metal-organic compounds
In the new ion-pair title complex, (C12H11N2O2)2[Ni(C4N2S2)2] or 2(NO2BzPy)+·[Ni(i-mnt)2]2−, where NO2BzPy+ 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—HN and C—HNi contacts are observed between anions and cations in the crystal structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041973/bh2049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041973/bh2049Isup2.hkl |
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
Computing details top
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.
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. |