The title compound, [Ni(NCS)(C6H6N4S2)(CH4O)]Cl, consists of an NiII complex cation and a Cl− anion. The NiII complex has an octahedral coordination, with the isothiocyanate and methanol ligands in cis positions. The diaminobithiazole ligands are each nearly planar, but the NiII atom is out of the planes of the thiazole rings, the deviations ranging from 0.113 (5) to 0.389 (4) Å.
Supporting information
CCDC reference: 238646
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.078
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.01 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for S5 - C13 .. 5.23 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni - O1 .. 6.36 su
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl .. S2 .. 3.40 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Bis(2,2'-diamino-4,4'-bi-1,3-thiazole-
κ2N,
N')(isothiocyanato-
κN)(methanol)nickel(II) chloride
top
Crystal data top
[Ni(NCS)(C6H6N4S2)(CH4O)]Cl | F(000) = 1184 |
Mr = 580.82 | Dx = 1.706 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 11826 reflections |
a = 8.6493 (17) Å | θ = 1.6–25.0° |
b = 32.089 (6) Å | µ = 1.47 mm−1 |
c = 8.3107 (17) Å | T = 298 K |
β = 101.42 (3)° | Prism, green |
V = 2261.0 (8) Å3 | 0.42 × 0.36 × 0.32 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4406 independent reflections |
Radiation source: fine-focus sealed tube | 2769 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 10.00 pixels mm-1 | θmax = 25.9°, θmin = 1.3° |
ω scans | h = −9→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −37→39 |
Tmin = 0.55, Tmax = 0.63 | l = −9→10 |
12745 measured reflections | |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 0.85 | w = 1/[σ2(Fo2) + (0.0238P)2] where P = (Fo2 + 2Fc2)/3 |
4406 reflections | (Δ/σ)max < 0.001 |
281 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−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 | |
Ni | 0.40430 (5) | 0.121095 (14) | 0.73748 (5) | 0.02072 (13) | |
Cl | 0.97574 (11) | 0.17976 (3) | 0.36991 (11) | 0.0332 (3) | |
S1 | 0.66683 (12) | 0.23493 (3) | 0.57596 (13) | 0.0370 (3) | |
S2 | 0.04856 (12) | 0.21604 (3) | 0.88916 (12) | 0.0346 (3) | |
S3 | 0.08453 (11) | 0.01080 (3) | 0.83349 (12) | 0.0327 (3) | |
S4 | 0.72113 (11) | 0.09092 (3) | 1.24498 (11) | 0.0302 (3) | |
S5 | 0.71825 (11) | 0.01099 (3) | 0.57049 (11) | 0.0252 (2) | |
O1 | 0.2630 (3) | 0.12817 (7) | 0.4944 (3) | 0.0296 (6) | |
N1 | 0.5226 (3) | 0.17574 (9) | 0.6931 (3) | 0.0225 (7) | |
N2 | 0.2575 (3) | 0.16670 (9) | 0.8111 (3) | 0.0226 (7) | |
N3 | 0.7575 (4) | 0.15461 (10) | 0.6162 (4) | 0.0326 (8) | |
N4 | 0.0688 (4) | 0.13310 (10) | 0.9372 (4) | 0.0345 (8) | |
N5 | 0.2739 (3) | 0.07011 (9) | 0.7918 (3) | 0.0220 (7) | |
