Buy article online - an online subscription or single-article purchase is required to access this article.
The structures of three copper-containing complexes, namely (benzoato-κ2O,O′)[(E)-2-({[2-(diethylamino)ethyl]imino}methyl)phenolato-κ3N,N′,O]copper(II) dihydrate, [Cu(C7H5O2)(C13H19N2O)]·2H2O, 1, [(E)-2-({[2-(diethylamino)ethyl]imino}methyl)phenolato-κ3N,N′,O](2-phenylacetato-κ2O,O′)copper(II), [Cu(C8H7O2)(C13H19N2O)], 2, and bis[μ-(E)-2-({[3-(diethylamino)propyl]imino}methyl)phenolato]-κ4N,N′,O:O;κ4O:N,N′,O-(μ-2-methylbenzoato-κ2O:O′)copper(II) perchlorate, [Cu2(C8H7O2)(C12H17N2O)2]ClO4, 3, have been reported and all have been tested for their activity in the oxidation of D-galactose. The results suggest that, unlike the enzyme galactose oxidase, due to the precipitation of Cu2O, this reaction is not catalytic as would have been expected. The structures of 1 and 2 are monomeric, while 3 consists of a dimeric cation and a perchlorate anion [which is disordered over two orientations, with occupancies of 0.64 (4) and 0.36 (4)]. In all three structures, the central Cu atom is five-coordinated in a distorted square-pyramidal arrangment (τ parameter of 0.0932 for 1, 0.0888 for 2, and 0.142 and 0.248 for the two Cu centers in 3). In each species, the environment about the Cu atom is such that the vacant sixth position is open, with very little steric crowding.
Supporting information
CCDC references: 1901536; 1901535; 1901534
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
(Benzoato-
κ2O,
O')[(
E)-2-({[2-(diethylamino)ethyl]imino}methyl)phenolato-
κ3N,
N',
O]copper(II) dihydrate (1)
top
Crystal data top
[Cu(C7H5O2)(C13H19N2O)]·2H2O | F(000) = 924 |
Mr = 439.98 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2427 (3) Å | Cell parameters from 20474 reflections |
b = 10.1287 (2) Å | θ = 3.8–40.9° |
c = 17.7683 (3) Å | µ = 1.11 mm−1 |
β = 92.501 (2)° | T = 100 K |
V = 2021.42 (8) Å3 | Multi-faceted prism, blue |
Z = 4 | 0.35 × 0.23 × 0.18 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 13125 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 10770 reflections with I > 2σ(I) |
Detector resolution: 10.6501 pixels mm-1 | Rint = 0.030 |
ω scans | θmax = 41.3°, θmin = 3.5° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018) | h = −20→20 |
Tmin = 0.474, Tmax = 1.000 | k = −18→18 |
51132 measured reflections | l = −25→32 |
Refinement top
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0327P)2 + 0.3747P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
13125 reflections | Δρmax = 0.57 e Å−3 |
270 parameters | Δρmin = −0.60 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu | 0.23818 (2) | 0.69525 (2) | 0.47778 (2) | 0.01137 (2) | |
O1 | 0.27766 (5) | 0.54601 (5) | 0.41727 (3) | 0.01650 (9) | |
O2 | 0.15402 (5) | 0.78344 (6) | 0.39331 (3) | 0.01670 (9) | |
O3 | 0.33453 (5) | 0.86472 (6) | 0.37715 (3) | 0.01897 (10) | |
O1W | 0.52308 (7) | 0.83109 (7) | 0.28425 (4) | 0.02636 (13) | |
H1W1 | 0.4716 (12) | 0.8598 (15) | 0.3113 (8) | 0.034 (4)* | |
H1W2 | 0.5502 (16) | 0.8967 (16) | 0.2641 (10) | 0.060 (5)* | |
O2W | 0.39643 (9) | 0.57738 (7) | 0.27758 (4) | 0.03167 (16) | |
H2W1 | 0.3575 (13) | 0.5822 (15) | 0.3162 (8) | 0.037 (4)* | |
H2W2 | 0.4310 (14) | 0.6492 (14) | 0.2765 (9) | 0.042 (4)* | |
N1 | 0.33000 (6) | 0.63419 (6) | 0.56489 (3) | 0.01338 (9) | |
N2 | 0.16538 (6) | 0.82506 (6) | 0.55446 (3) | 0.01380 (9) | |
C1 | 0.32672 (6) | 0.43555 (7) | 0.44259 (4) | 0.01414 (10) | |
C2 | 0.32873 (8) | 0.32474 (8) | 0.39411 (5) | 0.02019 (13) | |
H2A | 0.294165 | 0.331522 | 0.344513 | 0.024* | |
C3 | 0.38021 (8) | 0.20647 (8) | 0.41763 (6) | 0.02339 (15) | |
H3A | 0.378582 | 0.133178 | 0.384235 | 0.028* | |
C4 | 0.43441 (8) | 0.19302 (7) | 0.48948 (6) | 0.02259 (15) | |
H4A | 0.471294 | 0.112327 | 0.504607 | 0.027* | |
C5 | 0.43329 (8) | 0.29896 (7) | 0.53786 (5) | 0.01865 (12) | |
H5A | 0.469865 | 0.290767 | 0.586855 | 0.022* | |
C6 | 0.37906 (6) | 0.41938 (7) | 0.51635 (4) | 0.01382 (10) | |
C7 | 0.38029 (6) | 0.52083 (7) | 0.57282 (4) | 0.01411 (10) | |
H7A | 0.421362 | 0.502782 | 0.619548 | 0.017* | |
C8 | 0.32821 (7) | 0.72459 (8) | 0.62904 (4) | 0.01648 (11) | |
H8A | 0.383817 | 0.799046 | 0.622365 | 0.020* | |
H8B | 0.351197 | 0.678039 | 0.676465 | 0.020* | |
C9 | 0.20140 (7) | 0.77360 (8) | 0.63053 (4) | 0.01702 (12) | |
H9A | 0.147997 | 0.700558 | 0.644253 | 0.020* | |
H9B | 0.195502 | 0.844521 | 0.668525 | 0.020* | |
C10 | 0.21916 (7) | 0.95742 (7) | 0.54046 (4) | 0.01689 (12) | |
H10A | 0.188508 | 0.989212 | 0.490618 | 0.020* | |
H10B | 0.306310 | 0.946107 | 0.537607 | 0.020* | |
C11 | 0.19639 (9) | 1.06407 (8) | 0.59850 (5) | 0.02305 (15) | |
H11A | 0.226691 | 1.148804 | 0.580836 | 0.035* | |
H11B | 0.237177 | 1.040824 | 0.646542 | 0.035* | |
H11C | 0.110635 | 1.071227 | 0.605459 | 0.035* | |
C12 | 0.03368 (7) | 0.82973 (8) | 0.54397 (5) | 0.01943 (13) | |
H12A | 0.012276 | 0.883028 | 0.498678 | 0.023* | |
H12B | 0.000355 | 0.874369 | 0.587918 | 0.023* | |
C13 | −0.02251 (8) | 0.69370 (9) | 0.53516 (6) | 0.02444 (15) | |
H13A | −0.109103 | 0.702796 | 0.528447 | 0.037* | |
H13B | 0.008651 | 0.649662 | 0.491031 | 0.037* | |
H13C | −0.003276 | 0.640999 | 0.580316 | 0.037* | |
C14 | 0.22685 (7) | 0.85663 (7) | 0.35854 (4) | 0.01419 (10) | |
C15 | 0.17491 (7) | 0.93920 (7) | 0.29497 (4) | 0.01484 (11) | |
C16 | 0.24644 (8) | 1.02998 (8) | 0.25883 (4) | 0.01974 (13) | |
H16A | 0.328766 | 1.035916 | 0.272873 | 0.024* | |
C17 | 0.19839 (10) | 1.11179 (9) | 0.20249 (5) | 0.02590 (17) | |
H17A | 0.247678 | 1.173462 | 0.178319 | 0.031* | |
C18 | 0.07821 (10) | 1.10309 (9) | 0.18165 (5) | 0.02722 (18) | |
H18A | 0.045041 | 1.159443 | 0.143495 | 0.033* | |
C19 | 0.00625 (9) | 1.01191 (10) | 0.21660 (5) | 0.02489 (16) | |
H19A | −0.075915 | 1.005821 | 0.202140 | 0.030* | |
C20 | 0.05468 (8) | 0.92951 (8) | 0.27283 (4) | 0.01896 (12) | |
