Redetermination of diaqua­tetra­kis­(dimethyl­formamide-κO)magnesium dichloride

Reiss, G.J.; Boldog, I.; Janiak, C.

doi:10.1107/S1600536811027073

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages m1109-m1110

doi:10.1107/S1600536811027073

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Redetermination of diaquatetrakis(dimethylformamide-κO)magnesium dichloride

Guido J. Reiss,^a Ishtvan Boldog ^a and Christoph Janiak ^a ^*

^aInstitut für Anorganische Chemie und Strukturchemie, Heinrich Heine Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany
^*Correspondence e-mail: janiak@uni-duesseldorf.de

(Received 17 June 2011; accepted 6 July 2011; online 23 July 2011)

The crystal structure of the title compound, [Mg(C₃H₇NO)₄(H₂O)₂]Cl₂, in which the Mg ion lies on a crystallographic inversion centre, confirms that of the previous room-temperature study [Pavanello et al. (1995 ). Main Group Met. Chem. 18, 9–19]. This redetermination at 113 K has improved geometry precision by almost an order of magnitude [e.g. Mg—O(w) (w = water) distances = 2.094 (4) and 2.0899 (7) Å in the old and new structures, respectively] and allowed the water H atoms to be located and their positions refined. In the crystal, O—H⋯Cl hydrogen bonds between the two aqua ligands of the complex molecule and neighboring chloride counter-anions generate supramolecular chains propagating along [010]. The dicationic [Mg(DMF)₄(H₂O)₂] unit (DMF is dimethylformamide) adopts a slightly distorted octahedral geometry in which the Mg atom is coordinated by four DMF O atoms in a pseudo-tetragonal arrangement and two trans aqua ligands.

Related literature

For the previous structure determination, see: Pavanello et al. (1995). For related structures, see: Lebioda & Lewiński (1980 ); Castro et al. (2010 ). For discussion of hydrogen bonds, see: Etter et al. (1990 ); Janiak et al. (1996 ). Dorn et al. (2005 ); Aakeröy et al. (2010 ).

Experimental

Crystal data

[Mg(C₃H₇NO)₄(H₂O)₂]Cl₂
M_r = 423.62
Triclinic, $[P \overline 1]$
a = 8.0284 (3) Å
b = 8.0748 (3) Å
c = 8.8373 (4) Å
α = 90.803 (3)°
β = 91.330 (3)°
γ = 111.563 (4)°
V = 532.51 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 113 K
0.40 × 0.25 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.683, T_max = 1.000
8374 measured reflections
2443 independent reflections
2381 reflections with I > 2σ(I)
R_int = 0.017
3 standard frames every 30 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.048
S = 1.07
2443 reflections
136 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Selected bond lengths (Å)

Mg—O1	2.0221 (6)
Mg—O2	2.0839 (7)
Mg—O3	2.0899 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯Cl	0.810 (16)	2.348 (16)	3.1528 (8)	172.6 (14)
O3—H32⋯Clⁱ	0.817 (17)	2.326 (18)	3.1408 (8)	175.4 (15)
Symmetry code: (i) -x, -y-1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: DIAMOND (Crystal Impact, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811027073/hb5919sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027073/hb5919Isup2.hkl

checkCIF report

Comment top

In the structure of the title compound the complex cation trans-[Mg(H₂O)₂(DMF)₄]²⁺ (DMF = HCON(CH₃)₂) is located on a center of symmetry. Two DMF ligands show significantly shorter Mg—O bond lengths with 2.0221 (6) Å than the two other DMF ligands and the two aqua ligands (2.0839 (7), 2.0899 (7) Å, respectively).

This distortion is in accord with the reported room temperature structure of the title compound [2.021 (5), 2.094 (5) and 2.094 (4) Å, respectively] (Pavanello et al., 1995) and the structure of [MgK₂(croconate violet)(H₂O)₄] where one of the two Mg—O(croconate) bond distances is significantly longer (2.128 Å) than the other one or the Mg—O(H₂O) bond distance (2.072 (1), 2.053 (2) Å, respectively) (Castro et al., 2010). Whereas the structure of [Mg(H₂O)₂{OC(NH₂)₂}₂]Br₂ has similar Mg—O(urea) bond distances of 2.050 (1) and 2.078 (1) Å and a longer Mg—O(H₂O) contact (2.108 (2) Å) (Lebioda & Lewiński, 1980).

