Crystal structure of bis­{2-[bis­(2-hy­droxy­eth­yl)amino]­ethanol-κ3O,N,O′}zinc terephthalate

Li, Y.-P.; Zang, H.; Sun, D.; Ming, J.; Su, G.-F.

doi:10.1107/S1600536814021771

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages m361-m362

doi:10.1107/S1600536814021771

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Crystal structure of bis{2-[bis(2-hydroxyethyl)amino]ethanol-κ³O,N,O′}zinc terephthalate

Ya-Ping Li,^a Hu Zang,^b Dajun Sun,^c ^* Julia Ming ^d and Guan-Fang Su ^a

^aDepartment of Ophthalmology, The Second Hospital of Jilin University, 218 Ziqiang Street, Changchun 130041, People's Republic of China, ^bDepartment of Orthopedics, The China–Japan Union Hospital of Jilin University Changchun, Changchun 130033, People's Republic of China, ^cDepartment of Vascular Surgery, The China–Japan Union Hospital of Jilin University, Changchun 130033, People's Republic of China, and ^dSt Erik's Eye Hospital, Karolinska Institutet, Polhemsgatan 50, SE-112 82 Stockholm, Sweden
^*Correspondence e-mail: drsundj@163.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 27 September 2014; accepted 2 October 2014; online 11 October 2014)

In the title salt, [Zn(C₆H₁₅NO₃)₂](C₈H₄O₄), the Zn^II cation, located on a centre of inversion, is coordinated by four O atoms and two N atoms from two tridentate 2-[bis(2-hydroxyethyl)amino]ethanol (BHEA) ligands, giving rise to a slightly distorted octahedral geometry. The terephthalate dianion, located about a centre of inversion, is not coordinated to Zn^II but is connected through O—H⋯O contacts with [Zn(BHEA)₂]²⁺ cations, leading to a three-dimensional crystal structure.

Keywords: crystal structure; chelate; hydrogen bonding; terephthalate.

CCDC reference: 1027329

1. Related literature

For background and a related structure, see: Hamamci et al. (2002 ).

2. Experimental

2.1. Crystal data

[Zn(C₆H₁₅NO₃)₂](C₈H₄O₄)
M_r = 527.86
Triclinic, $[P \overline 1]$
a = 7.963 (5) Å
b = 8.823 (5) Å
c = 9.198 (5) Å
α = 89.315 (5)°
β = 72.421 (5)°
γ = 66.208 (5)°
V = 559.2 (6) Å³
Z = 1
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 293 K
0.26 × 0.24 × 0.23 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.725, T_max = 0.803
3145 measured reflections
2189 independent reflections
2165 reflections with I > 2σ(I)
R_int = 0.012

2.3. Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.072
S = 1.10
2189 reflections
160 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5ⁱ	0.82 (2)	1.82 (2)	2.632 (2)	177 (2)
O2—H2⋯O4ⁱⁱ	0.83 (2)	1.74 (2)	2.564 (2)	178 (2)
O3—H3⋯O5ⁱⁱⁱ	0.87 (2)	2.13 (2)	2.942 (3)	155 (2)
Symmetry codes: (i) -x+2, -y-1, -z; (ii) x-1, y+1, z; (iii) -x+2, -y-1, -z+1.

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1027329

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814021771/tk5343sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814021771/tk5343Isup2.hkl

checkCIF report

Preparation top

The synthesis was performed under hydrothermal conditions. A mixture of Zn(CH₃COO)₂^.2(H₂O), (0.2 mmol, 0.044 g), 2-[bis(2-hydroxyethyl)amino]ethanol (0.4 mmol, 0.062 g), sodium terephthalate (0.2 mmol, 0.042 g) and H₂O (20 mL) in a 30 mL stainless steel reactor with a Teflon liner was heated from 293 to 433 K in 2 h and then held at a constant temperature of 433 K for 72 h, after which the mixture was cooled to 298 K. Colourless crystals of the title compound were recovered from the reaction.

Refinement top

All C-bound H atoms were positioned with idealized geometry (0.93–0.97 Å) and refined isotropically with U_iso(H) = 1.2 U_eq(C) using a riding model. The hydroxy H-atoms were located in a different Fourier map and were refined with an O—H distance restrained to 0.85 (2) Å and with U_iso(H) = 1.5 U_eq(O).

