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

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Bis[N-benzyl-N-(2-phenyl­eth­yl)di­thio­carbamato-κ2S,S′]lead(II)

aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, India, and bDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India
*Correspondence e-mail: s_selvanayagam@rediffmail.com

(Received 13 July 2012; accepted 17 August 2012; online 25 August 2012)

The mol­ecule of the title compound, [Pb(C16H16NS2)2], is located on a twofold rotation axis, which runs through the PbII atom. The two dithio­carbamate ligands coordinate the metal in a pyramidal configuration through the S atoms. The two phenyl rings of each dithocarbamate ligand are aligned at a dihedral angle of 78.4 (1)°. The mol­ecular conformation is stabilized by intra­molecular C—H⋯S inter­actions.

Related literature

For general background of the title compound, see: Davidovich et al. (2010[Davidovich, R. L., Stavila, V. & Whitmire, K. H. (2010). Coord. Chem. Rev. 254, 2193-2226.]); Picket & O'Brien (2001[Picket, N. & O'Brien, P. (2001). Chem. Rec. 1, 467-479.]); Srinivasan & Thirumaran (2012[Srinivasan, N. & Thirumaran, S. (2012). Superlattices Microstruct. 51, 912-920.]); Sathiyaraj & Thirumaran (2012[Sathiyaraj, E. & Thirumaran, S. (2012). Spectrochim. Acta Part A, 97, 575-581.]); Green et al. (2004[Green, M., Prince, P. & Gardener, M. (2004). J. Adv. Mater. 16, 994-996.]); Koh et al. (2003[Koh, Y. W., Lai, C. S., Du, A. Y., Tiekeinsk, E. R. T. & Loh, K. P. (2003). Chem. Mater. 15, 4544-4554.]). For the preparation, see: Sathiyaraj & Thirumaran (2012[Sathiyaraj, E. & Thirumaran, S. (2012). Spectrochim. Acta Part A, 97, 575-581.]). For a related structure, see: Davidovich et al. (2010[Davidovich, R. L., Stavila, V. & Whitmire, K. H. (2010). Coord. Chem. Rev. 254, 2193-2226.])

[Scheme 1]

Experimental

Crystal data
  • [Pb(C16H16NS2)2]

  • Mr = 780.03

  • Monoclinic, C 2/c

  • a = 28.5467 (12) Å

  • b = 5.5321 (2) Å

  • c = 19.4158 (8) Å

  • β = 101.600 (2)°

  • V = 3003.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 5.92 mm−1

  • T = 292 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]) Tmin = 0.384, Tmax = 0.384

  • 13027 measured reflections

  • 3711 independent reflections

  • 3006 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.062

  • S = 1.04

  • 3711 reflections

  • 177 parameters

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −1.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9A⋯S2 0.97 2.49 2.986 (3) 112
C2—H2B⋯S1 0.97 2.55 2.990 (4) 107

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information


Comment top

The solid state structural chemistry of lead dithiocarbamates is rich and fascinating in that different structural motifs are found ranging from monomeric, dimeric, tetrameric to linear chain (Davidovich et al., 2010). Metal dithiocarbamate complexes have proven to be very successful as single source precursors for the preparation of metal sulfide nanoparticles (Picket & O'Brien, 2001; Srinivasan & Thirumaran, 2012). The title compound was also used as single source precursor for the synthesis of PbS nanoparticles (Sathiyaraj & Thirumaran, 2012). There is an indication that the molecular structure of the synthetic precursor may influence both the size and morphology of the nanoparticles (Green et al., 2004; Koh et al., 2003). In view of these importance we have undertaken the crystal structure determination of the title compound, and the results are presented here.

The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1.

The structure consists of monomeric molecules composed of one Pb atom and two chelating dithiocarbamate ligands. The two dithiocarbamate ligands are coordinated through S atoms to the metal pyramidally and in each chelate ring one Pb-S bond is significantly shorter than other. The relative bond distances and angles for the title compound agree with the presence of an electron lone pair at an equatorial position of a distorted trigonal bipyramid PbS4. Evidence for the presence of a stereochemically active electron lone pair of the lead atom has also been reported for other lead complexes (Davidovich et al., 2010).

The sum of the angles at N1 [359.8°] is in accordance with sp2 hybridization. Two phenyl rings in dithiocarbmate ligand is make a dihedral angle of 78.4 (1) °.

In addition to the van der Waals interactions, the molecular structure is influenced only by intramolecular C—H···S hydrogen bonds involving atoms S1 and S2. (Fig. 2 and Table 1).

Related literature top

For general background of the title compound, see: Davidovich et al. (2010); Picket & O'Brien (2001); Srinivasan & Thirumaran (2012); Sathiyaraj & Thirumaran (2012); Green et al. (2004); Koh et al. (2003). For the preparation, see: Sathiyaraj & Thirumaran (2012). For a related structure, see: Davidovich et al. (2010)

Experimental top

The title compound was prepared according to the literature procedure (Sathiyaraj & Thirumaran, 2012). Single crystals were obtained by slow evaporation of dichloromethane and acetone (1:1) solution of the title compound at room temperature.

Refinement top

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H distances of 0.93-0.97 Å, and Uiso(H) = 1.2Ueq(C) for H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound, viewed along the b axis; H-bonds are shown as dashed lines. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted.
Bis[N-benzyl-N-(2-phenylethyl)dithiocarbamato- κ2S,S']lead(II) top
Crystal data top
[Pb(C16H16NS2)2]F(000) = 1536
Mr = 780.03Dx = 1.725 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5527 reflections
a = 28.5467 (12) Åθ = 1.5–28.3°
b = 5.5321 (2) ŵ = 5.92 mm1
c = 19.4158 (8) ÅT = 292 K
β = 101.600 (2)°Block, brown
V = 3003.6 (2) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEXII area-detector
diffractometer
3711 independent reflections
Radiation source: fine-focus sealed tube3006 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω and ϕ scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 3731
Tmin = 0.384, Tmax = 0.384k = 77
13027 measured reflectionsl = 2525
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0254P)2 + 1.657P]
where P = (Fo2 + 2Fc2)/3
3711 reflections(Δ/σ)max = 0.001
177 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 1.25 e Å3
Crystal data top
[Pb(C16H16NS2)2]V = 3003.6 (2) Å3
Mr = 780.03Z = 4
Monoclinic, C2/cMo Kα radiation
a = 28.5467 (12) ŵ = 5.92 mm1
b = 5.5321 (2) ÅT = 292 K
c = 19.4158 (8) Å0.20 × 0.20 × 0.20 mm
β = 101.600 (2)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
3711 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
3006 reflections with I > 2σ(I)
Tmin = 0.384, Tmax = 0.384Rint = 0.038
13027 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.062H-atom parameters constrained
S = 1.04Δρmax = 0.43 e Å3
3711 reflectionsΔρmin = 1.25 e Å3
177 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Pb11.00001.14280 (3)0.75000.05084 (8)
S10.99115 (3)0.94809 (17)0.61154 (4)0.04494 (19)
S20.93213 (3)0.80487 (16)0.71424 (4)0.0473 (2)
N10.92789 (9)0.5899 (4)0.59107 (12)0.0373 (6)
C10.94871 (10)0.7651 (6)0.63419 (14)0.0339 (6)
C20.94211 (11)0.5417 (6)0.52408 (15)0.0440 (7)
H2A0.93970.36910.51530.053*
H2B0.97550.58620.52870.053*
C30.91358 (11)0.6706 (5)0.46061 (15)0.0343 (6)
C40.88722 (12)0.8758 (5)0.46490 (17)0.0427 (7)
H40.88530.93690.50890.051*
C50.86360 (12)0.9926 (6)0.40547 (17)0.0498 (8)
H50.84601.13170.40950.060*
C60.86593 (13)0.9041 (7)0.34018 (18)0.0571 (10)
