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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o311–o312.
Published online 2007 December 21. doi:  10.1107/S1600536807066780
PMCID: PMC2915357

Ethyl 3-(4-fluoro­phen­yl)-6-methyl-4-oxo-2-(1-cyclohexylamino)-3,4-dihydro­furo[2,3-d]pyrimidine-5-carboxyl­ate

Abstract

In the crystal structure of the title compound, C22H24FN3O4, the two fused rings of furo[2,3-d]pyrimidine form a dihedral angle of 0.88 (13)°. The attached benzene ring is twisted with respect to the heterocyclic pyrimidinone ring, making a dihedral angle of 75.07 (12)°. The cyclo­hexyl ring shows a distorted chair conformation. The mol­ecular structure is stabilized by intra­molecular C—H(...)O and C—H(...)N hydrogen-bonding inter­actions. The crystal packing is mainly stabilized by C—H(...)π hydrogen-bond inter­actions. Further stability is provided by C—F(...)π and C—O(...)π stacking inter­actions.

Related literature

The preparation and biological activity are described by Miyazaki et al. (2007 [triangle]), Gangjee et al. (2006 [triangle]) and Lagu et al. (2000 [triangle]). For related literature, see: Ding et al. (2004 [triangle]). For the crystal structure of another fused pyrimidinone derivative, see: Hu et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o311-scheme1.jpg

Experimental

Crystal data

  • C22H24FN3O4
  • M r = 413.44
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o311-efi1.jpg
  • a = 9.2051 (8) Å
  • b = 10.7957 (9) Å
  • c = 11.6601 (10) Å
  • α = 106.681 (1)°
  • β = 100.417 (2)°
  • γ = 101.550 (2)°
  • V = 1051.85 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 291 (2) K
  • 0.30 × 0.30 × 0.20 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.972, T max = 0.981
  • 10785 measured reflections
  • 4505 independent reflections
  • 2941 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.182
  • S = 1.09
  • 4505 reflections
  • 276 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2001 [triangle]).

Table 1
Hydrogen-bond and C—F(...)π and C—O(...)π interactions (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807066780/at2523sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066780/at2523Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (project No. 20102001) and the Key Science Research Project of Hubei Provincial Department of Education (grant No. D200724001).

supplementary crystallographic information

Comment

Fused pyrimidine compounds are valued not only for their rich and varied chemistry, but also for many important biological properties. Among them, the furopyrimidine ring system, because of a formal isoelectronic relationship with purine, is of special biological interest (Miyazaki et al., 2007; Gangjee et al. 2006; Lagu et al., 2000). Recently, we have focused on the synthesis of the heterocycle systems containing fused furopyrimidine via aza-Wittig reaction at room temperature (Hu,et al., 2007). Herein, we present X-ray crystallographic analysis of the compound (I) in this paper,(Fig. 1), which may be used as a new precursor for obtaining bioactive molecules.

In the molecule (I), the bond lengths and angles are unexceptional. The two fused rings of furo[2,3-d]pyrimidine form a dihedral angle of 0.88 (13)°. The C11—C16 phenyl ring is twisted with respect to pyrimidinone ring, with a dihedral angle of 75.07 (1)°. The cyclohexyl ring in (I) shows a distored chair conformation [[var phi] =30.0 (3)° and θ = 2.5 (3)°, puckering amplitude = 0.557 (3) Å]. The molecular structure is stabilized by intramolecular C—H···O and C—H···N hydrogen bonds interactions (Table 1). The crystal packing is mainly stabilized by C—H···π hydrogen bonding interactions. Further stability is provided by C—F···π and C—O···π stacking interactions.

Experimental

To a solution of the diethyl 2-((4-fluorophenylimino)methyleneamino)-5-methylfuran- 3,4-dicarboxylate (3 mmol) in dichloromethane (5 ml) was added cyclohexanamine (3 mmol). After stirring the reaction mixture for 1 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 3 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound in a yield of 84%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.

Refinement

All H atoms were located in difference maps and treated as riding atoms, with N—H = 0.86 Å and C—H = 0.93 - 0.98 Å, and Uiso = 1.2 or 1.5Ueq (C,N).

Figures

Fig. 1.
The molecular structure of the title compound (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Only the intramolecular C—H···O and C—H···N ...
Fig. 2.
A view of the packing and hydrogen bonding interactions of (I).

