catena-Poly[[[diaqua­(nitrato-κ2O,O′)cerium(III)]-bis­[μ-2-(4-hy­droxy­phen­yl)acetato]-κ3O,O′:O;κ3O:O,O′] mono­hydrate]

Guo, H.-M.

doi:10.1107/S1600536810047239

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1602

https://doi.org/10.1107/S1600536810047239

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catena-Poly[[[diaqua(nitrato-κ²O,O′)cerium(III)]-bis[μ-2-(4-hydroxyphenyl)acetato]-κ³O,O′:O;κ³O:O,O′] monohydrate]

Hang-Ming Guo ^a ^*

^aJinhua College of Vocation and Technology, Jinhua, Zhejiang 321017, People's Republic of China
^*Correspondence e-mail: guohm8282@sina.com

(Received 7 November 2010; accepted 15 November 2010; online 20 November 2010)

In the title compound, {[Ce(C₈H₇O₃)₂(NO₃)(H₂O)₂]·H₂O}_n, the Ce^III ion is coordinated by eight O atoms from four 2-(4-hydroxyphenyl)acetate (HPAA) ligands, two O atoms from the chelating nitrate anion and two water molecules in a distorted bis-capped quadrangular prismatic geometry. The HPAA ligands coordinate in a bridging tridentate mode. In the crystal, intermolecular O—H⋯O hydrogen bonds form a three-dimensional network which consolidates the packing.

Related literature

For the crystal structures of related carboxylic metal-organic complexes, see: Liu et al. (2010 ); Fang & Zhang (2006 ); Wang et al. (2008 , 2010 ).

Experimental

Crystal data

[Ce(C₈H₇O₃)₂(NO₃)(H₂O)₂]·H₂O
M_r = 558.45
Triclinic, $[P \overline 1]$
a = 8.1151 (3) Å
b = 9.8048 (4) Å
c = 13.2396 (5) Å
α = 92.120 (2)°
β = 90.829 (2)°
γ = 112.550 (2)°
V = 971.76 (6) Å³
Z = 2
Mo Kα radiation
μ = 2.41 mm⁻¹
T = 296 K
0.14 × 0.14 × 0.03 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.716, T_max = 0.935
15535 measured reflections
4492 independent reflections
4133 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.050
S = 0.98
4492 reflections
289 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2ⁱ	0.85 (2)	1.90 (2)	2.693 (2)	156 (3)
O1W—H1WB⋯O7ⁱⁱ	0.82 (2)	2.46 (2)	3.197 (3)	150 (3)
O1W—H1WB⋯O8ⁱⁱ	0.82 (2)	2.51 (2)	3.272 (3)	156 (3)
O2W—H2WA⋯O6ⁱⁱⁱ	0.83 (2)	1.91 (2)	2.721 (2)	165 (3)
O2W—H2WB⋯O4^iv	0.84 (2)	1.95 (2)	2.783 (3)	175 (3)
O3W—H3WA⋯O4ⁱ	0.85 (2)	2.58 (2)	3.352 (4)	152 (3)
O4—H4A⋯O1^v	0.82	1.83	2.649 (3)	173
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y-1, -z+1; (iii) -x, -y, -z+1; (iv) x, y, z-1; (v) x-1, y-1, z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810047239/cv2794sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047239/cv2794Isup2.hkl

checkCIF report

Comment top

The design and synthesis of carboxylic mental-organic complexes have attracted an interest owing to their potential practical applications exhibiting fluorescence and magnetism (Wang et al., 2008, 2010; Fang et al., 2006). In a continuation of our structural studies of such compounds (Liu et al., 2010), we report here the crystal structure of the title compound (I) - a new cerium^III complex with the p-hydroxyphenylacetato ligands.

In (I), each Ce^III ion is coordinated by eight O atoms from four 4–hydroxyphenylacetato (HPAA) ligands, two O atoms from nitrate anion and two water molecules in a distorted bis-capped quadrangular prism geometry. The HPAA ligands coordinate in bridging tridentate mode (Fig.1). The Ce—O(HPAA) bond lengths range from 2.4914 (14) to 2.7245 (15) Å. The Ce—O(water) bond lengths range from 2.5444 (16) to Å-2.5463 (16) Å.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) form three-dimensional network which concolidate the packing.

Related literature top

For the crystal structures of related carboxylic metal-organic complexes, see: Liu et al. (2010); Fang & Zhang (2006); Wang et al. (2008, 2010).

Experimental top

All reagents and solvents used were of commercially available quality and without purification. p-Hydroxyphenylacetic acid (0.456 g, 3 mmol) and sodium hydroxide (0.12 g, 3 mmol) were mixed together in water(10 ml), then Ce(NO₃)₃.6H₂O(0.434 g, 1 mmol) dissolved in water (10 ml) was added into the above solution, after stirred for an hour. After filtration, the filtrate was allowed to stand at room temperature, and single crystals suitable for X–ray work were obtained after a week.

Structure description top

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) form three-dimensional network which concolidate the packing.

For the crystal structures of related carboxylic metal-organic complexes, see: Liu et al. (2010); Fang & Zhang (2006); Wang et al. (2008, 2010).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A portion of the polymeric chain of (I), showing the atom-labeling scheme [symmetry code: (A) -x, -y, 1-z]. Displacement ellipsoids are drawn at the 30% probability level.

catena-Poly[[[diaqua(nitrato-κ²O,O')cerium(III)]- bis[µ-2-(4-hydroxyphenyl)acetato]- κ³O,O':O;κ³O:O,O'] monohydrate] top

Crystal data top

[Ce(C₈H₇O₃)₂(NO₃)(H₂O)₂]·H₂O	Z = 2
M_r = 558.45	F(000) = 554
Triclinic, P1	D_x = 1.909 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1151 (3) Å	Cell parameters from 8276 reflections
b = 9.8048 (4) Å	θ = 2.3–27.7°
c = 13.2396 (5) Å	µ = 2.41 mm⁻¹
α = 92.120 (2)°	T = 296 K
β = 90.829 (2)°	Block, colourless
γ = 112.550 (2)°	0.14 × 0.14 × 0.03 mm
V = 971.76 (6) Å³

Data collection top

Bruker APEXII diffractometer	4492 independent reflections
Radiation source: fine-focus sealed tube	4133 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.7°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.716, T_max = 0.935	k = −12→12
15535 measured reflections	l = −16→17

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0337P)² + 0.0249P] where P = (F_o² + 2F_c²)/3
4492 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.72 e Å⁻³
9 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Ce(C₈H₇O₃)₂(NO₃)(H₂O)₂]·H₂O	γ = 112.550 (2)°
M_r = 558.45	V = 971.76 (6) Å³
Triclinic, P1	Z = 2
a = 8.1151 (3) Å	Mo Kα radiation
b = 9.8048 (4) Å	µ = 2.41 mm⁻¹
c = 13.2396 (5) Å	T = 296 K
α = 92.120 (2)°	0.14 × 0.14 × 0.03 mm
β = 90.829 (2)°

Data collection top

Bruker APEXII diffractometer	4492 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4133 reflections with I > 2σ(I)
T_min = 0.716, T_max = 0.935	R_int = 0.026
15535 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	9 restraints
wR(F²) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.72 e Å⁻³
4492 reflections	Δρ_min = −0.36 e Å⁻³
289 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
Ce1	0.208699 (13)	−0.089222 (12)	0.466072 (8)	0.02011 (5)
N1	0.0546 (3)	−0.3859 (2)	0.33905 (16)	0.0335 (4)
O1W	0.2726 (2)	−0.28503 (19)	0.56174 (16)	0.0402 (4)
H1WA	0.379 (2)	−0.277 (3)	0.573 (2)	0.060*
H1WB	0.214 (3)	−0.364 (2)	0.587 (2)	0.060*
O1	0.7474 (3)	0.5608 (2)	0.07849 (16)	0.0632 (6)
H1A	0.7371	0.4920	0.0384	0.095*
O2	0.3683 (2)	0.18203 (18)	0.42823 (15)	0.0372 (4)
O2W	0.0678 (2)	−0.0555 (2)	0.30083 (12)	0.0346 (4)
H2WA	−0.019 (3)	−0.031 (3)	0.304 (2)	0.052*
H2WB	0.055 (4)	−0.101 (3)	0.2447 (16)	0.052*
O3	0.09817 (19)	0.14048 (17)	0.47414 (12)	0.0290 (3)
O3W	0.7347 (4)	0.4032 (3)	−0.09596 (17)	0.0650 (6)
H3WA	0.801 (5)	0.363 (4)	−0.120 (3)	0.098*
H3WB	0.721 (6)	0.448 (4)	−0.144 (2)	0.098*
O4	0.0288 (3)	−0.1882 (3)	1.10768 (14)	0.0645 (7)
H4A	−0.0557	−0.2660	1.0935	0.097*
O5	0.4853 (2)	0.03842 (17)	0.59596 (11)	0.0272 (3)
O6	0.2196 (2)	−0.0107 (2)	0.65299 (12)	0.0358 (4)
O7	−0.0071 (3)	−0.4974 (2)	0.2852 (2)	0.0635 (7)
O8	−0.0245 (2)	−0.3651 (2)	0.41577 (15)	0.0475 (5)
O9	0.2019 (2)	−0.28460 (19)	0.32163 (14)	0.0404 (4)
C1	0.6258 (3)	0.5107 (3)	0.1536 (2)	0.0408 (6)
C2	0.6439 (4)	0.6015 (3)	0.2378 (2)	0.0428 (6)
H2A	0.7371	0.6938	0.2434	0.051*
C3	0.5227 (3)	0.5555 (3)	0.3150 (2)	0.0390 (6)
H3A	0.5352	0.6178	0.3719	0.047*
C4	0.3841 (3)	0.4185 (3)	0.3082 (2)	0.0345 (5)
C5	0.3692 (5)	0.3305 (3)	0.2238 (3)	0.0555 (8)
H5A	0.2763	0.2381	0.2182	0.067*
C6	0.4886 (4)	0.3746 (3)	0.1456 (2)	0.0592 (9)
H6A	0.4754	0.3125	0.0886	0.071*
C7	0.2519 (4)	0.3655 (3)	0.3915 (2)	0.0427 (6)
H7A	0.2849	0.4411	0.4457	0.051*
H7B	0.1347	0.3536	0.3652	0.051*
C8	0.2399 (3)	0.2229 (2)	0.43422 (17)	0.0251 (4)
C9	0.1213 (3)	−0.1356 (3)	1.02159 (19)	0.0388 (6)
C10	0.2361 (4)	0.0088 (3)	1.0244 (2)	0.0555 (8)
H10A	0.2437	0.0702	1.0810	0.067*
C11	0.3413 (4)	0.0630 (3)	0.9425 (2)	0.0553 (8)
H11A	0.4198	0.1616	0.9448	0.066*
C12	0.3332 (3)	−0.0242 (3)	0.85785 (18)	0.0353 (5)
C13	0.2135 (4)	−0.1682 (3)	0.8556 (2)	0.0459 (7)
H13A	0.2035	−0.2289	0.7983	0.055*
C14	0.1074 (4)	−0.2248 (3)	0.9369 (2)	0.0492 (7)
H14A	0.0271	−0.3227	0.9342	0.059*
C15	0.4615 (3)	0.0341 (4)	0.77382 (19)	0.0479 (7)
H15A	0.5323	0.1378	0.7900	0.058*
H15B	0.5426	−0.0173	0.7732	0.058*
C16	0.3832 (3)	0.0212 (2)	0.66965 (16)	0.0242 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ce1	0.01487 (7)	0.02446 (7)	0.01999 (7)	0.00608 (5)	0.00407 (4)	0.00347 (4)
N1	0.0315 (11)	0.0260 (9)	0.0429 (13)	0.0112 (8)	−0.0058 (9)	−0.0002 (8)
O1W	0.0236 (8)	0.0339 (9)	0.0607 (13)	0.0071 (7)	−0.0001 (8)	0.0178 (8)
O1	0.0624 (14)	0.0546 (12)	0.0442 (13)	−0.0094 (10)	0.0298 (11)	−0.0038 (9)
O2	0.0210 (8)	0.0335 (9)	0.0589 (12)	0.0109 (7)	0.0102 (8)	0.0174 (8)
O2W	0.0340 (9)	0.0529 (11)	0.0230 (9)	0.0243 (8)	−0.0033 (7)	−0.0057 (7)
O3	0.0194 (7)	0.0307 (8)	0.0331 (9)	0.0048 (6)	0.0083 (7)	0.0039 (6)
O3W	0.0785 (17)	0.0687 (16)	0.0513 (15)	0.0324 (13)	0.0073 (13)	−0.0031 (11)
O4	0.0586 (14)	0.0721 (14)	0.0248 (11)	−0.0171 (11)	0.0180 (10)	−0.0021 (9)
O5	0.0219 (7)	0.0368 (8)	0.0207 (8)	0.0087 (6)	0.0063 (6)	0.0011 (6)
O6	0.0219 (8)	0.0644 (11)	0.0236 (9)	0.0192 (8)	0.0032 (7)	0.0003 (8)
O7	0.0589 (13)	0.0358 (10)	0.0941 (18)	0.0202 (10)	−0.0261 (13)	−0.0266 (11)
O8	0.0283 (9)	0.0636 (12)	0.0410 (11)	0.0064 (9)	0.0079 (8)	0.0069 (9)
O9	0.0352 (10)	0.0339 (9)	0.0484 (11)	0.0092 (8)	0.0131 (8)	−0.0003 (8)
C1	0.0383 (14)	0.0394 (13)	0.0352 (15)	0.0037 (11)	0.0138 (11)	0.0057 (11)
C2	0.0344 (14)	0.0401 (14)	0.0386 (16)	−0.0028 (11)	0.0087 (12)	0.0015 (11)
C3	0.0422 (14)	0.0419 (14)	0.0296 (14)	0.0124 (11)	0.0068 (11)	0.0025 (10)
C4	0.0386 (13)	0.0295 (11)	0.0391 (14)	0.0157 (10)	0.0147 (11)	0.0126 (10)
C5	0.0596 (19)	0.0303 (13)	0.058 (2)	−0.0042 (13)	0.0274 (16)	0.0008 (12)
C6	0.067 (2)	0.0388 (15)	0.0484 (19)	−0.0057 (14)	0.0284 (16)	−0.0081 (13)
C7	0.0450 (15)	0.0391 (13)	0.0534 (17)	0.0241 (12)	0.0268 (13)	0.0209 (12)
C8	0.0193 (10)	0.0288 (10)	0.0257 (12)	0.0073 (8)	0.0025 (8)	0.0040 (8)
C9	0.0373 (14)	0.0454 (14)	0.0220 (13)	0.0026 (11)	0.0068 (10)	0.0028 (10)
C10	0.062 (2)	0.0504 (17)	0.0303 (16)	−0.0042 (14)	0.0157 (14)	−0.0092 (12)
C11	0.0573 (18)	0.0456 (16)	0.0322 (16)	−0.0143 (13)	0.0101 (13)	−0.0032 (12)
C12	0.0259 (12)	0.0538 (15)	0.0174 (12)	0.0054 (11)	0.0007 (9)	0.0040 (10)
C13	0.0522 (17)	0.0505 (16)	0.0240 (14)	0.0080 (13)	0.0093 (12)	−0.0070 (11)
C14	0.0559 (18)	0.0397 (14)	0.0325 (16)	−0.0034 (13)	0.0117 (13)	−0.0011 (11)
C15	0.0229 (12)	0.083 (2)	0.0223 (13)	0.0018 (12)	0.0036 (10)	0.0068 (13)
C16	0.0204 (10)	0.0303 (10)	0.0208 (11)	0.0085 (8)	0.0036 (8)	0.0009 (8)

Geometric parameters (Å, º) top

Ce1—O3ⁱ	2.4914 (14)	O6—C16	1.256 (2)
Ce1—O5ⁱⁱ	2.4955 (14)	C1—C6	1.370 (4)
Ce1—O2W	2.5444 (16)	C1—C2	1.371 (4)
Ce1—O2	2.5451 (16)	C2—C3	1.392 (4)
Ce1—O1W	2.5463 (16)	C2—H2A	0.9300
Ce1—O6	2.5546 (17)	C3—C4	1.381 (4)
Ce1—O9	2.6411 (18)	C3—H3A	0.9300
Ce1—O5	2.6717 (15)	C4—C5	1.360 (4)
Ce1—O8	2.692 (2)	C4—C7	1.512 (3)
Ce1—O3	2.7245 (15)	C5—C6	1.393 (4)
Ce1—C16	2.990 (2)	C5—H5A	0.9300
N1—O7	1.211 (3)	C6—H6A	0.9300
N1—O9	1.258 (3)	C7—C8	1.497 (3)
N1—O8	1.261 (3)	C7—H7A	0.9700
O1W—H1WA	0.847 (16)	C7—H7B	0.9700
O1W—H1WB	0.819 (17)	C9—C10	1.362 (4)
O1—C1	1.377 (3)	C9—C14	1.372 (4)
O1—H1A	0.8200	C10—C11	1.382 (4)
O2—C8	1.253 (2)	C10—H10A	0.9300
O2W—H2WA	0.831 (16)	C11—C12	1.369 (4)
O2W—H2WB	0.835 (17)	C11—H11A	0.9300
O3—C8	1.262 (3)	C12—C13	1.371 (4)
O3—Ce1ⁱ	2.4914 (14)	C12—C15	1.508 (3)
O3W—H3WA	0.846 (18)	C13—C14	1.383 (4)
O3W—H3WB	0.818 (18)	C13—H13A	0.9300
O4—C9	1.378 (3)	C14—H14A	0.9300
O4—H4A	0.8200	C15—C16	1.491 (3)
O5—C16	1.263 (2)	C15—H15A	0.9700
O5—Ce1ⁱⁱ	2.4955 (14)	C15—H15B	0.9700

O3ⁱ—Ce1—O5ⁱⁱ	179.31 (5)	C8—O3—Ce1	90.79 (12)
O3ⁱ—Ce1—O2W	81.58 (5)	Ce1ⁱ—O3—Ce1	117.31 (6)
O5ⁱⁱ—Ce1—O2W	97.77 (5)	H3WA—O3W—H3WB	101 (3)
O3ⁱ—Ce1—O2	111.16 (5)	C9—O4—H4A	109.5
O5ⁱⁱ—Ce1—O2	68.82 (5)	C16—O5—Ce1ⁱⁱ	148.67 (14)
O2W—Ce1—O2	74.31 (6)	C16—O5—Ce1	91.74 (12)
O3ⁱ—Ce1—O1W	98.50 (5)	Ce1ⁱⁱ—O5—Ce1	118.06 (6)
O5ⁱⁱ—Ce1—O1W	81.87 (5)	C16—O6—Ce1	97.49 (13)
O2W—Ce1—O1W	141.07 (6)	N1—O8—Ce1	96.80 (13)
O2—Ce1—O1W	138.12 (5)	N1—O9—Ce1	99.36 (13)
O3ⁱ—Ce1—O6	69.62 (5)	C6—C1—C2	119.9 (2)
O5ⁱⁱ—Ce1—O6	111.05 (5)	C6—C1—O1	121.8 (2)
O2W—Ce1—O6	138.36 (5)	C2—C1—O1	118.2 (2)
O2—Ce1—O6	88.46 (6)	C1—C2—C3	120.0 (2)
O1W—Ce1—O6	74.55 (6)	C1—C2—H2A	120.0
O3ⁱ—Ce1—O9	110.48 (5)	C3—C2—H2A	120.0
O5ⁱⁱ—Ce1—O9	69.02 (5)	C4—C3—C2	120.7 (2)
O2W—Ce1—O9	67.10 (6)	C4—C3—H3A	119.6
O2—Ce1—O9	116.63 (6)	C2—C3—H3A	119.6
O1W—Ce1—O9	76.79 (6)	C5—C4—C3	118.1 (2)
O6—Ce1—O9	150.94 (6)	C5—C4—C7	120.2 (2)
O3ⁱ—Ce1—O5	118.73 (5)	C3—C4—C7	121.7 (2)
O5ⁱⁱ—Ce1—O5	61.94 (6)	C4—C5—C6	122.1 (3)
O2W—Ce1—O5	143.60 (5)	C4—C5—H5A	119.0
O2—Ce1—O5	70.22 (5)	C6—C5—H5A	119.0
O1W—Ce1—O5	69.76 (5)	C1—C6—C5	119.2 (3)
O6—Ce1—O5	49.13 (5)	C1—C6—H6A	120.4
O9—Ce1—O5	123.16 (5)	C5—C6—H6A	120.4
O3ⁱ—Ce1—O8	66.61 (5)	C8—C7—C4	114.46 (18)
O5ⁱⁱ—Ce1—O8	113.06 (5)	C8—C7—H7A	108.6
O2W—Ce1—O8	77.36 (6)	C4—C7—H7A	108.6
O2—Ce1—O8	151.55 (6)	C8—C7—H7B	108.6
O1W—Ce1—O8	67.42 (6)	C4—C7—H7B	108.6
O6—Ce1—O8	115.06 (6)	H7A—C7—H7B	107.6
O9—Ce1—O8	47.31 (5)	O2—C8—O3	119.32 (19)
O5—Ce1—O8	137.13 (6)	O2—C8—C7	120.53 (19)
O3ⁱ—Ce1—O3	62.69 (6)	O3—C8—C7	120.11 (18)
O5ⁱⁱ—Ce1—O3	117.26 (5)	C10—C9—C14	120.0 (2)
O2W—Ce1—O3	66.25 (5)	C10—C9—O4	117.6 (2)
O2—Ce1—O3	48.50 (5)	C14—C9—O4	122.3 (2)
O1W—Ce1—O3	147.40 (6)	C9—C10—C11	119.4 (3)
O6—Ce1—O3	73.89 (5)	C9—C10—H10A	120.3
O9—Ce1—O3	133.34 (5)	C11—C10—H10A	120.3
O5—Ce1—O3	95.12 (5)	C12—C11—C10	121.8 (3)
O8—Ce1—O3	120.31 (5)	C12—C11—H11A	119.1
O3ⁱ—Ce1—C16	94.08 (5)	C10—C11—H11A	119.1
O5ⁱⁱ—Ce1—C16	86.60 (5)	C11—C12—C13	117.8 (2)
O2W—Ce1—C16	152.02 (6)	C11—C12—C15	120.5 (2)
O2—Ce1—C16	81.73 (6)	C13—C12—C15	121.6 (2)
O1W—Ce1—C16	66.86 (6)	C12—C13—C14	121.3 (2)
O6—Ce1—C16	24.61 (5)	C12—C13—H13A	119.3
O9—Ce1—C16	138.72 (6)	C14—C13—H13A	119.3
O5—Ce1—C16	24.99 (5)	C9—C14—C13	119.6 (3)
O8—Ce1—C16	126.30 (6)	C9—C14—H14A	120.2
O3—Ce1—C16	87.12 (5)	C13—C14—H14A	120.2
O7—N1—O9	121.7 (2)	C16—C15—C12	117.1 (2)
O7—N1—O8	122.0 (2)	C16—C15—H15A	108.0
O9—N1—O8	116.4 (2)	C12—C15—H15A	108.0
Ce1—O1W—H1WA	120 (2)	C16—C15—H15B	108.0
Ce1—O1W—H1WB	137 (2)	C12—C15—H15B	108.0
H1WA—O1W—H1WB	103 (2)	H15A—C15—H15B	107.3
C1—O1—H1A	109.5	O6—C16—O5	119.4 (2)
C8—O2—Ce1	99.57 (13)	O6—C16—C15	122.36 (19)
Ce1—O2W—H2WA	118.0 (19)	O5—C16—C15	118.19 (19)
Ce1—O2W—H2WB	130 (2)	O6—C16—Ce1	57.90 (11)
H2WA—O2W—H2WB	104 (2)	O5—C16—Ce1	63.27 (11)
C8—O3—Ce1ⁱ	151.47 (14)	C15—C16—Ce1	164.79 (18)

O3ⁱ—Ce1—O2—C8	−9.94 (16)	O1W—Ce1—O9—N1	73.79 (13)
O5ⁱⁱ—Ce1—O2—C8	169.33 (16)	O6—Ce1—O9—N1	64.17 (18)
O2W—Ce1—O2—C8	64.29 (14)	O5—Ce1—O9—N1	128.49 (13)
O1W—Ce1—O2—C8	−141.93 (14)	O8—Ce1—O9—N1	2.46 (12)
O6—Ce1—O2—C8	−77.35 (15)	O3—Ce1—O9—N1	−91.75 (14)
O9—Ce1—O2—C8	117.92 (14)	C16—Ce1—O9—N1	102.24 (14)
O5—Ce1—O2—C8	−124.05 (15)	C6—C1—C2—C3	−0.1 (5)
O8—Ce1—O2—C8	69.7 (2)	O1—C1—C2—C3	179.4 (3)
O3—Ce1—O2—C8	−7.65 (13)	C1—C2—C3—C4	0.4 (4)
C16—Ce1—O2—C8	−101.13 (15)	C2—C3—C4—C5	−0.4 (4)
O3ⁱ—Ce1—O3—C8	−174.91 (17)	C2—C3—C4—C7	179.4 (2)
O5ⁱⁱ—Ce1—O3—C8	4.31 (15)	C3—C4—C5—C6	0.2 (5)
O2W—Ce1—O3—C8	−82.21 (13)	C7—C4—C5—C6	−179.7 (3)
O2—Ce1—O3—C8	7.49 (13)	C2—C1—C6—C5	−0.1 (5)
O1W—Ce1—O3—C8	124.99 (14)	O1—C1—C6—C5	−179.6 (3)
O6—Ce1—O3—C8	110.09 (14)	C4—C5—C6—C1	0.1 (6)
O9—Ce1—O3—C8	−81.81 (14)	C5—C4—C7—C8	57.1 (4)
O5—Ce1—O3—C8	65.30 (13)	C3—C4—C7—C8	−122.7 (3)
O8—Ce1—O3—C8	−139.93 (13)	Ce1—O2—C8—O3	14.3 (2)
C16—Ce1—O3—C8	88.99 (13)	Ce1—O2—C8—C7	−163.7 (2)
O3ⁱ—Ce1—O3—Ce1ⁱ	0.0	Ce1ⁱ—O3—C8—O2	176.4 (2)
O5ⁱⁱ—Ce1—O3—Ce1ⁱ	179.23 (5)	Ce1—O3—C8—O2	−13.1 (2)
O2W—Ce1—O3—Ce1ⁱ	92.70 (8)	Ce1ⁱ—O3—C8—C7	−5.7 (5)
O2—Ce1—O3—Ce1ⁱ	−177.60 (10)	Ce1—O3—C8—C7	164.8 (2)
O1W—Ce1—O3—Ce1ⁱ	−60.09 (12)	C4—C7—C8—O2	24.1 (4)
O6—Ce1—O3—Ce1ⁱ	−75.00 (7)	C4—C7—C8—O3	−153.9 (2)
O9—Ce1—O3—Ce1ⁱ	93.10 (8)	C14—C9—C10—C11	−1.7 (5)
O5—Ce1—O3—Ce1ⁱ	−119.79 (7)	O4—C9—C10—C11	175.2 (3)
O8—Ce1—O3—Ce1ⁱ	34.98 (9)	C9—C10—C11—C12	0.2 (6)
C16—Ce1—O3—Ce1ⁱ	−96.10 (7)	C10—C11—C12—C13	1.4 (5)
O3ⁱ—Ce1—O5—C16	10.28 (14)	C10—C11—C12—C15	−174.3 (3)
O5ⁱⁱ—Ce1—O5—C16	−169.91 (16)	C11—C12—C13—C14	−1.5 (5)
O2W—Ce1—O5—C16	127.78 (12)	C15—C12—C13—C14	174.0 (3)
O2—Ce1—O5—C16	114.18 (13)	C10—C9—C14—C13	1.5 (5)
O1W—Ce1—O5—C16	−78.44 (13)	O4—C9—C14—C13	−175.2 (3)
O6—Ce1—O5—C16	8.32 (12)	C12—C13—C14—C9	0.1 (5)
O9—Ce1—O5—C16	−136.31 (12)	C11—C12—C15—C16	−127.4 (3)
O8—Ce1—O5—C16	−75.42 (14)	C13—C12—C15—C16	57.1 (4)
O3—Ce1—O5—C16	71.84 (12)	Ce1—O6—C16—O5	15.6 (2)
O3ⁱ—Ce1—O5—Ce1ⁱⁱ	−179.81 (5)	Ce1—O6—C16—C15	−162.0 (2)
O5ⁱⁱ—Ce1—O5—Ce1ⁱⁱ	0.0	Ce1ⁱⁱ—O5—C16—O6	−177.51 (17)
O2W—Ce1—O5—Ce1ⁱⁱ	−62.31 (11)	Ce1—O5—C16—O6	−14.8 (2)
O2—Ce1—O5—Ce1ⁱⁱ	−75.91 (7)	Ce1ⁱⁱ—O5—C16—C15	0.2 (4)
O1W—Ce1—O5—Ce1ⁱⁱ	91.47 (8)	Ce1—O5—C16—C15	162.9 (2)
O6—Ce1—O5—Ce1ⁱⁱ	178.23 (10)	Ce1ⁱⁱ—O5—C16—Ce1	−162.7 (3)
O9—Ce1—O5—Ce1ⁱⁱ	33.60 (9)	C12—C15—C16—O6	12.9 (4)
O8—Ce1—O5—Ce1ⁱⁱ	94.49 (9)	C12—C15—C16—O5	−164.8 (2)
O3—Ce1—O5—Ce1ⁱⁱ	−118.25 (7)	C12—C15—C16—Ce1	−73.2 (6)
C16—Ce1—O5—Ce1ⁱⁱ	169.91 (16)	O3ⁱ—Ce1—C16—O6	−6.21 (14)
O3ⁱ—Ce1—O6—C16	173.39 (15)	O5ⁱⁱ—Ce1—C16—O6	173.67 (14)
O5ⁱⁱ—Ce1—O6—C16	−6.77 (15)	O2W—Ce1—C16—O6	73.49 (19)
O2W—Ce1—O6—C16	−137.39 (13)	O2—Ce1—C16—O6	104.60 (14)
O2—Ce1—O6—C16	−73.33 (14)	O1W—Ce1—C16—O6	−103.72 (15)
O1W—Ce1—O6—C16	67.94 (14)	O9—Ce1—C16—O6	−134.01 (14)
O9—Ce1—O6—C16	77.67 (18)	O5—Ce1—C16—O6	164.8 (2)
O5—Ce1—O6—C16	−8.44 (12)	O8—Ce1—C16—O6	−70.02 (15)
O8—Ce1—O6—C16	123.27 (14)	O3—Ce1—C16—O6	56.13 (14)
O3—Ce1—O6—C16	−120.32 (14)	O3ⁱ—Ce1—C16—O5	−170.98 (12)
O7—N1—O8—Ce1	−176.2 (2)	O5ⁱⁱ—Ce1—C16—O5	8.91 (14)
O9—N1—O8—Ce1	4.2 (2)	O2W—Ce1—C16—O5	−91.28 (16)
O3ⁱ—Ce1—O8—N1	154.13 (15)	O2—Ce1—C16—O5	−60.17 (12)
O5ⁱⁱ—Ce1—O8—N1	−25.22 (15)	O1W—Ce1—C16—O5	91.51 (12)
O2W—Ce1—O8—N1	67.94 (13)	O6—Ce1—C16—O5	−164.8 (2)
O2—Ce1—O8—N1	62.56 (19)	O9—Ce1—C16—O5	61.22 (15)
O1W—Ce1—O8—N1	−95.12 (14)	O8—Ce1—C16—O5	125.22 (12)
O6—Ce1—O8—N1	−154.27 (12)	O3—Ce1—C16—O5	−108.63 (12)
O9—Ce1—O8—N1	−2.44 (12)	O3ⁱ—Ce1—C16—C15	89.6 (6)
O5—Ce1—O8—N1	−98.19 (14)	O5ⁱⁱ—Ce1—C16—C15	−90.5 (6)
O3—Ce1—O8—N1	120.41 (13)	O2W—Ce1—C16—C15	169.3 (5)
C16—Ce1—O8—N1	−128.67 (13)	O2—Ce1—C16—C15	−159.6 (6)
O7—N1—O9—Ce1	176.07 (19)	O1W—Ce1—C16—C15	−7.9 (5)
O8—N1—O9—Ce1	−4.3 (2)	O6—Ce1—C16—C15	95.8 (6)
O3ⁱ—Ce1—O9—N1	−20.48 (15)	O9—Ce1—C16—C15	−38.2 (6)
O5ⁱⁱ—Ce1—O9—N1	160.03 (15)	O5—Ce1—C16—C15	−99.5 (6)
O2W—Ce1—O9—N1	−91.36 (14)	O8—Ce1—C16—C15	25.8 (6)
O2—Ce1—O9—N1	−148.66 (12)	O3—Ce1—C16—C15	151.9 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2ⁱⁱ	0.85 (2)	1.90 (2)	2.693 (2)	156 (3)
O1W—H1WB···O7ⁱⁱⁱ	0.82 (2)	2.46 (2)	3.197 (3)	150 (3)
O1W—H1WB···O8ⁱⁱⁱ	0.82 (2)	2.51 (2)	3.272 (3)	156 (3)
O2W—H2WA···O6ⁱ	0.83 (2)	1.91 (2)	2.721 (2)	165 (3)
O2W—H2WB···O4^iv	0.84 (2)	1.95 (2)	2.783 (3)	175 (3)
O3W—H3WA···O4ⁱⁱ	0.85 (2)	2.58 (2)	3.352 (4)	152 (3)
O4—H4A···O1^v	0.82	1.83	2.649 (3)	173

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

Experimental details

Crystal data
Chemical formula	[Ce(C₈H₇O₃)₂(NO₃)(H₂O)₂]·H₂O
M_r	558.45
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.1151 (3), 9.8048 (4), 13.2396 (5)
α, β, γ (°)	92.120 (2), 90.829 (2), 112.550 (2)
V (Å³)	971.76 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.41
Crystal size (mm)	0.14 × 0.14 × 0.03

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.716, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	15535, 4492, 4133
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.050, 0.98
No. of reflections	4492
No. of parameters	289
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.36

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2ⁱ	0.847 (16)	1.898 (18)	2.693 (2)	156 (3)
O1W—H1WB···O7ⁱⁱ	0.819 (17)	2.46 (2)	3.197 (3)	150 (3)
O1W—H1WB···O8ⁱⁱ	0.819 (17)	2.51 (2)	3.272 (3)	156 (3)
O2W—H2WA···O6ⁱⁱⁱ	0.831 (16)	1.911 (17)	2.721 (2)	165 (3)
O2W—H2WB···O4^iv	0.835 (17)	1.951 (17)	2.783 (3)	175 (3)
O3W—H3WA···O4ⁱ	0.846 (18)	2.58 (2)	3.352 (4)	152 (3)
O4—H4A···O1^v	0.82	1.83	2.649 (3)	172.7

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

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fang, R.-Q. & Zhang, X.-M. (2006). Inorg. Chem. 45, 4801–4810. Web of Science CSD CrossRef PubMed CAS Google Scholar
Liu, J.-L., Li, H.-Q. & Zhao, G.-L. (2010). Acta Cryst. E66, m9. Web of Science CSD CrossRef IUCr Journals 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
Wang, G.-H., Lei, Y.-Q. & Wang, N. (2010). Cryst. Growth Des. 10, 4060–4067. Google Scholar
Wang, X.-X. & Sevov, S. (2008). Inorg. Chem. 47, 1037–1043. Web of Science CSD CrossRef PubMed CAS Google Scholar

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