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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1513–o1514.
Published online 2009 June 6. doi:  10.1107/S1600536809021084
PMCID: PMC2969224

4,4′-Dianilino-3,3′-(4-chloro­benzyl­idene)bis­[furan-2(5H)-one]

Abstract

In the mol­ecule of the title compound, C27H21ClN2O4, the dihedral angle between the furan rings is 67.00 (3)°. The chloro­phenyl ring is oriented at dihedral angles of 76.61 (3) and 69.36 (3)° with respect to the furan rings. An intra­molecular N—H(...)O inter­action results in the formation of an eight-membered ring with a twisted conformation. In the crystal structure, inter­molecular N—H(...)O and C—H(...)O inter­actions link the mol­ecules into a three-dimensional network, forming R 2 2(16) ring motifs. Three weak C—H(...)π inter­actions are also found.

Related literature

For the biological activity of tetronic acid derivatives and their metabolites, see: Altenbach et al. (2006 [triangle]); Foden et al. (1975 [triangle]); Ley et al. (1991 [triangle]); Roggo et al. (1994 [triangle]); Witiak et al. (1982 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For hydrogen-bond ring motifs, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o1513-scheme1.jpg

Experimental

Crystal data

  • C27H21ClN2O4
  • M r = 472.91
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1513-efi1.jpg
  • a = 10.973 (5) Å
  • b = 11.566 (5) Å
  • c = 17.795 (8) Å
  • β = 100.232 (7)°
  • V = 2222.6 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 298 K
  • 0.28 × 0.15 × 0.12 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.943, T max = 0.975
  • 11368 measured reflections
  • 3913 independent reflections
  • 1802 reflections with I > 2σ(I)
  • R int = 0.087

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.251
  • S = 1.03
  • 3913 reflections
  • 307 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021084/hk2705sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021084/hk2705Isup2.hkl

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

Acknowledgments

We thank the Natural Science Foundation of China (grant No. 20672090), the Preliminary Item of Xuzhou Normal University on National Natural Science Foundation of China (grant No. 08XLY04) and the Science & Technology Found­ation of Xuzhou City (grant No. XM08C027) for support.

supplementary crystallographic information

Comment

Tetronic acid derivatives and their metabolites have gained much attention from synthetic and medicinal chemists because of their prominent antibiotic (Ley et al., 1991), antico-agulant (Witiak et al., 1982), anti-inflammatory (Foden et al., 1975) and anti-HIV (Roggo et al., 1994) activities. Among them, open-chain derivatives of bistetronic acid, which contain two tetronic acid skeletons in one molecule, may display important pharmacological activities (Altenbach et al., 2006). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (O1/C1-C4), B (O3/C5-C8), C (C10-C15), D (C16-C21) and E (C22-C27) are, of course, planar. The dihedral angles between them are A/B = 67.00 (3), A/C = 76.61 (3), B/C = 69.36 (3), A/D = 14.64 (3) and B/E = 32.61 (3) °. Intramolecular N-H···O interaction (Table 1) results in the formation of an eight-membered ring F (O4/N1/C2/C3/C5/C6/C9/H1), having twisted conformation.

In the crystal structure, intermolecular N-H···O and C-H···O interactions (Table 1) link the molecules into a three-dimensional network forming R22(16) ring motifs (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. There also exist three weak C—H···π interactions (Table 1).

Experimental

The title compound was prepared by the reaction of 4-chlorobenzaldehyde (0.5 mmol) with 4-phenylamino-2,5-dihydrofuran-2-one (1 mmol) in glycol at 373 K under microwave irradiation (maximum power 200 W, initial power 100 W) for 10 min (yield; 92%, m.p. 508–509 K). Crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation.

