Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616001509/ov3073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616001509/ov3073Isup2.hkl |
CCDC reference: 1449531
In recent years, the crystal engineering of coordination polymers has aroused interest due to their structural versatility, unique properties and applications in different areas of science. Therefore, a large body of research has been focused on the structure and topology of coordination polymers (Kim et al., 2015; Smith, 2013; Liu & Zhao, 2013). In these fields, the selection of appropriate ligands as building blocks is critical to afford a range of topologies. Multidentate N- and O-atom donors have attracted considerable attention due to their varying coordination modes (Galani et al., 2014; Mirzaei et al., 2013; Zhao et al., 2008). Alkali metal cations are known for their mainly ionic chemistry in aqueous media. Their coordination number varies depending on the size of the binding partners, and on the electrostatic interaction between ligands and the metal ions. Thus, the synthesis of coordination polymer networks with these metal ions is of crucial importance (Fromm, 2008; Golovnev & Molokeev, 2013).
Based on the interest in coordination polymers described above, we have prepared 4,4'-diazenediyl-bis(1H-1,2,4-triazol-5-one) (ZTO) and its coordination polymer networks with alkali metal ions. In this work, the bridging behaviour of the two-dimensional coordination polymer poly[tetra-µ-aqua-[µ4-4,4'-diazenediyl-bis(5-oxo-1H-1,2,4-triazolido)]disodium(I)], (I) (see Scheme 1), is reported. The structure of ZTO has been reported previously (Ma, Huang, Ma et al., 2013). The introduction of diazenediyl groups in triazole compounds could improve their enthalpy of formation, density and molecular stability. All eight N atoms in the ZTO molecule have potential to be coordinating atoms. Therefore, the ZTO ligand has a variety of potential coordination modes with metal centres (Vimal-Kumar & Radhakrishnan, 2011; Coropceanu et al., 2014; Wang et al., 2012). In addition, their structures contain a disproportionately large number of nitrogen-containing bonds, such as N—N, C—N, C═N and N═N (Sivabalan et al., 2006; Yang et al., 2008; Yan et al., 2015). They are of interest as high nitrogen energetic materials (Zhong et al., 2011) which could be used as high explosives or as intermediates in pyrotechnic mixtures in safety systems. The structures of alkali metal salts with ZTO are of interest because of their ability to form polymeric systems.
ATO and ZTO were prepared according to the literature procedures of Ma, Huang, Zhong et al. (2013). Compound (I) was obtained by dissolving ZTO (0.5 g, 2 mmol) and NaOH (0.4 g, 10 mmol) in water (5 ml). The reaction scheme, carried out at 418 K for 3 h, is shown in Scheme 2. The resulting mixture was cooled slowly to room temperature. Bright-yellow crystals of (I) formed and were filtered off and dried. IR (KBr, cm-1): νN—H 3297, νC—H 3140, νN═N 2986 , νC═N 1664, νC—N 1333. Elemental analysis calculated for C4H10N8Na2O6: C 15.39, H 3.24, N 35.89%; found: C 15.35, H 3.43, N 35.72%.
Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms bonded to C atoms was refined freely. H atoms bonded to water O atoms were located from difference Fourier maps and refined with O—H bond distances restrained to 0.82 (1) Å, with freely refined isotropic atomic displacement parameters.
The angles of the triazole ring of the 4,4'-diazenediyl-bis(5-oxo-1H-1,2,4-triazolide) (ZTO2-) ligand add up to 540° (Table 2), which indicates that atoms C1, C2, N2, N3 and N4 are located in the same plane. The N—C bond lengths are between normal C—N single- (1.471 Å) and C═N double-bond lengths (1.273 Å). The N3—N4 bond length is between isolated N—N (1.449 Å) and N═N (1.273 Å) bond lengths. The standard bond lengths above were collated according to Allen et al. (1987). Therefore, the C1, C2, N2, N3 and N4 of ZTO2- in (I) form a conjugated ring.
The X-ray single-crystal determination indicates that complex (I) is a polymer. The ZTO2- ligand is located about an inversion centre at the mid-point of the N1═N1i bond. The asymmetric unit of (I) consists of one Na+ cation, half a ZTO2- ligand and two water ligands. Each Na+ cation is octahedrally coordinated by six O atoms, i.e. two from two independent ZTO2- ligands and the remainder from four water molecules (Fig. 1). The Na—O distances are in the range 2.3214 (12)–2.5761 (13) Å (Table 2). The Na+ atom has an unusual trigonal antiprismatic geometry, reflected in the bond lengths and angles about this atom (Table 2), and is located near the a-glide, thus the two bridging O atoms from the two coordinating ZTO2- ligands are on adjacent apices of the trigonal antiprism, rather than being in an anti configuration. The Na+ ion in (I) and the K+ ion in [K(ZTO)(H2O)]n (Ma, Huang, Ma et al., 2013) both adopt a six-coordinated geometry; however, the coordination environment of the Na+ is different compared with that of the K+ ion. In the potassium salt, one K+ ion is coordinated by five adjacent ZTO2- ligands (through three K—O bonds and two K—N bonds) and by one water molecule, and the second K+ ion is coordinated by five adjacent ZTO ligands (through two K—O bonds and three K—N bonds) and by one water molecule. In (I), the Na+ atom is coordinated by four bridging water molecules and two O atoms of two ZTO2- ligands.
All the water molecules and ZTO2- ligands in complex (I) act as bridges between metal centres. Each Na+ centre is interlinked by four bridging water ligands to give rise to a one-dimensional [Na(H2O)2]n chain along the b axis (Fig. 2). Each O atom of the ZTO2- ligand bridges two Na+ ions, thus bridging the [Na(H2O)2]n chains to form two-dimensional sheets parallel to the b axis (Fig. 2).
The crystal structure of complex (I) is stabilized by hydrogen bonds. Water atom O1 is a donor to atoms N4ii and N3iv, while O2 donates hydrogen bonds to O3ii and N4iii (see Table 3 for geometric details and symmetry codes). These hydrogen bonds link the two-dimensional sheets into a three-dimensional hydrogen-bonded network (Fig. 3).
In recent years, the crystal engineering of coordination polymers has aroused interest due to their structural versatility, unique properties and applications in different areas of science. Therefore, a large body of research has been focused on the structure and topology of coordination polymers (Kim et al., 2015; Smith, 2013; Liu & Zhao, 2013). In these fields, the selection of appropriate ligands as building blocks is critical to afford a range of topologies. Multidentate N- and O-atom donors have attracted considerable attention due to their varying coordination modes (Galani et al., 2014; Mirzaei et al., 2013; Zhao et al., 2008). Alkali metal cations are known for their mainly ionic chemistry in aqueous media. Their coordination number varies depending on the size of the binding partners, and on the electrostatic interaction between ligands and the metal ions. Thus, the synthesis of coordination polymer networks with these metal ions is of crucial importance (Fromm, 2008; Golovnev & Molokeev, 2013).
Based on the interest in coordination polymers described above, we have prepared 4,4'-diazenediyl-bis(1H-1,2,4-triazol-5-one) (ZTO) and its coordination polymer networks with alkali metal ions. In this work, the bridging behaviour of the two-dimensional coordination polymer poly[tetra-µ-aqua-[µ4-4,4'-diazenediyl-bis(5-oxo-1H-1,2,4-triazolido)]disodium(I)], (I) (see Scheme 1), is reported. The structure of ZTO has been reported previously (Ma, Huang, Ma et al., 2013). The introduction of diazenediyl groups in triazole compounds could improve their enthalpy of formation, density and molecular stability. All eight N atoms in the ZTO molecule have potential to be coordinating atoms. Therefore, the ZTO ligand has a variety of potential coordination modes with metal centres (Vimal-Kumar & Radhakrishnan, 2011; Coropceanu et al., 2014; Wang et al., 2012). In addition, their structures contain a disproportionately large number of nitrogen-containing bonds, such as N—N, C—N, C═N and N═N (Sivabalan et al., 2006; Yang et al., 2008; Yan et al., 2015). They are of interest as high nitrogen energetic materials (Zhong et al., 2011) which could be used as high explosives or as intermediates in pyrotechnic mixtures in safety systems. The structures of alkali metal salts with ZTO are of interest because of their ability to form polymeric systems.
The angles of the triazole ring of the 4,4'-diazenediyl-bis(5-oxo-1H-1,2,4-triazolide) (ZTO2-) ligand add up to 540° (Table 2), which indicates that atoms C1, C2, N2, N3 and N4 are located in the same plane. The N—C bond lengths are between normal C—N single- (1.471 Å) and C═N double-bond lengths (1.273 Å). The N3—N4 bond length is between isolated N—N (1.449 Å) and N═N (1.273 Å) bond lengths. The standard bond lengths above were collated according to Allen et al. (1987). Therefore, the C1, C2, N2, N3 and N4 of ZTO2- in (I) form a conjugated ring.
The X-ray single-crystal determination indicates that complex (I) is a polymer. The ZTO2- ligand is located about an inversion centre at the mid-point of the N1═N1i bond. The asymmetric unit of (I) consists of one Na+ cation, half a ZTO2- ligand and two water ligands. Each Na+ cation is octahedrally coordinated by six O atoms, i.e. two from two independent ZTO2- ligands and the remainder from four water molecules (Fig. 1). The Na—O distances are in the range 2.3214 (12)–2.5761 (13) Å (Table 2). The Na+ atom has an unusual trigonal antiprismatic geometry, reflected in the bond lengths and angles about this atom (Table 2), and is located near the a-glide, thus the two bridging O atoms from the two coordinating ZTO2- ligands are on adjacent apices of the trigonal antiprism, rather than being in an anti configuration. The Na+ ion in (I) and the K+ ion in [K(ZTO)(H2O)]n (Ma, Huang, Ma et al., 2013) both adopt a six-coordinated geometry; however, the coordination environment of the Na+ is different compared with that of the K+ ion. In the potassium salt, one K+ ion is coordinated by five adjacent ZTO2- ligands (through three K—O bonds and two K—N bonds) and by one water molecule, and the second K+ ion is coordinated by five adjacent ZTO ligands (through two K—O bonds and three K—N bonds) and by one water molecule. In (I), the Na+ atom is coordinated by four bridging water molecules and two O atoms of two ZTO2- ligands.
All the water molecules and ZTO2- ligands in complex (I) act as bridges between metal centres. Each Na+ centre is interlinked by four bridging water ligands to give rise to a one-dimensional [Na(H2O)2]n chain along the b axis (Fig. 2). Each O atom of the ZTO2- ligand bridges two Na+ ions, thus bridging the [Na(H2O)2]n chains to form two-dimensional sheets parallel to the b axis (Fig. 2).
The crystal structure of complex (I) is stabilized by hydrogen bonds. Water atom O1 is a donor to atoms N4ii and N3iv, while O2 donates hydrogen bonds to O3ii and N4iii (see Table 3 for geometric details and symmetry codes). These hydrogen bonds link the two-dimensional sheets into a three-dimensional hydrogen-bonded network (Fig. 3).
ATO and ZTO were prepared according to the literature procedures of Ma, Huang, Zhong et al. (2013). Compound (I) was obtained by dissolving ZTO (0.5 g, 2 mmol) and NaOH (0.4 g, 10 mmol) in water (5 ml). The reaction scheme, carried out at 418 K for 3 h, is shown in Scheme 2. The resulting mixture was cooled slowly to room temperature. Bright-yellow crystals of (I) formed and were filtered off and dried. IR (KBr, cm-1): νN—H 3297, νC—H 3140, νN═N 2986 , νC═N 1664, νC—N 1333. Elemental analysis calculated for C4H10N8Na2O6: C 15.39, H 3.24, N 35.89%; found: C 15.35, H 3.43, N 35.72%.
Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms bonded to C atoms was refined freely. H atoms bonded to water O atoms were located from difference Fourier maps and refined with O—H bond distances restrained to 0.82 (1) Å, with freely refined isotropic atomic displacement parameters.
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al., 2006).
[Na2(C4H2N8O2)(H2O)4] | Dx = 1.768 Mg m−3 |
Mr = 312.18 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 2550 reflections |
a = 6.4055 (14) Å | θ = 2.6–27.7° |
b = 11.587 (3) Å | µ = 0.22 mm−1 |
c = 15.805 (4) Å | T = 296 K |
V = 1173.1 (4) Å3 | Block, yellow |
Z = 4 | 0.36 × 0.29 × 0.13 mm |
F(000) = 640 |
Bruker APEXII CCD diffractometer | 1212 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
φ and ω scans | θmax = 28.2°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −8→7 |
Tmin = 0.927, Tmax = 0.972 | k = −15→13 |
6117 measured reflections | l = −17→19 |
1405 independent reflections |
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)] = 0.034 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.087 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0392P)2 + 0.4139P] where P = (Fo2 + 2Fc2)/3 |
1405 reflections | (Δ/σ)max < 0.001 |
111 parameters | Δρmax = 0.22 e Å−3 |
5 restraints | Δρmin = −0.34 e Å−3 |
[Na2(C4H2N8O2)(H2O)4] | V = 1173.1 (4) Å3 |
Mr = 312.18 | Z = 4 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 6.4055 (14) Å | µ = 0.22 mm−1 |
b = 11.587 (3) Å | T = 296 K |
c = 15.805 (4) Å | 0.36 × 0.29 × 0.13 mm |
Bruker APEXII CCD diffractometer | 1405 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 1212 reflections with I > 2σ(I) |
Tmin = 0.927, Tmax = 0.972 | Rint = 0.040 |
6117 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 5 restraints |
wR(F2) = 0.087 | All H-atom parameters refined |
S = 1.05 | Δρmax = 0.22 e Å−3 |
1405 reflections | Δρmin = −0.34 e Å−3 |
111 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Na1 | 0.19648 (10) | 0.52927 (5) | 0.23877 (4) | 0.02991 (19) | |
N1 | 0.48906 (19) | 0.51774 (9) | 0.46287 (7) | 0.0219 (3) | |
N2 | 0.42821 (18) | 0.63169 (9) | 0.46264 (7) | 0.0207 (3) | |
N3 | 0.3768 (2) | 0.81037 (9) | 0.50095 (7) | 0.0244 (3) | |
N4 | 0.39312 (19) | 0.80744 (9) | 0.41183 (7) | 0.0242 (3) | |
O1 | 0.46737 (19) | 0.52938 (9) | 0.13650 (7) | 0.0311 (3) | |
O2 | 0.42366 (19) | 0.36848 (10) | 0.28232 (7) | 0.0318 (3) | |
O3 | 0.45508 (17) | 0.65968 (8) | 0.31472 (6) | 0.0272 (3) | |
C1 | 0.3986 (2) | 0.70624 (12) | 0.52894 (9) | 0.0227 (3) | |
C2 | 0.4280 (2) | 0.69868 (11) | 0.38842 (8) | 0.0201 (3) | |
H1A | 0.395 (3) | 0.6871 (14) | 0.5801 (6) | 0.030 (4)* | |
H2A | 0.443 (4) | 0.3085 (13) | 0.2554 (13) | 0.064 (7)* | |
H1B | 0.495 (4) | 0.4644 (11) | 0.1197 (14) | 0.056 (7)* | |
H2B | 0.344 (3) | 0.3508 (18) | 0.3214 (10) | 0.050 (6)* | |
H1C | 0.450 (3) | 0.5708 (15) | 0.0954 (9) | 0.047 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Na1 | 0.0287 (3) | 0.0303 (3) | 0.0307 (3) | 0.0051 (2) | 0.0020 (2) | 0.0039 (2) |
N1 | 0.0269 (6) | 0.0154 (5) | 0.0234 (6) | 0.0015 (4) | −0.0011 (5) | 0.0013 (4) |
N2 | 0.0279 (6) | 0.0146 (5) | 0.0194 (6) | 0.0017 (4) | −0.0006 (4) | 0.0009 (4) |
N3 | 0.0315 (7) | 0.0208 (6) | 0.0210 (6) | 0.0032 (5) | −0.0001 (5) | −0.0027 (5) |
N4 | 0.0338 (7) | 0.0173 (5) | 0.0214 (6) | 0.0025 (5) | 0.0007 (5) | 0.0011 (4) |
O1 | 0.0463 (7) | 0.0238 (5) | 0.0232 (6) | 0.0056 (5) | 0.0027 (5) | 0.0017 (4) |
O2 | 0.0406 (6) | 0.0282 (6) | 0.0268 (6) | −0.0028 (5) | 0.0058 (5) | 0.0017 (5) |
O3 | 0.0383 (6) | 0.0250 (5) | 0.0183 (5) | 0.0046 (4) | 0.0015 (4) | −0.0005 (4) |
C1 | 0.0275 (7) | 0.0226 (6) | 0.0180 (7) | 0.0020 (5) | −0.0005 (5) | −0.0007 (5) |
C2 | 0.0224 (6) | 0.0179 (6) | 0.0199 (7) | 0.0010 (5) | −0.0005 (5) | 0.0025 (5) |
Na1—O3i | 2.3214 (12) | N3—C1 | 1.2927 (17) |
Na1—O1 | 2.3714 (14) | N3—N4 | 1.4129 (17) |
Na1—O1i | 2.4575 (14) | N4—C2 | 1.3323 (17) |
Na1—O2 | 2.4623 (13) | O1—Na1ii | 2.4576 (14) |
Na1—O3 | 2.5433 (12) | O1—H1B | 0.818 (10) |
Na1—O2i | 2.5761 (13) | O1—H1C | 0.815 (9) |
Na1—Na1ii | 3.2223 (7) | O2—Na1ii | 2.5761 (13) |
Na1—Na1i | 3.2224 (7) | O2—H2A | 0.825 (10) |
Na1—H2B | 2.62 (2) | O2—H2B | 0.828 (9) |
N1—N1iii | 1.251 (2) | O3—C2 | 1.2614 (17) |
N1—N2 | 1.3767 (14) | O3—Na1ii | 2.3214 (12) |
N2—C1 | 1.3712 (17) | C1—H1A | 0.839 (9) |
N2—C2 | 1.4066 (17) | ||
O3i—Na1—O1 | 103.82 (4) | O3—Na1—H2B | 90.0 (4) |
O3i—Na1—O1i | 83.92 (4) | O2i—Na1—H2B | 74.8 (4) |
O1—Na1—O1i | 169.64 (5) | Na1ii—Na1—H2B | 65.6 (3) |
O3i—Na1—O2 | 171.12 (5) | Na1i—Na1—H2B | 107.6 (3) |
O1—Na1—O2 | 76.02 (4) | N1iii—N1—N2 | 110.45 (13) |
O1i—Na1—O2 | 97.42 (4) | C1—N2—N1 | 129.88 (11) |
O3i—Na1—O3 | 102.65 (5) | C1—N2—C2 | 106.83 (11) |
O1—Na1—O3 | 81.07 (4) | N1—N2—C2 | 122.12 (11) |
O1i—Na1—O3 | 90.58 (4) | C1—N3—N4 | 108.10 (11) |
O2—Na1—O3 | 86.14 (4) | C2—N4—N3 | 108.18 (10) |
O3i—Na1—O2i | 88.39 (5) | Na1—O1—Na1ii | 83.70 (4) |
O1—Na1—O2i | 114.11 (5) | Na1—O1—H1B | 112.3 (17) |
O1i—Na1—O2i | 72.49 (4) | Na1ii—O1—H1B | 97.5 (17) |
O2—Na1—O2i | 83.67 (4) | Na1—O1—H1C | 116.5 (15) |
O3—Na1—O2i | 158.85 (4) | Na1ii—O1—H1C | 136.0 (15) |
O3i—Na1—Na1ii | 134.60 (3) | H1B—O1—H1C | 108 (2) |
O1—Na1—Na1ii | 49.29 (3) | Na1—O2—Na1ii | 79.48 (4) |
O1i—Na1—Na1ii | 120.34 (4) | Na1—O2—H2A | 125.6 (18) |
O2—Na1—Na1ii | 51.82 (3) | Na1ii—O2—H2A | 116.1 (18) |
O3—Na1—Na1ii | 45.63 (3) | Na1—O2—H2B | 91.7 (15) |
O2i—Na1—Na1ii | 133.51 (3) | Na1ii—O2—H2B | 134.0 (15) |
O3i—Na1—Na1i | 51.54 (3) | H2A—O2—H2B | 106 (2) |
O1—Na1—Na1i | 143.35 (4) | C2—O3—Na1ii | 131.37 (9) |
O1i—Na1—Na1i | 47.01 (3) | C2—O3—Na1 | 124.00 (9) |
O2—Na1—Na1i | 123.82 (3) | Na1ii—O3—Na1 | 82.83 (4) |
O3—Na1—Na1i | 126.54 (3) | N3—C1—N2 | 109.96 (12) |
O2i—Na1—Na1i | 48.70 (3) | N3—C1—H1A | 125.0 (12) |
Na1ii—Na1—Na1i | 167.35 (4) | N2—C1—H1A | 125.0 (12) |
O3i—Na1—H2B | 159.2 (3) | O3—C2—N4 | 128.20 (12) |
O1—Na1—H2B | 94.4 (3) | O3—C2—N2 | 124.92 (12) |
O1i—Na1—H2B | 79.4 (3) | N4—C2—N2 | 106.89 (11) |
O2—Na1—H2B | 18.4 (2) | ||
N1iii—N1—N2—C1 | 2.5 (2) | Na1ii—O3—C2—N2 | −45.10 (19) |
N1iii—N1—N2—C2 | 168.54 (14) | Na1—O3—C2—N2 | 68.08 (16) |
C1—N3—N4—C2 | −0.81 (16) | N3—N4—C2—O3 | −178.85 (14) |
N4—N3—C1—N2 | −0.34 (16) | N3—N4—C2—N2 | 1.58 (15) |
N1—N2—C1—N3 | 168.94 (13) | C1—N2—C2—O3 | 178.64 (13) |
C2—N2—C1—N3 | 1.30 (16) | N1—N2—C2—O3 | 9.8 (2) |
Na1ii—O3—C2—N4 | 135.40 (13) | C1—N2—C2—N4 | −1.77 (15) |
Na1—O3—C2—N4 | −111.42 (14) | N1—N2—C2—N4 | −170.59 (12) |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x+1/2, y, −z+1/2; (iii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O3iv | 0.83 (1) | 2.15 (1) | 2.9679 (16) | 171 (3) |
O1—H1B···N4iv | 0.82 (1) | 2.02 (1) | 2.8277 (16) | 171 (2) |
O2—H2B···N4v | 0.83 (1) | 2.14 (1) | 2.9678 (17) | 173 (2) |
O1—H1C···N3vi | 0.82 (1) | 2.09 (1) | 2.8940 (16) | 172 (2) |
Symmetry codes: (iv) −x+1, y−1/2, −z+1/2; (v) −x+1/2, y−1/2, z; (vi) x, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Na2(C4H2N8O2)(H2O)4] |
Mr | 312.18 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 296 |
a, b, c (Å) | 6.4055 (14), 11.587 (3), 15.805 (4) |
V (Å3) | 1173.1 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.36 × 0.29 × 0.13 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.927, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6117, 1405, 1212 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.665 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.087, 1.05 |
No. of reflections | 1405 |
No. of parameters | 111 |
No. of restraints | 5 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.22, −0.34 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al., 2006).
Na1—O3i | 2.3214 (12) | N2—C1 | 1.3712 (17) |
Na1—O1 | 2.3714 (14) | N2—C2 | 1.4066 (17) |
Na1—O1i | 2.4575 (14) | N3—C1 | 1.2927 (17) |
Na1—O2 | 2.4623 (13) | N3—N4 | 1.4129 (17) |
Na1—O3 | 2.5433 (12) | N4—C2 | 1.3323 (17) |
Na1—O2i | 2.5761 (13) | ||
O3i—Na1—O1 | 103.82 (4) | O3i—Na1—O2i | 88.39 (5) |
O3i—Na1—O1i | 83.92 (4) | O1—Na1—O2i | 114.11 (5) |
O1—Na1—O1i | 169.64 (5) | O1i—Na1—O2i | 72.49 (4) |
O3i—Na1—O2 | 171.12 (5) | O2—Na1—O2i | 83.67 (4) |
O1—Na1—O2 | 76.02 (4) | O3—Na1—O2i | 158.85 (4) |
O1i—Na1—O2 | 97.42 (4) | C1—N2—C2 | 106.83 (11) |
O3i—Na1—O3 | 102.65 (5) | C1—N3—N4 | 108.10 (11) |
O1—Na1—O3 | 81.07 (4) | C2—N4—N3 | 108.18 (10) |
O1i—Na1—O3 | 90.58 (4) | N3—C1—N2 | 109.96 (12) |
O2—Na1—O3 | 86.14 (4) | N4—C2—N2 | 106.89 (11) |
Symmetry code: (i) x−1/2, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O3ii | 0.825 (10) | 2.151 (11) | 2.9679 (16) | 171 (3) |
O1—H1B···N4ii | 0.818 (10) | 2.017 (11) | 2.8277 (16) | 171 (2) |
O2—H2B···N4iii | 0.828 (9) | 2.144 (10) | 2.9678 (17) | 173 (2) |
O1—H1C···N3iv | 0.815 (9) | 2.085 (10) | 2.8940 (16) | 172 (2) |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1/2, y−1/2, z; (iv) x, −y+3/2, z−1/2. |