H60.85010.98320.29990.069*
C70.89154 (14)0.6993 (8)0.33484 (17)0.0569 (10)
H70.89310.63910.29060.068*
C80.91528 (12)0.5799 (6)0.39433 (16)0.0453 (8)
H80.93230.43930.39000.054*
C90.89245 (11)0.4222 (6)0.61033 (17)0.0419 (7)
H9A0.89570.42250.66100.050*
H9B0.89920.25980.59620.050*
C100.84215 (12)0.4865 (8)0.5771 (2)0.0612 (10)
H10A0.83820.47560.52640.073*
H10B0.83600.65230.58880.073*
C110.80629 (12)0.3225 (6)0.60110 (19)0.0492 (8)
C120.78865 (14)0.1181 (7)0.5636 (2)0.0564 (9)
H120.80000.07620.52360.068*
C130.75473 (12)0.0232 (7)0.58444 (19)0.0542 (9)
H130.74340.15990.55850.065*
C140.73735 (13)0.0338 (7)0.6428 (2)0.0579 (9)
H140.71370.06080.65610.070*
C150.75511 (14)0.2325 (8)0.68166 (19)0.0629 (10)
H150.74390.27190.72200.075*
C160.78937 (14)0.3730 (6)0.6612 (2)0.0584 (10)
H160.80150.50570.68850.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.05114 (13)0.03239 (11)0.05977 (12)0.0000.01087 (8)0.000
S10.0350 (4)0.0494 (5)0.0505 (4)0.0041 (4)0.0088 (3)0.0104 (4)
S20.0515 (5)0.0542 (5)0.0374 (4)0.0131 (4)0.0120 (4)0.0068 (4)
N10.0362 (14)0.0397 (14)0.0366 (12)0.0003 (11)0.0088 (11)0.0024 (11)
C10.0303 (15)0.0344 (15)0.0355 (14)0.0031 (13)0.0033 (12)0.0036 (13)
C20.0473 (19)0.0463 (18)0.0398 (15)0.0094 (16)0.0121 (14)0.0061 (15)
C30.0352 (16)0.0323 (16)0.0381 (14)0.0058 (12)0.0142 (13)0.0051 (12)
C40.0476 (19)0.0378 (18)0.0431 (16)0.0015 (14)0.0100 (14)0.0079 (14)
C50.054 (2)0.0366 (19)0.0565 (19)0.0008 (15)0.0067 (16)0.0025 (16)
C60.055 (2)0.068 (3)0.0470 (19)0.0091 (19)0.0068 (17)0.0178 (18)
C70.062 (2)0.075 (3)0.0374 (17)0.008 (2)0.0185 (17)0.0050 (17)
C80.0453 (19)0.0483 (19)0.0460 (17)0.0039 (15)0.0182 (15)0.0098 (15)
C90.0423 (18)0.0355 (16)0.0459 (16)0.0000 (14)0.0045 (14)0.0028 (14)
C100.041 (2)0.067 (3)0.076 (2)0.0087 (18)0.0135 (18)0.030 (2)
C110.0356 (18)0.052 (2)0.061 (2)0.0064 (15)0.0116 (16)0.0140 (17)
C120.052 (2)0.063 (3)0.057 (2)0.0107 (18)0.0173 (18)0.0014 (19)
C130.049 (2)0.043 (2)0.066 (2)0.0022 (16)0.0033 (17)0.0008 (18)
C140.047 (2)0.057 (2)0.071 (2)0.0051 (18)0.0141 (19)0.016 (2)
C150.069 (3)0.069 (3)0.058 (2)0.007 (2)0.029 (2)0.001 (2)
C160.058 (2)0.054 (2)0.063 (2)0.0103 (17)0.0127 (19)0.0096 (17)
Geometric parameters (Å, º) top
Pb1—S2i2.6813 (8)C7—C81.384 (5)
Pb1—S22.6813 (8)C7—H70.9300
Pb1—S1i2.8597 (9)C8—H80.9300
Pb1—S12.8597 (9)C9—C101.494 (4)
S1—C11.703 (3)C9—H9A0.9700
S2—C11.727 (3)C9—H9B0.9700
N1—C11.339 (4)C10—C111.510 (5)
N1—C21.463 (4)C10—H10A0.9700
N1—C91.475 (4)C10—H10B0.9700
C2—C31.512 (4)C11—C161.378 (5)
C2—H2A0.9700C11—C121.384 (5)
C2—H2B0.9700C12—C131.368 (5)
C3—C41.373 (4)C12—H120.9300
C3—C81.391 (4)C13—C141.362 (5)
C4—C51.375 (4)C13—H130.9300
C4—H40.9300C14—C151.372 (6)
C5—C61.373 (5)C14—H140.9300
C5—H50.9300C15—C161.369 (5)
C6—C71.363 (5)C15—H150.9300
C6—H60.9300C16—H160.9300
S2i—Pb1—S291.59 (4)C8—C7—H7119.6
S2i—Pb1—S1i64.61 (2)C7—C8—C3119.8 (3)
S2—Pb1—S1i84.46 (2)C7—C8—H8120.1
S2i—Pb1—S184.46 (2)C3—C8—H8120.1
S2—Pb1—S164.61 (2)N1—C9—C10112.9 (3)
S1i—Pb1—S1135.74 (4)N1—C9—H9A109.0
C1—S1—Pb185.08 (10)C10—C9—H9A109.0
C1—S2—Pb190.43 (11)N1—C9—H9B109.0
C1—N1—C2121.3 (3)C10—C9—H9B109.0
C1—N1—C9122.5 (2)H9A—C9—H9B107.8
C2—N1—C9116.0 (2)C9—C10—C11112.1 (3)
N1—C1—S1121.2 (2)C9—C10—H10A109.2
N1—C1—S2119.2 (2)C11—C10—H10A109.2
S1—C1—S2119.63 (17)C9—C10—H10B109.2
N1—C2—C3116.0 (2)C11—C10—H10B109.2
N1—C2—H2A108.3H10A—C10—H10B107.9
C3—C2—H2A108.3C16—C11—C12117.3 (3)
N1—C2—H2B108.3C16—C11—C10121.0 (3)
C3—C2—H2B108.3C12—C11—C10121.7 (3)
H2A—C2—H2B107.4C13—C12—C11121.1 (3)
C4—C3—C8118.4 (3)C13—C12—H12119.5
C4—C3—C2123.5 (3)C11—C12—H12119.5
C8—C3—C2118.1 (3)C14—C13—C12120.8 (3)
C3—C4—C5121.3 (3)C14—C13—H13119.6
C3—C4—H4119.3C12—C13—H13119.6
C5—C4—H4119.3C13—C14—C15119.2 (3)
C6—C5—C4120.0 (3)C13—C14—H14120.4
C6—C5—H5120.0C15—C14—H14120.4
C4—C5—H5120.0C16—C15—C14120.1 (3)
C7—C6—C5119.5 (3)C16—C15—H15119.9
C7—C6—H6120.2C14—C15—H15119.9
C5—C6—H6120.2C15—C16—C11121.5 (3)
C6—C7—C8120.9 (3)C15—C16—H16119.2
C6—C7—H7119.6C11—C16—H16119.2
S2i—Pb1—S1—C191.43 (10)C3—C4—C5—C60.3 (5)
S2—Pb1—S1—C12.98 (10)C4—C5—C6—C70.4 (5)
S1i—Pb1—S1—C147.21 (10)C5—C6—C7—C80.1 (6)
S2i—Pb1—S2—C180.18 (10)C6—C7—C8—C30.8 (5)
S1i—Pb1—S2—C1144.48 (10)C4—C3—C8—C71.4 (5)
S1—Pb1—S2—C12.93 (10)C2—C3—C8—C7176.9 (3)
C2—N1—C1—S12.6 (4)C1—N1—C9—C10101.6 (3)
C9—N1—C1—S1177.5 (2)C2—N1—C9—C1083.3 (3)
C2—N1—C1—S2177.3 (2)N1—C9—C10—C11176.3 (3)
C9—N1—C1—S22.4 (4)C9—C10—C11—C1687.0 (4)
Pb1—S1—C1—N1175.1 (2)C9—C10—C11—C1293.8 (4)
Pb1—S1—C1—S24.81 (16)C16—C11—C12—C131.9 (5)
Pb1—S2—C1—N1174.8 (2)C10—C11—C12—C13177.3 (3)
Pb1—S2—C1—S15.11 (17)C11—C12—C13—C140.1 (5)
C1—N1—C2—C392.9 (3)C12—C13—C14—C151.5 (6)
C9—N1—C2—C391.9 (3)C13—C14—C15—C161.0 (6)
N1—C2—C3—C420.9 (5)C14—C15—C16—C111.1 (6)
N1—C2—C3—C8160.9 (3)C12—C11—C16—C152.5 (5)
C8—C3—C4—C51.1 (5)C10—C11—C16—C15176.7 (4)
C2—C3—C4—C5177.0 (3)
Symmetry code: (i) x+2, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···S20.972.492.986 (3)112
C2—H2B···S10.972.552.990 (4)107

Experimental details

Crystal data
Chemical formula[Pb(C16H16NS2)2]
Mr780.03
Crystal system, space groupMonoclinic, C2/c
Temperature (K)292
a, b, c (Å)28.5467 (12), 5.5321 (2), 19.4158 (8)
β (°) 101.600 (2)
V3)3003.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)5.92
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.384, 0.384
No. of measured, independent and
observed [I > 2σ(I)] reflections
13027, 3711, 3006
Rint0.038
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.062, 1.04
No. of reflections3711
No. of parameters177
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 1.25

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SIR92 (Altomare et al., 1993), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···S20.972.492.986 (3)112
C2—H2B···S10.972.552.990 (4)107
 

Acknowledgements

The authors thank the CAS in Crystallography and Biophysics, University of Madras, Chennai for the data collection.

References

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