Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020438/bt6092sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020438/bt6092Isup2.hkl |
CCDC reference: 180512
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.036
- wR factor = 0.100
- Data-to-parameter ratio = 21.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Copper(I) chloride (98.0 mg, 1 mmol; freshly prepared according to Gmelin, 1958) and 2-ethylpyrazine (216.3 mg, 2 mmol; ACROS) were mixed in 2 ml acetonitrile in a glass container. Direct after mixing a red precipitate of CuCl(2-ethylpyrazine) had formed which transforms two large yellow crystals of the title compound within two days. [Please reword this final sentence as its meaning is not clear]
H atoms were positioned with idealized geometry and refined with fixed isotropic displacement parameters [Uiso(H) = 1.2UeqC(methylene) and C(aromatic) = 1.5UeqO(OH)/C(methyl)] using a riding model.
Data collection: IPDS Program Package (Stoe & Cie, 1998); cell refinement: IPDS Program Package; data reduction: IPDS Program Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: CIFTAB in SHELXL97.
Fig. 1. The crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level. |
[Cu4Cl6O(C6H8N2)4] | F(000) = 1832 |
Mr = 915.44 | Dx = 1.739 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1203 (10) Å | Cell parameters from 8000 reflections |
b = 13.0461 (7) Å | θ = 15–24° |
c = 20.7233 (16) Å | µ = 2.89 mm−1 |
β = 99.718 (9)° | T = 293 K |
V = 3496.3 (4) Å3 | Block, yellow |
Z = 4 | 0.14 × 0.10 × 0.06 mm |
Stoe Imaging Plate Diffraction System diffractometer | 8309 independent reflections |
Radiation source: fine-focus sealed tube | 6876 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ scans | θmax = 28.1°, θmin = 2.8° |
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 1998) | h = −17→17 |
Tmin = 0.717, Tmax = 0.849 | k = −16→17 |
30661 measured reflections | l = −27→27 |
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)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.066P)2 + 1.0923P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
8309 reflections | Δρmax = 0.57 e Å−3 |
389 parameters | Δρmin = −0.56 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0064 (5) |
[Cu4Cl6O(C6H8N2)4] | V = 3496.3 (4) Å3 |
Mr = 915.44 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.1203 (10) Å | µ = 2.89 mm−1 |
b = 13.0461 (7) Å | T = 293 K |
c = 20.7233 (16) Å | 0.14 × 0.10 × 0.06 mm |
β = 99.718 (9)° |
Stoe Imaging Plate Diffraction System diffractometer | 8309 independent reflections |
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 1998) | 6876 reflections with I > 2σ(I) |
