Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Page o782
https://doi.org/10.1107/S1600536814013518

N-Methyl-N-nitroso-p-toluene­sulfon­amide

Kartik Rai,a Vincent Wu,a Priya Gupta,a David A. Laviskaa and Benny C. Chana*

aDepartment of Chemistry, The College of New Jersey, 2000 Pennington Rd, Ewing, NJ 08628, USA
*Correspondence e-mail: chan@tcnj.edu

(Received 24 April 2014; accepted 10 June 2014; online 14 June 2014)

The crystal structure of the title compound, C8H10N2O3S, displays predominant C—H⋯O hydrogen-bonding and π–π stacking inter­actions. The hydrogen bonds are between the O atoms of the sulfonyl group and H atoms on methyl groups. The π–π stacking inter­actions occur between adjacent aromatic rings, with a centroid–centroid distance of 3.868 (11) Å. These inter­actions lead to the formation of chains parallel to (101).

CCDC reference: 1007700

Related literature

For the use of the title compound as a nitro­sylating agent, see: Mayer et al. (2014[Mayer, T., Mayer, P. & Bottcher, H. (2014). J. Organomet. Chem. 751, 368-373.]). For related structures, see: Hakkinen et al. (1988[Hakkinen, A., Ruostesuo, P. & Kivekas, R. (1988). J. Chem. Soc. Perkin Trans. 2, pp. 815-820.]); Lightfoot et al. (1993[Lightfoot, P., Tremayne, M., Glidewell, K. D. & Bruce, P. G. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 1625-1630.]). For the use of the title compound as a potential cancer chemotherapeutic, see: Garcia-Rio et al. (2011[Garcia-Rio, L., Raposa-Barreiro, M. L. & Rodriguez-Dafonte, P. (2011). Org. Chem. Argentina, 7, 272-282.]); Skinner et al. (1960[Skinner, W. A., Gram, H. F., Greene, M. O., Greenberg, J. & Baker, B. R. (1960). J. Med. Pharm. Chem. 2, 299-333.]). For its use as an anti­microbial, see: Uri & Scola (1992[Uri, J. V. & Scola, F. (1992). Acta Microbiol. Hung. 39, 317-322.]) and as a precursor in methyl­ene production and production of heterocyclic rings, see: Hudlicky (1980[Hudlicky, M. (1980). J. Org. Chem. 45, 5377-5378.]). For literature hydrogen-bond lengths between sulfonyl O atoms and methyl H atoms in sulfonamide structures, see: Dodoff et al. (2004[Dodoff, N. I., Varga, R. A. & Kovala-Demrtzi, D. (2004). Z. Naturforsch. Teil B, 59, 1070-1076.]). For the potential use of sulfonamide compounds as ligands for metal coordination, see: Jacobs et al. (2013[Jacobs, D. L., Chan, B. C. & O'Connor, A. R. (2013). Acta Cryst. C69, 1397-1401.]).

[Scheme 1]

Experimental

Crystal data

  • C8H10N2O3S

  • Mr = 214.24

  • Triclinic, [P \overline 1]

  • a = 6.8911 (8) Å

  • b = 8.4435 (10) Å

  • c = 8.6248 (10) Å

  • α = 81.458 (1)°

  • β = 85.883 (1)°

  • γ = 80.310 (1)°

  • V = 488.62 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 100 K

  • 0.84 × 0.29 × 0.10 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: numerical (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.687, Tmax = 0.746

  • 5753 measured reflections

  • 2275 independent reflections

  • 1892 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.096

  • S = 1.09

  • 2275 reflections

  • 137 parameters

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

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C8—H8b⋯O1i 0.95 (2) 2.49 (2) 3.401 (2) 160
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. 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: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalMaker (CrystalMaker, 2009[CrystalMaker (2009). CrystalMaker for Windows. CrystalMaker Software Ltd, Yarnton, England. www.CrystalMaker.com.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1007700

