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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2378.
Published online 2008 November 20. doi:  10.1107/S1600536808037604
PMCID: PMC2959817

N-[4-Chloro-2-methyl-6-(N-methyl­car­bam­oyl)phen­yl]-1-(3-chloro-2-pyrid­yl)-3-trifluoro­meth­yl-1H-pyrazole-5-carboxamide

Abstract

In the title compound, C19H14Cl2F3N5O2, which shows insecticidal activity, the dihedral angle between the pyrazole and pyridine rings is 68.15 (16)°. In the crystal structure, the mol­ecules are linked by N—H(...)O and C—H(...)O hydrogen bonds and an intra­molecular N—H(...)O inter­action also occurs. The F atoms of the –CF3 group are disordered over two sets of sites in a 0.800 (8):0.200 (8) ratio.

Related literature

For the synthesis and background to the insecticidal properties of the title compound, see: Lahm et al. (2003 [triangle], 2005 [triangle]).

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Object name is e-64-o2378-scheme1.jpg

Experimental

Crystal data

  • C19H14Cl2F3N5O2
  • M r = 472.25
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2378-efi1.jpg
  • a = 26.4612 (16) Å
  • b = 32.8657 (19) Å
  • c = 9.4679 (6) Å
  • V = 8233.9 (9) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.37 mm−1
  • T = 296 (2) K
  • 0.24 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1999 [triangle]) T min = 0.917, T max = 0.937
  • 10439 measured reflections
  • 3565 independent reflections
  • 3284 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.082
  • S = 1.04
  • 3565 reflections
  • 310 parameters
  • 49 restraints
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.20 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1621 Friedel pairs
  • Flack parameter: −0.01 (7)

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/S1600536808037604/hb2777sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037604/hb2777Isup2.hkl

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

supplementary crystallographic information

Comment

Anthranilamide compounds containing an N-pyridyl pyrazole grouping are a new class of inseticides showing potent activity against a broad spectrum of Lepidoptera and no-cross resistance to existing insecticides (Lahm et al., 2003) and their mode of action has been been established (Lahm et al., 2005). Anthranilamides show little effect on mammalian ryanodine receptors and as a result they show excellent insect versus mammalian selectivity. As part of our studies in this area, we now report the crystal structures of the title compound, (I), (Fig. 1) which possesses high insecticidal activity.

The pyrazole ring and pyridine rings are not coplanar, the dihedral angle formed by the least-squares planes of the rings being equal to 68.15 (16)°. The dihedral angle between the mean plane of the pyrazole ring and the plane of the C10/O1/N4 group is 23.4 (2)° and the dihedral angle between the mean plane of the phenyl ring and the plane of the C10/O1/N4 group is 59.9 (2)°.

An intramolecular N—H···O hydrogen bond (Table 1) is observed, which helps to establish the molecular conformation. Intermolecular N—H···O and C—H···O bonds result in a three-dimensional network.

Experimental

The title compound was prepared by the literature method (Lahm et al., 2003). The crude products were purified by silica-gel column chromatography and then grown from acetone to afford colourless blocks of (I).

Anal. Calcd for C12H14N4O3: C, 48.32; H, 2.99; N, 14.83. Found: C, 48.47; H, 3.04; N, 14.66. 1H NMR(CDCl3): 2.19 (s, 3H, CH3), 2.70 (d, J=4.5 Hz, 3H, CH3), 7.30–7.31 (m, 2H, Ph), 7.57 (dd, 1H), 8.05 (d, J=8.1 Hz, 1H), 8.22 (br s, J=4.5 Hz, 1H, NH), 8.46 (d, J=4.8 Hz, 1H), 7.64 (s, 1H), 10.43 (s, 1H, NH).

Refinement

Although all H atoms were visible in difference maps, they were placed in geometrically calculated positions, with C—H distances in the range 0.93–0.96Å and N—H distances of 0.86 Å, andincluded in the final refinement in the riding model approximation,with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C). The F atoms of the -CF3 are disordered over two sets of sites in a 0.800 (8):0.200 (8) ratio.

