Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016264/ya6136sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016264/ya6136Isup2.hkl |
CCDC reference: 198302
A mixture of nickel sulfate (1 mmol, 0.23 g), 1,10-phenanthroline (2 mmol, 0.36 g) and sodium azide (2 mmol, 0.13 g) in 50 ml of a water-ethanol mixture (1:2 v:v) was stirred for several hours at room temperature. The mixture was filtered; dark green crystals separated from the solution after a week.
The hydrogen atoms were positioned geometrically, and were allowed to ride on their parent carbon atoms, with U(H) = 1.2eq(C).
Data collection: XSCANS (Siemens, 1990); cell refinement: Siemens software PLEASE SPECIFY (Siemens, 1990); data reduction: Siemens software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C24H16N10Ni | Z = 2 |
Mr = 503.18 | F(000) = 516 |
Triclinic, P1 | Dx = 1.587 Mg m−3 |
a = 8.200 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.002 (2) Å | Cell parameters from 30 reflections |
c = 12.408 (2) Å | θ = 3.0–14.4° |
α = 82.28 (2)° | µ = 0.96 mm−1 |
β = 82.26 (2)° | T = 298 K |
γ = 72.57 (1)° | Prism, green |
V = 1053.0 (3) Å3 | 0.48 × 0.34 × 0.30 mm |
Siemens P4 four-circle diffractometer | 3277 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.012 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ω scan | h = 0→9 |
Absorption correction: empirical ψ scan (North et al., 1968) | k = −12→13 |
Tmin = 0.656, Tmax = 0.762 | l = −14→14 |
3984 measured reflections | 3 standard reflections every 97 reflections |
3697 independent reflections | intensity decay: 2.6% |
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) = 0.072 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0404P)2 + 0.2944P] where P = (Fo2 + 2Fc2)/3 |
3697 reflections | (Δ/σ)max < 0.001 |
316 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C24H16N10Ni | γ = 72.57 (1)° |
Mr = 503.18 | V = 1053.0 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.200 (1) Å | Mo Kα radiation |
b = 11.002 (2) Å | µ = 0.96 mm−1 |
c = 12.408 (2) Å | T = 298 K |
α = 82.28 (2)° | 0.48 × 0.34 × 0.30 mm |
β = 82.26 (2)° |
Siemens P4 four-circle diffractometer | 3277 reflections with I > 2σ(I) |
Absorption correction: empirical ψ scan (North et al., 1968) | Rint = 0.012 |
