The identification of the antibacterial action of nalidixic acid (nx) was central to the development of the quinolone antibacterial compounds. The ability of the nx naphthyridyl ring to interact with and inhibit some proteins has encouraged the investigation of similar structures in the search for more active compounds with less adverse effects. The possibility of structural modification by attachment of other biologically active moieties to the naphthyridyl ring of nx allowed the development of new active antimicrobial molecules. Hydrazone derivatives of nx can be synthesized easily based on the condensation of the hydrazide derivative of nx with the desired aldehyde or ketone. Only a few complexes with nx hydrazone derivatives have been described but for none were the crystal structures elucidated. The synthesis of a new one-dimensional CuII coordination polymer, namely catena-poly[[copper(II)-di-μ-chlorido-copper(II)-{μ-1-ethyl-N′-[(1H-imidazol-4-yl)methylidene]-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazidato}-[dimethanolcopper(II)]-{μ-1-ethyl-N′-[(1H-imidazol-3-yl)methylidene]-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazidato}] dichloride methanol tetrasolvate], {[Cu3(C16H15N6O2)2Cl2(CH3OH)2]Cl2·4CH3OH}n, with the (1H-imidazol-4-yl)methylidene carbohydrazide derivative of nalidixic acid (denoted h4imi), is presented and its structure is compared to the density functional theory (DFT) optimized structure of free h4imi. The title structure presents an octahedral CuII ion on an inversion centre alternating along a polymer chain with a square-pyramidal CuII ion, with the two CuII centres bridged by two chloride ligands. Hydrogen bonds involving chloride counter-ions and methanol solvent molecules mediate the three-dimensional packing of the polymer. Comparison of the geometrical results from the structure analysis with those derived from a DFT study of the free ligand reveal the differences that arise upon coordination.
Supporting information
CCDC reference: 1483258
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
catena-Poly[[copper(II)-di-µ-chlorido-copper(II)-{µ-1-ethyl-
N'-[(1
H-imidazol-3-yl)methylidene]-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazidato}-[dimethanolcopper(II)]-{µ-1-ethyl-
N'-[(1
H-imidazol-3-yl)methylidene]-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazidato}] dichloride
methanol tetrasolvate]
top
Crystal data top
[Cu3(C16H15N6O2)2Cl2(CH4O)2]Cl2·4CH4O | F(000) = 2260 |
Mr = 1107.26 | Dx = 1.671 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.5958 (11) Å | Cell parameters from 9900 reflections |
b = 16.6608 (10) Å | θ = 2.8–28.2° |
c = 14.2394 (9) Å | µ = 1.74 mm−1 |
β = 93.692 (2)° | T = 150 K |
V = 4402.5 (5) Å3 | Block, green |
Z = 4 | 0.26 × 0.17 × 0.13 mm |
Data collection top
Bruker APEXII CCD diffractometer | 4751 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.029 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 28.3°, θmin = 1.6° |
Tmin = 0.691, Tmax = 0.746 | h = −24→23 |
34794 measured reflections | k = −22→21 |
5471 independent reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0356P)2 + 7.5985P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5471 reflections | Δρmax = 0.54 e Å−3 |
294 parameters | Δρmin = −0.51 e Å−3 |
25 restraints | |
Special details top
Experimental. SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0498 before and 0.0405 after correction.
The Ratio of minimum to maximum transmission is 0.9269.
