Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023185/dn2174sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023185/dn2174Isup2.hkl |
CCDC reference: 650688
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.026
- wR factor = 0.063
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Bernstein et al. (1995); Etter et al. (1990); Gu et al. (2004); Iglesias et al. (2003); Kim et al. (2003); Moulton & Zaworotko (2001).
bis(2-pyridyl)amine(0.065 g, 7 mmol), Ni(CH3COO)2 (0.18 g, 12 mmol) and Na2CO3(0.23 g,10 mmol), were added in a mixed solvent of methanol and acetonitrile, the mixture was heated for five h under reflux. during the process stirring and influx were required. The resultant was then filtered to give a pure solution which was infiltrated by diethyl ether freely in a closed vessel, a weeks later some single crystals of the size suitable for X-Ray diffraction analysis.
H atoms attached to C and N atoms were placed at calculated positions and treated as riding on their parent atoms with C—H = 0.93 Å, N—H = 0.86 Å and with Uiso(H) = 1.2 Ueq(C, N). H atoms attached to water molecules were located in difference Fourier maps but were treated as riding with O—H distance restraints to 0.82 Å and H···H to 1.39 Å and with Uiso(H)= 1.5 Ueq(O).
Molecular self-assembly of supramolecular architectures has received much attention during recent decades (Kim et al., 2003; Iglesias et al., 2003; Moulton & Zaworotko, 2001). The structures and properties of such systems depend on the coordination and geometric preferences of both the central metals ions and bridging building blocks as well as the influence of weaker non-covalent interactions, such as hydrogen bonds and π-π stacking interactions. 4-Chlorobenzoic acid and imidazole are excellent candidates for the construction of supramolecular complexes, since they not only have multiple coordination modes but also can form regular hydrogen bonds by functioning as both hydrogen-bond donor and acceptor (Gu et al., 2004). Recently, we obtained the title polymer nickel complex (I) by the reaction of nickel carbonate, bis(2-pyridyl)amine in solution of methanol and acetonitrile.
In complex (I), each NiII centre is coordinated by three O atoms from two carbonate ligands, two N atoms from one bis(2-pyridyl)amine ligand, and displayed a distorted square pyramidal geometry (Fig. 1). The compound forms infinite chain via carbonate ligands bridging the Ni-bis(2-pyridyl)amine units and further linked into a neutral layer through N3—H···O3(carbonate) intermolecular hydrogen bonding interactions (Table 1) and weak slipped π-π stacking with centroid to centroid distance of 3.674 (1)Å and interplanar distance of 3.438\%A between pyridyl group of neighboring chain. The water molecules form infinite lamellar structure containing R55(10) graph set motif (Etter et al., 1990; Bernstein et al., 1995), which fill in the space between the chains and are connected through O—H···O hydrogen bonds with carbonate ligands (Table 1).
For related literature, see: Bernstein et al. (1995); Etter et al. (1990); Gu et al. (2004); Iglesias et al. (2003); Kim et al. (2003); Moulton & Zaworotko (2001).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.
