Bis(μ-pyridinium-2-carboxyl­ato-κ2O:O′)bis­[triaqua­(sulfato-κO)manganese(II)]

Rasekh, H.A.; Bahrami, B.

doi:10.1107/S1600536811054596

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page m88

doi:10.1107/S1600536811054596

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Bis(μ-pyridinium-2-carboxylato-κ²O:O′)bis[triaqua(sulfato-κO)manganese(II)]

Hossein Ali Rasekh ^a ^* and Bohlul Bahrami ^a

^aDepartment of Chemistry, Islamic Azad University, Firoozabad Branch, Firoozabad, Fars, Iran
^*Correspondence e-mail: Dr.H.A.Rasekh@gmail.com

(Received 11 December 2011; accepted 19 December 2011; online 23 December 2011)

The asymmetric unit of the title compound, [Mn₂(SO₄)₂(C₆H₅NO₂)₂(H₂O)₆], comprises half of a centrosymmetric dimer. The Mn^II atom is coordinated by two O atoms of the monodentate carboxylate ligand, an O atom of the sulfate anion in axial position and three water molecules in a distorted octahedral geometry. In the crystal, molecules are connected through N—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional network. The crystal structure is further stabilized by intermolecular π–π interactions [centroid–centroid distance = 3.842 (2) Å].

Related literature

For standard bond lengths, see: Allen et al. (1987 ). For background to the applications of Mn^II complexes, see: Lee et al. (2004 ); Mautner et al. (1997 ).

Experimental

Crystal data

[Mn₂(SO₄)₂(C₆H₅NO₂)₂(H₂O)₆]
M_r = 656.32
Orthorhombic, P b c a
a = 16.886 (3) Å
b = 7.6022 (15) Å
c = 18.070 (4) Å
V = 2319.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.36 mm⁻¹
T = 291 K
0.28 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.702, T_max = 0.792
5787 measured reflections
1945 independent reflections
1386 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.075
S = 1.26
1944 reflections
181 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.86	1.97	2.799 (3)	161
O1W—H11⋯O5ⁱⁱ	0.81 (2)	2.06 (2)	2.856 (3)	168 (3)
O1W—H12⋯O5ⁱ	0.84 (2)	1.91 (2)	2.735 (3)	173 (3)
O2W—H21⋯O4ⁱⁱ	0.82 (2)	1.90 (2)	2.704 (3)	167 (4)
O2W—H22⋯O4ⁱⁱⁱ	0.83 (2)	1.97 (2)	2.758 (3)	158 (3)
O3W—H31⋯O6ⁱⁱ	0.82 (2)	1.92 (2)	2.736 (3)	177 (4)
O3W—H32⋯O6^iv	0.83 (2)	1.84 (2)	2.660 (3)	172 (3)
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) -x+2, -y+1, -z+1; (iv) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811054596/bq2328sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054596/bq2328Isup2.hkl

checkCIF report

Comment top

As a part of a synthetic work on synthesis and characterization and applications (Lee et al., 2004; Mautner et al., 1997), of new Mn(II) complexes with aromatic carboxylic acid, we determined the X-ray structure of the title compound.

The molecule structure of the title compound (Fig. 1) is composed of a centerosymmetric dimer of a Mn(II) complex with pyridine-2-carboxylic acid. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The geometry around the Mn^II is a distorted octahedron which is coordinated by two oxygen atoms of the carboxylic ligand, an oxygen atom of the sulfate anion, and three oxygen atoms of the coordinated water molecules. Intermolecular N—H···O and O—H···O hydrogen bonds (Table 1), link neighboring molecules, forming three dimensional network (Fig. 2). The crystal structure is further stabilized by the intermolecular π-π interaction [Cg1···Cg1ⁱ = 3.842 (2) Å, (i) 3/2 - x, -1/2 + y, z; Cg1 is the centroid of the (N1/C1–C5) ring.

Related literature top

For standard bond lengths, see: Allen et al., (1987). For background to the applications of Mn^II complexes, see: Lee et al. (2004); Mautner et al. (1997).

Experimental top

The title compound was synthesized by adding 10 ml solution of pyridine-2-carboxylic acid (1.456 g, 11.832 mmol) to a 10 ml solution of manganese sulfate (2g, 11.832 mmol). The mixture was stirred for 24 h. Light-brown single crystals of the title compound suitable for X-ray structure determination were obtained by slow evaporation of the solvents at room temperature after 4 days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 40% probability displacement ellipsoids. Symmetry code for the unlabeled atoms: -x + 2, -y + 1, -z + 1
	Fig. 2. The packing diagram of the title compound viewed down the b-axis showing three dimensional networks. The dashed lines show the intermolecular interactions.

