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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 11| November 2010| Page o2840
https://doi.org/10.1107/S1600536810040778

1-Methane­sulfonyl-1H-1,2,3-benzotriazole

Petr Štěpnička,a* Hana Solařováa and Ivana Císařováa

aDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague; Hlavova 2030, 12840 Prague 2, Czech Republic
*Correspondence e-mail: stepnic@natur.cuni.cz

(Received 7 October 2010; accepted 11 October 2010; online 20 October 2010)

The mol­ecular geometry of the title compound, C7H7N3O2S, does not differ much from that of the previously reported 4-toluene­sulfonyl analogue. Unlike the latter compound, however, mol­ecules of the title compound associate primarily via π–π stacking inter­actions of their benzene rings [centroid–centroid distance = 3.5865 (8) Å], forming columnar stacks along the crystallographic 21 axes. These stacks are inter­connected via weak C—H⋯O and C—H⋯N hydrogen bonds.

Related literature

For crystal structure of 1-(p-toluene­sulfon­yl)-1H-1,2,3-benzotriazole, see: Rodríguez et al. (2005[Rodríguez, R., Nogueras, M., Cobo, J., Low, J. N. & Glidewell, C. (2005). Acta Cryst. E61, o2795-o2797.]). For the preparation of the title compound and examples of its synthetic use, see: Katritzky et al. (1992[Katritzky, A. R., Shobana, N., Pernak, J., Afridi, A. S. & Fan, W.-Q. (1992). Tetrahedron, 48, 7817-7822.], 2000[Katritzky, A. R., He, H.-Y. & Suzuki, K. (2000). J. Org. Chem. 65, 8210-8213.]).

[Scheme 1]

Experimental

Crystal data

  • C7H7N3O2S

  • Mr = 197.22

  • Monoclinic, P 21 /c

  • a = 9.3685 (3) Å

  • b = 7.0627 (2) Å

  • c = 12.4994 (3) Å

  • β = 92.984 (2)°

  • V = 825.93 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.36 mm−1

  • T = 150 K

  • 0.50 × 0.30 × 0.25 mm
Data collection

  • Nonius KappaCCD diffractometer

  • 14989 measured reflections

  • 1886 independent reflections

  • 1674 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.082

  • S = 1.09

  • 1886 reflections

  • 119 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯O2i 0.93 2.55 3.270 (2) 135
C6—H6⋯O1ii 0.93 2.55 3.451 (2) 164
C8—H8B⋯N3iii 0.96 2.61 3.446 (2) 145
C8—H8C⋯O2iv 0.96 2.40 3.325 (2) 161
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z+1; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999)[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810040778/im2237sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040778/im2237Isup2.hkl

checkCIF report


Comment top

The title compound, 1-(methanesulfonyl)-1H-1,2,3-benzotriazole, is a useful and readily accessible organic reagent, acting as a convenient source of the benzotriazolyl anion. For instance, it reacts smoothly with carboxylic acids in the presence of a base to afford the corresponding 1-acyl-1H-1,2,3-benzotriazoles, which can be subsequently converted to amides in typically good yields (Katritzky et al., 2000).

The molecular structure of the title compound (Fig. 1) is rather unexceptional, particularly in view of the geometric data reported earlier for the related 1H-1,2,3-benzotriazole derivative, 1-(p-toluenesulfonyl)-1H-1,2,3-benzotriazole (Rodríguez et al., 2005). The N—N bonds within the triazole ring clearly maintain their localized character (cf. N1—N2 = 1.389 (2) Å, N3—N2 = 1.288 (2) Å), which is, however, not reflected in the adjacent bonds. The lengths of the remaining in-ring bonds, N1—C7A, C7A—C3A and C3A—N3, differ by less than ca 0.006 Å, while all in-ring angles span a range of 103.5 (1)–109.9 (1) °. On the other hand, the variation in the analogous parameters describing the geometry of the annelating benzene ring is less pronounced (cf. C—C = 1.371 (2)–1.408 (2) Å, C—C—C = 115.5 (1)–122.7 (1) °).

The methanesulfonyl group binds to the triazole ring somewhat unsymmetrically, which is best demonstrated by the difference in the S—N1—N2 (120.12 (9) °) and S—N1—C7A (129.8 (1) °) angles. Moreover, it is angularly distorted: The bond angles around sulfur span a range of 103.43 (6)–120.31 (7) ° with the N1—S—C8 and O1—S—O2 angles being the lower and upper limit, respectively. The remaining angles do not differ much in the pairs: N1—S—O(1/2) (ca 105 °, difference ca 0.4 °), C8—S1—O(1/2) (ca 110 °, difference ca 1.2 °). Indeed, such a variation in bond angles corresponds with distances to the sulfur atom (S—O1 1.425 (1), S—O2 1.419 (1), S—N1 1.692 (1), S—C8 1.744 (2) Å) as the most acute angle is associated with the shortest bonds.

