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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o73–o74.
Published online 2009 December 9. doi:  10.1107/S1600536809051769
PMCID: PMC2980078

7-Benzenesulfonamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid monohydrate

Abstract

In the title compound, C14H14N2O5S2·H2O, the six-membered ring fused to the β-lactam unit has a twisted conformation. Weak intra­molecular N—H(...)S and C—H(...)O inter­actions occur. Inter­molecular C—H(...)S, N—H(...)O, C—H(...)O and O—H(...)O hydrogen-bonding inter­actions stabilize the crystal structure, forming a three-dimensional network. Weak C—H(...)π inter­actions are also present.

Related literature

For the production of 7-amino-deacetoxy­cephalosporanic acid-like components by direct fermentation, see: Schroen et al. (2000 [triangle]). For 7-benzene­sulfonamido-3-ethenyl-8-oxo-5-thia-1-aza­bicyclo­[4.2.0]oct-2-ene-2-carboxylic acid methanol solvate, see: Mariam et al. (2009 [triangle]). For structures with the β-lactam unit, see: Akkurt et al. (2008a [triangle],b [triangle],c [triangle]); Baktır et al. (2009 [triangle]); Pınar et al. (2006 [triangle]); Yalçın et al. (2009 [triangle]); Çelik et al. (2009a [triangle],b [triangle]). For puckering parameters, see: Cremer & Pople (1975 [triangle]).

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Object name is e-66-00o73-scheme1.jpg

Experimental

Crystal data

  • C14H14N2O5S2·H2O
  • M r = 372.43
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o73-efi1.jpg
  • a = 5.9535 (7) Å
  • b = 15.8248 (19) Å
  • c = 18.411 (2) Å
  • V = 1734.6 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 296 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer
  • 10847 measured reflections
  • 3572 independent reflections
  • 1890 reflections with I > 2σ(I)
  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.109
  • S = 0.97
  • 3572 reflections
  • 226 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1425 Friedel pairs
  • Flack parameter: −0.07 (11)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051769/vm2014sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051769/vm2014Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

One of the building blocks of cephalosporin antibiotics is 7-amino-deacetoxycephalosporanic acid (7-ADCA). It is currently produced from penicillin G using an elaborate chemical ring-expansion step followed by an enzyme-catalyzed hydrolysis. However, 7-ADCA-like components can also be produced by direct fermentation (Schroen et al. 2000).

In the title molecule (I) shown in Fig. 1, the β-lactam unit (N1/C6–C8) has a twisted conformation with the dihedral angles of 164.7 (4)° and 164.7 (4)° between the planes N1 C6 C7 and C6 C8 C7 and the planes N1 C6 C8 and N1 C8 C7, respectively. The six-membered ring fused to the β-lactam unit, (N1/S1/C1/C2/C4/C6) is puckered with the puckering parameters (Cremer & Pople, 1975): QT = 0.618 (3) Å, θ = 54.2 (4) °, [var phi] = 340.4 (5) °, respectively.

The crystal stucture is stabilized by intermolecular C—H···S, N—H···O, C—H···O and O—H···O hydrogen bonding interactions between symmetry-related molecules, forming a network in three dimensions (Table 1, Fig. 2). Furthermore, there is a weak C—H···π interaction [C3—H3B···Cg3(-x + 3/2, -y + 1, z + 1/2); H3B···Cg3 = 2.72 Å, C3···Cg3 = 3.640 (5) Å, C3—H3B···Cg3 = 161°, where Cg3 is a centroid of the phenyl ring C9–C14].

Experimental

7-ADCA (1 g, 4.7 mmol) was dissolved in distilled water (20 ml) in a round bottom flask (50 ml). Na2CO3 (3M) solution was added to maintain the solution at pH 8–9, then benzene sulfonyl chloride (0.82 g, 4.7 mmol) was added dropwise to the solution and stirred at room temperature. As all benzene sulfonyl chloride was consumed, pH becomes stable at 8–9, which confirms the completion of reaction. Then pH was adjusted to 1–2, by using 3 N HCl. The precipitate obtained was filtered, washed with distilled water, dried and recrystalized in ethyl acetate. Light yellow prisms of (I) appeared after two days.

