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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:O4O: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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619003267/fn3293sup1.cif
Contains datablocks 1, 2, 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003267/fn32931sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003267/fn32932sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003267/fn32933sup4.hkl
Contains datablock 3

CCDC references: 1901536; 1901535; 1901534

Computing details top

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)]·2H2OF(000) = 924
Mr = 439.98Dx = 1.446 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.2427 (3) ÅCell parameters from 20474 reflections
b = 10.1287 (2) Åθ = 3.8–40.9°
c = 17.7683 (3) ŵ = 1.11 mm1
β = 92.501 (2)°T = 100 K
V = 2021.42 (8) Å3Multi-faceted prism, blue
Z = 40.35 × 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 tube10770 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm-1Rint = 0.030
ω scansθmax = 41.3°, θmin = 3.5°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2018)
h = 2020
Tmin = 0.474, Tmax = 1.000k = 1818
51132 measured reflectionsl = 2532
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.028H 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 reflectionsΔρmax = 0.57 e Å3
270 parametersΔρmin = 0.60 e Å3
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
xyzUiso*/Ueq
Cu0.23818 (2)0.69525 (2)0.47778 (2)0.01137 (2)
O10.27766 (5)0.54601 (5)0.41727 (3)0.01650 (9)
O20.15402 (5)0.78344 (6)0.39331 (3)0.01670 (9)
O30.33453 (5)0.86472 (6)0.37715 (3)0.01897 (10)
O1W0.52308 (7)0.83109 (7)0.28425 (4)0.02636 (13)
H1W10.4716 (12)0.8598 (15)0.3113 (8)0.034 (4)*
H1W20.5502 (16)0.8967 (16)0.2641 (10)0.060 (5)*
O2W0.39643 (9)0.57738 (7)0.27758 (4)0.03167 (16)
H2W10.3575 (13)0.5822 (15)0.3162 (8)0.037 (4)*
H2W20.4310 (14)0.6492 (14)0.2765 (9)0.042 (4)*
N10.33000 (6)0.63419 (6)0.56489 (3)0.01338 (9)
N20.16538 (6)0.82506 (6)0.55446 (3)0.01380 (9)
C10.32672 (6)0.43555 (7)0.44259 (4)0.01414 (10)
C20.32873 (8)0.32474 (8)0.39411 (5)0.02019 (13)
H2A0.2941650.3315220.3445130.024*
C30.38021 (8)0.20647 (8)0.41763 (6)0.02339 (15)
H3A0.3785820.1331780.3842350.028*
C40.43441 (8)0.19302 (7)0.48948 (6)0.02259 (15)
H4A0.4712940.1123270.5046070.027*
C50.43329 (8)0.29896 (7)0.53786 (5)0.01865 (12)
H5A0.4698650.2907670.5868550.022*
C60.37906 (6)0.41938 (7)0.51635 (4)0.01382 (10)
C70.38029 (6)0.52083 (7)0.57282 (4)0.01411 (10)
H7A0.4213620.5027820.6195480.017*
C80.32821 (7)0.72459 (8)0.62904 (4)0.01648 (11)
H8A0.3838170.7990460.6223650.020*
H8B0.3511970.6780390.6764650.020*
C90.20140 (7)0.77360 (8)0.63053 (4)0.01702 (12)
H9A0.1479970.7005580.6442530.020*
H9B0.1955020.8445210.6685250.020*
C100.21916 (7)0.95742 (7)0.54046 (4)0.01689 (12)
H10A0.1885080.9892120.4906180.020*
H10B0.3063100.9461070.5376070.020*
C110.19639 (9)1.06407 (8)0.59850 (5)0.02305 (15)
H11A0.2266911.1488040.5808360.035*
H11B0.2371771.0408240.6465420.035*
H11C0.1106351.0712270.6054590.035*
C120.03368 (7)0.82973 (8)0.54397 (5)0.01943 (13)
H12A0.0122760.8830280.4986780.023*
H12B0.0003550.8743690.5879180.023*
C130.02251 (8)0.69370 (9)0.53516 (6)0.02444 (15)
H13A0.1091030.7027960.5284470.037*
H13B0.0086510.6496620.4910310.037*
H13C0.0032760.6409990.5803160.037*
C140.22685 (7)0.85663 (7)0.35854 (4)0.01419 (10)
C150.17491 (7)0.93920 (7)0.29497 (4)0.01484 (11)
C160.24644 (8)1.02998 (8)0.25883 (4)0.01974 (13)
H16A0.3287661.0359160.2728730.024*
C170.19839 (10)1.11179 (9)0.20249 (5)0.02590 (17)
H17A0.2476781.1734620.1783190.031*
C180.07821 (10)1.10309 (9)0.18165 (5)0.02722 (18)
H18A0.0450411.1594430.1434950.033*
C190.00625 (9)1.01191 (10)0.21660 (5)0.02489 (16)
H19A0.0759151.0058210.2021400.030*
C200.05468 (8)0.92951 (8)0.27283 (4)0.01896 (12)
H20A0.0056180.8665480.2961350.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.01340 (4)0.01114 (3)0.00955 (3)0.00143 (3)0.00042 (2)0.00089 (2)
O10.0219 (2)0.0150 (2)0.01244 (19)0.00371 (18)0.00101 (17)0.00138 (16)
O20.0184 (2)0.0180 (2)0.0136 (2)0.00053 (18)0.00005 (17)0.00472 (16)
O30.0171 (2)0.0228 (2)0.0169 (2)0.0019 (2)0.00086 (18)0.00397 (19)
O1W0.0273 (3)0.0280 (3)0.0243 (3)0.0005 (3)0.0065 (2)0.0045 (2)
O2W0.0522 (5)0.0228 (3)0.0208 (3)0.0024 (3)0.0110 (3)0.0015 (2)
N10.0154 (2)0.0137 (2)0.01093 (19)0.00220 (18)0.00039 (17)0.00069 (16)
N20.0142 (2)0.0133 (2)0.0142 (2)0.00149 (18)0.00314 (18)0.00104 (17)
C10.0148 (3)0.0126 (2)0.0152 (2)0.0006 (2)0.0022 (2)0.00182 (19)
C20.0212 (3)0.0175 (3)0.0219 (3)0.0010 (2)0.0017 (3)0.0070 (2)
C30.0236 (4)0.0142 (3)0.0329 (4)0.0017 (3)0.0062 (3)0.0075 (3)
C40.0245 (4)0.0112 (2)0.0327 (4)0.0017 (2)0.0079 (3)0.0017 (3)
C50.0209 (3)0.0128 (2)0.0225 (3)0.0027 (2)0.0043 (3)0.0042 (2)
C60.0150 (3)0.0113 (2)0.0153 (2)0.0008 (2)0.0027 (2)0.00123 (19)
C70.0149 (3)0.0148 (2)0.0126 (2)0.0018 (2)0.0004 (2)0.00160 (19)
C80.0193 (3)0.0177 (3)0.0123 (2)0.0021 (2)0.0010 (2)0.0027 (2)
C90.0204 (3)0.0184 (3)0.0126 (2)0.0026 (2)0.0042 (2)0.0003 (2)
C100.0183 (3)0.0130 (2)0.0198 (3)0.0000 (2)0.0056 (2)0.0008 (2)
C110.0270 (4)0.0181 (3)0.0243 (3)0.0015 (3)0.0043 (3)0.0066 (3)
C120.0139 (3)0.0198 (3)0.0248 (3)0.0024 (2)0.0038 (2)0.0009 (2)
C130.0206 (3)0.0264 (4)0.0263 (4)0.0059 (3)0.0004 (3)0.0052 (3)
C140.0186 (3)0.0139 (2)0.0101 (2)0.0031 (2)0.0004 (2)0.00105 (18)
C150.0200 (3)0.0148 (2)0.0097 (2)0.0042 (2)0.0003 (2)0.00078 (19)
C160.0270 (4)0.0176 (3)0.0146 (3)0.0018 (3)0.0011 (3)0.0038 (2)
C170.0419 (5)0.0192 (3)0.0168 (3)0.0050 (3)0.0027 (3)0.0063 (2)
C180.0429 (5)0.0236 (4)0.0148 (3)0.0152 (4)0.0030 (3)0.0031 (3)
C190.0284 (4)0.0287 (4)0.0171 (3)0.0129 (3)0.0048 (3)0.0009 (3)
C200.0205 (3)0.0219 (3)0.0144 (3)0.0065 (3)0.0005 (2)0.0002 (2)
Geometric parameters (Å, º) top
Cu—O11.9183 (5)C8—C91.5110 (11)
Cu—N11.9246 (6)C8—H8A0.9900
Cu—O21.9550 (6)C8—H8B0.9900
Cu—N22.0863 (6)C9—H9A0.9900
Cu—O32.7360 (6)C9—H9B0.9900
O1—C11.3178 (9)C10—C111.5228 (11)
O2—C141.2828 (9)C10—H10A0.9900
O3—C141.2437 (10)C10—H10B0.9900
O1W—H1W10.821 (12)C11—H11A0.9800
O1W—H1W20.820 (14)C11—H11B0.9800
O2W—H2W10.831 (12)C11—H11C0.9800
O2W—H2W20.825 (13)C12—C131.5210 (12)
N1—C71.2849 (9)C12—H12A0.9900
N1—C81.4630 (9)C12—H12B0.9900
N2—C121.4850 (10)C13—H13A0.9800
N2—C91.4881 (10)C13—H13B0.9800
N2—C101.4960 (9)C13—H13C0.9800
C1—C21.4156 (10)C14—C151.5029 (9)
C1—C61.4225 (10)C15—C201.3947 (11)
C2—C31.3870 (12)C15—C161.3963 (11)
C2—H2A0.9500C16—C171.3904 (12)
C3—C41.3970 (15)C16—H16A0.9500
C3—H3A0.9500C17—C181.3881 (16)
C4—C51.3754 (12)C17—H17A0.9500
C4—H4A0.9500C18—C191.3917 (15)
C5—C61.4089 (10)C18—H18A0.9500
C5—H5A0.9500C19—C201.3941 (11)
C6—C71.4359 (10)C19—H19A0.9500
C7—H7A0.9500C20—H20A0.9500
O1—Cu—N193.92 (2)N2—C9—C8108.59 (6)
O1—Cu—O292.62 (2)N2—C9—H9A110.0
N1—Cu—O2171.44 (3)C8—C9—H9A110.0
O1—Cu—N2165.85 (2)N2—C9—H9B110.0
N1—Cu—N283.64 (2)C8—C9—H9B110.0
O2—Cu—N291.31 (2)H9A—C9—H9B108.4
O1—Cu—O391.16 (2)N2—C10—C11116.23 (6)
N1—Cu—O3120.89 (2)N2—C10—H10A108.2
O2—Cu—O353.40 (2)C11—C10—H10A108.2
N2—Cu—O3102.08 (2)N2—C10—H10B108.2
C1—O1—Cu125.54 (5)C11—C10—H10B108.2
C14—O2—Cu109.64 (5)H10A—C10—H10B107.4
C14—O3—Cu73.97 (4)C10—C11—H11A109.5
H1W1—O1W—H1W2104.6 (15)C10—C11—H11B109.5
H2W1—O2W—H2W2103.5 (14)H11A—C11—H11B109.5
C7—N1—C8119.66 (6)C10—C11—H11C109.5
C7—N1—Cu126.40 (5)H11A—C11—H11C109.5
C8—N1—Cu113.60 (5)H11B—C11—H11C109.5
C12—N2—C9110.82 (6)N2—C12—C13113.04 (7)
C12—N2—C10111.01 (6)N2—C12—H12A109.0
C9—N2—C10111.65 (6)C13—C12—H12A109.0
C12—N2—Cu110.82 (5)N2—C12—H12B109.0
C9—N2—Cu105.87 (4)C13—C12—H12B109.0
C10—N2—Cu106.45 (4)H12A—C12—H12B107.8
O1—C1—C2118.88 (7)C12—C13—H13A109.5
O1—C1—C6124.23 (6)C12—C13—H13B109.5
C2—C1—C6116.89 (7)H13A—C13—H13B109.5
C3—C2—C1121.27 (8)C12—C13—H13C109.5
C3—C2—H2A119.4H13A—C13—H13C109.5
C1—C2—H2A119.4H13B—C13—H13C109.5
C2—C3—C4121.28 (7)O3—C14—O2122.98 (6)
C2—C3—H3A119.4O3—C14—C15120.33 (7)
C4—C3—H3A119.4O2—C14—C15116.63 (7)
C5—C4—C3118.66 (8)C20—C15—C16119.15 (7)
C5—C4—H4A120.7C20—C15—C14120.86 (7)
C3—C4—H4A120.7C16—C15—C14119.96 (7)
C4—C5—C6121.43 (8)C17—C16—C15120.67 (9)
C4—C5—H5A119.3C17—C16—H16A119.7
C6—C5—H5A119.3C15—C16—H16A119.7
C5—C6—C1120.43 (7)C18—C17—C16119.82 (9)
C5—C6—C7116.04 (7)C18—C17—H17A120.1
C1—C6—C7123.53 (6)C16—C17—H17A120.1
N1—C7—C6124.89 (6)C17—C18—C19120.08 (8)
N1—C7—H7A117.6C17—C18—H18A120.0
C6—C7—H7A117.6C19—C18—H18A120.0
N1—C8—C9105.33 (6)C18—C19—C20120.04 (9)
N1—C8—H8A110.7C18—C19—H19A120.0
C9—C8—H8A110.7C20—C19—H19A120.0
N1—C8—H8B110.7C19—C20—C15120.23 (8)
C9—C8—H8B110.7C19—C20—H20A119.9
H8A—C8—H8B108.8C15—C20—H20A119.9
Cu—O1—C1—C2167.40 (5)C12—N2—C10—C1169.58 (9)