[Ni(CO3)(C10H9N3)]·3H2O | F(000) = 712 |
Mr = 343.97 | Dx = 1.669 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2600 reflections |
a = 11.2453 (11) Å | θ = 1.7–26.0° |
b = 7.1554 (7) Å | µ = 1.45 mm−1 |
c = 17.3387 (16) Å | T = 298 K |
β = 101.106 (1)° | Block, blue |
V = 1369.0 (2) Å3 | 0.20 × 0.19 × 0.18 mm |
Z = 4 |
Bruker APEX-II area-detector diffractometer | 2671 independent reflections |
Radiation source: fine-focus sealed tube | 2068 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scan | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −13→13 |
Tmin = 0.760, Tmax = 0.780 | k = −8→8 |
7073 measured reflections | l = −16→21 |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0345P)2] where P = (Fo2 + 2Fc2)/3 |
2671 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.31 e Å−3 |
9 restraints | Δρmin = −0.31 e Å−3 |
[Ni(CO3)(C10H9N3)]·3H2O | V = 1369.0 (2) Å3 |
Mr = 343.97 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.2453 (11) Å | µ = 1.45 mm−1 |
b = 7.1554 (7) Å | T = 298 K |
c = 17.3387 (16) Å | 0.20 × 0.19 × 0.18 mm |
β = 101.106 (1)° |
Bruker APEX-II area-detector diffractometer | 2671 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | 2068 reflections with I > 2σ(I) |
Tmin = 0.760, Tmax = 0.780 | Rint = 0.027 |
7073 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 9 restraints |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.31 e Å−3 |
2671 reflections | Δρmin = −0.31 e Å−3 |
190 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 | ||
Ni1 | 0.96874 (2) | 0.68093 (3) | 0.128525 (13) | 0.02662 (9) | |
N2 | 1.08891 (15) | 0.6870 (2) | 0.05901 (9) | 0.0305 (4) | |
N3 | 0.95476 (15) | 0.8085 (2) | −0.05193 (9) | 0.0359 (4) | |
H3 | 0.9528 | 0.8552 | −0.0979 | 0.043* | |
O1 | 0.87293 (12) | 0.5970 (2) | 0.20646 (8) | 0.0398 (4) | |
N1 | 0.83439 (15) | 0.7605 (2) | 0.04433 (9) | 0.0311 (4) | |
C6 | 0.84388 (18) | 0.8087 (3) | −0.02909 (11) | 0.0311 (4) | |
O2 | 1.06489 (12) | 0.5455 (2) | 0.21974 (8) | 0.0442 (4) | |
C7 | 1.06774 (18) | 0.7483 (3) | −0.01579 (11) | 0.0308 (5) | |
C3 | 0.6207 (2) | 0.8162 (3) | 0.01007 (13) | 0.0456 (6) | |
H3A | 0.5456 | 0.8181 | 0.0250 | 0.055* | |
C11 | 1.20373 (19) | 0.6317 (3) | 0.09050 (13) | 0.0388 (5) | |
H11 | 1.2195 | 0.5891 | 0.1421 | 0.047* | |
C9 | 1.2734 (2) | 0.6984 (3) | −0.02676 (13) | 0.0429 (6) | |
H9 | 1.3351 | 0.7020 | −0.0555 | 0.051* | |
C8 | 1.1593 (2) | 0.7546 (3) | −0.05985 (12) | 0.0386 (5) | |
H8 | 1.1425 | 0.7970 | −0.1115 | 0.046* | |
C1 | 0.96998 (18) | 0.5327 (3) | 0.25138 (11) | 0.0308 (5) | |
C2 | 0.72183 (19) | 0.7660 (3) | 0.06210 (12) | 0.0372 (5) | |
H2 | 0.7137 | 0.7336 | 0.1128 | 0.045* | |
C10 | 1.2966 (2) | 0.6354 (3) | 0.05080 (13) | 0.0415 (5) | |
H10 | 1.3739 | 0.5968 | 0.0748 | 0.050* | |
