Hexaaqua­nickel(II) bis­{4-[(2-chlorothia­zol-5-yl)meth­oxy]benzoate} dihydrate

Zhang, H.-K.; Gao, J.-S.; Jiang, X.-H.; Hou, G.-F.

doi:10.1107/S1600536808007836

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page m585

doi:10.1107/S1600536808007836

Open

access

Hexaaquanickel(II) bis{4-[(2-chlorothiazol-5-yl)methoxy]benzoate} dihydrate

Hong-Kun Zhang,^a Jin-Sheng Gao,^b Xiao-Hui Jiang ^a ^* and Guang-Feng Hou ^b

^aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China, and ^bSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: zhanghongkun2000@163.com

(Received 19 March 2008; accepted 21 March 2008; online 29 March 2008)

In the title compound, [Ni(H₂O)₆](C₁₁H₇ClNO₃S)₂·2H₂O, the Ni^II atom lies on an inversion center and is six-coordinate in an octahedral environment of water molecules. The cation and anion are linked through O—H⋯O hydrogen bonding involving the coordinated and uncoordinated water molecules into a three-dimensional network.

Related literature

For the synthesis of 4-[(2-chloro-5-thiazolyl)methoxy]benzoic acid, see: Mirci (1990 ).

Experimental

Crystal data

[Ni(H₂O)₆](C₁₁H₇ClNO₃S)₂·2H₂O
M_r = 740.21
Triclinic, $[P \overline 1]$
a = 7.1844 (4) Å
b = 7.2084 (4) Å
c = 15.5621 (8) Å
α = 78.388 (1)°
β = 81.285 (1)°
γ = 71.734 (1)°
V = 746.26 (7) Å³
Z = 1
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 291 (2) K
0.20 × 0.18 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.819, T_max = 0.921
4613 measured reflections
2862 independent reflections
2496 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.075
S = 1.06
2862 reflections
196 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H8⋯O7ⁱ	0.85	2.05	2.903 (2)	175
O4—H9⋯O2ⁱⁱ	0.85	1.93	2.776 (2)	172
O5—H10⋯N1ⁱⁱⁱ	0.85	2.01	2.858 (2)	173
O5—H11⋯O7^iv	0.85	1.91	2.750 (2)	173
O6—H12⋯O1	0.85	1.94	2.781 (2)	171
O6—H13⋯O1ⁱ	0.85	1.90	2.747 (2)	177
O7—H14⋯O1	0.85	1.88	2.718 (2)	169
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y-1, z; (iii) -x+2, -y, -z; (iv) -x+1, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 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: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808007836/ng2435sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007836/ng2435Isup2.hkl

checkCIF report

Comment top

Simple carboxylic acids exhibit a variety of superamolecular aggregation patterns. Recenttly,our attention has been focused on 4-[(2-Chloro-5-thiazolyl)methoxy]Benzoic acid, it is a intermediate used in the synthesis of pesticide. In this paper, we reprot a new complex, (I), synthesized by the reaction of 4-[(2-chloro-5-thiazolyl)methoxy]benzoic acid and nickel(II) nitrate hexahydrate in an aqueous solution.

The asymmetric unit of (I) consists of a hexaaquanickel(II) cation, two 4-[(2-chloro-5-thiazolyl)methoxy]benzoate anions and noe uncoordinated water molecules(Fig. 1). The Ni(II) atom lies on an inversion and is coordinated by six water molecules in an octahedral environment. The anion is almost planar,the largest deviation being 0.136 (5) Å for atom Cl1.

All cations, anions and uncoordinated water molecules are linked through O—H···O hydrogen bonds,resulting in a three-dimensional supramolecular network(Fig. 2; Table 1).

Related literature top

For the synthesis of 4-[(2-chloro-5-thiazolyl)methoxy]benzoic acid, see: Mirci (1990) .

Experimental top

4-[(2-Chloro-5-thiazolyl)methoxy]benzoic acid was prepared by substitute reaction of 4-hydroxybenzoic acid and 2-chloro-5-chloromethoxythiazol under basic conditions(stephen et al.,2000). Nickel nitrate hexahydrate(0.582 g, 2 mmol) and 4-[(2-Chloro-5-thiazolyl)methoxy]benzoic acid(0.538 g, 2 mmol) were dissolved in water(15 ml) and the pH was adjusted to 7 with 0.01 mol/L sodium hydroxide. Jade-green crystals separated from filtered after several days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. A dashed line indicates the intermolecular O—H···O hydrogen-bonding interaction. [Symmetry code: (i) 2 - x, -y, 1 - z]
	Fig. 2. A partial packing view, showing the three-dimensional network. Dashed lines indicate the hydrogen-bonding interactions. The H atoms have been omitted for clarity.