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536814013518/fj2674sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013518/fj2674Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013518/fj2674Isup3.cml

checkCIF report


Comment top

Diazald (N-methyl-N-nitroso-p- toluenesulfonamide) has been known to be a versatile reagent used in the general synthesis of diazomethane, a useful compound that serves as a precursor for methylene production and is used in the production of heterocyclic rings. (Hudlicky, 1980) Recently, these N-nitroso compounds have gained attention due to their potential cancer chemotherapeutic abilities. (Skinner et al., 1960); (Garcia-Rio et al., 2011) Additionally, the title compound was also found to behave as an antimicrobial agent against yeasts, fungi, Gram-negative, and Gram-positive bacteria. (Uri & Scola, 1992) The title compound was also shown to behave as a nitrosylating reagent in the formation of a new diruthenium complex. (Mayer et al., 2014) Specifically, our group has investigated the potential of these sulfonamide structures as ligands for metal coordination. (Jacobs et al., 2013) Here we report on the crystal structure of this versatile compound. This compound forms hydrogen bonds of 2.49 (2) Å between the oxygen atom (O1) on the sulfonyl group of one molecule and the hydrogen atom (H10B) on the methyl group of another. These hydrogen bond lengths were confirmed to be in the normal range (2.31 (6) Å - 2.53 (12) Å) between sulfonyl O atoms and methyl H atoms on sulfonamide structures. (Dodoff et al., 2004) Additionally, pi-stacking interactions exist between adjacent aromatic rings and measure 3.868 (11) Å. These pi-stacking and hydrogen bonding interactions produce a stabilized dimerized crystal structure resulting in parallel chains.

Related literature top

For the use of the title compound as a nitrosylating agent, see: Mayer et al. (2014). For related structures, see: Hakkinen et al. (1988); Lightfoot et al. (1993). For the use of the title compound as a potential cancer chemotherapeutic, see: Garcia-Rio et al. (2011); Skinner et al. (1960). For its use as an antimicrobial, see: Uri & Scola (1992) and as a precursor in methylene production and production of heterocyclic rings, see: Hudlicky (1980). For literature hydrogen-bond lengths between sulfonyl O atoms and methyl H atoms in sulfonamide structures, see: Dodoff et al. (2004). For the potential use of sulfonamide compounds as ligands for metal coordination, see: Jacobs et al. (2013).

Experimental top

Approximately 100 mg of the title compound were dissolved in 2 ml of 100% isopropyl alcohol solution after being heated to boiling conditions. The solution was allowed to evaporate slowly for three days at approximately 4 C until clear, colorless crystals were formed. A crystal was manually separated and analyzed for crystallographic data using a Bruker APEXII CCD single-crystal X-ray diffractometer.

Refinement top

The structure was solved using direct methods (Bruker, 2011). Hydrogen 8 A, 8B, 8 C were found by electron difference maps and then allowed to vary in 3 dimensions. The isotropic parameter was held to -1.2.

Structure description top

Diazald (N-methyl-N-nitroso-p- toluenesulfonamide) has been known to be a versatile reagent used in the general synthesis of diazomethane, a useful compound that serves as a precursor for methylene production and is used in the production of heterocyclic rings. (Hudlicky, 1980) Recently, these N-nitroso compounds have gained attention due to their potential cancer chemotherapeutic abilities. (Skinner et al., 1960); (Garcia-Rio et al., 2011) Additionally, the title compound was also found to behave as an antimicrobial agent against yeasts, fungi, Gram-negative, and Gram-positive bacteria. (Uri & Scola, 1992) The title compound was also shown to behave as a nitrosylating reagent in the formation of a new diruthenium complex. (Mayer et al., 2014) Specifically, our group has investigated the potential of these sulfonamide structures as ligands for metal coordination. (Jacobs et al., 2013) Here we report on the crystal structure of this versatile compound. This compound forms hydrogen bonds of 2.49 (2) Å between the oxygen atom (O1) on the sulfonyl group of one molecule and the hydrogen atom (H10B) on the methyl group of another. These hydrogen bond lengths were confirmed to be in the normal range (2.31 (6) Å - 2.53 (12) Å) between sulfonyl O atoms and methyl H atoms on sulfonamide structures. (Dodoff et al., 2004) Additionally, pi-stacking interactions exist between adjacent aromatic rings and measure 3.868 (11) Å. These pi-stacking and hydrogen bonding interactions produce a stabilized dimerized crystal structure resulting in parallel chains.

