Bis(μ-2-{[2-(1,3-benzothia­zol-2-yl)hydrazinyl­idene]meth­yl}-6-meth­oxy­phenolato)bis­[dinitratodysprosium(III)] methanol disolvate

Xu, X.; Ding, S.; Shen, S.; Tang, J.; Liu, Z.

doi:10.1107/S1600536811019118

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m796-m797

doi:10.1107/S1600536811019118

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Bis(μ-2-{[2-(1,3-benzothiazol-2-yl)hydrazinylidene]methyl}-6-methoxyphenolato)bis[dinitratodysprosium(III)] methanol disolvate

Xuebin Xu,^a Shuai Ding,^a Si Shen,^b Jinkui Tang ^b and Zhiliang Liu ^a ^*

^aCollege of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, People's Republic of China, and ^bState Key Laboratory of Rare Earth Resource Utilization, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of China.
^*Correspondence e-mail: cezlliu@imu.edu.cn

(Received 23 March 2011; accepted 19 May 2011; online 25 May 2011)

In the centrosymmetric dinuclear title compound, [Dy₂(C₁₅H₁₂N₃O₂S)₂(NO₃)₄]·2CH₃OH, the two Dy^III atoms are coordinated by two deprotonated 2-{[2-(1,3-benzothiazol-2-yl)hydrazinylidene]methyl}-6-methoxyphenol ligands and four nitrate ions, all of which are chelating. The crystal packing is stabilized by intermolecular N—H⋯O hydrogen bonds and weak O—H⋯O interactions, forming a two-dimensional network parallel to (010).

Related literature

For applications of dysprosium complexes in data storage and processing, see: Lin et al. (2010 ). For the preparation of the 2-{[2-(1,3-benzothiazol-2-yl)hydrazinylidene]methyl}-6-methoxyphenol ligand, see: Patil et al. (2009 ). For related structures, see: Lin & Hong (2009 ); Lin et al. (2008 ); Xu et al. (2010 ).

Experimental

Crystal data

[Dy₂(C₁₅H₁₂N₃O₂S)₂(NO₃)₄]·2CH₄O
M_r = 1233.82
Triclinic, $[P \overline 1]$
a = 9.6191 (6) Å
b = 10.1002 (7) Å
c = 11.6151 (8) Å
α = 112.045 (1)°
β = 105.065 (1)°
γ = 93.154 (1)°
V = 995.23 (12) Å³
Z = 1
Mo Kα radiation
μ = 3.92 mm⁻¹
T = 159 K
0.20 × 0.10 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002 ) T_min = 0.631, T_max = 0.676
5083 measured reflections
3502 independent reflections
3162 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.057
S = 1.07
3502 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Selected bond lengths (Å)

Dy1—O2	2.280 (3)
Dy1—O2ⁱ	2.374 (2)
Dy1—O1ⁱ	2.394 (3)
Dy1—O4	2.422 (3)
Dy1—O3	2.433 (3)
Dy1—N4	2.461 (3)
Dy1—O6	2.471 (3)
Dy1—N5	2.494 (3)
Dy1—O8	2.530 (3)
Symmetry code: (i) -x+1, -y, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9A⋯O3ⁱⁱ	0.84	2.64	3.206 (4)	126
O9—H9A⋯O8ⁱⁱⁱ	0.84	2.24	3.049 (4)	161
N9—H9⋯O9^iv	0.88	1.91	2.751 (4)	160
Symmetry codes: (ii) x, y, z-1; (iii) -x+1, -y, -z+1; (iv) -x, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ) and XP (Siemens, 1994 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019118/jj2083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019118/jj2083Isup2.hkl

checkCIF report

Comment top

Dysprosium complexes continue to attract significant attention because of their potential applications in data storage and processing (Lin et al. 2010). In order to explore the relationship between these applications and their structures, a series of dinuclear dysprosium coordination compounds have been structural characterized (Lin et al. 2008; Xu et al. 2010). In support of our continued research in this area, we report here a new dinuclear dysprosium complex, [Dy₂(C₁₅H₁₂N₃O₂S)₂(NO₃)₄].CH₃OH.

In the title compound the asymmetric unit consists of one Dy^III ion, one deprotonated 2-[(benzothiazol-2-yl)hydrazonomethyl]-6-methoxyphenol ligand and two nitrate ions (Fig. 1). The centrosymmetric dinuclear complex is composed of two nine-coordinate Dy^III ions bridged by phenoxo groups (O2, O2a) from the ligands with a Dy1—O2—Dy1a angle of 106.041 (100) ° and a Dy···Dy distance equal to 3.7184 (3) Å. The central core Dy₂O₂ appears to be nearly rhombic with the two Dy—O2 distances being 2.37 Å and 2.28 Å, respectively. Crystal packing is stabiized by N—H···O hydrogen bonds and weak O—H···O intermolecular interactions forming a two-dimensional network (Fig. 2).

