Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113023846/wq3047sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113023846/wq3047Isup2.hkl |
CCDC reference: 969453
Metal–organic frameworks (MOFs) with carboxylate-containing ligands have been extensively studied because the carboxylate groups can have varied coordination modes resulting in the formation of a range of structures (Evans et al., 2002; Li et al., 2012; O'Keeffe et al., 2012). Using these types of ligands, MOFs have recently emerged which display intriguing architectures and topologies and have many potential applications, including catalysis, luminescence, ion exchange, magnetic materials and gas absorption (Férey et al., 2005; Banerjee et al., 2008; Chen et al., 2007; Zhang, Huang et al., 2012; OR Zhang, Zhang et al., 2012; Cook et al., 2013). Furthermore, carboxylate-containing ligands with N-donor functional groups acting as ancillary connectors provide another group of potential building blocks for constructing coordination polymers, particularly as they have strong coordination affinity and can meet the geometric requirements of a variety of metal centres. Therefore, there has been a boom in the synthesis and construction of metal–organic frameworks having carboxylate ligands with amide functionality (Xiong et al., 2013; Zheng et al., 2011). In the present study, in order to further investigate the influence of organic ligands with carboxamide group on the coordination architectures and related properties, reactions with 4-(isonicotinamido)phthalic acid (H2L) with nickel salts were carried out. We report the synthesis, crystal structure and properties of a new coordination polymer obtained by solvothermal reaction, namely poly[diaqua[µ4-4-(isonicotinamido)phthalato]nickel(II)], [Ni(L)(H2O)2]n, (I).
All reagents and solvents were used as obtained commercially and were used without further purification. A mixture of H2L (0.028 g, 0.1 mmol), NiCl2.6H2O (0.024 g, 0.1 mmol), N,N-dimethylformamide (DMF, 5 ml) and EtOH (5 ml) was placed in a Teflon-lined stainless-steel vessel, heated to 393 K for 4 d, and then cooled to room temperature within 24 h. Green block-shaped crystals of (I) were obtained (yield 32%). IR (KBr pellet, cm-1): 3420 (s), 2840 (w), 1628 (w), 1605 (s), 1519 (m), 1418 (m), 1389 (s), 1362 (m), 1288 (w), 789 (w), 741 (w), 720 (m), 589 (w).
Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms bonded to C atoms were placed geometrically and treated as riding, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). Aqua H atoms were determined from a difference Fourier synthesis and were refined with restrained O—H distances of 0.85–0.96 Å and free Uiso(H) values. The amide H atoms were located from difference maps and refined with the N—H distances restrained to 0.86 Å. In order to obtain the higher complete, we used the omit -1 52. On the other hand, the high-angle diffraction are too weak. [Unclear; please reword]
Structure analysis revealed that the title compound, (I), crystallizes as a three-dimensional non-interpenetrated framework which constrasts completely with the three-dimensional four-interpenetrated network of the previously reported complex {[Ni(INAIP)(H2O)2].H2O}n (INAIP is 5-(isonicotinamido)isophthalate; Chen et al., 2009), which was obtained by hydrothermal synthesis. This result demonstrates that the organic ligand plays an important role in the construction of these frameworks. The asymmetric unit of (I) contains one unique NiII atom, one L2- ligand and two coordinated water molecules (Fig. 1). The NiII atom has an NO5 coordination environment with a slightly distorted octahedral coordination geometry (Table 2). The Ni—N bond length is 2.332 (4) Å, and the average Ni—O bond length of 2.212 (3) Å (for carboxylate O atoms) is significantly longer than the Ni—OH2 distances, which average 2.125 (3) Å, suggesting that the water molecules have a stronger interaction with the NiII atom. Each L2- ligand connects four NiII atoms using its two carboxylate groups and the pyridinyl group of the ligand. Firstly, a one-dimensional chain is formed by connections between the anti–anti µ2-η1:η1-bridging carboxylate group and the NiII atoms with crosslinking to a second complex through the µ1-η1:η0-monodentate carboxylate group, forming a double chain (Fig. 2a). The double chains are crosslinked by coordination from the pyridine N atoms, leading to a three-dimensional extended network in which the terminal water molecules point into the rectangular straight channels extending along b axis, these channels are stabilized by amide–amide N1—H1···O5 hydrgen-bonding interactions (Fig. 2b).
To further understand this three-dimensional structure of (I), suitable connectors should be defined by using the topological approach. As discussed above, each L2- ligand is surrounded by four NiII atoms, thus each ligand could be considered as a four-connector, and the central NiII atom can also be considered as a four-connector by omitting the two coordinated water molecules. Therefore, the topology of (I), calculated by TOPOS (Blatov, 2012) is a uniform 4-connected three-dimensional sra net with Schläfli symbol (42.63.8) (Fig. 2c). Moreover, in (I), the uncoordinated amide-group N and O atoms provide hydrogen-bonding donors and acceptors, respectively. The hydrogen-bonding interactions have donor–acceptor (D···A) separations in the range 2.748 (3)–3.350 (4) Å and D—H···A angles in the range 114–169 ° (Table 3). These hydrogen bonds further consolidate the three-dimensional framework structure of (I).
The magnetic susceptibilities were measured on a crystalline sample of (I) in the temperature range 1.8–300 K under 2 kOe using a SQUID magnetometer. At room temperature, the observed χMT value is 2.05 emu K mol-1, which is slightly larger than the expected value of 2.0 emu K mol-1 corresponding to the binuclear NiII (S = 1) ion (Fig. 3). Upon cooling from 300 to 100 K, the values of χMT decrease slowly and then rapidly reach a value of 0.75 emu K mol-1 at 1.8 K. The χM versus T plot follows the Curie–Weiss law, with C = 3.01 emu K mol-1 and Θ = -4.22 K. The negative Θ value suggests that there is a weak antiferromagnetic interaction among the NiII atoms transferred through the ligands L2-, which is similar to the reported complex {[Ni(INAIP)(H2O)2].H2O}n (Chen et al., 2009). And it is entirely different from the antiferromagnetic complex [Ni2(Flu)3](ClO4).H2O (Flu is ????) bridged by three deprotonated µ2-O groups (Zhang, Huang et al., 2012; OR Zhang, Zhang et al., 2012;) and the ferromagnetic complex {[Ni(N3)0.5(L)1.5(H2O)].EtOH}n (Hu et al., 2008). The magnetic coupling through the L2- ligand in this bridging mode is very weak and usually antiferromagnetic, and it will only be important at very low temperatures (Liu et al., 2007).
To examine the thermal stability of the framework, thermogravimetric analyses (TGA) and temperature-dependent power X-ray diffraction (PXRD) measurements were carried out (Fig. 4). The TG curves show that the first weight loss between room temperature and 383 K was 9.45% in (I), corresponding to the loss of coordinated water (calculated 9.50%). As a check, an elemental analysis was carried out (C 48.98%, H 2.33% and O 23.31%) and agreed with the dehydrated phase. The dehydrated phase remains stable up to 648 K until the organic ligands start to be released and this exhibits the high framework stability of (I). As shown in Fig. 4(b), it is clear that the PXRD pattern of the as-synthesized sample is a little different from the simulated one which may be attributed to the framework dynamics of (I) due to the loss of some water molecules from the surface of the crystals. The other diffraction profiles below 648 K are almost the same, indicating that the framework is stable at this temperature and that the crystal lattice remains intact after removal of all the water molecules. When the temperature was raised to 653 K, the organic ligand began to decompose and the XRD of the framework is almost collapsed. The results show that complex (I) displays highly thermal stability.
Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).
[Ni(C14H8N2O5)(H2O)2] | F(000) = 776 |
Mr = 378.97 | Dx = 1.737 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1849 reflections |
a = 6.5322 (8) Å | θ = 2.1–23.3° |
b = 30.456 (4) Å | µ = 1.38 mm−1 |
c = 7.2856 (7) Å | T = 291 K |
β = 91.223 (3)° | Block, green |
V = 1449.1 (3) Å3 | 0.22 × 0.14 × 0.08 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 2810 independent reflections |
Radiation source: sealed tube | 2379 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.010 |
phi and ω scans | θmax = 26.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −7→8 |
Tmin = 0.751, Tmax = 0.898 | k = −37→36 |
7738 measured reflections | l = −8→8 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.09P)2 + 1.88P] where P = (Fo2 + 2Fc2)/3 |
2810 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.62 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
[Ni(C14H8N2O5)(H2O)2] | V = 1449.1 (3) Å3 |
Mr = 378.97 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.5322 (8) Å | µ = 1.38 mm−1 |
b = 30.456 (4) Å | T = 291 K |
c = 7.2856 (7) Å | 0.22 × 0.14 × 0.08 mm |
β = 91.223 (3)° |
Bruker SMART APEX CCD diffractometer | 2810 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2379 reflections with I > 2σ(I) |
Tmin = 0.751, Tmax = 0.898 | Rint = 0.010 |
7738 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.62 e Å−3 |
2810 reflections | Δρmin = −0.57 e Å−3 |
217 parameters |
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 | 0.2475 (5) | 0.31709 (11) | 0.0023 (5) | 0.0266 (8) | |
C2 | 0.2468 (5) | 0.32667 (11) | −0.1824 (5) | 0.0264 (7) | |
H2 | 0.2470 | 0.3038 | −0.2670 | 0.032* | |
C3 | 0.2457 (5) | 0.36948 (12) | −0.2446 (5) | 0.0265 (8) | |
H3 | 0.2505 | 0.3754 | −0.3696 | 0.032* | |
C4 | 0.2374 (5) | 0.40356 (11) | −0.1187 (5) | 0.0257 (7) | |
C5 | 0.2277 (5) | 0.39441 (11) | 0.0691 (5) | 0.0263 (7) | |
C6 | 0.2328 (5) | 0.35105 (11) | 0.1305 (5) | 0.0260 (7) | |
H6 | 0.2266 | 0.3448 | 0.2552 | 0.031* | |
C7 | 0.2091 (5) | 0.43132 (11) | 0.2082 (5) | 0.0253 (7) | |
C8 | 0.2308 (5) | 0.44982 (12) | −0.1934 (5) | 0.0256 (7) | |
C9 | 0.1771 (6) | 0.25165 (12) | 0.1943 (5) | 0.0288 (8) | |
C10 | 0.2168 (6) | 0.20326 (12) | 0.2045 (5) | 0.0283 (8) | |
C11 | 0.2155 (6) | 0.17614 (11) | 0.0514 (5) | 0.0295 (8) | |
H11 | 0.2056 | 0.1881 | −0.0659 | 0.035* | |
C12 | 0.2290 (6) | 0.13126 (12) | 0.0746 (5) | 0.0283 (8) | |
H12 | 0.2270 | 0.1136 | −0.0297 | 0.034* | |
C13 | 0.2510 (5) | 0.13832 (12) | 0.3860 (5) | 0.0279 (8) | |
H13 | 0.2668 | 0.1254 | 0.5011 | 0.033* | |
C14 | 0.2356 (5) | 0.18339 (11) | 0.3773 (5) | 0.0272 (8) | |
H14 | 0.2376 | 0.2002 | 0.4838 | 0.033* | |
N1 | 0.2670 (5) | 0.27217 (10) | 0.0523 (4) | 0.0273 (7) | |
H1 | 0.3444 | 0.2563 | −0.0150 | 0.033* | |
N2 | 0.2447 (4) | 0.11184 (11) | 0.2380 (4) | 0.0279 (7) | |
Ni1 | 0.73063 (7) | 0.464271 (15) | −0.22975 (6) | 0.0281 (2) | |
O1 | 0.3899 (4) | 0.46400 (7) | −0.2696 (3) | 0.0269 (6) | |
O2 | 0.0651 (4) | 0.47109 (8) | −0.1844 (3) | 0.0278 (6) | |
O3 | 0.3119 (4) | 0.46584 (7) | 0.1751 (3) | 0.0264 (6) | |
O4 | 0.0984 (4) | 0.42484 (8) | 0.3396 (3) | 0.0308 (6) | |
O5 | 0.0729 (4) | 0.27009 (8) | 0.3044 (3) | 0.0324 (6) | |
O1W | 0.7703 (4) | 0.46881 (8) | −0.5137 (4) | 0.0301 (6) | |
H1X | 0.8642 | 0.4561 | −0.5727 | 0.036* | |
H1Y | 0.6663 | 0.4874 | −0.5667 | 0.045* | |
O2W | 0.7044 (4) | 0.45178 (8) | 0.0600 (3) | 0.0279 (6) | |
H2X | 0.6112 | 0.4725 | 0.1118 | 0.042* | |
H2Y | 0.8365 | 0.4548 | 0.1191 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0296 (18) | 0.0258 (18) | 0.0249 (17) | 0.0080 (14) | 0.0087 (14) | 0.0082 (14) |
C2 | 0.0311 (19) | 0.0236 (17) | 0.0248 (17) | −0.0095 (14) | 0.0084 (14) | −0.0069 (14) |
C3 | 0.0283 (19) | 0.0249 (18) | 0.0266 (18) | −0.0027 (13) | 0.0096 (14) | 0.0067 (13) |
C4 | 0.0262 (18) | 0.0236 (17) | 0.0278 (18) | −0.0009 (13) | 0.0111 (14) | 0.0025 (14) |
C5 | 0.0282 (18) | 0.0230 (17) | 0.0281 (18) | 0.0081 (14) | 0.0065 (14) | 0.0004 (14) |
C6 | 0.0292 (19) | 0.0244 (17) | 0.0247 (17) | −0.0024 (14) | 0.0108 (14) | 0.0082 (13) |
C7 | 0.0265 (18) | 0.0218 (17) | 0.0276 (18) | 0.0041 (13) | −0.0036 (14) | −0.0058 (14) |
C8 | 0.0236 (18) | 0.0234 (17) | 0.0297 (18) | −0.0057 (14) | −0.0061 (14) | −0.0003 (15) |
C9 | 0.0320 (19) | 0.0258 (18) | 0.0290 (18) | 0.0101 (15) | 0.0102 (15) | 0.0082 (15) |
C10 | 0.0313 (19) | 0.0275 (18) | 0.0262 (18) | −0.0003 (15) | 0.0009 (14) | 0.0007 (15) |
C11 | 0.033 (2) | 0.0246 (18) | 0.031 (2) | 0.0092 (14) | 0.0080 (15) | 0.0072 (14) |
C12 | 0.0317 (19) | 0.0276 (18) | 0.0262 (18) | −0.0079 (15) | 0.0116 (14) | −0.0077 (14) |
C13 | 0.0305 (19) | 0.0261 (18) | 0.0267 (18) | −0.0063 (14) | −0.0087 (14) | 0.0080 (14) |
C14 | 0.0290 (19) | 0.0230 (17) | 0.0299 (19) | −0.0093 (14) | 0.0095 (14) | −0.0078 (14) |
N1 | 0.0292 (16) | 0.0247 (15) | 0.0287 (16) | −0.0078 (12) | 0.0124 (12) | −0.0070 (12) |
N2 | 0.0284 (16) | 0.0264 (16) | 0.0290 (16) | −0.0006 (12) | −0.0015 (12) | 0.0001 (12) |
Ni1 | 0.0288 (3) | 0.0268 (3) | 0.0282 (3) | 0.00786 (17) | −0.0074 (2) | −0.00772 (18) |
O1 | 0.0315 (14) | 0.0258 (13) | 0.0239 (13) | −0.0001 (10) | 0.0079 (10) | 0.0091 (9) |
O2 | 0.0291 (14) | 0.0269 (13) | 0.0274 (13) | 0.0084 (10) | −0.0005 (10) | 0.0094 (10) |
O3 | 0.0270 (13) | 0.0272 (14) | 0.0253 (13) | −0.0061 (9) | 0.0062 (10) | −0.0081 (10) |
O4 | 0.0306 (14) | 0.0266 (13) | 0.0356 (14) | −0.0102 (10) | 0.0090 (11) | −0.0094 (10) |
O5 | 0.0367 (15) | 0.0291 (13) | 0.0319 (14) | 0.0076 (11) | 0.0150 (11) | 0.0087 (11) |
O1W | 0.0292 (14) | 0.0282 (13) | 0.0332 (14) | 0.0100 (10) | 0.0106 (11) | 0.0083 (10) |
O2W | 0.0269 (13) | 0.0269 (13) | 0.0303 (13) | 0.0086 (10) | 0.0085 (10) | −0.0025 (10) |
C1—C2 | 1.376 (5) | C11—H11 | 0.9300 |
C1—C6 | 1.399 (5) | C12—N2 | 1.332 (5) |
C1—N1 | 1.421 (4) | C12—H12 | 0.9300 |
C2—C3 | 1.380 (5) | C13—N2 | 1.347 (5) |
C2—H2 | 0.9300 | C13—C14 | 1.378 (5) |
C3—C4 | 1.387 (5) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.399 (5) | N1—H1 | 0.8600 |
C4—C8 | 1.511 (5) | N2—Ni1i | 2.332 (3) |
C5—C6 | 1.394 (5) | Ni1—O1W | 2.095 (3) |
C5—C7 | 1.520 (5) | Ni1—O2W | 2.155 (2) |
C6—H6 | 0.9300 | Ni1—O3ii | 2.184 (2) |
C7—O4 | 1.228 (4) | Ni1—O2iii | 2.213 (3) |
C7—O3 | 1.274 (4) | Ni1—O1 | 2.239 (3) |
C8—O2 | 1.264 (4) | Ni1—N2iv | 2.332 (3) |
C8—O1 | 1.265 (4) | O2—Ni1v | 2.213 (3) |
C9—O5 | 1.202 (4) | O3—Ni1ii | 2.184 (2) |
C9—N1 | 1.354 (4) | O1W—H1X | 0.8500 |
C9—C10 | 1.498 (5) | O1W—H1Y | 0.9600 |
C10—C11 | 1.388 (5) | O2W—H2X | 0.9599 |
C10—C14 | 1.400 (5) | O2W—H2Y | 0.9600 |
C11—C12 | 1.380 (5) | ||
C2—C1—C6 | 119.8 (3) | N2—C13—C14 | 124.0 (3) |
C2—C1—N1 | 116.9 (3) | N2—C13—H13 | 118.0 |
C6—C1—N1 | 123.2 (3) | C14—C13—H13 | 118.0 |
C1—C2—C3 | 121.4 (3) | C13—C14—C10 | 118.5 (3) |
C1—C2—H2 | 119.3 | C13—C14—H14 | 120.8 |
C3—C2—H2 | 119.3 | C10—C14—H14 | 120.8 |
C2—C3—C4 | 119.3 (3) | C9—N1—C1 | 127.0 (3) |
C2—C3—H3 | 120.3 | C9—N1—H1 | 116.5 |
C4—C3—H3 | 120.3 | C1—N1—H1 | 116.5 |
C3—C4—C5 | 120.1 (3) | C12—N2—C13 | 116.8 (3) |
C3—C4—C8 | 117.5 (3) | C12—N2—Ni1i | 122.0 (2) |
C5—C4—C8 | 122.4 (3) | C13—N2—Ni1i | 121.0 (2) |
C6—C5—C4 | 120.1 (3) | O1W—Ni1—O2W | 173.16 (9) |
C6—C5—C7 | 119.2 (3) | O1W—Ni1—O3ii | 97.73 (9) |
C4—C5—C7 | 120.7 (3) | O2W—Ni1—O3ii | 88.88 (9) |
C5—C6—C1 | 119.2 (3) | O1W—Ni1—O2iii | 89.94 (10) |
C5—C6—H6 | 120.4 | O2W—Ni1—O2iii | 88.22 (9) |
C1—C6—H6 | 120.4 | O3ii—Ni1—O2iii | 90.59 (9) |
O4—C7—O3 | 127.0 (3) | O1W—Ni1—O1 | 90.89 (10) |
O4—C7—C5 | 117.2 (3) | O2W—Ni1—O1 | 91.54 (9) |
O3—C7—C5 | 115.7 (3) | O3ii—Ni1—O1 | 84.10 (9) |
O2—C8—O1 | 124.1 (3) | O2iii—Ni1—O1 | 174.69 (9) |
O2—C8—C4 | 118.5 (3) | O1W—Ni1—N2iv | 87.71 (10) |
O1—C8—C4 | 117.3 (3) | O2W—Ni1—N2iv | 85.84 (10) |
O5—C9—N1 | 123.7 (3) | O3ii—Ni1—N2iv | 172.97 (10) |
O5—C9—C10 | 121.8 (3) | O2iii—Ni1—N2iv | 93.87 (9) |
N1—C9—C10 | 114.5 (3) | O1—Ni1—N2iv | 91.40 (9) |
C11—C10—C14 | 117.7 (3) | C8—O1—Ni1 | 140.2 (2) |
C11—C10—C9 | 123.2 (3) | C8—O2—Ni1v | 142.0 (2) |
C14—C10—C9 | 118.8 (3) | C7—O3—Ni1ii | 134.5 (2) |
C12—C11—C10 | 119.5 (3) | Ni1—O1W—H1X | 125.1 |
C12—C11—H11 | 120.3 | Ni1—O1W—H1Y | 109.6 |
C10—C11—H11 | 120.3 | H1X—O1W—H1Y | 125.3 |
N2—C12—C11 | 123.6 (3) | Ni1—O2W—H2X | 109.5 |
N2—C12—H12 | 118.2 | Ni1—O2W—H2Y | 109.5 |
C11—C12—H12 | 118.2 | H2X—O2W—H2Y | 109.5 |
C6—C1—C2—C3 | 4.4 (5) | C14—C10—C11—C12 | 1.1 (5) |
N1—C1—C2—C3 | −174.5 (3) | C9—C10—C11—C12 | −172.2 (3) |
C1—C2—C3—C4 | −2.4 (5) | C10—C11—C12—N2 | −0.4 (6) |
C2—C3—C4—C5 | −0.8 (5) | N2—C13—C14—C10 | −1.5 (5) |
C2—C3—C4—C8 | −178.4 (3) | C11—C10—C14—C13 | −0.2 (5) |
C3—C4—C5—C6 | 2.1 (5) | C9—C10—C14—C13 | 173.4 (3) |
C8—C4—C5—C6 | 179.5 (3) | O5—C9—N1—C1 | −3.5 (6) |
C3—C4—C5—C7 | −177.3 (3) | C10—C9—N1—C1 | 176.3 (3) |
C8—C4—C5—C7 | 0.2 (5) | C2—C1—N1—C9 | −144.5 (4) |
C4—C5—C6—C1 | −0.1 (5) | C6—C1—N1—C9 | 36.6 (6) |
C7—C5—C6—C1 | 179.2 (3) | C11—C12—N2—C13 | −1.2 (5) |
C2—C1—C6—C5 | −3.1 (5) | C11—C12—N2—Ni1i | 173.1 (3) |
N1—C1—C6—C5 | 175.8 (3) | C14—C13—N2—C12 | 2.2 (5) |
C6—C5—C7—O4 | −37.6 (5) | C14—C13—N2—Ni1i | −172.2 (3) |
C4—C5—C7—O4 | 141.8 (4) | O2—C8—O1—Ni1 | 140.8 (3) |
C6—C5—C7—O3 | 142.2 (3) | C4—C8—O1—Ni1 | −42.9 (5) |
C4—C5—C7—O3 | −38.4 (5) | O1W—Ni1—O1—C8 | 151.9 (4) |
C3—C4—C8—O2 | 108.2 (4) | O2W—Ni1—O1—C8 | −21.7 (4) |
C5—C4—C8—O2 | −69.3 (5) | O3ii—Ni1—O1—C8 | −110.5 (4) |
C3—C4—C8—O1 | −68.4 (4) | N2iv—Ni1—O1—C8 | 64.1 (4) |
C5—C4—C8—O1 | 114.1 (4) | O1—C8—O2—Ni1v | 132.2 (3) |
O5—C9—C10—C11 | 138.4 (4) | C4—C8—O2—Ni1v | −44.0 (5) |
N1—C9—C10—C11 | −41.4 (5) | O4—C7—O3—Ni1ii | −31.4 (6) |
O5—C9—C10—C14 | −34.8 (6) | C5—C7—O3—Ni1ii | 148.8 (2) |
N1—C9—C10—C14 | 145.4 (4) |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) x+1/2, −y+1/2, z−1/2; (v) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5iv | 0.86 | 2.17 | 3.011 (4) | 167 |
O1W—H1X···O4vi | 0.85 | 1.92 | 2.762 (3) | 169 |
O1W—H1Y···O1vii | 0.96 | 1.93 | 2.775 (3) | 146 |
O2W—H2X···O3 | 0.96 | 2.03 | 2.748 (3) | 130 |
O2W—H2X···O1ii | 0.96 | 2.25 | 3.055 (3) | 141 |
O2W—H2Y···O2ii | 0.96 | 2.39 | 2.923 (4) | 114 |
O2W—H2Y···O4iii | 0.96 | 2.49 | 3.350 (4) | 148 |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) x+1/2, −y+1/2, z−1/2; (vi) x+1, y, z−1; (vii) −x+1, −y+1, −z−1. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C14H8N2O5)(H2O)2] |
Mr | 378.97 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 291 |
a, b, c (Å) | 6.5322 (8), 30.456 (4), 7.2856 (7) |
β (°) | 91.223 (3) |
V (Å3) | 1449.1 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.38 |
Crystal size (mm) | 0.22 × 0.14 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.751, 0.898 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7738, 2810, 2379 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.147, 1.05 |
No. of reflections | 2810 |
No. of parameters | 217 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.62, −0.57 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).
N2—Ni1i | 2.332 (3) | Ni1—O3ii | 2.184 (2) |
Ni1—O1W | 2.095 (3) | Ni1—O2iii | 2.213 (3) |
Ni1—O2W | 2.155 (2) | Ni1—O1 | 2.239 (3) |
O1W—Ni1—O2W | 173.16 (9) | O3ii—Ni1—O1 | 84.10 (9) |
O1W—Ni1—O3ii | 97.73 (9) | O2iii—Ni1—O1 | 174.69 (9) |
O2W—Ni1—O3ii | 88.88 (9) | O1W—Ni1—N2iv | 87.71 (10) |
O1W—Ni1—O2iii | 89.94 (10) | O2W—Ni1—N2iv | 85.84 (10) |
O2W—Ni1—O2iii | 88.22 (9) | O3ii—Ni1—N2iv | 172.97 (10) |
O3ii—Ni1—O2iii | 90.59 (9) | O2iii—Ni1—N2iv | 93.87 (9) |
O1W—Ni1—O1 | 90.89 (10) | O1—Ni1—N2iv | 91.40 (9) |
O2W—Ni1—O1 | 91.54 (9) |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) x+1/2, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5iv | 0.86 | 2.17 | 3.011 (4) | 167 |
O1W—H1X···O4v | 0.85 | 1.92 | 2.762 (3) | 169 |
O1W—H1Y···O1vi | 0.96 | 1.93 | 2.775 (3) | 146 |
O2W—H2X···O3 | 0.96 | 2.03 | 2.748 (3) | 130 |
O2W—H2X···O1ii | 0.96 | 2.25 | 3.055 (3) | 141 |
O2W—H2Y···O2ii | 0.96 | 2.39 | 2.923 (4) | 114 |
O2W—H2Y···O4iii | 0.96 | 2.49 | 3.350 (4) | 148 |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) x+1/2, −y+1/2, z−1/2; (v) x+1, y, z−1; (vi) −x+1, −y+1, −z−1. |