catena-Poly[[[2-({6-[(pyrimidin-2-ylsulfanyl-κS)meth­yl]pyridin-2-yl-κN}methyl­sulfan­yl)pyrimidine]­copper(I)]-μ-thio­cyanato-κ2N:S]

Peng, R.; Ng, S.W.

doi:10.1107/S160053681201063X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page m429

doi:10.1107/S160053681201063X

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catena-Poly[[[2-({6-[(pyrimidin-2-ylsulfanyl-κS)methyl]pyridin-2-yl-κN}methylsulfanyl)pyrimidine]copper(I)]-μ-thiocyanato-κ²N:S]

Rong Peng ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, Shantou University, Shantou 515063, Guangdong, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 2 March 2012; accepted 10 March 2012; online 17 March 2012)

The N-heterocyclic ligand in the title compound, [Cu(NCS)(C₁₅H₁₃N₅S₂)]_n, coordinates to the Cu^I atom through its pyridine N-donor site, and adjacent metal atoms are bridged by the thiocyanate ion, forming a helical chain along the b axis. The geometry of the metal atom is tetrahedral owing to a somewhat long intramolecular Cu—S interaction of 2.5621 (9) Å.

Related literature

For the synthesis of the N-heterocyle and its copper(I) adducts, see: Peng et al. (2006 ).

Experimental

Crystal data

[Cu(NCS)(C₁₅H₁₃N₅S₂)]
M_r = 449.04
Monoclinic, P 2₁ /n
a = 11.1706 (8) Å
b = 8.6735 (6) Å
c = 19.0956 (14) Å
β = 100.978 (1)°
V = 1816.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.56 mm⁻¹
T = 293 K
0.16 × 0.11 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.703, T_max = 1.000
10799 measured reflections
4077 independent reflections
3022 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.125
S = 1.04
4077 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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/S160053681201063X/zs2186sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201063X/zs2186Isup2.hkl

checkCIF report

Comment top

We have previously reported the crystal structures of the copper(I) bromide and iodide adducts of 2,6-bis(2-pyrimidinesulfanylmethyl)pyridine. The ligand is a flexible thioether than can coordinate through the nitrogen and sulfur sites (Peng et al., 2006). In the present copper(I) thiocyanate adduct (Scheme I), the N-heterocyclic ligand coordinates to the Cu^I atom through its pyridyl N-donor site (Fig. 1). Adjacent metal atoms are bridged by the thiocyanate ion to form a helical chain running along the b-axis of the monoclinic unit cell (Fig. 2). The geometry of the metal atom is a tetrahedron owing to a somewhat long intramolecular sulfur–copper interaction of 2.5621 (9) Å.

Related literature top

For the synthesis of the N-heterocyle and its copper(I) adducts, see: Peng et al. (2006).

Experimental top

The ligand was synthesized as described by Peng et al. (2006). Copper(I) thiocyanate (0.012 g, 1 mmol), 2,6-bis(2-pyrimidinesulfanylmethyl)pyridine (0.032 g, 0.1 mmol) and acetonitrile (4 ml) were placed in a 13-ml, Teflon-line, stainless-steel Parr bomb. This was heated at 373 K for 48 h, and then cooled at 3 K a minute. The solution was filtered and the solvent allowed to evaporate over two weeks to give brown prisms.

Structure description top

For the synthesis of the N-heterocyle and its copper(I) adducts, see: Peng et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 a portion of the polymeric chain structure of [Cu(NCS)(C₁₆H₁₃N₅S₂)]_n at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The chain structure of the title compound, extending along the b-axis of the unit cell.

catena-Poly[[[2-({6-[(pyrimidin-2-ylsulfanyl-κS)methyl]pyridin-2- yl-κN}methylsulfanyl)pyrimidine]copper(I)]-µ-thiocyanato- κ²N:S] top

