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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 5| May 2010| Page o1162
https://doi.org/10.1107/S1600536810013863

1-(4-Chloro­phen­yl)-3-(2-thienylcarbon­yl)thio­urea

Sohail Saeed,a* Naghmana Rashida and Wing-Tak Wongb

aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad, Pakistan, and bDepartment of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong SAR, People's Republic of China
*Correspondence e-mail: sohail262001@yahoo.com

(Received 22 March 2010; accepted 14 April 2010; online 24 April 2010)

The title compound, C12H9ClN2OS2, exists in the thio­amide form with an intra­molecular N—H⋯O hydrogen bond across the thio­urea and the carbonyl group. The dihedral angle between the rings is 10.36 (11)°. In the crystal structure, mol­ecules are linked into chains by weak inter­molecular C—H⋯Cl hydrogen-bonding inter­actions.

Related literature

For general background to the biological activity of thio­urea derivatives, see: Xu et al. (2004[Xu, Y., Hua, W., Liu, X. & Zhu, D. (2004). Chin. J. Org. Chem. 24, 1217-1222.]); Gu et al. (2007[Gu, C.-L., Liu, L., Sui, Y., Zhao, J.-L. D., Wang, D. & Chen, Y.-J. (2007). Tetrahedron, 18, 455-463.]). For related structures, see: Saeed et al. (2008[Saeed, S., Bhatti, M. H., Yunus, U. & Jones, P. G. (2008). Acta Cryst. E64, o1485.], 2009[Saeed, S., Rashid, N., Tahir, A. & Jones, P. G. (2009). Acta Cryst. E65, o1870-o1871.]). For the cytotoxicity of anti­cancer drugs to normal cells in cancer therapy, see: Saeed et al. (2010[Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010). Eur. J. Med. Chem. 45, 1323-1331.]).

[Scheme 1]

Experimental

Crystal data

  • C12H9ClN2OS2

  • Mr = 296.78

  • Monoclinic, P 21 /n

  • a = 4.6552 (7) Å

  • b = 11.660 (2) Å

  • c = 23.630 (4) Å

  • β = 95.626 (2)°

  • V = 1276.4 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.61 mm−1

  • T = 300 K

  • 0.42 × 0.19 × 0.08 mm
Data collection

  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, Göttingen University, Göttingen, Germany.]) Tmin = 0.783, Tmax = 0.953

  • 8549 measured reflections

  • 3102 independent reflections

  • 2578 reflections with I > 2σ(I)

  • Rint = 0.019
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.107

  • S = 1.07

  • 3102 reflections

  • 172 parameters

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

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1 0.87 (2) 1.91 (2) 2.651 (2) 143 (2)
C12—H12⋯Cl1i 0.93 2.69 3.523 (2) 149
Symmetry code: (i) [x-{\script{5\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and CrystalStructure (Rigaku/MSC and Rigaku, 2006[Rigaku/MSC and Rigaku (2006). CrystalStructure. Rigaku/MSC, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810013863/lx2142sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013863/lx2142Isup2.hkl

checkCIF report


Comment top

Thiourea and its derivatives are an important class of organic compounds in which sulfur is the major ligand atom which plays an important role in coordination chemistry with transition metals. Thiourea and its derivatives have found extensive applications in the fields of medicine, agriculture and analytical chemistry. Thioureas are also known to exhibit a wide range of biological activities including anticancer (Saeed et al., 2010), antifungal (Saeed et al., 2008), antiviral, antibacterial, anti-tubercular, anti-thyroidal, herbicidal and insecticidal activities, organocatalyst (Gu et al., 2007) and as agrochemicals (Xu et al., 2004).

The 4-chlorophenyl ring is slightly twisted {15.04 (8)°} from the thiourea plane. The thioureido group is also slightly twisted {5.0 (1)°} from the thiophene ring plane of S2/C9/C10/C11/C12. The molecular packing (Fig. 2) exhibits the thioamide form with an intramolecular N–H···O hydrogen bond across the thiourea system, with a N1–H1N···O1 (Table 1). The crystal packing (Fig. 2) is stabilized by weak intermolecular C–H···Cl hydrogen bonds between the thiophene H atom and the chlorine of an adjacent molecule, with a C12–H12···Cl1i (Table 1).

Related literature top

For general background to the biological activity of thiourea derivatives, see: Xu et al. (2004); Gu et al. (2007). For related structures, see: Saeed et al. (2008, 2009). For the cytotoxicity of anticancer drugs to normal cells in cancer therapy, see: Saeed et al. (2010).

