Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046430/bt2517sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046430/bt2517Isup2.hkl |
CCDC reference: 663658
In a long 0.8 cm diameter tube was placed an aqueous (5 ml) solution of copper(II) acetate monohydrate (0.5 mmol). A methanol solution (5 ml) of 2,4,5-triiodobenzoic acid (1 mmol) was layered over this. After several days, blue prisms separated from solution. The C&H elemental percentages were C 16.43 and H 0.58% (versus calculated values of C 16.35 and H 0.82%).
The aromatic rings were refined as rigid hexagons of 1.39 Å sides. The anisotropic temperature factors of the free methanol molecule were restrained to be nearly isotropic. Carbon-bound H atoms were generated geometrically (C–H 0.93 – 0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C). The water and methanolic H atoms were placed in chemically sensible positions on the basis of hydrogen bonding interactions but they were not refined; U(H) was set to 1.5Ueq(O). The final difference Fourier map had peaks/holes in the vicinity of the iodine atoms.
There are many examples of di(ligand)tetra(carboxylato)dicopper compounds in which the carboxylate group bridges two copper atoms that are separated by a distance less than the sum of the van der Waals radius of copper. The Cambridge Structural Database (Version 5.28, Nov. 2006) lists more than 500 entries.
There are many examples of such di(ligand)tetra(carboxylato)dicopper compounds in which the carboxylate group bridges two copper atoms that are separated by a distance less than the sum of the van der Waals radius of copper. The Cambridge Structural Database (Version 5.28, November 2006) lists more than 500 entries.
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
[Cu2(C7H2I3O2)4(H2O)2][Cu2(C7H2I3O2)4(CH4O)2]·2CH4O | Z = 1 |
Mr = 4408.65 | F(000) = 1960 |
Triclinic, P1 | Dx = 2.971 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9321 (6) Å | Cell parameters from 18920 reflections |
b = 11.9345 (6) Å | θ = 3.0–27.5° |
c = 17.921 (1) Å | µ = 8.43 mm−1 |
α = 96.799 (1)° | T = 295 K |
β = 103.136 (1)° | Prism, blue |
γ = 91.532 (1)° | 0.24 × 0.19 × 0.14 mm |
V = 2464.0 (2) Å3 |
Rigaku R-AXIS RAPID IP diffractometer | 11203 independent reflections |
Radiation source: fine-focus sealed tube | 9161 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→15 |
Tmin = 0.084, Tmax = 1.00 | k = −15→14 |
24361 measured reflections | l = −23→23 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.078P)2 + 3.5241P] where P = (Fo2 + 2Fc2)/3 |
11203 reflections | (Δ/σ)max = 0.001 |
449 parameters | Δρmax = 2.37 e Å−3 |
14 restraints | Δρmin = −1.51 e Å−3 |
