Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039888/hg2278sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039888/hg2278Isup2.hkl |
CCDC reference: 660127
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.014 Å
- R factor = 0.052
- wR factor = 0.198
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for N8 - C14 .. 5.63 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 14
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 PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 2.05 PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni2 (2) 2.07 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
The title compound was prepared by the reaction of 1-vinylimidazole (1.88 g, 20 mmol) with NiCl2.6H2O(1.19 g, 5 mmol) and potassium thiocyanate (0.98 g, 10 mmol) by means of hydrothermal synthesis in a stainless-steel reactor with Teflon liner at 383 K for 24 h. Single crystals suitable for X-ray measurements were obtained by recrystallization from methanol at room temperature.
H atoms were positioned geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93–0.96 Å, and with Uiso(H) = 1.2–1.5Ueq(C).
The title compound, (I), crystallizes with two independent molecules in the asymmetric unit (Fig. 1). In the two independent molecules, each NiII ion, which are located on crystallographic centres of symmetry, displays a compressed octahedral coordination geometry, with six N atoms from two thiocyanate anions and four 1-vinylimidazole ligands building the NiN6 chromophore. The equatorial planes in the two independent molecules are formed by four Ni—N(1-vinylimadazole) bonds with lengths ranging from 2.106 (5) to 2.118 (6) Å, and the axial positions are occupied by two N-bonded NCS groups [Ni—N(NCS) = 2.067 (6) and 2.065 (5) Å]. These values agree well with those observed in [Ni(NCS)2(1-methylimidazole)4] (Liu et al., 2005) and [Ni(NCS)2(1-ethylimidazole)4] (Liu et al., 2006). In the crystal, the distance of 4.685 (3)Å of Cg1···Cg1 [Cg1 is centroids of N9–N10/C18–C20; symmetry code: 1-X,-Y,1-Z] shows a presence of π···π stacking interactions which link the two independent molecules into 1-D chain running along the a axis. Intermolecular C—H···S hydrogen bonds further stabilize the crystal structure.
For related literature, see: Liu et al. (2005, 2006).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. The packing of (I), viewed down the b axis. |
