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In the new ion-pair title complex, (C
12H
11N
2O
2)
2[Ni(C
4N
2S
2)
2] or 2(NO
2BzPy)
+·[Ni(i-mnt)
2]
2−, where NO
2BzPy
+ is 1-(4-nitrobenzyl)pyridinium and i-mnt is 2,2-dicyanoethylene-1,1-dithiolate, the [Ni(i-mnt)
2]
2− complex anion lies on an inversion centre and exhibits an almost structure. Weak C—H
N and C—H
Ni contacts are observed between anions and cations in the crystal structure.
Supporting information
CCDC reference: 627315
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.054
- wR factor = 0.095
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3 ... 1.42 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C4 ... 1.42 Ang.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Bis[1-(4-nitrobenzyl)pyridinium]
bis(2,2-dicyanoethylene-1,1-dithiolato-
κ2S,
S')nickel(II)
top
Crystal data top
(C12H11N2O2)2[Ni(C4N2S2)2] | F(000) = 788 |
Mr = 769.53 | Dx = 1.491 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 607 reflections |
a = 9.825 (1) Å | θ = 2.7–26.5° |
b = 12.092 (1) Å | µ = 0.86 mm−1 |
c = 14.660 (2) Å | T = 293 K |
β = 100.11 (1)° | Block, brown |
V = 1714.6 (3) Å3 | 0.46 × 0.32 × 0.24 mm |
Z = 2 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3017 independent reflections |
Radiation source: fine-focus sealed tube | 1649 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.716, Tmax = 0.804 | k = −14→12 |
16784 measured reflections | l = −17→15 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 0.85 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
3017 reflections | (Δ/σ)max < 0.001 |
223 parameters | Δρmax = 0.35 e Å−3 |
2 restraints | Δρmin = −0.27 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.0000 | 0.0000 | 0.0000 | 0.0459 (2) | |
S1 | −0.10543 (12) | 0.15741 (9) | 0.01222 (9) | 0.0564 (4) | |
S2 | 0.17713 (11) | 0.11399 (9) | 0.02447 (8) | 0.0534 (3) | |
N1 | −0.1117 (4) | 0.4509 (3) | 0.0844 (3) | 0.0822 (14) | |
N2 | 0.3353 (4) | 0.3941 (3) | 0.0902 (3) | 0.0806 (14) | |
N3 | 0.9123 (4) | 1.0135 (3) | 0.2841 (3) | 0.0523 (10) | |
N4 | 1.0560 (5) | 0.4937 (4) | 0.3312 (3) | 0.0674 (12) | |
O1 | 1.0226 (4) | 0.4438 (3) | 0.3963 (3) | 0.0976 (13) | |
O2 | 1.1361 (4) | 0.4583 (3) | 0.2845 (3) | 0.0926 (13) | |
C1 | 0.0577 (4) | 0.2150 (3) | 0.0357 (3) | 0.0471 (11) | |
C2 | 0.0870 (5) | 0.3222 (3) | 0.0622 (3) | 0.0481 (11) | |
C3 | −0.0223 (5) | 0.3942 (4) | 0.0748 (3) | 0.0569 (13) | |
C4 | 0.2247 (5) | 0.3633 (4) | 0.0781 (3) | 0.0556 (13) | |
C5 | 0.8601 (4) | 0.7541 (4) | 0.3465 (3) | 0.0605 (13) | |
H5 | 0.8054 | 0.7860 | 0.3851 | 0.073* | |
C6 | 0.9183 (5) | 0.6513 (4) | 0.3678 (3) | 0.0627 (13) | |
H6 | 0.9049 | 0.6144 | 0.4212 | 0.075* | |
