catena-Poly[[[pentaaquaeuropium(III)]-μ-5-sulfonatoisophthalato-κ4O1,O1′:O3,O3′] 4,4'-bipyridine N,N′-dioxide hemisolvate trihydrate]

Wu, A.-Z.; Ng, S.W.

doi:10.1107/S1600536810041838

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1433

https://doi.org/10.1107/S1600536810041838

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catena-Poly[[[pentaaquaeuropium(III)]-μ-5-sulfonatoisophthalato-κ⁴O¹,O^1′:O³,O^3′] 4,4'-bipyridine N,N′-dioxide hemisolvate trihydrate]

Ai-Zhi Wu ^a and Seik Weng Ng ^b ^*

^aSchool of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou 510006, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 October 2010; accepted 15 October 2010; online 23 October 2010)

In the crystal structure of the title compound, {[Eu(C₈H₃O₇S)(H₂O)₅]·0.5C₁₀H₈N₂O₂·3H₂O}_n, the Eu^III coordination polymer displays a ribbon motif as the 5-sulfoisopthalate anion uses one of carboxyl –CO₂ units to chelate to a Eu atom and the other to bind to other two Eu atoms; the sulfonyl –SO₃ unit is not involved in coordination. Adjacent ribbons are linked by O—H⋯O hydrogen bonds, generating a three-dimensional network. The 4,4′-bipyridine-N,N′-dioxide molecule lies on an inversion centre and is hydrogen-bonded to the complex network. The coordination geometry of the Eu atom is a monocapped square antiprism.

Related literature

For a related structure, see: Hu et al. (2005 ).

Experimental

Crystal data

[Eu(C₈H₃O₇S)(H₂O)₅]·0.5C₁₀H₈N₂O₂·3H₂O
M_r = 633.34
Triclinic, $[P \overline 1]$
a = 10.7800 (4) Å
b = 10.8978 (3) Å
c = 11.4048 (3) Å
α = 89.383 (2)°
β = 62.989 (1)°
γ = 62.678 (6)°
V = 1026.90 (9) Å³
Z = 2
Mo Kα radiation
μ = 3.24 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.631, T_max = 1.000
10108 measured reflections
4658 independent reflections
4509 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.091
S = 1.20
4658 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 3.40 e Å⁻³
Δρ_min = −1.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O8	0.84	1.87	2.673 (4)	159
O1w—H12⋯O6w	0.84	1.91	2.710 (4)	160
O2w—H22⋯O1ⁱ	0.84	2.11	2.804 (4)	140
O2w—H21⋯O3wⁱ	0.84	2.46	3.148 (5)	140
O3w—H31⋯O7w	0.84	1.91	2.742 (4)	175
O3w—H32⋯O8w	0.84	1.87	2.704 (4)	172
O4w—H41⋯O8ⁱⁱ	0.83	1.82	2.648 (4)	171
O4w—H42⋯O5ⁱⁱⁱ	0.83	2.02	2.840 (4)	166
O5w—H51⋯O7w	0.83	2.30	3.026 (5)	146
O6w—H62⋯O6^iv	0.85	2.18	2.955 (5)	151
O6w—H61⋯O6^v	0.85	2.18	2.807 (5)	130
O7w—H71⋯O1ⁱ	0.84	2.49	3.191 (4)	142
O7w—H72⋯O7^vi	0.84	2.03	2.860 (5)	169
O8w—H81⋯O2^vii	0.85	2.17	2.867 (4)	140
O8w—H82⋯O5^viii	0.85	2.07	2.879 (5)	159
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x, -y+2, -z+1; (iii) x-1, y, z; (iv) -x+1, -y+2, -z+1; (v) x-1, y+1, z; (vi) x, y, z-1; (vii) -x+1, -y+1, -z; (viii) -x+2, -y+1, -z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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: https://doi.org/10.1107/S1600536810041838/xu5055sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041838/xu5055Isup2.hkl