H20A | 0.005618 | 0.866548 | 0.296135 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.01340 (4) | 0.01114 (3) | 0.00955 (3) | 0.00143 (3) | 0.00042 (2) | 0.00089 (2) |
O1 | 0.0219 (2) | 0.0150 (2) | 0.01244 (19) | 0.00371 (18) | −0.00101 (17) | −0.00138 (16) |
O2 | 0.0184 (2) | 0.0180 (2) | 0.0136 (2) | 0.00053 (18) | −0.00005 (17) | 0.00472 (16) |
O3 | 0.0171 (2) | 0.0228 (2) | 0.0169 (2) | 0.0019 (2) | −0.00086 (18) | 0.00397 (19) |
O1W | 0.0273 (3) | 0.0280 (3) | 0.0243 (3) | 0.0005 (3) | 0.0065 (2) | 0.0045 (2) |
O2W | 0.0522 (5) | 0.0228 (3) | 0.0208 (3) | 0.0024 (3) | 0.0110 (3) | −0.0015 (2) |
N1 | 0.0154 (2) | 0.0137 (2) | 0.01093 (19) | 0.00220 (18) | −0.00039 (17) | −0.00069 (16) |
N2 | 0.0142 (2) | 0.0133 (2) | 0.0142 (2) | 0.00149 (18) | 0.00314 (18) | 0.00104 (17) |
C1 | 0.0148 (3) | 0.0126 (2) | 0.0152 (2) | −0.0006 (2) | 0.0022 (2) | −0.00182 (19) |
C2 | 0.0212 (3) | 0.0175 (3) | 0.0219 (3) | −0.0010 (2) | 0.0017 (3) | −0.0070 (2) |
C3 | 0.0236 (4) | 0.0142 (3) | 0.0329 (4) | −0.0017 (3) | 0.0062 (3) | −0.0075 (3) |
C4 | 0.0245 (4) | 0.0112 (2) | 0.0327 (4) | 0.0017 (2) | 0.0079 (3) | 0.0017 (3) |
C5 | 0.0209 (3) | 0.0128 (2) | 0.0225 (3) | 0.0027 (2) | 0.0043 (3) | 0.0042 (2) |
C6 | 0.0150 (3) | 0.0113 (2) | 0.0153 (2) | 0.0008 (2) | 0.0027 (2) | 0.00123 (19) |
C7 | 0.0149 (3) | 0.0148 (2) | 0.0126 (2) | 0.0018 (2) | 0.0004 (2) | 0.00160 (19) |
C8 | 0.0193 (3) | 0.0177 (3) | 0.0123 (2) | 0.0021 (2) | −0.0010 (2) | −0.0027 (2) |
C9 | 0.0204 (3) | 0.0184 (3) | 0.0126 (2) | 0.0026 (2) | 0.0042 (2) | 0.0003 (2) |
C10 | 0.0183 (3) | 0.0130 (2) | 0.0198 (3) | 0.0000 (2) | 0.0056 (2) | −0.0008 (2) |
C11 | 0.0270 (4) | 0.0181 (3) | 0.0243 (3) | −0.0015 (3) | 0.0043 (3) | −0.0066 (3) |
C12 | 0.0139 (3) | 0.0198 (3) | 0.0248 (3) | 0.0024 (2) | 0.0038 (2) | 0.0009 (2) |
C13 | 0.0206 (3) | 0.0264 (4) | 0.0263 (4) | −0.0059 (3) | 0.0004 (3) | 0.0052 (3) |
C14 | 0.0186 (3) | 0.0139 (2) | 0.0101 (2) | 0.0031 (2) | 0.0004 (2) | 0.00105 (18) |
C15 | 0.0200 (3) | 0.0148 (2) | 0.0097 (2) | 0.0042 (2) | 0.0003 (2) | 0.00078 (19) |
C16 | 0.0270 (4) | 0.0176 (3) | 0.0146 (3) | 0.0018 (3) | 0.0011 (3) | 0.0038 (2) |
C17 | 0.0419 (5) | 0.0192 (3) | 0.0168 (3) | 0.0050 (3) | 0.0027 (3) | 0.0063 (2) |
C18 | 0.0429 (5) | 0.0236 (4) | 0.0148 (3) | 0.0152 (4) | −0.0030 (3) | 0.0031 (3) |
C19 | 0.0284 (4) | 0.0287 (4) | 0.0171 (3) | 0.0129 (3) | −0.0048 (3) | −0.0009 (3) |
C20 | 0.0205 (3) | 0.0219 (3) | 0.0144 (3) | 0.0065 (3) | −0.0005 (2) | 0.0002 (2) |
Geometric parameters (Å, º) top
Cu—O1 | 1.9183 (5) | C8—C9 | 1.5110 (11) |
Cu—N1 | 1.9246 (6) | C8—H8A | 0.9900 |
Cu—O2 | 1.9550 (6) | C8—H8B | 0.9900 |
Cu—N2 | 2.0863 (6) | C9—H9A | 0.9900 |
Cu—O3 | 2.7360 (6) | C9—H9B | 0.9900 |
O1—C1 | 1.3178 (9) | C10—C11 | 1.5228 (11) |
O2—C14 | 1.2828 (9) | C10—H10A | 0.9900 |
O3—C14 | 1.2437 (10) | C10—H10B | 0.9900 |
O1W—H1W1 | 0.821 (12) | C11—H11A | 0.9800 |
O1W—H1W2 | 0.820 (14) | C11—H11B | 0.9800 |
O2W—H2W1 | 0.831 (12) | C11—H11C | 0.9800 |
O2W—H2W2 | 0.825 (13) | C12—C13 | 1.5210 (12) |
N1—C7 | 1.2849 (9) | C12—H12A | 0.9900 |
N1—C8 | 1.4630 (9) | C12—H12B | 0.9900 |
N2—C12 | 1.4850 (10) | C13—H13A | 0.9800 |
N2—C9 | 1.4881 (10) | C13—H13B | 0.9800 |
N2—C10 | 1.4960 (9) | C13—H13C | 0.9800 |
C1—C2 | 1.4156 (10) | C14—C15 | 1.5029 (9) |
C1—C6 | 1.4225 (10) | C15—C20 | 1.3947 (11) |
C2—C3 | 1.3870 (12) | C15—C16 | 1.3963 (11) |
C2—H2A | 0.9500 | C16—C17 | 1.3904 (12) |
C3—C4 | 1.3970 (15) | C16—H16A | 0.9500 |
C3—H3A | 0.9500 | C17—C18 | 1.3881 (16) |
C4—C5 | 1.3754 (12) | C17—H17A | 0.9500 |
C4—H4A | 0.9500 | C18—C19 | 1.3917 (15) |
C5—C6 | 1.4089 (10) | C18—H18A | 0.9500 |
C5—H5A | 0.9500 | C19—C20 | 1.3941 (11) |
C6—C7 | 1.4359 (10) | C19—H19A | 0.9500 |
C7—H7A | 0.9500 | C20—H20A | 0.9500 |
| | | |
O1—Cu—N1 | 93.92 (2) | N2—C9—C8 | 108.59 (6) |
O1—Cu—O2 | 92.62 (2) | N2—C9—H9A | 110.0 |
N1—Cu—O2 | 171.44 (3) | C8—C9—H9A | 110.0 |
O1—Cu—N2 | 165.85 (2) | N2—C9—H9B | 110.0 |
N1—Cu—N2 | 83.64 (2) | C8—C9—H9B | 110.0 |
O2—Cu—N2 | 91.31 (2) | H9A—C9—H9B | 108.4 |
O1—Cu—O3 | 91.16 (2) | N2—C10—C11 | 116.23 (6) |
N1—Cu—O3 | 120.89 (2) | N2—C10—H10A | 108.2 |
O2—Cu—O3 | 53.40 (2) | C11—C10—H10A | 108.2 |
N2—Cu—O3 | 102.08 (2) | N2—C10—H10B | 108.2 |
C1—O1—Cu | 125.54 (5) | C11—C10—H10B | 108.2 |
C14—O2—Cu | 109.64 (5) | H10A—C10—H10B | 107.4 |
C14—O3—Cu | 73.97 (4) | C10—C11—H11A | 109.5 |
H1W1—O1W—H1W2 | 104.6 (15) | C10—C11—H11B | 109.5 |
H2W1—O2W—H2W2 | 103.5 (14) | H11A—C11—H11B | 109.5 |
C7—N1—C8 | 119.66 (6) | C10—C11—H11C | 109.5 |
C7—N1—Cu | 126.40 (5) | H11A—C11—H11C | 109.5 |
C8—N1—Cu | 113.60 (5) | H11B—C11—H11C | 109.5 |
C12—N2—C9 | 110.82 (6) | N2—C12—C13 | 113.04 (7) |
C12—N2—C10 | 111.01 (6) | N2—C12—H12A | 109.0 |
C9—N2—C10 | 111.65 (6) | C13—C12—H12A | 109.0 |
C12—N2—Cu | 110.82 (5) | N2—C12—H12B | 109.0 |
C9—N2—Cu | 105.87 (4) | C13—C12—H12B | 109.0 |
C10—N2—Cu | 106.45 (4) | H12A—C12—H12B | 107.8 |
O1—C1—C2 | 118.88 (7) | C12—C13—H13A | 109.5 |
O1—C1—C6 | 124.23 (6) | C12—C13—H13B | 109.5 |
C2—C1—C6 | 116.89 (7) | H13A—C13—H13B | 109.5 |
C3—C2—C1 | 121.27 (8) | C12—C13—H13C | 109.5 |
C3—C2—H2A | 119.4 | H13A—C13—H13C | 109.5 |
C1—C2—H2A | 119.4 | H13B—C13—H13C | 109.5 |
C2—C3—C4 | 121.28 (7) | O3—C14—O2 | 122.98 (6) |
C2—C3—H3A | 119.4 | O3—C14—C15 | 120.33 (7) |
C4—C3—H3A | 119.4 | O2—C14—C15 | 116.63 (7) |
C5—C4—C3 | 118.66 (8) | C20—C15—C16 | 119.15 (7) |
C5—C4—H4A | 120.7 | C20—C15—C14 | 120.86 (7) |
C3—C4—H4A | 120.7 | C16—C15—C14 | 119.96 (7) |
C4—C5—C6 | 121.43 (8) | C17—C16—C15 | 120.67 (9) |
C4—C5—H5A | 119.3 | C17—C16—H16A | 119.7 |
C6—C5—H5A | 119.3 | C15—C16—H16A | 119.7 |
C5—C6—C1 | 120.43 (7) | C18—C17—C16 | 119.82 (9) |
C5—C6—C7 | 116.04 (7) | C18—C17—H17A | 120.1 |
C1—C6—C7 | 123.53 (6) | C16—C17—H17A | 120.1 |
N1—C7—C6 | 124.89 (6) | C17—C18—C19 | 120.08 (8) |
N1—C7—H7A | 117.6 | C17—C18—H18A | 120.0 |