Tmin = 0.656, Tmax = 0.762 | 3 standard reflections every 97 reflections |
3984 measured reflections | intensity decay: 2.6% |
3697 independent reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.24 e Å−3 |
3697 reflections | Δρmin = −0.30 e Å−3 |
316 parameters |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.48265 (3) | 0.28823 (2) | 0.23492 (2) | 0.0271 (1) | |
N1 | 0.6351 (3) | 0.4097 (2) | 0.1853 (2) | 0.0427 (4) | |
N2 | 0.7839 (3) | 0.3741 (2) | 0.1600 (2) | 0.0479 (5) | |
N3 | 0.9284 (4) | 0.3436 (3) | 0.1339 (3) | 0.115 (1) | |
N4 | 0.6984 (2) | 0.1301 (2) | 0.2538 (2) | 0.0433 (5) | |
N5 | 0.7032 (2) | 0.0339 (2) | 0.3089 (1) | 0.0372 (4) | |
N6 | 0.7137 (3) | −0.0632 (2) | 0.3617 (2) | 0.0674 (7) | |
N7 | 0.4621 (2) | 0.2553 (2) | 0.0767 (1) | 0.0300 (4) | |
N8 | 0.3272 (2) | 0.1624 (2) | 0.2659 (1) | 0.0310 (4) | |
N9 | 0.4475 (2) | 0.3285 (2) | 0.3981 (1) | 0.0299 (4) | |
N10 | 0.2663 (2) | 0.4518 (2) | 0.2317 (1) | 0.0302 (4) | |
C1 | 0.5289 (3) | 0.3040 (2) | −0.0164 (2) | 0.0380 (5) | |
C2 | 0.5069 (3) | 0.2752 (2) | −0.1182 (2) | 0.0429 (5) | |
C3 | 0.4149 (3) | 0.1918 (2) | −0.1245 (2) | 0.0414 (5) | |
C4 | 0.3404 (3) | 0.1390 (2) | −0.0278 (2) | 0.0356 (5) | |
C5 | 0.2423 (3) | 0.0502 (2) | −0.0249 (2) | 0.0450 (6) | |
C6 | 0.1745 (3) | 0.0035 (2) | 0.0712 (2) | 0.0468 (6) | |
C7 | 0.1976 (3) | 0.0389 (2) | 0.1735 (2) | 0.0375 (5) | |
C8 | 0.1328 (3) | −0.0081 (2) | 0.2757 (2) | 0.0486 (6) | |
C9 | 0.1687 (3) | 0.0279 (2) | 0.3686 (2) | 0.0487 (6) | |
C10 | 0.2668 (3) | 0.1128 (2) | 0.3609 (2) | 0.0391 (5) | |
C11 | 0.2949 (2) | 0.1247 (2) | 0.1735 (2) | 0.0298 (4) | |
C12 | 0.3677 (2) | 0.1747 (2) | 0.0713 (2) | 0.0290 (4) | |
C13 | 0.5355 (3) | 0.2639 (2) | 0.4804 (2) | 0.0367 (5) | |
C14 | 0.5008 (3) | 0.3021 (2) | 0.5854 (2) | 0.0414 (5) | |
C15 | 0.3731 (3) | 0.4108 (2) | 0.6069 (2) | 0.0417 (5) | |
C16 | 0.2767 (3) | 0.4818 (2) | 0.5221 (2) | 0.0357 (5) | |
C17 | 0.1401 (3) | 0.5981 (2) | 0.5356 (2) | 0.0456 (6) | |
C18 | 0.0521 (3) | 0.6621 (2) | 0.4509 (2) | 0.0452 (6) | |
C19 | 0.0901 (3) | 0.6159 (2) | 0.3448 (2) | 0.0368 (5) | |
C20 | −0.0007 (3) | 0.6767 (2) | 0.2549 (2) | 0.0468 (6) | |
C21 | 0.0425 (3) | 0.6250 (2) | 0.1579 (2) | 0.0481 (6) | |
C22 | 0.1768 (3) | 0.5117 (2) | 0.1493 (2) | 0.0393 (5) | |
