catena-Poly[[nickel(II)-μ3-1,1-dicyano­ethene-2,2-dithiol­ato-κ4S,S′:N:N′-bis­[(15-crown-5)magnesium(II)]-μ3-1,1-dicyano­ethene-2,2-dithiol­ato-κ4N:N′:S,S′] dichloride]

Yang, J.; Li, C.; Li, D.; Wang, D.

doi:10.1107/S1600536807065622

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m174

https://doi.org/10.1107/S1600536807065622

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catena-Poly[[nickel(II)-μ₃-1,1-dicyanoethene-2,2-dithiolato-κ⁴S,S′:N:N′-bis[(15-crown-5)magnesium(II)]-μ₃-1,1-dicyanoethene-2,2-dithiolato-κ⁴N:N′:S,S′] dichloride]

Junli Yang,^a Chengjuan Li,^a ^* Dacheng Li ^a and Daqi Wang ^a

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: dougroup@163.com

(Received 15 November 2007; accepted 4 December 2007; online 12 December 2007)

The reaction of MgCl₂, NiCl₂, and Na₂(i-mnt) (i-mnt is 1,1-dicyanothene-2,2-dithiolate) with 15-crown-5 (15-C-5) leads to an infinite chain polymer, {[NiMg₂(C₄N₂S₂)₂(C₁₀H₂₀O₅)₂]Cl₂}_n or {[Mg(15-C-5)]₂[Ni(i-mnt)₂]Cl₂}_n, which consists of two [Mg(15-C-5)]²⁺ complex cations, one [Ni(i-mnt)₂]²⁻ complex anion and two Cl⁻ ions per formula unit. In the [Ni(i-mnt)₂]²⁻ complex anion, Ni²⁺ is located on a crystallographic mirror plane with a slightly distorted square-planar coordination by four S atoms. In the [Mg(15-C-5)]²⁺ complex cations, the Mg and one O atom of the crown lie on mirror planes and the Mg atoms are in sevenfold coordination environments of five O atoms from the crown and two N atoms from two i-mnt anions. The bridging of the two complexes via the Mg—N bonds leads to the formation of one-dimensional chains along the a axis.

Related literature

For studies on crown ether complexes of alkaline earth metals, see: Junk & Steed (1999 ). For comparative data on Ni–S bonds, see: Gao et al. (2005 ). For comparative data on Mg–O bonds, see: Chadwick et al. (1999 ).

Experimental

Crystal data

[NiMg₂(C₄N₂S₂)₂(C₁₀H₂₀O₅)₂]Cl₂
M_r = 899.11
Orthorhombic, C m c 2₁
a = 13.6227 (16) Å
b = 20.591 (3) Å
c = 15.148 (2) Å
V = 4249 (1) Å³
Z = 4
Mo Kα radiation
μ = 0.86 mm⁻¹
T = 298 (2) K
0.41 × 0.32 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.719, T_max = 0.783
10632 measured reflections
1979 independent reflections
1651 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.192
S = 1.06
1979 reflections
242 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ), 1979 Friedel pairs
Flack parameter: 0.02 (5)

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807065622/sq2001sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065622/sq2001Isup2.hkl

checkCIF report

Comment top

Crown ethers have gained special attention due to their coordination abilities with not only alkali metal ions, but also alkaline earth ions (Junk & Steed, 1999). In this work, we report the synthesis and structure of a crown ether complex of Mg²⁺ networked with a dithiolate Ni^II complex. As shown in Fig. 1, the asymmetric unit of title complex is made up of two half [Mg(15—C-5)]²⁺ complex cations, one half [Ni(i-mnt)₂]^2- complex anion and two dissociative Cl^- ions on mirror planes. For the two crystallographically independent [Mg(15—C-5)]²⁺ complex cations, each Mg²⁺ is coordinated by five O atoms of the crown ether with the average Mg–O distance of 2.566 (12) Å, which is far longer than the value in the complex [Mg(15—C-5)(SCPh₃)₂](2.177 Å) (Chadwick et al., 1999). The additional coordination sites of Mg²⁺ are occupied by two N atoms from cyano groups of the neighboring complex anions [Ni(i-mnt)₂]^2-, with the average Mg–N bond length of 2.531 (12) Å. For the complex anion, the Ni²⁺ is coordinated by four S atoms of two (i-mnt)^2- anions in a square planar geometry. The Ni–S bond lengths are in the range of 2.207 (3) to 2.212 (3) Å, which is in perfect agreement with the values (average 2.215 Å) reported in the complex [Na(N15—C-5)]₂[Ni(i-mnt)₂] (Gao et al., 2005). Fig. 2 shows that the title complex is assembled into a one-dimensional polymer by the Mg–N bonds between the adjacent [Mg(15—C-5)]²⁺ complex cations and the [Ni(i-mnt)₂]^2- complex anions along the a axis. This motif is similar to what is found in the complex [Na(N15—C-5)]₂[Ni(i-mnt)₂], which is also assembled into a one-dimensional stucture by the Na–N bonds between the complex cations and the complex anions. [Na(N15—C-5)]₂[Ni(i-mnt)₂] further exhibits a two-dimensional supramolecular structure resulting from π-π stacking interactions between the naphthylene moieties of N15—C-5, which is not observed in the title complex.