[Cu2(C7H2I3O2)4(H2O)2][Cu2(C7H2I3O2)4(CH4O)2]·2CH4O | γ = 91.532 (1)° |
Mr = 4408.65 | V = 2464.0 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 11.9321 (6) Å | Mo Kα radiation |
b = 11.9345 (6) Å | µ = 8.43 mm−1 |
c = 17.921 (1) Å | T = 295 K |
α = 96.799 (1)° | 0.24 × 0.19 × 0.14 mm |
β = 103.136 (1)° |
Rigaku R-AXIS RAPID IP diffractometer | 11203 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 9161 reflections with I > 2σ(I) |
Tmin = 0.084, Tmax = 1.00 | Rint = 0.050 |
24361 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 14 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.06 | Δρmax = 2.37 e Å−3 |
11203 reflections | Δρmin = −1.51 e Å−3 |
449 parameters |
x | y | z | Uiso*/Ueq | ||
I1 | 1.21746 (5) | 1.31313 (5) | 0.68454 (3) | 0.05455 (15) | |
I2 | 1.16902 (5) | 1.60545 (5) | 0.74506 (4) | 0.05628 (16) | |
I3 | 0.72402 (5) | 1.56610 (5) | 0.50800 (4) | 0.05953 (17) | |
I4 | 0.41538 (4) | 0.71789 (4) | 0.45628 (3) | 0.04599 (14) | |
I5 | 0.66311 (5) | 1.18239 (5) | 0.33814 (3) | 0.05117 (15) | |
I6 | 0.35562 (5) | 1.14333 (5) | 0.31042 (4) | 0.05908 (17) | |
I7 | 1.38248 (5) | 0.89448 (5) | 1.14510 (4) | 0.06038 (17) | |
I8 | 1.55290 (4) | 0.64621 (5) | 1.12823 (4) | 0.06330 (18) | |
I9 | 1.13581 (5) | 0.38570 (4) | 0.93389 (4) | 0.05658 (16) | |
I10 | 0.88626 (5) | 0.63810 (5) | 0.81397 (4) | 0.06055 (17) | |
I11 | 0.61385 (5) | 0.49247 (5) | 0.71699 (4) | 0.05900 (16) | |
I12 | 0.37236 (4) | 0.80116 (5) | 0.90462 (3) | 0.05159 (15) | |
Cu1 | 0.98855 (7) | 0.97560 (7) | 0.56782 (5) | 0.03541 (19) | |
Cu2 | 1.02862 (6) | 1.00342 (6) | 0.93345 (4) | 0.02765 (16) | |
O1 | 0.9864 (5) | 1.1416 (4) | 0.5920 (3) | 0.0445 (12) | |
O2 | 1.0072 (5) | 1.1823 (4) | 0.4774 (3) | 0.0487 (13) | |
O3 | 0.8236 (4) | 0.9712 (5) | 0.5188 (3) | 0.0488 (13) | |
O4 | 0.8441 (4) | 1.0097 (5) | 0.4027 (3) | 0.0443 (12) | |
O5 | 1.1244 (4) | 0.8783 (4) | 0.9646 (3) | 0.0408 (11) | |
O6 | 1.0761 (4) | 0.8700 (4) | 1.0779 (3) | 0.0440 (12) | |
O7 | 0.8965 (4) | 0.8963 (4) | 0.8912 (3) | 0.0427 (11) | |
O8 | 0.8489 (4) | 0.8904 (4) | 1.0042 (3) | 0.0380 (11) | |
O9 | 1.0766 (6) | 1.0293 (7) | 0.8275 (4) | 0.077 (2) | |
H9o | 1.0351 | 1.0832 | 0.8096 | 0.115* | |
O10 | 0.9491 (14) | 1.1794 (14) | 0.7471 (9) | 0.181 (6) | |
H10o | 1.0010 | 1.2137 | 0.7270 | 0.272* | |
O1w | 0.9549 (6) | 0.9362 (10) | 0.6753 (4) | 0.097 (3) | |
H1w1 | 1.0140 | 0.9077 | 0.7008 | 0.145* | |
H1w2 | 0.9426 | 0.9975 | 0.7015 | 0.145* | |
C1 | 0.9970 (6) | 1.2078 (6) | 0.5447 (4) | 0.0386 (15) | |
C2 | 0.9899 (4) | 1.3311 (3) | 0.5709 (3) | 0.0394 (15) | |
C3 | 1.0703 (3) | 1.3925 (4) | 0.6314 (3) | 0.0384 (15) | |
C4 | 1.0540 (4) | 1.5050 (4) | 0.6545 (2) | 0.0447 (17) | |
