Structures of four polymorphs of the pesticide dithianon solved from X-ray powder diffraction data

Halasz, I.; Dinnebier, R.; Chiodo, T.; Saxell, H.

doi:10.1107/S0108768112036191

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Structures of four polymorphs of the pesticide dithianon solved from X-ray powder diffraction data

I. Halasz, R. Dinnebier, T. Chiodo and H. Saxell

The crystal structures of four polymorphs of the pesticide dithianon (5,10-dihydro-5,10-dioxonaphtho[2,3-b]-1,4-dithiine-2,3-dicarbonitrile) have been solved from powder diffraction data and refined using the Rietveld method. Three polymorphs crystallize in non-centrosymmetric space groups. Two polymorphs have Z' > 1. The structures are assembled via interactions between carbonyl groups of quinoid fragments into layers which further interact only by weak interactions.

Keywords: polymorphism; dithianon; X-ray powder diffraction; structure solution; carbonyl interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112036191/kd5066sup1.cif Contains datablocks global, I, II, III, IV
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768112036191/kd5066Isup2.rtv Contains datablock I
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768112036191/kd5066IIsup3.rtv Contains datablock II
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768112036191/kd5066IIIsup4.rtv Contains datablock III
	Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768112036191/kd5066IVsup5.rtv Contains datablock IV

CCDC references: 914865; 914866; 914867; 914868

Computing details top

For all compounds, data collection: Bruker; cell refinement: Topas; data reduction: none; program(s) used to solve structure: Topas; program(s) used to refine structure: Topas.

Figures top

(I) top

Crystal data top

C₁₄H₄N₂O₂S₂	V = 1287.44 (7) Å³
M_r = 296.33	Z = 4
Orthorhombic, Pna2₁	D_x = 1.53 Mg m⁻³
a = 8.49373 (19) Å	Cu Kα_1 radiation, λ = 1.54059 Å
b = 6.2466 (2) Å	T = 293 K
c = 24.2652 (10) Å	?, ? × ? × ? mm

Data collection top

Bruker D8 diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 2°, 2θ_max = 70°, 2θ_step = 0.009°
Data collection mode: transmission

Refinement top

Refinement on F²	? data points
R_p = 0.030	106 parameters
R_wp = 0.039	65 restraints
R_exp = 0.002	All H-atom parameters refined
χ² = 1.742	(Δ/σ)_max < 0.01

Crystal data top

C₁₄H₄N₂O₂S₂	V = 1287.44 (7) Å³
M_r = 296.33	Z = 4
Orthorhombic, Pna2₁	Cu Kα_1 radiation, λ = 1.54059 Å
a = 8.49373 (19) Å	T = 293 K
b = 6.2466 (2) Å	?, ? × ? × ? mm
c = 24.2652 (10) Å

Data collection top

Bruker D8 diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 2°, 2θ_max = 70°, 2θ_step = 0.009°
Data collection mode: transmission

Refinement top

R_p = 0.030	? data points
R_wp = 0.039	106 parameters
R_exp = 0.002	65 restraints
χ² = 1.742	All H-atom parameters refined

Special details top

Refinement. The crystal structure (all atoms) was refined with restraints on bond lenghts and angles as well as planarity restraints.