Crystal data

C22H24FN3O4Z = 2
Mr = 413.44F000 = 436
Triclinic, P1Dx = 1.305 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.2051 (8) ÅCell parameters from 1930 reflections
b = 10.7957 (9) Åθ = 2.3–22.7º
c = 11.6601 (10) ŵ = 0.10 mm1
α = 106.681 (1)ºT = 291 (2) K
β = 100.417 (2)ºBlock, colourless
γ = 101.550 (2)º0.30 × 0.30 × 0.20 mm
V = 1051.85 (16) Å3

Data collection

Bruker SMART 4K CCD area-detector diffractometer4505 independent reflections
Radiation source: fine-focus sealed tube2941 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.036
T = 291(2) Kθmax = 27.0º
[var phi] and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −11→11
Tmin = 0.972, Tmax = 0.981k = −13→13
10785 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.182  w = 1/[σ2(Fo2) + (0.084P)2 + 0.0618P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
4505 reflectionsΔρmax = 0.27 e Å3
276 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
C10.3069 (4)1.3641 (3)0.4580 (4)0.0893 (11)
H1A0.20111.32430.45050.134*
H1B0.31601.44510.43790.134*
H1C0.36511.38460.54130.134*
C20.3654 (4)1.2701 (3)0.3728 (3)0.0611 (8)
H2A0.30831.24980.28810.073*
H2B0.47261.30910.38000.073*
C30.3773 (3)1.0444 (2)0.3310 (2)0.0405 (6)
C40.3423 (3)0.9266 (2)0.37091 (19)0.0382 (5)
C50.3652 (3)0.8068 (3)0.3117 (2)0.0436 (6)
C60.4214 (4)0.7543 (3)0.2014 (2)0.0621 (8)
H6A0.41010.80810.14940.093*
H6B0.36310.66320.15630.093*
H6C0.52760.75730.22690.093*
C70.2826 (2)0.9094 (2)0.47482 (18)0.0346 (5)
C80.2770 (3)0.7808 (2)0.46902 (19)0.0388 (5)
C90.2328 (3)0.9897 (2)0.5730 (2)0.0404 (6)
C100.1892 (3)0.7846 (2)0.6342 (2)0.0402 (6)
C110.1584 (3)0.9935 (2)0.76523 (19)0.0372 (5)
C120.0208 (3)1.0263 (2)0.7601 (2)0.0433 (6)
H12−0.05141.00000.68470.052*
C13−0.0090 (3)1.0983 (3)0.8672 (2)0.0486 (6)
H13−0.10131.12130.86530.058*
C140.0991 (3)1.1353 (2)0.9765 (2)0.0480 (6)
C150.2366 (3)1.1045 (3)0.9847 (2)0.0512 (7)
H150.30801.13111.06050.061*
C160.2661 (3)1.0329 (2)0.8772 (2)0.0442 (6)
H160.35911.01100.87980.053*
C170.1711 (3)0.6040 (2)0.7262 (2)0.0482 (6)
H170.18610.55170.64750.058*
C180.0384 (3)0.5200 (3)0.7535 (3)0.0711 (9)
H18A−0.05250.49560.68620.085*
H18B0.01750.57190.82860.085*
C190.0750 (4)0.3927 (3)0.7692 (3)0.0855 (11)
H19A−0.00890.34310.79180.103*
H19B0.08430.33620.69100.103*
C220.3165 (3)0.6368 (3)0.8250 (3)0.0721 (9)
H22A0.30630.69370.90270.087*
H22B0.40090.68630.80280.087*
C210.3524 (4)0.5105 (4)0.8417 (4)0.0887 (11)
H21A0.37570.45940.76750.106*
H21B0.44230.53560.91000.106*
F10.0682 (2)1.20612 (17)1.08220 (14)0.0762 (5)