C5 | 0.7433 (2) | 0.8611 (3) | −0.08549 (13) | 0.0430 (6) | |
H5 | 0.7525 | 0.8932 | −0.1360 | 0.052* | |
O3 | 0.97143 (13) | 0.46848 (19) | 0.31877 (8) | 0.0387 (4) | |
O4 | 0.69188 (15) | 0.0454 (3) | 0.20442 (10) | 0.0679 (5) | |
H4A | 0.6744 | 0.1583 | 0.2043 | 0.102* | |
H4B | 0.7660 | 0.0306 | 0.2211 | 0.102* | |
O5 | 0.65269 (16) | 0.4323 (3) | 0.21925 (11) | 0.0731 (6) | |
H5A | 0.6025 | 0.5150 | 0.2043 | 0.110* | |
H5B | 0.7226 | 0.4699 | 0.2157 | 0.110* | |
O6 | 0.52597 (17) | 0.7637 (3) | 0.19881 (12) | 0.0799 (6) | |
H6A | 0.4651 | 0.8016 | 0.2150 | 0.120* | |
H6B | 0.5797 | 0.8459 | 0.2053 | 0.120* | |
C4 | 0.6314 (2) | 0.8648 (3) | −0.06583 (14) | 0.0474 (6) | |
H4 | 0.5635 | 0.8993 | −0.1027 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02843 (15) | 0.03306 (16) | 0.01923 (14) | 0.00066 (11) | 0.00676 (10) | 0.00453 (11) |
N2 | 0.0360 (9) | 0.0311 (9) | 0.0249 (9) | −0.0002 (8) | 0.0069 (7) | 0.0007 (7) |
N3 | 0.0410 (10) | 0.0451 (11) | 0.0222 (9) | 0.0009 (8) | 0.0072 (7) | 0.0074 (8) |
O1 | 0.0331 (8) | 0.0548 (10) | 0.0316 (8) | 0.0015 (7) | 0.0065 (6) | 0.0109 (7) |
N1 | 0.0355 (9) | 0.0323 (9) | 0.0266 (9) | −0.0017 (7) | 0.0086 (7) | 0.0003 (7) |
C6 | 0.0394 (11) | 0.0285 (11) | 0.0255 (10) | −0.0011 (9) | 0.0066 (8) | −0.0001 (9) |
O2 | 0.0377 (8) | 0.0619 (11) | 0.0355 (8) | 0.0077 (7) | 0.0131 (7) | 0.0173 (7) |
C7 | 0.0392 (12) | 0.0257 (10) | 0.0286 (11) | −0.0026 (9) | 0.0097 (9) | −0.0024 (9) |
C3 | 0.0377 (13) | 0.0528 (15) | 0.0466 (14) | 0.0057 (11) | 0.0086 (10) | 0.0048 (12) |
C11 | 0.0411 (12) | 0.0445 (14) | 0.0309 (12) | 0.0016 (10) | 0.0070 (10) | 0.0003 (10) |
C9 | 0.0413 (13) | 0.0483 (15) | 0.0437 (13) | −0.0053 (11) | 0.0198 (10) | −0.0038 (11) |
C8 | 0.0476 (13) | 0.0413 (12) | 0.0303 (12) | −0.0040 (10) | 0.0159 (10) | 0.0011 (10) |
C1 | 0.0418 (12) | 0.0275 (11) | 0.0242 (11) | −0.0014 (9) | 0.0089 (9) | −0.0019 (9) |
C2 | 0.0382 (12) | 0.0420 (13) | 0.0333 (12) | 0.0018 (10) | 0.0117 (10) | 0.0052 (10) |
C10 | 0.0362 (12) | 0.0477 (14) | 0.0416 (13) | 0.0010 (10) | 0.0102 (10) | −0.0011 (11) |
C5 | 0.0527 (14) | 0.0453 (14) | 0.0291 (12) | 0.0024 (11) | 0.0031 (10) | 0.0078 (10) |
O3 | 0.0559 (9) | 0.0366 (8) | 0.0253 (8) | 0.0049 (7) | 0.0118 (7) | 0.0044 (6) |
O4 | 0.0499 (10) | 0.0764 (14) | 0.0763 (13) | −0.0059 (9) | 0.0096 (9) | −0.0186 (10) |
O5 | 0.0521 (11) | 0.0642 (13) | 0.1086 (17) | −0.0082 (9) | 0.0295 (11) | 0.0081 (11) |
O6 | 0.0583 (12) | 0.0697 (13) | 0.1189 (18) | −0.0003 (10) | 0.0345 (12) | −0.0102 (12) |
C4 | 0.0397 (13) | 0.0547 (16) | 0.0446 (14) | 0.0085 (11) | 0.0002 (11) | 0.0083 (11) |
Ni1—N1 | 1.9718 (17) | C11—C10 | 1.357 (3) |
Ni1—O1 | 1.9769 (13) | C11—H11 | 0.9300 |
Ni1—N2 | 1.9770 (16) | C9—C8 | 1.361 (3) |
Ni1—O2 | 1.9877 (14) | C9—C10 | 1.395 (3) |