Related literature top

For background and related structures, see: Hökelek & Necefouglu (1996); Necefoglu et al. (2002); Li et al. (2014).

Computing details top

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

A view of the ions in the title salt. Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms in the cation are related by 1-x, -y, -z, and those in the dianion by 1-x, -1-y, 1-z.

A view of the crystal structure of the title salt. Hydrogen bonds are shown as dashed lines.

Bis{2-[bis(2-hydroxyethyl)amino]ethanol-κ³O,N,O'}zinc terephthalate top

Crystal data top

[Zn(C₆H₁₅NO₃)₂](C₈H₄O₄)	Z = 1
M_r = 527.86	F(000) = 278
Triclinic, P1	D_x = 1.567 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.963 (5) Å	Cell parameters from 2165 reflections
b = 8.823 (5) Å	θ = 1.7–22.8°
c = 9.198 (5) Å	µ = 1.16 mm⁻¹
α = 89.315 (5)°	T = 293 K
β = 72.421 (5)°	Block, colourless
γ = 66.208 (5)°	0.26 × 0.24 × 0.23 mm
V = 559.2 (6) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	2189 independent reflections
Radiation source: fine-focus sealed tube	2165 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ϕ and ω scans	θ_max = 26.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→8
T_min = 0.725, T_max = 0.803	k = −10→10
3145 measured reflections	l = −10→11

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0381P)² + 0.3177P] where P = (F_o² + 2F_c²)/3
2189 reflections	(Δ/σ)_max < 0.001
160 parameters	Δρ_max = 0.45 e Å⁻³
3 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Zn(C₆H₁₅NO₃)₂](C₈H₄O₄)	γ = 66.208 (5)°
M_r = 527.86	V = 559.2 (6) Å³
Triclinic, P1	Z = 1
a = 7.963 (5) Å	Mo Kα radiation
b = 8.823 (5) Å	µ = 1.16 mm⁻¹
c = 9.198 (5) Å	T = 293 K
α = 89.315 (5)°	0.26 × 0.24 × 0.23 mm
β = 72.421 (5)°

Data collection top

Bruker SMART APEXII CCD diffractometer	2189 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2165 reflections with I > 2σ(I)
T_min = 0.725, T_max = 0.803	R_int = 0.012
3145 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	3 restraints
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.45 e Å⁻³
2189 reflections	Δρ_min = −0.51 e Å⁻³
160 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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) top