Refinement

H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93, 0.98 and 0.97 Å for aromatic, methine and methylene H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C27H21ClN2O4F(000) = 984
Mr = 472.91Dx = 1.413 Mg m3
Monoclinic, P21/nMelting point = 508–509 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.973 (5) ÅCell parameters from 1079 reflections
b = 11.566 (5) Åθ = 2.4–19.9°
c = 17.795 (8) ŵ = 0.21 mm1
β = 100.232 (7)°T = 298 K
V = 2222.6 (17) Å3Block, yellow
Z = 40.28 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer3913 independent reflections
Radiation source: fine-focus sealed tube1802 reflections with I > 2σ(I)
graphiteRint = 0.087
[var phi] and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→12
Tmin = 0.943, Tmax = 0.975k = −13→13
11368 measured reflectionsl = −11→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.251H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2)]
3913 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

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)

xyzUiso*/Ueq
Cl10.72987 (15)0.38409 (13)0.15930 (11)0.0740 (6)
O10.5201 (3)1.0941 (3)0.2030 (2)0.0537 (10)
O20.5296 (3)1.0511 (3)0.0810 (2)0.0620 (11)
O30.0934 (3)0.7208 (3)0.0853 (2)0.0498 (10)
O40.2460 (3)0.6755 (3)0.1814 (2)0.0502 (10)
N10.3811 (4)0.8428 (4)0.2747 (3)0.0503 (12)
H10.36910.77670.25250.060*
N20.2308 (4)0.9098 (4)−0.0373 (3)0.0517 (12)
H20.30810.9226−0.03670.062*
C10.5027 (5)1.0208 (4)0.1418 (4)0.0487 (14)
C20.4502 (4)0.9143 (4)0.1609 (3)0.0385 (12)
C30.4320 (4)0.9225 (4)0.2347 (3)0.0388 (12)
C40.4770 (5)1.0372 (4)0.2651 (3)0.0458 (13)
H4A0.41051.08090.28100.055*
H4B0.54381.02870.30850.055*
C50.2134 (4)0.7262 (4)0.1207 (3)0.0407 (13)
C60.2842 (4)0.7961 (4)0.0774 (3)0.0384 (12)
C70.2060 (4)0.8381 (4)0.0164 (3)0.0414 (13)
C80.0777 (4)0.7922 (5)0.0181 (3)0.0482 (14)
H8A0.02030.85480.02170.058*
H8B0.04730.7471−0.02730.058*
C90.4220 (4)0.8188 (4)0.1024 (3)0.0403 (13)
H90.45040.84810.05670.048*
C100.4950 (4)0.7072 (4)0.1233 (3)0.0379 (12)
C110.4592 (5)0.6052 (4)0.0851 (3)0.0508 (15)
H110.38580.60390.04970.061*
C120.5286 (5)0.5052 (5)0.0977 (3)0.0560 (15)
H120.50150.43710.07230.067*
C130.6382 (5)0.5084 (4)0.1484 (3)0.0474 (14)
C140.6747 (5)0.6063 (5)0.1892 (3)0.0526 (15)
H140.74670.60660.22580.063*
C150.6030 (4)0.7050 (5)0.1754 (3)0.0469 (14)
H150.62900.77200.20240.056*
C160.3439 (5)0.8482 (4)0.3466 (3)0.0442 (13)
C170.2643 (5)0.7626 (5)0.3627 (3)0.0541 (15)
H170.23860.70490.32700.065*
C180.2233 (6)0.7624 (5)0.4310 (4)0.0669 (18)
H180.16890.70490.44080.080*
C190.2606 (5)0.8448 (5)0.4849 (4)0.0625 (17)
H190.23320.84300.53150.075*
