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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 67| Part 4| April 2011| Page o786
doi:10.1107/S160053681100732X

2-(1,3-Benzo­thia­zol-2-yl)guanidine

Shaaban Kamel Mohamed,a Mahmoud A. A. El-Remaily,b Ahmed M. Soliman,b Atash V. Gurbanovc and Seik Weng Ngd*

aChemistry & Environmental Science Division, School of Science, Manchester Metropolitan University, England, bDepartment of Chemistry, Sohag University, Sohag, Egypt, cDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 21 February 2011; accepted 25 February 2011; online 5 March 2011)

In the title comound, C8H8N4S, one of the two independent mol­ecules is essentially planar (r.m.s. deviation = 0.025 Å), while the other is slightly buckled (r.m.s. deviation = 0.131 Å) with the guanidine unit bent out of the plane of the fused-ring system by 16.8 (1)°. In the crystal, inter­molecular N—H⋯N hydrogen bonds between the two independent mol­ecules give rise to a hydrogen-bonded dimer. Addtional weak inter­molecular N—H⋯N hydrogen bonds connect these dimers into chains along [010]. An intra­molecular N—H⋯N hydrogen bond is also observed in each independent mol­ecule.

Related literature

For the synthesis, see: Dolzhenko et al. (2006[Dolzhenko, A. V., Chui, W.-K. & Dolzhenko, A. V. (2006). Synthesis, pp. 597-602.]).

[Scheme 1]

Experimental

Crystal data

  • C8H8N4S

  • Mr = 192.24

  • Orthorhombic, P b c a

  • a = 10.2970 (3) Å

  • b = 10.0817 (3) Å

  • c = 33.5158 (11) Å

  • V = 3479.32 (18) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 295 K

  • 0.30 × 0.30 × 0.30 mm
Data collection

  • Bruker APEXII diffractometer

  • 35704 measured reflections

  • 3996 independent reflections

  • 3345 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.111

  • S = 1.13

  • 3996 reflections

  • 267 parameters

  • 8 restraints

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

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H31⋯N1 0.86 (1) 2.00 (2) 2.679 (2) 134 (2)
N3—H32⋯N2i 0.86 (1) 2.40 (2) 3.228 (2) 161 (2)
N4—H41⋯N6 0.86 (1) 2.25 (1) 3.084 (3) 165 (3)
N4—H42⋯N8i 0.86 (1) 2.50 (2) 3.350 (3) 176 (2)
N7—H71⋯N5 0.86 (1) 2.03 (2) 2.717 (3) 136 (2)
N8—H81⋯N2 0.86 (1) 2.24 (1) 3.096 (3) 177 (2)
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, 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: 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, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100732X/lh5214sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100732X/lh5214Isup2.hkl

checkCIF report


Comment top

The title compound was synthesized as an intermediate for the synthesis of other heterocyclic compounds (Dolzhenko et al., 2006). In the title comound, C8H8N4, one of the two independent molecules of is essentially planar (r.m.s. deviation 0.025 Å) while the other is slightly buckled (r.m.s. deviation 0.131 Å) with the guanidine unit bent out of the plane of the fused-ring system by 16.8 (1) °. In the crystal a pair of intermolecular N-H···N hydrogen bonds between the two independent molecules give rise to a hydrogen-bonded dimer (Fig. 1). Addtional weak intermolecular N-H···N hydrogen bonds connect these dimers into one-dimensional chains along [010].

Related literature top

For the synthesis, see: Dolzhenko et al. (2006).

Experimental top

2-Aminothiophenol (0.050 mol) was dissolved in 10% sulfuric acid (50 ml) and to the solution was added cyanoduanidine (0.075 mol). The mixture was heated to give a clear solution. To the cool solution was added 50% sodium hydroxide (10 mol) to precipitate the product. X-ray quality crystals were recrystallized from ethanol in 90% yield. The synthesis was based on a reported procedure (Dolzhenko et al., 2006).

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C–H 0.93 Å; Uiso(H) 1.2Ueq(C)] and were included in the refinement in a riding-model approximation. The amino H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.86±0.01 Å; the Uiso(H) values were refined.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C8H8N4 with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Hydrogen bonds are denoted by dashed lines.
2-(1,3-Benzothiazol-2-yl)guanidine top
Crystal data top
C8H8N4SF(000) = 1600
Mr = 192.24Dx = 1.468 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9882 reflections
a = 10.2970 (3) Åθ = 2.3–27.7°
b = 10.0817 (3) ŵ = 0.33 mm−1
c = 33.5158 (11) ÅT = 295 K
V = 3479.32 (18) Å3Prism, colorless
Z = 160.30 × 0.30 × 0.30 mm
Data collection top
Bruker APEXII
diffractometer		3345 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
ϕ and ω scansh = −13→13
35704 measured reflectionsk = −13→13
3996 independent reflectionsl = −43→43
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0453P)2 + 1.2618P]
where P = (Fo2 + 2Fc2)/3
3996 reflections(Δ/σ)max = 0.001
267 parametersΔρmax = 0.22 e Å−3
8 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C8H8N4SV = 3479.32 (18) Å3
Mr = 192.24Z = 16
Orthorhombic, PbcaMo Kα radiation
a = 10.2970 (3) ŵ = 0.33 mm−1
b = 10.0817 (3) ÅT = 295 K
c = 33.5158 (11) Å0.30 × 0.30 × 0.30 mm
Data collection top
Bruker APEXII
diffractometer		3345 reflections with I > 2σ(I)
35704 measured reflectionsRint = 0.026
3996 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0398 restraints
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.22 e Å−3
3996 reflectionsΔρmin = −0.28 e Å−3
267 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.48382 (5)0.66100 (5)0.659730 (17)0.05839 (16)
S20.84372 (5)0.47427 (6)0.472576 (17)0.06418 (17)
N10.55487 (14)0.42140 (14)0.67760 (4)0.0474 (3)
N20.64035 (14)0.51382 (15)0.61637 (5)0.0485 (3)
N30.71411 (18)0.29516 (18)0.62708 (6)0.0605 (4)
H310.6709 (19)0.293 (2)0.6491 (4)0.064 (7)*
H320.756 (2)0.2272 (16)0.6184 (7)0.073 (7)*
N40.77196 (19)0.4128 (2)0.57119 (5)0.0649 (5)
H410.753 (3)0.4781 (19)0.5560 (6)0.087 (9)*
H420.8259 (19)0.3507 (18)0.5657 (7)0.071 (7)*
N50.67826 (16)0.63000 (15)0.43811 (5)0.0537 (4)
N60.66455 (16)0.61327 (15)0.51004 (5)0.0534 (4)
N70.47131 (19)0.70197 (19)0.48350 (6)0.0612 (4)
H710.505 (2)0.692 (3)0.4602 (4)0.079 (9)*
H720.3919 (12)0.722 (2)0.4882 (7)0.074 (7)*
N80.5036 (2)0.68148 (19)0.55135 (6)0.0649 (5)