Related literature top

For studies on crown ether complexes of alkaline earth metals, see: Junk & Steed (1999). For comparative data on Ni–S bonds, see: Gao et al. (2005). For comparative data on Mg–O bonds, see: Chadwick et al. (1999).

Experimental top

A solution of NiCl₂ (0.2377 g, 0.1 mmol), Na₂(i-mnt) and MgCl₂ in methanol (10 ml), was added to a solution of 15-C-5 (0.44 g, 2 mmol) in CH₂Cl₂ (10 ml). The mixture was stirred for 3 hrs at room temperature, and then separated. The underlayer was recrystallized in a mixture of CH₂Cl₂ and ether, and crystals suitable for X-ray diffraction were obtained after two weeks (m.p. 471–473 K). Analysis calc. for C₂₈H₄₀Cl₂Mg₂N₄O₁₀S₄: C 37.37, H 4.49, N 6.23%; found: C 37.29, H 4.40, N 6.32%.

Structure description top

For studies on crown ether complexes of alkaline earth metals, see: Junk & Steed (1999). For comparative data on Ni–S bonds, see: Gao et al. (2005). For comparative data on Mg–O bonds, see: Chadwick et al. (1999).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 20% probability displacement ellipsoids for non-H atoms. Symmetry codes: (A) 1 - x, +y, +z; (B) -x, +y, +z.
	Fig. 2. One-dimensional chain-like structure of the title complex (Cl^- ions are omitted).

catena-Poly[[nickel(II)-µ₃-1,1-dicyanothene-2,2-dithiolato-κ⁴S,S':N:N'- bis[(15-crown-5)magnesium(II)]-µ₃-1,1-dicyanoethene-2,2-dithiolato- κ⁴N:N':S,S'] dichloride] top

Crystal data top

[NiMg₂(C₄N₂S₂)₂(C₁₀H₂₀O₅)₂]Cl₂	F(000) = 1864
M_r = 899.11	D_x = 1.406 Mg m⁻³
Orthorhombic, Cmc2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 4296 reflections
a = 13.6227 (16) Å	θ = 2.2–24.9°
b = 20.591 (3) Å	µ = 0.86 mm⁻¹
c = 15.148 (2) Å	T = 298 K
V = 4249 (1) Å³	Block, brown
Z = 4	0.41 × 0.32 × 0.30 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1979 independent reflections
Radiation source: fine-focus sealed tube	1651 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; Sheldrick, 1996)	h = −16→16
T_min = 0.719, T_max = 0.783	k = −24→23
10632 measured reflections	l = −9→18

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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.192	w = 1/[σ²(F_o²) + (0.1309P)² + 12.7693P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
1979 reflections	Δρ_max = 0.92 e Å⁻³
242 parameters	Δρ_min = −0.47 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)

Crystal data top

[NiMg₂(C₄N₂S₂)₂(C₁₀H₂₀O₅)₂]Cl₂	V = 4249 (1) Å³
M_r = 899.11	Z = 4
Orthorhombic, Cmc2₁	Mo Kα radiation
a = 13.6227 (16) Å	µ = 0.86 mm⁻¹
b = 20.591 (3) Å	T = 298 K
c = 15.148 (2) Å	0.41 × 0.32 × 0.30 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1979 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1651 reflections with I > 2σ(I)
T_min = 0.719, T_max = 0.783	R_int = 0.033
10632 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	H-atom parameters constrained
wR(F²) = 0.192	w = 1/[σ²(F_o²) + (0.1309P)² + 12.7693P] where P = (F_o² + 2F_c²)/3
S = 1.06	Δρ_max = 0.92 e Å⁻³
1979 reflections	Δρ_min = −0.47 e Å⁻³
242 parameters	Absolute structure: Flack (1983)
1 restraint	Absolute structure parameter: 0.02 (5)

