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

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

doi:10.1107/S1600536812003467

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m226

doi:10.1107/S1600536812003467

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Poly[[diaqua(1,10-phenanthroline-κ²N,N′)(μ₃-4-sulfonatobenzene-1,2-dicarboxylato-κ⁴O¹:O²,O^2′:O⁴)erbium(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 23 January 2012; accepted 26 January 2012; online 31 January 2012)

The 4-sulfophthalate trianion in the polymeric complex, {[Er(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O}_n, bridges three water/phenanthroline-coordinated Er^III ions 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 as well as to a monodentate sulfonate group in a distorted square antiprismatic geometry. The coordinating water molecules and the lattice water molecules, one of which is disordered over two positions [major component 65 (3)%], are hydrogen bonded to the network.

Related literature

For a related aqua(1,10-phenanthroline)Eu^III derivative, see: Xiao et al. (2010 ).

Experimental

Crystal data

[Er(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O
M_r = 662.69
Monoclinic, P 2₁ /n
a = 14.3924 (1) Å
b = 9.6206 (2) Å
c = 17.4245 (3) Å
β = 105.840 (1)°
V = 2321.04 (6) Å³
Z = 4
Mo Kα radiation
μ = 3.77 mm⁻¹
T = 293 K
0.50 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.500, T_max = 1.000
7081 measured reflections
4014 independent reflections
3799 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.095
S = 1.09
4014 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 = −1.21 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 (2)	2.813 (6)	172 (7)
O1w—H12⋯O7ⁱⁱ	0.84 (1)	1.94 (2)	2.774 (6)	171 (8)
O2w—H21⋯O2	0.84 (1)	1.92 (2)	2.738 (7)	164 (7)
O2w—H22⋯O3w	0.84 (1)	1.84 (3)	2.65 (1)	162 (8)
O3w—H31⋯O7ⁱⁱⁱ	0.84 (1)	2.03 (2)	2.80 (1)	152 (4)
O3w′—H33⋯O7ⁱⁱⁱ	0.84 (1)	2.03 (2)	2.70 (2)	136 (3)
O4w—H41⋯O2^iv	0.84 (1)	2.08 (3)	2.91 (1)	170 (13)
O4w—H42⋯O3w	0.84 (1)	1.98 (8)	2.65 (1)	136 (10)
O4w—H42⋯O3w′	0.84 (1)	1.99 (4)	2.79 (2)	159 (10)
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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812003467/xu5455sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003467/xu5455Isup2.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 (Xiao et al., 2010). The title Er^III analog is instead a diaqua coordination polymer adopting a three-dimensional network motif. The 4-sulfophthalate trianion bridges three water/phenanthroline-coordinated Er^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 (Fig. 2). 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 a related aqua(1,10-phenanthroline)Eu^III derivative, see: Xiao et al. (2010).

Experimental top

4-Sulfophthalic acid (0.080 g), 1,10-phenanthroline (0.057 g), erbium trichloride hexahydrate (0.114 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. Faint pink crystals were obtained when the vessel was cooled to room temperature slowly in about 40% 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 [Er(H₂O)₂(C₁₂H₈N₂)(C₈H₃O₇S)]_n^.2nH₂O at the 570% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
	Fig. 2. Square-antiprismatic geometry of Er.

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

Crystal data top

[Er(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O	F(000) = 1300
M_r = 662.69	D_x = 1.896 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5782 reflections
a = 14.3924 (1) Å	θ = 1.6–25.0°
b = 9.6206 (2) Å	µ = 3.77 mm⁻¹
c = 17.4245 (3) Å	T = 293 K
β = 105.840 (1)°	Block, pink
V = 2321.04 (6) Å³	0.50 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4014 independent reflections
Radiation source: fine-focus sealed tube	3799 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→14
T_min = 0.500, T_max = 1.000	k = −10→11
7081 measured reflections	l = −18→20