Related literature top

For applications of dysprosium complexes in data storage and processing, see: Lin et al. (2010). For the preparation of the 2-[(benzothiazol-2-yl)hydrazonomethyl]-6-methoxyphenol ligand, see: Patil et al. (2009). For related structures, see: Lin & Hong (2009); Lin et al. (2008); Xu et al. (2010).

Experimental top

A mixture of Dy(NO₃)₃.6H₂O (0.1 mmol), 2-hydrazino benzothiazole (0.1 mmol), 2-hydroxy-3-methoxy-5-((4-methoxyphenyl)diazenyl)benzaldehyde (0.1 mmol), methanol (10 ml), Et₃N (0.3 mmol) was sealed in a glass vessel (20 ml, capacity) and the solution was heated at 363 K for 1 h under autogenous pressure. After the mixture was allowed to cool to room temperature, yellow block single crystals were isolated from the vessel.

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006) and XP (Siemens, 1994); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.
	Fig. 2. Packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Bis(µ-2-{[2-(1,3-benzothiazol-2-yl)hydrazinylidene]methyl}-6- methoxyphenolato)bis[dinitratodysprosium(III)] methanol disolvate top

Crystal data top

[Dy₂(C₁₅H₁₂N₃O₂S)₂(NO₃)₄]·2CH₄O	Z = 1
M_r = 1233.82	F(000) = 602
Triclinic, P1	D_x = 2.059 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6191 (6) Å	Cell parameters from 3776 reflections
b = 10.1002 (7) Å	θ = 2.3–25.1°
c = 11.6151 (8) Å	µ = 3.92 mm⁻¹
α = 112.045 (1)°	T = 159 K
β = 105.065 (1)°	Block, yellow
γ = 93.154 (1)°	0.20 × 0.10 × 0.10 mm
V = 995.23 (12) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3502 independent reflections
Radiation source: rotating anode	3162 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.016
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.1°, θ_min = 2.0°
ω and ϕ scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	k = −12→7
T_min = 0.631, T_max = 0.676	l = −13→13
5083 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0289P)² + 0.127P] where P = (F_o² + 2F_c²)/3
3502 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Dy₂(C₁₅H₁₂N₃O₂S)₂(NO₃)₄]·2CH₄O	γ = 93.154 (1)°
M_r = 1233.82	V = 995.23 (12) Å³
Triclinic, P1	Z = 1
a = 9.6191 (6) Å	Mo Kα radiation
b = 10.1002 (7) Å	µ = 3.92 mm⁻¹
c = 11.6151 (8) Å	T = 159 K
α = 112.045 (1)°	0.20 × 0.10 × 0.10 mm
β = 105.065 (1)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3502 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	3162 reflections with I > 2σ(I)
T_min = 0.631, T_max = 0.676	R_int = 0.016
5083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.07	Δρ_max = 0.83 e Å⁻³
3502 reflections	Δρ_min = −0.51 e Å⁻³
292 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	0.5488 (5)	−0.1481 (6)	1.3423 (4)	0.0419 (12)
H1A	0.4829	−0.0989	1.3895	0.063*
H1B	0.6488	−0.0946	1.3876	0.063*
H1C	0.5453	−0.2468	1.3387	0.063*
C2	0.3550 (4)	−0.2085 (4)	1.1420 (4)	0.0262 (9)
C3	0.2744 (5)	−0.3007 (5)	1.1704 (4)	0.0328 (10)
H3	0.3194	−0.3323	1.2363	0.039*
C4	0.1277 (5)	−0.3481 (5)	1.1034 (4)	0.0349 (10)
H4	0.0711	−0.4143	1.1208	0.042*
C5	0.0654 (4)	−0.2974 (5)	1.0113 (4)	0.0314 (10)
H5	−0.0365	−0.3263	0.9677	0.038*
C6	0.1455 (4)	−0.2054 (4)	0.9789 (4)	0.0259 (9)
C7	0.2972 (4)	−0.1615 (4)	1.0421 (4)	0.0237 (8)
C8	0.0613 (4)	−0.1613 (5)	0.8805 (4)	0.0308 (10)
H8	−0.0395	−0.2025	0.8423	0.037*
C9	0.0364 (4)	0.0701 (5)	0.7244 (4)	0.0285 (9)
C10	0.1564 (4)	0.2767 (4)	0.7467 (4)	0.0265 (9)
C11	0.2636 (4)	0.3998 (5)	0.7988 (4)	0.0309 (10)
H11	0.3530	0.4075	0.8617	0.037*
C12	0.2378 (5)	0.5099 (5)	0.7573 (4)	0.0335 (10)
H12	0.3112	0.5930	0.7904	0.040*