H810.539 (2)0.635 (2)0.5699 (5)0.066 (7)*
H820.4247 (12)0.706 (3)0.5554 (7)0.082 (8)*
C10.47271 (17)0.46403 (18)0.70777 (6)0.0477 (4)
C20.4344 (2)0.3899 (2)0.74069 (6)0.0609 (5)
H20.46610.30430.74430.073*
C30.3497 (2)0.4436 (3)0.76785 (7)0.0682 (6)
H30.32470.39390.78990.082*
C40.3009 (2)0.5704 (2)0.76293 (7)0.0690 (6)
H40.24340.60470.78170.083*
C50.3367 (2)0.6461 (2)0.73061 (7)0.0626 (5)
H50.30370.73120.72720.075*
C60.42309 (18)0.59256 (18)0.70318 (6)0.0504 (4)
C70.56907 (17)0.51333 (16)0.65055 (5)0.0448 (4)
C80.70785 (17)0.40623 (18)0.60589 (6)0.0488 (4)
C90.75591 (18)0.57694 (17)0.40817 (5)0.0495 (4)
C100.7460 (2)0.6048 (2)0.36749 (6)0.0604 (5)
H100.68330.66370.35820.072*
C110.8292 (2)0.5445 (2)0.34137 (7)0.0640 (6)
H110.82210.56240.31420.077*
C120.9238 (2)0.4574 (2)0.35448 (7)0.0685 (6)
H120.97910.41750.33610.082*
C130.9367 (2)0.4293 (2)0.39439 (7)0.0697 (6)
H131.00060.37120.40330.084*
C140.85219 (19)0.48948 (19)0.42113 (6)0.0545 (5)
C150.71308 (18)0.58623 (17)0.47312 (6)0.0494 (4)
C160.5469 (2)0.66392 (17)0.51381 (6)0.0529 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0643 (3)0.0367 (2)0.0742 (3)0.0069 (2)0.0233 (2)0.0041 (2)
S20.0636 (3)0.0691 (3)0.0598 (3)0.0202 (3)−0.0057 (2)0.0084 (2)
N10.0456 (8)0.0428 (7)0.0537 (8)0.0032 (6)−0.0053 (6)0.0014 (6)
N20.0488 (8)0.0429 (8)0.0537 (8)0.0055 (6)0.0022 (7)−0.0031 (6)
N30.0647 (11)0.0507 (9)0.0660 (11)0.0193 (8)−0.0024 (9)−0.0044 (8)
N40.0678 (11)0.0718 (12)0.0551 (10)0.0255 (10)0.0021 (8)−0.0080 (9)
N50.0621 (9)0.0436 (8)0.0554 (9)0.0028 (7)−0.0127 (7)−0.0002 (7)
N60.0627 (10)0.0432 (8)0.0544 (9)0.0061 (7)−0.0108 (7)−0.0043 (7)
N70.0544 (10)0.0582 (10)0.0710 (12)0.0035 (8)−0.0113 (9)−0.0030 (9)
N80.0742 (13)0.0538 (10)0.0667 (12)0.0118 (9)−0.0006 (10)−0.0019 (8)
C10.0418 (9)0.0473 (9)0.0539 (10)−0.0037 (7)−0.0055 (7)−0.0004 (8)
C20.0602 (12)0.0626 (12)0.0601 (12)−0.0020 (10)−0.0054 (9)0.0120 (9)
C30.0689 (14)0.0793 (15)0.0564 (12)−0.0138 (12)0.0052 (10)0.0083 (11)
C40.0622 (12)0.0731 (14)0.0716 (14)−0.0145 (11)0.0189 (11)−0.0118 (11)
C50.0596 (12)0.0514 (11)0.0768 (14)−0.0064 (9)0.0183 (10)−0.0085 (10)
C60.0478 (9)0.0437 (9)0.0596 (11)−0.0064 (8)0.0075 (8)−0.0032 (8)
C70.0410 (8)0.0382 (8)0.0551 (10)0.0016 (7)−0.0019 (7)−0.0037 (7)
C80.0435 (9)0.0503 (10)0.0526 (10)0.0070 (8)−0.0115 (8)−0.0111 (8)
C90.0520 (10)0.0376 (8)0.0588 (10)−0.0089 (8)−0.0089 (8)0.0002 (8)
C100.0686 (12)0.0525 (11)0.0602 (11)−0.0076 (10)−0.0137 (10)0.0056 (9)
C110.0776 (14)0.0571 (12)0.0571 (12)−0.0192 (11)−0.0018 (10)0.0028 (9)
C120.0769 (15)0.0618 (12)0.0669 (13)−0.0092 (11)0.0149 (11)0.0024 (10)
C130.0686 (13)0.0658 (13)0.0748 (14)0.0097 (11)0.0105 (11)0.0092 (11)
C140.0559 (11)0.0475 (10)0.0600 (11)−0.0040 (8)−0.0032 (9)0.0054 (8)
C150.0543 (10)0.0355 (8)0.0583 (10)−0.0008 (7)−0.0134 (8)−0.0021 (7)
C160.0625 (11)0.0325 (8)0.0637 (11)−0.0023 (8)−0.0099 (9)−0.0051 (8)
Geometric parameters (Å, º) top
S1—C61.7285 (19)N8—H810.860 (10)
S1—C71.7555 (17)N8—H820.861 (10)
S2—C141.733 (2)C1—C21.390 (3)
S2—C151.7562 (19)C1—C61.401 (3)
N1—C71.305 (2)C2—C31.372 (3)
N1—C11.387 (2)C2—H20.9300
N2—C81.335 (2)C3—C41.383 (3)
N2—C71.360 (2)C3—H30.9300
N3—C81.328 (3)C4—C51.375 (3)
N3—H310.863 (9)C4—H40.9300
N3—H320.860 (10)C5—C61.389 (3)
N4—C81.339 (3)C5—H50.9300
N4—H410.855 (10)C9—C101.396 (3)
N4—H420.857 (10)C9—C141.396 (3)
N5—C151.304 (2)C10—C111.368 (3)
N5—C91.390 (3)C10—H100.9300
N6—C161.321 (3)C11—C121.382 (3)
N6—C151.362 (2)C11—H110.9300
N7—C161.336 (3)C12—C131.374 (3)
N7—H710.862 (10)C12—H120.9300
N7—H720.856 (10)C13—C141.388 (3)
N8—C161.347 (3)C13—H130.9300
C6—S1—C789.43 (9)C5—C6—C1121.36 (18)
C14—S2—C1589.54 (9)C5—C6—S1129.38 (16)
C7—N1—C1110.79 (15)C1—C6—S1109.25 (14)
C8—N2—C7119.96 (16)N1—C7—N2130.40 (16)
C8—N3—H31117.0 (16)N1—C7—S1115.11 (13)
C8—N3—H32121.0 (16)N2—C7—S1114.48 (12)
H31—N3—H32122 (2)N3—C8—N2124.73 (18)
C8—N4—H41116.5 (19)N3—C8—N4118.86 (18)
C8—N4—H42118.1 (17)N2—C8—N4116.41 (18)
H41—N4—H42125 (2)N5—C9—C10125.84 (18)
C15—N5—C9111.18 (16)N5—C9—C14115.27 (17)
C16—N6—C15120.07 (16)C10—C9—C14118.89 (19)
C16—N7—H71115.0 (18)C11—C10—C9119.3 (2)
C16—N7—H72118.9 (17)C11—C10—H10120.3
H71—N7—H72125 (2)C9—C10—H10120.3
C16—N8—H81117.6 (16)C10—C11—C12121.4 (2)
C16—N8—H82119.8 (17)C10—C11—H11119.3
H81—N8—H82116 (2)C12—C11—H11119.3
N1—C1—C2125.81 (18)C13—C12—C11120.6 (2)
N1—C1—C6115.41 (16)C13—C12—H12119.7
C2—C1—C6118.76 (18)C11—C12—H12119.7
C3—C2—C1119.6 (2)C12—C13—C14118.5 (2)
C3—C2—H2120.2C12—C13—H13120.7
C1—C2—H2120.2C14—C13—H13120.7
C2—C3—C4121.1 (2)C13—C14—C9121.3 (2)
C2—C3—H3119.5C13—C14—S2129.41 (17)
C4—C3—H3119.5C9—C14—S2109.25 (15)
C5—C4—C3120.6 (2)N5—C15—N6130.46 (18)
C5—C4—H4119.7N5—C15—S2114.76 (15)
C3—C4—H4119.7N6—C15—S2114.79 (13)
C4—C5—C6118.5 (2)N6—C16—N7124.9 (2)
C4—C5—H5120.7N6—C16—N8116.38 (18)
C6—C5—H5120.7N7—C16—N8118.7 (2)
C7—N1—C1—C2178.46 (18)C15—N5—C9—C10−178.95 (18)
C7—N1—C1—C60.1 (2)C15—N5—C9—C140.4 (2)
N1—C1—C2—C3−178.35 (19)N5—C9—C10—C11−179.80 (18)
C6—C1—C2—C3−0.1 (3)C14—C9—C10—C110.9 (3)
C1—C2—C3—C40.4 (3)C9—C10—C11—C12−0.6 (3)
C2—C3—C4—C5−0.2 (4)C10—C11—C12—C13−0.1 (3)
C3—C4—C5—C6−0.2 (3)C11—C12—C13—C140.5 (4)
C4—C5—C6—C10.5 (3)C12—C13—C14—C9−0.1 (3)
C4—C5—C6—S1178.91 (17)C12—C13—C14—S2179.90 (18)
N1—C1—C6—C5178.08 (17)N5—C9—C14—C13−179.97 (19)
C2—C1—C6—C5−0.4 (3)C10—C9—C14—C13−0.6 (3)
N1—C1—C6—S1−0.6 (2)N5—C9—C14—S20.0 (2)
C2—C1—C6—S1−179.04 (15)C10—C9—C14—S2179.40 (14)
C7—S1—C6—C5−177.9 (2)C15—S2—C14—C13179.7 (2)
C7—S1—C6—C10.65 (14)C15—S2—C14—C9−0.30 (14)
C1—N1—C7—N2179.79 (18)C9—N5—C15—N6179.41 (18)
C1—N1—C7—S10.39 (19)C9—N5—C15—S2−0.6 (2)
C8—N2—C7—N11.6 (3)C16—N6—C15—N519.2 (3)
C8—N2—C7—S1−178.99 (13)C16—N6—C15—S2−160.82 (14)
C6—S1—C7—N1−0.63 (15)C14—S2—C15—N50.53 (15)
C6—S1—C7—N2179.88 (14)C14—S2—C15—N6−179.47 (15)
C7—N2—C8—N3−1.5 (3)C15—N6—C16—N7−5.5 (3)
C7—N2—C8—N4177.80 (17)C15—N6—C16—N8176.74 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H31···N10.86 (1)2.00 (2)2.679 (2)134 (2)
N3—H32···N2i0.86 (1)2.40 (2)3.228 (2)161 (2)
N4—H41···N60.86 (1)2.25 (1)3.084 (3)165 (3)
N4—H42···N8i0.86 (1)2.50 (2)3.350 (3)176 (2)
N7—H71···N50.86 (1)2.03 (2)2.717 (3)136 (2)
N8—H81···N20.86 (1)2.24 (1)3.096 (3)177 (2)
Symmetry code: (i) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formulaC8H8N4S
Mr192.24
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)295
a, b, c (Å)10.2970 (3), 10.0817 (3), 33.5158 (11)
V (Å3)3479.32 (18)
Z16
Radiation typeMo Kα
µ (mm−1)0.33
Crystal size (mm)0.30 × 0.30 × 0.30
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		35704, 3996, 3345
Rint0.026
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.111, 1.13
No. of reflections3996
No. of parameters267
No. of restraints8
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.22, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H31···N10.86 (1)2.00 (2)2.679 (2)134 (2)
N3—H32···N2i0.86 (1)2.40 (2)3.228 (2)161 (2)
N4—H41···N60.86 (1)2.25 (1)3.084 (3)165 (3)
N4—H42···N8i0.86 (1)2.50 (2)3.350 (3)176 (2)
N7—H71···N50.86 (1)2.03 (2)2.717 (3)136 (2)
N8—H81···N20.86 (1)2.24 (1)3.096 (3)177 (2)
Symmetry code: (i) −x+3/2, y−1/2, z.
 

Acknowledgements

We thank Manchester Metropolitan University, Baku State University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDolzhenko, A. V., Chui, W.-K. & Dolzhenko, A. V. (2006). Synthesis, pp. 597–602.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 67| Part 4| April 2011| Page o786
doi:10.1107/S160053681100732X
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