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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o589–o590.
Published online 2010 February 13. doi:  10.1107/S1600536810005064
PMCID: PMC2983650

α-Costic anhydride

Abstract

The title compound [systematic name: 2-(4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octa­hydro­naphthalen-2-yl)acrylic acid anhydride], C30H42O3, is a new isocostic anhydride which was synthesized from the aerial part of Inula Viscosa­ (L) Aiton [or Dittrichia Viscosa­ (L) Greuter]. The mol­ecule adopts an essentially linear shape with two terminal fused-rings bridged by the anhydride group. The external rings have the same conformation (half-chair) while each of the two inner rings has an almost ideal chair conformation. In the crystal, inter­molecular C—H(...)O inter­actions link the mol­ecules into a two-dimensional array in the bc plane.

Related literature

For background to the medicinal inter­est in Inula Viscosa­ (L) Aiton [or Dittrichia Viscosa­ (L) Greuter], see: Shtacher & Kasshman (1970 [triangle]); Bohlman & Gupta (1982 [triangle]); Azoulay et al. (1986 [triangle]); Bohlmann et al. (1977 [triangle]); Ceccherelli et al. (1988 [triangle]); Grande et al. (1985 [triangle]); Chiappini et al. (1982 [triangle]). For background to the phytochemical study of Moroccan plants, see: Tebaa et al. (2009 [triangle]); Zeroual et al. (2007 [triangle]). For conformational analysis, see: Cremer & Pople (1975 [triangle]).

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Object name is e-66-0o589-scheme1.jpg

Experimental

Crystal data

  • C30H42O3
  • M r = 450.64
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o589-efi1.jpg
  • a = 6.6699 (2) Å
  • b = 6.6335 (2) Å
  • c = 30.2948 (8) Å
  • β = 92.799 (1)°
  • V = 1338.79 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 298 K
  • 0.28 × 0.17 × 0.12 mm

Data collection

  • Bruker X8 APEX CCD area-detector diffractometer
  • 15300 measured reflections
  • 2914 independent reflections
  • 2604 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.109
  • S = 1.05
  • 2914 reflections
  • 304 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT-Plus (Bruker, 2009 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810005064/tk2617sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005064/tk2617Isup2.hkl

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

Acknowledgments

The authors thank the CNRST and RéPAM for financial support and the Unit of Support for Technical and Scientific Research (UATRS, CNRST: URAC 16 and URAC 26) for making possible the present work. They also thank H. Zouihri for his helpful technical assistance during the X-ray measurements.

supplementary crystallographic information

Comment

Inula Viscosa (L) Aiton or Dittrichia Viscosa (L) Greuter is widespread in Mediterranean area and extends to the Atlantic cost of Morocco. It is a well known medicinal plant (Shtacher & Kasshman, 1970 ; Bohlman & Gupta, 1982) and has some pharmacological activities (Azoulay et al., 1986). This plant has been the subject of chemical investigation in terms of isolating sesquiterpene lactones (Bohlmann et al., 1977), sesquiterpene acids (Ceccherelli et al.,1988) and flavonoids (Grande et al., 1985; Chiappini et al., 1982).

The work of our research group has focused upon the phytochemical study of Moroccan plants (Tebaa et al., 2009 ; Zeroual et al., 2007) with the aim to discover new compounds which could be used as precursors or intermediates for the synthesis of novel molecules. In this way, we have investigated Inula Viscosa (L) which is rich in sesquiterpene derivatives. The title compound C30H42O3, (I), was obtained through a chemical modification of 2-(4a,8-dimethyl-1,2,3,4,4a,,5,6,8a-octahdro-naphtaen-2-yl)- acrylic acid,which was isolated in high yield from Inula viscosa (L). The dimerisation of the above compound was obtained by the treatment of iscostic acid by the ethyl chloroformate in the presence of triethylamine.

The molecular structure of (I), Fig. 1, shows each of the external rings (labelled A and D in the Scheme) to adopt a half-chair conformation, as indicated by the total puckering amplitude QT = 0.504 (3) Å and spherical polar angle θ = 131.4 (3) ° with [var phi] = 286.2 (4) ° for ring (A), and QT = 0.504 (2) Å and θ =131.1 (3) ° with [var phi] = 168.5 (4) ° for ring (D). By contrast, the inners rings (B and C) have a chair conformation with QT = 0.57 (2) Å, θ =1.3 (2) °,[var phi] = 67 (5) ° for ring (B), and QT = 0.57 (2) Å, θ =2.0 (2) °, [var phi] = 168.5 (4) ° for ring (C) (Cremer & Pople, 1975). In the crystal structure, there are two intermolecular C–H···O contacts, involving the carbonyl-O2 and -O3 atoms (Fig. 2; Table 1), which cooperate to form a 2-D array in the bc plane.

