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
CCDC reference: 647331
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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 = 536.11 | Dx = 1.400 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 34803 reflections |
a = 10.4570 (1) Å | θ = 2.9–27.5° |
b = 10.4520 (1) Å | µ = 0.90 mm−1 |
c = 23.2770 (4) Å | T = 150 K |
V = 2544.10 (6) Å3 | Block, pale turquoise |
Z = 4 | 0.25 × 0.20 × 0.20 mm |
Data collection top
Nonius KappaCCD diffractometer | 2913 independent reflections |
Radiation source: fine-focus sealed tube | 2210 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
KappaCCD scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −13→13 |
Tmin = 0.763, Tmax = 0.835 | k = −13→13 |
34803 measured reflections | l = −30→30 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H 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 reflections | Δρmax = 0.42 e Å−3 |
178 parameters | Δρmin = −0.39 e Å−3 |
9 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.72313 (16) | −0.03852 (18) | 0.57656 (8) | 0.0231 (4) | |
C2 | 0.82838 (17) | 0.03099 (18) | 0.60617 (8) | 0.0248 (4) | |
H2 | 0.8413 | 0.1189 | 0.5976 | 0.030* | |
C3 | 0.90499 (16) | −0.02489 (17) | 0.64408 (7) | 0.0232 (4) | |
H3 | 0.8943 | −0.1144 | 0.6493 | 0.028* | |
C4 | 1.00455 (14) | 0.0370 (2) | 0.67889 (8) | 0.0225 (4) | |
C5 | 1.02622 (17) | 0.16855 (19) | 0.67799 (8) | 0.0290 (4) | |
H5 | 0.9764 | 0.2218 | 0.6537 | 0.035* | |
C6 | 1.12054 (18) | 0.2222 (2) | 0.71256 (8) | 0.0342 (5) | |
H6 | 1.1355 | 0.3118 | 0.7113 | 0.041* | |
C7 | 1.19285 (19) | 0.1460 (2) | 0.74877 (9) | 0.0371 (5) | |
H7 | 1.2565 | 0.1831 | 0.7726 | 0.045* | |
C8 | 1.1719 (2) | 0.01596 (19) | 0.75000 (9) | 0.0367 (5) | |
H8 | 1.2212 | −0.0367 | 0.7748 | 0.044* | |
C9 | 1.07902 (18) | −0.0385 (2) | 0.71522 (8) | 0.0299 (4) | |
H9 | 1.0660 | −0.1284 | 0.7161 | 0.036* | |
C10A | 0.4830 (2) | 0.2843 (2) | 0.51709 (11) | 0.0380 (5) | 0.876 (2) |
H10A | 0.4570 | 0.3718 | 0.5057 | 0.046* | 0.876 (2) |
H10B | 0.5597 | 0.2916 | 0.5418 | 0.046* | 0.876 (2) |
C11A | 0.3775 (2) | 0.2237 (2) | 0.55055 (10) | 0.0357 (5) | 0.876 (2) |
H11A | 0.3585 | 0.2774 | 0.5845 | 0.043* | 0.876 (2) |
H11B | 0.2996 | 0.2209 | 0.5264 | 0.043* | 0.876 (2) |
C12A | 0.2908 (2) | 0.0225 (3) | 0.58604 (12) | 0.0414 (7) | 0.876 (2) |
H12A | 0.2481 | 0.0669 | 0.6178 | 0.062* | 0.876 (2) |
H12B | 0.3134 | −0.0645 | 0.5981 | 0.062* | 0.876 (2) |
H12C | 0.2331 | 0.0183 | 0.5529 | 0.062* | 0.876 (2) |
C13A | 0.4872 (2) | 0.1012 (3) | 0.62330 (10) | 0.0349 (6) | 0.876 (2) |
H13A | 0.5625 | 0.1545 | 0.6160 | 0.052* | 0.876 (2) |
H13B | 0.5146 | 0.0152 | 0.6347 | 0.052* | 0.876 (2) |
H13C | 0.4362 | 0.1393 | 0.6542 | 0.052* | 0.876 (2) |
C10B | 0.4830 (2) | 0.2843 (2) | 0.51709 (11) | 0.0380 (5) | 0.124 (2) |
H10C | 0.4035 | 0.3321 | 0.5085 | 0.046* | 0.124 (2) |
H10D | 0.5513 | 0.3487 | 0.5226 | 0.046* | 0.124 (2) |
C11B | 0.4646 (17) | 0.2216 (12) | 0.5714 (6) | 0.0357 (5) | 0.124 (2) |
H11C | 0.4091 | 0.2767 | 0.5954 | 0.043* | 0.124 (2) |
H11D | 0.5486 | 0.2158 | 0.5908 | 0.043* | 0.124 (2) |
C12B | 0.4164 (17) | 0.0223 (17) | 0.6232 (6) | 0.0414 (7) | 0.124 (2) |
H12D | 0.5055 | −0.0021 | 0.6303 | 0.062* | 0.124 (2) |
H12E | 0.3635 | −0.0549 | 0.6206 | 0.062* | 0.124 (2) |
H12F | 0.3858 | 0.0760 | 0.6549 | 0.062* | 0.124 (2) |
C13B | 0.2641 (11) | 0.1099 (17) | 0.5594 (7) | 0.0349 (6) | 0.124 (2) |
H13D | 0.2241 | 0.1466 | 0.5937 | 0.052* | 0.124 (2) |
H13E | 0.2254 | 0.0265 | 0.5510 | 0.052* | 0.124 (2) |
H13F | 0.2509 | 0.1674 | 0.5267 | 0.052* | 0.124 (2) |
Cu1 | 0.5000 | 0.0000 | 0.5000 | 0.01941 (15) | |
N1 | 0.40817 (14) | 0.09281 (15) | 0.56994 (6) | 0.0279 (4) | |
O1 | 0.66630 (11) | 0.02623 (12) | 0.53766 (5) | 0.0259 (3) | |
O2 | 0.69552 (12) | −0.14999 (12) | 0.59127 (6) | 0.0318 (3) | |
O3 | 0.51449 (12) | 0.21311 (13) | 0.46707 (6) | 0.0302 (3) | |
H3A | 0.4506 (18) | 0.207 (2) | 0.4486 (9) | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0204 (8) | 0.0238 (9) | 0.0250 (9) | 0.0012 (7) | −0.0018 (7) | −0.0004 (8) |
C2 | 0.0245 (9) | 0.0226 (8) | 0.0272 (9) | −0.0024 (7) | 0.0002 (7) | 0.0004 (7) |
C3 | 0.0214 (9) | 0.0240 (8) | 0.0241 (9) | 0.0002 (7) | 0.0019 (7) | −0.0018 (7) |
C4 | 0.0182 (9) | 0.0291 (9) | 0.0201 (9) | 0.0013 (7) | 0.0020 (6) | −0.0022 (8) |
C5 | 0.0275 (9) | 0.0308 (10) | 0.0288 (10) | 0.0001 (8) | −0.0025 (7) | 0.0010 (8) |