In the crystal, molecules of the title compound assemble via π–π stacking interactions of their benzene rings (Fig. 2a). Since this interaction involves molecules related by the crystallographic 21 screw axes, it results in the formation of infinite columnar stacks in the direction of the crystallographic b axis. It is worth pointing out that the observed separation of the ring centroids [Cg···Cg (-x, 1/2 + y, 1/2-z; 3.5865 (8) Å] is slightly shorter than that reported for α-graphite (ca 3.65 Å), where, however, the rings are slipped by ca 1.42 Å. Finally, the neighboring columnar stacks are interlinked by soft C—H···O and C—H···N hydrogen bonds (Table 1) into a complicated three-dimensional array (Figs. 2b and 2c).

Related literature top

For crystal structure of 1-(p-toluenesulfonyl)-1H-1,2,3-benzotriazole, see: Rodríguez et al. (2005). For the preparation of the title compound and examples of its synthetic use, see: Katritzky et al. (1992, 2000).

Experimental top

The title compound was synthesized from 1H-1,2,3-benzotriazole and methanesulfonyl chloride as described in the literature with a yield of 91% (Katritzky et al., 2000). Crystals suitable for X-ray diffraction analysis were obtained by crystallization from warm benzene.

Refinement top

H-atoms were included in calculated positions and refined as riding atoms with fixed C—H distances [C—H = 0.96 Å for CH3, and 0.93 Å for aromatic CH] and Uiso(H) assigned to 1.5Ueq(C) (CH3) or 1.2Ueq(C) (aromatic CH) of their bonding carbon atom.

Structure description top

The title compound, 1-(methanesulfonyl)-1H-1,2,3-benzotriazole, is a useful and readily accessible organic reagent, acting as a convenient source of the benzotriazolyl anion. For instance, it reacts smoothly with carboxylic acids in the presence of a base to afford the corresponding 1-acyl-1H-1,2,3-benzotriazoles, which can be subsequently converted to amides in typically good yields (Katritzky et al., 2000).

The molecular structure of the title compound (Fig. 1) is rather unexceptional, particularly in view of the geometric data reported earlier for the related 1H-1,2,3-benzotriazole derivative, 1-(p-toluenesulfonyl)-1H-1,2,3-benzotriazole (Rodríguez et al., 2005). The N—N bonds within the triazole ring clearly maintain their localized character (cf. N1—N2 = 1.389 (2) Å, N3—N2 = 1.288 (2) Å), which is, however, not reflected in the adjacent bonds. The lengths of the remaining in-ring bonds, N1—C7A, C7A—C3A and C3A—N3, differ by less than ca 0.006 Å, while all in-ring angles span a range of 103.5 (1)–109.9 (1) °. On the other hand, the variation in the analogous parameters describing the geometry of the annelating benzene ring is less pronounced (cf. C—C = 1.371 (2)–1.408 (2) Å, C—C—C = 115.5 (1)–122.7 (1) °).

The methanesulfonyl group binds to the triazole ring somewhat unsymmetrically, which is best demonstrated by the difference in the S—N1—N2 (120.12 (9) °) and S—N1—C7A (129.8 (1) °) angles. Moreover, it is angularly distorted: The bond angles around sulfur span a range of 103.43 (6)–120.31 (7) ° with the N1—S—C8 and O1—S—O2 angles being the lower and upper limit, respectively. The remaining angles do not differ much in the pairs: N1—S—O(1/2) (ca 105 °, difference ca 0.4 °), C8—S1—O(1/2) (ca 110 °, difference ca 1.2 °). Indeed, such a variation in bond angles corresponds with distances to the sulfur atom (S—O1 1.425 (1), S—O2 1.419 (1), S—N1 1.692 (1), S—C8 1.744 (2) Å) as the most acute angle is associated with the shortest bonds.

In the crystal, molecules of the title compound assemble via π–π stacking interactions of their benzene rings (Fig. 2a). Since this interaction involves molecules related by the crystallographic 21 screw axes, it results in the formation of infinite columnar stacks in the direction of the crystallographic b axis. It is worth pointing out that the observed separation of the ring centroids [Cg···Cg (-x, 1/2 + y, 1/2-z; 3.5865 (8) Å] is slightly shorter than that reported for α-graphite (ca 3.65 Å), where, however, the rings are slipped by ca 1.42 Å. Finally, the neighboring columnar stacks are interlinked by soft C—H···O and C—H···N hydrogen bonds (Table 1) into a complicated three-dimensional array (Figs. 2b and 2c).