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

	x	y	z	B_iso*/B_eq
C1	0.52082 (15)	0.29473 (16)	0.40146 (3)
C2	0.43823 (15)	0.49291 (13)	0.39346 (3)
C3	0.39941 (16)	0.62139 (14)	0.43888 (3)
C4	0.43982 (12)	0.55590 (14)	0.49181 (3)
C5	0.52256 (11)	0.35672 (15)	0.49938 (3)
C6	0.56098 (16)	0.22917 (17)	0.45404 (3)
C7	0.39736 (13)	0.69230 (14)	0.53969 (3)
C8	0.44316 (19)	0.61527 (18)	0.59496 (4)
C9	0.52280 (16)	0.4204 (2)	0.60217 (4)
C10	0.56754 (16)	0.28214 (18)	0.55424 (4)
S11	0.39236 (16)	0.7890 (2)	0.65055 (6)
C12	0.36056 (9)	0.61133 (13)	0.70560 (3)
C13	0.44338 (10)	0.41415 (13)	0.71205 (3)
S14	0.58569 (14)	0.3234 (2)	0.66626 (6)
C15	0.41128 (10)	0.28177 (16)	0.75714 (4)
N16	0.38425 (16)	0.1722 (3)	0.79460 (6)
C17	0.24786 (11)	0.67302 (15)	0.74425 (4)
N18	0.1541 (2)	0.7238 (3)	0.77649 (6)
O19	0.6351 (3)	0.1180 (4)	0.56135 (6)
O20	0.3289 (3)	0.8570 (4)	0.53481 (6)
H21	0.5489 (5)	0.2011 (7)	0.3684 (2)
H22	0.4098 (6)	0.5415 (7)	0.3555 (3)
H23	0.3437 (6)	0.7601 (8)	0.43311 (15)
H24	0.6173 (5)	0.0902 (8)	0.45962 (14)

(II) top

Crystal data top

C₁₄H₄N₂O₂S₂	γ = 90.975 (2)°
M_r = 296.33	V = 612.02 (5) Å³
Triclinic, P1	Z = 2
a = 3.89671 (11) Å	D_x = 1.61 Mg m⁻³
b = 12.1707 (3) Å	Cu Kα_1 radiation, λ = 1.54059 Å
c = 13.0436 (9) Å	T = 293 K
α = 90.710 (9)°	?, ? × ? × ? mm
β = 81.707 (10)°

Data collection top

Bruker D8 diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 2°, 2θ_max = 65°, 2θ_step = 0.009°
Data collection mode: transmission

Refinement top

Refinement on F²	? data points
R_p = 0.034	129 parameters
R_wp = 0.048	65 restraints
R_exp = 0.014	All H-atom parameters refined
χ² = 3.349	(Δ/σ)_max < 0.01

Crystal data top

C₁₄H₄N₂O₂S₂	β = 81.707 (10)°
M_r = 296.33	γ = 90.975 (2)°
Triclinic, P1	V = 612.02 (5) Å³
a = 3.89671 (11) Å	Z = 2
b = 12.1707 (3) Å	Cu Kα_1 radiation, λ = 1.54059 Å
c = 13.0436 (9) Å	T = 293 K
α = 90.710 (9)°	?, ? × ? × ? mm

Data collection top

Bruker D8 diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 2°, 2θ_max = 65°, 2θ_step = 0.009°
Data collection mode: transmission

Refinement top

R_p = 0.034	? data points
R_wp = 0.048	129 parameters
R_exp = 0.014	65 restraints
χ² = 3.349	All H-atom parameters refined

Special details top

Refinement. The crystal structure (all atoms) was refined with restraints on bond lenghts and angles as well as planarity restraints.

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

	x	y	z	B_iso*/B_eq
C1	0.2537 (5)	0.22960 (9)	0.46146 (8)
C2	0.4345 (5)	0.33349 (9)	0.45351 (8)
C3	0.5494 (6)	0.37813 (12)	0.35717 (8)
C4	0.4979 (5)	0.31968 (9)	0.26565 (7)
C5	0.3161 (6)	0.21521 (12)	0.27402 (8)
C6	0.2000 (5)	0.17076 (10)	0.37119 (8)
C7	0.6305 (3)	0.36684 (7)	0.16218 (5)
C8	0.5630 (6)	0.30206 (11)	0.06900 (8)
C9	0.3851 (6)	0.20211 (12)	0.07624 (8)
C10	0.2486 (3)	0.15142 (7)	0.17806 (5)
S11	0.7273 (9)	0.36386 (16)	−0.04496 (18)
C12	0.6500 (5)	0.28853 (11)	−0.15550 (9)
C13	0.4719 (5)	0.18531 (13)	−0.14883 (9)
S14	0.3004 (9)	0.12675 (16)	−0.02973 (19)
C15	0.4090 (3)	0.12679 (11)	−0.23632 (13)
N16	0.3565 (7)	0.07788 (19)	−0.3089 (2)
C17	0.7740 (3)	0.33682 (11)	−0.24984 (13)
N18	0.8782 (6)	0.3779 (2)	−0.3284 (2)
O19	0.0980 (11)	0.0652 (3)	0.18184 (5)
O20	0.7847 (11)	0.4525 (3)	0.15235 (5)
H21	0.171 (2)	0.1973 (4)	0.5316 (4)
H22	0.4721 (18)	0.3755 (4)	0.5177 (5)
H23	0.6741 (17)	0.4504 (4)	0.3523 (3)
H24	0.0752 (18)	0.0984 (3)	0.3767 (3)