	x	y	z	U_iso*/U_eq
C1	0.6774 (3)	−0.3639 (2)	−0.0601 (2)	0.0370 (5)
H1A	0.7747	−0.4664	−0.1248	0.044*
H1B	0.5597	−0.3796	−0.0138	0.044*
C2	0.7484 (3)	−0.3279 (2)	0.0655 (2)	0.0331 (4)
H2A	0.7475	−0.4087	0.1378	0.040*
H2B	0.8814	−0.3417	0.0199	0.040*
C3	0.3010 (3)	−0.1603 (3)	0.2345 (2)	0.0363 (5)
H3A	0.3374	−0.2759	0.1998	0.044*
H3B	0.1832	−0.1228	0.3224	0.044*
C4	0.4611 (3)	−0.1470 (3)	0.2818 (2)	0.0325 (4)
H4A	0.4091	−0.0417	0.3462	0.039*
H4B	0.5057	−0.2361	0.3426	0.039*
C5	0.7460 (3)	−0.0863 (3)	0.2013 (3)	0.0371 (5)
H5A	0.6741	0.0341	0.2208	0.044*
H5B	0.8648	−0.1107	0.1168	0.044*
C6	0.8006 (4)	−0.1462 (3)	0.3430 (3)	0.0463 (5)
H6A	0.8579	−0.0793	0.3745	0.056*
H6B	0.6851	−0.1329	0.4268	0.056*
C7	0.9062 (2)	−0.7092 (2)	0.3337 (2)	0.0260 (4)
C8	0.6957 (2)	−0.5992 (2)	0.4202 (2)	0.0228 (3)
C9	0.5509 (3)	−0.6072 (2)	0.3698 (2)	0.0253 (4)
H9	0.5846	−0.6789	0.2823	0.030*
C10	0.6436 (3)	−0.4910 (2)	0.5508 (2)	0.0250 (4)
H10	0.7392	−0.4844	0.5852	0.030*
N1	0.6286 (2)	−0.15730 (18)	0.14967 (17)	0.0229 (3)
O1	0.63918 (19)	−0.23022 (16)	−0.15252 (15)	0.0273 (3)
O2	0.26592 (18)	−0.06108 (17)	0.11409 (15)	0.0283 (3)
O3	0.9319 (3)	−0.3128 (2)	0.3114 (2)	0.0553 (5)
O4	0.9393 (2)	−0.8061 (2)	0.21957 (18)	0.0411 (4)
O5	1.03466 (19)	−0.69733 (19)	0.37935 (16)	0.0357 (3)
Zn1	0.5000	0.0000	0.0000	0.01988 (10)
H1	0.738 (3)	−0.249 (3)	−0.224 (2)	0.030*
H2	0.160 (3)	0.020 (2)	0.150 (3)	0.030*
H3	0.954 (3)	−0.343 (3)	0.397 (2)	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0491 (12)	0.0214 (9)	0.0346 (10)	−0.0125 (9)	−0.0086 (9)	−0.0021 (8)
C2	0.0334 (10)	0.0202 (9)	0.0327 (10)	−0.0003 (7)	−0.0084 (8)	0.0034 (7)
C3	0.0277 (9)	0.0398 (11)	0.0383 (11)	−0.0150 (9)	−0.0056 (8)	0.0149 (9)
C4	0.0298 (9)	0.0384 (10)	0.0218 (9)	−0.0095 (8)	−0.0049 (7)	0.0076 (8)
C5	0.0427 (11)	0.0357 (11)	0.0466 (12)	−0.0202 (9)	−0.0284 (10)	0.0128 (9)
C6	0.0430 (12)	0.0505 (14)	0.0519 (14)	−0.0171 (11)	−0.0281 (11)	0.0066 (11)
C7	0.0202 (8)	0.0259 (9)	0.0237 (8)	−0.0041 (7)	−0.0038 (7)	0.0040 (7)
C8	0.0184 (8)	0.0208 (8)	0.0238 (8)	−0.0053 (6)	−0.0038 (6)	0.0041 (6)
C9	0.0231 (8)	0.0249 (9)	0.0233 (8)	−0.0071 (7)	−0.0055 (7)	−0.0011 (6)
C10	0.0205 (8)	0.0271 (9)	0.0263 (9)	−0.0084 (7)	−0.0082 (7)	0.0027 (7)
N1	0.0215 (7)	0.0215 (7)	0.0236 (7)	−0.0066 (6)	−0.0078 (6)	0.0031 (6)
O1	0.0249 (6)	0.0268 (6)	0.0237 (6)	−0.0075 (5)	−0.0038 (5)	−0.0028 (5)
O2	0.0189 (6)	0.0293 (7)	0.0303 (7)	−0.0059 (5)	−0.0050 (5)	0.0047 (5)
O3	0.0529 (10)	0.0576 (11)	0.0483 (10)	−0.0096 (9)	−0.0261 (9)	0.0130 (8)
O4	0.0226 (7)	0.0423 (8)	0.0432 (8)	−0.0025 (6)	−0.0049 (6)	−0.0157 (7)
O5	0.0188 (6)	0.0481 (9)	0.0311 (7)	−0.0068 (6)	−0.0056 (5)	−0.0038 (6)
Zn1	0.01853 (15)	0.01801 (15)	0.01999 (15)	−0.00478 (11)	−0.00604 (10)	0.00264 (10)