N6 | 0.5277 (3) | 0.10748 (9) | 0.9750 (3) | 0.0198 (7) | |
N7 | 0.0577 (3) | 0.06186 (10) | 0.5715 (4) | 0.0309 (8) | |
N8 | 0.7357 (4) | 0.15594 (9) | 1.0427 (4) | 0.0302 (8) | |
N9 | 0.5512 (3) | 0.08078 (10) | 0.6476 (3) | 0.0249 (7) | |
C1 | 0.6487 (4) | 0.18330 (12) | 0.6300 (4) | 0.0247 (9) | |
C2 | 0.4929 (4) | 0.24633 (12) | 0.6408 (4) | 0.0335 (10) | |
H2 | 0.4472 | 0.2726 | 0.6367 | 0.040* | |
C3 | 0.4333 (4) | 0.21198 (12) | 0.6979 (4) | 0.0236 (9) | |
C4 | 0.2922 (4) | 0.20725 (11) | 0.7662 (4) | 0.0236 (9) | |
C5 | 0.1935 (4) | 0.23693 (12) | 0.7999 (4) | 0.0313 (10) | |
H5 | 0.2026 | 0.2651 | 0.7776 | 0.038* | |
C6 | 0.1302 (4) | 0.16701 (12) | 0.8779 (4) | 0.0260 (9) | |
C7 | 0.1426 (4) | 0.05103 (11) | 0.7177 (4) | 0.0231 (9) | |
C8 | 0.2468 (4) | 0.02046 (12) | 0.9854 (5) | 0.0331 (10) | |
H8 | 0.2709 | 0.0059 | 1.0840 | 0.040* | |
C9 | 0.3340 (4) | 0.05161 (11) | 0.9435 (4) | 0.0236 (9) | |
C10 | 0.4781 (4) | 0.07040 (11) | 1.0377 (4) | 0.0225 (9) | |
C11 | 0.5672 (4) | 0.05749 (12) | 1.1799 (4) | 0.0295 (9) | |
H11 | 0.5479 | 0.0335 | 1.2357 | 0.035* | |
C12 | 0.6547 (4) | 0.12146 (12) | 1.0720 (4) | 0.0232 (8) | |
C13 | 0.6205 (4) | 0.05156 (12) | 0.6165 (4) | 0.0207 (8) | |
C14 | 0.3243 (5) | 0.12535 (16) | 0.3541 (5) | 0.0625 (15) | |
H14A | 0.4060 | 0.1458 | 0.3578 | 0.094* | |
H14B | 0.2422 | 0.1303 | 0.2599 | 0.094* | |
H14C | 0.3674 | 0.0980 | 0.3468 | 0.094* | |
H1 | 0.1764 | 0.1477 | 0.4752 | 0.080* | |
H3A | 0.8387 | 0.1607 | 0.5566 | 0.080* | |
H3B | 0.7386 | 0.1255 | 0.6295 | 0.080* | |
H4A | 0.1126 | 0.1069 | 0.9453 | 0.080* | |
H4B | −0.0152 | 0.1332 | 0.9670 | 0.080* | |
H7A | 0.1105 | 0.0763 | 0.4979 | 0.080* | |
H7B | −0.0442 | 0.0529 | 0.5254 | 0.080* | |
H8A | 0.7018 | 0.1712 | 0.9648 | 0.080* | |
H8B | 0.8279 | 0.1644 | 1.1014 | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni | 0.0176 (3) | 0.0221 (3) | 0.0228 (3) | 0.0009 (2) | 0.0048 (2) | 0.0008 (2) |
Cl | 0.0243 (5) | 0.0370 (6) | 0.0375 (6) | −0.0054 (5) | 0.0041 (5) | 0.0057 (5) |
S1 | 0.0354 (6) | 0.0318 (6) | 0.0443 (7) | −0.0064 (5) | 0.0091 (5) | 0.0100 (5) |
S2 | 0.0293 (6) | 0.0344 (6) | 0.0403 (6) | 0.0104 (5) | 0.0076 (5) | −0.0060 (5) |
S3 | 0.0242 (6) | 0.0353 (6) | 0.0370 (6) | −0.0085 (5) | 0.0020 (5) | 0.0094 (5) |
S4 | 0.0247 (6) | 0.0355 (6) | 0.0273 (5) | −0.0017 (5) | −0.0027 (5) | 0.0037 (5) |
S5 | 0.0196 (5) | 0.0240 (5) | 0.0316 (5) | 0.0029 (4) | 0.0035 (4) | −0.0002 (4) |
O1 | 0.0270 (15) | 0.0281 (16) | 0.0336 (15) | 0.0039 (12) | 0.0059 (13) | −0.0024 (12) |
N1 | 0.0211 (17) | 0.0253 (18) | 0.0217 (16) | 0.0005 (14) | 0.0055 (14) | 0.0016 (14) |
N2 | 0.0203 (17) | 0.0256 (19) | 0.0213 (16) | 0.0028 (14) | 0.0031 (14) | −0.0016 (14) |
