Poly[triaqua-μ4-pyridine-3,5-dicarboxyl­ato-barium(II)]

Aghabozorg, H.; Nemati, A.; Derikvand, Z.; Ghadermazi, M.; Daneshvar, S.

doi:10.1107/S1600536808001323

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m375

doi:10.1107/S1600536808001323

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Poly[triaqua-μ₄-pyridine-3,5-dicarboxylato-barium(II)]

Hossein Aghabozorg,^a ^* Andya Nemati,^a Zohreh Derikvand,^a Mohammad Ghadermazi ^b and Shirin Daneshvar ^c

^aFaculty of Chemistry, Teacher Training University, 49 Mofateh Avenue 15614, Tehran, Iran, ^bDepartment of Chemistry, University of Kurdistan, Sanandaj, Iran, and ^cIslamic Azad University, North Tehran Branch, Tehran, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 17 November 2007; accepted 13 January 2008; online 23 January 2008)

The reaction of the proton-transfer compound (pdaH₂)(py-3,5-dc)·H₂O (pda = propane-1,3-diamine and py-3,5-dcH₂ = pyridine-3,5-dicarboxylic acid) with Ba(NO₃)₂ leads to the formation of the title polymeric compound, [Ba(C₇H₃NO₄)(H₂O)₃]_n. The Ba^II atom is nine-coordinated by six carboxylate O atoms from the (py-3,5-dc)²⁻ ligands, and three O atoms from the coordinated water molecules. The coordination polyhedron around the Ba^II atom is best described as tricapped trigonal-prismatic. In the crystal structure, intermolecular interactions, such as X—H⋯O hydrogen bonds (X = O and C) and π–π stacking [centroid–centroid distances between pyridine rings of 3.6191 (13) and 3.6192 (13) Å] play an important role in stabilizing the supramolecular structure.

Related literature

For related literature, see: Aghabozorg et al. (2006 , 2007 , 2008 ); Dorazco-Gonzalez et al. (2006 ); Starosta et al. (2002a ,b ).

Experimental

Crystal data

[Ba(C₇H₃NO₄)(H₂O)₃]
M_r = 356.49
Monoclinic, P 2₁ /c
a = 7.5922 (4) Å
b = 18.5576 (10) Å
c = 7.1832 (4) Å
β = 90.499 (5)°
V = 1012.02 (9) Å³
Z = 4
Mo Kα radiation
μ = 3.95 mm⁻¹
T = 100 (2) K
0.25 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (APEX2; Bruker, 2005 ) T_min = 0.386, T_max = 0.455
10713 measured reflections
2664 independent reflections
2575 reflections with I > 2/s(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.048
S = 1.00
2664 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1ⁱ	0.84	2.13	2.924 (2)	158
O1W—H1WB⋯O1ⁱⁱ	0.84	1.89	2.730 (2)	176
O2W—H2WA⋯O2ⁱⁱⁱ	0.81	1.96	2.761 (2)	172
O2W—H2WB⋯N1^iv	0.83	2.06	2.873 (3)	165
O3W—H3WA⋯N1^v	0.85	2.48	3.284 (3)	159
O3W—H3WB⋯O1W^vi	0.85	2.02	2.851 (3)	165
C3—H3⋯O2W^vii	0.93	2.47	3.362 (3)	161
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x-1, y, z+1; (v) x-1, y, z; (vi) -x, -y+1, -z+1; (vii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001323/su2029sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001323/su2029Isup2.hkl

checkCIF report

Comment top

Recent interest of our researching group has focused on the synthesis and characterization of novel metal complexes of proton transfer compounds obtained using dipicolinic acid (Aghabozorg et al., 2007). A convenient path to obtain polymeric structures is to use a multifunctional ligand to link metal ions to form an infinite arrangement (Starosta et al., 2002a,b); Dorazco-Gonzalez et al., 2006). The reaction of the proton transfer compound (pdaH₂)(py-3,5-dc).H₂O [pda = propane-1,3-diamine and py-3,5-dcH₂ = pyridine-3,5-dicarboxylic acid (Aghabozorg et al., 2006)] with Ba(NO₃)₂, in aqueous solution with a 1:2 molar ratio, lead to the formation of the title polymeric compound, (I).