For crystal structure of 1-(p-toluenesulfonyl)-1H-1,2,3-benzotriazole, see: Rodríguez et al. (2005). For the preparation of the title compound and examples of its synthetic use, see: Katritzky et al. (1992, 2000).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing displacement ellipsoids for the non-H atoms at the 50% probability level. Hydrogen atoms are presented as spheres with arbitrary radii.
[Figure 2] Fig. 2. (a) Section of columnar stacks connected by π–π interactions of the benzene rings [Cg···Cg = 3.5865 (8) Å]. (b) H-bond interactions generated by the molecules of the title compounds. (c) View of the unit cell along the crystallographic a axis.
1-Methanesulfonyl-1H-1,2,3-benzotriazole top
Crystal data top
C7H7N3O2SF(000) = 408
Mr = 197.22Dx = 1.586 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2027 reflections
a = 9.3685 (3) Åθ = 1.0–27.5°
b = 7.0627 (2) ŵ = 0.36 mm−1
c = 12.4994 (3) ÅT = 150 K
β = 92.984 (2)°Block, colourless
V = 825.93 (4) Å30.50 × 0.30 × 0.25 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer		1674 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Horizontally mounted graphite crystal monochromatorθmax = 27.5°, θmin = 2.2°
Detector resolution: 9.091 pixels mm-1h = −12→12
ω and π scans to fill the Ewald spherek = −9→9
14989 measured reflectionsl = −16→16
1886 independent reflections
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0431P)2 + 0.2983P]
where P = (Fo2 + 2Fc2)/3
1886 reflections(Δ/σ)max < 0.001
119 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
C7H7N3O2SV = 825.93 (4) Å3
Mr = 197.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.3685 (3) ŵ = 0.36 mm−1
b = 7.0627 (2) ÅT = 150 K
c = 12.4994 (3) Å0.50 × 0.30 × 0.25 mm
β = 92.984 (2)°
Data collection top
Nonius KappaCCD
diffractometer		1674 reflections with I > 2σ(I)
14989 measured reflectionsRint = 0.023
1886 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.082H-atom parameters constrained
S = 1.09Δρmax = 0.29 e Å−3
1886 reflectionsΔρmin = −0.42 e Å−3
119 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two least-squares 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 least-squares planes.

