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The synthesis and characterization of a copper(II) complex of salicylaldimine, [Cu2(C2O4)2(C13H20N2O2)2]·2H2O, is de­scrib­ed. The reaction of 2,4-dihydroxy­benzaldehyde and N,N-diethyl­ethylenediamine with K2[Cu(C2O4)2] produces a centrosymmetric binuclear CuII complex. Its structure reveals that the copper(II) ion is five-coordinate and situated in a distorted square-pyramidal environment.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011700/ci6562sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011700/ci6562Isup2.hkl
Contains datablock I

CCDC reference: 241541

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.081
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C14 - C15 ... 1.55 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Bis{[N-(4-hydroxysalicylidene)-N',N'-diethylethyldiamine-κ2N,O] copper(II)oxalate} dihydrate top
Crystal data top
[Cu(C13H20N2O2)2(C2O4)2]·2H2OZ = 1
Mr = 811.79F(000) = 422
Triclinic, P1Dx = 1.573 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.372 (3) ÅCell parameters from 843 reflections
b = 10.449 (3) Åθ = 3.0–26.3°
c = 10.781 (3) ŵ = 1.32 mm1
α = 96.099 (5)°T = 293 K
β = 110.379 (5)°Block, green
γ = 99.826 (5)°0.24 × 0.20 × 0.16 mm
V = 857.0 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3482 independent reflections
Radiation source: fine-focus sealed tube2871 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.737, Tmax = 0.810k = 913
4966 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0427P)2 + 0.0467P]
where P = (Fo2 + 2Fc2)/3
3482 reflections(Δ/σ)max = 0.001
229 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.68053 (4)0.59968 (3)0.58104 (3)0.02960 (10)
N10.7357 (2)0.66085 (17)0.43212 (18)0.0284 (4)
N20.4213 (2)0.72709 (18)0.24261 (17)0.0304 (4)
H2A0.41820.64420.26180.037*
O10.6615 (2)0.41781 (14)0.51685 (15)0.0331 (4)
O20.8314 (3)0.06267 (15)0.33285 (18)0.0448 (4)
H20.86750.04020.27420.067*
O30.7123 (2)0.77806 (15)0.67491 (16)0.0360 (4)
O40.7647 (3)0.88293 (18)0.87933 (19)0.0528 (5)
O50.6519 (2)0.54687 (15)0.74117 (15)0.0356 (4)
O60.6665 (3)0.6356 (2)0.94337 (18)0.0546 (5)
C10.7984 (3)0.4543 (2)0.3566 (2)0.0295 (5)
C20.7328 (3)0.3732 (2)0.4341 (2)0.0269 (5)
C30.7456 (3)0.2413 (2)0.4202 (2)0.0331 (5)
H30.70240.18630.46910.040*
C40.8205 (3)0.1897 (2)0.3361 (2)0.0291 (5)
C50.8841 (3)0.2687 (2)0.2598 (2)0.0343 (5)
H50.93380.23430.20270.041*
C60.8718 (3)0.3973 (2)0.2707 (2)0.0349 (5)
H60.91370.45000.21940.042*
C70.7910 (3)0.5894 (2)0.3581 (2)0.0316 (5)
H70.83060.63090.29870.038*
C80.7347 (3)0.7971 (2)0.4093 (2)0.0321 (5)
H8A0.78120.81350.34030.039*
H8B0.80910.85840.49150.039*
C90.5518 (3)0.8200 (2)0.3664 (2)0.0312 (5)
H9A0.51150.81210.43990.037*
H9B0.55530.90970.34990.037*
C100.2433 (3)0.7532 (3)0.2194 (2)0.0412 (6)
H10A0.21670.74300.29900.049*
H10B0.24520.84390.20690.049*
