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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2349.
Published online 2008 November 13. doi:  10.1107/S160053680803688X
PMCID: PMC2960019

(E)-3-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino­meth­yl]phenyl 4-bromo­benzene­sulfonate

Abstract

In the title compound, C24H20BrN3O4S, the central benzene ring makes dihedral angles of 24.55 (8), 49.52 (12) and 59.65 (7)°, respectively, with the pyrazolone ring, the bromo­benzene ring and the terminal phenyl ring. The packing is stabilized by weak non-classical inter­molecular C—H(...)O=C hydrogen bonds that form inversion-related dimers.

Related literature

For general background to Schiff base ligands, see: Chen & Yu (2006 [triangle]); Kahwa et al. (1986 [triangle]); Santos et al. (2001 [triangle]); Zhao et al. (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]);

An external file that holds a picture, illustration, etc.
Object name is e-64-o2349-scheme1.jpg

Experimental

Crystal data

  • C24H20BrN3O4S
  • M r = 526.40
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2349-efi1.jpg
  • a = 9.3152 (17) Å
  • b = 10.1223 (18) Å
  • c = 13.472 (3) Å
  • α = 94.507 (3)°
  • β = 109.034 (3)°
  • γ = 102.953 (3)°
  • V = 1154.3 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.91 mm−1
  • T = 294 (2) K
  • 0.20 × 0.18 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.623, T max = 0.826
  • 6027 measured reflections
  • 4035 independent reflections
  • 3133 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.088
  • S = 1.02
  • 4035 reflections
  • 301 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 1999 [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 I, global. DOI: 10.1107/S160053680803688X/at2667sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803688X/at2667Isup2.hkl

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

supplementary crystallographic information

Comment

Schiff-base ligands have received a good deal of attention in biology and chemistry (Kahwa et al., 1986). Many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). Among the large number of compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them, such as (E)-5-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro- 1H-pyrazol-4-yliminomethyl)-2-methoxyphenyl benzenesulfonate (Chen & Yu, 2006) and (E)-4-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro- 1H-pyrazol-4-yliminomethyl)-2-methoxyphenyl benzenesulfonate (Zhao et al., 2006) have been reported. Structural information is useful when investigating the coordination properties of Schiff bases functioning as ligands. We report here the synthesis and molecular structure of the title Schiff base compound, (I), (Fig. 1)

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The pyrazolone ring (C14—C16/N1—N3/O4) is almost planar, with an r.m.s. deviation for fitted atoms of 0.0345 Å. It makes a dihedral angle of 42.12 (8)° with the attached phenyl ring (C19—C24). The central benzene ring (C7—C13/O3) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.0264 Å. This group makes dihedral angles of 24.55 (8)°, 49.52 (12)° and 59.65 (7)°, respectively, with the the pyrazolone ring (C14—C16/N1—N3/O4), the bromobenzene ring (C1—C6) and the terminal phenyl ring (C19—C24).

An intramolecular C13—H13···O4═C15 hydrogen bond is found in (I) (Table 1), which helps to stabilize the conformation of the molecule. Packing is stabilized by weak, non-classical intermolecular C21—H21···O4═C15 hydrogen bonds that form inversion related dimers (Table 1, Fig. 2).

Experimental

An anhydrous ethanol solution (50 ml) of 3-formylphenyl 4-bromobenzenesulfonate (3.41 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (2.03 g, 10 mmol) and the mixture stirred at 350 K for 3 h under N2, giving a yellow precipitate. The product was isolated, recrystallized from acetonitrile, and then dried in a vacuum to give pure compound (I) in 81% yield. Yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.

Refinement

The H atoms were included in calculated positions and refined using a riding model approximation. Constrained C—H and N—H bond lengths and isotropic U parameters: 0.93 Å and Uiso(H) = 1.2Ueq(C) for Csp2—H; 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl C—H.

Figures

Fig. 1.
The structure of (I), with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
Fig. 2.
A packing diagram for (I), with hydrogen bonds drawn as dashed lines.