Refinement

The H atoms of the water molecule were located in difference Fourier maps and were refined with O—H distances restrained to 0.83 (1) Å and H···H distances restrained to 1.30 (1) Å, with displacement parameters fixed at 1.5 times Ueq of the parent O atoms. H atom on O1 was calculated and refined with a riding model [O—H = 0.82Å and Uiso(H) = 1.5Ueq(O)]. The other H atoms were placed geometrically, with N—H = 0.86 Å, C—H = 0.96–0.98 Å, and included in the refinement using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(parent atom).

Figures

Fig. 1.
The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
Fig. 2.
The packing and hydrogen bonding of the title compound viewed down a axis. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C14H14N2O5S2·H2OF(000) = 776
Mr = 372.43Dx = 1.426 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1402 reflections
a = 5.9535 (7) Åθ = 2.8–17.3°
b = 15.8248 (19) ŵ = 0.34 mm1
c = 18.411 (2) ÅT = 296 K
V = 1734.6 (3) Å3Prismatic, light yellow
Z = 40.20 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer1890 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.064
graphiteθmax = 26.8°, θmin = 2.6°
[var phi] and ω scansh = −4→7
10847 measured reflectionsk = −12→20
3572 independent reflectionsl = −15→23

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.055w = 1/[σ2(Fo2) + (0.0407P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109(Δ/σ)max < 0.001
S = 0.97Δρmax = 0.20 e Å3
3572 reflectionsΔρmin = −0.25 e Å3
226 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.0083 (10)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1425 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.07 (11)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)

xyzUiso*/Ueq
S10.8308 (2)0.30975 (7)0.07531 (7)0.0628 (5)
S21.06325 (17)0.48679 (7)−0.11299 (6)0.0452 (4)
O10.1740 (7)0.4774 (2)0.21094 (17)0.0880 (16)
O20.1461 (5)0.51706 (18)0.09585 (15)0.0573 (11)
O30.6341 (5)0.56743 (17)0.05463 (18)0.0719 (13)
O41.3013 (4)0.48188 (19)−0.11039 (15)0.0595 (11)
O50.9420 (5)0.44363 (17)−0.16919 (15)0.0554 (10)
N10.5130 (5)0.42642 (19)0.06042 (18)0.0410 (11)
N20.9775 (5)0.44881 (19)−0.03638 (18)0.0447 (12)
C10.6086 (8)0.2712 (3)0.1326 (3)0.072 (2)
C20.4335 (7)0.3333 (3)0.1575 (2)0.0500 (17)
C30.2901 (9)0.2995 (3)0.2184 (2)0.077 (2)
C40.3988 (6)0.4074 (3)0.1247 (2)0.0427 (16)
C50.2262 (7)0.4725 (3)0.1418 (3)0.0507 (17)
C60.6407 (7)0.3665 (2)0.0176 (2)0.0500 (17)