C23 | 0.2230 (2) | 0.5031 (2) | 0.3289 (2) | 0.0299 (4) | |
C24 | 0.3186 (2) | 0.4359 (2) | 0.4187 (2) | 0.0296 (4) | |
H1 | 0.5933 | 0.3599 | −0.0133 | 0.046* | |
H2 | 0.5544 | 0.3125 | −0.1816 | 0.051* | |
H3 | 0.4016 | 0.1701 | −0.1920 | 0.050* | |
H5 | 0.2253 | 0.0245 | −0.0899 | 0.054* | |
H6 | 0.1107 | −0.0535 | 0.0708 | 0.056* | |
H8 | 0.0654 | −0.0635 | 0.2801 | 0.058* | |
H9 | 0.1279 | −0.0041 | 0.4367 | 0.058* | |
H10 | 0.2911 | 0.1358 | 0.4250 | 0.047* | |
H13 | 0.6241 | 0.1900 | 0.4672 | 0.044* | |
H14 | 0.5646 | 0.2535 | 0.6409 | 0.050* | |
H15 | 0.3502 | 0.4377 | 0.6768 | 0.050* | |
H17 | 0.1120 | 0.6297 | 0.6036 | 0.055* | |
H18 | −0.0348 | 0.7376 | 0.4615 | 0.054* | |
H20 | −0.0898 | 0.7519 | 0.2616 | 0.056* | |
H21 | −0.0166 | 0.6645 | 0.0977 | 0.058* | |
H22 | 0.2043 | 0.4769 | 0.0826 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0306 (2) | 0.0245 (1) | 0.0242 (1) | −0.0047 (1) | −0.0017 (1) | −0.0041 (1) |
N1 | 0.045 (1) | 0.034 (1) | 0.050 (1) | −0.013 (1) | 0.000 (1) | −0.005 (1) |
N2 | 0.045 (1) | 0.044 (1) | 0.058 (1) | −0.018 (1) | −0.005 (1) | −0.003 (1) |
N3 | 0.045 (2) | 0.091 (2) | 0.199 (4) | −0.022 (2) | 0.016 (2) | 0.001 (2) |
N4 | 0.039 (1) | 0.033 (1) | 0.050 (1) | −0.002 (1) | −0.001 (1) | 0.002 (1) |
N5 | 0.035 (1) | 0.034 (1) | 0.037 (1) | 0.000 (1) | −0.002 (1) | −0.010 (1) |
N6 | 0.077 (2) | 0.038 (1) | 0.066 (2) | 0.002 (1) | 0.006 (1) | 0.012 (1) |
N7 | 0.035 (1) | 0.026 (1) | 0.027 (1) | −0.005 (1) | −0.002 (1) | −0.003 (1) |
N8 | 0.031 (1) | 0.030 (1) | 0.029 (1) | −0.005 (1) | 0.000 (1) | −0.004 (1) |
N9 | 0.035 (1) | 0.027 (1) | 0.027 (1) | −0.006 (1) | −0.003 (1) | −0.006 (1) |
N10 | 0.031 (1) | 0.028 (1) | 0.030 (1) | −0.006 (1) | −0.003 (1) | −0.004 (1) |
C1 | 0.050 (1) | 0.035 (1) | 0.029 (1) | −0.013 (1) | −0.001 (1) | −0.001 (1) |
C2 | 0.053 (1) | 0.045 (1) | 0.027 (1) | −0.009 (1) | −0.002 (1) | 0.001 (1) |
C3 | 0.044 (1) | 0.047 (1) | 0.028 (1) | 0.002 (1) | −0.012 (1) | −0.009 (1) |
C4 | 0.032 (1) | 0.034 (1) | 0.037 (1) | 0.002 (1) | −0.013 (1) | −0.008 (1) |
C5 | 0.040 (1) | 0.048 (1) | 0.051 (1) | −0.006 (1) | −0.020 (1) | −0.016 (1) |
C6 | 0.036 (1) | 0.042 (1) | 0.068 (2) | −0.013 (1) | −0.016 (1) | −0.011 (1) |
C7 | 0.026 (1) | 0.034 (1) | 0.052 (1) | −0.006 (1) | −0.006 (1) | −0.004 (1) |