Crystal data top

[Cu(NCS)(C₁₅H₁₃N₅S₂)]	F(000) = 912
M_r = 449.04	D_x = 1.642 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2743 reflections
a = 11.1706 (8) Å	θ = 2.6–25.0°
b = 8.6735 (6) Å	µ = 1.56 mm⁻¹
c = 19.0956 (14) Å	T = 293 K
β = 100.978 (1)°	Prism, brown
V = 1816.3 (2) Å³	0.16 × 0.11 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	4077 independent reflections
Radiation source: fine-focus sealed tube	3022 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
T_min = 0.703, T_max = 1.000	k = −11→4
10799 measured reflections	l = −24→23

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0592P)² + 0.7767P] where P = (F_o² + 2F_c²)/3
4077 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 1.18 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Cu(NCS)(C₁₅H₁₃N₅S₂)]	V = 1816.3 (2) Å³
M_r = 449.04	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.1706 (8) Å	µ = 1.56 mm⁻¹
b = 8.6735 (6) Å	T = 293 K
c = 19.0956 (14) Å	0.16 × 0.11 × 0.06 mm
β = 100.978 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	4077 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3022 reflections with I > 2σ(I)
T_min = 0.703, T_max = 1.000	R_int = 0.028
10799 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	Δρ_max = 1.18 e Å⁻³
4077 reflections	Δρ_min = −0.51 e Å⁻³
235 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.40542 (4)	0.22472 (5)	0.23431 (3)	0.06021 (17)
S1	0.39013 (7)	0.38008 (9)	0.11883 (4)	0.0492 (2)
S2	0.51157 (8)	0.14604 (12)	0.39459 (5)	0.0604 (2)
S3	0.05933 (8)	0.47654 (10)	0.29022 (5)	0.0583 (2)
N1	0.4820 (3)	0.2133 (3)	0.02977 (15)	0.0547 (7)
N2	0.6034 (2)	0.4274 (3)	0.07782 (14)	0.0522 (6)
N3	0.5545 (2)	0.3694 (3)	0.26678 (12)	0.0404 (5)
N4	0.6536 (3)	0.3205 (4)	0.49195 (15)	0.0615 (8)
N5	0.4632 (3)	0.2354 (4)	0.51544 (18)	0.0740 (9)
N6	0.2579 (3)	0.3150 (3)	0.25756 (16)	0.0560 (7)
C1	0.5066 (3)	0.3375 (4)	0.07088 (15)	0.0425 (6)
C2	0.5642 (3)	0.1795 (4)	−0.00998 (18)	0.0573 (8)
H2	0.5505	0.0949	−0.0404	0.069*
C3	0.6680 (3)	0.2642 (4)	−0.00794 (18)	0.0565 (9)
H3	0.7248	0.2391	−0.0360	0.068*
C4	0.6842 (3)	0.3875 (4)	0.03729 (18)	0.0578 (9)
H4	0.7544	0.4465	0.0401	0.069*
C5	0.4517 (3)	0.5411 (4)	0.17298 (17)	0.0508 (7)
H5A	0.4792	0.6173	0.1424	0.061*
H5B	0.3865	0.5875	0.1928	0.061*
C6	0.5557 (3)	0.5052 (3)	0.23334 (15)	0.0428 (7)
C7	0.6469 (3)	0.6129 (4)	0.25452 (18)	0.0542 (8)
H7	0.6454	0.7066	0.2307	0.065*
C8	0.7392 (3)	0.5806 (5)	0.31075 (19)	0.0611 (9)
H8	0.8015	0.6513	0.3254	0.073*
C9	0.7378 (3)	0.4420 (4)	0.34490 (18)	0.0549 (8)