C6 | 0.0310 (10) | 0.0332 (10) | 0.0383 (11) | −0.0041 (8) | −0.0022 (8) | −0.0051 (9) |
C7 | 0.0268 (9) | 0.0499 (13) | 0.0346 (11) | −0.0008 (9) | −0.0076 (8) | −0.0111 (10) |
C8 | 0.0329 (11) | 0.0467 (12) | 0.0307 (11) | 0.0090 (9) | −0.0095 (9) | −0.0018 (9) |
C9 | 0.0297 (10) | 0.0317 (10) | 0.0283 (10) | 0.0039 (8) | −0.0014 (8) | −0.0024 (8) |
C10A | 0.0529 (13) | 0.0211 (11) | 0.0400 (11) | −0.0057 (9) | −0.0057 (10) | −0.0049 (10) |
C11A | 0.0380 (12) | 0.0303 (12) | 0.0390 (13) | 0.0115 (10) | −0.0032 (10) | −0.0092 (10) |
C12A | 0.0322 (13) | 0.0547 (16) | 0.0372 (14) | −0.0110 (11) | 0.0123 (10) | −0.0071 (12) |
C13A | 0.0376 (13) | 0.0408 (14) | 0.0262 (12) | 0.0055 (10) | −0.0020 (9) | −0.0068 (10) |
C10B | 0.0529 (13) | 0.0211 (11) | 0.0400 (11) | −0.0057 (9) | −0.0057 (10) | −0.0049 (10) |
C11B | 0.0380 (12) | 0.0303 (12) | 0.0390 (13) | 0.0115 (10) | −0.0032 (10) | −0.0092 (10) |
C12B | 0.0322 (13) | 0.0547 (16) | 0.0372 (14) | −0.0110 (11) | 0.0123 (10) | −0.0071 (12) |
C13B | 0.0376 (13) | 0.0408 (14) | 0.0262 (12) | 0.0055 (10) | −0.0020 (9) | −0.0068 (10) |
Cu1 | 0.0191 (2) | 0.0185 (2) | 0.0206 (2) | 0.00029 (10) | −0.00222 (10) | −0.00095 (11) |
N1 | 0.0283 (8) | 0.0278 (8) | 0.0276 (8) | −0.0008 (6) | 0.0017 (6) | −0.0041 (6) |
O1 | 0.0231 (6) | 0.0272 (6) | 0.0274 (7) | −0.0012 (5) | −0.0053 (5) | 0.0024 (5) |
O2 | 0.0333 (7) | 0.0224 (7) | 0.0398 (8) | −0.0043 (5) | −0.0106 (6) | 0.0035 (6) |
O3 | 0.0323 (7) | 0.0260 (8) | 0.0322 (8) | −0.0051 (6) | −0.0071 (5) | 0.0023 (6) |
Geometric parameters (Å, º) top
C1—O2 | 1.248 (2) | C12A—H12A | 0.9800 |
C1—O1 | 1.277 (2) | C12A—H12B | 0.9800 |
C1—C2 | 1.488 (2) | C12A—H12C | 0.9800 |
C2—C3 | 1.327 (3) | C13A—N1 | 1.494 (3) |
C2—H2 | 0.9500 | C13A—H13A | 0.9800 |
C3—C4 | 1.470 (2) | C13A—H13B | 0.9800 |
C3—H3 | 0.9500 | C13A—H13C | 0.9800 |
C4—C5 | 1.393 (3) | C11B—N1 | 1.470 (13) |
C4—C9 | 1.394 (3) | C11B—H11C | 0.9900 |
C5—C6 | 1.391 (3) | C11B—H11D | 0.9900 |
C5—H5 | 0.9500 | C12B—N1 | 1.445 (13) |
C6—C7 | 1.385 (3) | C12B—H12D | 0.9800 |
C6—H6 | 0.9500 | C12B—H12E | 0.9800 |
C7—C8 | 1.377 (3) | C12B—H12F | 0.9800 |
C7—H7 | 0.9500 | C13B—N1 | 1.537 (12) |
C8—C9 | 1.386 (3) | C13B—H13D | 0.9800 |
