules and one nitrogen atom of thiadiazole ring of adjacent molecules. While another thiadiazole nitrogen atom forms hydrogen bonding interaction with another water molecule in packing, O1—H1A···N1i [O1···N1i = 2.872 (3) Å]. In addition, The packing is also stabilized by the another type of hydrogen bond, O—H···O, among water molecules [O1···O2iv = 2.780 (3) Å, O2···O1v = 2.867 (3) Å, O2···O1vi = 2.806 (3) Å; iv, v and vi are the symmetry codes as given in Table 1]. The hydrogen bonds are shown in Fig. 3. The interactions in packings are generated the three-dimensional interaction networks and the interaction views down three axes are depicted in Fig. 4, 5 and 6.

Related literature top

For background to the pharmacutical properties of thiadiazoles, see: Chapleo et al.(1986; 1987); Stillings et al. (1986); Clerici et al. (2001). For their tribological behavior, see: Zhu et al. (2009) and for their pesticidal activity, see: Fan et al. (2010).

Experimental top

The 5-amino-1,3,4-thiadiazole-2-thiol (0.28 g, 2.1 mmol) was dissolved in acetronitile (40 ml) and then copper(I) thiocyanate salt (0.16 g, 1.3 mmol) was added. After that, the reaction of mixture was performed under ultrasonic activation (338–340 K, 40 kHz) for 2 h. The light yellow filtration was kept and allowed to slowly to room temperature. Colourless blocks and rods of the title compound were recovered after a few days. Insufficient crystalline material was obtained for elemental analysis.

Refinement top

All hydrogen atoms were located in a difference Fourier map and restrained to ride on their parent atoms, N—H = 0.87–0.89 Å with Uiso(H) = 1.2Ueq(N) and O—H = 0.81–0.84 Å with Uiso(H) = 1.2Ueq(O), respectively.

Structure description top

Most of Shift bases, five membered heterocyclic thiadiazole derivatives containg N and S atoms were studied and reported due to the various applications. Different classes of thiadiazole compounds were found to be pharmacologically active using antihypertensive, anticonvulsant (Chapleo et al., 1986; 1987; Stillings et al., 1986), anti-depressant and anxiolytic activities (Clerici et al., 2001). Recently, the friction and wear properties of 1,3,4-thiadiazole-2-thione derivatives have attracted a considerable amount of research effort. The compounds were synthesized and tested their tribological behavior as additive in rapeseed oil (ROS) to possess good thermal stabilities and anti-corrosive abilities and excellent load-carrying capacities. Moreover, they have good anti-wear and friction-reducing properties (Zhu et al., 2009). In the agriculture, these compounds are widely use as pesticides activities and they have been comercialed as agrochemicals (Fan et al., 2010)

In the present work, the title compound is the by-product of the reaction between copper(I) thiocyanate and 5-amino-1,3,4-thiadiazole-2-thiol ligand. Its crystal structure is reported here. The compound crystallizes in monoclinic system, space group C2/c. The asymetric unit contains half the molecules of the title compound. The crystal structure consists of discrete molecules (Fig. 1) and 5,5'-amine-(2,2'-1,3,4-thiadiazole) molecules arrange as alternated sheets lying parallel to [010]. In addition, each set of sheets are separated by the layer of water molecules runing in same direction. The dihedral angle between mean plane of two thiadiazole rings is 10.24 (3)°. It could be indicated the effect of centroid-centroid interactions with the distances of 3.530 (3) and 3.600 (3)Å between the adjacent thidiazole rings in the same layer as depicted in Fig. 2. In the crystal lattice, amide nitrogen protons form N3—H3A···O2ii [N3···O2ii = 2.953 (3) Å] and N3—H3B···N2iii [N3···N2iii = 2.981 (3) Å] intermolecular hydrogen bonds with oxygen atoms of water molecules and one nitrogen atom of thiadiazole ring of adjacent molecules. While another thiadiazole nitrogen atom forms hydrogen bonding interaction with another water molecule in packing, O1—H1A···N1i [O1···N1i = 2.872 (3) Å]. In addition, The packing is also stabilized by the another type of hydrogen bond, O—H···O, among water molecules [O1···O2iv = 2.780 (3) Å, O2···O1v = 2.867 (3) Å, O2···O1vi = 2.806 (3) Å; iv, v and vi are the symmetry codes as given in Table 1]. The hydrogen bonds are shown in Fig. 3. The interactions in packings are generated the three-dimensional interaction networks and the interaction views down three axes are depicted in Fig. 4, 5 and 6.

