The crystal structure of yellow [Ni(L)(N3)2]·H2O, where L is N,N'-bis[2-(2-pyridyl)ethylene]-1,3-diaminopropane (C15H16N4), containing six-coordinate nickel(II) with an octahedral [NiIIN6] core, is reported. Four N atoms of the Schiff base ligand form the equatorial plane and two N atoms of two azide ligands occupy the axial positions.
Supporting information
CCDC reference: 177186
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.100
- Data-to-parameter ratio = 17.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL, SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL, DENZO (Otwinowski & Minor, 1997) and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.
Crystal data top
[Ni(C15H16N4)(N3)2]·H2O | Dx = 1.509 Mg m−3 |
Mr = 413.10 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 48907 reflections |
a = 13.5783 (3) Å | θ = 3.5–27.9° |
b = 15.2608 (3) Å | µ = 1.10 mm−1 |
c = 17.5449 (4) Å | T = 293 K |
V = 3635.58 (14) Å3 | Block, yellow |
Z = 8 | 0.24 × 0.20 × 0.18 mm |
F(000) = 1712 | |
Data collection top
Nonius KappaCCD diffractometer | 4317 independent reflections |
Radiation source: fine-focus sealed tube | 2828 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 0.76 pixels mm-1 | θmax = 27.9°, θmin = 3.5° |
CCD scans | h = −17→17 |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995, 1997) | k = −20→20 |
Tmin = 0.710, Tmax = 0.821 | l = −23→23 |
48907 measured reflections | |
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)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0425P)2 + 1.9396P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4317 reflections | Δρmax = 0.68 e Å−3 |
252 parameters | Δρmin = −0.37 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0014 (3) |
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 | |
O1 | 0.13664 (16) | 0.12665 (12) | 0.23559 (12) | 0.0652 (6) | |
Ni1 | 0.37530 (2) | 0.002947 (16) | 0.345462 (14) | 0.03204 (11) | |
N1 | 0.38617 (14) | 0.12410 (12) | 0.40560 (11) | 0.0375 (4) | |
N2 | 0.38323 (15) | 0.09055 (13) | 0.25658 (11) | 0.0439 (5) | |
N3 | 0.36859 (14) | −0.10221 (12) | 0.27297 (10) | 0.0374 (4) | |
N4 | 0.36751 (13) | −0.10302 (11) | 0.42495 (10) | 0.0339 (4) | |
N5 | 0.22050 (16) | 0.01497 (14) | 0.35186 (12) | 0.0478 (5) | |
N6 | 0.18588 (16) | 0.01708 (12) | 0.41386 (13) | 0.0450 (5) | |
N7 | 0.1515 (2) | 0.01869 (16) | 0.47386 (16) | 0.0773 (9) | |
N8 | 0.53171 (15) | −0.00650 (12) | 0.35000 (11) | 0.0406 (5) | |
N9 | 0.57131 (15) | −0.07339 (13) | 0.33263 (11) | 0.0400 (5) | |