N10.1902 (2)0.91680 (18)0.65370 (16)0.0378 (5)
N20.2326 (2)0.71226 (19)0.54199 (17)0.0446 (5)
N30.1374 (3)0.7269 (2)0.71300 (19)0.0498 (6)
H30.117 (3)0.781 (3)0.774 (2)0.060*
O10.3480 (2)1.14890 (17)0.40502 (15)0.0509 (5)
O20.4260 (2)1.04606 (19)0.24179 (15)0.0588 (5)
O30.32637 (19)0.71581 (16)0.37123 (14)0.0467 (4)
O40.2239 (2)1.10393 (18)0.59732 (17)0.0639 (6)
C200.2211 (4)0.4244 (3)0.8669 (3)0.0785 (10)
H20A0.20730.47050.94720.094*
H20B0.24470.34140.86940.094*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.116 (3)0.060 (2)0.113 (3)0.040 (2)0.051 (2)0.036 (2)
C20.078 (2)0.0520 (18)0.0698 (18)0.0230 (15)0.0288 (15)0.0349 (15)
C30.0412 (13)0.0461 (15)0.0371 (12)0.0116 (11)0.0116 (10)0.0170 (11)
C40.0408 (13)0.0407 (14)0.0353 (11)0.0116 (11)0.0115 (10)0.0144 (10)
C50.0492 (15)0.0439 (15)0.0394 (12)0.0130 (12)0.0139 (11)0.0143 (11)
C60.087 (2)0.0552 (18)0.0517 (15)0.0236 (16)0.0370 (15)0.0135 (13)
C70.0377 (12)0.0329 (13)0.0336 (11)0.0083 (10)0.0088 (9)0.0128 (9)
C80.0445 (13)0.0371 (13)0.0334 (11)0.0116 (11)0.0092 (10)0.0095 (10)
C90.0524 (15)0.0373 (14)0.0413 (12)0.0160 (11)0.0189 (11)0.0208 (11)
C100.0493 (14)0.0361 (14)0.0413 (12)0.0132 (11)0.0141 (11)0.0191 (11)
C110.0491 (14)0.0311 (13)0.0392 (12)0.0116 (11)0.0180 (10)0.0187 (10)
C120.0499 (15)0.0432 (14)0.0465 (13)0.0154 (12)0.0194 (11)0.0233 (11)
C130.0530 (16)0.0496 (16)0.0607 (16)0.0240 (13)0.0294 (13)0.0286 (13)
C140.0699 (18)0.0384 (14)0.0444 (13)0.0172 (13)0.0284 (12)0.0167 (11)
C150.0608 (17)0.0560 (17)0.0397 (13)0.0137 (14)0.0151 (12)0.0201 (12)
C160.0469 (14)0.0488 (15)0.0457 (13)0.0179 (12)0.0162 (11)0.0225 (12)
C170.0732 (18)0.0363 (14)0.0472 (13)0.0219 (13)0.0229 (12)0.0224 (11)
C180.066 (2)0.0461 (17)0.107 (2)0.0083 (14)0.0117 (17)0.0453 (18)
C190.094 (3)0.0490 (19)0.118 (3)0.0104 (17)0.013 (2)0.049 (2)
C220.064 (2)0.067 (2)0.094 (2)0.0068 (16)0.0143 (17)0.0515 (18)
C210.083 (2)0.095 (3)0.114 (3)0.033 (2)0.017 (2)0.072 (2)
F10.1084 (14)0.0745 (12)0.0571 (9)0.0383 (10)0.0431 (9)0.0164 (8)
N10.0501 (12)0.0334 (11)0.0378 (9)0.0148 (9)0.0169 (8)0.0176 (8)
N20.0613 (13)0.0339 (11)0.0444 (11)0.0145 (10)0.0197 (10)0.0164 (9)
N30.0759 (16)0.0355 (13)0.0520 (12)0.0212 (11)0.0302 (11)0.0228 (10)
O10.0728 (12)0.0399 (10)0.0524 (10)0.0168 (9)0.0321 (9)0.0228 (8)
O20.0806 (14)0.0645 (13)0.0517 (10)0.0286 (10)0.0368 (10)0.0311 (9)
O30.0627 (11)0.0374 (10)0.0440 (9)0.0158 (8)0.0218 (8)0.0128 (8)
O40.1135 (16)0.0423 (11)0.0695 (12)0.0402 (11)0.0578 (11)0.0346 (9)
C200.104 (3)0.070 (2)0.086 (2)0.032 (2)0.0246 (19)0.0550 (19)

Geometric parameters (Å, °)

C1—C21.463 (4)C12—C131.375 (3)
C1—H1A0.9600C12—H120.9300
C1—H1B0.9600C13—C141.365 (4)
C1—H1C0.9600C13—H130.9300
C2—O11.449 (3)C14—F11.363 (3)
C2—H2A0.9700C14—C151.365 (4)
C2—H2B0.9700C15—C161.377 (3)
C3—O21.208 (3)C15—H150.9300
C3—O11.318 (3)C16—H160.9300
C3—C41.472 (3)C17—N31.464 (3)
C4—C51.357 (3)C17—C221.505 (4)
C4—C71.461 (3)C17—C181.509 (4)
C5—O31.384 (3)C17—H170.9800
C5—C61.478 (3)C18—C191.531 (4)
C6—H6A0.9600C18—H18A0.9700
C6—H6B0.9600C18—H18B0.9700
C6—H6C0.9600C19—C201.504 (4)
C7—C81.361 (3)C19—H19A0.9700
C7—C91.432 (3)C19—H19B0.9700
C8—N21.343 (3)C22—C211.522 (4)
C8—O31.362 (3)C22—H22A0.9700
C9—O41.207 (3)C22—H22B0.9700
C9—N11.446 (3)C21—C201.498 (5)
C10—N21.313 (3)C21—H21A0.9700
C10—N31.352 (3)C21—H21B0.9700
C10—N11.377 (3)N3—H30.86 (3)
C11—C121.378 (3)C20—H20A0.9700
C11—C161.383 (3)C20—H20B0.9700
C11—N11.442 (3)
C2—C1—H1A109.5C14—C15—C16117.9 (2)
C2—C1—H1B109.5C14—C15—H15121.1
H1A—C1—H1B109.5C16—C15—H15121.1
C2—C1—H1C109.5C15—C16—C11120.4 (2)
H1A—C1—H1C109.5C15—C16—H16119.8
H1B—C1—H1C109.5C11—C16—H16119.8
O1—C2—C1107.8 (2)N3—C17—C22110.7 (2)
O1—C2—H2A110.1N3—C17—C18110.7 (2)
C1—C2—H2A110.1C22—C17—C18111.0 (2)
O1—C2—H2B110.1N3—C17—H17108.1
C1—C2—H2B110.1C22—C17—H17108.1
H2A—C2—H2B108.5C18—C17—H17108.1
O2—C3—O1123.8 (2)C17—C18—C19110.6 (3)
O2—C3—C4124.9 (2)C17—C18—H18A109.5
O1—C3—C4111.31 (19)C19—C18—H18A109.5
C5—C4—C7106.1 (2)C17—C18—H18B109.5
C5—C4—C3123.0 (2)C19—C18—H18B109.5
C7—C4—C3130.9 (2)H18A—C18—H18B108.1
C4—C5—O3110.5 (2)C20—C19—C18111.8 (3)
C4—C5—C6134.8 (2)C20—C19—H19A109.2
O3—C5—C6114.8 (2)C18—C19—H19A109.2
C5—C6—H6A109.5C20—C19—H19B109.2
C5—C6—H6B109.5C18—C19—H19B109.2
H6A—C6—H6B109.5H19A—C19—H19B107.9
C5—C6—H6C109.5C17—C22—C21111.6 (3)
H6A—C6—H6C109.5C17—C22—H22A109.3
H6B—C6—H6C109.5C21—C22—H22A109.3
C8—C7—C9117.43 (19)C17—C22—H22B109.3
C8—C7—C4105.55 (19)C21—C22—H22B109.3
C9—C7—C4137.0 (2)H22A—C22—H22B108.0
N2—C8—C7130.9 (2)C20—C21—C22111.9 (3)
N2—C8—O3117.8 (2)C20—C21—H21A109.2
C7—C8—O3111.33 (19)C22—C21—H21A109.2
O4—C9—C7130.5 (2)C20—C21—H21B109.2
O4—C9—N1118.1 (2)C22—C21—H21B109.2
C7—C9—N1111.35 (19)H21A—C21—H21B107.9
N2—C10—N3119.0 (2)C10—N1—C11119.56 (17)
N2—C10—N1123.2 (2)C10—N1—C9124.19 (19)
N3—C10—N1117.7 (2)C11—N1—C9116.10 (17)