Crystal data

C24H20BrN3O4SZ = 2
Mr = 526.40F000 = 536
Triclinic, P1Dx = 1.515 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.3152 (17) ÅCell parameters from 2541 reflections
b = 10.1223 (18) Åθ = 2.4–26.1º
c = 13.472 (3) ŵ = 1.91 mm1
α = 94.507 (3)ºT = 294 (2) K
β = 109.034 (3)ºBlock, yellow
γ = 102.953 (3)º0.20 × 0.18 × 0.10 mm
V = 1154.3 (4) Å3

Data collection

Bruker SMART APEX CCD area-detector diffractometer4035 independent reflections
Radiation source: fine-focus sealed tube3133 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
T = 294(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −6→11
Tmin = 0.623, Tmax = 0.826k = −12→11
6027 measured reflectionsl = −16→15

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035  w = 1/[σ2(Fo2) + (0.038P)2 + 0.609P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.27 e Å3
4035 reflectionsΔρmin = −0.36 e Å3
301 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0475 (19)
Secondary atom site location: difference Fourier map

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 > 2σ(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
Br11.29069 (4)0.88146 (3)0.88042 (3)0.05949 (16)
S11.23680 (9)0.25329 (8)0.93033 (8)0.0591 (3)
N10.6951 (3)0.4506 (2)0.71737 (18)0.0415 (6)
N20.4487 (3)0.6559 (2)0.57841 (19)0.0422 (6)
N30.5999 (3)0.7481 (2)0.61946 (19)0.0434 (6)
O11.1993 (3)0.2290 (2)1.02189 (19)0.0751 (7)
O21.3668 (3)0.2167 (3)0.9141 (3)0.0903 (10)
O31.0922 (2)0.1687 (2)0.82766 (17)0.0521 (5)
O40.3384 (2)0.4347 (2)0.59904 (17)0.0511 (5)
C11.1929 (4)0.5050 (3)0.9740 (2)0.0508 (8)
H11.15010.46791.02230.061*
C21.2014 (3)0.6396 (3)0.9614 (2)0.0481 (7)
H21.16200.69350.99960.058*
C31.2687 (3)0.6936 (3)0.8917 (2)0.0429 (7)
C41.3231 (5)0.6147 (4)0.8332 (3)0.0708 (10)
H41.36740.65250.78580.085*
C51.3127 (5)0.4803 (4)0.8442 (3)0.0718 (11)
H51.34910.42620.80400.086*
C61.2479 (3)0.4251 (3)0.9152 (2)0.0466 (7)
C70.9359 (3)0.1566 (3)0.8247 (2)0.0411 (7)
C80.8593 (3)0.2500 (3)0.7803 (2)0.0408 (7)
H80.91150.32390.75720.049*
C90.7025 (3)0.2331 (3)0.7700 (2)0.0402 (7)
C100.6279 (4)0.1203 (3)0.8041 (2)0.0477 (7)
H100.52240.10680.79630.057*
C110.7077 (4)0.0283 (3)0.8491 (2)0.0511 (8)
H110.6562−0.04610.87210.061*
C120.8633 (4)0.0457 (3)0.8604 (2)0.0459 (7)
H120.9181−0.01580.89120.055*
C130.6187 (3)0.3337 (3)0.7256 (2)0.0423 (7)
H130.50940.31180.70330.051*
C140.6199 (3)0.5460 (3)0.6704 (2)0.0386 (6)
C150.4552 (3)0.5307 (3)0.6145 (2)0.0380 (6)
C160.7007 (3)0.6739 (3)0.6675 (2)0.0414 (7)
C170.8746 (3)0.7324 (3)0.7076 (3)0.0617 (9)
H17A0.92360.68040.75890.093*
H17B0.90030.82640.74060.093*
H17C0.91210.72820.64930.093*
C180.6390 (4)0.8479 (3)0.5533 (3)0.0575 (9)
H18A0.72880.92110.59620.086*
H18B0.55090.88480.52290.086*
