catena-Poly[[[diaqua­manganese(II)]-bis­[μ-1,3-bis­(1H-imidazol-1-ylmeth­yl)benzene-κ2N3:N3′]] dinitrate]

Wang, X.-D.; Hou, G.-F.; Yu, Y.-H.; Gao, J.-S.

doi:10.1107/S1600536811039882

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1480

doi:10.1107/S1600536811039882

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catena-Poly[[[diaquamanganese(II)]-bis[μ-1,3-bis(1H-imidazol-1-ylmethyl)benzene-κ²N³:N^3′]] dinitrate]

Xiao-Dan Wang,^a Guang-Feng Hou,^a,^b Ying-Hui Yu ^a,^b and Jin-Sheng Gao ^a,^b ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bEngineering Research Center of Pesticide of Heilongjiang University, Heilongjiang University, Harbin 150050, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 16 September 2011; accepted 28 September 2011; online 5 October 2011)

In the title compound, {[Mn(C₁₄H₁₄N₄)₂(H₂O)₂](NO₃)₂}_n, the Mn^II ion is located on an inversion center and is coordinated by four N atoms from four 1,3-bis(1H-imidazol-1-ylmethyl)benzene (L) ligands and two water molecules in a distorted octahedral geometry. Two L ligands are related by a centre of symmetry and bridge Mn^II ions, forming a positively charged polymeric chain in [101]. Uncoordinated nitrate anions further link these chains into layers parallel to the ac plane via O—H⋯O hydrogen bonds.

Related literature

For details of the synthesis, see: Yang et al. (2006 ). For related structures, see: Dobrzańska et al. (2008 ); Dobrzańska (2009 ); Yao et al. (2008 ).

Experimental

Crystal data

[Mn(C₁₄H₁₄N₄)₂(H₂O)₂](NO₃)₂
M_r = 691.58
Triclinic, $[P \overline 1]$
a = 8.393 (7) Å
b = 9.843 (7) Å
c = 10.634 (7) Å
α = 98.11 (3)°
β = 108.42 (3)°
γ = 98.77 (3)°
V = 806.8 (10) Å³
Z = 1
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 293 K
0.38 × 0.22 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.842, T_max = 0.923
6692 measured reflections
3567 independent reflections
2387 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.124
S = 1.07
3567 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O1	0.85	1.96	2.701 (3)	146
O4—H42⋯O3ⁱ	0.85	2.11	2.800 (3)	138
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (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 global. DOI: 10.1107/S1600536811039882/cv5155sup1.cif

checkCIF report

Comment top

In recent years, much study has been focused on using nitrogen-containing ligands to construct the supramolecular coordination compounds. The reason is that the supramolecular coordination assemblies not only own variety of architectures but also have the potential applications as functional materials. Recently, several supramolecular complexes based on the 1,3-bis(imidazol-1-yl-methyl)-benzene ligand (L) were reported (Dobrzanska et al., 2008; Dobrzanska, 2009; Yao et al., 2008). In this paper, we report the new title compound (I) synthesized by the reaction of 1,3-bis(imidazol-1-yl-methyl)benzene and manganese dinitrate in an aqueous solution, which forms an infinite one-dimensional chain structure.

In (I) (Fig. 1), six-coordinated Mn^II ion locates on an inversion center. Its environment formed by four N atoms and two O atoms has a distorted octahedral geometry. Two ligands L related by centre of symmetry bridge Mn^II ions to form positively charged polymeric chain in [101] (Fig. 2). Uncoordinated nitrate anions link further these chains into layers parallel to ac plane via O—H···O hydrogen bonds (Table 1).

Related literature top

For details of the synthesis, see: Yang et al. (2006). For related structures, see: Dobrzanska et al. (2008); Dobrzanska (2009); Yao et al. (2008).