Tmin = 0.717, Tmax = 0.849 | Rint = 0.035 |
30661 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.57 e Å−3 |
8309 reflections | Δρmin = −0.56 e Å−3 |
389 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.97673 (2) | 0.68144 (2) | 0.640542 (15) | 0.02778 (9) | |
Cu2 | 0.78367 (3) | 0.58623 (2) | 0.556605 (16) | 0.02861 (9) | |
Cu3 | 0.76909 (3) | 0.80295 (2) | 0.615185 (16) | 0.03001 (10) | |
Cu4 | 0.89305 (3) | 0.77131 (2) | 0.502459 (15) | 0.02815 (9) | |
Cl1 | 0.93912 (6) | 0.50756 (5) | 0.61684 (4) | 0.04550 (19) | |
Cl2 | 0.66697 (6) | 0.64707 (6) | 0.62402 (4) | 0.04377 (19) | |
Cl3 | 0.77018 (7) | 0.90313 (6) | 0.52114 (4) | 0.0471 (2) | |
Cl4 | 1.06317 (5) | 0.77869 (6) | 0.56465 (4) | 0.03844 (16) | |
Cl5 | 0.90440 (6) | 0.79803 (6) | 0.71022 (3) | 0.03663 (15) | |
Cl6 | 0.80582 (6) | 0.62756 (6) | 0.44598 (3) | 0.04104 (17) | |
O1 | 0.85550 (13) | 0.71076 (12) | 0.57852 (8) | 0.0237 (3) | |
N1 | 1.3003 (2) | 0.6240 (2) | 0.77794 (14) | 0.0474 (7) | |
N2 | 1.10898 (18) | 0.65483 (17) | 0.70042 (11) | 0.0302 (5) | |
C1 | 1.2717 (2) | 0.5695 (2) | 0.72397 (15) | 0.0390 (6) | |
C2 | 1.1752 (2) | 0.5850 (2) | 0.68524 (14) | 0.0370 (6) | |
H2 | 1.1566 | 0.5456 | 0.6477 | 0.044* | |
C3 | 1.1372 (3) | 0.7077 (2) | 0.75534 (16) | 0.0410 (7) | |
H3 | 1.0923 | 0.7556 | 0.7683 | 0.049* | |
C4 | 1.2329 (3) | 0.6917 (3) | 0.79311 (18) | 0.0515 (9) | |
H4 | 1.2510 | 0.7303 | 0.8311 | 0.062* | |
C5 | 1.3459 (3) | 0.4911 (3) | 0.7067 (2) | 0.0549 (9) | |
H5A | 1.3083 | 0.4413 | 0.6770 | 0.066* | |
H5B | 1.3770 | 0.4551 | 0.7461 | 0.066* | |
C6 | 1.4302 (4) | 0.5376 (5) | 0.6749 (3) | 0.0843 (15) | |
H6A | 1.4758 | 0.4845 | 0.6649 | 0.126* | |
H6B | 1.4686 | 0.5861 | 0.7043 | 0.126* | |
H6C | 1.4000 | 0.5719 | 0.6353 | 0.126* | |
N3 | 0.6158 (2) | 0.2703 (2) | 0.49142 (17) | 0.0530 (8) | |
N4 | 0.71094 (19) | 0.45544 (17) | 0.53010 (12) | 0.0326 (5) | |
C11 | 0.5715 (2) | 0.3375 (2) | 0.52564 (16) | 0.0384 (6) | |
C12 | 0.6188 (2) | 0.4306 (2) | 0.54473 (15) | 0.0359 (6) | |
H12 | 0.5854 | 0.4767 | 0.5683 | 0.043* | |
C13 | 0.7564 (3) | 0.3872 (2) | 0.49693 (17) | 0.0433 (7) | |
H13 | 0.8211 | 0.4012 | 0.4864 | 0.052* | |
C14 | 0.7082 (3) | 0.2953 (3) | 0.4779 (2) | 0.0576 (10) | |
H14 | 0.7417 | 0.2489 | 0.4545 | 0.069* | |
C15 | 0.4696 (3) | 0.3082 (3) | 0.54448 (19) | 0.0483 (8) | |
H15A | 0.4407 | 0.3671 | 0.5636 | 0.058* | |
H15B | 0.4218 | 0.2884 | 0.5055 | 0.058* | |
C16 | 0.4811 (5) | 0.2222 (5) | 0.5921 (3) | 0.104 (2) | |
H16A | 0.4148 | 0.2055 | 0.6030 | 0.155* | |
H16B | 0.5273 | 0.2420 | 0.6311 | 0.155* | |
H16C | 0.5086 | 0.1634 | 0.5731 | 0.155* | |
N5 | 0.5349 (2) | 1.0215 (2) | 0.70053 (16) | 0.0484 (7) | |
N6 | 0.6735 (2) | 0.89547 (18) | 0.65139 (12) | 0.0345 (5) | |
C21 | 0.5017 (3) | 0.9511 (2) | 0.65537 (17) | 0.0435 (7) | |
C22 | 0.5721 (2) | 0.8872 (2) | 0.63135 (16) | 0.0411 (7) | |
H22 | 0.5474 | 0.8375 | 0.6005 | 0.049* | |
C23 | 0.7070 (3) | 0.9677 (2) | 0.69517 (16) | 0.0391 (6) | |
H23 | 0.7775 | 0.9766 | 0.7095 | 0.047* | |
C24 | 0.6365 (3) | 1.0298 (3) | 0.71931 (18) | 0.0476 (8) | |
H24 | 0.6614 | 1.0795 | 0.7501 | 0.057* | |
C25 | 0.3878 (3) | 0.9388 (3) | 0.6337 (2) | 0.0651 (11) | |
H25A | 0.3550 | 1.0056 | 0.6327 | 0.078* | |
H25B | 0.3750 | 0.9112 | 0.5896 | 0.078* | |
C26 | 0.3407 (4) | 0.8695 (5) | 0.6779 (3) | 0.0922 (17) | |
H26A | 0.2677 | 0.8639 | 0.6623 | 0.138* | |
H26B | 0.3521 | 0.8972 | 0.7214 | 0.138* | |
H26C | 0.3719 | 0.8029 | 0.6783 | 0.138* | |
N7 | 1.0571 (2) | 0.9156 (2) | 0.33784 (13) | 0.0388 (6) | |
N8 | 0.94503 (18) | 0.83233 (17) | 0.42692 (11) | 0.0304 (5) | |
C31 | 1.0478 (2) | 0.8152 (2) | 0.34338 (14) | 0.0351 (6) | |
C32 | 0.9918 (2) | 0.7729 (2) | 0.38859 (14) | 0.0342 (6) | |
H32 | 0.9872 | 0.7020 | 0.3920 | 0.041* | |
C33 | 0.9507 (2) | 0.9334 (2) | 0.41990 (14) | 0.0343 (6) | |
H33 | 0.9168 | 0.9766 | 0.4450 | 0.041* | |
C34 | 1.0071 (3) | 0.9746 (2) | 0.37515 (15) | 0.0400 (7) | |
H34 | 1.0102 | 1.0454 | 0.3710 | 0.048* | |
C35 | 1.1037 (3) | 0.7484 (3) | 0.30189 (17) | 0.0507 (8) | |
H35A | 1.1002 | 0.7795 | 0.2590 | 0.061* | |
H35B | 1.0698 | 0.6822 | 0.2961 | 0.061* | |
C36 | 1.2153 (4) | 0.7336 (4) | 0.3325 (3) | 0.0730 (13) | |
H36A | 1.2488 | 0.6908 | 0.3047 | 0.110* | |
H36B | 1.2189 | 0.7016 | 0.3745 | 0.110* | |
H36C | 1.2492 | 0.7990 | 0.3377 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.02445 (17) | 0.02944 (16) | 0.02865 (16) | 0.00116 (11) | 0.00215 (12) | −0.00022 (11) |
Cu2 | 0.02686 (18) | 0.02703 (16) | 0.03318 (17) | −0.00399 (11) | 0.00865 (13) | −0.00356 (12) |
Cu3 | 0.02969 (19) | 0.03035 (16) | 0.03218 (17) | 0.00490 (12) | 0.01158 (14) | −0.00290 (12) |
Cu4 | 0.02925 (18) | 0.03081 (16) | 0.02599 (16) | −0.00092 (12) | 0.00930 (13) | 0.00284 (11) |
Cl1 | 0.0415 (4) | 0.0261 (3) | 0.0627 (5) | 0.0023 (3) | −0.0092 (4) | −0.0010 (3) |
Cl2 | 0.0414 (4) | 0.0389 (3) | 0.0583 (4) | −0.0088 (3) | 0.0293 (4) | −0.0111 (3) |
Cl3 | 0.0531 (5) | 0.0467 (4) | 0.0465 (4) | 0.0230 (3) | 0.0226 (4) | 0.0160 (3) |
Cl4 | 0.0250 (3) | 0.0531 (4) | 0.0379 (3) | −0.0038 (3) | 0.0073 (3) | 0.0088 (3) |
Cl5 | 0.0370 (4) | 0.0436 (3) | 0.0292 (3) | 0.0086 (3) | 0.0052 (3) | −0.0062 (3) |