N10 | 0.61005 (18) | −0.13800 (16) | 0.31629 (16) | 0.0687 (7) | |
C1 | 0.38638 (18) | 0.14266 (15) | 0.47986 (14) | 0.0445 (6) | |
H1 | 0.3846 | 0.0965 | 0.5144 | 0.053* | |
C2 | 0.38913 (19) | 0.22733 (16) | 0.50802 (17) | 0.0540 (7) | |
H2 | 0.3896 | 0.2373 | 0.5603 | 0.065* | |
C3 | 0.3912 (2) | 0.29613 (17) | 0.4582 (2) | 0.0616 (8) | |
H3 | 0.3929 | 0.3535 | 0.4760 | 0.074* | |
C4 | 0.39069 (19) | 0.27898 (16) | 0.38129 (18) | 0.0539 (7) | |
H4 | 0.3916 | 0.3246 | 0.3462 | 0.065* | |
C5 | 0.38876 (17) | 0.19283 (15) | 0.35698 (15) | 0.0432 (6) | |
C6 | 0.38864 (18) | 0.16990 (16) | 0.27580 (16) | 0.0501 (7) | |
H6 | 0.3925 | 0.2135 | 0.2389 | 0.060* | |
C7 | 0.3849 (2) | 0.0673 (2) | 0.17481 (14) | 0.0604 (8) | |
H7A | 0.4219 | 0.1114 | 0.1471 | 0.072* | |
H7B | 0.3180 | 0.0675 | 0.1553 | 0.072* | |
C8 | 0.4307 (3) | −0.0218 (2) | 0.16067 (14) | 0.0664 (9) | |
H8A | 0.4410 | −0.0290 | 0.1063 | 0.080* | |
H8B | 0.4947 | −0.0237 | 0.1852 | 0.080* | |
C9 | 0.3704 (2) | −0.09681 (18) | 0.18903 (13) | 0.0533 (7) | |
H9A | 0.3036 | −0.0907 | 0.1704 | 0.064* | |
H9B | 0.3970 | −0.1510 | 0.1687 | 0.064* | |
C10 | 0.36995 (18) | −0.17618 (15) | 0.30474 (14) | 0.0432 (6) | |
H10 | 0.3725 | −0.2271 | 0.2757 | 0.052* | |
C11 | 0.36742 (16) | −0.18093 (14) | 0.38863 (13) | 0.0367 (5) | |
C12 | 0.36409 (18) | −0.25992 (15) | 0.42595 (15) | 0.0466 (6) | |
H12 | 0.3657 | −0.3122 | 0.3987 | 0.056* | |
C13 | 0.35836 (19) | −0.26074 (16) | 0.50465 (15) | 0.0502 (7) | |
H13 | 0.3553 | −0.3133 | 0.5314 | 0.060* | |
C14 | 0.35738 (18) | −0.18193 (17) | 0.54220 (14) | 0.0483 (6) | |
H14 | 0.3531 | −0.1802 | 0.5951 | 0.058* | |
C15 | 0.36272 (17) | −0.10537 (15) | 0.50095 (13) | 0.0408 (6) | |
H15 | 0.3630 | −0.0525 | 0.5274 | 0.049* | |
H1A | 0.157 (2) | 0.0913 (17) | 0.2764 (13) | 0.092 (8)* | |
H1B | 0.104 (2) | 0.0886 (17) | 0.2024 (14) | 0.092 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0808 (15) | 0.0408 (10) | 0.0740 (14) | −0.0021 (10) | −0.0275 (12) | −0.0039 (10) |
Ni1 | 0.03995 (18) | 0.02971 (16) | 0.02644 (16) | 0.00016 (12) | −0.00010 (11) | 0.00052 (11) |
N1 | 0.0391 (11) | 0.0305 (9) | 0.0430 (11) | 0.0011 (8) | 0.0013 (8) | 0.0015 (8) |
N2 | 0.0485 (13) | 0.0475 (12) | 0.0359 (10) | 0.0042 (9) | 0.0006 (9) | 0.0121 (9) |
N3 | 0.0397 (11) | 0.0453 (11) | 0.0272 (9) | −0.0025 (8) | −0.0012 (8) | −0.0066 (8) |
N4 | 0.0384 (11) | 0.0309 (9) | 0.0324 (9) | −0.0033 (8) | −0.0018 (8) | −0.0016 (8) |