H9	0.7993	0.4179	0.3834	0.066*
C10	0.6455 (3)	0.3388 (4)	0.32216 (16)	0.0463 (7)
C11	0.6440 (3)	0.1836 (4)	0.35597 (19)	0.0582 (8)
H11A	0.7163	0.1736	0.3930	0.070*
H11B	0.6487	0.1055	0.3202	0.070*
C12	0.5486 (3)	0.2465 (4)	0.47565 (18)	0.0514 (8)
C13	0.6736 (4)	0.3913 (5)	0.5549 (2)	0.0738 (11)
H13	0.7461	0.4454	0.5686	0.089*
C14	0.5936 (4)	0.3884 (6)	0.5997 (2)	0.0797 (12)
H14	0.6095	0.4388	0.6435	0.096*
C15	0.4898 (4)	0.3090 (7)	0.5780 (2)	0.0903 (15)
H15	0.4334	0.3051	0.6080	0.108*
C16	0.1773 (3)	0.3838 (3)	0.26969 (16)	0.0443 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0529 (3)	0.0354 (2)	0.0982 (4)	0.00026 (17)	0.0294 (2)	−0.0022 (2)
S1	0.0522 (4)	0.0427 (4)	0.0549 (4)	0.0001 (3)	0.0157 (3)	0.0011 (3)
S2	0.0644 (5)	0.0590 (6)	0.0588 (5)	−0.0066 (4)	0.0142 (4)	0.0121 (4)
S3	0.0532 (5)	0.0343 (4)	0.0968 (7)	0.0037 (3)	0.0376 (4)	0.0064 (4)
N1	0.0595 (17)	0.0439 (16)	0.0633 (16)	−0.0106 (13)	0.0185 (13)	−0.0113 (13)
N2	0.0567 (16)	0.0472 (16)	0.0533 (15)	−0.0099 (13)	0.0123 (12)	−0.0070 (12)
N3	0.0459 (13)	0.0321 (13)	0.0478 (13)	0.0040 (10)	0.0206 (11)	0.0004 (10)
N4	0.0522 (17)	0.075 (2)	0.0563 (17)	−0.0033 (15)	0.0080 (13)	0.0150 (15)
N5	0.0558 (18)	0.095 (3)	0.076 (2)	−0.0009 (17)	0.0254 (15)	0.0030 (19)
N6	0.0511 (15)	0.0437 (15)	0.0782 (18)	0.0038 (13)	0.0252 (14)	0.0003 (14)
C1	0.0507 (16)	0.0363 (15)	0.0401 (14)	0.0009 (13)	0.0080 (12)	0.0061 (12)
C2	0.066 (2)	0.0468 (18)	0.0612 (19)	−0.0061 (16)	0.0175 (17)	−0.0147 (16)
C3	0.057 (2)	0.058 (2)	0.0585 (19)	0.0017 (16)	0.0199 (16)	−0.0053 (16)
C4	0.0519 (18)	0.061 (2)	0.063 (2)	−0.0144 (16)	0.0168 (16)	−0.0090 (17)
C5	0.066 (2)	0.0342 (16)	0.0550 (17)	0.0072 (15)	0.0190 (15)	0.0018 (14)
C6	0.0543 (16)	0.0332 (15)	0.0477 (15)	0.0029 (13)	0.0268 (13)	−0.0035 (12)
C7	0.068 (2)	0.0411 (17)	0.0615 (19)	−0.0099 (16)	0.0331 (17)	−0.0036 (15)
C8	0.059 (2)	0.063 (2)	0.067 (2)	−0.0173 (18)	0.0274 (18)	−0.0150 (18)
C9	0.0469 (17)	0.065 (2)	0.0551 (18)	0.0031 (16)	0.0159 (14)	−0.0075 (17)
C10	0.0495 (17)	0.0447 (17)	0.0506 (17)	0.0086 (14)	0.0244 (14)	0.0015 (14)
C11	0.063 (2)	0.057 (2)	0.0587 (19)	0.0121 (17)	0.0203 (16)	0.0087 (17)
C12	0.0459 (17)	0.0512 (19)	0.0583 (18)	0.0115 (14)	0.0133 (14)	0.0189 (15)
C13	0.075 (3)	0.076 (3)	0.064 (2)	−0.008 (2)	−0.001 (2)	0.010 (2)
C14	0.091 (3)	0.081 (3)	0.067 (2)	0.017 (3)	0.014 (2)	−0.004 (2)
C15	0.078 (3)	0.128 (4)	0.076 (3)	0.016 (3)	0.040 (2)	−0.006 (3)
C16	0.0457 (16)	0.0334 (15)	0.0566 (17)	−0.0040 (13)	0.0166 (13)	0.0032 (13)

