The crystal structure of the title compound, [Ni(C20H24N8)]Cl2·2H2O, consists of NiII complex cations, Cl− anions and uncoordinated water molecules. The NiII ion is located on an inversion center and is chelated by two (imidazol-4-ylmethyl)(2-pyridylmethyl)amine (IPA) ligands in a distorted octahedral coordination. The tridentate IPA ligand displays the facial configuration. Hydrogen bonding stabilizes the crystal structure.
Supporting information
CCDC reference: 611241
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.029
- wR factor = 0.085
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
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Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Bis[(imidazol-4-ylmethyl)(2-pyridylmethyl)amine-
κ3N,
N',
N'']nickel(II) dichloride dihydrate
top
Crystal data top
[Ni(C10H12N4)2]Cl2·2H2O | F(000) = 564 |
Mr = 542.12 | Dx = 1.484 Mg m−3 |
Monoclinic, P21/c | Melting point: 252(2)°C decomposed K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7738 (18) Å | Cell parameters from 25 reflections |
b = 19.066 (4) Å | θ = 8.4–12.2° |
c = 7.9456 (16) Å | µ = 1.05 mm−1 |
β = 114.09 (3)° | T = 298 K |
V = 1213.4 (5) Å3 | Prism, purple |
Z = 2 | 0.58 × 0.42 × 0.36 mm |
Data collection top
Rigaku AFC-7S diffractometer | 1928 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 26.0°, θmin = 2.1° |
ω–2θ scans | h = −10→0 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→23 |
Tmin = 0.657, Tmax = 0.689 | l = −8→9 |
2533 measured reflections | 3 standard reflections every 150 reflections |
2381 independent reflections | intensity decay: 0.1% |
Refinement top
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0421P)2 + 0.5253P] where P = (Fo2 + 2Fc2)/3 |
2381 reflections | (Δ/σ)max < 0.001 |
151 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Experimental. The scan width was 1.58 + 0.30tanθ)° with an ω scan speed of 16° per minute
(up to 5 scans to achieve I/σ(I) > 15). Stationary background counts were
recorded at each end of the scan, and the scan time:background time ratio was
2:1. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni | 0.5000 | 0.5000 | 0.5000 | 0.03705 (13) | |
Cl | 0.96725 (8) | 0.35589 (3) | 0.77621 (10) | 0.0633 (2) | |
O1 | 0.1825 (3) | 0.71746 (12) | 0.9600 (3) | 0.0838 (7) | |
H1W | 0.1394 | 0.7591 | 0.9053 | 0.126* | |
H2W | 0.1276 | 0.7078 | 1.0349 | 0.126* | |
N1 | 0.5823 (2) | 0.59898 (9) | 0.4578 (2) | 0.0404 (4) | |
N2 | 0.7471 (2) | 0.49902 (9) | 0.7137 (3) | 0.0439 (4) | |
H2N | 0.7920 | 0.4557 | 0.7184 | 0.053* | |
N3 | 0.4445 (2) | 0.54798 (9) | 0.7013 (3) | 0.0452 (4) | |
N4 | 0.3919 (3) | 0.62518 (11) | 0.8759 (3) | 0.0607 (6) | |
H4N | 0.3387 | 0.6547 | 0.9136 | 0.073* | |
C1 | 0.4888 (3) | 0.65189 (11) | 0.3550 (3) | 0.0467 (5) | |
H1 | 0.3747 | 0.6447 | 0.2899 | 0.056* | |
C2 | 0.5542 (3) | 0.71563 (13) | 0.3425 (4) | 0.0555 (6) | |
H2 | 0.4860 | 0.7505 | 0.2673 | 0.067* | |
C3 | 0.7205 (3) | 0.72778 (13) | 0.4412 (4) | 0.0617 (7) | |
H3 | 0.7674 | 0.7708 | 0.4343 | 0.074* | |
C4 | 0.8165 (3) | 0.67525 (13) | 0.5504 (4) | 0.0564 (6) | |
H4 | 0.9296 | 0.6827 | 0.6211 | 0.068* | |
C5 | 0.7456 (3) | 0.61135 (12) | 0.5555 (3) | 0.0437 (5) | |
C6 | 0.8476 (3) | 0.55058 (13) | 0.6650 (4) | 0.0559 (6) | |
H6A | 0.9001 | 0.5274 | 0.5939 | 0.067* | |
H6B | 0.9354 | 0.5682 | 0.7772 | 0.067* | |
C7 | 0.7361 (3) | 0.51295 (13) | 0.8902 (3) | 0.0541 (6) | |
H7A | 0.8357 | 0.5376 | 0.9717 | 0.065* | |
H7B | 0.7306 | 0.4688 | 0.9482 | 0.065* | |
C8 | 0.5853 (3) | 0.55610 (12) | 0.8630 (3) | 0.0461 (5) | |
C9 | 0.5561 (4) | 0.60332 (14) | 0.9721 (3) | 0.0572 (6) | |
H9 | 0.6304 | 0.6183 | 1.0881 | 0.069* | |
C10 | 0.3315 (3) | 0.59140 (13) | 0.7123 (4) | 0.0529 (6) | |
H10 | 0.2251 | 0.5978 | 0.6200 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni | 0.02828 (19) | 0.0346 (2) | 0.0413 (2) | −0.00179 (14) | 0.00716 (15) | −0.00352 (16) |
Cl | 0.0423 (3) | 0.0526 (4) | 0.0797 (5) | 0.0067 (3) | 0.0094 (3) | −0.0039 (3) |
O1 | 0.0800 (14) | 0.0953 (16) | 0.0796 (14) | 0.0421 (12) | 0.0360 (12) | 0.0278 (12) |
N1 | 0.0326 (9) | 0.0389 (9) | 0.0453 (10) | −0.0032 (7) | 0.0113 (7) | −0.0040 (7) |
N2 | 0.0336 (9) | 0.0366 (9) | 0.0517 (11) | 0.0011 (7) | 0.0074 (8) | −0.0015 (8) |
N3 | 0.0413 (10) | 0.0426 (10) | 0.0469 (10) | −0.0015 (8) | 0.0131 (8) | −0.0030 (8) |
N4 | 0.0745 (15) | 0.0511 (12) | 0.0694 (14) | 0.0041 (11) | 0.0425 (13) | −0.0032 (10) |
C1 | 0.0403 (11) | 0.0422 (12) | 0.0510 (13) | 0.0003 (9) | 0.0118 (10) | −0.0029 (10) |
C2 | 0.0588 (15) | 0.0403 (12) | 0.0627 (15) | 0.0011 (11) | 0.0200 (12) | 0.0005 (11) |
C3 | 0.0627 (16) | 0.0461 (14) | 0.0737 (18) | −0.0126 (12) | 0.0250 (14) | −0.0018 (12) |
C4 | 0.0419 (12) | 0.0546 (14) | 0.0669 (16) | −0.0132 (11) | 0.0164 (11) | −0.0042 (12) |
C5 | 0.0337 (10) | 0.0470 (12) | 0.0474 (12) | −0.0035 (9) | 0.0136 (9) | −0.0031 (10) |
C6 | 0.0312 (11) | 0.0533 (14) | 0.0732 (17) | −0.0014 (10) | 0.0113 (11) | 0.0071 (12) |
C7 | 0.0502 (14) | 0.0492 (14) | 0.0472 (13) | 0.0029 (10) | 0.0040 (11) | 0.0005 (10) |
C8 | 0.0499 (13) | 0.0426 (12) | 0.0399 (11) | −0.0056 (10) | 0.0125 (10) | −0.0011 (9) |
C9 | 0.0665 (16) | 0.0560 (15) | 0.0470 (13) | −0.0063 (12) | 0.0211 (12) | −0.0055 (11) |