C6—C7—H7A | 117.6 | C19—C18—H18A | 120.0 |
N1—C8—C9 | 105.33 (6) | C18—C19—C20 | 120.04 (9) |
N1—C8—H8A | 110.7 | C18—C19—H19A | 120.0 |
C9—C8—H8A | 110.7 | C20—C19—H19A | 120.0 |
N1—C8—H8B | 110.7 | C19—C20—C15 | 120.23 (8) |
C9—C8—H8B | 110.7 | C19—C20—H20A | 119.9 |
H8A—C8—H8B | 108.8 | C15—C20—H20A | 119.9 |
| | | |
Cu—O1—C1—C2 | 167.40 (5) | C12—N2—C10—C11 | 69.58 (9) |
Cu—O1—C1—C6 | −12.80 (10) | C9—N2—C10—C11 | −54.64 (9) |
O1—C1—C2—C3 | 179.39 (8) | Cu—N2—C10—C11 | −169.73 (6) |
C6—C1—C2—C3 | −0.42 (11) | C9—N2—C12—C13 | −71.87 (8) |
C1—C2—C3—C4 | −1.45 (13) | C10—N2—C12—C13 | 163.45 (7) |
C2—C3—C4—C5 | 1.69 (13) | Cu—N2—C12—C13 | 45.36 (8) |
C3—C4—C5—C6 | −0.04 (12) | Cu—O3—C14—O2 | −0.92 (6) |
C4—C5—C6—C1 | −1.84 (11) | Cu—O3—C14—C15 | 176.22 (6) |
C4—C5—C6—C7 | 177.93 (7) | Cu—O2—C14—O3 | 1.32 (9) |
O1—C1—C6—C5 | −177.78 (7) | Cu—O2—C14—C15 | −175.93 (5) |
C2—C1—C6—C5 | 2.02 (10) | O3—C14—C15—C20 | 179.00 (7) |
O1—C1—C6—C7 | 2.47 (11) | O2—C14—C15—C20 | −3.67 (10) |
C2—C1—C6—C7 | −177.73 (7) | O3—C14—C15—C16 | −3.00 (10) |
C8—N1—C7—C6 | 174.37 (7) | O2—C14—C15—C16 | 174.33 (7) |
Cu—N1—C7—C6 | 1.60 (11) | C20—C15—C16—C17 | 1.29 (11) |
C5—C6—C7—N1 | −176.20 (7) | C14—C15—C16—C17 | −176.75 (7) |
C1—C6—C7—N1 | 3.56 (11) | C15—C16—C17—C18 | −0.21 (13) |
C7—N1—C8—C9 | −133.03 (7) | C16—C17—C18—C19 | −0.57 (13) |
Cu—N1—C8—C9 | 40.63 (7) | C17—C18—C19—C20 | 0.26 (13) |
C12—N2—C9—C8 | 159.78 (6) | C18—C19—C20—C15 | 0.83 (12) |
C10—N2—C9—C8 | −75.90 (7) | C16—C15—C20—C19 | −1.60 (11) |
Cu—N2—C9—C8 | 39.55 (7) | C14—C15—C20—C19 | 176.42 (7) |
N1—C8—C9—N2 | −52.20 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O3 | 0.82 (1) | 1.98 (1) | 2.7641 (9) | 161 (2) |
O1W—H1W2···O2Wi | 0.82 (1) | 2.07 (1) | 2.8871 (10) | 172 (2) |
O2W—H2W1···O1 | 0.83 (1) | 2.08 (1) | 2.8868 (9) | 165 (2) |
O2W—H2W2···O1W | 0.83 (1) | 2.12 (1) | 2.9378 (11) | 175 (2) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
[(
E)-2-({[2-(Diethylamino)ethyl]imino}methyl)phenolato-
κ3N,
N',
O](2-phenylacetato-
κ2O,
O')copper(II) (2)
top
Crystal data top
[Cu(C8H7O2)(C13H19N2O)] | Dx = 1.418 Mg m−3 |
Mr = 417.98 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 6436 reflections |
a = 23.1862 (10) Å | θ = 3.9–33.6° |
b = 6.4178 (3) Å | µ = 1.14 mm−1 |
c = 13.1598 (6) Å | T = 100 K |
V = 1958.22 (15) Å3 | Plate, blue |
Z = 4 | 0.20 × 0.11 × 0.03 mm |
F(000) = 876 | |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 11501 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 7093 reflections with I > 2σ(I) |
Detector resolution: 10.6501 pixels mm-1 | Rint = 0.089 |
ω scans | θmax = 41.3°, θmin = 3.5° |
Absorption correction: gaussian CrysAlis PRO (Rigaku OD, 2018)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model. Empirical absorption correction
using spherical harmonics, implemented in SCALE3 ABSPACK scaling
algorithm. | h = −37→42 |
Tmin = 0.684, Tmax = 1.000 | k = −11→11 |
46196 measured reflections | l = −23→22 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.056 | w = 1/[σ2(Fo2) + (0.0359P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.121 | (Δ/σ)max = 0.002 |
S = 1.04 | Δρmax = 1.20 e Å−3 |
11501 reflections | Δρmin = −1.04 e Å−3 |
245 parameters | Absolute structure: Flack x determined using 1976 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
1 restraint | Absolute structure parameter: −0.035 (10) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu | 0.50251 (2) | 0.67151 (4) | 0.58234 (5) | 0.01478 (6) | |
O1 | 0.55832 (9) | 0.8376 (3) | 0.51299 (18) | 0.0204 (4) | |
O2 | 0.44362 (8) | 0.8849 (3) | 0.55955 (16) | 0.0185 (4) | |
O3 | 0.43374 (10) | 0.6755 (3) | 0.42593 (18) | 0.0219 (5) | |
N1 | 0.55334 (9) | 0.4358 (3) | 0.5937 (2) | 0.0180 (5) | |
N2 | 0.45221 (10) | 0.5167 (4) | 0.68793 (19) | 0.0176 (4) | |
C1 | 0.61121 (12) | 0.7875 (4) | 0.4914 (2) | 0.0167 (5) | |
C2 | 0.64665 (13) | 0.9369 (5) | 0.4416 (2) | 0.0186 (5) | |
H2A | 0.630815 | 1.069146 | 0.425069 | 0.022* | |
C3 | 0.70285 (13) | 0.8961 (5) | 0.4169 (2) | 0.0201 (5) | |
H3A | 0.725123 | 1.000151 | 0.383750 | 0.024* | |
C4 | 0.72806 (13) | 0.7032 (5) | 0.4396 (2) | 0.0215 (6) | |
H4A | 0.767133 | 0.675768 | 0.422466 | 0.026* | |
C5 | 0.69497 (12) | 0.5539 (5) | 0.4874 (2) | 0.0200 (5) | |
H5A | 0.711564 | 0.422133 | 0.502459 | 0.024* | |
C6 | 0.63715 (12) | 0.5921 (5) | 0.5145 (2) | 0.0176 (5) | |
C7 | 0.60647 (11) | 0.4276 (4) | 0.5657 (2) | 0.0181 (6) | |
H7A | 0.627107 | 0.303159 | 0.580009 | 0.022* | |
C8 | 0.52631 (13) | 0.2571 (5) | 0.6443 (3) | 0.0224 (6) | |
H8A | 0.556181 | 0.164060 | 0.673164 | 0.027* | |
H8B | 0.502894 | 0.176370 | 0.595273 | 0.027* | |
C9 | 0.48849 (14) | 0.3425 (5) | 0.7279 (3) | 0.0226 (6) | |
H9A | 0.463338 | 0.230491 | 0.754515 | 0.027* | |
H9B | 0.512849 | 0.393847 | 0.784358 | 0.027* | |
C10 | 0.43476 (15) | 0.6603 (5) | 0.7715 (3) | 0.0222 (6) | |
H10A | 0.415201 | 0.578917 | 0.825322 | 0.027* | |
H10B | 0.406761 | 0.762946 | 0.744670 | 0.027* | |
C11 | 0.48557 (16) | 0.7759 (6) | 0.8177 (3) | 0.0283 (7) | |
H11A | 0.471804 | 0.867734 | 0.872038 | 0.043* | |
H11B | 0.513054 | 0.675182 | 0.845802 | 0.043* | |
H11C | 0.504613 | 0.859261 | 0.765128 | 0.043* | |
C12 | 0.40028 (13) | 0.4385 (5) | 0.6321 (2) | 0.0222 (6) | |
H12A | 0.413673 | 0.356314 | 0.572965 | 0.027* | |
H12B | 0.378887 | 0.560191 | 0.605402 | 0.027* | |
C13 | 0.35861 (15) | 0.3051 (6) | 0.6926 (3) | 0.0319 (8) | |
H13A | 0.324823 | 0.272829 | 0.650745 | 0.048* | |
H13B | 0.346350 | 0.381139 | 0.753507 | 0.048* | |
H13C | 0.377714 | 0.175336 | 0.712744 | 0.048* | |
C14 | 0.42161 (12) | 0.8351 (5) | 0.4727 (2) | 0.0170 (5) | |
C15 | 0.37829 (13) | 0.9942 (5) | 0.4325 (2) | 0.0215 (6) | |
H15A | 0.351429 | 1.028904 | 0.488492 | 0.026* | |
H15B | 0.399690 | 1.123004 | 0.415505 | 0.026* | |
C16 | 0.34295 (12) | 0.9344 (5) | 0.3416 (2) | 0.0192 (5) | |