Cu—O1—C1—C612.80 (10)C9—N2—C10—C1154.64 (9)
O1—C1—C2—C3179.39 (8)Cu—N2—C10—C11169.73 (6)
C6—C1—C2—C30.42 (11)C9—N2—C12—C1371.87 (8)
C1—C2—C3—C41.45 (13)C10—N2—C12—C13163.45 (7)
C2—C3—C4—C51.69 (13)Cu—N2—C12—C1345.36 (8)
C3—C4—C5—C60.04 (12)Cu—O3—C14—O20.92 (6)
C4—C5—C6—C11.84 (11)Cu—O3—C14—C15176.22 (6)
C4—C5—C6—C7177.93 (7)Cu—O2—C14—O31.32 (9)
O1—C1—C6—C5177.78 (7)Cu—O2—C14—C15175.93 (5)
C2—C1—C6—C52.02 (10)O3—C14—C15—C20179.00 (7)
O1—C1—C6—C72.47 (11)O2—C14—C15—C203.67 (10)
C2—C1—C6—C7177.73 (7)O3—C14—C15—C163.00 (10)
C8—N1—C7—C6174.37 (7)O2—C14—C15—C16174.33 (7)
Cu—N1—C7—C61.60 (11)C20—C15—C16—C171.29 (11)
C5—C6—C7—N1176.20 (7)C14—C15—C16—C17176.75 (7)
C1—C6—C7—N13.56 (11)C15—C16—C17—C180.21 (13)
C7—N1—C8—C9133.03 (7)C16—C17—C18—C190.57 (13)
Cu—N1—C8—C940.63 (7)C17—C18—C19—C200.26 (13)
C12—N2—C9—C8159.78 (6)C18—C19—C20—C150.83 (12)
C10—N2—C9—C875.90 (7)C16—C15—C20—C191.60 (11)
Cu—N2—C9—C839.55 (7)C14—C15—C20—C19176.42 (7)
N1—C8—C9—N252.20 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O30.82 (1)1.98 (1)2.7641 (9)161 (2)
O1W—H1W2···O2Wi0.82 (1)2.07 (1)2.8871 (10)172 (2)
O2W—H2W1···O10.83 (1)2.08 (1)2.8868 (9)165 (2)
O2W—H2W2···O1W0.83 (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 m3
Mr = 417.98Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 6436 reflections
a = 23.1862 (10) Åθ = 3.9–33.6°
b = 6.4178 (3) ŵ = 1.14 mm1
c = 13.1598 (6) ÅT = 100 K
V = 1958.22 (15) Å3Plate, blue
Z = 40.20 × 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 tube7093 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm-1Rint = 0.089
ω scansθmax = 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 = 3742
Tmin = 0.684, Tmax = 1.000k = 1111
46196 measured reflectionsl = 2322
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.04Δρmax = 1.20 e Å3
11501 reflectionsΔρmin = 1.04 e Å3
245 parametersAbsolute structure: Flack x determined using 1976 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute 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
xyzUiso*/Ueq
Cu0.50251 (2)0.67151 (4)0.58234 (5)0.01478 (6)
O10.55832 (9)0.8376 (3)0.51299 (18)0.0204 (4)
O20.44362 (8)0.8849 (3)0.55955 (16)0.0185 (4)
O30.43374 (10)0.6755 (3)0.42593 (18)0.0219 (5)
N10.55334 (9)0.4358 (3)0.5937 (2)0.0180 (5)
N20.45221 (10)0.5167 (4)0.68793 (19)0.0176 (4)
C10.61121 (12)0.7875 (4)0.4914 (2)0.0167 (5)
C20.64665 (13)0.9369 (5)0.4416 (2)0.0186 (5)
H2A0.6308151.0691460.4250690.022*
C30.70285 (13)0.8961 (5)0.4169 (2)0.0201 (5)
H3A0.7251231.0001510.3837500.024*
C40.72806 (13)0.7032 (5)0.4396 (2)0.0215 (6)
H4A0.7671330.6757680.4224660.026*
C50.69497 (12)0.5539 (5)0.4874 (2)0.0200 (5)
H5A0.7115640.4221330.5024590.024*
C60.63715 (12)0.5921 (5)0.5145 (2)0.0176 (5)
C70.60647 (11)0.4276 (4)0.5657 (2)0.0181 (6)
H7A0.6271070.3031590.5800090.022*
C80.52631 (13)0.2571 (5)0.6443 (3)0.0224 (6)
H8A0.5561810.1640600.6731640.027*
H8B0.5028940.1763700.5952730.027*
C90.48849 (14)0.3425 (5)0.7279 (3)0.0226 (6)
H9A0.4633380.2304910.7545150.027*
H9B0.5128490.3938470.7843580.027*
C100.43476 (15)0.6603 (5)0.7715 (3)0.0222 (6)
H10A0.4152010.5789170.8253220.027*
H10B0.4067610.7629460.7446700.027*
C110.48557 (16)0.7759 (6)0.8177 (3)0.0283 (7)
H11A0.4718040.8677340.8720380.043*
H11B0.5130540.6751820.8458020.043*
H11C0.5046130.8592610.7651280.043*
C120.40028 (13)0.4385 (5)0.6321 (2)0.0222 (6)
H12A0.4136730.3563140.5729650.027*
H12B0.3788870.5601910.6054020.027*
C130.35861 (15)0.3051 (6)0.6926 (3)0.0319 (8)
H13A0.3248230.2728290.6507450.048*
H13B0.3463500.3811390.7535070.048*
H13C0.3777140.1753360.7127440.048*
C140.42161 (12)0.8351 (5)0.4727 (2)0.0170 (5)
C150.37829 (13)0.9942 (5)0.4325 (2)0.0215 (6)
H15A0.3514291.0289040.4884920.026*
H15B0.3996901.1230040.4155050.026*
C160.34295 (12)0.9344 (5)0.3416 (2)0.0192 (5)
C170.33190 (13)1.0802 (5)0.2656 (2)0.0212 (6)
H17A0.3509111.2112340.2676920.025*
C180.29376 (14)1.0383 (6)0.1867 (3)0.0258 (6)
H18A0.2862851.1407700.1363010.031*
C190.26675 (14)0.8464 (6)0.1823 (3)0.0278 (7)
H19A0.2400390.8176260.1293610.033*
C200.27865 (15)0.6955 (6)0.2551 (3)0.0275 (7)
H20A0.2607720.5626180.2509090.033*
C210.31655 (13)0.7385 (5)0.3340 (3)0.0226 (6)
H21A0.3246980.6342100.3831640.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.01389 (12)0.01448 (11)0.01595 (12)0.00064 (11)0.00013 (14)0.00139 (17)
O10.0152 (9)0.0202 (10)0.0257 (11)0.0031 (7)0.0032 (8)0.0053 (8)
O20.0156 (8)0.0208 (10)0.0191 (11)0.0012 (7)0.0011 (7)0.0018 (7)
O30.0217 (10)0.0242 (11)0.0197 (11)0.0051 (8)0.0012 (8)0.0013 (8)
N10.0176 (9)0.0150 (9)0.0214 (14)0.0002 (7)0.0000 (9)0.0003 (9)
N20.0165 (10)0.0200 (11)0.0165 (11)0.0005 (8)0.0008 (8)0.0026 (9)
C10.0169 (12)0.0184 (12)0.0148 (12)0.0005 (9)0.0008 (9)0.0001 (9)
C20.0173 (12)0.0192 (13)0.0192 (13)0.0007 (10)0.0010 (9)0.0000 (10)
C30.0175 (13)0.0249 (14)0.0178 (14)0.0032 (10)0.0012 (10)0.0004 (11)
C40.0161 (13)0.0275 (16)0.0210 (14)0.0014 (10)0.0037 (10)0.0019 (11)
C50.0174 (13)0.0202 (14)0.0226 (14)0.0035 (10)0.0011 (10)0.0011 (11)
C60.0162 (12)0.0182 (13)0.0186 (13)0.0005 (9)0.0015 (9)0.0016 (10)
C70.0171 (11)0.0148 (11)0.0225 (16)0.0022 (8)0.0020 (9)0.0017 (10)
C80.0204 (14)0.0187 (14)0.0281 (16)0.0010 (11)0.0003 (11)0.0025 (12)
C90.0237 (14)0.0216 (15)0.0227 (15)0.0014 (11)0.0015 (11)0.0057 (11)
C100.0245 (15)0.0240 (16)0.0180 (14)0.0005 (12)0.0042 (11)0.0002 (11)
C110.0327 (17)0.0254 (16)0.0269 (18)0.0012 (13)0.0006 (13)0.0014 (13)
C120.0192 (13)0.0270 (15)0.0205 (15)0.0046 (11)0.0002 (10)0.0010 (12)
C130.0255 (17)0.038 (2)0.0323 (19)0.0116 (14)0.0027 (14)0.0040 (15)
C140.0127 (11)0.0224 (13)0.0160 (12)0.0005 (9)0.0020 (8)0.0042 (10)
C150.0208 (14)0.0203 (14)0.0234 (15)0.0027 (10)0.0039 (11)0.0018 (11)
C160.0154 (12)0.0226 (14)0.0196 (14)0.0018 (10)0.0002 (10)0.0026 (10)
C170.0164 (13)0.0243 (15)0.0228 (15)0.0026 (11)0.0031 (10)0.0049 (11)
C180.0254 (15)0.0350 (18)0.0170 (14)0.0087 (13)0.0026 (11)0.0055 (12)
C190.0232 (15)0.041 (2)0.0193 (15)0.0076 (13)0.0038 (11)0.0079 (13)
C200.0245 (16)0.0287 (18)0.0294 (18)0.0011 (12)0.0019 (13)0.0047 (13)
C210.0214 (13)0.0220 (14)0.0244 (15)0.0003 (11)0.0015 (12)0.0021 (12)
Geometric parameters (Å, º) top
Cu—O11.909 (2)C9—H9B0.9900
Cu—N11.923 (2)C10—C111.519 (5)
Cu—O21.957 (2)C10—H10A0.9900
Cu—N22.068 (2)C10—H10B0.9900
Cu—O32.604 (2)C11—H11A0.9800
O1—C11.299 (3)C11—H11B0.9800
O2—C141.292 (4)C11—H11C0.9800
O3—C141.228 (4)C12—C131.517 (4)
N1—C71.287 (3)C12—H12A0.9900
N1—C81.467 (4)C12—H12B0.9900
N2—C101.490 (4)C13—H13A0.9800
N2—C91.495 (4)C13—H13B0.9800
N2—C121.497 (4)C13—H13C0.9800
C1—C21.423 (4)C14—C151.526 (4)
C1—C61.424 (4)C15—C161.500 (4)
C2—C31.368 (4)C15—H15A0.9900
C2—H2A0.9500C15—H15B0.9900
C3—C41.402 (4)C16—C171.394 (4)
C3—H3A0.9500C16—C211.402 (4)
C4—C51.379 (4)C17—C181.390 (5)
C4—H4A0.9500C17—H17A0.9500
C5—C61.408 (4)C18—C191.383 (5)
C5—H5A0.9500C18—H18A0.9500
C6—C71.441 (4)C19—C201.390 (5)
C7—H7A0.9500C19—H19A0.9500
C8—C91.509 (5)C20—C211.387 (5)
C8—H8A0.9900C20—H20A0.9500
C8—H8B0.9900C21—H21A0.9500
C9—H9A0.9900
O1—Cu—N193.49 (9)C8—C9—H9B109.7
O1—Cu—O290.51 (9)H9A—C9—H9B108.2
N1—Cu—O2171.79 (10)N2—C10—C11112.8 (3)
O1—Cu—N2166.33 (11)N2—C10—H10A109.0
N1—Cu—N285.17 (10)C11—C10—H10A109.0
O2—Cu—N292.61 (9)N2—C10—H10B109.0
O1—Cu—O391.81 (9)C11—C10—H10B109.0
N1—Cu—O3116.37 (10)H10A—C10—H10B107.8
O2—Cu—O356.27 (8)C10—C11—H11A109.5
N2—Cu—O3100.98 (9)C10—C11—H11B109.5
C1—O1—Cu127.30 (19)H11A—C11—H11B109.5
C14—O2—Cu103.79 (18)C10—C11—H11C109.5
C14—O3—Cu75.67 (17)H11A—C11—H11C109.5
C7—N1—C8120.5 (2)H11B—C11—H11C109.5
C7—N1—Cu126.6 (2)N2—C12—C13116.4 (3)
C8—N1—Cu112.84 (18)N2—C12—H12A108.2
C10—N2—C9110.8 (3)C13—C12—H12A108.2
C10—N2—C12110.6 (2)N2—C12—H12B108.2
C9—N2—C12112.0 (2)C13—C12—H12B108.2
C10—N2—Cu110.60 (19)H12A—C12—H12B107.4
C9—N2—Cu106.15 (18)C12—C13—H13A109.5
C12—N2—Cu106.56 (18)C12—C13—H13B109.5
O1—C1—C2118.6 (3)H13A—C13—H13B109.5
O1—C1—C6124.8 (3)C12—C13—H13C109.5
C2—C1—C6116.6 (3)H13A—C13—H13C109.5
C3—C2—C1122.1 (3)H13B—C13—H13C109.5
C3—C2—H2A119.0O3—C14—O2124.0 (3)
C1—C2—H2A119.0O3—C14—C15122.4 (3)
C2—C3—C4121.0 (3)O2—C14—C15113.6 (3)
C2—C3—H3A119.5C16—C15—C14117.7 (3)
C4—C3—H3A119.5C16—C15—H15A107.9
C5—C4—C3118.6 (3)C14—C15—H15A107.9
C5—C4—H4A120.7C16—C15—H15B107.9
C3—C4—H4A120.7C14—C15—H15B107.9
C4—C5—C6121.6 (3)H15A—C15—H15B107.2
C4—C5—H5A119.2C17—C16—C21118.0 (3)
C6—C5—H5A119.2C17—C16—C15120.1 (3)
C5—C6—C1120.1 (3)C21—C16—C15121.7 (3)
C5—C6—C7117.4 (3)C18—C17—C16121.6 (3)
C1—C6—C7122.4 (3)C18—C17—H17A119.2
N1—C7—C6125.2 (3)C16—C17—H17A119.2
N1—C7—H7A117.4C19—C18—C17119.5 (3)
C6—C7—H7A117.4C19—C18—H18A120.3
N1—C8—C9107.2 (3)C17—C18—H18A120.3
N1—C8—H8A110.3C18—C19—C20120.1 (3)
C9—C8—H8A110.3C18—C19—H19A120.0
N1—C8—H8B110.3C20—C19—H19A120.0
C9—C8—H8B110.3C21—C20—C19120.2 (3)
H8A—C8—H8B108.5C21—C20—H20A119.9
N2—C9—C8110.0 (3)C19—C20—H20A119.9
N2—C9—H9A109.7C20—C21—C16120.6 (3)
C8—C9—H9A109.7C20—C21—H21A119.7
N2—C9—H9B109.7C16—C21—H21A119.7
Cu—O1—C1—C2178.1 (2)C9—N2—C10—C1166.1 (3)
Cu—O1—C1—C61.5 (4)C12—N2—C10—C11169.2 (3)
O1—C1—C2—C3179.7 (3)Cu—N2—C10—C1151.4 (3)
C6—C1—C2—C30.0 (4)C10—N2—C12—C1364.0 (4)
C1—C2—C3—C40.1 (5)C9—N2—C12—C1360.1 (4)
C2—C3—C4—C50.2 (5)Cu—N2—C12—C13175.8 (3)
C3—C4—C5—C60.7 (5)Cu—O3—C14—O24.8 (2)
C4—C5—C6—C10.8 (5)Cu—O3—C14—C15175.4 (3)
C4—C5—C6—C7179.0 (3)Cu—O2—C14—O36.4 (3)
O1—C1—C6—C5179.9 (3)Cu—O2—C14—C15173.84 (19)
C2—C1—C6—C50.5 (4)O3—C14—C15—C1610.0 (4)
O1—C1—C6—C70.4 (5)O2—C14—C15—C16169.8 (3)
C2—C1—C6—C7179.3 (3)C14—C15—C16—C17139.8 (3)
C8—N1—C7—C6179.2 (3)C14—C15—C16—C2145.1 (4)
Cu—N1—C7—C64.0 (4)C21—C16—C17—C183.1 (5)
C5—C6—C7—N1178.5 (3)C15—C16—C17—C18172.1 (3)
C1—C6—C7—N11.7 (5)C16—C17—C18—C191.2 (5)
C7—N1—C8—C9139.9 (3)C17—C18—C19—C201.2 (5)
Cu—N1—C8—C937.3 (3)C18—C19—C20—C211.6 (5)
C10—N2—C9—C8155.3 (3)C19—C20—C21—C160.5 (5)
C12—N2—C9—C880.7 (3)C17—C16—C21—C202.8 (5)
Cu—N2—C9—C835.2 (3)C15—C16—C21—C20172.4 (3)
N1—C8—C9—N247.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O2i0.992.373.260 (4)149
C9—H9B···O3ii0.992.283.172 (4)149
C12—H12B···O20.992.643.183 (4)115
Symmetry codes: (i) x, y1, 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]ClO4Dx = 1.521 Mg m3
Mr = 772.22Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 21097 reflections
a = 10.51085 (16) Åθ = 3.7–36.4°
b = 22.2419 (5) ŵ = 1.40 mm1
c = 28.8403 (5) ÅT = 100 K
V = 6742.3 (2) Å3Plate, green-blue
Z = 80.26 × 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 tube12413 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm-1Rint = 0.090
ω scansθmax = 41.6°, θmin = 3.4°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2018)
h = 1819
Tmin = 0.614, Tmax = 1.000k = 3340
154652 measured reflectionsl = 3552
Refinement top
Refinement on F244 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-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 reflectionsΔρmax = 1.13 e Å3
467 parametersΔρmin = 1.10 e Å3
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
xyzUiso*/UeqOcc. (<1)
Cu10.28173 (2)1.08502 (2)0.16413 (2)0.01838 (4)
Cu20.32761 (2)0.99599 (2)0.08706 (2)0.01958 (4)
O10.18853 (12)1.01143 (6)0.14771 (5)0.0219 (2)
O20.44003 (11)1.05731 (6)0.11374 (5)0.0215 (2)
O30.18608 (13)1.12125 (6)0.11331 (5)0.0241 (3)
O40.24510 (13)1.06268 (6)0.05351 (5)0.0255 (3)
N10.32825 (14)1.17468 (7)0.18137 (6)0.0223 (3)
N20.35486 (14)1.04593 (7)0.21946 (5)0.0229 (3)
N30.42640 (14)0.93093 (7)0.11619 (6)0.0232 (3)
N40.24861 (19)0.93856 (9)0.03741 (7)0.0353 (4)
C10.15786 (15)0.96685 (8)0.17591 (6)0.0204 (3)
C20.06056 (16)0.92586 (8)0.16282 (8)0.0259 (3)
H2A0.0181930.9311680.1340180.031*
C30.02630 (19)0.87838 (9)0.19118 (9)0.0326 (4)
H3A0.0401460.8521230.1817670.039*
C40.0877 (2)0.86842 (10)0.23339 (9)0.0377 (5)
H4A0.0639320.8356170.2526240.045*
C50.1835 (2)0.90699 (10)0.24663 (8)0.0340 (4)
H5A0.2268340.9000520.2750260.041*
C60.21861 (18)0.95663 (8)0.21897 (7)0.0238 (3)
C70.31918 (17)0.99510 (8)0.23622 (7)0.0235 (3)
H7A0.3636610.9812580.2628300.028*
C80.45833 (19)1.07664 (10)0.24478 (7)0.0305 (4)
H8A0.5353251.0783790.2250580.037*
H8B0.4795091.0536890.2731620.037*
C90.4179 (2)1.13985 (10)0.25785 (7)0.0310 (4)
H9A0.3287411.1389930.2689070.037*
H9B0.4718831.1543150.2836680.037*
C100.42827 (18)1.18331 (10)0.21765 (7)0.0297 (4)
H10A0.4223901.2248790.2297330.036*
H10B0.5129981.1786250.2031000.036*
C110.20745 (19)1.20172 (11)0.19811 (8)0.0338 (5)
H11A0.2200591.2447730.2036780.051*
H11B0.1815861.1820860.2270280.051*
H11C0.1410261.1961360.1746530.051*
C120.3685 (2)1.21036 (10)0.14034 (8)0.0314 (4)
H12A0.3906091.2512430.1501330.047*
H12B0.2987171.2120110.1178530.047*
H12C0.4428561.1913600.1259730.047*
C130.56329 (16)1.04925 (8)0.12129 (6)0.0195 (3)
C140.64547 (17)1.09933 (8)0.12300 (7)0.0232 (3)
H14A0.6112301.1386210.1196590.028*
C150.77541 (17)1.09226 (9)0.12948 (7)0.0243 (3)
H15A0.8286591.1267630.1301310.029*
C160.82929 (17)1.03539 (9)0.13505 (8)0.0273 (4)
H16A0.9185771.0308190.1387550.033*
C170.75007 (18)0.98594 (9)0.13505 (8)0.0276 (4)
H17A0.7854870.9471300.1398030.033*
C180.61758 (16)0.99162 (8)0.12815 (6)0.0216 (3)
C190.54316 (17)0.93722 (8)0.12929 (7)0.0247 (3)
H19A0.5843200.9023050.1409150.030*
C200.37186 (19)0.87002 (9)0.12140 (8)0.0295 (4)
H20A0.2942070.8720190.1407700.035*
H20B0.4339960.8435460.1371700.035*
C210.3391 (2)0.84414 (11)0.07424 (11)0.0425 (6)
H21A0.4142510.8478070.0537340.051*
H21B0.3199060.8008100.0777730.051*
C220.2275 (3)0.87454 (11)0.05142 (10)0.0431 (6)
H22A0.2039330.8512220.0234800.052*
H22B0.1543640.8730920.0730080.052*
C230.3397 (3)0.94346 (15)0.00141 (10)0.0532 (7)
H23A0.3097840.9190790.0275270.080*
H23B0.4233710.9289750.0086270.080*
H23C0.3465010.9855750.0110920.080*
C240.1215 (3)0.95918 (14)0.02074 (11)0.0534 (7)
H24A0.0895330.9310730.0026880.080*
H24B0.1294790.9993410.0070710.080*
H24C0.0620630.9606630.0468910.080*
C250.19144 (16)1.10812 (8)0.07068 (6)0.0209 (3)
C260.12577 (17)1.15150 (8)0.03844 (6)0.0220 (3)
C270.02568 (18)1.18557 (9)0.05705 (7)0.0259 (3)
H27A0.0030351.1806220.0887150.031*
C280.0408 (2)1.22642 (10)0.02983 (8)0.0333 (4)
H28A0.1100831.2483840.0424770.040*
C290.0050 (2)1.23482 (10)0.01588 (9)0.0388 (5)
H29A0.0489231.2632270.0345600.047*
C300.0943 (2)1.20205 (11)0.03445 (8)0.0358 (5)
H30A0.1178591.2086140.0658400.043*
C310.16139 (19)1.15931 (9)0.00827 (7)0.0277 (4)
C320.2693 (2)1.12608 (12)0.03120 (8)0.0384 (5)
H32A0.2906211.1457160.0606130.058*
H32B0.2437261.0844180.0371150.058*
H32C0.3438581.1265120.0107810.058*
Cl10.71528 (4)0.76845 (2)0.15982 (2)0.02309 (8)
O11A0.7359 (13)0.8310 (3)0.1481 (5)0.0305 (14)0.64 (4)
O12A0.5835 (7)0.7574 (6)0.1677 (4)0.0448 (17)0.64 (4)
O13A0.7872 (10)0.7544 (7)0.2006 (4)0.054 (2)0.64 (4)
O14A0.7590 (13)0.7325 (4)0.1220 (4)0.059 (2)0.64 (4)
O11B0.752 (2)0.8298 (6)0.1535 (9)0.030 (2)0.36 (4)
O12B0.5852 (13)0.7673 (13)0.1760 (10)0.058 (5)0.36 (4)
O13B0.7955 (17)0.7392 (9)0.1922 (7)0.053 (3)0.36 (4)
O14B0.722 (3)0.7377 (9)0.1163 (5)0.068 (4)0.36 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02042 (9)0.01657 (9)0.01815 (8)0.00045 (7)0.00320 (7)0.00008 (7)
Cu20.01951 (9)0.01557 (9)0.02365 (10)0.00206 (7)0.00306 (7)0.00206 (7)
O10.0221 (5)0.0193 (6)0.0244 (6)0.0017 (4)0.0033 (4)0.0001 (5)
O20.0177 (5)0.0171 (6)0.0296 (6)0.0018 (4)0.0019 (4)0.0030 (5)
O30.0316 (6)0.0205 (6)0.0203 (6)0.0060 (5)0.0060 (5)0.0016 (5)
O40.0320 (6)0.0224 (6)0.0221 (6)0.0068 (5)0.0036 (5)0.0010 (5)
N10.0204 (6)0.0199 (7)0.0266 (7)0.0024 (5)0.0026 (5)0.0039 (5)
N20.0220 (6)0.0246 (8)0.0221 (7)0.0023 (5)0.0050 (5)0.0014 (5)
N30.0204 (6)0.0166 (6)0.0326 (8)0.0014 (5)0.0028 (5)0.0002 (6)
N40.0414 (10)0.0278 (9)0.0367 (10)0.0033 (7)0.0122 (8)0.0086 (8)
C10.0184 (7)0.0159 (7)0.0269 (8)0.0019 (5)0.0015 (6)0.0010 (6)
C20.0187 (7)0.0201 (8)0.0388 (10)0.0010 (6)0.0001 (7)0.0048 (7)
C30.0257 (8)0.0181 (9)0.0539 (13)0.0036 (6)0.0070 (8)0.0052 (8)
C40.0469 (12)0.0214 (10)0.0449 (13)0.0063 (8)0.0116 (10)0.0046 (9)
C50.0463 (12)0.0223 (9)0.0333 (10)0.0012 (8)0.0021 (9)0.0057 (8)
C60.0266 (8)0.0182 (8)0.0266 (8)0.0004 (6)0.0000 (6)0.0029 (6)
C70.0263 (8)0.0209 (8)0.0234 (7)0.0009 (6)0.0046 (6)0.0031 (6)
C80.0257 (8)0.0383 (12)0.0273 (9)0.0082 (7)0.0091 (7)0.0042 (8)
C90.0307 (9)0.0371 (11)0.0253 (9)0.0117 (8)0.0039 (7)0.0058 (8)
C100.0251 (8)0.0297 (10)0.0343 (10)0.0091 (7)0.0013 (7)0.0045 (8)
C110.0246 (8)0.0384 (12)0.0383 (11)0.0001 (8)0.0053 (8)0.0165 (9)
C120.0315 (9)0.0228 (9)0.0399 (11)0.0001 (7)0.0057 (8)0.0068 (8)
C130.0198 (6)0.0180 (7)0.0207 (7)0.0006 (5)0.0001 (5)0.0011 (5)
C140.0215 (7)0.0190 (8)0.0291 (8)0.0001 (6)0.0005 (6)0.0031 (6)
C150.0208 (7)0.0238 (9)0.0282 (8)0.0026 (6)0.0001 (6)0.0037 (7)
C160.0192 (7)0.0260 (9)0.0367 (10)0.0003 (6)0.0047 (7)0.0010 (7)
C170.0221 (7)0.0228 (9)0.0380 (10)0.0017 (6)0.0064 (7)0.0031 (7)
C180.0199 (7)0.0188 (8)0.0261 (8)0.0016 (5)0.0033 (6)0.0013 (6)
C190.0231 (7)0.0173 (8)0.0336 (9)0.0034 (6)0.0028 (6)0.0025 (7)
C200.0240 (8)0.0161 (8)0.0484 (12)0.0015 (6)0.0005 (8)0.0024 (8)
C210.0417 (12)0.0216 (10)0.0643 (17)0.0029 (8)0.0073 (11)0.0096 (10)
C220.0471 (13)0.0308 (12)0.0514 (15)0.0087 (10)0.0051 (11)0.0138 (11)
C230.0700 (19)0.0531 (18)0.0365 (13)0.0012 (14)0.0041 (13)0.0218 (12)
C240.0475 (14)0.0573 (18)0.0553 (16)0.0143 (13)0.0279 (13)0.0002 (14)
C250.0232 (7)0.0175 (7)0.0221 (7)0.0004 (5)0.0037 (6)0.0010 (6)
C260.0249 (7)0.0184 (8)0.0227 (7)0.0014 (6)0.0050 (6)0.0029 (6)
C270.0275 (8)0.0199 (8)0.0303 (9)0.0012 (6)0.0056 (7)0.0012 (7)