Experimental top

The 1,3-bis(imidazol-1-yl-methyl)benzene ligand was synthesized following the reference method (Yang et al., 2006). 1,3-Bis(imidazol-1-yl-methyl)benzene (0.2143 g, 1 mmol) and 10 ml (0.1 mol/L) manganese dinitrate aqueous solution were dissolved in 10 ml ethanol. The mixture was stirred at 60 °C for 10 min. The resulting white precipitate was removed. Suitable single crystals were grown by slow evaporation from the mixed solution. White block crystals were obtained in 63 % yield based on manganese.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (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. A portion of the crystal structure of (I) showing the atomic numbering and 50% probability displacement ellipsoids [symmetry codes: (i) 1-x, 1-y, 1-z; (ii) 1+x, y, 1+z; (iii) 2-x, 1-y, 2-z].
	Fig. 2. A portion of the positively charged polymeric chain in (I). C-bound H atoms omitted for clarity.

catena-Poly[[[diaquamanganese(II)]-bis[µ-1,3-bis(1H-imidazol-1- ylmethyl)benzene-κ²N³:N^3']] dinitrate] top

Crystal data top

[Mn(C₁₄H₁₄N₄)₂(H₂O)₂](NO₃)₂	Z = 1
M_r = 691.58	F(000) = 359
Triclinic, P1	D_x = 1.423 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.393 (7) Å	Cell parameters from 4631 reflections
b = 9.843 (7) Å	θ = 3.0–27.4°
c = 10.634 (7) Å	µ = 0.47 mm⁻¹
α = 98.11 (3)°	T = 293 K
β = 108.42 (3)°	Block, colourless
γ = 98.77 (3)°	0.38 × 0.22 × 0.17 mm
V = 806.8 (10) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3567 independent reflections
Radiation source: fine-focus sealed tube	2387 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.842, T_max = 0.923	k = −12→12
6692 measured reflections	l = −12→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0481P)² + 0.2405P] where P = (F_o² + 2F_c²)/3
3567 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Mn(C₁₄H₁₄N₄)₂(H₂O)₂](NO₃)₂	γ = 98.77 (3)°
M_r = 691.58	V = 806.8 (10) Å³
Triclinic, P1	Z = 1
a = 8.393 (7) Å	Mo Kα radiation
b = 9.843 (7) Å	µ = 0.47 mm⁻¹
c = 10.634 (7) Å	T = 293 K
α = 98.11 (3)°	0.38 × 0.22 × 0.17 mm
β = 108.42 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3567 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2387 reflections with I > 2σ(I)
T_min = 0.842, T_max = 0.923	R_int = 0.031
6692 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.07	Δρ_max = 0.23 e Å⁻³
3567 reflections	Δρ_min = −0.31 e Å⁻³
214 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
O1	0.6014 (3)	0.7225 (3)	0.8857 (3)	0.0887 (8)
C1	0.3199 (3)	0.0680 (3)	0.6811 (2)	0.0441 (6)
C2	0.3261 (4)	−0.0279 (3)	0.5759 (3)	0.0540 (7)
H2	0.3826	−0.1010	0.5939	0.065*
C3	0.2480 (4)	−0.0154 (4)	0.4432 (3)	0.0663 (8)
H3	0.2505	−0.0810	0.3722	0.080*
C4	0.1670 (4)	0.0941 (3)	0.4168 (3)	0.0610 (8)
H4	0.1166	0.1027	0.3276	0.073*
C5	0.1594 (4)	0.1912 (3)	0.5202 (3)	0.0511 (7)
C6	0.2370 (3)	0.1769 (3)	0.6523 (2)	0.0485 (6)
H6	0.2331	0.2419	0.7232	0.058*
C7	0.0640 (4)	0.3091 (4)	0.4925 (3)	0.0651 (9)
H7A	−0.0582	0.2696	0.4525	0.078*
H7B	0.0840	0.3715	0.5776	0.078*
C8	0.0300 (4)	0.3810 (3)	0.2698 (3)	0.0557 (7)
H8	−0.0755	0.3206	0.2225	0.067*
C9	0.2586 (4)	0.5332 (4)	0.3180 (3)	0.0655 (8)
H9	0.3438	0.6005	0.3103	0.079*
C10	0.2641 (4)	0.4879 (4)	0.4333 (3)	0.0681 (9)
H10	0.3512	0.5174	0.5173	0.082*
C11	0.4068 (4)	0.0573 (3)	0.8265 (3)	0.0504 (6)
H11A	0.3511	0.1026	0.8827	0.061*
H11B	0.3933	−0.0409	0.8329	0.061*
C12	0.6573 (4)	0.2604 (3)	0.9098 (3)	0.0478 (6)
H12	0.5922	0.3292	0.9070	0.057*
C13	0.8680 (4)	0.1583 (3)	0.9358 (3)	0.0524 (7)
H13	0.9792	0.1431	0.9551	0.063*
C14	0.7247 (4)	0.0567 (3)	0.8936 (3)	0.0511 (7)
H14	0.7188	−0.0397	0.8784	0.061*
N1	0.5897 (3)	0.1223 (2)	0.87739 (19)	0.0428 (5)
N2	0.8254 (3)	0.2879 (2)	0.9461 (2)	0.0457 (5)
N3	0.1169 (3)	0.3907 (3)	0.4016 (2)	0.0530 (6)
N4	0.1113 (3)	0.4668 (2)	0.2149 (2)	0.0531 (6)
N5	0.4591 (3)	0.6495 (3)	0.8143 (3)	0.0552 (6)
O2	0.3562 (4)	0.6999 (3)	0.7364 (3)	0.1026 (9)
O3	0.4241 (3)	0.5255 (2)	0.8242 (3)	0.0767 (7)
O4	0.8056 (3)	0.5934 (2)	1.0595 (2)	0.0590 (5)
H41	0.7729	0.6628	1.0273	0.089*
H42	0.7398	0.5217	1.0653	0.089*
Mn1	1.0000	0.5000	1.0000	0.04181 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0743 (17)	0.0536 (14)	0.117 (2)	0.0082 (13)	0.0038 (16)	0.0225 (14)
C1	0.0396 (14)	0.0493 (15)	0.0368 (13)	−0.0001 (11)	0.0066 (11)	0.0134 (11)
C2	0.0550 (17)	0.0573 (18)	0.0498 (15)	0.0138 (14)	0.0155 (14)	0.0146 (13)
C3	0.079 (2)	0.076 (2)	0.0404 (15)	0.0232 (19)	0.0160 (15)	0.0071 (14)
C4	0.065 (2)	0.081 (2)	0.0344 (14)	0.0198 (17)	0.0108 (13)	0.0167 (14)
C5	0.0486 (16)	0.0669 (19)	0.0402 (13)	0.0150 (14)	0.0132 (12)	0.0205 (13)
C6	0.0516 (16)	0.0531 (16)	0.0367 (13)	0.0042 (13)	0.0131 (12)	0.0087 (11)
C7	0.066 (2)	0.088 (2)	0.0552 (17)	0.0299 (18)	0.0248 (16)	0.0338 (17)
C8	0.0487 (16)	0.0636 (19)	0.0472 (15)	0.0081 (14)	0.0037 (13)	0.0211 (13)
C9	0.0556 (19)	0.072 (2)	0.0518 (17)	−0.0038 (16)	0.0010 (14)	0.0159 (15)
C10	0.059 (2)	0.084 (2)	0.0426 (16)	0.0064 (18)	−0.0037 (14)	0.0134 (15)
C11	0.0515 (16)	0.0490 (16)	0.0394 (13)	−0.0061 (13)	0.0056 (12)	0.0140 (11)
C12	0.0471 (16)	0.0419 (15)	0.0471 (14)	0.0089 (12)	0.0047 (12)	0.0128 (11)
C13	0.0520 (17)	0.0491 (17)	0.0521 (15)	0.0151 (14)	0.0089 (13)	0.0140 (13)
C14	0.0639 (19)	0.0358 (14)	0.0477 (15)	0.0105 (13)	0.0101 (14)	0.0110 (11)
N1	0.0467 (12)	0.0379 (12)	0.0332 (10)	−0.0003 (10)	0.0026 (9)	0.0102 (8)
N2	0.0422 (13)	0.0405 (12)	0.0439 (12)	0.0038 (10)	0.0022 (10)	0.0098 (9)
N3	0.0522 (14)	0.0656 (16)	0.0412 (12)	0.0190 (12)	0.0084 (11)	0.0211 (11)
N4	0.0503 (14)	0.0571 (15)	0.0429 (12)	0.0083 (12)	0.0022 (10)	0.0172 (11)
N5	0.0592 (16)	0.0522 (15)	0.0580 (14)	0.0208 (13)	0.0195 (13)	0.0157 (12)
O2	0.098 (2)	0.101 (2)	0.0990 (19)	0.0415 (18)	0.0018 (16)	0.0411 (17)
O3	0.0809 (17)	0.0468 (14)	0.1141 (19)	0.0123 (12)	0.0465 (15)	0.0250 (12)
O4	0.0575 (12)	0.0531 (12)	0.0705 (13)	0.0177 (10)	0.0226 (11)	0.0174 (10)
Mn1	0.0392 (3)	0.0404 (3)	0.0387 (3)	0.0059 (2)	0.0039 (2)	0.0101 (2)

