[μ-1,2,3,4-Tetra­kis(pyridin-4-yl)butane-κ2N1:N4]bis­[trimeth­yl(thio­cyanato-κN)tin(IV)]

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S160053681204737X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1550

doi:10.1107/S160053681204737X

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[μ-1,2,3,4-Tetrakis(pyridin-4-yl)butane-κ²N¹:N⁴]bis[trimethyl(thiocyanato-κN)tin(IV)]

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 17 November 2012; accepted 18 November 2012; online 28 November 2012)

In the title compound, [Sn₂(CH₃)₆(NCS)₂(C₂₄H₂₂N₄)], the 1,2,3,4-tetrakis(pyridin-4-yl)butane ligand uses the pyridine N atoms at the ends of the butyl chain to coordinate to two trimethylthiocyanatotin(IV) units, forming a dinuclear structure. The Sn^IV atom in the molecule shows a distorted trans-trigonal–bipyramidal coordination with the methyl groups in equatorial positions. The molecule lies on a center of inversion, with the mid-point of the butyl chain coinciding with this symmetry element. In the crystal, weak C—H⋯π interactions occur between pyridine rings of adjacent molecules.

Related literature

For trimethyltin(IV) thiocyanate, see: Forder & Sheldrick (1970 ).

Experimental

Crystal data

[Sn₂(CH₃)₆(NCS)₂(C₂₄H₂₂N₄)]
M_r = 810.20
Triclinic, $[P \overline 1]$
a = 9.2959 (8) Å
b = 9.7210 (7) Å
c = 10.2448 (9) Å
α = 90.388 (7)°
β = 94.381 (7)°
γ = 103.646 (7)°
V = 896.72 (13) Å³
Z = 1
Mo Kα radiation
μ = 1.54 mm⁻¹
T = 295 K
0.25 × 0.25 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.700, T_max = 0.927
8527 measured reflections
4153 independent reflections
3645 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.076
S = 1.05
4153 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N2-pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cgⁱ	0.93	2.79	3.631 (4)	151
Symmetry code: (i) -x+1, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681204737X/xu5652sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204737X/xu5652Isup2.hkl

checkCIF report

Comment top

Unlike trimethyltin chloride, the pseudohalide, trimethyltin thiocyanate, furnishes only few coordination compounds with aromatic amines. Trimethyltin thiocyanate itself exists as a zigzag chain in which the thiocyanate unit bridges adjacent trimethyltin cations (Forder & Sheldrick, 1970). The title adduct (Scheme I, Fig. 1) is the first crystal structure report of such an adduct. The tetrapyridyl-substitutent butane ligand, C₂₄H₂₂N₄, uses the pyridine N-atoms at the either ends of the butyl chain to coordinate to a trimethylthiocyanatotin unit. The dinuclear molecule lies on a center-of-inversion, with the mid-point of the butyl chain coinciding with this symmetry element.

The Sn atom is displaced out of the trigonal plane, in the direction of the thiocyanate ion, by 0.036 (2) Å.

Related literature top

For trimethyltin(IV) thiocyanate, see: Forder & Sheldrick (1970).

Experimental top

Trimethyltin thiocyanate (0.19 g, 1 mmol) and 4-[1,3,4-tris(pyridin-4-yl)butan-2-yl]pyridine (0.73 g, 2 mmol) were loaded into a convection tube; the tube was filled with ethyl alcohol andkept at 333 K. Colorless crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [(CH₃)₃Sn(NCS)]₂(C₂₄H₂₂N₄) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

[µ-1,2,3,4-Tetrakis(pyridin-4-yl)butane- κ²N¹:N⁴]bis[trimethyl(thiocyanato-κN)tin(IV)] top