(III) top

Crystal data top

C₁₄H₄N₂O₂S₂	V = 1908.57 (19) Å³
M_r = 296.33	Z = 6
Monoclinic, P2₁	D_x = 1.55 Mg m⁻³
a = 12.4934 (8) Å	Cu Kα_1 radiation, λ = 1.54059 Å
b = 24.6720 (12) Å	T = 293 K
c = 6.2769 (3) Å	?, ? × ? × ? mm
β = 99.442 (4)°

Data collection top

Stoe Stadi-P diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 5°, 2θ_max = 70°, 2θ_step = 0.012°
Data collection mode: transmission

Refinement top

Refinement on F²	? data points
R_p = 0.020	260 parameters
R_wp = 0.027	204 restraints
R_exp = 0.007	All H-atom parameters refined
χ² = 3.572	(Δ/σ)_max < 0.01

Crystal data top

C₁₄H₄N₂O₂S₂	β = 99.442 (4)°
M_r = 296.33	V = 1908.57 (19) Å³
Monoclinic, P2₁	Z = 6
a = 12.4934 (8) Å	Cu Kα_1 radiation, λ = 1.54059 Å
b = 24.6720 (12) Å	T = 293 K
c = 6.2769 (3) Å	?, ? × ? × ? mm

Data collection top

Stoe Stadi-P diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 5°, 2θ_max = 70°, 2θ_step = 0.012°
Data collection mode: transmission

Refinement top

R_p = 0.020	? data points
R_wp = 0.027	260 parameters
R_exp = 0.007	204 restraints
χ² = 3.572	All H-atom parameters refined

Special details top

Refinement. The crystal structure (all atoms) was refined with restraints on bond lenghts and angles as well as planarity restraints.