Hydrogen bonding as a primary interaction in crytal engineering and supramolecular chemistry is of continous interest (Aakeröy et al., 2010). The hydrogen bonding between the aqua ligands and the chloride counter anions is in the typical range (Dorn et al., 2005; Janiak et al., 1996). The cyclic hydrogen bond motif (Fig.1) which is formed by two aqua ligands of neigboring complexes and two chloride anions features the well known R₂⁴(8) motif (Etter et al., 1990).

Fig. 1 shows the molecular structure with the hydrogen bonding from the aqua ligands to the chloride ions which leads to the supramolecular chain.

Related literature top

For the previous structure determination, see: Pavanello et al. (1995). For related structures, see: Lebioda & Lewiński (1980); Castro et al. (2010). For discussion of hydrogen bonds, see: Etter et al. (1990); Janiak et al. (1996). Dorn et al. (2005); Aakeröy et al. (2010).

Experimental top

Synthesis

42 mg (0.44 mmol) of anhydrous MgCl₂ (Merck, >98%) and 500 µL of DMF (ACS, H₂O content max. 0.1%) in a 1.5 ml vial were shaken at r.t. until complete dissolution of the solid. 16 mL of H₂O (0.88 mmol) were added to the formed solution at once, the solution was homogenized and the vial was placed in an oven preheated at 70°C. After one day the vial was cooled down to r.t. with a rate of 2 K/h to yield large and thick plates of perfect optical quality with dimensions significantly outreaching the millimeter scale. Rapid cooling in an alternative experiment resulted in complete crystallization within one hour. Yet, the formed crystals were of lower quality and their opaqueness indicated some solvent occlusion.The crystalline product redissolves readily in the mother liquor under heating.

The isolated crystals deliquesce quickly in air, whereby hindering the exact determination of the yield. A repeated experiment was performed and the crystals were separated by decanting-off the mother solution, washing the residue with 3 × 1ml of diethyl ether and drying it in an argon stream during a few minutes thus yielding 140 mg (75%) of product.

For IR (ATR) measurements a few transparent crystals were separated directly from the mother solution, dried on a filter paper, ground and measured immediately allowing less then one minute contact with air. IR (ATR): ν (cm^-1) = 3226(s, br, sh), 2933(m), 1649(vs), 1501(m), 1445(m), 1433(m),1417(m), 1394(s), 1252(m), 1116(s), 1063(m),867(w), 679(s). The ether washed product had the same spectrum but with an additional weak line at 805 cm^-1.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Crystal Impact, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. : Molecular structure of [Mg(H₂O)₂{(CH₃)₂NCHO}₄]Cl₂. Hydrogen bonds are indicated as dashed lines (see Table for bond distances and angles). Displacement ellipsoids are drawn at the 60% probability level; H atoms as spheres of arbitrary radii.

Diaquatetrakis(dimethylformamide-κO)magnesium dichloride top

Crystal data top

[Mg(C₃H₇NO)₄(H₂O)₂]Cl₂	Z = 1
M_r = 423.62	F(000) = 226
Triclinic, P1	D_x = 1.321 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0284 (3) Å	Cell parameters from 9519 reflections
b = 8.0748 (3) Å	θ = 3.1–31.8°
c = 8.8373 (4) Å	µ = 0.37 mm⁻¹
α = 90.803 (3)°	T = 113 K
β = 91.330 (3)°	Plate, colourless
γ = 111.563 (4)°	0.40 × 0.25 × 0.10 mm
V = 532.51 (4) Å³

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2381 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
Graphite monochromator	θ_max = 27.5°, θ_min = 5.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −10→10
T_min = 0.683, T_max = 1.000	l = −11→11
8374 measured reflections	3 standard reflections every 30 min
2443 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.01P)² + 0.25P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2443 reflections	Δρ_max = 0.29 e Å⁻³
136 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.058 (3)

Crystal data top

[Mg(C₃H₇NO)₄(H₂O)₂]Cl₂	γ = 111.563 (4)°
M_r = 423.62	V = 532.51 (4) Å³
Triclinic, P1	Z = 1
a = 8.0284 (3) Å	Mo Kα radiation
b = 8.0748 (3) Å	µ = 0.37 mm⁻¹
c = 8.8373 (4) Å	T = 113 K
α = 90.803 (3)°	0.40 × 0.25 × 0.10 mm
β = 91.330 (3)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2381 reflections with I > 2σ(I)
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	R_int = 0.017
T_min = 0.683, T_max = 1.000	3 standard reflections every 30 min
8374 measured reflections	intensity decay: none
2443 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.29 e Å⁻³
2443 reflections	Δρ_min = −0.18 e Å⁻³
136 parameters

Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Oxford Diffraction, 2010).