The λ/2 correction factor is 0.00150. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.47615 (2) | 0.68901 (2) | 0.36649 (2) | 0.01472 (6) | |
Cl1 | 0.64032 (3) | 0.05663 (3) | 0.32933 (5) | 0.04294 (16) | |
Cu2 | 0.2500 | 0.7500 | 0.5000 | 0.01651 (8) | |
Cl2 | 0.41153 (2) | 0.67586 (3) | 0.19402 (3) | 0.01953 (10) | |
O2 | 0.28293 (7) | 0.64150 (7) | 0.49541 (9) | 0.0181 (3) | |
C18 | 0.22719 (13) | 0.73844 (17) | 0.26149 (16) | 0.0379 (6) | |
H18A | 0.1956 | 0.7328 | 0.2040 | 0.057* | |
H18B | 0.2632 | 0.6954 | 0.2642 | 0.057* | |
H18C | 0.2516 | 0.7905 | 0.2612 | 0.057* | |
C5 | 0.34270 (9) | 0.63378 (10) | 0.45766 (12) | 0.0142 (3) | |
C10 | 0.32155 (10) | 0.49200 (11) | 0.47609 (13) | 0.0191 (4) | |
H10 | 0.2781 | 0.5089 | 0.5016 | 0.023* | |
N6 | 0.40462 (9) | 0.30580 (9) | 0.42752 (11) | 0.0200 (3) | |
C7 | 0.43359 (9) | 0.52754 (11) | 0.41004 (12) | 0.0143 (3) | |
O1 | 0.48136 (7) | 0.57491 (8) | 0.38402 (9) | 0.0199 (3) | |
N2 | 0.48830 (8) | 0.80569 (9) | 0.37265 (11) | 0.0169 (3) | |
C2 | 0.54366 (10) | 0.85055 (12) | 0.35118 (13) | 0.0210 (4) | |
H2 | 0.5879 | 0.8299 | 0.3317 | 0.025* | |
N1 | 0.52919 (9) | 0.92866 (10) | 0.36055 (13) | 0.0254 (4) | |
H1 | 0.5587 | 0.9685 | 0.3500 | 0.030* | |
C1 | 0.46128 (11) | 0.93587 (12) | 0.38905 (15) | 0.0239 (4) | |
H1A | 0.4364 | 0.9843 | 0.4010 | 0.029* | |
C3 | 0.43578 (10) | 0.85916 (11) | 0.39719 (13) | 0.0184 (4) | |
C4 | 0.36732 (10) | 0.83710 (11) | 0.42980 (13) | 0.0185 (4) | |
H4 | 0.3357 | 0.8803 | 0.4412 | 0.022* | |
N3 | 0.34300 (8) | 0.76657 (9) | 0.44565 (11) | 0.0158 (3) | |
C6 | 0.36748 (9) | 0.55065 (10) | 0.44654 (12) | 0.0145 (3) | |
N5 | 0.33399 (8) | 0.41321 (9) | 0.47135 (12) | 0.0206 (3) | |
C9 | 0.39648 (10) | 0.38588 (11) | 0.43381 (12) | 0.0170 (3) | |
C13 | 0.46479 (11) | 0.27836 (12) | 0.39315 (13) | 0.0214 (4) | |
C12 | 0.51965 (11) | 0.32959 (12) | 0.36530 (13) | 0.0218 (4) | |
H12 | 0.5629 | 0.3080 | 0.3437 | 0.026* | |
C11 | 0.51000 (10) | 0.41102 (12) | 0.36973 (12) | 0.0187 (4) | |
H11 | 0.5460 | 0.4464 | 0.3497 | 0.022* | |
C8 | 0.44637 (9) | 0.44187 (11) | 0.40417 (12) | 0.0155 (3) | |
C14 | 0.47078 (13) | 0.18882 (12) | 0.38232 (15) | 0.0287 (5) | |