The monomeric units in the polymer (I) consist of one Ba^II atom, one (py-3,5-dc)^2- dianion and three aqua (H₂O) ligands. The Ba^II atom is nine-coordinate with six carboxylate oxygen atoms from the bridging (py-3,5-dc)^2- ligands and three oxygen atoms from the coordinated water molecules (Figs. 1 and 2). The summation of bond angles O2W—Ba1—O3ⁱⁱ, O3ⁱⁱ —Ba1—O1 and O2W—Ba1—O1 is 360.94° hence, the Ba1 atom is located in the center of the plane (O1,O2,O3Wⁱⁱ). Atoms O2, O3W and O3ⁱ form a triangle, and atoms O1W, O4ⁱⁱ, O4ⁱⁱⁱ form another triangle. So a prism, consisting of six O-atoms and three caps (O2W, O3ⁱⁱⁱ and O1) on the faces around the Ba(II) atom is formed. The coordination polyhedron around the Ba^II atom is hence, best described as a tricapped trigonal prism (Fig. 3).

In the molecular structure of (I) atoms O1 and O2, from one of the carboxylate groups, have only one Ba—O bond, while atoms O3 and O4 from three neighboring carboxylate groups have two Ba—O bonds. The bond distances between barium and the oxygen atoms are in the range 2.7399 (18)–2.8669 (16) Å.

In the crystal structure of (I) there are several O—H···O hydrogen bonds [in the range 2.730 (2)–2.924 (2) Å], and the pyridine N-atoms have N—H···O hydrogen bonds with neighboring coordinated water molecules [in the range 2.873 (3)–3.284 (3) Å]. C—H···O hydrogen bonds [with D···A distance 3.362 (3) Å], are also present (Table 1). There are π-π stacking interactions between symmetry related pyridine (N1/C1—C5) rings with centroid···centroid distances of 3.6191 (13) and 3.6192 (13) Å (symmetry codes: (i) = x, -y + 3/2, z + 1/2 and x; (ii) = -y + 3/2, z - 1/2, respectively] (Fig.4).

All of these intermolecular interactions play an important role in forming the three dimensional polymeric system and stabilizing the structure.

Related literature top

For related literature, see: Aghabozorg et al. (2006, 2007); Dorazco-Gonzalez et al. (2006); Starosta et al. (2002a, 2002b).

Experimental top

The proton transfer compound (pdaH₂)(py-3,5-dc), was prepared by the reaction of pyridine-3,5-dicarboxylic acid [py-3,5-dcH₂], with propane-1,3-diamine [pda], (Aghabozorg et al., 2006). Compound (I) was prepared by the reaction between Ba(NO₃)₂ (292.5 mg, 0.5 mmol in water 25 ml) and the proton transfer compound (pdaH₂)(py-3,5-dc) (241 mg, 1.0 mmol in water 25 ml), in a 1:2 molar ratio. Crystals were obtained by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound (I), with displacement ellipsoids drawn at the 50% probability level [A—C symmetry codes are: A = -x, 1 – y, 1 – z; B = 1 – x, -1/2 + y, 1/2 – z; C = -1 + x, 3/2 – y, 1/2 + z].
	Fig. 2. A view, along the c axis, of the crystal packing of compound (I).
	Fig. 3. A view of the distorted tricapped trigonal prism around the Ba^II atom [D: -1 + x, 3/2 - y, 1/2 + z; E: x, 3/2 - y, -1/2 + z; F: x, 3/2 - y, 1/2 + z].
	Fig. 4. π-π Stacking interactions (Cg1—Cg1ⁱ) in compound (I). [Cg1: N1/C1—C5; symmetry code: (i) = x, -y + 3/2, z + 1/2].

Poly[triaqua-µ₄-pyridine-3,5-dicarboxylato-barium(II)] top

Crystal data top

[Ba(C₇H₃NO₄)(H₂O)₃]	F(000) = 680
M_r = 356.49	D_x = 2.340 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 523 reflections
a = 7.5922 (4) Å	θ = 3–30°
b = 18.5576 (10) Å	µ = 3.95 mm⁻¹
c = 7.1832 (4) Å	T = 100 K
β = 90.499 (5)°	Prism, colourless
V = 1012.02 (9) Å³	0.25 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	2664 independent reflections
Radiation source: fine-focus sealed tube	2575 reflections with I > 2/s(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 0 pixels mm^-1	θ_max = 29.0°, θ_min = 2.7°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (APEX2; Bruker, 2005)	k = −25→25
T_min = 0.386, T_max = 0.455	l = −9→9
10713 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.019	H-atom parameters constrained
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.0132P)² + 2.3675P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.003
2664 reflections	Δρ_max = 1.18 e Å⁻³
146 parameters	Δρ_min = −0.66 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 1998), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0155 (5)

Crystal data top

[Ba(C₇H₃NO₄)(H₂O)₃]	V = 1012.02 (9) Å³
M_r = 356.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5922 (4) Å	µ = 3.95 mm⁻¹
b = 18.5576 (10) Å	T = 100 K
c = 7.1832 (4) Å	0.25 × 0.25 × 0.20 mm
β = 90.499 (5)°

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	2664 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2005)	2575 reflections with I > 2/s(I)
T_min = 0.386, T_max = 0.455	R_int = 0.035
10713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.048	H-atom parameters constrained
S = 1.00	Δρ_max = 1.18 e Å⁻³
2664 reflections	Δρ_min = −0.66 e Å⁻³
146 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
Ba1	0.246077 (15)	0.566051 (6)	0.470978 (17)	0.00707 (6)
O1	0.4431 (2)	0.58907 (9)	0.1397 (2)	0.0115 (3)
O2	0.3179 (2)	0.68921 (8)	0.2430 (2)	0.0125 (3)
O3	0.8918 (2)	0.92324 (9)	0.0350 (3)	0.0153 (3)
O4	0.6006 (2)	0.92670 (8)	0.0586 (3)	0.0120 (3)
N1	0.8720 (3)	0.70081 (10)	−0.0669 (3)	0.0109 (3)
C1	0.7279 (3)	0.66597 (12)	−0.0073 (3)	0.0106 (4)
H1	0.7236	0.6162	−0.0206	0.013*
C2	0.5847 (3)	0.70043 (12)	0.0734 (3)	0.0083 (4)
C3	0.5887 (3)	0.77518 (11)	0.0851 (3)	0.0085 (4)
H3	0.4940	0.7999	0.1356	0.010*
C4	0.7341 (3)	0.81285 (12)	0.0214 (3)	0.0098 (4)
C5	0.8739 (3)	0.77268 (12)	−0.0512 (3)	0.0099 (4)
H5	0.9735	0.7973	−0.0908	0.012*
C6	0.4364 (3)	0.65684 (12)	0.1556 (3)	0.0090 (4)
C7	0.7438 (3)	0.89332 (12)	0.0389 (3)	0.0091 (4)
O1W	0.2873 (2)	0.50776 (9)	0.8310 (2)	0.0135 (3)
H1WA	0.3062	0.5376	0.9167	0.016*
H1WB	0.3736	0.4798	0.8421	0.016*
O2W	0.1920 (2)	0.67121 (9)	0.7367 (2)	0.0149 (3)
H2WA	0.2290	0.7117	0.7494	0.018*
H2WB	0.0948	0.6718	0.7890	0.018*
O3W	0.0471 (3)	0.56144 (11)	0.1471 (3)	0.0259 (4)
H3WA	0.0302	0.6021	0.0954	0.031*
H3WB	−0.0540	0.5424	0.1327	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ba1	0.00503 (8)	0.00616 (8)	0.01003 (9)	0.00006 (4)	−0.00019 (4)	0.00054 (4)
O1	0.0118 (8)	0.0072 (7)	0.0154 (8)	−0.0009 (6)	0.0004 (6)	−0.0004 (6)
O2	0.0120 (8)	0.0075 (7)	0.0179 (8)	0.0002 (6)	0.0034 (6)	0.0013 (6)
O3	0.0073 (8)	0.0101 (7)	0.0286 (10)	−0.0015 (6)	−0.0001 (7)	0.0019 (7)
O4	0.0078 (8)	0.0099 (7)	0.0182 (8)	0.0009 (6)	−0.0008 (6)	0.0001 (6)
N1	0.0102 (9)	0.0111 (8)	0.0114 (8)	0.0005 (7)	−0.0003 (7)	−0.0005 (7)
C1	0.0114 (10)	0.0101 (10)	0.0104 (9)	−0.0003 (8)	−0.0002 (8)	0.0000 (8)
C2	0.0087 (9)	0.0090 (9)	0.0072 (9)	−0.0017 (7)	−0.0019 (7)	0.0017 (7)
C3	0.0077 (9)	0.0088 (9)	0.0090 (9)	0.0012 (7)	−0.0017 (7)	0.0002 (7)
C4	0.0106 (10)	0.0071 (9)	0.0116 (10)	0.0012 (7)	−0.0031 (8)	0.0013 (7)
C5	0.0071 (9)	0.0120 (10)	0.0107 (9)	−0.0008 (7)	−0.0004 (7)	0.0008 (7)
C6	0.0088 (9)	0.0092 (9)	0.0087 (9)	−0.0014 (7)	−0.0026 (7)	0.0020 (7)
C7	0.0083 (10)	0.0084 (9)	0.0107 (9)	−0.0006 (7)	−0.0014 (7)	0.0017 (7)
O1W	0.0138 (8)	0.0129 (8)	0.0137 (8)	0.0029 (6)	−0.0017 (6)	−0.0005 (6)
O2W	0.0115 (8)	0.0094 (7)	0.0237 (9)	−0.0008 (6)	0.0048 (6)	−0.0048 (6)
O3W	0.0181 (10)	0.0359 (12)	0.0236 (10)	−0.0038 (8)	−0.0046 (8)	0.0020 (8)

Geometric parameters (Å, º) top

Ba1—O3ⁱ	2.7399 (18)	N1—C1	1.344 (3)
Ba1—O4ⁱⁱ	2.7621 (17)	C1—C2	1.392 (3)
Ba1—O2W	2.7631 (17)	C1—H1	0.9300
Ba1—O3W	2.764 (2)	C2—C3	1.390 (3)
Ba1—O1W	2.8184 (17)	C2—C6	1.510 (3)
Ba1—O4ⁱⁱⁱ	2.8447 (16)	C3—C4	1.388 (3)
Ba1—O3ⁱⁱⁱ	2.8496 (17)	C3—H3	0.9300
Ba1—O1	2.8540 (17)	C4—C5	1.402 (3)
Ba1—O2	2.8669 (16)	C4—C7	1.500 (3)
Ba1—C6	3.181 (2)	C5—H5	0.9300
Ba1—C7ⁱⁱⁱ	3.207 (2)	C7—Ba1^v	3.207 (2)
Ba1—Ba1^iv	4.4914 (3)	O1W—H1WA	0.8399
O1—C6	1.264 (3)	O1W—H1WB	0.8385
O2—C6	1.255 (3)	O2W—H2WA	0.8061
O3—C7	1.254 (3)	O2W—H2WB	0.8314
O4—C7	1.260 (3)	O3W—H3WA	0.8500
N1—C5	1.338 (3)	O3W—H3WB	0.8508

O3ⁱ—Ba1—O4ⁱⁱ	156.10 (5)	O4ⁱⁱ—Ba1—Ba1^iv	144.61 (3)
O3ⁱ—Ba1—O2W	71.39 (5)	O2W—Ba1—Ba1^iv	101.11 (4)
O4ⁱⁱ—Ba1—O2W	87.61 (5)	O3W—Ba1—Ba1^iv	67.19 (4)
O3ⁱ—Ba1—O3W	67.27 (6)	O1W—Ba1—Ba1^iv	77.95 (4)
O4ⁱⁱ—Ba1—O3W	135.86 (6)	O4ⁱⁱⁱ—Ba1—Ba1^iv	81.49 (3)
O2W—Ba1—O3W	121.34 (6)	O3ⁱⁱⁱ—Ba1—Ba1^iv	35.71 (4)
O3ⁱ—Ba1—O1W	88.58 (5)	O1—Ba1—Ba1^iv	126.99 (3)
O4ⁱⁱ—Ba1—O1W	73.10 (5)	O2—Ba1—Ba1^iv	130.60 (3)
O2W—Ba1—O1W	69.70 (5)	C6—Ba1—Ba1^iv	137.63 (4)
O3W—Ba1—O1W	144.69 (6)	C7ⁱⁱⁱ—Ba1—Ba1^iv	58.45 (4)
O3ⁱ—Ba1—O4ⁱⁱⁱ	118.78 (5)	C6—O1—Ba1	92.98 (13)
O4ⁱⁱ—Ba1—O4ⁱⁱⁱ	70.29 (5)	C6—O2—Ba1	92.58 (13)
O2W—Ba1—O4ⁱⁱⁱ	139.20 (5)	C7—O3—Ba1^vi	156.50 (16)
O3W—Ba1—O4ⁱⁱⁱ	97.46 (6)	C7—O3—Ba1^v	94.76 (14)
O1W—Ba1—O4ⁱⁱⁱ	71.18 (5)	Ba1^vi—O3—Ba1^v	106.92 (6)
O3ⁱ—Ba1—O3ⁱⁱⁱ	73.08 (6)	C7—O4—Ba1^vii	146.93 (14)
O4ⁱⁱ—Ba1—O3ⁱⁱⁱ	113.94 (5)	C7—O4—Ba1^v	94.85 (13)
O2W—Ba1—O3ⁱⁱⁱ	127.63 (5)	Ba1^vii—O4—Ba1^v	109.71 (5)
O3W—Ba1—O3ⁱⁱⁱ	76.14 (6)	C5—N1—C1	117.4 (2)
O1W—Ba1—O3ⁱⁱⁱ	72.23 (5)	N1—C1—C2	123.5 (2)
O4ⁱⁱⁱ—Ba1—O3ⁱⁱⁱ	45.89 (5)	N1—C1—H1	118.2
O3ⁱ—Ba1—O1	130.66 (5)	C2—C1—H1	118.2
O4ⁱⁱ—Ba1—O1	70.49 (5)	C3—C2—C1	117.8 (2)
O2W—Ba1—O1	123.54 (5)	C3—C2—C6	121.8 (2)
O3W—Ba1—O1	65.75 (6)	C1—C2—C6	120.27 (19)
O1W—Ba1—O1	140.15 (5)	C4—C3—C2	120.0 (2)
O4ⁱⁱⁱ—Ba1—O1	81.72 (5)	C4—C3—H3	120.0
O3ⁱⁱⁱ—Ba1—O1	108.77 (5)	C2—C3—H3	120.0
O3ⁱ—Ba1—O2	103.30 (5)	C3—C4—C5	117.5 (2)
O4ⁱⁱ—Ba1—O2	84.35 (5)	C3—C4—C7	120.8 (2)
O2W—Ba1—O2	82.06 (5)	C5—C4—C7	121.6 (2)
O3W—Ba1—O2	69.46 (6)	N1—C5—C4	123.6 (2)
O1W—Ba1—O2	144.10 (5)	N1—C5—H5	118.2
O4ⁱⁱⁱ—Ba1—O2	127.01 (5)	C4—C5—H5	118.2
O3ⁱⁱⁱ—Ba1—O2	143.56 (5)	O2—C6—O1	123.4 (2)
O1—Ba1—O2	45.62 (5)	O2—C6—C2	118.63 (19)
O3ⁱ—Ba1—C6	122.28 (5)	O1—C6—C2	117.9 (2)
O4ⁱⁱ—Ba1—C6	71.86 (5)	O2—C6—Ba1	64.21 (11)
O2W—Ba1—C6	100.90 (5)	O1—C6—Ba1	63.64 (12)
O3W—Ba1—C6	70.44 (6)	C2—C6—Ba1	155.07 (14)
O1W—Ba1—C6	144.04 (5)	O3—C7—O4	124.0 (2)
O4ⁱⁱⁱ—Ba1—C6	103.86 (5)	O3—C7—C4	118.8 (2)
O3ⁱⁱⁱ—Ba1—C6	130.61 (6)	O4—C7—C4	117.20 (19)
O1—Ba1—C6	23.38 (5)	O3—C7—Ba1^v	62.31 (12)
O2—Ba1—C6	23.21 (5)	O4—C7—Ba1^v	62.10 (12)
O3ⁱ—Ba1—C7ⁱⁱⁱ	95.74 (5)	C4—C7—Ba1^v	173.78 (14)
O4ⁱⁱ—Ba1—C7ⁱⁱⁱ	91.73 (5)	Ba1—O1W—H1WA	115.9
O2W—Ba1—C7ⁱⁱⁱ	136.46 (5)	Ba1—O1W—H1WB	113.9
O3W—Ba1—C7ⁱⁱⁱ	87.91 (6)	H1WA—O1W—H1WB	102.1
O1W—Ba1—C7ⁱⁱⁱ	68.54 (5)	Ba1—O2W—H2WA	133.0
O4ⁱⁱⁱ—Ba1—C7ⁱⁱⁱ	23.05 (5)	Ba1—O2W—H2WB	117.3
O3ⁱⁱⁱ—Ba1—C7ⁱⁱⁱ	22.94 (5)	H2WA—O2W—H2WB	104.3
O1—Ba1—C7ⁱⁱⁱ	96.79 (5)	Ba1—O3W—H3WA	114.8
O2—Ba1—C7ⁱⁱⁱ	141.21 (5)	Ba1—O3W—H3WB	127.0
C6—Ba1—C7ⁱⁱⁱ	120.17 (6)	H3WA—O3W—H3WB	100.5
O3ⁱ—Ba1—Ba1^iv	37.37 (3)

O3ⁱ—Ba1—O1—C6	77.70 (14)	O3W—Ba1—C6—O2	83.32 (13)
O4ⁱⁱ—Ba1—O1—C6	−89.28 (13)	O1W—Ba1—C6—O2	−106.62 (14)
O2W—Ba1—O1—C6	−16.01 (14)	O4ⁱⁱⁱ—Ba1—C6—O2	176.43 (12)
O3W—Ba1—O1—C6	96.69 (13)	O3ⁱⁱⁱ—Ba1—C6—O2	133.56 (12)
O1W—Ba1—O1—C6	−114.31 (13)	O1—Ba1—C6—O2	157.3 (2)
O4ⁱⁱⁱ—Ba1—O1—C6	−161.22 (13)	C7ⁱⁱⁱ—Ba1—C6—O2	158.77 (12)
O3ⁱⁱⁱ—Ba1—O1—C6	161.19 (12)	Ba1^iv—Ba1—C6—O2	83.90 (13)
O2—Ba1—O1—C6	12.30 (12)	O3ⁱ—Ba1—C6—O1	−118.76 (12)
C7ⁱⁱⁱ—Ba1—O1—C6	−178.70 (13)	O4ⁱⁱ—Ba1—C6—O1	82.65 (13)
Ba1^iv—Ba1—O1—C6	126.05 (12)	O2W—Ba1—C6—O1	166.46 (12)
O3ⁱ—Ba1—O2—C6	−147.25 (13)	O3W—Ba1—C6—O1	−73.95 (13)
O4ⁱⁱ—Ba1—O2—C6	55.73 (13)	O1W—Ba1—C6—O1	96.11 (14)
O2W—Ba1—O2—C6	144.10 (13)	O4ⁱⁱⁱ—Ba1—C6—O1	19.16 (13)
O3W—Ba1—O2—C6	−88.09 (13)	O3ⁱⁱⁱ—Ba1—C6—O1	−23.71 (15)
O1W—Ba1—O2—C6	106.31 (14)	O2—Ba1—C6—O1	−157.3 (2)
O4ⁱⁱⁱ—Ba1—O2—C6	−4.34 (15)	C7ⁱⁱⁱ—Ba1—C6—O1	1.49 (14)
O3ⁱⁱⁱ—Ba1—O2—C6	−67.82 (15)	Ba1^iv—Ba1—C6—O1	−73.38 (14)
O1—Ba1—O2—C6	−12.38 (12)	O3ⁱ—Ba1—C6—C2	141.4 (3)
C7ⁱⁱⁱ—Ba1—O2—C6	−29.99 (16)	O4ⁱⁱ—Ba1—C6—C2	−17.2 (3)
Ba1^iv—Ba1—O2—C6	−118.05 (12)	O2W—Ba1—C6—C2	66.6 (4)
C5—N1—C1—C2	−1.8 (3)	O3W—Ba1—C6—C2	−173.8 (4)
N1—C1—C2—C3	2.9 (3)	O1W—Ba1—C6—C2	−3.7 (4)
N1—C1—C2—C6	−173.38 (19)	O4ⁱⁱⁱ—Ba1—C6—C2	−80.7 (3)
C1—C2—C3—C4	−1.5 (3)	O3ⁱⁱⁱ—Ba1—C6—C2	−123.6 (3)
C6—C2—C3—C4	174.74 (19)	O1—Ba1—C6—C2	−99.8 (4)
C2—C3—C4—C5	−0.8 (3)	O2—Ba1—C6—C2	102.9 (4)
C2—C3—C4—C7	−177.84 (19)	C7ⁱⁱⁱ—Ba1—C6—C2	−98.3 (3)
C1—N1—C5—C4	−0.7 (3)	Ba1^iv—Ba1—C6—C2	−173.2 (3)
C3—C4—C5—N1	2.0 (3)	Ba1^vi—O3—C7—O4	−165.2 (3)
C7—C4—C5—N1	179.0 (2)	Ba1^v—O3—C7—O4	−7.7 (2)
Ba1—O2—C6—O1	24.5 (2)	Ba1^vi—O3—C7—C4	15.6 (5)
Ba1—O2—C6—C2	−152.08 (16)	Ba1^v—O3—C7—C4	173.06 (17)
Ba1—O1—C6—O2	−24.6 (2)	Ba1^vi—O3—C7—Ba1^v	−157.5 (4)
Ba1—O1—C6—C2	151.98 (16)	Ba1^vii—O4—C7—O3	146.4 (2)
C3—C2—C6—O2	−2.9 (3)	Ba1^v—O4—C7—O3	7.7 (2)
C1—C2—C6—O2	173.2 (2)	Ba1^vii—O4—C7—C4	−34.4 (4)
C3—C2—C6—O1	−179.68 (19)	Ba1^v—O4—C7—C4	−173.03 (16)
C1—C2—C6—O1	−3.6 (3)	Ba1^vii—O4—C7—Ba1^v	138.6 (3)
C3—C2—C6—Ba1	−92.8 (4)	C3—C4—C7—O3	158.3 (2)
C1—C2—C6—Ba1	83.3 (4)	C5—C4—C7—O3	−18.7 (3)
O3ⁱ—Ba1—C6—O2	38.51 (14)	C3—C4—C7—O4	−21.0 (3)
O4ⁱⁱ—Ba1—C6—O2	−120.08 (13)	C5—C4—C7—O4	162.1 (2)
O2W—Ba1—C6—O2	−36.26 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1^viii	0.84	2.13	2.924 (2)	158
O1W—H1WB···O1^ix	0.84	1.89	2.730 (2)	176
O2W—H2WA···O2ⁱⁱ	0.81	1.96	2.761 (2)	172
O2W—H2WB···N1^x	0.83	2.06	2.873 (3)	165
O3W—H3WA···N1^xi	0.85	2.48	3.284 (3)	159
O3W—H3WB···O1W^iv	0.85	2.02	2.851 (3)	165
C3—H3···O2W^vii	0.93	2.47	3.362 (3)	161

Symmetry codes: (ii) x, −y+3/2, z+1/2; (iv) −x, −y+1, −z+1; (vii) x, −y+3/2, z−1/2; (viii) x, y, z+1; (ix) −x+1, −y+1, −z+1; (x) x−1, y, z+1; (xi) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Ba(C₇H₃NO₄)(H₂O)₃]
M_r	356.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.5922 (4), 18.5576 (10), 7.1832 (4)
β (°)	90.499 (5)
V (Å³)	1012.02 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.95
Crystal size (mm)	0.25 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (APEX2; Bruker, 2005)
T_min, T_max	0.386, 0.455
No. of measured, independent and observed [I > 2/s(I)] reflections	10713, 2664, 2575
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.048, 1.00
No. of reflections	2664
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.66

Computer programs: APEX2 (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1ⁱ	0.84	2.13	2.924 (2)	158
O1W—H1WB···O1ⁱⁱ	0.84	1.89	2.730 (2)	176
O2W—H2WA···O2ⁱⁱⁱ	0.81	1.96	2.761 (2)	172
O2W—H2WB···N1^iv	0.83	2.06	2.873 (3)	165
O3W—H3WA···N1^v	0.85	2.48	3.284 (3)	159
O3W—H3WB···O1W^vi	0.85	2.02	2.851 (3)	165
C3—H3···O2W^vii	0.93	2.47	3.362 (3)	161

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

References

Aghabozorg, H., Attar Gharamaleki, J., Ghasemikhah, P., Ghadermazi, M. & Soleimannejad, J.(2007). Acta Cryst. E63, m1710–m1711. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Ghadermazi, M. & Nemati, A. (2006). Anal. Sci. 22, x233–x234. CAS Google Scholar
Aghabozorg, H., Nemati, A., Derikvand, Z., Ghadermazi, M. & Daneshvar, S. (2008). Acta Cryst. E64, m376. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dorazco-Gonzalez, A., Toscano, R. A., Gómez-Vidales, V. & Valdés-Martínez, J. (2006). Acta Cryst. E62, m1027–m1029. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Starosta, W., Ptasiewicz-Bak, H. & Leciejewicz, J. (2002a). J. Coord. Chem. 55, 1–9. Web of Science CSD CrossRef CAS Google Scholar
Starosta, W., Ptasiewicz-Bak, H. & Leciejewicz, J. (2002b). J. Coord. Chem. 55, 985–990. Web of Science CSD CrossRef CAS Google Scholar

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Volume 64| Part 2| February 2008| Page m375

doi:10.1107/S1600536808001323

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