C5 | 0.9575 (4) | 1.5562 (3) | 0.6172 (3) | 0.0449 (17) | |
H5 | 0.9466 | 1.6315 | 0.6327 | 0.054* | |
C6 | 0.8771 (3) | 1.4948 (4) | 0.5568 (3) | 0.0416 (16) | |
C7 | 0.8933 (3) | 1.3823 (4) | 0.5336 (2) | 0.0426 (16) | |
H7 | 0.8396 | 1.3412 | 0.4932 | 0.051* | |
C8 | 0.7861 (6) | 0.9872 (6) | 0.4502 (4) | 0.0392 (15) | |
C9 | 0.6566 (2) | 0.9741 (3) | 0.4221 (3) | 0.0340 (14) | |
C10 | 0.5875 (3) | 1.0486 (3) | 0.3809 (3) | 0.0350 (14) | |
C11 | 0.4683 (3) | 1.0310 (3) | 0.3632 (3) | 0.0346 (14) | |
C12 | 0.4181 (2) | 0.9388 (4) | 0.3866 (3) | 0.0408 (16) | |
H12 | 0.3383 | 0.9270 | 0.3748 | 0.049* | |
C13 | 0.4872 (3) | 0.8643 (3) | 0.4278 (3) | 0.0374 (14) | |
C14 | 0.6064 (3) | 0.8819 (3) | 0.4455 (3) | 0.0355 (14) | |
H14 | 0.6526 | 0.8321 | 0.4730 | 0.043* | |
C15 | 1.1284 (6) | 0.8369 (5) | 1.0268 (4) | 0.0339 (14) | |
C16 | 1.1994 (3) | 0.7351 (3) | 1.0369 (3) | 0.0368 (14) | |
C17 | 1.3128 (3) | 0.7405 (3) | 1.0795 (3) | 0.0354 (14) | |
C18 | 1.3761 (3) | 0.6444 (3) | 1.0802 (3) | 0.0394 (15) | |
C19 | 1.3261 (3) | 0.5429 (3) | 1.0382 (3) | 0.0397 (15) | |
H19 | 1.3685 | 0.4786 | 1.0386 | 0.048* | |
C20 | 1.2127 (3) | 0.5375 (3) | 0.9956 (3) | 0.0385 (15) | |
C21 | 1.1493 (3) | 0.6335 (3) | 0.9950 (3) | 0.0365 (15) | |
H21 | 1.0735 | 0.6299 | 0.9665 | 0.044* | |
C22 | 0.8351 (6) | 0.8618 (5) | 0.9338 (4) | 0.0337 (14) | |
C23 | 0.7314 (3) | 0.7821 (3) | 0.8958 (2) | 0.0351 (14) | |
C24 | 0.7315 (3) | 0.6902 (3) | 0.8404 (3) | 0.0358 (14) | |
C25 | 0.6289 (4) | 0.6292 (3) | 0.8038 (2) | 0.0357 (14) | |
C26 | 0.5263 (3) | 0.6601 (3) | 0.8228 (3) | 0.0402 (16) | |
H26 | 0.4577 | 0.6192 | 0.7983 | 0.048* | |
C27 | 0.5263 (3) | 0.7520 (4) | 0.8782 (3) | 0.0364 (14) | |
C28 | 0.6289 (3) | 0.8130 (3) | 0.9147 (2) | 0.0379 (15) | |
H28 | 0.6288 | 0.8745 | 0.9518 | 0.045* | |
C29 | 1.1933 (8) | 1.0578 (10) | 0.8206 (7) | 0.083 (4) | |
H29A | 1.1922 | 1.0662 | 0.7679 | 0.125* | |
H29B | 1.2425 | 0.9985 | 0.8366 | 0.125* | |
H29C | 1.2219 | 1.1274 | 0.8529 | 0.125* | |
C30 | 0.8630 (11) | 1.2632 (11) | 0.7502 (8) | 0.087 (3) | |
H30A | 0.8062 | 1.2359 | 0.7750 | 0.131* | |
H30B | 0.8264 | 1.2762 | 0.6987 | 0.131* | |
H30C | 0.8997 | 1.3326 | 0.7790 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0427 (3) | 0.0641 (3) | 0.0515 (3) | 0.0108 (2) | −0.0035 (2) | 0.0118 (2) |
I2 | 0.0454 (3) | 0.0580 (3) | 0.0587 (3) | −0.0114 (3) | 0.0063 (2) | −0.0049 (2) |
I3 | 0.0456 (3) | 0.0604 (3) | 0.0766 (4) | 0.0172 (3) | 0.0102 (3) | 0.0293 (3) |
I4 | 0.0468 (3) | 0.0389 (2) | 0.0528 (3) | −0.0049 (2) | 0.0148 (2) | 0.0034 (2) |
I5 | 0.0510 (3) | 0.0535 (3) | 0.0531 (3) | 0.0009 (2) | 0.0138 (2) | 0.0205 (2) |
I6 | 0.0471 (3) | 0.0586 (3) | 0.0710 (4) | 0.0181 (3) | 0.0022 (3) | 0.0256 (3) |
I7 | 0.0575 (3) | 0.0460 (3) | 0.0636 (4) | 0.0062 (3) | −0.0065 (3) | −0.0103 (2) |
I8 | 0.0321 (2) | 0.0648 (3) | 0.0835 (4) | 0.0146 (2) | −0.0063 (3) | 0.0067 (3) |
I9 | 0.0474 (3) | 0.0323 (2) | 0.0854 (4) | 0.0019 (2) | 0.0109 (3) | −0.0023 (2) |
I10 | 0.0411 (3) | 0.0685 (3) | 0.0666 (4) | 0.0092 (3) | 0.0138 (2) | −0.0174 (3) |
I11 | 0.0632 (3) | 0.0478 (3) | 0.0585 (3) | −0.0039 (3) | 0.0112 (3) | −0.0166 (2) |
I12 | 0.0370 (2) | 0.0694 (3) | 0.0492 (3) | 0.0042 (2) | 0.0141 (2) | 0.0025 (2) |
Cu1 | 0.0273 (4) | 0.0489 (5) | 0.0301 (4) | 0.0029 (3) | 0.0070 (3) | 0.0044 (3) |
Cu2 | 0.0285 (3) | 0.0262 (3) | 0.0290 (4) | 0.0054 (3) | 0.0078 (3) | 0.0037 (3) |
O1 | 0.047 (3) | 0.045 (3) | 0.042 (3) | 0.007 (2) | 0.012 (2) | 0.005 (2) |
O2 | 0.059 (3) | 0.047 (3) | 0.042 (3) | 0.002 (3) | 0.016 (2) | 0.003 (2) |
O3 | 0.028 (2) | 0.077 (4) | 0.041 (3) | 0.004 (2) | 0.004 (2) | 0.018 (3) |
O4 | 0.033 (2) | 0.061 (3) | 0.041 (3) | 0.007 (2) | 0.010 (2) | 0.013 (2) |
O5 | 0.041 (3) | 0.037 (2) | 0.047 (3) | 0.016 (2) | 0.012 (2) | 0.007 (2) |
O6 | 0.044 (3) | 0.043 (3) | 0.049 (3) | 0.020 (2) | 0.014 (2) | 0.013 (2) |
O7 | 0.036 (2) | 0.047 (3) | 0.042 (3) | −0.007 (2) | 0.008 (2) | −0.002 (2) |
O8 | 0.040 (2) | 0.038 (2) | 0.035 (3) | −0.005 (2) | 0.009 (2) | 0.0035 (19) |
O9 | 0.091 (5) | 0.101 (5) | 0.049 (4) | −0.007 (4) | 0.040 (4) | 0.010 (4) |
O10 | 0.214 (10) | 0.183 (9) | 0.150 (9) | 0.073 (8) | 0.039 (7) | 0.030 (7) |
O1w | 0.062 (4) | 0.191 (10) | 0.040 (4) | 0.009 (5) | 0.013 (3) | 0.025 (5) |
C1 | 0.032 (3) | 0.047 (4) | 0.034 (4) | 0.007 (3) | 0.003 (3) | 0.006 (3) |
C2 | 0.032 (3) | 0.047 (4) | 0.038 (4) | 0.003 (3) | 0.006 (3) | 0.007 (3) |
C3 | 0.028 (3) | 0.051 (4) | 0.039 (4) | 0.006 (3) | 0.009 (3) | 0.010 (3) |
C4 | 0.038 (4) | 0.044 (4) | 0.052 (4) | −0.003 (3) | 0.009 (3) | 0.006 (3) |
C5 | 0.047 (4) | 0.041 (4) | 0.047 (4) | 0.004 (3) | 0.013 (3) | 0.004 (3) |
C6 | 0.032 (3) | 0.047 (4) | 0.049 (4) | 0.010 (3) | 0.010 (3) | 0.017 (3) |
C7 | 0.037 (3) | 0.047 (4) | 0.042 (4) | 0.004 (3) | 0.005 (3) | 0.005 (3) |
C8 | 0.026 (3) | 0.042 (3) | 0.044 (4) | −0.001 (3) | 0.005 (3) | −0.005 (3) |
C9 | 0.025 (3) | 0.036 (3) | 0.040 (4) | 0.005 (3) | 0.008 (3) | −0.001 (3) |
C10 | 0.042 (3) | 0.032 (3) | 0.031 (3) | 0.000 (3) | 0.010 (3) | 0.002 (2) |
C11 | 0.030 (3) | 0.039 (3) | 0.035 (3) | 0.011 (3) | 0.004 (3) | 0.011 (3) |
C12 | 0.027 (3) | 0.044 (4) | 0.046 (4) | 0.004 (3) | −0.001 (3) | 0.002 (3) |
C13 | 0.036 (3) | 0.037 (3) | 0.037 (4) | 0.003 (3) | 0.006 (3) | 0.000 (3) |
C14 | 0.029 (3) | 0.037 (3) | 0.036 (3) | 0.000 (3) | 0.001 (3) | 0.003 (3) |
C15 | 0.035 (3) | 0.025 (3) | 0.040 (4) | 0.009 (3) | 0.004 (3) | 0.003 (2) |