Geometric parameters (Å, º) top

C1—O1	1.431 (2)	C6—H6B	0.9700
C1—C2	1.518 (3)	C7—O4	1.255 (2)
C1—H1A	0.9700	C7—O5	1.257 (2)
C1—H1B	0.9700	C7—C8	1.511 (2)
C2—N1	1.483 (2)	C8—C10	1.390 (3)
C2—H2A	0.9700	C8—C9	1.393 (3)
C2—H2B	0.9700	C9—C10ⁱ	1.390 (3)
C3—O2	1.427 (2)	C9—H9	0.9300
C3—C4	1.511 (3)	C10—C9ⁱ	1.390 (3)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	N1—Zn1	2.1282 (16)
C4—N1	1.480 (2)	O1—Zn1	2.1529 (16)
C4—H4A	0.9700	O1—H1	0.815 (16)
C4—H4B	0.9700	O2—Zn1	2.1169 (16)
C5—N1	1.496 (2)	O2—H2	0.825 (16)
C5—C6	1.519 (3)	O3—H3	0.870 (16)
C5—H5A	0.9700	Zn1—O2ⁱⁱ	2.1169 (16)
C5—H5B	0.9700	Zn1—N1ⁱⁱ	2.1282 (16)
C6—O3	1.388 (3)	Zn1—O1ⁱⁱ	2.1529 (16)
C6—H6A	0.9700

O1—C1—C2	111.27 (16)	O5—C7—C8	118.64 (16)
O1—C1—H1A	109.4	C10—C8—C9	119.17 (16)
C2—C1—H1A	109.4	C10—C8—C7	121.09 (16)
O1—C1—H1B	109.4	C9—C8—C7	119.74 (16)
C2—C1—H1B	109.4	C10ⁱ—C9—C8	120.58 (17)
H1A—C1—H1B	108.0	C10ⁱ—C9—H9	119.7
N1—C2—C1	112.93 (16)	C8—C9—H9	119.7
N1—C2—H2A	109.0	C9ⁱ—C10—C8	120.26 (17)
C1—C2—H2A	109.0	C9ⁱ—C10—H10	119.9
N1—C2—H2B	109.0	C8—C10—H10	119.9
C1—C2—H2B	109.0	C4—N1—C2	113.25 (15)
H2A—C2—H2B	107.8	C4—N1—C5	109.91 (16)
O2—C3—C4	110.59 (16)	C2—N1—C5	112.28 (16)
O2—C3—H3A	109.5	C4—N1—Zn1	104.11 (11)
C4—C3—H3A	109.5	C2—N1—Zn1	108.27 (12)
O2—C3—H3B	109.5	C5—N1—Zn1	108.59 (12)
C4—C3—H3B	109.5	C1—O1—Zn1	107.34 (11)
H3A—C3—H3B	108.1	C1—O1—H1	108.2 (17)
N1—C4—C3	113.26 (16)	Zn1—O1—H1	120.1 (16)
N1—C4—H4A	108.9	C3—O2—Zn1	112.52 (11)
C3—C4—H4A	108.9	C3—O2—H2	108.0 (16)
N1—C4—H4B	108.9	Zn1—O2—H2	114.6 (16)
C3—C4—H4B	108.9	C6—O3—H3	106.6 (15)
H4A—C4—H4B	107.7	O2ⁱⁱ—Zn1—O2	180.00 (4)
N1—C5—C6	117.31 (18)	O2ⁱⁱ—Zn1—N1ⁱⁱ	81.99 (7)
N1—C5—H5A	108.0	O2—Zn1—N1ⁱⁱ	98.01 (7)
C6—C5—H5A	108.0	O2ⁱⁱ—Zn1—N1	98.01 (7)
N1—C5—H5B	108.0	O2—Zn1—N1	81.99 (7)
C6—C5—H5B	108.0	N1ⁱⁱ—Zn1—N1	180.0
H5A—C5—H5B	107.2	O2ⁱⁱ—Zn1—O1ⁱⁱ	90.41 (6)
O3—C6—C5	110.1 (2)	O2—Zn1—O1ⁱⁱ	89.59 (6)
O3—C6—H6A	109.6	N1ⁱⁱ—Zn1—O1ⁱⁱ	82.73 (7)
C5—C6—H6A	109.6	N1—Zn1—O1ⁱⁱ	97.27 (7)
O3—C6—H6B	109.6	O2ⁱⁱ—Zn1—O1	89.59 (6)
C5—C6—H6B	109.6	O2—Zn1—O1	90.41 (6)
H6A—C6—H6B	108.2	N1ⁱⁱ—Zn1—O1	97.27 (7)
O4—C7—O5	124.72 (16)	N1—Zn1—O1	82.73 (7)
O4—C7—C8	116.64 (16)	O1ⁱⁱ—Zn1—O1	180.00 (12)

O1—C1—C2—N1	47.2 (2)	C3—O2—Zn1—N1	4.13 (13)
O2—C3—C4—N1	−43.7 (2)	C3—O2—Zn1—O1ⁱⁱ	−93.26 (13)
N1—C5—C6—O3	68.3 (3)	C3—O2—Zn1—O1	86.74 (13)
O4—C7—C8—C10	178.15 (17)	C4—N1—Zn1—O2ⁱⁱ	154.45 (12)
O5—C7—C8—C10	−2.2 (3)	C2—N1—Zn1—O2ⁱⁱ	−84.78 (12)
O4—C7—C8—C9	−1.1 (3)	C5—N1—Zn1—O2ⁱⁱ	37.38 (13)
O5—C7—C8—C9	178.52 (17)	C4—N1—Zn1—O2	−25.55 (12)
C10—C8—C9—C10ⁱ	−0.3 (3)	C2—N1—Zn1—O2	95.22 (12)
C7—C8—C9—C10ⁱ	179.03 (16)	C5—N1—Zn1—O2	−142.62 (13)
C9—C8—C10—C9ⁱ	0.3 (3)	C4—N1—Zn1—N1ⁱⁱ	−80 (100)
C7—C8—C10—C9ⁱ	−179.02 (16)	C2—N1—Zn1—N1ⁱⁱ	41 (100)
C3—C4—N1—C2	−72.9 (2)	C5—N1—Zn1—N1ⁱⁱ	163 (100)
C3—C4—N1—C5	160.62 (17)	C4—N1—Zn1—O1ⁱⁱ	63.01 (12)
C3—C4—N1—Zn1	44.47 (18)	C2—N1—Zn1—O1ⁱⁱ	−176.22 (12)
C1—C2—N1—C4	87.9 (2)	C5—N1—Zn1—O1ⁱⁱ	−54.06 (13)
C1—C2—N1—C5	−146.89 (18)	C4—N1—Zn1—O1	−116.99 (12)
C1—C2—N1—Zn1	−27.01 (19)	C2—N1—Zn1—O1	3.78 (12)
C6—C5—N1—C4	48.9 (2)	C5—N1—Zn1—O1	125.94 (13)
C6—C5—N1—C2	−78.1 (2)	C1—O1—Zn1—O2ⁱⁱ	118.61 (13)
C6—C5—N1—Zn1	162.17 (16)	C1—O1—Zn1—O2	−61.39 (13)
C2—C1—O1—Zn1	−40.83 (19)	C1—O1—Zn1—N1ⁱⁱ	−159.52 (12)
C4—C3—O2—Zn1	18.7 (2)	C1—O1—Zn1—N1	20.48 (12)
C3—O2—Zn1—O2ⁱⁱ	116 (100)	C1—O1—Zn1—O1ⁱⁱ	−79 (100)
C3—O2—Zn1—N1ⁱⁱ	−175.87 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱⁱⁱ	0.82 (2)	1.82 (2)	2.632 (2)	177 (2)
O2—H2···O4^iv	0.83 (2)	1.74 (2)	2.564 (2)	178 (2)
O3—H3···O5^v	0.87 (2)	2.13 (2)	2.942 (3)	155 (2)

Symmetry codes: (iii) −x+2, −y−1, −z; (iv) x−1, y+1, z; (v) −x+2, −y−1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.815 (16)	1.818 (17)	2.632 (2)	177 (2)
O2—H2···O4ⁱⁱ	0.825 (16)	1.740 (16)	2.564 (2)	178 (2)
O3—H3···O5ⁱⁱⁱ	0.870 (16)	2.129 (18)	2.942 (3)	155 (2)

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

Acknowledgements

The project is supported by the International Scientific and Technological Cooperation Foundation of Jilin Province (20120722).

References

Bruker (2002). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hamamci, S., Yilmaz, V. T. & Thöne, C. (2002). Acta Cryst. E58, m369–m371. Web of Science CSD CrossRef CAS IUCr Journals 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 70| Part 11| November 2014| Pages m361-m362

doi:10.1107/S1600536814021771

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