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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 6| June 2011| Page o1504
doi:10.1107/S1600536811016370

Methyl c-1-cyano-t-2-methyl­sulfonyl-3-phenyl­cyclo­propane­carboxyl­ate

Victor A. Vasin,a* Irina Yu. Bolusheva,a Vyacheslav A. Neverovb and Nikolai V. Somovc

aDepartment of Chemistry, N. P. Ogarev Mordovian State University, 430005 Saransk, Russian Federation, bDepartment of Physics, N. P. Ogarev Mordovian State University, 430005 Saransk, Russian Federation, and cDepartment of Physics, N. I. Lobachevsky State University of Nizhni Novgorod, 603950 Nizhni Novgorod, Russian Federation
*Correspondence e-mail: vasin@mrsu.ru

(Received 19 March 2011; accepted 29 April 2011; online 25 May 2011)

The title compound, C13H13NO4S, is a racemic mixture of enanti­omers. Short intra­molecular contacts between sulfonyl O and ester carbonyl C atoms are observed [C⋯O = 2.881 (1), 2.882 (1) and 2.686 (1) Å], indicating the possibility of donor—acceptor inter­actions between these groups. The dihedral angle between the phenyl and cyclopropyl rings is 79.3 (1)°.

Related literature

Some α-bromo­vinyl sulfones react with primary amines in DMSO to give the products of aza-Michael ring closure reactions (MIRCR), viz. 2-sulfonyl-substituted aziridines, see: Galliot et al. (1979[Galliot, J.-M., Gellas-Mialhe, Y. & Vessiere, R. (1979). Can. J. Chem. 57, 1958-1966.]). Similarly, MIRCR of phenyl-(Z)-(2-phenyl-2-chloro­ethen­yl)sulfone with diethyl sodium malonate leads to the formation of a sulfonyl-substituted cyclo­propane, see: Yamamoto et al. (1985[Yamamoto, I., Sakai, T., Ohta, K. & Matsuzaki, K. (1985). J. Chem. Soc. Perkin Trans. 1, pp. 2785-2787.]). For related structures, see: Vasin et al. (2008[Vasin, V. A., Bolusheva, I. Yu. & Razin, V. V. (2008). Chem. Heterocycl. Compd, 44, 419-429.], 2010[Vasin, V. A., Petrov, P. S., Genaev, A. M., Gindin, V. A. & Razin, V. V. (2010). J. Struct. Chem. 51, 949-955.]); Zefirov & Zorkii (1989[Zefirov, Yu. V. & Zorkii, P. M. (1989). Russ. Chem. Rev. 58, 421-440.]).

[Scheme 1]

Experimental

Crystal data

  • C13H13NO4S

  • Mr = 279.3

  • Orthorhombic, P n a 21

  • a = 10.7323 (4) Å

  • b = 20.0790 (6) Å

  • c = 6.2663 (2) Å

  • V = 1350.35 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 293 K

  • 0.20 × 0.15 × 0.12 mm
Data collection

  • Xcalibur, Sapphire3, Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.964, Tmax = 1

  • 21704 measured reflections

  • 3353 independent reflections

  • 3044 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.078

  • S = 0.98

  • 3353 reflections

  • 172 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.14 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1523 Friedel pairs

  • Flack parameter: 0.05 (5)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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/S1600536811016370/aa2006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016370/aa2006Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016370/aa2006Isup3.cml

checkCIF report


Comment top

It is know, that some alpha-bromovinyl sulfones react with primary amines in DMSO to give the products of aza-Michael Ring Closure reaction (MIRCR) - 2-sulfonylsubstituted aziridines (Galliot et al., 1979). Similarly MIRCR of phenyl-(Z)-(2-phenyl-2-chloroethenyl)sulfone with diethyl sodium malonate leads to formation of a sulfonylsubstituted cyclopropane (Yamamoto et al., 1985). We have carried out MIRCR between compound (1) (see Fig. 2) and monosodium salt of methyl cyanoacetate in THF at 20 °C and a cyclopropane derivative, (2), was obtained. The product, (2), was isolated by chromatography, crystallized and studied by X-ray diffraction.

In compound (2) three short intramolecular contacts C···O, which appreciable less sum of the van der Vaals radii given atoms = 3.000Å (Zefirov et al., 1989), are found out. The first of them takes place between atoms O2 of sulfonyl and C5 of methoxycarbonyl groups (2.881 Å). The second contact length 2.882Å is observed between atoms O4 of methoxycarbonyl and C10 of cyclopropane fragment. The third is shorted (2.686 Å). It arises between atoms O1 of methoxycarbonyl group and C2 of cyano group. Given contacts are evidence of possible donor-acceptor interaction between cys-located sulfonyl and methoxycarbonyl groups, and also between methoxycarbonyl on the one hand,cyano group and cyclopropene fragment - with another.

We shall note, that strong interaction between drawing together sulfonyl and methoxycarbonyl groups in structure of cyclobutane fragment, hardly fixed in space by trimethylene bridge, where free rotation of given groups was revealed earlier; interatomic distance C···O in this case is 2.489Å (Vasin et al., 2010). At the same time, in analogue of compound (2) - dimethyl 3-phenyl-2-(t)-phenylsulfonyl-1,1-cyclopropanecarboxylate, as it has been established by X-ray analysis, mutual, close to parallel, an arrangement of sulfonyl and ethoxycarbonyl groups the dipole-dipole interaction between them does not promote (Yamamoto et al., 1985).

The values of valent angles at atom C5 in compound (2), most likely, are consequence of noted donor-acceptor interaction: a little overestimated for C4—C5—O4 (124.35°) and O4—C5—O1 (126.02°), essentially underestimated for O1—C5—C4 (109.62°), and also value of angle C5—C4—C2 (114.35°).

The structure of compound (2) consists of separate molecules between which only van der Vaals interaction is carried out.

Related literature top

Some \a-bromovinyl sulfones react with primary amines in DMSO to give the products of aza-Michael ring closure reactions (MIRCR), viz. 2-sulfonyl-substituted aziridines, see: Galliot et al. (1979). Similarly, MIRCR of phenyl-(Z)-(2-phenyl-2-chloroethenyl)sulfone with diethyl sodium malonate leads to the formation of a sulfonyl-substituted cyclopropane, see: Yamamoto et al. (1985). For related structures, see: Vasin et al. (2008, 2010); Zefirov & Zorkii (1989).

Experimental top

Compound (2) was obtained by the reaction between the previously reported compound (1) (Vasin et al., 2008) and monosodium salt of methyl cyanoacetate (see Fig. 2). Sodium hydride (0.23 g 60% suspension in mineral oil) was freed of mineral oil by washing with hexane and was added dry THF (5 ml). Methyl cyanoacetate (4.2 g) in THF (10 ml) was added drop wise for 10 min at stirring. The stirring was continued for 1.5 h at 20 °C. After drop wise addition of compound (1) (1.0 g) in THF (10 ml), stirring was continued at 20° C for 20 h. The mixture was diluted with water (250 ml), neutralized with aqueous (1: 1) HCl, extracted with CHCl3 (3 x 15 ml), washed with water, and dried over MgSO4. Evaporation of solvent in vacuo gave 0.7 g semisolid product. Compound (2) was isolated by column chromatography on silicagel and crystallized from an acetone - hexane (1: 3) mixture [yield 0.21 g (20%); m. p. 417–418 K].

Refinement top

The initial fragment of structure was solved by a direct method; other non-hydrogen atoms were received from the analysis by successive synthesis of electron density. Floating origin restraint had been used. Hydrogen atoms were placed in geometrically calculated positions and refined in riding model with U (H) = 1.5 U (C) for hydrogen atoms in methyl groups and U (H) = 1.2 U (C) for all other hydrogen atoms, where U (C) – the equivalent temperature factor of carbon atom with which the corresponding hydrogen atom is bonded.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip 2010).

