Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000494/qb0169sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000494/qb0169Isup2.hkl |
CCDC reference: 142933
2-Imidazolecarboxaldehyde (2 mmol) was reacted with bis(3-aminopropyl)amine (1 mmol) in 50 ml of methanol. To the yellow solution, Cu(ClO4)·6H2O (1 mmol) was added with continuous stirring. The resulting blue solution was allowed to stand at room temperature for one day, upon which blue needle-like crystals of the compound were obtained.
The H5 atom of the methanol molecule was refined in a riding model with an O—H bond length of 0.85 Å and all other H-atom coordinates were constrained using the SHELXL97 default N—H and C—H distances.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993a); cell refinement: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993a); data reduction: TEXSAN PROCESS (Molecular Structure Corporation, 1993b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Cu(C10H18N5)(CH4O)]ClO4 | F(000) = 836 |
Mr = 403.33 | Dx = 1.590 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.488 (3) Å | Cell parameters from 25 reflections |
b = 12.475 (5) Å | θ = 6.4–10.1° |
c = 18.176 (6) Å | µ = 1.49 mm−1 |
β = 97.15 (3)° | T = 193 K |
V = 1684.7 (11) Å3 | Needle, blue |
Z = 4 | 0.45 × 0.30 × 0.30 mm |
Rigaku AFC 7S diffractometer | 3122 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 26.5°, θmin = 2.7° |
2θ/ω scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→15 |
Tmin = 0.565, Tmax = 0.640 | l = −22→22 |
3676 measured reflections | 3 standard reflections every 200 reflections |
3501 independent reflections | intensity decay: −0.1% |
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)] = 0.041 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0541P)2 + 2.3975P] where P = (Fo2 + 2Fc2)/3 |
3501 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.70 e Å−3 |
[Cu(C10H18N5)(CH4O)]ClO4 | V = 1684.7 (11) Å3 |
Mr = 403.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.488 (3) Å | µ = 1.49 mm−1 |
b = 12.475 (5) Å | T = 193 K |
c = 18.176 (6) Å | 0.45 × 0.30 × 0.30 mm |
β = 97.15 (3)° |
Rigaku AFC 7S diffractometer | 3122 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.022 |
Tmin = 0.565, Tmax = 0.640 | 3 standard reflections every 200 reflections |
3676 measured reflections | intensity decay: −0.1% |
3501 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.73 e Å−3 |
3501 reflections | Δρmin = −0.70 e Å−3 |
208 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 | ||
Cu | 0.28951 (4) | 0.15313 (3) | 0.408792 (18) | 0.02844 (13) | |
Cl | 0.64242 (11) | 0.16484 (7) | 0.15727 (4) | 0.0410 (2) | |
O1 | 0.4630 (4) | 0.1600 (2) | 0.11883 (16) | 0.0595 (8) | |
O2 | 0.6417 (5) | 0.1233 (4) | 0.22867 (17) | 0.0885 (12) | |
O3 | 0.7025 (7) | 0.2693 (4) | 0.1593 (4) | 0.164 (3) | |
O4 | 0.7582 (5) | 0.1006 (5) | 0.1207 (2) | 0.1248 (19) | |
O5 | 0.0315 (3) | 0.24613 (18) | 0.42281 (13) | 0.0408 (5) | |
H5 | −0.0449 | 0.1966 | 0.4263 | 0.049* | |
N1 | 0.2976 (3) | 0.0671 (2) | 0.50190 (13) | 0.0313 (5) | |
N2 | 0.2200 (3) | −0.0905 (2) | 0.55052 (15) | 0.0361 (6) | |
N3 | 0.1486 (3) | 0.0217 (2) | 0.36674 (14) | 0.0331 (5) | |
N4 | 0.3138 (4) | 0.2136 (2) | 0.30639 (14) | 0.0376 (6) | |
H41 | 0.4135 | 0.1832 | 0.2927 | 0.045* | |
N5 | 0.4710 (3) | 0.2559 (2) | 0.46126 (15) | 0.0348 (5) | |
H51 | 0.5789 | 0.2233 | 0.4641 | 0.042* | |
H52 | 0.4447 | 0.2621 | 0.5080 | 0.042* | |
C1 | 0.3628 (4) | 0.0663 (3) | 0.57553 (16) | 0.0349 (6) | |
H1 | 0.4297 | 0.1219 | 0.6019 | 0.042* | |
C2 | 0.3141 (4) | −0.0299 (3) | 0.60454 (17) | 0.0376 (7) | |
H2 | 0.3420 | −0.0509 | 0.6549 | 0.045* | |
C3 | 0.2147 (4) | −0.0280 (2) | 0.49006 (16) | 0.0312 (6) | |
C4 | 0.1328 (4) | −0.0503 (2) | 0.41575 (17) | 0.0341 (6) | |
H4 | 0.0699 | −0.1153 | 0.4036 | 0.041* | |
C5 | 0.0608 (4) | 0.0034 (3) | 0.29100 (17) | 0.0428 (8) | |
H5A | −0.0660 | 0.0275 | 0.2872 | 0.051* | |
H5B | 0.0610 | −0.0743 | 0.2798 | 0.051* | |
C6 | 0.1565 (5) | 0.0633 (3) | 0.23499 (18) | 0.0478 (9) | |
H6A | 0.0937 | 0.0493 | 0.1847 | 0.057* | |
H6B | 0.2806 | 0.0352 | 0.2368 | 0.057* | |
C7 | 0.1649 (5) | 0.1833 (3) | 0.24795 (18) | 0.0464 (8) | |
H7A | 0.1825 | 0.2199 | 0.2010 | 0.056* | |
H7B | 0.0491 | 0.2080 | 0.2629 | 0.056* | |
C8 | 0.3449 (5) | 0.3308 (3) | 0.3039 (2) | 0.0488 (9) | |
H8A | 0.2405 | 0.3684 | 0.3204 | 0.059* | |
H8B | 0.3532 | 0.3523 | 0.2520 | 0.059* | |
C9 | 0.5152 (5) | 0.3658 (3) | 0.3522 (2) | 0.0501 (9) | |
H9A | 0.6146 | 0.3169 | 0.3436 | 0.060* | |
H9B | 0.5481 | 0.4388 | 0.3372 | 0.060* | |
C10 | 0.4963 (5) | 0.3666 (3) | 0.4340 (2) | 0.0422 (7) | |
H10A | 0.6055 | 0.3985 | 0.4619 | 0.051* | |
H10B | 0.3918 | 0.4113 | 0.4427 | 0.051* | |
C11 | 0.0275 (6) | 0.3265 (4) | 0.4787 (3) | 0.0766 (15) | |
H11A | −0.0939 | 0.3569 | 0.4757 | 0.115* | |
H11B | 0.1134 | 0.3834 | 0.4710 | 0.115* | |
H11C | 0.0601 | 0.2943 | 0.5277 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0287 (2) | 0.0305 (2) | 0.0258 (2) | 0.00042 (13) | 0.00220 (13) | 0.00113 (13) |