C7 | 0.9958 (5) | 0.6050 (4) | 0.3094 (3) | 0.0496 (12) | |
C8 | 1.0183 (5) | 0.6561 (4) | 0.2313 (3) | 0.0625 (13) | |
H8 | 1.0713 | 0.6227 | 0.1924 | 0.075* | |
C9 | 0.9600 (5) | 0.7601 (4) | 0.2106 (3) | 0.0672 (14) | |
H9 | 0.9738 | 0.7966 | 0.1571 | 0.081* | |
C10 | 0.8822 (4) | 0.8093 (3) | 0.2690 (3) | 0.0496 (12) | |
C11 | 0.8193 (4) | 0.9214 (3) | 0.2448 (3) | 0.0612 (14) | |
H11A | 0.7985 | 0.9289 | 0.1779 | 0.073* | |
H11B | 0.7329 | 0.9269 | 0.2680 | 0.073* | |
C12 | 0.8938 (5) | 1.0647 (4) | 0.3610 (4) | 0.0692 (15) | |
H12 | 0.8239 | 1.0414 | 0.3919 | 0.083* | |
C13 | 0.9763 (6) | 1.1508 (4) | 0.3951 (4) | 0.0848 (17) | |
H13 | 0.9618 | 1.1875 | 0.4483 | 0.102* | |
C14 | 1.0806 (6) | 1.1828 (4) | 0.3505 (4) | 0.0796 (17) | |
H14 | 1.1378 | 1.2415 | 0.3734 | 0.095* | |
C15 | 1.1007 (5) | 1.1287 (4) | 0.2726 (4) | 0.0751 (16) | |
H15 | 1.1717 | 1.1494 | 0.2417 | 0.090* | |
C16 | 1.0150 (6) | 1.0440 (4) | 0.2410 (3) | 0.0674 (14) | |
H16 | 1.0282 | 1.0061 | 0.1880 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0456 (5) | 0.0457 (5) | 0.0459 (5) | 0.0053 (4) | 0.0069 (4) | −0.0042 (4) |
S1 | 0.0427 (7) | 0.0497 (7) | 0.0768 (9) | 0.0037 (6) | 0.0103 (6) | −0.0070 (6) |
S2 | 0.0445 (7) | 0.0520 (7) | 0.0625 (8) | 0.0076 (6) | 0.0061 (6) | −0.0049 (6) |
N1 | 0.072 (3) | 0.056 (3) | 0.124 (4) | 0.007 (2) | 0.033 (3) | −0.001 (3) |
N2 | 0.058 (3) | 0.083 (3) | 0.098 (4) | −0.007 (3) | 0.005 (3) | −0.008 (2) |
N3 | 0.055 (3) | 0.052 (2) | 0.049 (2) | 0.006 (2) | 0.007 (2) | 0.006 (2) |
N4 | 0.069 (3) | 0.053 (3) | 0.076 (3) | −0.004 (3) | 0.002 (3) | −0.006 (3) |
O1 | 0.119 (3) | 0.066 (2) | 0.116 (4) | 0.006 (2) | 0.043 (3) | 0.027 (2) |
O2 | 0.100 (3) | 0.081 (3) | 0.096 (3) | 0.030 (2) | 0.016 (3) | −0.009 (2) |
C1 | 0.045 (3) | 0.049 (3) | 0.046 (3) | 0.006 (2) | 0.004 (2) | 0.000 (2) |
C2 | 0.048 (2) | 0.043 (3) | 0.052 (3) | 0.006 (2) | 0.006 (2) | −0.001 (2) |
C3 | 0.060 (4) | 0.042 (3) | 0.069 (4) | −0.007 (3) | 0.014 (3) | 0.004 (3) |
C4 | 0.051 (3) | 0.052 (3) | 0.062 (3) | 0.005 (3) | 0.005 (3) | −0.008 (2) |
C5 | 0.056 (3) | 0.055 (3) | 0.077 (4) | 0.010 (3) | 0.029 (3) | 0.001 (3) |
C6 | 0.061 (3) | 0.064 (3) | 0.066 (4) | −0.007 (3) | 0.019 (3) | 0.010 (3) |
C7 | 0.047 (3) | 0.048 (3) | 0.054 (3) | −0.005 (2) | 0.009 (3) | −0.004 (2) |
C8 | 0.070 (4) | 0.064 (3) | 0.056 (3) | 0.007 (3) | 0.015 (3) | −0.014 (3) |
C9 | 0.088 (4) | 0.065 (3) | 0.047 (3) | 0.004 (3) | 0.008 (3) | 0.003 (3) |
C10 | 0.043 (3) | 0.048 (3) | 0.054 (3) | 0.002 (2) | −0.002 (3) | −0.008 (2) |
C11 | 0.052 (3) | 0.059 (3) | 0.066 (3) | 0.001 (3) | −0.006 (3) | −0.002 (3) |
C12 | 0.067 (4) | 0.068 (3) | 0.079 (4) | −0.012 (3) | 0.031 (3) | −0.015 (3) |