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
Ni1	0.0000	0.12793 (7)	0.9803 (2)	0.0492 (4)
Mg1	0.5000	0.3176 (3)	1.0866 (4)	0.0713 (14)
Mg2	0.5000	−0.0308 (2)	0.8135 (3)	0.0565 (11)
N1	0.3850 (8)	0.2476 (5)	0.9910 (9)	0.093 (4)
N2	0.3863 (6)	0.0587 (5)	0.8547 (8)	0.074 (3)
O1	0.5000	0.4399 (6)	1.1122 (9)	0.084 (3)
O2	0.3268 (7)	0.3721 (4)	1.1116 (7)	0.084 (2)
O3	0.3963 (10)	0.2655 (6)	1.2030 (8)	0.112 (4)
O4	0.5000	−0.0908 (6)	0.9581 (9)	0.109 (5)
O5	0.6412 (9)	−0.1054 (5)	0.8323 (8)	0.103 (3)
O6	0.5988 (12)	−0.0446 (7)	0.6826 (9)	0.131 (4)
Cl1	0.0000	0.9064 (4)	0.8312 (9)	0.159 (4)
Cl2	0.0000	0.2859 (4)	0.2265 (8)	0.149 (3)
S1	0.12480 (17)	0.18894 (12)	1.02320 (19)	0.0571 (6)
S2	0.12522 (16)	0.07215 (11)	0.9274 (2)	0.0564 (6)
C1	0.4140 (11)	0.4707 (7)	1.1444 (12)	0.095 (4)
H1A	0.4158	0.5167	1.1309	0.114*
H1B	0.4095	0.4655	1.2079	0.114*
C2	0.3302 (12)	0.4407 (6)	1.1020 (12)	0.098 (4)
H2A	0.2706	0.4591	1.1265	0.118*
H2B	0.3316	0.4512	1.0395	0.118*
C3	0.2781 (12)	0.3557 (9)	1.1909 (12)	0.100 (4)
H3A	0.2084	0.3647	1.1863	0.120*
H3B	0.3047	0.3803	1.2401	0.120*
C4	0.2959 (14)	0.2843 (9)	1.2035 (13)	0.108 (5)
H4A	0.2670	0.2712	1.2592	0.129*
H4B	0.2620	0.2609	1.1569	0.129*
C5	0.4508 (14)	0.2588 (10)	1.2820 (11)	0.116 (6)
H5A	0.4301	0.2936	1.3210	0.140*
H5B	0.4301	0.2185	1.3093	0.140*
C6	0.589 (2)	−0.1249 (9)	0.9749 (16)	0.132 (7)
H6A	0.5784	−0.1707	0.9635	0.159*
H6B	0.6055	−0.1202	1.0368	0.159*
C7	0.674 (2)	−0.1019 (10)	0.9200 (15)	0.130 (7)
H7A	0.6922	−0.0577	0.9353	0.156*
H7B	0.7311	−0.1297	0.9287	0.156*
C8	0.7145 (16)	−0.0869 (10)	0.7714 (16)	0.123 (6)
H8A	0.7715	−0.1148	0.7775	0.147*
H8B	0.7347	−0.0425	0.7823	0.147*
C9	0.6722 (17)	−0.0931 (10)	0.6793 (15)	0.127 (7)
H9A	0.7209	−0.0838	0.6343	0.152*
H9B	0.6445	−0.1358	0.6691	0.152*
C10	0.552 (2)	−0.0474 (13)	0.600 (2)	0.172 (11)
H10A	0.5743	−0.0863	0.5698	0.206*
H10B	0.5743	−0.0105	0.5652	0.206*
C11	0.1961 (6)	0.1356 (4)	0.9620 (6)	0.051 (2)
C12	0.2935 (7)	0.1459 (4)	0.9403 (7)	0.0521 (19)