C8—H8 | 0.9500 | C13B—H13E | 0.9800 |
C9—H9 | 0.9500 | C13B—H13F | 0.9800 |
C10A—O3 | 1.421 (3) | Cu1—O1 | 1.9666 (12) |
C10A—C11A | 1.492 (3) | Cu1—O1i | 1.9667 (12) |
C10A—H10A | 0.9900 | Cu1—N1 | 2.1246 (14) |
C10A—H10B | 0.9900 | Cu1—N1i | 2.1246 (14) |
C11A—N1 | 1.476 (3) | Cu1—O3i | 2.3605 (14) |
C11A—H11A | 0.9900 | Cu1—O3 | 2.3605 (14) |
C11A—H11B | 0.9900 | O3—H3A | 0.797 (16) |
C12A—N1 | 1.479 (3) | | |
| | | |
O2—C1—O1 | 125.55 (16) | N1—C11B—H11D | 108.1 |
O2—C1—C2 | 119.98 (16) | H11C—C11B—H11D | 107.3 |
O1—C1—C2 | 114.45 (16) | N1—C12B—H12D | 109.5 |
C3—C2—C1 | 122.65 (17) | N1—C12B—H12E | 109.5 |
C3—C2—H2 | 118.7 | H12D—C12B—H12E | 109.5 |
C1—C2—H2 | 118.7 | N1—C12B—H12F | 109.5 |
C2—C3—C4 | 126.90 (18) | H12D—C12B—H12F | 109.5 |
C2—C3—H3 | 116.6 | H12E—C12B—H12F | 109.5 |
C4—C3—H3 | 116.6 | N1—C13B—H13D | 109.5 |
C5—C4—C9 | 118.47 (17) | N1—C13B—H13E | 109.5 |
C5—C4—C3 | 122.78 (17) | H13D—C13B—H13E | 109.5 |
C9—C4—C3 | 118.73 (19) | N1—C13B—H13F | 109.5 |
C6—C5—C4 | 120.28 (18) | H13D—C13B—H13F | 109.5 |
C6—C5—H5 | 119.9 | H13E—C13B—H13F | 109.5 |
C4—C5—H5 | 119.9 | O1—Cu1—O1i | 180.0 |
C7—C6—C5 | 120.50 (19) | O1—Cu1—N1 | 89.68 (5) |
C7—C6—H6 | 119.7 | O1i—Cu1—N1 | 90.32 (5) |
C5—C6—H6 | 119.7 | O1—Cu1—N1i | 90.32 (5) |
C8—C7—C6 | 119.57 (18) | O1i—Cu1—N1i | 89.68 (5) |
C8—C7—H7 | 120.2 | N1—Cu1—N1i | 180.0 |
C6—C7—H7 | 120.2 | O1—Cu1—O3i | 92.50 (5) |
C7—C8—C9 | 120.31 (19) | O1i—Cu1—O3i | 87.50 (5) |
C7—C8—H8 | 119.8 | N1—Cu1—O3i | 98.80 (6) |
C9—C8—H8 | 119.8 | N1i—Cu1—O3i | 81.20 (6) |
C8—C9—C4 | 120.9 (2) | O1—Cu1—O3 | 87.50 (5) |
C8—C9—H9 | 119.6 | O1i—Cu1—O3 | 92.50 (5) |
C4—C9—H9 | 119.6 | N1—Cu1—O3 | 81.20 (6) |
O3—C10A—C11A | 112.13 (17) | N1i—Cu1—O3 | 98.80 (6) |
O3—C10A—H10A | 109.2 | O3i—Cu1—O3 | 179.998 (1) |
C11A—C10A—H10A | 109.2 | C12B—N1—C11B | 115.1 (9) |
O3—C10A—H10B | 109.2 | C11A—N1—C12A | 110.98 (17) |
C11A—C10A—H10B | 109.2 | C11A—N1—C13A | 108.67 (16) |
H10A—C10A—H10B | 107.9 | C12A—N1—C13A | 106.10 (17) |
N1—C11A—C10A | 113.14 (17) | C12B—N1—C13B | 104.8 (10) |
N1—C11A—H11A | 109.0 | C11B—N1—C13B | 106.9 (10) |
C10A—C11A—H11A | 109.0 | C12B—N1—Cu1 | 113.4 (7) |
N1—C11A—H11B | 109.0 | C11B—N1—Cu1 | 104.7 (6) |