Geometric parameters (Å, º) top

O1—N5	1.237 (4)	C10—H10	0.9300
C1—C2	1.377 (4)	C11—N1	1.462 (4)
C1—C6	1.383 (4)	C11—H11A	0.9700
C1—C11	1.513 (3)	C11—H11B	0.9700
C2—C3	1.387 (4)	C12—N2	1.313 (3)
C2—H2	0.9300	C12—N1	1.340 (3)
C3—C4	1.375 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.347 (4)
C4—C5	1.376 (4)	C13—N2	1.376 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.387 (4)	C14—N1	1.364 (3)
C5—C7	1.518 (4)	C14—H14	0.9300
C6—H6	0.9300	N2—Mn1	2.243 (3)
C7—N3	1.469 (3)	N4—Mn1ⁱ	2.270 (2)
C7—H7A	0.9700	N5—O2	1.214 (3)
C7—H7B	0.9700	N5—O3	1.238 (3)
C8—N4	1.317 (4)	O4—Mn1	2.203 (2)
C8—N3	1.342 (3)	O4—H41	0.8499
C8—H8	0.9300	O4—H42	0.8501
C9—C10	1.352 (4)	Mn1—O4ⁱⁱ	2.203 (2)
C9—N4	1.361 (4)	Mn1—N2ⁱⁱ	2.243 (3)
C9—H9	0.9300	Mn1—N4ⁱⁱⁱ	2.270 (2)
C10—N3	1.357 (4)	Mn1—N4^iv	2.270 (2)

C2—C1—C6	119.1 (2)	N1—C12—H12	123.7
C2—C1—C11	120.7 (2)	C14—C13—N2	109.9 (3)
C6—C1—C11	120.2 (2)	C14—C13—H13	125.1
C1—C2—C3	120.0 (3)	N2—C13—H13	125.1
C1—C2—H2	120.0	C13—C14—N1	106.7 (2)
C3—C2—H2	120.0	C13—C14—H14	126.6
C4—C3—C2	120.0 (3)	N1—C14—H14	126.6
C4—C3—H3	120.0	C12—N1—C14	106.3 (2)
C2—C3—H3	120.0	C12—N1—C11	126.1 (2)
C3—C4—C5	121.0 (3)	C14—N1—C11	127.5 (2)
C3—C4—H4	119.5	C12—N2—C13	104.6 (2)
C5—C4—H4	119.5	C12—N2—Mn1	127.07 (18)
C4—C5—C6	118.4 (3)	C13—N2—Mn1	128.24 (19)
C4—C5—C7	121.6 (2)	C8—N3—C10	106.6 (2)
C6—C5—C7	120.0 (3)	C8—N3—C7	126.4 (3)
C1—C6—C5	121.5 (2)	C10—N3—C7	126.9 (2)
C1—C6—H6	119.2	C8—N4—C9	104.3 (2)
C5—C6—H6	119.2	C8—N4—Mn1ⁱ	124.1 (2)
N3—C7—C5	112.9 (2)	C9—N4—Mn1ⁱ	131.3 (2)
N3—C7—H7A	109.0	O2—N5—O1	119.9 (3)
C5—C7—H7A	109.0	O2—N5—O3	121.1 (3)
N3—C7—H7B	109.0	O1—N5—O3	119.0 (3)
C5—C7—H7B	109.0	Mn1—O4—H41	119.7
H7A—C7—H7B	107.8	Mn1—O4—H42	102.0
N4—C8—N3	112.3 (3)	H41—O4—H42	125.4
N4—C8—H8	123.8	O4ⁱⁱ—Mn1—O4	180.000 (1)
N3—C8—H8	123.8	O4ⁱⁱ—Mn1—N2	90.62 (9)
C10—C9—N4	110.8 (3)	O4—Mn1—N2	89.38 (9)
C10—C9—H9	124.6	O4ⁱⁱ—Mn1—N2ⁱⁱ	89.38 (9)
N4—C9—H9	124.6	O4—Mn1—N2ⁱⁱ	90.62 (9)
C9—C10—N3	106.0 (3)	N2—Mn1—N2ⁱⁱ	180.00 (11)
C9—C10—H10	127.0	O4ⁱⁱ—Mn1—N4ⁱⁱⁱ	91.51 (9)
N3—C10—H10	127.0	O4—Mn1—N4ⁱⁱⁱ	88.49 (9)
N1—C11—C1	112.2 (2)	N2—Mn1—N4ⁱⁱⁱ	88.86 (9)
N1—C11—H11A	109.2	N2ⁱⁱ—Mn1—N4ⁱⁱⁱ	91.14 (9)
C1—C11—H11A	109.2	O4ⁱⁱ—Mn1—N4^iv	88.49 (9)
N1—C11—H11B	109.2	O4—Mn1—N4^iv	91.51 (9)
C1—C11—H11B	109.2	N2—Mn1—N4^iv	91.14 (9)
H11A—C11—H11B	107.9	N2ⁱⁱ—Mn1—N4^iv	88.86 (9)
N2—C12—N1	112.6 (2)	N4ⁱⁱⁱ—Mn1—N4^iv	180.000 (1)
N2—C12—H12	123.7

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O1	0.85	1.96	2.701 (3)	146
O4—H42···O3^v	0.85	2.11	2.800 (3)	138

Symmetry code: (v) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₄H₁₄N₄)₂(H₂O)₂](NO₃)₂
M_r	691.58
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.393 (7), 9.843 (7), 10.634 (7)
α, β, γ (°)	98.11 (3), 108.42 (3), 98.77 (3)
V (Å³)	806.8 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.38 × 0.22 × 0.17

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.842, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	6692, 3567, 2387
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.124, 1.07
No. of reflections	3567
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.31

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (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—H41···O1	0.85	1.96	2.701 (3)	145.7
O4—H42···O3ⁱ	0.85	2.11	2.800 (3)	137.6

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

The authors thank the Project of Innovation Service Platform of Heilongjiang Province (grant No. PG09J001) and Heilongjiang University for supporting this work.

References

Dobrzańska, L. (2009). Acta Cryst. E65, m1326–m1327. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dobrzańska, L., Kleinhans, D. J. & Barbour, L. J. (2008). New J. Chem. 32, 813–819 Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. 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
Yang, J., Ma, J.-F., Liu, Y.-Y., Ma, J.-C., Jia, H.-Q. & Hu, N.-H. (2006). Eur. J. Inorg. Chem. pp. 1208–1215. Web of Science CSD CrossRef Google Scholar
Yao, J., Xing, Y.-Y., Xu, Y.-Y., Meng, Q.-J., Gao, S. & Lu, C.-S. (2008). Wuji Huaxue Xuebao, 24, 1636–1642. CAS Google Scholar

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