C70.6267 (6)0.4950 (3)0.0341 (2)0.0480 (16)
C80.7372 (7)0.4416 (3)−0.0250 (2)0.0470 (17)
C90.9814 (6)0.5938 (2)−0.1135 (2)0.0430 (14)
C101.1108 (7)0.6515 (3)−0.0765 (2)0.0587 (17)
C111.0450 (10)0.7349 (3)−0.0734 (3)0.074 (2)
C120.8513 (10)0.7598 (3)−0.1058 (3)0.069 (2)
C130.7206 (8)0.7021 (3)−0.1421 (3)0.0683 (19)
C140.7853 (7)0.6178 (3)−0.1457 (3)0.0577 (19)
OW10.8355 (9)0.5874 (3)0.2110 (3)0.128 (2)
H10.079600.514500.216900.1320*
H1A0.532600.226100.106900.0860*
H1B0.676900.246500.175500.0860*
H21.071300.43340−0.003400.0530*
H3A0.171500.338800.228700.1160*
H3B0.380800.292000.261000.1160*
H3C0.226800.246200.204300.1160*
H60.546000.32940−0.012100.0600*
H80.657100.44840−0.071100.0560*
H101.242400.63430−0.053700.0710*
H111.133500.77410−0.049100.0890*
H120.806900.81610−0.103300.0830*
H130.588200.71950−0.164300.0820*
H140.696200.57840−0.169700.0690*
HW10.706 (6)0.587 (5)0.228 (3)0.1920*
HW20.819 (12)0.614 (4)0.172 (2)0.1920*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0590 (8)0.0401 (6)0.0892 (10)0.0106 (6)0.0078 (8)0.0044 (6)
S20.0366 (6)0.0512 (7)0.0479 (7)0.0031 (5)0.0001 (6)0.0012 (6)
O10.104 (3)0.110 (3)0.050 (2)0.032 (3)0.014 (2)−0.012 (2)
O20.0538 (19)0.0611 (19)0.057 (2)0.0140 (18)0.0046 (17)−0.0017 (17)
O30.062 (2)0.0368 (17)0.117 (3)0.0035 (17)0.029 (2)−0.0053 (18)
O40.0328 (16)0.080 (2)0.0656 (19)0.0071 (16)0.0052 (15)0.0055 (18)
O50.0591 (18)0.0585 (17)0.0485 (19)−0.0021 (16)−0.0076 (17)−0.0051 (15)
N10.0398 (19)0.0353 (18)0.048 (2)0.0017 (17)0.0067 (18)−0.0016 (17)
N20.029 (2)0.054 (2)0.051 (2)0.0090 (16)0.0011 (16)0.0119 (18)
C10.077 (4)0.048 (3)0.091 (4)−0.003 (3)−0.002 (3)0.012 (3)
C20.043 (3)0.057 (3)0.050 (3)−0.010 (3)0.000 (2)0.007 (2)
C30.080 (4)0.086 (4)0.066 (3)−0.013 (3)−0.005 (3)0.017 (3)
C40.038 (2)0.050 (3)0.040 (3)−0.005 (2)−0.001 (2)−0.002 (2)
C50.040 (3)0.063 (3)0.049 (3)−0.005 (2)0.004 (2)−0.012 (3)
C60.048 (3)0.046 (3)0.056 (3)−0.010 (2)0.000 (2)−0.011 (2)
C70.041 (3)0.039 (2)0.064 (3)0.005 (2)0.003 (2)0.010 (2)
C80.037 (3)0.054 (3)0.050 (3)0.006 (2)−0.003 (2)0.004 (2)
C90.037 (2)0.044 (2)0.048 (3)−0.005 (2)0.004 (2)0.007 (2)
C100.052 (3)0.058 (3)0.066 (3)−0.005 (3)−0.012 (3)0.001 (3)
C110.094 (4)0.046 (3)0.083 (4)−0.015 (3)−0.020 (4)−0.004 (3)
C120.082 (4)0.044 (3)0.081 (4)0.001 (3)0.009 (4)0.000 (3)
C130.053 (3)0.062 (3)0.090 (4)0.012 (3)−0.012 (3)0.013 (3)
C140.047 (3)0.048 (3)0.078 (4)−0.004 (2)−0.004 (3)0.002 (2)
OW10.152 (4)0.104 (3)0.129 (4)0.035 (3)0.085 (4)0.000 (3)

