The central NiII ion of the title complex, [Ni(C2N3)2(C10H9N3)2], has an approximate octahedral geometry, coordinated by four N atoms from the pyridine rings of the two bidentate di-2-pyridylamine ligands, and by two terminal N atoms from the two dicyanamide ligands. The coordination octahedron around each nickel ion has C2 symmetry and the two dicyanamide ligands are in cis positions.
Supporting information
CCDC reference: 627650
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.115
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for N5
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C12
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.36
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Bis(dicyanamidato-
κN)(di-2-pyridylamine-
κ2N,
N')nickel(II)
top
Crystal data top
[Ni(C2N3)2(C10H9N3)2] | F(000) = 1096 |
Mr = 533.21 | Dx = 1.402 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5866 reflections |
a = 8.6421 (2) Å | θ = 1.0–26.0° |
b = 13.6999 (3) Å | µ = 0.81 mm−1 |
c = 21.3983 (5) Å | T = 293 K |
β = 94.344 (2)° | Plate, blue |
V = 2526.19 (10) Å3 | 0.30 × 0.30 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker APEX2 CCD diffractometer | 2464 independent reflections |
Radiation source: fine-focus sealed tube | 1661 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −10→10 |
Tmin = 0.794, Tmax = 0.924 | k = −16→16 |
10852 measured reflections | l = −21→26 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0586P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
2464 reflections | Δρmax = 0.28 e Å−3 |
169 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0018 (4) |
Special details top
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 | |
Ni1 | 1.0000 | 0.35998 (4) | 0.7500 | 0.0403 (2) | |
N1 | 1.1183 (3) | 0.46318 (18) | 0.80667 (11) | 0.0445 (6) | |
N2 | 0.8385 (3) | 0.35883 (19) | 0.81968 (11) | 0.0471 (7) | |
N3 | 1.0315 (3) | 0.39776 (19) | 0.90005 (11) | 0.0496 (7) | |
H3B | 1.0664 | 0.3779 | 0.9365 | 0.060* | |
N4 | 0.8737 (3) | 0.2526 (2) | 0.69866 (11) | 0.0503 (7) | |
N5 | 0.7452 (5) | 0.1239 (2) | 0.63669 (16) | 0.0918 (12) | |
N6 | 0.6141 (4) | 0.1239 (3) | 0.53344 (15) | 0.0965 (12) | |
C1 | 1.1316 (3) | 0.4559 (2) | 0.86931 (14) | 0.0453 (8) | |
C2 | 1.2459 (4) | 0.5053 (3) | 0.90622 (15) | 0.0607 (10) | |
H2A | 1.2561 | 0.4958 | 0.9494 | 0.073* | |