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
Mg	0.0000	0.0000	0.0000	0.00919 (10)
Cl	0.24638 (3)	−0.39591 (3)	0.17847 (3)	0.01591 (8)
O1	0.24626 (9)	0.07858 (9)	0.10106 (8)	0.01376 (14)
C11	0.37264 (12)	0.22376 (12)	0.12339 (10)	0.01210 (18)
H11	0.3638 (16)	0.3329 (16)	0.0934 (13)	0.014 (3)*
N1	0.52502 (10)	0.23979 (10)	0.19295 (9)	0.01220 (16)
C12	0.66252 (13)	0.41472 (13)	0.22648 (12)	0.0181 (2)
H121	0.6217	0.5055	0.1910	0.027*
H122	0.7705	0.4241	0.1767	0.027*
H123	0.6858	0.4296	0.3338	0.027*
C13	0.56012 (13)	0.08489 (13)	0.24367 (13)	0.0190 (2)
H131	0.4636	−0.0216	0.2097	0.029*
H132	0.5696	0.0877	0.3522	0.029*
H133	0.6702	0.0862	0.2026	0.029*
O2	0.11438 (9)	0.09777 (9)	−0.20529 (7)	0.01321 (14)
C21	0.04046 (12)	0.16098 (12)	−0.30109 (10)	0.01128 (18)
H21	−0.0740 (16)	0.1740 (15)	−0.2843 (13)	0.012 (3)*
N2	0.10760 (11)	0.21837 (10)	−0.43429 (9)	0.01286 (17)
C22	0.00617 (15)	0.27866 (13)	−0.54511 (11)	0.0188 (2)
H221	−0.0977	0.2868	−0.4989	0.028*
H222	−0.0306	0.1953	−0.6292	0.028*
H223	0.0801	0.3936	−0.5802	0.028*
C23	0.28056 (14)	0.21630 (14)	−0.47797 (12)	0.0186 (2)
H231	0.3473	0.2065	−0.3893	0.028*
H232	0.3459	0.3246	−0.5282	0.028*
H233	0.2625	0.1164	−0.5453	0.028*
O3	0.02957 (10)	−0.24245 (9)	−0.04443 (8)	0.01385 (15)
H31	0.094 (2)	−0.2735 (19)	0.0112 (17)	0.030 (4)*
H32	−0.046 (2)	−0.333 (2)	−0.0815 (19)	0.039 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mg	0.0095 (2)	0.0089 (2)	0.0092 (2)	0.00346 (16)	−0.00043 (15)	0.00063 (15)
Cl	0.01812 (12)	0.01091 (11)	0.01905 (13)	0.00586 (9)	−0.00115 (8)	−0.00009 (8)
O1	0.0110 (3)	0.0130 (3)	0.0159 (3)	0.0029 (3)	−0.0024 (2)	0.0007 (3)
C11	0.0140 (4)	0.0124 (4)	0.0107 (4)	0.0057 (4)	0.0016 (3)	0.0010 (3)
N1	0.0102 (4)	0.0101 (4)	0.0154 (4)	0.0026 (3)	0.0004 (3)	−0.0009 (3)
C12	0.0130 (4)	0.0135 (4)	0.0240 (5)	0.0008 (4)	0.0002 (4)	−0.0050 (4)
C13	0.0130 (4)	0.0159 (5)	0.0294 (6)	0.0071 (4)	−0.0036 (4)	0.0018 (4)
O2	0.0143 (3)	0.0143 (3)	0.0119 (3)	0.0063 (3)	0.0014 (2)	0.0027 (2)
C21	0.0127 (4)	0.0081 (4)	0.0122 (4)	0.0030 (3)	0.0005 (3)	−0.0013 (3)
N2	0.0161 (4)	0.0115 (4)	0.0108 (4)	0.0048 (3)	0.0011 (3)	0.0006 (3)
C22	0.0289 (5)	0.0159 (5)	0.0131 (5)	0.0099 (4)	−0.0020 (4)	0.0022 (4)
C23	0.0185 (5)	0.0189 (5)	0.0171 (5)	0.0050 (4)	0.0074 (4)	0.0003 (4)
O3	0.0161 (3)	0.0106 (3)	0.0154 (3)	0.0058 (3)	−0.0029 (3)	−0.0009 (3)

Geometric parameters (Å, º) top

Mg—O1ⁱ	2.0221 (6)	C13—H132	0.9600
Mg—O1	2.0221 (6)	C13—H133	0.9600
Mg—O2	2.0839 (7)	O2—C21	1.2413 (11)
Mg—O2ⁱ	2.0839 (7)	C21—N2	1.3237 (12)
Mg—O3ⁱ	2.0899 (7)	C21—H21	0.977 (12)
Mg—O3	2.0899 (7)	N2—C23	1.4557 (12)
O1—C11	1.2461 (11)	N2—C22	1.4584 (12)
C11—N1	1.3182 (12)	C22—H221	0.9600
C11—H11	0.951 (12)	C22—H222	0.9600
N1—C13	1.4539 (12)	C22—H223	0.9600
N1—C12	1.4589 (12)	C23—H231	0.9600
C12—H121	0.9600	C23—H232	0.9600
C12—H122	0.9600	C23—H233	0.9600
C12—H123	0.9600	O3—H31	0.810 (16)
C13—H131	0.9600	O3—H32	0.817 (17)

O1ⁱ—Mg—O1	180.00 (2)	H122—C12—H123	109.5
O1ⁱ—Mg—O2	89.71 (3)	N1—C13—H131	109.5
O1—Mg—O2	90.29 (3)	N1—C13—H132	109.5
O1ⁱ—Mg—O2ⁱ	90.29 (3)	H131—C13—H132	109.5
O1—Mg—O2ⁱ	89.71 (3)	N1—C13—H133	109.5
O2—Mg—O2ⁱ	180.00 (6)	H131—C13—H133	109.5
O1ⁱ—Mg—O3ⁱ	86.14 (3)	H132—C13—H133	109.5
O1—Mg—O3ⁱ	93.86 (3)	C21—O2—Mg	123.01 (6)
O2—Mg—O3ⁱ	89.34 (3)	O2—C21—N2	124.11 (9)
O2ⁱ—Mg—O3ⁱ	90.66 (3)	O2—C21—H21	122.6 (7)
O1ⁱ—Mg—O3	93.86 (3)	N2—C21—H21	113.3 (7)
O1—Mg—O3	86.14 (3)	C21—N2—C23	121.50 (8)
O2—Mg—O3	90.66 (3)	C21—N2—C22	120.72 (8)
O2ⁱ—Mg—O3	89.34 (3)	C23—N2—C22	117.73 (8)
O3ⁱ—Mg—O3	180.00 (4)	N2—C22—H221	109.5
C11—O1—Mg	135.31 (6)	N2—C22—H222	109.5
O1—C11—N1	123.58 (9)	H221—C22—H222	109.5
O1—C11—H11	121.5 (7)	N2—C22—H223	109.5
N1—C11—H11	114.9 (7)	H221—C22—H223	109.5
C11—N1—C13	121.47 (8)	H222—C22—H223	109.5
C11—N1—C12	121.02 (8)	N2—C23—H231	109.5
C13—N1—C12	117.48 (8)	N2—C23—H232	109.5
N1—C12—H121	109.5	H231—C23—H232	109.5
N1—C12—H122	109.5	N2—C23—H233	109.5
H121—C12—H122	109.5	H231—C23—H233	109.5
N1—C12—H123	109.5	H232—C23—H233	109.5
H121—C12—H123	109.5	H31—O3—H32	106.7 (15)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Cl	0.810 (16)	2.348 (16)	3.1528 (8)	172.6 (14)
O3—H32···Clⁱⁱ	0.817 (17)	2.326 (18)	3.1408 (8)	175.4 (15)

Symmetry code: (ii) −x, −y−1, −z.

Experimental details

Crystal data
Chemical formula	[Mg(C₃H₇NO)₄(H₂O)₂]Cl₂
M_r	423.62
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	8.0284 (3), 8.0748 (3), 8.8373 (4)
α, β, γ (°)	90.803 (3), 91.330 (3), 111.563 (4)
V (Å³)	532.51 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.40 × 0.25 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.683, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8374, 2443, 2381
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.048, 1.07
No. of reflections	2443
No. of parameters	136
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Crystal Impact, 2009), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Mg—O1	2.0221 (6)	Mg—O3	2.0899 (7)
Mg—O2	2.0839 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Cl	0.810 (16)	2.348 (16)	3.1528 (8)	172.6 (14)
O3—H32···Clⁱ	0.817 (17)	2.326 (18)	3.1408 (8)	175.4 (15)

Symmetry code: (i) −x, −y−1, −z.

References

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages m1109-m1110

doi:10.1107/S1600536811027073

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Redetermination of di­aqua­tetra­kis­(di­methyl­formamide-κO)magnesium dichloride

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Redetermination of diaquatetrakis(dimethylformamide-κO)magnesium dichloride