catena-Poly[[bis­(nitrato-κ2O,O′)barium]-bis­(μ-l-histidine-κ3O,O′:O]

Arularasan, P.; Chakkaravarthi, G.; Mohan, R.

doi:10.1107/S1600536813027402

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page m597

doi:10.1107/S1600536813027402

Open

access

catena-Poly[[bis(nitrato-κ²O,O′)barium]-bis(μ-L-histidine-κ³O,O′:O]

P. Arularasan,^a G. Chakkaravarthi ^b ^* and R. Mohan ^a ^*

^aDepartment of Physics, Presidency College, Chennai 600 005, India, and ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, professormohan@yahoo.co.in

(Received 28 September 2013; accepted 6 October 2013; online 12 October 2013)

In the polymeric title compound, [Ba(NO₃)₂(C₆H₉N₃O₂)₂]_n, the Ba^II atom is located on a crystallographic twofold axis and is coordinated by ten O atoms. Six are derived from two zwitterionic L-histidine molecules that simultaneously chelate one Ba^II atom and bridge to another. The remaining four O atoms are derived from two chelating nitrates. The molecules assemble to form a chain along [010]. In the crystal, chains are linked via N—H⋯O and N—H⋯N hydrogen bonds, generating a three-dimensional network.

CCDC reference: 965078

Related literature

For the biological activity of histidine, see: Eichler et al. (2005 ); Wimalasena et al. (2007 ). For standard bond lengths, see: Allen et al. (1987 ). For related structures, see: Andra et al. (2010 ); Gokul Raj et al. (2006 ).

Experimental

Crystal data

[Ba(NO₃)₂(C₆H₉N₃O₂)₂]
M_r = 571.68
Monoclinic, C 2
a = 24.9063 (8) Å
b = 4.7226 (1) Å
c = 8.3180 (3) Å
β = 105.432 (1)°
V = 943.11 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.18 mm⁻¹
T = 295 K
0.18 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.695, T_max = 0.780
6598 measured reflections
3281 independent reflections
3281 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.048
S = 1.15
3281 reflections
142 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.40 e Å⁻³
Δρ_min = −1.32 e Å⁻³
Absolute structure: Flack (1983 ), 1164 Friedel pairs
Absolute structure parameter: 0.004 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.86	2.29	2.854 (3)	123
N1—H1⋯O5ⁱⁱ	0.86	2.37	3.121 (3)	146
N3—H3B⋯O1ⁱⁱⁱ	0.89	2.19	3.029 (2)	158
N3—H3C⋯O3^iv	0.89	2.05	2.867 (3)	153
N3—H3A⋯N2^v	0.89	1.94	2.827 (3)	174
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1]$ ; (iii) -x+1, y, -z+1; (iv) x, y+1, z-1; (v) x, y-1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 965078

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813027402/tk5259sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813027402/tk5259Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813027402/tk5259Isup3.cml

checkCIF report

Comment top

Histidine derivatives are used in enzyme mechanisms and biomolecular interactions (Eichler et al., 2005; Wimalasena et al., 2007). We herein, report the crystal structure of the title compound (I), (Fig. 1). The geometric parameters of L-histidine moiety of (I) are comparable with the reported related structures (Andra et al., 2010; Gokul Raj et al., 2006).

The Ba atom sits on a crystallographic twofold axis and is co-ordinated by 10 O atoms, with six O atoms from carboxylate groups of L-Histidine and four O atoms from two nitrates. The Ba—O distances, ranging from 2.767 (5) to 2.966 (2) Å, are within normal range (Allen et al., 1987).

The molecule coordinate through O to form a one dimensional chain, extending along [010]. The chains are interlinked through N—H···N and N—H···O hydrogen bonds (Table 1 & Fig. 2).

Related literature top

For the biological activity of histidine, see: Eichler et al. (2005); Wimalasena et al. (2007). For standard bond lengths, see: Allen et al. (1987). For related structures, see: Andra et al. (2010); Gokul Raj et al. (2006).

Experimental top

The title compound was synthesized from the starting materials of L –histidine (3.1030 g) and barium nitrate (2.6133 g) which were taken in water. Single crystals suitable for X-ray diffraction were grown by the slow evaporation technique at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A portion of the polymeric structure in (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. The symmetry codes are : (a) x, -1+y, z; (c) 1-x, -1+y, 2-z; (d) 1-x, y, 2-z.
	Fig. 2. The packing of (I), viewed down the b axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

catena-Poly[[bis(nitrato-κ²O,O')barium]-bis(µ-L-histidine-κ³O,O':O] top

Crystal data top

[Ba(NO₃)₂(C₆H₉N₃O₂)₂]	F(000) = 564
M_r = 571.68	D_x = 2.013 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 6604 reflections
a = 24.9063 (8) Å	θ = 2.6–34.9°
b = 4.7226 (1) Å	µ = 2.18 mm⁻¹
c = 8.3180 (3) Å	T = 295 K
β = 105.432 (1)°	Block, colourless
V = 943.11 (5) Å³	0.18 × 0.14 × 0.12 mm
Z = 2

Data collection top

Bruker Kappa APEXII diffractometer	3281 independent reflections
Radiation source: fine-focus sealed tube	3281 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scan	θ_max = 34.9°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −39→40
T_min = 0.695, T_max = 0.780	k = −6→7
6598 measured reflections	l = −13→11

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)] = 0.019	H-atom parameters constrained
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.021P)²] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
3281 reflections	Δρ_max = 1.40 e Å⁻³
142 parameters	Δρ_min = −1.32 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1164 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (13)

Crystal data top

[Ba(NO₃)₂(C₆H₉N₃O₂)₂]	V = 943.11 (5) Å³
M_r = 571.68	Z = 2
Monoclinic, C2	Mo Kα radiation
a = 24.9063 (8) Å	µ = 2.18 mm⁻¹
b = 4.7226 (1) Å	T = 295 K
c = 8.3180 (3) Å	0.18 × 0.14 × 0.12 mm
β = 105.432 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	3281 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3281 reflections with I > 2σ(I)
T_min = 0.695, T_max = 0.780	R_int = 0.030
6598 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	H-atom parameters constrained
wR(F²) = 0.048	Δρ_max = 1.40 e Å⁻³
S = 1.15	Δρ_min = −1.32 e Å⁻³
3281 reflections	Absolute structure: Flack (1983), 1164 Friedel pairs
142 parameters	Absolute structure parameter: 0.004 (13)
2 restraints

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
C1	0.31466 (7)	0.2871 (5)	0.4170 (3)	0.0239 (4)
C2	0.26202 (8)	0.1922 (6)	0.3475 (3)	0.0304 (4)
H2	0.2451	0.0343	0.3795	0.036*
C3	0.27774 (8)	0.5757 (17)	0.2181 (3)	0.0335 (5)
H3	0.2722	0.7264	0.1436	0.040*
C4	0.35756 (8)	0.1666 (6)	0.5623 (3)	0.0290 (5)
H4A	0.3439	−0.0118	0.5935	0.035*
H4B	0.3623	0.2948	0.6561	0.035*
C5	0.41435 (6)	0.1163 (13)	0.5298 (2)	0.0215 (7)
H5	0.4297	0.3001	0.5099	0.026*
C6	0.45415 (7)	−0.0175 (5)	0.6835 (2)	0.0210 (3)
N1	0.23922 (7)	0.3754 (6)	0.2217 (3)	0.0325 (4)
H1	0.2062	0.3656	0.1559	0.039*
N2	0.32423 (7)	0.5272 (4)	0.3354 (3)	0.0295 (5)
N3	0.40970 (7)	−0.0632 (4)	0.3806 (2)	0.0228 (3)
H3A	0.3830	−0.1914	0.3737	0.034*
H3B	0.4420	−0.1508	0.3889	0.034*
H3C	0.4014	0.0447	0.2896	0.034*
N4	0.37614 (8)	−0.6072 (6)	1.0220 (3)	0.0332 (4)
O1	0.47815 (7)	−0.2417 (4)	0.6626 (2)	0.0307 (3)
O2	0.45918 (6)	0.1055 (13)	0.81973 (19)	0.0294 (4)
O3	0.41918 (7)	−0.6466 (7)	1.1390 (3)	0.0470 (6)
O4	0.33641 (9)	−0.7646 (8)	1.0069 (4)	0.0721 (10)
O5	0.37673 (8)	−0.4073 (15)	0.9258 (3)	0.0556 (6)
Ba1	0.5000	−0.4123	1.0000	0.01742 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0190 (6)	0.0295 (10)	0.0223 (8)	0.0045 (7)	0.0037 (6)	−0.0027 (7)
C2	0.0230 (7)	0.0366 (11)	0.0318 (10)	0.0004 (7)	0.0078 (7)	−0.0016 (9)
C3	0.0314 (7)	0.0362 (14)	0.0296 (8)	0.0084 (12)	0.0024 (6)	0.004 (2)
C4	0.0245 (7)	0.0423 (15)	0.0203 (8)	0.0088 (7)	0.0060 (6)	0.0015 (7)
C5	0.0199 (5)	0.026 (2)	0.0174 (6)	0.0013 (9)	0.0026 (4)	0.0025 (9)
C6	0.0183 (6)	0.0243 (8)	0.0183 (7)	−0.0019 (6)	0.0015 (5)	0.0044 (6)
N1	0.0196 (6)	0.0449 (12)	0.0288 (9)	0.0058 (7)	−0.0007 (6)	−0.0050 (8)
N2	0.0245 (6)	0.0315 (14)	0.0288 (8)	0.0010 (6)	0.0006 (6)	−0.0009 (7)
N3	0.0214 (6)	0.0292 (9)	0.0173 (7)	0.0016 (6)	0.0043 (5)	0.0019 (6)
N4	0.0239 (7)	0.0451 (13)	0.0306 (10)	−0.0018 (8)	0.0074 (7)	−0.0103 (9)
O1	0.0340 (7)	0.0345 (9)	0.0228 (7)	0.0136 (7)	0.0059 (6)	0.0055 (6)
O2	0.0357 (5)	0.0258 (12)	0.0207 (5)	−0.0022 (12)	−0.0031 (4)	−0.0052 (12)
O3	0.0274 (7)	0.0762 (18)	0.0357 (10)	−0.0054 (9)	0.0056 (7)	0.0222 (11)
O4	0.0427 (11)	0.092 (2)	0.088 (2)	−0.0382 (13)	0.0288 (13)	−0.0513 (19)
O5	0.0467 (9)	0.0721 (16)	0.0462 (11)	0.020 (2)	0.0091 (8)	0.018 (3)
Ba1	0.01895 (5)	0.01937 (6)	0.01343 (5)	0.000	0.00342 (3)	0.000

Geometric parameters (Å, º) top

C1—C2	1.360 (3)	N3—H3B	0.8900
C1—N2	1.374 (3)	N3—H3C	0.8900
C1—C4	1.496 (3)	N4—O4	1.217 (3)
C2—N1	1.360 (4)	N4—O5	1.240 (6)
C2—H2	0.9300	N4—O3	1.255 (3)
C3—N2	1.320 (3)	N4—Ba1	3.271 (2)
C3—N1	1.353 (7)	O1—Ba1	2.8300 (17)
C3—H3	0.9300	O2—Ba1ⁱ	2.767 (5)
C4—C5	1.528 (3)	O2—Ba1	2.907 (5)
C4—H4A	0.9700	O3—Ba1	2.8022 (19)
C4—H4B	0.9700	O5—Ba1	2.9664 (18)
C5—N3	1.482 (4)	Ba1—O2ⁱⁱ	2.767 (5)
C5—C6	1.530 (3)	Ba1—O2ⁱⁱⁱ	2.767 (5)
C5—H5	0.9800	Ba1—O3^iv	2.8022 (19)
C6—O2	1.249 (4)	Ba1—O1^iv	2.8300 (17)
C6—O1	1.251 (3)	Ba1—O2^iv	2.907 (5)
C6—Ba1	3.180 (2)	Ba1—O5^iv	2.9664 (18)
N1—H1	0.8600	Ba1—C6^iv	3.180 (2)
N3—H3A	0.8900

C2—C1—N2	109.63 (19)	O3—Ba1—O1^iv	70.91 (6)
C2—C1—C4	128.2 (2)	O2ⁱⁱ—Ba1—O1	75.58 (9)
N2—C1—C4	122.15 (19)	O2ⁱⁱⁱ—Ba1—O1	135.86 (7)
N1—C2—C1	106.0 (2)	O3^iv—Ba1—O1	70.91 (6)
N1—C2—H2	127.0	O3—Ba1—O1	123.50 (5)
C1—C2—H2	127.0	O1^iv—Ba1—O1	146.92 (9)
N2—C3—N1	110.5 (5)	O2ⁱⁱ—Ba1—O2^iv	178.12 (13)
N2—C3—H3	124.8	O2ⁱⁱⁱ—Ba1—O2^iv	112.65 (5)
N1—C3—H3	124.8	O3^iv—Ba1—O2^iv	110.73 (6)
C1—C4—C5	114.35 (19)	O3—Ba1—O2^iv	108.08 (8)
C1—C4—H4A	108.7	O1^iv—Ba1—O2^iv	45.61 (7)
C5—C4—H4A	108.7	O1—Ba1—O2^iv	102.75 (7)
C1—C4—H4B	108.7	O2ⁱⁱ—Ba1—O2	112.65 (5)
C5—C4—H4B	108.7	O2ⁱⁱⁱ—Ba1—O2	178.12 (14)
H4A—C4—H4B	107.6	O3^iv—Ba1—O2	108.08 (8)
N3—C5—C4	111.5 (2)	O3—Ba1—O2	110.73 (6)
N3—C5—C6	110.6 (3)	O1^iv—Ba1—O2	102.75 (7)
C4—C5—C6	109.95 (18)	O1—Ba1—O2	45.61 (7)
N3—C5—H5	108.2	O2^iv—Ba1—O2	65.47 (13)
C4—C5—H5	108.2	O2ⁱⁱ—Ba1—O5^iv	109.27 (11)
C6—C5—H5	108.2	O2ⁱⁱⁱ—Ba1—O5^iv	71.53 (14)
O2—C6—O1	125.7 (3)	O3^iv—Ba1—O5^iv	43.25 (9)
O2—C6—C5	116.9 (3)	O3—Ba1—O5^iv	137.28 (10)
O1—C6—C5	117.4 (2)	O1^iv—Ba1—O5^iv	82.88 (6)
O2—C6—Ba1	66.1 (3)	O1—Ba1—O5^iv	96.85 (7)
O1—C6—Ba1	62.55 (11)	O2^iv—Ba1—O5^iv	71.66 (13)
C5—C6—Ba1	160.70 (18)	O2—Ba1—O5^iv	107.53 (13)
C3—N1—C2	107.9 (2)	O2ⁱⁱ—Ba1—O5	71.53 (14)
C3—N1—H1	126.0	O2ⁱⁱⁱ—Ba1—O5	109.27 (11)
C2—N1—H1	126.0	O3^iv—Ba1—O5	137.28 (10)
C3—N2—C1	105.9 (3)	O3—Ba1—O5	43.25 (9)
C5—N3—H3A	109.5	O1^iv—Ba1—O5	96.85 (7)
C5—N3—H3B	109.5	O1—Ba1—O5	82.88 (6)
H3A—N3—H3B	109.5	O2^iv—Ba1—O5	107.53 (13)
C5—N3—H3C	109.5	O2—Ba1—O5	71.66 (13)
H3A—N3—H3C	109.5	O5^iv—Ba1—O5	179.1 (3)
H3B—N3—H3C	109.5	O2ⁱⁱ—Ba1—C6^iv	158.50 (8)
O4—N4—O5	123.2 (3)	O2ⁱⁱⁱ—Ba1—C6^iv	91.99 (9)
O4—N4—O3	119.5 (3)	O3^iv—Ba1—C6^iv	115.73 (5)
O5—N4—O3	117.3 (2)	O3—Ba1—C6^iv	91.67 (7)
O4—N4—Ba1	156.8 (2)	O1^iv—Ba1—C6^iv	23.09 (6)
O5—N4—Ba1	64.94 (12)	O1—Ba1—C6^iv	125.88 (6)
O3—N4—Ba1	57.42 (12)	O2^iv—Ba1—C6^iv	23.14 (7)
C6—O1—Ba1	94.36 (13)	O2—Ba1—C6^iv	86.16 (8)
C6—O2—Ba1ⁱ	143.9 (3)	O5^iv—Ba1—C6^iv	72.50 (9)
C6—O2—Ba1	90.8 (3)	O5—Ba1—C6^iv	106.94 (10)
Ba1ⁱ—O2—Ba1	112.65 (5)	O2ⁱⁱ—Ba1—C6	91.99 (9)
N4—O3—Ba1	100.40 (16)	O2ⁱⁱⁱ—Ba1—C6	158.50 (8)
N4—O5—Ba1	92.81 (15)	O3^iv—Ba1—C6	91.67 (7)
O2ⁱⁱ—Ba1—O2ⁱⁱⁱ	69.23 (15)	O3—Ba1—C6	115.73 (5)
O2ⁱⁱ—Ba1—O3^iv	69.64 (6)	O1^iv—Ba1—C6	125.88 (6)
O2ⁱⁱⁱ—Ba1—O3^iv	72.42 (8)	O1—Ba1—C6	23.09 (6)
O2ⁱⁱ—Ba1—O3	72.42 (8)	O2^iv—Ba1—C6	86.16 (8)
O2ⁱⁱⁱ—Ba1—O3	69.64 (6)	O2—Ba1—C6	23.14 (7)
O3^iv—Ba1—O3	133.48 (13)	O5^iv—Ba1—C6	106.94 (10)
O2ⁱⁱ—Ba1—O1^iv	135.86 (7)	O5—Ba1—C6	72.50 (9)
O2ⁱⁱⁱ—Ba1—O1^iv	75.58 (9)	C6^iv—Ba1—C6	108.20 (8)
O3^iv—Ba1—O1^iv	123.50 (5)

N2—C1—C2—N1	0.3 (3)	C6—O2—Ba1—O1^iv	178.66 (13)
C4—C1—C2—N1	178.7 (2)	Ba1ⁱ—O2—Ba1—O1^iv	26.92 (7)
C2—C1—C4—C5	129.1 (3)	C6—O2—Ba1—O1	9.91 (11)
N2—C1—C4—C5	−52.6 (4)	Ba1ⁱ—O2—Ba1—O1	−141.84 (10)
C1—C4—C5—N3	−54.6 (4)	C6—O2—Ba1—O2^iv	151.75 (17)
C1—C4—C5—C6	−177.8 (3)	Ba1ⁱ—O2—Ba1—O2^iv	0.0
N3—C5—C6—O2	−176.0 (3)	C6—O2—Ba1—O5^iv	92.20 (15)
C4—C5—C6—O2	−52.3 (4)	Ba1ⁱ—O2—Ba1—O5^iv	−59.54 (9)
N3—C5—C6—O1	3.0 (3)	C6—O2—Ba1—O5	−88.25 (17)
C4—C5—C6—O1	126.7 (3)	Ba1ⁱ—O2—Ba1—O5	120.00 (11)
N3—C5—C6—Ba1	−81.9 (5)	C6—O2—Ba1—C6^iv	162.49 (12)
C4—C5—C6—Ba1	41.8 (9)	Ba1ⁱ—O2—Ba1—C6^iv	10.74 (6)
N2—C3—N1—C2	0.4 (4)	Ba1ⁱ—O2—Ba1—C6	−151.75 (17)
C1—C2—N1—C3	−0.4 (3)	N4—O5—Ba1—O2ⁱⁱ	69.8 (3)
N1—C3—N2—C1	−0.3 (4)	N4—O5—Ba1—O2ⁱⁱⁱ	10.7 (3)
C2—C1—N2—C3	0.0 (3)	N4—O5—Ba1—O3^iv	95.3 (2)
C4—C1—N2—C3	−178.6 (3)	N4—O5—Ba1—O3	−13.90 (19)
O2—C6—O1—Ba1	20.7 (3)	N4—O5—Ba1—O1^iv	−66.4 (3)
C5—C6—O1—Ba1	−158.23 (19)	N4—O5—Ba1—O1	146.9 (3)
O1—C6—O2—Ba1ⁱ	112.2 (4)	N4—O5—Ba1—O2^iv	−111.9 (3)
C5—C6—O2—Ba1ⁱ	−68.9 (4)	N4—O5—Ba1—O2	−167.6 (3)
Ba1—C6—O2—Ba1ⁱ	132.2 (3)	N4—O5—Ba1—C6^iv	−87.7 (3)
O1—C6—O2—Ba1	−20.0 (3)	N4—O5—Ba1—C6	168.1 (3)
C5—C6—O2—Ba1	158.9 (2)	O2—C6—Ba1—O2ⁱⁱ	154.08 (15)
O4—N4—O3—Ba1	153.1 (2)	O1—C6—Ba1—O2ⁱⁱ	−44.19 (13)
O5—N4—O3—Ba1	−26.4 (3)	C5—C6—Ba1—O2ⁱⁱ	50.8 (6)
O4—N4—O5—Ba1	−155.0 (3)	O2—C6—Ba1—O2ⁱⁱⁱ	−177.57 (18)
O3—N4—O5—Ba1	24.4 (3)	O1—C6—Ba1—O2ⁱⁱⁱ	−15.8 (2)
N4—O3—Ba1—O2ⁱⁱ	−67.5 (2)	C5—C6—Ba1—O2ⁱⁱⁱ	79.2 (6)
N4—O3—Ba1—O2ⁱⁱⁱ	−141.3 (2)	O2—C6—Ba1—O3^iv	−136.24 (14)
N4—O3—Ba1—O3^iv	−104.1 (2)	O1—C6—Ba1—O3^iv	25.49 (14)
N4—O3—Ba1—O1^iv	137.5 (2)	C5—C6—Ba1—O3^iv	120.5 (6)
N4—O3—Ba1—O1	−9.1 (2)	O2—C6—Ba1—O3	82.67 (16)
N4—O3—Ba1—O2^iv	110.6 (2)	O1—C6—Ba1—O3	−115.60 (14)
N4—O3—Ba1—O2	40.7 (2)	C5—C6—Ba1—O3	−20.6 (6)
N4—O3—Ba1—O5^iv	−167.1 (2)	O2—C6—Ba1—O1^iv	−1.61 (15)
N4—O3—Ba1—O5	14.0 (2)	O1—C6—Ba1—O1^iv	160.12 (10)
N4—O3—Ba1—C6^iv	127.2 (2)	C5—C6—Ba1—O1^iv	−104.9 (6)
N4—O3—Ba1—C6	16.0 (2)	O2—C6—Ba1—O1	−161.7 (2)
C6—O1—Ba1—O2ⁱⁱ	134.00 (14)	C5—C6—Ba1—O1	95.0 (6)
C6—O1—Ba1—O2ⁱⁱⁱ	171.74 (13)	O2—C6—Ba1—O2^iv	−25.57 (16)
C6—O1—Ba1—O3^iv	−152.92 (15)	O1—C6—Ba1—O2^iv	136.16 (13)
C6—O1—Ba1—O3	76.98 (16)	C5—C6—Ba1—O2^iv	−128.8 (6)
C6—O1—Ba1—O1^iv	−30.33 (12)	O1—C6—Ba1—O2	161.7 (2)
C6—O1—Ba1—O2^iv	−45.12 (14)	C5—C6—Ba1—O2	−103.3 (6)
C6—O1—Ba1—O2	−9.93 (12)	O2—C6—Ba1—O5^iv	−95.07 (16)
C6—O1—Ba1—O5^iv	−117.80 (18)	O1—C6—Ba1—O5^iv	66.65 (17)
C6—O1—Ba1—O5	61.31 (18)	C5—C6—Ba1—O5^iv	161.7 (6)
C6—O1—Ba1—C6^iv	−44.47 (16)	O2—C6—Ba1—O5	84.17 (19)
C6—O2—Ba1—O2ⁱⁱ	−28.25 (17)	O1—C6—Ba1—O5	−114.11 (18)
Ba1ⁱ—O2—Ba1—O2ⁱⁱ	180.000 (1)	C5—C6—Ba1—O5	−19.1 (6)
C6—O2—Ba1—O3^iv	46.66 (15)	O2—C6—Ba1—C6^iv	−18.42 (12)
Ba1ⁱ—O2—Ba1—O3^iv	−105.09 (7)	O1—C6—Ba1—C6^iv	143.31 (14)
C6—O2—Ba1—O3	−107.18 (14)	C5—C6—Ba1—C6^iv	−121.7 (6)
Ba1ⁱ—O2—Ba1—O3	101.07 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4^v	0.86	2.29	2.854 (3)	123
N1—H1···O5^vi	0.86	2.37	3.121 (3)	146
N3—H3B···O1^vii	0.89	2.19	3.029 (2)	158
N3—H3C···O3^viii	0.89	2.05	2.867 (3)	153
N3—H3A···N2ⁱⁱ	0.89	1.94	2.827 (3)	174

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.86	2.29	2.854 (3)	123
N1—H1···O5ⁱⁱ	0.86	2.37	3.121 (3)	146
N3—H3B···O1ⁱⁱⁱ	0.89	2.19	3.029 (2)	158
N3—H3C···O3^iv	0.89	2.05	2.867 (3)	153
N3—H3A···N2^v	0.89	1.94	2.827 (3)	174

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

Acknowledgements

The authors wish to acknowledge the SAIF, IIT Madras, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Andra, K. K., Bullinger, J. C., Bann, J. G. & Eichhorn, D. M. (2010). Acta Cryst. E66, o2713. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Eichler, J. F., Cramer, J. C., Kirk, K. L. & Bann, J. G. (2005). ChemBioChem, 6, 2170–2173. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gokul Raj, S., Ramesh Kumar, G., Raghavalu, T., Mohan, R. & Jayavel, R. (2006). Acta Cryst. E62, o1178–o1180. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wimalasena, D. S., Cramer, J. C., Janowiak, B. E., Juris, S. J., Melnyk, R. A., Anderson, D. E., Kirk, K. L., Collier, R. J. & Bann, J. G. (2007). Biochemistry, 46, 14928–14936. Web of Science CrossRef PubMed CAS Google Scholar