For background to the pharmacutical properties of thiadiazoles, see: Chapleo et al.(1986; 1987); Stillings et al. (1986); Clerici et al. (2001). For their tribological behavior, see: Zhu et al. (2009) and for their pesticidal activity, see: Fan et al. (2010).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids plotted at the 30% probability level. H atoms are omitted.
[Figure 2] Fig. 2. Centriod-centriod interaction distances between thiadiazoline rings in packing plot down a axis. Water layers are omitted.
[Figure 3] Fig. 3. The interactions of the [5,5'-amine-(2,2'-1,3,4-thiadiazole)] tetrahydrate compound. Symmetry code: i= x, y - 1,z; ii = 1 - x,y,1.5 - z; iii = 1 - x, y 2.5 - z; iv = 1 - x, y, 2.5 - z; v = x, -y, 1/2 + z; vi = 1/2 - x, 1/2 - y, 1 - z; vii = 1/2 - x, y - 1/2, 1 - z; viii = 1 - x, 1 - y, 2 - z; ix = 1/2 + x, y - 1/2, z; x = 1/2 + x, 1.5 - y, 1/2 - z.
[Figure 4] Fig. 4. The interactions packing plot down a axis.
[Figure 5] Fig. 5. The interactions packing plot down b axis.
[Figure 6] Fig. 6. The interactions packing plot down c axis.
2,2'-Bi-1,3,4-thiadiazole-5,5'-diamine tetrahydrate top
Crystal data top
C4H4N6S2·4H2OF(000) = 568
Mr = 272.32Dx = 1.573 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1375 reflections
a = 19.977 (6) Åθ = 2.2–27.5°
b = 6.678 (2) ŵ = 0.48 mm−1
c = 9.328 (3) ÅT = 293 K
β = 112.514 (6)°Rod, colourless
V = 1149.7 (6) Å30.29 × 0.06 × 0.03 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer		1015 independent reflections
Radiation source: fine-focus sealed tube902 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Frames, each covering 0.3 ° in ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		h = −23→23
Tmin = 0.659, Tmax = 1.000k = −7→7
5047 measured reflectionsl = −11→11
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.046P)2 + 0.8924P]
where P = (Fo2 + 2Fc2)/3
1015 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.36 e Å−3
6 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C4H4N6S2·4H2OV = 1149.7 (6) Å3
Mr = 272.32Z = 4
Monoclinic, C2/cMo Kα radiation
a = 19.977 (6) ŵ = 0.48 mm−1
b = 6.678 (2) ÅT = 293 K
c = 9.328 (3) Å0.29 × 0.06 × 0.03 mm
β = 112.514 (6)°
Data collection top
Bruker APEX CCD
diffractometer		1015 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		902 reflections with I > 2σ(I)
Tmin = 0.659, Tmax = 1.000Rint = 0.040
5047 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0346 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.36 e Å−3
1015 reflectionsΔρmin = −0.29 e Å−3
91 parameters
Special details top

