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The Cu atom in the title complex, [Cu(C9H7O2)(C4H11NO)2], lies on an inversion centre in an octa­hedral geometry and is coordinated by two bidentate chelating 2-(dimethyl­amino)ethanol groups and two monodentate cinnamate groups which are mutually trans to each other. The non-coordinated O atoms of the cinnamate ligands form intra­molecular hydrogen bonds to the OH groups of the 2-(dimethyl­amino)ethanol ligands, generating six-membered rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013396/sj2247sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013396/sj2247Isup2.hkl
Contains datablock I

CCDC reference: 647331

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.038
  • wR factor = 0.108
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour. PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 19.00 Perc.
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 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(cinnamato-κO)bis[2-(dimethylamino)ethanol-κ2N,O]copper(II) top
Crystal data top
[Cu(C9H7O2)(C4H11NO)2]F(000) = 1132
Mr = 536.11Dx = 1.400 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 34803 reflections
a = 10.4570 (1) Åθ = 2.9–27.5°
b = 10.4520 (1) ŵ = 0.90 mm1
c = 23.2770 (4) ÅT = 150 K
V = 2544.10 (6) Å3Block, pale turquoise
Z = 40.25 × 0.20 × 0.20 mm
Data collection top
Nonius KappaCCD
diffractometer
2913 independent reflections
Radiation source: fine-focus sealed tube2210 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
KappaCCD scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1313
Tmin = 0.763, Tmax = 0.835k = 1313
34803 measured reflectionsl = 3030
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0621P)2 + 0.3589P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
2913 reflectionsΔρmax = 0.42 e Å3
178 parametersΔρmin = 0.39 e Å3
9 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0251 (19)
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.72313 (16)0.03852 (18)0.57656 (8)0.0231 (4)
C20.82838 (17)0.03099 (18)0.60617 (8)0.0248 (4)
H20.84130.11890.59760.030*
C30.90499 (16)0.02489 (17)0.64408 (7)0.0232 (4)
H30.89430.11440.64930.028*
C41.00455 (14)0.0370 (2)0.67889 (8)0.0225 (4)
C51.02622 (17)0.16855 (19)0.67799 (8)0.0290 (4)
H50.97640.22180.65370.035*
C61.12054 (18)0.2222 (2)0.71256 (8)0.0342 (5)
H61.13550.31180.71130.041*