C13	0.3435 (7)	0.2023 (5)	0.9693 (8)	0.061 (2)
C14	0.3456 (7)	0.0975 (5)	0.8923 (8)	0.057 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0437 (7)	0.0506 (8)	0.0532 (8)	0.000	0.000	−0.0009 (7)
Mg1	0.077 (3)	0.067 (3)	0.069 (3)	0.000	0.000	−0.006 (3)
Mg2	0.057 (2)	0.058 (2)	0.055 (2)	0.000	0.000	−0.009 (2)
N1	0.075 (6)	0.090 (7)	0.116 (9)	−0.019 (5)	0.025 (6)	−0.051 (7)
N2	0.044 (4)	0.075 (6)	0.104 (7)	0.008 (4)	0.006 (5)	−0.033 (6)
O1	0.080 (8)	0.071 (7)	0.101 (9)	0.000	0.000	−0.023 (6)
O2	0.078 (5)	0.086 (5)	0.089 (6)	0.005 (4)	0.003 (5)	−0.012 (5)
O3	0.121 (9)	0.138 (9)	0.077 (6)	0.016 (7)	0.026 (6)	0.007 (6)
O4	0.185 (16)	0.072 (7)	0.069 (8)	0.000	0.000	0.007 (6)
O5	0.126 (9)	0.080 (6)	0.103 (8)	0.020 (6)	−0.031 (7)	−0.013 (6)
O6	0.173 (12)	0.117 (9)	0.103 (9)	0.033 (9)	0.043 (9)	0.004 (7)
Cl1	0.130 (6)	0.122 (5)	0.225 (11)	0.000	0.000	0.018 (7)
Cl2	0.115 (5)	0.136 (5)	0.197 (9)	0.000	0.000	0.046 (6)
S1	0.0443 (12)	0.0618 (13)	0.0652 (14)	0.0027 (9)	0.0003 (11)	−0.0202 (12)
S2	0.0471 (12)	0.0464 (11)	0.0757 (15)	0.0005 (8)	0.0012 (12)	−0.0051 (11)
C1	0.092 (9)	0.084 (8)	0.108 (11)	0.010 (7)	−0.009 (9)	−0.006 (8)
C2	0.096 (10)	0.081 (8)	0.117 (11)	0.016 (7)	−0.011 (9)	−0.009 (8)
C3	0.085 (9)	0.116 (12)	0.100 (11)	−0.005 (8)	0.004 (8)	−0.006 (9)
C4	0.103 (11)	0.120 (12)	0.101 (11)	−0.014 (9)	0.026 (9)	−0.002 (10)
C5	0.132 (13)	0.136 (14)	0.081 (9)	−0.036 (10)	0.006 (9)	0.012 (9)
C6	0.21 (2)	0.098 (11)	0.085 (9)	0.031 (14)	−0.032 (16)	0.003 (9)
C7	0.161 (19)	0.104 (12)	0.126 (16)	0.037 (12)	−0.043 (15)	−0.029 (12)
C8	0.121 (15)	0.108 (12)	0.140 (16)	0.038 (11)	0.015 (14)	−0.022 (12)
C9	0.138 (16)	0.110 (13)	0.132 (16)	0.022 (12)	0.044 (14)	−0.013 (11)
C10	0.20 (3)	0.18 (2)	0.135 (18)	0.064 (19)	0.041 (18)	−0.006 (17)
C11	0.046 (4)	0.052 (4)	0.055 (6)	0.007 (4)	−0.005 (4)	0.001 (4)
C12	0.052 (5)	0.049 (4)	0.055 (5)	0.006 (4)	−0.002 (4)	−0.005 (4)
C13	0.053 (5)	0.062 (5)	0.066 (6)	−0.002 (4)	0.004 (5)	−0.017 (5)
C14	0.048 (5)	0.052 (5)	0.072 (6)	0.000 (4)	−0.003 (5)	−0.006 (5)