checkCIF report

Comment top

In the crystal structure of pentaqua(5-sulfoisophthalato)europium monohydrate sesqui-4,4'-bipyridine, the 5-sulfoisophthalate trianion O,O'-chelates to two metal atoms to furnish a polymeric chain structure. The chains are linked by hydrogen bonds into a three-dimensional network, and the N-heterocycles occupy the cavities of the network. The geometry of the metal atom is a monocapped square-antiprism (Hu et al., 2005). A similar hydrothermal synthesis with 4,4'-bipyridine N-oxide in place of 4,4'-bipyridine affords the corresponding co-crystal, but the co-crystal is a trihydrated1:0.5 co-crystal. In Eu(H₂O)₅(C₈H₃O₇S)^.3H₂O^.0.5C₁₀H₈N₂O₂ (Scheme I), the 5-sulfoisopthalate group uses one of carboxyl –CO₂ units to chelate to a Eu(III) atom and uses the other to bind to two other metal atoms; the sulfonyl –SO₃ unit is not involved in coordination (Fig. 1). The geometry of the europium atom is a monocapped square-antiprism (Fig. 2). Adjacent ribbons (Fig. 3) are linked by O–H···O hydrogen bonds to generate a three-dimensional network (Table 3). The 4,4'-bipyridine N-oxide molecule, which lies on a center-of-inversion, is hydrogen-bonded to the network.

Related literature top

For a related structure, see: Hu et al. (2005).

Experimental top

Europium nitrate hexahydrate (0.22 g, 0.5 mmol), monosodium 5-sulfoisophthalate (0.16 g, 0.5 mmol) and 4,4'-bipyridine-N,N'-dioxide (0.095 g, 0.5 mmol) were placed in a 25-ml Teflon-lined, stainless-steel Parr bomb along with water (15 ml). The bomb was heated to 433 K for 72 h. It was then cooled down to room temperature at a rate of 5 K an hour. Colorless crystals were collected and washed with water (0.195 g, yield 55% based on Eu). The product is stable in air and and is insoluble in water and common organic solvents. CH&N elemental analysis. Calc. for C₁₈H₂₅N₂EuO₁₆S (709.42): C 34.45, H 3.55, N 3.97%. Found: C 34.24, H 3.50, N 4.08%.

Structure description top

For a related structure, see: Hu et al. (2005).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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 a portion of the polymeric structure of Eu(H₂O)₅(C₈H₃O₇S)^.3H₂O^.0.5C₁₀H₈N₂O₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The 4,4'-bipyridine N-oxide molecule lies on a center-of-inversion.
	Fig. 2. Nine-coordinate geometry of Eu.
	Fig. 3. Ribbon structure.

catena-Poly[[[pentaaquaeuropium(III)]\-m-5-sulfonatoisophthalato- κ⁴O¹,O^1':O³,O^3'] 4,4'-bipyridine N,N'-dioxide hemisolvate trihydrate] top

Crystal data top

[Eu(C₈H₃O₇S)(H₂O)₅]·0.5C₁₀H₈N₂O₂·3H₂O	Z = 2
M_r = 633.34	F(000) = 630
Triclinic, P1	D_x = 2.048 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7800 (4) Å	Cell parameters from 9807 reflections
b = 10.8978 (3) Å	θ = 3.5–27.5°
c = 11.4048 (3) Å	µ = 3.24 mm⁻¹
α = 89.383 (2)°	T = 293 K
β = 62.989 (1)°	Prism, colorless
γ = 62.678 (6)°	0.25 × 0.20 × 0.15 mm
V = 1026.90 (9) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4658 independent reflections
Radiation source: fine-focus sealed tube	4509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 3.5°
ω scans	h = −13→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→14
T_min = 0.631, T_max = 1.000	l = −14→14
10108 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.0569P)² + 0.4859P] where P = (F_o² + 2F_c²)/3
4658 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 3.40 e Å⁻³
0 restraints	Δρ_min = −1.13 e Å⁻³