For the use of the title compound as a nitrosylating agent, see: Mayer et al. (2014). For related structures, see: Hakkinen et al. (1988); Lightfoot et al. (1993). For the use of the title compound as a potential cancer chemotherapeutic, see: Garcia-Rio et al. (2011); Skinner et al. (1960). For its use as an antimicrobial, see: Uri & Scola (1992) and as a precursor in methylene production and production of heterocyclic rings, see: Hudlicky (1980). For literature hydrogen-bond lengths between sulfonyl O atoms and methyl H atoms in sulfonamide structures, see: Dodoff et al. (2004). For the potential use of sulfonamide compounds as ligands for metal coordination, see: Jacobs et al. (2013).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: CrystalMaker (CrystalMaker, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot at 50% probability.
[Figure 2] Fig. 2. The title structure is stabilized by a hydrogen bond between O2 and H8C, which measures 2.49 (2) Å and pi-stacking interactions between adjacent benzene rings, which measures 3.871 (11) Å. Oxygen atoms are shown in red, carbon atoms in black, hydrogen atoms in white, and nitrogen atoms in blue. Symmetry equivalent pi-stacking and hydrogen bonding are indicated by red and blue dashed lines, respectively.
N-Methyl-N-nitroso-p-toluenesulfonamide top
Crystal data top
C8H10N2O3SZ = 2
Mr = 214.24F(000) = 224
Triclinic, P1Dx = 1.456 Mg m−3
a = 6.8911 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.4435 (10) ÅCell parameters from 3237 reflections
c = 8.6248 (10) Åθ = 2.5–28.1°
α = 81.458 (1)°µ = 0.31 mm−1
β = 85.883 (1)°T = 100 K
γ = 80.310 (1)°Block, colorless
V = 488.62 (10) Å30.84 × 0.29 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer		2275 independent reflections
Radiation source: fine-focus sealed tube1892 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.3333 pixels mm-1θmax = 28.4°, θmin = 2.4°
ω and φ scansh = −9→9
Absorption correction: numerical
(SADABS; Bruker, 2011)		k = −10→11
Tmin = 0.687, Tmax = 0.746l = −11→11
5753 measured 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)] = 0.037Hydrogen site location: mixed
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0425P)2 + 0.2042P]
where P = (Fo2 + 2Fc2)/3
2275 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.36 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C8H10N2O3Sγ = 80.310 (1)°
Mr = 214.24V = 488.62 (10) Å3
Triclinic, P1Z = 2
a = 6.8911 (8) ÅMo Kα radiation
b = 8.4435 (10) ŵ = 0.31 mm−1
c = 8.6248 (10) ÅT = 100 K
α = 81.458 (1)°0.84 × 0.29 × 0.10 mm
β = 85.883 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		2275 independent reflections
Absorption correction: numerical
(SADABS; Bruker, 2011)		1892 reflections with I > 2σ(I)
Tmin = 0.687, Tmax = 0.746Rint = 0.024
5753 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.36 e Å−3
2275 reflectionsΔρmin = −0.37 e Å−3
137 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
xyzUiso*/Ueq
S10.20728 (6)0.03322 (5)0.28268 (5)0.01794 (13)
O10.33666 (19)−0.07228 (14)0.38895 (14)0.0234 (3)
O20.05198 (18)−0.02289 (15)0.21663 (15)0.0239 (3)
O3−0.1436 (2)0.37946 (16)0.40008 (15)0.0301 (3)
N10.0960 (2)0.18010 (17)0.38888 (16)0.0184 (3)
N2−0.0760 (2)0.26414 (19)0.33146 (18)0.0246 (3)
C10.3438 (2)0.13715 (19)0.13431 (19)0.0167 (3)
C20.5359 (3)0.1532 (2)0.1589 (2)0.0200 (4)
H20.59710.10250.25280.024*