Hexaaquanickel(II) bis{4-[(2-chlorothiazol-5-yl)methoxy]benzoate} dihydrate top

Crystal data top

[Ni(H₂O)₆](C₁₁H₇ClNO₃S)₂·2H₂O	Z = 1
M_r = 740.21	F(000) = 382
Triclinic, P1	D_x = 1.647 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1844 (4) Å	Cell parameters from 4613 reflections
b = 7.2084 (4) Å	θ = 2.7–28.2°
c = 15.5621 (8) Å	µ = 1.04 mm⁻¹
α = 78.388 (1)°	T = 291 K
β = 81.285 (1)°	Block, green
γ = 71.734 (1)°	0.20 × 0.18 × 0.08 mm
V = 746.26 (7) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	2496 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ω scan	θ_max = 26.0°, θ_min = 2.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
T_min = 0.819, T_max = 0.922	k = −4→8
4613 measured reflections	l = −19→19

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0324P)² + 0.4113P] where P = (F_o² + 2F_c²)/3
2862 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Ni(H₂O)₆](C₁₁H₇ClNO₃S)₂·2H₂O	γ = 71.734 (1)°
M_r = 740.21	V = 746.26 (7) Å³
Triclinic, P1	Z = 1
a = 7.1844 (4) Å	Mo Kα radiation
b = 7.2084 (4) Å	µ = 1.04 mm⁻¹
c = 15.5621 (8) Å	T = 291 K
α = 78.388 (1)°	0.20 × 0.18 × 0.08 mm
β = 81.285 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2862 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2496 reflections with I > 2σ(I)
T_min = 0.819, T_max = 0.922	R_int = 0.012
4613 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.06	Δρ_max = 0.36 e Å⁻³
2862 reflections	Δρ_min = −0.22 e Å⁻³
196 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.4407 (3)	0.4075 (3)	0.34973 (14)	0.0299 (5)
C2	0.5199 (3)	0.3065 (3)	0.27064 (14)	0.0290 (4)
C3	0.5491 (3)	0.4165 (3)	0.18875 (14)	0.0341 (5)
H1	0.5231	0.5528	0.1836	0.041*
C4	0.6166 (3)	0.3275 (3)	0.11385 (15)	0.0377 (5)
H2	0.6367	0.4031	0.0593	0.045*
C5	0.6532 (3)	0.1257 (3)	0.12194 (14)	0.0357 (5)
C6	0.6261 (4)	0.0128 (3)	0.20322 (15)	0.0454 (6)
H3	0.6515	−0.1234	0.2081	0.055*
C7	0.5612 (4)	0.1027 (3)	0.27714 (15)	0.0414 (6)
H4	0.5450	0.0260	0.3318	0.050*
C8	0.7285 (4)	0.1271 (3)	−0.03345 (14)	0.0404 (5)
H6	0.8182	0.2060	−0.0388	0.048*
H5	0.5999	0.2151	−0.0474	0.048*
C9	0.8018 (3)	−0.0208 (3)	−0.09460 (14)	0.0336 (5)
C10	0.8419 (4)	0.0072 (4)	−0.18299 (15)	0.0444 (6)
H7	0.8252	0.1330	−0.2162	0.053*
C11	0.9178 (3)	−0.3136 (3)	−0.16161 (15)	0.0369 (5)
Cl1	0.99611 (11)	−0.54983 (9)	−0.18443 (5)	0.05607 (19)
N1	0.9093 (3)	−0.1615 (3)	−0.22133 (13)	0.0431 (5)
Ni1	1.0000	0.0000	0.5000	0.02618 (11)
O1	0.4168 (2)	0.2996 (2)	0.42325 (10)	0.0360 (4)
O2	0.4022 (2)	0.5919 (2)	0.33923 (10)	0.0420 (4)
O3	0.7165 (3)	0.0213 (2)	0.05258 (10)	0.0521 (5)
O4	1.0411 (2)	−0.1930 (2)	0.41173 (11)	0.0435 (4)
H8	0.9563	−0.2515	0.4097	0.065*
H9	1.1530	−0.2663	0.3946	0.065*
O5	0.9559 (3)	0.2269 (2)	0.39824 (11)	0.0519 (5)
H10	1.0058	0.2093	0.3463	0.078*
H11	0.8994	0.3483	0.4014	0.078*
O6	0.7076 (2)	0.0327 (2)	0.52300 (11)	0.0403 (4)
H12	0.6286	0.1176	0.4888	0.061*
H13	0.6671	−0.0686	0.5411	0.061*
O7	0.2566 (2)	0.3897 (2)	0.58489 (11)	0.0418 (4)
H15	0.3537	0.3765	0.6131	0.063*
H14	0.3016	0.3778	0.5319	0.063*
S1	0.84843 (10)	−0.26984 (9)	−0.05532 (4)	0.04168 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0288 (10)	0.0311 (12)	0.0304 (11)	−0.0066 (9)	−0.0005 (8)	−0.0112 (9)
C2	0.0305 (10)	0.0267 (11)	0.0279 (11)	−0.0039 (8)	−0.0003 (8)	−0.0090 (9)
C3	0.0447 (12)	0.0248 (11)	0.0319 (12)	−0.0084 (9)	0.0001 (9)	−0.0082 (9)
C4	0.0515 (13)	0.0326 (12)	0.0258 (11)	−0.0108 (10)	0.0030 (10)	−0.0049 (9)
C5	0.0450 (12)	0.0313 (12)	0.0270 (11)	−0.0040 (10)	0.0032 (9)	−0.0126 (9)
C6	0.0708 (17)	0.0232 (12)	0.0336 (13)	−0.0049 (11)	0.0067 (12)	−0.0080 (10)
C7	0.0600 (15)	0.0301 (12)	0.0268 (11)	−0.0074 (11)	0.0080 (10)	−0.0065 (10)
C8	0.0577 (14)	0.0332 (13)	0.0272 (12)	−0.0087 (11)	0.0025 (10)	−0.0104 (10)
C9	0.0417 (12)	0.0282 (11)	0.0291 (11)	−0.0076 (9)	0.0003 (9)	−0.0075 (9)
C10	0.0702 (16)	0.0297 (12)	0.0284 (12)	−0.0098 (11)	0.0028 (11)	−0.0071 (10)
C11	0.0434 (12)	0.0328 (12)	0.0327 (12)	−0.0067 (10)	0.0022 (10)	−0.0126 (10)
Cl1	0.0756 (5)	0.0341 (3)	0.0554 (4)	−0.0099 (3)	0.0077 (3)	−0.0205 (3)
N1	0.0622 (13)	0.0352 (11)	0.0283 (10)	−0.0085 (9)	0.0044 (9)	−0.0130 (9)
Ni1	0.0301 (2)	0.0224 (2)	0.0240 (2)	−0.00492 (15)	0.00206 (14)	−0.00691 (15)
O1	0.0464 (9)	0.0331 (8)	0.0274 (8)	−0.0104 (7)	0.0037 (7)	−0.0098 (7)
O2	0.0575 (10)	0.0278 (8)	0.0362 (9)	−0.0050 (7)	0.0040 (7)	−0.0130 (7)
O3	0.0902 (14)	0.0318 (9)	0.0255 (8)	−0.0070 (9)	0.0071 (8)	−0.0114 (7)
O4	0.0432 (9)	0.0421 (10)	0.0493 (10)	−0.0121 (7)	0.0064 (7)	−0.0255 (8)
O5	0.0836 (13)	0.0268 (9)	0.0277 (8)	0.0023 (8)	0.0087 (8)	−0.0048 (7)
O6	0.0340 (8)	0.0358 (9)	0.0482 (10)	−0.0101 (7)	0.0004 (7)	−0.0035 (7)
O7	0.0494 (9)	0.0378 (9)	0.0371 (9)	−0.0085 (7)	0.0032 (7)	−0.0159 (7)
S1	0.0599 (4)	0.0318 (3)	0.0279 (3)	−0.0089 (3)	0.0050 (3)	−0.0064 (2)

Geometric parameters (Å, º) top

C1—O2	1.251 (3)	C10—N1	1.380 (3)
C1—O1	1.269 (3)	C10—H7	0.9300
C1—C2	1.503 (3)	C11—N1	1.279 (3)
C2—C3	1.383 (3)	C11—Cl1	1.710 (2)
C2—C7	1.390 (3)	C11—S1	1.716 (2)
C3—C4	1.393 (3)	Ni1—O5	2.0167 (16)
C3—H1	0.9300	Ni1—O5ⁱ	2.0167 (16)
C4—C5	1.378 (3)	Ni1—O6ⁱ	2.0230 (15)
C4—H2	0.9300	Ni1—O6	2.0230 (15)
C5—O3	1.379 (3)	Ni1—O4ⁱ	2.0732 (15)
C5—C6	1.382 (3)	Ni1—O4	2.0732 (15)
C6—C7	1.381 (3)	O4—H8	0.8499
C6—H3	0.9300	O4—H9	0.8500
C7—H4	0.9300	O5—H10	0.8500
C8—O3	1.406 (3)	O5—H11	0.8500
C8—C9	1.492 (3)	O6—H12	0.8499
C8—H6	0.9700	O6—H13	0.8500
C8—H5	0.9700	O7—H15	0.8499
C9—C10	1.349 (3)	O7—H14	0.8501
C9—S1	1.718 (2)