Crystal data top

[Eu(C₈H₃O₇S)(H₂O)₅]·0.5C₁₀H₈N₂O₂·3H₂O	γ = 62.678 (6)°
M_r = 633.34	V = 1026.90 (9) Å³
Triclinic, P1	Z = 2
a = 10.7800 (4) Å	Mo Kα radiation
b = 10.8978 (3) Å	µ = 3.24 mm⁻¹
c = 11.4048 (3) Å	T = 293 K
α = 89.383 (2)°	0.25 × 0.20 × 0.15 mm
β = 62.989 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4658 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4509 reflections with I > 2σ(I)
T_min = 0.631, T_max = 1.000	R_int = 0.033
10108 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.20	Δρ_max = 3.40 e Å⁻³
4658 reflections	Δρ_min = −1.13 e Å⁻³
289 parameters

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

	x	y	z	U_iso*/U_eq
Eu1	0.222361 (16)	0.944055 (13)	0.073400 (13)	0.01756 (8)
S1	0.84263 (11)	0.67200 (9)	0.32120 (9)	0.02471 (18)
O1	0.4314 (3)	0.8569 (3)	0.1429 (3)	0.0305 (6)
O2	0.3992 (3)	0.6830 (3)	0.0953 (3)	0.0285 (5)
O3	0.8412 (4)	0.1844 (3)	0.0243 (3)	0.0346 (6)
O4	0.9706 (3)	0.1556 (3)	0.1368 (3)	0.0295 (6)
O5	1.0036 (4)	0.6411 (4)	0.2226 (3)	0.0418 (7)
O6	0.8400 (4)	0.6030 (3)	0.4321 (3)	0.0396 (7)
O7	0.7229 (4)	0.8236 (3)	0.3736 (3)	0.0375 (6)
O8	0.1731 (4)	0.9846 (3)	0.4955 (3)	0.0329 (6)
O1W	0.1051 (3)	1.0804 (3)	0.3032 (3)	0.0310 (6)
H11	0.1453	1.0318	0.3474	0.047*
H12	0.0801	1.1650	0.3258	0.047*
O2W	0.3042 (4)	1.1235 (3)	0.0498 (4)	0.0410 (7)
H21	0.3387	1.1230	0.1028	0.061*
H22	0.3771	1.1045	−0.0306	0.061*
O3W	0.4909 (4)	0.8044 (3)	−0.1330 (3)	0.0506 (9)
H31	0.5216	0.8429	−0.1957	0.076*
H32	0.5598	0.7170	−0.1571	0.076*
O4W	0.0462 (4)	0.8763 (3)	0.2470 (3)	0.0410 (7)
H41	−0.0306	0.9237	0.3254	0.061*
H42	0.0447	0.8044	0.2251	0.061*
O5W	0.2265 (4)	1.0292 (4)	−0.1370 (3)	0.0441 (8)
H51	0.3014	1.0388	−0.1953	0.066*
H52	0.1451	1.0708	−0.1456	0.066*
O6W	0.1006 (6)	1.3246 (4)	0.3568 (5)	0.0661 (12)
H61	0.0007	1.3802	0.4141	0.099*
H62	0.1513	1.3186	0.3980	0.099*
O7W	0.5761 (4)	0.9318 (4)	−0.3410 (3)	0.0442 (8)
H71	0.6177	0.9731	−0.3246	0.066*
H72	0.6113	0.9114	−0.4245	0.066*
O8W	0.6904 (4)	0.5181 (3)	−0.2118 (3)	0.0423 (7)
H81	0.6327	0.4968	−0.1455	0.064*
H82	0.7768	0.4929	−0.2110	0.064*
N1	0.2607 (4)	0.8511 (3)	0.4986 (3)	0.0260 (6)
C1	0.4710 (4)	0.7263 (4)	0.1275 (3)	0.0211 (6)
C2	0.6071 (4)	0.6265 (3)	0.1492 (3)	0.0182 (6)
C3	0.6773 (4)	0.4793 (3)	0.1120 (3)	0.0199 (6)
H3	0.6427	0.4402	0.0698	0.024*
C4	0.7996 (4)	0.3904 (3)	0.1383 (3)	0.0185 (6)
C5	0.8531 (4)	0.4479 (3)	0.1990 (3)	0.0216 (6)
H5	0.9366	0.3882	0.2142	0.026*
C6	0.7815 (4)	0.5957 (3)	0.2375 (4)	0.0217 (6)
C7	0.6609 (4)	0.6842 (3)	0.2107 (3)	0.0203 (6)
H7	0.6157	0.7825	0.2338	0.024*
C8	0.8774 (4)	0.2302 (3)	0.0962 (3)	0.0201 (6)
C9	0.3563 (5)	0.8243 (4)	0.5518 (4)	0.0305 (8)
H9	0.3592	0.8988	0.5872	0.037*
C10	0.4495 (5)	0.6877 (4)	0.5543 (4)	0.0320 (8)
H10	0.5150	0.6705	0.5916	0.038*