Cl | 0.0368 (4) | 0.0508 (5) | 0.0348 (4) | −0.0015 (3) | 0.0016 (3) | 0.0138 (3) |
O1 | 0.0416 (14) | 0.082 (2) | 0.0520 (16) | −0.0041 (13) | −0.0068 (12) | 0.0200 (14) |
O2 | 0.069 (2) | 0.154 (4) | 0.0421 (16) | 0.022 (2) | 0.0056 (14) | 0.040 (2) |
O3 | 0.116 (4) | 0.077 (3) | 0.271 (7) | −0.046 (3) | −0.086 (4) | 0.075 (4) |
O4 | 0.066 (2) | 0.229 (6) | 0.081 (3) | 0.033 (3) | 0.017 (2) | −0.039 (3) |
O5 | 0.0341 (11) | 0.0379 (12) | 0.0520 (14) | 0.0004 (9) | 0.0109 (10) | −0.0001 (10) |
N1 | 0.0317 (12) | 0.0318 (12) | 0.0301 (12) | −0.0008 (10) | 0.0022 (10) | 0.0002 (10) |
N2 | 0.0311 (12) | 0.0358 (14) | 0.0420 (14) | 0.0037 (10) | 0.0073 (11) | 0.0096 (11) |
N3 | 0.0283 (12) | 0.0370 (13) | 0.0326 (13) | 0.0036 (10) | −0.0015 (10) | −0.0031 (10) |
N4 | 0.0355 (13) | 0.0465 (15) | 0.0309 (13) | 0.0036 (12) | 0.0049 (10) | 0.0060 (11) |
N5 | 0.0331 (13) | 0.0336 (13) | 0.0373 (14) | −0.0016 (10) | 0.0032 (10) | 0.0016 (11) |
C1 | 0.0360 (15) | 0.0398 (16) | 0.0285 (14) | −0.0003 (13) | 0.0021 (12) | −0.0005 (12) |
C2 | 0.0350 (15) | 0.0455 (18) | 0.0327 (15) | 0.0070 (13) | 0.0054 (12) | 0.0080 (13) |
C3 | 0.0246 (13) | 0.0345 (15) | 0.0344 (15) | 0.0034 (11) | 0.0037 (11) | 0.0020 (12) |
C4 | 0.0269 (13) | 0.0337 (15) | 0.0412 (16) | −0.0002 (12) | 0.0015 (12) | −0.0043 (13) |
C5 | 0.0381 (17) | 0.053 (2) | 0.0342 (16) | −0.0004 (15) | −0.0066 (13) | −0.0086 (14) |
C6 | 0.0397 (17) | 0.073 (3) | 0.0296 (16) | 0.0035 (17) | 0.0006 (13) | −0.0096 (16) |
C7 | 0.0437 (18) | 0.064 (2) | 0.0298 (16) | 0.0064 (16) | −0.0007 (13) | 0.0067 (15) |
C8 | 0.057 (2) | 0.047 (2) | 0.0426 (19) | 0.0017 (16) | 0.0072 (16) | 0.0146 (15) |
C9 | 0.053 (2) | 0.0439 (19) | 0.055 (2) | −0.0077 (16) | 0.0146 (17) | 0.0123 (16) |
C10 | 0.0417 (18) | 0.0322 (16) | 0.052 (2) | −0.0032 (13) | 0.0045 (15) | 0.0040 (14) |
C11 | 0.054 (2) | 0.068 (3) | 0.114 (4) | −0.007 (2) | 0.035 (3) | −0.039 (3) |
Cu—N1 | 1.998 (2) | C1—H1 | 0.9500 |
Cu—N5 | 2.020 (3) | C2—H2 | 0.9500 |
Cu—N4 | 2.037 (3) | C3—C4 | 1.439 (4) |
Cu—N3 | 2.046 (3) | C4—H4 | 0.9500 |
Cu—O5 | 2.295 (2) | C5—C6 | 1.513 (5) |
Cl—O3 | 1.378 (4) | C5—H5A | 0.9900 |
Cl—O2 | 1.398 (3) | C5—H5B | 0.9900 |
Cl—O4 | 1.407 (4) | C6—C7 | 1.516 (6) |
Cl—O1 | 1.436 (3) | C6—H6A | 0.9900 |
O5—C11 | 1.431 (5) | C6—H6B | 0.9900 |
O5—H5 | 0.8500 | C7—H7A | 0.9900 |
N1—C3 | 1.345 (4) | C7—H7B | 0.9899 |
N1—C1 | 1.366 (4) | C8—C9 | 1.520 (6) |
N2—C3 | 1.344 (4) | C8—H8A | 0.9900 |
N2—C2 | 1.364 (4) | C8—H8B | 0.9899 |
N3—C4 | 1.281 (4) | C9—C10 | 1.510 (5) |
N3—C5 | 1.468 (4) | C9—H9A | 0.9900 |
N4—C8 | 1.482 (5) | C9—H9B | 0.9900 |
N4—C7 | 1.490 (4) | C10—H10A | 0.9900 |
N4—H41 | 0.9000 | C10—H10B | 0.9900 |
N5—C10 | 1.487 (4) | C11—H11A | 0.9800 |
N5—H51 | 0.9000 | C11—H11B | 0.9800 |
N5—H52 | 0.9000 | C11—H11C | 0.9799 |
C1—C2 | 1.378 (5) | ||
N1—Cu—N5 | 89.61 (11) | N1—C3—C4 | 117.1 (3) |
N1—Cu—N4 | 167.36 (11) | N3—C4—C3 | 116.9 (3) |
N5—Cu—N4 | 93.73 (11) | N3—C4—H4 | 121.6 |
N1—Cu—N3 | 81.15 (10) | C3—C4—H4 | 121.6 |
N5—Cu—N3 | 166.12 (10) | N3—C5—C6 | 111.1 (3) |
N4—Cu—N3 | 93.20 (11) | N3—C5—H5A | 109.4 |
N1—Cu—O5 | 96.58 (10) | C6—C5—H5A | 109.4 |
N5—Cu—O5 | 98.80 (10) | N3—C5—H5B | 109.4 |
N4—Cu—O5 | 94.95 (10) | C6—C5—H5B | 109.4 |
N3—Cu—O5 | 92.57 (9) | H5A—C5—H5B | 108.0 |
O3—Cl—O2 | 111.4 (3) | C5—C6—C7 | 113.4 (3) |
O3—Cl—O4 | 109.5 (4) | C5—C6—H6A | 108.9 |
O2—Cl—O4 | 107.5 (3) | C7—C6—H6A | 108.9 |
O3—Cl—O1 | 109.6 (2) | C5—C6—H6B | 108.9 |
O2—Cl—O1 | 108.96 (19) | C7—C6—H6B | 108.9 |
O4—Cl—O1 | 109.9 (2) | H6A—C6—H6B | 107.7 |
C11—O5—Cu | 121.7 (2) | N4—C7—C6 | 112.0 (3) |
C11—O5—H5 | 112.5 | N4—C7—H7A | 109.2 |
Cu—O5—H5 | 103.0 | C6—C7—H7A | 109.2 |
C3—N1—C1 | 104.6 (2) | N4—C7—H7B | 109.2 |
C3—N1—Cu | 111.94 (19) | C6—C7—H7B | 109.2 |
C1—N1—Cu | 143.5 (2) | H7A—C7—H7B | 107.9 |
C3—N2—C2 | 103.1 (3) | N4—C8—C9 | 113.0 (3) |
C4—N3—C5 | 118.3 (3) | N4—C8—H8A | 109.0 |
C4—N3—Cu | 113.0 (2) | C9—C8—H8A | 109.0 |
C5—N3—Cu | 128.7 (2) | N4—C8—H8B | 109.0 |
C8—N4—C7 | 109.6 (3) | C9—C8—H8B | 109.0 |
C8—N4—Cu | 115.2 (2) | H8A—C8—H8B | 107.8 |
C7—N4—Cu | 114.4 (2) | C10—C9—C8 | 113.3 (3) |
C8—N4—H41 | 105.6 | C10—C9—H9A | 108.9 |
C7—N4—H41 | 105.6 | C8—C9—H9A | 108.9 |
Cu—N4—H41 | 105.6 | C10—C9—H9B | 108.9 |
C10—N5—Cu | 122.6 (2) | C8—C9—H9B | 108.9 |
C10—N5—H51 | 106.7 | H9A—C9—H9B | 107.7 |
Cu—N5—H51 | 106.7 | N5—C10—C9 | 110.7 (3) |
C10—N5—H52 | 106.7 | N5—C10—H10A | 109.5 |
Cu—N5—H52 | 106.7 | C9—C10—H10A | 109.5 |
H51—N5—H52 | 106.6 | N5—C10—H10B | 109.5 |
N1—C1—C2 | 107.6 (3) | C9—C10—H10B | 109.5 |
N1—C1—H1 | 126.2 | H10A—C10—H10B | 108.1 |
C2—C1—H1 | 126.2 | O5—C11—H11A | 109.5 |
N2—C2—C1 | 110.2 (3) | O5—C11—H11B | 109.5 |
N2—C2—H2 | 124.9 | H11A—C11—H11B | 109.5 |
C1—C2—H2 | 124.9 | O5—C11—H11C | 109.5 |
N2—C3—N1 | 114.5 (3) | H11A—C11—H11C | 109.5 |
N2—C3—C4 | 128.4 (3) | H11B—C11—H11C | 109.5 |
N1—Cu—O5—C11 | 70.3 (3) | N4—Cu—N5—C10 | 32.0 (3) |