Crystal data

C19H14Cl2F3N5O2Dx = 1.524 Mg m3
Mr = 472.25Melting point: 492(1) K
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
a = 26.4612 (16) ÅCell parameters from 3952 reflections
b = 32.8657 (19) Åθ = 2.4–23.9°
c = 9.4679 (6) ŵ = 0.37 mm1
V = 8233.9 (9) Å3T = 296 K
Z = 16Block, colourless
F(000) = 38400.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer3565 independent reflections
Radiation source: fine-focus sealed tube3284 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)h = −31→24
Tmin = 0.917, Tmax = 0.937k = −34→38
10439 measured reflectionsl = −11→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.082w = 1/[σ2(Fo2) + (0.0387P)2 + 8.8659P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3565 reflectionsΔρmax = 0.18 e Å3
310 parametersΔρmin = −0.20 e Å3
49 restraintsAbsolute structure: Flack (1983), 1621 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.01 (7)

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)
Cl10.28309 (3)1.00598 (3)0.40561 (10)0.0647 (3)
Cl20.46782 (4)0.85540 (5)−0.17854 (12)0.1075 (5)
F10.39895 (14)1.06805 (12)0.8595 (6)0.1059 (17)0.800 (8)
F20.4312 (2)1.01859 (14)0.9614 (4)0.1148 (18)0.800 (8)
F30.47071 (12)1.04708 (16)0.7981 (5)0.0958 (15)0.800 (8)
F1'0.4028 (5)1.0381 (5)0.9535 (11)0.074 (4)0.200 (8)
F2'0.4714 (4)1.0263 (5)0.8653 (18)0.087 (5)0.200 (8)
F3'0.4283 (7)1.0724 (3)0.7878 (16)0.106 (6)0.200 (8)
O10.36097 (7)0.91496 (6)0.4022 (2)0.0453 (5)
O20.52136 (8)0.96046 (6)0.3535 (3)0.0576 (6)
N10.35642 (9)0.99358 (8)0.7518 (3)0.0445 (6)
N20.34753 (8)0.97021 (6)0.6376 (2)0.0360 (5)
N30.28654 (9)0.92344 (8)0.7109 (3)0.0479 (6)
N40.42127 (8)0.95772 (6)0.3170 (2)0.0342 (5)
H40.43590.98080.32910.041*
N50.56488 (8)0.90701 (7)0.2779 (3)0.0419 (6)
H50.56720.88730.21860.050*
C10.26575 (11)0.96695 (9)0.5174 (3)0.0448 (7)
C20.21856 (11)0.94974 (11)0.5056 (4)0.0566 (9)
H20.19580.95870.43750.068*
C30.20605 (12)0.91908 (11)0.5966 (4)0.0602 (10)
H30.17470.90640.58990.072*
C40.23980 (14)0.90720 (10)0.6975 (4)0.0592 (9)
H4A0.23020.88690.76040.071*
C50.29811 (10)0.95245 (8)0.6209 (3)0.0379 (6)
C60.40279 (10)1.00776 (9)0.7321 (3)0.0434 (7)
C70.42585 (12)1.03518 (11)0.8368 (4)0.0596 (9)
C80.42392 (10)0.99401 (9)0.6056 (3)0.0429 (7)
H80.45581.00000.56950.052*
C90.38752 (10)0.96987 (8)0.5464 (3)0.0346 (6)
C100.38824 (9)0.94496 (7)0.4152 (3)0.0329 (6)
C110.43316 (10)0.93476 (7)0.1941 (3)0.0323 (6)
C120.48281 (9)0.92011 (7)0.1738 (3)0.0319 (6)
C130.49293 (10)0.89622 (9)0.0565 (3)0.0415 (6)
H130.52540.88640.04100.050*
C140.45484 (12)0.88718 (10)−0.0367 (3)0.0534 (8)
C150.40693 (11)0.90324 (10)−0.0207 (3)0.0507 (8)
H150.38220.8976−0.08750.061*
C160.39557 (10)0.92751 (9)0.0935 (3)0.0401 (6)