C8 | 0.033 (1) | 0.043 (1) | 0.070 (2) | −0.017 (1) | −0.001 (1) | 0.001 (1) |
C9 | 0.042 (1) | 0.052 (1) | 0.047 (1) | −0.016 (1) | 0.011 (1) | 0.004 (1) |
C10 | 0.037 (1) | 0.041 (1) | 0.035 (1) | −0.009 (1) | 0.006 (1) | −0.003 (1) |
C11 | 0.023 (1) | 0.026 (1) | 0.036 (1) | −0.001 (1) | −0.004 (1) | −0.003 (1) |
C12 | 0.027 (1) | 0.026 (1) | 0.030 (1) | −0.001 (1) | −0.006 (1) | −0.004 (1) |
C13 | 0.042 (1) | 0.035 (1) | 0.032 (1) | −0.007 (1) | −0.007 (1) | −0.005 (1) |
C14 | 0.053 (1) | 0.046 (1) | 0.028 (1) | −0.018 (1) | −0.008 (1) | −0.002 (1) |
C15 | 0.053 (1) | 0.050 (1) | 0.027 (1) | −0.024 (1) | 0.004 (1) | −0.012 (1) |
C16 | 0.040 (1) | 0.037 (1) | 0.034 (1) | −0.018 (1) | 0.006 (1) | −0.010 (1) |
C17 | 0.047 (1) | 0.045 (1) | 0.046 (1) | −0.014 (1) | 0.013 (1) | −0.022 (1) |
C18 | 0.039 (1) | 0.035 (1) | 0.058 (2) | −0.005 (1) | 0.010 (1) | −0.018 (1) |
C19 | 0.030 (1) | 0.030 (1) | 0.048 (1) | −0.007 (1) | 0.003 (1) | −0.008 (1) |
C20 | 0.035 (1) | 0.032 (1) | 0.066 (2) | 0.002 (1) | −0.006 (1) | −0.005 (1) |
C21 | 0.042 (1) | 0.043 (1) | 0.054 (1) | 0.000 (1) | −0.016 (1) | 0.001 (1) |
C22 | 0.038 (1) | 0.037 (1) | 0.039 (1) | −0.004 (1) | −0.008 (1) | −0.003 (1) |
C23 | 0.028 (1) | 0.027 (1) | 0.035 (1) | −0.009 (1) | 0.003 (1) | −0.005 (1) |
C24 | 0.032 (1) | 0.029 (1) | 0.030 (1) | −0.012 (1) | 0.003 (1) | −0.006 (1) |
Ni1—N1 | 2.073 (2) | C11—C12 | 1.439 (3) |
Ni1—N4 | 2.091 (2) | C13—C14 | 1.389 (3) |
Ni1—N7 | 2.081 (2) | C14—C15 | 1.364 (3) |
Ni1—N8 | 2.115 (2) | C15—C16 | 1.405 (3) |
Ni1—N9 | 2.094 (2) | C16—C24 | 1.404 (3) |
Ni1—N10 | 2.115 (2) | C16—C17 | 1.439 (3) |
N1—N2 | 1.177 (3) | C17—C18 | 1.349 (3) |
N2—N3 | 1.144 (3) | C18—C19 | 1.436 (3) |
N4—N5 | 1.174 (3) | C19—C23 | 1.402 (3) |
N5—N6 | 1.162 (3) | C19—C20 | 1.405 (3) |
N7—C1 | 1.326 (3) | C20—C21 | 1.359 (3) |
N7—C12 | 1.353 (3) | C21—C22 | 1.400 (3) |
N8—C10 | 1.328 (3) | C23—C24 | 1.439 (3) |
N8—C11 | 1.354 (3) | C1—H1 | 0.9300 |
N9—C13 | 1.329 (3) | C2—H2 | 0.9300 |
N9—C24 | 1.356 (2) | C3—H3 | 0.9300 |
N10—C22 | 1.323 (3) | C5—H5 | 0.9300 |
N10—C23 | 1.359 (2) | C6—H6 | 0.9300 |
C1—C2 | 1.391 (3) | C8—H8 | 0.9300 |
C2—C3 | 1.366 (3) | C9—H9 | 0.9300 |
C3—C4 | 1.406 (3) | C10—H10 | 0.9300 |
C4—C12 | 1.404 (3) | C13—H13 | 0.9300 |
C4—C5 | 1.434 (3) | C14—H14 | 0.9300 |