N5—Cu—O5—C11 | −20.3 (3) | N3—Cu—N5—C10 | 151.8 (4) |
N4—Cu—O5—C11 | −114.8 (3) | O5—Cu—N5—C10 | −63.6 (3) |
N3—Cu—O5—C11 | 151.7 (3) | C3—N1—C1—C2 | −0.5 (3) |
N5—Cu—N1—C3 | −168.5 (2) | Cu—N1—C1—C2 | −177.3 (3) |
N4—Cu—N1—C3 | −63.0 (5) | C3—N2—C2—C1 | −0.2 (3) |
N3—Cu—N1—C3 | 1.09 (19) | N1—C1—C2—N2 | 0.4 (4) |
O5—Cu—N1—C3 | 92.7 (2) | C2—N2—C3—N1 | −0.2 (3) |
N5—Cu—N1—C1 | 8.2 (4) | C2—N2—C3—C4 | 179.8 (3) |
N4—Cu—N1—C1 | 113.6 (5) | C1—N1—C3—N2 | 0.4 (3) |
N3—Cu—N1—C1 | 177.8 (4) | Cu—N1—C3—N2 | 178.38 (19) |
O5—Cu—N1—C1 | −90.6 (4) | C1—N1—C3—C4 | −179.5 (3) |
N1—Cu—N3—C4 | −0.4 (2) | Cu—N1—C3—C4 | −1.6 (3) |
N5—Cu—N3—C4 | 48.3 (5) | C5—N3—C4—C3 | −177.7 (3) |
N4—Cu—N3—C4 | 168.2 (2) | Cu—N3—C4—C3 | −0.3 (3) |
O5—Cu—N3—C4 | −96.7 (2) | N2—C3—C4—N3 | −178.7 (3) |
N1—Cu—N3—C5 | 176.6 (3) | N1—C3—C4—N3 | 1.3 (4) |
N5—Cu—N3—C5 | −134.6 (4) | C4—N3—C5—C6 | −153.7 (3) |
N4—Cu—N3—C5 | −14.7 (3) | Cu—N3—C5—C6 | 29.4 (4) |
O5—Cu—N3—C5 | 80.4 (3) | N3—C5—C6—C7 | −58.5 (4) |
N1—Cu—N4—C8 | −140.1 (4) | C8—N4—C7—C6 | 166.0 (3) |
N5—Cu—N4—C8 | −35.1 (2) | Cu—N4—C7—C6 | −62.8 (3) |
N3—Cu—N4—C8 | 156.9 (2) | C5—C6—C7—N4 | 81.3 (4) |
O5—Cu—N4—C8 | 64.1 (2) | C7—N4—C8—C9 | −169.8 (3) |
N1—Cu—N4—C7 | 91.5 (5) | Cu—N4—C8—C9 | 59.4 (4) |
N5—Cu—N4—C7 | −163.4 (2) | N4—C8—C9—C10 | −75.4 (4) |
N3—Cu—N4—C7 | 28.6 (2) | Cu—N5—C10—C9 | −48.8 (4) |
O5—Cu—N4—C7 | −64.3 (2) | C8—C9—C10—N5 | 66.2 (4) |
N1—Cu—N5—C10 | −160.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···N2i | 0.85 | 1.95 | 2.789 (4) | 171 |
N4—H41···O2 | 0.90 | 2.31 | 3.188 (5) | 166 |
N5—H51···N2ii | 0.90 | 2.28 | 3.127 (4) | 158 |
N5—H52···O1iii | 0.90 | 2.22 | 3.057 (4) | 154 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C10H18N5)(CH4O)]ClO4 |
Mr | 403.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 193 |
a, b, c (Å) | 7.488 (3), 12.475 (5), 18.176 (6) |
β (°) | 97.15 (3) |
V (Å3) | 1684.7 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.49 |
Crystal size (mm) | 0.45 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Rigaku AFC 7S diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.565, 0.640 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3676, 3501, 3122 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.111, 1.09 |
No. of reflections | 3501 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.73, −0.70 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993a), TEXSAN PROCESS (Molecular Structure Corporation, 1993b), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990).
Cu—N1 | 1.998 (2) | N1—C3 | 1.345 (4) |
Cu—N5 | 2.020 (3) | N1—C1 | 1.366 (4) |
Cu—N4 | 2.037 (3) | N2—C3 | 1.344 (4) |
Cu—N3 | 2.046 (3) | N2—C2 | 1.364 (4) |
Cu—O5 | 2.295 (2) | C1—C2 | 1.378 (5) |
N5—Cu—N4 | 93.73 (11) | N5—Cu—O5 | 98.80 (10) |
N1—Cu—N3 | 81.15 (10) | N4—Cu—O5 | 94.95 (10) |
N4—Cu—N3 | 93.20 (11) | N3—Cu—O5 | 92.57 (9) |
N1—Cu—O5 | 96.58 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···N2i | 0.85 | 1.95 | 2.789 (4) | 171.4 |
N4—H41···O2 | 0.90 | 2.31 | 3.188 (5) | 165.5 |
N5—H51···N2ii | 0.90 | 2.28 | 3.127 (4) | 157.5 |
N5—H52···O1iii | 0.90 | 2.22 | 3.057 (4) | 153.8 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x, −y+1/2, z+1/2. |
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A good strategy to prepare heteronuclear complexes is that of using metal complexes as ligands. Among the precursors that have been commonly used to prepare heteronuclear complexes the mononuclear complexes containing imidazole ligands (Dominques-Vera et al., 1996) deserve special attention. In basic medium, these precursors can coordinate to another metal ion or metal complex leading to a heteronuclear complex (Dominques-Vera et al., 1998). In this paper, we report the synthesis of a new mononuclear copper(II) complex, (I), containing an imidazole ligand, which may be used as a precursor in the preparation of homo- and heteronuclear complexes.
The structure consists of a mononuclear complex cation and a perchlorate anion. Although the amine:aldehyde ratio was 1:2, the ligand is formed by condensation of only one aldehyde molecule with one amine molecule. The ligand contains two imidazole, two amine and one imino N atoms. In the title compound, the ligand coordinates by four of its five N atoms in its deprotonated form leaving the deprotonated N2 atom uncoordinated. The tetradentate behaviour of the ligand results in the formation of one five- and two six-membered chelate rings around the Cu atom. The four N atoms of the coordination plane are almost coplanar with deviations from the least-squares plane < 0.006 Å. The Cu atom deviates by 0.203 (1) Å from the basal plane towards the O atom of the coordinated methanol molecule at 2.295 (2) Å. The nearest atom in the direction of the sixth coordination position is N2(1 − x,-y,1 − z) at 3.738 (3) Å. The five-membered chelate ring and the imidazole ring are planar, the six-membered rings adopt chair conformations. The complex cations and anions are connected by hydrogen bonds involving the methanol O—H, the three amino H atoms, the deprotonated N2 of the imidazole ring, and O1 and O2 of the perchlorate ion.