C170.34412 (11)0.94686 (11)0.1030 (4)0.0565 (8)
H17A0.32900.94760.01080.085*
H17B0.34740.97410.13850.085*
H17C0.32320.93130.16560.085*
C180.52432 (10)0.93058 (8)0.2762 (3)0.0334 (6)
C190.60538 (12)0.91391 (11)0.3778 (4)0.0597 (9)
H19A0.62160.93940.35710.090*
H19B0.62960.89230.37080.090*
H19C0.59180.91470.47180.090*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0572 (5)0.0631 (5)0.0737 (6)0.0044 (4)−0.0053 (4)0.0203 (5)
Cl20.0781 (7)0.1621 (12)0.0821 (8)0.0360 (7)−0.0273 (6)−0.0839 (8)
F10.090 (2)0.090 (2)0.137 (3)0.0050 (19)−0.020 (2)−0.063 (2)
F20.168 (4)0.117 (3)0.059 (2)−0.042 (3)−0.040 (2)−0.0052 (18)
F30.067 (2)0.132 (3)0.088 (3)−0.0499 (19)0.0139 (17)−0.043 (2)
F1'0.067 (6)0.095 (6)0.060 (6)−0.014 (5)0.009 (4)−0.021 (5)
F2'0.072 (6)0.094 (6)0.094 (7)0.004 (5)−0.017 (5)−0.018 (5)
F3'0.121 (8)0.094 (7)0.103 (7)−0.008 (5)−0.014 (5)−0.004 (5)
O10.0485 (11)0.0440 (11)0.0433 (11)−0.0146 (9)0.0108 (10)−0.0005 (9)
O20.0434 (12)0.0537 (12)0.0757 (17)0.0105 (10)−0.0185 (11)−0.0324 (12)
N10.0407 (13)0.0564 (15)0.0365 (13)−0.0054 (11)0.0038 (10)−0.0095 (11)
N20.0312 (11)0.0441 (12)0.0326 (12)−0.0019 (9)0.0043 (9)−0.0051 (10)
N30.0511 (15)0.0500 (14)0.0426 (14)−0.0052 (12)0.0153 (11)−0.0014 (12)
N40.0332 (11)0.0331 (11)0.0364 (13)−0.0044 (9)0.0052 (10)−0.0030 (10)
N50.0347 (12)0.0433 (13)0.0478 (14)0.0065 (10)−0.0059 (10)−0.0128 (11)
C10.0378 (16)0.0472 (16)0.0492 (18)0.0027 (13)0.0053 (13)−0.0069 (14)
C20.0356 (17)0.067 (2)0.067 (2)−0.0003 (15)−0.0020 (16)−0.0149 (18)
C30.0381 (17)0.068 (2)0.075 (2)−0.0137 (16)0.0124 (17)−0.022 (2)
C40.065 (2)0.0553 (19)0.058 (2)−0.0176 (17)0.0271 (17)−0.0078 (16)
C50.0335 (14)0.0422 (15)0.0380 (16)−0.0023 (11)0.0100 (12)−0.0074 (12)
C60.0380 (16)0.0545 (17)0.0376 (16)−0.0054 (13)−0.0001 (12)−0.0042 (13)
C70.0503 (19)0.077 (2)0.052 (2)−0.0108 (18)0.0062 (16)−0.0155 (18)
C80.0326 (14)0.0557 (17)0.0405 (16)−0.0058 (13)0.0051 (12)−0.0010 (13)
C90.0337 (14)0.0392 (14)0.0307 (13)0.0022 (11)0.0021 (11)0.0020 (11)
C100.0288 (13)0.0351 (13)0.0347 (14)0.0006 (11)0.0028 (11)0.0050 (11)
C110.0330 (13)0.0329 (13)0.0310 (14)−0.0043 (11)0.0016 (11)0.0042 (10)
C120.0314 (13)0.0310 (12)0.0333 (14)−0.0044 (10)0.0008 (11)0.0008 (11)
C130.0357 (14)0.0499 (16)0.0391 (15)0.0027 (12)0.0002 (12)−0.0068 (13)
C140.0502 (18)0.069 (2)0.0405 (17)0.0035 (16)−0.0066 (13)−0.0218 (16)
C150.0422 (17)0.071 (2)0.0392 (17)−0.0054 (15)−0.0108 (13)−0.0092 (16)
C160.0319 (14)0.0501 (16)0.0383 (16)−0.0040 (12)0.0012 (11)0.0034 (13)
C170.0365 (15)0.085 (2)0.0481 (19)0.0068 (16)−0.0051 (14)0.0040 (16)
C180.0335 (14)0.0308 (13)0.0359 (15)−0.0015 (11)−0.0003 (11)−0.0020 (11)
C190.0393 (17)0.073 (2)0.067 (2)0.0107 (15)−0.0141 (15)−0.0186 (19)

Geometric parameters (Å, °)

