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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2927.
Published online 2009 October 31. doi:  10.1107/S1600536809044274
PMCID: PMC2971169

Trimethyl 5-(2-chloro-4-fluoro­phen­yl)-2-phenyl­pyrrolidine-2,3,4-tricarboxyl­ate

Abstract

The title compound, C22H21ClFNO6, was synthesized by the 1,3-dipolar cyclo­addition reaction of dimethyl maleate, methyl 2-amino-2-phenyl­acetate and 2-chloro-4-fluoro­benzaldehyde. The pyrrolidine ring possesses an envelope conformation and the two benzene rings are oriented at a dihedral angle of 68.28 (7)°. Weak inter­molecular C—H(...)O hydrogen bonding is present in the crystal structure. One methyl group is disordered over two positions with a site-occupancy ratio of 0.651 (12):0.349 (12).

Related literature

For the biological activity of pyrrolidine derivatives, see: Coldham & Hufton (2005 [triangle]); Nair & Suja (2007 [triangle]); Pandey et al. (2006 [triangle]); Sardina & Rapoport (1996 [triangle]); Witherup et al. (1995 [triangle]). For a related structure, see: Yu et al. (2007 [triangle]).

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Object name is e-65-o2927-scheme1.jpg

Experimental

Crystal data

  • C22H21ClFNO6
  • M r = 449.85
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2927-efi1.jpg
  • a = 9.474 (3) Å
  • b = 15.057 (8) Å
  • c = 15.182 (5) Å
  • V = 2165.7 (15) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 1.98 mm−1
  • T = 298 K
  • 0.38 × 0.36 × 0.03 mm

Data collection

  • Oxford Diffraction Gemini S Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 [triangle]) T min = 0.520, T max = 0.943
  • 32943 measured reflections
  • 3442 independent reflections
  • 3332 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.060
  • S = 1.05
  • 3442 reflections
  • 290 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.16 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1456 Friedel pairs
  • Flack parameter: −0.001 (11)

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044274/xu2655sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044274/xu2655Isup2.hkl

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

Acknowledgments

The diffraction measurements were made at Sichuan University. We acknowledge financial support from China West Normal University.

supplementary crystallographic information

Comment

Substituted pyrrolidine compound is an important class of heterocyclic compounds with wide spread applications to the synthesis of biologically active compounds and natural products (Coldham et al., 2005; Nair et al., 2007; Pandey et al., 2006; Sardina et al., 1996; Witherup et al. 1995).

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The pyrrolidine ring possesses an envelope conformation. The dihedral angle between the C1—C6 and C11—C16 benzene planes is 68.28 (7)°.

Experimental

2-Chloro-4-fluorobenzaldehyde (0.063 g, 0.4 mmol), anhydrous sodium sulfate (200 mg) and dimethyl maleate (0.029 g, 0.2 mmol) were added to a solution of methyl 2-amino-2-phenylacetate(0.049 g, 0.3 mmol) in chloroform (2 ml). To the stirred mixture, acetic acid (0.012 g, 0.2 mmol) was added. After the mixture had been stirred at 323k for 10 h, the reaction was quenched with a saturated solution of sodium bicarbonate (5 ml). The mixture was extracted with diethyl ether, evaporated and separated by flash chromatograghy. A colourless powder was obtained. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution.

Refinement

Imino H atom was located in a difference Fourier map and positional parameters were refined, Uiso(H) = 1.2Ueq(N). The carbon-bound hydrogen atoms were placed in calculated positions, with C—H = 0.93–0.98 Å, and refined using a riding model, with Uiso(H) =1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others. One of methyl groups is disordered over two positions, site occupancy factors were refined to 0.651 (12):0.349 (12).