C10 | 0.0471 (13) | 0.0540 (14) | 0.0586 (15) | −0.0021 (11) | 0.0226 (11) | 0.0022 (12) |
Geometric parameters (Å, º) top
Ni—N1 | 2.0960 (18) | C1—C2 | 1.365 (3) |
Ni—N1i | 2.0960 (18) | C1—H1 | 0.9300 |
Ni—N2i | 2.140 (2) | C2—C3 | 1.365 (4) |
Ni—N2 | 2.140 (2) | C2—H2 | 0.9300 |
Ni—N3 | 2.0657 (19) | C3—C4 | 1.367 (4) |
Ni—N3i | 2.0657 (19) | C3—H3 | 0.9300 |
O1—H1W | 0.9092 | C4—C5 | 1.376 (3) |
O1—H2W | 0.9242 | C4—H4 | 0.9300 |
N1—C5 | 1.343 (3) | C5—C6 | 1.505 (3) |
N1—C1 | 1.346 (3) | C6—H6A | 0.9700 |
N2—C7 | 1.469 (3) | C6—H6B | 0.9700 |
N2—C6 | 1.474 (3) | C7—C8 | 1.497 (3) |
N2—H2N | 0.9100 | C7—H7A | 0.9700 |
N3—C10 | 1.322 (3) | C7—H7B | 0.9700 |
N3—C8 | 1.380 (3) | C8—C9 | 1.345 (3) |
N4—C10 | 1.350 (3) | C9—H9 | 0.9300 |
N4—C9 | 1.390 (3) | C10—H10 | 0.9300 |
N4—H4N | 0.8600 | | |
| | | |
N1—Ni—N2 | 80.29 (7) | C3—C2—C1 | 119.5 (2) |
N1i—Ni—N2 | 99.71 (7) | C3—C2—H2 | 120.3 |
N3—Ni—N3i | 180.00 (6) | C1—C2—H2 | 120.3 |
N1—Ni—N3 | 86.03 (7) | C2—C3—C4 | 118.5 (2) |
N3i—Ni—N1 | 93.97 (7) | C2—C3—H3 | 120.7 |
N3—Ni—N1i | 93.97 (7) | C4—C3—H3 | 120.7 |
N3i—Ni—N1i | 86.03 (7) | C3—C4—C5 | 119.9 (2) |
N1—Ni—N1i | 180.0 | C3—C4—H4 | 120.1 |
N3—Ni—N2i | 97.34 (7) | C5—C4—H4 | 120.1 |
N3i—Ni—N2i | 82.66 (7) | N1—C5—C4 | 121.8 (2) |
N1—Ni—N2i | 99.71 (7) | N1—C5—C6 | 116.19 (19) |
N1i—Ni—N2i | 80.29 (7) | C4—C5—C6 | 122.0 (2) |
N2—Ni—N3 | 82.66 (7) | N2—C6—C5 | 112.79 (18) |
N3i—Ni—N2 | 97.34 (7) | N2—C6—H6A | 109.0 |
N2i—Ni—N2 | 180.0 | C5—C6—H6A | 109.0 |
H1W—O1—H2W | 105.0 | N2—C6—H6B | 109.0 |
C5—N1—C1 | 117.49 (19) | C5—C6—H6B | 109.0 |
C5—N1—Ni | 114.94 (14) | H6A—C6—H6B | 107.8 |
C1—N1—Ni | 127.41 (14) | N2—C7—C8 | 111.09 (19) |
C7—N2—C6 | 114.17 (19) | N2—C7—H7A | 109.4 |
C7—N2—Ni | 108.44 (14) | C8—C7—H7A | 109.4 |
C6—N2—Ni | 107.86 (14) | N2—C7—H7B | 109.4 |
C7—N2—H2N | 108.8 | C8—C7—H7B | 109.4 |
C6—N2—H2N | 108.8 | H7A—C7—H7B | 108.0 |
Ni—N2—H2N | 108.8 | C9—C8—N3 | 109.9 (2) |
C10—N3—C8 | 106.19 (19) | C9—C8—C7 | 131.7 (2) |
C10—N3—Ni | 138.49 (17) | N3—C8—C7 | 118.4 (2) |
C8—N3—Ni | 111.46 (15) | C8—C9—N4 | 105.9 (2) |
C10—N4—C9 | 107.3 (2) | C8—C9—H9 | 127.1 |
C10—N4—H4N | 126.3 | N4—C9—H9 | 127.1 |
C9—N4—H4N | 126.3 | N3—C10—N4 | 110.6 (2) |
N1—C1—C2 | 122.8 (2) | N3—C10—H10 | 124.7 |
N1—C1—H1 | 118.6 | N4—C10—H10 | 124.7 |
C2—C1—H1 | 118.6 | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1W···Clii | 0.91 | 2.29 | 3.194 (2) | 170 |
O1—H2W···Cliii | 0.92 | 2.33 | 3.213 (3) | 159 |
N2—H2N···Cl | 0.91 | 2.37 | 3.262 (2) | 167 |
N4—H4N···O1 | 0.86 | 1.96 | 2.814 (4) | 170 |
Symmetry codes: (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+2. |