N3 | 0.0252 (19) | 0.033 (2) | 0.044 (2) | −0.0019 (16) | 0.0190 (16) | −0.0003 (16) |
N4 | 0.029 (2) | 0.037 (2) | 0.042 (2) | 0.0045 (16) | 0.0194 (17) | 0.0058 (17) |
N5 | 0.0185 (17) | 0.0262 (18) | 0.0209 (17) | 0.0017 (14) | 0.0028 (14) | 0.0040 (14) |
N6 | 0.0167 (16) | 0.0208 (18) | 0.0228 (17) | −0.0008 (14) | 0.0063 (14) | −0.0011 (13) |
N7 | 0.0217 (18) | 0.040 (2) | 0.0279 (18) | −0.0036 (15) | −0.0023 (15) | 0.0056 (16) |
N8 | 0.0279 (19) | 0.029 (2) | 0.0321 (19) | −0.0059 (15) | 0.0013 (15) | 0.0023 (15) |
N9 | 0.0206 (18) | 0.0255 (19) | 0.0294 (18) | −0.0019 (15) | 0.0065 (15) | −0.0008 (15) |
C1 | 0.024 (2) | 0.031 (2) | 0.019 (2) | −0.0065 (18) | 0.0034 (17) | −0.0005 (17) |
C2 | 0.033 (2) | 0.025 (2) | 0.040 (2) | 0.0008 (19) | 0.001 (2) | 0.0056 (19) |
C3 | 0.024 (2) | 0.025 (2) | 0.019 (2) | 0.0023 (17) | −0.0033 (17) | 0.0015 (17) |
C4 | 0.022 (2) | 0.022 (2) | 0.024 (2) | 0.0029 (17) | −0.0008 (17) | −0.0024 (17) |
C5 | 0.028 (2) | 0.029 (2) | 0.034 (2) | 0.0032 (19) | −0.0016 (19) | −0.0038 (19) |
C6 | 0.022 (2) | 0.031 (2) | 0.023 (2) | 0.0064 (18) | −0.0005 (17) | −0.0021 (18) |
C7 | 0.020 (2) | 0.026 (2) | 0.024 (2) | 0.0026 (17) | 0.0054 (17) | 0.0011 (17) |
C8 | 0.029 (2) | 0.033 (3) | 0.034 (2) | −0.0008 (19) | −0.0011 (19) | 0.0104 (19) |
C9 | 0.018 (2) | 0.029 (2) | 0.024 (2) | 0.0022 (17) | 0.0029 (17) | 0.0048 (17) |
C10 | 0.018 (2) | 0.026 (2) | 0.024 (2) | 0.0022 (17) | 0.0065 (17) | −0.0004 (17) |
C11 | 0.027 (2) | 0.030 (2) | 0.031 (2) | −0.0051 (19) | 0.0036 (19) | 0.0045 (19) |
C12 | 0.023 (2) | 0.029 (2) | 0.0194 (19) | 0.0054 (18) | 0.0090 (17) | −0.0019 (18) |
C13 | 0.016 (2) | 0.027 (2) | 0.018 (2) | −0.0064 (17) | 0.0015 (16) | 0.0046 (17) |
C14 | 0.050 (3) | 0.099 (5) | 0.034 (3) | 0.027 (3) | −0.001 (2) | 0.006 (3) |
Geometric parameters (Å, º) top
Ni—O1 | 2.156 (2) | N4—H4B | 0.814 |
Ni—N1 | 2.099 (3) | N5—C7 | 1.329 (4) |
Ni—N2 | 2.106 (3) | N5—C9 | 1.397 (4) |
Ni—N5 | 2.087 (3) | N6—C12 | 1.306 (4) |
Ni—N6 | 2.096 (3) | N6—C10 | 1.400 (4) |
Ni—N9 | 2.055 (3) | N7—C7 | 1.335 (4) |
S1—C1 | 1.732 (4) | N7—H7A | 0.953 |
S1—C2 | 1.734 (4) | N7—H7B | 0.934 |
S2—C5 | 1.714 (4) | N8—C12 | 1.357 (4) |
S2—C6 | 1.734 (4) | N8—H8A | 0.819 |
S3—C8 | 1.720 (4) | N8—H8B | 0.892 |
S3—C7 | 1.742 (4) | N9—C13 | 1.169 (4) |
S4—C11 | 1.712 (4) | C2—C3 | 1.343 (5) |
S4—C12 | 1.740 (4) | C2—H2 | 0.9300 |
S5—C13 | 1.638 (4) | C3—C4 | 1.453 (5) |
O1—C14 | 1.376 (4) | C4—C5 | 1.345 (5) |
O1—H1 | 0.965 | C5—H5 | 0.9300 |
N1—C1 | 1.323 (4) | C8—C9 | 1.339 (5) |
N1—C3 | 1.401 (4) | C8—H8 | 0.9300 |
N2—C6 | 1.328 (4) | C9—C10 | 1.465 (5) |
N2—C4 | 1.402 (4) | C10—C11 | 1.342 (4) |
N3—C1 | 1.337 (4) | C11—H11 | 0.9300 |
N3—H3A | 0.956 | C14—H14A | 0.9600 |
N3—H3B | 0.958 | C14—H14B | 0.9600 |
N4—C6 | 1.346 (4) | C14—H14C | 0.9600 |
N4—H4A | 0.919 | | |
| | | |
N1—Ni—N2 | 79.26 (11) | H8A—N8—H8B | 113.0 |
N5—Ni—N6 | 80.15 (11) | C13—N9—Ni | 165.1 (3) |
N9—Ni—N5 | 89.13 (11) | N1—C1—N3 | 123.9 (3) |
N9—Ni—N6 | 88.57 (11) | N1—C1—S1 | 113.7 (3) |
N9—Ni—N1 | 95.97 (11) | N3—C1—S1 | 122.3 (3) |
N5—Ni—N1 | 174.89 (11) | C3—C2—S1 | 110.7 (3) |
N6—Ni—N1 | 99.48 (11) | C3—C2—H2 | 124.6 |
N9—Ni—N2 | 174.19 (11) | S1—C2—H2 | 124.6 |
N5—Ni—N2 | 95.68 (11) | C2—C3—N1 | 114.8 (3) |
N6—Ni—N2 | 95.46 (10) | C2—C3—C4 | 129.4 (4) |
N9—Ni—O1 | 90.14 (10) | N1—C3—C4 | 115.8 (3) |
N5—Ni—O1 | 93.15 (10) | C5—C4—N2 | 115.1 (3) |
N6—Ni—O1 | 173.19 (10) | C5—C4—C3 | 128.6 (4) |
N1—Ni—O1 | 87.31 (10) | N2—C4—C3 | 116.2 (3) |
N2—Ni—O1 | 86.34 (10) | C4—C5—S2 | 111.2 (3) |
C1—S1—C2 | 89.58 (18) | C4—C5—H5 | 124.4 |
C5—S2—C6 | 89.51 (19) | S2—C5—H5 | 124.4 |
C8—S3—C7 | 89.39 (18) | N2—C6—N4 | 124.5 (3) |
C11—S4—C12 | 89.03 (18) | N2—C6—S2 | 114.2 (3) |
C14—O1—Ni | 123.0 (2) | N4—C6—S2 | 121.3 (3) |
C14—O1—H1 | 108.6 | N5—C7—N7 | 124.5 (3) |
Ni—O1—H1 | 120.06 | N5—C7—S3 | 113.5 (3) |
C1—N1—C3 | 111.2 (3) | N7—C7—S3 | 121.9 (3) |
C1—N1—Ni | 133.8 (3) | C9—C8—S3 | 111.3 (3) |
C3—N1—Ni | 113.4 (2) | C9—C8—H8 | 124.3 |
C6—N2—C4 | 110.1 (3) | S3—C8—H8 | 124.3 |
C6—N2—Ni | 136.4 (3) | C8—C9—N5 | 115.1 (3) |
C4—N2—Ni | 113.2 (2) | C8—C9—C10 | 129.2 (3) |
C1—N3—H3A | 120.3 | N5—C9—C10 | 115.6 (3) |
C1—N3—H3B | 121.4 | C11—C10—N6 | 115.2 (3) |
H3A—N3—H3B | 114.8 | C11—C10—C9 | 128.5 (3) |
C6—N4—H4A | 125.5 | N6—C10—C9 | 116.2 (3) |
C6—N4—H4B | 123.2 | C10—C11—S4 | 111.1 (3) |
H4A—N4—H4B | 111.3 | C10—C11—H11 | 124.5 |
C7—N5—C9 | 110.7 (3) | S4—C11—H11 | 124.5 |
C7—N5—Ni | 135.2 (2) | N6—C12—N8 | 124.7 (3) |
C9—N5—Ni | 114.1 (2) | N6—C12—S4 | 114.6 (3) |
C12—N6—C10 | 110.1 (3) | N8—C12—S4 | 120.6 (3) |
C12—N6—Ni | 135.9 (2) | N9—C13—S5 | 179.1 (3) |
C10—N6—Ni | 113.0 (2) | O1—C14—H14A | 109.5 |
C7—N7—H7A | 117.6 | O1—C14—H14B | 109.5 |
C7—N7—H7B | 126.7 | H14A—C14—H14B | 109.5 |
H7A—N7—H7B | 114.8 | O1—C14—H14C | 109.5 |
C12—N8—H8A | 121.0 | H14A—C14—H14C | 109.5 |
C12—N8—H8B | 126.1 | H14B—C14—H14C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cli | 0.97 | 2.06 | 2.994 (3) | 163 |
N3—H3A···Cl | 0.96 | 2.22 | 3.152 (4) | 166 |
N3—H3B···N9 | 0.96 | 2.19 | 3.008 (5) | 142 |
N4—H4A···N5 | 0.92 | 2.38 | 3.089 (4) | 134 |
N4—H4B···N8i | 0.81 | 2.47 | 3.257 (5) | 163 |
N7—H7A···O1 | 0.95 | 2.13 | 2.923 (4) | 140 |
N7—H7B···S5i | 0.93 | 2.54 | 3.358 (3) | 146 |
N8—H8A···N1 | 0.82 | 2.48 | 3.181 (4) | 145 |
N8—H8B···Clii | 0.89 | 2.39 | 3.171 (3) | 146 |
Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1. |