catena-Poly[[[penta­aqua­cerium(III)]-μ-pyridine-2,4,6-tricarboxyl­ato-κ4N,O2,O6:O6′] tetra­hydrate]

Sharif, S.; Khan, I.U.; Zaheer, S.; Ng, S.W.

doi:10.1107/S1600536812015887

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m624-m625

doi:10.1107/S1600536812015887

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catena-Poly[[[pentaaquacerium(III)]-μ-pyridine-2,4,6-tricarboxylato-κ⁴N,O²,O⁶:O^6′] tetrahydrate]

Shahzad Sharif,^a Islam Ullah Khan,^a Samia Zaheer ^a and Seik Weng Ng ^b,^c ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore, Pakistan, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 4 April 2012; accepted 11 April 2012; online 18 April 2012)

The Ce^III atom in the title compound, {[Ce(C₈H₂NO₆)(H₂O)₅]·4H₂O}_n, is N,O,O′-chelated by the carboxylate trianion and is coordinated by five water molecules; a carboxyl O atom from an adjacent trianion bridges the Ce^III atom, resulting in a chain running along the a axis. The nine atoms surrounding the metal atom comprise a tricapped trigonal-prismatic polyhedron. The coordinated and lattice water molecules interact with each other and with the carboxyl O atoms by O—H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For the isotypic Sm^III, Eu^III, Tb^III and Ho^III analogs, see: Wang et al. (2007 ). For the synthesis of 2,4,6-pyridinetricarboxylic acid, see: Syper et al. (1980 ).

Experimental

Crystal data

[Ce(C₈H₂NO₆)(H₂O)₅]·4H₂O
M_r = 510.37
Orthorhombic, P n a 2₁
a = 6.8437 (3) Å
b = 13.3207 (5) Å
c = 17.9045 (7) Å
V = 1632.23 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.87 mm⁻¹
T = 293 K
0.21 × 0.06 × 0.04 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.584, T_max = 0.894
19512 measured reflections
3690 independent reflections
3336 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.078
S = 1.07
3690 reflections
226 parameters
25 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.51 e Å⁻³
Absolute structure: Flack (1983 ), 1757 Friedel pairs
Flack parameter: −0.05 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H12⋯O6wⁱ	0.84	2.00	2.789 (7)	157
O1w—H11⋯O5ⁱⁱ	0.84	2.00	2.723 (7)	144
O2w—H21⋯O3ⁱⁱⁱ	0.84	2.05	2.762 (7)	142
O2w—H22⋯O6w	0.84	2.31	2.699 (7)	109
O3w—H31⋯O9w	0.84	1.89	2.710 (10)	165
O4w—H41⋯O4ⁱⁱ	0.84	2.03	2.693 (7)	136
O4w—H42⋯O4ⁱⁱⁱ	0.84	2.02	2.713 (7)	139
O5w—H52⋯O7w	0.84	2.25	2.762 (9)	119
O6w—H61⋯O1^iv	0.84	2.04	2.751 (7)	142
O6w—H62⋯O8wⁱⁱ	0.84	2.09	2.825 (9)	146
O7w—H71⋯O3^iv	0.84	1.99	2.818 (9)	169
O7w—H72⋯O8w^v	0.84	2.36	3.169 (10)	162
O8w—H81⋯O5	0.84	2.22	2.778 (8)	124
O8w—H82⋯O9w	0.84	2.45	2.756 (11)	103
O9w—H91⋯O4w^vi	0.84	2.29	2.895 (9)	130
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (v) x+1, y, z; (vi) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2011); 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/S1600536812015887/xu5510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015887/xu5510Isup2.hkl

checkCIF report

Comment top

Some lanthanide coordination polymers of 2,4,6-pyridinetricarboxylic acid exhibit photoluminescence; the Sm, Eu, Tb and Ho derivatives are isostructural pentaaqua-coordinated tetrahydrates having the rare-earth atoms in tricapped trigonal prismatic geometries (Wang et al., 2007). The cerium analog is also isostructural; The Ce(III) atom in Ce(H₂O)₅(C₈H₂NO₆)^.4H₂O (Scheme I, Fig. 1) is N,O,O'-chelated by the carboxylate trianion and is coordinated by five water molecules. A carboxyl O atom from an adjacent trianion results in a chain running along the a-axis of the orthorhombic unit cell. The nine atoms surrounding the metal atom comprises a tricapped trigonal prismatic polyhedron (Fig. 2). The coordinated and lattice water molecules interact by themselves and with the carboxyl O-atoms by O–H···O hydrogen bonds to generate a three-dimensional network (Table 1).

Related literature top

For the isotypic Sm^III, Eu^III, Tb^III and Ho^III analogs, see: Wang et al. (2007). For the synthesis of 2,4,6-pyridinetricarboxylic acid, see: Syper et al. (1980).

Experimental top

Pyridinetricarboxylic acid was synthesized by using a reported method (Syper et al., 1980). The compound (0.110 g, 0.5 mmol) was dissolved in water (7 ml) and added to a solution of cerium nitrate (0.054 g. 0.5 mmol) dissolved in 50% aqueous methanol (5 ml). The solution was heated for a hour, and then set aside for the growth of yellow prisms. These appeared after three weeks. mixture was refluxed for two hours. Yellow prisms like crystals were obtained after three weeks.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); 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 formular unit of polymeric Ce(H₂O)₅(C₈H₂NO₆)^.4H₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Tricapped trigonal prismatic geometry of the Ce(III) atom in Ce(H₂O)₅(C₈H₂NO₆)^.4H₂O.

catena-Poly[[[pentaaquacerium(III)]-µ-pyridine-2,4,6-tricarboxylato- κ⁴N,\<i>O²,O⁶:O^6')] tetrahydrate] top

Crystal data top

[Ce(C₈H₂NO₆)(H₂O)₅]·4H₂O	F(000) = 1012
M_r = 510.37	D_x = 2.077 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 7136 reflections
a = 6.8437 (3) Å	θ = 3.1–28.2°
b = 13.3207 (5) Å	µ = 2.87 mm⁻¹
c = 17.9045 (7) Å	T = 293 K
V = 1632.23 (11) Å³	Prism, yellow
Z = 4	0.21 × 0.06 × 0.04 mm

Data collection top

Bruker APEXII diffractometer	3690 independent reflections
Radiation source: fine-focus sealed tube	3336 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→5
T_min = 0.584, T_max = 0.894	k = −17→16
19512 measured reflections	l = −23→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0295P)² + 6.9973P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3690 reflections	Δρ_max = 0.68 e Å⁻³
226 parameters	Δρ_min = −0.51 e Å⁻³
25 restraints	Absolute structure: Flack (1983), 1757 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (2)

Crystal data top

[Ce(C₈H₂NO₆)(H₂O)₅]·4H₂O	V = 1632.23 (11) Å³
M_r = 510.37	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 6.8437 (3) Å	µ = 2.87 mm⁻¹
b = 13.3207 (5) Å	T = 293 K
c = 17.9045 (7) Å	0.21 × 0.06 × 0.04 mm

Data collection top

Bruker APEXII diffractometer	3690 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3336 reflections with I > 2σ(I)
T_min = 0.584, T_max = 0.894	R_int = 0.034
19512 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.68 e Å⁻³
S = 1.07	Δρ_min = −0.51 e Å⁻³
3690 reflections	Absolute structure: Flack (1983), 1757 Friedel pairs
226 parameters	Absolute structure parameter: −0.05 (2)
25 restraints

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

	x	y	z	U_iso*/U_eq
Ce1	0.48574 (3)	0.464973 (17)	0.49983 (4)	0.01583 (8)
O1	0.5984 (6)	0.2872 (3)	0.5134 (2)	0.0230 (10)
O2	0.6815 (6)	0.1363 (3)	0.4705 (2)	0.0245 (9)
O3	0.5476 (11)	0.0845 (5)	0.1892 (4)	0.0538 (19)
O4	0.6142 (9)	0.2190 (4)	0.1212 (3)	0.0446 (14)
O5	0.4457 (8)	0.5584 (3)	0.2552 (3)	0.0346 (11)
O6	0.4253 (7)	0.5458 (3)	0.3787 (2)	0.0279 (9)
O1w	0.3428 (7)	0.4311 (4)	0.6266 (3)	0.0392 (12)
H11	0.4322	0.4136	0.6560	0.059*
H12	0.2597	0.3850	0.6233	0.059*
O2w	0.7604 (7)	0.4543 (3)	0.5942 (3)	0.0336 (11)
H21	0.7783	0.5110	0.6135	0.050*
H22	0.8633	0.4356	0.5727	0.050*
O3w	0.1808 (6)	0.5787 (4)	0.5174 (3)	0.0368 (13)
H31	0.1733	0.6194	0.4817	0.055*
H32	0.1907	0.6105	0.5577	0.055*
O4w	0.5804 (7)	0.6370 (3)	0.5462 (3)	0.0308 (10)
H41	0.5090	0.6528	0.5826	0.046*
H42	0.6977	0.6360	0.5600	0.046*
O5w	0.8185 (7)	0.5032 (4)	0.4421 (3)	0.0386 (11)
H51	0.8272	0.5650	0.4335	0.058*
H52	0.8305	0.4712	0.4019	0.058*
O6w	1.0103 (8)	0.3123 (4)	0.6438 (3)	0.0423 (13)
H61	1.0118	0.2610	0.6165	0.063*
H62	0.9898	0.2961	0.6884	0.063*
O7w	0.9175 (12)	0.5539 (6)	0.2974 (4)	0.0593 (19)
H71	0.9540	0.5066	0.2697	0.089*
H72	1.0053	0.5977	0.3007	0.089*
O8w	0.2199 (9)	0.7304 (5)	0.2708 (4)	0.0668 (18)
H81	0.3388	0.7149	0.2686	0.100*
H82	0.1979	0.7848	0.2931	0.100*
O9w	0.1128 (17)	0.7295 (6)	0.4192 (5)	0.113 (3)
H91	0.1622	0.7812	0.4383	0.169*
H92	−0.0087	0.7384	0.4195	0.169*
N1	0.5422 (7)	0.3589 (3)	0.3789 (3)	0.0167 (9)
C1	0.6225 (7)	0.2232 (4)	0.4618 (3)	0.0174 (11)
C2	0.5789 (8)	0.2597 (4)	0.3837 (3)	0.0159 (10)
C3	0.5835 (8)	0.1987 (4)	0.3213 (4)	0.0205 (11)
H3	0.6024	0.1298	0.3262	0.025*
C4	0.5595 (8)	0.2415 (4)	0.2508 (3)	0.0201 (11)
C5	0.5308 (8)	0.3449 (4)	0.2457 (3)	0.0192 (11)
H5	0.5228	0.3763	0.1994	0.023*
C6	0.5142 (7)	0.4002 (4)	0.3112 (3)	0.0172 (10)
C7	0.4583 (8)	0.5113 (4)	0.3140 (3)	0.0199 (11)
C8	0.5716 (9)	0.1763 (5)	0.1811 (4)	0.0272 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ce1	0.02002 (12)	0.01382 (12)	0.01366 (12)	−0.00054 (9)	−0.0016 (3)	−0.0023 (2)
O1	0.041 (2)	0.0170 (17)	0.011 (3)	0.0042 (15)	−0.0039 (16)	−0.0025 (15)
O2	0.029 (2)	0.019 (2)	0.025 (2)	0.0062 (16)	−0.0011 (17)	0.0015 (16)
O3	0.082 (5)	0.035 (3)	0.045 (4)	−0.009 (3)	0.024 (3)	−0.021 (3)
O4	0.067 (4)	0.043 (3)	0.024 (3)	0.027 (3)	0.005 (2)	0.000 (2)
O5	0.058 (3)	0.027 (2)	0.019 (2)	0.011 (2)	0.003 (2)	0.0068 (19)
O6	0.043 (2)	0.021 (2)	0.019 (2)	0.0103 (19)	0.0019 (19)	−0.0015 (17)
O1w	0.040 (3)	0.062 (3)	0.016 (2)	−0.012 (2)	0.0009 (19)	0.000 (2)
O2w	0.038 (3)	0.030 (2)	0.033 (3)	0.003 (2)	−0.019 (2)	−0.010 (2)
O3w	0.033 (2)	0.040 (3)	0.038 (4)	0.0065 (19)	0.0004 (19)	−0.012 (2)
O4w	0.032 (2)	0.025 (2)	0.036 (3)	0.0027 (18)	−0.004 (2)	−0.0116 (19)
O5w	0.031 (2)	0.051 (3)	0.033 (3)	−0.006 (2)	0.005 (2)	−0.007 (2)
O6w	0.055 (3)	0.034 (3)	0.038 (3)	0.004 (2)	0.003 (2)	−0.007 (2)
O7w	0.065 (4)	0.065 (4)	0.048 (4)	0.003 (3)	0.010 (3)	0.003 (3)
O8w	0.057 (4)	0.067 (4)	0.077 (4)	0.014 (3)	−0.002 (3)	0.001 (3)
O9w	0.172 (8)	0.076 (5)	0.090 (5)	0.046 (5)	−0.008 (6)	−0.014 (4)
N1	0.018 (2)	0.016 (2)	0.017 (2)	0.0018 (17)	−0.0022 (17)	−0.0001 (18)
C1	0.015 (2)	0.014 (3)	0.023 (3)	−0.0001 (19)	−0.002 (2)	0.002 (2)
C2	0.017 (2)	0.013 (2)	0.018 (3)	0.0021 (19)	0.000 (2)	−0.002 (2)
C3	0.018 (3)	0.018 (3)	0.026 (3)	0.001 (2)	−0.001 (2)	0.001 (2)
C4	0.018 (2)	0.022 (3)	0.020 (3)	0.003 (2)	0.004 (2)	−0.002 (2)
C5	0.021 (3)	0.022 (3)	0.015 (3)	0.003 (2)	0.000 (2)	−0.001 (2)
C6	0.018 (2)	0.019 (3)	0.015 (3)	−0.0012 (19)	0.001 (2)	0.001 (2)
C7	0.024 (3)	0.018 (3)	0.018 (3)	0.001 (2)	0.001 (2)	0.003 (2)
C8	0.028 (3)	0.034 (3)	0.020 (3)	0.006 (3)	−0.004 (2)	−0.010 (3)

Geometric parameters (Å, º) top

Ce1—O6	2.456 (4)	O4w—H42	0.8399
Ce1—O1	2.502 (4)	O5w—H51	0.8400
Ce1—O1w	2.512 (5)	O5w—H52	0.8399
Ce1—O4w	2.523 (4)	O6w—H61	0.8399
Ce1—O2w	2.532 (4)	O6w—H62	0.8401
Ce1—O2ⁱ	2.536 (4)	O7w—H71	0.8399
Ce1—O5w	2.552 (5)	O7w—H72	0.8401
Ce1—O3w	2.598 (4)	O8w—H81	0.8400
Ce1—N1	2.615 (5)	O8w—H82	0.8400
O1—C1	1.268 (6)	O9w—H91	0.8400
O2—C1	1.237 (6)	O9w—H92	0.8399
O2—Ce1ⁱⁱ	2.536 (4)	N1—C6	1.344 (7)
O3—C8	1.242 (9)	N1—C2	1.347 (7)
O4—C8	1.249 (8)	C1—C2	1.509 (8)
O5—C7	1.228 (7)	C2—C3	1.383 (8)
O6—C7	1.266 (7)	C3—C4	1.394 (8)
O1w—H11	0.8399	C3—H3	0.9300
O1w—H12	0.8400	C4—C5	1.395 (8)
O2w—H21	0.8399	C4—C8	1.523 (8)
O2w—H22	0.8400	C5—C6	1.390 (8)
O3w—H31	0.8401	C5—H5	0.9300
O3w—H32	0.8399	C6—C7	1.530 (8)
O4w—H41	0.8401

O6—Ce1—O1	123.53 (13)	Ce1—O2w—H22	109.5
O6—Ce1—O1w	144.17 (17)	H21—O2w—H22	109.5
O1—Ce1—O1w	82.09 (16)	Ce1—O3w—H31	109.5
O6—Ce1—O4w	86.32 (15)	Ce1—O3w—H32	109.5
O1—Ce1—O4w	138.49 (14)	H31—O3w—H32	109.5
O1w—Ce1—O4w	88.02 (17)	Ce1—O4w—H41	109.4
O6—Ce1—O2w	137.65 (17)	Ce1—O4w—H42	109.1
O1—Ce1—O2w	69.70 (14)	H41—O4w—H42	109.5
O1w—Ce1—O2w	71.10 (17)	Ce1—O5w—H51	109.4
O4w—Ce1—O2w	68.94 (14)	Ce1—O5w—H52	109.5
O6—Ce1—O2ⁱ	84.95 (15)	H51—O5w—H52	109.5
O1—Ce1—O2ⁱ	76.68 (13)	H61—O6w—H62	110.3
O1w—Ce1—O2ⁱ	76.83 (15)	H71—O7w—H72	110.5
O4w—Ce1—O2ⁱ	139.67 (14)	H81—O8w—H82	114.1
O2w—Ce1—O2ⁱ	135.89 (16)	H91—O9w—H92	106.3
O6—Ce1—O5w	72.86 (17)	C6—N1—C2	119.1 (5)
O1—Ce1—O5w	87.32 (17)	C6—N1—Ce1	120.3 (4)
O1w—Ce1—O5w	138.51 (17)	C2—N1—Ce1	120.3 (3)
O4w—Ce1—O5w	73.92 (17)	O2—C1—O1	125.5 (5)
O2w—Ce1—O5w	67.60 (18)	O2—C1—C2	118.9 (5)
O2ⁱ—Ce1—O5w	139.01 (16)	O1—C1—C2	115.6 (4)
O6—Ce1—O3w	73.51 (15)	N1—C2—C3	121.9 (5)
O1—Ce1—O3w	141.96 (15)	N1—C2—C1	114.4 (4)
O1w—Ce1—O3w	71.48 (17)	C3—C2—C1	123.7 (5)
O4w—Ce1—O3w	68.68 (14)	C2—C3—C4	119.2 (5)
O2w—Ce1—O3w	123.26 (15)	C2—C3—H3	120.4
O2ⁱ—Ce1—O3w	71.08 (13)	C4—C3—H3	120.4
O5w—Ce1—O3w	130.50 (17)	C3—C4—C5	118.7 (5)
O6—Ce1—N1	62.00 (14)	C3—C4—C8	120.1 (5)
O1—Ce1—N1	61.53 (13)	C5—C4—C8	121.1 (5)
O1w—Ce1—N1	135.14 (16)	C6—C5—C4	118.6 (5)
O4w—Ce1—N1	136.56 (16)	C6—C5—H5	120.7
O2w—Ce1—N1	114.37 (15)	C4—C5—H5	120.7
O2ⁱ—Ce1—N1	70.25 (14)	N1—C6—C5	122.2 (5)
O5w—Ce1—N1	68.94 (16)	N1—C6—C7	113.8 (5)
O3w—Ce1—N1	122.29 (14)	C5—C6—C7	124.1 (5)
C1—O1—Ce1	127.3 (3)	O5—C7—O6	125.9 (5)
C1—O2—Ce1ⁱⁱ	142.4 (4)	O5—C7—C6	118.9 (5)
C7—O6—Ce1	128.2 (4)	O6—C7—C6	115.1 (5)
Ce1—O1w—H11	109.4	O3—C8—O4	125.4 (7)
Ce1—O1w—H12	109.4	O3—C8—C4	117.3 (6)
H11—O1w—H12	109.5	O4—C8—C4	117.2 (6)
Ce1—O2w—H21	109.4

O6—Ce1—O1—C1	−4.4 (5)	Ce1ⁱⁱ—O2—C1—C2	105.5 (6)
O1w—Ce1—O1—C1	148.5 (5)	Ce1—O1—C1—O2	178.7 (4)
O4w—Ce1—O1—C1	−133.6 (4)	Ce1—O1—C1—C2	0.4 (7)
O2w—Ce1—O1—C1	−138.8 (5)	C6—N1—C2—C3	−1.8 (8)
O2ⁱ—Ce1—O1—C1	70.2 (4)	Ce1—N1—C2—C3	171.2 (4)
O5w—Ce1—O1—C1	−71.7 (5)	C6—N1—C2—C1	175.7 (5)
O3w—Ce1—O1—C1	102.7 (5)	Ce1—N1—C2—C1	−11.3 (6)
N1—Ce1—O1—C1	−4.3 (4)	O2—C1—C2—N1	−171.1 (5)
O1—Ce1—O6—C7	−6.2 (6)	O1—C1—C2—N1	7.3 (7)
O1w—Ce1—O6—C7	−135.7 (5)	O2—C1—C2—C3	6.3 (8)
O4w—Ce1—O6—C7	142.8 (5)	O1—C1—C2—C3	−175.2 (5)
O2w—Ce1—O6—C7	90.0 (5)	N1—C2—C3—C4	3.4 (8)
O2ⁱ—Ce1—O6—C7	−76.6 (5)	C1—C2—C3—C4	−173.9 (5)
O5w—Ce1—O6—C7	68.5 (5)	C2—C3—C4—C5	−0.3 (8)
O3w—Ce1—O6—C7	−148.3 (5)	C2—C3—C4—C8	177.7 (5)
N1—Ce1—O6—C7	−6.3 (5)	C3—C4—C5—C6	−4.2 (8)
O6—Ce1—N1—C6	1.1 (4)	C8—C4—C5—C6	177.8 (5)
O1—Ce1—N1—C6	−178.8 (4)	C2—N1—C6—C5	−3.0 (8)
O1w—Ce1—N1—C6	141.2 (4)	Ce1—N1—C6—C5	−176.0 (4)
O4w—Ce1—N1—C6	−47.1 (5)	C2—N1—C6—C7	175.5 (5)
O2w—Ce1—N1—C6	−131.6 (4)	Ce1—N1—C6—C7	2.6 (6)
O2ⁱ—Ce1—N1—C6	96.0 (4)	C4—C5—C6—N1	6.0 (8)
O5w—Ce1—N1—C6	−80.1 (4)	C4—C5—C6—C7	−172.4 (5)
O3w—Ce1—N1—C6	45.3 (4)	Ce1—O6—C7—O5	−171.5 (5)
O6—Ce1—N1—C2	−171.8 (5)	Ce1—O6—C7—C6	9.8 (7)
O1—Ce1—N1—C2	8.3 (4)	N1—C6—C7—O5	173.9 (5)
O1w—Ce1—N1—C2	−31.7 (5)	C5—C6—C7—O5	−7.6 (8)
O4w—Ce1—N1—C2	140.1 (4)	N1—C6—C7—O6	−7.4 (7)
O2w—Ce1—N1—C2	55.5 (4)	C5—C6—C7—O6	171.1 (5)
O2ⁱ—Ce1—N1—C2	−76.9 (4)	C3—C4—C8—O3	19.8 (9)
O5w—Ce1—N1—C2	107.0 (4)	C5—C4—C8—O3	−162.2 (7)
O3w—Ce1—N1—C2	−127.5 (4)	C3—C4—C8—O4	−156.7 (6)
Ce1ⁱⁱ—O2—C1—O1	−72.8 (9)	C5—C4—C8—O4	21.2 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H12···O6wⁱⁱⁱ	0.84	2.00	2.789 (7)	157
O1w—H11···O5^iv	0.84	2.00	2.723 (7)	144
O2w—H21···O3^v	0.84	2.05	2.762 (7)	142
O2w—H22···O6w	0.84	2.31	2.699 (7)	109
O3w—H31···O9w	0.84	1.89	2.710 (10)	165
O4w—H41···O4^iv	0.84	2.03	2.693 (7)	136
O4w—H42···O4^v	0.84	2.02	2.713 (7)	139
O5w—H52···O7w	0.84	2.25	2.762 (9)	119
O6w—H61···O1ⁱⁱ	0.84	2.04	2.751 (7)	142
O6w—H62···O8w^iv	0.84	2.09	2.825 (9)	146
O7w—H71···O3ⁱⁱ	0.84	1.99	2.818 (9)	169
O7w—H72···O8w^vi	0.84	2.36	3.169 (10)	162
O8w—H81···O5	0.84	2.22	2.778 (8)	124
O8w—H82···O9w	0.84	2.45	2.756 (11)	103
O9w—H91···O4w^vii	0.84	2.29	2.895 (9)	130

Symmetry codes: (ii) x+1/2, −y+1/2, z; (iii) x−1, y, z; (iv) −x+1, −y+1, z+1/2; (v) −x+3/2, y+1/2, z+1/2; (vi) x+1, y, z; (vii) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	[Ce(C₈H₂NO₆)(H₂O)₅]·4H₂O
M_r	510.37
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	6.8437 (3), 13.3207 (5), 17.9045 (7)
V (Å³)	1632.23 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.87
Crystal size (mm)	0.21 × 0.06 × 0.04

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.584, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	19512, 3690, 3336
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.078, 1.07
No. of reflections	3690
No. of parameters	226
No. of restraints	25
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.51
Absolute structure	Flack (1983), 1757 Friedel pairs
Absolute structure parameter	−0.05 (2)

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), 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—H12···O6wⁱ	0.84	2.00	2.789 (7)	157
O1w—H11···O5ⁱⁱ	0.84	2.00	2.723 (7)	144
O2w—H21···O3ⁱⁱⁱ	0.84	2.05	2.762 (7)	142
O2w—H22···O6w	0.84	2.31	2.699 (7)	109
O3w—H31···O9w	0.84	1.89	2.710 (10)	165
O4w—H41···O4ⁱⁱ	0.84	2.03	2.693 (7)	136
O4w—H42···O4ⁱⁱⁱ	0.84	2.02	2.713 (7)	139
O5w—H52···O7w	0.84	2.25	2.762 (9)	119
O6w—H61···O1^iv	0.84	2.04	2.751 (7)	142
O6w—H62···O8wⁱⁱ	0.84	2.09	2.825 (9)	146
O7w—H71···O3^iv	0.84	1.99	2.818 (9)	169
O7w—H72···O8w^v	0.84	2.36	3.169 (10)	162
O8w—H81···O5	0.84	2.22	2.778 (8)	124
O8w—H82···O9w	0.84	2.45	2.756 (11)	103
O9w—H91···O4w^vi	0.84	2.29	2.895 (9)	130

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, z+1/2; (iii) −x+3/2, y+1/2, z+1/2; (iv) x+1/2, −y+1/2, z; (v) x+1, y, z; (vi) x−1/2, −y+3/2, z.

Acknowledgements

We thank the Higher Education Commission of Pakistan, the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) and the University of Malaya for supporting this study.

References

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