H18C0.66280.80350.49730.086*
C190.3137 (3)0.7097 (3)0.5527 (2)0.0424 (7)
C200.1735 (3)0.6289 (3)0.4787 (2)0.0513 (8)
H200.16740.54200.44680.062*
C210.0424 (4)0.6802 (4)0.4531 (3)0.0666 (10)
H21−0.05330.62650.40450.080*
C220.0526 (5)0.8098 (5)0.4988 (4)0.0758 (12)
H22−0.03550.84410.47970.091*
C230.1922 (5)0.8887 (4)0.5725 (3)0.0729 (11)
H230.19850.97610.60370.087*
C240.3232 (4)0.8382 (3)0.6003 (3)0.0575 (8)
H240.41760.89080.65100.069*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0675 (3)0.03803 (19)0.0694 (3)0.00752 (14)0.02286 (17)0.01353 (15)
S10.0468 (5)0.0447 (4)0.0819 (6)0.0191 (4)0.0097 (4)0.0255 (4)
N10.0401 (13)0.0415 (13)0.0438 (14)0.0172 (11)0.0109 (11)0.0109 (11)
N20.0332 (12)0.0372 (12)0.0536 (15)0.0124 (10)0.0087 (11)0.0134 (11)
N30.0360 (13)0.0368 (12)0.0551 (15)0.0087 (10)0.0122 (11)0.0136 (11)
O10.0811 (17)0.0595 (15)0.0663 (16)0.0108 (12)0.0024 (13)0.0320 (12)
O20.0494 (15)0.0619 (16)0.161 (3)0.0314 (12)0.0258 (16)0.0295 (17)
O30.0504 (13)0.0454 (12)0.0675 (14)0.0236 (9)0.0218 (11)0.0122 (10)
O40.0360 (11)0.0454 (12)0.0679 (14)0.0091 (9)0.0120 (10)0.0196 (10)
C10.0534 (19)0.0499 (18)0.0507 (19)0.0076 (14)0.0228 (15)0.0153 (15)
C20.0526 (18)0.0402 (16)0.0526 (19)0.0080 (13)0.0237 (15)0.0040 (14)
C30.0439 (16)0.0379 (15)0.0430 (17)0.0076 (12)0.0123 (13)0.0074 (13)
C40.103 (3)0.055 (2)0.082 (3)0.024 (2)0.063 (2)0.0270 (19)
C50.101 (3)0.056 (2)0.092 (3)0.037 (2)0.064 (2)0.022 (2)
C60.0444 (17)0.0411 (16)0.0542 (19)0.0139 (13)0.0136 (14)0.0167 (14)
C70.0419 (16)0.0369 (15)0.0437 (17)0.0155 (12)0.0109 (13)0.0056 (12)
C80.0464 (17)0.0360 (15)0.0417 (16)0.0116 (12)0.0158 (13)0.0121 (12)
C90.0413 (16)0.0382 (15)0.0383 (16)0.0113 (12)0.0092 (12)0.0082 (12)
C100.0425 (17)0.0459 (17)0.0507 (18)0.0088 (13)0.0127 (14)0.0102 (14)
C110.057 (2)0.0392 (16)0.0540 (19)0.0058 (14)0.0182 (15)0.0143 (14)
C120.0564 (19)0.0313 (14)0.0466 (18)0.0143 (13)0.0107 (14)0.0123 (13)
C130.0385 (16)0.0458 (17)0.0433 (17)0.0142 (13)0.0118 (13)0.0126 (13)
C140.0361 (15)0.0405 (15)0.0410 (16)0.0153 (12)0.0115 (12)0.0107 (12)
C150.0372 (16)0.0386 (15)0.0411 (16)0.0137 (13)0.0137 (12)0.0121 (12)
C160.0366 (15)0.0414 (16)0.0468 (17)0.0143 (12)0.0120 (13)0.0111 (13)
C170.0378 (17)0.0502 (19)0.087 (3)0.0096 (14)0.0105 (17)0.0128 (17)
C180.0542 (19)0.0484 (18)0.070 (2)0.0110 (15)0.0201 (17)0.0249 (16)
C190.0411 (16)0.0506 (17)0.0445 (17)0.0204 (13)0.0182 (13)0.0221 (14)
C200.0414 (17)0.065 (2)0.0489 (19)0.0165 (15)0.0136 (14)0.0203 (16)
C210.0413 (19)0.097 (3)0.068 (2)0.0250 (19)0.0174 (17)0.039 (2)
C220.062 (3)0.102 (3)0.098 (3)0.054 (2)0.042 (2)0.058 (3)
C230.084 (3)0.070 (2)0.094 (3)0.049 (2)0.047 (2)0.035 (2)
C240.060 (2)0.0531 (19)0.064 (2)0.0269 (16)0.0192 (17)0.0161 (16)