For related literature, see: .

Experimental top

A solution of 2-thiophenecarbonyl chloride (0.01 mol) in anhydrous acetone (80 ml) was added dropwise to a suspension of ammonium thiocyanate (0.01 mol) in anhydrous acetone (50 ml) and the reaction mixture was refluxed for 50 minutes. After cooling to room temperature, a solution of 4-chloroaniline (0.01 mol) in dry acetone (25 ml) was added and the resulting mixture refluxed for 2 h. The reaction mixture was poured into five times its volume of cold water, upon which the thiourea precipitated. The product was recrystallized from ethanol as white block crystals.

Refinement top

The H atoms bound C atoms were located from difference Fourier map and refined freely. All H atoms of C atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 Å for aryl and thiophenyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl thiophenyl H atoms.

Structure description top

Thiourea and its derivatives are an important class of organic compounds in which sulfur is the major ligand atom which plays an important role in coordination chemistry with transition metals. Thiourea and its derivatives have found extensive applications in the fields of medicine, agriculture and analytical chemistry. Thioureas are also known to exhibit a wide range of biological activities including anticancer (Saeed et al., 2010), antifungal (Saeed et al., 2008), antiviral, antibacterial, anti-tubercular, anti-thyroidal, herbicidal and insecticidal activities, organocatalyst (Gu et al., 2007) and as agrochemicals (Xu et al., 2004).

The 4-chlorophenyl ring is slightly twisted {15.04 (8)°} from the thiourea plane. The thioureido group is also slightly twisted {5.0 (1)°} from the thiophene ring plane of S2/C9/C10/C11/C12. The molecular packing (Fig. 2) exhibits the thioamide form with an intramolecular N–H···O hydrogen bond across the thiourea system, with a N1–H1N···O1 (Table 1). The crystal packing (Fig. 2) is stabilized by weak intermolecular C–H···Cl hydrogen bonds between the thiophene H atom and the chlorine of an adjacent molecule, with a C12–H12···Cl1i (Table 1).

For general background to the biological activity of thiourea derivatives, see: Xu et al. (2004); Gu et al. (2007). For related structures, see: Saeed et al. (2008, 2009). For the cytotoxicity of anticancer drugs to normal cells in cancer therapy, see: Saeed et al. (2010).

For related literature, see: .