C3 | 1.3416 (4) | 0.5668 (3) | 0.87883 (18) | 0.0793 (12) | |
H3A | 1.4182 | 0.6004 | 0.9030 | 0.095* | |
C4 | 1.3257 (4) | 0.5799 (3) | 0.81448 (18) | 0.0753 (12) | |
H4A | 1.3892 | 0.6231 | 0.7947 | 0.090* | |
C5 | 1.2133 (4) | 0.5272 (2) | 0.78100 (16) | 0.0612 (10) | |
H5A | 1.2017 | 0.5362 | 0.7378 | 0.073* | |
C6 | 0.8836 (3) | 0.3668 (2) | 0.88092 (14) | 0.0475 (8) | |
C7 | 0.7845 (4) | 0.3452 (3) | 0.92738 (16) | 0.0647 (10) | |
H7A | 0.8201 | 0.3489 | 0.9694 | 0.078* | |
C8 | 0.6349 (4) | 0.3185 (3) | 0.91097 (18) | 0.0855 (14) | |
H8A | 0.5674 | 0.3033 | 0.9414 | 0.103* | |
C9 | 0.5862 (4) | 0.3147 (4) | 0.84832 (18) | 0.0863 (14) | |
H9A | 0.4838 | 0.2993 | 0.8357 | 0.104* | |
C10 | 0.6892 (4) | 0.3337 (3) | 0.80516 (16) | 0.0675 (11) | |
H10A | 0.6548 | 0.3292 | 0.7630 | 0.081* | |
C11 | 0.8125 (4) | 0.1969 (3) | 0.66606 (15) | 0.0496 (8) | |
C12 | 0.6804 (4) | 0.1296 (3) | 0.58041 (17) | 0.0580 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0462 (3) | 0.0454 (4) | 0.0278 (3) | 0.000 | −0.0072 (2) | 0.000 |
N1 | 0.0566 (14) | 0.0453 (17) | 0.0306 (15) | −0.0088 (13) | −0.0038 (11) | 0.0036 (12) |
N2 | 0.0475 (13) | 0.0619 (18) | 0.0303 (14) | −0.0059 (13) | −0.0073 (11) | −0.0008 (13) |
N3 | 0.0588 (15) | 0.0651 (19) | 0.0234 (14) | −0.0124 (14) | −0.0073 (11) | 0.0045 (12) |
N4 | 0.0601 (15) | 0.0522 (18) | 0.0364 (16) | −0.0044 (13) | −0.0111 (12) | −0.0007 (14) |
N5 | 0.144 (3) | 0.062 (2) | 0.061 (2) | −0.020 (2) | −0.047 (2) | 0.0005 (17) |
N6 | 0.116 (3) | 0.124 (3) | 0.045 (2) | −0.007 (2) | −0.025 (2) | −0.0164 (19) |
C1 | 0.0531 (17) | 0.052 (2) | 0.0300 (18) | −0.0067 (15) | −0.0032 (13) | −0.0017 (15) |
C2 | 0.069 (2) | 0.072 (3) | 0.038 (2) | −0.0235 (19) | −0.0105 (16) | −0.0016 (18) |
C3 | 0.083 (2) | 0.093 (3) | 0.059 (3) | −0.038 (2) | −0.016 (2) | −0.004 (2) |
C4 | 0.089 (3) | 0.080 (3) | 0.056 (3) | −0.037 (2) | −0.003 (2) | 0.006 (2) |
C5 | 0.083 (2) | 0.055 (2) | 0.044 (2) | −0.017 (2) | −0.0037 (17) | 0.0087 (18) |
C6 | 0.0551 (17) | 0.054 (2) | 0.0329 (18) | −0.0037 (16) | 0.0000 (14) | 0.0029 (16) |
C7 | 0.071 (2) | 0.089 (3) | 0.035 (2) | −0.013 (2) | 0.0064 (16) | 0.0029 (18) |
C8 | 0.068 (2) | 0.136 (4) | 0.053 (3) | −0.023 (3) | 0.0125 (19) | 0.008 (3) |
C9 | 0.052 (2) | 0.142 (4) | 0.064 (3) | −0.025 (2) | 0.0001 (19) | 0.003 (3) |
C10 | 0.0547 (19) | 0.103 (3) | 0.044 (2) | −0.015 (2) | −0.0080 (16) | 0.000 (2) |