Geometric parameters (Å, º) top

Ni1—S2ⁱ	2.207 (3)	O6—C10	1.41 (3)
Ni1—S2	2.207 (3)	O6—C9	1.41 (2)
Ni1—S1	2.212 (3)	S1—C11	1.734 (9)
Ni1—S1ⁱ	2.212 (3)	S2—C11	1.708 (9)
Mg1—O3	2.502 (13)	C1—C2	1.45 (2)
Mg1—O3ⁱⁱ	2.502 (13)	C1—H1A	0.9700
Mg1—O1	2.548 (13)	C1—H1B	0.9700
Mg1—N1	2.575 (12)	C2—H2A	0.9700
Mg1—N1ⁱⁱ	2.575 (12)	C2—H2B	0.9700
Mg1—O2ⁱⁱ	2.640 (10)	C3—C4	1.50 (2)
Mg1—O2	2.640 (10)	C3—H3A	0.9700
Mg2—O6ⁱⁱ	2.414 (12)	C3—H3B	0.9700
Mg2—O6	2.414 (12)	C4—H4A	0.9700
Mg2—O5ⁱⁱ	2.478 (11)	C4—H4B	0.9700
Mg2—O5	2.478 (11)	C5—H5A	0.9700
Mg2—N2ⁱⁱ	2.487 (10)	C5—H5B	0.9700
Mg2—N2	2.487 (9)	C6—C7	1.51 (3)
Mg2—O4	2.514 (14)	C6—H6A	0.9700
N1—C13	1.140 (13)	C6—H6B	0.9700
N2—C14	1.128 (13)	C7—H7A	0.9700
O1—C1ⁱⁱ	1.418 (16)	C7—H7B	0.9700
O1—C1	1.418 (16)	C8—C9	1.51 (3)
O2—C3	1.41 (2)	C8—H8A	0.9700
O2—C2	1.420 (15)	C8—H8B	0.9700
O3—C5	1.41 (2)	C9—H9A	0.9700
O3—C4	1.42 (2)	C9—H9B	0.9700
O4—C6	1.42 (2)	C10—H10A	0.9700
O4—C6ⁱⁱ	1.42 (2)	C10—H10B	0.9700
O5—C7	1.40 (2)	C11—C12	1.383 (13)
O5—C8	1.41 (2)

