Poly[tri-μ2-aqua-(μ3-pyridine-2,4-dicarboxyl­ato-κ4N,O2:O2:O2′)barium]

Pasdar, H.; Siabi, S.; Notash, B.; Aghabozorg, H.; Foroughifar, N.

doi:10.1107/S1600536811020204

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m848

doi:10.1107/S1600536811020204

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Poly[tri-μ₂-aqua-(μ₃-pyridine-2,4-dicarboxylato-κ⁴N,O²:O²:O^2′)barium]

Hoda Pasdar,^a ^* Shadi Siabi,^a Behrouz Notash,^b Hossein Aghabozorg ^a and Naser Foroughifar ^a

^aDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C. Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: h_pasdar@iau-tnb.ac.ir

(Received 9 May 2011; accepted 26 May 2011; online 4 June 2011)

In the polymeric title compound, [Ba(C₇H₃NO₄)(H₂O)₃]_n, the Ba^II ion is ten-coordinated in an NO₉ environment by one N atom and three O atoms from three pyridine-2,4-dicarboxylate (pydc) ligands and six water molecules. The μ₃-pydc ligands and the bridging water molecules connect the Ba atoms into a layer parallel to (100). The crystal packing is stabilized by O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related compounds with pyridine dicarboxylic acid derivatives, see: Aghabozorg et al. (2008 , 2011a ,b ,c ,d ); Noro et al. (2005 ); Pasdar et al. (2011a ,b ); Wang et al. (2007 ).

Experimental

Crystal data

[Ba(C₇H₃NO₄)(H₂O)₃]
M_r = 356.48
Monoclinic, P 2₁ /c
a = 11.079 (2) Å
b = 13.714 (3) Å
c = 6.5961 (13) Å
β = 94.13 (3)°
V = 999.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 4.00 mm⁻¹
T = 298 K
0.39 × 0.38 × 0.33 mm

Data collection

Stoe IPDS-2T diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ) T_min = 0.410, T_max = 0.460
7321 measured reflections
2681 independent reflections
2515 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.057
S = 1.10
2681 reflections
170 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.20 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2ⁱ	0.93	2.48	3.161 (3)	130
O5—H5A⋯O1ⁱⁱ	0.77 (5)	2.14 (4)	2.881 (3)	162 (4)
O5—H5B⋯O4ⁱⁱⁱ	0.77 (5)	2.02 (5)	2.785 (3)	174 (4)
O6—H6A⋯O4^iv	0.91 (4)	2.03 (4)	2.865 (3)	151 (3)
O6—H6B⋯O3^v	0.76 (4)	2.08 (4)	2.816 (3)	167 (4)
O7—H7A⋯O3^v	0.85 (5)	1.96 (5)	2.809 (3)	175 (4)
O7—H7B⋯O4^vi	0.75 (4)	2.11 (4)	2.810 (3)	155 (4)
Symmetry codes: (i) x, y, z-1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) x-1, y, z; (v) x-1, y, z-1; (vi) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020204/hy2431sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020204/hy2431Isup2.hkl

checkCIF report

Comment top

Pyridine dicarboxylic acid derivatives, depending on the composition and situation of carboxylic groups and the number of deprotonated carboxylic groups, can form wide variety of compounds from organic proton transfer compounds (Aghabozorg et al., 2011a,c,d) to discrete coordination compounds (Aghabozorg et al., 2008, 2011b; Noro et al., 2005; Pasdar et al., 2011a) and coordination polymers (Pasdar et al., 2011b).

The asymmetric unit of the title compound is shown in Fig. 1. Two carboxylate groups of the pyridine-2,4-dicarboxylate (pydc) ligand are deprotonated and Ba^II ion is ten-coordinated in an NO₉ environment (Fig. 2). The crystal structure shows that the compound is a two-dimensional polymer (Fig. 3). O—H···O and C—H···O hydrogen bonds stabilize the crystal packing (Table 1).

Related literature top

For related compounds with pyridine dicarboxylic acid derivatives, see: Aghabozorg et al. (2008, 2011a,b,c,d); Noro et al. (2005); Pasdar et al. (2011a,b); Wang et al. (2007).

Experimental top

A mixture of Ba(NO₃)₂ (0.132 g), pyridine-2,4-dicarboxylic acid (0.085 g), 2,2'-bipyridine (0.156 g) in H₂O (60 ml) was stirred at 40°C for 1 h. The solution was filtered, and the filtrate was stand at room temperature. After two weaks, colorless block-shaped crystals of the title compound were obtained.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of the title compound, with displacement ellipsoids drawn at 50% probability level.
	Fig. 2. The coordination environment around Ba^II ion in the title compound. [Symmetry codes: (i) -x, -y+1, -z; (ii) x, -y+3/2, z-1/2; (iii) x, y, z-1; (iv) x, -y+3/2, z+1/2.]
	Fig. 3. A view of the two-dimensional structure of the title compound viewed down the a axis. H atoms have been omitted for clarity.

Poly[tri-µ₂-aqua-(µ₃-pyridine-2,4-dicarboxylato- κ⁴N,O²:O²:O^2')barium] top

Crystal data top

[Ba(C₇H₃NO₄)(H₂O)₃]	F(000) = 680
M_r = 356.48	D_x = 2.369 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2681 reflections
a = 11.079 (2) Å	θ = 2.4–29.1°
b = 13.714 (3) Å	µ = 4.00 mm⁻¹
c = 6.5961 (13) Å	T = 298 K
β = 94.13 (3)°	Block, colorless
V = 999.6 (3) Å³	0.39 × 0.38 × 0.33 mm
Z = 4

Data collection top

Stoe IPDS-2T diffractometer	2681 independent reflections
Radiation source: fine-focus sealed tube	2515 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 29.1°, θ_min = 2.4°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −15→13
T_min = 0.410, T_max = 0.460	k = −18→18
7321 measured reflections	l = −9→9

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)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0343P)² + 0.2871P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.002
2681 reflections	Δρ_max = 2.20 e Å⁻³
170 parameters	Δρ_min = −0.60 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0182 (7)

Crystal data top

[Ba(C₇H₃NO₄)(H₂O)₃]	V = 999.6 (3) Å³
M_r = 356.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.079 (2) Å	µ = 4.00 mm⁻¹
b = 13.714 (3) Å	T = 298 K
c = 6.5961 (13) Å	0.39 × 0.38 × 0.33 mm
β = 94.13 (3)°

Data collection top

Stoe IPDS-2T diffractometer	2681 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	2515 reflections with I > 2σ(I)
T_min = 0.410, T_max = 0.460	R_int = 0.041
7321 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	1 restraint
wR(F²) = 0.057	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 2.20 e Å⁻³
2681 reflections	Δρ_min = −0.60 e Å⁻³
170 parameters

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

	x	y	z	U_iso*/U_eq
H6B	−0.211 (3)	0.577 (3)	−0.019 (6)	0.045 (11)*
O6	−0.16582 (16)	0.54989 (14)	0.0517 (3)	0.0245 (3)
O7	−0.09028 (16)	0.75423 (14)	−0.1846 (3)	0.0234 (3)
O5	0.02949 (17)	0.45857 (14)	0.2957 (3)	0.0233 (3)
Ba1	0.074526 (10)	0.638147 (8)	0.073630 (17)	0.01506 (7)
C2	0.4566 (2)	0.63768 (15)	0.5688 (4)	0.0179 (4)
H2	0.4672	0.6508	0.7073	0.021*
N1	0.32012 (18)	0.61649 (17)	0.2709 (3)	0.0223 (4)
C1	0.3411 (2)	0.63417 (14)	0.4713 (4)	0.0166 (4)
C5	0.4167 (2)	0.6023 (2)	0.1646 (4)	0.0290 (5)
H5	0.4040	0.5907	0.0258	0.035*
O1	0.13032 (15)	0.66224 (14)	0.4870 (3)	0.0227 (3)
O2	0.24279 (19)	0.65068 (17)	0.7766 (3)	0.0341 (5)
C6	0.2301 (2)	0.64984 (16)	0.5894 (4)	0.0175 (4)
C7	0.6829 (2)	0.62030 (18)	0.5578 (4)	0.0206 (4)
C3	0.5562 (2)	0.62132 (17)	0.4560 (4)	0.0186 (4)
C4	0.5348 (2)	0.6037 (2)	0.2492 (4)	0.0268 (5)
H4	0.5990	0.5930	0.1685	0.032*
O3	0.69566 (19)	0.64657 (16)	0.7382 (3)	0.0340 (5)
O4	0.76764 (15)	0.59321 (15)	0.4537 (3)	0.0278 (4)
H5A	−0.019 (4)	0.438 (3)	0.361 (6)	0.047 (11)*
H5B	0.087 (4)	0.448 (3)	0.364 (6)	0.048 (12)*
H7B	−0.116 (4)	0.792 (3)	−0.116 (6)	0.039 (10)*
H6A	−0.209 (4)	0.550 (3)	0.164 (6)	0.043 (10)*
H7A	−0.155 (4)	0.723 (3)	−0.215 (7)	0.060 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O6	0.0208 (8)	0.0317 (9)	0.0211 (8)	0.0043 (7)	0.0026 (7)	0.0017 (7)
O7	0.0204 (8)	0.0251 (8)	0.0246 (8)	−0.0010 (7)	0.0016 (7)	−0.0014 (7)
O5	0.0192 (8)	0.0316 (9)	0.0191 (8)	0.0005 (7)	0.0014 (7)	0.0040 (7)
Ba1	0.01347 (9)	0.01844 (9)	0.01335 (10)	0.00009 (4)	0.00141 (5)	−0.00001 (4)
C2	0.0153 (10)	0.0255 (11)	0.0128 (10)	−0.0002 (7)	0.0004 (8)	0.0007 (7)
N1	0.0169 (9)	0.0350 (10)	0.0148 (9)	0.0023 (8)	−0.0012 (7)	−0.0034 (8)
C1	0.0128 (9)	0.0217 (10)	0.0156 (10)	0.0007 (7)	0.0026 (8)	0.0003 (7)
C5	0.0177 (10)	0.0535 (16)	0.0157 (10)	0.0048 (11)	0.0003 (8)	−0.0053 (11)
O1	0.0135 (7)	0.0330 (8)	0.0218 (8)	0.0041 (6)	0.0017 (6)	0.0010 (7)
O2	0.0216 (9)	0.0644 (14)	0.0170 (9)	−0.0006 (8)	0.0052 (7)	−0.0048 (8)
C6	0.0138 (9)	0.0202 (9)	0.0189 (10)	−0.0006 (7)	0.0042 (8)	−0.0010 (8)
C7	0.0137 (9)	0.0240 (9)	0.0237 (11)	−0.0005 (8)	−0.0013 (8)	0.0044 (9)
C3	0.0146 (9)	0.0227 (9)	0.0182 (10)	0.0006 (8)	0.0002 (8)	0.0014 (8)
C4	0.0160 (10)	0.0466 (15)	0.0179 (11)	0.0017 (10)	0.0026 (8)	−0.0032 (10)
O3	0.0237 (10)	0.0518 (12)	0.0252 (10)	0.0041 (8)	−0.0065 (8)	−0.0064 (8)
O4	0.0156 (7)	0.0406 (10)	0.0272 (9)	0.0030 (7)	0.0023 (6)	0.0028 (8)

Geometric parameters (Å, º) top

O6—H6B	0.75 (3)	C2—C1	1.391 (3)
O6—H6A	0.91 (4)	C2—C3	1.393 (3)
O7—H7B	0.75 (4)	C2—H2	0.9300
O7—H7A	0.85 (5)	N1—C5	1.336 (3)
O5—H5A	0.77 (5)	N1—C1	1.347 (3)
O5—H5B	0.77 (5)	C1—C6	1.518 (3)
Ba1—O1	2.7720 (19)	C5—C4	1.385 (3)
Ba1—O2ⁱ	2.805 (2)	C5—H5	0.9300
Ba1—O1ⁱⁱ	2.8728 (19)	O1—C6	1.265 (3)
Ba1—O7ⁱⁱⁱ	2.9111 (18)	O2—C6	1.233 (3)
Ba1—O7	2.8846 (19)	C7—O3	1.242 (3)
Ba1—O6^iv	2.9115 (19)	C7—O4	1.258 (3)
Ba1—O5^iv	2.935 (2)	C7—C3	1.511 (3)
Ba1—O5	2.9263 (19)	C3—C4	1.389 (3)
Ba1—N1	2.945 (2)	C4—H4	0.9300
Ba1—O6	2.9190 (19)

Ba1^iv—O6—Ba1	92.69 (5)	O7—Ba1—N1	147.33 (6)
Ba1^iv—O6—H6B	119 (3)	O7ⁱⁱⁱ—Ba1—N1	113.88 (6)
Ba1—O6—H6B	113 (3)	O6^iv—Ba1—N1	72.99 (6)
Ba1^iv—O6—H6A	117 (2)	O6—Ba1—N1	142.22 (6)
Ba1—O6—H6A	119 (2)	O5—Ba1—N1	83.07 (6)
H6B—O6—H6A	98 (4)	O5^iv—Ba1—N1	128.03 (6)
Ba1—O7—Ba1ⁱⁱ	102.01 (6)	O1—Ba1—C6ⁱⁱ	77.88 (6)
Ba1—O7—H7B	106 (3)	O2ⁱ—Ba1—C6ⁱⁱ	66.76 (6)
Ba1ⁱⁱ—O7—H7B	105 (3)	O1ⁱⁱ—Ba1—C6ⁱⁱ	21.45 (5)
Ba1—O7—H7A	110 (3)	O7—Ba1—C6ⁱⁱ	80.97 (6)
Ba1ⁱⁱ—O7—H7A	133 (3)	O7ⁱⁱⁱ—Ba1—C6ⁱⁱ	83.42 (5)
H7B—O7—H7A	98 (4)	O6^iv—Ba1—C6ⁱⁱ	125.75 (5)
Ba1—O5—Ba1^iv	92.06 (5)	O6—Ba1—C6ⁱⁱ	145.09 (5)
Ba1—O5—H5A	138 (3)	O5—Ba1—C6ⁱⁱ	144.49 (6)
Ba1^iv—O5—H5A	93 (3)	O5^iv—Ba1—C6ⁱⁱ	125.70 (5)
Ba1—O5—H5B	107 (3)	N1—Ba1—C6ⁱⁱ	67.67 (6)
Ba1^iv—O5—H5B	131 (3)	O1—Ba1—Ba1^iv	112.92 (4)
H5A—O5—H5B	101 (4)	O2ⁱ—Ba1—Ba1^iv	99.38 (5)
O1—Ba1—O2ⁱ	124.57 (6)	O1ⁱⁱ—Ba1—Ba1^iv	153.68 (4)
O1—Ba1—O1ⁱⁱ	92.64 (5)	O7—Ba1—Ba1^iv	98.00 (4)
O2ⁱ—Ba1—O1ⁱⁱ	68.86 (6)	O7ⁱⁱⁱ—Ba1—Ba1^iv	109.33 (4)
O1—Ba1—O7	127.00 (5)	O6^iv—Ba1—Ba1^iv	43.72 (4)
O2ⁱ—Ba1—O7	88.74 (6)	O6—Ba1—Ba1^iv	43.58 (4)
O1ⁱⁱ—Ba1—O7	59.52 (5)	O5—Ba1—Ba1^iv	44.06 (4)
O1—Ba1—O7ⁱⁱⁱ	60.32 (5)	O5^iv—Ba1—Ba1^iv	43.89 (4)
O2ⁱ—Ba1—O7ⁱⁱⁱ	145.70 (6)	N1—Ba1—Ba1^iv	110.18 (5)
O1ⁱⁱ—Ba1—O7ⁱⁱⁱ	77.19 (5)	C1—C2—C3	119.0 (2)
O7—Ba1—O7ⁱⁱⁱ	69.42 (3)	C1—C2—H2	120.5
O1—Ba1—O6^iv	109.12 (5)	C3—C2—H2	120.5
O2ⁱ—Ba1—O6^iv	66.05 (6)	C5—N1—C1	116.9 (2)
O1ⁱⁱ—Ba1—O6^iv	134.70 (5)	C5—N1—Ba1	122.17 (16)
O7—Ba1—O6^iv	122.63 (6)	C1—N1—Ba1	120.28 (14)
O7ⁱⁱⁱ—Ba1—O6^iv	148.11 (5)	N1—C1—C2	123.3 (2)
O1—Ba1—O6	103.66 (6)	N1—C1—C6	116.1 (2)
O2ⁱ—Ba1—O6	129.84 (6)	C2—C1—C6	120.7 (2)
O1ⁱⁱ—Ba1—O6	126.43 (5)	N1—C5—C4	123.8 (2)
O7—Ba1—O6	70.32 (5)	N1—C5—H5	118.1
O7ⁱⁱⁱ—Ba1—O6	68.38 (5)	C4—C5—H5	118.1
O6^iv—Ba1—O6	87.31 (5)	C6—O1—Ba1	129.32 (14)
O1—Ba1—O5	69.02 (5)	C6—O1—Ba1ⁱⁱⁱ	102.37 (14)
O2ⁱ—Ba1—O5	123.15 (6)	Ba1—O1—Ba1ⁱⁱⁱ	105.86 (6)
O1ⁱⁱ—Ba1—O5	161.49 (5)	C6—O2—Ba1^v	131.70 (16)
O7—Ba1—O5	129.53 (5)	O2—C6—O1	124.5 (2)
O7ⁱⁱⁱ—Ba1—O5	90.93 (5)	O2—C6—C1	118.5 (2)
O6^iv—Ba1—O5	58.13 (5)	O1—C6—C1	117.0 (2)
O6—Ba1—O5	59.20 (6)	O2—C6—Ba1ⁱⁱⁱ	92.52 (15)
O1—Ba1—O5^iv	156.43 (5)	O1—C6—Ba1ⁱⁱⁱ	56.18 (12)
O2ⁱ—Ba1—O5^iv	71.89 (6)	C1—C6—Ba1ⁱⁱⁱ	122.45 (13)
O1ⁱⁱ—Ba1—O5^iv	110.05 (5)	O3—C7—O4	124.8 (2)
O7—Ba1—O5^iv	64.24 (6)	O3—C7—C3	117.5 (2)
O7ⁱⁱⁱ—Ba1—O5^iv	117.35 (5)	O4—C7—C3	117.8 (2)
O6^iv—Ba1—O5^iv	59.19 (5)	C4—C3—C2	117.8 (2)
O6—Ba1—O5^iv	57.95 (5)	C4—C3—C7	121.5 (2)
O5—Ba1—O5^iv	87.94 (5)	C2—C3—C7	120.7 (2)
O1—Ba1—N1	56.21 (6)	C5—C4—C3	119.2 (2)
O2ⁱ—Ba1—N1	71.07 (6)	C5—C4—H4	120.4
O1ⁱⁱ—Ba1—N1	88.79 (6)	C3—C4—H4	120.4

Ba1ⁱⁱ—O7—Ba1—O1	108.60 (7)	C5—N1—C1—C2	−0.2 (4)
Ba1ⁱⁱ—O7—Ba1—O2ⁱ	−25.36 (7)	Ba1—N1—C1—C2	−171.43 (15)
Ba1ⁱⁱ—O7—Ba1—O1ⁱⁱ	40.72 (5)	C5—N1—C1—C6	−179.8 (2)
Ba1ⁱⁱ—O7—Ba1—O7ⁱⁱⁱ	127.63 (8)	Ba1—N1—C1—C6	9.0 (3)
Ba1ⁱⁱ—O7—Ba1—O6^iv	−85.61 (7)	C3—C2—C1—N1	−0.6 (3)
Ba1ⁱⁱ—O7—Ba1—O6	−158.86 (7)	C3—C2—C1—C6	178.93 (19)
Ba1ⁱⁱ—O7—Ba1—O5	−159.07 (5)	C1—N1—C5—C4	0.7 (4)
Ba1ⁱⁱ—O7—Ba1—O5^iv	−95.80 (7)	Ba1—N1—C5—C4	171.8 (2)
Ba1ⁱⁱ—O7—Ba1—N1	25.18 (13)	O2ⁱ—Ba1—O1—C6	−24.9 (2)
Ba1ⁱⁱ—O7—Ba1—C6ⁱⁱ	41.31 (6)	O1ⁱⁱ—Ba1—O1—C6	−90.95 (18)
Ba1ⁱⁱ—O7—Ba1—Ba1^iv	−124.66 (5)	O7—Ba1—O1—C6	−144.00 (18)
Ba1^iv—O6—Ba1—O1	−109.03 (5)	O7ⁱⁱⁱ—Ba1—O1—C6	−164.6 (2)
Ba1^iv—O6—Ba1—O2ⁱ	55.35 (9)	O6^iv—Ba1—O1—C6	48.6 (2)
Ba1^iv—O6—Ba1—O1ⁱⁱ	147.19 (5)	O6—Ba1—O1—C6	140.52 (19)
Ba1^iv—O6—Ba1—O7	126.16 (6)	O5—Ba1—O1—C6	91.6 (2)
Ba1^iv—O6—Ba1—O7ⁱⁱⁱ	−158.90 (7)	O5^iv—Ba1—O1—C6	104.5 (2)
Ba1^iv—O6—Ba1—O6^iv	0.0	N1—Ba1—O1—C6	−4.18 (18)
Ba1^iv—O6—Ba1—O5	−54.04 (5)	C6ⁱⁱ—Ba1—O1—C6	−75.3 (2)
Ba1^iv—O6—Ba1—O5^iv	54.86 (5)	Ba1^iv—Ba1—O1—C6	95.48 (19)
Ba1^iv—O6—Ba1—N1	−57.40 (10)	O2ⁱ—Ba1—O1—Ba1ⁱⁱⁱ	96.43 (7)
Ba1^iv—O6—Ba1—C6ⁱⁱ	162.67 (7)	O1ⁱⁱ—Ba1—O1—Ba1ⁱⁱⁱ	30.42 (8)
Ba1^iv—O5—Ba1—O1	174.89 (6)	O7—Ba1—O1—Ba1ⁱⁱⁱ	−22.64 (8)
Ba1^iv—O5—Ba1—O2ⁱ	−66.73 (8)	O7ⁱⁱⁱ—Ba1—O1—Ba1ⁱⁱⁱ	−43.21 (5)
Ba1^iv—O5—Ba1—O1ⁱⁱ	166.78 (13)	O6^iv—Ba1—O1—Ba1ⁱⁱⁱ	170.00 (5)
Ba1^iv—O5—Ba1—O7	53.60 (8)	O6—Ba1—O1—Ba1ⁱⁱⁱ	−98.11 (6)
Ba1^iv—O5—Ba1—O7ⁱⁱⁱ	117.34 (5)	O5—Ba1—O1—Ba1ⁱⁱⁱ	−147.01 (7)
Ba1^iv—O5—Ba1—O6^iv	−54.46 (5)	O5^iv—Ba1—O1—Ba1ⁱⁱⁱ	−134.14 (11)
Ba1^iv—O5—Ba1—O6	53.36 (6)	N1—Ba1—O1—Ba1ⁱⁱⁱ	117.19 (8)
Ba1^iv—O5—Ba1—O5^iv	0.0	C6ⁱⁱ—Ba1—O1—Ba1ⁱⁱⁱ	46.08 (6)
Ba1^iv—O5—Ba1—N1	−128.71 (6)	Ba1^iv—Ba1—O1—Ba1ⁱⁱⁱ	−143.15 (4)
Ba1^iv—O5—Ba1—C6ⁱⁱ	−162.71 (6)	Ba1^v—O2—C6—O1	14.9 (4)
O1—Ba1—N1—C5	−174.1 (2)	Ba1^v—O2—C6—C1	−165.84 (15)
O2ⁱ—Ba1—N1—C5	−12.0 (2)	Ba1^v—O2—C6—Ba1ⁱⁱⁱ	64.7 (2)
O1ⁱⁱ—Ba1—N1—C5	−80.1 (2)	Ba1—O1—C6—O2	−170.54 (18)
O7—Ba1—N1—C5	−66.7 (3)	Ba1ⁱⁱⁱ—O1—C6—O2	66.7 (3)
O7ⁱⁱⁱ—Ba1—N1—C5	−155.5 (2)	Ba1—O1—C6—C1	10.2 (3)
O6^iv—Ba1—N1—C5	57.8 (2)	Ba1ⁱⁱⁱ—O1—C6—C1	−112.54 (17)
O6—Ba1—N1—C5	119.5 (2)	Ba1—O1—C6—Ba1ⁱⁱⁱ	122.77 (18)
O5—Ba1—N1—C5	116.6 (2)	N1—C1—C6—O2	168.6 (2)
O5^iv—Ba1—N1—C5	34.7 (2)	C2—C1—C6—O2	−11.0 (3)
C6ⁱⁱ—Ba1—N1—C5	−84.0 (2)	N1—C1—C6—O1	−12.2 (3)
Ba1^iv—Ba1—N1—C5	81.3 (2)	C2—C1—C6—O1	168.2 (2)
O1—Ba1—N1—C1	−3.35 (16)	N1—C1—C6—Ba1ⁱⁱⁱ	−77.6 (2)
O2ⁱ—Ba1—N1—C1	158.68 (19)	C2—C1—C6—Ba1ⁱⁱⁱ	102.8 (2)
O1ⁱⁱ—Ba1—N1—C1	90.65 (18)	C1—C2—C3—C4	1.0 (3)
O7—Ba1—N1—C1	103.99 (18)	C1—C2—C3—C7	−177.42 (19)
O7ⁱⁱⁱ—Ba1—N1—C1	15.24 (19)	O3—C7—C3—C4	172.7 (3)
O6^iv—Ba1—N1—C1	−131.43 (19)	O4—C7—C3—C4	−7.1 (4)
O6—Ba1—N1—C1	−69.8 (2)	O3—C7—C3—C2	−8.9 (3)
O5—Ba1—N1—C1	−72.70 (18)	O4—C7—C3—C2	171.3 (2)
O5^iv—Ba1—N1—C1	−154.60 (16)	N1—C5—C4—C3	−0.4 (5)
C6ⁱⁱ—Ba1—N1—C1	86.74 (18)	C2—C3—C4—C5	−0.5 (4)
Ba1^iv—Ba1—N1—C1	−108.02 (17)	C7—C3—C4—C5	177.9 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.93	2.48	3.161 (3)	130
O5—H5A···O1^vi	0.77 (5)	2.14 (4)	2.881 (3)	162 (4)
O5—H5B···O4^vii	0.77 (5)	2.02 (5)	2.785 (3)	174 (4)
O6—H6A···O4^viii	0.91 (4)	2.03 (4)	2.865 (3)	151 (3)
O6—H6B···O3^ix	0.76 (4)	2.08 (4)	2.816 (3)	167 (4)
O7—H7A···O3^ix	0.85 (5)	1.96 (5)	2.809 (3)	175 (4)
O7—H7B···O4^x	0.75 (4)	2.11 (4)	2.810 (3)	155 (4)

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

Experimental details

Crystal data
Chemical formula	[Ba(C₇H₃NO₄)(H₂O)₃]
M_r	356.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.079 (2), 13.714 (3), 6.5961 (13)
β (°)	94.13 (3)
V (Å³)	999.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.00
Crystal size (mm)	0.39 × 0.38 × 0.33

Data collection
Diffractometer	Stoe IPDS2T diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)
T_min, T_max	0.410, 0.460
No. of measured, independent and observed [I > 2σ(I)] reflections	7321, 2681, 2515
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.057, 1.10
No. of reflections	2681
No. of parameters	170
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.20, −0.60

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.93	2.48	3.161 (3)	130
O5—H5A···O1ⁱⁱ	0.77 (5)	2.14 (4)	2.881 (3)	162 (4)
O5—H5B···O4ⁱⁱⁱ	0.77 (5)	2.02 (5)	2.785 (3)	174 (4)
O6—H6A···O4^iv	0.91 (4)	2.03 (4)	2.865 (3)	151 (3)
O6—H6B···O3^v	0.76 (4)	2.08 (4)	2.816 (3)	167 (4)
O7—H7A···O3^v	0.85 (5)	1.96 (5)	2.809 (3)	175 (4)
O7—H7B···O4^vi	0.75 (4)	2.11 (4)	2.810 (3)	155 (4)

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

Acknowledgements

The authors gratefully acknowledge the Islamic Azad University, North Tehran Branch, for financial support.

References

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