Geometric parameters (Å, °)

S1—C11.799 (5)C6—C81.535 (6)
S1—C61.793 (4)C7—C81.527 (6)
S2—O41.420 (3)C9—C141.363 (6)
S2—O51.435 (3)C9—C101.375 (6)
S2—N21.616 (3)C10—C111.378 (7)
S2—C91.762 (3)C11—C121.357 (8)
O1—C51.313 (6)C12—C131.373 (7)
O2—C51.200 (6)C13—C141.390 (7)
O3—C71.208 (5)C1—H1B0.9700
O1—H10.8200C1—H1A0.9700
OW1—HW20.84 (5)C3—H3C0.9600
OW1—HW10.83 (4)C3—H3A0.9600
N1—C41.398 (5)C3—H3B0.9600
N1—C71.368 (5)C6—H60.9800
N1—C61.449 (5)C8—H80.9800
N2—C81.450 (5)C10—H100.9300
N2—H20.8600C11—H110.9300
C1—C21.504 (7)C12—H120.9300
C2—C41.335 (6)C13—H130.9300
C2—C31.507 (6)C14—H140.9300
C4—C51.489 (6)
S1···N23.136 (3)C5···OW1iii3.216 (7)
S1···C5i3.698 (5)C7···O4iii3.297 (5)
S1···H22.8200C7···O2i3.313 (5)
S1···H6ii2.8000C7···O23.099 (5)
O1···OW1iii2.663 (6)C8···C143.577 (7)
O1···C32.902 (6)C8···O4iii3.100 (5)
OW1···O2i3.025 (6)C11···O3vii3.192 (6)
OW1···O33.135 (6)C12···O3vii3.346 (6)
OW1···C5i3.216 (7)C14···C83.577 (7)
OW1···O5iv2.799 (6)C4···H2iii3.0900
OW1···O1i2.663 (6)C5···H3A2.6700
O2···N12.693 (4)C5···H2iii2.8900
O2···C7iii3.313 (5)C9···H3Bvi3.0500
O2···C73.099 (5)C12···H3Bvi3.0400
O2···OW1iii3.025 (6)C13···H3Bvi2.9700
O2···O33.107 (4)C14···H3Bvi2.9900
O2···N2iii2.846 (4)H1···HW2iii2.3600
O3···O23.107 (4)H1···OW1iii1.8600
O3···OW13.135 (6)H1···HW1iii2.5100
O3···C53.276 (6)HW1···O5iv2.14 (5)
O3···C12v3.346 (6)HW1···H1i2.5100
O3···N23.242 (4)H1A···H3C2.5800
O3···C11v3.192 (6)H1B···H3B2.4700
O4···C7i3.297 (5)H2···O2i2.3000
O4···C8i3.100 (5)H2···N1i2.8800
O5···OW1vi2.799 (6)H2···S12.8200
O1···H3A2.2200H2···C5i2.8900
OW1···H1i1.8600H2···C4i3.0900
O2···HW2iii2.85 (6)HW2···O32.54 (5)
O2···H2iii2.3000HW2···O2i2.85 (6)
O2···H12v2.8100HW2···H1i2.3600
O3···HW22.54 (5)H3A···O12.2200
O3···H12v2.8300H3A···C52.6700
O3···H11v2.5100H3B···C12iv3.0400
O4···H102.6500H3B···C14iv2.9900
O4···H8i2.3000H3B···C9iv3.0500
O5···HW1vi2.14 (5)H3B···C13iv2.9700
O5···H142.5900H3B···H1B2.4700
O5···H82.4800H3C···H1A2.5800
N1···O22.693 (4)H6···S1viii2.8000
N2···O2i2.846 (4)H8···O52.4800
N2···S13.136 (3)H8···O4iii2.3000
N2···O33.242 (4)H10···O42.6500
N1···H2iii2.8800H11···O3vii2.5100
C3···O12.902 (6)H12···O3vii2.8300
C5···O33.276 (6)H12···O2vii2.8100
C5···S1iii3.698 (5)H14···O52.5900
C1—S1—C693.1 (2)S2—C9—C14120.5 (3)
O4—S2—O5120.03 (18)C10—C9—C14120.7 (4)
O4—S2—N2105.40 (17)C9—C10—C11119.8 (4)
O4—S2—C9109.19 (18)C10—C11—C12120.1 (5)
O5—S2—N2107.07 (17)C11—C12—C13120.2 (5)
O5—S2—C9108.33 (17)C12—C13—C14120.3 (5)
N2—S2—C9105.95 (17)C9—C14—C13118.9 (4)
C5—O1—H1110.00S1—C1—H1A108.00
HW1—OW1—HW2103 (6)S1—C1—H1B108.00
C6—N1—C793.8 (3)C2—C1—H1B108.00
C4—N1—C6125.1 (3)H1A—C1—H1B107.00
C4—N1—C7135.4 (3)C2—C1—H1A108.00
S2—N2—C8117.8 (3)C2—C3—H3B109.00
C8—N2—H2121.00C2—C3—H3C109.00
S2—N2—H2121.00H3A—C3—H3B109.00
S1—C1—C2117.8 (3)H3A—C3—H3C110.00
C1—C2—C4122.9 (4)H3B—C3—H3C109.00
C3—C2—C4124.1 (4)C2—C3—H3A109.00
C1—C2—C3112.8 (4)S1—C6—H6113.00
N1—C4—C2119.8 (4)C8—C6—H6113.00
N1—C4—C5111.5 (4)N1—C6—H6113.00
C2—C4—C5128.2 (4)C6—C8—H8110.00
O1—C5—C4114.2 (4)C7—C8—H8110.00
O2—C5—C4122.1 (5)N2—C8—H8110.00
O1—C5—O2123.7 (4)C11—C10—H10120.00
S1—C6—N1109.7 (3)C9—C10—H10120.00
S1—C6—C8117.0 (3)C10—C11—H11120.00
N1—C6—C888.2 (3)C12—C11—H11120.00
N1—C7—C891.5 (3)C13—C12—H12120.00
O3—C7—N1131.3 (4)C11—C12—H12120.00
O3—C7—C8137.1 (4)C12—C13—H13120.00
N2—C8—C7119.0 (3)C14—C13—H13120.00
C6—C8—C784.4 (3)C9—C14—H14121.00
N2—C8—C6120.3 (4)C13—C14—H14121.00
S2—C9—C10118.7 (3)
C6—S1—C1—C2−46.4 (4)S1—C1—C2—C3−166.4 (3)
C1—S1—C6—N157.8 (3)S1—C1—C2—C418.8 (6)
C1—S1—C6—C8156.1 (3)C1—C2—C4—N16.2 (6)
O4—S2—N2—C8−176.8 (3)C1—C2—C4—C5177.2 (4)
O5—S2—N2—C8−47.9 (3)C3—C2—C4—N1−168.1 (4)
C9—S2—N2—C867.6 (3)C3—C2—C4—C53.0 (7)
O4—S2—C9—C10−32.7 (4)N1—C4—C5—O1−155.7 (4)
O4—S2—C9—C14151.9 (4)N1—C4—C5—O223.2 (6)
O5—S2—C9—C10−165.0 (3)C2—C4—C5—O132.6 (6)
O5—S2—C9—C1419.5 (4)C2—C4—C5—O2−148.5 (5)
N2—S2—C9—C1080.4 (3)S1—C6—C8—N219.3 (5)
N2—S2—C9—C14−95.1 (4)S1—C6—C8—C7−101.1 (3)
C6—N1—C4—C211.5 (6)N1—C6—C8—N2130.5 (4)
C6—N1—C4—C5−161.0 (4)N1—C6—C8—C710.1 (3)
C7—N1—C4—C2−134.5 (5)O3—C7—C8—N245.1 (7)
C7—N1—C4—C553.1 (6)O3—C7—C8—C6166.7 (5)
C4—N1—C6—S1−49.9 (4)N1—C7—C8—N2−132.3 (4)
C4—N1—C6—C8−168.0 (3)N1—C7—C8—C6−10.7 (3)
C7—N1—C6—S1106.9 (3)S2—C9—C10—C11−177.2 (4)
C7—N1—C6—C8−11.2 (3)C14—C9—C10—C11−1.7 (6)
C4—N1—C7—O3−13.7 (7)S2—C9—C14—C13177.0 (4)
C4—N1—C7—C8164.0 (4)C10—C9—C14—C131.6 (7)
C6—N1—C7—O3−166.4 (4)C9—C10—C11—C121.0 (7)
C6—N1—C7—C811.3 (3)C10—C11—C12—C13−0.3 (8)
S2—N2—C8—C6143.8 (3)C11—C12—C13—C140.2 (8)
S2—N2—C8—C7−114.9 (3)C12—C13—C14—C9−0.8 (8)

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, −z; (iii) x−1, y, z; (iv) −x+3/2, −y+1, z+1/2; (v) x−1/2, −y+3/2, −z; (vi) −x+3/2, −y+1, z−1/2; (vii) x+1/2, −y+3/2, −z; (viii) x−1/2, −y+1/2, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···OW1iii0.821.862.663 (6)166
OW1—HW1···O5iv0.83 (4)2.14 (5)2.799 (6)136 (5)
N2—H2···S10.862.823.136 (3)103
N2—H2···O2i0.862.302.846 (4)122
OW1—HW2···O30.84 (5)2.54 (5)3.135 (6)129 (5)
C3—H3A···O10.962.222.902 (6)127
C6—H6···S1viii0.982.803.756 (4)165
C8—H8···O4iii0.982.303.100 (5)138
C8—H8···O50.982.482.922 (5)107
C11—H11···O3vii0.932.513.192 (6)130
C14—H14···O50.932.592.942 (5)103
C3—H3B···Cg3iv0.962.723.640 (5)161

Symmetry codes: (iii) x−1, y, z; (iv) −x+3/2, −y+1, z+1/2; (i) x+1, y, z; (viii) x−1/2, −y+1/2, −z; (vii) x+1/2, −y+3/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2014).

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