C5—C6 | 1.350 (3) | C15—H15 | 0.9300 |
C6—C7 | 1.427 (3) | C17—H17 | 0.9300 |
C7—C8 | 1.402 (3) | C18—H18 | 0.9300 |
C7—C11 | 1.407 (3) | C20—H20 | 0.9300 |
C8—C9 | 1.362 (3) | C21—H21 | 0.9300 |
C9—C10 | 1.390 (3) | C22—H22 | 0.9300 |
N1—Ni1—N4 | 91.6 (1) | C15—C14—C13 | 119.9 (2) |
N1—Ni1—N7 | 94.3 (1) | C14—C15—C16 | 119.1 (2) |
N1—Ni1—N8 | 173.3 (1) | C15—C16—C24 | 117.4 (2) |
N1—Ni1—N9 | 93.6 (1) | C15—C16—C17 | 123.7 (2) |
N1—Ni1—N10 | 87.9 (1) | C24—C16—C17 | 118.9 (2) |
N4—Ni1—N7 | 93.4 (1) | C18—C17—C16 | 121.0 (2) |
N4—Ni1—N8 | 88.8 (1) | C17—C18—C19 | 121.3 (2) |
N4—Ni1—N9 | 95.3 (1) | C23—C19—C20 | 117.2 (2) |
N4—Ni1—N10 | 174.3 (1) | C23—C19—C18 | 119.1 (2) |
N7—Ni1—N8 | 78.9 (1) | C20—C19—C18 | 123.6 (2) |
N7—Ni1—N9 | 168.0 (1) | C21—C20—C19 | 119.5 (2) |
N7—Ni1—N10 | 92.3 (1) | C20—C21—C22 | 119.4 (2) |
N8—Ni1—N9 | 93.0 (1) | N10—C22—C21 | 123.0 (2) |
N8—Ni1—N10 | 92.3 (1) | N10—C23—C19 | 123.1 (2) |
N9—Ni1—N10 | 79.0 (1) | N10—C23—C24 | 117.3 (2) |
N2—N1—Ni1 | 123.9 (1) | C19—C23—C24 | 119.6 (2) |
N1—N2—N3 | 177.8 (3) | N9—C24—C16 | 122.9 (2) |
N5—N4—Ni1 | 126.6 (2) | N9—C24—C23 | 117.0 (2) |
N4—N5—N6 | 177.6 (2) | C16—C24—C23 | 120.1 (2) |
C1—N7—C12 | 118.1 (2) | N7—C1—H1 | 118.5 |
C1—N7—Ni1 | 127.8 (1) | C2—C1—H1 | 118.5 |
C12—N7—Ni1 | 114.2 (1) | C3—C2—H2 | 120.3 |
C10—N8—C11 | 117.8 (2) | C1—C2—H2 | 120.3 |
C10—N8—Ni1 | 129.3 (2) | C2—C3—H3 | 120.3 |
C11—N8—Ni1 | 112.9 (1) | C4—C3—H3 | 120.3 |
C13—N9—C24 | 117.9 (2) | C6—C5—H5 | 119.7 |
C13—N9—Ni1 | 128.4 (1) | C4—C5—H5 | 119.7 |
C24—N9—Ni1 | 113.7 (1) | C5—C6—H6 | 119.0 |
C22—N10—C23 | 117.7 (2) | C7—C6—H6 | 119.0 |
C22—N10—Ni1 | 129.5 (1) | C9—C8—H8 | 120.1 |
C23—N10—Ni1 | 112.7 (1) | C7—C8—H8 | 120.1 |
N7—C1—C2 | 122.9 (2) | C8—C9—H9 | 120.2 |
C3—C2—C1 | 119.5 (2) | C10—C9—H9 | 120.2 |
C2—C3—C4 | 119.4 (2) | N8—C10—H10 | 118.6 |
C3—C4—C12 | 117.2 (2) | C9—C10—H10 | 118.6 |
C3—C4—C5 | 123.9 (2) | N9—C13—H13 | 118.6 |
C12—C4—C5 | 118.8 (2) | C14—C13—H13 | 118.6 |
C6—C5—C4 | 120.7 (2) | C15—C14—H14 | 120.0 |
C5—C6—C7 | 122.1 (2) | C13—C14—H14 | 120.0 |
C8—C7—C11 | 116.8 (2) | C14—C15—H15 | 120.5 |
C8—C7—C6 | 124.6 (2) | C16—C15—H15 | 120.5 |
C11—C7—C6 | 118.6 (2) | C18—C17—H17 | 119.5 |
C9—C8—C7 | 119.7 (2) | C16—C17—H17 | 119.5 |
C8—C9—C10 | 119.6 (2) | C17—C18—H18 | 119.3 |
