Poly[[diaqua­(1,10-phenanthroline-κ2N,N′)(μ3-4-sulfonato­benzene-1,2-dicarboxyl­ato-κ4O1:O2,O2′:O4)dysprosium(III)] dihydrate]

Zhang, K.-L.; Lin, J.-G.; Ng, S.W.

doi:10.1107/S1600536812003613

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m241

doi:10.1107/S1600536812003613

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Poly[[diaqua(1,10-phenanthroline-κ²N,N′)(μ₃-4-sulfonatobenzene-1,2-dicarboxylato-κ⁴O¹:O²,O^2′:O⁴)dysprosium(III)] dihydrate]

Kou-Lin Zhang,^a Jian-Guo Lin ^a and Seik Weng Ng ^b,^c ^*

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 24 January 2012; accepted 27 January 2012; online 4 February 2012)

The 4-sulfophthalate trianion in the polymeric title complex, {[Dy(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O}_n, bridges three water/phenanthroline-coordinated Dy^III atoms to form a three-dimensional network architecture. The metal atom is further chelated by a carboxylate group and is covalently bonded to a monodentate carboxylate group and to a monodentate sulfonate group in a distorted square-antiprismatic geometry. The coordinating and the solvent water molecules are hydrogen bonded to the network. In the crystal, one solvent water molecule is disordered over two positions [major component = 59 (3)%].

Related literature

For the isostructural Er^III complex, see: Zhang et al. (2012 ).

Experimental

Crystal data

[Dy(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O
M_r = 657.93
Monoclinic, P 2₁ /n
a = 14.3852 (7) Å
b = 9.6487 (5) Å
c = 17.4280 (9) Å
β = 105.770 (1)°
V = 2327.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 3.36 mm⁻¹
T = 293 K
0.50 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.473, T_max = 1.000
6452 measured reflections
4022 independent reflections
3864 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.093
S = 1.20
4022 reflections
353 parameters
33 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.97 e Å⁻³
Δρ_min = −1.85 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O5ⁱ	0.84 (1)	1.98 (1)	2.817 (6)	175 (7)
O1w—H12⋯O7ⁱⁱ	0.84 (1)	1.94 (2)	2.760 (6)	166 (6)
O2w—H21⋯O2	0.84 (1)	1.96 (3)	2.744 (7)	156 (7)
O2w—H22⋯O3w	0.84 (1)	1.83 (2)	2.66 (1)	169 (7)
O3W—H31⋯O7ⁱⁱⁱ	0.84 (1)	2.05 (1)	2.81 (1)	151 (2)
O3w′—H33⋯O7ⁱⁱⁱ	0.84 (1)	2.05 (1)	2.74 (2)	139 (2)
O4w—H41⋯O2^iv	0.84 (1)	2.11 (5)	2.897 (8)	155 (11)
O4w—H41⋯O2^iv	0.84 (1)	2.11 (5)	2.897 (8)	155 (11)
O4w—H42⋯O3^v	0.84 (1)	2.04 (6)	2.787 (9)	148 (11)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) -x+1, -y+1, -z; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x, y+1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003613/xu5457sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003613/xu5457Isup2.hkl

checkCIF report

Comment top

The deprotonated 4-sulfophthalic acid trianion forms a number of coordination polymers as its carboxyl and sulfo groups are capable of a variety of bonding modes. Among these, the 1,10-phenanthroline-coordinated europium derivative exists as a monoaqua coordination polymer adopting a chain motif. The Er^III analog is instead a diaqua coordination polymer adopting a three-dimensional network motif. The title Dy_III analog is isostructural with the Er^III derivative (Zhang et al., 2012). The 4-sulfophthalate trianion bridges three water/phenanthroline-coordinated Dy^III atoms to form a three-dimensional network architecture (Scheme I, Fig. 1). The metal atom is chelated by a carboxyl group and is covalently bonded to a unidentate carboxyl as well as to a unidentate sulfo group in a square antiprismatic geometry. The lattice water molecules are hydrogen-bonded to the network. Other O–H···O hydrogen bonds are also present (Table 1).

Related literature top

For the isostructural Er^III complex, see: Zhang et al. (2012).