Experimental

A solution containing equimolar quantities of isocostic acid (500 mg) and triethyl amine (0.5 mL) was stirred at 263 K for 10 mins. To this was added a 0.5 equivalent of ethyl chloroformate (0.3 mL) and the reaction mixture was stirred for 1 h. The residue obtained was purified on a silica gel column using hexane-ethyl acetate (99:1) as an eluent which yielded compound (I) in 70% yield.

Refinement

All H atoms were fixed geometrically and treated as riding with C—H = 0.93–0.98 Å with Uiso(H) = 1.2–1.5Ueq(C). In the absence of significant anomalous scattering, the absolute configuration could not be reliably determined and thus 2403 Friedel pairs were merged.

Figures

Fig. 1.
: Molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
: A partial packing digram of (I), showing intermolecular C–H···O contacts (dashed lines). [Symmetry code: (i) x, -1+y, z; (ii) -1+x, y, z]

Crystal data

C30H42O3F(000) = 492
Mr = 450.64Dx = 1.118 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 15300 reflections
a = 6.6699 (2) Åθ = 0.7–26.1°
b = 6.6335 (2) ŵ = 0.07 mm1
c = 30.2948 (8) ÅT = 298 K
β = 92.799 (1)°Prism, colourless
V = 1338.79 (7) Å30.28 × 0.17 × 0.12 mm
Z = 2

Data collection

Bruker X8 APEX CCD area-detector diffractometer2604 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
graphiteθmax = 26.1°, θmin = 0.7°
[var phi] and ω scansh = −8→8
15300 measured reflectionsk = −8→8
2914 independent reflectionsl = −37→37