O2—C1—O1	124.10 (19)	N1—C10—H7	121.9
O2—C1—C2	118.33 (19)	N1—C11—Cl1	122.70 (17)
O1—C1—C2	117.58 (19)	N1—C11—S1	116.45 (17)
C3—C2—C7	118.43 (19)	Cl1—C11—S1	120.85 (14)
C3—C2—C1	120.19 (19)	C11—N1—C10	109.39 (19)
C7—C2—C1	121.36 (19)	O5—Ni1—O5ⁱ	180.000 (1)
C2—C3—C4	121.4 (2)	O5—Ni1—O6ⁱ	88.79 (7)
C2—C3—H1	119.3	O5ⁱ—Ni1—O6ⁱ	91.21 (7)
C4—C3—H1	119.3	O5—Ni1—O6	91.21 (7)
C5—C4—C3	118.9 (2)	O5ⁱ—Ni1—O6	88.79 (7)
C5—C4—H2	120.5	O6ⁱ—Ni1—O6	180.00 (9)
C3—C4—H2	120.5	O5—Ni1—O4ⁱ	91.14 (7)
C4—C5—O3	124.3 (2)	O5ⁱ—Ni1—O4ⁱ	88.86 (7)
C4—C5—C6	120.6 (2)	O6ⁱ—Ni1—O4ⁱ	92.92 (6)
O3—C5—C6	115.1 (2)	O6—Ni1—O4ⁱ	87.08 (6)
C7—C6—C5	119.9 (2)	O5—Ni1—O4	88.86 (7)
C7—C6—H3	120.0	O5ⁱ—Ni1—O4	91.14 (7)
C5—C6—H3	120.0	O6ⁱ—Ni1—O4	87.08 (6)
C6—C7—C2	120.7 (2)	O6—Ni1—O4	92.92 (6)
C6—C7—H4	119.6	O4ⁱ—Ni1—O4	180.0
C2—C7—H4	119.6	C5—O3—C8	118.64 (18)
O3—C8—C9	107.34 (18)	Ni1—O4—H8	121.8
O3—C8—H6	110.2	Ni1—O4—H9	123.8
C9—C8—H6	110.2	H8—O4—H9	107.5
O3—C8—H5	110.2	Ni1—O5—H10	121.0
C9—C8—H5	110.2	Ni1—O5—H11	126.5
H6—C8—H5	108.5	H10—O5—H11	112.2
C10—C9—C8	129.8 (2)	Ni1—O6—H12	120.0
C10—C9—S1	109.38 (17)	Ni1—O6—H13	119.8
C8—C9—S1	120.84 (16)	H12—O6—H13	109.8
C9—C10—N1	116.1 (2)	H15—O7—H14	107.2
C9—C10—H7	121.9	C11—S1—C9	88.63 (11)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H8···O7ⁱⁱ	0.85	2.05	2.903 (2)	175
O4—H9···O2ⁱⁱⁱ	0.85	1.93	2.776 (2)	172
O5—H10···N1^iv	0.85	2.01	2.858 (2)	173
O5—H11···O7^v	0.85	1.91	2.750 (2)	173
O6—H12···O1	0.85	1.94	2.781 (2)	171
O6—H13···O1ⁱⁱ	0.85	1.90	2.747 (2)	177
O7—H14···O1	0.85	1.88	2.718 (2)	169

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

Experimental details

Crystal data
Chemical formula	[Ni(H₂O)₆](C₁₁H₇ClNO₃S)₂·2H₂O
M_r	740.21
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.1844 (4), 7.2084 (4), 15.5621 (8)
α, β, γ (°)	78.388 (1), 81.285 (1), 71.734 (1)
V (Å³)	746.26 (7)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.20 × 0.18 × 0.08

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.819, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	4613, 2862, 2496
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.076, 1.06
No. of reflections	2862
No. of parameters	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.22

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H8···O7ⁱ	0.85	2.05	2.903 (2)	175.4
O4—H9···O2ⁱⁱ	0.85	1.93	2.776 (2)	171.6
O5—H10···N1ⁱⁱⁱ	0.85	2.01	2.858 (2)	172.5
O5—H11···O7^iv	0.85	1.91	2.750 (2)	172.6
O6—H12···O1	0.85	1.94	2.781 (2)	171.3
O6—H13···O1ⁱ	0.85	1.90	2.747 (2)	177.4
O7—H14···O1	0.85	1.88	2.718 (2)	169.1

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

Acknowledgements

The authors gratefully acknowledge financial support from the China West Normal University and Heilongjiang University.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Mirci, L. E. (1990). Rom. Patent No. 0 743 205. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.