3-[2-(1,3-Benzothia­zol-2-ylsulfan­yl)eth­yl]-1,3-oxazolidin-2-one

Ma, C.-H.; Li, X.-F.; An, Y.; Wen, Y.-H.

doi:10.1107/S1600536810034264

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2472

doi:10.1107/S1600536810034264

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3-[2-(1,3-Benzothiazol-2-ylsulfanyl)ethyl]-1,3-oxazolidin-2-one

Cong-Hui Ma,^a Xiao-Feng Li,^b Yan An ^b and Yong-Hong Wen ^a ^*

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China, and ^bInstitute of Marine Materials Science and Engineering, Shanghai Maritime University, Shanghai 201305, People's Republic of China
^*Correspondence e-mail: wenyyhh@126.com

(Received 21 July 2010; accepted 25 August 2010; online 4 September 2010)

The title compound, C₁₂H₁₂N₂S₂O₂, consists of a benzothiazole group and a oxazolidin-1-one linked via a flexible ethane-1,2-diyl spacer. The benzothiazole group and the oxazolidine ring are each almost planar [with maximum deviations of 0.007 (2) and 0.044 (3) Å, respectively] and make a dihedral angle of 9.35 (10)°. In the crystal structure, adjacent molecules were connected through C—H⋯O and C—H⋯N hydrogen bonds, and further extended into a three-dimensional network structure through intermolecular aromatic π–π stacking interactions in which the centroid–centroid distance is 3.590 (1) Å.

Related literature

For background to the applications of 2-oxazolidinones, see: Ippolito et al. (2008 ); Mullera et al. (1999 ).

Experimental

Crystal data

C₁₂H₁₂N₂O₂S₂
M_r = 280.36
Triclinic, $[P \overline 1]$
a = 6.5804 (4) Å
b = 7.8331 (5) Å
c = 12.5890 (7) Å
α = 99.864 (5)°
β = 97.715 (5)°
γ = 97.011 (5)°
V = 626.49 (7) Å³
Z = 2
Cu Kα radiation
μ = 3.83 mm⁻¹
T = 293 K
0.16 × 0.14 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.572, T_max = 1.000
4029 measured reflections
2396 independent reflections
2081 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.111
S = 1.05
2396 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O1ⁱ	0.97	2.58	3.466 (3)	152
C3—H3⋯O1ⁱⁱ	0.93	2.59	3.282 (2)	132
C5—H5⋯N1ⁱ	0.93	2.54	3.445 (2)	163
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z-1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034264/bv2154sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810034264/bv2154Isup2.hkl

checkCIF report

Comment top

N-substituted 2-oxazolidinones have been widely used as antibiotics which are effective against gram-positive bacteria (Ippolito et al., 2008; Mullera et al., 1999). In this article we provide a new synthetic route of a 2-oxazolidinone derivative. Even though the reaction mechanism has not been established, the reproducibility and high yield of the reaction should prove useful for the synthesis of this type of compound.

Herein, we report the synthesis and structure of the title compound, namely 3-(2-(benzo[d]thiazol-2-ylthio)ethyl)-oxazolidin-2-one (Fig.1). As shown in Fig. 2, a two-dimensional supramolecular network was formed by hydrogen bonds (Table 1) and weak π-π stacking interactions between the phenyl rings and the thiazolyl rings of adjacent molecules with a centroid-centroid distances of 3.590 Å along b direction.

Related literature top

For background to the applications of 2-oxazolidinones, see: Ippolito et al. (2008); Mullera et al. (1999).

Experimental top

A mixture of 2-mercaptobenzothiazole (6.69 g, 0.04 mol), potassium carbonate (8.29 g, 0.06 mol) and ethanol (250 ml) was heated and stirred in a 500 ml flask. Bis(2-chloroethyl)amine hydrochloride (7.14 g, 0.04 mol, dissolved in 100 ml ethanol) was added dropwise into the flask when the mixture was heated to 353 K, and the mixture was further stired at 353 K for 8 h. After cooling, the precipitate was filtered, washed with ethanol and water, and recrystallized from ethanol to obtain a flaxen powder. Yield: 68%. ¹H NMR (CDCl₃, 400 MHz):3.60 (t, 2H), 3.74 (m, 4H), 4.3 (t, 2H), 7.45 (m, 2H), 7.77 (d, 1H), 7.79 (d, 1H). ¹³C NMR (CDCl₃, 125 MHz): 31.17, 43.81, 45.58, 61.97, 121.40, 121.41, 124.55, 126.20, 135.26, 152.86, 158.40, 165.71.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis CCD (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. The three-dimensional structure by molecular packing, showing the hydrogen bonds as blue dashed lines, and π-π stacking interactions as red dashed lines.

