Bis(1-methyl-1H-imidazole-κN³)dithio­cyanato­copper(II)

In the title compound, [Cu(NCS)₂(C₄H₆N₂)₂], each Cu atom is located on an inversion center, in a distorted octa­hedral environment. The equatorial plane is occupied by four N atoms from two 1-methyl­imidazole ligands and two thio­cyanate anions. Thio­cyanate S atoms are weakly coordinated to Cu in the axial positions, linking the copper centers to form extended zigzag chains.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.034
• wR factor = 0.114
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C5      ..       6.95 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.17 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(1-methyl-1H-imidazole-κN³)dithiocyanatocopper(II)

Crystal data

[Cu(NCS)2(C4H6N2)2]	F(000) = 350
Mr = 343.95	Dx = 1.577 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.7200 (11) Å	θ = 4–14°
b = 15.020 (3) Å	µ = 1.79 mm^−1
c = 8.4340 (17) Å	T = 293 K
β = 91.46 (3)°	Block, blue
V = 724.4 (2) Å^3	0.35 × 0.25 × 0.25 mm
Z = 2

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 2.7°
Graphite monochromator	h = 0→7
ω scans	k = 0→19
1723 measured reflections	l = −10→10
1573 independent reflections	3 standard reflections every 100 reflections
1164 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.08P)^2] where P = (Fo^2 + 2Fc^2)/3
1573 reflections	(Δ/σ)max < 0.001
89 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6340 (7)	0.6877 (2)	0.5538 (4)	0.0560 (9)
H1A	0.7782	0.7095	0.5128	0.084*
H1B	0.6657	0.6545	0.6492	0.084*
H1C	0.5335	0.7370	0.5767	0.084*
C2	0.3017 (6)	0.5923 (2)	0.4477 (4)	0.0482 (8)
H2A	0.2004	0.5984	0.5315	0.058*
C3	0.2637 (6)	0.5445 (2)	0.3134 (4)	0.0476 (7)
H3A	0.1294	0.5118	0.2893	0.057*
C4	0.6024 (5)	0.6043 (2)	0.2975 (3)	0.0408 (7)
H4A	0.7478	0.6214	0.2610	0.049*
C5	0.9413 (5)	0.61250 (19)	−0.0662 (3)	0.0372 (6)
N1	0.5187 (4)	0.62977 (16)	0.4356 (3)	0.0410 (6)
N2	0.4558 (4)	0.55175 (17)	0.2174 (3)	0.0385 (5)
N3	0.7743 (4)	0.57651 (17)	−0.0267 (3)	0.0458 (6)
S1	1.17591 (16)	0.66199 (7)	−0.12540 (12)	0.0621 (3)
Cu1	0.5000	0.5000	0.0000	0.0377 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.059 (2)	0.059 (2)	0.0500 (18)	−0.0072 (16)	−0.0068 (16)	−0.0067 (16)
C2	0.0438 (17)	0.0517 (18)	0.0497 (18)	−0.0010 (14)	0.0137 (14)	−0.0050 (15)
C3	0.0382 (16)	0.0545 (19)	0.0506 (18)	−0.0068 (14)	0.0110 (13)	−0.0056 (15)
C4	0.0352 (14)	0.0491 (17)	0.0382 (15)	−0.0007 (12)	0.0010 (12)	0.0053 (13)
C5	0.0356 (14)	0.0444 (15)	0.0317 (14)	−0.0017 (12)	0.0013 (12)	−0.0078 (12)
N1	0.0449 (14)	0.0402 (13)	0.0379 (13)	−0.0004 (11)	−0.0002 (10)	0.0009 (11)
N2	0.0334 (12)	0.0458 (14)	0.0365 (13)	−0.0006 (10)	0.0049 (9)	0.0016 (10)
N3	0.0357 (13)	0.0516 (15)	0.0505 (15)	−0.0081 (11)	0.0116 (11)	−0.0028 (12)
S1	0.0470 (5)	0.0794 (6)	0.0606 (6)	−0.0280 (4)	0.0137 (4)	−0.0014 (5)
Cu1	0.0292 (3)	0.0476 (3)	0.0367 (3)	−0.0070 (2)	0.00682 (19)	−0.0010 (2)

Geometric parameters (Å, º)

C1—N1	1.467 (4)	C4—N1	1.327 (4)
C1—H1A	0.9600	C4—H4A	0.9300
C1—H1B	0.9600	C5—N3	1.154 (4)
C1—H1C	0.9600	C5—S1	1.624 (3)
C2—C3	1.354 (4)	N2—Cu1	2.013 (2)
C2—N1	1.369 (4)	N3—Cu1	1.963 (2)
C2—H2A	0.9300	Cu1—N3^i	1.963 (2)
C3—N2	1.386 (4)	Cu1—N2^i	2.013 (2)
C3—H3A	0.9300	Cu1—S1^ii	3.221 (1)
C4—N2	1.324 (4)	Cu1—S1^iii	3.221 (1)
N1—C1—H1A	109.5	N3—C5—S1	178.8 (3)
N1—C1—H1B	109.5	C4—N1—C2	107.1 (3)
H1A—C1—H1B	109.5	C4—N1—C1	127.0 (3)
N1—C1—H1C	109.5	C2—N1—C1	125.9 (3)
H1A—C1—H1C	109.5	C4—N2—C3	104.5 (2)
H1B—C1—H1C	109.5	C4—N2—Cu1	127.0 (2)
C3—C2—N1	106.4 (3)	C3—N2—Cu1	128.4 (2)
C3—C2—H2A	126.8	C5—N3—Cu1	167.8 (2)
N1—C2—H2A	126.8	N3^i—Cu1—N3	180.00 (12)
C2—C3—N2	109.6 (3)	N3^i—Cu1—N2	90.12 (10)
C2—C3—H3A	125.2	N3—Cu1—N2	89.88 (10)
N2—C3—H3A	125.2	N3^i—Cu1—N2^i	89.88 (10)
N2—C4—N1	112.4 (3)	N3—Cu1—N2^i	90.12 (10)
N2—C4—H4A	123.8	N2—Cu1—N2^i	180.00 (5)
N1—C4—H4A	123.8

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···N3	0.93	2.52	2.959 (4)	109