Cl1—C11.725 (3)C2—H20.9300
Cl2—C141.736 (3)C3—C41.365 (5)
F1—C71.311 (4)C3—H30.9300
F2—C71.307 (4)C4—H4A0.9300
F3—C71.303 (4)C6—C81.397 (4)
F1'—C71.266 (8)C6—C71.472 (4)
F2'—C71.269 (8)C8—C91.368 (4)
F3'—C71.310 (8)C8—H80.9300
O1—C101.228 (3)C9—C101.488 (4)
O2—C181.227 (3)C11—C161.397 (4)
N1—C61.326 (4)C11—C121.412 (4)
N1—N21.347 (3)C12—C131.387 (4)
N2—C91.366 (3)C12—C181.505 (3)
N2—C51.441 (3)C13—C141.372 (4)
N3—C51.315 (4)C13—H130.9300
N3—C41.353 (4)C14—C151.382 (4)
N4—C101.343 (3)C15—C161.377 (4)
N4—C111.423 (3)C15—H150.9300
N4—H40.8600C16—C171.505 (4)
N5—C181.324 (3)C17—H17A0.9600
N5—C191.447 (4)C17—H17B0.9600
N5—H50.8600C17—H17C0.9600
C1—C21.375 (4)C19—H19A0.9600
C1—C51.386 (4)C19—H19B0.9600
C2—C31.367 (5)C19—H19C0.9600
C6—N1—N2104.4 (2)F3—C7—C6111.8 (3)
N1—N2—C9112.1 (2)F2—C7—C6113.4 (3)
N1—N2—C5118.5 (2)F3'—C7—C6110.7 (7)
C9—N2—C5129.1 (2)F1—C7—C6112.9 (3)
C5—N3—C4116.0 (3)C9—C8—C6104.9 (2)
C10—N4—C11123.0 (2)C9—C8—H8127.5
C10—N4—H4118.5C6—C8—H8127.5
C11—N4—H4118.5N2—C9—C8106.3 (2)
C18—N5—C19121.1 (2)N2—C9—C10122.9 (2)
C18—N5—H5119.5C8—C9—C10130.7 (2)
C19—N5—H5119.5O1—C10—N4124.3 (2)
C2—C1—C5118.5 (3)O1—C10—C9121.2 (2)
C2—C1—Cl1119.8 (3)N4—C10—C9114.5 (2)
C5—C1—Cl1121.7 (2)C16—C11—C12120.8 (2)
C3—C2—C1118.1 (3)C16—C11—N4119.4 (2)
C3—C2—H2120.9C12—C11—N4119.8 (2)
C1—C2—H2120.9C13—C12—C11118.8 (2)
C4—C3—C2119.6 (3)C13—C12—C18120.3 (2)
C4—C3—H3120.2C11—C12—C18120.9 (2)
C2—C3—H3120.2C14—C13—C12119.7 (3)
N3—C4—C3123.4 (3)C14—C13—H13120.1
N3—C4—H4A118.3C12—C13—H13120.1
C3—C4—H4A118.3C13—C14—C15121.4 (3)
N3—C5—C1124.3 (3)C13—C14—Cl2118.8 (2)
N3—C5—N2115.7 (3)C15—C14—Cl2119.8 (2)
C1—C5—N2119.9 (2)C16—C15—C14120.5 (3)
N1—C6—C8112.2 (3)C16—C15—H15119.7
N1—C6—C7120.2 (3)C14—C15—H15119.7
C8—C6—C7127.6 (3)C15—C16—C11118.6 (3)
F1'—C7—F2'106.9 (8)C15—C16—C17119.3 (3)
F1'—C7—F3131.5 (6)C11—C16—C17122.1 (3)
F2'—C7—F342.6 (7)C16—C17—H17A109.5
F1'—C7—F245.3 (7)C16—C17—H17B109.5
F2'—C7—F267.0 (8)H17A—C17—H17B109.5
F3—C7—F2106.3 (4)C16—C17—H17C109.5
F1'—C7—F3'105.2 (8)H17A—C17—H17C109.5
F2'—C7—F3'104.1 (8)H17B—C17—H17C109.5
F3—C7—F3'64.8 (8)O2—C18—N5120.9 (2)
F2—C7—F3'134.7 (7)O2—C18—C12121.4 (2)
F1'—C7—F162.1 (7)N5—C18—C12117.7 (2)
F2'—C7—F1132.1 (7)N5—C19—H19A109.5
F3—C7—F1107.1 (4)N5—C19—H19B109.5
F2—C7—F1104.8 (4)H19A—C19—H19B109.5
F3'—C7—F146.8 (8)N5—C19—H19C109.5
F1'—C7—C6115.8 (6)H19A—C19—H19C109.5