[Ni(NCS)2(C5H6N2)4] | Z = 2 |
Mr = 551.34 | F(000) = 572 |
Triclinic, P1 | Dx = 1.362 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6400 (19) Å | Cell parameters from 3253 reflections |
b = 10.242 (2) Å | θ = 4–14° |
c = 14.705 (3) Å | µ = 0.91 mm−1 |
α = 109.46 (3)° | T = 293 K |
β = 90.16 (3)° | Block, blue |
γ = 100.16 (3)° | 0.30 × 0.30 × 0.20 mm |
V = 1344.5 (6) Å3 |
Bruker SMART 1K CCD area-detector diffractometer | 5257 independent reflections |
Radiation source: fine-focus sealed tube | 3080 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
thin–slice ω scans | θmax = 26.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = 0→11 |
Tmin = 0.773, Tmax = 0.839 | k = −12→12 |
5593 measured reflections | l = −18→18 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.1152P)2 + 2.8055P] where P = (Fo2 + 2Fc2)/3 |
5257 reflections | (Δ/σ)max = 0.032 |
307 parameters | Δρmax = 0.66 e Å−3 |
1 restraint | Δρmin = −1.65 e Å−3 |
[Ni(NCS)2(C5H6N2)4] | γ = 100.16 (3)° |
Mr = 551.34 | V = 1344.5 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6400 (19) Å | Mo Kα radiation |
b = 10.242 (2) Å | µ = 0.91 mm−1 |
c = 14.705 (3) Å | T = 293 K |
α = 109.46 (3)° | 0.30 × 0.30 × 0.20 mm |
β = 90.16 (3)° |
Bruker SMART 1K CCD area-detector diffractometer | 5257 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 3080 reflections with I > 2σ(I) |
Tmin = 0.773, Tmax = 0.839 | Rint = 0.034 |
5593 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 1 restraint |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.66 e Å−3 |
5257 reflections | Δρmin = −1.65 e Å−3 |
307 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.0000 | 0.0000 | 0.0496 (4) | |
S1 | 0.0867 (3) | 0.2078 (3) | 0.07754 (18) | 0.0870 (8) | |
N1 | 0.3250 (7) | 0.0951 (7) | 0.0234 (4) | 0.0646 (17) | |
N3 | 0.3709 (9) | −0.3102 (8) | 0.1314 (6) | 0.080 (2) | |
N2 | 0.4058 (6) | −0.1414 (7) | 0.0687 (4) | 0.0597 (16) | |
N5 | 0.7598 (6) | 0.2755 (6) | 0.2474 (4) | 0.0493 (13) | |
N4 | 0.5948 (6) | 0.1415 (6) | 0.1351 (4) | 0.0530 (14) | |
C6 | 0.3214 (10) | −0.4777 (10) | 0.2129 (7) | 0.085 | |
H6A | 0.2422 | −0.4401 | 0.2361 | 0.102* | |
H6B | 0.3430 | −0.5524 | 0.2293 | 0.102* | |
C5 | 0.4024 (15) | −0.4254 (13) | 0.1574 (9) | 0.122 (4) | |
H5A | 0.4815 | −0.4634 | 0.1345 | 0.147* | |