C16 | 0.037 (3) | 0.033 (3) | 0.044 (4) | 0.015 (3) | 0.013 (3) | 0.008 (3) |
C17 | 0.036 (3) | 0.034 (3) | 0.036 (3) | 0.008 (3) | 0.005 (3) | 0.006 (3) |
C18 | 0.031 (3) | 0.046 (4) | 0.040 (4) | 0.018 (3) | 0.001 (3) | 0.009 (3) |
C19 | 0.038 (3) | 0.032 (3) | 0.049 (4) | 0.014 (3) | 0.005 (3) | 0.012 (3) |
C20 | 0.036 (3) | 0.029 (3) | 0.051 (4) | 0.008 (3) | 0.008 (3) | 0.008 (3) |
C21 | 0.030 (3) | 0.028 (3) | 0.050 (4) | 0.004 (3) | 0.005 (3) | 0.008 (3) |
C22 | 0.035 (3) | 0.028 (3) | 0.038 (4) | 0.001 (3) | 0.006 (3) | 0.009 (3) |
C23 | 0.033 (3) | 0.032 (3) | 0.040 (4) | 0.005 (3) | 0.007 (3) | 0.007 (3) |
C24 | 0.036 (3) | 0.030 (3) | 0.039 (4) | 0.006 (3) | 0.006 (3) | 0.001 (3) |
C25 | 0.043 (3) | 0.029 (3) | 0.035 (3) | 0.007 (3) | 0.008 (3) | 0.004 (3) |
C26 | 0.039 (3) | 0.035 (3) | 0.041 (4) | −0.003 (3) | 0.002 (3) | 0.001 (3) |
C27 | 0.032 (3) | 0.041 (3) | 0.038 (4) | 0.000 (3) | 0.009 (3) | 0.012 (3) |
C28 | 0.034 (3) | 0.040 (3) | 0.039 (4) | 0.004 (3) | 0.008 (3) | 0.003 (3) |
C29 | 0.095 (8) | 0.093 (8) | 0.095 (9) | 0.039 (6) | 0.067 (7) | 0.053 (7) |
C30 | 0.086 (6) | 0.098 (7) | 0.084 (7) | 0.017 (6) | 0.026 (5) | 0.023 (6) |
I1—C3 | 2.105 (3) | C1—C2 | 1.501 (8) |
I2—C4 | 2.095 (3) | C2—C3 | 1.3900 |
I3—C6 | 2.088 (3) | C2—C7 | 1.3900 |
I4—C13 | 2.092 (3) | C3—C4 | 1.3900 |
I5—C10 | 2.116 (3) | C4—C5 | 1.3900 |
I6—C11 | 2.078 (3) | C5—C6 | 1.3900 |
I7—C17 | 2.100 (3) | C5—H5 | 0.9300 |
I8—C18 | 2.088 (3) | C6—C7 | 1.3900 |
I9—C20 | 2.079 (3) | C7—H7 | 0.9300 |
I10—C24 | 2.100 (3) | C8—C9 | 1.511 (7) |
I11—C25 | 2.091 (3) | C9—C10 | 1.3900 |
I12—C27 | 2.081 (3) | C9—C14 | 1.3900 |
Cu1—O4i | 1.944 (5) | C10—C11 | 1.3900 |
Cu1—O3 | 1.961 (5) | C11—C12 | 1.3900 |
Cu1—O2i | 1.968 (5) | C12—C13 | 1.3900 |
Cu1—O1 | 1.979 (5) | C12—H12 | 0.9300 |
Cu1—O1w | 2.156 (7) | C13—C14 | 1.3900 |
Cu1—Cu1i | 2.6365 (17) | C14—H14 | 0.9300 |
Cu2—O8ii | 1.952 (4) | C15—C16 | 1.505 (7) |
Cu2—O7 | 1.953 (5) | C16—C17 | 1.3900 |
Cu2—O5 | 1.961 (5) | C16—C21 | 1.3900 |
Cu2—O6ii | 1.986 (5) | C17—C18 | 1.3900 |
Cu2—O9 | 2.156 (6) | C18—C19 | 1.3900 |
Cu2—Cu2ii | 2.6355 (15) | C19—C20 | 1.3900 |
O1—C1 | 1.249 (9) | C19—H19 | 0.9300 |
O2—C1 | 1.244 (9) | C20—C21 | 1.3900 |
O2—Cu1i | 1.968 (5) | C21—H21 | 0.9300 |
O3—C8 | 1.248 (9) | C22—C23 | 1.516 (7) |
O4—C8 | 1.259 (9) | C23—C24 | 1.3900 |
O4—Cu1i | 1.944 (5) | C23—C28 | 1.3900 |
O5—C15 | 1.263 (9) | C24—C25 | 1.3900 |
O6—C15 | 1.254 (9) | C25—C26 | 1.3900 |
O6—Cu2ii | 1.986 (5) | C26—C27 | 1.3900 |
O7—C22 | 1.265 (8) | C26—H26 | 0.9300 |
O8—C22 | 1.240 (8) | C27—C28 | 1.3900 |
O8—Cu2ii | 1.952 (4) | C28—H28 | 0.9300 |
O9—C29 | 1.460 (8) | C29—H29A | 0.9600 |
O9—H9o | 0.87 | C29—H29B | 0.9600 |
O10—C30 | 1.457 (9) | C29—H29C | 0.9600 |
O10—H10o | 0.90 | C30—H30A | 0.9600 |
O1w—H1w1 | 0.85 | C30—H30B | 0.9600 |
O1w—H1w2 | 0.86 | C30—H30C | 0.9600 |
O4i—Cu1—O3 | 168.5 (2) | C14—C9—C8 | 114.2 (4) |
O4i—Cu1—O2i | 90.9 (2) | C9—C10—C11 | 120.0 |
O3—Cu1—O2i | 89.1 (3) | C9—C10—I5 | 120.3 (2) |
O4i—Cu1—O1 | 88.6 (2) | C11—C10—I5 | 119.6 (2) |
O3—Cu1—O1 | 89.0 (2) | C12—C11—C10 | 120.0 |
O2i—Cu1—O1 | 168.2 (2) | C12—C11—I6 | 116.2 (2) |
O4i—Cu1—O1w | 99.3 (3) | C10—C11—I6 | 123.6 (2) |
O3—Cu1—O1w | 92.2 (3) | C13—C12—C11 | 120.0 |
O2i—Cu1—O1w | 95.8 (3) | C13—C12—H12 | 120.0 |
O1—Cu1—O1w | 95.9 (3) | C11—C12—H12 | 120.0 |
O4i—Cu1—Cu1i | 85.34 (16) | C12—C13—C14 | 120.0 |
O3—Cu1—Cu1i | 83.20 (16) | C12—C13—I4 | 121.0 (2) |
O2i—Cu1—Cu1i | 84.59 (17) | C14—C13—I4 | 118.9 (2) |
O1—Cu1—Cu1i | 83.64 (16) | C13—C14—C9 | 120.0 |
O1w—Cu1—Cu1i | 175.3 (2) | C13—C14—H14 | 120.0 |
O8ii—Cu2—O7 | 168.1 (2) | C9—C14—H14 | 120.0 |
O8ii—Cu2—O5 | 89.1 (2) | O6—C15—O5 | 126.3 (6) |
O7—Cu2—O5 | 89.9 (2) | O6—C15—C16 | 118.4 (6) |
O8ii—Cu2—O6ii | 89.1 (2) | O5—C15—C16 | 115.2 (6) |
O7—Cu2—O6ii | 89.6 (2) | C17—C16—C21 | 120.0 |
O5—Cu2—O6ii | 168.7 (2) | C17—C16—C15 | 123.5 (3) |
O8ii—Cu2—O9 | 92.7 (2) | C21—C16—C15 | 116.2 (3) |
O7—Cu2—O9 | 99.1 (3) | C16—C17—C18 | 120.0 |
O5—Cu2—O9 | 100.8 (3) | C16—C17—I7 | 118.5 (2) |
O6ii—Cu2—O9 | 90.5 (3) | C18—C17—I7 | 121.5 (2) |
O8ii—Cu2—Cu2ii | 83.02 (15) | C19—C18—C17 | 120.0 |
O7—Cu2—Cu2ii | 85.12 (16) | C19—C18—I8 | 115.8 (2) |
O5—Cu2—Cu2ii | 83.98 (16) | C17—C18—I8 | 123.6 (2) |
O6ii—Cu2—Cu2ii | 84.68 (17) | C18—C19—C20 | 120.0 |
O9—Cu2—Cu2ii | 173.6 (2) | C18—C19—H19 | 120.0 |
C1—O1—Cu1 | 122.6 (5) | C20—C19—H19 | 120.0 |
C1—O2—Cu1i | 122.1 (5) | C19—C20—C21 | 120.0 |
C8—O3—Cu1 | 123.0 (5) | C19—C20—I9 | 120.5 (2) |
C8—O4—Cu1i | 121.1 (4) | C21—C20—I9 | 119.5 (2) |
C15—O5—Cu2 | 123.4 (5) | C20—C21—C16 | 120.0 |
C15—O6—Cu2ii | 121.6 (4) | C20—C21—H21 | 120.0 |
C22—O7—Cu2 | 121.4 (4) | C16—C21—H21 | 120.0 |
C22—O8—Cu2ii | 124.5 (4) | O8—C22—O7 | 126.0 (6) |
C29—O9—Cu2 | 125.2 (6) | O8—C22—C23 | 116.0 (6) |
C29—O9—H9o | 105.5 | O7—C22—C23 | 118.0 (6) |
Cu2—O9—H9o | 105.7 | C24—C23—C28 | 120.0 |
C30—O10—H10o | 103.6 | C24—C23—C22 | 124.8 (4) |
Cu1—O1w—H1w1 | 109.0 | C28—C23—C22 | 114.9 (4) |
Cu1—O1w—H1w2 | 108.7 | C25—C24—C23 | 120.0 |
H1w1—O1w—H1w2 | 108.7 | C25—C24—I10 | 119.3 (2) |
O2—C1—O1 | 127.1 (7) | C23—C24—I10 | 120.7 (2) |
O2—C1—C2 | 116.7 (6) | C26—C25—C24 | 120.0 |
O1—C1—C2 | 116.1 (6) | C26—C25—I11 | 115.4 (2) |
C3—C2—C7 | 120.0 | C24—C25—I11 | 124.6 (2) |
C3—C2—C1 | 123.7 (4) | C25—C26—C27 | 120.0 |
C7—C2—C1 | 116.2 (4) | C25—C26—H26 | 120.0 |
C4—C3—C2 | 120.0 | C27—C26—H26 | 120.0 |
C4—C3—I1 | 121.1 (2) | C26—C27—C28 | 120.0 |
C2—C3—I1 | 118.8 (2) | C26—C27—I12 | 120.2 (2) |
C3—C4—C5 | 120.0 | C28—C27—I12 | 119.8 (2) |
C3—C4—I2 | 123.3 (2) | C27—C28—C23 | 120.0 |
C5—C4—I2 | 116.7 (2) | C27—C28—H28 | 120.0 |
C6—C5—C4 | 120.0 | C23—C28—H28 | 120.0 |
C6—C5—H5 | 120.0 | O9—C29—H29A | 109.5 |
C4—C5—H5 | 120.0 | O9—C29—H29B | 109.5 |
C7—C6—C5 | 120.0 | H29A—C29—H29B | 109.5 |
C7—C6—I3 | 119.6 (2) | O9—C29—H29C | 109.5 |
C5—C6—I3 | 120.1 (2) | H29A—C29—H29C | 109.5 |
C6—C7—C2 | 120.0 | H29B—C29—H29C | 109.5 |
C6—C7—H7 | 120.0 | O10—C30—H30A | 109.5 |
C2—C7—H7 | 120.0 | O10—C30—H30B | 109.5 |
O3—C8—O4 | 127.3 (6) | H30A—C30—H30B | 109.5 |
O3—C8—C9 | 114.9 (6) | O10—C30—H30C | 109.5 |
O4—C8—C9 | 117.8 (6) | H30A—C30—H30C | 109.5 |
C10—C9—C14 | 120.0 | H30B—C30—H30C | 109.5 |
C10—C9—C8 | 125.7 (4) | ||
O4i—Cu1—O1—C1 | 84.2 (6) | C9—C10—C11—C12 | 0.0 |
O3—Cu1—O1—C1 | −84.5 (6) | I5—C10—C11—C12 | 175.7 (3) |
O2i—Cu1—O1—C1 | −3.5 (14) | C9—C10—C11—I6 | 174.6 (4) |
O1w—Cu1—O1—C1 | −176.6 (6) | I5—C10—C11—I6 | −9.7 (3) |
Cu1i—Cu1—O1—C1 | −1.2 (5) | C10—C11—C12—C13 | 0.0 |
O4i—Cu1—O3—C8 | 7.2 (17) | I6—C11—C12—C13 | −175.0 (3) |
O2i—Cu1—O3—C8 | −83.1 (6) | C11—C12—C13—C14 | 0.0 |
O1—Cu1—O3—C8 | 85.2 (6) | C11—C12—C13—I4 | −175.1 (3) |
O1w—Cu1—O3—C8 | −178.9 (7) | C12—C13—C14—C9 | 0.0 |
Cu1i—Cu1—O3—C8 | 1.5 (6) | I4—C13—C14—C9 | 175.2 (3) |
O8ii—Cu2—O5—C15 | 84.4 (5) | C10—C9—C14—C13 | 0.0 |
O7—Cu2—O5—C15 | −83.8 (5) | C8—C9—C14—C13 | 175.9 (5) |
O6ii—Cu2—O5—C15 | 3.2 (14) | Cu2ii—O6—C15—O5 | 1.5 (9) |
O9—Cu2—O5—C15 | 176.9 (5) | Cu2ii—O6—C15—C16 | −175.6 (4) |
Cu2ii—Cu2—O5—C15 | 1.3 (5) | Cu2—O5—C15—O6 | −2.1 (9) |
O8ii—Cu2—O7—C22 | −1.6 (14) | Cu2—O5—C15—C16 | 175.1 (3) |
O5—Cu2—O7—C22 | 83.5 (5) | O6—C15—C16—C17 | −85.1 (6) |
O6ii—Cu2—O7—C22 | −85.2 (5) | O5—C15—C16—C17 | 97.5 (6) |
O9—Cu2—O7—C22 | −175.7 (6) | O6—C15—C16—C21 | 100.8 (6) |
Cu2ii—Cu2—O7—C22 | −0.5 (5) | O5—C15—C16—C21 | −76.6 (6) |
O8ii—Cu2—O9—C29 | 30.5 (9) | C21—C16—C17—C18 | 0.0 |
O7—Cu2—O9—C29 | −150.7 (8) | C15—C16—C17—C18 | −173.9 (5) |
O5—Cu2—O9—C29 | −59.1 (9) | C21—C16—C17—I7 | −177.8 (3) |
O6ii—Cu2—O9—C29 | 119.7 (9) | C15—C16—C17—I7 | 8.3 (5) |
Cu1i—O2—C1—O1 | −1.2 (11) | C16—C17—C18—C19 | 0.0 |
Cu1i—O2—C1—C2 | −177.5 (4) | I7—C17—C18—C19 | 177.8 (4) |
Cu1—O1—C1—O2 | 1.9 (10) | C16—C17—C18—I8 | 170.8 (4) |
Cu1—O1—C1—C2 | 178.2 (4) | I7—C17—C18—I8 | −11.4 (4) |
O2—C1—C2—C3 | −117.9 (6) | C17—C18—C19—C20 | 0.0 |
O1—C1—C2—C3 | 65.4 (7) | I8—C18—C19—C20 | −171.5 (3) |
O2—C1—C2—C7 | 65.3 (7) | C18—C19—C20—C21 | 0.0 |
O1—C1—C2—C7 | −111.4 (6) | C18—C19—C20—I9 | −179.1 (4) |
C7—C2—C3—C4 | 0.0 | C19—C20—C21—C16 | 0.0 |
C1—C2—C3—C4 | −176.7 (6) | I9—C20—C21—C16 | 179.1 (4) |