Geometric parameters (Å, º) top

Cu1—N6	1.951 (3)	C2—H2	0.9300
Cu1—N3	2.083 (2)	C3—C4	1.364 (5)
Cu1—S3ⁱ	2.2536 (9)	C3—H3	0.9300
Cu1—S1	2.5621 (9)	C4—H4	0.9300
S1—C1	1.767 (3)	C5—C6	1.505 (4)
S1—C5	1.794 (3)	C5—H5A	0.9700
S2—C12	1.756 (4)	C5—H5B	0.9700
S2—C11	1.804 (3)	C6—C7	1.385 (4)
S3—C16	1.653 (3)	C7—C8	1.369 (5)
S3—Cu1ⁱⁱ	2.2536 (9)	C7—H7	0.9300
N1—C1	1.331 (4)	C8—C9	1.369 (5)
N1—C2	1.331 (4)	C8—H8	0.9300
N2—C1	1.319 (4)	C9—C10	1.372 (5)
N2—C4	1.341 (4)	C9—H9	0.9300
N3—C6	1.341 (4)	C10—C11	1.494 (5)
N3—C10	1.346 (4)	C11—H11A	0.9700
N4—C12	1.322 (4)	C11—H11B	0.9700
N4—C13	1.329 (5)	C13—C14	1.351 (6)
N5—C12	1.331 (4)	C13—H13	0.9300
N5—C15	1.337 (6)	C14—C15	1.344 (7)
N6—C16	1.140 (4)	C14—H14	0.9300
C2—C3	1.367 (5)	C15—H15	0.9300

N6—Cu1—N3	110.66 (11)	H5A—C5—H5B	107.4
N6—Cu1—S3ⁱ	128.26 (9)	N3—C6—C7	121.8 (3)
N3—Cu1—S3ⁱ	118.42 (7)	N3—C6—C5	118.0 (3)
N6—Cu1—S1	93.67 (9)	C7—C6—C5	120.1 (3)
N3—Cu1—S1	81.83 (7)	C8—C7—C6	119.6 (3)
S3ⁱ—Cu1—S1	108.00 (4)	C8—C7—H7	120.2
C1—S1—C5	102.84 (15)	C6—C7—H7	120.2
C1—S1—Cu1	113.65 (10)	C7—C8—C9	118.6 (3)
C5—S1—Cu1	87.58 (10)	C7—C8—H8	120.7
C12—S2—C11	101.37 (17)	C9—C8—H8	120.7
C16—S3—Cu1ⁱⁱ	103.70 (10)	C8—C9—C10	119.9 (3)
C1—N1—C2	115.3 (3)	C8—C9—H9	120.1
C1—N2—C4	114.7 (3)	C10—C9—H9	120.1
C6—N3—C10	118.2 (3)	N3—C10—C9	122.0 (3)
C6—N3—Cu1	117.9 (2)	N3—C10—C11	116.6 (3)
C10—N3—Cu1	123.8 (2)	C9—C10—C11	121.4 (3)
C12—N4—C13	115.2 (3)	C10—C11—S2	114.6 (2)
C12—N5—C15	114.5 (3)	C10—C11—H11A	108.6
C16—N6—Cu1	172.1 (3)	S2—C11—H11A	108.6
N2—C1—N1	127.7 (3)	C10—C11—H11B	108.6
N2—C1—S1	119.7 (2)	S2—C11—H11B	108.6
N1—C1—S1	112.6 (2)	H11A—C11—H11B	107.6
N1—C2—C3	122.7 (3)	N4—C12—N5	127.0 (3)
N1—C2—H2	118.7	N4—C12—S2	119.9 (2)
C3—C2—H2	118.7	N5—C12—S2	113.2 (3)
C4—C3—C2	116.6 (3)	N4—C13—C14	123.2 (4)
C4—C3—H3	121.7	N4—C13—H13	118.4
C2—C3—H3	121.7	C14—C13—H13	118.4
N2—C4—C3	123.0 (3)	C15—C14—C13	116.7 (4)
N2—C4—H4	118.5	C15—C14—H14	121.7
C3—C4—H4	118.5	C13—C14—H14	121.7
C6—C5—S1	115.8 (2)	N5—C15—C14	123.5 (4)
C6—C5—H5A	108.3	N5—C15—H15	118.2
S1—C5—H5A	108.3	C14—C15—H15	118.2
C6—C5—H5B	108.3	N6—C16—S3	177.0 (3)
S1—C5—H5B	108.3