C71.19285 (19)0.1460 (2)0.74877 (9)0.0371 (5)
H71.25650.18310.77260.045*
C81.1719 (2)0.01596 (19)0.75000 (9)0.0367 (5)
H81.22120.03670.77480.044*
C91.07902 (18)0.0385 (2)0.71522 (8)0.0299 (4)
H91.06600.12840.71610.036*
C10A0.4830 (2)0.2843 (2)0.51709 (11)0.0380 (5)0.876 (2)
H10A0.45700.37180.50570.046*0.876 (2)
H10B0.55970.29160.54180.046*0.876 (2)
C11A0.3775 (2)0.2237 (2)0.55055 (10)0.0357 (5)0.876 (2)
H11A0.35850.27740.58450.043*0.876 (2)
H11B0.29960.22090.52640.043*0.876 (2)
C12A0.2908 (2)0.0225 (3)0.58604 (12)0.0414 (7)0.876 (2)
H12A0.24810.06690.61780.062*0.876 (2)
H12B0.31340.06450.59810.062*0.876 (2)
H12C0.23310.01830.55290.062*0.876 (2)
C13A0.4872 (2)0.1012 (3)0.62330 (10)0.0349 (6)0.876 (2)
H13A0.56250.15450.61600.052*0.876 (2)
H13B0.51460.01520.63470.052*0.876 (2)
H13C0.43620.13930.65420.052*0.876 (2)
C10B0.4830 (2)0.2843 (2)0.51709 (11)0.0380 (5)0.124 (2)
H10C0.40350.33210.50850.046*0.124 (2)
H10D0.55130.34870.52260.046*0.124 (2)
C11B0.4646 (17)0.2216 (12)0.5714 (6)0.0357 (5)0.124 (2)
H11C0.40910.27670.59540.043*0.124 (2)
H11D0.54860.21580.59080.043*0.124 (2)
C12B0.4164 (17)0.0223 (17)0.6232 (6)0.0414 (7)0.124 (2)
H12D0.50550.00210.63030.062*0.124 (2)
H12E0.36350.05490.62060.062*0.124 (2)
H12F0.38580.07600.65490.062*0.124 (2)
C13B0.2641 (11)0.1099 (17)0.5594 (7)0.0349 (6)0.124 (2)
H13D0.22410.14660.59370.052*0.124 (2)
H13E0.22540.02650.55100.052*0.124 (2)
H13F0.25090.16740.52670.052*0.124 (2)
Cu10.50000.00000.50000.01941 (15)
N10.40817 (14)0.09281 (15)0.56994 (6)0.0279 (4)
O10.66630 (11)0.02623 (12)0.53766 (5)0.0259 (3)
O20.69552 (12)0.14999 (12)0.59127 (6)0.0318 (3)
O30.51449 (12)0.21311 (13)0.46707 (6)0.0302 (3)
H3A0.4506 (18)0.207 (2)0.4486 (9)0.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0204 (8)0.0238 (9)0.0250 (9)0.0012 (7)0.0018 (7)0.0004 (8)
C20.0245 (9)0.0226 (8)0.0272 (9)0.0024 (7)0.0002 (7)0.0004 (7)
C30.0214 (9)0.0240 (8)0.0241 (9)0.0002 (7)0.0019 (7)0.0018 (7)
C40.0182 (9)0.0291 (9)0.0201 (9)0.0013 (7)0.0020 (6)0.0022 (8)
C50.0275 (9)0.0308 (10)0.0288 (10)0.0001 (8)0.0025 (7)0.0010 (8)
C60.0310 (10)0.0332 (10)0.0383 (11)0.0041 (8)0.0022 (8)0.0051 (9)
C70.0268 (9)0.0499 (13)0.0346 (11)0.0008 (9)0.0076 (8)0.0111 (10)
C80.0329 (11)0.0467 (12)0.0307 (11)0.0090 (9)0.0095 (9)0.0018 (9)
C90.0297 (10)0.0317 (10)0.0283 (10)0.0039 (8)0.0014 (8)0.0024 (8)
C10A0.0529 (13)0.0211 (11)0.0400 (11)0.0057 (9)0.0057 (10)0.0049 (10)
C11A0.0380 (12)0.0303 (12)0.0390 (13)0.0115 (10)0.0032 (10)0.0092 (10)
C12A0.0322 (13)0.0547 (16)0.0372 (14)0.0110 (11)0.0123 (10)0.0071 (12)
C13A0.0376 (13)0.0408 (14)0.0262 (12)0.0055 (10)0.0020 (9)0.0068 (10)
C10B0.0529 (13)0.0211 (11)0.0400 (11)0.0057 (9)0.0057 (10)0.0049 (10)
C11B0.0380 (12)0.0303 (12)0.0390 (13)0.0115 (10)0.0032 (10)0.0092 (10)
C12B0.0322 (13)0.0547 (16)0.0372 (14)0.0110 (11)0.0123 (10)0.0071 (12)
C13B0.0376 (13)0.0408 (14)0.0262 (12)0.0055 (10)0.0020 (9)0.0068 (10)
Cu10.0191 (2)0.0185 (2)0.0206 (2)0.00029 (10)0.00222 (10)0.00095 (11)
N10.0283 (8)0.0278 (8)0.0276 (8)0.0008 (6)0.0017 (6)0.0041 (6)
O10.0231 (6)0.0272 (6)0.0274 (7)0.0012 (5)0.0053 (5)0.0024 (5)
O20.0333 (7)0.0224 (7)0.0398 (8)0.0043 (5)0.0106 (6)0.0035 (6)
O30.0323 (7)0.0260 (8)0.0322 (8)0.0051 (6)0.0071 (5)0.0023 (6)
Geometric parameters (Å, º) top
C1—O21.248 (2)C12A—H12A0.9800
C1—O11.277 (2)C12A—H12B0.9800
C1—C21.488 (2)C12A—H12C0.9800
C2—C31.327 (3)C13A—N11.494 (3)
C2—H20.9500C13A—H13A0.9800
C3—C41.470 (2)C13A—H13B0.9800
C3—H30.9500C13A—H13C0.9800
C4—C51.393 (3)C11B—N11.470 (13)
C4—C91.394 (3)C11B—H11C0.9900
C5—C61.391 (3)C11B—H11D0.9900
C5—H50.9500C12B—N11.445 (13)
C6—C71.385 (3)C12B—H12D0.9800
C6—H60.9500C12B—H12E0.9800
C7—C81.377 (3)C12B—H12F0.9800
C7—H70.9500C13B—N11.537 (12)
C8—C91.386 (3)C13B—H13D0.9800
C8—H80.9500C13B—H13E0.9800
C9—H90.9500C13B—H13F0.9800
C10A—O31.421 (3)Cu1—O11.9666 (12)
C10A—C11A1.492 (3)Cu1—O1i1.9667 (12)
C10A—H10A0.9900Cu1—N12.1246 (14)
C10A—H10B0.9900Cu1—N1i2.1246 (14)
C11A—N11.476 (3)Cu1—O3i2.3605 (14)
C11A—H11A0.9900Cu1—O32.3605 (14)
C11A—H11B0.9900O3—H3A0.797 (16)
C12A—N11.479 (3)
O2—C1—O1125.55 (16)N1—C11B—H11D108.1
O2—C1—C2119.98 (16)H11C—C11B—H11D107.3
O1—C1—C2114.45 (16)N1—C12B—H12D109.5
C3—C2—C1122.65 (17)N1—C12B—H12E109.5
C3—C2—H2118.7H12D—C12B—H12E109.5
C1—C2—H2118.7N1—C12B—H12F109.5
C2—C3—C4126.90 (18)H12D—C12B—H12F109.5
C2—C3—H3116.6H12E—C12B—H12F109.5
C4—C3—H3116.6N1—C13B—H13D109.5
C5—C4—C9118.47 (17)N1—C13B—H13E109.5
C5—C4—C3122.78 (17)H13D—C13B—H13E109.5
C9—C4—C3118.73 (19)N1—C13B—H13F109.5
C6—C5—C4120.28 (18)H13D—C13B—H13F109.5
C6—C5—H5119.9H13E—C13B—H13F109.5
C4—C5—H5119.9O1—Cu1—O1i180.0
C7—C6—C5120.50 (19)O1—Cu1—N189.68 (5)
C7—C6—H6119.7O1i—Cu1—N190.32 (5)
C5—C6—H6119.7O1—Cu1—N1i90.32 (5)
C8—C7—C6119.57 (18)O1i—Cu1—N1i89.68 (5)
C8—C7—H7120.2N1—Cu1—N1i180.0
C6—C7—H7120.2O1—Cu1—O3i92.50 (5)
C7—C8—C9120.31 (19)O1i—Cu1—O3i87.50 (5)