Ni1—O3i | 2.2988 (14) | C9—H9 | 0.9300 |
Ni1—C1 | 2.3772 (19) | C8—H8 | 0.9300 |
N2—C7 | 1.346 (2) | C1—O3 | 1.253 (2) |
N2—C11 | 1.360 (3) | C2—H2 | 0.9300 |
N3—C7 | 1.373 (2) | C10—H10 | 0.9300 |
N3—C6 | 1.379 (2) | C5—C4 | 1.366 (3) |
N3—H3 | 0.8600 | C5—H5 | 0.9300 |
O1—C1 | 1.297 (2) | O3—Ni1ii | 2.2988 (14) |
N1—C6 | 1.343 (2) | O4—H4A | 0.8316 |
N1—C2 | 1.360 (2) | O4—H4B | 0.8353 |
C6—C5 | 1.396 (3) | O5—H5A | 0.8244 |
O2—C1 | 1.294 (2) | O5—H5B | 0.8446 |
C7—C8 | 1.396 (3) | O6—H6A | 0.8328 |
C3—C2 | 1.357 (3) | O6—H6B | 0.8352 |
C3—C4 | 1.389 (3) | C4—H4 | 0.9300 |
C3—H3A | 0.9300 | ||
N1—Ni1—O1 | 98.81 (6) | C2—C3—H3A | 120.6 |
N1—Ni1—N2 | 93.36 (7) | C4—C3—H3A | 120.6 |
O1—Ni1—N2 | 161.80 (6) | C10—C11—N2 | 123.7 (2) |
N1—Ni1—O2 | 162.12 (6) | C10—C11—H11 | 118.2 |
O1—Ni1—O2 | 65.96 (6) | N2—C11—H11 | 118.2 |
N2—Ni1—O2 | 99.49 (6) | C8—C9—C10 | 119.2 (2) |
N1—Ni1—O3i | 99.19 (6) | C8—C9—H9 | 120.4 |
O1—Ni1—O3i | 99.00 (6) | C10—C9—H9 | 120.4 |
N2—Ni1—O3i | 92.33 (6) | C9—C8—C7 | 119.6 (2) |
O2—Ni1—O3i | 92.71 (6) | C9—C8—H8 | 120.2 |
N1—Ni1—C1 | 131.58 (7) | C7—C8—H8 | 120.2 |
O1—Ni1—C1 | 33.06 (6) | O3—C1—O2 | 123.91 (19) |
N2—Ni1—C1 | 132.02 (7) | O3—C1—O1 | 123.26 (18) |
O2—Ni1—C1 | 32.97 (6) | O2—C1—O1 | 112.82 (17) |
O3i—Ni1—C1 | 95.30 (6) | O3—C1—Ni1 | 175.00 (15) |
C7—N2—C11 | 117.36 (17) | O2—C1—Ni1 | 56.73 (10) |
C7—N2—Ni1 | 125.43 (14) | O1—C1—Ni1 | 56.26 (9) |
C11—N2—Ni1 | 117.16 (13) | C3—C2—N1 | 123.67 (19) |
C7—N3—C6 | 132.66 (17) | C3—C2—H2 | 118.2 |
C7—N3—H3 | 113.7 | N1—C2—H2 | 118.2 |
C6—N3—H3 | 113.7 | C11—C10—C9 | 118.4 (2) |
C1—O1—Ni1 | 90.68 (11) | C11—C10—H10 | 120.8 |
C6—N1—C2 | 117.05 (17) | C9—C10—H10 | 120.8 |
C6—N1—Ni1 | 125.91 (14) | C4—C5—C6 | 119.4 (2) |
C2—N1—Ni1 | 117.03 (13) | C4—C5—H5 | 120.3 |
N1—C6—N3 | 120.88 (18) | C6—C5—H5 | 120.3 |
N1—C6—C5 | 122.10 (19) | C1—O3—Ni1ii | 130.49 (12) |
N3—C6—C5 | 117.02 (18) | H4A—O4—H4B | 110.1 |
C1—O2—Ni1 | 90.29 (12) | H5A—O5—H5B | 109.8 |
N2—C7—N3 | 121.21 (17) | H6A—O6—H6B | 110.2 |
N2—C7—C8 | 121.70 (19) | C5—C4—C3 | 118.9 (2) |
N3—C7—C8 | 117.09 (18) | C5—C4—H4 | 120.5 |
C2—C3—C4 | 118.8 (2) | C3—C4—H4 | 120.5 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O3iii | 0.86 | 1.96 | 2.788 (2) | 161 |
O4—H4A···O5 | 0.83 | 2.00 | 2.823 (3) | 171 |
O4—H4B···O2ii | 0.84 | 1.98 | 2.797 (2) | 165 |
O5—H5A···O6 | 0.82 | 1.97 | 2.754 (3) | 158 |
O5—H5B···O1 | 0.84 | 1.95 | 2.790 (2) | 171 |
O6—H6A···O5iv | 0.83 | 2.12 | 2.934 (2) | 164 |
O6—H6B···O4v | 0.84 | 1.91 | 2.735 (3) | 171 |
Symmetry codes: (ii) −x+2, y−1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(CO3)(C10H9N3)]·3H2O |
Mr | 343.97 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 11.2453 (11), 7.1554 (7), 17.3387 (16) |
β (°) | 101.106 (1) |
V (Å3) | 1369.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.45 |
Crystal size (mm) | 0.20 × 0.19 × 0.18 |
Data collection | |
Diffractometer | Bruker APEX-II area-detector diffractometer |
Absorption correction | Multi-scan SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.760, 0.780 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7073, 2671, 2068 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.063, 0.99 |
No. of reflections | 2671 |
No. of parameters | 190 |
No. of restraints | 9 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.31 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O3i | 0.86 | 1.96 | 2.788 (2) | 161.1 |
O4—H4A···O5 | 0.83 | 2.00 | 2.823 (3) | 171.0 |
O4—H4B···O2ii | 0.84 | 1.98 | 2.797 (2) | 165.3 |
O5—H5A···O6 | 0.82 | 1.97 | 2.754 (3) | 158.4 |
O5—H5B···O1 | 0.84 | 1.95 | 2.790 (2) | 170.8 |
O6—H6A···O5iii | 0.83 | 2.12 | 2.934 (2) | 164.0 |
O6—H6B···O4iv | 0.84 | 1.91 | 2.735 (3) | 171.3 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x, y+1, z. |
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Molecular self-assembly of supramolecular architectures has received much attention during recent decades (Kim et al., 2003; Iglesias et al., 2003; Moulton & Zaworotko, 2001). The structures and properties of such systems depend on the coordination and geometric preferences of both the central metals ions and bridging building blocks as well as the influence of weaker non-covalent interactions, such as hydrogen bonds and π-π stacking interactions. 4-Chlorobenzoic acid and imidazole are excellent candidates for the construction of supramolecular complexes, since they not only have multiple coordination modes but also can form regular hydrogen bonds by functioning as both hydrogen-bond donor and acceptor (Gu et al., 2004). Recently, we obtained the title polymer nickel complex (I) by the reaction of nickel carbonate, bis(2-pyridyl)amine in solution of methanol and acetonitrile.
In complex (I), each NiII centre is coordinated by three O atoms from two carbonate ligands, two N atoms from one bis(2-pyridyl)amine ligand, and displayed a distorted square pyramidal geometry (Fig. 1). The compound forms infinite chain via carbonate ligands bridging the Ni-bis(2-pyridyl)amine units and further linked into a neutral layer through N3—H···O3(carbonate) intermolecular hydrogen bonding interactions (Table 1) and weak slipped π-π stacking with centroid to centroid distance of 3.674 (1)Å and interplanar distance of 3.438\%A between pyridyl group of neighboring chain. The water molecules form infinite lamellar structure containing R55(10) graph set motif (Etter et al., 1990; Bernstein et al., 1995), which fill in the space between the chains and are connected through O—H···O hydrogen bonds with carbonate ligands (Table 1).