In the title salt (C7H11N2)2[Cu(C4N2S2)2], the Cu2+ ion is coordinated by four S atoms of two 1,2-dicyanoethene-1,2-dithiolate (or maleonitriledithiolate, mnt2−) ligands in an approximate square-planar geometry. The Cu atom is located on an inversion centre. Strong hydrogen-bonding interactions between the pyridinium proton and the CN groups of the mnt2− ligand link anions and cations into a one-dimensional chain structure.
Supporting information
CCDC reference: 608345
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.061
- wR factor = 0.138
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level A
ABSTM02_ALERT_3_A Test not performed as the _exptl_absorpt_correction_type
has not been identified. See test ABSTY_01.
ABSTY01_ALERT_1_A The absorption correction should be one of the following
* none
* analytical
* integration
* numerical
* gaussian
* empirical
* psi-scan
* multi-scan
* refdelf
* sphere
* cylinder
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.124
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06
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 C1 - C2 ... 1.42 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C4 ... 1.43 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C11
PLAT412_ALERT_2_C Short Intra XH3 .. XHn H6A .. H10A .. 1.86 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn H8A .. H11A .. 1.82 Ang.
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 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
4 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
Bis[4-(dimethylamino)pyridinium]
bis(1,2-dicyanoethene-1,2-dithiolato-
κ2S,
S')cuprate(II)
top
Crystal data top
(C7H11N2)2[Cu(C4N2S2)2] | F(000) = 606 |
Mr = 590.26 | Dx = 1.568 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 657 reflections |
a = 12.271 (2) Å | θ = 2.6–25.0° |
b = 6.0279 (11) Å | µ = 1.24 mm−1 |
c = 17.236 (3) Å | T = 293 K |
β = 101.219 (4)° | Needle, brown |
V = 1250.5 (4) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2196 independent reflections |
Radiation source: fine-focus sealed tube | 1588 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.124 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −14→14 |
Tmin = 0.847, Tmax = 0.901 | k = −7→6 |
5947 measured reflections | l = −20→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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0409P)2] where P = (Fo2 + 2Fc2)/3 |
2196 reflections | (Δ/σ)max < 0.001 |
160 parameters | Δρmax = 0.78 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 | |
Cu1 | 1.0000 | 0.0000 | 0.0000 | 0.0287 (3) | |
S1 | 1.03531 (13) | −0.1464 (2) | 0.12415 (8) | 0.0394 (4) | |
S2 | 0.91822 (12) | 0.2993 (2) | 0.04339 (8) | 0.0361 (4) | |
N1 | 0.9782 (4) | −0.0273 (8) | 0.3233 (3) | 0.0485 (13) | |
N2 | 0.8360 (4) | 0.5089 (8) | 0.2254 (3) | 0.0483 (13) | |
N3 | 0.8543 (4) | 0.5924 (8) | 0.3969 (3) | 0.0411 (12) | |
H3A | 0.8640 | 0.6416 | 0.3519 | 0.049* | |
N4 | 0.8071 (4) | 0.3651 (7) | 0.6118 (3) | 0.0369 (11) | |
C1 | 0.9769 (4) | 0.0070 (8) | 0.2580 (3) | 0.0331 (13) | |
C2 | 0.9757 (4) | 0.0494 (8) | 0.1765 (3) | 0.0302 (13) | |
C3 | 0.9248 (4) | 0.2358 (8) | 0.1412 (3) | 0.0272 (12) | |
C4 | 0.8754 (4) | 0.3894 (9) | 0.1878 (3) | 0.0322 (13) | |
C5 | 0.8000 (5) | 0.4005 (10) | 0.4014 (3) | 0.0418 (15) | |
H5A | 0.7733 | 0.3214 | 0.3553 | 0.050* | |
C6 | 0.7834 (5) | 0.3208 (9) | 0.4707 (3) | 0.0372 (14) | |
H6A | 0.7459 | 0.1871 | 0.4719 | 0.045* | |
C7 | 0.8223 (4) | 0.4378 (8) | 0.5423 (3) | 0.0297 (13) | |
C8 | 0.8807 (4) | 0.6353 (9) | 0.5340 (3) | 0.0373 (14) | |
H8A | 0.9107 | 0.7171 | 0.5788 | 0.045* | |
C9 | 0.8934 (5) | 0.7063 (9) | 0.4636 (3) | 0.0398 (15) | |
H9A | 0.9306 | 0.8392 | 0.4601 | 0.048* | |
C10 | 0.7433 (5) | 0.1662 (10) | 0.6206 (4) | 0.0538 (17) | |
H10A | 0.7218 | 0.0949 | 0.5701 | 0.081* | |
H10B | 0.6781 | 0.2061 | 0.6404 | 0.081* | |
H10C | 0.7880 | 0.0665 | 0.6570 | 0.081* | |
C11 | 0.8445 (5) | 0.4887 (10) | 0.6842 (3) | 0.0541 (17) | |
H11A | 0.8860 | 0.6160 | 0.6732 | 0.081* | |
H11B | 0.8909 | 0.3957 | 0.7221 | 0.081* | |
H11C | 0.7813 | 0.5363 | 0.7051 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0384 (5) | 0.0250 (5) | 0.0210 (5) | −0.0002 (4) | 0.0014 (4) | −0.0006 (4) |
S1 | 0.0618 (10) | 0.0310 (8) | 0.0242 (8) | 0.0117 (7) | 0.0054 (7) | 0.0024 (6) |
S2 | 0.0555 (9) | 0.0287 (8) | 0.0237 (8) | 0.0085 (7) | 0.0068 (7) | 0.0037 (6) |
N1 | 0.069 (3) | 0.049 (3) | 0.027 (3) | 0.002 (3) | 0.007 (3) | 0.006 (3) |
N2 | 0.071 (4) | 0.043 (3) | 0.033 (3) | 0.010 (3) | 0.013 (3) | 0.000 (3) |
N3 | 0.051 (3) | 0.044 (3) | 0.028 (3) | 0.002 (2) | 0.007 (2) | 0.006 (2) |
N4 | 0.050 (3) | 0.033 (3) | 0.027 (3) | −0.002 (2) | 0.005 (2) | −0.001 (2) |
C1 | 0.041 (3) | 0.023 (3) | 0.034 (4) | −0.001 (3) | 0.004 (3) | 0.002 (3) |
C2 | 0.037 (3) | 0.031 (3) | 0.021 (3) | −0.003 (2) | 0.003 (2) | 0.003 (2) |
C3 | 0.031 (3) | 0.028 (3) | 0.021 (3) | −0.004 (2) | 0.002 (2) | −0.004 (2) |
C4 | 0.039 (3) | 0.032 (3) | 0.022 (3) | −0.001 (3) | −0.004 (3) | 0.005 (3) |