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) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0395P)² + 16.686P] where P = (F_o² + 2F_c²)/3
4014 reflections	(Δ/σ)_max = 0.001
353 parameters	Δρ_max = 0.97 e Å⁻³
33 restraints	Δρ_min = −1.21 e Å⁻³

Crystal data top

[Er(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O	V = 2321.04 (6) Å³
M_r = 662.69	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.3924 (1) Å	µ = 3.77 mm⁻¹
b = 9.6206 (2) Å	T = 293 K
c = 17.4245 (3) Å	0.50 × 0.20 × 0.20 mm
β = 105.840 (1)°

Data collection top

Bruker SMART APEX diffractometer	4014 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3799 reflections with I > 2σ(I)
T_min = 0.500, T_max = 1.000	R_int = 0.023
7081 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	33 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0395P)² + 16.686P] where P = (F_o² + 2F_c²)/3
4014 reflections	Δρ_max = 0.97 e Å⁻³
353 parameters	Δρ_min = −1.21 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Er1	0.605750 (18)	0.47360 (3)	0.260342 (15)	0.02117 (11)
S1	0.36918 (11)	0.32578 (18)	0.16175 (9)	0.0306 (3)
O1	0.4701 (3)	0.3319 (5)	0.2100 (3)	0.0306 (10)
O2	0.3281 (4)	0.4647 (6)	0.1432 (3)	0.0458 (13)
O3	0.3114 (4)	0.2373 (7)	0.1977 (3)	0.0556 (15)
O4	0.4072 (4)	0.4853 (5)	−0.1229 (3)	0.0418 (13)
O5	0.3523 (3)	0.3144 (4)	−0.2054 (2)	0.0281 (9)
O6	0.2667 (3)	0.0313 (4)	−0.1963 (3)	0.0316 (10)
O7	0.4246 (3)	−0.0030 (5)	−0.1691 (3)	0.0376 (11)
O1w	0.6548 (3)	0.2506 (5)	0.2388 (3)	0.0363 (11)
H11	0.7135 (16)	0.234 (7)	0.260 (4)	0.054*
H12	0.628 (4)	0.181 (5)	0.213 (4)	0.054*
O2w	0.4707 (4)	0.6125 (5)	0.2474 (3)	0.0421 (12)
H21	0.421 (4)	0.582 (7)	0.215 (4)	0.063*
H22	0.471 (5)	0.6997 (12)	0.245 (5)	0.063*
O3w	0.4830 (11)	0.8838 (11)	0.2752 (10)	0.067 (4)	0.65 (3)
H31	0.491 (5)	0.915 (11)	0.2327 (18)	0.100*	0.65 (3)
H32	0.524 (9)	0.918 (16)	0.314 (2)	0.100*	0.65 (3)
O3w'	0.4387 (18)	0.872 (2)	0.2221 (18)	0.062 (7)	0.35 (3)
H33	0.491 (5)	0.915 (11)	0.2327 (18)	0.093*	0.35 (3)
H34	0.421 (13)	0.86 (3)	0.173 (4)	0.093*	0.35 (3)
O4w	0.3479 (5)	1.0333 (8)	0.3134 (5)	0.077 (2)
H41	0.293 (4)	1.015 (11)	0.320 (8)	0.116*
H42	0.362 (8)	0.972 (9)	0.284 (7)	0.116*
N1	0.5895 (4)	0.3629 (6)	0.3847 (3)	0.0305 (12)
N2	0.6445 (4)	0.6325 (6)	0.3796 (3)	0.0333 (12)
C1	0.5629 (6)	0.2322 (8)	0.3879 (4)	0.0421 (17)
H1	0.5473	0.1810	0.3408	0.051*
C2	0.5567 (7)	0.1661 (9)	0.4578 (5)	0.056 (2)
H2	0.5377	0.0735	0.4568	0.067*
C3	0.5786 (6)	0.2385 (10)	0.5265 (5)	0.053 (2)
H3	0.5750	0.1959	0.5735	0.064*
C4	0.6070 (5)	0.3794 (9)	0.5274 (4)	0.0421 (18)
C5	0.6311 (6)	0.4650 (10)	0.5974 (4)	0.052 (2)
H5	0.6265	0.4279	0.6456	0.063*
C6	0.6601 (6)	0.5979 (10)	0.5955 (4)	0.051 (2)
H6	0.6758	0.6503	0.6421	0.061*
C7	0.6671 (5)	0.6591 (9)	0.5224 (4)	0.0440 (19)
C8	0.6992 (6)	0.7949 (10)	0.5171 (5)	0.059 (2)
H8	0.7183	0.8497	0.5627	0.070*
C9	0.7025 (7)	0.8470 (9)	0.4456 (5)	0.061 (2)
H9	0.7233	0.9376	0.4418	0.073*
C10	0.6744 (6)	0.7634 (8)	0.3780 (5)	0.0468 (19)
H10	0.6766	0.8008	0.3293	0.056*
