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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005367/om6223sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005367/om6223Isup2.hkl
Contains datablock I

CCDC reference: 238646

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Computing details top

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)]ClF(000) = 1184
Mr = 580.82Dx = 1.706 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 11826 reflections
a = 8.6493 (17) Åθ = 1.6–25.0°
b = 32.089 (6) ŵ = 1.47 mm1
c = 8.3107 (17) ÅT = 298 K
β = 101.42 (3)°Prism, green
V = 2261.0 (8) Å30.42 × 0.36 × 0.32 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4406 independent reflections
Radiation source: fine-focus sealed tube2769 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 10.00 pixels mm-1θmax = 25.9°, θmin = 1.3°
ω scansh = 910
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 3739
Tmin = 0.55, Tmax = 0.63l = 910
12745 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-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 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.41 e Å3
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
xyzUiso*/Ueq
Ni0.40430 (5)0.121095 (14)0.73748 (5)0.02072 (13)
Cl0.97574 (11)0.17976 (3)0.36991 (11)0.0332 (3)
S10.66683 (12)0.23493 (3)0.57596 (13)0.0370 (3)
S20.04856 (12)0.21604 (3)0.88916 (12)0.0346 (3)
S30.08453 (11)0.01080 (3)0.83349 (12)0.0327 (3)
S40.72113 (11)0.09092 (3)1.24498 (11)0.0302 (3)
S50.71825 (11)0.01099 (3)0.57049 (11)0.0252 (2)
O10.2630 (3)0.12817 (7)0.4944 (3)0.0296 (6)
N10.5226 (3)0.17574 (9)0.6931 (3)0.0225 (7)
N20.2575 (3)0.16670 (9)0.8111 (3)0.0226 (7)
N30.7575 (4)0.15461 (10)0.6162 (4)0.0326 (8)
N40.0688 (4)0.13310 (10)0.9372 (4)0.0345 (8)
N50.2739 (3)0.07011 (9)0.7918 (3)0.0220 (7)
N60.5277 (3)0.10748 (9)0.9750 (3)0.0198 (7)
N70.0577 (3)0.06186 (10)0.5715 (4)0.0309 (8)
N80.7357 (4)0.15594 (9)1.0427 (4)0.0302 (8)
N90.5512 (3)0.08078 (10)0.6476 (3)0.0249 (7)
C10.6487 (4)0.18330 (12)0.6300 (4)0.0247 (9)
C20.4929 (4)0.24633 (12)0.6408 (4)0.0335 (10)
H20.44720.27260.63670.040*
C30.4333 (4)0.21198 (12)0.6979 (4)0.0236 (9)
C40.2922 (4)0.20725 (11)0.7662 (4)0.0236 (9)
C50.1935 (4)0.23693 (12)0.7999 (4)0.0313 (10)
H50.20260.26510.77760.038*
C60.1302 (4)0.16701 (12)0.8779 (4)0.0260 (9)
C70.1426 (4)0.05103 (11)0.7177 (4)0.0231 (9)
C80.2468 (4)0.02046 (12)0.9854 (5)0.0331 (10)
H80.27090.00591.08400.040*
C90.3340 (4)0.05161 (11)0.9435 (4)0.0236 (9)
C100.4781 (4)0.07040 (11)1.0377 (4)0.0225 (9)
C110.5672 (4)0.05749 (12)1.1799 (4)0.0295 (9)
H110.54790.03351.23570.035*