C7—C2—C3—I1 | −178.4 (4) | C17—C16—C21—C20 | 0.0 |
C1—C2—C3—I1 | 4.9 (5) | C15—C16—C21—C20 | 174.3 (5) |
C2—C3—C4—C5 | 0.0 | Cu2ii—O8—C22—O7 | −0.4 (10) |
I1—C3—C4—C5 | 178.4 (4) | Cu2ii—O8—C22—C23 | −177.5 (4) |
C2—C3—C4—I2 | 179.8 (4) | Cu2—O7—C22—O8 | 0.7 (10) |
I1—C3—C4—I2 | −1.8 (4) | Cu2—O7—C22—C23 | 177.7 (4) |
C3—C4—C5—C6 | 0.0 | O8—C22—C23—C24 | −138.5 (5) |
I2—C4—C5—C6 | −179.8 (4) | O7—C22—C23—C24 | 44.2 (7) |
C4—C5—C6—C7 | 0.0 | O8—C22—C23—C28 | 47.5 (6) |
C4—C5—C6—I3 | 173.8 (4) | O7—C22—C23—C28 | −129.8 (5) |
C5—C6—C7—C2 | 0.0 | C28—C23—C24—C25 | 0.0 |
I3—C6—C7—C2 | −173.8 (4) | C22—C23—C24—C25 | −173.7 (5) |
C3—C2—C7—C6 | 0.0 | C28—C23—C24—I10 | −177.6 (3) |
C1—C2—C7—C6 | 176.9 (5) | C22—C23—C24—I10 | 8.7 (5) |
Cu1—O3—C8—O4 | −1.1 (11) | C23—C24—C25—C26 | 0.0 |
Cu1—O3—C8—C9 | 176.9 (4) | I10—C24—C25—C26 | 177.6 (3) |
Cu1i—O4—C8—O3 | −0.4 (11) | C23—C24—C25—I11 | 178.0 (3) |
Cu1i—O4—C8—C9 | −178.4 (4) | I10—C24—C25—I11 | −4.4 (3) |
O3—C8—C9—C10 | 133.2 (6) | C24—C25—C26—C27 | 0.0 |
O4—C8—C9—C10 | −48.6 (8) | I11—C25—C26—C27 | −178.1 (3) |
O3—C8—C9—C14 | −42.4 (7) | C25—C26—C27—C28 | 0.0 |
O4—C8—C9—C14 | 135.8 (6) | C25—C26—C27—I12 | 178.4 (3) |
C14—C9—C10—C11 | 0.0 | C26—C27—C28—C23 | 0.0 |
C8—C9—C10—C11 | −175.4 (5) | I12—C27—C28—C23 | −178.4 (3) |
C14—C9—C10—I5 | −175.6 (3) | C24—C23—C28—C27 | 0.0 |
C8—C9—C10—I5 | 9.0 (5) | C22—C23—C28—C27 | 174.3 (5) |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w2···O9 | 0.86 | 2.43 | 2.86 (1) | 112 |
O1w—H1w2···O10 | 0.86 | 2.22 | 3.04 (2) | 161 |
O9—H9o···O10 | 0.87 | 1.86 | 2.71 (2) | 165 |
O10—H10o···I1 | 0.90 | 3.10 | 3.98 (2) | 168 |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C7H2I3O2)4(H2O)2][Cu2(C7H2I3O2)4(CH4O)2]·2CH4O |
Mr | 4408.65 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 11.9321 (6), 11.9345 (6), 17.921 (1) |
α, β, γ (°) | 96.799 (1), 103.136 (1), 91.532 (1) |
V (Å3) | 2464.0 (2) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 8.43 |
Crystal size (mm) | 0.24 × 0.19 × 0.14 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.084, 1.00 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24361, 11203, 9161 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.146, 1.06 |
No. of reflections | 11203 |
No. of parameters | 449 |
No. of restraints | 14 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.37, −1.51 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
There are many examples of di(ligand)tetra(carboxylato)dicopper compounds in which the carboxylate group bridges two copper atoms that are separated by a distance less than the sum of the van der Waals radius of copper. The Cambridge Structural Database (Version 5.28, Nov. 2006) lists more than 500 entries.