C11	0.6411 (5)	0.5800 (8)	0.4513 (4)	0.0315 (14)
C12	0.6118 (4)	0.4375 (7)	0.4544 (4)	0.0310 (14)
C13	0.3714 (4)	0.2483 (7)	0.0701 (3)	0.0275 (13)
C14	0.3788 (4)	0.3306 (7)	0.0066 (4)	0.0288 (13)
H14	0.3870	0.4262	0.0132	0.035*
C15	0.3741 (4)	0.2703 (6)	−0.0666 (3)	0.0247 (12)
C16	0.3647 (4)	0.1252 (6)	−0.0760 (3)	0.0238 (12)
C17	0.3641 (5)	0.0436 (6)	−0.0099 (4)	0.0300 (14)
H17	0.3625	−0.0528	−0.0144	0.036*
C18	0.3657 (5)	0.1048 (7)	0.0627 (4)	0.0327 (15)
H18	0.3630	0.0500	0.1060	0.039*
C19	0.3780 (4)	0.3614 (7)	−0.1350 (3)	0.0263 (13)
C20	0.3527 (4)	0.0479 (6)	−0.1535 (4)	0.0266 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Er1	0.02381 (16)	0.01893 (16)	0.02072 (16)	−0.00118 (10)	0.00599 (11)	−0.00058 (10)
S1	0.0253 (8)	0.0428 (9)	0.0233 (7)	−0.0038 (7)	0.0058 (6)	−0.0019 (7)
O1	0.024 (2)	0.029 (2)	0.032 (2)	−0.0041 (18)	−0.0026 (18)	−0.0005 (19)
O2	0.042 (3)	0.053 (3)	0.037 (3)	0.015 (2)	0.001 (2)	−0.006 (2)
O3	0.054 (3)	0.080 (4)	0.039 (3)	−0.030 (3)	0.023 (3)	−0.009 (3)
O4	0.076 (4)	0.023 (2)	0.026 (2)	−0.013 (2)	0.013 (2)	0.0003 (19)
O5	0.033 (2)	0.022 (2)	0.027 (2)	−0.0055 (18)	0.0060 (18)	0.0010 (17)
O6	0.027 (2)	0.027 (2)	0.037 (2)	−0.0018 (18)	0.0021 (19)	−0.0045 (19)
O7	0.027 (2)	0.036 (3)	0.048 (3)	0.003 (2)	0.007 (2)	−0.012 (2)
O1w	0.030 (2)	0.020 (2)	0.057 (3)	0.0006 (19)	0.008 (2)	−0.014 (2)
O2w	0.036 (3)	0.027 (3)	0.063 (3)	0.004 (2)	0.014 (2)	−0.002 (2)
O3w	0.082 (7)	0.046 (5)	0.081 (8)	0.004 (5)	0.040 (6)	0.004 (5)
O3w'	0.058 (10)	0.059 (9)	0.075 (11)	0.009 (7)	0.029 (8)	0.004 (8)
O4w	0.067 (4)	0.084 (5)	0.093 (5)	0.010 (4)	0.044 (4)	0.009 (4)
N1	0.033 (3)	0.033 (3)	0.026 (3)	−0.003 (2)	0.008 (2)	0.003 (2)
N2	0.038 (3)	0.035 (3)	0.030 (3)	−0.008 (2)	0.014 (2)	−0.008 (2)
C1	0.056 (5)	0.032 (4)	0.040 (4)	−0.005 (3)	0.017 (3)	0.010 (3)
C2	0.069 (6)	0.049 (5)	0.055 (5)	−0.006 (4)	0.025 (4)	0.022 (4)
C3	0.055 (5)	0.069 (6)	0.040 (4)	0.004 (4)	0.022 (4)	0.023 (4)
C4	0.036 (4)	0.065 (5)	0.024 (3)	0.005 (3)	0.008 (3)	0.008 (3)
C5	0.050 (5)	0.091 (7)	0.018 (3)	0.020 (5)	0.013 (3)	0.007 (4)
C6	0.051 (5)	0.070 (6)	0.032 (4)	0.014 (4)	0.011 (3)	−0.011 (4)
C7	0.031 (4)	0.065 (5)	0.035 (4)	0.003 (3)	0.008 (3)	−0.016 (4)
C8	0.058 (5)	0.069 (6)	0.047 (5)	−0.012 (4)	0.011 (4)	−0.030 (4)
C9	0.078 (6)	0.046 (5)	0.062 (6)	−0.019 (4)	0.026 (5)	−0.025 (4)
C10	0.062 (5)	0.033 (4)	0.052 (5)	−0.009 (4)	0.025 (4)	−0.012 (3)
C11	0.029 (3)	0.042 (4)	0.024 (3)	−0.002 (3)	0.008 (3)	−0.007 (3)
C12	0.028 (3)	0.045 (4)	0.021 (3)	0.004 (3)	0.008 (3)	0.001 (3)
C13	0.024 (3)	0.035 (3)	0.022 (3)	−0.001 (3)	0.003 (2)	−0.001 (3)
C14	0.029 (3)	0.027 (3)	0.031 (3)	−0.002 (3)	0.009 (3)	0.000 (3)
C15	0.025 (3)	0.026 (3)	0.019 (3)	0.001 (2)	0.001 (2)	−0.001 (2)
C16	0.020 (3)	0.025 (3)	0.023 (3)	0.003 (2)	0.001 (2)	0.002 (2)
C17	0.036 (3)	0.022 (3)	0.028 (3)	0.001 (3)	0.001 (3)	0.000 (2)
C18	0.032 (3)	0.037 (4)	0.025 (3)	−0.003 (3)	0.000 (3)	0.009 (3)
C19	0.029 (3)	0.029 (3)	0.019 (3)	0.000 (3)	0.005 (2)	−0.004 (2)
C20	0.023 (3)	0.024 (3)	0.033 (3)	−0.002 (2)	0.008 (3)	0.002 (3)