N8—C10—C9 | 122.8 (2) | C19—C18—H18 | 119.3 |
N8—C11—C7 | 123.3 (2) | C21—C20—H20 | 120.2 |
N8—C11—C12 | 117.1 (2) | C19—C20—H20 | 120.2 |
C7—C11—C12 | 119.6 (2) | C20—C21—H21 | 120.3 |
N7—C12—C4 | 122.9 (2) | C22—C21—H21 | 120.3 |
N7—C12—C11 | 116.9 (2) | N10—C22—H22 | 118.5 |
C4—C12—C11 | 120.2 (2) | C21—C22—H22 | 118.5 |
N9—C13—C14 | 122.8 (2) | ||
N7—Ni1—N1—N2 | −80.2 (2) | Ni1—N8—C10—C9 | −178.3 (2) |
N4—Ni1—N1—N2 | 13.4 (2) | C8—C9—C10—N8 | 0.6 (3) |
N9—Ni1—N1—N2 | 108.8 (2) | C10—N8—C11—C7 | 1.7 (3) |
N10—Ni1—N1—N2 | −172.3 (2) | Ni1—N8—C11—C7 | 178.6 (2) |
N1—Ni1—N4—N5 | 157.5 (2) | C10—N8—C11—C12 | −177.3 (2) |
N7—Ni1—N4—N5 | −108.1 (2) | Ni1—N8—C11—C12 | −0.4 (2) |
N9—Ni1—N4—N5 | 63.7 (2) | C8—C7—C11—N8 | 0.0 (3) |
N8—Ni1—N4—N5 | −29.2 (2) | C6—C7—C11—N8 | −178.7 (2) |
N1—Ni1—N7—C1 | −0.9 (2) | C8—C7—C11—C12 | 178.9 (2) |
N4—Ni1—N7—C1 | −92.8 (2) | C6—C7—C11—C12 | 0.2 (3) |
N9—Ni1—N7—C1 | 130.5 (3) | C1—N7—C12—C4 | 1.2 (3) |
N8—Ni1—N7—C1 | 179.1 (2) | Ni1—N7—C12—C4 | −179.2 (1) |
N10—Ni1—N7—C1 | 87.2 (2) | C1—N7—C12—C11 | −179.2 (2) |
N1—Ni1—N7—C12 | 179.5 (1) | Ni1—N7—C12—C11 | 0.5 (2) |
N4—Ni1—N7—C12 | 87.6 (1) | C3—C4—C12—N7 | −0.6 (3) |
N9—Ni1—N7—C12 | −49.1 (3) | C5—C4—C12—N7 | 178.3 (2) |
N8—Ni1—N7—C12 | −0.5 (1) | C3—C4—C12—C11 | 179.8 (2) |
N10—Ni1—N7—C12 | −92.4 (1) | C5—C4—C12—C11 | −1.3 (3) |
N7—Ni1—N8—C10 | 176.9 (2) | N8—C11—C12—N7 | −0.1 (3) |
N4—Ni1—N8—C10 | 83.2 (2) | C7—C11—C12—N7 | −179.1 (2) |
N9—Ni1—N8—C10 | −12.1 (1) | N8—C11—C12—C4 | 179.6 (2) |
N10—Ni1—N8—C10 | −91.2 (2) | C7—C11—C12—C4 | 0.6 (3) |
N7—Ni1—N8—C11 | 0.5 (1) | C24—N9—C13—C14 | −0.1 (3) |
N4—Ni1—N8—C11 | −93.3 (1) | Ni1—N9—C13—C14 | 179.0 (2) |
N9—Ni1—N8—C11 | 171.5 (1) | N9—C13—C14—C15 | −0.8 (3) |
N10—Ni1—N8—C11 | 92.4 (1) | C13—C14—C15—C16 | 0.9 (3) |
N1—Ni1—N9—C13 | −95.1 (2) | C14—C15—C16—C24 | −0.2 (3) |
N7—Ni1—N9—C13 | 133.4 (3) | C14—C15—C16—C17 | −179.6 (2) |
N4—Ni1—N9—C13 | −3.2 (2) | C15—C16—C17—C18 | 180.0 (2) |
N8—Ni1—N9—C13 | 85.9 (2) | C24—C16—C17—C18 | 0.5 (3) |
N10—Ni1—N9—C13 | 177.7 (2) | C16—C17—C18—C19 | 0.7 (4) |
N1—Ni1—N9—C24 | 84.0 (1) | C17—C18—C19—C23 | −1.0 (3) |
N7—Ni1—N9—C24 | −47.4 (4) | C17—C18—C19—C20 | 178.1 (2) |
N4—Ni1—N9—C24 | 176.0 (1) | C23—C19—C20—C21 | 0.1 (3) |
N8—Ni1—N9—C24 | −95.0 (1) | C18—C19—C20—C21 | −179.0 (2) |