3-[2-(1,3-Benzothiazol-2-ylsulfanyl)ethyl]-1,3-oxazolidin-2-one top

Crystal data top

C₁₂H₁₂N₂O₂S₂	Z = 2
M_r = 280.36	F(000) = 292
Triclinic, P1	D_x = 1.486 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.5804 (4) Å	Cell parameters from 2669 reflections
b = 7.8331 (5) Å	θ = 3.6–72.2°
c = 12.5890 (7) Å	µ = 3.83 mm⁻¹
α = 99.864 (5)°	T = 293 K
β = 97.715 (5)°	Rhombus, colourless
γ = 97.011 (5)°	0.16 × 0.14 × 0.10 mm
V = 626.49 (7) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2396 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2081 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 16.0355 pixels mm^-1	θ_max = 72.4°, θ_min = 3.6°
ω scans	h = −7→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	k = −9→8
T_min = 0.572, T_max = 1.000	l = −15→15
4029 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.081P)² + 0.008P] where P = (F_o² + 2F_c²)/3
2396 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₂H₁₂N₂O₂S₂	γ = 97.011 (5)°
M_r = 280.36	V = 626.49 (7) Å³
Triclinic, P1	Z = 2
a = 6.5804 (4) Å	Cu Kα radiation
b = 7.8331 (5) Å	µ = 3.83 mm⁻¹
c = 12.5890 (7) Å	T = 293 K
α = 99.864 (5)°	0.16 × 0.14 × 0.10 mm
β = 97.715 (5)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2396 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	2081 reflections with I > 2σ(I)
T_min = 0.572, T_max = 1.000	R_int = 0.020
4029 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.05	Δρ_max = 0.25 e Å⁻³
2396 reflections	Δρ_min = −0.38 e Å⁻³
163 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 > σ(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

	x	y	z	U_iso*/U_eq
S1	0.35142 (6)	0.68528 (6)	0.47728 (3)	0.04252 (17)
S2	−0.03291 (7)	0.79117 (6)	0.57333 (4)	0.04677 (17)
O1	0.2992 (3)	1.2011 (2)	0.90981 (13)	0.0693 (5)
O2	0.6287 (3)	1.1616 (2)	0.95686 (12)	0.0661 (4)
N1	−0.0218 (2)	0.6472 (2)	0.36963 (12)	0.0407 (3)
N2	0.4734 (2)	1.0512 (2)	0.78894 (12)	0.0465 (4)
C1	0.1020 (3)	0.5814 (2)	0.29599 (14)	0.0370 (4)
C2	0.0334 (3)	0.5093 (3)	0.18583 (15)	0.0466 (4)
H2	−0.1048	0.5029	0.1556	0.056*
C3	0.1746 (3)	0.4474 (3)	0.12252 (15)	0.0500 (4)
H3	0.1301	0.3982	0.0492	0.060*
C4	0.3836 (3)	0.4578 (2)	0.16706 (16)	0.0474 (4)
H4	0.4757	0.4152	0.1228	0.057*
C5	0.4548 (3)	0.5301 (2)	0.27549 (15)	0.0424 (4)
H5	0.5937	0.5382	0.3050	0.051*
C6	0.3115 (3)	0.5908 (2)	0.33941 (14)	0.0358 (3)
C7	0.0866 (3)	0.7046 (2)	0.46521 (14)	0.0370 (4)
C8	0.1759 (3)	0.8424 (2)	0.68809 (14)	0.0441 (4)
H8A	0.1174	0.8441	0.7549	0.053*
H8B	0.2621	0.7503	0.6824	0.053*
C9	0.3115 (3)	1.0177 (2)	0.69552 (15)	0.0474 (4)
H9A	0.3729	1.0166	0.6296	0.057*
H9B	0.2267	1.1109	0.7014	0.057*
C10	0.6791 (3)	1.0058 (3)	0.78669 (19)	0.0533 (5)
H10A	0.7520	1.0668	0.7389	0.064*
H10B	0.6755	0.8806	0.7642	0.064*
C11	0.7754 (4)	1.0685 (4)	0.9048 (2)	0.0683 (6)
H11A	0.8023	0.9698	0.9390	0.082*
H11B	0.9054	1.1453	0.9106	0.082*
C12	0.4514 (3)	1.1428 (2)	0.88637 (15)	0.0480 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0296 (2)	0.0517 (3)	0.0405 (3)	0.00659 (18)	−0.00164 (17)	−0.00180 (18)
S2	0.0372 (3)	0.0556 (3)	0.0451 (3)	0.0092 (2)	0.00809 (19)	−0.0001 (2)
O1	0.0739 (11)	0.0767 (11)	0.0617 (9)	0.0256 (9)	0.0276 (8)	0.0019 (8)
O2	0.0723 (10)	0.0682 (10)	0.0476 (8)	0.0023 (8)	−0.0068 (7)	0.0007 (7)
N1	0.0317 (7)	0.0481 (8)	0.0408 (8)	0.0079 (6)	0.0018 (6)	0.0062 (6)
N2	0.0426 (9)	0.0500 (8)	0.0431 (8)	0.0105 (7)	0.0052 (7)	−0.0030 (7)
C1	0.0337 (8)	0.0381 (8)	0.0395 (8)	0.0059 (6)	0.0031 (7)	0.0097 (7)
C2	0.0420 (10)	0.0542 (10)	0.0397 (9)	0.0055 (8)	−0.0022 (7)	0.0063 (8)
C3	0.0567 (11)	0.0524 (10)	0.0382 (9)	0.0068 (9)	0.0046 (8)	0.0043 (8)
C4	0.0509 (11)	0.0448 (9)	0.0485 (10)	0.0101 (8)	0.0163 (8)	0.0055 (8)
C5	0.0355 (9)	0.0411 (9)	0.0497 (10)	0.0065 (7)	0.0073 (7)	0.0055 (7)
C6	0.0325 (8)	0.0348 (7)	0.0380 (8)	0.0026 (6)	0.0021 (6)	0.0055 (6)
C7	0.0304 (8)	0.0379 (8)	0.0412 (9)	0.0049 (6)	0.0027 (7)	0.0055 (7)
C8	0.0489 (10)	0.0438 (9)	0.0393 (9)	0.0074 (8)	0.0074 (8)	0.0061 (7)
C9	0.0554 (11)	0.0409 (9)	0.0434 (9)	0.0079 (8)	0.0032 (8)	0.0044 (7)
C10	0.0478 (11)	0.0488 (10)	0.0680 (13)	0.0128 (8)	0.0168 (10)	0.0146 (9)
C11	0.0440 (12)	0.0807 (16)	0.0786 (16)	0.0031 (11)	−0.0035 (11)	0.0250 (13)
C12	0.0544 (11)	0.0448 (9)	0.0431 (10)	0.0062 (8)	0.0100 (8)	0.0028 (8)

Geometric parameters (Å, º) top

S1—C6	1.7376 (17)	C3—C4	1.401 (3)
S1—C7	1.7564 (17)	C3—H3	0.9300
S2—C7	1.7412 (17)	C4—C5	1.379 (3)
S2—C8	1.8083 (19)	C4—H4	0.9300
O1—C12	1.202 (2)	C5—C6	1.394 (2)
O2—C12	1.343 (2)	C5—H5	0.9300
O2—C11	1.439 (3)	C8—C9	1.525 (3)
N1—C7	1.290 (2)	C8—H8A	0.9700
N1—C1	1.389 (2)	C8—H8B	0.9700
N2—C12	1.346 (2)	C9—H9A	0.9700
N2—C9	1.441 (2)	C9—H9B	0.9700
N2—C10	1.444 (3)	C10—C11	1.509 (3)
C1—C2	1.396 (2)	C10—H10A	0.9700
C1—C6	1.401 (2)	C10—H10B	0.9700
C2—C3	1.382 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700

C6—S1—C7	88.66 (8)	C9—C8—S2	113.55 (13)
C7—S2—C8	103.28 (8)	C9—C8—H8A	108.9
C12—O2—C11	109.30 (16)	S2—C8—H8A	108.9
C7—N1—C1	110.61 (14)	C9—C8—H8B	108.9
C12—N2—C9	122.28 (17)	S2—C8—H8B	108.9
C12—N2—C10	112.88 (17)	H8A—C8—H8B	107.7
C9—N2—C10	124.61 (16)	N2—C9—C8	110.74 (16)
N1—C1—C2	125.28 (16)	N2—C9—H9A	109.5
N1—C1—C6	115.23 (15)	C8—C9—H9A	109.5
C2—C1—C6	119.48 (17)	N2—C9—H9B	109.5
C3—C2—C1	118.82 (18)	C8—C9—H9B	109.5
C3—C2—H2	120.6	H9A—C9—H9B	108.1
C1—C2—H2	120.6	N2—C10—C11	100.92 (18)
C2—C3—C4	121.05 (18)	N2—C10—H10A	111.6
C2—C3—H3	119.5	C11—C10—H10A	111.6
C4—C3—H3	119.5	N2—C10—H10B	111.6
C5—C4—C3	120.99 (18)	C11—C10—H10B	111.6
C5—C4—H4	119.5	H10A—C10—H10B	109.4
C3—C4—H4	119.5	O2—C11—C10	106.53 (17)
C4—C5—C6	117.81 (17)	O2—C11—H11A	110.4
C4—C5—H5	121.1	C10—C11—H11A	110.4
C6—C5—H5	121.1	O2—C11—H11B	110.4
C5—C6—C1	121.83 (16)	C10—C11—H11B	110.4
C5—C6—S1	128.83 (14)	H11A—C11—H11B	108.6
C1—C6—S1	109.34 (13)	O1—C12—O2	123.44 (19)
N1—C7—S2	119.85 (13)	O1—C12—N2	126.8 (2)
N1—C7—S1	116.15 (13)	O2—C12—N2	109.76 (17)
S2—C7—S1	123.99 (10)

C7—N1—C1—C2	179.93 (17)	C8—S2—C7—S1	−1.39 (13)
C7—N1—C1—C6	0.0 (2)	C6—S1—C7—N1	0.16 (14)
N1—C1—C2—C3	−179.38 (17)	C6—S1—C7—S2	179.01 (12)
C6—C1—C2—C3	0.5 (3)	C7—S2—C8—C9	82.41 (15)
C1—C2—C3—C4	−0.6 (3)	C12—N2—C9—C8	−92.9 (2)
C2—C3—C4—C5	0.0 (3)	C10—N2—C9—C8	92.9 (2)
C3—C4—C5—C6	0.7 (3)	S2—C8—C9—N2	179.53 (12)
C4—C5—C6—C1	−0.7 (3)	C12—N2—C10—C11	6.1 (2)
C4—C5—C6—S1	179.22 (14)	C9—N2—C10—C11	−179.26 (19)
N1—C1—C6—C5	−179.97 (15)	C12—O2—C11—C10	7.0 (3)
C2—C1—C6—C5	0.1 (3)	N2—C10—C11—O2	−7.6 (2)
N1—C1—C6—S1	0.08 (19)	C11—O2—C12—O1	176.9 (2)
C2—C1—C6—S1	−179.82 (14)	C11—O2—C12—N2	−3.2 (2)
C7—S1—C6—C5	179.93 (17)	C9—N2—C12—O1	3.0 (3)
C7—S1—C6—C1	−0.13 (13)	C10—N2—C12—O1	177.8 (2)
C1—N1—C7—S2	−179.04 (12)	C9—N2—C12—O2	−176.91 (16)
C1—N1—C7—S1	−0.14 (19)	C10—N2—C12—O2	−2.1 (2)
C8—S2—C7—N1	177.42 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1ⁱ	0.97	2.58	3.466 (3)	152
C3—H3···O1ⁱⁱ	0.93	2.59	3.282 (2)	132
C5—H5···N1ⁱ	0.93	2.54	3.445 (2)	163

Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂O₂S₂
M_r	280.36
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.5804 (4), 7.8331 (5), 12.5890 (7)
α, β, γ (°)	99.864 (5), 97.715 (5), 97.011 (5)
V (Å³)	626.49 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	3.83
Crystal size (mm)	0.16 × 0.14 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2005)
T_min, T_max	0.572, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4029, 2396, 2081
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.111, 1.05
No. of reflections	2396
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.38

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1ⁱ	0.97	2.58	3.466 (3)	152.3
C3—H3···O1ⁱⁱ	0.93	2.59	3.282 (2)	131.5
C5—H5···N1ⁱ	0.93	2.54	3.445 (2)	163.3

Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z−1.

Acknowledgements

The authors acknowledge the Project of Shanghai Municipal Education Commission (09YZ245, 10YZ111, 10ZZ98), the `Chen Guang' project supported by Shanghai Municipal Education Commission and Shanghai Education Development Foundation (09 C G52) and the State Key Laboratory of Pollution Control and Resource Reuse Foundation (PCRRF09001) for financial support.

References

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