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

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Benzyl N′-(1H-indol-3-ylmethyl­­idene)­hydrazinecarbodi­thio­ate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 22 September 2008; accepted 5 October 2008; online 11 October 2008)

The C10H8N3S2 portion of the title mol­ecule, C17H15N3S3, is nearly planar (r.m.s. deviation 0.05 Å); this unit and the phenyl ring subtend an angle of 114.5 (2)° at the methyl­ene C atom.

Related literature

For other Schiff bases derived by condensing S-benzyl hydrazinecarbodithio­ate with either aromatic aldehydes or ketones, see: Ali et al. (2004[Ali, M. A., Mirza, A. H., Hamid, M. H. S. A., Bujang, F. H. & Bernhardt, P. V. (2004). Polyhedron, 23, 2405-2412.]); Chan et al. (2003[Chan, M.-H. E., Crouse, K. A., Tarafder, M. T. H. & Yamin, B. M. (2003). Acta Cryst. E59, o628-o629.]); Fun et al. (1995[Fun, H.-K., Sivakumar, K., Yip, B.-C., Tian, Y.-P., Duan, C.-Y., Lu, Z.-L. & You, X.-Z. (1995). Acta Cryst. C51, 2080-2083.]); How et al. (2007a[How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007a). Acta Cryst. E63, o3023-o3024.],b[How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007b). Acta Cryst. E63, o3133-o3134.],c[How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007c). Acta Cryst. E63, o3135-o3136.]); Khoo et al. (2005[Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441-o2443.]); Qiu & Luo (2007[Qiu, X.-Y. & Luo, Z.-G. (2007). Acta Cryst. E63, o4339.]); Roy et al. (2007[Roy, S., Mandal, T. N., Barik, A. K., Pal, S., Gupta, S., Hazra, A., Butcher, R. J., Hunter, A. D., Zeller, M. & Kar, S. K. (2007). Polyhedron, 26, 2603-2611.]); Tarafder et al. (2002[Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2002). Polyhedron, 21, 2691-2698.]); Xu et al. (1991[Xu, Z., Alyea, E., Ferguson, G. & Jennings, M. C. (1991). Polyhedron, 10, 1625-1629.]); Zhang et al. (2004[Zhang, M.-L., Tian, Y.-P., Zhang, X.-J., Wu, J.-Y., Zhang, S.-Y., Wang, D., Jiang, M. H., Chantrapromma, S. & Fun, H.-K. (2004). Transition Met. Chem. 29, 596-602.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15N3S2

  • Mr = 325.44

  • Monoclinic, P 21 /c

  • a = 15.4936 (7) Å

  • b = 9.8114 (4) Å

  • c = 10.2531 (4) Å

  • β = 98.432 (3)°

  • V = 1541.8 (1) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.34 mm−1

  • T = 100 (2) K

  • 0.25 × 0.10 × 0.03 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.919, Tmax = 0.990

  • 8531 measured reflections

  • 3383 independent reflections

  • 2323 reflections with I > 2σ(I)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.118

  • S = 1.01

  • 3383 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

The structure of (I), Fig. 1, shows bond distances for N1—N2 and N2—C9 of 1.382 (3) and 1.287 (3) Å, respectively, confirming the assignment shown in the Scheme. The molecule is bent about the methylene-C7 atom so that the residues on either side are approximately orthogonal. The amino groups do not form any hydrogen bonds.

Related literature top

For other Schiff bases derived by condensing S-benzyl hydrazinecarbodithioate with either aromatic aldehydes or ketones, see: Ali et al. (2004); Chan et al. (2003); Fun et al. (1995); How et al. (2007a,b,c); Khoo et al. (2005); Qiu & Luo (2007); Roy et al. (2007); Tarafder et al. (2002); Xu et al. (1991); Zhang et al. (2004).

Experimental top

Indole-3-carbaldehyde (0.37 g, 2.5 mmol) and S-benzyl dithiocarbazate (0.50 g, 2.5 mmol) were heated in methanol (40 ml) for 3 h. The solution was set aside for the formation of yellow crystals.

Refinement top

Hydrogen atoms were placed at calculated positions (C—H 0.95–0.99, N—H 0.88 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2 times Ueq(C,N).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C17H15N2S3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Benzyl N'-(1H-indol-3-ylmethylidene)hydrazinecarbodithioate top
Crystal data top
C17H15N3S2F(000) = 680
Mr = 325.44Dx = 1.402 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1305 reflections
a = 15.4936 (7) Åθ = 2.5–23.2°
b = 9.8114 (4) ŵ = 0.34 mm1
c = 10.2531 (4) ÅT = 100 K
β = 98.432 (3)°Prism, light yellow
V = 1541.8 (1) Å30.25 × 0.10 × 0.03 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
3383 independent reflections
Radiation source: fine-focus sealed tube2323 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω scansθmax = 27°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2020
Tmin = 0.919, Tmax = 0.990k = 1212
8531 measured reflectionsl = 138
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0391P)2 + 1.1115P]
where P = (Fo2 + 2Fc2)/3
3383 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C17H15N3S2V = 1541.8 (1) Å3
Mr = 325.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.4936 (7) ŵ = 0.34 mm1
b = 9.8114 (4) ÅT = 100 K
c = 10.2531 (4) Å0.25 × 0.10 × 0.03 mm
β = 98.432 (3)°
Data collection top
Bruker SMART APEX
diffractometer
3383 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2323 reflections with I > 2σ(I)
Tmin = 0.919, Tmax = 0.990Rint = 0.058
8531 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.01Δρmax = 0.48 e Å3
3383 reflectionsΔρmin = 0.33 e Å3
199 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.75015 (5)0.74458 (7)0.47255 (7)0.02090 (18)
S20.87340 (5)0.53986 (7)0.36891 (7)0.02198 (19)
N10.70350 (15)0.5227 (2)0.3457 (2)0.0217 (5)
H10.70860.44400.30630.026*
N20.62145 (15)0.5704 (2)0.3596 (2)0.0212 (5)
N30.32371 (16)0.5105 (2)0.2983 (2)0.0253 (6)
H30.27060.47950.27320.030*
C10.87962 (17)0.9360 (3)0.4432 (3)0.0188 (6)
C20.89308 (18)0.9185 (3)0.3115 (3)0.0216 (6)
H20.88550.83120.27140.026*
C30.91737 (18)1.0283 (3)0.2403 (3)0.0242 (7)
H3a0.92721.01560.15180.029*
C40.92738 (18)1.1564 (3)0.2970 (3)0.0259 (7)
H40.94361.23160.24750.031*
C50.91353 (19)1.1742 (3)0.4261 (3)0.0245 (7)
H50.92021.26190.46540.029*
C60.89010 (18)1.0647 (3)0.4983 (3)0.0212 (6)
H60.88111.07800.58710.025*
C70.85739 (18)0.8174 (3)0.5249 (3)0.0210 (6)
H7A0.86090.84750.61760.025*
H7B0.90180.74530.52200.025*
C80.77530 (18)0.5938 (3)0.3909 (3)0.0191 (6)
C90.55868 (18)0.4859 (3)0.3251 (3)0.0209 (6)
H90.57170.39760.29530.025*
C100.46972 (19)0.5221 (3)0.3305 (3)0.0204 (6)