H14A | 0.4522 | 0.1623 | 0.4372 | 0.043* | |
H14B | 0.5214 | 0.1741 | 0.3775 | 0.043* | |
H14C | 0.4426 | 0.1718 | 0.3253 | 0.043* | |
N4 | 0.38150 (8) | 0.69624 (9) | 0.42930 (10) | 0.0137 (3) | |
O3 | 0.18547 (8) | 0.73350 (9) | 0.34110 (11) | 0.0269 (3) | |
H3 | 0.1699 | 0.6865 | 0.3462 | 0.040* | |
O4 | 0.72490 (11) | −0.01627 (17) | 0.16711 (16) | 0.0682 (7) | |
H4A | 0.6959 | −0.0077 | 0.2089 | 0.102* | |
C17 | 0.79330 (15) | −0.03305 (19) | 0.20971 (18) | 0.0463 (6) | |
H17A | 0.7883 | −0.0541 | 0.2732 | 0.069* | |
H17B | 0.8221 | 0.0163 | 0.2135 | 0.069* | |
H17C | 0.8174 | −0.0730 | 0.1722 | 0.069* | |
C15A | 0.2775 (4) | 0.3515 (7) | 0.4911 (7) | 0.0275 (5) | 0.326 (4) |
H15A | 0.2700 | 0.3163 | 0.4353 | 0.033* | 0.326 (4) |
H15B | 0.2962 | 0.3176 | 0.5443 | 0.033* | 0.326 (4) |
C16A | 0.2070 (3) | 0.3846 (4) | 0.5139 (5) | 0.0275 (5) | 0.326 (4) |
H16A | 0.1871 | 0.4170 | 0.4610 | 0.041* | 0.326 (4) |
H16B | 0.2133 | 0.4183 | 0.5703 | 0.041* | 0.326 (4) |
H16C | 0.1739 | 0.3405 | 0.5257 | 0.041* | 0.326 (4) |
C15B | 0.2817 (2) | 0.3587 (3) | 0.5150 (3) | 0.0275 (5) | 0.674 (4) |
H15C | 0.2727 | 0.3778 | 0.5790 | 0.033* | 0.674 (4) |
H15D | 0.3019 | 0.3038 | 0.5203 | 0.033* | 0.674 (4) |
C16B | 0.21244 (16) | 0.35759 (19) | 0.4550 (2) | 0.0275 (5) | 0.674 (4) |
H16D | 0.2212 | 0.3362 | 0.3927 | 0.041* | 0.674 (4) |
H16E | 0.1935 | 0.4123 | 0.4486 | 0.041* | 0.674 (4) |
H16F | 0.1774 | 0.3235 | 0.4846 | 0.041* | 0.674 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.01062 (11) | 0.01627 (11) | 0.01774 (11) | −0.00031 (8) | 0.00466 (7) | 0.00048 (8) |
Cl1 | 0.0347 (3) | 0.0247 (3) | 0.0716 (4) | −0.0144 (2) | 0.0205 (3) | −0.0068 (3) |
Cu2 | 0.01243 (15) | 0.01206 (15) | 0.02623 (16) | 0.00088 (11) | 0.01043 (12) | 0.00055 (11) |
Cl2 | 0.01096 (19) | 0.0261 (2) | 0.0220 (2) | −0.00067 (16) | 0.00461 (15) | −0.00184 (17) |
O2 | 0.0140 (6) | 0.0136 (6) | 0.0279 (7) | 0.0008 (5) | 0.0116 (5) | 0.0008 (5) |
C18 | 0.0325 (12) | 0.0531 (16) | 0.0286 (11) | −0.0070 (11) | 0.0046 (9) | 0.0044 (10) |
C5 | 0.0114 (8) | 0.0159 (8) | 0.0156 (7) | 0.0004 (6) | 0.0021 (6) | −0.0007 (6) |
C10 | 0.0147 (8) | 0.0155 (8) | 0.0277 (9) | 0.0023 (7) | 0.0065 (7) | 0.0005 (7) |
N6 | 0.0205 (8) | 0.0155 (8) | 0.0238 (8) | 0.0039 (6) | −0.0001 (6) | −0.0011 (6) |
C7 | 0.0118 (8) | 0.0170 (8) | 0.0140 (7) | 0.0021 (6) | 0.0010 (6) | 0.0011 (6) |
O1 | 0.0144 (6) | 0.0190 (6) | 0.0272 (7) | 0.0018 (5) | 0.0087 (5) | 0.0044 (5) |
N2 | 0.0124 (7) | 0.0199 (8) | 0.0188 (7) | −0.0031 (6) | 0.0035 (5) | −0.0015 (6) |
C2 | 0.0152 (8) | 0.0246 (10) | 0.0234 (9) | −0.0053 (7) | 0.0037 (7) | −0.0028 (7) |
N1 | 0.0199 (8) | 0.0218 (8) | 0.0351 (9) | −0.0096 (7) | 0.0068 (7) | −0.0010 (7) |
C1 | 0.0194 (9) | 0.0189 (9) | 0.0343 (11) | −0.0051 (8) | 0.0080 (8) | −0.0013 (8) |
C3 | 0.0160 (8) | 0.0177 (9) | 0.0219 (9) | −0.0021 (7) | 0.0041 (7) | −0.0002 (7) |
C4 | 0.0162 (9) | 0.0149 (8) | 0.0249 (9) | 0.0018 (7) | 0.0060 (7) | 0.0000 (7) |
N3 | 0.0137 (7) | 0.0142 (7) | 0.0203 (7) | 0.0001 (6) | 0.0061 (5) | 0.0005 (6) |
C6 | 0.0126 (8) | 0.0140 (8) | 0.0172 (8) | −0.0004 (6) | 0.0036 (6) | −0.0005 (6) |
N5 | 0.0145 (7) | 0.0139 (7) | 0.0340 (9) | 0.0008 (6) | 0.0066 (6) | 0.0034 (6) |
C9 | 0.0149 (8) | 0.0159 (8) | 0.0198 (8) | 0.0032 (7) | −0.0005 (6) | 0.0001 (7) |
C13 | 0.0249 (10) | 0.0197 (9) | 0.0190 (8) | 0.0087 (8) | −0.0022 (7) | −0.0014 (7) |
C12 | 0.0201 (9) | 0.0259 (10) | 0.0196 (8) | 0.0095 (8) | 0.0016 (7) | −0.0024 (7) |
C11 | 0.0158 (9) | 0.0235 (9) | 0.0168 (8) | 0.0045 (7) | 0.0019 (6) | 0.0006 (7) |
C8 | 0.0136 (8) | 0.0187 (9) | 0.0141 (8) | 0.0042 (7) | 0.0004 (6) | −0.0005 (6) |
C14 | 0.0352 (12) | 0.0199 (10) | 0.0311 (11) | 0.0097 (9) | 0.0029 (9) | −0.0032 (8) |
N4 | 0.0123 (7) | 0.0134 (7) | 0.0159 (7) | 0.0014 (5) | 0.0041 (5) | 0.0005 (5) |
O3 | 0.0258 (7) | 0.0222 (7) | 0.0336 (8) | −0.0020 (6) | 0.0088 (6) | −0.0022 (6) |
O4 | 0.0375 (11) | 0.108 (2) | 0.0586 (13) | 0.0008 (12) | 0.0000 (9) | −0.0433 (13) |
C17 | 0.0439 (15) | 0.0617 (18) | 0.0333 (13) | −0.0011 (13) | 0.0017 (11) | −0.0019 (12) |
C15A | 0.0185 (8) | 0.0213 (11) | 0.0430 (16) | −0.0039 (7) | 0.0045 (10) | 0.0080 (11) |
C16A | 0.0185 (8) | 0.0213 (11) | 0.0430 (16) | −0.0039 (7) | 0.0045 (10) | 0.0080 (11) |
C15B | 0.0185 (8) | 0.0213 (11) | 0.0430 (16) | −0.0039 (7) | 0.0045 (10) | 0.0080 (11) |
C16B | 0.0185 (8) | 0.0213 (11) | 0.0430 (16) | −0.0039 (7) | 0.0045 (10) | 0.0080 (11) |
Geometric parameters (Å, º) top
Cu1—Cl2i | 2.3206 (5) | C4—N3 | 1.284 (2) |
Cu1—Cl2 | 2.6727 (5) | N3—N4 | 1.400 (2) |
Cu1—O1 | 1.9190 (13) | N5—C9 | 1.387 (2) |
Cu1—N4 | 2.0285 (14) | N5—C15A | 1.509 (11) |
Cu2—O2 | 1.9110 (12) | N5—C15B | 1.495 (5) |
Cu2—O2ii | 1.9110 (12) | C9—C8 | 1.400 (3) |
Cu2—N3ii | 1.9593 (15) | C13—C12 | 1.407 (3) |
Cl2—Cu1i | 2.3206 (5) | C13—C14 | 1.505 (3) |
O2—C5 | 1.272 (2) | C12—H12 | 0.9500 |
C18—H18A | 0.9800 | C12—C11 | 1.371 (3) |
C18—H18B | 0.9800 | C11—H11 | 0.9500 |
C18—H18C | 0.9800 | C11—C8 | 1.407 (2) |
C18—O3 | 1.417 (3) | C14—H14A | 0.9800 |
C5—C6 | 1.472 (2) | C14—H14B | 0.9800 |
C5—N4 | 1.343 (2) | C14—H14C | 0.9800 |
C10—H10 | 0.9500 | O3—H3 | 0.8400 |
C10—C6 | 1.381 (2) | O4—H4A | 0.8400 |
C10—N5 | 1.335 (2) | O4—C17 | 1.402 (3) |
N6—C9 | 1.346 (2) | C17—H17A | 0.9800 |
N6—C13 | 1.331 (2) | C17—H17B | 0.9800 |
C7—O1 | 1.262 (2) | C17—H17C | 0.9800 |
C7—C6 | 1.418 (2) | C15A—H15A | 0.9900 |
C7—C8 | 1.450 (2) | C15A—H15B | 0.9900 |
N2—C2 | 1.324 (2) | C15A—C16A | 1.478 (8) |
N2—C3 | 1.383 (2) | C16A—H16A | 0.9800 |
C2—H2 | 0.9500 | C16A—H16B | 0.9800 |
C2—N1 | 1.337 (3) | C16A—H16C | 0.9800 |
N1—H1 | 0.8800 | C15B—H15C | 0.9900 |
N1—C1 | 1.356 (3) | C15B—H15D | 0.9900 |
C1—H1A | 0.9500 | C15B—C16B | 1.499 (4) |
C1—C3 | 1.371 (3) | C16B—H16D | 0.9800 |
C3—C4 | 1.431 (2) | C16B—H16E | 0.9800 |
C4—H4 | 0.9500 | C16B—H16F | 0.9800 |
| | | |
Cl2i—Cu1—Cl2 | 90.757 (16) | N5—C9—C8 | 119.05 (16) |
O1—Cu1—Cl2i | 85.16 (4) | N6—C13—C12 | 122.51 (18) |
O1—Cu1—Cl2 | 93.11 (4) | N6—C13—C14 | 116.60 (19) |
O1—Cu1—N4 | 92.27 (6) | C12—C13—C14 | 120.87 (18) |
N4—Cu1—Cl2 | 93.35 (4) | C13—C12—H12 | 120.4 |
N4—Cu1—Cl2i | 175.27 (4) | C11—C12—C13 | 119.22 (17) |
O2ii—Cu2—O2 | 180.0 | C11—C12—H12 | 120.4 |
O2—Cu2—N3ii | 99.97 (6) | C12—C11—H11 | 120.2 |
O2ii—Cu2—N3ii | 80.03 (6) | C12—C11—C8 | 119.56 (18) |
Cu1i—Cl2—Cu1 | 88.356 (16) | C8—C11—H11 | 120.2 |
C5—O2—Cu2 | 113.63 (11) | C9—C8—C7 | 121.61 (16) |
H18A—C18—H18B | 109.5 | C9—C8—C11 | 116.76 (17) |
H18A—C18—H18C | 109.5 | C11—C8—C7 | 121.62 (17) |
H18B—C18—H18C | 109.5 | C13—C14—H14A | 109.5 |
O3—C18—H18A | 109.5 | C13—C14—H14B | 109.5 |
O3—C18—H18B | 109.5 | C13—C14—H14C | 109.5 |
O3—C18—H18C | 109.5 | H14A—C14—H14B | 109.5 |
O2—C5—C6 | 115.40 (15) | H14A—C14—H14C | 109.5 |
O2—C5—N4 | 123.35 (16) | H14B—C14—H14C | 109.5 |
N4—C5—C6 | 121.25 (15) | C5—N4—Cu1 | 125.78 (12) |
C6—C10—H10 | 117.7 | C5—N4—N3 | 107.93 (14) |
N5—C10—H10 | 117.7 | N3—N4—Cu1 | 126.19 (11) |
N5—C10—C6 | 124.58 (17) | C18—O3—H3 | 109.5 |
C13—N6—C9 | 117.76 (17) | C17—O4—H4A | 109.5 |
O1—C7—C6 | 125.53 (16) | O4—C17—H17A | 109.5 |
O1—C7—C8 | 118.53 (15) | O4—C17—H17B | 109.5 |
C6—C7—C8 | 115.93 (15) | O4—C17—H17C | 109.5 |
C7—O1—Cu1 | 128.84 (12) | H17A—C17—H17B | 109.5 |
C2—N2—C3 | 105.49 (16) | H17A—C17—H17C | 109.5 |
N2—C2—H2 | 124.4 | H17B—C17—H17C | 109.5 |
N2—C2—N1 | 111.22 (17) | N5—C15A—H15A | 108.5 |
N1—C2—H2 | 124.4 | N5—C15A—H15B | 108.5 |
C2—N1—H1 | 125.9 | H15A—C15A—H15B | 107.5 |
C2—N1—C1 | 108.25 (16) | C16A—C15A—N5 | 115.1 (8) |
C1—N1—H1 | 125.9 | C16A—C15A—H15A | 108.5 |
N1—C1—H1A | 127.0 | C16A—C15A—H15B | 108.5 |
N1—C1—C3 | 106.06 (17) | C15A—C16A—H16A | 109.5 |
C3—C1—H1A | 127.0 | C15A—C16A—H16B | 109.5 |
N2—C3—C4 | 125.04 (16) | C15A—C16A—H16C | 109.5 |
C1—C3—N2 | 108.98 (16) | H16A—C16A—H16B | 109.5 |
C1—C3—C4 | 125.93 (18) | H16A—C16A—H16C | 109.5 |
C3—C4—H4 | 115.7 | H16B—C16A—H16C | 109.5 |
N3—C4—C3 | 128.51 (17) | N5—C15B—H15C | 109.8 |
N3—C4—H4 | 115.7 | N5—C15B—H15D | 109.8 |
C4—N3—N4 | 123.15 (15) | N5—C15B—C16B | 109.2 (3) |
C10—C6—C5 | 115.40 (15) | H15C—C15B—H15D | 108.3 |
C10—C6—C7 | 119.16 (16) | C16B—C15B—H15C | 109.8 |
C7—C6—C5 | 125.43 (16) | C16B—C15B—H15D | 109.8 |
C10—N5—C9 | 119.62 (16) | C15B—C16B—H16D | 109.5 |
C10—N5—C15A | 122.4 (4) | C15B—C16B—H16E | 109.5 |
C10—N5—C15B | 117.2 (2) | C15B—C16B—H16F | 109.5 |
C9—N5—C15A | 117.3 (4) | H16D—C16B—H16E | 109.5 |
C9—N5—C15B | 123.0 (2) | H16D—C16B—H16F | 109.5 |
N6—C9—N5 | 116.84 (16) | H16E—C16B—H16F | 109.5 |
N6—C9—C8 | 124.10 (17) | | |
| | | |
Cu2—O2—C5—C6 | −175.80 (11) | C6—C5—N4—N3 | 177.71 (15) |
Cu2—O2—C5—N4 | 4.2 (2) | C6—C10—N5—C9 | −0.6 (3) |
O2—C5—C6—C10 | 1.8 (2) | C6—C10—N5—C15A | −170.8 (4) |
O2—C5—C6—C7 | −177.27 (16) | C6—C10—N5—C15B | 174.3 (2) |
O2—C5—N4—Cu1 | −178.81 (12) | C6—C7—O1—Cu1 | −10.4 (3) |
O2—C5—N4—N3 | −2.3 (2) | C6—C7—C8—C9 | −0.6 (2) |
C10—N5—C9—N6 | −177.46 (17) | C6—C7—C8—C11 | −179.65 (16) |
C10—N5—C9—C8 | 1.9 (3) | N5—C10—C6—C5 | 179.52 (18) |
C10—N5—C15A—C16A | 1.3 (9) | N5—C10—C6—C7 | −1.4 (3) |
C10—N5—C15B—C16B | 72.4 (4) | N5—C9—C8—C7 | −1.3 (3) |
N6—C9—C8—C7 | 178.04 (17) | N5—C9—C8—C11 | 177.82 (16) |
N6—C9—C8—C11 | −2.9 (3) | C9—N6—C13—C12 | 1.1 (3) |
N6—C13—C12—C11 | −2.8 (3) | C9—N6—C13—C14 | −176.99 (17) |
O1—C7—C6—C5 | 1.8 (3) | C9—N5—C15A—C16A | −169.1 (5) |
O1—C7—C6—C10 | −177.20 (17) | C9—N5—C15B—C16B | −112.9 (3) |
O1—C7—C8—C9 | 178.52 (16) | C13—N6—C9—N5 | −178.89 (16) |
O1—C7—C8—C11 | −0.5 (3) | C13—N6—C9—C8 | 1.8 (3) |
N2—C2—N1—C1 | −0.3 (2) | C13—C12—C11—C8 | 1.6 (3) |
N2—C3—C4—N3 | 2.8 (3) | C12—C11—C8—C7 | −179.86 (17) |
C2—N2—C3—C1 | 0.4 (2) | C12—C11—C8—C9 | 1.1 (3) |
C2—N2—C3—C4 | −177.00 (18) | C8—C7—O1—Cu1 | 170.57 (12) |
C2—N1—C1—C3 | 0.5 (2) | C8—C7—C6—C5 | −179.10 (16) |
N1—C1—C3—N2 | −0.5 (2) | C8—C7—C6—C10 | 1.9 (2) |
N1—C1—C3—C4 | 176.82 (18) | C14—C13—C12—C11 | 175.23 (18) |
C1—C3—C4—N3 | −174.1 (2) | N4—C5—C6—C10 | −178.20 (16) |
C3—N2—C2—N1 | −0.1 (2) | N4—C5—C6—C7 | 2.7 (3) |
C3—C4—N3—N4 | −2.3 (3) | C15A—N5—C9—N6 | −6.8 (5) |
C4—N3—N4—Cu1 | −6.7 (2) | C15A—N5—C9—C8 | 172.5 (4) |
C4—N3—N4—C5 | 176.81 (17) | C15B—N5—C9—N6 | 7.9 (3) |
C6—C5—N4—Cu1 | 1.2 (2) | C15B—N5—C9—C8 | −172.7 (2) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+3/2, −z+1. |
Hydrogen-bond geometry (Å) top
D—H···A | D···A |
O3—H3···Cl1iii | 3.066 (2) |
N1—H1···Cl1iv | 3.022 (2) |
O4—H4A···Cl1 | 3.123 (2) |
Symmetry codes: (iii) x−1/2, y+1/2, z; (iv) x, y+1, z. |
Selected bonds lengths (Å) from the
{[Cu1.5(h4imi)Cl(MeOH)]Cl.2MeOH}n complex and
similar nx complexes found in the CSD topBond | Bond length | Mean CSD value |
Cu1—N4 | 2.029 (2) | 2.00 (3)/1.98 (5) |
Cu1—N2 | 1.958 (2) | |
Cu1—O1 | 1.919 (1) | 1.94 (4) |
Cu1—Cl2 | 2.6727 (5) | 2.7 (2)/2.4 (2) |
Cu1—Cl2i | 2.3205 (5) | |
Cu2—N3 | 1.959 (15) | 1.99 (3) |
Cu2—O2 | 1.911 (12) | 1.96 (3) |
Cu2—O3 | 2.5070 (16) | 2.47 (7) |
Symmetry codes: (i) -x+1, y, -z+1/2;
(ii) ??? [please provide]. |