C280.0336 (10)0.0224 (9)0.0440 (12)0.0036 (7)0.0117 (9)0.0037 (8)
C290.0462 (12)0.0262 (11)0.0439 (12)0.0001 (9)0.0183 (10)0.0131 (9)
C300.0474 (12)0.0314 (11)0.0287 (10)0.0057 (9)0.0092 (9)0.0105 (8)
C310.0333 (9)0.0251 (9)0.0249 (8)0.0049 (7)0.0045 (7)0.0045 (7)
C320.0481 (13)0.0394 (13)0.0277 (10)0.0012 (10)0.0058 (9)0.0043 (9)
Cl10.02552 (18)0.01891 (18)0.02484 (18)0.00209 (14)0.00050 (14)0.00546 (14)
O11A0.040 (4)0.0144 (16)0.037 (3)0.0024 (15)0.008 (3)0.0036 (14)
O12A0.026 (2)0.051 (4)0.057 (3)0.010 (2)0.0030 (17)0.013 (2)
O13A0.040 (3)0.069 (5)0.052 (3)0.001 (3)0.013 (2)0.037 (3)
O14A0.092 (5)0.0242 (19)0.060 (4)0.003 (3)0.038 (3)0.010 (3)
O11B0.031 (4)0.018 (3)0.041 (6)0.001 (3)0.015 (3)0.000 (3)
O12B0.026 (4)0.056 (8)0.092 (11)0.007 (4)0.008 (5)0.019 (7)
O13B0.042 (4)0.050 (6)0.066 (7)0.020 (4)0.016 (4)0.025 (5)
O14B0.135 (12)0.036 (6)0.033 (4)0.032 (7)0.001 (6)0.010 (3)
Geometric parameters (Å, º) top
Cu1—O31.9514 (13)C12—H12C0.9800
Cu1—O11.9654 (13)C13—C141.410 (2)
Cu1—N21.9731 (15)C13—C181.417 (2)
Cu1—N12.1126 (16)C14—C151.387 (2)
Cu1—O22.2935 (13)C14—H14A0.9500
Cu1—Cu23.0155 (3)C15—C161.395 (3)
Cu2—O21.9615 (13)C15—H15A0.9500
Cu2—N31.9693 (15)C16—C171.379 (3)
Cu2—O41.9719 (14)C16—H16A0.9500
Cu2—N42.0909 (18)C17—C181.412 (3)
Cu2—O12.3053 (14)C17—H17A0.9500
O1—C11.322 (2)C18—C191.441 (3)
O2—C131.326 (2)C19—H19A0.9500
O3—C251.265 (2)C20—C211.517 (4)
O4—C251.259 (2)C20—H20A0.9900
N1—C111.485 (2)C20—H20B0.9900
N1—C121.486 (3)C21—C221.505 (4)
N1—C101.496 (3)C21—H21A0.9900
N2—C71.285 (2)C21—H21B0.9900
N2—C81.477 (2)C22—H22A0.9900
N3—C191.292 (2)C22—H22B0.9900
N3—C201.479 (2)C23—H23A0.9800
N4—C231.478 (4)C23—H23B0.9800
N4—C241.492 (3)C23—H23C0.9800
N4—C221.497 (3)C24—H24A0.9800
C1—C61.415 (3)C24—H24B0.9800
C1—C21.421 (2)C24—H24C0.9800
C2—C31.383 (3)C25—C261.507 (2)
C2—H2A0.9500C26—C271.403 (3)
C3—C41.396 (4)C26—C311.409 (3)
C3—H3A0.9500C27—C281.389 (3)
C4—C51.376 (3)C27—H27A0.9500
C4—H4A0.9500C28—C291.383 (4)
C5—C61.411 (3)C28—H28A0.9500
C5—H5A0.9500C29—C301.381 (4)
C6—C71.448 (3)C29—H29A0.9500
C7—H7A0.9500C30—C311.404 (3)
C8—C91.516 (3)C30—H30A0.9500
C8—H8A0.9900C31—C321.507 (3)
C8—H8B0.9900C32—H32A0.9800
C9—C101.513 (3)C32—H32B0.9800
C9—H9A0.9900C32—H32C0.9800
C9—H9B0.9900Cl1—O13B1.417 (11)
C10—H10A0.9900Cl1—O12A1.425 (7)
C10—H10B0.9900Cl1—O11B1.428 (12)
C11—H11A0.9800Cl1—O14A1.430 (6)
C11—H11B0.9800Cl1—O14B1.433 (11)
C11—H11C0.9800Cl1—O13A1.433 (7)
C12—H12A0.9800Cl1—O12B1.445 (12)
C12—H12B0.9800Cl1—O11A1.448 (7)
O3—Cu1—O184.62 (6)H11A—C11—H11C109.5
O3—Cu1—N2171.91 (6)H11B—C11—H11C109.5
O1—Cu1—N291.26 (6)N1—C12—H12A109.5
O3—Cu1—N184.62 (6)N1—C12—H12B109.5
O1—Cu1—N1163.37 (6)H12A—C12—H12B109.5
N2—Cu1—N197.79 (7)N1—C12—H12C109.5
O3—Cu1—O290.51 (5)H12A—C12—H12C109.5
O1—Cu1—O289.15 (5)H12B—C12—H12C109.5
N2—Cu1—O296.40 (6)O2—C13—C14119.83 (16)
N1—Cu1—O2103.59 (5)O2—C13—C18122.59 (15)
O3—Cu1—Cu278.46 (4)C14—C13—C18117.58 (15)
O1—Cu1—Cu249.86 (4)C15—C14—C13121.20 (17)
N2—Cu1—Cu2104.15 (5)C15—C14—H14A119.4
N1—Cu1—Cu2139.14 (4)C13—C14—H14A119.4
O2—Cu1—Cu240.58 (3)C14—C15—C16121.19 (17)
O2—Cu2—N391.49 (6)C14—C15—H15A119.4
O2—Cu2—O486.24 (6)C16—C15—H15A119.4
N3—Cu2—O4173.70 (6)C17—C16—C15118.55 (17)
O2—Cu2—N4158.84 (7)C17—C16—H16A120.7
N3—Cu2—N493.01 (7)C15—C16—H16A120.7
O4—Cu2—N487.06 (7)C16—C17—C18121.59 (18)
O2—Cu2—O188.90 (5)C16—C17—H17A119.2
N3—Cu2—O196.90 (6)C18—C17—H17A119.2
O4—Cu2—O188.94 (5)C17—C18—C13119.84 (16)
N4—Cu2—O1111.03 (7)C17—C18—C19117.18 (16)
O2—Cu2—Cu149.52 (4)C13—C18—C19122.97 (15)
N3—Cu2—Cu1104.63 (5)N3—C19—C18126.86 (17)
O4—Cu2—Cu178.32 (4)N3—C19—H19A116.6
N4—Cu2—Cu1147.40 (6)C18—C19—H19A116.6
O1—Cu2—Cu140.67 (3)N3—C20—C21110.15 (19)
C1—O1—Cu1126.72 (12)N3—C20—H20A109.6
C1—O1—Cu2120.64 (11)C21—C20—H20A109.6
Cu1—O1—Cu289.47 (5)N3—C20—H20B109.6
C13—O2—Cu2123.99 (11)C21—C20—H20B109.6
C13—O2—Cu1129.87 (11)H20A—C20—H20B108.1
Cu2—O2—Cu189.91 (5)C22—C21—C20113.5 (2)
C25—O3—Cu1127.72 (12)C22—C21—H21A108.9
C25—O4—Cu2127.43 (12)C20—C21—H21A108.9
C11—N1—C12106.62 (17)C22—C21—H21B108.9
C11—N1—C10108.75 (15)C20—C21—H21B108.9
C12—N1—C10106.75 (15)H21A—C21—H21B107.7
C11—N1—Cu1105.12 (12)N4—C22—C21115.5 (2)
C12—N1—Cu1112.50 (13)N4—C22—H22A108.4
C10—N1—Cu1116.64 (13)C21—C22—H22A108.4
C7—N2—C8115.82 (16)N4—C22—H22B108.4
C7—N2—Cu1125.31 (13)C21—C22—H22B108.4
C8—N2—Cu1118.87 (13)H22A—C22—H22B107.5
C19—N3—C20115.97 (16)N4—C23—H23A109.5
C19—N3—Cu2123.10 (13)N4—C23—H23B109.5
C20—N3—Cu2120.81 (12)H23A—C23—H23B109.5
C23—N4—C24108.3 (2)N4—C23—H23C109.5
C23—N4—C22111.8 (2)H23A—C23—H23C109.5
C24—N4—C22104.3 (2)H23B—C23—H23C109.5
C23—N4—Cu2102.51 (15)N4—C24—H24A109.5
C24—N4—Cu2112.86 (16)N4—C24—H24B109.5
C22—N4—Cu2117.07 (15)H24A—C24—H24B109.5
O1—C1—C6123.39 (16)N4—C24—H24C109.5
O1—C1—C2119.55 (17)H24A—C24—H24C109.5
C6—C1—C2117.05 (17)H24B—C24—H24C109.5
C3—C2—C1121.3 (2)O4—C25—O3125.98 (16)
C3—C2—H2A119.3O4—C25—C26118.45 (16)
C1—C2—H2A119.3O3—C25—C26115.56 (16)
C2—C3—C4121.09 (19)C27—C26—C31119.90 (17)
C2—C3—H3A119.5C27—C26—C25116.94 (16)
C4—C3—H3A119.5C31—C26—C25123.16 (17)
C5—C4—C3118.8 (2)C28—C27—C26120.9 (2)
C5—C4—H4A120.6C28—C27—H27A119.5
C3—C4—H4A120.6C26—C27—H27A119.5
C4—C5—C6121.5 (2)C29—C28—C27119.4 (2)
C4—C5—H5A119.3C29—C28—H28A120.3
C6—C5—H5A119.3C27—C28—H28A120.3
C5—C6—C1120.24 (18)C30—C29—C28120.2 (2)
C5—C6—C7117.34 (18)C30—C29—H29A119.9
C1—C6—C7122.41 (16)C28—C29—H29A119.9
N2—C7—C6127.13 (17)C29—C30—C31121.9 (2)
N2—C7—H7A116.4C29—C30—H30A119.0
C6—C7—H7A116.4C31—C30—H30A119.0
N2—C8—C9110.19 (16)C30—C31—C26117.7 (2)
N2—C8—H8A109.6C30—C31—C32118.3 (2)
C9—C8—H8A109.6C26—C31—C32124.01 (18)
N2—C8—H8B109.6C31—C32—H32A109.5
C9—C8—H8B109.6C31—C32—H32B109.5
H8A—C8—H8B108.1H32A—C32—H32B109.5
C10—C9—C8112.43 (17)C31—C32—H32C109.5
C10—C9—H9A109.1H32A—C32—H32C109.5
C8—C9—H9A109.1H32B—C32—H32C109.5
C10—C9—H9B109.1O13B—Cl1—O11B111.3 (10)
C8—C9—H9B109.1O12A—Cl1—O14A109.8 (5)
H9A—C9—H9B107.8O13B—Cl1—O14B109.3 (9)
N1—C10—C9113.79 (16)O11B—Cl1—O14B109.4 (11)
N1—C10—H10A108.8O12A—Cl1—O13A110.1 (5)
C9—C10—H10A108.8O14A—Cl1—O13A109.6 (5)
N1—C10—H10B108.8O13B—Cl1—O12B110.0 (11)
C9—C10—H10B108.8O11B—Cl1—O12B108.2 (11)
H10A—C10—H10B107.7O14B—Cl1—O12B108.6 (9)
N1—C11—H11A109.5O12A—Cl1—O11A110.4 (6)
N1—C11—H11B109.5O14A—Cl1—O11A108.1 (6)
H11A—C11—H11B109.5O13A—Cl1—O11A108.8 (5)
N1—C11—H11C109.5
Cu1—O1—C1—C619.3 (2)C16—C17—C18—C19179.3 (2)
Cu2—O1—C1—C696.02 (18)O2—C13—C18—C17178.64 (18)
Cu1—O1—C1—C2161.71 (13)C14—C13—C18—C171.7 (3)
Cu2—O1—C1—C282.93 (17)O2—C13—C18—C192.5 (3)
O1—C1—C2—C3179.52 (17)C14—C13—C18—C19177.14 (18)
C6—C1—C2—C30.5 (3)C20—N3—C19—C18179.53 (19)
C1—C2—C3—C41.1 (3)Cu2—N3—C19—C184.4 (3)
C2—C3—C4—C50.3 (3)C17—C18—C19—N3167.3 (2)
C3—C4—C5—C61.2 (4)C13—C18—C19—N313.8 (3)
C4—C5—C6—C11.8 (3)C19—N3—C20—C21115.9 (2)
C4—C5—C6—C7179.1 (2)Cu2—N3—C20—C2160.3 (2)
O1—C1—C6—C5178.04 (18)N3—C20—C21—C2270.2 (2)
C2—C1—C6—C50.9 (3)C23—N4—C22—C2169.0 (3)
O1—C1—C6—C71.0 (3)C24—N4—C22—C21174.2 (2)
C2—C1—C6—C7179.95 (17)Cu2—N4—C22—C2148.7 (3)
C8—N2—C7—C6178.45 (19)C20—C21—C22—N467.0 (3)
Cu1—N2—C7—C60.9 (3)Cu2—O4—C25—O34.0 (3)
C5—C6—C7—N2171.1 (2)Cu2—O4—C25—C26175.52 (12)
C1—C6—C7—N29.9 (3)Cu1—O3—C25—O411.9 (3)
C7—N2—C8—C9125.45 (19)Cu1—O3—C25—C26168.62 (12)
Cu1—N2—C8—C954.0 (2)O4—C25—C26—C27153.93 (18)
N2—C8—C9—C1079.2 (2)O3—C25—C26—C2725.6 (2)
C11—N1—C10—C977.9 (2)O4—C25—C26—C3126.8 (3)
C12—N1—C10—C9167.42 (18)O3—C25—C26—C31153.65 (18)
Cu1—N1—C10—C940.7 (2)C31—C26—C27—C281.1 (3)
C8—C9—C10—N172.8 (2)C25—C26—C27—C28179.63 (18)
Cu2—O2—C13—C14155.33 (13)C26—C27—C28—C291.9 (3)
Cu1—O2—C13—C1480.6 (2)C27—C28—C29—C301.2 (3)
Cu2—O2—C13—C1825.1 (2)C28—C29—C30—C310.4 (4)
Cu1—O2—C13—C1899.03 (18)C29—C30—C31—C261.2 (3)
O2—C13—C14—C15178.08 (17)C29—C30—C31—C32179.4 (2)
C18—C13—C14—C152.3 (3)C27—C26—C31—C300.5 (3)
C13—C14—C15—C160.7 (3)C25—C26—C31—C30178.74 (18)
C14—C15—C16—C171.5 (3)C27—C26—C31—C32178.5 (2)
C15—C16—C17—C182.0 (3)C25—C26—C31—C320.7 (3)
C16—C17—C18—C130.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O13Aai0.992.693.418 (12)130
C10—H10B···O13Bbi0.992.443.242 (14)138
C11—H11B···O13Aaii0.982.653.148 (8)111
C11—H11C···O30.982.483.039 (2)116
C12—H12B···O30.982.342.866 (3)113
C14—H14A···O14Aai0.952.493.127 (10)124
C19—H19A···O11Aa0.952.263.159 (12)158
C20—H20B···O12Aa0.992.633.606 (13)169
C24—H24B···O40.982.292.807 (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 top
Assigned peaks (m/z)Benzoate, 1Phenylacetate, 23-Methylbenzoate, 3
CuL+268282282
(L + H)+207221221
(Gal + Na)+203203203
(Oxidized Gal + OH)-195195195
(Gal – H)-179179179
X-121135135
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.
 

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