Figures

Fig. 1.
The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

Crystal data

C22H21ClFNO6F(000) = 936
Mr = 449.85Dx = 1.380 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2abCell parameters from 23516 reflections
a = 9.474 (3) Åθ = 2.9–62.8°
b = 15.057 (8) ŵ = 1.98 mm1
c = 15.182 (5) ÅT = 298 K
V = 2165.7 (15) Å3Platelet, colourless
Z = 40.38 × 0.36 × 0.03 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer3442 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source3332 reflections with I > 2σ(I)
mirrorRint = 0.025
Detector resolution: 15.9149 pixels mm-1θmax = 62.6°, θmin = 4.1°
ω scansh = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −17→17
Tmin = 0.520, Tmax = 0.943l = −17→17
32943 measured reflections

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)] = 0.024w = 1/[σ2(Fo2) + (0.0318P)2 + 0.3155P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.060(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.12 e Å3
3442 reflectionsΔρmin = −0.16 e Å3
290 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0055 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1456 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.001 (11)

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*/UeqOcc. (<1)
Cl10.87819 (6)0.40571 (3)0.69190 (3)0.06039 (14)
F11.10815 (14)0.42498 (8)0.39470 (7)0.0789 (4)
O10.64936 (15)0.70388 (7)0.55124 (8)0.0578 (3)
O20.59938 (18)0.55992 (8)0.53671 (8)0.0715 (4)
O30.50206 (14)0.80786 (9)0.73253 (11)0.0735 (4)
O40.41937 (11)0.67622 (8)0.68953 (9)0.0568 (3)
O50.79799 (13)0.86655 (7)0.67762 (8)0.0553 (3)
O60.74501 (13)0.87248 (7)0.82137 (7)0.0509 (3)
N10.89048 (14)0.69866 (8)0.69034 (9)0.0390 (3)
H10.870 (2)0.7278 (11)0.6438 (12)0.047*
C11.0498 (2)0.46980 (13)0.46390 (11)0.0546 (4)
C21.00115 (19)0.42137 (12)0.53368 (11)0.0500 (4)
H21.00940.35980.53500.060*
C30.93922 (17)0.46752 (10)0.60228 (10)0.0417 (4)
C40.92532 (15)0.55915 (10)0.60251 (10)0.0386 (3)
C50.98023 (19)0.60471 (12)0.53049 (11)0.0509 (4)
H50.97450.66640.52930.061*
C61.0431 (2)0.56086 (13)0.46054 (12)0.0588 (5)
H61.07960.59210.41280.071*
C70.85178 (16)0.60535 (9)0.67778 (9)0.0379 (3)
H70.87830.57380.73180.045*
C80.68738 (15)0.60534 (10)0.67347 (10)0.0393 (3)
H80.64910.54730.69020.047*
C90.65018 (15)0.67691 (10)0.74326 (10)0.0390 (3)
H90.62960.64500.79800.047*
C100.79423 (16)0.72962 (10)0.75935 (10)0.0372 (3)
C110.85468 (17)0.70603 (9)0.85036 (10)0.0386 (3)
C120.99477 (17)0.68067 (11)0.86012 (11)0.0468 (4)
H121.05370.67880.81110.056*
C131.0475 (2)0.65805 (12)0.94231 (13)0.0589 (5)
H131.14100.64010.94770.071*
C140.9633 (2)0.66181 (12)1.01602 (12)0.0604 (5)
H140.99920.64641.07100.073*
C150.8256 (2)0.68856 (12)1.00731 (12)0.0565 (5)
H150.76850.69281.05690.068*
C160.77124 (19)0.70915 (11)0.92558 (11)0.0478 (4)
H160.67690.72540.92070.057*
C170.77865 (16)0.83067 (10)0.74725 (11)0.0409 (3)
C180.7123 (2)0.96590 (11)0.81177 (15)0.0666 (5)
H18A0.70120.99220.86900.100*
H18B0.62630.97240.77900.100*
H18C0.78780.99500.78100.100*
C190.51912 (18)0.73007 (12)0.72121 (11)0.0462 (4)
C200.2893 (2)0.71857 (16)0.66086 (19)0.0810 (7)
H20A0.22290.67390.64290.121*
H20B0.30880.75730.61210.121*
H20C0.25020.75240.70860.121*
C210.64215 (18)0.63050 (10)0.58152 (10)0.0442 (4)
C22A0.5863 (10)0.5705 (4)0.4390 (3)0.0813 (19)0.651 (12)
H22A0.67150.55050.41120.122*0.651 (12)
H22B0.57080.63190.42510.122*0.651 (12)
H22C0.50810.53580.41810.122*0.651 (12)
C22B0.5167 (16)0.5848 (8)0.4569 (7)0.0813 (19)0.349 (12)
H22D0.42600.60700.47440.122*0.349 (12)
H22E0.50460.53350.42010.122*0.349 (12)
H22F0.56640.63000.42480.122*0.349 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0909 (3)0.0400 (2)0.0503 (2)0.0019 (2)0.0084 (2)0.00626 (17)
F10.0926 (9)0.0837 (8)0.0604 (6)0.0170 (7)0.0228 (6)−0.0173 (6)
O10.0762 (9)0.0468 (7)0.0505 (7)−0.0035 (6)−0.0099 (6)0.0073 (5)
O20.1081 (12)0.0502 (7)0.0562 (7)−0.0174 (7)−0.0325 (7)0.0010 (6)
O30.0495 (7)0.0544 (8)0.1167 (13)0.0096 (6)−0.0117 (7)−0.0141 (8)
O40.0371 (6)0.0568 (7)0.0766 (8)−0.0006 (5)−0.0088 (6)−0.0026 (7)
O50.0692 (8)0.0449 (6)0.0519 (7)0.0018 (5)0.0049 (6)0.0112 (5)
O60.0651 (8)0.0368 (5)0.0507 (6)0.0065 (5)−0.0016 (6)−0.0044 (5)
N10.0423 (7)0.0352 (6)0.0393 (6)−0.0019 (5)0.0035 (6)−0.0011 (5)
C10.0541 (10)0.0627 (11)0.0468 (10)0.0104 (9)0.0073 (8)−0.0100 (8)
C20.0556 (10)0.0442 (9)0.0502 (9)0.0081 (8)−0.0030 (8)−0.0062 (7)
C30.0452 (9)0.0401 (8)0.0399 (8)0.0012 (7)−0.0021 (7)0.0014 (6)
C40.0372 (8)0.0399 (8)0.0387 (8)0.0003 (6)−0.0026 (6)0.0005 (6)
C50.0582 (10)0.0446 (9)0.0499 (9)0.0028 (8)0.0104 (8)0.0041 (7)
C60.0666 (12)0.0620 (12)0.0478 (10)0.0016 (10)0.0155 (9)0.0046 (8)
C70.0412 (8)0.0349 (7)0.0376 (7)−0.0011 (6)0.0000 (6)0.0004 (6)
C80.0409 (8)0.0351 (7)0.0419 (8)−0.0020 (6)−0.0008 (6)0.0021 (6)
C90.0374 (8)0.0407 (8)0.0389 (8)−0.0026 (7)0.0007 (7)0.0022 (6)
C100.0365 (8)0.0372 (8)0.0380 (8)0.0002 (6)0.0017 (6)0.0001 (6)
C110.0420 (8)0.0329 (7)0.0410 (8)−0.0010 (6)−0.0030 (7)0.0002 (6)
C120.0405 (9)0.0459 (9)0.0541 (10)−0.0006 (7)−0.0036 (7)−0.0052 (7)
C130.0521 (11)0.0548 (10)0.0697 (12)0.0039 (9)−0.0210 (10)0.0005 (9)
C140.0737 (14)0.0547 (11)0.0529 (11)−0.0088 (10)−0.0200 (10)0.0087 (9)
C150.0655 (12)0.0618 (10)0.0421 (9)−0.0092 (9)−0.0007 (8)0.0058 (8)
C160.0450 (9)0.0541 (9)0.0443 (9)0.0005 (7)0.0005 (7)0.0030 (7)
C170.0386 (8)0.0377 (8)0.0465 (9)−0.0006 (6)−0.0021 (7)0.0002 (7)
C180.0837 (13)0.0395 (9)0.0766 (13)0.0132 (9)−0.0060 (12)−0.0070 (9)
C190.0404 (9)0.0466 (10)0.0517 (9)0.0001 (7)0.0018 (7)−0.0010 (7)
C200.0436 (11)0.0816 (15)0.1177 (19)0.0075 (10)−0.0185 (12)−0.0039 (14)
C210.0432 (9)0.0443 (9)0.0450 (8)−0.0014 (7)−0.0051 (7)−0.0002 (7)
C22A0.126 (6)0.070 (2)0.0474 (18)−0.010 (3)−0.027 (2)−0.0089 (17)
C22B0.126 (6)0.070 (2)0.0474 (18)−0.010 (3)−0.027 (2)−0.0089 (17)

Geometric parameters (Å, °)