N10—Ni1—N9—C24 | −3.2 (1) | C19—C20—C21—C22 | 0.1 (4) |
N1—Ni1—N10—C22 | 86.4 (2) | C23—N10—C22—C21 | 0.7 (3) |
N7—Ni1—N10—C22 | −7.9 (2) | Ni1—N10—C22—C21 | −175.5 (2) |
N9—Ni1—N10—C22 | −179.5 (2) | C20—C21—C22—N10 | −0.6 (4) |
N8—Ni1—N10—C22 | −86.9 (2) | C22—N10—C23—C19 | −0.5 (3) |
N1—Ni1—N10—C23 | −90.0 (1) | Ni1—N10—C23—C19 | 176.3 (2) |
N7—Ni1—N10—C23 | 175.8 (1) | C22—N10—C23—C24 | 178.7 (2) |
N9—Ni1—N10—C23 | 4.1 (1) | Ni1—N10—C23—C24 | −4.5 (2) |
N8—Ni1—N10—C23 | 96.7 (1) | C20—C19—C23—N10 | 0.1 (3) |
C12—N7—C1—C2 | −0.4 (3) | C18—C19—C23—N10 | 179.2 (2) |
Ni1—N7—C1—C2 | 180.0 (2) | C20—C19—C23—C24 | −179.1 (2) |
N7—C1—C2—C3 | −1.0 (3) | C18—C19—C23—C24 | 0.0 (3) |
C1—C2—C3—C4 | 1.6 (3) | C13—N9—C24—C16 | 1.0 (3) |
C2—C3—C4—C12 | −0.8 (3) | Ni1—N9—C24—C16 | −178.3 (2) |
C2—C3—C4—C5 | −179.7 (2) | C13—N9—C24—C23 | −178.9 (2) |
C3—C4—C5—C6 | −180.0 (2) | Ni1—N9—C24—C23 | 1.8 (2) |
C12—C4—C5—C6 | 1.3 (3) | C15—C16—C24—N9 | −0.8 (3) |
C4—C5—C6—C7 | −0.5 (3) | C17—C16—C24—N9 | 178.7 (2) |
C5—C6—C7—C8 | −178.9 (2) | C15—C16—C24—C23 | 179.1 (2) |
C5—C6—C7—C11 | −0.3 (3) | C17—C16—C24—C23 | −1.4 (3) |
C11—C7—C8—C9 | −1.5 (3) | N10—C23—C24—N9 | 1.8 (3) |
C6—C7—C8—C9 | 177.2 (2) | C19—C23—C24—N9 | −178.9 (2) |
C7—C8—C9—C10 | 1.2 (3) | N10—C23—C24—C16 | −178.1 (2) |
C11—N8—C10—C9 | −2.0 (3) | C19—C23—C24—C16 | 1.2 (3) |
Experimental details
Crystal data | |
Chemical formula | C24H16N10Ni |
Mr | 503.18 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.200 (1), 11.002 (2), 12.408 (2) |
α, β, γ (°) | 82.28 (2), 82.26 (2), 72.57 (1) |
V (Å3) | 1053.0 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.96 |
Crystal size (mm) | 0.48 × 0.34 × 0.30 |
Data collection | |
Diffractometer | Siemens P4 four-circle diffractometer |
Absorption correction | Empirical ψ scan (North et al., 1968) |
Tmin, Tmax | 0.656, 0.762 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3984, 3697, 3277 |
Rint | 0.012 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.072, 1.03 |
No. of reflections | 3697 |
No. of parameters | 316 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.30 |
Computer programs: XSCANS (Siemens, 1990), Siemens software PLEASE SPECIFY (Siemens, 1990), Siemens software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-II (Johnson, 1976).