Figures top
[Figure 1] Fig. 1. A view of the compound (2). The non-H atoms are shown with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. MIRCR between compound (1) and monosodium salt of methyl cyanoacetate in THF
Methyl c-1-cyano-t-2-methylsulfonyl-3-phenylcyclopropanecarboxylate top
Crystal data top
C13H13NO4SF(000) = 584
Mr = 279.3Dx = 1.374 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 10874 reflections
a = 10.7323 (4) Åθ = 3.4–32.9°
b = 20.0790 (6) ŵ = 0.25 mm−1
c = 6.2663 (2) ÅT = 293 K
V = 1350.35 (8) Å3Prism, colorless
Z = 40.20 × 0.15 × 0.12 mm
Data collection top
Xcalibur, Sapphire3, Gemini
diffractometer		3353 independent reflections
Graphite monochromator3044 reflections with I > 2σ(I)
Detector resolution: 16.0302 pixels mm-1Rint = 0.026
ω scansθmax = 28.3°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		h = −14→14
Tmin = 0.964, Tmax = 1k = −26→26
21704 measured reflectionsl = −8→8
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0559P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
3353 reflectionsΔρmax = 0.23 e Å−3
172 parametersΔρmin = −0.14 e Å−3
1 restraintAbsolute structure: Flack (1983), 1523 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (5)
Crystal data top
C13H13NO4SV = 1350.35 (8) Å3
Mr = 279.3Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 10.7323 (4) ŵ = 0.25 mm−1
b = 20.0790 (6) ÅT = 293 K
c = 6.2663 (2) Å0.20 × 0.15 × 0.12 mm
Data collection top
Xcalibur, Sapphire3, Gemini
diffractometer		3353 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		3044 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 1Rint = 0.026
21704 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.078Δρmax = 0.23 e Å−3
S = 0.98Δρmin = −0.14 e Å−3
3353 reflectionsAbsolute structure: Flack (1983), 1523 Friedel pairs
172 parametersAbsolute structure parameter: 0.05 (5)
1 restraint
Special details top

Experimental. CrysAlisPro (Oxford Diffraction Ltd., 2010) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. The one restraint corresponded to floating origin restraints. 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
S10.29436 (2)0.295171 (11)0.76310 (4)0.04011 (6)
O1−0.01457 (7)0.35848 (4)1.05436 (11)0.04777 (19)
O20.27636 (12)0.27721 (5)0.98035 (16)0.0874 (4)
O30.41644 (8)0.29350 (4)0.67581 (19)0.0666 (3)
O40.16184 (7)0.38091 (4)1.22923 (10)0.04745 (19)
N1−0.03319 (10)0.47196 (5)0.65545 (16)0.0532 (3)
C1−0.07127 (13)0.33421 (7)1.2490 (2)0.0652 (3)
H1A−0.15410.31881.21910.098*
H1B−0.07490.36961.35190.098*
H1C−0.02250.29821.30520.098*
C20.04443 (9)0.44609 (4)0.74669 (15)0.0345 (2)
C30.20022 (12)0.24604 (6)0.5992 (3)0.0643 (4)
H3A0.11660.24600.65330.097*
H3B0.23170.20130.59710.097*
H3C0.20070.26380.45690.097*
C40.14145 (8)0.41098 (4)0.86151 (14)0.02960 (19)
C50.10008 (9)0.38160 (5)1.07244 (13)0.0337 (2)
C60.28383 (11)0.51912 (5)0.55263 (17)0.0454 (3)
H60.23050.49300.47070.054*
C70.40648 (13)0.61805 (6)0.5922 (2)0.0642 (4)
H70.43570.65820.53760.077*
C80.31902 (8)0.49822 (4)0.75425 (17)0.0354 (2)
C90.44182 (12)0.59803 (6)0.7918 (2)0.0617 (4)
H90.49470.62470.87260.074*
C100.27718 (8)0.43416 (5)0.85051 (15)0.0327 (2)
H100.32620.42110.97570.039*
C110.23653 (9)0.37605 (5)0.71750 (14)0.0319 (2)
H110.22670.38680.56590.038*
C120.39901 (11)0.53807 (5)0.8741 (2)0.0475 (3)
H120.42380.52451.00950.057*
C130.32830 (14)0.57925 (6)0.4726 (2)0.0600 (3)
H130.30470.59320.33690.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.03721 (11)0.03399 (9)0.04912 (13)0.00838 (9)0.00024 (12)0.00378 (12)
O10.0483 (4)0.0622 (4)0.0328 (3)−0.0185 (3)−0.0033 (3)0.0071 (3)
O20.1419 (10)0.0668 (5)0.0534 (5)0.0470 (6)0.0050 (6)0.0223 (5)
O30.0311 (4)0.0541 (4)0.1144 (8)0.0099 (3)0.0021 (4)0.0004 (5)
O40.0514 (4)0.0653 (4)0.0257 (3)−0.0055 (4)−0.0068 (3)0.0087 (3)
N10.0513 (5)0.0676 (6)0.0406 (4)0.0219 (5)−0.0035 (4)0.0105 (4)
C10.0665 (7)0.0860 (8)0.0431 (6)−0.0335 (6)0.0020 (6)0.0121 (6)
C20.0395 (4)0.0375 (4)0.0265 (4)0.0062 (3)0.0006 (4)−0.0002 (4)
C30.0489 (7)0.0460 (6)0.0982 (10)−0.0072 (5)−0.0028 (7)−0.0096 (7)
C40.0331 (4)0.0326 (4)0.0230 (4)0.0039 (3)−0.0016 (4)0.0010 (3)
C50.0418 (5)0.0348 (4)0.0245 (4)0.0006 (4)−0.0005 (4)0.0006 (4)
C60.0544 (6)0.0414 (5)0.0404 (5)−0.0058 (5)0.0006 (5)0.0068 (4)
C70.0624 (7)0.0420 (5)0.0882 (9)−0.0070 (6)0.0216 (7)0.0101 (6)
C80.0339 (4)0.0359 (4)0.0365 (4)0.0011 (3)0.0024 (4)−0.0001 (5)
C90.0505 (6)0.0458 (5)0.0888 (10)−0.0107 (5)0.0006 (7)−0.0115 (6)
C100.0318 (4)0.0376 (5)0.0286 (4)0.0012 (4)−0.0045 (4)0.0035 (4)
C110.0328 (4)0.0343 (4)0.0287 (4)0.0064 (4)−0.0018 (3)0.0028 (3)
C120.0440 (5)0.0464 (5)0.0521 (6)−0.0034 (5)−0.0037 (5)−0.0062 (5)
C130.0739 (8)0.0492 (6)0.0569 (7)0.0020 (6)0.0098 (6)0.0166 (6)
Geometric parameters (Å, º) top
S1—O31.4202 (9)C4—C111.5320 (12)
S1—O21.4215 (10)C6—C81.3838 (15)
S1—C31.7462 (14)C6—C131.3918 (17)
S1—C111.7619 (9)C6—H60.9300
O1—C51.3199 (12)C7—C91.367 (2)
O1—C11.4477 (14)C7—C131.368 (2)
O4—C51.1853 (11)C7—H70.9300
N1—C21.1360 (13)C8—C121.3934 (15)
C1—H1A0.9600C8—C101.4899 (13)
C1—H1B0.9600C9—C121.3879 (16)
C1—H1C0.9600C9—H90.9300
C2—C41.4488 (12)C10—C111.4988 (13)
C3—H3A0.9600C10—H100.9800
C3—H3B0.9600C11—H110.9800
C3—H3C0.9600C12—H120.9300
C4—C51.5140 (12)C13—H130.9300
C4—C101.5308 (13)
O3—S1—O2119.22 (7)C8—C6—H6120.1
O3—S1—C3107.09 (6)C13—C6—H6120.1
O2—S1—C3109.97 (8)C9—C7—C13120.25 (12)
O3—S1—C11106.52 (5)C9—C7—H7119.9
O2—S1—C11109.95 (5)C13—C7—H7119.9
C3—S1—C11102.80 (5)C6—C8—C12119.08 (9)
C5—O1—C1115.97 (8)C6—C8—C10123.31 (9)
O1—C1—H1A109.5C12—C8—C10117.60 (10)
O1—C1—H1B109.5C7—C9—C12120.20 (12)
H1A—C1—H1B109.5C7—C9—H9119.9
O1—C1—H1C109.5C12—C9—H9119.9
H1A—C1—H1C109.5C8—C10—C11122.32 (9)
H1B—C1—H1C109.5C8—C10—C4124.58 (8)
N1—C2—C4178.08 (10)C11—C10—C460.74 (6)
S1—C3—H3A109.5C8—C10—H10113.2
S1—C3—H3B109.5C11—C10—H10113.2
H3A—C3—H3B109.5C4—C10—H10113.2
S1—C3—H3C109.5C10—C11—C460.66 (6)
H3A—C3—H3C109.5C10—C11—S1121.66 (7)
H3B—C3—H3C109.5C4—C11—S1124.13 (6)
C2—C4—C5114.35 (8)C10—C11—H11113.5
C2—C4—C10120.90 (8)C4—C11—H11113.5
C5—C4—C10115.90 (8)S1—C11—H11113.5
C2—C4—C11114.14 (8)C9—C12—C8120.13 (12)
C5—C4—C11122.09 (7)C9—C12—H12119.9
C10—C4—C1158.60 (6)C8—C12—H12119.9
O4—C5—O1126.04 (9)C7—C13—C6120.45 (13)
O4—C5—C4124.35 (9)C7—C13—H13119.8
O1—C5—C4109.60 (7)C6—C13—H13119.8
C8—C6—C13119.89 (11)