Cl1—C31.7469 (16)C8—H80.9800
F1—C11.366 (2)C9—C191.515 (2)
O1—C211.1987 (19)C9—C101.597 (2)
O2—C211.325 (2)C9—H90.9800
O2—C22B1.490 (7)C10—C111.537 (2)
O2—C22A1.497 (4)C10—C171.540 (2)
O3—C191.195 (2)C11—C121.389 (2)
O4—C191.335 (2)C11—C161.390 (2)
O4—C201.454 (2)C12—C131.387 (3)
O5—C171.201 (2)C12—H120.9300
O6—C171.3283 (19)C13—C141.375 (3)
O6—C181.448 (2)C13—H130.9300
N1—C71.4645 (18)C14—C151.371 (3)
N1—C101.465 (2)C14—H140.9300
N1—H10.855 (18)C15—C161.379 (2)
C1—C21.366 (3)C15—H150.9300
C1—C61.373 (3)C16—H160.9300
C2—C31.383 (2)C18—H18A0.9600
C2—H20.9300C18—H18B0.9600
C3—C41.386 (2)C18—H18C0.9600
C4—C51.392 (2)C20—H20A0.9600
C4—C71.508 (2)C20—H20B0.9600
C5—C61.385 (2)C20—H20C0.9600
C5—H50.9300C22A—H22A0.9600
C6—H60.9300C22A—H22B0.9600
C7—C81.559 (2)C22A—H22C0.9600
C7—H70.9800C22B—H22D0.9600
C8—C211.509 (2)C22B—H22E0.9600
C8—C91.552 (2)C22B—H22F0.9600
C21—O2—C22B112.1 (5)C12—C11—C10121.02 (14)
C21—O2—C22A116.7 (3)C16—C11—C10121.26 (14)
C22B—O2—C22A28.9 (4)C13—C12—C11120.50 (17)
C19—O4—C20116.19 (15)C13—C12—H12119.7
C17—O6—C18115.25 (14)C11—C12—H12119.7
C7—N1—C10104.04 (11)C14—C13—C12120.89 (17)
C7—N1—H1109.1 (12)C14—C13—H13119.6
C10—N1—H1106.6 (12)C12—C13—H13119.6
F1—C1—C2117.99 (17)C15—C14—C13119.02 (17)
F1—C1—C6118.91 (17)C15—C14—H14120.5
C2—C1—C6123.10 (16)C13—C14—H14120.5
C1—C2—C3117.32 (16)C14—C15—C16120.55 (18)
C1—C2—H2121.3C14—C15—H15119.7
C3—C2—H2121.3C16—C15—H15119.7
C2—C3—C4122.85 (15)C15—C16—C11121.28 (17)
C2—C3—Cl1117.35 (12)C15—C16—H16119.4
C4—C3—Cl1119.79 (12)C11—C16—H16119.4
C3—C4—C5116.95 (14)O5—C17—O6124.68 (14)
C3—C4—C7120.33 (13)O5—C17—C10122.33 (14)
C5—C4—C7122.72 (14)O6—C17—C10112.97 (13)
C6—C5—C4121.88 (16)O6—C18—H18A109.5
C6—C5—H5119.1O6—C18—H18B109.5
C4—C5—H5119.1H18A—C18—H18B109.5
C1—C6—C5117.86 (17)O6—C18—H18C109.5
C1—C6—H6121.1H18A—C18—H18C109.5
C5—C6—H6121.1H18B—C18—H18C109.5
N1—C7—C4115.18 (12)O3—C19—O4123.47 (16)
N1—C7—C8104.82 (12)O3—C19—C9126.67 (16)
C4—C7—C8115.45 (12)O4—C19—C9109.81 (14)
N1—C7—H7107.0O4—C20—H20A109.5
C4—C7—H7107.0O4—C20—H20B109.5
C8—C7—H7107.0H20A—C20—H20B109.5
C21—C8—C9113.13 (12)O4—C20—H20C109.5
C21—C8—C7108.82 (12)H20A—C20—H20C109.5
C9—C8—C7101.43 (11)H20B—C20—H20C109.5
C21—C8—H8111.0O1—C21—O2124.03 (15)
C9—C8—H8111.0O1—C21—C8124.77 (14)
C7—C8—H8111.0O2—C21—C8111.13 (13)
C19—C9—C8113.72 (13)O2—C22A—H22A109.5