Refinement. Refinement of F2 against all diffractions. 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 > 2σ(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
S0.39056 (3)0.07483 (5)0.36695 (2)0.02263 (12)
O10.32920 (11)−0.04099 (16)0.44586 (8)0.0318 (3)
O20.51042 (11)0.01011 (18)0.31253 (8)0.0337 (3)
N10.25880 (13)0.10614 (17)0.27080 (9)0.0236 (3)
N20.29032 (13)0.10541 (18)0.16344 (9)0.0274 (3)
N30.17185 (13)0.11648 (19)0.10673 (9)0.0289 (3)
C3A0.05897 (15)0.1243 (2)0.17395 (11)0.0233 (3)
C4−0.08866 (16)0.1336 (2)0.14889 (12)0.0290 (3)
H4−0.12530.13810.07840.035*
C5−0.17615 (16)0.1359 (2)0.23349 (12)0.0295 (3)
H5−0.27460.14130.22000.035*
C6−0.12050 (16)0.1302 (2)0.34029 (12)0.0290 (3)
H6−0.18370.13180.39530.035*
C70.02458 (16)0.1222 (2)0.36641 (11)0.0273 (3)
H70.06110.11990.43700.033*
C7A0.11237 (14)0.11801 (19)0.27980 (11)0.0218 (3)
C80.41970 (16)0.3025 (2)0.41766 (11)0.0277 (3)
H8A0.49010.29770.47620.042*
H8B0.33190.35210.44240.042*
H8C0.45310.38280.36230.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.02097 (19)0.0276 (2)0.01921 (18)0.00087 (12)0.00002 (12)0.00117 (12)
O10.0327 (6)0.0361 (6)0.0263 (5)−0.0063 (5)−0.0026 (4)0.0100 (4)
O20.0245 (5)0.0461 (7)0.0306 (5)0.0088 (5)0.0010 (4)−0.0071 (5)
N10.0209 (6)0.0317 (6)0.0183 (5)0.0002 (5)0.0016 (4)0.0007 (4)
N20.0275 (6)0.0369 (7)0.0180 (5)−0.0017 (5)0.0030 (4)0.0007 (5)
N30.0264 (6)0.0402 (7)0.0201 (6)−0.0023 (5)0.0002 (5)0.0017 (5)
C3A0.0252 (7)0.0222 (7)0.0223 (6)−0.0016 (5)−0.0002 (5)0.0008 (5)
C40.0266 (7)0.0293 (7)0.0304 (7)−0.0015 (6)−0.0052 (6)0.0009 (6)
C50.0220 (7)0.0251 (7)0.0413 (8)−0.0012 (6)0.0005 (6)0.0008 (6)
C60.0263 (7)0.0262 (7)0.0352 (8)0.0000 (6)0.0100 (6)0.0008 (6)
C70.0290 (7)0.0294 (7)0.0238 (7)0.0010 (6)0.0038 (5)0.0010 (6)
C7A0.0212 (6)0.0217 (6)0.0225 (6)0.0001 (5)0.0005 (5)0.0006 (5)
C80.0301 (7)0.0290 (7)0.0239 (6)−0.0017 (6)0.0001 (5)−0.0003 (6)
Geometric parameters (Å, º) top
S—O21.4185 (10)C4—H40.9300
S—O11.4254 (11)C5—C61.408 (2)
S—N11.6919 (12)C5—H50.9300
S—C81.7444 (15)C6—C71.382 (2)
N1—C7A1.3848 (17)C6—H60.9300
N1—N21.3890 (16)C7—C7A1.3936 (19)
N2—N31.2878 (17)C7—H70.9300
N3—C3A1.3856 (18)C8—H8A0.9600
C3A—C7A1.3905 (18)C8—H8B0.9600
C3A—C41.4037 (19)C8—H8C0.9600
C4—C51.371 (2)
O2—S—O1120.31 (7)C4—C5—H5119.2
O2—S—N1105.55 (6)C6—C5—H5119.2
O1—S—N1105.13 (6)C7—C6—C5122.41 (14)
O2—S—C8111.01 (7)C7—C6—H6118.8
O1—S—C8109.79 (7)C5—C6—H6118.8
N1—S—C8103.43 (6)C6—C7—C7A115.48 (13)
C7A—N1—N2109.87 (11)C6—C7—H7122.3
C7A—N1—S129.75 (9)C7A—C7—H7122.3
N2—N1—S120.12 (9)N1—C7A—C3A103.50 (11)
N3—N2—N1108.12 (11)N1—C7A—C7133.75 (13)
N2—N3—C3A109.37 (11)C3A—C7A—C7122.74 (13)
N3—C3A—C7A109.12 (12)S—C8—H8A109.5
N3—C3A—C4129.85 (13)S—C8—H8B109.5
C7A—C3A—C4121.02 (13)H8A—C8—H8B109.5
C5—C4—C3A116.74 (13)S—C8—H8C109.5
C5—C4—H4121.6H8A—C8—H8C109.5
C3A—C4—H4121.6H8B—C8—H8C109.5
C4—C5—C6121.60 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.932.553.270 (2)135
C6—H6···O1ii0.932.553.451 (2)164
C8—H8B···N3iii0.962.613.446 (2)145
C8—H8C···O2iv0.962.403.325 (2)161
Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC7H7N3O2S
Mr197.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)9.3685 (3), 7.0627 (2), 12.4994 (3)
β (°) 92.984 (2)
V (Å3)825.93 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.36
Crystal size (mm)0.50 × 0.30 × 0.25
Data collection
DiffractometerNonius KappaCCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		14989, 1886, 1674
Rint0.023
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.082, 1.09
No. of reflections1886
No. of parameters119
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.29, −0.42

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.932.553.270 (2)135
C6—H6···O1ii0.932.553.451 (2)164
C8—H8B···N3iii0.962.613.446 (2)145
C8—H8C···O2iv0.962.403.325 (2)161
Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

Financial support from the Ministry of Education of the Czech Republic (project No. MSM0021620857) is gratefully acknowledged.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationKatritzky, A. R., He, H.-Y. & Suzuki, K. (2000). J. Org. Chem. 65, 8210–8213.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationKatritzky, A. R., Shobana, N., Pernak, J., Afridi, A. S. & Fan, W.-Q. (1992). Tetrahedron, 48, 7817–7822.  CrossRef CAS Web of Science Google Scholar
 First citationNonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationRodríguez, R., Nogueras, M., Cobo, J., Low, J. N. & Glidewell, C. (2005). Acta Cryst. E61, o2795–o2797.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2840
https://doi.org/10.1107/S1600536810040778
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