Crystal data top

[Sn₂(CH₃)₆(NCS)₂(C₂₄H₂₂N₄)]	Z = 1
M_r = 810.20	F(000) = 406
Triclinic, P1	D_x = 1.500 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2959 (8) Å	Cell parameters from 3676 reflections
b = 9.7210 (7) Å	θ = 2.9–27.5°
c = 10.2448 (9) Å	µ = 1.54 mm⁻¹
α = 90.388 (7)°	T = 295 K
β = 94.381 (7)°	Prism, colorless
γ = 103.646 (7)°	0.25 × 0.25 × 0.05 mm
V = 896.72 (13) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4153 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3645 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
ω scan	h = −10→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −12→12
T_min = 0.700, T_max = 0.927	l = −12→13
8527 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0324P)² + 0.1997P] where P = (F_o² + 2F_c²)/3
4153 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Sn₂(CH₃)₆(NCS)₂(C₂₄H₂₂N₄)]	γ = 103.646 (7)°
M_r = 810.20	V = 896.72 (13) Å³
Triclinic, P1	Z = 1
a = 9.2959 (8) Å	Mo Kα radiation
b = 9.7210 (7) Å	µ = 1.54 mm⁻¹
c = 10.2448 (9) Å	T = 295 K
α = 90.388 (7)°	0.25 × 0.25 × 0.05 mm
β = 94.381 (7)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4153 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3645 reflections with I > 2σ(I)
T_min = 0.700, T_max = 0.927	R_int = 0.030
8527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.05	Δρ_max = 0.50 e Å⁻³
4153 reflections	Δρ_min = −0.52 e Å⁻³
190 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.76200 (2)	0.553034 (18)	0.347974 (18)	0.03890 (8)
S1	1.20140 (12)	0.90346 (10)	0.55879 (11)	0.0742 (3)
N1	0.9749 (3)	0.7032 (3)	0.4286 (3)	0.0656 (9)
N2	0.5239 (3)	0.3899 (2)	0.2637 (2)	0.0347 (5)
N3	0.3574 (3)	−0.2627 (3)	0.0683 (3)	0.0566 (7)
C1	0.6775 (5)	0.7271 (3)	0.2837 (4)	0.0666 (11)
H1A	0.7503	0.8136	0.3056	0.100*
H1B	0.5888	0.7273	0.3259	0.100*
H1C	0.6549	0.7193	0.1906	0.100*
C2	0.7196 (4)	0.4771 (3)	0.5374 (3)	0.0531 (8)
H2A	0.7987	0.5248	0.5993	0.080*
H2B	0.7133	0.3771	0.5381	0.080*
H2C	0.6275	0.4948	0.5608	0.080*
C3	0.8759 (4)	0.4507 (4)	0.2210 (3)	0.0579 (9)
H3A	0.9803	0.4938	0.2321	0.087*
H3B	0.8397	0.4597	0.1319	0.087*
H3C	0.8592	0.3522	0.2414	0.087*
C4	1.0677 (4)	0.7876 (3)	0.4841 (3)	0.0458 (7)
C5	0.4359 (3)	0.4259 (3)	0.1683 (3)	0.0382 (6)
H5	0.4698	0.5106	0.1264	0.046*
C6	0.2962 (3)	0.3436 (3)	0.1280 (3)	0.0403 (6)
H6	0.2388	0.3734	0.0606	0.048*
C7	0.2420 (3)	0.2165 (3)	0.1887 (3)	0.0351 (6)
C8	0.3340 (3)	0.1789 (3)	0.2859 (3)	0.0437 (7)
H8	0.3030	0.0944	0.3290	0.052*
C9	0.4726 (3)	0.2655 (3)	0.3204 (3)	0.0439 (7)
H9	0.5332	0.2365	0.3857	0.053*
C10	0.0880 (3)	0.1277 (3)	0.1497 (3)	0.0427 (7)
H10A	0.0202	0.1894	0.1367	0.051*
H10B	0.0551	0.0649	0.2203	0.051*
C11	0.0817 (3)	0.0381 (2)	0.0226 (3)	0.0315 (5)
H11	0.1201	0.1030	−0.0463	0.038*
C12	0.1783 (3)	−0.0664 (3)	0.0395 (2)	0.0314 (5)
C13	0.2892 (3)	−0.0683 (3)	−0.0411 (3)	0.0373 (6)
H13	0.3068	−0.0037	−0.1079	0.045*
C14	0.3750 (4)	−0.1665 (3)	−0.0230 (3)	0.0483 (7)
H14	0.4498	−0.1644	−0.0789	0.058*
C15	0.2501 (5)	−0.2597 (4)	0.1456 (4)	0.0619 (10)
H15	0.2353	−0.3257	0.2115	0.074*
C16	0.1589 (4)	−0.1668 (3)	0.1362 (3)	0.0510 (8)
H16	0.0854	−0.1712	0.1939	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03404 (13)	0.03835 (12)	0.04120 (12)	0.00409 (8)	−0.00196 (8)	−0.00293 (8)
S1	0.0695 (7)	0.0535 (5)	0.0823 (7)	−0.0110 (5)	−0.0211 (5)	−0.0118 (4)
N1	0.0449 (18)	0.0651 (18)	0.076 (2)	−0.0031 (15)	−0.0090 (15)	−0.0174 (15)
N2	0.0307 (12)	0.0330 (11)	0.0389 (12)	0.0063 (9)	−0.0018 (9)	−0.0036 (9)
N3	0.0480 (18)	0.0529 (16)	0.072 (2)	0.0224 (13)	−0.0095 (15)	−0.0021 (14)
C1	0.071 (3)	0.0364 (16)	0.086 (3)	0.0074 (16)	−0.018 (2)	0.0022 (15)
C2	0.056 (2)	0.066 (2)	0.0380 (16)	0.0187 (16)	−0.0005 (14)	−0.0060 (14)
C3	0.0422 (19)	0.070 (2)	0.058 (2)	0.0038 (16)	0.0117 (15)	−0.0171 (16)
C4	0.0440 (18)	0.0423 (15)	0.0475 (17)	0.0043 (14)	−0.0004 (14)	−0.0002 (12)
C5	0.0411 (16)	0.0313 (13)	0.0384 (14)	0.0028 (11)	−0.0019 (12)	0.0001 (10)
C6	0.0413 (17)	0.0400 (14)	0.0388 (15)	0.0126 (12)	−0.0102 (12)	−0.0044 (11)
C7	0.0282 (14)	0.0332 (13)	0.0416 (14)	0.0035 (11)	0.0010 (11)	−0.0113 (10)
C8	0.0444 (18)	0.0332 (13)	0.0480 (16)	−0.0003 (12)	−0.0025 (13)	0.0029 (11)
C9	0.0397 (17)	0.0365 (14)	0.0511 (17)	0.0053 (12)	−0.0116 (13)	0.0025 (12)
C10	0.0279 (15)	0.0472 (15)	0.0509 (17)	0.0054 (12)	0.0017 (12)	−0.0149 (12)
C11	0.0221 (13)	0.0306 (12)	0.0394 (13)	0.0020 (10)	0.0011 (10)	−0.0032 (10)
C12	0.0245 (13)	0.0342 (12)	0.0333 (13)	0.0048 (10)	−0.0038 (10)	−0.0044 (10)
C13	0.0323 (15)	0.0351 (13)	0.0438 (15)	0.0065 (11)	0.0041 (12)	0.0003 (11)
C14	0.0366 (17)	0.0446 (16)	0.065 (2)	0.0120 (13)	0.0039 (14)	−0.0089 (14)
C15	0.068 (3)	0.0549 (19)	0.064 (2)	0.0211 (18)	−0.0032 (19)	0.0193 (16)
C16	0.050 (2)	0.0559 (18)	0.0497 (18)	0.0151 (15)	0.0096 (15)	0.0136 (14)

Geometric parameters (Å, º) top

Sn1—C1	2.116 (3)	C6—C7	1.390 (4)
Sn1—C3	2.119 (3)	C6—H6	0.9300
Sn1—C2	2.113 (3)	C7—C8	1.371 (4)
Sn1—N1	2.258 (3)	C7—C10	1.509 (4)
Sn1—N2	2.489 (2)	C8—C9	1.381 (4)
S1—C4	1.606 (3)	C8—H8	0.9300
N1—C4	1.152 (4)	C9—H9	0.9300
N2—C5	1.328 (3)	C10—C11	1.551 (4)
N2—C9	1.344 (3)	C10—H10A	0.9700
N3—C14	1.319 (4)	C10—H10B	0.9700
N3—C15	1.326 (5)	C11—C12	1.509 (4)
C1—H1A	0.9600	C11—C11ⁱ	1.557 (5)
C1—H1B	0.9600	C11—H11	0.9800
C1—H1C	0.9600	C12—C13	1.373 (4)
C2—H2A	0.9600	C12—C16	1.388 (4)
C2—H2B	0.9600	C13—C14	1.385 (4)
C2—H2C	0.9600	C13—H13	0.9300
C3—H3A	0.9600	C14—H14	0.9300
C3—H3B	0.9600	C15—C16	1.376 (5)
C3—H3C	0.9600	C15—H15	0.9300
C5—C6	1.386 (4)	C16—H16	0.9300
C5—H5	0.9300