C13	0.1059 (5)	0.5011 (5)	0.6680 (4)	0.0354 (10)
H13	0.0902	0.5791	0.6421	0.042*
C14	−0.0026 (5)	0.3818 (5)	0.6163 (4)	0.0335 (10)
H14	−0.0930	0.3764	0.5557	0.040*
C15	0.0251 (4)	0.2701 (5)	0.6558 (4)	0.0284 (9)
C16	0.2951 (6)	0.3287 (6)	0.4354 (5)	0.0540 (14)
H16A	0.2585	0.3862	0.3858	0.081*
H16C	0.3978	0.3682	0.4862	0.081*
H16B	0.2374	0.3326	0.4945	0.081*
Dy1	0.358298 (18)	0.05304 (2)	0.890365 (17)	0.02346 (8)
N4	0.1097 (3)	−0.0726 (4)	0.8405 (3)	0.0283 (8)
N5	0.1632 (3)	0.1587 (4)	0.7829 (3)	0.0274 (8)
N6	0.3542 (4)	0.3093 (4)	1.1063 (3)	0.0345 (9)
N7	0.3601 (4)	−0.1898 (4)	0.6517 (3)	0.0327 (8)
N9	0.0038 (3)	−0.0478 (4)	0.7456 (3)	0.0327 (8)
H9	−0.0802	−0.1070	0.7020	0.039*
O1	0.5034 (3)	−0.1543 (3)	1.2102 (3)	0.0291 (6)
O2	0.3863 (3)	−0.0823 (3)	1.0113 (2)	0.0249 (6)
O3	0.2717 (3)	0.1897 (3)	1.0724 (3)	0.0340 (7)
O4	0.4335 (3)	0.3079 (3)	1.0330 (3)	0.0337 (7)
O5	0.3585 (4)	0.4152 (4)	1.2012 (3)	0.0574 (10)
O6	0.2613 (3)	−0.1127 (3)	0.6575 (3)	0.0371 (7)
O7	0.3620 (4)	−0.2850 (4)	0.5512 (3)	0.0580 (10)
O8	0.4579 (3)	−0.1600 (3)	0.7589 (3)	0.0416 (8)
O9	0.2828 (3)	0.1836 (4)	0.3486 (3)	0.0452 (8)
H9A	0.3398	0.1790	0.3038	0.068*
S1	−0.09430 (11)	0.11034 (12)	0.61321 (10)	0.0315 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.033 (2)	0.062 (3)	0.028 (2)	0.002 (2)	0.0030 (19)	0.020 (2)
C2	0.021 (2)	0.029 (2)	0.027 (2)	0.0045 (17)	0.0058 (17)	0.0110 (18)
C3	0.036 (2)	0.029 (2)	0.033 (2)	0.006 (2)	0.0075 (19)	0.014 (2)
C4	0.033 (2)	0.033 (2)	0.041 (3)	0.002 (2)	0.011 (2)	0.017 (2)
C5	0.022 (2)	0.035 (2)	0.034 (2)	0.0027 (18)	0.0075 (18)	0.011 (2)
C6	0.0188 (19)	0.028 (2)	0.030 (2)	0.0037 (17)	0.0051 (17)	0.0118 (18)
C7	0.0183 (19)	0.022 (2)	0.028 (2)	0.0031 (16)	0.0038 (16)	0.0095 (18)
C8	0.016 (2)	0.037 (3)	0.033 (2)	0.0030 (18)	0.0006 (17)	0.013 (2)
C9	0.019 (2)	0.037 (2)	0.028 (2)	0.0086 (18)	0.0036 (17)	0.013 (2)
C10	0.023 (2)	0.032 (2)	0.024 (2)	0.0070 (18)	0.0049 (17)	0.0117 (18)
C11	0.022 (2)	0.039 (3)	0.030 (2)	0.0060 (19)	0.0039 (17)	0.014 (2)
C12	0.029 (2)	0.035 (2)	0.032 (2)	0.003 (2)	0.0046 (19)	0.012 (2)
C13	0.039 (2)	0.039 (3)	0.031 (2)	0.011 (2)	0.006 (2)	0.019 (2)
C14	0.031 (2)	0.042 (3)	0.028 (2)	0.012 (2)	0.0021 (19)	0.019 (2)
C15	0.020 (2)	0.038 (2)	0.022 (2)	0.0059 (18)	0.0028 (16)	0.0086 (19)
C16	0.043 (3)	0.069 (4)	0.044 (3)	0.009 (3)	0.011 (2)	0.018 (3)
Dy1	0.01390 (10)	0.03118 (12)	0.02375 (11)	0.00321 (8)	0.00021 (7)	0.01318 (9)
N4	0.0175 (16)	0.033 (2)	0.0301 (18)	−0.0005 (15)	−0.0019 (14)	0.0156 (16)
N5	0.0207 (17)	0.0310 (19)	0.0281 (18)	0.0054 (15)	0.0046 (14)	0.0110 (16)
N6	0.033 (2)	0.039 (2)	0.029 (2)	0.0144 (18)	0.0035 (17)	0.0152 (19)
N7	0.0199 (18)	0.036 (2)	0.031 (2)	0.0019 (16)	−0.0010 (15)	0.0067 (18)
N9	0.0144 (16)	0.045 (2)	0.0347 (19)	−0.0018 (16)	−0.0072 (14)	0.0229 (18)
O1	0.0195 (13)	0.0415 (17)	0.0277 (15)	0.0034 (13)	0.0010 (11)	0.0199 (14)
O2	0.0146 (13)	0.0316 (16)	0.0279 (14)	0.0016 (12)	0.0007 (11)	0.0156 (13)
O3	0.0291 (16)	0.0430 (19)	0.0312 (16)	0.0091 (15)	0.0063 (13)	0.0177 (15)
O4	0.0285 (15)	0.0393 (18)	0.0298 (15)	0.0044 (14)	0.0036 (13)	0.0138 (14)
O5	0.086 (3)	0.041 (2)	0.041 (2)	0.021 (2)	0.0250 (19)	0.0073 (18)
O6	0.0229 (15)	0.0449 (19)	0.0318 (16)	0.0119 (14)	−0.0016 (13)	0.0087 (15)
O7	0.0373 (19)	0.066 (3)	0.037 (2)	0.0132 (18)	−0.0008 (16)	−0.0066 (19)
O8	0.0351 (17)	0.0463 (19)	0.0321 (16)	0.0152 (15)	−0.0033 (14)	0.0117 (15)
O9	0.0258 (17)	0.057 (2)	0.046 (2)	−0.0010 (16)	0.0079 (14)	0.0163 (18)
S1	0.0212 (5)	0.0388 (6)	0.0302 (5)	0.0037 (5)	−0.0020 (4)	0.0161 (5)