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006) and CrystalStructure (Rigaku/MSC and Rigaku, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. N–H···O and C–H···Cl interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x - 5/2, - y + 1/2, z - 1/2 (ii) x + 5/2, - y + 1/2, z + 1/2.]
1-(4-Chlorophenyl)-3-(2-thienylcarbonyl)thiourea top
Crystal data top
C12H9ClN2OS2F(000) = 608
Mr = 296.78Dx = 1.544 Mg m−3
Monoclinic, P21/nMelting point: 412 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 4.6552 (7) ÅCell parameters from 8801 reflections
b = 11.660 (2) Åθ = 1.7–28.3°
c = 23.630 (4) ŵ = 0.61 mm−1
β = 95.626 (2)°T = 300 K
V = 1276.4 (4) Å3Prism, yellow
Z = 40.42 × 0.19 × 0.08 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer		3102 independent reflections
Radiation source: fine-focus sealed tube2578 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ω scanθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −6→6
Tmin = 0.783, Tmax = 0.953k = −9→15
8549 measured reflectionsl = −30→31
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0546P)2 + 0.3548P]
where P = (Fo2 + 2Fc2)/3
3102 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C12H9ClN2OS2V = 1276.4 (4) Å3
Mr = 296.78Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.6552 (7) ŵ = 0.61 mm−1
b = 11.660 (2) ÅT = 300 K
c = 23.630 (4) Å0.42 × 0.19 × 0.08 mm
β = 95.626 (2)°
Data collection top
Bruker SMART 1000 CCD
diffractometer		3102 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2578 reflections with I > 2σ(I)
Tmin = 0.783, Tmax = 0.953Rint = 0.019
8549 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.31 e Å−3
3102 reflectionsΔρmin = −0.20 e Å−3
172 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
Cl11.37357 (11)0.14501 (5)0.54454 (2)0.06174 (17)
S10.42417 (13)0.54355 (4)0.38816 (3)0.06558 (19)
S2−0.38487 (12)0.23708 (4)0.20193 (2)0.05870 (17)
O10.0745 (3)0.22204 (11)0.29637 (6)0.0549 (3)
N10.4375 (3)0.31315 (13)0.37757 (6)0.0426 (3)
H1N0.357 (5)0.2572 (18)0.3578 (9)0.053 (6)*
N20.0880 (3)0.41119 (13)0.32158 (7)0.0446 (3)
H2N0.001 (5)0.475 (2)0.3134 (10)0.063 (7)*
C11.1034 (4)0.19841 (16)0.49542 (8)0.0448 (4)
C20.9940 (4)0.12913 (16)0.45099 (8)0.0470 (4)
H21.06550.05540.44700.056*
C30.7761 (4)0.17123 (15)0.41242 (7)0.0446 (4)
H30.70100.12540.38230.053*
C40.6685 (4)0.28161 (15)0.41829 (7)0.0395 (3)
C50.7819 (4)0.34955 (16)0.46329 (8)0.0486 (4)
H50.71110.42330.46770.058*
C61.0007 (4)0.30746 (17)0.50170 (8)0.0506 (4)
H61.07770.35310.53170.061*
C70.3216 (4)0.41540 (14)0.36378 (7)0.0409 (4)
C8−0.0182 (4)0.32019 (15)0.28912 (7)0.0408 (4)
C9−0.2510 (4)0.34711 (15)0.24497 (7)0.0413 (4)
C10−0.3865 (4)0.44880 (17)0.22982 (8)0.0499 (4)
H10−0.34390.51830.24810.060*
C11−0.5988 (5)0.43535 (18)0.18316 (9)0.0574 (5)
H11−0.71090.49520.16710.069*
C12−0.6202 (5)0.32616 (19)0.16464 (9)0.0586 (5)
H12−0.75030.30220.13460.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0533 (3)0.0688 (3)0.0585 (3)−0.0017 (2)−0.0177 (2)0.0113 (2)
S10.0745 (4)0.0364 (2)0.0783 (4)−0.0039 (2)−0.0311 (3)−0.0049 (2)
S20.0706 (3)0.0434 (3)0.0563 (3)0.0030 (2)−0.0228 (2)−0.0074 (2)
O10.0672 (9)0.0381 (6)0.0547 (8)0.0023 (6)−0.0187 (6)−0.0028 (6)
N10.0463 (8)0.0358 (7)0.0429 (8)−0.0042 (6)−0.0088 (6)−0.0016 (6)
N20.0469 (8)0.0372 (7)0.0466 (8)0.0002 (6)−0.0105 (6)−0.0020 (6)
C10.0384 (8)0.0518 (10)0.0427 (9)−0.0060 (7)−0.0035 (7)0.0076 (7)
C20.0494 (10)0.0429 (9)0.0473 (9)0.0012 (8)−0.0023 (7)0.0025 (7)
C30.0491 (9)0.0403 (9)0.0423 (9)−0.0046 (7)−0.0060 (7)−0.0026 (7)
C40.0387 (8)0.0392 (8)0.0394 (8)−0.0047 (6)−0.0026 (6)0.0029 (7)
C50.0552 (10)0.0416 (9)0.0465 (9)−0.0005 (8)−0.0075 (8)−0.0035 (7)
C60.0526 (10)0.0501 (10)0.0460 (9)−0.0084 (8)−0.0113 (8)−0.0045 (8)
C70.0418 (8)0.0395 (8)0.0401 (8)−0.0048 (7)−0.0030 (6)−0.0010 (7)
C80.0428 (8)0.0395 (8)0.0388 (8)−0.0031 (7)−0.0020 (6)0.0002 (7)
C90.0436 (8)0.0394 (9)0.0392 (8)−0.0041 (7)−0.0042 (6)0.0001 (7)
C100.0528 (10)0.0419 (10)0.0519 (10)0.0004 (8)−0.0098 (8)0.0005 (8)
C110.0578 (11)0.0509 (11)0.0595 (12)0.0041 (9)−0.0146 (9)0.0077 (9)
C120.0620 (12)0.0570 (12)0.0514 (10)−0.0013 (9)−0.0214 (9)0.0007 (9)
Geometric parameters (Å, º) top
Cl1—C11.7408 (18)C2—H20.9300
S1—C71.6548 (17)C3—C41.393 (2)
S2—C121.693 (2)C3—H30.9300
S2—C91.7158 (17)C4—C51.388 (2)
O1—C81.229 (2)C5—C61.386 (3)
N1—C71.336 (2)C5—H50.9300
N1—C41.419 (2)C6—H60.9300
N1—H1N0.87 (2)C8—C91.463 (2)
N2—C81.373 (2)C9—C101.374 (2)
N2—C71.402 (2)C10—C111.415 (3)
N2—H2N0.86 (2)C10—H100.9300
C1—C61.372 (3)C11—C121.347 (3)
C1—C21.382 (3)C11—H110.9300
C2—C31.385 (2)C12—H120.9300
C12—S2—C991.64 (10)C1—C6—C5119.94 (17)
C7—N1—C4131.12 (15)C1—C6—H6120.0
C7—N1—H1N113.5 (14)C5—C6—H6120.0
C4—N1—H1N115.4 (14)N1—C7—N2114.12 (15)
C8—N2—C7129.51 (16)N1—C7—S1128.69 (13)
C8—N2—H2N113.9 (16)N2—C7—S1117.15 (13)
C7—N2—H2N116.5 (16)O1—C8—N2122.64 (16)
C6—C1—C2121.18 (16)O1—C8—C9121.65 (16)
C6—C1—Cl1119.75 (14)N2—C8—C9115.71 (15)
C2—C1—Cl1119.06 (15)C10—C9—C8131.32 (16)
C1—C2—C3118.96 (17)C10—C9—S2111.10 (13)
C1—C2—H2120.5C8—C9—S2117.57 (13)
C3—C2—H2120.5C9—C10—C11112.03 (17)
C2—C3—C4120.61 (16)C9—C10—H10124.0
C2—C3—H3119.7C11—C10—H10124.0
C4—C3—H3119.7C12—C11—C10112.44 (18)
C5—C4—C3119.35 (16)C12—C11—H11123.8
C5—C4—N1125.26 (16)C10—C11—H11123.8
C3—C4—N1115.33 (15)C11—C12—S2112.79 (15)
C6—C5—C4119.96 (18)C11—C12—H12123.6
C6—C5—H5120.0S2—C12—H12123.6
C4—C5—H5120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.87 (2)1.91 (2)2.651 (2)143 (2)
C12—H12···Cl1i0.932.693.523 (2)149
Symmetry code: (i) x−5/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC12H9ClN2OS2
Mr296.78
Crystal system, space groupMonoclinic, P21/n
Temperature (K)300
a, b, c (Å)4.6552 (7), 11.660 (2), 23.630 (4)
β (°) 95.626 (2)
V (Å3)1276.4 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.61
Crystal size (mm)0.42 × 0.19 × 0.08
Data collection
DiffractometerBruker SMART 1000 CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.783, 0.953
No. of measured, independent and
observed [I > 2σ(I)] reflections		8549, 3102, 2578
Rint0.019
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.107, 1.07
No. of reflections3102
No. of parameters172
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.31, −0.20