Experimental details

Crystal data
Chemical formulaC13H13NO4S
Mr279.3
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)293
a, b, c (Å)10.7323 (4), 20.0790 (6), 6.2663 (2)
V (Å3)1350.35 (8)
Z4
Radiation typeMo Kα
µ (mm−1)0.25
Crystal size (mm)0.20 × 0.15 × 0.12
Data collection
DiffractometerXcalibur, Sapphire3, Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.964, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections		21704, 3353, 3044
Rint0.026
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.078, 0.98
No. of reflections3353
No. of parameters172
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.23, −0.14
Absolute structureFlack (1983), 1523 Friedel pairs
Absolute structure parameter0.05 (5)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip 2010).

 

References

First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationGalliot, J.-M., Gellas-Mialhe, Y. & Vessiere, R. (1979). Can. J. Chem. 57, 1958–1966.  Google Scholar
 First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  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
 First citationVasin, V. A., Bolusheva, I. Yu. & Razin, V. V. (2008). Chem. Heterocycl. Compd, 44, 419–429.  CrossRef CAS Google Scholar
 First citationVasin, V. A., Petrov, P. S., Genaev, A. M., Gindin, V. A. & Razin, V. V. (2010). J. Struct. Chem. 51, 949–955.  CrossRef CAS Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationYamamoto, I., Sakai, T., Ohta, K. & Matsuzaki, K. (1985). J. Chem. Soc. Perkin Trans. 1, pp. 2785–2787.  CrossRef Google Scholar
 First citationZefirov, Yu. V. & Zorkii, P. M. (1989). Russ. Chem. Rev. 58, 421–440.  CrossRef Google Scholar

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 6| June 2011| Page o1504
doi:10.1107/S1600536811016370
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