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The crystal structure of the title compound, (C
12H
12N
2)[CuCl
4], consists of Cu
II complex anions and diprotonated bis(4-pyridyl)ethylene. The cations and anions lie across individual inversion centers. The square-planar Cu
II complex anions link with cations
via N—H
Cl hydrogen bonding.
Supporting information
CCDC reference: 215193
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.006 Å
- R factor = 0.043
- wR factor = 0.127
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 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, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 1999) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL.
4,4'-Ethylenebipyridinium tetrachlorocuprate
top
Crystal data top
(C12H12N2)[CuCl4] | Z = 1 |
Mr = 389.58 | F(000) = 195 |
Triclinic, P1 | Dx = 1.801 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0207 (14) Å | Cell parameters from 1725 reflections |
b = 7.0602 (11) Å | θ = 3.1–27.1° |
c = 8.1978 (19) Å | µ = 2.25 mm−1 |
α = 68.66 (1)° | T = 273 K |
β = 73.748 (6)° | Block, blue |
γ = 76.204 (11)° | 0.43 × 0.24 × 0.23 mm |
V = 359.10 (12) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1547 independent reflections |
Radiation source: fine-focus sealed tube | 1357 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 27.2°, θmin = 2.7° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = 0→9 |
Tmin = 0.531, Tmax = 0.603 | k = −8→9 |
3071 measured reflections | l = −9→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.374P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max < 0.001 |
1547 reflections | Δρmax = 0.56 e Å−3 |
89 parameters | Δρmin = −0.82 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.086 (11) |
Special details top
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 | 0.5000 | 0.5000 | 0.5000 | 0.0338 (2) | |
Cl1 | 0.26992 (17) | 0.78630 (16) | 0.46614 (15) | 0.0535 (3) | |
Cl2 | 0.56858 (15) | 0.55362 (15) | 0.73305 (13) | 0.0470 (3) | |
N1 | 0.2762 (4) | −0.0354 (5) | 0.7682 (4) | 0.0392 (7) | |
H1 | 0.3227 | −0.1295 | 0.7178 | 0.047* | |
C1 | 0.3045 (6) | −0.0705 (6) | 0.9299 (6) | 0.0434 (8) | |
H1A | 0.3744 | −0.1958 | 0.9873 | 0.052* | |
C2 | 0.2321 (6) | 0.0755 (6) | 1.0133 (5) | 0.0422 (8) | |
H2 | 0.2514 | 0.0485 | 1.1279 | 0.051* | |
C3 | 0.1310 (5) | 0.2618 (5) | 0.9293 (5) | 0.0372 (8) | |
C4 | 0.1036 (6) | 0.2938 (6) | 0.7593 (5) | 0.0417 (8) | |
H4 | 0.0350 | 0.4181 | 0.6985 | 0.050* | |
C5 | 0.1779 (6) | 0.1416 (6) | 0.6816 (5) | 0.0418 (8) | |
H5 | 0.1593 | 0.1624 | 0.5680 | 0.050* | |
C6 | 0.0564 (6) | 0.4131 (6) | 1.0271 (6) | 0.0450 (9) | |
H6 | 0.0934 | 0.3809 | 1.1356 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0372 (4) | 0.0323 (4) | 0.0339 (4) | 0.0013 (2) | −0.0119 (2) | −0.0139 (2) |
Cl1 | 0.0663 (7) | 0.0458 (6) | 0.0584 (6) | 0.0200 (5) | −0.0356 (5) | −0.0293 (5) |
Cl2 | 0.0564 (6) | 0.0470 (5) | 0.0448 (5) | 0.0112 (4) | −0.0247 (4) | −0.0247 (4) |
N1 | 0.0384 (16) | 0.0326 (15) | 0.0480 (18) | −0.0027 (12) | −0.0033 (13) | −0.0206 (13) |
C1 | 0.0405 (19) | 0.0378 (19) | 0.049 (2) | −0.0020 (15) | −0.0125 (16) | −0.0112 (16) |
C2 | 0.0436 (19) | 0.050 (2) | 0.0353 (18) | −0.0085 (16) | −0.0110 (15) | −0.0141 (16) |
C3 | 0.0331 (17) | 0.0374 (18) | 0.0432 (19) | −0.0057 (14) | −0.0025 (14) | −0.0191 (15) |
C4 | 0.0425 (19) | 0.0353 (18) | 0.043 (2) | −0.0011 (15) | −0.0086 (16) | −0.0105 (15) |
C5 | 0.047 (2) | 0.045 (2) | 0.0347 (18) | −0.0092 (16) | −0.0079 (15) | −0.0137 (15) |
C6 | 0.048 (2) | 0.049 (2) | 0.046 (2) | −0.0028 (16) | −0.0132 (16) | −0.0247 (18) |
Geometric parameters (Å, º) top
Cu1—Cl1 | 2.2489 (10) | C2—C3 | 1.370 (5) |
Cu1—Cl1i | 2.2489 (10) | C2—H2 | 0.9300 |
Cu1—Cl2i | 2.2701 (10) | C3—C4 | 1.389 (5) |
Cu1—Cl2 | 2.2701 (10) | C3—C6 | 1.477 (5) |
N1—C1 | 1.320 (5) | C4—C5 | 1.371 (5) |
N1—C5 | 1.326 (5) | C4—H4 | 0.9300 |
N1—H1 | 0.8600 | C5—H5 | 0.9300 |
C1—C2 | 1.363 (6) | C6—C6ii | 1.291 (8) |
C1—H1A | 0.9300 | C6—H6 | 0.9300 |
| | | |
Cl1—Cu1—Cl1i | 180.0 | C3—C2—H2 | 119.8 |
Cl1—Cu1—Cl2i | 90.10 (3) | C2—C3—C4 | 117.7 (3) |
Cl1i—Cu1—Cl2i | 89.90 (3) | C2—C3—C6 | 117.6 (3) |
Cl1—Cu1—Cl2 | 89.90 (3) | C4—C3—C6 | 124.7 (3) |
Cl1i—Cu1—Cl2 | 90.10 (3) | C5—C4—C3 | 119.8 (4) |
Cl2i—Cu1—Cl2 | 180.0 | C5—C4—H4 | 120.1 |
C1—N1—C5 | 121.6 (3) | C3—C4—H4 | 120.1 |
C1—N1—H1 | 119.2 | N1—C5—C4 | 120.1 (3) |
C5—N1—H1 | 119.2 | N1—C5—H5 | 120.0 |
N1—C1—C2 | 120.5 (3) | C4—C5—H5 | 120.0 |
N1—C1—H1A | 119.7 | C6ii—C6—C3 | 124.8 (5) |
C2—C1—H1A | 119.7 | C6ii—C6—H6 | 117.6 |
C1—C2—C3 | 120.3 (3) | C3—C6—H6 | 117.6 |
C1—C2—H2 | 119.8 | | |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1iii | 0.86 | 2.48 | 3.174 (3) | 138 |
N1—H1···Cl2iii | 0.86 | 2.47 | 3.187 (3) | 142 |
Symmetry code: (iii) x, y−1, z. |
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