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 > 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
S10.40277 (3)0.22880 (9)0.80732 (6)0.0302 (2)
C10.49090 (11)0.2498 (3)0.8184 (2)0.0254 (5)
C20.43905 (11)0.2386 (3)1.0092 (2)0.0250 (5)
N10.53913 (9)0.2631 (2)0.9582 (2)0.0275 (4)
N20.51008 (10)0.2557 (3)1.0700 (2)0.0278 (4)
N30.39755 (11)0.2341 (3)1.0925 (2)0.0346 (5)
H3A0.3518 (10)0.196 (4)1.049 (3)0.042*
H3B0.4198 (14)0.236 (4)1.194 (2)0.042*
O10.30903 (9)0.3504 (3)0.3923 (2)0.0468 (5)
H1A0.3539 (10)0.338 (5)0.434 (3)0.056*
H1B0.2881 (16)0.242 (3)0.391 (4)0.056*
O20.25880 (9)1.0305 (3)0.9186 (2)0.0451 (5)
H2A0.2393 (14)0.997 (5)0.977 (3)0.054*
H2B0.2376 (14)1.067 (4)0.827 (2)0.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0234 (3)0.0449 (4)0.0199 (3)0.0004 (2)0.0057 (2)−0.0007 (2)
C10.0253 (11)0.0284 (11)0.0227 (11)0.0003 (8)0.0096 (9)0.0001 (8)
C20.0270 (11)0.0256 (11)0.0206 (11)0.0016 (8)0.0071 (9)−0.0001 (8)
N10.0273 (10)0.0324 (10)0.0230 (10)0.0002 (7)0.0100 (8)0.0004 (7)
N20.0269 (9)0.0364 (11)0.0203 (9)0.0005 (7)0.0093 (8)0.0002 (7)
N30.0275 (10)0.0542 (13)0.0232 (10)−0.0021 (8)0.0109 (9)−0.0003 (9)
O10.0292 (9)0.0543 (12)0.0501 (11)−0.0052 (8)0.0076 (8)0.0054 (9)
O20.0356 (10)0.0546 (11)0.0420 (11)−0.0013 (8)0.0113 (8)0.0006 (9)
Geometric parameters (Å, º) top
S1—C11.729 (2)N3—H3A0.882 (17)
S1—C21.741 (2)N3—H3B0.875 (17)
C1—N11.294 (3)O1—H1A0.834 (18)
C1—C1i1.455 (4)O1—H1B0.833 (17)
C2—N21.316 (3)O2—H2A0.815 (17)
C2—N31.337 (3)O2—H2B0.834 (17)
N1—N21.375 (3)
C1—S1—C286.53 (10)C2—N2—N1111.99 (17)
C1—S1—C286.53 (10)C2—N2—N1111.99 (17)
N1—C1—C1i122.9 (2)C2—N3—H3A120.2 (17)
N1—C1—S1114.49 (16)C2—N3—H3A120.2 (17)
C1i—C1—S1122.6 (2)C2—N3—H3B117.0 (19)
N2—C2—N3123.9 (2)C2—N3—H3B117.0 (19)
N2—C2—S1113.78 (16)H3A—N3—H3B121 (3)
N3—C2—S1122.30 (17)H1A—O1—H1B111 (3)
C1—N1—N2113.20 (17)H2A—O2—H2B126 (3)
C2—S1—C1—N1−0.35 (15)C1i—C1—N1—N2−178.63 (10)
C2—S1—C1—N1−0.35 (15)S1—C1—N1—N20.6 (2)
C2—S1—C1—C1i178.91 (8)N3—C2—N2—N1−178.00 (19)
C2—S1—C1—C1i178.91 (8)S1—C2—N2—N10.4 (2)
C1—S1—C2—N2−0.02 (16)C1—N1—N2—C2−0.6 (2)
C1—S1—C2—N3178.36 (19)C1—N1—N2—C2−0.6 (2)
Symmetry code: (i) −x+1, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2ii0.88 (2)2.11 (2)2.953 (3)161 (2)
N3—H3B···N2iii0.88 (2)2.12 (2)2.981 (3)170 (3)
O1—H1A···N1i0.83 (2)2.05 (2)2.872 (3)171 (3)
O1—H1B···O2iv0.83 (2)1.96 (2)2.780 (3)168 (3)
O2—H2A···O1v0.82 (2)2.07 (2)2.867 (3)167 (3)
O2—H2B···O1vi0.83 (2)1.97 (2)2.806 (3)178 (3)
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, y−1, z; (iii) −x+1, y, −z+5/2; (iv) x, −y+1, z−1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formulaC4H4N6S2·4H2O
Mr272.32
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)19.977 (6), 6.678 (2), 9.328 (3)
β (°) 112.514 (6)
V (Å3)1149.7 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.48
Crystal size (mm)0.29 × 0.06 × 0.03
Data collection
DiffractometerBruker APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.659, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		5047, 1015, 902
Rint0.040
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.091, 1.12
No. of reflections1015
No. of parameters91
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.36, −0.29

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.882 (17)2.105 (18)2.953 (3)161 (2)
N3—H3B···N2ii0.875 (17)2.116 (18)2.981 (3)170 (3)
O1—H1A···N1iii0.834 (18)2.045 (19)2.872 (3)171 (3)
O1—H1B···O2iv0.833 (17)1.960 (18)2.780 (3)168 (3)
O2—H2A···O1v0.815 (17)2.066 (19)2.867 (3)167 (3)
O2—H2B···O1vi0.834 (17)1.972 (18)2.806 (3)178 (3)
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y, −z+5/2; (iii) −x+1, y, −z+3/2; (iv) x, −y+1, z−1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) −x+1/2, −y+3/2, −z+1.
 

Acknowledgements

We gratefully acknowledge financial support from the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Commission on Higher Education, Ministry of Education, and the Department of Chemistry, Faculty of Science, Prince of Songkla University.

References

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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2195
https://doi.org/10.1107/S160053681002996X
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