C11 | 0.0587 (19) | 0.049 (2) | 0.0385 (19) | 0.0042 (17) | −0.0115 (15) | 0.0045 (17) |
C12 | 0.065 (2) | 0.064 (3) | 0.044 (2) | 0.0016 (18) | −0.0048 (17) | −0.0086 (18) |
Geometric parameters (Å, º) top
Ni1—N1 | 2.080 (2) | C1—C2 | 1.393 (4) |
Ni1—N1i | 2.080 (2) | C2—C3 | 1.346 (5) |
Ni1—N4 | 2.093 (3) | C2—H2A | 0.9300 |
Ni1—N4i | 2.093 (3) | C3—C4 | 1.385 (5) |
Ni1—N2i | 2.118 (2) | C3—H3A | 0.9300 |
Ni1—N2 | 2.118 (2) | C4—C5 | 1.368 (4) |
N1—C1 | 1.340 (3) | C4—H4A | 0.9300 |
N1—C5 | 1.347 (4) | C5—H5A | 0.9300 |
N2—C6 | 1.343 (4) | C6—C7 | 1.393 (4) |
N2—C10 | 1.349 (4) | C7—C8 | 1.364 (5) |
N3—C6 | 1.379 (4) | C7—H7A | 0.9300 |
N3—C1 | 1.379 (4) | C8—C9 | 1.375 (5) |
N3—H3B | 0.8600 | C8—H8A | 0.9300 |
N4—C11 | 1.137 (4) | C9—C10 | 1.355 (5) |
N5—C12 | 1.291 (4) | C9—H9A | 0.9300 |
N5—C11 | 1.295 (4) | C10—H10A | 0.9300 |
N6—C12 | 1.121 (4) | | |
| | | |
N1—Ni1—N1i | 94.35 (14) | C3—C2—C1 | 119.4 (3) |
N1—Ni1—N4 | 175.91 (9) | C3—C2—H2A | 120.3 |
N1i—Ni1—N4 | 87.60 (10) | C1—C2—H2A | 120.3 |
N1—Ni1—N4i | 87.60 (10) | C2—C3—C4 | 119.7 (3) |
N1i—Ni1—N4i | 175.91 (9) | C2—C3—H3A | 120.1 |
N4—Ni1—N4i | 90.68 (14) | C4—C3—H3A | 120.1 |
N1—Ni1—N2i | 95.43 (10) | C5—C4—C3 | 117.7 (3) |
N1i—Ni1—N2i | 85.15 (9) | C5—C4—H4A | 121.1 |
N4—Ni1—N2i | 88.31 (10) | C3—C4—H4A | 121.1 |
N4i—Ni1—N2i | 91.10 (9) | N1—C5—C4 | 124.1 (3) |
N1—Ni1—N2 | 85.15 (9) | N1—C5—H5A | 117.9 |
N1i—Ni1—N2 | 95.43 (10) | C4—C5—H5A | 117.9 |
N4—Ni1—N2 | 91.10 (9) | N2—C6—N3 | 120.6 (3) |
N4i—Ni1—N2 | 88.31 (10) | N2—C6—C7 | 122.0 (3) |
N2i—Ni1—N2 | 179.15 (15) | N3—C6—C7 | 117.4 (3) |
C1—N1—C5 | 116.6 (3) | C8—C7—C6 | 119.7 (3) |
C1—N1—Ni1 | 122.2 (2) | C8—C7—H7A | 120.1 |
C5—N1—Ni1 | 119.5 (2) | C6—C7—H7A | 120.1 |
C6—N2—C10 | 116.6 (3) | C7—C8—C9 | 118.4 (3) |
C6—N2—Ni1 | 121.90 (19) | C7—C8—H8A | 120.8 |
C10—N2—Ni1 | 120.6 (2) | C9—C8—H8A | 120.8 |
C6—N3—C1 | 129.5 (2) | C10—C9—C8 | 119.3 (3) |
C6—N3—H3B | 115.2 | C10—C9—H9A | 120.4 |
C1—N3—H3B | 115.2 | C8—C9—H9A | 120.4 |
C11—N4—Ni1 | 173.5 (3) | N2—C10—C9 | 123.9 (3) |
C12—N5—C11 | 123.6 (3) | N2—C10—H10A | 118.0 |
N1—C1—N3 | 120.7 (3) | C9—C10—H10A | 118.0 |
N1—C1—C2 | 122.3 (3) | N4—C11—N5 | 170.7 (4) |
N3—C1—C2 | 117.0 (3) | N6—C12—N5 | 171.1 (4) |
Symmetry code: (i) −x+2, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···N6ii | 0.86 | 2.08 | 2.905 (4) | 160 |
Symmetry code: (ii) x+1/2, −y+1/2, z+1/2. |