Experimental top

4-Sulfophthalic acid (0.080 g), 1,10-phenanthroline (0.057 g), erbium trichloride hexahydrate (0.113 g) and water (10 ml) were placed in a 25 -ml Teflon-lined stainless-steel Parr bomb. The vessel was heated at 443 K for 3 days. Red crystals were obtained when the vessel was cooled to room temperature slowly in about 30% yield.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the formula unit of polymeric [Dy(H₂O)₂(C₁₂H₈N₂)(C₈H₃O₇S)]_n^.2nH₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

Poly[[diaqua(1,10-phenanthroline-κ²N,N')(µ₃-4- sulfonatobenzene-1,2-dicarboxylato- κ⁴O¹:O²,O^2':O⁴)dysprosium(III)] dihydrate] top

Crystal data top

[Dy(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O	F(000) = 1292
M_r = 657.93	D_x = 1.877 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5412 reflections
a = 14.3852 (7) Å	θ = 2.2–25.1°
b = 9.6487 (5) Å	µ = 3.36 mm⁻¹
c = 17.4280 (9) Å	T = 293 K
β = 105.770 (1)°	Block, red
V = 2327.9 (2) Å³	0.50 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4022 independent reflections
Radiation source: fine-focus sealed tube	3864 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→16
T_min = 0.473, T_max = 1.000	k = −11→9
6452 measured reflections	l = −20→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ²(F_o²) + (0.0378P)² + 10.2868P] where P = (F_o² + 2F_c²)/3
4022 reflections	(Δ/σ)_max = 0.001
353 parameters	Δρ_max = 0.97 e Å⁻³
33 restraints	Δρ_min = −1.85 e Å⁻³

Crystal data top

[Dy(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O	V = 2327.9 (2) Å³
M_r = 657.93	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.3852 (7) Å	µ = 3.36 mm⁻¹
b = 9.6487 (5) Å	T = 293 K
c = 17.4280 (9) Å	0.50 × 0.30 × 0.20 mm
β = 105.770 (1)°

Data collection top

Bruker SMART APEX diffractometer	4022 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3864 reflections with I > 2σ(I)
T_min = 0.473, T_max = 1.000	R_int = 0.023
6452 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	33 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ²(F_o²) + (0.0378P)² + 10.2868P] where P = (F_o² + 2F_c²)/3
4022 reflections	Δρ_max = 0.97 e Å⁻³
353 parameters	Δρ_min = −1.85 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Dy1	0.604921 (17)	0.47289 (2)	0.259769 (14)	0.02131 (11)
S1	0.36749 (10)	0.32357 (16)	0.16213 (8)	0.0313 (3)
O1	0.4682 (3)	0.3307 (4)	0.2104 (2)	0.0319 (9)
O2	0.3258 (3)	0.4612 (5)	0.1434 (3)	0.0473 (12)
O3	0.3103 (4)	0.2348 (6)	0.1978 (3)	0.0562 (14)
O4	0.4063 (4)	0.4842 (4)	−0.1216 (3)	0.0452 (12)
O5	0.3528 (3)	0.3141 (4)	−0.2043 (2)	0.0292 (8)
O6	0.2670 (3)	0.0319 (4)	−0.1959 (2)	0.0303 (9)
O7	0.4245 (3)	−0.0030 (5)	−0.1685 (3)	0.0400 (10)
O1w	0.6545 (3)	0.2479 (4)	0.2389 (3)	0.0390 (10)
H11	0.7126 (15)	0.224 (6)	0.256 (4)	0.059*
H12	0.622 (4)	0.180 (4)	0.217 (4)	0.059*
O2w	0.4682 (3)	0.6129 (5)	0.2456 (3)	0.0432 (11)
H21	0.422 (4)	0.589 (7)	0.207 (3)	0.065*
H22	0.465 (5)	0.6988 (19)	0.253 (4)	0.065*
O3w	0.4836 (11)	0.8837 (11)	0.2752 (11)	0.069 (4)	0.59 (3)
H31	0.492 (4)	0.911 (11)	0.2318 (17)	0.103*	0.59 (3)
H32	0.523 (10)	0.923 (16)	0.313 (2)	0.103*	0.59 (3)
O3w'	0.4379 (15)	0.8711 (16)	0.2234 (15)	0.062 (6)	0.41 (3)
H33	0.492 (4)	0.911 (11)	0.2318 (17)	0.093*	0.41 (3)
H34	0.417 (10)	0.85 (3)	0.174 (3)	0.093*	0.41 (3)
O4w	0.3507 (5)	1.0315 (7)	0.3158 (4)	0.0733 (18)
H41	0.304 (5)	0.986 (11)	0.323 (6)	0.110*
H42	0.335 (7)	1.064 (12)	0.269 (3)	0.110*
N1	0.5893 (4)	0.3636 (5)	0.3864 (3)	0.0321 (11)
N2	0.6436 (4)	0.6324 (5)	0.3796 (3)	0.0334 (11)
C1	0.5629 (5)	0.2329 (7)	0.3899 (4)	0.0439 (16)
H1	0.5472	0.1816	0.3430	0.053*
C2	0.5574 (6)	0.1671 (8)	0.4602 (5)	0.057 (2)
H2	0.5386	0.0749	0.4598	0.068*
C3	0.5804 (5)	0.2422 (9)	0.5294 (4)	0.0536 (19)
H3	0.5777	0.2006	0.5769	0.064*
C4	0.6079 (4)	0.3812 (8)	0.5291 (4)	0.0409 (16)
C5	0.6328 (5)	0.4680 (10)	0.5983 (4)	0.054 (2)
H5	0.6293	0.4317	0.6469	0.065*
C6	0.6607 (5)	0.5984 (10)	0.5956 (4)	0.055 (2)
H6	0.6764	0.6508	0.6421	0.066*
C7	0.6673 (5)	0.6603 (8)	0.5226 (4)	0.0426 (16)
C8	0.6981 (6)	0.7960 (9)	0.5163 (5)	0.060 (2)
H8	0.7165	0.8514	0.5616	0.072*
C9	0.7016 (6)	0.8474 (9)	0.4453 (5)	0.064 (2)
H9	0.7225	0.9377	0.4414	0.076*
C10	0.6732 (5)	0.7635 (7)	0.3775 (4)	0.0464 (17)
H10	0.6751	0.8004	0.3286	0.056*
C11	0.6409 (4)	0.5806 (7)	0.4521 (3)	0.0324 (13)
C12	0.6114 (4)	0.4385 (7)	0.4552 (3)	0.0306 (12)
C13	0.3692 (4)	0.2467 (6)	0.0699 (3)	0.0288 (12)
C14	0.3764 (4)	0.3288 (6)	0.0069 (3)	0.0292 (12)
H14	0.3835	0.4242	0.0136	0.035*
C15	0.3730 (4)	0.2696 (6)	−0.0663 (3)	0.0268 (11)
C16	0.3638 (4)	0.1247 (6)	−0.0757 (3)	0.0245 (11)
C17	0.3649 (4)	0.0425 (6)	−0.0092 (3)	0.0305 (12)
H17	0.3652	−0.0535	−0.0134	0.037*
C18	0.3655 (4)	0.1044 (7)	0.0627 (3)	0.0340 (13)
H18	0.3635	0.0498	0.1061	0.041*
C19	0.3777 (4)	0.3615 (6)	−0.1346 (3)	0.0295 (12)
C20	0.3526 (4)	0.0487 (6)	−0.1538 (3)	0.0274 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Dy1	0.02671 (16)	0.01852 (16)	0.01882 (15)	−0.00121 (9)	0.00642 (10)	−0.00062 (9)
S1	0.0288 (7)	0.0446 (9)	0.0204 (7)	−0.0047 (6)	0.0065 (5)	−0.0014 (6)
O1	0.029 (2)	0.032 (2)	0.028 (2)	−0.0017 (16)	−0.0031 (16)	−0.0001 (17)
O2	0.045 (3)	0.057 (3)	0.037 (3)	0.019 (2)	0.005 (2)	−0.004 (2)
O3	0.055 (3)	0.083 (4)	0.036 (3)	−0.033 (3)	0.023 (2)	−0.012 (3)
O4	0.084 (4)	0.027 (2)	0.027 (2)	−0.014 (2)	0.019 (2)	−0.0056 (18)
O5	0.042 (2)	0.024 (2)	0.0197 (19)	−0.0047 (16)	0.0042 (16)	−0.0012 (15)
O6	0.024 (2)	0.028 (2)	0.035 (2)	−0.0025 (15)	0.0009 (17)	−0.0058 (16)
O7	0.035 (2)	0.037 (2)	0.049 (3)	0.0041 (19)	0.012 (2)	−0.009 (2)
O1w	0.033 (2)	0.024 (2)	0.058 (3)	0.0032 (17)	0.010 (2)	−0.011 (2)
O2w	0.042 (3)	0.029 (2)	0.057 (3)	0.0053 (19)	0.012 (2)	0.000 (2)
O3w	0.082 (8)	0.048 (5)	0.084 (9)	0.005 (5)	0.035 (7)	0.004 (5)
O3w'	0.066 (9)	0.043 (7)	0.081 (10)	0.012 (6)	0.027 (7)	0.011 (6)
O4w	0.078 (4)	0.077 (4)	0.077 (4)	−0.001 (3)	0.042 (3)	0.010 (3)
N1	0.040 (3)	0.032 (3)	0.025 (2)	−0.003 (2)	0.009 (2)	−0.001 (2)
N2	0.041 (3)	0.032 (3)	0.029 (3)	−0.005 (2)	0.011 (2)	−0.009 (2)
C1	0.060 (4)	0.037 (4)	0.037 (4)	−0.006 (3)	0.018 (3)	0.005 (3)
C2	0.069 (5)	0.048 (4)	0.059 (5)	−0.006 (4)	0.027 (4)	0.021 (4)
C3	0.055 (4)	0.073 (5)	0.038 (4)	0.007 (4)	0.022 (3)	0.024 (4)
C4	0.031 (3)	0.066 (5)	0.026 (3)	0.008 (3)	0.009 (2)	0.008 (3)
C5	0.047 (4)	0.095 (7)	0.021 (3)	0.015 (4)	0.010 (3)	0.006 (3)
C6	0.046 (4)	0.083 (6)	0.031 (4)	0.008 (4)	0.004 (3)	−0.021 (4)
C7	0.034 (3)	0.062 (5)	0.032 (3)	0.006 (3)	0.009 (3)	−0.012 (3)
C8	0.071 (5)	0.066 (5)	0.045 (4)	−0.015 (4)	0.019 (4)	−0.032 (4)
C9	0.084 (6)	0.049 (5)	0.065 (5)	−0.017 (4)	0.032 (5)	−0.033 (4)
C10	0.067 (5)	0.036 (4)	0.042 (4)	−0.016 (3)	0.024 (3)	−0.012 (3)
C11	0.030 (3)	0.044 (4)	0.023 (3)	−0.002 (3)	0.007 (2)	−0.008 (3)
C12	0.023 (3)	0.045 (3)	0.023 (3)	0.006 (2)	0.006 (2)	0.001 (2)
C13	0.027 (3)	0.038 (3)	0.021 (3)	−0.003 (2)	0.005 (2)	−0.002 (2)
C14	0.038 (3)	0.026 (3)	0.024 (3)	−0.003 (2)	0.008 (2)	−0.001 (2)
C15	0.032 (3)	0.024 (3)	0.023 (3)	−0.003 (2)	0.006 (2)	0.003 (2)
C16	0.021 (3)	0.028 (3)	0.021 (3)	0.000 (2)	0.000 (2)	0.002 (2)
C17	0.031 (3)	0.026 (3)	0.030 (3)	0.002 (2)	0.002 (2)	0.007 (2)
C18	0.033 (3)	0.042 (4)	0.027 (3)	−0.004 (3)	0.007 (2)	0.010 (3)
C19	0.038 (3)	0.025 (3)	0.027 (3)	0.001 (2)	0.011 (2)	0.001 (2)
C20	0.030 (3)	0.021 (3)	0.031 (3)	−0.001 (2)	0.007 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Dy1—O6ⁱ	2.249 (4)	N2—C11	1.368 (8)
Dy1—O2w	2.343 (4)	C1—C2	1.401 (9)
Dy1—O1w	2.344 (4)	C1—H1	0.9300
Dy1—O1	2.360 (4)	C2—C3	1.368 (12)
Dy1—O4ⁱⁱ	2.406 (4)	C2—H2	0.9300
Dy1—O5ⁱⁱ	2.418 (4)	C3—C4	1.399 (11)
Dy1—N1	2.511 (5)	C3—H3	0.9300
Dy1—N2	2.532 (5)	C4—C12	1.415 (8)
S1—O3	1.440 (5)	C4—C5	1.432 (10)
S1—O2	1.458 (5)	C5—C6	1.325 (12)
S1—O1	1.466 (4)	C5—H5	0.9300
S1—C13	1.776 (6)	C6—C7	1.432 (11)
O4—C19	1.253 (7)	C6—H6	0.9300
O4—Dy1ⁱⁱ	2.406 (4)	C7—C8	1.396 (11)
O5—C19	1.256 (7)	C7—C11	1.411 (8)
O5—Dy1ⁱⁱ	2.418 (4)	C8—C9	1.346 (12)
O6—C20	1.260 (7)	C8—H8	0.9300
O6—Dy1ⁱⁱⁱ	2.249 (4)	C9—C10	1.400 (10)
O7—C20	1.236 (7)	C9—H9	0.9300
O1w—H11	0.840 (10)	C10—H10	0.9300
O1w—H12	0.839 (10)	C11—C12	1.441 (9)
O2w—H21	0.840 (10)	C13—C18	1.378 (9)
O2w—H22	0.840 (10)	C13—C14	1.380 (8)
O3w—H31	0.838 (10)	C14—C15	1.386 (8)
O3w—H32	0.838 (11)	C14—H14	0.9300
O3w—H33	0.838 (10)	C15—C16	1.410 (8)
O3w'—H31	0.842 (10)	C15—C19	1.502 (7)
O3w'—H33	0.842 (10)	C16—C17	1.399 (8)
O3w'—H34	0.840 (10)	C16—C20	1.516 (8)
O4w—H41	0.842 (10)	C17—C18	1.386 (9)
O4w—H42	0.842 (10)	C17—H17	0.9300
N1—C1	1.323 (8)	C18—H18	0.9300
N1—C12	1.361 (7)	C19—Dy1ⁱⁱ	2.769 (6)
N2—C10	1.338 (8)

O6ⁱ—Dy1—O2w	144.11 (16)	C3—C2—H2	120.9
O6ⁱ—Dy1—O1w	72.76 (14)	C1—C2—H2	120.9
O2w—Dy1—O1w	143.10 (16)	C2—C3—C4	120.3 (6)
O6ⁱ—Dy1—O1	142.83 (14)	C2—C3—H3	119.8
O2w—Dy1—O1	72.81 (16)	C4—C3—H3	119.8
O1w—Dy1—O1	70.34 (14)	C3—C4—C12	117.3 (6)
O6ⁱ—Dy1—O4ⁱⁱ	97.40 (17)	C3—C4—C5	124.3 (6)
O2w—Dy1—O4ⁱⁱ	88.24 (18)	C12—C4—C5	118.4 (7)
O1w—Dy1—O4ⁱⁱ	86.81 (16)	C6—C5—C4	122.3 (7)
O1—Dy1—O4ⁱⁱ	84.97 (15)	C6—C5—H5	118.9
O6ⁱ—Dy1—O5ⁱⁱ	78.73 (14)	C4—C5—H5	118.9
O2w—Dy1—O5ⁱⁱ	76.29 (15)	C5—C6—C7	121.5 (7)
O1w—Dy1—O5ⁱⁱ	127.22 (15)	C5—C6—H6	119.3
O1—Dy1—O5ⁱⁱ	128.57 (13)	C7—C6—H6	119.3
O4ⁱⁱ—Dy1—O5ⁱⁱ	53.80 (13)	C8—C7—C11	117.3 (6)
O6ⁱ—Dy1—N1	91.24 (15)	C8—C7—C6	124.1 (7)
O2w—Dy1—N1	93.53 (17)	C11—C7—C6	118.6 (7)
O1w—Dy1—N1	81.44 (17)	C9—C8—C7	120.6 (7)
O1—Dy1—N1	79.13 (15)	C9—C8—H8	119.7
O4ⁱⁱ—Dy1—N1	162.68 (15)	C7—C8—H8	119.7
O5ⁱⁱ—Dy1—N1	143.20 (14)	C8—C9—C10	119.2 (8)
O6ⁱ—Dy1—N2	75.75 (16)	C8—C9—H9	120.4
O2w—Dy1—N2	74.13 (17)	C10—C9—H9	120.4
O1w—Dy1—N2	133.09 (17)	N2—C10—C9	123.0 (7)
O1—Dy1—N2	128.97 (15)	N2—C10—H10	118.5
O4ⁱⁱ—Dy1—N2	131.39 (15)	C9—C10—H10	118.5
O5ⁱⁱ—Dy1—N2	77.89 (15)	N2—C11—C7	122.4 (6)
N1—Dy1—N2	65.32 (16)	N2—C11—C12	117.7 (5)
O3—S1—O2	113.0 (3)	C7—C11—C12	119.9 (6)
O3—S1—O1	111.8 (3)	N1—C12—C4	122.4 (6)
O2—S1—O1	111.6 (3)	N1—C12—C11	118.2 (5)
O3—S1—C13	107.0 (3)	C4—C12—C11	119.3 (6)
O2—S1—C13	106.5 (3)	C18—C13—C14	120.5 (5)
O1—S1—C13	106.5 (3)	C18—C13—S1	119.3 (4)
S1—O1—Dy1	146.3 (3)	C14—C13—S1	120.2 (5)
C19—O4—Dy1ⁱⁱ	92.9 (3)	C13—C14—C15	120.3 (5)
C19—O5—Dy1ⁱⁱ	92.3 (3)	C13—C14—H14	119.9
C20—O6—Dy1ⁱⁱⁱ	163.8 (4)	C15—C14—H14	119.9
Dy1—O1w—H11	121 (4)	C14—C15—C16	119.6 (5)
Dy1—O1w—H12	130 (4)	C14—C15—C19	119.3 (5)
H11—O1w—H12	109.6 (18)	C16—C15—C19	121.1 (5)
Dy1—O2w—H21	113 (5)	C17—C16—C15	119.1 (5)
Dy1—O2w—H22	129 (5)	C17—C16—C20	116.3 (5)
H21—O2w—H22	109 (2)	C15—C16—C20	124.6 (5)
H31—O3w—H32	110 (2)	C18—C17—C16	120.0 (5)
H32—O3w—H33	110 (2)	C18—C17—H17	120.0
H31—O3w'—H34	109 (2)	C16—C17—H17	120.0
H33—O3w'—H34	109 (2)	C13—C18—C17	120.2 (5)
H41—O4w—H42	109 (2)	C13—C18—H18	119.9
C1—N1—C12	117.8 (5)	C17—C18—H18	119.9
C1—N1—Dy1	122.4 (4)	O4—C19—O5	120.9 (5)
C12—N1—Dy1	119.7 (4)	O4—C19—C15	119.8 (5)
C10—N2—C11	117.4 (5)	O5—C19—C15	119.3 (5)
C10—N2—Dy1	123.5 (4)	O4—C19—Dy1ⁱⁱ	60.2 (3)
C11—N2—Dy1	118.9 (4)	O5—C19—Dy1ⁱⁱ	60.8 (3)
N1—C1—C2	123.9 (7)	C15—C19—Dy1ⁱⁱ	177.4 (4)
N1—C1—H1	118.1	O7—C20—O6	124.6 (5)
C2—C1—H1	118.1	O7—C20—C16	119.4 (5)
C3—C2—C1	118.3 (7)	O6—C20—C16	115.7 (5)

O3—S1—O1—Dy1	−140.2 (4)	C8—C9—C10—N2	−0.8 (13)
O2—S1—O1—Dy1	−12.6 (6)	C10—N2—C11—C7	0.4 (9)
C13—S1—O1—Dy1	103.2 (5)	Dy1—N2—C11—C7	176.0 (4)
O6ⁱ—Dy1—O1—S1	−155.1 (4)	C10—N2—C11—C12	−178.5 (6)
O2w—Dy1—O1—S1	30.2 (4)	Dy1—N2—C11—C12	−2.8 (7)
O1w—Dy1—O1—S1	−147.9 (5)	C8—C7—C11—N2	−0.8 (10)
O4ⁱⁱ—Dy1—O1—S1	−59.5 (5)	C6—C7—C11—N2	179.0 (6)
O5ⁱⁱ—Dy1—O1—S1	−25.5 (5)	C8—C7—C11—C12	178.0 (6)
N1—Dy1—O1—S1	127.4 (5)	C6—C7—C11—C12	−2.2 (9)
N2—Dy1—O1—S1	82.0 (5)	C1—N1—C12—C4	0.5 (9)
O6ⁱ—Dy1—N1—C1	−106.3 (5)	Dy1—N1—C12—C4	−177.3 (4)
O2w—Dy1—N1—C1	109.3 (5)	C1—N1—C12—C11	179.5 (6)
O1w—Dy1—N1—C1	−33.9 (5)	Dy1—N1—C12—C11	1.7 (7)
O1—Dy1—N1—C1	37.6 (5)	C3—C4—C12—N1	0.0 (9)
O4ⁱⁱ—Dy1—N1—C1	13.9 (9)	C5—C4—C12—N1	179.8 (6)
O5ⁱⁱ—Dy1—N1—C1	−179.0 (4)	C3—C4—C12—C11	−179.0 (6)
N2—Dy1—N1—C1	−179.9 (6)	C5—C4—C12—C11	0.8 (8)
O6ⁱ—Dy1—N1—C12	71.5 (4)	N2—C11—C12—N1	0.8 (8)
O2w—Dy1—N1—C12	−72.9 (4)	C7—C11—C12—N1	−178.1 (5)
O1w—Dy1—N1—C12	143.9 (4)	N2—C11—C12—C4	179.8 (5)
O1—Dy1—N1—C12	−144.6 (4)	C7—C11—C12—C4	1.0 (8)
O4ⁱⁱ—Dy1—N1—C12	−168.3 (5)	O3—S1—C13—C18	−31.9 (6)
O5ⁱⁱ—Dy1—N1—C12	−1.2 (6)	O2—S1—C13—C18	−153.0 (5)
N2—Dy1—N1—C12	−2.2 (4)	O1—S1—C13—C18	87.8 (5)
O6ⁱ—Dy1—N2—C10	79.8 (5)	O3—S1—C13—C14	149.5 (5)
O2w—Dy1—N2—C10	−80.5 (5)	O2—S1—C13—C14	28.5 (5)
O1w—Dy1—N2—C10	128.8 (5)	O1—S1—C13—C14	−90.7 (5)
O1—Dy1—N2—C10	−131.8 (5)	C18—C13—C14—C15	4.6 (9)
O4ⁱⁱ—Dy1—N2—C10	−7.5 (6)	S1—C13—C14—C15	−176.8 (4)
O5ⁱⁱ—Dy1—N2—C10	−1.5 (5)	C13—C14—C15—C16	−1.0 (9)
N1—Dy1—N2—C10	177.9 (6)	C13—C14—C15—C19	178.0 (5)
O6ⁱ—Dy1—N2—C11	−95.5 (4)	C14—C15—C16—C17	−4.3 (8)
O2w—Dy1—N2—C11	104.2 (4)	C19—C15—C16—C17	176.6 (5)
O1w—Dy1—N2—C11	−46.6 (5)	C14—C15—C16—C20	175.7 (5)
O1—Dy1—N2—C11	52.9 (5)	C19—C15—C16—C20	−3.3 (8)
O4ⁱⁱ—Dy1—N2—C11	177.1 (4)	C15—C16—C17—C18	6.2 (8)
O5ⁱⁱ—Dy1—N2—C11	−176.8 (4)	C20—C16—C17—C18	−173.8 (5)
N1—Dy1—N2—C11	2.6 (4)	C14—C13—C18—C17	−2.7 (9)
C12—N1—C1—C2	−0.6 (10)	S1—C13—C18—C17	178.7 (4)
Dy1—N1—C1—C2	177.2 (6)	C16—C17—C18—C13	−2.8 (9)
N1—C1—C2—C3	0.1 (12)	Dy1ⁱⁱ—O4—C19—O5	−3.1 (6)
C1—C2—C3—C4	0.5 (12)	Dy1ⁱⁱ—O4—C19—C15	177.0 (5)
C2—C3—C4—C12	−0.5 (10)	Dy1ⁱⁱ—O5—C19—O4	3.1 (6)
C2—C3—C4—C5	179.7 (7)	Dy1ⁱⁱ—O5—C19—C15	−177.0 (5)
C3—C4—C5—C6	178.4 (7)	C14—C15—C19—O4	16.2 (9)
C12—C4—C5—C6	−1.4 (10)	C16—C15—C19—O4	−164.7 (6)
C4—C5—C6—C7	0.2 (11)	C14—C15—C19—O5	−163.7 (5)
C5—C6—C7—C8	−178.6 (8)	C16—C15—C19—O5	15.3 (8)
C5—C6—C7—C11	1.6 (10)	Dy1ⁱⁱⁱ—O6—C20—O7	166.1 (10)
C11—C7—C8—C9	0.4 (12)	Dy1ⁱⁱⁱ—O6—C20—C16	−6.8 (16)
C6—C7—C8—C9	−179.4 (8)	C17—C16—C20—O7	−82.9 (7)
C7—C8—C9—C10	0.3 (13)	C15—C16—C20—O7	97.1 (7)
C11—N2—C10—C9	0.5 (11)	C17—C16—C20—O6	90.4 (6)
Dy1—N2—C10—C9	−174.9 (6)	C15—C16—C20—O6	−89.6 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O5ⁱ	0.84 (1)	1.98 (1)	2.817 (6)	175 (7)
O1w—H12···O7^iv	0.84 (1)	1.94 (2)	2.760 (6)	166 (6)
O2w—H21···O2	0.84 (1)	1.96 (3)	2.744 (7)	156 (7)
O2w—H22···O3w	0.84 (1)	1.83 (2)	2.66 (1)	169 (7)
O3w—H31···O7ⁱⁱ	0.84 (1)	2.05 (1)	2.81 (1)	151 (2)
O3w′—H33···O7ⁱⁱ	0.84 (1)	2.05 (1)	2.74 (2)	139 (2)
O4w—H41···O2^v	0.84 (1)	2.11 (5)	2.897 (8)	155 (11)
O4w—H41···O2^v	0.84 (1)	2.11 (5)	2.897 (8)	155 (11)
O4w—H42···O3^vi	0.84 (1)	2.04 (6)	2.787 (9)	148 (11)

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

Experimental details

Crystal data
Chemical formula	[Dy(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O
M_r	657.93
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.3852 (7), 9.6487 (5), 17.4280 (9)
β (°)	105.770 (1)
V (Å³)	2327.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.36
Crystal size (mm)	0.50 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.473, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6452, 4022, 3864
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.093, 1.20
No. of reflections	4022
No. of parameters	353
No. of restraints	33
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0378P)² + 10.2868P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.97, −1.85

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O5ⁱ	0.84 (1)	1.98 (1)	2.817 (6)	175 (7)
O1w—H12···O7ⁱⁱ	0.84 (1)	1.94 (2)	2.760 (6)	166 (6)
O2w—H21···O2	0.84 (1)	1.96 (3)	2.744 (7)	156 (7)
O2w—H22···O3w	0.84 (1)	1.83 (2)	2.66 (1)	169 (7)
O3w—H31···O7ⁱⁱⁱ	0.84 (1)	2.05 (1)	2.81 (1)	151 (2)
O3w'—H33···O7ⁱⁱⁱ	0.84 (1)	2.05 (1)	2.74 (2)	139 (2)
O4w—H41···O2^iv	0.84 (1)	2.11 (5)	2.897 (8)	155 (11)
O4w—H41···O2^iv	0.84 (1)	2.11 (5)	2.897 (8)	155 (11)
O4w—H42···O3^v	0.84 (1)	2.04 (6)	2.787 (9)	148 (11)

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

Acknowledgements

We thank the Priority Academic Development Program of Jiangsu Higher Education Institution and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, K.-L., Lin, J.-G. & Ng, S. W. (2012). Acta Cryst. E68, m226. Web of Science CSD CrossRef IUCr Journals Google Scholar

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