C19—C9—C10118.14 (13)O2—C22A—H22B109.5
C8—C9—C10104.80 (12)H22A—C22A—H22B109.5
C19—C9—H9106.5O2—C22A—H22C109.5
C8—C9—H9106.5H22A—C22A—H22C109.5
C10—C9—H9106.5H22B—C22A—H22C109.5
N1—C10—C11109.71 (12)O2—C22B—H22D109.5
N1—C10—C17106.78 (12)O2—C22B—H22E109.5
C11—C10—C17111.80 (12)H22D—C22B—H22E109.5
N1—C10—C9105.33 (12)O2—C22B—H22F109.5
C11—C10—C9109.94 (12)H22D—C22B—H22F109.5
C17—C10—C9113.00 (12)H22E—C22B—H22F109.5
C12—C11—C16117.72 (15)
F1—C1—C2—C3−178.45 (16)N1—C10—C11—C1214.85 (19)
C6—C1—C2—C31.8 (3)C17—C10—C11—C12−103.41 (16)
C1—C2—C3—C40.0 (3)C9—C10—C11—C12130.23 (15)
C1—C2—C3—Cl1−179.53 (14)N1—C10—C11—C16−165.02 (14)
C2—C3—C4—C5−1.5 (2)C17—C10—C11—C1676.71 (18)
Cl1—C3—C4—C5177.95 (12)C9—C10—C11—C16−49.64 (18)
C2—C3—C4—C7177.68 (14)C16—C11—C12—C131.0 (2)
Cl1—C3—C4—C7−2.8 (2)C10—C11—C12—C13−178.87 (15)
C3—C4—C5—C61.5 (3)C11—C12—C13—C14−1.2 (3)
C7—C4—C5—C6−177.73 (16)C12—C13—C14—C15−0.1 (3)
F1—C1—C6—C5178.39 (17)C13—C14—C15—C161.7 (3)
C2—C1—C6—C5−1.9 (3)C14—C15—C16—C11−1.9 (3)
C4—C5—C6—C10.2 (3)C12—C11—C16—C150.6 (2)
C10—N1—C7—C4173.79 (12)C10—C11—C16—C15−179.57 (15)
C10—N1—C7—C845.80 (14)C18—O6—C17—O58.4 (2)
C3—C4—C7—N1156.57 (14)C18—O6—C17—C10−172.84 (15)
C5—C4—C7—N1−24.3 (2)N1—C10—C17—O524.6 (2)
C3—C4—C7—C8−80.97 (18)C11—C10—C17—O5144.60 (15)
C5—C4—C7—C898.19 (18)C9—C10—C17—O5−90.74 (18)
N1—C7—C8—C2181.72 (14)N1—C10—C17—O6−154.16 (13)
C4—C7—C8—C21−46.10 (17)C11—C10—C17—O6−34.15 (18)
N1—C7—C8—C9−37.78 (14)C9—C10—C17—O690.51 (15)
C4—C7—C8—C9−165.60 (12)C20—O4—C19—O35.6 (3)
C21—C8—C9—C1930.15 (18)C20—O4—C19—C9−176.82 (16)
C7—C8—C9—C19146.52 (13)C8—C9—C19—O3−140.85 (18)
C21—C8—C9—C10−100.31 (14)C10—C9—C19—O3−17.4 (3)
C7—C8—C9—C1016.07 (14)C8—C9—C19—O441.67 (18)
C7—N1—C10—C1184.15 (14)C10—C9—C19—O4165.13 (13)
C7—N1—C10—C17−154.52 (12)C22B—O2—C21—O1−19.4 (7)
C7—N1—C10—C9−34.13 (14)C22A—O2—C21—O112.0 (5)
C19—C9—C10—N1−117.73 (14)C22B—O2—C21—C8163.6 (7)
C8—C9—C10—N110.09 (15)C22A—O2—C21—C8−165.1 (5)
C19—C9—C10—C11124.14 (14)C9—C8—C21—O138.7 (2)
C8—C9—C10—C11−108.04 (13)C7—C8—C21—O1−73.2 (2)
C19—C9—C10—C17−1.53 (19)C9—C8—C21—O2−144.27 (15)
C8—C9—C10—C17126.29 (13)C7—C8—C21—O2103.82 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O5i0.932.563.380 (3)147

Symmetry codes: (i) x+1/2, −y+3/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2655).

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