C10A—C11A—H11B | 109.0 | C11A—N1—Cu1 | 106.68 (12) |
H11A—C11A—H11B | 107.8 | C12A—N1—Cu1 | 110.02 (13) |
N1—C12A—H12A | 109.5 | C13A—N1—Cu1 | 114.44 (12) |
N1—C12A—H12B | 109.5 | C13B—N1—Cu1 | 111.9 (6) |
N1—C12A—H12C | 109.5 | C1—O1—Cu1 | 130.82 (12) |
N1—C13A—H13A | 109.5 | C10A—O3—Cu1 | 102.32 (12) |
N1—C13A—H13B | 109.5 | C10A—O3—H3A | 106.7 (17) |
N1—C13A—H13C | 109.5 | Cu1—O3—H3A | 92.9 (18) |
N1—C11B—H11C | 108.1 | | |
| | | |
O2—C1—C2—C3 | 7.4 (3) | O1—Cu1—N1—C11A | 102.10 (13) |
O1—C1—C2—C3 | −173.90 (17) | O1i—Cu1—N1—C11A | −77.90 (13) |
C1—C2—C3—C4 | −174.79 (16) | O3i—Cu1—N1—C11A | −165.42 (12) |
C2—C3—C4—C5 | 3.4 (3) | O3—Cu1—N1—C11A | 14.58 (12) |
C2—C3—C4—C9 | −177.79 (18) | O1—Cu1—N1—C12A | −137.44 (15) |
C9—C4—C5—C6 | 0.2 (3) | O1i—Cu1—N1—C12A | 42.56 (15) |
C3—C4—C5—C6 | 178.99 (17) | O3i—Cu1—N1—C12A | −44.96 (15) |
C4—C5—C6—C7 | −0.8 (3) | O3—Cu1—N1—C12A | 135.04 (15) |
C5—C6—C7—C8 | 0.7 (3) | O1—Cu1—N1—C13A | −18.11 (15) |
C6—C7—C8—C9 | 0.0 (3) | O1i—Cu1—N1—C13A | 161.89 (15) |
C7—C8—C9—C4 | −0.6 (3) | O3i—Cu1—N1—C13A | 74.37 (14) |
C5—C4—C9—C8 | 0.5 (3) | O3—Cu1—N1—C13A | −105.63 (14) |
C3—C4—C9—C8 | −178.31 (18) | O1—Cu1—N1—C13B | 174.9 (7) |
O3—C10A—C11A—N1 | 59.4 (3) | O1i—Cu1—N1—C13B | −5.1 (7) |
C10A—C11A—N1—C12B | 122.4 (11) | O3i—Cu1—N1—C13B | −92.6 (7) |
C10A—C11A—N1—C11B | 51.3 (9) | O3—Cu1—N1—C13B | 87.4 (7) |
C10A—C11A—N1—C12A | −161.99 (19) | O2—C1—O1—Cu1 | 15.8 (3) |
C10A—C11A—N1—C13A | 81.7 (2) | C2—C1—O1—Cu1 | −162.77 (12) |
C10A—C11A—N1—C13B | −149.6 (6) | N1—Cu1—O1—C1 | 83.37 (16) |
C10A—C11A—N1—Cu1 | −42.1 (2) | N1i—Cu1—O1—C1 | −96.63 (16) |
O1—Cu1—N1—C12B | −66.8 (8) | O3i—Cu1—O1—C1 | −15.43 (16) |
O1i—Cu1—N1—C12B | 113.2 (8) | O3—Cu1—O1—C1 | 164.57 (16) |
O3i—Cu1—N1—C12B | 25.7 (8) | C11A—C10A—O3—Cu1 | −39.50 (19) |
O3—Cu1—N1—C12B | −154.3 (8) | O1—Cu1—O3—C10A | −76.72 (11) |
O1—Cu1—N1—C11B | 59.5 (7) | O1i—Cu1—O3—C10A | 103.28 (11) |
O1i—Cu1—N1—C11B | −120.5 (7) | N1—Cu1—O3—C10A | 13.34 (11) |
O3i—Cu1—N1—C11B | 152.0 (7) | N1i—Cu1—O3—C10A | −166.66 (11) |
O3—Cu1—N1—C11B | −28.0 (7) | | |
Symmetry code: (i) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2i | 0.80 (2) | 1.89 (2) | 2.6650 (18) | 166 (2) |
Symmetry code: (i) −x+1, −y, −z+1. |