Geometric parameters (Å, º) top

Er1—O6ⁱ	2.233 (4)	N2—C10	1.334 (9)
Er1—O2w	2.319 (5)	N2—C11	1.362 (8)
Er1—O1w	2.321 (4)	C1—C2	1.399 (10)
Er1—O1	2.346 (4)	C1—H1	0.9300
Er1—O4ⁱⁱ	2.384 (5)	C2—C3	1.346 (12)
Er1—O5ⁱⁱ	2.399 (4)	C2—H2	0.9300
Er1—N1	2.483 (5)	C3—C4	1.414 (12)
Er1—N2	2.516 (5)	C3—H3	0.9300
S1—O3	1.447 (5)	C4—C12	1.409 (9)
S1—O2	1.462 (5)	C4—C5	1.434 (11)
S1—O1	1.468 (4)	C5—C6	1.348 (13)
S1—C13	1.771 (6)	C5—H5	0.9300
O4—C19	1.263 (8)	C6—C7	1.430 (11)
O4—Er1ⁱⁱ	2.384 (5)	C6—H6	0.9300
O5—C19	1.264 (7)	C7—C8	1.398 (13)
O5—Er1ⁱⁱ	2.399 (4)	C7—C11	1.415 (9)
O6—C20	1.268 (8)	C8—C9	1.356 (13)
O6—Er1ⁱⁱⁱ	2.233 (4)	C8—H8	0.9300
O7—C20	1.240 (8)	C9—C10	1.392 (11)
O1w—H11	0.84 (1)	C9—H9	0.9300
O1w—H12	0.84 (1)	C10—H10	0.9300
O2w—H21	0.84 (1)	C11—C12	1.439 (10)
O2w—H22	0.84 (1)	C13—C18	1.386 (9)
O3w—H31	0.84 (1)	C13—C14	1.388 (9)
O3w—H32	0.84 (1)	C14—C15	1.385 (8)
O3w—H33	0.84 (1)	C14—H14	0.9300
O3w'—H31	0.84 (1)	C15—C16	1.408 (9)
O3w'—H33	0.84 (1)	C15—C19	1.494 (8)
O3w'—H34	0.84 (1)	C16—C17	1.397 (9)
O4w—H41	0.84 (1)	C16—C20	1.510 (8)
O4w—H42	0.84 (1)	C17—C18	1.390 (9)
N1—C1	1.320 (9)	C17—H17	0.9300
N1—C12	1.371 (8)	C18—H18	0.9300

O6ⁱ—Er1—O2w	144.10 (17)	C3—C2—C1	118.9 (8)
O6ⁱ—Er1—O1w	72.66 (16)	C3—C2—H2	120.5
O2w—Er1—O1w	143.22 (17)	C1—C2—H2	120.5
O6ⁱ—Er1—O1	142.63 (15)	C2—C3—C4	120.2 (7)
O2w—Er1—O1	73.08 (17)	C2—C3—H3	119.9
O1w—Er1—O1	70.17 (16)	C4—C3—H3	119.9
O6ⁱ—Er1—O4ⁱⁱ	97.62 (19)	C12—C4—C3	117.1 (7)
O2w—Er1—O4ⁱⁱ	88.5 (2)	C12—C4—C5	118.7 (8)
O1w—Er1—O4ⁱⁱ	86.24 (18)	C3—C4—C5	124.2 (7)
O1—Er1—O4ⁱⁱ	83.77 (16)	C6—C5—C4	121.9 (7)
O6ⁱ—Er1—O5ⁱⁱ	78.60 (15)	C6—C5—H5	119.1
O2w—Er1—O5ⁱⁱ	76.50 (17)	C4—C5—H5	119.1
O1w—Er1—O5ⁱⁱ	126.94 (16)	C5—C6—C7	120.7 (7)
O1—Er1—O5ⁱⁱ	128.25 (14)	C5—C6—H6	119.7
O4ⁱⁱ—Er1—O5ⁱⁱ	54.39 (15)	C7—C6—H6	119.7
O6ⁱ—Er1—N1	91.84 (17)	C8—C7—C11	117.3 (7)
O2w—Er1—N1	93.20 (19)	C8—C7—C6	123.2 (7)
O1w—Er1—N1	81.37 (18)	C11—C7—C6	119.5 (8)
O1—Er1—N1	79.05 (16)	C9—C8—C7	120.1 (7)
O4ⁱⁱ—Er1—N1	161.43 (17)	C9—C8—H8	120.0
O5ⁱⁱ—Er1—N1	143.79 (16)	C7—C8—H8	120.0
O6ⁱ—Er1—N2	75.99 (17)	C8—C9—C10	119.3 (8)
O2w—Er1—N2	73.81 (19)	C8—C9—H9	120.4
O1w—Er1—N2	133.36 (19)	C10—C9—H9	120.4
O1—Er1—N2	129.52 (16)	N2—C10—C9	123.3 (8)
O4ⁱⁱ—Er1—N2	131.89 (17)	N2—C10—H10	118.3
O5ⁱⁱ—Er1—N2	77.84 (16)	C9—C10—H10	118.3
N1—Er1—N2	65.95 (18)	N2—C11—C7	122.5 (7)
O3—S1—O2	112.9 (4)	N2—C11—C12	118.2 (5)
O3—S1—O1	111.8 (3)	C7—C11—C12	119.3 (6)
O2—S1—O1	111.6 (3)	N1—C12—C4	122.3 (7)
O3—S1—C13	107.3 (3)	N1—C12—C11	117.8 (5)
O2—S1—C13	106.9 (3)	C4—C12—C11	119.9 (6)
O1—S1—C13	105.9 (3)	C18—C13—C14	120.7 (6)
S1—O1—Er1	146.1 (3)	C18—C13—S1	119.1 (5)
C19—O4—Er1ⁱⁱ	93.2 (4)	C14—C13—S1	120.2 (5)
C19—O5—Er1ⁱⁱ	92.5 (4)	C15—C14—C13	119.9 (6)
C20—O6—Er1ⁱⁱⁱ	163.2 (4)	C15—C14—H14	120.0
Er1—O1w—H11	115 (4)	C13—C14—H14	120.0
Er1—O1w—H12	136 (4)	C14—C15—C16	120.1 (6)
H11—O1w—H12	110 (2)	C14—C15—C19	119.1 (5)
Er1—O2w—H21	114 (6)	C16—C15—C19	120.8 (5)
Er1—O2w—H22	125 (6)	C17—C16—C15	118.9 (5)
H21—O2w—H22	109 (2)	C17—C16—C20	115.9 (5)
H31—O3w—H32	110 (2)	C15—C16—C20	125.2 (5)
H32—O3w—H33	110 (2)	C18—C17—C16	120.7 (6)
H31—O3w'—H34	109 (2)	C18—C17—H17	119.6
H33—O3w'—H34	109 (2)	C16—C17—H17	119.6
H41—O4w—H42	109 (2)	C13—C18—C17	119.4 (6)
C1—N1—C12	117.6 (6)	C13—C18—H18	120.3
C1—N1—Er1	122.9 (5)	C17—C18—H18	120.3
C12—N1—Er1	119.5 (4)	O4—C19—O5	119.8 (6)
C10—N2—C11	117.5 (6)	O4—C19—C15	120.2 (5)
C10—N2—Er1	123.9 (5)	O5—C19—C15	120.0 (5)
C11—N2—Er1	118.5 (4)	O7—C20—O6	124.1 (6)
N1—C1—C2	123.9 (7)	O7—C20—C16	119.4 (5)
N1—C1—H1	118.0	O6—C20—C16	116.3 (5)
C2—C1—H1	118.0