Bis(µ-pyridinium-2-carboxylato-κ²O:O')bis[triaqua(sulfato- κO)manganese(II)] top

Crystal data top

[Mn₂(SO₄)₂(C₆H₅NO₂)₂(H₂O)₆]	F(000) = 1336
M_r = 656.32	D_x = 1.879 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2525 reflections
a = 16.886 (3) Å	θ = 2.5–27.4°
b = 7.6022 (15) Å	µ = 1.36 mm⁻¹
c = 18.070 (4) Å	T = 291 K
V = 2319.6 (8) Å³	Block, light-brown
Z = 4	0.28 × 0.22 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1945 independent reflections
Radiation source: fine-focus sealed tube	1386 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→20
T_min = 0.702, T_max = 0.792	k = −8→9
5787 measured reflections	l = −21→18

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ²(F_o²) + (0.0261P)²] where P = (F_o² + 2F_c²)/3
1944 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.28 e Å⁻³
9 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Mn₂(SO₄)₂(C₆H₅NO₂)₂(H₂O)₆]	V = 2319.6 (8) Å³
M_r = 656.32	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 16.886 (3) Å	µ = 1.36 mm⁻¹
b = 7.6022 (15) Å	T = 291 K
c = 18.070 (4) Å	0.28 × 0.22 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1945 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1386 reflections with I > 2σ(I)
T_min = 0.702, T_max = 0.792	R_int = 0.033
5787 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	9 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	Δρ_max = 0.28 e Å⁻³
1944 reflections	Δρ_min = −0.24 e Å⁻³
181 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.

the reflection "2 0 0" was removed because it was affected by the beam stop

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

	x	y	z	U_iso*/U_eq
C1	0.80634 (14)	0.4943 (3)	0.39991 (16)	0.0274 (6)
C2	0.73913 (18)	0.5011 (4)	0.44213 (18)	0.0441 (8)
H2	0.7429	0.5010	0.4935	0.053*
C3	0.66613 (19)	0.5082 (5)	0.4087 (2)	0.0608 (10)
H3	0.6204	0.5132	0.4373	0.073*
C4	0.66096 (19)	0.5077 (5)	0.3323 (2)	0.0580 (10)
H4	0.6119	0.5134	0.3089	0.070*
C5	0.72870 (19)	0.4990 (4)	0.29191 (19)	0.0513 (9)
H5	0.7263	0.4971	0.2405	0.062*
C6	0.88940 (16)	0.4876 (3)	0.43176 (16)	0.0281 (6)
Mn1	1.06804 (2)	0.42796 (5)	0.39782 (2)	0.02431 (11)
N1	0.79903 (13)	0.4929 (3)	0.32634 (13)	0.0341 (6)
H1	0.8413	0.4879	0.2999	0.041*
O1	0.94438 (10)	0.5098 (3)	0.38689 (11)	0.0369 (5)
O2	1.10645 (13)	0.5419 (2)	0.50058 (11)	0.0407 (5)
O3	1.11498 (11)	0.6541 (2)	0.34100 (11)	0.0326 (5)
O4	1.03729 (12)	0.8763 (2)	0.40293 (11)	0.0413 (5)
O5	1.08436 (11)	0.9258 (2)	0.28009 (10)	0.0364 (5)
O6	1.17596 (11)	0.9245 (2)	0.38020 (12)	0.0439 (6)
S1	1.10322 (4)	0.84382 (8)	0.35237 (4)	0.02353 (15)
O1W	1.04261 (13)	0.2883 (3)	0.29403 (12)	0.0443 (6)
H11	1.0473 (18)	0.183 (2)	0.2892 (18)	0.066*
H12	1.0020 (14)	0.322 (3)	0.2717 (18)	0.066*
O2W	1.02785 (15)	0.2033 (3)	0.46116 (13)	0.0499 (6)
H21	1.023 (2)	0.104 (3)	0.4449 (17)	0.075*
H22	1.007 (2)	0.208 (4)	0.5024 (12)	0.075*
O3W	1.18013 (11)	0.2837 (3)	0.38886 (16)	0.0541 (7)
H31	1.1775 (19)	0.177 (2)	0.385 (2)	0.081*
H32	1.2266 (12)	0.317 (4)	0.386 (2)	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0269 (15)	0.0338 (14)	0.0214 (16)	0.0010 (10)	0.0006 (13)	−0.0029 (13)
C2	0.0358 (19)	0.069 (2)	0.0275 (18)	0.0012 (15)	0.0040 (15)	−0.0017 (15)
C3	0.0265 (17)	0.092 (3)	0.064 (3)	0.0010 (16)	0.0128 (19)	−0.004 (2)
C4	0.0307 (19)	0.084 (3)	0.060 (3)	0.0043 (16)	−0.0178 (18)	−0.008 (2)
C5	0.041 (2)	0.079 (2)	0.034 (2)	0.0091 (16)	−0.0136 (16)	−0.0051 (17)
C6	0.0309 (16)	0.0268 (15)	0.0268 (17)	−0.0002 (11)	−0.0045 (14)	−0.0049 (12)
Mn1	0.02487 (19)	0.0253 (2)	0.0228 (2)	−0.00078 (16)	0.0004 (2)	0.0016 (2)
N1	0.0271 (13)	0.0522 (15)	0.0231 (14)	0.0037 (10)	0.0008 (10)	−0.0015 (11)
O1	0.0254 (11)	0.0471 (12)	0.0381 (13)	0.0007 (8)	−0.0027 (10)	0.0033 (9)
O2	0.0474 (13)	0.0493 (14)	0.0254 (12)	−0.0007 (10)	−0.0098 (10)	−0.0025 (10)
O3	0.0453 (13)	0.0190 (10)	0.0336 (12)	−0.0011 (8)	0.0102 (9)	−0.0012 (9)
O4	0.0517 (12)	0.0352 (12)	0.0369 (12)	0.0031 (8)	0.0185 (11)	−0.0012 (10)
O5	0.0460 (12)	0.0352 (11)	0.0280 (11)	−0.0014 (9)	−0.0035 (9)	0.0077 (9)
O6	0.0364 (11)	0.0309 (11)	0.0643 (16)	0.0000 (9)	−0.0172 (10)	−0.0037 (11)
S1	0.0258 (3)	0.0226 (3)	0.0222 (4)	−0.0006 (3)	0.0009 (3)	0.0009 (3)
O1W	0.0555 (14)	0.0397 (12)	0.0376 (13)	0.0123 (10)	−0.0153 (11)	−0.0104 (11)
O2W	0.0808 (17)	0.0247 (12)	0.0441 (15)	−0.0037 (11)	0.0313 (13)	0.0021 (11)
O3W	0.0279 (10)	0.0296 (11)	0.105 (2)	0.0007 (8)	0.0048 (14)	−0.0058 (14)

Geometric parameters (Å, º) top

C1—N1	1.335 (3)	Mn1—O1	2.1878 (18)
C1—C2	1.368 (4)	Mn1—O3W	2.1934 (19)
C1—C6	1.517 (3)	Mn1—O1W	2.198 (2)
C2—C3	1.374 (4)	N1—H1	0.8600
C2—H2	0.9300	O2—C6ⁱ	1.245 (3)
C3—C4	1.383 (5)	O3—S1	1.4703 (17)
C3—H3	0.9300	O4—S1	1.4613 (19)
C4—C5	1.358 (5)	O5—S1	1.4817 (19)
C4—H4	0.9300	O6—S1	1.4622 (19)
C5—N1	1.342 (4)	O1W—H11	0.811 (17)
C5—H5	0.9300	O1W—H12	0.835 (17)
C6—O1	1.244 (3)	O2W—H21	0.817 (17)
C6—O2ⁱ	1.245 (3)	O2W—H22	0.827 (17)
Mn1—O2	2.1492 (19)	O3W—H31	0.818 (17)
Mn1—O3	2.1536 (18)	O3W—H32	0.826 (17)
Mn1—O2W	2.1652 (19)

N1—C1—C2	118.6 (3)	O1—Mn1—O3W	163.57 (8)
N1—C1—C6	117.6 (2)	O2—Mn1—O1W	172.34 (8)
C2—C1—C6	123.8 (3)	O3—Mn1—O1W	92.91 (8)
C1—C2—C3	120.0 (3)	O2W—Mn1—O1W	90.50 (9)
C1—C2—H2	120.0	O1—Mn1—O1W	82.76 (8)
C3—C2—H2	120.0	O3W—Mn1—O1W	82.19 (9)
C2—C3—C4	119.7 (3)	C1—N1—C5	122.9 (3)
C2—C3—H3	120.1	C1—N1—H1	118.5
C4—C3—H3	120.1	C5—N1—H1	118.5
C5—C4—C3	118.9 (3)	C6—O1—Mn1	127.94 (18)
C5—C4—H4	120.6	C6ⁱ—O2—Mn1	142.42 (18)
C3—C4—H4	120.6	S1—O3—Mn1	131.82 (11)
N1—C5—C4	119.9 (3)	O4—S1—O6	110.72 (12)
N1—C5—H5	120.1	O4—S1—O3	110.86 (10)
C4—C5—H5	120.1	O6—S1—O3	110.26 (11)
O1—C6—O2ⁱ	128.5 (3)	O4—S1—O5	108.44 (12)
O1—C6—C1	116.0 (2)	O6—S1—O5	107.90 (12)
O2ⁱ—C6—C1	115.5 (3)	O3—S1—O5	108.57 (11)
O2—Mn1—O3	88.79 (7)	Mn1—O1W—H11	123 (2)
O2—Mn1—O2W	87.48 (9)	Mn1—O1W—H12	115 (2)
O3—Mn1—O2W	175.65 (9)	H11—O1W—H12	109 (2)
O2—Mn1—O1	104.56 (8)	Mn1—O2W—H21	125 (2)
O3—Mn1—O1	94.65 (7)	Mn1—O2W—H22	125 (2)
O2W—Mn1—O1	88.46 (9)	H21—O2W—H22	109 (2)
O2—Mn1—O3W	90.28 (9)	Mn1—O3W—H31	117 (2)
O3—Mn1—O3W	92.65 (8)	Mn1—O3W—H32	132 (2)
O2W—Mn1—O3W	85.13 (9)	H31—O3W—H32	111 (3)

N1—C1—C2—C3	−0.7 (4)	O3—Mn1—O1—C6	−145.0 (2)
C6—C1—C2—C3	179.5 (3)	O2W—Mn1—O1—C6	32.0 (2)
C1—C2—C3—C4	0.2 (5)	O3W—Mn1—O1—C6	98.9 (4)
C2—C3—C4—C5	0.5 (5)	O1W—Mn1—O1—C6	122.7 (2)
C3—C4—C5—N1	−0.8 (5)	O3—Mn1—O2—C6ⁱ	−176.0 (3)
N1—C1—C6—O1	11.2 (3)	O2W—Mn1—O2—C6ⁱ	1.7 (3)
C2—C1—C6—O1	−169.0 (3)	O1—Mn1—O2—C6ⁱ	89.5 (3)
N1—C1—C6—O2ⁱ	−167.9 (2)	O3W—Mn1—O2—C6ⁱ	−83.4 (3)
C2—C1—C6—O2ⁱ	11.9 (4)	O2—Mn1—O3—S1	−51.74 (16)
C2—C1—N1—C5	0.4 (4)	O1—Mn1—O3—S1	52.77 (16)
C6—C1—N1—C5	−179.8 (2)	O3W—Mn1—O3—S1	−141.97 (17)
C4—C5—N1—C1	0.3 (5)	O1W—Mn1—O3—S1	135.73 (16)
O2ⁱ—C6—O1—Mn1	21.0 (4)	Mn1—O3—S1—O4	−12.1 (2)
C1—C6—O1—Mn1	−157.90 (17)	Mn1—O3—S1—O6	110.89 (16)
O2—Mn1—O1—C6	−55.0 (2)	Mn1—O3—S1—O5	−131.11 (14)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱⁱ	0.86	1.97	2.799 (3)	161
O1W—H11···O5ⁱⁱⁱ	0.81 (2)	2.06 (2)	2.856 (3)	168 (3)
O1W—H12···O5ⁱⁱ	0.84 (2)	1.91 (2)	2.735 (3)	173 (3)
O2W—H21···O4ⁱⁱⁱ	0.82 (2)	1.90 (2)	2.704 (3)	167 (4)
O2W—H22···O4ⁱ	0.83 (2)	1.97 (2)	2.758 (3)	158 (3)
O3W—H31···O6ⁱⁱⁱ	0.82 (2)	1.92 (2)	2.736 (3)	177 (4)
O3W—H32···O6^iv	0.83 (2)	1.84 (2)	2.660 (3)	172 (3)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y−1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+5/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	[Mn₂(SO₄)₂(C₆H₅NO₂)₂(H₂O)₆]
M_r	656.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	291
a, b, c (Å)	16.886 (3), 7.6022 (15), 18.070 (4)
V (Å³)	2319.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.36
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.702, 0.792
No. of measured, independent and observed [I > 2σ(I)] reflections	5787, 1945, 1386
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.26
No. of reflections	1944
No. of parameters	181
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.86	1.97	2.799 (3)	161.2
O1W—H11···O5ⁱⁱ	0.811 (17)	2.058 (17)	2.856 (3)	168 (3)
O1W—H12···O5ⁱ	0.835 (17)	1.905 (17)	2.735 (3)	173 (3)
O2W—H21···O4ⁱⁱ	0.817 (17)	1.901 (17)	2.704 (3)	167 (4)
O2W—H22···O4ⁱⁱⁱ	0.827 (17)	1.97 (2)	2.758 (3)	158 (3)
O3W—H31···O6ⁱⁱ	0.818 (17)	1.919 (18)	2.736 (3)	177 (4)
O3W—H32···O6^iv	0.826 (17)	1.840 (17)	2.660 (3)	172 (3)

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1; (iv) −x+5/2, y−1/2, z.

Acknowledgements

HAR and BB thank Islamic Azad University, Firoozabad Branch. BB thanks Dr Reza Kia for the data collection, structure determination, refinement and manuscript preparation.

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