C30.6369 (3)0.2450 (2)0.0434 (2)0.0219 (4)
H30.76910.25570.05840.026*
C40.5484 (3)0.3215 (2)−0.0938 (2)0.0204 (4)
C50.3552 (3)0.3032 (2)−0.1148 (2)0.0220 (4)
H50.29320.3554−0.20790.026*
C60.2519 (3)0.2107 (2)−0.0028 (2)0.0204 (4)
H60.12090.1976−0.01900.024*
C70.6590 (3)0.4220 (2)−0.2174 (2)0.0282 (4)
H7A0.73010.4901−0.16690.042*
H7B0.56570.4911−0.28910.042*
H7C0.75320.3502−0.27640.042*
C80.1981 (3)0.2380 (2)0.5075 (2)0.0219 (4)
H8A0.194 (3)0.352 (3)0.480 (2)0.033*
H8B0.329 (3)0.181 (3)0.512 (2)0.033*
H8C0.137 (3)0.215 (3)0.609 (3)0.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0207 (2)0.0151 (2)0.0183 (2)−0.00448 (16)0.00224 (16)−0.00297 (15)
O10.0286 (7)0.0165 (6)0.0228 (6)−0.0012 (5)0.0013 (5)0.0012 (5)
O20.0252 (7)0.0247 (7)0.0254 (7)−0.0118 (5)0.0032 (5)−0.0084 (5)
O30.0338 (8)0.0250 (7)0.0277 (7)0.0064 (6)0.0014 (6)−0.0053 (6)
N10.0195 (7)0.0190 (7)0.0165 (7)−0.0018 (6)0.0003 (6)−0.0037 (6)
N20.0249 (8)0.0241 (8)0.0223 (8)0.0016 (6)−0.0004 (6)−0.0019 (6)
C10.0203 (8)0.0131 (8)0.0170 (8)−0.0030 (6)0.0025 (6)−0.0040 (6)
C20.0186 (8)0.0207 (9)0.0203 (8)−0.0015 (7)−0.0015 (7)−0.0026 (7)
C30.0177 (9)0.0226 (9)0.0259 (9)−0.0052 (7)0.0016 (7)−0.0039 (7)
C40.0274 (9)0.0148 (8)0.0192 (8)−0.0039 (7)0.0064 (7)−0.0062 (7)
C50.0298 (10)0.0199 (9)0.0158 (8)−0.0020 (7)−0.0025 (7)−0.0020 (7)
C60.0197 (9)0.0226 (9)0.0197 (9)−0.0038 (7)−0.0010 (7)−0.0056 (7)
C70.0372 (11)0.0228 (10)0.0251 (10)−0.0092 (8)0.0092 (8)−0.0046 (8)
C80.0269 (10)0.0215 (9)0.0187 (9)−0.0063 (8)−0.0008 (7)−0.0046 (7)
Geometric parameters (Å, º) top
S1—O21.4258 (13)C3—H30.9500
S1—O11.4268 (13)C4—C51.393 (3)
S1—N11.6975 (14)C4—C71.506 (2)
S1—C11.7504 (17)C5—C61.384 (2)
O3—N21.2224 (19)C5—H50.9500
N1—N21.360 (2)C6—H60.9500
N1—C81.466 (2)C7—H7A0.9800
C1—C21.388 (2)C7—H7B0.9800
C1—C61.394 (2)C7—H7C0.9800
C2—C31.390 (2)C8—H8A0.96 (2)
C2—H20.9500C8—H8B0.95 (2)
C3—C41.391 (2)C8—H8C0.96 (2)
O2—S1—O1121.43 (8)C3—C4—C7120.73 (17)
O2—S1—N1105.80 (7)C5—C4—C7120.63 (16)
O1—S1—N1104.15 (7)C6—C5—C4121.35 (16)
O2—S1—C1109.93 (8)C6—C5—H5119.3
O1—S1—C1110.06 (8)C4—C5—H5119.3
N1—S1—C1103.75 (7)C5—C6—C1118.66 (16)
N2—N1—C8121.69 (14)C5—C6—H6120.7
N2—N1—S1114.33 (11)C1—C6—H6120.7
C8—N1—S1122.36 (12)C4—C7—H7A109.5
O3—N2—N1113.28 (14)C4—C7—H7B109.5
C2—C1—C6121.41 (16)H7A—C7—H7B109.5
C2—C1—S1119.72 (13)C4—C7—H7C109.5
C6—C1—S1118.76 (13)H7A—C7—H7C109.5
C1—C2—C3118.62 (16)H7B—C7—H7C109.5
C1—C2—H2120.7N1—C8—H8A108.3 (13)
C3—C2—H2120.7N1—C8—H8B108.9 (13)
C2—C3—C4121.31 (16)H8A—C8—H8B112.2 (19)
C2—C3—H3119.3N1—C8—H8C110.6 (13)
C4—C3—H3119.3H8A—C8—H8C110.3 (18)
C3—C4—C5118.64 (16)H8B—C8—H8C106.5 (18)
O2—S1—N1—N2−30.84 (14)O1—S1—C1—C6162.52 (13)
O1—S1—N1—N2−159.92 (12)N1—S1—C1—C6−86.55 (14)
C1—S1—N1—N284.88 (13)C6—C1—C2—C30.0 (2)
O2—S1—N1—C8163.44 (13)S1—C1—C2—C3−175.94 (13)
O1—S1—N1—C834.37 (15)C1—C2—C3—C40.8 (3)
C1—S1—N1—C8−80.84 (15)C2—C3—C4—C5−0.6 (3)
C8—N1—N2—O3−7.3 (2)C2—C3—C4—C7179.38 (16)
S1—N1—N2—O3−173.13 (12)C3—C4—C5—C6−0.3 (3)
O2—S1—C1—C2−157.71 (13)C7—C4—C5—C6179.71 (16)
O1—S1—C1—C2−21.41 (16)C4—C5—C6—C11.0 (3)
N1—S1—C1—C289.53 (14)C2—C1—C6—C5−0.9 (3)
O2—S1—C1—C626.22 (15)S1—C1—C6—C5175.10 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8b···O1i0.95 (2)2.49 (2)3.401 (2)160
Symmetry code: (i) −x+1, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8b···O1i0.95 (2)2.49 (2)3.401 (2)160
Symmetry code: (i) −x+1, −y, −z+1.
 