O3—S1—O1—Er1	−138.7 (5)	C8—C9—C10—N2	−0.5 (14)
O2—S1—O1—Er1	−11.2 (6)	C10—N2—C11—C7	0.5 (10)
C13—S1—O1—Er1	104.8 (5)	Er1—N2—C11—C7	176.3 (5)
O6ⁱ—Er1—O1—S1	−155.0 (4)	C10—N2—C11—C12	−178.1 (6)
O2w—Er1—O1—S1	29.7 (5)	Er1—N2—C11—C12	−2.3 (8)
O1w—Er1—O1—S1	−148.9 (5)	C8—C7—C11—N2	−1.4 (11)
O4ⁱⁱ—Er1—O1—S1	−60.6 (5)	C6—C7—C11—N2	178.9 (6)
O5ⁱⁱ—Er1—O1—S1	−26.9 (6)	C8—C7—C11—C12	177.2 (7)
N1—Er1—O1—S1	126.5 (5)	C6—C7—C11—C12	−2.5 (10)
N2—Er1—O1—S1	80.7 (5)	C1—N1—C12—C4	−0.1 (10)
O6ⁱ—Er1—N1—C1	−106.2 (6)	Er1—N1—C12—C4	−178.0 (5)
O2w—Er1—N1—C1	109.3 (6)	C1—N1—C12—C11	179.9 (6)
O1w—Er1—N1—C1	−34.1 (5)	Er1—N1—C12—C11	2.0 (7)
O1—Er1—N1—C1	37.3 (5)	C3—C4—C12—N1	0.5 (10)
O4ⁱⁱ—Er1—N1—C1	14.6 (9)	C5—C4—C12—N1	−179.6 (6)
O5ⁱⁱ—Er1—N1—C1	−179.3 (5)	C3—C4—C12—C11	−179.5 (6)
N2—Er1—N1—C1	−180.0 (6)	C5—C4—C12—C11	0.4 (10)
O6ⁱ—Er1—N1—C12	71.5 (5)	N2—C11—C12—N1	0.3 (9)
O2w—Er1—N1—C12	−72.9 (5)	C7—C11—C12—N1	−178.4 (6)
O1w—Er1—N1—C12	143.7 (5)	N2—C11—C12—C4	−179.8 (6)
O1—Er1—N1—C12	−145.0 (5)	C7—C11—C12—C4	1.6 (9)
O4ⁱⁱ—Er1—N1—C12	−167.6 (5)	O3—S1—C13—C18	−30.7 (6)
O5ⁱⁱ—Er1—N1—C12	−1.6 (6)	O2—S1—C13—C18	−152.0 (5)
N2—Er1—N1—C12	−2.2 (4)	O1—S1—C13—C18	88.9 (5)
O6ⁱ—Er1—N2—C10	79.3 (6)	O3—S1—C13—C14	149.3 (5)
O2w—Er1—N2—C10	−81.0 (6)	O2—S1—C13—C14	28.0 (6)
O1w—Er1—N2—C10	128.2 (6)	O1—S1—C13—C14	−91.1 (5)
O1—Er1—N2—C10	−131.8 (6)	C18—C13—C14—C15	4.3 (9)
O4ⁱⁱ—Er1—N2—C10	−8.4 (7)	S1—C13—C14—C15	−175.7 (5)
O5ⁱⁱ—Er1—N2—C10	−1.8 (6)	C13—C14—C15—C16	−1.9 (9)
N1—Er1—N2—C10	177.8 (6)	C13—C14—C15—C19	177.4 (6)
O6ⁱ—Er1—N2—C11	−96.1 (5)	C14—C15—C16—C17	−2.5 (9)
O2w—Er1—N2—C11	103.5 (5)	C19—C15—C16—C17	178.2 (6)
O1w—Er1—N2—C11	−47.3 (6)	C14—C15—C16—C20	176.1 (5)
O1—Er1—N2—C11	52.7 (5)	C19—C15—C16—C20	−3.2 (9)
O4ⁱⁱ—Er1—N2—C11	176.2 (4)	C15—C16—C17—C18	4.6 (9)
O5ⁱⁱ—Er1—N2—C11	−177.2 (5)	C20—C16—C17—C18	−174.1 (6)
N1—Er1—N2—C11	2.3 (4)	C14—C13—C18—C17	−2.2 (10)
C12—N1—C1—C2	−0.3 (11)	S1—C13—C18—C17	177.8 (5)
Er1—N1—C1—C2	177.5 (6)	C16—C17—C18—C13	−2.3 (10)
N1—C1—C2—C3	0.2 (13)	Er1ⁱⁱ—O4—C19—O5	−2.9 (6)
C1—C2—C3—C4	0.2 (13)	Er1ⁱⁱ—O4—C19—C15	176.8 (5)
C2—C3—C4—C12	−0.5 (12)	Er1ⁱⁱ—O5—C19—O4	2.8 (6)
C2—C3—C4—C5	179.6 (8)	Er1ⁱⁱ—O5—C19—C15	−176.9 (5)
C12—C4—C5—C6	−1.6 (11)	C14—C15—C19—O4	16.2 (9)
C3—C4—C5—C6	178.3 (8)	C16—C15—C19—O4	−164.5 (6)
C4—C5—C6—C7	0.6 (12)	C14—C15—C19—O5	−164.1 (6)
C5—C6—C7—C8	−178.2 (8)	C16—C15—C19—O5	15.2 (9)
C5—C6—C7—C11	1.4 (11)	Er1ⁱⁱⁱ—O6—C20—O7	165.7 (11)
C11—C7—C8—C9	1.4 (12)	Er1ⁱⁱⁱ—O6—C20—C16	−9.2 (18)
C6—C7—C8—C9	−178.9 (8)	C17—C16—C20—O7	−85.4 (7)
C7—C8—C9—C10	−0.5 (14)	C15—C16—C20—O7	96.0 (8)
C11—N2—C10—C9	0.5 (12)	C17—C16—C20—O6	89.7 (7)
Er1—N2—C10—C9	−175.0 (7)	C15—C16—C20—O6	−88.8 (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 (2)	2.813 (6)	172 (7)
O1w—H12···O7^iv	0.84 (1)	1.94 (2)	2.774 (6)	171 (8)
O2w—H21···O2	0.84 (1)	1.92 (2)	2.738 (7)	164 (7)
O2w—H22···O3w	0.84 (1)	1.84 (3)	2.65 (1)	162 (8)
O3w—H31···O7ⁱⁱ	0.84 (1)	2.03 (2)	2.80 (1)	152 (4)
O3w′—H33···O7ⁱⁱ	0.84 (1)	2.03 (2)	2.70 (2)	136 (3)
O4w—H41···O2^v	0.84 (1)	2.08 (3)	2.91 (1)	170 (13)
O4w—H42···O3w	0.84 (1)	1.98 (8)	2.65 (1)	136 (10)
O4w—H42···O3w′	0.84 (1)	1.99 (4)	2.79 (2)	159 (10)

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.

Experimental details

Crystal data
Chemical formula	[Er(C₈H₃O₇S)(C₁₂H₈N₂)(H₂O)₂]·2H₂O
M_r	662.69
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.3924 (1), 9.6206 (2), 17.4245 (3)
β (°)	105.840 (1)
V (Å³)	2321.04 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.77
Crystal size (mm)	0.50 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.500, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7081, 4014, 3799
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.095, 1.09
No. of reflections	4014
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) + (0.0395P)² + 16.686P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.97, −1.21

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 (2)	2.813 (6)	172 (7)
O1w—H12···O7ⁱⁱ	0.84 (1)	1.94 (2)	2.774 (6)	171 (8)
O2w—H21···O2	0.84 (1)	1.92 (2)	2.738 (7)	164 (7)
O2w—H22···O3w	0.84 (1)	1.84 (3)	2.65 (1)	162 (8)
O3w—H31···O7ⁱⁱⁱ	0.84 (1)	2.03 (2)	2.80 (1)	152 (4)
O3w'—H33···O7ⁱⁱⁱ	0.84 (1)	2.03 (2)	2.70 (2)	136 (3)
O4w—H41···O2^iv	0.84 (1)	2.08 (3)	2.91 (1)	170 (13)
O4w—H42···O3w	0.84 (1)	1.98 (8)	2.65 (1)	136 (10)
O4w—H42···O3w'	0.84 (1)	1.99 (4)	2.79 (2)	159 (10)

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.

Acknowledgements

The authors thank the Priority Academic Program Development 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

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Xiao, S.-S., Zheng, X.-J., Yan, S.-H. & Deng, X.-B. (2010). CrystEngComm, 12, 3145–3151. CrossRef CAS Google Scholar

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