C1—Sn1—C3	120.57 (17)	C5—C6—H6	120.1
C1—Sn1—C2	118.37 (16)	C7—C6—H6	120.1
C3—Sn1—C2	120.97 (15)	C8—C7—C6	116.6 (2)
C1—Sn1—N1	90.01 (13)	C8—C7—C10	122.7 (2)
C3—Sn1—N1	92.20 (13)	C6—C7—C10	120.7 (3)
C2—Sn1—N1	90.71 (12)	C7—C8—C9	120.5 (2)
C1—Sn1—N2	89.41 (11)	C7—C8—H8	119.8
C3—Sn1—N2	89.29 (10)	C9—C8—H8	119.8
C2—Sn1—N2	88.33 (10)	N2—C9—C8	123.0 (3)
N1—Sn1—N2	178.49 (10)	N2—C9—H9	118.5
C4—N1—Sn1	168.1 (3)	C8—C9—H9	118.5
C5—N2—C9	116.8 (2)	C7—C10—C11	112.5 (2)
C5—N2—Sn1	121.93 (16)	C7—C10—H10A	109.1
C9—N2—Sn1	121.08 (18)	C11—C10—H10A	109.1
C14—N3—C15	115.2 (3)	C7—C10—H10B	109.1
Sn1—C1—H1A	109.5	C11—C10—H10B	109.1
Sn1—C1—H1B	109.5	H10A—C10—H10B	107.8
H1A—C1—H1B	109.5	C12—C11—C10	111.5 (2)
Sn1—C1—H1C	109.5	C12—C11—C11ⁱ	111.1 (2)
H1A—C1—H1C	109.5	C10—C11—C11ⁱ	110.7 (3)
H1B—C1—H1C	109.5	C12—C11—H11	107.8
Sn1—C2—H2A	109.5	C10—C11—H11	107.8
Sn1—C2—H2B	109.5	C11ⁱ—C11—H11	107.8
H2A—C2—H2B	109.5	C13—C12—C16	116.3 (3)
Sn1—C2—H2C	109.5	C13—C12—C11	121.8 (2)
H2A—C2—H2C	109.5	C16—C12—C11	121.9 (3)
H2B—C2—H2C	109.5	C12—C13—C14	120.1 (3)
Sn1—C3—H3A	109.5	C12—C13—H13	119.9
Sn1—C3—H3B	109.5	C14—C13—H13	119.9
H3A—C3—H3B	109.5	N3—C14—C13	124.2 (3)
Sn1—C3—H3C	109.5	N3—C14—H14	117.9
H3A—C3—H3C	109.5	C13—C14—H14	117.9
H3B—C3—H3C	109.5	N3—C15—C16	125.3 (3)
N1—C4—S1	178.0 (3)	N3—C15—H15	117.4
N2—C5—C6	123.3 (2)	C16—C15—H15	117.4
N2—C5—H5	118.3	C15—C16—C12	119.0 (3)
C6—C5—H5	118.3	C15—C16—H16	120.5
C5—C6—C7	119.8 (3)	C12—C16—H16	120.5

C1—Sn1—N1—C4	64.3 (14)	C7—C8—C9—N2	1.0 (5)
C3—Sn1—N1—C4	−175.1 (14)	C8—C7—C10—C11	−101.4 (3)
C2—Sn1—N1—C4	−54.0 (14)	C6—C7—C10—C11	79.9 (3)
C1—Sn1—N2—C5	24.7 (2)	C7—C10—C11—C12	62.2 (3)
C3—Sn1—N2—C5	−95.9 (2)	C7—C10—C11—C11ⁱ	−173.6 (3)
C2—Sn1—N2—C5	143.1 (2)	C10—C11—C12—C13	−123.3 (3)
C1—Sn1—N2—C9	−149.7 (3)	C11ⁱ—C11—C12—C13	112.7 (3)
C3—Sn1—N2—C9	89.7 (2)	C10—C11—C12—C16	57.5 (3)
C2—Sn1—N2—C9	−31.3 (2)	C11ⁱ—C11—C12—C16	−66.6 (4)
C9—N2—C5—C6	1.3 (4)	C16—C12—C13—C14	−0.3 (4)
Sn1—N2—C5—C6	−173.4 (2)	C11—C12—C13—C14	−179.6 (2)
N2—C5—C6—C7	0.1 (4)	C15—N3—C14—C13	−0.6 (5)
C5—C6—C7—C8	−1.0 (4)	C12—C13—C14—N3	0.5 (4)
C5—C6—C7—C10	177.9 (3)	C14—N3—C15—C16	0.5 (5)
C6—C7—C8—C9	0.4 (4)	N3—C15—C16—C12	−0.3 (6)
C10—C7—C8—C9	−178.4 (3)	C13—C12—C16—C15	0.2 (4)
C5—N2—C9—C8	−1.8 (4)	C11—C12—C16—C15	179.5 (3)
Sn1—N2—C9—C8	172.9 (2)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N2-pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cgⁱⁱ	0.93	2.79	3.631 (4)	151

Symmetry code: (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Sn₂(CH₃)₆(NCS)₂(C₂₄H₂₂N₄)]
M_r	810.20
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.2959 (8), 9.7210 (7), 10.2448 (9)
α, β, γ (°)	90.388 (7), 94.381 (7), 103.646 (7)
V (Å³)	896.72 (13)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.54
Crystal size (mm)	0.25 × 0.25 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.700, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	8527, 4153, 3645
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.076, 1.05
No. of reflections	4153
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.52

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N2-pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cgⁱ	0.93	2.7905	3.631 (4)	151

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

The authors thank Shahid Beheshti University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Forder, R. A. & Sheldrick, G. M. (1970). J. Organomet. Chem. 21, 115–120. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 12| December 2012| Page m1550

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