C12—C11—C16120.3 (2)C10—N2—C8112.82 (19)
C12—C11—N1120.03 (19)C10—N3—C17122.8 (2)
C16—C11—N1119.7 (2)C10—N3—H3114.2 (19)
C13—C12—C11119.5 (2)C17—N3—H3118.7 (18)
C13—C12—H12120.2C3—O1—C2118.03 (18)
C11—C12—H12120.2C8—O3—C5106.58 (18)
C14—C13—C12118.9 (2)C21—C20—C19111.4 (2)
C14—C13—H13120.5C21—C20—H20A109.3
C12—C13—H13120.5C19—C20—H20A109.3
F1—C14—C13118.4 (2)C21—C20—H20B109.3
F1—C14—C15118.5 (2)C19—C20—H20B109.3
C13—C14—C15123.0 (2)H20A—C20—H20B108.0
O2—C3—C4—C51.6 (4)N3—C17—C22—C21179.1 (2)
O1—C3—C4—C5−178.7 (2)C18—C17—C22—C2155.7 (4)
O2—C3—C4—C7−179.5 (2)C17—C22—C21—C20−54.7 (4)
O1—C3—C4—C70.2 (3)N2—C10—N1—C11−172.6 (2)
C7—C4—C5—O3−0.8 (3)N3—C10—N1—C118.9 (3)
C3—C4—C5—O3178.38 (19)N2—C10—N1—C92.7 (4)
C7—C4—C5—C6179.5 (3)N3—C10—N1—C9−175.9 (2)
C3—C4—C5—C6−1.3 (4)C12—C11—N1—C10−107.4 (2)
C5—C4—C7—C80.7 (2)C16—C11—N1—C1072.2 (3)
C3—C4—C7—C8−178.3 (2)C12—C11—N1—C977.0 (3)
C5—C4—C7—C9−179.3 (3)C16—C11—N1—C9−103.4 (2)
C3—C4—C7—C91.6 (4)O4—C9—N1—C10177.3 (2)
C9—C7—C8—N2−0.6 (4)C7—C9—N1—C10−3.6 (3)
C4—C7—C8—N2179.4 (2)O4—C9—N1—C11−7.3 (3)
C9—C7—C8—O3179.58 (18)C7—C9—N1—C11171.78 (18)
C4—C7—C8—O3−0.4 (2)N3—C10—N2—C8178.2 (2)
C8—C7—C9—O4−178.6 (3)N1—C10—N2—C8−0.3 (3)
C4—C7—C9—O41.4 (5)C7—C8—N2—C10−0.7 (4)
C8—C7—C9—N12.5 (3)O3—C8—N2—C10179.16 (19)
C4—C7—C9—N1−177.5 (2)N2—C10—N3—C1719.9 (4)
C16—C11—C12—C13−0.2 (3)N1—C10—N3—C17−161.5 (2)
N1—C11—C12—C13179.3 (2)C22—C17—N3—C1090.1 (3)
C11—C12—C13—C14−0.1 (3)C18—C17—N3—C10−146.4 (3)
C12—C13—C14—F1−179.7 (2)O2—C3—O1—C24.3 (3)
C12—C13—C14—C150.2 (4)C4—C3—O1—C2−175.4 (2)
F1—C14—C15—C16180.0 (2)C1—C2—O1—C3172.4 (2)
C13—C14—C15—C160.1 (4)N2—C8—O3—C5−179.9 (2)
C14—C15—C16—C11−0.4 (4)C7—C8—O3—C50.0 (2)
C12—C11—C16—C150.5 (3)C4—C5—O3—C80.5 (3)
N1—C11—C16—C15−179.1 (2)C6—C5—O3—C8−179.7 (2)
N3—C17—C18—C19−179.1 (2)C22—C21—C20—C1953.8 (4)
C22—C17—C18—C19−55.8 (4)C18—C19—C20—C21−54.4 (4)
C17—C18—C19—C2055.4 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C17—H17···N20.982.412.813 (3)104
C6—H6A···O20.962.453.039 (3)120
C20—H20B···Cg3i0.972.973.820 (4)147
C14—F···Cg3ii1.363 (3)3.358 (2)3.732 (3)95
C3—O2···Cg2iii1.208 (3)3.309 (2)3.409 (3)84

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2523).

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