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0425P)2 + 0.3687P] where P = (Fo2 + 2Fc2)/3
2914 reflections(Δ/σ)max < 0.001
304 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = −0.12 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C1−0.4278 (5)0.3168 (6)0.92476 (10)0.0684 (9)
H1−0.50860.20290.92630.087 (11)*
C2−0.3866 (6)0.4312 (7)0.96587 (11)0.0807 (12)
H2A−0.30270.35010.98600.097*
H2B−0.51230.45570.97980.097*
C3−0.2841 (5)0.6299 (7)0.95871 (9)0.0705 (9)
H3A−0.22020.67480.98640.085*
H3B−0.38400.72950.94950.085*
C4−0.1256 (4)0.6164 (5)0.92373 (8)0.0494 (6)
C5−0.0308 (5)0.8240 (5)0.91750 (9)0.0623 (8)
H5A0.04490.86110.94440.075*
H5B−0.13660.92290.91250.075*
C60.1087 (5)0.8304 (5)0.87881 (9)0.0598 (8)
H6A0.15710.96700.87510.072*
H6B0.22380.74420.88530.072*
C70.0003 (4)0.7606 (4)0.83602 (8)0.0423 (6)
H7−0.11000.85540.82960.051*
C8−0.0936 (4)0.5527 (4)0.84179 (8)0.0450 (6)
H8A0.01150.45370.84750.054*
H8B−0.16820.51460.81480.054*
C9−0.2345 (4)0.5549 (4)0.88021 (8)0.0424 (6)
H9−0.33180.66240.87330.051*
C10−0.3577 (4)0.3643 (5)0.88525 (9)0.0502 (7)
C11−0.4056 (6)0.2386 (6)0.84572 (12)0.0796 (10)
H11A−0.48340.12400.85400.119*
H11B−0.28330.19340.83350.119*
H11C−0.48120.31680.82410.119*
C120.0350 (5)0.4630 (7)0.93871 (11)0.0737 (10)
H12A0.14110.46370.91840.111*
H12B−0.02360.33090.93940.111*
H12C0.08850.49800.96770.111*
C130.1364 (4)0.7703 (4)0.79758 (9)0.0449 (6)
C140.2112 (6)0.6149 (5)0.77756 (12)0.0845 (12)
H14A0.29010.63420.75340.101*
H14B0.18550.48510.78740.101*
C150.1767 (4)0.9763 (4)0.78202 (8)0.0426 (6)
C160.3228 (3)1.1350 (4)0.72013 (8)0.0415 (6)
C170.5257 (3)1.1794 (4)0.70471 (8)0.0436 (6)
C180.6835 (4)1.0992 (7)0.72518 (11)0.0753 (11)
H18A0.66811.01470.74930.090*
H18B0.81101.12660.71560.090*
C190.5274 (3)1.3227 (4)0.66603 (7)0.0417 (6)
H190.43491.43300.67210.050*
C200.4477 (4)1.2199 (6)0.62350 (8)0.0591 (8)
H20A0.53051.10360.61760.071*
H20B0.31191.17280.62730.071*
C210.4484 (4)1.3633 (6)0.58433 (8)0.0630 (9)
H21A0.35141.46960.58860.076*
H21B0.40581.29030.55780.076*
C220.6533 (4)1.4587 (5)0.57758 (8)0.0508 (7)
C230.7253 (4)1.5623 (4)0.62083 (8)0.0415 (6)
H230.62031.66000.62720.050*
C240.7336 (4)1.4171 (4)0.65969 (8)0.0447 (6)
H24A0.77771.48860.68640.054*
H24B0.83031.31150.65460.054*
C250.9128 (4)1.6862 (5)0.61507 (9)0.0529 (7)
C260.9537 (5)1.7582 (5)0.57536 (11)0.0681 (9)
H261.06741.83840.57360.074 (10)*
C270.8326 (6)1.7205 (7)0.53396 (11)0.0801 (11)
H27A0.90851.63540.51480.096*
H27B0.80801.84770.51890.096*
C280.6343 (5)1.6208 (7)0.54171 (10)0.0717 (9)
H28A0.58241.56010.51440.086*
H28B0.53911.72230.55030.086*
C291.0455 (5)1.7295 (6)0.65482 (12)0.0789 (10)
H29A1.15751.80940.64650.118*
H29B1.09341.60500.66760.118*
H29C0.97121.80200.67610.118*
C300.8016 (6)1.2973 (6)0.56362 (11)0.0736 (10)
H30A0.93301.35540.56240.110*
H30B0.75961.24600.53500.110*
H30C0.80521.18930.58470.110*
O10.3244 (3)0.9824 (3)0.75129 (6)0.0519 (5)
O20.0998 (3)1.1250 (3)0.79450 (7)0.0590 (5)
O30.1723 (3)1.2153 (4)0.70730 (6)0.0600 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0541 (16)0.078 (2)0.074 (2)−0.0201 (17)0.0141 (14)0.0170 (19)
C20.077 (2)0.105 (3)0.0628 (19)−0.015 (2)0.0278 (16)0.017 (2)
C30.084 (2)0.084 (2)0.0460 (15)−0.007 (2)0.0241 (15)−0.0028 (18)
C40.0552 (15)0.0556 (16)0.0378 (12)−0.0088 (14)0.0081 (10)0.0062 (13)
C50.084 (2)0.061 (2)0.0425 (14)−0.0198 (18)0.0090 (13)−0.0091 (14)
C60.0707 (18)0.0589 (19)0.0502 (15)−0.0273 (16)0.0081 (12)−0.0005 (15)
C70.0535 (14)0.0331 (13)0.0411 (12)−0.0028 (11)0.0101 (10)0.0045 (11)
C80.0552 (14)0.0405 (14)0.0399 (12)−0.0079 (12)0.0086 (10)0.0021 (11)
C90.0423 (12)0.0421 (14)0.0433 (13)0.0021 (11)0.0086 (10)0.0071 (11)
C100.0407 (13)0.0517 (17)0.0583 (15)−0.0056 (12)0.0031 (11)0.0072 (14)
C110.079 (2)0.072 (2)0.089 (2)−0.035 (2)0.0108 (17)−0.003 (2)
C120.0582 (17)0.095 (3)0.0669 (18)−0.0035 (18)−0.0069 (14)0.032 (2)
C130.0557 (14)0.0345 (13)0.0458 (13)−0.0037 (11)0.0147 (11)0.0045 (11)
C140.128 (3)0.0383 (17)0.093 (2)−0.002 (2)0.067 (2)0.0088 (19)
C150.0462 (13)0.0386 (14)0.0435 (13)−0.0029 (12)0.0084 (10)0.0055 (12)
C160.0401 (13)0.0424 (14)0.0428 (12)−0.0048 (12)0.0091 (10)0.0047 (12)
C170.0383 (12)0.0520 (16)0.0411 (12)−0.0035 (11)0.0082 (9)0.0067 (12)
C180.0452 (15)0.105 (3)0.0771 (19)0.0025 (18)0.0132 (13)0.042 (2)
C190.0386 (11)0.0476 (16)0.0396 (12)−0.0052 (12)0.0074 (9)0.0040 (12)
C200.0589 (16)0.072 (2)0.0471 (14)−0.0277 (16)0.0050 (12)0.0014 (16)
C210.0638 (17)0.086 (2)0.0390 (13)−0.0177 (18)−0.0034 (11)0.0025 (16)
C220.0540 (14)0.0620 (18)0.0371 (12)−0.0056 (14)0.0090 (10)0.0056 (14)
C230.0428 (12)0.0409 (14)0.0418 (12)0.0014 (11)0.0114 (10)0.0023 (11)
C240.0423 (12)0.0508 (17)0.0411 (12)−0.0091 (12)0.0025 (9)0.0049 (12)
C250.0507 (14)0.0443 (16)0.0647 (16)−0.0053 (13)0.0124 (12)0.0059 (14)
C260.0652 (18)0.061 (2)0.079 (2)−0.0125 (17)0.0203 (15)0.0178 (18)
C270.095 (2)0.083 (3)0.0640 (19)−0.007 (2)0.0216 (17)0.032 (2)
C280.078 (2)0.087 (3)0.0501 (16)−0.004 (2)0.0049 (14)0.0217 (18)
C290.070 (2)0.075 (3)0.091 (2)−0.032 (2)0.0022 (17)0.008 (2)
C300.094 (2)0.066 (2)0.0630 (19)0.001 (2)0.0318 (17)−0.0088 (18)
O10.0483 (9)0.0472 (11)0.0620 (10)0.0037 (9)0.0215 (8)0.0176 (10)
O20.0766 (13)0.0362 (10)0.0664 (12)−0.0011 (10)0.0270 (10)0.0048 (10)
O30.0373 (9)0.0784 (15)0.0652 (11)−0.0008 (10)0.0099 (8)0.0263 (12)