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

	x	y	z	B_iso*/B_eq
C1	0.50963 (18)	0.6329 (2)	0.5234 (4)
C3	0.6218 (2)	0.6447 (3)	0.6376 (6)
C4	0.6365 (2)	0.6719 (2)	0.8152 (5)
C5	0.41060 (19)	0.64666 (17)	0.6207 (5)
C2	0.5391 (2)	0.6867 (2)	0.9185 (5)
C6	0.42505 (19)	0.67318 (16)	0.8110 (5)
O1	0.4969 (3)	0.6132 (6)	0.3538 (15)
O2	0.5520 (3)	0.7058 (6)	1.0900 (15)
C7	0.30225 (19)	0.63424 (18)	0.5068 (5)
C8	0.3400 (2)	0.6861 (2)	0.9063 (6)
C9	0.2150 (2)	0.64478 (18)	0.6010 (4)
C10	0.2293 (2)	0.67546 (18)	0.7946 (5)
S1	0.7266 (5)	0.6254 (3)	0.5109 (7)
S2	0.7705 (4)	0.6849 (2)	0.9716 (7)
C11	0.8545 (2)	0.61566 (15)	0.7009 (5)
C12	0.8723 (2)	0.63987 (13)	0.8878 (5)
C13	0.9310 (3)	0.58090 (14)	0.6246 (6)
N1	0.9937 (5)	0.5528 (3)	0.5640 (11)
C14	0.9699 (3)	0.63320 (12)	1.0427 (5)
N2	1.0513 (5)	0.6273 (2)	1.1708 (9)
H7	0.2931 (13)	0.6165 (7)	0.376 (4)
H8	0.3511 (13)	0.7049 (7)	1.036 (3)
H9	0.1445 (13)	0.6335 (9)	0.531 (3)
H10	0.1705 (13)	0.6852 (7)	0.859 (4)
C21	0.4950 (3)	0.4708 (2)	0.4316 (5)
C23	0.6024 (3)	0.4817 (3)	0.3678 (6)
C24	0.6076 (2)	0.5103 (2)	0.1927 (5)
C25	0.3903 (2)	0.4859 (2)	0.2872 (6)
C22	0.5039 (2)	0.5243 (2)	0.0403 (4)
C26	0.3948 (2)	0.51269 (18)	0.0981 (5)
O21	0.4910 (4)	0.4539 (6)	0.5963 (15)
O22	0.5084 (3)	0.5453 (5)	−0.1252 (16)
C27	0.2913 (2)	0.4749 (2)	0.3540 (5)
C28	0.2992 (2)	0.52837 (18)	−0.0421 (6)
C29	0.1943 (2)	0.4866 (2)	0.2193 (5)
C30	0.1982 (2)	0.5184 (2)	0.0148 (5)
S21	0.7215 (5)	0.4547 (2)	0.5441 (6)
S22	0.7297 (4)	0.5256 (2)	0.1038 (7)
C31	0.8303 (2)	0.44696 (15)	0.3847 (5)
C32	0.8321 (2)	0.47550 (13)	0.2009 (5)
C33	0.9082 (3)	0.40954 (15)	0.4675 (6)
N21	0.9756 (5)	0.3775 (3)	0.5386 (10)
C34	0.9117 (3)	0.46929 (12)	0.0685 (6)
N22	0.9785 (5)	0.4638 (2)	−0.0429 (9)
H27	0.2901 (13)	0.4570 (7)	0.482 (3)
H28	0.3039 (13)	0.5461 (8)	−0.166 (4)
H29	0.1279 (16)	0.4771 (8)	0.263 (4)
H30	0.1295 (14)	0.5264 (7)	−0.094 (3)
C41	0.5160 (3)	0.35216 (19)	0.9253 (5)
C43	0.4080 (3)	0.3472 (2)	0.7828 (7)
C44	0.3997 (3)	0.3212 (2)	0.6063 (6)
C45	0.6181 (3)	0.32947 (15)	0.8581 (6)
C42	0.4996 (3)	0.2997 (2)	0.5348 (5)
C46	0.6094 (2)	0.30389 (19)	0.6751 (5)
O41	0.5244 (4)	0.3772 (6)	1.0933 (18)
O42	0.4933 (4)	0.2782 (5)	0.3684 (16)
C47	0.7249 (2)	0.33453 (18)	0.9966 (5)
C48	0.7042 (2)	0.2821 (2)	0.5987 (6)
C49	0.8231 (2)	0.31233 (18)	0.9203 (5)
C50	0.8104 (2)	0.28454 (17)	0.7313 (5)
S41	0.2915 (5)	0.3712 (2)	0.8865 (7)
S42	0.2694 (5)	0.3071 (3)	0.4305 (6)
C51	0.1827 (2)	0.32760 (13)	0.7957 (6)
C52	0.1730 (2)	0.30032 (16)	0.5961 (5)
C53	0.1123 (3)	0.32254 (12)	0.9398 (6)
N41	0.0523 (6)	0.3179 (2)	1.0634 (10)
C54	0.0880 (3)	0.26578 (15)	0.5123 (6)
N42	0.0171 (5)	0.2373 (3)	0.4434 (10)
H47	0.7324 (15)	0.3538 (7)	1.127 (3)
H48	0.6962 (14)	0.2651 (6)	0.469 (4)
H49	0.8961 (17)	0.3136 (8)	1.018 (3)
H50	0.8702 (15)	0.2714 (6)	0.677 (4)