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2006) and CrystalStructure (Rigaku/MSC and Rigaku, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.87 (2)1.91 (2)2.651 (2)143 (2)
C12—H12···Cl1i0.932.693.523 (2)149.3
Symmetry code: (i) x−5/2, −y+1/2, z−1/2.
 

Acknowledgements

The authors are grateful to the Department of Chemistry, Research Complex, Allama Iqbal Open University, Islama­bad, and The Hong Kong Polytechnic University for providing laboratory and analytical facilities.

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2006). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationGu, C.-L., Liu, L., Sui, Y., Zhao, J.-L. D., Wang, D. & Chen, Y.-J. (2007). Tetrahedron, 18, 455–463.  CSD CrossRef CAS Google Scholar
 First citationJohnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
 First citationRigaku/MSC and Rigaku (2006). CrystalStructure. Rigaku/MSC, Texas, USA, and Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSaeed, S., Bhatti, M. H., Yunus, U. & Jones, P. G. (2008). Acta Cryst. E64, o1485.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSaeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010). Eur. J. Med. Chem. 45, 1323–1331.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationSaeed, S., Rashid, N., Tahir, A. & Jones, P. G. (2009). Acta Cryst. E65, o1870–o1871.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS, Göttingen University, Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXu, Y., Hua, W., Liu, X. & Zhu, D. (2004). Chin. J. Org. Chem. 24, 1217–1222.  CAS Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 5| May 2010| Page o1162
https://doi.org/10.1107/S1600536810013863
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