Cl6 | 0.0507 (4) | 0.0454 (4) | 0.0281 (3) | −0.0163 (3) | 0.0096 (3) | −0.0064 (3) |
O1 | 0.0228 (9) | 0.0242 (8) | 0.0253 (8) | 0.0000 (6) | 0.0074 (7) | −0.0007 (6) |
N1 | 0.0358 (15) | 0.0560 (16) | 0.0458 (15) | 0.0089 (12) | −0.0064 (12) | −0.0140 (12) |
N2 | 0.0287 (12) | 0.0314 (10) | 0.0296 (10) | −0.0002 (8) | 0.0018 (9) | 0.0009 (8) |
C1 | 0.0328 (16) | 0.0422 (15) | 0.0405 (15) | 0.0004 (12) | 0.0021 (12) | −0.0056 (12) |
C2 | 0.0336 (16) | 0.0413 (14) | 0.0336 (13) | 0.0030 (11) | −0.0013 (12) | −0.0067 (11) |
C3 | 0.0355 (16) | 0.0425 (15) | 0.0419 (16) | 0.0066 (12) | −0.0018 (13) | −0.0130 (12) |
C4 | 0.0412 (19) | 0.064 (2) | 0.0449 (17) | 0.0095 (15) | −0.0064 (15) | −0.0212 (16) |
C5 | 0.0384 (19) | 0.060 (2) | 0.061 (2) | 0.0137 (15) | −0.0082 (16) | −0.0200 (17) |
C6 | 0.068 (3) | 0.113 (4) | 0.078 (3) | 0.016 (3) | 0.029 (3) | −0.023 (3) |
N3 | 0.0423 (17) | 0.0449 (15) | 0.076 (2) | −0.0123 (12) | 0.0208 (15) | −0.0210 (14) |
N4 | 0.0299 (12) | 0.0324 (11) | 0.0369 (12) | −0.0052 (9) | 0.0093 (10) | −0.0034 (9) |
C11 | 0.0294 (15) | 0.0382 (14) | 0.0486 (16) | −0.0062 (11) | 0.0092 (13) | −0.0043 (12) |
C12 | 0.0301 (15) | 0.0352 (13) | 0.0445 (15) | −0.0032 (11) | 0.0126 (12) | −0.0049 (11) |
C13 | 0.0347 (16) | 0.0426 (15) | 0.0571 (19) | −0.0095 (12) | 0.0206 (14) | −0.0178 (14) |
C14 | 0.044 (2) | 0.0498 (18) | 0.086 (3) | −0.0123 (15) | 0.029 (2) | −0.0313 (19) |
C15 | 0.0319 (17) | 0.0543 (19) | 0.061 (2) | −0.0122 (13) | 0.0154 (15) | −0.0084 (16) |
C16 | 0.071 (3) | 0.135 (5) | 0.111 (5) | −0.014 (3) | 0.033 (3) | 0.061 (4) |
N5 | 0.0467 (17) | 0.0452 (14) | 0.0570 (17) | 0.0123 (12) | 0.0195 (14) | −0.0094 (12) |
N6 | 0.0365 (13) | 0.0334 (11) | 0.0365 (12) | 0.0056 (9) | 0.0142 (10) | −0.0020 (9) |
C21 | 0.0384 (17) | 0.0407 (15) | 0.0536 (18) | 0.0092 (13) | 0.0141 (14) | −0.0026 (13) |
C22 | 0.0370 (17) | 0.0397 (15) | 0.0474 (16) | 0.0069 (12) | 0.0092 (13) | −0.0114 (13) |
C23 | 0.0371 (16) | 0.0336 (13) | 0.0480 (16) | −0.0004 (11) | 0.0115 (13) | −0.0086 (12) |
C24 | 0.051 (2) | 0.0414 (16) | 0.0530 (18) | 0.0055 (14) | 0.0153 (16) | −0.0150 (14) |
C25 | 0.039 (2) | 0.066 (2) | 0.089 (3) | 0.0151 (17) | 0.008 (2) | −0.016 (2) |
C26 | 0.059 (3) | 0.107 (4) | 0.116 (5) | −0.022 (3) | 0.031 (3) | −0.018 (4) |
N7 | 0.0383 (14) | 0.0430 (13) | 0.0373 (12) | −0.0064 (10) | 0.0123 (11) | 0.0030 (10) |
N8 | 0.0300 (12) | 0.0340 (11) | 0.0277 (10) | −0.0016 (9) | 0.0066 (9) | 0.0023 (8) |
C31 | 0.0349 (15) | 0.0414 (14) | 0.0301 (13) | 0.0003 (11) | 0.0087 (12) | 0.0034 (11) |
C32 | 0.0392 (16) | 0.0322 (13) | 0.0326 (13) | 0.0017 (11) | 0.0105 (12) | 0.0020 (10) |
C33 | 0.0392 (16) | 0.0318 (13) | 0.0331 (13) | −0.0039 (11) | 0.0096 (12) | −0.0014 (10) |
C34 | 0.0491 (18) | 0.0324 (13) | 0.0400 (15) | −0.0095 (12) | 0.0119 (14) | −0.0008 (11) |
C35 | 0.062 (2) | 0.0537 (18) | 0.0426 (17) | 0.0075 (16) | 0.0258 (17) | 0.0025 (14) |
C36 | 0.055 (3) | 0.087 (3) | 0.084 (3) | 0.018 (2) | 0.031 (2) | 0.001 (2) |
Cu1—O1 | 1.9073 (18) | C12—H12 | 0.9300 |
Cu1—N2 | 1.986 (2) | C13—C14 | 1.381 (4) |
Cu1—Cl1 | 2.3555 (8) | C13—H13 | 0.9300 |
Cu1—Cl5 | 2.4005 (7) | C14—H14 | 0.9300 |
Cu1—Cl4 | 2.4438 (7) | C15—C16 | 1.486 (6) |
Cu2—O1 | 1.8946 (17) | C15—H15A | 0.9700 |
Cu2—N4 | 1.987 (2) | C15—H15B | 0.9700 |
Cu2—Cl2 | 2.3765 (7) | C16—H16A | 0.9600 |
Cu2—Cl6 | 2.4199 (8) | C16—H16B | 0.9600 |
Cu2—Cl1 | 2.4314 (9) | C16—H16C | 0.9600 |
Cu3—O1 | 1.8974 (16) | N5—C24 | 1.329 (5) |
Cu3—N6 | 1.978 (2) | N5—C21 | 1.331 (5) |
Cu3—Cl3 | 2.3485 (8) | N6—C22 | 1.329 (4) |
Cu3—Cl5 | 2.4196 (8) | N6—C23 | 1.331 (4) |
Cu3—Cl2 | 2.4591 (8) | C21—C22 | 1.397 (4) |
Cu4—O1 | 1.9010 (17) | C21—C25 | 1.494 (5) |
Cu4—N8 | 1.977 (2) | C22—H22 | 0.9300 |
Cu4—Cl4 | 2.3835 (8) | C23—C24 | 1.384 (4) |
Cu4—Cl6 | 2.3968 (8) | C23—H23 | 0.9300 |
Cu4—Cl3 | 2.4325 (8) | C24—H24 | 0.9300 |
N1—C4 | 1.325 (4) | C25—C26 | 1.493 (7) |
N1—C1 | 1.325 (4) | C25—H25A | 0.9700 |
N2—C3 | 1.329 (4) | C25—H25B | 0.9700 |
N2—C2 | 1.333 (4) | C26—H26A | 0.9600 |
C1—C2 | 1.394 (4) | C26—H26B | 0.9600 |
C1—C5 | 1.497 (4) | C26—H26C | 0.9600 |
C2—H2 | 0.9300 | N7—C31 | 1.323 (4) |
C3—C4 | 1.378 (5) | N7—C34 | 1.339 (4) |
C3—H3 | 0.9300 | N8—C33 | 1.330 (3) |
C4—H4 | 0.9300 | N8—C32 | 1.332 (4) |
C5—C6 | 1.507 (7) | C31—C32 | 1.398 (4) |
C5—H5A | 0.9700 | C31—C35 | 1.499 (4) |
C5—H5B | 0.9700 | C32—H32 | 0.9300 |
C6—H6A | 0.9600 | C33—C34 | 1.389 (4) |
C6—H6B | 0.9600 | C33—H33 | 0.9300 |
C6—H6C | 0.9600 | C34—H34 | 0.9300 |
N3—C11 | 1.322 (4) | C35—C36 | 1.507 (6) |
N3—C14 | 1.330 (4) | C35—H35A | 0.9700 |
N4—C13 | 1.327 (4) | C35—H35B | 0.9700 |
N4—C12 | 1.335 (4) | C36—H36A | 0.9600 |
C11—C12 | 1.390 (4) | C36—H36B | 0.9600 |
C11—C15 | 1.503 (4) | C36—H36C | 0.9600 |
O1—Cu1—N2 | 175.83 (8) | C13—N4—Cu2 | 118.9 (2) |
O1—Cu1—Cl1 | 86.05 (5) | C12—N4—Cu2 | 123.86 (19) |
N2—Cu1—Cl1 | 95.29 (7) | N3—C11—C12 | 121.0 (3) |
O1—Cu1—Cl5 | 84.77 (5) | N3—C11—C15 | 117.5 (3) |
N2—Cu1—Cl5 | 97.31 (7) | C12—C11—C15 | 121.5 (3) |
Cl1—Cu1—Cl5 | 130.20 (3) | N4—C12—C11 | 121.7 (3) |
O1—Cu1—Cl4 | 83.51 (5) | N4—C12—H12 | 119.1 |
N2—Cu1—Cl4 | 92.37 (7) | C11—C12—H12 | 119.1 |
Cl1—Cu1—Cl4 | 118.00 (3) | N4—C13—C14 | 120.4 (3) |
Cl5—Cu1—Cl4 | 109.37 (3) | N4—C13—H13 | 119.8 |
O1—Cu2—N4 | 177.53 (8) | C14—C13—H13 | 119.8 |
O1—Cu2—Cl2 | 85.20 (5) | N3—C14—C13 | 122.8 (3) |
N4—Cu2—Cl2 | 97.03 (7) | N3—C14—H14 | 118.6 |
O1—Cu2—Cl6 | 84.36 (5) | C13—C14—H14 | 118.6 |
N4—Cu2—Cl6 | 93.34 (7) | C16—C15—C11 | 111.7 (4) |
Cl2—Cu2—Cl6 | 132.44 (3) | C16—C15—H15A | 109.3 |
O1—Cu2—Cl1 | 84.18 (6) | C11—C15—H15A | 109.3 |
N4—Cu2—Cl1 | 95.83 (8) | C16—C15—H15B | 109.3 |
Cl2—Cu2—Cl1 | 114.02 (3) | C11—C15—H15B | 109.3 |
Cl6—Cu2—Cl1 | 110.85 (3) | H15A—C15—H15B | 107.9 |
O1—Cu3—N6 | 177.38 (10) | C15—C16—H16A | 109.5 |
O1—Cu3—Cl3 | 86.14 (5) | C15—C16—H16B | 109.5 |
N6—Cu3—Cl3 | 93.91 (7) | H16A—C16—H16B | 109.5 |
O1—Cu3—Cl5 | 84.44 (6) | C15—C16—H16C | 109.5 |
N6—Cu3—Cl5 | 97.62 (8) | H16A—C16—H16C | 109.5 |
Cl3—Cu3—Cl5 | 125.72 (3) | H16B—C16—H16C | 109.5 |
O1—Cu3—Cl2 | 82.84 (5) | C24—N5—C21 | 117.0 (3) |
N6—Cu3—Cl2 | 95.05 (7) | C22—N6—C23 | 117.9 (2) |
Cl3—Cu3—Cl2 | 126.99 (4) | C22—N6—Cu3 | 119.8 (2) |
Cl5—Cu3—Cl2 | 104.57 (3) | C23—N6—Cu3 | 122.3 (2) |
O1—Cu4—N8 | 174.92 (9) | N5—C21—C22 | 120.3 (3) |
O1—Cu4—Cl4 | 85.33 (6) | N5—C21—C25 | 118.5 (3) |
N8—Cu4—Cl4 | 89.72 (7) | C22—C21—C25 | 121.1 (3) |
O1—Cu4—Cl6 | 84.87 (5) | N6—C22—C21 | 121.8 (3) |
N8—Cu4—Cl6 | 97.38 (7) | N6—C22—H22 | 119.1 |
Cl4—Cu4—Cl6 | 128.47 (3) | C21—C22—H22 | 119.1 |
O1—Cu4—Cl3 | 83.70 (5) | N6—C23—C24 | 119.8 (3) |
N8—Cu4—Cl3 | 99.66 (7) | N6—C23—H23 | 120.1 |
Cl4—Cu4—Cl3 | 118.08 (3) | C24—C23—H23 | 120.1 |
Cl6—Cu4—Cl3 | 110.87 (4) | N5—C24—C23 | 123.1 (3) |
Cu1—Cl1—Cu2 | 80.13 (2) | N5—C24—H24 | 118.5 |
Cu2—Cl2—Cu3 | 79.59 (2) | C23—C24—H24 | 118.5 |
Cu3—Cl3—Cu4 | 80.54 (2) | C26—C25—C21 | 112.2 (4) |
Cu4—Cl4—Cu1 | 80.39 (2) | C26—C25—H25A | 109.2 |
Cu1—Cl5—Cu3 | 80.64 (2) | C21—C25—H25A | 109.2 |
Cu4—Cl6—Cu2 | 80.53 (2) | C26—C25—H25B | 109.2 |
Cu2—O1—Cu3 | 109.45 (8) | C21—C25—H25B | 109.2 |
Cu2—O1—Cu4 | 110.22 (8) | H25A—C25—H25B | 107.9 |
Cu3—O1—Cu4 | 108.94 (8) | C25—C26—H26A | 109.5 |
Cu2—O1—Cu1 | 108.30 (8) | C25—C26—H26B | 109.5 |
Cu3—O1—Cu1 | 110.12 (9) | H26A—C26—H26B | 109.5 |
Cu4—O1—Cu1 | 109.80 (8) | C25—C26—H26C | 109.5 |
C4—N1—C1 | 116.9 (3) | H26A—C26—H26C | 109.5 |
C3—N2—C2 | 117.3 (3) | H26B—C26—H26C | 109.5 |
C3—N2—Cu1 | 122.2 (2) | C31—N7—C34 | 117.2 (2) |
C2—N2—Cu1 | 120.52 (19) | C33—N8—C32 | 118.2 (2) |
N1—C1—C2 | 120.5 (3) | C33—N8—Cu4 | 121.25 (19) |
N1—C1—C5 | 117.8 (3) | C32—N8—Cu4 | 119.54 (19) |
C2—C1—C5 | 121.7 (3) | N7—C31—C32 | 121.0 (3) |
N2—C2—C1 | 121.9 (3) | N7—C31—C35 | 117.7 (3) |
N2—C2—H2 | 119.0 | C32—C31—C35 | 121.2 (3) |
C1—C2—H2 | 119.0 | N8—C32—C31 | 121.2 (3) |
N2—C3—C4 | 120.2 (3) | N8—C32—H32 | 119.4 |
N2—C3—H3 | 119.9 | C31—C32—H32 | 119.4 |
C4—C3—H3 | 119.9 | N8—C33—C34 | 120.2 (3) |
N1—C4—C3 | 123.1 (3) | N8—C33—H33 | 119.9 |
N1—C4—H4 | 118.4 | C34—C33—H33 | 119.9 |
C3—C4—H4 | 118.4 | N7—C34—C33 | 122.1 (3) |
C1—C5—C6 | 112.6 (4) | N7—C34—H34 | 118.9 |
C1—C5—H5A | 109.1 | C33—C34—H34 | 118.9 |
C6—C5—H5A | 109.1 | C31—C35—C36 | 111.6 (3) |
C1—C5—H5B | 109.1 | C31—C35—H35A | 109.3 |
C6—C5—H5B | 109.1 | C36—C35—H35A | 109.3 |
H5A—C5—H5B | 107.8 | C31—C35—H35B | 109.3 |
C5—C6—H6A | 109.5 | C36—C35—H35B | 109.3 |
C5—C6—H6B | 109.5 | H35A—C35—H35B | 108.0 |
H6A—C6—H6B | 109.5 | C35—C36—H36A | 109.5 |
C5—C6—H6C | 109.5 | C35—C36—H36B | 109.5 |
H6A—C6—H6C | 109.5 | H36A—C36—H36B | 109.5 |
H6B—C6—H6C | 109.5 | C35—C36—H36C | 109.5 |
C11—N3—C14 | 116.7 (3) | H36A—C36—H36C | 109.5 |
C13—N4—C12 | 117.2 (2) | H36B—C36—H36C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Cu4Cl6O(C6H8N2)4] |
Mr | 915.44 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 13.1203 (10), 13.0461 (7), 20.7233 (16) |
β (°) | 99.718 (9) |
V (Å3) | 3496.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.89 |
Crystal size (mm) | 0.14 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Stoe Imaging Plate Diffraction System diffractometer |
Absorption correction | Numerical (X-SHAPE; Stoe & Cie, 1998) |
Tmin, Tmax | 0.717, 0.849 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30661, 8309, 6876 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.663 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.100, 1.03 |
No. of reflections | 8309 |
No. of parameters | 389 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.57, −0.56 |
Computer programs: IPDS Program Package (Stoe & Cie, 1998), IPDS Program Package, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1998), CIFTAB in SHELXL97.
Cu1—O1 | 1.9073 (18) | Cu3—O1 | 1.8974 (16) |
Cu1—N2 | 1.986 (2) | Cu3—N6 | 1.978 (2) |
Cu1—Cl1 | 2.3555 (8) | Cu3—Cl3 | 2.3485 (8) |
Cu1—Cl5 | 2.4005 (7) | Cu3—Cl5 | 2.4196 (8) |
Cu1—Cl4 | 2.4438 (7) | Cu3—Cl2 | 2.4591 (8) |
Cu2—O1 | 1.8946 (17) | Cu4—O1 | 1.9010 (17) |
Cu2—N4 | 1.987 (2) | Cu4—N8 | 1.977 (2) |
Cu2—Cl2 | 2.3765 (7) | Cu4—Cl4 | 2.3835 (8) |
Cu2—Cl6 | 2.4199 (8) | Cu4—Cl6 | 2.3968 (8) |
Cu2—Cl1 | 2.4314 (9) | Cu4—Cl3 | 2.4325 (8) |
O1—Cu1—N2 | 175.83 (8) | O1—Cu3—Cl2 | 82.84 (5) |
O1—Cu1—Cl1 | 86.05 (5) | N6—Cu3—Cl2 | 95.05 (7) |
N2—Cu1—Cl1 | 95.29 (7) | Cl3—Cu3—Cl2 | 126.99 (4) |
O1—Cu1—Cl5 | 84.77 (5) | Cl5—Cu3—Cl2 | 104.57 (3) |
N2—Cu1—Cl5 | 97.31 (7) | O1—Cu4—N8 | 174.92 (9) |
Cl1—Cu1—Cl5 | 130.20 (3) | O1—Cu4—Cl4 | 85.33 (6) |
O1—Cu1—Cl4 | 83.51 (5) | N8—Cu4—Cl4 | 89.72 (7) |
N2—Cu1—Cl4 | 92.37 (7) | O1—Cu4—Cl6 | 84.87 (5) |
Cl1—Cu1—Cl4 | 118.00 (3) | N8—Cu4—Cl6 | 97.38 (7) |
Cl5—Cu1—Cl4 | 109.37 (3) | Cl4—Cu4—Cl6 | 128.47 (3) |
O1—Cu2—N4 | 177.53 (8) | O1—Cu4—Cl3 | 83.70 (5) |
O1—Cu2—Cl2 | 85.20 (5) | N8—Cu4—Cl3 | 99.66 (7) |
N4—Cu2—Cl2 | 97.03 (7) | Cl4—Cu4—Cl3 | 118.08 (3) |
O1—Cu2—Cl6 | 84.36 (5) | Cl6—Cu4—Cl3 | 110.87 (4) |
N4—Cu2—Cl6 | 93.34 (7) | Cu1—Cl1—Cu2 | 80.13 (2) |
Cl2—Cu2—Cl6 | 132.44 (3) | Cu2—Cl2—Cu3 | 79.59 (2) |
O1—Cu2—Cl1 | 84.18 (6) | Cu3—Cl3—Cu4 | 80.54 (2) |
N4—Cu2—Cl1 | 95.83 (8) | Cu4—Cl4—Cu1 | 80.39 (2) |
Cl2—Cu2—Cl1 | 114.02 (3) | Cu1—Cl5—Cu3 | 80.64 (2) |
Cl6—Cu2—Cl1 | 110.85 (3) | Cu4—Cl6—Cu2 | 80.53 (2) |
O1—Cu3—N6 | 177.38 (10) | Cu2—O1—Cu3 | 109.45 (8) |
O1—Cu3—Cl3 | 86.14 (5) | Cu2—O1—Cu4 | 110.22 (8) |
N6—Cu3—Cl3 | 93.91 (7) | Cu3—O1—Cu4 | 108.94 (8) |
O1—Cu3—Cl5 | 84.44 (6) | Cu2—O1—Cu1 | 108.30 (8) |
N6—Cu3—Cl5 | 97.62 (8) | Cu3—O1—Cu1 | 110.12 (9) |
Cl3—Cu3—Cl5 | 125.72 (3) | Cu4—O1—Cu1 | 109.80 (8) |
This work is a part of a project dealing with the synthesis, structures and properties of coordination polymers based on copper halides and multidentate amino ligands (Näther, Jess & Greve, 2001; Näther & Greve, 2001; Näther & Jess, 2001). Crystals of the title compound, (I), were obtained by the reaction of copper(I) chloride with 2-ethylpyrazine in acetonitrile. In the crystal structure of the title compound, four copper(II) cations form an slightly distorted tetrahedron which is centred by an interstitiel O atom. The Cu—O bond lengths are between 1.895 (2) and 1.907 (2) Å, and the Cu—O—Cu angles between 108.30 (8) and 110.22 (8)°. The edges of the Cu4 tetrahedron are each connected via µ2-chloro ligands. The chlorine ligands are not symmetrically surrounded by the copper(II) cations and the Cu—Cl bond lengths range between 2.3485 (8) and 2.4591 (8) Å. The copper coordination is completed by one additional 2-ethylpyrazine ligand which is coordinated by the N atom which is not adjacent to the ethyl group. The Cu—N bond lengths are between 1.977 (3) and 1.987 (2) Å. Presumably due to steric repulsion the second N atom of the 2-ethylpyrazine ligand is not involved in copper coordination. Bond lengths and angles are comparable to those in other amine-coordinated Cu4Cl6O clusters, like in µ4-oxo-hexakis(µ2-chloro)tetrakis(nicotine-N)tetracopper(II) (Haendler, 1990), µ4-oxo-hexakis(µ2-chloro)tetrakis(acetonitrile-N)tetracopper(II) acetonitrile solvate (Hiller et al., 1990), µ4-oxo-hexakis(µ2-chloro)tetrakis(imidazole-N)tetracopper(II) (Atria et al., 1999) and µ4-oxo-hexakis(µ2-chloro)tris(N-methyl-2- pyrrolidinone-O)aquatetracopper(II) (Churchill & Rotella, 1978).