N5 | 0.0431 (12) | 0.0575 (13) | 0.0427 (12) | 0.0044 (10) | −0.0010 (9) | 0.0001 (10) |
N6 | 0.0473 (13) | 0.0307 (10) | 0.0571 (14) | 0.0001 (9) | 0.0060 (10) | 0.0013 (9) |
N7 | 0.103 (2) | 0.0584 (15) | 0.0703 (18) | 0.0037 (14) | 0.0436 (16) | 0.0033 (13) |
N8 | 0.0388 (11) | 0.0382 (11) | 0.0448 (11) | −0.0023 (9) | 0.0006 (9) | −0.0049 (9) |
N9 | 0.0404 (12) | 0.0398 (11) | 0.0397 (11) | −0.0032 (9) | −0.0011 (9) | −0.0007 (9) |
N10 | 0.0653 (17) | 0.0501 (13) | 0.0906 (19) | 0.0124 (12) | 0.0021 (14) | −0.0173 (14) |
C1 | 0.0483 (15) | 0.0368 (12) | 0.0484 (14) | 0.0003 (11) | −0.0015 (11) | −0.0053 (11) |
C2 | 0.0569 (18) | 0.0449 (14) | 0.0603 (17) | 0.0034 (12) | −0.0037 (13) | −0.0144 (13) |
C3 | 0.0616 (19) | 0.0320 (13) | 0.091 (2) | 0.0013 (12) | −0.0014 (16) | −0.0143 (15) |
C4 | 0.0562 (17) | 0.0312 (12) | 0.074 (2) | −0.0002 (11) | 0.0015 (14) | 0.0081 (13) |
C5 | 0.0379 (14) | 0.0336 (11) | 0.0581 (16) | 0.0018 (10) | 0.0019 (11) | 0.0050 (11) |
C6 | 0.0535 (17) | 0.0427 (14) | 0.0542 (15) | 0.0022 (12) | 0.0014 (12) | 0.0195 (12) |
C7 | 0.082 (2) | 0.0660 (18) | 0.0330 (12) | 0.0080 (16) | 0.0003 (13) | 0.0127 (13) |
C8 | 0.073 (2) | 0.092 (2) | 0.0339 (14) | −0.0008 (18) | 0.0028 (13) | −0.0004 (14) |
C9 | 0.0619 (18) | 0.0695 (18) | 0.0285 (12) | −0.0094 (14) | −0.0009 (12) | −0.0107 (12) |
C10 | 0.0512 (15) | 0.0376 (12) | 0.0408 (13) | −0.0057 (11) | −0.0001 (11) | −0.0112 (11) |
C11 | 0.0382 (13) | 0.0313 (11) | 0.0408 (12) | −0.0034 (10) | −0.0024 (10) | −0.0034 (10) |
C12 | 0.0547 (16) | 0.0315 (12) | 0.0536 (15) | −0.0016 (11) | −0.0043 (12) | −0.0016 (11) |
C13 | 0.0599 (18) | 0.0388 (13) | 0.0518 (15) | −0.0051 (12) | −0.0060 (13) | 0.0114 (12) |
C14 | 0.0561 (17) | 0.0532 (14) | 0.0356 (12) | −0.0026 (12) | −0.0043 (11) | 0.0079 (12) |
C15 | 0.0523 (16) | 0.0377 (12) | 0.0325 (11) | −0.0027 (10) | −0.0031 (10) | −0.0034 (10) |
Geometric parameters (Å, º) top
O1—H1A | 0.941 (17) | C3—C4 | 1.375 (4) |
O1—H1B | 0.937 (17) | C3—H3 | 0.9300 |
Ni1—N3 | 2.0497 (18) | C4—C5 | 1.382 (3) |
Ni1—N2 | 2.0569 (18) | C4—H4 | 0.9300 |
Ni1—N5 | 2.113 (2) | C5—C6 | 1.467 (4) |
Ni1—N8 | 2.130 (2) | C6—H6 | 0.9300 |
Ni1—N1 | 2.1339 (18) | C7—C8 | 1.516 (4) |
Ni1—N4 | 2.1380 (18) | C7—H7A | 0.9700 |
N1—C1 | 1.333 (3) | C7—H7B | 0.9700 |
N1—C5 | 1.352 (3) | C8—C9 | 1.492 (4) |
N2—C6 | 1.259 (3) | C8—H8A | 0.9700 |
N2—C7 | 1.478 (3) | C8—H8B | 0.9700 |
N3—C10 | 1.259 (3) | C9—H9A | 0.9700 |
N3—C9 | 1.475 (3) | C9—H9B | 0.9700 |
N4—C15 | 1.335 (3) | C10—C11 | 1.474 (3) |
N4—C11 | 1.349 (3) | C10—H10 | 0.9300 |