Geometric parameters (Å, °)

Br1—C31.890 (3)C9—C101.390 (4)
S1—O11.412 (3)C9—C131.467 (4)
S1—O21.419 (3)C10—C111.376 (4)
S1—O31.594 (2)C10—H100.9300
S1—C61.751 (3)C11—C121.376 (4)
N1—C131.270 (3)C11—H110.9300
N1—C141.390 (3)C12—H120.9300
N2—C151.399 (3)C13—H130.9300
N2—N31.408 (3)C14—C161.355 (4)
N2—C191.432 (3)C14—C151.437 (4)
N3—C161.364 (3)C16—C171.488 (4)
N3—C181.462 (4)C17—H17A0.9600
O3—C71.420 (3)C17—H17B0.9600
O4—C151.232 (3)C17—H17C0.9600
C1—C21.375 (4)C18—H18A0.9600
C1—C61.376 (4)C18—H18B0.9600
C1—H10.9300C18—H18C0.9600
C2—C31.373 (4)C19—C241.374 (4)
C2—H20.9300C19—C201.383 (4)
C3—C41.363 (4)C20—C211.385 (4)
C4—C51.366 (5)C20—H200.9300
C4—H40.9300C21—C221.374 (6)
C5—C61.378 (4)C21—H210.9300
C5—H50.9300C22—C231.372 (6)
C7—C81.368 (4)C22—H220.9300
C7—C121.380 (4)C23—C241.380 (5)
C8—C91.391 (4)C23—H230.9300
C8—H80.9300C24—H240.9300
O1—S1—O2121.47 (17)C10—C11—H11119.8
O1—S1—O3108.79 (13)C11—C12—C7118.3 (3)
O2—S1—O3102.68 (16)C11—C12—H12120.8
O1—S1—C6109.11 (16)C7—C12—H12120.8
O2—S1—C6109.41 (15)N1—C13—C9120.1 (3)
O3—S1—C6103.86 (13)N1—C13—H13119.9
C13—N1—C14121.9 (2)C9—C13—H13119.9
C15—N2—N3109.4 (2)C16—C14—N1122.1 (2)
C15—N2—C19125.0 (2)C16—C14—C15108.3 (2)
N3—N2—C19119.0 (2)N1—C14—C15129.5 (2)
C16—N3—N2106.3 (2)O4—C15—N2123.9 (2)
C16—N3—C18121.9 (2)O4—C15—C14131.5 (2)
N2—N3—C18116.9 (2)N2—C15—C14104.6 (2)
C7—O3—S1119.49 (18)C14—C16—N3110.7 (2)
C2—C1—C6120.0 (3)C14—C16—C17127.6 (3)
C2—C1—H1120.0N3—C16—C17121.7 (2)
C6—C1—H1120.0C16—C17—H17A109.5
C3—C2—C1119.1 (3)C16—C17—H17B109.5
C3—C2—H2120.4H17A—C17—H17B109.5
C1—C2—H2120.4C16—C17—H17C109.5
C4—C3—C2121.0 (3)H17A—C17—H17C109.5
C4—C3—Br1120.0 (2)H17B—C17—H17C109.5
C2—C3—Br1119.0 (2)N3—C18—H18A109.5
C3—C4—C5120.1 (3)N3—C18—H18B109.5
C3—C4—H4120.0H18A—C18—H18B109.5
C5—C4—H4120.0N3—C18—H18C109.5
C4—C5—C6119.7 (3)H18A—C18—H18C109.5
C4—C5—H5120.2H18B—C18—H18C109.5
C6—C5—H5120.2C24—C19—C20120.9 (3)
C1—C6—C5120.1 (3)C24—C19—N2120.9 (3)
C1—C6—S1120.3 (2)C20—C19—N2118.2 (3)
C5—C6—S1119.6 (3)C19—C20—C21118.6 (3)
C8—C7—C12122.4 (3)C19—C20—H20120.7
C8—C7—O3118.9 (2)C21—C20—H20120.7
C12—C7—O3118.6 (2)C22—C21—C20120.5 (3)
C7—C8—C9119.3 (3)C22—C21—H21119.7
C7—C8—H8120.4C20—C21—H21119.7
C9—C8—H8120.4C23—C22—C21120.3 (3)
C10—C9—C8118.7 (3)C23—C22—H22119.9
C10—C9—C13120.8 (3)C21—C22—H22119.9
C8—C9—C13120.5 (2)C22—C23—C24119.9 (4)
C11—C10—C9121.0 (3)C22—C23—H23120.1
C11—C10—H10119.5C24—C23—H23120.1
C9—C10—H10119.5C19—C24—C23119.8 (3)
C12—C11—C10120.4 (3)C19—C24—H24120.1
C12—C11—H11119.8C23—C24—H24120.1
C15—N2—N3—C168.2 (3)O3—C7—C12—C11−174.7 (3)
C19—N2—N3—C16161.0 (2)C14—N1—C13—C9176.4 (2)
C15—N2—N3—C18148.2 (3)C10—C9—C13—N1163.9 (3)
C19—N2—N3—C18−58.9 (3)C8—C9—C13—N1−15.1 (4)
O1—S1—O3—C737.5 (2)C13—N1—C14—C16175.7 (3)
O2—S1—O3—C7167.5 (2)C13—N1—C14—C15−7.4 (5)
C6—S1—O3—C7−78.6 (2)N3—N2—C15—O4173.4 (3)
C6—C1—C2—C3−1.6 (5)C19—N2—C15—O422.5 (4)
C1—C2—C3—C41.7 (5)N3—N2—C15—C14−5.7 (3)
C1—C2—C3—Br1−176.5 (2)C19—N2—C15—C14−156.6 (3)
C2—C3—C4—C5−0.7 (6)C16—C14—C15—O4−177.8 (3)
Br1—C3—C4—C5177.5 (3)N1—C14—C15—O45.0 (5)
C3—C4—C5—C6−0.4 (6)C16—C14—C15—N21.2 (3)
C2—C1—C6—C50.5 (5)N1—C14—C15—N2−176.0 (3)
C2—C1—C6—S1−179.7 (2)N1—C14—C16—N3−178.6 (2)
C4—C5—C6—C10.5 (6)C15—C14—C16—N34.0 (3)
C4—C5—C6—S1−179.2 (3)N1—C14—C16—C172.4 (5)
O1—S1—C6—C1−12.4 (3)C15—C14—C16—C17−175.1 (3)
O2—S1—C6—C1−147.5 (3)N2—N3—C16—C14−7.5 (3)
O3—S1—C6—C1103.5 (3)C18—N3—C16—C14−145.0 (3)
O1—S1—C6—C5167.3 (3)N2—N3—C16—C17171.7 (3)
O2—S1—C6—C532.3 (3)C18—N3—C16—C1734.1 (4)
O3—S1—C6—C5−76.8 (3)C15—N2—C19—C24124.7 (3)
S1—O3—C7—C893.0 (3)N3—N2—C19—C24−23.7 (4)
S1—O3—C7—C12−91.3 (3)C15—N2—C19—C20−55.3 (4)
C12—C7—C8—C9−0.2 (4)N3—N2—C19—C20156.3 (3)
O3—C7—C8—C9175.3 (2)C24—C19—C20—C210.2 (4)
C7—C8—C9—C10−0.9 (4)N2—C19—C20—C21−179.8 (3)
C7—C8—C9—C13178.2 (3)C19—C20—C21—C221.3 (5)
C8—C9—C10—C111.3 (4)C20—C21—C22—C23−1.6 (5)
C13—C9—C10—C11−177.8 (3)C21—C22—C23—C240.4 (6)
C9—C10—C11—C12−0.6 (5)C20—C19—C24—C23−1.3 (5)
C10—C11—C12—C7−0.4 (4)N2—C19—C24—C23178.7 (3)
C8—C7—C12—C110.9 (4)C22—C23—C24—C191.0 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13···O40.932.403.056 (3)127
C21—H21···O4i0.932.573.290 (4)135

Symmetry codes: (i) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2667).

References

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