N6—Cu1—S1—C1	−178.20 (14)	C10—N3—C6—C5	−178.1 (2)
N3—Cu1—S1—C1	71.44 (13)	Cu1—N3—C6—C5	−2.2 (3)
S3ⁱ—Cu1—S1—C1	−45.88 (12)	S1—C5—C6—N3	−35.0 (3)
N6—Cu1—S1—C5	78.83 (14)	S1—C5—C6—C7	147.2 (2)
N3—Cu1—S1—C5	−31.53 (12)	N3—C6—C7—C8	0.5 (4)
S3ⁱ—Cu1—S1—C5	−148.84 (11)	C5—C6—C7—C8	178.2 (3)
N6—Cu1—N3—C6	−67.0 (2)	C6—C7—C8—C9	−0.5 (5)
S3ⁱ—Cu1—N3—C6	129.96 (18)	C7—C8—C9—C10	0.4 (5)
S1—Cu1—N3—C6	23.86 (18)	C6—N3—C10—C9	0.2 (4)
N6—Cu1—N3—C10	108.6 (2)	Cu1—N3—C10—C9	−175.4 (2)
S3ⁱ—Cu1—N3—C10	−54.4 (2)	C6—N3—C10—C11	−177.3 (2)
S1—Cu1—N3—C10	−160.5 (2)	Cu1—N3—C10—C11	7.0 (3)
C4—N2—C1—N1	1.0 (5)	C8—C9—C10—N3	−0.3 (5)
C4—N2—C1—S1	−177.9 (2)	C8—C9—C10—C11	177.2 (3)
C2—N1—C1—N2	−1.8 (5)	N3—C10—C11—S2	−61.7 (3)
C2—N1—C1—S1	177.2 (3)	C9—C10—C11—S2	120.8 (3)
C5—S1—C1—N2	−4.7 (3)	C12—S2—C11—C10	−79.1 (3)
Cu1—S1—C1—N2	−97.7 (2)	C13—N4—C12—N5	−0.5 (6)
C5—S1—C1—N1	176.2 (2)	C13—N4—C12—S2	−179.2 (3)
Cu1—S1—C1—N1	83.2 (2)	C15—N5—C12—N4	0.3 (6)
C1—N1—C2—C3	1.2 (5)	C15—N5—C12—S2	179.1 (3)
N1—C2—C3—C4	−0.2 (6)	C11—S2—C12—N4	−0.6 (3)
C1—N2—C4—C3	0.3 (5)	C11—S2—C12—N5	−179.5 (3)
C2—C3—C4—N2	−0.7 (5)	C12—N4—C13—C14	0.3 (6)
C1—S1—C5—C6	−71.3 (2)	N4—C13—C14—C15	0.0 (7)
Cu1—S1—C5—C6	42.4 (2)	C12—N5—C15—C14	0.1 (7)
C10—N3—C6—C7	−0.3 (4)	C13—C14—C15—N5	−0.2 (8)
Cu1—N3—C6—C7	175.6 (2)

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

Experimental details

Crystal data
Chemical formula	[Cu(NCS)(C₁₅H₁₃N₅S₂)]
M_r	449.04
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.1706 (8), 8.6735 (6), 19.0956 (14)
β (°)	100.978 (1)
V (Å³)	1816.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.16 × 0.11 × 0.06

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.703, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10799, 4077, 3022
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.125, 1.04
No. of reflections	4077
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.51

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Shantou University and the Ministry of Higher Education of Malaysia (grant No. UM·C/HIR/MOHE/SC/12) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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