C3 | 0.2604 (12) | −0.2492 (12) | 0.1510 (8) | 0.099 (3) | |
H3A | 0.1837 | −0.2739 | 0.1841 | 0.118* | |
C4 | 0.2797 (9) | −0.1443 (11) | 0.1141 (7) | 0.086 (3) | |
H4A | 0.2178 | −0.0827 | 0.1182 | 0.104* | |
C2 | 0.4563 (10) | −0.2409 (9) | 0.0822 (7) | 0.076 (2) | |
H2A | 0.5425 | −0.2637 | 0.0607 | 0.091* | |
C11 | 0.9296 (9) | 0.4409 (8) | 0.3719 (6) | 0.068 (2) | |
H11A | 0.8578 | 0.4784 | 0.4077 | 0.082* | |
H11B | 1.0235 | 0.4767 | 0.3948 | 0.082* | |
C10 | 0.8991 (8) | 0.3395 (8) | 0.2904 (5) | 0.0562 (18) | |
H10A | 0.9740 | 0.3051 | 0.2569 | 0.067* | |
C8 | 0.6330 (8) | 0.3001 (8) | 0.2836 (5) | 0.0569 (18) | |
H8A | 0.6186 | 0.3615 | 0.3441 | 0.068* | |
C9 | 0.5329 (8) | 0.2177 (8) | 0.2143 (5) | 0.0584 (19) | |
H9A | 0.4361 | 0.2131 | 0.2194 | 0.070* | |
C7 | 0.7300 (8) | 0.1789 (8) | 0.1588 (5) | 0.0566 (18) | |
H7A | 0.7984 | 0.1424 | 0.1185 | 0.068* | |
C1 | 0.2269 (7) | 0.1420 (8) | 0.0464 (5) | 0.0520 (17) | |
Ni2 | 0.0000 | 0.0000 | 0.5000 | 0.0402 (3) | |
S2 | 0.3353 (2) | 0.3734 (2) | 0.4538 (2) | 0.0853 (8) | |
N6 | 0.1136 (6) | 0.1787 (6) | 0.4808 (5) | 0.0547 (15) | |
N8 | −0.1142 (8) | −0.2379 (10) | 0.2048 (5) | 0.086 (3) | |
N7 | −0.0582 (6) | −0.0859 (6) | 0.3503 (4) | 0.0514 (14) | |
N10 | 0.3853 (6) | −0.1437 (6) | 0.4179 (4) | 0.0526 (14) | |
N9 | 0.1789 (5) | −0.0955 (5) | 0.4706 (4) | 0.0459 (13) | |
C17 | −0.1907 (10) | −0.4674 (10) | 0.1355 (8) | 0.087 | |
H17A | −0.1961 | −0.4693 | 0.1982 | 0.104* | |
H17B | −0.2163 | −0.5504 | 0.0831 | 0.104* | |
C16 | −0.1493 (15) | −0.3543 (14) | 0.1217 (11) | 0.145 (5) | |
H16A | −0.1424 | −0.3481 | 0.0601 | 0.174* | |
C14 | −0.0759 (10) | −0.1120 (11) | 0.1937 (7) | 0.079 (3) | |
H14A | −0.0746 | −0.0929 | 0.1361 | 0.095* | |
C15 | −0.0403 (8) | −0.0209 (9) | 0.2817 (5) | 0.065 (2) | |
H15A | −0.0074 | 0.0751 | 0.2956 | 0.077* | |
C13 | −0.1039 (9) | −0.2177 (9) | 0.3013 (7) | 0.074 (2) | |
H13A | −0.1265 | −0.2886 | 0.3281 | 0.089* | |
C22 | 0.5619 (9) | −0.0592 (11) | 0.3267 (7) | 0.087 (3) | |
H22A | 0.5062 | −0.0005 | 0.3147 | 0.104* | |
H22B | 0.6506 | −0.0615 | 0.3022 | 0.104* | |
C21 | 0.5170 (8) | −0.1359 (9) | 0.3762 (6) | 0.067 (2) | |
H21A | 0.5765 | −0.1928 | 0.3862 | 0.080* | |
C19 | 0.3321 (9) | −0.2359 (8) | 0.4646 (6) | 0.065 (2) | |
H19A | 0.3747 | −0.3059 | 0.4733 | 0.079* | |
C20 | 0.2070 (8) | −0.2054 (8) | 0.4953 (6) | 0.0607 (19) | |
H20A | 0.1478 | −0.2527 | 0.5287 | 0.073* | |
C18 | 0.2891 (7) | −0.0618 (7) | 0.4241 (5) | 0.0493 (16) | |
H18A | 0.2988 | 0.0108 | 0.3985 | 0.059* | |
C12 | 0.2049 (7) | 0.2587 (6) | 0.4678 (5) | 0.0449 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0353 (7) | 0.0620 (8) | 0.0486 (8) | 0.0122 (6) | 0.0028 (5) | 0.0136 (6) |
S1 | 0.0682 (14) | 0.123 (2) | 0.0795 (16) | 0.0500 (14) | 0.0290 (12) | 0.0312 (15) |
N1 | 0.054 (4) | 0.076 (5) | 0.057 (4) | 0.023 (3) | 0.006 (3) | 0.009 (3) |
N3 | 0.090 (6) | 0.069 (5) | 0.082 (5) | −0.001 (4) | −0.009 (4) | 0.034 (4) |
N2 | 0.052 (4) | 0.067 (4) | 0.055 (4) | 0.002 (3) | −0.005 (3) | 0.019 (3) |
N5 | 0.048 (3) | 0.056 (3) | 0.043 (3) | 0.011 (3) | 0.006 (3) | 0.015 (3) |
N4 | 0.045 (3) | 0.062 (4) | 0.047 (3) | 0.010 (3) | 0.003 (3) | 0.011 (3) |
C6 | 0.085 | 0.085 | 0.085 | 0.016 | 0.006 | 0.029 |
C5 | 0.046 (4) | 0.065 (5) | 0.039 (4) | 0.011 (4) | 0.001 (3) | 0.010 (3) |
C3 | 0.083 (7) | 0.120 (9) | 0.100 (8) | −0.003 (7) | 0.003 (6) | 0.058 (7) |
C4 | 0.064 (6) | 0.112 (8) | 0.097 (7) | 0.010 (5) | 0.018 (5) | 0.057 (6) |
C2 | 0.069 (6) | 0.072 (6) | 0.086 (6) | 0.010 (5) | −0.002 (5) | 0.026 (5) |
C11 | 0.072 (5) | 0.063 (5) | 0.061 (5) | 0.006 (4) | −0.004 (4) | 0.014 (4) |
C10 | 0.055 (4) | 0.058 (4) | 0.048 (4) | 0.005 (3) | 0.003 (3) | 0.011 (4) |
C8 | 0.062 (5) | 0.060 (4) | 0.043 (4) | 0.013 (4) | 0.006 (3) | 0.011 (3) |
C9 | 0.052 (4) | 0.075 (5) | 0.050 (4) | 0.020 (4) | 0.006 (3) | 0.020 (4) |
C7 | 0.049 (4) | 0.068 (5) | 0.046 (4) | 0.009 (3) | 0.004 (3) | 0.011 (4) |
C1 | 0.046 (4) | 0.065 (5) | 0.039 (4) | 0.011 (4) | 0.001 (3) | 0.010 (3) |
Ni2 | 0.0363 (6) | 0.0390 (6) | 0.0454 (7) | −0.0030 (5) | −0.0010 (5) | 0.0197 (5) |
S2 | 0.0629 (13) | 0.0617 (13) | 0.134 (2) | −0.0008 (10) | 0.0420 (14) | 0.0422 (14) |
N6 | 0.052 (3) | 0.047 (3) | 0.068 (4) | −0.002 (3) | 0.004 (3) | 0.029 (3) |
N8 | 0.073 (4) | 0.103 (5) | 0.054 (3) | 0.022 (3) | −0.020 (3) | −0.012 (3) |
N7 | 0.049 (3) | 0.053 (4) | 0.052 (3) | 0.005 (3) | −0.004 (3) | 0.019 (3) |
N10 | 0.043 (3) | 0.054 (3) | 0.059 (4) | 0.012 (3) | 0.002 (3) | 0.017 (3) |
N9 | 0.042 (3) | 0.046 (3) | 0.053 (3) | 0.004 (2) | −0.001 (3) | 0.022 (3) |
C17 | 0.087 | 0.087 | 0.087 | 0.016 | 0.006 | 0.029 |
C16 | 0.148 (3) | 0.067 (4) | 0.037 (3) | 0.009 (3) | 0.000 (2) | 0.010 (3) |