S2ⁱ—Ni1—S2	101.24 (16)	C11—S2—Ni1	85.8 (3)
S2ⁱ—Ni1—S1	175.2 (2)	O1—C1—C2	108.0 (12)
S2—Ni1—S1	78.94 (8)	O1—C1—H1A	110.1
S2ⁱ—Ni1—S1ⁱ	78.94 (8)	C2—C1—H1A	110.1
S2—Ni1—S1ⁱ	175.2 (2)	O1—C1—H1B	110.1
S1—Ni1—S1ⁱ	100.48 (15)	C2—C1—H1B	110.1
O3—Mg1—O3ⁱⁱ	68.8 (6)	H1A—C1—H1B	108.4
O3—Mg1—O1	108.5 (4)	O2—C2—C1	113.8 (12)
O3ⁱⁱ—Mg1—O1	108.5 (4)	O2—C2—H2A	108.8
O3—Mg1—N1	79.2 (4)	C1—C2—H2A	108.8
O3ⁱⁱ—Mg1—N1	120.0 (5)	O2—C2—H2B	108.8
O1—Mg1—N1	129.7 (4)	C1—C2—H2B	108.8
O3—Mg1—N1ⁱⁱ	120.0 (5)	H2A—C2—H2B	107.7
O3ⁱⁱ—Mg1—N1ⁱⁱ	79.2 (4)	O2—C3—C4	105.4 (13)
O1—Mg1—N1ⁱⁱ	129.7 (4)	O2—C3—H3A	110.7
N1—Mg1—N1ⁱⁱ	74.9 (5)	C4—C3—H3A	110.7
O3—Mg1—O2ⁱⁱ	125.9 (4)	O2—C3—H3B	110.7
O3ⁱⁱ—Mg1—O2ⁱⁱ	64.9 (4)	C4—C3—H3B	110.7
O1—Mg1—O2ⁱⁱ	63.8 (2)	H3A—C3—H3B	108.8
N1—Mg1—O2ⁱⁱ	149.6 (4)	O3—C4—C3	114.9 (14)
N1ⁱⁱ—Mg1—O2ⁱⁱ	77.0 (3)	O3—C4—H4A	108.5
O3—Mg1—O2	64.9 (4)	C3—C4—H4A	108.5
O3ⁱⁱ—Mg1—O2	125.9 (4)	O3—C4—H4B	108.5
O1—Mg1—O2	63.8 (2)	C3—C4—H4B	108.5
N1—Mg1—O2	77.0 (3)	H4A—C4—H4B	107.5
N1ⁱⁱ—Mg1—O2	149.6 (4)	C5ⁱⁱ—C5—O3	121.6 (8)
O2ⁱⁱ—Mg1—O2	126.7 (4)	C5ⁱⁱ—C5—H5A	106.9
O6ⁱⁱ—Mg2—O6	67.8 (9)	O3—C5—H5A	106.9
O6ⁱⁱ—Mg2—O5ⁱⁱ	65.7 (5)	C5ⁱⁱ—C5—H5B	106.9
O6—Mg2—O5ⁱⁱ	117.0 (5)	O3—C5—H5B	106.9
O6ⁱⁱ—Mg2—O5	117.0 (5)	H5A—C5—H5B	106.7
O6—Mg2—O5	65.7 (5)	O4—C6—C7	113.9 (16)
O5ⁱⁱ—Mg2—O5	101.9 (6)	O4—C6—H6A	108.8
O6ⁱⁱ—Mg2—N2ⁱⁱ	129.8 (5)	C7—C6—H6A	108.8
O6—Mg2—N2ⁱⁱ	86.9 (5)	O4—C6—H6B	108.8
O5ⁱⁱ—Mg2—N2ⁱⁱ	156.1 (4)	C7—C6—H6B	108.8
O5—Mg2—N2ⁱⁱ	87.0 (3)	H6A—C6—H6B	107.7
O6ⁱⁱ—Mg2—N2	86.9 (5)	O5—C7—C6	104.8 (19)
O6—Mg2—N2	129.8 (5)	O5—C7—H7A	110.8
O5ⁱⁱ—Mg2—N2	87.0 (3)	C6—C7—H7A	110.8
O5—Mg2—N2	156.1 (4)	O5—C7—H7B	110.8
N2ⁱⁱ—Mg2—N2	77.0 (4)	C6—C7—H7B	110.8
O6ⁱⁱ—Mg2—O4	131.1 (4)	H7A—C7—H7B	108.9
O6—Mg2—O4	131.1 (4)	O5—C8—C9	108.1 (17)
O5ⁱⁱ—Mg2—O4	66.1 (4)	O5—C8—H8A	110.1
O5—Mg2—O4	66.1 (4)	C9—C8—H8A	110.1
N2ⁱⁱ—Mg2—O4	98.4 (4)	O5—C8—H8B	110.1
N2—Mg2—O4	98.4 (4)	C9—C8—H8B	110.1
C13—N1—Mg1	157.3 (12)	H8A—C8—H8B	108.4
C14—N2—Mg2	163.5 (10)	O6—C9—C8	100.3 (15)
C1ⁱⁱ—O1—C1	111.5 (14)	O6—C9—H9A	111.7
C1ⁱⁱ—O1—Mg1	119.6 (7)	C8—C9—H9A	111.7
C1—O1—Mg1	119.6 (8)	O6—C9—H9B	111.7
C3—O2—C2	109.9 (13)	C8—C9—H9B	111.7
C3—O2—Mg1	116.1 (9)	H9A—C9—H9B	109.5
C2—O2—Mg1	112.2 (9)	O6—C10—C10ⁱⁱ	116.9 (12)
C5—O3—C4	121.8 (13)	O6—C10—H10A	108.1
C5—O3—Mg1	110.0 (10)	C10ⁱⁱ—C10—H10A	108.1
C4—O3—Mg1	115.4 (10)	O6—C10—H10B	108.1
C6—O4—C6ⁱⁱ	117 (2)	C10ⁱⁱ—C10—H10B	108.1
C6—O4—Mg2	113.4 (13)	H10A—C10—H10B	107.3
C6ⁱⁱ—O4—Mg2	113.4 (13)	C12—C11—S2	125.9 (7)
C7—O5—C8	112.1 (18)	C12—C11—S1	124.6 (7)
C7—O5—Mg2	109.1 (11)	S2—C11—S1	109.4 (5)
C8—O5—Mg2	107.9 (10)	C11—C12—C13	120.9 (8)
C10—O6—C9	105.1 (16)	C11—C12—C14	119.5 (8)
C10—O6—Mg2	119.0 (14)	C13—C12—C14	119.5 (8)
C9—O6—Mg2	120.5 (12)	N1—C13—C12	178.5 (12)
C11—S1—Ni1	85.1 (3)	N2—C14—C12	179.3 (13)

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

Experimental details

Crystal data
Chemical formula	[NiMg₂(C₄N₂S₂)₂(C₁₀H₂₀O₅)₂]Cl₂
M_r	899.11
Crystal system, space group	Orthorhombic, Cmc2₁
Temperature (K)	298
a, b, c (Å)	13.6227 (16), 20.591 (3), 15.148 (2)
V (Å³)	4249 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.41 × 0.32 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.719, 0.783
No. of measured, independent and observed [I > 2σ(I)] reflections	10632, 1979, 1651
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.192, 1.06
No. of reflections	1979
No. of parameters	242
No. of restraints	1
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.1309P)² + 12.7693P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.47
Absolute structure	Flack (1983)
Absolute structure parameter	0.02 (5)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of China.

References

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