C200.3380 (5)0.9292 (5)0.4697 (3)0.0584 (16)
H200.36250.98620.50600.070*
C210.3816 (5)0.9328 (5)0.4016 (3)0.0526 (15)
H210.43560.99110.39250.063*
C220.1487 (5)0.9681 (5)−0.0949 (3)0.0485 (14)
C230.0411 (6)0.9218 (5)−0.1334 (4)0.0694 (19)
H230.01890.8469−0.12240.083*
C24−0.0353 (6)0.9854 (6)−0.1886 (4)0.0719 (19)
H24−0.10870.9525−0.21370.086*
C25−0.0056 (6)1.0951 (5)−0.2070 (4)0.0646 (17)
H25−0.05761.1376−0.24390.078*
C260.1045 (6)1.1405 (5)−0.1688 (4)0.0619 (17)
H260.12761.2147−0.18060.074*
C270.1799 (5)1.0788 (5)−0.1142 (3)0.0543 (15)
H270.25361.1116−0.08950.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0781 (11)0.0616 (10)0.0802 (14)0.0182 (8)0.0080 (10)0.0048 (9)
O10.063 (2)0.047 (2)0.054 (3)−0.0074 (18)0.020 (2)−0.006 (2)
O20.068 (3)0.067 (3)0.057 (3)−0.015 (2)0.027 (2)0.007 (2)
O30.039 (2)0.059 (2)0.049 (2)−0.0080 (16)0.0042 (19)0.011 (2)
O40.055 (2)0.059 (2)0.037 (2)−0.0088 (17)0.0071 (19)0.0074 (19)
N10.067 (3)0.047 (3)0.041 (3)−0.008 (2)0.020 (3)−0.007 (2)
N20.039 (2)0.063 (3)0.051 (3)−0.001 (2)0.002 (2)0.018 (3)
C10.043 (3)0.047 (3)0.059 (4)−0.001 (2)0.016 (3)0.001 (3)
C20.026 (2)0.056 (3)0.033 (3)−0.002 (2)0.003 (2)−0.003 (3)
C30.035 (3)0.041 (3)0.041 (3)−0.001 (2)0.007 (3)0.001 (3)
C40.050 (3)0.052 (3)0.037 (3)0.000 (3)0.013 (3)−0.002 (3)
C50.034 (3)0.048 (3)0.040 (3)−0.004 (2)0.005 (3)−0.004 (3)
C60.033 (2)0.046 (3)0.036 (3)−0.003 (2)0.005 (2)−0.003 (3)
C70.042 (3)0.045 (3)0.038 (3)−0.004 (2)0.008 (3)−0.002 (3)
C80.040 (3)0.058 (3)0.045 (4)−0.006 (2)0.003 (3)0.007 (3)
C90.033 (3)0.051 (3)0.037 (3)−0.007 (2)0.006 (2)−0.001 (3)
C100.039 (3)0.045 (3)0.029 (3)−0.002 (2)0.005 (2)−0.007 (3)
C110.041 (3)0.065 (4)0.041 (4)−0.004 (3)−0.009 (3)−0.010 (3)
C120.054 (3)0.058 (4)0.054 (4)0.001 (3)0.003 (3)−0.011 (3)
C130.048 (3)0.045 (3)0.049 (4)0.002 (2)0.008 (3)0.000 (3)
C140.041 (3)0.069 (4)0.044 (4)−0.002 (3)−0.005 (3)−0.001 (3)
C150.042 (3)0.051 (3)0.047 (4)−0.004 (3)0.004 (3)−0.009 (3)
C160.051 (3)0.050 (3)0.032 (3)0.005 (3)0.009 (3)0.003 (3)
C170.058 (3)0.064 (4)0.041 (4)−0.015 (3)0.011 (3)−0.004 (3)
C180.070 (4)0.077 (4)0.058 (5)−0.013 (3)0.023 (4)−0.002 (4)
C190.064 (4)0.083 (4)0.041 (4)0.005 (3)0.010 (3)0.008 (4)
C200.071 (4)0.064 (4)0.039 (4)0.007 (3)0.005 (3)−0.004 (3)
C210.061 (4)0.056 (3)0.040 (4)−0.009 (3)0.007 (3)−0.005 (3)
C220.051 (3)0.054 (3)0.039 (3)0.001 (3)0.004 (3)0.005 (3)
C230.065 (4)0.063 (4)0.068 (5)−0.020 (3)−0.020 (4)0.014 (4)
C240.060 (4)0.087 (5)0.061 (5)−0.016 (3)−0.013 (4)0.009 (4)
C250.060 (4)0.072 (4)0.058 (4)0.014 (3)0.002 (3)0.010 (4)
C260.070 (4)0.055 (4)0.061 (4)0.002 (3)0.012 (4)0.007 (3)
C270.051 (3)0.060 (4)0.051 (4)0.000 (3)0.004 (3)−0.001 (3)

Geometric parameters (Å, °)

Cl1—C131.745 (5)C11—H110.9300
O1—C11.366 (6)C12—C131.369 (7)
O1—C41.436 (6)C12—H120.9300
O2—C11.223 (6)C13—C141.367 (7)
O3—C51.357 (6)C14—C151.383 (7)
O3—C81.439 (6)C14—H140.9300
O4—C51.224 (6)C15—H150.9300
N1—C31.345 (6)C16—C171.384 (7)
N1—C161.412 (6)C16—C211.394 (7)
N1—H10.8600C17—C181.369 (8)
N2—C71.329 (6)C17—H170.9300
N2—C221.410 (6)C18—C191.362 (8)
N2—H20.8600C18—H180.9300
C1—C21.427 (7)C19—C201.353 (8)
C2—C31.366 (7)C19—H190.9300
C2—C91.512 (7)C20—C211.381 (8)
C3—C41.484 (7)C20—H200.9300
C4—H4A0.9700C21—H210.9300
C4—H4B0.9700C22—C231.365 (7)
C5—C61.436 (7)C22—C271.385 (7)
C6—C71.349 (7)C23—C241.384 (8)
C6—C91.522 (6)C23—H230.9300
C7—C81.509 (6)C24—C251.364 (8)
C8—H8A0.9700C24—H240.9300
C8—H8B0.9700C25—C261.381 (8)
C9—C101.530 (6)C25—H250.9300
C9—H90.9800C26—C271.360 (8)
C10—C151.369 (7)C26—H260.9300
C10—C111.383 (6)C27—H270.9300
C11—C121.381 (7)
C1—O1—C4108.2 (4)C10—C11—H11118.8
C5—O3—C8108.8 (4)C13—C12—C11118.6 (5)
C3—N1—C16131.5 (5)C13—C12—H12120.7
C3—N1—H1114.2C11—C12—H12120.7
C16—N1—H1114.2C14—C13—C12120.9 (5)
C7—N2—C22129.4 (4)C14—C13—Cl1121.0 (5)
C7—N2—H2115.3C12—C13—Cl1118.2 (4)
C22—N2—H2115.3C13—C14—C15119.0 (5)
O2—C1—O1120.4 (5)C13—C14—H14120.5
O2—C1—C2129.0 (5)C15—C14—H14120.5
O1—C1—C2110.5 (5)C10—C15—C14122.2 (5)
C3—C2—C1107.7 (5)C10—C15—H15118.9
C3—C2—C9131.7 (5)C14—C15—H15118.9
C1—C2—C9120.6 (5)C17—C16—C21118.5 (5)
N1—C3—C2127.3 (5)C17—C16—N1116.8 (5)
N1—C3—C4124.2 (5)C21—C16—N1124.7 (5)
C2—C3—C4108.4 (4)C18—C17—C16120.3 (6)
O1—C4—C3105.2 (4)C18—C17—H17119.8
O1—C4—H4A110.7C16—C17—H17119.8
C3—C4—H4A110.7C19—C18—C17121.3 (6)
O1—C4—H4B110.7C19—C18—H18119.4
C3—C4—H4B110.7C17—C18—H18119.4
H4A—C4—H4B108.8C20—C19—C18118.9 (6)
O4—C5—O3119.6 (4)C20—C19—H19120.5
O4—C5—C6129.9 (5)C18—C19—H19120.5
O3—C5—C6110.4 (5)C19—C20—C21121.8 (6)
C7—C6—C5107.9 (4)C19—C20—H20119.1
C7—C6—C9129.1 (5)C21—C20—H20119.1
C5—C6—C9123.0 (5)C20—C21—C16119.2 (5)
N2—C7—C6128.4 (5)C20—C21—H21120.4
N2—C7—C8123.0 (5)C16—C21—H21120.4
C6—C7—C8108.6 (5)C23—C22—C27117.9 (5)
O3—C8—C7104.2 (4)C23—C22—N2124.2 (5)
O3—C8—H8A110.9C27—C22—N2118.0 (5)
C7—C8—H8A110.9C22—C23—C24120.6 (6)
O3—C8—H8B110.9C22—C23—H23119.7
C7—C8—H8B110.9C24—C23—H23119.7
H8A—C8—H8B108.9C25—C24—C23121.6 (6)
C2—C9—C6113.4 (4)C25—C24—H24119.2
C2—C9—C10114.5 (4)C23—C24—H24119.2
C6—C9—C10112.1 (4)C24—C25—C26117.4 (6)
C2—C9—H9105.2C24—C25—H25121.3
C6—C9—H9105.2C26—C25—H25121.3
C10—C9—H9105.2C27—C26—C25121.3 (6)
C15—C10—C11116.9 (5)C27—C26—H26119.3
C15—C10—C9122.2 (4)C25—C26—H26119.3
C11—C10—C9120.7 (4)C26—C27—C22121.1 (6)
C12—C11—C10122.3 (5)C26—C27—H27119.4
C12—C11—H11118.8C22—C27—H27119.4
C4—O1—C1—O2178.2 (5)C7—C6—C9—C10−133.2 (5)
C4—O1—C1—C2−0.8 (5)C5—C6—C9—C1049.9 (6)
O2—C1—C2—C3−177.5 (5)C2—C9—C10—C15−20.6 (7)
O1—C1—C2—C31.3 (6)C6—C9—C10—C15−151.7 (5)
O2—C1—C2—C91.1 (8)C2—C9—C10—C11164.8 (4)
O1—C1—C2—C9180.0 (4)C6—C9—C10—C1133.7 (7)
C16—N1—C3—C2−170.5 (5)C15—C10—C11—C12−0.6 (8)
C16—N1—C3—C48.6 (8)C9—C10—C11—C12174.3 (5)
C1—C2—C3—N1177.9 (5)C10—C11—C12—C13−1.7 (8)
C9—C2—C3—N1−0.5 (9)C11—C12—C13—C144.0 (8)
C1—C2—C3—C4−1.3 (5)C11—C12—C13—Cl1−176.0 (4)
C9—C2—C3—C4−179.7 (5)C12—C13—C14—C15−3.9 (8)
C1—O1—C4—C30.0 (5)Cl1—C13—C14—C15176.1 (4)
N1—C3—C4—O1−178.4 (4)C11—C10—C15—C140.8 (8)
C2—C3—C4—O10.9 (5)C9—C10—C15—C14−174.1 (5)
C8—O3—C5—O4176.8 (5)C13—C14—C15—C101.5 (8)
C8—O3—C5—C6−2.7 (5)C3—N1—C16—C17162.7 (5)
O4—C5—C6—C7−176.9 (5)C3—N1—C16—C21−17.4 (9)
O3—C5—C6—C72.5 (6)C21—C16—C17—C180.6 (8)
O4—C5—C6—C90.5 (8)N1—C16—C17—C18−179.5 (5)
O3—C5—C6—C9179.9 (4)C16—C17—C18—C19−0.9 (9)
C22—N2—C7—C6−169.7 (5)C17—C18—C19—C201.1 (9)
C22—N2—C7—C88.8 (9)C18—C19—C20—C21−1.1 (9)
C5—C6—C7—N2177.4 (5)C19—C20—C21—C160.8 (9)
C9—C6—C7—N20.2 (9)C17—C16—C21—C20−0.6 (8)
C5—C6—C7—C8−1.2 (6)N1—C16—C21—C20179.6 (5)
C9—C6—C7—C8−178.4 (5)C7—N2—C22—C23−37.0 (9)
C5—O3—C8—C71.9 (5)C7—N2—C22—C27143.6 (6)
N2—C7—C8—O3−179.0 (5)C27—C22—C23—C24−1.5 (9)
C6—C7—C8—O3−0.3 (6)N2—C22—C23—C24179.1 (6)
C3—C2—C9—C665.9 (7)C22—C23—C24—C250.7 (10)
C1—C2—C9—C6−112.3 (5)C23—C24—C25—C260.5 (10)
C3—C2—C9—C10−64.5 (7)C24—C25—C26—C27−0.8 (9)
C1—C2—C9—C10117.3 (5)C25—C26—C27—C22−0.1 (9)
C7—C6—C9—C295.1 (7)C23—C22—C27—C261.2 (9)
C5—C6—C9—C2−81.7 (6)N2—C22—C27—C26−179.4 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O40.862.052.797 (3)145
N2—H2···O2i0.862.092.907 (3)158
C4—H4A···O4ii0.972.243.206 (3)178
C8—H8A···Cg5iii0.972.983.721 (3)134
C8—H8B···Cg4iv0.972.913.617 (3)131
C19—H19···Cg3v0.932.903.766 (3)156

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2705).

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