Geometric parameters (Å, °)

C1—C101.344 (4)C16—O31.185 (3)
C1—C21.473 (5)C16—O11.384 (3)
C1—H10.9300C16—C171.482 (3)
C2—C31.506 (6)C17—C181.308 (4)
C2—H2A0.9700C17—C191.509 (3)
C2—H2B0.9700C18—H18A0.9300
C3—C41.535 (3)C18—H18B0.9300
C3—H3A0.9700C19—C201.530 (4)
C3—H3B0.9700C19—C241.532 (3)
C4—C91.529 (4)C19—H190.9800
C4—C121.531 (5)C20—C211.521 (4)
C4—C51.531 (4)C20—H20A0.9700
C5—C61.532 (4)C20—H20B0.9700
C5—H5A0.9700C21—C221.529 (4)
C5—H5B0.9700C21—H21A0.9700
C6—C71.525 (4)C21—H21B0.9700
C6—H6A0.9700C22—C281.530 (4)
C6—H6B0.9700C22—C301.531 (4)
C7—C131.512 (3)C22—C231.536 (4)
C7—C81.528 (4)C23—C251.514 (4)
C7—H70.9800C23—C241.520 (3)
C8—C91.531 (3)C23—H230.9800
C8—H8A0.9700C24—H24A0.9700
C8—H8B0.9700C24—H24B0.9700
C9—C101.520 (4)C25—C261.335 (4)
C9—H90.9800C25—C291.487 (4)
C10—C111.481 (5)C26—C271.479 (5)
C11—H11A0.9600C26—H260.9300
C11—H11B0.9600C27—C281.507 (5)
C11—H11C0.9600C27—H27A0.9700
C12—H12A0.9600C27—H27B0.9700
C12—H12B0.9600C28—H28A0.9700
C12—H12C0.9600C28—H28B0.9700
C13—C141.307 (4)C29—H29A0.9600
C13—C151.475 (4)C29—H29B0.9600
C14—H14A0.9300C29—H29C0.9600
C14—H14B0.9300C30—H30A0.9600
C15—O21.182 (3)C30—H30B0.9600
C15—O11.389 (3)C30—H30C0.9600
C10—C1—C2125.0 (3)O3—C16—C17125.3 (2)
C10—C1—H1117.5O1—C16—C17112.6 (2)
C2—C1—H1117.5C18—C17—C16119.7 (2)
C1—C2—C3113.4 (3)C18—C17—C19126.0 (2)
C1—C2—H2A108.9C16—C17—C19114.3 (2)
C3—C2—H2A108.9C17—C18—H18A120.0
C1—C2—H2B108.9C17—C18—H18B120.0
C3—C2—H2B108.9H18A—C18—H18B120.0
H2A—C2—H2B107.7C17—C19—C20111.0 (2)
C2—C3—C4112.4 (3)C17—C19—C24113.3 (2)
C2—C3—H3A109.1C20—C19—C24110.71 (19)
C4—C3—H3A109.1C17—C19—H19107.2
C2—C3—H3B109.1C20—C19—H19107.2
C4—C3—H3B109.1C24—C19—H19107.2
H3A—C3—H3B107.9C21—C20—C19111.3 (3)
C9—C4—C12112.0 (3)C21—C20—H20A109.4
C9—C4—C5108.4 (2)C19—C20—H20A109.4
C12—C4—C5110.3 (3)C21—C20—H20B109.4
C9—C4—C3107.3 (2)C19—C20—H20B109.4
C12—C4—C3109.2 (3)H20A—C20—H20B108.0
C5—C4—C3109.6 (3)C20—C21—C22113.6 (2)
C4—C5—C6112.9 (3)C20—C21—H21A108.9
C4—C5—H5A109.0C22—C21—H21A108.9
C6—C5—H5A109.0C20—C21—H21B108.9
C4—C5—H5B109.0C22—C21—H21B108.9
C6—C5—H5B109.0H21A—C21—H21B107.7
H5A—C5—H5B107.8C21—C22—C28110.0 (2)
C7—C6—C5111.2 (2)C21—C22—C30109.9 (3)
C7—C6—H6A109.4C28—C22—C30109.1 (2)
C5—C6—H6A109.4C21—C22—C23108.4 (2)
C7—C6—H6B109.4C28—C22—C23107.7 (3)
C5—C6—H6B109.4C30—C22—C23111.7 (2)
H6A—C6—H6B108.0C25—C23—C24115.7 (2)
C13—C7—C6111.4 (2)C25—C23—C22111.7 (2)
C13—C7—C8113.0 (2)C24—C23—C22112.0 (2)
C6—C7—C8110.9 (2)C25—C23—H23105.4
C13—C7—H7107.1C24—C23—H23105.4
C6—C7—H7107.1C22—C23—H23105.4
C8—C7—H7107.1C23—C24—C19110.9 (2)
C7—C8—C9110.4 (2)C23—C24—H24A109.5
C7—C8—H8A109.6C19—C24—H24A109.5
C9—C8—H8A109.6C23—C24—H24B109.5
C7—C8—H8B109.6C19—C24—H24B109.5
C9—C8—H8B109.6H24A—C24—H24B108.0
H8A—C8—H8B108.1C26—C25—C29121.4 (3)
C10—C9—C4111.8 (2)C26—C25—C23120.3 (3)
C10—C9—C8115.1 (2)C29—C25—C23118.3 (2)
C4—C9—C8112.0 (2)C25—C26—C27125.2 (3)
C10—C9—H9105.7C25—C26—H26117.4
C4—C9—H9105.7C27—C26—H26117.4
C8—C9—H9105.7C26—C27—C28112.9 (3)
C1—C10—C11121.2 (3)C26—C27—H27A109.0
C1—C10—C9119.9 (3)C28—C27—H27A109.0
C11—C10—C9118.9 (2)C26—C27—H27B109.0
C10—C11—H11A109.5C28—C27—H27B109.0
C10—C11—H11B109.5H27A—C27—H27B107.8
H11A—C11—H11B109.5C27—C28—C22112.1 (3)
C10—C11—H11C109.5C27—C28—H28A109.2
H11A—C11—H11C109.5C22—C28—H28A109.2
H11B—C11—H11C109.5C27—C28—H28B109.2
C4—C12—H12A109.5C22—C28—H28B109.2
C4—C12—H12B109.5H28A—C28—H28B107.9
H12A—C12—H12B109.5C25—C29—H29A109.5
C4—C12—H12C109.5C25—C29—H29B109.5
H12A—C12—H12C109.5H29A—C29—H29B109.5
H12B—C12—H12C109.5C25—C29—H29C109.5
C14—C13—C15120.2 (2)H29A—C29—H29C109.5
C14—C13—C7125.5 (3)H29B—C29—H29C109.5
C15—C13—C7114.3 (2)C22—C30—H30A109.5
C13—C14—H14A120.0C22—C30—H30B109.5
C13—C14—H14B120.0H30A—C30—H30B109.5
H14A—C14—H14B120.0C22—C30—H30C109.5
O2—C15—O1121.6 (2)H30A—C30—H30C109.5
O2—C15—C13125.6 (2)H30B—C30—H30C109.5
O1—C15—C13112.8 (2)C16—O1—C15119.8 (2)
O3—C16—O1122.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14B···O2i0.932.473.378 (4)166
C18—H18B···O3ii0.932.513.419 (3)168

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2617).

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