C13 | 0.089 (5) | 0.071 (4) | 0.102 (5) | −0.016 (3) | 0.037 (4) | −0.034 (3) |
C14 | 0.071 (4) | 0.049 (3) | 0.117 (5) | −0.010 (3) | 0.013 (4) | 0.004 (3) |
C15 | 0.072 (4) | 0.070 (4) | 0.088 (5) | −0.007 (3) | 0.026 (3) | 0.013 (3) |
C16 | 0.077 (4) | 0.070 (4) | 0.059 (4) | 0.009 (3) | 0.021 (3) | 0.011 (3) |
Geometric parameters (Å, º) top
Ni1—S1 | 2.1894 (11) | C6—C7 | 1.363 (6) |
Ni1—S1i | 2.1894 (11) | C6—H6 | 0.9300 |
Ni1—S2 | 2.1996 (11) | C7—C8 | 1.352 (6) |
Ni1—S2i | 2.1996 (11) | C8—C9 | 1.393 (5) |
S1—C1 | 1.725 (4) | C8—H8 | 0.9300 |
S2—C1 | 1.721 (4) | C9—C10 | 1.378 (6) |
N1—C3 | 1.142 (5) | C9—H9 | 0.9300 |
N2—C4 | 1.133 (5) | C10—C11 | 1.507 (5) |
N3—C12 | 1.325 (5) | C11—H11A | 0.9700 |
N3—C16 | 1.334 (6) | C11—H11B | 0.9700 |
N3—C11 | 1.491 (5) | C12—C13 | 1.360 (6) |
N4—O2 | 1.210 (5) | C12—H12 | 0.9300 |
N4—O1 | 1.221 (5) | C13—C14 | 1.365 (7) |
N4—C7 | 1.482 (5) | C13—H13 | 0.9300 |
C1—C2 | 1.370 (5) | C14—C15 | 1.361 (7) |
C2—C3 | 1.419 (6) | C14—H14 | 0.9300 |
C2—C4 | 1.421 (6) | C15—C16 | 1.355 (6) |
C5—C10 | 1.367 (6) | C15—H15 | 0.9300 |
C5—C6 | 1.381 (5) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | | |
| | | |
S1—Ni1—S1i | 180.00 (8) | C7—C8—C9 | 118.4 (5) |
S1—Ni1—S2 | 79.28 (4) | C7—C8—H8 | 120.8 |
S1i—Ni1—S2 | 100.72 (4) | C9—C8—H8 | 120.8 |
S1—Ni1—S2i | 100.72 (4) | C10—C9—C8 | 120.4 (5) |
S1i—Ni1—S2i | 79.28 (4) | C10—C9—H9 | 119.8 |
S2—Ni1—S2i | 180.00 (8) | C8—C9—H9 | 119.8 |
C1—S1—Ni1 | 86.03 (14) | C5—C10—C9 | 119.5 (4) |
C1—S2—Ni1 | 85.80 (15) | C5—C10—C11 | 121.1 (4) |
C12—N3—C16 | 120.1 (4) | C9—C10—C11 | 119.4 (5) |
C12—N3—C11 | 120.8 (4) | N3—C11—C10 | 112.5 (3) |
C16—N3—C11 | 119.1 (4) | N3—C11—H11A | 109.1 |
O2—N4—O1 | 124.0 (5) | C10—C11—H11A | 109.1 |
O2—N4—C7 | 118.2 (5) | N3—C11—H11B | 109.1 |
O1—N4—C7 | 117.8 (5) | C10—C11—H11B | 109.1 |
C2—C1—S2 | 125.8 (3) | H11A—C11—H11B | 107.8 |
C2—C1—S1 | 125.5 (3) | N3—C12—C13 | 120.6 (5) |
S2—C1—S1 | 108.7 (2) | N3—C12—H12 | 119.7 |
C1—C2—C3 | 119.4 (4) | C13—C12—H12 | 119.7 |
C1—C2—C4 | 121.6 (4) | C12—C13—C14 | 119.4 (5) |
C3—C2—C4 | 119.0 (4) | C12—C13—H13 | 120.3 |
N1—C3—C2 | 178.9 (5) | C14—C13—H13 | 120.3 |
N2—C4—C2 | 178.7 (5) | C15—C14—C13 | 119.8 (5) |
C10—C5—C6 | 120.5 (4) | C15—C14—H14 | 120.1 |
C10—C5—H5 | 119.8 | C13—C14—H14 | 120.1 |
C6—C5—H5 | 119.8 | C16—C15—C14 | 118.5 (5) |
C7—C6—C5 | 118.9 (5) | C16—C15—H15 | 120.7 |
C7—C6—H6 | 120.6 | C14—C15—H15 | 120.7 |
C5—C6—H6 | 120.6 | N3—C16—C15 | 121.5 (5) |
C8—C7—C6 | 122.4 (5) | N3—C16—H16 | 119.2 |
C8—C7—N4 | 118.7 (5) | C15—C16—H16 | 119.2 |
C6—C7—N4 | 118.9 (5) | | |
Symmetry code: (i) −x, −y, −z. |
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