C5 | 0.049 (4) | 0.042 (4) | 0.031 (4) | 0.003 (3) | −0.001 (3) | −0.011 (3) |
C6 | 0.048 (4) | 0.031 (3) | 0.031 (3) | 0.000 (3) | 0.003 (3) | −0.002 (3) |
C7 | 0.033 (3) | 0.029 (3) | 0.027 (3) | 0.009 (2) | 0.006 (3) | −0.004 (2) |
C8 | 0.045 (4) | 0.031 (3) | 0.034 (4) | 0.000 (3) | 0.001 (3) | −0.006 (3) |
C9 | 0.046 (4) | 0.033 (3) | 0.039 (4) | −0.005 (3) | 0.003 (3) | −0.001 (3) |
C10 | 0.067 (4) | 0.052 (4) | 0.044 (4) | 0.001 (3) | 0.014 (3) | 0.010 (3) |
C11 | 0.073 (4) | 0.061 (4) | 0.027 (3) | −0.002 (4) | 0.009 (3) | −0.002 (3) |
Geometric parameters (Å, º) top
Cu1—S2 | 2.2613 (14) | C3—C4 | 1.435 (8) |
Cu1—S2i | 2.2613 (14) | C5—C6 | 1.338 (7) |
Cu1—S1 | 2.2770 (14) | C5—H5A | 0.9300 |
Cu1—S1i | 2.2770 (14) | C6—C7 | 1.421 (7) |
S1—C2 | 1.732 (5) | C6—H6A | 0.9300 |
S2—C3 | 1.715 (5) | C7—C8 | 1.410 (7) |
N1—C1 | 1.141 (7) | C8—C9 | 1.325 (7) |
N2—C4 | 1.138 (7) | C8—H8A | 0.9300 |
N3—C9 | 1.344 (7) | C9—H9A | 0.9300 |
N3—C5 | 1.345 (7) | C10—H10A | 0.9600 |
N3—H3A | 0.8600 | C10—H10B | 0.9600 |
N4—C7 | 1.323 (6) | C10—H10C | 0.9600 |
N4—C11 | 1.449 (7) | C11—H11A | 0.9600 |
N4—C10 | 1.455 (7) | C11—H11B | 0.9600 |
C1—C2 | 1.425 (7) | C11—H11C | 0.9600 |
C2—C3 | 1.369 (7) | | |
| | | |
S2—Cu1—S2i | 180.00 (9) | C5—C6—C7 | 120.8 (5) |
S2—Cu1—S1 | 90.80 (5) | C5—C6—H6A | 119.6 |
S2i—Cu1—S1 | 89.20 (5) | C7—C6—H6A | 119.6 |
S2—Cu1—S1i | 89.20 (5) | N4—C7—C8 | 122.3 (5) |
S2i—Cu1—S1i | 90.80 (5) | N4—C7—C6 | 122.6 (5) |
S1—Cu1—S1i | 180.00 (8) | C8—C7—C6 | 115.0 (5) |
C2—S1—Cu1 | 101.70 (17) | C9—C8—C7 | 121.2 (5) |
C3—S2—Cu1 | 102.00 (18) | C9—C8—H8A | 119.4 |
C9—N3—C5 | 119.2 (5) | C7—C8—H8A | 119.4 |
C9—N3—H3A | 120.4 | C8—C9—N3 | 122.2 (5) |
C5—N3—H3A | 120.4 | C8—C9—H9A | 118.9 |
C7—N4—C11 | 122.2 (5) | N3—C9—H9A | 118.9 |
C7—N4—C10 | 122.7 (5) | N4—C10—H10A | 109.5 |
C11—N4—C10 | 114.9 (5) | N4—C10—H10B | 109.5 |
N1—C1—C2 | 179.8 (6) | H10A—C10—H10B | 109.5 |
C3—C2—C1 | 120.1 (5) | N4—C10—H10C | 109.5 |
C3—C2—S1 | 122.0 (4) | H10A—C10—H10C | 109.5 |
C1—C2—S1 | 117.8 (4) | H10B—C10—H10C | 109.5 |
C2—C3—C4 | 119.1 (5) | N4—C11—H11A | 109.5 |
C2—C3—S2 | 123.4 (4) | N4—C11—H11B | 109.5 |
C4—C3—S2 | 117.5 (4) | H11A—C11—H11B | 109.5 |
N2—C4—C3 | 179.1 (6) | N4—C11—H11C | 109.5 |
C6—C5—N3 | 121.6 (5) | H11A—C11—H11C | 109.5 |
C6—C5—H5A | 119.2 | H11B—C11—H11C | 109.5 |
N3—C5—H5A | 119.2 | | |
Symmetry code: (i) −x+2, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N2 | 0.86 | 2.29 | 2.964 (7) | 136 |
N3—H3A···N1ii | 0.86 | 2.54 | 3.151 (7) | 129 |
Symmetry code: (ii) x, y+1, z. |