C11	0.4475 (4)	0.5746 (4)	0.5022 (3)	0.0248 (7)
C12	0.3437 (5)	0.6074 (4)	0.4505 (4)	0.0292 (7)
H12A	0.3361	0.5351	0.4174	0.035*
C13	0.2525 (5)	0.7454 (4)	0.4480 (4)	0.0311 (8)
H13	0.1856	0.7657	0.4116	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.01783 (11)	0.01261 (11)	0.02442 (12)	−0.00607 (8)	−0.01399 (8)	0.00504 (7)
S1	0.0289 (4)	0.0182 (4)	0.0365 (4)	−0.0127 (3)	−0.0228 (4)	0.0062 (3)
O1	0.0349 (14)	0.0155 (11)	0.0467 (15)	−0.0070 (11)	−0.0306 (13)	0.0079 (11)
O2	0.0316 (14)	0.0250 (12)	0.0428 (14)	−0.0151 (11)	−0.0283 (12)	0.0145 (11)
O3	0.0466 (17)	0.0176 (11)	0.0531 (17)	−0.0123 (12)	−0.0389 (14)	0.0047 (11)
O4	0.0291 (13)	0.0154 (10)	0.0412 (14)	−0.0024 (10)	−0.0248 (12)	0.0052 (10)
O5	0.0353 (16)	0.0459 (17)	0.0472 (17)	−0.0255 (14)	−0.0181 (14)	0.0017 (14)
O6	0.063 (2)	0.0370 (15)	0.0425 (15)	−0.0283 (15)	−0.0416 (15)	0.0158 (13)
O7	0.0460 (17)	0.0197 (12)	0.0515 (17)	−0.0116 (12)	−0.0333 (15)	0.0025 (12)
O8	0.0399 (15)	0.0218 (12)	0.0321 (13)	−0.0094 (12)	−0.0210 (12)	0.0075 (11)
O1W	0.0447 (16)	0.0234 (12)	0.0295 (12)	−0.0136 (11)	−0.0260 (12)	0.0065 (10)
O2W	0.0412 (17)	0.0359 (15)	0.064 (2)	−0.0283 (14)	−0.0311 (16)	0.0240 (15)
O3W	0.0385 (17)	0.0373 (16)	0.0340 (15)	−0.0015 (14)	−0.0059 (13)	0.0146 (13)
O4W	0.0450 (17)	0.0279 (13)	0.0320 (13)	−0.0247 (13)	0.0001 (12)	−0.0031 (11)
O5W	0.0452 (18)	0.0478 (18)	0.0304 (14)	−0.0162 (15)	−0.0202 (13)	0.0166 (14)
O6W	0.085 (3)	0.0321 (17)	0.117 (4)	−0.0247 (19)	−0.082 (3)	0.021 (2)
O7W	0.0430 (18)	0.0456 (18)	0.0454 (18)	−0.0269 (16)	−0.0190 (15)	0.0187 (15)
O8W	0.0333 (15)	0.0390 (16)	0.0533 (18)	−0.0186 (13)	−0.0208 (14)	0.0149 (14)
N1	0.0280 (15)	0.0233 (14)	0.0203 (12)	−0.0103 (12)	−0.0103 (11)	0.0060 (11)
C1	0.0186 (15)	0.0184 (15)	0.0246 (15)	−0.0064 (13)	−0.0130 (13)	0.0089 (13)
C2	0.0204 (14)	0.0155 (14)	0.0199 (13)	−0.0065 (12)	−0.0139 (12)	0.0065 (11)
C3	0.0219 (15)	0.0166 (13)	0.0249 (14)	−0.0090 (12)	−0.0153 (13)	0.0064 (13)
C4	0.0199 (14)	0.0122 (12)	0.0233 (14)	−0.0060 (11)	−0.0131 (12)	0.0038 (11)
C5	0.0213 (15)	0.0163 (14)	0.0290 (15)	−0.0057 (12)	−0.0180 (13)	0.0046 (12)
C6	0.0234 (16)	0.0157 (14)	0.0314 (16)	−0.0099 (13)	−0.0179 (14)	0.0051 (12)
C7	0.0231 (15)	0.0134 (13)	0.0269 (15)	−0.0080 (12)	−0.0157 (13)	0.0054 (12)
C8	0.0193 (14)	0.0132 (13)	0.0257 (15)	−0.0051 (12)	−0.0131 (12)	0.0030 (12)
C9	0.035 (2)	0.0258 (17)	0.0312 (17)	−0.0146 (16)	−0.0185 (16)	0.0045 (15)
C10	0.036 (2)	0.0304 (18)	0.0378 (19)	−0.0156 (16)	−0.0256 (17)	0.0089 (16)
C11	0.0223 (16)	0.0251 (17)	0.0244 (15)	−0.0126 (14)	−0.0095 (13)	0.0096 (13)
C12	0.0340 (19)	0.0270 (17)	0.0312 (17)	−0.0159 (16)	−0.0194 (16)	0.0062 (15)
C13	0.0314 (19)	0.0312 (18)	0.0351 (18)	−0.0151 (16)	−0.0210 (16)	0.0075 (15)