(IV) top

Crystal data top

C₁₄H₄N₂O₂S₂	V = 1269.02 (11) Å³
M_r = 296.33	Z = 4
Monoclinic, P2₁	D_x = 1.55 Mg m⁻³
a = 13.0945 (6) Å	Cu Kα_1 radiation, λ = 1.54059 Å
b = 6.0103 (4) Å	T = 293 K
c = 17.1209 (6) Å	?, ? × ? × ? mm
β = 109.646 (4)°

Data collection top

Bruker D8 diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 5°, 2θ_max = 60°, 2θ_step = 0.009°
Data collection mode: transmission

Refinement top

Refinement on F²	? data points
R_p = 0.048	177 parameters
R_wp = 0.065	139 restraints
R_exp = 0.007	All H-atom parameters refined
χ² = 9.000	(Δ/σ)_max < 0.01

Crystal data top

C₁₄H₄N₂O₂S₂	β = 109.646 (4)°
M_r = 296.33	V = 1269.02 (11) Å³
Monoclinic, P2₁	Z = 4
a = 13.0945 (6) Å	Cu Kα_1 radiation, λ = 1.54059 Å
b = 6.0103 (4) Å	T = 293 K
c = 17.1209 (6) Å	?, ? × ? × ? mm

Data collection top

Bruker D8 diffractometer	Scan method: step
Specimen mounting: capillary	2θ_min = 5°, 2θ_max = 60°, 2θ_step = 0.009°
Data collection mode: transmission

Refinement top

R_p = 0.048	? data points
R_wp = 0.065	177 parameters
R_exp = 0.007	139 restraints
χ² = 9.000	All H-atom parameters refined

Special details top

Refinement. The crystal structure (all atoms) was refined with restraints on bond lenghts and angles as well as planarity restraints.

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

	x	y	z	B_iso*/B_eq
S1	0.2615 (7)	0.2641 (16)	0.1099 (5)
S2	0.2664 (7)	0.7363 (10)	0.0107 (5)
S3	0.2794 (6)	1.2616 (11)	0.3754 (5)
S4	0.2627 (7)	0.8021 (14)	0.2600 (5)
O1	0.4779 (7)	0.115 (2)	0.1976 (10)
O2	0.4873 (6)	0.867 (2)	0.0525 (9)
O3	0.5050 (6)	1.367 (2)	0.4526 (8)
O4	0.4755 (6)	0.604 (2)	0.2938 (8)
N1	0.0322 (9)	0.041 (2)	−0.0613 (5)
N2	0.0327 (10)	0.553 (3)	−0.1818 (6)
N3	0.0516 (8)	1.107 (2)	0.4515 (8)
N4	0.0426 (7)	0.524 (2)	0.3096 (6)
C1	0.0922 (5)	0.1588 (15)	−0.0331 (3)
C2	0.1756 (5)	0.3224 (18)	0.0054 (3)
C3	0.3844 (3)	0.3995 (15)	0.1151 (4)
C4	0.4850 (4)	0.2803 (12)	0.1644 (4)
C5	0.5904 (3)	0.3907 (14)	0.1755 (5)
C6	0.6903 (3)	0.2898 (14)	0.2217 (5)
H6	0.6908 (19)	0.142 (9)	0.2467 (15)
C7	0.7859 (3)	0.4068 (13)	0.2345 (4)
H7	0.851 (2)	0.349 (10)	0.2677 (14)
C8	0.7852 (4)	0.6301 (13)	0.1953 (4)
H8	0.851 (2)	0.717 (10)	0.2051 (14)
C9	0.6951 (3)	0.7154 (13)	0.1509 (5)
H9	0.6959 (19)	0.857 (9)	0.1265 (15)
C10	0.5937 (3)	0.5942 (12)	0.1386 (5)
C11	0.4894 (5)	0.7033 (11)	0.0865 (6)
C12	0.3887 (3)	0.5859 (13)	0.0784 (5)
C13	0.1781 (6)	0.5077 (14)	−0.0327 (4)
C14	0.0964 (5)	0.5410 (18)	−0.1166 (4)
C15	0.1055 (7)	1.0754 (17)	0.4079 (5)
C16	0.1786 (4)	1.0485 (15)	0.3569 (4)
C17	0.3948 (3)	1.0957 (13)	0.3695 (5)
C18	0.5009 (5)	1.1923 (10)	0.4166 (5)
C19	0.6001 (3)	1.0672 (14)	0.4172 (3)
C20	0.7101 (3)	1.1640 (13)	0.4634 (5)
H20	0.7218 (18)	1.311 (10)	0.4925 (17)
C21	0.7939 (3)	1.0302 (14)	0.4567 (3)
H21	0.8695 (19)	1.078 (10)	0.4884 (19)
C22	0.7740 (3)	0.8128 (14)	0.4165 (3)
H22	0.8356 (18)	0.705 (11)	0.4190 (14)
C23	0.6748 (3)	0.7467 (13)	0.3747 (4)
H23	0.6644 (19)	0.610 (10)	0.3467 (15)
C24	0.5889 (3)	0.8630 (13)	0.3749 (3)
C25	0.4868 (4)	0.7745 (12)	0.3299 (4)
C26	0.3886 (4)	0.9054 (14)	0.3286 (4)
C27	0.1766 (3)	0.8599 (16)	0.3123 (4)
C28	0.1005 (5)	0.6753 (15)	0.3113 (3)