C17 | 0.33190 (13) | 1.0802 (5) | 0.2656 (2) | 0.0212 (6) | |
H17A | 0.350911 | 1.211234 | 0.267692 | 0.025* | |
C18 | 0.29376 (14) | 1.0383 (6) | 0.1867 (3) | 0.0258 (6) | |
H18A | 0.286285 | 1.140770 | 0.136301 | 0.031* | |
C19 | 0.26675 (14) | 0.8464 (6) | 0.1823 (3) | 0.0278 (7) | |
H19A | 0.240039 | 0.817626 | 0.129361 | 0.033* | |
C20 | 0.27865 (15) | 0.6955 (6) | 0.2551 (3) | 0.0275 (7) | |
H20A | 0.260772 | 0.562618 | 0.250909 | 0.033* | |
C21 | 0.31655 (13) | 0.7385 (5) | 0.3340 (3) | 0.0226 (6) | |
H21A | 0.324698 | 0.634210 | 0.383164 | 0.027* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.01389 (12) | 0.01448 (11) | 0.01595 (12) | 0.00064 (11) | 0.00013 (14) | 0.00139 (17) |
O1 | 0.0152 (9) | 0.0202 (10) | 0.0257 (11) | 0.0031 (7) | 0.0032 (8) | 0.0053 (8) |
O2 | 0.0156 (8) | 0.0208 (10) | 0.0191 (11) | 0.0012 (7) | −0.0011 (7) | 0.0018 (7) |
O3 | 0.0217 (10) | 0.0242 (11) | 0.0197 (11) | 0.0051 (8) | 0.0012 (8) | −0.0013 (8) |
N1 | 0.0176 (9) | 0.0150 (9) | 0.0214 (14) | −0.0002 (7) | 0.0000 (9) | 0.0003 (9) |
N2 | 0.0165 (10) | 0.0200 (11) | 0.0165 (11) | −0.0005 (8) | 0.0008 (8) | 0.0026 (9) |
C1 | 0.0169 (12) | 0.0184 (12) | 0.0148 (12) | 0.0005 (9) | −0.0008 (9) | 0.0001 (9) |
C2 | 0.0173 (12) | 0.0192 (13) | 0.0192 (13) | 0.0007 (10) | 0.0010 (9) | 0.0000 (10) |
C3 | 0.0175 (13) | 0.0249 (14) | 0.0178 (14) | −0.0032 (10) | 0.0012 (10) | −0.0004 (11) |
C4 | 0.0161 (13) | 0.0275 (16) | 0.0210 (14) | 0.0014 (10) | 0.0037 (10) | −0.0019 (11) |
C5 | 0.0174 (13) | 0.0202 (14) | 0.0226 (14) | 0.0035 (10) | 0.0011 (10) | −0.0011 (11) |
C6 | 0.0162 (12) | 0.0182 (13) | 0.0186 (13) | 0.0005 (9) | −0.0015 (9) | −0.0016 (10) |
C7 | 0.0171 (11) | 0.0148 (11) | 0.0225 (16) | 0.0022 (8) | −0.0020 (9) | −0.0017 (10) |
C8 | 0.0204 (14) | 0.0187 (14) | 0.0281 (16) | −0.0010 (11) | 0.0003 (11) | 0.0025 (12) |
C9 | 0.0237 (14) | 0.0216 (15) | 0.0227 (15) | 0.0014 (11) | 0.0015 (11) | 0.0057 (11) |
C10 | 0.0245 (15) | 0.0240 (16) | 0.0180 (14) | 0.0005 (12) | 0.0042 (11) | 0.0002 (11) |
C11 | 0.0327 (17) | 0.0254 (16) | 0.0269 (18) | −0.0012 (13) | 0.0006 (13) | −0.0014 (13) |
C12 | 0.0192 (13) | 0.0270 (15) | 0.0205 (15) | −0.0046 (11) | −0.0002 (10) | 0.0010 (12) |
C13 | 0.0255 (17) | 0.038 (2) | 0.0323 (19) | −0.0116 (14) | 0.0027 (14) | 0.0040 (15) |
C14 | 0.0127 (11) | 0.0224 (13) | 0.0160 (12) | 0.0005 (9) | 0.0020 (8) | 0.0042 (10) |
C15 | 0.0208 (14) | 0.0203 (14) | 0.0234 (15) | 0.0027 (10) | −0.0039 (11) | 0.0018 (11) |
C16 | 0.0154 (12) | 0.0226 (14) | 0.0196 (14) | 0.0018 (10) | −0.0002 (10) | 0.0026 (10) |
C17 | 0.0164 (13) | 0.0243 (15) | 0.0228 (15) | 0.0026 (11) | 0.0031 (10) | 0.0049 (11) |
C18 | 0.0254 (15) | 0.0350 (18) | 0.0170 (14) | 0.0087 (13) | 0.0026 (11) | 0.0055 (12) |
C19 | 0.0232 (15) | 0.041 (2) | 0.0193 (15) | 0.0076 (13) | −0.0038 (11) | −0.0079 (13) |
C20 | 0.0245 (16) | 0.0287 (18) | 0.0294 (18) | 0.0011 (12) | −0.0019 (13) | −0.0047 (13) |
C21 | 0.0214 (13) | 0.0220 (14) | 0.0244 (15) | 0.0003 (11) | −0.0015 (12) | 0.0021 (12) |
Geometric parameters (Å, º) top
Cu—O1 | 1.909 (2) | C9—H9B | 0.9900 |
Cu—N1 | 1.923 (2) | C10—C11 | 1.519 (5) |
Cu—O2 | 1.957 (2) | C10—H10A | 0.9900 |
Cu—N2 | 2.068 (2) | C10—H10B | 0.9900 |
Cu—O3 | 2.604 (2) | C11—H11A | 0.9800 |
O1—C1 | 1.299 (3) | C11—H11B | 0.9800 |
O2—C14 | 1.292 (4) | C11—H11C | 0.9800 |
O3—C14 | 1.228 (4) | C12—C13 | 1.517 (4) |
N1—C7 | 1.287 (3) | C12—H12A | 0.9900 |
N1—C8 | 1.467 (4) | C12—H12B | 0.9900 |
N2—C10 | 1.490 (4) | C13—H13A | 0.9800 |
N2—C9 | 1.495 (4) | C13—H13B | 0.9800 |
N2—C12 | 1.497 (4) | C13—H13C | 0.9800 |
C1—C2 | 1.423 (4) | C14—C15 | 1.526 (4) |
C1—C6 | 1.424 (4) | C15—C16 | 1.500 (4) |
C2—C3 | 1.368 (4) | C15—H15A | 0.9900 |
C2—H2A | 0.9500 | C15—H15B | 0.9900 |
C3—C4 | 1.402 (4) | C16—C17 | 1.394 (4) |
C3—H3A | 0.9500 | C16—C21 | 1.402 (4) |
C4—C5 | 1.379 (4) | C17—C18 | 1.390 (5) |
C4—H4A | 0.9500 | C17—H17A | 0.9500 |
C5—C6 | 1.408 (4) | C18—C19 | 1.383 (5) |
C5—H5A | 0.9500 | C18—H18A | 0.9500 |
C6—C7 | 1.441 (4) | C19—C20 | 1.390 (5) |
C7—H7A | 0.9500 | C19—H19A | 0.9500 |
C8—C9 | 1.509 (5) | C20—C21 | 1.387 (5) |
C8—H8A | 0.9900 | C20—H20A | 0.9500 |
C8—H8B | 0.9900 | C21—H21A | 0.9500 |
C9—H9A | 0.9900 | | |
| | | |
O1—Cu—N1 | 93.49 (9) | C8—C9—H9B | 109.7 |
O1—Cu—O2 | 90.51 (9) | H9A—C9—H9B | 108.2 |
N1—Cu—O2 | 171.79 (10) | N2—C10—C11 | 112.8 (3) |
O1—Cu—N2 | 166.33 (11) | N2—C10—H10A | 109.0 |
N1—Cu—N2 | 85.17 (10) | C11—C10—H10A | 109.0 |
O2—Cu—N2 | 92.61 (9) | N2—C10—H10B | 109.0 |
O1—Cu—O3 | 91.81 (9) | C11—C10—H10B | 109.0 |
N1—Cu—O3 | 116.37 (10) | H10A—C10—H10B | 107.8 |
O2—Cu—O3 | 56.27 (8) | C10—C11—H11A | 109.5 |
N2—Cu—O3 | 100.98 (9) | C10—C11—H11B | 109.5 |
C1—O1—Cu | 127.30 (19) | H11A—C11—H11B | 109.5 |
C14—O2—Cu | 103.79 (18) | C10—C11—H11C | 109.5 |
C14—O3—Cu | 75.67 (17) | H11A—C11—H11C | 109.5 |
C7—N1—C8 | 120.5 (2) | H11B—C11—H11C | 109.5 |
C7—N1—Cu | 126.6 (2) | N2—C12—C13 | 116.4 (3) |
C8—N1—Cu | 112.84 (18) | N2—C12—H12A | 108.2 |
C10—N2—C9 | 110.8 (3) | C13—C12—H12A | 108.2 |
C10—N2—C12 | 110.6 (2) | N2—C12—H12B | 108.2 |
C9—N2—C12 | 112.0 (2) | C13—C12—H12B | 108.2 |
C10—N2—Cu | 110.60 (19) | H12A—C12—H12B | 107.4 |
C9—N2—Cu | 106.15 (18) | C12—C13—H13A | 109.5 |
C12—N2—Cu | 106.56 (18) | C12—C13—H13B | 109.5 |
O1—C1—C2 | 118.6 (3) | H13A—C13—H13B | 109.5 |
O1—C1—C6 | 124.8 (3) | C12—C13—H13C | 109.5 |
C2—C1—C6 | 116.6 (3) | H13A—C13—H13C | 109.5 |
C3—C2—C1 | 122.1 (3) | H13B—C13—H13C | 109.5 |
C3—C2—H2A | 119.0 | O3—C14—O2 | 124.0 (3) |
C1—C2—H2A | 119.0 | O3—C14—C15 | 122.4 (3) |
C2—C3—C4 | 121.0 (3) | O2—C14—C15 | 113.6 (3) |
C2—C3—H3A | 119.5 | C16—C15—C14 | 117.7 (3) |
C4—C3—H3A | 119.5 | C16—C15—H15A | 107.9 |
C5—C4—C3 | 118.6 (3) | C14—C15—H15A | 107.9 |
C5—C4—H4A | 120.7 | C16—C15—H15B | 107.9 |
C3—C4—H4A | 120.7 | C14—C15—H15B | 107.9 |
C4—C5—C6 | 121.6 (3) | H15A—C15—H15B | 107.2 |
C4—C5—H5A | 119.2 | C17—C16—C21 | 118.0 (3) |
C6—C5—H5A | 119.2 | C17—C16—C15 | 120.1 (3) |
C5—C6—C1 | 120.1 (3) | C21—C16—C15 | 121.7 (3) |
C5—C6—C7 | 117.4 (3) | C18—C17—C16 | 121.6 (3) |
C1—C6—C7 | 122.4 (3) | C18—C17—H17A | 119.2 |
N1—C7—C6 | 125.2 (3) | C16—C17—H17A | 119.2 |
N1—C7—H7A | 117.4 | C19—C18—C17 | 119.5 (3) |
C6—C7—H7A | 117.4 | C19—C18—H18A | 120.3 |
N1—C8—C9 | 107.2 (3) | C17—C18—H18A | 120.3 |
N1—C8—H8A | 110.3 | C18—C19—C20 | 120.1 (3) |
C9—C8—H8A | 110.3 | C18—C19—H19A | 120.0 |
N1—C8—H8B | 110.3 | C20—C19—H19A | 120.0 |
C9—C8—H8B | 110.3 | C21—C20—C19 | 120.2 (3) |
H8A—C8—H8B | 108.5 | C21—C20—H20A | 119.9 |
N2—C9—C8 | 110.0 (3) | C19—C20—H20A | 119.9 |
N2—C9—H9A | 109.7 | C20—C21—C16 | 120.6 (3) |
C8—C9—H9A | 109.7 | C20—C21—H21A | 119.7 |
N2—C9—H9B | 109.7 | C16—C21—H21A | 119.7 |
| | | |
Cu—O1—C1—C2 | −178.1 (2) | C9—N2—C10—C11 | 66.1 (3) |
Cu—O1—C1—C6 | 1.5 (4) | C12—N2—C10—C11 | −169.2 (3) |
O1—C1—C2—C3 | 179.7 (3) | Cu—N2—C10—C11 | −51.4 (3) |
C6—C1—C2—C3 | 0.0 (4) | C10—N2—C12—C13 | −64.0 (4) |
C1—C2—C3—C4 | 0.1 (5) | C9—N2—C12—C13 | 60.1 (4) |
C2—C3—C4—C5 | 0.2 (5) | Cu—N2—C12—C13 | 175.8 (3) |
C3—C4—C5—C6 | −0.7 (5) | Cu—O3—C14—O2 | −4.8 (2) |
C4—C5—C6—C1 | 0.8 (5) | Cu—O3—C14—C15 | 175.4 (3) |
C4—C5—C6—C7 | −179.0 (3) | Cu—O2—C14—O3 | 6.4 (3) |
O1—C1—C6—C5 | 179.9 (3) | Cu—O2—C14—C15 | −173.84 (19) |
C2—C1—C6—C5 | −0.5 (4) | O3—C14—C15—C16 | 10.0 (4) |
O1—C1—C6—C7 | −0.4 (5) | O2—C14—C15—C16 | −169.8 (3) |
C2—C1—C6—C7 | 179.3 (3) | C14—C15—C16—C17 | −139.8 (3) |
C8—N1—C7—C6 | 179.2 (3) | C14—C15—C16—C21 | 45.1 (4) |
Cu—N1—C7—C6 | −4.0 (4) | C21—C16—C17—C18 | 3.1 (5) |
C5—C6—C7—N1 | −178.5 (3) | C15—C16—C17—C18 | −172.1 (3) |
C1—C6—C7—N1 | 1.7 (5) | C16—C17—C18—C19 | −1.2 (5) |
C7—N1—C8—C9 | 139.9 (3) | C17—C18—C19—C20 | −1.2 (5) |
Cu—N1—C8—C9 | −37.3 (3) | C18—C19—C20—C21 | 1.6 (5) |
C10—N2—C9—C8 | −155.3 (3) | C19—C20—C21—C16 | 0.5 (5) |
C12—N2—C9—C8 | 80.7 (3) | C17—C16—C21—C20 | −2.8 (5) |
Cu—N2—C9—C8 | −35.2 (3) | C15—C16—C21—C20 | 172.4 (3) |
N1—C8—C9—N2 | 47.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O2i | 0.99 | 2.37 | 3.260 (4) | 149 |
C9—H9B···O3ii | 0.99 | 2.28 | 3.172 (4) | 149 |
C12—H12B···O2 | 0.99 | 2.64 | 3.183 (4) | 115 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, z+1/2. |
Bis[µ-(
E)-2-({[3-(diethylamino)propyl]imino}methyl)phenolato]-
κ4N,
N',
O:
O;
κ4O:
N,
N',
O-(µ-2-methylbenzoato-
κ2O:
O')copper(II) perchlorate (3)
top
Crystal data top
[Cu2(C8H7O2)(C12H17N2O)2]ClO4 | Dx = 1.521 Mg m−3 |
Mr = 772.22 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 21097 reflections |
a = 10.51085 (16) Å | θ = 3.7–36.4° |
b = 22.2419 (5) Å | µ = 1.40 mm−1 |
c = 28.8403 (5) Å | T = 100 K |
V = 6742.3 (2) Å3 | Plate, green-blue |
Z = 8 | 0.26 × 0.21 × 0.03 mm |
F(000) = 3200 | |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 22070 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 12413 reflections with I > 2σ(I) |
Detector resolution: 10.6501 pixels mm-1 | Rint = 0.090 |
ω scans | θmax = 41.6°, θmin = 3.4° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018) | h = −18→19 |
Tmin = 0.614, Tmax = 1.000 | k = −33→40 |
154652 measured reflections | l = −35→52 |
Refinement top
Refinement on F2 | 44 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.039P)2 + 5.3824P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
22070 reflections | Δρmax = 1.13 e Å−3 |
467 parameters | Δρmin = −1.10 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.28173 (2) | 1.08502 (2) | 0.16413 (2) | 0.01838 (4) | |
Cu2 | 0.32761 (2) | 0.99599 (2) | 0.08706 (2) | 0.01958 (4) | |
O1 | 0.18853 (12) | 1.01143 (6) | 0.14771 (5) | 0.0219 (2) | |
O2 | 0.44003 (11) | 1.05731 (6) | 0.11374 (5) | 0.0215 (2) | |
O3 | 0.18608 (13) | 1.12125 (6) | 0.11331 (5) | 0.0241 (3) | |
O4 | 0.24510 (13) | 1.06268 (6) | 0.05351 (5) | 0.0255 (3) | |
N1 | 0.32825 (14) | 1.17468 (7) | 0.18137 (6) | 0.0223 (3) | |
N2 | 0.35486 (14) | 1.04593 (7) | 0.21946 (5) | 0.0229 (3) | |
N3 | 0.42640 (14) | 0.93093 (7) | 0.11619 (6) | 0.0232 (3) | |
N4 | 0.24861 (19) | 0.93856 (9) | 0.03741 (7) | 0.0353 (4) | |
C1 | 0.15786 (15) | 0.96685 (8) | 0.17591 (6) | 0.0204 (3) | |
C2 | 0.06056 (16) | 0.92586 (8) | 0.16282 (8) | 0.0259 (3) | |
H2A | 0.018193 | 0.931168 | 0.134018 | 0.031* | |
C3 | 0.02630 (19) | 0.87838 (9) | 0.19118 (9) | 0.0326 (4) | |
H3A | −0.040146 | 0.852123 | 0.181767 | 0.039* | |
C4 | 0.0877 (2) | 0.86842 (10) | 0.23339 (9) | 0.0377 (5) | |
H4A | 0.063932 | 0.835617 | 0.252624 | 0.045* | |
C5 | 0.1835 (2) | 0.90699 (10) | 0.24663 (8) | 0.0340 (4) | |
H5A | 0.226834 | 0.900052 | 0.275026 | 0.041* | |
C6 | 0.21861 (18) | 0.95663 (8) | 0.21897 (7) | 0.0238 (3) | |
C7 | 0.31918 (17) | 0.99510 (8) | 0.23622 (7) | 0.0235 (3) | |
H7A | 0.363661 | 0.981258 | 0.262830 | 0.028* | |
C8 | 0.45833 (19) | 1.07664 (10) | 0.24478 (7) | 0.0305 (4) | |
H8A | 0.535325 | 1.078379 | 0.225058 | 0.037* | |
H8B | 0.479509 | 1.053689 | 0.273162 | 0.037* | |
C9 | 0.4179 (2) | 1.13985 (10) | 0.25785 (7) | 0.0310 (4) | |
H9A | 0.328741 | 1.138993 | 0.268907 | 0.037* | |
H9B | 0.471883 | 1.154315 | 0.283668 | 0.037* | |
C10 | 0.42827 (18) | 1.18331 (10) | 0.21765 (7) | 0.0297 (4) | |
H10A | 0.422390 | 1.224879 | 0.229733 | 0.036* | |
H10B | 0.512998 | 1.178625 | 0.203100 | 0.036* | |
C11 | 0.20745 (19) | 1.20172 (11) | 0.19811 (8) | 0.0338 (5) | |
H11A | 0.220059 | 1.244773 | 0.203678 | 0.051* | |
H11B | 0.181586 | 1.182086 | 0.227028 | 0.051* | |
H11C | 0.141026 | 1.196136 | 0.174653 | 0.051* | |
C12 | 0.3685 (2) | 1.21036 (10) | 0.14034 (8) | 0.0314 (4) | |
H12A | 0.390609 | 1.251243 | 0.150133 | 0.047* | |
H12B | 0.298717 | 1.212011 | 0.117853 | 0.047* | |
H12C | 0.442856 | 1.191360 | 0.125973 | 0.047* | |
C13 | 0.56329 (16) | 1.04925 (8) | 0.12129 (6) | 0.0195 (3) | |
C14 | 0.64547 (17) | 1.09933 (8) | 0.12300 (7) | 0.0232 (3) | |
H14A | 0.611230 | 1.138621 | 0.119659 | 0.028* | |
C15 | 0.77541 (17) | 1.09226 (9) | 0.12948 (7) | 0.0243 (3) | |
H15A | 0.828659 | 1.126763 | 0.130131 | 0.029* | |
C16 | 0.82929 (17) | 1.03539 (9) | 0.13505 (8) | 0.0273 (4) | |
H16A | 0.918577 | 1.030819 | 0.138755 | 0.033* | |
C17 | 0.75007 (18) | 0.98594 (9) | 0.13505 (8) | 0.0276 (4) | |
H17A | 0.785487 | 0.947130 | 0.139803 | 0.033* | |
C18 | 0.61758 (16) | 0.99162 (8) | 0.12815 (6) | 0.0216 (3) | |
C19 | 0.54316 (17) | 0.93722 (8) | 0.12929 (7) | 0.0247 (3) | |
H19A | 0.584320 | 0.902305 | 0.140915 | 0.030* | |
C20 | 0.37186 (19) | 0.87002 (9) | 0.12140 (8) | 0.0295 (4) | |
H20A | 0.294207 | 0.872019 | 0.140770 | 0.035* | |
H20B | 0.433996 | 0.843546 | 0.137170 | 0.035* | |
C21 | 0.3391 (2) | 0.84414 (11) | 0.07424 (11) | 0.0425 (6) | |
H21A | 0.414251 | 0.847807 | 0.053734 | 0.051* | |
H21B | 0.319906 | 0.800810 | 0.077773 | 0.051* | |
C22 | 0.2275 (3) | 0.87454 (11) | 0.05142 (10) | 0.0431 (6) | |
H22A | 0.203933 | 0.851222 | 0.023480 | 0.052* | |
H22B | 0.154364 | 0.873092 | 0.073008 | 0.052* | |
C23 | 0.3397 (3) | 0.94346 (15) | −0.00141 (10) | 0.0532 (7) | |
H23A | 0.309784 | 0.919079 | −0.027527 | 0.080* | |
H23B | 0.423371 | 0.928975 | 0.008627 | 0.080* | |
H23C | 0.346501 | 0.985575 | −0.011092 | 0.080* | |
C24 | 0.1215 (3) | 0.95918 (14) | 0.02074 (11) | 0.0534 (7) | |
H24A | 0.089533 | 0.931073 | −0.002688 | 0.080* | |
H24B | 0.129479 | 0.999341 | 0.007071 | 0.080* | |
H24C | 0.062063 | 0.960663 | 0.046891 | 0.080* | |
C25 | 0.19144 (16) | 1.10812 (8) | 0.07068 (6) | 0.0209 (3) | |
C26 | 0.12577 (17) | 1.15150 (8) | 0.03844 (6) | 0.0220 (3) | |
C27 | 0.02568 (18) | 1.18557 (9) | 0.05705 (7) | 0.0259 (3) | |
H27A | 0.003035 | 1.180622 | 0.088715 | 0.031* | |
C28 | −0.0408 (2) | 1.22642 (10) | 0.02983 (8) | 0.0333 (4) | |
H28A | −0.110083 | 1.248384 | 0.042477 | 0.040* | |
C29 | −0.0050 (2) | 1.23482 (10) | −0.01588 (9) | 0.0388 (5) | |
H29A | −0.048923 | 1.263227 | −0.034560 | 0.047* | |
C30 | 0.0943 (2) | 1.20205 (11) | −0.03445 (8) | 0.0358 (5) | |
H30A | 0.117859 | 1.208614 | −0.065840 | 0.043* | |
C31 | 0.16139 (19) | 1.15931 (9) | −0.00827 (7) | 0.0277 (4) | |
C32 | 0.2693 (2) | 1.12608 (12) | −0.03120 (8) | 0.0384 (5) | |
H32A | 0.290621 | 1.145716 | −0.060613 | 0.058* | |
H32B | 0.243726 | 1.084418 | −0.037115 | 0.058* | |
H32C | 0.343858 | 1.126512 | −0.010781 | 0.058* | |
Cl1 | 0.71528 (4) | 0.76845 (2) | 0.15982 (2) | 0.02309 (8) | |
O11A | 0.7359 (13) | 0.8310 (3) | 0.1481 (5) | 0.0305 (14) | 0.64 (4) |
O12A | 0.5835 (7) | 0.7574 (6) | 0.1677 (4) | 0.0448 (17) | 0.64 (4) |
O13A | 0.7872 (10) | 0.7544 (7) | 0.2006 (4) | 0.054 (2) | 0.64 (4) |
O14A | 0.7590 (13) | 0.7325 (4) | 0.1220 (4) | 0.059 (2) | 0.64 (4) |
O11B | 0.752 (2) | 0.8298 (6) | 0.1535 (9) | 0.030 (2) | 0.36 (4) |
O12B | 0.5852 (13) | 0.7673 (13) | 0.1760 (10) | 0.058 (5) | 0.36 (4) |
O13B | 0.7955 (17) | 0.7392 (9) | 0.1922 (7) | 0.053 (3) | 0.36 (4) |
O14B | 0.722 (3) | 0.7377 (9) | 0.1163 (5) | 0.068 (4) | 0.36 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02042 (9) | 0.01657 (9) | 0.01815 (8) | −0.00045 (7) | −0.00320 (7) | −0.00008 (7) |
Cu2 | 0.01951 (9) | 0.01557 (9) | 0.02365 (10) | 0.00206 (7) | −0.00306 (7) | −0.00206 (7) |
O1 | 0.0221 (5) | 0.0193 (6) | 0.0244 (6) | −0.0017 (4) | −0.0033 (4) | −0.0001 (5) |
O2 | 0.0177 (5) | 0.0171 (6) | 0.0296 (6) | 0.0018 (4) | −0.0019 (4) | −0.0030 (5) |
O3 | 0.0316 (6) | 0.0205 (6) | 0.0203 (6) | 0.0060 (5) | −0.0060 (5) | −0.0016 (5) |
O4 | 0.0320 (6) | 0.0224 (6) | 0.0221 (6) | 0.0068 (5) | −0.0036 (5) | −0.0010 (5) |
N1 | 0.0204 (6) | 0.0199 (7) | 0.0266 (7) | −0.0024 (5) | 0.0026 (5) | −0.0039 (5) |
N2 | 0.0220 (6) | 0.0246 (8) | 0.0221 (7) | −0.0023 (5) | −0.0050 (5) | 0.0014 (5) |
N3 | 0.0204 (6) | 0.0166 (6) | 0.0326 (8) | 0.0014 (5) | −0.0028 (5) | −0.0002 (6) |
N4 | 0.0414 (10) | 0.0278 (9) | 0.0367 (10) | −0.0033 (7) | −0.0122 (8) | −0.0086 (8) |
C1 | 0.0184 (7) | 0.0159 (7) | 0.0269 (8) | 0.0019 (5) | 0.0015 (6) | −0.0010 (6) |
C2 | 0.0187 (7) | 0.0201 (8) | 0.0388 (10) | 0.0010 (6) | −0.0001 (7) | −0.0048 (7) |
C3 | 0.0257 (8) | 0.0181 (9) | 0.0539 (13) | −0.0036 (6) | 0.0070 (8) | −0.0052 (8) |
C4 | 0.0469 (12) | 0.0214 (10) | 0.0449 (13) | −0.0063 (8) | 0.0116 (10) | 0.0046 (9) |
C5 | 0.0463 (12) | 0.0223 (9) | 0.0333 (10) | −0.0012 (8) | 0.0021 (9) | 0.0057 (8) |
C6 | 0.0266 (8) | 0.0182 (8) | 0.0266 (8) | 0.0004 (6) | 0.0000 (6) | 0.0029 (6) |
C7 | 0.0263 (8) | 0.0209 (8) | 0.0234 (7) | 0.0009 (6) | −0.0046 (6) | 0.0031 (6) |
C8 | 0.0257 (8) | 0.0383 (12) | 0.0273 (9) | −0.0082 (7) | −0.0091 (7) | 0.0042 (8) |
C9 | 0.0307 (9) | 0.0371 (11) | 0.0253 (9) | −0.0117 (8) | −0.0039 (7) | −0.0058 (8) |
C10 | 0.0251 (8) | 0.0297 (10) | 0.0343 (10) | −0.0091 (7) | −0.0013 (7) | −0.0045 (8) |
C11 | 0.0246 (8) | 0.0384 (12) | 0.0383 (11) | 0.0001 (8) | 0.0053 (8) | −0.0165 (9) |
C12 | 0.0315 (9) | 0.0228 (9) | 0.0399 (11) | 0.0001 (7) | 0.0057 (8) | 0.0068 (8) |
C13 | 0.0198 (6) | 0.0180 (7) | 0.0207 (7) | 0.0006 (5) | −0.0001 (5) | −0.0011 (5) |
C14 | 0.0215 (7) | 0.0190 (8) | 0.0291 (8) | −0.0001 (6) | 0.0005 (6) | −0.0031 (6) |
C15 | 0.0208 (7) | 0.0238 (9) | 0.0282 (8) | −0.0026 (6) | 0.0001 (6) | −0.0037 (7) |
C16 | 0.0192 (7) | 0.0260 (9) | 0.0367 (10) | −0.0003 (6) | −0.0047 (7) | −0.0010 (7) |
C17 | 0.0221 (7) | 0.0228 (9) | 0.0380 (10) | 0.0017 (6) | −0.0064 (7) | 0.0031 (7) |
C18 | 0.0199 (7) | 0.0188 (8) | 0.0261 (8) | 0.0016 (5) | −0.0033 (6) | 0.0013 (6) |
C19 | 0.0231 (7) | 0.0173 (8) | 0.0336 (9) | 0.0034 (6) | −0.0028 (6) | 0.0025 (7) |
C20 | 0.0240 (8) | 0.0161 (8) | 0.0484 (12) | 0.0015 (6) | −0.0005 (8) | 0.0024 (8) |
C21 | 0.0417 (12) | 0.0216 (10) | 0.0643 (17) | −0.0029 (8) | 0.0073 (11) | −0.0096 (10) |
C22 | 0.0471 (13) | 0.0308 (12) | 0.0514 (15) | −0.0087 (10) | −0.0051 (11) | −0.0138 (11) |