C110.1009 (4)0.6636 (3)0.1001 (3)0.0535 (7)
H11A0.11380.68470.01910.080*
H11B0.01070.67530.09940.080*
H11C0.10830.57360.10530.080*
C120.4698 (3)0.7281 (2)0.1202 (2)0.0386 (6)
H12A0.58560.71030.14240.046*
H12B0.38860.65730.04920.046*
C130.4685 (4)0.8564 (3)0.0681 (3)0.0488 (7)
H13A0.35400.87430.04460.073*
H13B0.49890.84980.01000.073*
H13C0.55180.92660.13650.073*
C140.7195 (3)0.7812 (2)0.7952 (2)0.0352 (5)
C150.6737 (3)0.6446 (2)0.8342 (2)0.0342 (5)
O70.0501 (2)0.04607 (19)0.84101 (18)0.0514 (5)
H7A0.12420.07360.92080.077*
H7B0.04540.00390.84220.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03940 (17)0.02189 (15)0.02811 (16)0.00457 (11)0.01505 (12)0.00230 (10)
N10.0308 (10)0.0213 (9)0.0331 (10)0.0043 (8)0.0122 (8)0.0062 (8)
N20.0382 (10)0.0259 (10)0.0302 (10)0.0089 (8)0.0149 (8)0.0073 (8)
O10.0476 (9)0.0223 (8)0.0365 (9)0.0041 (7)0.0269 (8)0.0022 (7)
O20.0682 (12)0.0252 (9)0.0558 (11)0.0130 (9)0.0402 (10)0.0061 (8)
O30.0464 (10)0.0264 (8)0.0353 (9)0.0061 (7)0.0173 (8)0.0020 (7)
O40.0699 (13)0.0360 (10)0.0478 (10)0.0002 (9)0.0276 (9)0.0129 (8)
O50.0505 (10)0.0277 (8)0.0329 (8)0.0074 (7)0.0219 (8)0.0044 (7)
O60.0769 (13)0.0571 (12)0.0409 (10)0.0147 (11)0.0360 (10)0.0070 (9)
C10.0317 (11)0.0295 (11)0.0313 (11)0.0087 (10)0.0150 (10)0.0085 (9)
C20.0280 (11)0.0260 (11)0.0245 (10)0.0022 (9)0.0094 (9)0.0019 (9)
C30.0439 (13)0.0243 (11)0.0357 (12)0.0026 (10)0.0227 (11)0.0052 (10)
C40.0308 (11)0.0247 (11)0.0302 (11)0.0044 (9)0.0114 (9)0.0004 (9)
C50.0373 (12)0.0366 (13)0.0379 (12)0.0135 (11)0.0225 (11)0.0064 (10)
C60.0413 (13)0.0350 (13)0.0389 (13)0.0111 (11)0.0245 (11)0.0136 (10)
C70.0340 (12)0.0314 (12)0.0346 (12)0.0048 (10)0.0181 (10)0.0129 (10)
C80.0390 (12)0.0232 (11)0.0359 (12)0.0032 (10)0.0173 (10)0.0075 (9)
C90.0411 (13)0.0249 (11)0.0305 (11)0.0094 (10)0.0165 (10)0.0037 (9)
C100.0376 (13)0.0495 (15)0.0412 (14)0.0149 (12)0.0176 (11)0.0098 (12)
C110.0444 (15)0.0598 (18)0.0513 (16)0.0070 (14)0.0129 (13)0.0136 (14)
C120.0481 (14)0.0410 (14)0.0315 (12)0.0120 (12)0.0201 (11)0.0058 (11)
C130.0571 (17)0.0525 (16)0.0396 (14)0.0053 (14)0.0225 (13)0.0165 (13)
C140.0300 (12)0.0352 (13)0.0387 (13)0.0055 (10)0.0144 (10)0.0032 (11)
C150.0341 (12)0.0371 (13)0.0332 (12)0.0100 (10)0.0148 (10)0.0021 (10)
O70.0570 (11)0.0509 (11)0.0475 (11)0.0087 (9)0.0265 (9)0.0047 (9)
Geometric parameters (Å, º) top
Cu1—O11.9121 (16)C5—C61.361 (3)
Cu1—O51.9462 (16)C5—H50.93
Cu1—O31.9523 (16)C6—H60.93
Cu1—N11.9579 (19)C7—H70.93
N1—C71.287 (3)C8—C91.507 (3)
N1—C81.472 (3)C8—H8A0.97
N2—C101.500 (3)C8—H8B0.97
N2—C91.505 (3)C9—H9A0.97
N2—C121.511 (3)C9—H9B0.97
N2—H2A0.91C10—C111.499 (4)
O1—C21.321 (2)C10—H10A0.97
O2—C41.344 (3)C10—H10B0.97
O2—H20.82C11—H11A0.96
O3—C141.274 (3)C11—H11B0.96
O4—C141.230 (3)C11—H11C0.96
O5—C151.293 (3)C12—C131.507 (4)
O6—C151.212 (3)C12—H12A0.97
C1—C61.412 (3)C12—H12B0.97
C1—C71.422 (3)C13—H13A0.96
C1—C21.424 (3)C13—H13B0.96
C2—C31.397 (3)C13—H13C0.96
C3—C41.383 (3)C14—C151.554 (3)
C3—H30.93O7—H7A0.85
C4—C51.393 (3)O7—H7B0.85
O1—Cu1—O587.76 (6)C9—C8—H8A109.5
O1—Cu1—O3170.92 (7)N1—C8—H8B109.5
O5—Cu1—O383.98 (7)C9—C8—H8B109.5
O1—Cu1—N194.05 (7)H8A—C8—H8B108.1
O5—Cu1—N1173.84 (7)N2—C9—C8114.74 (18)
O3—Cu1—N193.78 (7)N2—C9—H9A108.6
C7—N1—C8116.54 (19)C8—C9—H9A108.6
C7—N1—Cu1122.13 (16)N2—C9—H9B108.6
C8—N1—Cu1120.98 (14)C8—C9—H9B108.6
C10—N2—C9108.79 (17)H9A—C9—H9B107.6
C10—N2—C12113.39 (18)C11—C10—N2113.7 (2)
C9—N2—C12114.09 (17)C11—C10—H10A108.8
C10—N2—H2A106.7N2—C10—H10A108.8
C9—N2—H2A106.7C11—C10—H10B108.8
C12—N2—H2A106.7N2—C10—H10B108.8
C2—O1—Cu1125.53 (13)H10A—C10—H10B107.7
C4—O2—H2109.5C10—C11—H11A109.5
C14—O3—Cu1112.91 (15)C10—C11—H11B109.5
C15—O5—Cu1114.13 (15)H11A—C11—H11B109.5
C6—C1—C7117.6 (2)C10—C11—H11C109.5
C6—C1—C2118.5 (2)H11A—C11—H11C109.5
C7—C1—C2123.8 (2)H11B—C11—H11C109.5
O1—C2—C3119.72 (19)C13—C12—N2113.9 (2)
O1—C2—C1122.8 (2)C13—C12—H12A108.8
C3—C2—C1117.47 (19)N2—C12—H12A108.8
C4—C3—C2122.2 (2)C13—C12—H12B108.8
C4—C3—H3118.9N2—C12—H12B108.8
C2—C3—H3118.9H12A—C12—H12B107.7
O2—C4—C3117.6 (2)C12—C13—H13A109.5
O2—C4—C5121.9 (2)C12—C13—H13B109.5
C3—C4—C5120.4 (2)H13A—C13—H13B109.5
C6—C5—C4118.5 (2)C12—C13—H13C109.5
C6—C5—H5120.7H13A—C13—H13C109.5
C4—C5—H5120.7H13B—C13—H13C109.5
C5—C6—C1122.8 (2)O4—C14—O3124.2 (2)
C5—C6—H6118.6O4—C14—C15120.3 (2)
C1—C6—H6118.6O3—C14—C15115.47 (19)
N1—C7—C1127.5 (2)O6—C15—O5125.8 (2)
N1—C7—H7116.3O6—C15—C14121.3 (2)
C1—C7—H7116.3O5—C15—C14112.9 (2)
N1—C8—C9110.70 (18)H7A—O7—H7B110.1
N1—C8—H8A109.5
O1—Cu1—N1—C718.56 (18)C7—C1—C6—C5179.3 (2)
O3—Cu1—N1—C7156.84 (18)C2—C1—C6—C50.6 (4)
O1—Cu1—N1—C8168.43 (16)C8—N1—C7—C1177.3 (2)
O3—Cu1—N1—C816.18 (16)Cu1—N1—C7—C19.4 (3)
O5—Cu1—O1—C2152.05 (18)C6—C1—C7—N1177.2 (2)
N1—Cu1—O1—C222.05 (18)C2—C1—C7—N14.3 (4)
O5—Cu1—O3—C146.99 (15)C7—N1—C8—C9119.2 (2)
N1—Cu1—O3—C14167.25 (15)Cu1—N1—C8—C967.4 (2)
O1—Cu1—O5—C15173.03 (16)C10—N2—C9—C8174.83 (19)
O3—Cu1—O5—C153.19 (16)C12—N2—C9—C857.5 (3)
Cu1—O1—C2—C3164.55 (16)N1—C8—C9—N256.8 (3)
Cu1—O1—C2—C115.5 (3)C9—N2—C10—C11178.5 (2)
C6—C1—C2—O1179.9 (2)C12—N2—C10—C1153.4 (3)
C7—C1—C2—O11.3 (3)C10—N2—C12—C1358.7 (3)
C6—C1—C2—C30.1 (3)C9—N2—C12—C1366.6 (3)
C7—C1—C2—C3178.6 (2)Cu1—O3—C14—O4168.6 (2)
O1—C2—C3—C4179.3 (2)Cu1—O3—C14—C159.0 (2)
C1—C2—C3—C40.7 (3)Cu1—O5—C15—O6178.1 (2)
C2—C3—C4—O2178.0 (2)Cu1—O5—C15—C140.6 (2)
C2—C3—C4—C51.0 (4)O4—C14—C15—O66.5 (4)
O2—C4—C5—C6178.5 (2)O3—C14—C15—O6175.8 (2)
C3—C4—C5—C60.4 (4)O4—C14—C15—O5171.2 (2)
C4—C5—C6—C10.4 (4)O3—C14—C15—O56.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O5i0.911.982.861 (3)164
O2—H2···O7ii0.821.842.648 (2)166
O7—H7A···O4iii0.851.992.815 (3)163
O7—H7B···O4iv0.852.042.869 (3)166
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1; (iii) x+1, y+1, z+2; (iv) x1, y1, z.
 

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