Experimental details

	(I)	(II)	(III)	(IV)
Crystal data
Chemical formula	C₁₄H₄N₂O₂S₂	C₁₄H₄N₂O₂S₂	C₁₄H₄N₂O₂S₂	C₁₄H₄N₂O₂S₂
M_r	296.33	296.33	296.33	296.33
Crystal system, space group	Orthorhombic, Pna2₁	Triclinic, P1	Monoclinic, P2₁	Monoclinic, P2₁
Temperature (K)	293	293	293	293
a, b, c (Å)	8.49373 (19), 6.2466 (2), 24.2652 (10)	3.89671 (11), 12.1707 (3), 13.0436 (9)	12.4934 (8), 24.6720 (12), 6.2769 (3)	13.0945 (6), 6.0103 (4), 17.1209 (6)
α, β, γ (°)	90, 90, 90	90.710 (9), 81.707 (10), 90.975 (2)	90, 99.442 (4), 90	90, 109.646 (4), 90
V (Å³)	1287.44 (7)	612.02 (5)	1908.57 (19)	1269.02 (11)
Z	4	2	6	4
Radiation type	Cu Kα_1, λ = 1.54059 Å	Cu Kα_1, λ = 1.54059 Å	Cu Kα_1, λ = 1.54059 Å	Cu Kα_1, λ = 1.54059 Å
µ (mm⁻¹)	?	?	?	?
Specimen shape, size (mm)	?, ? × ? × ?	?, ? × ? × ?	?, ? × ? × ?	?, ? × ? × ?

Data collection
Diffractometer	Bruker D8 diffractometer	Bruker D8 diffractometer	Stoe Stadi-P diffractometer	Bruker D8 diffractometer
Specimen mounting	Capillary	Capillary	Capillary	Capillary
Data collection mode	Transmission	Transmission	Transmission	Transmission
Scan method	Step	Step	Step	Step
2θ values (°)	2θ_min = 2 2θ_max = 70 2θ_step = 0.009	2θ_min = 2 2θ_max = 65 2θ_step = 0.009	2θ_min = 5 2θ_max = 70 2θ_step = 0.012	2θ_min = 5 2θ_max = 60 2θ_step = 0.009

Refinement
R factors and goodness of fit	R_p = 0.030, R_wp = 0.039, R_exp = 0.002, χ² = 1.742	R_p = 0.034, R_wp = 0.048, R_exp = 0.014, χ² = 3.349	R_p = 0.020, R_wp = 0.027, R_exp = 0.007, χ² = 3.572	R_p = 0.048, R_wp = 0.065, R_exp = 0.007, χ² = 9.000
No. of data points	?	?	?	?
No. of parameters	106	129	260	177
No. of restraints	65	65	204	139
H-atom treatment	All H-atom parameters refined	All H-atom parameters refined	All H-atom parameters refined	All H-atom parameters refined

Computer programs: Bruker, Topas, none.

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