C120.6547 (4)0.12146 (12)1.0720 (4)0.0232 (8)
C130.6205 (4)0.05156 (12)0.6165 (4)0.0207 (8)
C140.3243 (5)0.12535 (16)0.3541 (5)0.0625 (15)
H14A0.40600.14580.35780.094*
H14B0.24220.13030.25990.094*
H14C0.36740.09800.34680.094*
H10.17640.14770.47520.080*
H3A0.83870.16070.55660.080*
H3B0.73860.12550.62950.080*
H4A0.11260.10690.94530.080*
H4B0.01520.13320.96700.080*
H7A0.11050.07630.49790.080*
H7B0.04420.05290.52540.080*
H8A0.70180.17120.96480.080*
H8B0.82790.16441.10140.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.0176 (3)0.0221 (3)0.0228 (3)0.0009 (2)0.0048 (2)0.0008 (2)
Cl0.0243 (5)0.0370 (6)0.0375 (6)0.0054 (5)0.0041 (5)0.0057 (5)
S10.0354 (6)0.0318 (6)0.0443 (7)0.0064 (5)0.0091 (5)0.0100 (5)
S20.0293 (6)0.0344 (6)0.0403 (6)0.0104 (5)0.0076 (5)0.0060 (5)
S30.0242 (6)0.0353 (6)0.0370 (6)0.0085 (5)0.0020 (5)0.0094 (5)
S40.0247 (6)0.0355 (6)0.0273 (5)0.0017 (5)0.0027 (5)0.0037 (5)
S50.0196 (5)0.0240 (5)0.0316 (5)0.0029 (4)0.0035 (4)0.0002 (4)
O10.0270 (15)0.0281 (16)0.0336 (15)0.0039 (12)0.0059 (13)0.0024 (12)
N10.0211 (17)0.0253 (18)0.0217 (16)0.0005 (14)0.0055 (14)0.0016 (14)
N20.0203 (17)0.0256 (19)0.0213 (16)0.0028 (14)0.0031 (14)0.0016 (14)
N30.0252 (19)0.033 (2)0.044 (2)0.0019 (16)0.0190 (16)0.0003 (16)
N40.029 (2)0.037 (2)0.042 (2)0.0045 (16)0.0194 (17)0.0058 (17)
N50.0185 (17)0.0262 (18)0.0209 (17)0.0017 (14)0.0028 (14)0.0040 (14)
N60.0167 (16)0.0208 (18)0.0228 (17)0.0008 (14)0.0063 (14)0.0011 (13)
N70.0217 (18)0.040 (2)0.0279 (18)0.0036 (15)0.0023 (15)0.0056 (16)
N80.0279 (19)0.029 (2)0.0321 (19)0.0059 (15)0.0013 (15)0.0023 (15)
N90.0206 (18)0.0255 (19)0.0294 (18)0.0019 (15)0.0065 (15)0.0008 (15)
C10.024 (2)0.031 (2)0.019 (2)0.0065 (18)0.0034 (17)0.0005 (17)
C20.033 (2)0.025 (2)0.040 (2)0.0008 (19)0.001 (2)0.0056 (19)
C30.024 (2)0.025 (2)0.019 (2)0.0023 (17)0.0033 (17)0.0015 (17)
C40.022 (2)0.022 (2)0.024 (2)0.0029 (17)0.0008 (17)0.0024 (17)
C50.028 (2)0.029 (2)0.034 (2)0.0032 (19)0.0016 (19)0.0038 (19)
C60.022 (2)0.031 (2)0.023 (2)0.0064 (18)0.0005 (17)0.0021 (18)
C70.020 (2)0.026 (2)0.024 (2)0.0026 (17)0.0054 (17)0.0011 (17)
C80.029 (2)0.033 (3)0.034 (2)0.0008 (19)0.0011 (19)0.0104 (19)
C90.018 (2)0.029 (2)0.024 (2)0.0022 (17)0.0029 (17)0.0048 (17)
C100.018 (2)0.026 (2)0.024 (2)0.0022 (17)0.0065 (17)0.0004 (17)
C110.027 (2)0.030 (2)0.031 (2)0.0051 (19)0.0036 (19)0.0045 (19)
C120.023 (2)0.029 (2)0.0194 (19)0.0054 (18)0.0090 (17)0.0019 (18)
C130.016 (2)0.027 (2)0.018 (2)0.0064 (17)0.0015 (16)0.0046 (17)
C140.050 (3)0.099 (5)0.034 (3)0.027 (3)0.001 (2)0.006 (3)
Geometric parameters (Å, º) top
Ni—O12.156 (2)N4—H4B0.814
Ni—N12.099 (3)N5—C71.329 (4)
Ni—N22.106 (3)N5—C91.397 (4)
