catena-Poly[[bis-(nitrato-κ(2) O,O')barium]-bis-(μ-l-histidine-κ(3) O,O':O].

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 mol-ecules that simultaneously chelate one Ba(II) atom and bridge to another. The remaining four O atoms are derived from two chelating nitrates. The mol-ecules 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.

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 = 571.68

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.048

S = 1.15

3281 reflections

142 parameters

2 restraints

H-atom parameters constrained

Δρmax = 1.40 e Å−3

Δρmin = −1.32 e Å−3

Absolute structure: Flack (1983 ▶), 1164 Friedel pairs

Absolute structure parameter: 0.004 (13)

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813027402/tk5259sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027402/tk5259Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ba(NO3)2(C6H9N3O2)2]	F(000) = 564
Mr = 571.68	Dx = 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

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

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(Fo2) + (0.021P)2] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
3281 reflections	Δρmax = 1.40 e Å−3
142 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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

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—O3iv	2.8022 (19)
C6—O2	1.249 (4)	Ba1—O1iv	2.8300 (17)
C6—O1	1.251 (3)	Ba1—O2iv	2.907 (5)
C6—Ba1	3.180 (2)	Ba1—O5iv	2.9664 (18)
N1—H1	0.8600	Ba1—C6iv	3.180 (2)
N3—H3A	0.8900
C2—C1—N2	109.63 (19)	O3—Ba1—O1iv	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)	O3iv—Ba1—O1	70.91 (6)
N1—C2—H2	127.0	O3—Ba1—O1	123.50 (5)
C1—C2—H2	127.0	O1iv—Ba1—O1	146.92 (9)
N2—C3—N1	110.5 (5)	O2ii—Ba1—O2iv	178.12 (13)
N2—C3—H3	124.8	O2iii—Ba1—O2iv	112.65 (5)
N1—C3—H3	124.8	O3iv—Ba1—O2iv	110.73 (6)
C1—C4—C5	114.35 (19)	O3—Ba1—O2iv	108.08 (8)
C1—C4—H4A	108.7	O1iv—Ba1—O2iv	45.61 (7)
C5—C4—H4A	108.7	O1—Ba1—O2iv	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	O3iv—Ba1—O2	108.08 (8)
N3—C5—C4	111.5 (2)	O3—Ba1—O2	110.73 (6)
N3—C5—C6	110.6 (3)	O1iv—Ba1—O2	102.75 (7)
C4—C5—C6	109.95 (18)	O1—Ba1—O2	45.61 (7)
N3—C5—H5	108.2	O2iv—Ba1—O2	65.47 (13)
C4—C5—H5	108.2	O2ii—Ba1—O5iv	109.27 (11)
C6—C5—H5	108.2	O2iii—Ba1—O5iv	71.53 (14)
O2—C6—O1	125.7 (3)	O3iv—Ba1—O5iv	43.25 (9)
O2—C6—C5	116.9 (3)	O3—Ba1—O5iv	137.28 (10)
O1—C6—C5	117.4 (2)	O1iv—Ba1—O5iv	82.88 (6)
O2—C6—Ba1	66.1 (3)	O1—Ba1—O5iv	96.85 (7)
O1—C6—Ba1	62.55 (11)	O2iv—Ba1—O5iv	71.66 (13)
C5—C6—Ba1	160.70 (18)	O2—Ba1—O5iv	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	O3iv—Ba1—O5	137.28 (10)
C3—N2—C1	105.9 (3)	O3—Ba1—O5	43.25 (9)
C5—N3—H3A	109.5	O1iv—Ba1—O5	96.85 (7)
C5—N3—H3B	109.5	O1—Ba1—O5	82.88 (6)
H3A—N3—H3B	109.5	O2iv—Ba1—O5	107.53 (13)
C5—N3—H3C	109.5	O2—Ba1—O5	71.66 (13)
H3A—N3—H3C	109.5	O5iv—Ba1—O5	179.1 (3)
H3B—N3—H3C	109.5	O2ii—Ba1—C6iv	158.50 (8)
O4—N4—O5	123.2 (3)	O2iii—Ba1—C6iv	91.99 (9)
O4—N4—O3	119.5 (3)	O3iv—Ba1—C6iv	115.73 (5)
O5—N4—O3	117.3 (2)	O3—Ba1—C6iv	91.67 (7)
O4—N4—Ba1	156.8 (2)	O1iv—Ba1—C6iv	23.09 (6)
O5—N4—Ba1	64.94 (12)	O1—Ba1—C6iv	125.88 (6)
O3—N4—Ba1	57.42 (12)	O2iv—Ba1—C6iv	23.14 (7)
C6—O1—Ba1	94.36 (13)	O2—Ba1—C6iv	86.16 (8)
C6—O2—Ba1i	143.9 (3)	O5iv—Ba1—C6iv	72.50 (9)
C6—O2—Ba1	90.8 (3)	O5—Ba1—C6iv	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)	O3iv—Ba1—C6	91.67 (7)
O2ii—Ba1—O2iii	69.23 (15)	O3—Ba1—C6	115.73 (5)
O2ii—Ba1—O3iv	69.64 (6)	O1iv—Ba1—C6	125.88 (6)
O2iii—Ba1—O3iv	72.42 (8)	O1—Ba1—C6	23.09 (6)
O2ii—Ba1—O3	72.42 (8)	O2iv—Ba1—C6	86.16 (8)
O2iii—Ba1—O3	69.64 (6)	O2—Ba1—C6	23.14 (7)
O3iv—Ba1—O3	133.48 (13)	O5iv—Ba1—C6	106.94 (10)
O2ii—Ba1—O1iv	135.86 (7)	O5—Ba1—C6	72.50 (9)
O2iii—Ba1—O1iv	75.58 (9)	C6iv—Ba1—C6	108.20 (8)
O3iv—Ba1—O1iv	123.50 (5)
N2—C1—C2—N1	0.3 (3)	C6—O2—Ba1—O1iv	178.66 (13)
C4—C1—C2—N1	178.7 (2)	Ba1i—O2—Ba1—O1iv	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—O2iv	151.75 (17)
C1—C4—C5—C6	−177.8 (3)	Ba1i—O2—Ba1—O2iv	0.0
N3—C5—C6—O2	−176.0 (3)	C6—O2—Ba1—O5iv	92.20 (15)
C4—C5—C6—O2	−52.3 (4)	Ba1i—O2—Ba1—O5iv	−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—C6iv	162.49 (12)
C4—C5—C6—Ba1	41.8 (9)	Ba1i—O2—Ba1—C6iv	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—O3iv	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—O1iv	−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—O2iv	−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—C6iv	−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—O3iv	−136.24 (14)
N4—O3—Ba1—O3iv	−104.1 (2)	O1—C6—Ba1—O3iv	25.49 (14)
N4—O3—Ba1—O1iv	137.5 (2)	C5—C6—Ba1—O3iv	120.5 (6)
N4—O3—Ba1—O1	−9.1 (2)	O2—C6—Ba1—O3	82.67 (16)
N4—O3—Ba1—O2iv	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—O5iv	−167.1 (2)	O2—C6—Ba1—O1iv	−1.61 (15)
N4—O3—Ba1—O5	14.0 (2)	O1—C6—Ba1—O1iv	160.12 (10)
N4—O3—Ba1—C6iv	127.2 (2)	C5—C6—Ba1—O1iv	−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—O2iv	−25.57 (16)
C6—O1—Ba1—O3iv	−152.92 (15)	O1—C6—Ba1—O2iv	136.16 (13)
C6—O1—Ba1—O3	76.98 (16)	C5—C6—Ba1—O2iv	−128.8 (6)
C6—O1—Ba1—O1iv	−30.33 (12)	O1—C6—Ba1—O2	161.7 (2)
C6—O1—Ba1—O2iv	−45.12 (14)	C5—C6—Ba1—O2	−103.3 (6)
C6—O1—Ba1—O2	−9.93 (12)	O2—C6—Ba1—O5iv	−95.07 (16)
C6—O1—Ba1—O5iv	−117.80 (18)	O1—C6—Ba1—O5iv	66.65 (17)
C6—O1—Ba1—O5	61.31 (18)	C5—C6—Ba1—O5iv	161.7 (6)
C6—O1—Ba1—C6iv	−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—O3iv	46.66 (15)	O2—C6—Ba1—C6iv	−18.42 (12)
Ba1i—O2—Ba1—O3iv	−105.09 (7)	O1—C6—Ba1—C6iv	143.31 (14)
C6—O2—Ba1—O3	−107.18 (14)	C5—C6—Ba1—C6iv	−121.7 (6)
Ba1i—O2—Ba1—O3	101.07 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4v	0.86	2.29	2.854 (3)	123
N1—H1···O5vi	0.86	2.37	3.121 (3)	146
N3—H3B···O1vii	0.89	2.19	3.029 (2)	158
N3—H3C···O3viii	0.89	2.05	2.867 (3)	153
N3—H3A···N2ii	0.89	1.94	2.827 (3)	174

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⋯O3iv	0.89	2.05	2.867 (3)	153
N3—H3A⋯N2v	0.89	1.94	2.827 (3)	174

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .