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The stepwise addition of Cu2+ ions to the nonplanar cyclic Schiff base 5,9,14,18-tetramethyl-1,4,10,13-tetraazacyclooctadeca-5,8,14,17-tetraene-7,16-dione (H4daaden, C18H28N4O2), yields a one-end-open dinuclear copper chelate. The pyridine adduct of the dinuclear copper chelate, namely, [μ-6,11-dimethyl-7,10-diazahexadeca-5,11-diene-2,4,13,15-tetraolato(4−)](pyridine)dicopper(II), [Cu2(C16H20N2O4)(C5H5N)], was characterized by single-crystal X-ray crystallography. The two CuII atoms of the copper chelate display different coordination modes, i.e. inner-N2O2 and outer-O2O2. The Cu atom which is bonded in the outer-O2O2 mode is axially bonded to a pyridine molecule, which suggests that the electron-donating ability of the O2O2 site to the Cu atom is poor. As a result, the O2O2-bonded Cu atom has a coordination number of five, showing square-bipyramidal geometry around the Cu atom. The N2O2-coordinated site provides sufficient electron density to the other Cu atom to be stabilized with a coordination number of four, showing square-planar geometry around the Cu atom. The electron-donating ability of the ligand coordination sites plays a key role in determining the coordination number of the Cu atoms of the dicopper chelate.
Supporting information
CCDC reference: 2231909
Data collection: APEX4 (Bruker, 2021); cell refinement: APEX4 (Bruker, 2021); data reduction: SAINT (Bruker, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXTL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020) and POV-RAY (Cason, 2004); software used to prepare material for publication: APEX4 (Bruker, 2021).
[µ-6,11-Dimethyl-7,10-diazahexadeca-5,11-diene-2,4,13,15-tetraolato(4-)-1
κ4O2,
O4,
O13,
O15:2
κ4N7,
N10,
O4,
O13](pyridine-1
κN)dicopper(II)
top
Crystal data top
[Cu2(C16H20N2O4)(C5H5N)] | Z = 2 |
Mr = 510.52 | F(000) = 524 |
Triclinic, P1 | Dx = 1.671 Mg m−3 |
a = 8.0549 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.8811 (6) Å | Cell parameters from 1540 reflections |
c = 13.7189 (8) Å | θ = 1.6–28.5° |
α = 106.451 (1)° | µ = 2.13 mm−1 |
β = 103.271 (1)° | T = 296 K |
γ = 91.482 (1)° | Prism frag, colorless |
V = 1014.40 (11) Å3 | 0.30 × 0.08 × 0.08 mm |
Data collection top
Bruker D8 Venture diffractometer | 4293 reflections with I > 2σ(I) |
profile data from θ/2θ scans | Rint = 0.015 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 28.5°, θmin = 1.6° |
Tmin = 0.567, Tmax = 0.848 | h = −10→10 |
12405 measured reflections | k = −13→13 |
4680 independent reflections | l = −18→17 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.021 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.055 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0266P)2 + 0.5267P] where P = (Fo2 + 2Fc2)/3 |
4680 reflections | (Δ/σ)max = 0.002 |
275 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Special details top
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. |
Refinement. A brown-coloured plate-like single crystal of Cu2(daaen)(py), having
approximate dimensions 0.080 × 0.080 × 0.300 mm was selected for
the X-ray crystallographic analysis and mounted on a cryo-loop using an oil
cryo-protectant. The X-ray intensity data were measured at T = 296 K,
using a three-circle goniometer platform geometry with a fixed χ angle =
54.74°. A Bruker SMART 1000 diffractometer, equipped with a CCD
detector. Monochromatic Mo X-ray radiation (λ = 0.71073 Å) was selected
for the measurement. All frames were integrated with the aid of the Bruker
SAINT software using a narrow-frame algorithm. The integration of the
data using a triclinic unit cell yielded a total of 12405 reflections to a
maximum θ angle of 28.50° (0.74 Å resolution), of which 4680 were
independent (average redundancy = 2.651, completeness = 91.1%,
Rint = 1.53%, Rsig = 1.74%) and 4293 (91.73%) were greater
than 2σ (F2). The final unit-cell constants of a =
8.0549 (5) Å, b = 9.8811 (6) Å, c = 13.7189 (8)Å, α =
106.4510 (10)°, β = 103.2710 (10)°, γ = 91.4820 (10)° and V =
1014.40 (11) Å3, are based upon the refinement of the 1540 XYZ-centroids
of reflections above 20σ(I). The calculated minimum and maximum
transmission coefficients (based on crystal size) are 0.5670 and 0.8480. The
structure was solved in a triclinic unit cell; ppace group: P1,
with Z = 2 for the formula unit, C21H25Cu2N3O4.
Using the Bruker SHELXT software package, refinement of the structure
was carried out by least-squares procedures on weighted F2 values
using the SHELXTL2018 (Sheldrick, 2015b) included in the
APEX4 (Bruker, 2021) program. The final anisotropic full-matrix least-squares refinement on
F2 with 276 variables converged at R1 = 2.05%, for
the observed data and wR2 = 5.53% for all data. The goodness-of-fit
was 1.044.
The largest peak in the final difference electron density synthesis
was 0.340 e- Å-3 and the largest hole was -0.306 e- Å-3
with an r.m.s. deviation of 0.054 e- Å-3. Based on the final model, the
calculated density was 1.671 g cm-3 and F(000) = 524 e-. Graphics
were performed using software Mercury V.4.2.0: (https://www.ccdc.cam.ac.uk/)
and POV-Ray v 3.7: (The Persistence of Vision Raytracer, high quality, Free
Software tool). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.67560 (2) | 0.69842 (2) | 0.78376 (2) | 0.01441 (5) | |
Cu2 | 0.74398 (2) | 0.47982 (2) | 0.59601 (2) | 0.01529 (5) | |
N1 | 0.84460 (16) | 0.30766 (13) | 0.57589 (10) | 0.0174 (2) | |
N2 | 0.74679 (16) | 0.47544 (14) | 0.45833 (10) | 0.0187 (3) | |
N3 | 0.94332 (16) | 0.81239 (13) | 0.84007 (10) | 0.0180 (2) | |
O1 | 0.65027 (13) | 0.67677 (11) | 0.91465 (8) | 0.0181 (2) | |
O2 | 0.74876 (14) | 0.50802 (11) | 0.74018 (8) | 0.0174 (2) | |
O3 | 0.66075 (14) | 0.66147 (11) | 0.63315 (8) | 0.0183 (2) | |
O4 | 0.55647 (13) | 0.86413 (11) | 0.78924 (8) | 0.0188 (2) | |
C1 | 0.6968 (2) | 0.59164 (17) | 1.06208 (12) | 0.0215 (3) | |
H1A | 0.798563 | 0.647035 | 1.109045 | 0.032* | |
H1B | 0.688525 | 0.500378 | 1.073311 | 0.032* | |
H1C | 0.598137 | 0.639346 | 1.075005 | 0.032* | |
C2 | 0.70478 (18) | 0.57295 (16) | 0.94990 (11) | 0.0171 (3) | |
C3 | 0.7684 (2) | 0.45196 (16) | 0.89819 (12) | 0.0191 (3) | |
H3 | 0.802498 | 0.388154 | 0.935667 | 0.023* | |
C4 | 0.78706 (18) | 0.41521 (15) | 0.79329 (11) | 0.0165 (3) | |
C5 | 0.8455 (2) | 0.28646 (16) | 0.74729 (12) | 0.0200 (3) | |
H13 | 0.867341 | 0.225331 | 0.788305 | 0.024* | |
C6 | 0.87582 (19) | 0.23728 (16) | 0.64569 (12) | 0.0192 (3) | |
C7 | 0.8840 (2) | 0.25573 (17) | 0.47290 (12) | 0.0213 (3) | |
H7A | 0.830832 | 0.159632 | 0.438267 | 0.026* | |
H7B | 1.006961 | 0.253681 | 0.482675 | 0.026* | |
C8 | 0.8191 (2) | 0.35063 (16) | 0.40248 (12) | 0.0207 (3) | |
H8A | 0.913531 | 0.381478 | 0.378369 | 0.025* | |
H8B | 0.732266 | 0.295644 | 0.341362 | 0.025* | |
C9 | 0.68559 (19) | 0.57112 (17) | 0.41322 (12) | 0.0194 (3) | |
C10 | 0.6165 (2) | 0.69437 (17) | 0.46544 (12) | 0.0217 (3) | |
H10 | 0.569839 | 0.751143 | 0.424439 | 0.026* | |
C11 | 0.61003 (19) | 0.74071 (16) | 0.57067 (12) | 0.0180 (3) | |
C12 | 0.5485 (2) | 0.87312 (16) | 0.61445 (12) | 0.0207 (3) | |
H12 | 0.521759 | 0.930978 | 0.571213 | 0.025* | |
C13 | 0.52491 (18) | 0.92382 (16) | 0.71465 (12) | 0.0189 (3) | |
C14 | 0.4520 (2) | 1.06472 (18) | 0.74577 (14) | 0.0275 (4) | |
H14A | 0.346067 | 1.051050 | 0.764106 | 0.041* | |
H14B | 0.431660 | 1.103913 | 0.688040 | 0.041* | |
H14C | 0.532032 | 1.128651 | 0.804933 | 0.041* | |
C15 | 0.9508 (2) | 0.09704 (18) | 0.61936 (14) | 0.0276 (4) | |
H15A | 0.872528 | 0.030649 | 0.560754 | 0.041* | |
H15B | 0.970034 | 0.061321 | 0.678814 | 0.041* | |
H15C | 1.057625 | 0.109900 | 0.601769 | 0.041* | |
C16 | 0.6906 (2) | 0.55399 (18) | 0.30118 (12) | 0.0234 (3) | |
H16A | 0.807382 | 0.565340 | 0.297329 | 0.035* | |
H16B | 0.628017 | 0.624467 | 0.276943 | 0.035* | |
H16C | 0.639422 | 0.461260 | 0.257930 | 0.035* | |
C17 | 0.9586 (2) | 0.95341 (16) | 0.86038 (12) | 0.0210 (3) | |
H17 | 0.861655 | 0.997153 | 0.839373 | 0.025* | |
C18 | 1.1110 (2) | 1.03733 (17) | 0.91091 (13) | 0.0241 (3) | |
H18 | 1.115733 | 1.135193 | 0.924179 | 0.029* | |
C19 | 1.2563 (2) | 0.97349 (18) | 0.94140 (14) | 0.0276 (4) | |
H19 | 1.360332 | 1.027555 | 0.976354 | 0.033* | |
C20 | 1.2440 (2) | 0.82729 (19) | 0.91890 (14) | 0.0293 (4) | |
H20 | 1.340221 | 0.780985 | 0.936801 | 0.035* | |
C21 | 1.0856 (2) | 0.75152 (17) | 0.86922 (13) | 0.0222 (3) | |
H21 | 1.077474 | 0.653523 | 0.855383 | 0.027* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.01791 (9) | 0.01383 (9) | 0.01186 (9) | 0.00351 (6) | 0.00342 (7) | 0.00444 (7) |
Cu2 | 0.01905 (10) | 0.01593 (9) | 0.01119 (9) | 0.00390 (7) | 0.00379 (7) | 0.00424 (7) |
N1 | 0.0187 (6) | 0.0174 (6) | 0.0152 (6) | 0.0025 (5) | 0.0048 (5) | 0.0028 (5) |
N2 | 0.0194 (6) | 0.0221 (6) | 0.0145 (6) | 0.0023 (5) | 0.0045 (5) | 0.0053 (5) |
N3 | 0.0187 (6) | 0.0194 (6) | 0.0160 (6) | 0.0019 (5) | 0.0045 (5) | 0.0054 (5) |
O1 | 0.0238 (5) | 0.0165 (5) | 0.0147 (5) | 0.0038 (4) | 0.0054 (4) | 0.0050 (4) |
O2 | 0.0247 (5) | 0.0153 (5) | 0.0132 (5) | 0.0048 (4) | 0.0048 (4) | 0.0054 (4) |
O3 | 0.0247 (5) | 0.0178 (5) | 0.0137 (5) | 0.0059 (4) | 0.0042 (4) | 0.0066 (4) |
O4 | 0.0205 (5) | 0.0195 (5) | 0.0176 (5) | 0.0058 (4) | 0.0048 (4) | 0.0071 (4) |
C1 | 0.0294 (8) | 0.0216 (7) | 0.0145 (7) | 0.0021 (6) | 0.0066 (6) | 0.0060 (6) |
C2 | 0.0178 (7) | 0.0186 (7) | 0.0143 (7) | −0.0010 (5) | 0.0026 (5) | 0.0053 (6) |
C3 | 0.0247 (7) | 0.0186 (7) | 0.0168 (7) | 0.0051 (6) | 0.0054 (6) | 0.0092 (6) |
C4 | 0.0172 (7) | 0.0166 (7) | 0.0156 (7) | 0.0017 (5) | 0.0023 (5) | 0.0062 (6) |
C5 | 0.0260 (8) | 0.0183 (7) | 0.0191 (7) | 0.0065 (6) | 0.0076 (6) | 0.0090 (6) |
C6 | 0.0187 (7) | 0.0172 (7) | 0.0209 (8) | 0.0030 (5) | 0.0047 (6) | 0.0045 (6) |
C7 | 0.0222 (7) | 0.0247 (8) | 0.0166 (7) | 0.0067 (6) | 0.0065 (6) | 0.0036 (6) |
C8 | 0.0245 (8) | 0.0210 (7) | 0.0164 (7) | 0.0004 (6) | 0.0082 (6) | 0.0029 (6) |
C9 | 0.0168 (7) | 0.0267 (8) | 0.0152 (7) | −0.0007 (6) | 0.0029 (5) | 0.0080 (6) |
C10 | 0.0232 (8) | 0.0272 (8) | 0.0190 (8) | 0.0057 (6) | 0.0054 (6) | 0.0130 (6) |
C11 | 0.0172 (7) | 0.0212 (7) | 0.0182 (7) | 0.0023 (5) | 0.0031 (6) | 0.0108 (6) |
C12 | 0.0228 (7) | 0.0219 (7) | 0.0229 (8) | 0.0060 (6) | 0.0070 (6) | 0.0140 (6) |
C13 | 0.0155 (7) | 0.0188 (7) | 0.0238 (8) | 0.0029 (5) | 0.0047 (6) | 0.0087 (6) |
C14 | 0.0336 (9) | 0.0244 (8) | 0.0316 (9) | 0.0127 (7) | 0.0136 (7) | 0.0138 (7) |
C15 | 0.0387 (10) | 0.0242 (8) | 0.0253 (8) | 0.0149 (7) | 0.0146 (7) | 0.0092 (7) |
C16 | 0.0260 (8) | 0.0297 (8) | 0.0167 (7) | 0.0023 (6) | 0.0063 (6) | 0.0093 (6) |
C17 | 0.0213 (7) | 0.0206 (7) | 0.0226 (8) | 0.0025 (6) | 0.0040 (6) | 0.0100 (6) |
C18 | 0.0268 (8) | 0.0201 (7) | 0.0250 (8) | −0.0014 (6) | 0.0049 (6) | 0.0077 (6) |
C19 | 0.0192 (8) | 0.0296 (9) | 0.0307 (9) | −0.0037 (6) | 0.0029 (7) | 0.0070 (7) |
C20 | 0.0185 (8) | 0.0324 (9) | 0.0357 (10) | 0.0064 (6) | 0.0037 (7) | 0.0102 (8) |
C21 | 0.0225 (8) | 0.0186 (7) | 0.0247 (8) | 0.0049 (6) | 0.0060 (6) | 0.0047 (6) |
Geometric parameters (Å, º) top
Cu1—O4 | 1.9110 (10) | C7—C8 | 1.547 (2) |
Cu1—O1 | 1.9223 (10) | C7—H7A | 0.9700 |
Cu1—O2 | 1.9561 (10) | C7—H7B | 0.9700 |
Cu1—O3 | 1.9682 (10) | C8—H8A | 0.9700 |
Cu1—N3 | 2.2654 (13) | C8—H8B | 0.9700 |
Cu1—Cu2 | 3.0275 (3) | C9—C10 | 1.425 (2) |
Cu2—N1 | 1.8801 (12) | C9—C16 | 1.508 (2) |
Cu2—N2 | 1.8823 (13) | C10—C11 | 1.399 (2) |
Cu2—O3 | 1.9057 (10) | C10—H10 | 0.9300 |
Cu2—O2 | 1.9088 (10) | C11—C12 | 1.429 (2) |
N1—C6 | 1.319 (2) | C12—C13 | 1.383 (2) |
N1—C7 | 1.4711 (19) | C12—H12 | 0.9300 |
N2—C9 | 1.317 (2) | C13—C14 | 1.512 (2) |
N2—C8 | 1.4679 (19) | C14—H14A | 0.9600 |
N3—C17 | 1.3379 (19) | C14—H14B | 0.9600 |
N3—C21 | 1.3404 (19) | C14—H14C | 0.9600 |
O1—C2 | 1.2985 (18) | C15—H15A | 0.9600 |
O2—C4 | 1.3255 (17) | C15—H15B | 0.9600 |
O3—C11 | 1.3232 (17) | C15—H15C | 0.9600 |
O4—C13 | 1.2999 (18) | C16—H16A | 0.9600 |
C1—C2 | 1.514 (2) | C16—H16B | 0.9600 |
C1—H1A | 0.9600 | C16—H16C | 0.9600 |
C1—H1B | 0.9600 | C17—C18 | 1.381 (2) |
C1—H1C | 0.9600 | C17—H17 | 0.9300 |
C2—C3 | 1.383 (2) | C18—C19 | 1.380 (2) |
C3—C4 | 1.425 (2) | C18—H18 | 0.9300 |
C3—H3 | 0.9300 | C19—C20 | 1.385 (2) |
C4—C5 | 1.397 (2) | C19—H19 | 0.9300 |
C5—C6 | 1.420 (2) | C20—C21 | 1.384 (2) |
C5—H13 | 0.9300 | C20—H20 | 0.9300 |
C6—C15 | 1.508 (2) | C21—H21 | 0.9300 |
| | | |
O4—Cu1—O1 | 96.96 (4) | C5—C6—C15 | 116.55 (14) |
O4—Cu1—O2 | 163.66 (5) | N1—C7—C8 | 111.64 (12) |
O1—Cu1—O2 | 92.26 (4) | N1—C7—H7A | 109.3 |
O4—Cu1—O3 | 91.98 (4) | C8—C7—H7A | 109.3 |
O1—Cu1—O3 | 161.95 (5) | N1—C7—H7B | 109.3 |
O2—Cu1—O3 | 75.68 (4) | C8—C7—H7B | 109.3 |
O4—Cu1—N3 | 96.36 (5) | H7A—C7—H7B | 108.0 |
O1—Cu1—N3 | 98.64 (5) | N2—C8—C7 | 111.93 (12) |
O2—Cu1—N3 | 95.55 (5) | N2—C8—H8A | 109.2 |
O3—Cu1—N3 | 95.90 (5) | C7—C8—H8A | 109.2 |
O4—Cu1—Cu2 | 129.40 (3) | N2—C8—H8B | 109.2 |
O1—Cu1—Cu2 | 129.34 (3) | C7—C8—H8B | 109.2 |
O2—Cu1—Cu2 | 37.88 (3) | H8A—C8—H8B | 107.9 |
O3—Cu1—Cu2 | 37.87 (3) | N2—C9—C10 | 123.47 (14) |
N3—Cu1—Cu2 | 95.51 (3) | N2—C9—C16 | 119.63 (14) |
N1—Cu2—N2 | 89.11 (5) | C10—C9—C16 | 116.89 (14) |
N1—Cu2—O3 | 172.95 (5) | C11—C10—C9 | 128.15 (14) |
N2—Cu2—O3 | 96.15 (5) | C11—C10—H10 | 115.9 |
N1—Cu2—O2 | 96.14 (5) | C9—C10—H10 | 115.9 |
N2—Cu2—O2 | 173.15 (5) | O3—C11—C10 | 120.35 (14) |
O3—Cu2—O2 | 78.27 (4) | O3—C11—C12 | 117.70 (13) |
N1—Cu2—Cu1 | 134.73 (4) | C10—C11—C12 | 121.95 (14) |
N2—Cu2—Cu1 | 135.12 (4) | C13—C12—C11 | 126.53 (14) |
O3—Cu2—Cu1 | 39.35 (3) | C13—C12—H12 | 116.7 |
O2—Cu2—Cu1 | 39.00 (3) | C11—C12—H12 | 116.7 |
C6—N1—C7 | 122.22 (13) | O4—C13—C12 | 127.96 (14) |
C6—N1—Cu2 | 124.18 (10) | O4—C13—C14 | 113.09 (13) |
C7—N1—Cu2 | 113.59 (10) | C12—C13—C14 | 118.95 (14) |
C9—N2—C8 | 121.97 (13) | C13—C14—H14A | 109.5 |
C9—N2—Cu2 | 124.47 (11) | C13—C14—H14B | 109.5 |
C8—N2—Cu2 | 113.53 (10) | H14A—C14—H14B | 109.5 |
C17—N3—C21 | 117.19 (13) | C13—C14—H14C | 109.5 |
C17—N3—Cu1 | 117.85 (10) | H14A—C14—H14C | 109.5 |
C21—N3—Cu1 | 124.18 (10) | H14B—C14—H14C | 109.5 |
C2—O1—Cu1 | 123.78 (9) | C6—C15—H15A | 109.5 |
C4—O2—Cu2 | 126.53 (9) | C6—C15—H15B | 109.5 |
C4—O2—Cu1 | 130.30 (9) | H15A—C15—H15B | 109.5 |
Cu2—O2—Cu1 | 103.12 (5) | C6—C15—H15C | 109.5 |
C11—O3—Cu2 | 126.89 (10) | H15A—C15—H15C | 109.5 |
C11—O3—Cu1 | 130.31 (10) | H15B—C15—H15C | 109.5 |
Cu2—O3—Cu1 | 102.78 (5) | C9—C16—H16A | 109.5 |
C13—O4—Cu1 | 124.28 (10) | C9—C16—H16B | 109.5 |
C2—C1—H1A | 109.5 | H16A—C16—H16B | 109.5 |
C2—C1—H1B | 109.5 | C9—C16—H16C | 109.5 |
H1A—C1—H1B | 109.5 | H16A—C16—H16C | 109.5 |
C2—C1—H1C | 109.5 | H16B—C16—H16C | 109.5 |
H1A—C1—H1C | 109.5 | N3—C17—C18 | 123.38 (15) |
H1B—C1—H1C | 109.5 | N3—C17—H17 | 118.3 |
O1—C2—C3 | 128.09 (13) | C18—C17—H17 | 118.3 |
O1—C2—C1 | 113.90 (13) | C19—C18—C17 | 118.85 (15) |
C3—C2—C1 | 118.01 (13) | C19—C18—H18 | 120.6 |
C2—C3—C4 | 126.58 (14) | C17—C18—H18 | 120.6 |
C2—C3—H3 | 116.7 | C18—C19—C20 | 118.67 (15) |
C4—C3—H3 | 116.7 | C18—C19—H19 | 120.7 |
O2—C4—C5 | 120.43 (13) | C20—C19—H19 | 120.7 |
O2—C4—C3 | 117.93 (13) | C21—C20—C19 | 118.63 (15) |
C5—C4—C3 | 121.63 (14) | C21—C20—H20 | 120.7 |
C4—C5—C6 | 128.09 (14) | C19—C20—H20 | 120.7 |
C4—C5—H13 | 116.0 | N3—C21—C20 | 123.25 (15) |
C6—C5—H13 | 116.0 | N3—C21—H21 | 118.4 |
N1—C6—C5 | 123.86 (14) | C20—C21—H21 | 118.4 |
N1—C6—C15 | 119.59 (14) | | |
Selected bond lengths (Å) of the H4daaden ligand, the mononuclear complex
Cu(H2daaen) and the dinuclear complex Cu2(daaen)(py) topBond | H4daaden | Cu(H2daaen) | Cu2(daaen)(py) |
C2—C3 | 1.379 (1) | 1.505 (8) | 1.383 (2) |
C4—C5 | 1.448 (1) | 1.366 (5) | 1.399 (2) |
C5—C6 | 1.376 (1) | 1.416 (6) | 1.425 (2) |
C6—N1 | 1.346 (1) | 1.301 (5) | 1.317 (2) |
Bond valence sum of the CuN2O2 and CuO2O2
coordination sites topCuN2O2 | | CuO2O2 | |
Bond | Valence | Bond | Valence |
Cu1—N1 | 0.633 | Cu2—O2 | 0.443 |
Cu1—N2 | 0.633 | Cu2—O4 | 0.429 |
Cu1—O2 | 0.503 | Cu2—O1 | 0.485 |
Cu1—O4 | 0.503 | Cu2—O3 | 0.500 |
Sum | 2.272 | Cu2—N3 | 0.225 |
| | Sum | 2.082 |
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