Geometric parameters (Å, º) top

Eu1—O1	2.500 (2)	O6W—H61	0.8513
Eu1—O2	2.688 (2)	O6W—H62	0.8503
Eu1—O3ⁱ	2.298 (3)	O7W—H71	0.8376
Eu1—O4ⁱⁱ	2.390 (2)	O7W—H72	0.8365
Eu1—O1W	2.455 (2)	O8W—H81	0.8459
Eu1—O2W	2.456 (3)	O8W—H82	0.8457
Eu1—O3W	2.466 (3)	N1—C9	1.343 (5)
Eu1—O4W	2.431 (3)	N1—C13	1.350 (5)
Eu1—O5W	2.552 (3)	C1—C2	1.502 (4)
S1—O5	1.445 (3)	C2—C7	1.391 (4)
S1—O7	1.454 (3)	C2—C3	1.392 (4)
S1—O6	1.460 (3)	C3—C4	1.395 (4)
S1—C6	1.769 (3)	C3—H3	0.9300
O1—C1	1.273 (4)	C4—C5	1.381 (4)
O2—C1	1.246 (4)	C4—C8	1.513 (4)
O3—C8	1.245 (4)	C5—C6	1.396 (4)
O4—C8	1.245 (4)	C5—H5	0.9300
O8—N1	1.333 (4)	C6—C7	1.385 (4)
O1W—H11	0.8386	C7—H7	0.9300
O1W—H12	0.8384	C9—C10	1.371 (5)
O2W—H21	0.8400	C9—H9	0.9300
O2W—H22	0.8380	C10—C11	1.387 (5)
O3W—H31	0.8383	C10—H10	0.9300
O3W—H32	0.8396	C11—C12	1.398 (5)
O4W—H41	0.8345	C11—C11ⁱⁱⁱ	1.479 (7)
O4W—H42	0.8346	C12—C13	1.378 (5)
O5W—H51	0.8333	C12—H12A	0.9300
O5W—H52	0.8349	C13—H13	0.9300