C7—C8—H8119.8N1—Cu1—O3i98.80 (6)
C9—C8—H8119.8N1i—Cu1—O3i81.20 (6)
C8—C9—C4120.9 (2)O1—Cu1—O387.50 (5)
C8—C9—H9119.6O1i—Cu1—O392.50 (5)
C4—C9—H9119.6N1—Cu1—O381.20 (6)
O3—C10A—C11A112.13 (17)N1i—Cu1—O398.80 (6)
O3—C10A—H10A109.2O3i—Cu1—O3179.998 (1)
C11A—C10A—H10A109.2C12B—N1—C11B115.1 (9)
O3—C10A—H10B109.2C11A—N1—C12A110.98 (17)
C11A—C10A—H10B109.2C11A—N1—C13A108.67 (16)
H10A—C10A—H10B107.9C12A—N1—C13A106.10 (17)
N1—C11A—C10A113.14 (17)C12B—N1—C13B104.8 (10)
N1—C11A—H11A109.0C11B—N1—C13B106.9 (10)
C10A—C11A—H11A109.0C12B—N1—Cu1113.4 (7)
N1—C11A—H11B109.0C11B—N1—Cu1104.7 (6)
C10A—C11A—H11B109.0C11A—N1—Cu1106.68 (12)
H11A—C11A—H11B107.8C12A—N1—Cu1110.02 (13)
N1—C12A—H12A109.5C13A—N1—Cu1114.44 (12)
N1—C12A—H12B109.5C13B—N1—Cu1111.9 (6)
N1—C12A—H12C109.5C1—O1—Cu1130.82 (12)
N1—C13A—H13A109.5C10A—O3—Cu1102.32 (12)
N1—C13A—H13B109.5C10A—O3—H3A106.7 (17)
N1—C13A—H13C109.5Cu1—O3—H3A92.9 (18)
N1—C11B—H11C108.1
O2—C1—C2—C37.4 (3)O1—Cu1—N1—C11A102.10 (13)
O1—C1—C2—C3173.90 (17)O1i—Cu1—N1—C11A77.90 (13)
C1—C2—C3—C4174.79 (16)O3i—Cu1—N1—C11A165.42 (12)
C2—C3—C4—C53.4 (3)O3—Cu1—N1—C11A14.58 (12)
C2—C3—C4—C9177.79 (18)O1—Cu1—N1—C12A137.44 (15)
C9—C4—C5—C60.2 (3)O1i—Cu1—N1—C12A42.56 (15)
C3—C4—C5—C6178.99 (17)O3i—Cu1—N1—C12A44.96 (15)
C4—C5—C6—C70.8 (3)O3—Cu1—N1—C12A135.04 (15)
C5—C6—C7—C80.7 (3)O1—Cu1—N1—C13A18.11 (15)
C6—C7—C8—C90.0 (3)O1i—Cu1—N1—C13A161.89 (15)
C7—C8—C9—C40.6 (3)O3i—Cu1—N1—C13A74.37 (14)
C5—C4—C9—C80.5 (3)O3—Cu1—N1—C13A105.63 (14)
C3—C4—C9—C8178.31 (18)O1—Cu1—N1—C13B174.9 (7)
O3—C10A—C11A—N159.4 (3)O1i—Cu1—N1—C13B5.1 (7)
C10A—C11A—N1—C12B122.4 (11)O3i—Cu1—N1—C13B92.6 (7)
C10A—C11A—N1—C11B51.3 (9)O3—Cu1—N1—C13B87.4 (7)
C10A—C11A—N1—C12A161.99 (19)O2—C1—O1—Cu115.8 (3)
C10A—C11A—N1—C13A81.7 (2)C2—C1—O1—Cu1162.77 (12)
C10A—C11A—N1—C13B149.6 (6)N1—Cu1—O1—C183.37 (16)
C10A—C11A—N1—Cu142.1 (2)N1i—Cu1—O1—C196.63 (16)
O1—Cu1—N1—C12B66.8 (8)O3i—Cu1—O1—C115.43 (16)
O1i—Cu1—N1—C12B113.2 (8)O3—Cu1—O1—C1164.57 (16)
O3i—Cu1—N1—C12B25.7 (8)C11A—C10A—O3—Cu139.50 (19)
O3—Cu1—N1—C12B154.3 (8)O1—Cu1—O3—C10A76.72 (11)
O1—Cu1—N1—C11B59.5 (7)O1i—Cu1—O3—C10A103.28 (11)
O1i—Cu1—N1—C11B120.5 (7)N1—Cu1—O3—C10A13.34 (11)
O3i—Cu1—N1—C11B152.0 (7)N1i—Cu1—O3—C10A166.66 (11)
O3—Cu1—N1—C11B28.0 (7)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O2i0.80 (2)1.89 (2)2.6650 (18)166 (2)
Symmetry code: (i) x+1, y, z+1.
 

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