F2'—C7—C6113.3 (7)H19B—C19—H19C109.5
C6—N1—N2—C9−0.5 (3)N1—N2—C9—C10177.2 (2)
C6—N1—N2—C5−175.3 (2)C5—N2—C9—C10−8.7 (4)
C5—C1—C2—C3−0.1 (4)C6—C8—C9—N2−0.2 (3)
Cl1—C1—C2—C3−179.5 (3)C6—C8—C9—C10−176.6 (3)
C1—C2—C3—C41.5 (5)C11—N4—C10—O1−8.6 (4)
C5—N3—C4—C31.0 (4)C11—N4—C10—C9170.3 (2)
C2—C3—C4—N3−2.0 (5)N2—C9—C10—O1−22.0 (4)
C4—N3—C5—C10.5 (4)C8—C9—C10—O1154.0 (3)
C4—N3—C5—N2178.7 (2)N2—C9—C10—N4159.1 (2)
C2—C1—C5—N3−1.0 (4)C8—C9—C10—N4−24.9 (4)
Cl1—C1—C5—N3178.5 (2)C10—N4—C11—C1664.7 (3)
C2—C1—C5—N2−179.1 (3)C10—N4—C11—C12−116.2 (3)
Cl1—C1—C5—N20.4 (4)C16—C11—C12—C13−3.9 (4)
N1—N2—C5—N3−69.8 (3)N4—C11—C12—C13177.1 (2)
C9—N2—C5—N3116.4 (3)C16—C11—C12—C18175.2 (2)
N1—N2—C5—C1108.4 (3)N4—C11—C12—C18−3.8 (3)
C9—N2—C5—C1−65.4 (4)C11—C12—C13—C14−0.3 (4)
N2—N1—C6—C80.4 (3)C18—C12—C13—C14−179.4 (3)
N2—N1—C6—C7179.6 (3)C12—C13—C14—C153.7 (5)
N1—C6—C7—F1'11.8 (10)C12—C13—C14—Cl2−177.2 (2)
C8—C6—C7—F1'−169.1 (10)C13—C14—C15—C16−2.8 (5)
N1—C6—C7—F2'135.8 (10)Cl2—C14—C15—C16178.0 (3)
C8—C6—C7—F2'−45.1 (11)C14—C15—C16—C11−1.4 (4)
N1—C6—C7—F3−177.9 (4)C14—C15—C16—C17175.9 (3)
C8—C6—C7—F31.1 (6)C12—C11—C16—C154.7 (4)
N1—C6—C7—F261.9 (5)N4—C11—C16—C15−176.2 (2)
C8—C6—C7—F2−119.0 (5)C12—C11—C16—C17−172.5 (3)
N1—C6—C7—F3'−107.7 (10)N4—C11—C16—C176.6 (4)
C8—C6—C7—F3'71.4 (11)C19—N5—C18—O24.6 (4)
N1—C6—C7—F1−57.1 (5)C19—N5—C18—C12−177.1 (3)
C8—C6—C7—F1122.0 (4)C13—C12—C18—O2157.4 (3)
N1—C6—C8—C9−0.2 (3)C11—C12—C18—O2−21.8 (4)
C7—C6—C8—C9−179.3 (3)C13—C12—C18—N5−21.0 (4)
N1—N2—C9—C80.4 (3)C11—C12—C18—N5159.9 (2)
C5—N2—C9—C8174.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4···O20.862.372.673 (3)101
N4—H4···O2i0.862.253.107 (3)176
N5—H5···O1ii0.862.162.915 (3)146
C8—H8···O2i0.932.503.168 (4)129

Symmetry codes: (i) −x+1, −y+2, z; (ii) x+1/4, −y+7/4, z−1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2777).

References

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  • Lahm, G. P., Selby, T. P., Freudenberger, J. H., Stevenson, T. M., Myers, B. M., Seburyamo, G., Smith, B. K., Flexner, L., Clark, C. E. & Cordova, D. (2005). Bioorg. Med. Chem. Lett.15, 4898–4906. [PubMed]
  • Lahm, G. P., Selby, T. P. & Stevenson, T. M. (2003). International Patent Number WO 03/015 519.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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