Ni—N52.087 (3)N6—C121.306 (4)
Ni—N62.096 (3)N6—C101.400 (4)
Ni—N92.055 (3)N7—C71.335 (4)
S1—C11.732 (4)N7—H7A0.953
S1—C21.734 (4)N7—H7B0.934
S2—C51.714 (4)N8—C121.357 (4)
S2—C61.734 (4)N8—H8A0.819
S3—C81.720 (4)N8—H8B0.892
S3—C71.742 (4)N9—C131.169 (4)
S4—C111.712 (4)C2—C31.343 (5)
S4—C121.740 (4)C2—H20.9300
S5—C131.638 (4)C3—C41.453 (5)
O1—C141.376 (4)C4—C51.345 (5)
O1—H10.965C5—H50.9300
N1—C11.323 (4)C8—C91.339 (5)
N1—C31.401 (4)C8—H80.9300
N2—C61.328 (4)C9—C101.465 (5)
N2—C41.402 (4)C10—C111.342 (4)
N3—C11.337 (4)C11—H110.9300
N3—H3A0.956C14—H14A0.9600
N3—H3B0.958C14—H14B0.9600
N4—C61.346 (4)C14—H14C0.9600
N4—H4A0.919
N1—Ni—N279.26 (11)H8A—N8—H8B113.0
N5—Ni—N680.15 (11)C13—N9—Ni165.1 (3)
N9—Ni—N589.13 (11)N1—C1—N3123.9 (3)
N9—Ni—N688.57 (11)N1—C1—S1113.7 (3)
N9—Ni—N195.97 (11)N3—C1—S1122.3 (3)
N5—Ni—N1174.89 (11)C3—C2—S1110.7 (3)
N6—Ni—N199.48 (11)C3—C2—H2124.6
N9—Ni—N2174.19 (11)S1—C2—H2124.6
N5—Ni—N295.68 (11)C2—C3—N1114.8 (3)
N6—Ni—N295.46 (10)C2—C3—C4129.4 (4)
N9—Ni—O190.14 (10)N1—C3—C4115.8 (3)
N5—Ni—O193.15 (10)C5—C4—N2115.1 (3)
N6—Ni—O1173.19 (10)C5—C4—C3128.6 (4)
N1—Ni—O187.31 (10)N2—C4—C3116.2 (3)
N2—Ni—O186.34 (10)C4—C5—S2111.2 (3)
C1—S1—C289.58 (18)C4—C5—H5124.4
C5—S2—C689.51 (19)S2—C5—H5124.4
C8—S3—C789.39 (18)N2—C6—N4124.5 (3)
C11—S4—C1289.03 (18)N2—C6—S2114.2 (3)
C14—O1—Ni123.0 (2)N4—C6—S2121.3 (3)
C14—O1—H1108.6N5—C7—N7124.5 (3)
Ni—O1—H1120.06N5—C7—S3113.5 (3)
C1—N1—C3111.2 (3)N7—C7—S3121.9 (3)
C1—N1—Ni133.8 (3)C9—C8—S3111.3 (3)
C3—N1—Ni113.4 (2)C9—C8—H8124.3
C6—N2—C4110.1 (3)S3—C8—H8124.3
C6—N2—Ni136.4 (3)C8—C9—N5115.1 (3)
C4—N2—Ni113.2 (2)C8—C9—C10129.2 (3)
C1—N3—H3A120.3N5—C9—C10115.6 (3)
C1—N3—H3B121.4C11—C10—N6115.2 (3)
H3A—N3—H3B114.8C11—C10—C9128.5 (3)
C6—N4—H4A125.5N6—C10—C9116.2 (3)
C6—N4—H4B123.2C10—C11—S4111.1 (3)
H4A—N4—H4B111.3C10—C11—H11124.5
C7—N5—C9110.7 (3)S4—C11—H11124.5
C7—N5—Ni135.2 (2)N6—C12—N8124.7 (3)
C9—N5—Ni114.1 (2)N6—C12—S4114.6 (3)
C12—N6—C10110.1 (3)N8—C12—S4120.6 (3)
C12—N6—Ni135.9 (2)N9—C13—S5179.1 (3)
C10—N6—Ni113.0 (2)O1—C14—H14A109.5
C7—N7—H7A117.6O1—C14—H14B109.5
C7—N7—H7B126.7H14A—C14—H14B109.5
H7A—N7—H7B114.8O1—C14—H14C109.5
C12—N8—H8A121.0H14A—C14—H14C109.5
C12—N8—H8B126.1H14B—C14—H14C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Cli0.972.062.994 (3)163
N3—H3A···Cl0.962.223.152 (4)166
N3—H3B···N90.962.193.008 (5)142
N4—H4A···N50.922.383.089 (4)134
N4—H4B···N8i0.812.473.257 (5)163
N7—H7A···O10.952.132.923 (4)140
N7—H7B···S5i0.932.543.358 (3)146
N8—H8A···N10.822.483.181 (4)145
N8—H8B···Clii0.892.393.171 (3)146
Symmetry codes: (i) x1, y, z; (ii) x, y, z+1.
 

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