N5—N6 | 1.185 (3) | C11—C12 | 1.373 (3) |
N6—N7 | 1.152 (3) | C12—C13 | 1.383 (3) |
N8—N9 | 1.193 (2) | C12—H12 | 0.9300 |
N9—N10 | 1.154 (3) | C13—C14 | 1.371 (4) |
C1—C2 | 1.384 (3) | C13—H13 | 0.9300 |
C1—H1 | 0.9300 | C14—C15 | 1.376 (3) |
C2—C3 | 1.367 (4) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
| | | |
H1A—O1—H1B | 105.2 (19) | C5—C4—H4 | 120.5 |
N3—Ni1—N2 | 92.34 (8) | N1—C5—C4 | 122.9 (3) |
N3—Ni1—N5 | 93.25 (8) | N1—C5—C6 | 115.3 (2) |
N2—Ni1—N5 | 92.06 (8) | C4—C5—C6 | 121.8 (2) |
N3—Ni1—N8 | 90.83 (7) | N2—C6—C5 | 119.3 (2) |
N2—Ni1—N8 | 91.15 (8) | N2—C6—H6 | 120.3 |
N5—Ni1—N8 | 174.70 (8) | C5—C6—H6 | 120.3 |
N3—Ni1—N1 | 171.21 (7) | N2—C7—C8 | 112.3 (2) |
N2—Ni1—N1 | 78.93 (8) | N2—C7—H7A | 109.1 |
N5—Ni1—N1 | 88.13 (8) | C8—C7—H7A | 109.1 |
N8—Ni1—N1 | 88.35 (7) | N2—C7—H7B | 109.1 |
N3—Ni1—N4 | 79.07 (7) | C8—C7—H7B | 109.1 |
N2—Ni1—N4 | 171.39 (7) | H7A—C7—H7B | 107.9 |
N5—Ni1—N4 | 88.96 (7) | C9—C8—C7 | 114.1 (3) |
N8—Ni1—N4 | 88.50 (7) | C9—C8—H8A | 108.7 |
N1—Ni1—N4 | 109.65 (7) | C7—C8—H8A | 108.7 |
C1—N1—C5 | 116.8 (2) | C9—C8—H8B | 108.7 |
C1—N1—Ni1 | 131.86 (16) | C7—C8—H8B | 108.7 |
C5—N1—Ni1 | 111.22 (16) | H8A—C8—H8B | 107.6 |
C6—N2—C7 | 119.3 (2) | N3—C9—C8 | 112.6 (2) |
C6—N2—Ni1 | 115.16 (17) | N3—C9—H9A | 109.1 |
C7—N2—Ni1 | 125.51 (17) | C8—C9—H9A | 109.1 |
C10—N3—C9 | 119.5 (2) | N3—C9—H9B | 109.1 |
C10—N3—Ni1 | 115.25 (15) | C8—C9—H9B | 109.1 |
C9—N3—Ni1 | 125.10 (16) | H9A—C9—H9B | 107.8 |
C15—N4—C11 | 116.61 (19) | N3—C10—C11 | 119.1 (2) |
C15—N4—Ni1 | 132.37 (15) | N3—C10—H10 | 120.5 |
C11—N4—Ni1 | 111.02 (14) | C11—C10—H10 | 120.5 |
N6—N5—Ni1 | 116.46 (17) | N4—C11—C12 | 123.3 (2) |
N7—N6—N5 | 179.4 (3) | N4—C11—C10 | 115.36 (19) |
N9—N8—Ni1 | 119.84 (15) | C12—C11—C10 | 121.4 (2) |
N10—N9—N8 | 179.5 (3) | C11—C12—C13 | 119.1 (2) |
N1—C1—C2 | 123.2 (2) | C11—C12—H12 | 120.5 |
N1—C1—H1 | 118.4 | C13—C12—H12 | 120.5 |
C2—C1—H1 | 118.4 | C14—C13—C12 | 118.2 (2) |
C3—C2—C1 | 119.3 (3) | C14—C13—H13 | 120.9 |
C3—C2—H2 | 120.3 | C12—C13—H13 | 120.9 |
C1—C2—H2 | 120.3 | C13—C14—C15 | 119.4 (2) |
C2—C3—C4 | 118.8 (2) | C13—C14—H14 | 120.3 |
C2—C3—H3 | 120.6 | C15—C14—H14 | 120.3 |
C4—C3—H3 | 120.6 | N4—C15—C14 | 123.4 (2) |
C3—C4—C5 | 119.0 (2) | N4—C15—H15 | 118.3 |
C3—C4—H4 | 120.5 | C14—C15—H15 | 118.3 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N5 | 0.94 (2) | 1.96 (2) | 2.892 (3) | 171 (3) |
O1—H1B···N8i | 0.94 (2) | 1.98 (3) | 2.901 (3) | 169 (2) |
Symmetry code: (i) x−1/2, y, −z+1/2. |