O3ⁱ—Eu1—O4ⁱⁱ	90.47 (9)	Eu1—O3W—H32	130.2
O3ⁱ—Eu1—O4W	70.06 (11)	H31—O3W—H32	109.5
O4ⁱⁱ—Eu1—O4W	82.34 (10)	Eu1—O4W—H41	129.1
O3ⁱ—Eu1—O2W	144.73 (11)	Eu1—O4W—H42	119.2
O4ⁱⁱ—Eu1—O2W	79.72 (10)	H41—O4W—H42	110.4
O4W—Eu1—O2W	140.17 (11)	Eu1—O5W—H51	123.4
O3ⁱ—Eu1—O1W	135.51 (11)	Eu1—O5W—H52	124.1
O4ⁱⁱ—Eu1—O1W	70.13 (9)	H51—O5W—H52	110.6
O4W—Eu1—O1W	67.97 (10)	H61—O6W—H62	106.3
O2W—Eu1—O1W	72.54 (11)	H71—O7W—H72	110.2
O3ⁱ—Eu1—O3W	82.80 (13)	H81—O8W—H82	107.4
O4ⁱⁱ—Eu1—O3W	137.24 (10)	O8—N1—C9	119.1 (3)
O4W—Eu1—O3W	132.75 (10)	O8—N1—C13	119.7 (3)
O2W—Eu1—O3W	81.93 (12)	C9—N1—C13	121.2 (3)
O1W—Eu1—O3W	138.25 (12)	O2—C1—O1	121.0 (3)
O3ⁱ—Eu1—O1	129.26 (8)	O2—C1—C2	121.4 (3)
O4ⁱⁱ—Eu1—O1	137.26 (9)	O1—C1—C2	117.6 (3)
O4W—Eu1—O1	95.95 (11)	C7—C2—C3	119.8 (3)
O2W—Eu1—O1	74.72 (9)	C7—C2—C1	118.7 (3)
O1W—Eu1—O1	69.79 (9)	C3—C2—C1	121.5 (3)
O3W—Eu1—O1	71.94 (11)	C2—C3—C4	119.8 (3)
O3ⁱ—Eu1—O5W	72.39 (11)	C2—C3—H3	120.1
O4ⁱⁱ—Eu1—O5W	69.93 (10)	C4—C3—H3	120.1
O4W—Eu1—O5W	132.53 (12)	C5—C4—C3	120.3 (3)
O2W—Eu1—O5W	72.42 (11)	C5—C4—C8	119.9 (3)
O1W—Eu1—O5W	130.36 (10)	C3—C4—C8	119.8 (3)
O3W—Eu1—O5W	67.78 (10)	C4—C5—C6	119.9 (3)
O1—Eu1—O5W	130.58 (11)	C4—C5—H5	120.1
O3ⁱ—Eu1—O2	80.16 (8)	C6—C5—H5	120.1
O4ⁱⁱ—Eu1—O2	152.27 (9)	C7—C6—C5	120.0 (3)
O4W—Eu1—O2	69.93 (10)	C7—C6—S1	119.3 (2)
O2W—Eu1—O2	122.10 (9)	C5—C6—S1	120.7 (3)
O1W—Eu1—O2	98.56 (8)	C6—C7—C2	120.2 (3)
O3W—Eu1—O2	67.78 (9)	C6—C7—H7	119.9
O1—Eu1—O2	49.82 (8)	C2—C7—H7	119.9
O5W—Eu1—O2	129.85 (10)	O3—C8—O4	125.6 (3)
O5—S1—O7	113.70 (19)	O3—C8—C4	116.8 (3)
O5—S1—O6	112.2 (2)	O4—C8—C4	117.7 (3)
O7—S1—O6	110.88 (19)	N1—C9—C10	120.3 (4)
O5—S1—C6	107.16 (17)	N1—C9—H9	119.8
O7—S1—C6	106.77 (16)	C10—C9—H9	119.8
O6—S1—C6	105.62 (16)	C9—C10—C11	121.0 (3)
C1—O1—Eu1	98.7 (2)	C9—C10—H10	119.5
C1—O2—Eu1	90.40 (19)	C11—C10—H10	119.5
C8—O3—Eu1ⁱ	164.5 (2)	C10—C11—C12	116.8 (3)
C8—O4—Eu1^iv	144.6 (2)	C10—C11—C11ⁱⁱⁱ	122.1 (4)
Eu1—O1W—H11	113.1	C12—C11—C11ⁱⁱⁱ	121.0 (4)
Eu1—O1W—H12	126.6	C13—C12—C11	120.9 (3)
H11—O1W—H12	109.5	C13—C12—H12A	119.5
Eu1—O2W—H21	109.7	C11—C12—H12A	119.5
Eu1—O2W—H22	109.1	N1—C13—C12	119.6 (3)
H21—O2W—H22	109.8	N1—C13—H13	120.2
Eu1—O3W—H31	120.1	C12—C13—H13	120.2

O3ⁱ—Eu1—O1—C1	−9.5 (3)	C4—C5—C6—C7	−2.2 (5)
O4ⁱⁱ—Eu1—O1—C1	144.7 (2)	C4—C5—C6—S1	177.6 (3)
O4W—Eu1—O1—C1	59.5 (2)	O5—S1—C6—C7	−109.9 (3)
O2W—Eu1—O1—C1	−160.0 (2)	O7—S1—C6—C7	12.3 (3)
O1W—Eu1—O1—C1	123.4 (2)	O6—S1—C6—C7	130.4 (3)
O3W—Eu1—O1—C1	−73.6 (2)	O5—S1—C6—C5	70.4 (3)
O5W—Eu1—O1—C1	−110.2 (2)	O7—S1—C6—C5	−167.5 (3)
O2—Eu1—O1—C1	2.17 (19)	O6—S1—C6—C5	−49.4 (3)
O3ⁱ—Eu1—O2—C1	168.6 (2)	C5—C6—C7—C2	2.0 (5)
O4ⁱⁱ—Eu1—O2—C1	−119.5 (2)	S1—C6—C7—C2	−177.8 (3)
O4W—Eu1—O2—C1	−119.1 (2)	C3—C2—C7—C6	−1.3 (5)
O2W—Eu1—O2—C1	18.3 (2)	C1—C2—C7—C6	177.3 (3)
O1W—Eu1—O2—C1	−56.4 (2)	Eu1ⁱ—O3—C8—O4	36.9 (12)
O3W—Eu1—O2—C1	82.5 (2)	Eu1ⁱ—O3—C8—C4	−142.6 (8)
O1—Eu1—O2—C1	−2.2 (2)	Eu1^iv—O4—C8—O3	42.7 (7)
O5W—Eu1—O2—C1	111.6 (2)	Eu1^iv—O4—C8—C4	−137.8 (3)
Eu1—O2—C1—O1	3.8 (3)	C5—C4—C8—O3	−169.6 (3)
Eu1—O2—C1—C2	−176.0 (3)	C3—C4—C8—O3	8.6 (5)
Eu1—O1—C1—O2	−4.2 (4)	C5—C4—C8—O4	10.9 (5)
Eu1—O1—C1—C2	175.7 (2)	C3—C4—C8—O4	−170.9 (3)
O2—C1—C2—C7	−167.3 (3)	O8—N1—C9—C10	−179.0 (3)
O1—C1—C2—C7	12.8 (5)	C13—N1—C9—C10	0.8 (6)
O2—C1—C2—C3	11.2 (5)	N1—C9—C10—C11	0.1 (6)
O1—C1—C2—C3	−168.6 (3)	C9—C10—C11—C12	−1.5 (6)
C7—C2—C3—C4	0.8 (5)	C9—C10—C11—C11ⁱⁱⁱ	177.1 (4)
C1—C2—C3—C4	−177.7 (3)	C10—C11—C12—C13	2.2 (6)
C2—C3—C4—C5	−1.0 (5)	C11ⁱⁱⁱ—C11—C12—C13	−176.5 (4)
C2—C3—C4—C8	−179.2 (3)	O8—N1—C13—C12	179.6 (3)
C3—C4—C5—C6	1.7 (5)	C9—N1—C13—C12	−0.1 (6)
C8—C4—C5—C6	179.9 (3)	C11—C12—C13—N1	−1.4 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O8	0.84	1.87	2.673 (4)	159
O1w—H12···O6w	0.84	1.91	2.710 (4)	160
O2w—H22···O1^v	0.84	2.11	2.804 (4)	140
O2w—H21···O3w^v	0.84	2.46	3.148 (5)	140
O3w—H31···O7w	0.84	1.91	2.742 (4)	175
O3w—H32···O8w	0.84	1.87	2.704 (4)	172
O4w—H41···O8^vi	0.83	1.82	2.648 (4)	171
O4w—H42···O5^vii	0.83	2.02	2.840 (4)	166
O5w—H51···O7w	0.83	2.30	3.026 (5)	146
O6w—H62···O6^viii	0.85	2.18	2.955 (5)	151
O6w—H61···O6ⁱⁱ	0.85	2.18	2.807 (5)	130
O7w—H71···O1^v	0.84	2.49	3.191 (4)	142
O7w—H72···O7^ix	0.84	2.03	2.860 (5)	169
O8w—H81···O2ⁱ	0.85	2.17	2.867 (4)	140
O8w—H82···O5^x	0.85	2.07	2.879 (5)	159

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y+1, z; (v) −x+1, −y+2, −z; (vi) −x, −y+2, −z+1; (vii) x−1, y, z; (viii) −x+1, −y+2, −z+1; (ix) x, y, z−1; (x) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Eu(C₈H₃O₇S)(H₂O)₅]·0.5C₁₀H₈N₂O₂·3H₂O
M_r	633.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.7800 (4), 10.8978 (3), 11.4048 (3)
α, β, γ (°)	89.383 (2), 62.989 (1), 62.678 (6)
V (Å³)	1026.90 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.24
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.631, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10108, 4658, 4509
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.091, 1.20
No. of reflections	4658
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	3.40, −1.13

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), 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···O8	0.84	1.87	2.673 (4)	159
O1w—H12···O6w	0.84	1.91	2.710 (4)	160
O2w—H22···O1ⁱ	0.84	2.11	2.804 (4)	140
O2w—H21···O3wⁱ	0.84	2.46	3.148 (5)	140
O3w—H31···O7w	0.84	1.91	2.742 (4)	175
O3w—H32···O8w	0.84	1.87	2.704 (4)	172
O4w—H41···O8ⁱⁱ	0.83	1.82	2.648 (4)	171
O4w—H42···O5ⁱⁱⁱ	0.83	2.02	2.840 (4)	166
O5w—H51···O7w	0.83	2.30	3.026 (5)	146
O6w—H62···O6^iv	0.85	2.18	2.955 (5)	151
O6w—H61···O6^v	0.85	2.18	2.807 (5)	130
O7w—H71···O1ⁱ	0.84	2.49	3.191 (4)	142
O7w—H72···O7^vi	0.84	2.03	2.860 (5)	169
O8w—H81···O2^vii	0.85	2.17	2.867 (4)	140
O8w—H82···O5^viii	0.85	2.07	2.879 (5)	159

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

Acknowledgements

We thank Guangzhou University of Chinese Medicine and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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