Ni1—N1 | 2.073 (2) | Ni1—N10 | 2.115 (2) |
Ni1—N4 | 2.091 (2) | N1—N2 | 1.177 (3) |
Ni1—N7 | 2.081 (2) | N2—N3 | 1.144 (3) |
Ni1—N8 | 2.115 (2) | N4—N5 | 1.174 (3) |
Ni1—N9 | 2.094 (2) | N5—N6 | 1.162 (3) |
N1—Ni1—N4 | 91.6 (1) | N7—Ni1—N9 | 168.0 (1) |
N1—Ni1—N7 | 94.3 (1) | N7—Ni1—N10 | 92.3 (1) |
N1—Ni1—N8 | 173.3 (1) | N8—Ni1—N9 | 93.0 (1) |
N1—Ni1—N9 | 93.6 (1) | N8—Ni1—N10 | 92.3 (1) |
N1—Ni1—N10 | 87.9 (1) | N9—Ni1—N10 | 79.0 (1) |
N4—Ni1—N7 | 93.4 (1) | N2—N1—Ni1 | 123.9 (1) |
N4—Ni1—N8 | 88.8 (1) | N1—N2—N3 | 177.8 (3) |
N4—Ni1—N9 | 95.3 (1) | N5—N4—Ni1 | 126.6 (2) |
N4—Ni1—N10 | 174.3 (1) | N4—N5—N6 | 177.6 (2) |
N7—Ni1—N8 | 78.9 (1) |
The azide anion, which has the ability to bind in several modes (Sheppard et al., 1996), is an excellent unit for bridging divalent transition metal atoms such as copper, manganese and nickel. Such metal–azide complexes serve as models for the investigation of metalloenzymes and ferromagnetic/antiferromagnetic interactions (Aebersold et al., 1998; Baffert et al., 2001). The 1,10-phenanthroline complex of copper diazide exists as a dinuclear compound, which is bridged by the pseudohalide group; adjacent molecules are linked by lattice water molecules into a layer structure (Cheng et al., 2002; Prabakaran, 2002). On the other hand, manganese diazide.2(1,10-phenanthroline) is a monomeric compound (Shen et al., 1999).
Bis(1,10-phenanthroline)diazidonickel, (I), also exists as a monomeric molecule; the metal atom adopts an NiN6 octahedral geometry, and the two azido groups occupy cis positions (Fig. 1). The four dative Ni—N distances are not much different from the two Ni—N distances; the distortion of the geometry arises from the small bite of the heterocyclic donor ligands. The bond distances involving the metal atom are not significantly different from those found in the 2,2'-bipyridine analog, which crystallizes as a monohydrate (Urtiaga et al., 1995).
Adjacent molecules in the title complex are linked by a weak C20—H20···N6i interaction [C20···N6i = 3.405 (3) Å; C20—H20···N6i = 155°; symmetry code (i): x − 1, y + 1, z] into a linear chain along the diagonal direction in the ab plane (Fig. 2). Some evidence for this interaction, which involves the terminal nitrogen end of one the two azido groups, is suggested by the temperature factor of atom N6, which is only about half as large as that of the terminal nitrogen end of the second azido group, N3, which does not participate in any noticeable intermolecular interactions.