C23 | 0.0700 (19) | 0.0531 (18) | 0.0365 (13) | −0.0012 (14) | 0.0041 (13) | −0.0218 (12) |
C24 | 0.0475 (14) | 0.0573 (18) | 0.0553 (16) | −0.0143 (13) | −0.0279 (13) | 0.0002 (14) |
C25 | 0.0232 (7) | 0.0175 (7) | 0.0221 (7) | 0.0004 (5) | −0.0037 (6) | 0.0010 (6) |
C26 | 0.0249 (7) | 0.0184 (8) | 0.0227 (7) | −0.0014 (6) | −0.0050 (6) | 0.0029 (6) |
C27 | 0.0275 (8) | 0.0199 (8) | 0.0303 (9) | 0.0012 (6) | −0.0056 (7) | 0.0012 (7) |
C28 | 0.0336 (10) | 0.0224 (9) | 0.0440 (12) | 0.0036 (7) | −0.0117 (9) | 0.0037 (8) |
C29 | 0.0462 (12) | 0.0262 (11) | 0.0439 (12) | 0.0001 (9) | −0.0183 (10) | 0.0131 (9) |
C30 | 0.0474 (12) | 0.0314 (11) | 0.0287 (10) | −0.0057 (9) | −0.0092 (9) | 0.0105 (8) |
C31 | 0.0333 (9) | 0.0251 (9) | 0.0249 (8) | −0.0049 (7) | −0.0045 (7) | 0.0045 (7) |
C32 | 0.0481 (13) | 0.0394 (13) | 0.0277 (10) | 0.0012 (10) | 0.0058 (9) | 0.0043 (9) |
Cl1 | 0.02552 (18) | 0.01891 (18) | 0.02484 (18) | 0.00209 (14) | −0.00050 (14) | 0.00546 (14) |
O11A | 0.040 (4) | 0.0144 (16) | 0.037 (3) | 0.0024 (15) | −0.008 (3) | 0.0036 (14) |
O12A | 0.026 (2) | 0.051 (4) | 0.057 (3) | −0.010 (2) | −0.0030 (17) | 0.013 (2) |
O13A | 0.040 (3) | 0.069 (5) | 0.052 (3) | −0.001 (3) | −0.013 (2) | 0.037 (3) |
O14A | 0.092 (5) | 0.0242 (19) | 0.060 (4) | 0.003 (3) | 0.038 (3) | −0.010 (3) |
O11B | 0.031 (4) | 0.018 (3) | 0.041 (6) | 0.001 (3) | −0.015 (3) | 0.000 (3) |
O12B | 0.026 (4) | 0.056 (8) | 0.092 (11) | 0.007 (4) | 0.008 (5) | 0.019 (7) |
O13B | 0.042 (4) | 0.050 (6) | 0.066 (7) | 0.020 (4) | −0.016 (4) | 0.025 (5) |
O14B | 0.135 (12) | 0.036 (6) | 0.033 (4) | −0.032 (7) | −0.001 (6) | −0.010 (3) |
Geometric parameters (Å, º) top
Cu1—O3 | 1.9514 (13) | C12—H12C | 0.9800 |
Cu1—O1 | 1.9654 (13) | C13—C14 | 1.410 (2) |
Cu1—N2 | 1.9731 (15) | C13—C18 | 1.417 (2) |
Cu1—N1 | 2.1126 (16) | C14—C15 | 1.387 (2) |
Cu1—O2 | 2.2935 (13) | C14—H14A | 0.9500 |
Cu1—Cu2 | 3.0155 (3) | C15—C16 | 1.395 (3) |
Cu2—O2 | 1.9615 (13) | C15—H15A | 0.9500 |
Cu2—N3 | 1.9693 (15) | C16—C17 | 1.379 (3) |
Cu2—O4 | 1.9719 (14) | C16—H16A | 0.9500 |
Cu2—N4 | 2.0909 (18) | C17—C18 | 1.412 (3) |
Cu2—O1 | 2.3053 (14) | C17—H17A | 0.9500 |
O1—C1 | 1.322 (2) | C18—C19 | 1.441 (3) |
O2—C13 | 1.326 (2) | C19—H19A | 0.9500 |
O3—C25 | 1.265 (2) | C20—C21 | 1.517 (4) |
O4—C25 | 1.259 (2) | C20—H20A | 0.9900 |
N1—C11 | 1.485 (2) | C20—H20B | 0.9900 |
N1—C12 | 1.486 (3) | C21—C22 | 1.505 (4) |
N1—C10 | 1.496 (3) | C21—H21A | 0.9900 |
N2—C7 | 1.285 (2) | C21—H21B | 0.9900 |
N2—C8 | 1.477 (2) | C22—H22A | 0.9900 |
N3—C19 | 1.292 (2) | C22—H22B | 0.9900 |
N3—C20 | 1.479 (2) | C23—H23A | 0.9800 |
N4—C23 | 1.478 (4) | C23—H23B | 0.9800 |
N4—C24 | 1.492 (3) | C23—H23C | 0.9800 |
N4—C22 | 1.497 (3) | C24—H24A | 0.9800 |
C1—C6 | 1.415 (3) | C24—H24B | 0.9800 |
C1—C2 | 1.421 (2) | C24—H24C | 0.9800 |
C2—C3 | 1.383 (3) | C25—C26 | 1.507 (2) |
C2—H2A | 0.9500 | C26—C27 | 1.403 (3) |
C3—C4 | 1.396 (4) | C26—C31 | 1.409 (3) |
C3—H3A | 0.9500 | C27—C28 | 1.389 (3) |
C4—C5 | 1.376 (3) | C27—H27A | 0.9500 |
C4—H4A | 0.9500 | C28—C29 | 1.383 (4) |
C5—C6 | 1.411 (3) | C28—H28A | 0.9500 |
C5—H5A | 0.9500 | C29—C30 | 1.381 (4) |
C6—C7 | 1.448 (3) | C29—H29A | 0.9500 |
C7—H7A | 0.9500 | C30—C31 | 1.404 (3) |
C8—C9 | 1.516 (3) | C30—H30A | 0.9500 |
C8—H8A | 0.9900 | C31—C32 | 1.507 (3) |
C8—H8B | 0.9900 | C32—H32A | 0.9800 |
C9—C10 | 1.513 (3) | C32—H32B | 0.9800 |
C9—H9A | 0.9900 | C32—H32C | 0.9800 |
C9—H9B | 0.9900 | Cl1—O13B | 1.417 (11) |
C10—H10A | 0.9900 | Cl1—O12A | 1.425 (7) |
C10—H10B | 0.9900 | Cl1—O11B | 1.428 (12) |
C11—H11A | 0.9800 | Cl1—O14A | 1.430 (6) |
C11—H11B | 0.9800 | Cl1—O14B | 1.433 (11) |
C11—H11C | 0.9800 | Cl1—O13A | 1.433 (7) |
C12—H12A | 0.9800 | Cl1—O12B | 1.445 (12) |
C12—H12B | 0.9800 | Cl1—O11A | 1.448 (7) |
| | | |
O3—Cu1—O1 | 84.62 (6) | H11A—C11—H11C | 109.5 |
O3—Cu1—N2 | 171.91 (6) | H11B—C11—H11C | 109.5 |
O1—Cu1—N2 | 91.26 (6) | N1—C12—H12A | 109.5 |
O3—Cu1—N1 | 84.62 (6) | N1—C12—H12B | 109.5 |
O1—Cu1—N1 | 163.37 (6) | H12A—C12—H12B | 109.5 |
N2—Cu1—N1 | 97.79 (7) | N1—C12—H12C | 109.5 |
O3—Cu1—O2 | 90.51 (5) | H12A—C12—H12C | 109.5 |
O1—Cu1—O2 | 89.15 (5) | H12B—C12—H12C | 109.5 |
N2—Cu1—O2 | 96.40 (6) | O2—C13—C14 | 119.83 (16) |
N1—Cu1—O2 | 103.59 (5) | O2—C13—C18 | 122.59 (15) |
O3—Cu1—Cu2 | 78.46 (4) | C14—C13—C18 | 117.58 (15) |
O1—Cu1—Cu2 | 49.86 (4) | C15—C14—C13 | 121.20 (17) |
N2—Cu1—Cu2 | 104.15 (5) | C15—C14—H14A | 119.4 |
N1—Cu1—Cu2 | 139.14 (4) | C13—C14—H14A | 119.4 |
O2—Cu1—Cu2 | 40.58 (3) | C14—C15—C16 | 121.19 (17) |
O2—Cu2—N3 | 91.49 (6) | C14—C15—H15A | 119.4 |
O2—Cu2—O4 | 86.24 (6) | C16—C15—H15A | 119.4 |
N3—Cu2—O4 | 173.70 (6) | C17—C16—C15 | 118.55 (17) |
O2—Cu2—N4 | 158.84 (7) | C17—C16—H16A | 120.7 |
N3—Cu2—N4 | 93.01 (7) | C15—C16—H16A | 120.7 |
O4—Cu2—N4 | 87.06 (7) | C16—C17—C18 | 121.59 (18) |
O2—Cu2—O1 | 88.90 (5) | C16—C17—H17A | 119.2 |
N3—Cu2—O1 | 96.90 (6) | C18—C17—H17A | 119.2 |
O4—Cu2—O1 | 88.94 (5) | C17—C18—C13 | 119.84 (16) |
N4—Cu2—O1 | 111.03 (7) | C17—C18—C19 | 117.18 (16) |
O2—Cu2—Cu1 | 49.52 (4) | C13—C18—C19 | 122.97 (15) |
N3—Cu2—Cu1 | 104.63 (5) | N3—C19—C18 | 126.86 (17) |
O4—Cu2—Cu1 | 78.32 (4) | N3—C19—H19A | 116.6 |
N4—Cu2—Cu1 | 147.40 (6) | C18—C19—H19A | 116.6 |
O1—Cu2—Cu1 | 40.67 (3) | N3—C20—C21 | 110.15 (19) |
C1—O1—Cu1 | 126.72 (12) | N3—C20—H20A | 109.6 |
C1—O1—Cu2 | 120.64 (11) | C21—C20—H20A | 109.6 |
Cu1—O1—Cu2 | 89.47 (5) | N3—C20—H20B | 109.6 |
C13—O2—Cu2 | 123.99 (11) | C21—C20—H20B | 109.6 |
C13—O2—Cu1 | 129.87 (11) | H20A—C20—H20B | 108.1 |
Cu2—O2—Cu1 | 89.91 (5) | C22—C21—C20 | 113.5 (2) |
C25—O3—Cu1 | 127.72 (12) | C22—C21—H21A | 108.9 |
C25—O4—Cu2 | 127.43 (12) | C20—C21—H21A | 108.9 |
C11—N1—C12 | 106.62 (17) | C22—C21—H21B | 108.9 |
C11—N1—C10 | 108.75 (15) | C20—C21—H21B | 108.9 |
C12—N1—C10 | 106.75 (15) | H21A—C21—H21B | 107.7 |
C11—N1—Cu1 | 105.12 (12) | N4—C22—C21 | 115.5 (2) |
C12—N1—Cu1 | 112.50 (13) | N4—C22—H22A | 108.4 |
C10—N1—Cu1 | 116.64 (13) | C21—C22—H22A | 108.4 |
C7—N2—C8 | 115.82 (16) | N4—C22—H22B | 108.4 |
C7—N2—Cu1 | 125.31 (13) | C21—C22—H22B | 108.4 |
C8—N2—Cu1 | 118.87 (13) | H22A—C22—H22B | 107.5 |
C19—N3—C20 | 115.97 (16) | N4—C23—H23A | 109.5 |
C19—N3—Cu2 | 123.10 (13) | N4—C23—H23B | 109.5 |
C20—N3—Cu2 | 120.81 (12) | H23A—C23—H23B | 109.5 |
C23—N4—C24 | 108.3 (2) | N4—C23—H23C | 109.5 |
C23—N4—C22 | 111.8 (2) | H23A—C23—H23C | 109.5 |
C24—N4—C22 | 104.3 (2) | H23B—C23—H23C | 109.5 |
C23—N4—Cu2 | 102.51 (15) | N4—C24—H24A | 109.5 |
C24—N4—Cu2 | 112.86 (16) | N4—C24—H24B | 109.5 |
C22—N4—Cu2 | 117.07 (15) | H24A—C24—H24B | 109.5 |
O1—C1—C6 | 123.39 (16) | N4—C24—H24C | 109.5 |
O1—C1—C2 | 119.55 (17) | H24A—C24—H24C | 109.5 |
C6—C1—C2 | 117.05 (17) | H24B—C24—H24C | 109.5 |
C3—C2—C1 | 121.3 (2) | O4—C25—O3 | 125.98 (16) |
C3—C2—H2A | 119.3 | O4—C25—C26 | 118.45 (16) |
C1—C2—H2A | 119.3 | O3—C25—C26 | 115.56 (16) |
C2—C3—C4 | 121.09 (19) | C27—C26—C31 | 119.90 (17) |
C2—C3—H3A | 119.5 | C27—C26—C25 | 116.94 (16) |
C4—C3—H3A | 119.5 | C31—C26—C25 | 123.16 (17) |
C5—C4—C3 | 118.8 (2) | C28—C27—C26 | 120.9 (2) |
C5—C4—H4A | 120.6 | C28—C27—H27A | 119.5 |
C3—C4—H4A | 120.6 | C26—C27—H27A | 119.5 |
C4—C5—C6 | 121.5 (2) | C29—C28—C27 | 119.4 (2) |
C4—C5—H5A | 119.3 | C29—C28—H28A | 120.3 |
C6—C5—H5A | 119.3 | C27—C28—H28A | 120.3 |
C5—C6—C1 | 120.24 (18) | C30—C29—C28 | 120.2 (2) |
C5—C6—C7 | 117.34 (18) | C30—C29—H29A | 119.9 |
C1—C6—C7 | 122.41 (16) | C28—C29—H29A | 119.9 |
N2—C7—C6 | 127.13 (17) | C29—C30—C31 | 121.9 (2) |
N2—C7—H7A | 116.4 | C29—C30—H30A | 119.0 |
C6—C7—H7A | 116.4 | C31—C30—H30A | 119.0 |
N2—C8—C9 | 110.19 (16) | C30—C31—C26 | 117.7 (2) |
N2—C8—H8A | 109.6 | C30—C31—C32 | 118.3 (2) |
C9—C8—H8A | 109.6 | C26—C31—C32 | 124.01 (18) |
N2—C8—H8B | 109.6 | C31—C32—H32A | 109.5 |
C9—C8—H8B | 109.6 | C31—C32—H32B | 109.5 |
H8A—C8—H8B | 108.1 | H32A—C32—H32B | 109.5 |
C10—C9—C8 | 112.43 (17) | C31—C32—H32C | 109.5 |
C10—C9—H9A | 109.1 | H32A—C32—H32C | 109.5 |
C8—C9—H9A | 109.1 | H32B—C32—H32C | 109.5 |
C10—C9—H9B | 109.1 | O13B—Cl1—O11B | 111.3 (10) |
C8—C9—H9B | 109.1 | O12A—Cl1—O14A | 109.8 (5) |
H9A—C9—H9B | 107.8 | O13B—Cl1—O14B | 109.3 (9) |
N1—C10—C9 | 113.79 (16) | O11B—Cl1—O14B | 109.4 (11) |
N1—C10—H10A | 108.8 | O12A—Cl1—O13A | 110.1 (5) |
C9—C10—H10A | 108.8 | O14A—Cl1—O13A | 109.6 (5) |
N1—C10—H10B | 108.8 | O13B—Cl1—O12B | 110.0 (11) |
C9—C10—H10B | 108.8 | O11B—Cl1—O12B | 108.2 (11) |
H10A—C10—H10B | 107.7 | O14B—Cl1—O12B | 108.6 (9) |
N1—C11—H11A | 109.5 | O12A—Cl1—O11A | 110.4 (6) |
N1—C11—H11B | 109.5 | O14A—Cl1—O11A | 108.1 (6) |
H11A—C11—H11B | 109.5 | O13A—Cl1—O11A | 108.8 (5) |
N1—C11—H11C | 109.5 | | |
| | | |
Cu1—O1—C1—C6 | −19.3 (2) | C16—C17—C18—C19 | −179.3 (2) |
Cu2—O1—C1—C6 | 96.02 (18) | O2—C13—C18—C17 | 178.64 (18) |
Cu1—O1—C1—C2 | 161.71 (13) | C14—C13—C18—C17 | −1.7 (3) |
Cu2—O1—C1—C2 | −82.93 (17) | O2—C13—C18—C19 | −2.5 (3) |
O1—C1—C2—C3 | 179.52 (17) | C14—C13—C18—C19 | 177.14 (18) |
C6—C1—C2—C3 | 0.5 (3) | C20—N3—C19—C18 | −179.53 (19) |
C1—C2—C3—C4 | −1.1 (3) | Cu2—N3—C19—C18 | 4.4 (3) |
C2—C3—C4—C5 | 0.3 (3) | C17—C18—C19—N3 | −167.3 (2) |
C3—C4—C5—C6 | 1.2 (4) | C13—C18—C19—N3 | 13.8 (3) |
C4—C5—C6—C1 | −1.8 (3) | C19—N3—C20—C21 | −115.9 (2) |
C4—C5—C6—C7 | 179.1 (2) | Cu2—N3—C20—C21 | 60.3 (2) |
O1—C1—C6—C5 | −178.04 (18) | N3—C20—C21—C22 | −70.2 (2) |
C2—C1—C6—C5 | 0.9 (3) | C23—N4—C22—C21 | 69.0 (3) |
O1—C1—C6—C7 | 1.0 (3) | C24—N4—C22—C21 | −174.2 (2) |
C2—C1—C6—C7 | 179.95 (17) | Cu2—N4—C22—C21 | −48.7 (3) |
C8—N2—C7—C6 | 178.45 (19) | C20—C21—C22—N4 | 67.0 (3) |
Cu1—N2—C7—C6 | −0.9 (3) | Cu2—O4—C25—O3 | 4.0 (3) |
C5—C6—C7—N2 | −171.1 (2) | Cu2—O4—C25—C26 | −175.52 (12) |
C1—C6—C7—N2 | 9.9 (3) | Cu1—O3—C25—O4 | 11.9 (3) |
C7—N2—C8—C9 | −125.45 (19) | Cu1—O3—C25—C26 | −168.62 (12) |
Cu1—N2—C8—C9 | 54.0 (2) | O4—C25—C26—C27 | 153.93 (18) |
N2—C8—C9—C10 | −79.2 (2) | O3—C25—C26—C27 | −25.6 (2) |
C11—N1—C10—C9 | 77.9 (2) | O4—C25—C26—C31 | −26.8 (3) |
C12—N1—C10—C9 | −167.42 (18) | O3—C25—C26—C31 | 153.65 (18) |
Cu1—N1—C10—C9 | −40.7 (2) | C31—C26—C27—C28 | 1.1 (3) |
C8—C9—C10—N1 | 72.8 (2) | C25—C26—C27—C28 | −179.63 (18) |
Cu2—O2—C13—C14 | 155.33 (13) | C26—C27—C28—C29 | −1.9 (3) |
Cu1—O2—C13—C14 | −80.6 (2) | C27—C28—C29—C30 | 1.2 (3) |
Cu2—O2—C13—C18 | −25.1 (2) | C28—C29—C30—C31 | 0.4 (4) |
Cu1—O2—C13—C18 | 99.03 (18) | C29—C30—C31—C26 | −1.2 (3) |
O2—C13—C14—C15 | −178.08 (17) | C29—C30—C31—C32 | −179.4 (2) |
C18—C13—C14—C15 | 2.3 (3) | C27—C26—C31—C30 | 0.5 (3) |
C13—C14—C15—C16 | −0.7 (3) | C25—C26—C31—C30 | −178.74 (18) |
C14—C15—C16—C17 | −1.5 (3) | C27—C26—C31—C32 | 178.5 (2) |
C15—C16—C17—C18 | 2.0 (3) | C25—C26—C31—C32 | −0.7 (3) |
C16—C17—C18—C13 | −0.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O13Aai | 0.99 | 2.69 | 3.418 (12) | 130 |
C10—H10B···O13Bbi | 0.99 | 2.44 | 3.242 (14) | 138 |
C11—H11B···O13Aaii | 0.98 | 2.65 | 3.148 (8) | 111 |
C11—H11C···O3 | 0.98 | 2.48 | 3.039 (2) | 116 |
C12—H12B···O3 | 0.98 | 2.34 | 2.866 (3) | 113 |
C14—H14A···O14Aai | 0.95 | 2.49 | 3.127 (10) | 124 |
C19—H19A···O11Aa | 0.95 | 2.26 | 3.159 (12) | 158 |
C20—H20B···O12Aa | 0.99 | 2.63 | 3.606 (13) | 169 |
C24—H24B···O4 | 0.98 | 2.29 | 2.807 (3) | 112 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1, y+1/2, −z+1/2. |
Positive- and negative-ion electrospray mass spectra of CuLX plus
D-galactose (Gal) in CH3CN/H2O solution topAssigned peaks (m/z) | Benzoate, 1 | Phenylacetate, 2 | 3-Methylbenzoate, 3 |
CuL+ | 268 | 282 | 282 |
(L + H)+ | 207 | 221 | 221 |
(Gal + Na)+ | 203 | 203 | 203 |
(Oxidized Gal + OH)- | 195 | 195 | 195 |
(Gal – H)- | 179 | 179 | 179 |
X- | 121 | 135 | 135 |
The mass spectral peaks (m/z) for CuL+ and
X- appear for each compound. These data indicate the
dissociation scheme implied by the peak assignments. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.