Acknowledgements

The authors gratefully acknowledge The College of New Jersey's School of Science for research funding and the National Science Foundation for major research instrumentation grant (NSF-0922931) for diffractometer acquisition.

References

First citationBruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCrystalMaker (2009). CrystalMaker for Windows. CrystalMaker Software Ltd, Yarnton, England. www.CrystalMaker.com.  Google Scholar
 First citationDodoff, N. I., Varga, R. A. & Kovala-Demrtzi, D. (2004). Z. Naturforsch. Teil B, 59, 1070–1076.  CAS Google Scholar
 First citationGarcia-Rio, L., Raposa-Barreiro, M. L. & Rodriguez-Dafonte, P. (2011). Org. Chem. Argentina, 7, 272–282.  Google Scholar
 First citationHakkinen, A., Ruostesuo, P. & Kivekas, R. (1988). J. Chem. Soc. Perkin Trans. 2, pp. 815–820.  Google Scholar
 First citationHudlicky, M. (1980). J. Org. Chem. 45, 5377–5378.  CrossRef CAS Web of Science Google Scholar
 First citationJacobs, D. L., Chan, B. C. & O'Connor, A. R. (2013). Acta Cryst. C69, 1397–1401.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationLightfoot, P., Tremayne, M., Glidewell, K. D. & Bruce, P. G. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 1625–1630.  CSD CrossRef Web of Science Google Scholar
 First citationMayer, T., Mayer, P. & Bottcher, H. (2014). J. Organomet. Chem. 751, 368–373.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSkinner, W. A., Gram, H. F., Greene, M. O., Greenberg, J. & Baker, B. R. (1960). J. Med. Pharm. Chem. 2, 299–333.  CrossRef PubMed CAS Web of Science Google Scholar
 First citationUri, J. V. & Scola, F. (1992). Acta Microbiol. Hung. 39, 317–322.  PubMed CAS Web of Science Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Page o782
https://doi.org/10.1107/S1600536814013518
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS