Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011302012X/sf3203sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011302012X/sf3203Isup2.hkl |
CCDC reference: 965301
Recently, the design and synthesis of metal–organic coordination polymers have attracted muuch interest because of their interesting structural diversity and special properties, such as porosity, nonlinear optical activity, luminescence, magnetism and catalytic activity, as well as their intriguing variety of architectures and molecular topologies (Ni et al., 2005; Rowsell & Yaghi, 2005; Coronado et al., 2000; Guo et al., 2009). To construct novel coordination polymers, we usually choose carboxylate-containing ligands which have varied coordination modes as the main connectors, and mixed ligands with N-donor groups as ancillary bridges (Deng et al., 2012; Dai et al., 2004; Sun et al., 2003). In the present case, we chose naphthalene-2,6-dicarboxylic acid (H2NDC) as our main ligand and 4-{4-[4-(pyridin-4-yl)phenoxy]phenyl}pyridine (BPDPE) as the N-donor assistant ligand to synthesize a nickel complex. Compared with the linear bis(pyridine) ligand, BPDPE is a V-shaped pyridine ligand, which can be regarded as a half-flexible ligand to construct more interesting structures (Hu et al., 2012). We report here the synthesis and structure of the title compound, [Ni(NDC)(BPDPE)2(H2O)2]n, (I).
All starting chemicals and solvents used in this synthesis were of reagent quality and purchased from commercial sources without further purification. A mixture of NiCl2.6H2O (48 mg, 0.2 mmol), H2NDC (22 mg, 0.1 mmol), BPDPE (32 mg, 0.1 mmol), DMF (7 ml) and water (7 ml) was placed in a Parr Teflon-lined stainless steel vessel (23 ml), heated to 393 K for 3 d, then cooled to room temperature slowly. Green diamond-like crystals of complex (I) (yield 34 mg, 70%) were collected at the bottom of the glass vessel.
Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms bonded to C atoms were positioned geometrically and treated as riding, with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C). The aqua H atoms were placed so as to form a reasonable hydrogen-bond network, with O—H = 0.85 Å, and were refined as riding, with Uiso(H) = 1.2UUeq(O).
Compound (I) crystallizes in the monoclinic space group P21/c, and the asymmetric unit contains half of a central NiII cation, half of a doubly deprotonated H2NDC ligand, a BPDPE ligand and a coordinated water molecule. As shown in Fig. 1, the NiII centre is six-coordinated by two carboxylate O atoms from two NDC2- ligands, two N atoms from two BPDPE ligands and two O atoms from two water molecules to form a slightly distorted octahedron. The NiII cation resides on a centre of inversion, as does the NDC2- ligand. The two carboxylate groups of each NDC2- ligand coordinate with the NiII cation in a monodentate manner and only one N atom of each BPDPE ligand coordinates with the NiII cation, so a one-dimensional chain structure is formed extending along the c axis, with an Ni···Ni distance within the chain of about 13.653 Å. There are two types of chain which are related by an ac glide and these are arranged alternately, which may reduce repulsion for a greater stabilization of the structure (Fig. 2).
There are intermolecular O4—H4C···N2i (see Table 2 for details and symmetry code) and intramolecular O4—H4B···O2ii hydrogen bonds (Table 2) in complex (I). The intermolecular hydrogen bonds are formed between identical chains, so the same types of chain extend into a (4,4)-topological layered network via these intermolecular hydrogen bonds (Fig. 3). Because of the spacious nature of the network, it allows the crossed layers to interpenetrate with each other to form inclined polycatenation networks, which accomplishes the transition from a two-dimensional to a three-dimensional structure for (I) (Fig. 4) (Batten & Robson, 1998). This demonstrates that the uncoordinated N atom and coordinated water molecules can be well used in the synthesis of unusual coordination frameworks (Hu et al., 2012). Additionally, there are weak π–π stacking interactions between the nearest C6–C10/N2 pyridine and C11–C16 benzene rings, with an interplanar distance of 3.68 Å. The dihedral angle α defined by the stacked rings is 12.12° and the slippage angles are β = 20.64 and γ = 17.78° (Fig. 5). This moderate stacking interaction further enhances the stability of complex (I).
Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 30%
probability level. All H atoms have been omitted for clarity. [Symmetry codes:
(i) -x + 3, -y + 1, -z + 2; (ii) x, y,
z.] Fig. 2. The two types of one-dimensional chain structure of (I), extending along the c axis. Fig. 3. A view of the two-dimensional supramolecular layer stacked via intermolecular O—H···N hydrogen bonds (dashed lines). Different layers are shown in different colours and intramolecular hydrogen bonds have been omitted for clarity. Fig. 4. (a) The three-dimensional network formed by the interlocking interaction in complex (I). (b) A space-filling model, showing the inclined interpenetration between the layers. Fig. 5. The π–π stacking interactions in (I), shown as thin solid lines (light green in the electronic version of the journal). Dashed lines indicate intermolecular hydrogen bonds. |
[Ni(C12H6O4)(C22H16N2O)2(H2O)2] | F(000) = 996 |
Mr = 957.65 | Dx = 1.418 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2556 reflections |
a = 11.4739 (6) Å | θ = 3.0–28.6° |
b = 15.9431 (7) Å | µ = 0.50 mm−1 |
c = 13.4291 (8) Å | T = 290 K |
β = 114.048 (7)° | Diamond-like, green |
V = 2243.4 (2) Å3 | 0.21 × 0.19 × 0.15 mm |
Z = 2 |
Bruker APEXII CCD area-detector diffractometer | 4407 independent reflections |
Radiation source: fine-focus sealed tube | 3337 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ϕ and ω scans | θmax = 26.0°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −11→14 |
Tmin = 0.890, Tmax = 0.916 | k = −19→12 |
9294 measured reflections | l = −16→16 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.4401P] where P = (Fo2 + 2Fc2)/3 |
4407 reflections | (Δ/σ)max < 0.001 |
313 parameters | Δρmax = 0.47 e Å−3 |
1 restraint | Δρmin = −0.36 e Å−3 |
[Ni(C12H6O4)(C22H16N2O)2(H2O)2] | V = 2243.4 (2) Å3 |
Mr = 957.65 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.4739 (6) Å | µ = 0.50 mm−1 |
b = 15.9431 (7) Å | T = 290 K |
c = 13.4291 (8) Å | 0.21 × 0.19 × 0.15 mm |
β = 114.048 (7)° |
Bruker APEXII CCD area-detector diffractometer | 4407 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 3337 reflections with I > 2σ(I) |
Tmin = 0.890, Tmax = 0.916 | Rint = 0.033 |
9294 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 1 restraint |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.47 e Å−3 |
4407 reflections | Δρmin = −0.36 e Å−3 |
313 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 | ||
C28 | 1.5548 (2) | 0.39910 (19) | 1.0747 (2) | 0.0480 (7) | |
H28 | 1.5310 | 0.3429 | 1.0678 | 0.058* | |
C1 | 0.8999 (2) | 0.63210 (17) | 0.6008 (2) | 0.0411 (7) | |
H1 | 0.9834 | 0.6509 | 0.6227 | 0.049* | |
C2 | 0.8213 (2) | 0.67478 (17) | 0.6381 (2) | 0.0431 (7) | |
H2 | 0.8516 | 0.7217 | 0.6822 | 0.052* | |
C3 | 0.6972 (2) | 0.64781 (17) | 0.6097 (2) | 0.0385 (6) | |
C4 | 0.6583 (2) | 0.58020 (18) | 0.5387 (2) | 0.0443 (7) | |
H4 | 0.5749 | 0.5606 | 0.5146 | 0.053* | |
C5 | 0.7424 (2) | 0.54190 (18) | 0.5035 (2) | 0.0425 (7) | |
H5 | 0.7130 | 0.4973 | 0.4550 | 0.051* | |
C6 | 0.0121 (4) | 1.1782 (2) | 0.4638 (3) | 0.0695 (10) | |
H6 | 0.0204 | 1.2030 | 0.4044 | 0.083* | |
C7 | 0.0923 (3) | 1.11316 (19) | 0.5138 (3) | 0.0617 (9) | |
H7 | 0.1542 | 1.0967 | 0.4897 | 0.074* | |
C8 | 0.0816 (2) | 1.07171 (17) | 0.6006 (2) | 0.0424 (7) | |
C9 | −0.0189 (3) | 1.0983 (2) | 0.6247 (3) | 0.0547 (8) | |
H9 | −0.0370 | 1.0706 | 0.6778 | 0.066* | |
C10 | −0.0921 (3) | 1.1658 (2) | 0.5700 (3) | 0.0655 (9) | |
H10 | −0.1580 | 1.1822 | 0.5892 | 0.079* | |
C11 | 0.1694 (3) | 1.00347 (17) | 0.6605 (2) | 0.0428 (7) | |
C12 | 0.1460 (3) | 0.95092 (19) | 0.7323 (3) | 0.0509 (8) | |
H12 | 0.0751 | 0.9611 | 0.7476 | 0.061* | |
C13 | 0.2241 (3) | 0.8842 (2) | 0.7818 (3) | 0.0534 (8) | |
H13 | 0.2066 | 0.8500 | 0.8301 | 0.064* | |
C14 | 0.3280 (3) | 0.8685 (2) | 0.7589 (3) | 0.0542 (8) | |
C15 | 0.3585 (3) | 0.9217 (2) | 0.6946 (3) | 0.0783 (12) | |
H15 | 0.4323 | 0.9128 | 0.6832 | 0.094* | |
C16 | 0.2804 (3) | 0.9890 (2) | 0.6458 (3) | 0.0659 (10) | |
H16 | 0.3027 | 1.0253 | 0.6022 | 0.079* | |
C17 | 0.4718 (3) | 0.7634 (2) | 0.7554 (3) | 0.0575 (9) | |
C18 | 0.4114 (3) | 0.7278 (3) | 0.6543 (3) | 0.0680 (10) | |
H18 | 0.3229 | 0.7292 | 0.6186 | 0.082* | |
C19 | 0.4837 (3) | 0.6898 (2) | 0.6058 (3) | 0.0584 (9) | |
H19 | 0.4433 | 0.6655 | 0.5373 | 0.070* | |
C20 | 0.6160 (2) | 0.68767 (17) | 0.6584 (2) | 0.0419 (7) | |
C21 | 0.6722 (3) | 0.7247 (2) | 0.7604 (3) | 0.0536 (8) | |
H21 | 0.7607 | 0.7244 | 0.7969 | 0.064* | |
C22 | 0.6007 (3) | 0.7619 (2) | 0.8091 (3) | 0.0589 (9) | |
H22 | 0.6403 | 0.7857 | 0.8780 | 0.071* | |
C23 | 1.1790 (2) | 0.46317 (19) | 0.7315 (2) | 0.0367 (6) | |
C24 | 1.3388 (3) | 0.5745 (2) | 0.8383 (2) | 0.0490 (7) | |
H24 | 1.2918 | 0.6130 | 0.7851 | 0.059* | |
C25 | 1.2988 (2) | 0.49020 (17) | 0.8275 (2) | 0.0370 (6) | |
C26 | 1.3672 (2) | 0.43308 (19) | 0.9036 (2) | 0.0404 (7) | |
H26 | 1.3402 | 0.3775 | 0.8964 | 0.048* | |
C27 | 1.4817 (2) | 0.45770 (17) | 0.9958 (2) | 0.0358 (6) | |
N1 | 0.86374 (18) | 0.56559 (13) | 0.53535 (17) | 0.0336 (5) | |
N2 | −0.0763 (3) | 1.20860 (17) | 0.4932 (3) | 0.0668 (8) | |
Ni1 | 1.0000 | 0.5000 | 0.5000 | 0.02874 (15) | |
O1 | 1.13149 (16) | 0.51694 (11) | 0.65671 (14) | 0.0400 (5) | |
O2 | 1.13494 (17) | 0.39159 (13) | 0.73173 (16) | 0.0546 (6) | |
O3 | 0.4003 (2) | 0.79838 (16) | 0.8081 (2) | 0.0760 (7) | |
O4 | 1.06571 (15) | 0.61064 (11) | 0.45375 (14) | 0.0367 (4) | |
H4B | 1.0046 | 0.6333 | 0.4007 | 0.055* | |
H4C | 1.0928 | 0.6443 | 0.5075 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C28 | 0.0459 (16) | 0.0455 (17) | 0.0403 (16) | 0.0010 (13) | 0.0049 (14) | 0.0079 (14) |
C1 | 0.0352 (13) | 0.0425 (16) | 0.0482 (17) | −0.0030 (12) | 0.0198 (13) | −0.0075 (14) |
C2 | 0.0447 (15) | 0.0416 (16) | 0.0481 (17) | −0.0005 (13) | 0.0240 (13) | −0.0116 (14) |
C3 | 0.0376 (14) | 0.0380 (15) | 0.0436 (16) | 0.0077 (12) | 0.0204 (12) | 0.0066 (13) |
C4 | 0.0309 (13) | 0.0478 (17) | 0.0555 (18) | 0.0000 (12) | 0.0191 (13) | −0.0042 (15) |
C5 | 0.0364 (14) | 0.0403 (16) | 0.0489 (17) | −0.0012 (12) | 0.0154 (13) | −0.0092 (14) |
C6 | 0.093 (3) | 0.043 (2) | 0.079 (3) | 0.0029 (18) | 0.043 (2) | 0.0121 (19) |
C7 | 0.074 (2) | 0.0441 (18) | 0.080 (2) | 0.0038 (17) | 0.044 (2) | 0.0067 (17) |
C8 | 0.0486 (15) | 0.0336 (15) | 0.0476 (16) | −0.0018 (13) | 0.0223 (14) | −0.0058 (13) |
C9 | 0.0561 (18) | 0.0548 (19) | 0.060 (2) | 0.0116 (15) | 0.0304 (16) | 0.0089 (17) |
C10 | 0.059 (2) | 0.065 (2) | 0.074 (2) | 0.0168 (17) | 0.0296 (18) | 0.002 (2) |
C11 | 0.0452 (15) | 0.0447 (17) | 0.0460 (16) | −0.0004 (13) | 0.0262 (14) | −0.0047 (14) |
C12 | 0.0531 (17) | 0.0533 (19) | 0.061 (2) | 0.0113 (15) | 0.0385 (16) | 0.0069 (16) |
C13 | 0.0626 (18) | 0.0569 (19) | 0.0592 (19) | 0.0153 (16) | 0.0436 (16) | 0.0139 (16) |
C14 | 0.0595 (18) | 0.062 (2) | 0.0543 (19) | 0.0247 (16) | 0.0367 (16) | 0.0131 (16) |
C15 | 0.069 (2) | 0.096 (3) | 0.100 (3) | 0.037 (2) | 0.065 (2) | 0.042 (2) |
C16 | 0.069 (2) | 0.069 (2) | 0.083 (3) | 0.0189 (18) | 0.055 (2) | 0.032 (2) |
C17 | 0.068 (2) | 0.063 (2) | 0.059 (2) | 0.0332 (17) | 0.0448 (18) | 0.0241 (18) |
C18 | 0.0458 (17) | 0.104 (3) | 0.060 (2) | 0.0281 (18) | 0.0269 (16) | 0.019 (2) |
C19 | 0.0460 (16) | 0.083 (2) | 0.0492 (18) | 0.0143 (16) | 0.0223 (15) | 0.0039 (17) |
C20 | 0.0420 (14) | 0.0430 (16) | 0.0468 (16) | 0.0104 (12) | 0.0243 (13) | 0.0091 (14) |
C21 | 0.0517 (17) | 0.059 (2) | 0.0564 (19) | 0.0122 (15) | 0.0281 (15) | −0.0023 (16) |
C22 | 0.067 (2) | 0.065 (2) | 0.0545 (19) | 0.0170 (17) | 0.0347 (17) | −0.0015 (17) |
C23 | 0.0268 (12) | 0.0522 (17) | 0.0283 (14) | 0.0042 (12) | 0.0083 (11) | −0.0057 (13) |
C24 | 0.0413 (15) | 0.0576 (19) | 0.0366 (16) | 0.0002 (14) | 0.0040 (13) | 0.0029 (15) |
C25 | 0.0290 (12) | 0.0524 (18) | 0.0273 (13) | 0.0067 (12) | 0.0090 (11) | −0.0004 (13) |
C26 | 0.0345 (14) | 0.0527 (18) | 0.0322 (14) | −0.0019 (13) | 0.0119 (12) | −0.0013 (13) |
C27 | 0.0335 (13) | 0.0438 (15) | 0.0317 (14) | 0.0045 (12) | 0.0148 (12) | 0.0026 (13) |
N1 | 0.0334 (11) | 0.0330 (12) | 0.0353 (12) | 0.0023 (9) | 0.0150 (9) | −0.0028 (10) |
N2 | 0.083 (2) | 0.0403 (15) | 0.079 (2) | 0.0101 (15) | 0.0359 (17) | 0.0057 (15) |
Ni1 | 0.0261 (2) | 0.0321 (3) | 0.0248 (2) | 0.00333 (18) | 0.00703 (18) | −0.0026 (2) |
O1 | 0.0354 (9) | 0.0456 (11) | 0.0282 (10) | 0.0038 (8) | 0.0019 (8) | −0.0036 (9) |
O2 | 0.0451 (11) | 0.0585 (14) | 0.0413 (12) | −0.0046 (10) | −0.0017 (9) | 0.0076 (11) |
O3 | 0.0946 (16) | 0.0898 (18) | 0.0713 (16) | 0.0552 (14) | 0.0623 (14) | 0.0368 (14) |
O4 | 0.0338 (9) | 0.0397 (10) | 0.0320 (10) | 0.0017 (8) | 0.0088 (8) | −0.0001 (8) |
C28—C24i | 1.368 (4) | C15—C16 | 1.381 (4) |
C28—C27 | 1.405 (4) | C15—H15 | 0.9300 |
C28—H28 | 0.9300 | C16—H16 | 0.9300 |
C1—N1 | 1.331 (3) | C17—C22 | 1.357 (4) |
C1—C2 | 1.375 (4) | C17—C18 | 1.370 (5) |
C1—H1 | 0.9300 | C17—O3 | 1.400 (3) |
C2—C3 | 1.385 (4) | C18—C19 | 1.385 (4) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.387 (4) | C19—C20 | 1.390 (4) |
C3—C20 | 1.481 (4) | C19—H19 | 0.9300 |
C4—C5 | 1.378 (4) | C20—C21 | 1.386 (4) |
C4—H4 | 0.9300 | C21—C22 | 1.374 (4) |
C5—N1 | 1.334 (3) | C21—H21 | 0.9300 |
C5—H5 | 0.9300 | C22—H22 | 0.9300 |
C6—N2 | 1.321 (4) | C23—O2 | 1.249 (3) |
C6—C7 | 1.367 (4) | C23—O1 | 1.263 (3) |
C6—H6 | 0.9300 | C23—C25 | 1.514 (4) |
C7—C8 | 1.388 (4) | C24—C28i | 1.368 (4) |
C7—H7 | 0.9300 | C24—C25 | 1.408 (4) |
C8—C9 | 1.386 (4) | C24—H24 | 0.9300 |
C8—C11 | 1.478 (4) | C25—C26 | 1.355 (4) |
C9—C10 | 1.378 (4) | C26—C27 | 1.445 (3) |
C9—H9 | 0.9300 | C26—H26 | 0.9300 |
C10—N2 | 1.311 (4) | C27—C27i | 1.403 (5) |
C10—H10 | 0.9300 | N1—Ni1 | 2.0900 (19) |
C11—C12 | 1.384 (4) | Ni1—O1 | 2.0470 (17) |
C11—C16 | 1.385 (4) | Ni1—O1ii | 2.0470 (17) |
C12—C13 | 1.376 (4) | Ni1—N1ii | 2.0900 (19) |
C12—H12 | 0.9300 | Ni1—O4ii | 2.1089 (17) |
C13—C14 | 1.369 (4) | Ni1—O4 | 2.1089 (17) |
C13—H13 | 0.9300 | O4—H4B | 0.8500 |
C14—C15 | 1.354 (4) | O4—H4C | 0.8501 |
C14—O3 | 1.389 (4) | ||
C24i—C28—C27 | 119.3 (3) | C17—C18—C19 | 119.3 (3) |
C24i—C28—H28 | 120.3 | C17—C18—H18 | 120.4 |
C27—C28—H28 | 120.3 | C19—C18—H18 | 120.4 |
N1—C1—C2 | 124.1 (2) | C18—C19—C20 | 120.8 (3) |
N1—C1—H1 | 118.0 | C18—C19—H19 | 119.6 |
C2—C1—H1 | 118.0 | C20—C19—H19 | 119.6 |
C1—C2—C3 | 120.0 (3) | C21—C20—C19 | 117.6 (3) |
C1—C2—H2 | 120.0 | C21—C20—C3 | 119.7 (2) |
C3—C2—H2 | 120.0 | C19—C20—C3 | 122.6 (3) |
C2—C3—C4 | 115.9 (2) | C22—C21—C20 | 121.8 (3) |
C2—C3—C20 | 120.4 (3) | C22—C21—H21 | 119.1 |
C4—C3—C20 | 123.6 (2) | C20—C21—H21 | 119.1 |
C5—C4—C3 | 120.4 (2) | C17—C22—C21 | 119.2 (3) |
C5—C4—H4 | 119.8 | C17—C22—H22 | 120.4 |
C3—C4—H4 | 119.8 | C21—C22—H22 | 120.4 |
N1—C5—C4 | 123.4 (3) | O2—C23—O1 | 125.3 (2) |
N1—C5—H5 | 118.3 | O2—C23—C25 | 119.0 (2) |
C4—C5—H5 | 118.3 | O1—C23—C25 | 115.6 (3) |
N2—C6—C7 | 125.3 (4) | C28i—C24—C25 | 121.5 (3) |
N2—C6—H6 | 117.4 | C28i—C24—H24 | 119.3 |
C7—C6—H6 | 117.4 | C25—C24—H24 | 119.3 |
C6—C7—C8 | 120.0 (3) | C26—C25—C24 | 120.0 (2) |
C6—C7—H7 | 120.0 | C26—C25—C23 | 119.8 (3) |
C8—C7—H7 | 120.0 | C24—C25—C23 | 120.3 (2) |
C9—C8—C7 | 114.7 (3) | C25—C26—C27 | 120.6 (3) |
C9—C8—C11 | 123.1 (3) | C25—C26—H26 | 119.7 |
C7—C8—C11 | 122.2 (3) | C27—C26—H26 | 119.7 |
C10—C9—C8 | 119.9 (3) | C27i—C27—C28 | 120.8 (3) |
C10—C9—H9 | 120.0 | C27i—C27—C26 | 117.9 (3) |
C8—C9—H9 | 120.0 | C28—C27—C26 | 121.3 (3) |
N2—C10—C9 | 125.2 (3) | C1—N1—C5 | 116.2 (2) |
N2—C10—H10 | 117.4 | C1—N1—Ni1 | 119.22 (16) |
C9—C10—H10 | 117.4 | C5—N1—Ni1 | 124.43 (18) |
C12—C11—C16 | 116.7 (3) | C10—N2—C6 | 114.4 (3) |
C12—C11—C8 | 122.8 (2) | O1—Ni1—O1ii | 180.0 |
C16—C11—C8 | 120.5 (3) | O1—Ni1—N1 | 90.38 (8) |
C13—C12—C11 | 122.1 (3) | O1ii—Ni1—N1 | 89.62 (8) |
C13—C12—H12 | 119.0 | O1—Ni1—N1ii | 89.62 (8) |
C11—C12—H12 | 119.0 | O1ii—Ni1—N1ii | 90.38 (8) |
C14—C13—C12 | 119.2 (3) | N1—Ni1—N1ii | 180.00 (6) |
C14—C13—H13 | 120.4 | O1—Ni1—O4ii | 90.56 (7) |
C12—C13—H13 | 120.4 | O1ii—Ni1—O4ii | 89.44 (7) |
C15—C14—C13 | 120.3 (3) | N1—Ni1—O4ii | 87.78 (7) |
C15—C14—O3 | 123.2 (3) | N1ii—Ni1—O4ii | 92.22 (7) |
C13—C14—O3 | 116.5 (3) | O1—Ni1—O4 | 89.44 (7) |
C14—C15—C16 | 120.2 (3) | O1ii—Ni1—O4 | 90.56 (7) |
C14—C15—H15 | 119.9 | N1—Ni1—O4 | 92.22 (7) |
C16—C15—H15 | 119.9 | N1ii—Ni1—O4 | 87.78 (7) |
C15—C16—C11 | 121.2 (3) | O4ii—Ni1—O4 | 180.0 |
C15—C16—H16 | 119.4 | C23—O1—Ni1 | 128.79 (18) |
C11—C16—H16 | 119.4 | C14—O3—C17 | 116.1 (2) |
C22—C17—C18 | 121.4 (3) | Ni1—O4—H4B | 109.3 |
C22—C17—O3 | 118.4 (3) | Ni1—O4—H4C | 109.2 |
C18—C17—O3 | 120.2 (3) | H4B—O4—H4C | 109.5 |
N1—C1—C2—C3 | 1.6 (5) | O3—C17—C22—C21 | 177.4 (3) |
C1—C2—C3—C4 | −3.5 (4) | C20—C21—C22—C17 | −0.8 (5) |
C1—C2—C3—C20 | 173.6 (3) | C28i—C24—C25—C26 | −0.9 (4) |
C2—C3—C4—C5 | 2.3 (4) | C28i—C24—C25—C23 | 178.8 (3) |
C20—C3—C4—C5 | −174.6 (3) | O2—C23—C25—C26 | 10.2 (4) |
C3—C4—C5—N1 | 0.9 (5) | O1—C23—C25—C26 | −170.2 (2) |
N2—C6—C7—C8 | 2.2 (6) | O2—C23—C25—C24 | −169.5 (3) |
C6—C7—C8—C9 | 3.9 (5) | O1—C23—C25—C24 | 10.2 (4) |
C6—C7—C8—C11 | −177.3 (3) | C24—C25—C26—C27 | −0.4 (4) |
C7—C8—C9—C10 | −5.3 (4) | C23—C25—C26—C27 | 180.0 (2) |
C11—C8—C9—C10 | 176.0 (3) | C24i—C28—C27—C27i | 1.3 (5) |
C8—C9—C10—N2 | 0.8 (5) | C24i—C28—C27—C26 | −178.8 (3) |
C9—C8—C11—C12 | 11.6 (4) | C25—C26—C27—C27i | 0.8 (4) |
C7—C8—C11—C12 | −167.1 (3) | C25—C26—C27—C28 | −179.1 (3) |
C9—C8—C11—C16 | −169.0 (3) | C2—C1—N1—C5 | 1.7 (4) |
C7—C8—C11—C16 | 12.4 (5) | C2—C1—N1—Ni1 | −173.3 (2) |
C16—C11—C12—C13 | −4.0 (5) | C4—C5—N1—C1 | −2.9 (4) |
C8—C11—C12—C13 | 175.5 (3) | C4—C5—N1—Ni1 | 171.8 (2) |
C11—C12—C13—C14 | −0.5 (5) | C9—C10—N2—C6 | 5.1 (5) |
C12—C13—C14—C15 | 4.7 (5) | C7—C6—N2—C10 | −6.7 (5) |
C12—C13—C14—O3 | −177.6 (3) | C1—N1—Ni1—O1 | 38.0 (2) |
C13—C14—C15—C16 | −4.2 (6) | C5—N1—Ni1—O1 | −136.6 (2) |
O3—C14—C15—C16 | 178.3 (4) | C1—N1—Ni1—O1ii | −142.0 (2) |
C14—C15—C16—C11 | −0.5 (6) | C5—N1—Ni1—O1ii | 43.4 (2) |
C12—C11—C16—C15 | 4.5 (5) | C1—N1—Ni1—O4ii | 128.5 (2) |
C8—C11—C16—C15 | −175.0 (3) | C5—N1—Ni1—O4ii | −46.0 (2) |
C22—C17—C18—C19 | −0.2 (5) | C1—N1—Ni1—O4 | −51.5 (2) |
O3—C17—C18—C19 | −176.8 (3) | C5—N1—Ni1—O4 | 134.0 (2) |
C17—C18—C19—C20 | −0.2 (5) | O2—C23—O1—Ni1 | −16.5 (4) |
C18—C19—C20—C21 | 0.0 (5) | C25—C23—O1—Ni1 | 163.91 (16) |
C18—C19—C20—C3 | −180.0 (3) | N1—Ni1—O1—C23 | 110.7 (2) |
C2—C3—C20—C21 | −26.9 (4) | N1ii—Ni1—O1—C23 | −69.3 (2) |
C4—C3—C20—C21 | 149.9 (3) | O4ii—Ni1—O1—C23 | 22.9 (2) |
C2—C3—C20—C19 | 153.1 (3) | O4—Ni1—O1—C23 | −157.1 (2) |
C4—C3—C20—C19 | −30.1 (4) | C15—C14—O3—C17 | −26.7 (5) |
C19—C20—C21—C22 | 0.5 (5) | C13—C14—O3—C17 | 155.7 (3) |
C3—C20—C21—C22 | −179.5 (3) | C22—C17—O3—C14 | 117.8 (3) |
C18—C17—C22—C21 | 0.7 (5) | C18—C17—O3—C14 | −65.4 (4) |
Symmetry codes: (i) −x+3, −y+1, −z+2; (ii) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4C···N2iii | 0.85 | 2.35 | 2.959 (3) | 129 |
O4—H4B···O2ii | 0.85 | 1.89 | 2.614 (2) | 143 |
Symmetry codes: (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C12H6O4)(C22H16N2O)2(H2O)2] |
Mr | 957.65 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 290 |
a, b, c (Å) | 11.4739 (6), 15.9431 (7), 13.4291 (8) |
β (°) | 114.048 (7) |
V (Å3) | 2243.4 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.50 |
Crystal size (mm) | 0.21 × 0.19 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.890, 0.916 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9294, 4407, 3337 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.124, 1.07 |
No. of reflections | 4407 |
No. of parameters | 313 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.36 |
Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4C···N2i | 0.85 | 2.35 | 2.959 (3) | 128.7 |
O4—H4B···O2ii | 0.85 | 1.89 | 2.614 (2) | 142.5 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1. |