Geometric parameters (Å, º) top

C1—O1	1.459 (5)	C13—H13	0.9500
C1—H1A	0.9800	C14—C15	1.384 (6)
C1—H1B	0.9800	C14—H14	0.9500
C1—H1C	0.9800	C15—S1	1.752 (4)
C2—C3	1.364 (6)	C16—O9	1.410 (6)
C2—O1	1.402 (4)	C16—H16A	0.9800
C2—C7	1.410 (5)	C16—H16C	0.9800
C3—C4	1.379 (6)	C16—H16B	0.9800
C3—H3	0.9500	Dy1—O2	2.280 (3)
C4—C5	1.370 (6)	Dy1—O2ⁱ	2.374 (2)
C4—H4	0.9500	Dy1—O1ⁱ	2.394 (3)
C5—C6	1.390 (5)	Dy1—O4	2.422 (3)
C5—H5	0.9500	Dy1—O3	2.433 (3)
C6—C7	1.412 (5)	Dy1—N4	2.461 (3)
C6—C8	1.451 (5)	Dy1—O6	2.471 (3)
C7—O2	1.342 (4)	Dy1—N5	2.494 (3)
C8—N4	1.270 (5)	Dy1—O8	2.530 (3)
C8—H8	0.9500	Dy1—Dy1ⁱ	3.7184 (4)
C9—N5	1.320 (5)	N4—N9	1.402 (4)
C9—N9	1.340 (5)	N6—O5	1.203 (5)
C9—S1	1.738 (4)	N6—O3	1.273 (5)
C10—C11	1.395 (6)	N6—O4	1.279 (4)
C10—C15	1.399 (5)	N7—O7	1.208 (5)
C10—N5	1.405 (5)	N7—O6	1.261 (4)
C11—C12	1.379 (6)	N7—O8	1.266 (4)
C11—H11	0.9500	N9—H9	0.8800
C12—C13	1.388 (6)	O1—Dy1ⁱ	2.394 (3)
C12—H12	0.9500	O2—Dy1ⁱ	2.374 (2)
C13—C14	1.376 (6)	O9—H9A	0.8400

O1—C1—H1A	109.5	O4—Dy1—O3	52.63 (10)
O1—C1—H1B	109.5	O2—Dy1—N4	75.53 (10)
H1A—C1—H1B	109.5	O2ⁱ—Dy1—N4	149.07 (10)
O1—C1—H1C	109.5	O1ⁱ—Dy1—N4	138.80 (10)
H1A—C1—H1C	109.5	O4—Dy1—N4	121.11 (11)
H1B—C1—H1C	109.5	O3—Dy1—N4	74.17 (11)
C3—C2—O1	122.0 (4)	O2—Dy1—O6	108.45 (10)
C3—C2—C7	123.2 (4)	O2ⁱ—Dy1—O6	116.45 (9)
O1—C2—C7	114.8 (3)	O1ⁱ—Dy1—O6	76.95 (10)
C2—C3—C4	120.1 (4)	O4—Dy1—O6	141.79 (10)
C2—C3—H3	120.0	O3—Dy1—O6	139.92 (10)
C4—C3—H3	120.0	N4—Dy1—O6	69.16 (10)
C5—C4—C3	118.5 (4)	O2—Dy1—N5	139.17 (10)
C5—C4—H4	120.8	O2ⁱ—Dy1—N5	144.17 (10)
C3—C4—H4	120.8	O1ⁱ—Dy1—N5	81.46 (10)
C4—C5—C6	122.6 (4)	O4—Dy1—N5	79.22 (10)
C4—C5—H5	118.7	O3—Dy1—N5	79.08 (10)
C6—C5—H5	118.7	N4—Dy1—N5	66.52 (11)
C5—C6—C7	119.6 (4)	O6—Dy1—N5	72.05 (10)
C5—C6—C8	115.0 (4)	O2—Dy1—O8	77.32 (10)
C7—C6—C8	125.3 (4)	O2ⁱ—Dy1—O8	70.22 (9)
O2—C7—C2	119.8 (3)	O1ⁱ—Dy1—O8	76.42 (10)
O2—C7—C6	124.3 (3)	O4—Dy1—O8	140.65 (10)
C2—C7—C6	115.8 (3)	O3—Dy1—O8	153.86 (10)
N4—C8—C6	126.1 (4)	N4—Dy1—O8	98.23 (11)
N4—C8—H8	117.0	O6—Dy1—O8	50.52 (9)
C6—C8—H8	117.0	N5—Dy1—O8	121.51 (10)
N5—C9—N9	123.9 (4)	O2—Dy1—Dy1ⁱ	37.86 (6)
N5—C9—S1	117.3 (3)	O2ⁱ—Dy1—Dy1ⁱ	36.10 (6)
N9—C9—S1	118.8 (3)	O1ⁱ—Dy1—Dy1ⁱ	103.10 (6)
C11—C10—C15	119.0 (4)	O4—Dy1—Dy1ⁱ	92.27 (7)
C11—C10—N5	125.8 (3)	O3—Dy1—Dy1ⁱ	90.23 (7)
C15—C10—N5	115.2 (4)	N4—Dy1—Dy1ⁱ	113.24 (8)
C12—C11—C10	118.9 (4)	O6—Dy1—Dy1ⁱ	118.59 (7)
C12—C11—H11	120.6	N5—Dy1—Dy1ⁱ	169.00 (8)
C10—C11—H11	120.6	O8—Dy1—Dy1ⁱ	69.47 (6)
C11—C12—C13	120.9 (4)	C8—N4—N9	114.2 (3)
C11—C12—H12	119.5	C8—N4—Dy1	131.6 (3)
C13—C12—H12	119.5	N9—N4—Dy1	114.1 (2)
C14—C13—C12	121.5 (4)	C9—N5—C10	109.1 (3)
C14—C13—H13	119.3	C9—N5—Dy1	113.1 (3)
C12—C13—H13	119.3	C10—N5—Dy1	136.6 (2)
C13—C14—C15	117.4 (4)	O5—N6—O3	122.4 (4)
C13—C14—H14	121.3	O5—N6—O4	122.6 (4)
C15—C14—H14	121.3	O3—N6—O4	115.0 (3)
C14—C15—C10	122.3 (4)	O7—N7—O6	122.5 (4)
C14—C15—S1	127.6 (3)	O7—N7—O8	122.2 (4)
C10—C15—S1	109.9 (3)	O6—N7—O8	115.2 (3)
O9—C16—H16A	109.5	C9—N9—N4	117.0 (3)
O9—C16—H16C	109.5	C9—N9—H9	121.5
H16A—C16—H16C	109.5	N4—N9—H9	121.5
O9—C16—H16B	109.5	C2—O1—C1	114.9 (3)
H16A—C16—H16B	109.5	C2—O1—Dy1ⁱ	116.7 (2)
H16C—C16—H16B	109.5	C1—O1—Dy1ⁱ	127.7 (2)
O2—Dy1—O2ⁱ	73.96 (10)	C7—O2—Dy1	136.2 (2)
O2—Dy1—O1ⁱ	139.27 (9)	C7—O2—Dy1ⁱ	117.7 (2)
O2ⁱ—Dy1—O1ⁱ	68.12 (9)	Dy1—O2—Dy1ⁱ	106.04 (10)
O2—Dy1—O4	109.76 (9)	N6—O3—Dy1	95.9 (2)
O2ⁱ—Dy1—O4	74.78 (9)	N6—O4—Dy1	96.3 (2)
O1ⁱ—Dy1—O4	74.29 (10)	N7—O6—Dy1	98.6 (2)
O2—Dy1—O3	76.56 (10)	N7—O8—Dy1	95.6 (2)
O2ⁱ—Dy1—O3	103.27 (9)	C16—O9—H9A	109.5
O1ⁱ—Dy1—O3	125.83 (10)	C9—S1—C15	88.36 (19)

O1—C2—C3—C4	178.1 (4)	C8—N4—N9—C9	162.8 (4)
C7—C2—C3—C4	−2.5 (7)	Dy1—N4—N9—C9	−20.4 (4)
C2—C3—C4—C5	−1.7 (6)	C3—C2—O1—C1	−25.7 (5)
C3—C4—C5—C6	2.8 (7)	C7—C2—O1—C1	154.9 (4)
C4—C5—C6—C7	0.2 (6)	C3—C2—O1—Dy1ⁱ	162.7 (3)
C4—C5—C6—C8	−179.3 (4)	C7—C2—O1—Dy1ⁱ	−16.7 (4)
C3—C2—C7—O2	−173.5 (4)	C2—C7—O2—Dy1	−167.5 (3)
O1—C2—C7—O2	6.0 (5)	C6—C7—O2—Dy1	13.8 (6)
C3—C2—C7—C6	5.3 (6)	C2—C7—O2—Dy1ⁱ	7.9 (5)
O1—C2—C7—C6	−175.2 (3)	C6—C7—O2—Dy1ⁱ	−170.8 (3)
C5—C6—C7—O2	174.7 (4)	O2ⁱ—Dy1—O2—C7	175.7 (4)
C8—C6—C7—O2	−6.0 (6)	O1ⁱ—Dy1—O2—C7	−162.4 (3)
C5—C6—C7—C2	−4.1 (6)	O4—Dy1—O2—C7	108.9 (3)
C8—C6—C7—C2	175.3 (4)	O3—Dy1—O2—C7	67.4 (3)
C5—C6—C8—N4	176.4 (4)	N4—Dy1—O2—C7	−9.4 (3)
C7—C6—C8—N4	−3.0 (7)	O6—Dy1—O2—C7	−71.2 (3)
C15—C10—C11—C12	−1.1 (6)	N5—Dy1—O2—C7	12.5 (4)
N5—C10—C11—C12	−176.9 (4)	O8—Dy1—O2—C7	−111.5 (3)
C10—C11—C12—C13	1.8 (6)	Dy1ⁱ—Dy1—O2—C7	175.7 (4)
C11—C12—C13—C14	−1.0 (7)	O2ⁱ—Dy1—O2—Dy1ⁱ	0.0
C12—C13—C14—C15	−0.5 (6)	O1ⁱ—Dy1—O2—Dy1ⁱ	21.83 (19)
C13—C14—C15—C10	1.2 (6)	O4—Dy1—O2—Dy1ⁱ	−66.82 (12)
C13—C14—C15—S1	176.6 (3)	O3—Dy1—O2—Dy1ⁱ	−108.32 (12)
C11—C10—C15—C14	−0.5 (6)	N4—Dy1—O2—Dy1ⁱ	174.87 (13)
N5—C10—C15—C14	175.8 (4)	O6—Dy1—O2—Dy1ⁱ	113.12 (11)
C11—C10—C15—S1	−176.5 (3)	N5—Dy1—O2—Dy1ⁱ	−163.24 (12)
N5—C10—C15—S1	−0.2 (4)	O8—Dy1—O2—Dy1ⁱ	72.77 (11)
C6—C8—N4—N9	−179.2 (4)	O5—N6—O3—Dy1	−175.9 (4)
C6—C8—N4—Dy1	4.8 (7)	O4—N6—O3—Dy1	3.2 (3)
O2—Dy1—N4—C8	0.1 (4)	O2—Dy1—O3—N6	126.4 (2)
O2ⁱ—Dy1—N4—C8	9.7 (5)	O2ⁱ—Dy1—O3—N6	56.8 (2)
O1ⁱ—Dy1—N4—C8	153.4 (3)	O1ⁱ—Dy1—O3—N6	−15.6 (2)
O4—Dy1—N4—C8	−104.5 (4)	O4—Dy1—O3—N6	−1.92 (19)
O3—Dy1—N4—C8	−79.8 (4)	N4—Dy1—O3—N6	−155.1 (2)
O6—Dy1—N4—C8	116.7 (4)	O6—Dy1—O3—N6	−130.8 (2)
N5—Dy1—N4—C8	−164.5 (4)	N5—Dy1—O3—N6	−86.6 (2)
O8—Dy1—N4—C8	74.6 (4)	O8—Dy1—O3—N6	128.8 (3)
Dy1ⁱ—Dy1—N4—C8	3.5 (4)	Dy1ⁱ—Dy1—O3—N6	90.8 (2)
O2—Dy1—N4—N9	−176.0 (3)	O5—N6—O4—Dy1	175.9 (4)
O2ⁱ—Dy1—N4—N9	−166.4 (2)	O3—N6—O4—Dy1	−3.2 (3)
O1ⁱ—Dy1—N4—N9	−22.7 (3)	O2—Dy1—O4—N6	−52.3 (2)
O4—Dy1—N4—N9	79.4 (3)	O2ⁱ—Dy1—O4—N6	−118.6 (2)
O3—Dy1—N4—N9	104.2 (3)	O1ⁱ—Dy1—O4—N6	170.4 (2)
O6—Dy1—N4—N9	−59.4 (3)	O3—Dy1—O4—N6	1.91 (19)
N5—Dy1—N4—N9	19.4 (2)	N4—Dy1—O4—N6	32.4 (2)
O8—Dy1—N4—N9	−101.4 (3)	O6—Dy1—O4—N6	127.8 (2)
Dy1ⁱ—Dy1—N4—N9	−172.6 (2)	N5—Dy1—O4—N6	86.3 (2)
N9—C9—N5—C10	−175.2 (4)	O8—Dy1—O4—N6	−146.3 (2)
S1—C9—N5—C10	5.1 (4)	Dy1ⁱ—Dy1—O4—N6	−86.6 (2)
N9—C9—N5—Dy1	15.4 (5)	O7—N7—O6—Dy1	−176.6 (4)
S1—C9—N5—Dy1	−164.29 (19)	O8—N7—O6—Dy1	3.1 (4)
C11—C10—N5—C9	173.0 (4)	O2—Dy1—O6—N7	−56.8 (2)
C15—C10—N5—C9	−3.0 (5)	O2ⁱ—Dy1—O6—N7	24.1 (3)
C11—C10—N5—Dy1	−21.3 (6)	O1ⁱ—Dy1—O6—N7	81.2 (2)
C15—C10—N5—Dy1	162.7 (3)	O4—Dy1—O6—N7	123.1 (2)
O2—Dy1—N5—C9	−40.9 (3)	O3—Dy1—O6—N7	−147.7 (2)
O2ⁱ—Dy1—N5—C9	167.3 (2)	N4—Dy1—O6—N7	−122.6 (2)
O1ⁱ—Dy1—N5—C9	135.7 (3)	N5—Dy1—O6—N7	166.3 (3)
O4—Dy1—N5—C9	−148.7 (3)	O8—Dy1—O6—N7	−1.8 (2)
O3—Dy1—N5—C9	−95.1 (3)	Dy1ⁱ—Dy1—O6—N7	−16.8 (2)
N4—Dy1—N5—C9	−17.7 (3)	O7—N7—O8—Dy1	176.7 (4)
O6—Dy1—N5—C9	56.8 (3)	O6—N7—O8—Dy1	−3.0 (4)
O8—Dy1—N5—C9	67.5 (3)	O2—Dy1—O8—N7	129.1 (2)
Dy1ⁱ—Dy1—N5—C9	−108.9 (4)	O2ⁱ—Dy1—O8—N7	−153.6 (3)
O2—Dy1—N5—C10	153.8 (3)	O1ⁱ—Dy1—O8—N7	−82.3 (2)
O2ⁱ—Dy1—N5—C10	2.0 (5)	O4—Dy1—O8—N7	−125.1 (2)
O1ⁱ—Dy1—N5—C10	−29.6 (4)	O3—Dy1—O8—N7	126.7 (3)
O4—Dy1—N5—C10	46.0 (4)	N4—Dy1—O8—N7	56.0 (2)
O3—Dy1—N5—C10	99.6 (4)	O6—Dy1—O8—N7	1.8 (2)
N4—Dy1—N5—C10	177.0 (4)	N5—Dy1—O8—N7	−11.4 (3)
O6—Dy1—N5—C10	−108.5 (4)	Dy1ⁱ—Dy1—O8—N7	167.8 (3)
O8—Dy1—N5—C10	−97.8 (4)	N5—C9—S1—C15	−4.6 (3)
Dy1ⁱ—Dy1—N5—C10	85.8 (5)	N9—C9—S1—C15	175.7 (4)
N5—C9—N9—N4	3.2 (6)	C14—C15—S1—C9	−173.3 (4)
S1—C9—N9—N4	−177.1 (3)	C10—C15—S1—C9	2.4 (3)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O3ⁱⁱ	0.84	2.64	3.206 (4)	126
O9—H9A···O8ⁱⁱⁱ	0.84	2.24	3.049 (4)	161
N9—H9···O9^iv	0.88	1.91	2.751 (4)	160

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

Experimental details

Crystal data
Chemical formula	[Dy₂(C₁₅H₁₂N₃O₂S)₂(NO₃)₄]·2CH₄O
M_r	1233.82
Crystal system, space group	Triclinic, P1
Temperature (K)	159
a, b, c (Å)	9.6191 (6), 10.1002 (7), 11.6151 (8)
α, β, γ (°)	112.045 (1), 105.065 (1), 93.154 (1)
V (Å³)	995.23 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.92
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2002)
T_min, T_max	0.631, 0.676
No. of measured, independent and observed [I > 2σ(I)] reflections	5083, 3502, 3162
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.057, 1.07
No. of reflections	3502
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.51

Computer programs: CrystalClear (Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2006) and XP (Siemens, 1994), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Dy1—O2	2.280 (3)	Dy1—N4	2.461 (3)
Dy1—O2ⁱ	2.374 (2)	Dy1—O6	2.471 (3)
Dy1—O1ⁱ	2.394 (3)	Dy1—N5	2.494 (3)
Dy1—O4	2.422 (3)	Dy1—O8	2.530 (3)
Dy1—O3	2.433 (3)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O3ⁱⁱ	0.84	2.64	3.206 (4)	126
O9—H9A···O8ⁱⁱⁱ	0.84	2.24	3.049 (4)	161
N9—H9···O9^iv	0.88	1.91	2.751 (4)	160

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

Acknowledgements

Financial support by the NSFC (20761004, 21061009) and the Inner Mongolia Autonomous Region Fund for Natural Science (2010MS0201) is gratefully acknowledged. This work was supported by the "211 project" of the postgraduate student programme of Inner Mongolia University.

References

Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Lin, P.-H., Burchell, T. J., Clérac, R. & Murugesu, M. (2008). Angew. Chem. Int. Ed. 47, 8848–8851. Web of Science CSD CrossRef CAS Google Scholar
Lin, S.-Y., Guo, Y.-N., Xu, G.-F. & Tang, J.-K. (2010). Chin. J. Appl. Chem. 27, 1365–1371. CAS Google Scholar
Lin, Y.-C. & Hong, F.-E. (2009). Acta Cryst. E65, m1077. Web of Science CSD CrossRef IUCr Journals Google Scholar
Patil, S. A., Weng, C.-M., Huang, P.-C. & Hong, F.-E. (2009). Tetrahedron, 65, 2889–2897. Web of Science CSD CrossRef CAS Google Scholar
Rigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1994). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, G.-F., Wang, Q.-L., Gamez, P., Ma, Y., Clérac, R., Tang, J.-K., Yan, S.-P., Cheng, P. & Liao, D.-Z. (2010). Chem. Commun. 46, 1506–1508. CrossRef CAS Google Scholar

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Volume 67| Part 6| June 2011| Pages m796-m797

doi:10.1107/S1600536811019118

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

Bis(μ-2-{[2-(1,3-benzo­thia­zol-2-yl)hydrazinyl­­idene]meth­yl}-6-meth­­oxy­phenolato)bis­­[dinitratodysprosium(III)] methanol disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(μ-2-{[2-(1,3-benzothiazol-2-yl)hydrazinylidene]methyl}-6-methoxyphenolato)bis[dinitratodysprosium(III)] methanol disolvate