C110.39833 (19)0.4445 (3)0.2826 (3)0.0230 (6)
H110.40090.35690.24380.028*
C120.43633 (18)0.6451 (3)0.3827 (3)0.0197 (6)
C130.47407 (19)0.7591 (3)0.4513 (3)0.0217 (6)
H130.53570.76940.46800.026*
C140.42007 (19)0.8557 (3)0.4939 (3)0.0255 (7)
H140.44520.93280.54120.031*
C150.3294 (2)0.8434 (3)0.4694 (3)0.0285 (7)
H150.29410.91220.49970.034*
C160.2901 (2)0.7323 (3)0.4016 (3)0.0284 (7)
H160.22840.72380.38420.034*
C170.34423 (19)0.6341 (3)0.3602 (3)0.0222 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0225 (4)0.0184 (3)0.0229 (4)0.0009 (3)0.0070 (3)0.0025 (3)
S20.0234 (4)0.0212 (4)0.0226 (4)0.0034 (3)0.0075 (3)0.0014 (3)
N10.0231 (13)0.0194 (12)0.0234 (14)0.0005 (10)0.0060 (11)0.0047 (10)
N20.0197 (12)0.0236 (13)0.0211 (14)0.0023 (10)0.0062 (10)0.0016 (11)
N30.0220 (13)0.0285 (14)0.0249 (14)0.0048 (11)0.0022 (11)0.0006 (11)
C10.0166 (14)0.0203 (14)0.0195 (16)0.0007 (11)0.0027 (12)0.0006 (12)
C20.0223 (15)0.0239 (15)0.0181 (16)0.0013 (12)0.0012 (12)0.0037 (12)
C30.0235 (15)0.0337 (17)0.0158 (15)0.0008 (13)0.0038 (12)0.0034 (13)
C40.0236 (15)0.0250 (15)0.0295 (19)0.0006 (13)0.0045 (13)0.0106 (14)
C50.0262 (16)0.0198 (15)0.0277 (18)0.0005 (12)0.0041 (13)0.0016 (13)
C60.0228 (15)0.0218 (15)0.0196 (16)0.0036 (12)0.0050 (12)0.0002 (12)
C70.0227 (15)0.0209 (15)0.0196 (16)0.0006 (12)0.0032 (12)0.0010 (12)
C80.0265 (15)0.0170 (14)0.0149 (15)0.0008 (11)0.0064 (12)0.0024 (11)
C90.0277 (16)0.0217 (15)0.0142 (15)0.0022 (12)0.0058 (12)0.0003 (12)
C100.0268 (15)0.0201 (14)0.0140 (15)0.0048 (12)0.0020 (12)0.0024 (12)
C110.0297 (16)0.0217 (15)0.0180 (16)0.0046 (13)0.0054 (13)0.0009 (13)
C120.0233 (15)0.0220 (15)0.0143 (15)0.0039 (12)0.0044 (12)0.0040 (12)
C130.0227 (15)0.0248 (15)0.0177 (16)0.0043 (12)0.0037 (12)0.0041 (13)
C140.0315 (17)0.0253 (16)0.0205 (17)0.0039 (13)0.0063 (13)0.0028 (13)
C150.0291 (17)0.0296 (17)0.0277 (18)0.0022 (14)0.0077 (14)0.0038 (14)
C160.0231 (16)0.0340 (18)0.0281 (18)0.0034 (13)0.0040 (13)0.0005 (15)
C170.0272 (16)0.0228 (15)0.0163 (15)0.0057 (12)0.0025 (12)0.0034 (12)
Geometric parameters (Å, º) top
S1—C81.771 (3)C5—H50.9500
S1—C71.816 (3)C6—H60.9500
S2—C81.656 (3)C7—H7A0.9900
N1—C81.337 (4)C7—H7B0.9900
N1—N21.382 (3)C9—C101.432 (4)
N1—H10.8800C9—H90.9500
N2—C91.287 (3)C10—C111.373 (4)
N3—C111.355 (4)C10—C121.446 (4)
N3—C171.384 (4)C11—H110.9500
N3—H30.8800C12—C131.402 (4)
C1—C61.383 (4)C12—C171.416 (4)
C1—C21.407 (4)C13—C141.377 (4)
C1—C71.503 (4)C13—H130.9500
C2—C31.384 (4)C14—C151.395 (4)
C2—H20.9500C14—H140.9500
C3—C41.384 (4)C15—C161.385 (4)
C3—H3a0.9500C15—H150.9500
C4—C51.384 (4)C16—C171.384 (4)
C4—H40.9500C16—H160.9500
C5—C61.383 (4)
C8—S1—C7102.30 (13)H7A—C7—H7B107.6
C8—N1—N2121.2 (2)N1—C8—S2121.3 (2)
C8—N1—H1119.4N1—C8—S1111.7 (2)
N2—N1—H1119.4S2—C8—S1126.97 (17)
C9—N2—N1115.0 (2)N2—C9—C10121.5 (3)
C11—N3—C17109.3 (2)N2—C9—H9119.3
C11—N3—H3125.4C10—C9—H9119.3
C17—N3—H3125.4C11—C10—C9125.3 (3)
C6—C1—C2118.6 (3)C11—C10—C12106.4 (3)
C6—C1—C7120.1 (3)C9—C10—C12128.3 (3)
C2—C1—C7121.2 (3)N3—C11—C10110.4 (3)
C3—C2—C1120.1 (3)N3—C11—H11124.8
C3—C2—H2119.9C10—C11—H11124.8
C1—C2—H2119.9C13—C12—C17118.6 (3)
C4—C3—C2120.5 (3)C13—C12—C10134.9 (3)
C4—C3—H3a119.8C17—C12—C10106.4 (2)
C2—C3—H3a119.8C14—C13—C12118.7 (3)
C3—C4—C5119.5 (3)C14—C13—H13120.7
C3—C4—H4120.2C12—C13—H13120.7
C5—C4—H4120.2C13—C14—C15121.7 (3)
C4—C5—C6120.3 (3)C13—C14—H14119.2
C4—C5—H5119.9C15—C14—H14119.2
C6—C5—H5119.9C16—C15—C14121.0 (3)
C5—C6—C1121.0 (3)C16—C15—H15119.5
C5—C6—H6119.5C14—C15—H15119.5
C1—C6—H6119.5C17—C16—C15117.4 (3)
C1—C7—S1114.5 (2)C17—C16—H16121.3
C1—C7—H7A108.6C15—C16—H16121.3
S1—C7—H7A108.6C16—C17—N3129.9 (3)
C1—C7—H7B108.6C16—C17—C12122.6 (3)
S1—C7—H7B108.6N3—C17—C12107.4 (2)
C8—N1—N2—C9172.7 (3)C9—C10—C11—N3177.4 (3)
C6—C1—C2—C30.8 (4)C12—C10—C11—N31.3 (3)
C7—C1—C2—C3177.1 (3)C11—C10—C12—C13175.2 (3)
C1—C2—C3—C41.0 (4)C9—C10—C12—C136.2 (5)
C2—C3—C4—C50.5 (4)C11—C10—C12—C171.0 (3)
C3—C4—C5—C60.2 (4)C9—C10—C12—C17177.7 (3)
C4—C5—C6—C10.3 (4)C17—C12—C13—C140.0 (4)
C2—C1—C6—C50.2 (4)C10—C12—C13—C14175.8 (3)
C7—C1—C6—C5177.7 (3)C12—C13—C14—C150.6 (4)
C6—C1—C7—S1113.9 (3)C13—C14—C15—C160.4 (5)
C2—C1—C7—S168.2 (3)C14—C15—C16—C170.4 (5)
C8—S1—C7—C1103.7 (2)C15—C16—C17—N3175.7 (3)
N2—N1—C8—S2177.5 (2)C15—C16—C17—C121.1 (4)
N2—N1—C8—S12.6 (3)C11—N3—C17—C16176.7 (3)
C7—S1—C8—N1179.0 (2)C11—N3—C17—C120.4 (3)
C7—S1—C8—S20.9 (2)C13—C12—C17—C160.9 (4)
N1—N2—C9—C10178.3 (2)C10—C12—C17—C16177.8 (3)
N2—C9—C10—C11172.6 (3)C13—C12—C17—N3176.6 (2)
N2—C9—C10—C125.8 (5)C10—C12—C17—N30.3 (3)
C17—N3—C11—C101.1 (3)

Experimental details

Crystal data
Chemical formulaC17H15N3S2
Mr325.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)15.4936 (7), 9.8114 (4), 10.2531 (4)
β (°) 98.432 (3)
V3)1541.8 (1)
Z4
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.25 × 0.10 × 0.03
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.919, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
8531, 3383, 2323
Rint0.058
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.118, 1.01
No. of reflections3383
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

 

Acknowledgements

The authors thank the University of Malaya for funding this study (Science Fund Grants 12-02-03-2031 and 12-02-03-2051).

References

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