C14 | 0.072 (6) | 0.101 (8) | 0.068 (6) | 0.021 (5) | 0.000 (5) | 0.032 (6) |
C15 | 0.067 (5) | 0.080 (5) | 0.050 (5) | 0.014 (4) | −0.001 (4) | 0.025 (4) |
C13 | 0.069 (5) | 0.067 (5) | 0.075 (6) | 0.003 (4) | −0.017 (4) | 0.016 (5) |
C22 | 0.053 (5) | 0.124 (8) | 0.080 (6) | 0.009 (5) | 0.002 (4) | 0.033 (6) |
C21 | 0.052 (5) | 0.076 (5) | 0.071 (5) | 0.013 (4) | 0.010 (4) | 0.020 (5) |
C19 | 0.072 (5) | 0.055 (4) | 0.084 (6) | 0.028 (4) | 0.015 (4) | 0.035 (4) |
C20 | 0.067 (5) | 0.052 (4) | 0.073 (5) | 0.011 (4) | 0.013 (4) | 0.034 (4) |
C18 | 0.049 (4) | 0.054 (4) | 0.045 (4) | 0.002 (3) | 0.001 (3) | 0.022 (3) |
C12 | 0.049 (4) | 0.039 (3) | 0.050 (4) | 0.011 (3) | 0.011 (3) | 0.017 (3) |
Ni1—N1i | 2.067 (6) | Ni2—N6ii | 2.065 (5) |
Ni1—N1 | 2.067 (6) | Ni2—N6 | 2.065 (5) |
Ni1—N2 | 2.111 (6) | Ni2—N9 | 2.106 (5) |
Ni1—N2i | 2.111 (6) | Ni2—N9ii | 2.106 (5) |
Ni1—N4i | 2.118 (6) | Ni2—N7 | 2.113 (6) |
Ni1—N4 | 2.118 (6) | Ni2—N7ii | 2.113 (6) |
S1—C1 | 1.615 (7) | S2—C12 | 1.626 (7) |
N1—C1 | 1.138 (9) | N6—C12 | 1.155 (8) |
N3—C3 | 1.313 (13) | N8—C14 | 1.341 (12) |
N3—C2 | 1.358 (11) | N8—C13 | 1.366 (11) |
N3—C5 | 1.434 (14) | N8—C16 | 1.383 (15) |
N2—C2 | 1.276 (10) | N7—C13 | 1.294 (10) |
N2—C4 | 1.388 (10) | N7—C15 | 1.378 (9) |
N5—C7 | 1.341 (9) | N10—C18 | 1.340 (9) |
N5—C8 | 1.366 (9) | N10—C19 | 1.375 (9) |
N5—C10 | 1.429 (9) | N10—C21 | 1.413 (9) |
N4—C7 | 1.303 (8) | N9—C18 | 1.321 (8) |
N4—C9 | 1.373 (9) | N9—C20 | 1.361 (8) |
C6—C5 | 1.308 (14) | C17—C16 | 1.240 (19) |
C6—H6A | 0.9300 | C17—H17A | 0.9300 |
C6—H6B | 0.9300 | C17—H17B | 0.9300 |
C5—H5A | 0.9300 | C16—H16A | 0.9300 |
C3—C4 | 1.343 (13) | C14—C15 | 1.320 (11) |
C3—H3A | 0.9300 | C14—H14A | 0.9300 |
C4—H4A | 0.9300 | C15—H15A | 0.9300 |
C2—H2A | 0.9300 | C13—H13A | 0.9300 |
C11—C10 | 1.288 (10) | C22—C21 | 1.264 (12) |
C11—H11A | 0.9300 | C22—H22A | 0.9300 |
C11—H11B | 0.9300 | C22—H22B | 0.9300 |
C10—H10A | 0.9300 | C21—H21A | 0.9300 |
C8—C9 | 1.348 (10) | C19—C20 | 1.340 (10) |
C8—H8A | 0.9300 | C19—H19A | 0.9300 |
C9—H9A | 0.9300 | C20—H20A | 0.9300 |
C7—H7A | 0.9300 | C18—H18A | 0.9300 |
N1i—Ni1—N1 | 180.0 (3) | N6ii—Ni2—N6 | 180.00 (18) |
N1i—Ni1—N2 | 90.5 (3) | N6ii—Ni2—N9 | 90.4 (2) |
N1—Ni1—N2 | 89.5 (3) | N6—Ni2—N9 | 89.6 (2) |
N1i—Ni1—N2i | 89.5 (3) | N6ii—Ni2—N9ii | 89.6 (2) |
N1—Ni1—N2i | 90.5 (3) | N6—Ni2—N9ii | 90.4 (2) |
N2—Ni1—N2i | 180.0 (3) | N9—Ni2—N9ii | 180.0 (3) |
N1i—Ni1—N4i | 89.7 (2) | N6ii—Ni2—N7 | 90.2 (2) |
N1—Ni1—N4i | 90.3 (2) | N6—Ni2—N7 | 89.8 (2) |
N2—Ni1—N4i | 90.2 (2) | N9—Ni2—N7 | 87.7 (2) |
N2i—Ni1—N4i | 89.8 (2) | N9ii—Ni2—N7 | 92.3 (2) |
N1i—Ni1—N4 | 90.3 (2) | N6ii—Ni2—N7ii | 89.8 (2) |
N1—Ni1—N4 | 89.7 (2) | N6—Ni2—N7ii | 90.2 (2) |
N2—Ni1—N4 | 89.8 (2) | N9—Ni2—N7ii | 92.3 (2) |
N2i—Ni1—N4 | 90.2 (2) | N9ii—Ni2—N7ii | 87.7 (2) |
N4i—Ni1—N4 | 180.0 (2) | N7—Ni2—N7ii | 180.000 (1) |
C1—N1—Ni1 | 171.2 (7) | C12—N6—Ni2 | 162.1 (6) |
C3—N3—C2 | 107.0 (8) | C14—N8—C13 | 107.9 (7) |
C3—N3—C5 | 128.4 (10) | C14—N8—C16 | 117.1 (9) |
C2—N3—C5 | 124.6 (10) | C13—N8—C16 | 134.9 (10) |
C2—N2—C4 | 103.6 (8) | C13—N7—C15 | 104.7 (7) |
C2—N2—Ni1 | 127.3 (6) | C13—N7—Ni2 | 126.1 (6) |
C4—N2—Ni1 | 129.0 (6) | C15—N7—Ni2 | 128.7 (5) |
C7—N5—C8 | 106.2 (6) | C18—N10—C19 | 105.5 (6) |
C7—N5—C10 | 124.8 (6) | C18—N10—C21 | 128.4 (7) |
C8—N5—C10 | 128.9 (6) | C19—N10—C21 | 126.1 (7) |
C7—N4—C9 | 104.8 (6) | C18—N9—C20 | 104.6 (6) |
C7—N4—Ni1 | 125.7 (5) | C18—N9—Ni2 | 127.7 (5) |
C9—N4—Ni1 | 129.4 (5) | C20—N9—Ni2 | 127.8 (5) |
C5—C6—H6A | 120.0 | C16—C17—H17A | 120.0 |
C5—C6—H6B | 120.0 | C16—C17—H17B | 120.0 |
H6A—C6—H6B | 120.0 | H17A—C17—H17B | 120.0 |
C6—C5—N3 | 120.9 (13) | C17—C16—N8 | 114.9 (13) |
C6—C5—H5A | 119.6 | C17—C16—H16A | 122.5 |
N3—C5—H5A | 119.6 | N8—C16—H16A | 122.6 |
N3—C3—C4 | 106.6 (9) | C15—C14—N8 | 105.5 (8) |
N3—C3—H3A | 126.7 | C15—C14—H14A | 127.2 |
C4—C3—H3A | 126.7 | N8—C14—H14A | 127.2 |
C3—C4—N2 | 109.9 (9) | C14—C15—N7 | 111.5 (8) |
C3—C4—H4A | 125.0 | C14—C15—H15A | 124.3 |
N2—C4—H4A | 125.0 | N7—C15—H15A | 124.3 |
N2—C2—N3 | 112.8 (9) | N7—C13—N8 | 110.4 (8) |
N2—C2—H2A | 123.6 | N7—C13—H13A | 124.8 |
N3—C2—H2A | 123.6 | N8—C13—H13A | 124.8 |
C10—C11—H11A | 120.0 | C21—C22—H22A | 120.0 |
C10—C11—H11B | 120.0 | C21—C22—H22B | 120.0 |
H11A—C11—H11B | 120.0 | H22A—C22—H22B | 120.0 |
C11—C10—N5 | 125.5 (7) | C22—C21—N10 | 126.4 (9) |
C11—C10—H10A | 117.3 | C22—C21—H21A | 116.8 |
N5—C10—H10A | 117.3 | N10—C21—H21A | 116.8 |
C9—C8—N5 | 106.4 (6) | C20—C19—N10 | 106.9 (6) |
C9—C8—H8A | 126.8 | C20—C19—H19A | 126.6 |
N5—C8—H8A | 126.8 | N10—C19—H19A | 126.6 |
C8—C9—N4 | 109.9 (7) | C19—C20—N9 | 110.4 (7) |
C8—C9—H9A | 125.0 | C19—C20—H20A | 124.8 |
N4—C9—H9A | 125.0 | N9—C20—H20A | 124.8 |
N4—C7—N5 | 112.7 (6) | N9—C18—N10 | 112.6 (6) |
N4—C7—H7A | 123.7 | N9—C18—H18A | 123.7 |
N5—C7—H7A | 123.7 | N10—C18—H18A | 123.7 |
N1—C1—S1 | 179.2 (7) | N6—C12—S2 | 177.9 (7) |
N1i—Ni1—N2—C2 | −0.4 (7) | N7ii—Ni2—N6—C12 | 87.5 (19) |
N1—Ni1—N2—C2 | 179.6 (7) | N6ii—Ni2—N7—C13 | −19.3 (7) |
N4i—Ni1—N2—C2 | 89.2 (7) | N6—Ni2—N7—C13 | 160.7 (7) |
N4—Ni1—N2—C2 | −90.8 (7) | N9—Ni2—N7—C13 | 71.0 (7) |
N1i—Ni1—N2—C4 | 175.8 (7) | N9ii—Ni2—N7—C13 | −109.0 (7) |
N1—Ni1—N2—C4 | −4.2 (7) | N6ii—Ni2—N7—C15 | 169.7 (6) |
N4i—Ni1—N2—C4 | −94.6 (7) | N6—Ni2—N7—C15 | −10.3 (6) |
N4—Ni1—N2—C4 | 85.4 (7) | N9—Ni2—N7—C15 | −100.0 (6) |
N1i—Ni1—N4—C7 | 25.0 (7) | N9ii—Ni2—N7—C15 | 80.0 (6) |
N1—Ni1—N4—C7 | −155.0 (7) | N6ii—Ni2—N9—C18 | 159.1 (6) |
N2—Ni1—N4—C7 | 115.5 (6) | N6—Ni2—N9—C18 | −20.9 (6) |
N2i—Ni1—N4—C7 | −64.5 (6) | N7—Ni2—N9—C18 | 69.0 (6) |
N1—Ni1—N4—C9 | 22.0 (7) | N7ii—Ni2—N9—C18 | −111.0 (6) |
N2—Ni1—N4—C9 | −67.5 (6) | N6ii—Ni2—N9—C20 | −21.0 (6) |
N2i—Ni1—N4—C9 | 112.5 (6) | N6—Ni2—N9—C20 | 159.0 (6) |
C3—N3—C5—C6 | −4.9 (18) | N7—Ni2—N9—C20 | −111.1 (6) |
C2—N3—C5—C6 | 173.2 (10) | N7ii—Ni2—N9—C20 | 68.9 (6) |
C2—N3—C3—C4 | −0.1 (11) | C14—N8—C16—C17 | −176.6 (11) |
C5—N3—C3—C4 | 178.3 (10) | C13—N8—C16—C17 | 6 (2) |
N3—C3—C4—N2 | 0.8 (12) | C13—N8—C14—C15 | 1.6 (10) |
C2—N2—C4—C3 | −1.3 (11) | C16—N8—C14—C15 | −176.5 (9) |
Ni1—N2—C4—C3 | −178.2 (6) | N8—C14—C15—N7 | −1.4 (10) |
C4—N2—C2—N3 | 1.2 (10) | C13—N7—C15—C14 | 0.6 (9) |
Ni1—N2—C2—N3 | 178.2 (5) | Ni2—N7—C15—C14 | 173.1 (6) |
C3—N3—C2—N2 | −0.8 (11) | C15—N7—C13—N8 | 0.5 (9) |
C5—N3—C2—N2 | −179.3 (9) | Ni2—N7—C13—N8 | −172.3 (5) |
C7—N5—C10—C11 | 173.7 (8) | C14—N8—C13—N7 | −1.4 (10) |
C8—N5—C10—C11 | −4.3 (12) | C16—N8—C13—N7 | 176.3 (11) |
C7—N5—C8—C9 | −0.6 (8) | C18—N10—C21—C22 | −8.8 (14) |
C10—N5—C8—C9 | 177.6 (7) | C19—N10—C21—C22 | 174.1 (9) |
N5—C8—C9—N4 | 0.1 (9) | C18—N10—C19—C20 | 0.6 (8) |
C7—N4—C9—C8 | 0.4 (9) | C21—N10—C19—C20 | 178.3 (7) |
Ni1—N4—C9—C8 | −177.1 (5) | N10—C19—C20—N9 | −0.7 (9) |
C9—N4—C7—N5 | −0.9 (9) | C18—N9—C20—C19 | 0.4 (8) |
Ni1—N4—C7—N5 | 176.7 (5) | Ni2—N9—C20—C19 | −179.5 (5) |
C8—N5—C7—N4 | 1.0 (9) | C20—N9—C18—N10 | 0.0 (8) |
C10—N5—C7—N4 | −177.4 (6) | Ni2—N9—C18—N10 | 179.9 (4) |
N9—Ni2—N6—C12 | −4.8 (19) | C19—N10—C18—N9 | −0.4 (8) |
N9ii—Ni2—N6—C12 | 175.2 (19) | C21—N10—C18—N9 | −178.0 (6) |
N7—Ni2—N6—C12 | −92.5 (19) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···S1iii | 0.93 | 2.86 | 3.638 (8) | 142 |
C10—H10A···S1iii | 0.93 | 2.79 | 3.601 (8) | 146 |
C16—H16A···S1iv | 0.93 | 2.85 | 3.717 (18) | 155 |
Symmetry codes: (iii) x+1, y, z; (iv) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(NCS)2(C5H6N2)4] |
Mr | 551.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.6400 (19), 10.242 (2), 14.705 (3) |
α, β, γ (°) | 109.46 (3), 90.16 (3), 100.16 (3) |
V (Å3) | 1344.5 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.91 |
Crystal size (mm) | 0.30 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.773, 0.839 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5593, 5257, 3080 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.198, 1.01 |
No. of reflections | 5257 |
No. of parameters | 307 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.66, −1.65 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2001), SHELXTL and local programs.
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···S1i | 0.93 | 2.86 | 3.638 (8) | 142 |
C10—H10A···S1i | 0.93 | 2.79 | 3.601 (8) | 146 |
C16—H16A···S1ii | 0.93 | 2.85 | 3.717 (18) | 155 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z. |
The title compound, (I), crystallizes with two independent molecules in the asymmetric unit (Fig. 1). In the two independent molecules, each NiII ion, which are located on crystallographic centres of symmetry, displays a compressed octahedral coordination geometry, with six N atoms from two thiocyanate anions and four 1-vinylimidazole ligands building the NiN6 chromophore. The equatorial planes in the two independent molecules are formed by four Ni—N(1-vinylimadazole) bonds with lengths ranging from 2.106 (5) to 2.118 (6) Å, and the axial positions are occupied by two N-bonded NCS groups [Ni—N(NCS) = 2.067 (6) and 2.065 (5) Å]. These values agree well with those observed in [Ni(NCS)2(1-methylimidazole)4] (Liu et al., 2005) and [Ni(NCS)2(1-ethylimidazole)4] (Liu et al., 2006). In the crystal, the distance of 4.685 (3)Å of Cg1···Cg1 [Cg1 is centroids of N9–N10/C18–C20; symmetry code: 1-X,-Y,1-Z] shows a presence of π···π stacking interactions which link the two independent molecules into 1-D chain running along the a axis. Intermolecular C—H···S hydrogen bonds further stabilize the crystal structure.