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In the crystal structure of the title compound, [Cu(C6H15NO3)2](C4O4), the cations and anions are located on inversion centres and a supramolecular architecture is formed. Two triethanolamine (TEA) ligands coordinate to the CuII ion through four O atoms and two N atoms acting as N,O,O′-tridentate ligands, resulting in a distorted octahedral environment, with Cu—O bond distances of 2.0199 (17) and 2.288 (2) Å and a Cu—N distance of 2.0340 (18) Å. The squarate (C4O42−) anions and [Cu(TEA)2]2+ cations are linked to each other by hydrogen bonding between coordinated hydroxyl H atoms of TEA and squarate O atoms, forming layers. Adjacent layers are interlinked by hydrogen bonding between free hydroxyl H atoms of TEA and one of the squarate O atoms.
Supporting information
CCDC reference: 236044
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.026
- wR factor = 0.050
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 0.774
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 = 5.96 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O2 = 6.95 su
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.50
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Bis(triethanolamine-
κ3N,
O,
O')copper(II) squarate
top
Crystal data top
[Cu(C6H15NO3)2](C4O4) | F(000) = 498 |
Mr = 473.97 | Dx = 1.591 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 9392 reflections |
a = 8.145 (5) Å | θ = 2.3–25.8° |
b = 13.634 (5) Å | µ = 1.16 mm−1 |
c = 9.082 (5) Å | T = 293 K |
β = 101.206 (5)° | Prismatic, green |
V = 989.3 (9) Å3 | 0.4 × 0.3 × 0.2 mm |
Z = 2 | |
Data collection top
Stoe IPDS-2 diffractometer | 1912 independent reflections |
Radiation source: fine-focus sealed tube | 1256 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.9°, θmin = 2.6° |
φ scans | h = −9→9 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −16→0 |
Tmin = 0.783, Tmax = 0.928 | l = −11→11 |
3720 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.77 | w = 1/[σ2(Fo2) + (0.0189P)2] where P = (Fo2 + 2Fc2)/3 |
1912 reflections | (Δ/σ)max = 0.001 |
141 parameters | Δρmax = 0.24 e Å−3 |
2 restraints | Δρmin = −0.32 e Å−3 |
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 | |
Cu1 | 0.0000 | 0.5000 | 0.5000 | 0.03181 (11) | |
O1 | −0.1684 (2) | 0.39398 (11) | 0.42375 (19) | 0.0390 (4) | |
O2 | −0.0055 (2) | 0.56581 (12) | 0.26736 (19) | 0.0442 (4) | |
O3 | 0.5575 (2) | 0.30807 (13) | 0.6652 (2) | 0.0624 (5) | |
H3 | 0.5799 | 0.2494 | 0.6708 | 0.094* | |
N1 | 0.1678 (2) | 0.40960 (12) | 0.4296 (2) | 0.0323 (4) | |
C1 | −0.0764 (3) | 0.30399 (16) | 0.4278 (3) | 0.0467 (7) | |
H1A | −0.1463 | 0.2537 | 0.3717 | 0.056* | |
H1B | −0.0425 | 0.2818 | 0.5307 | 0.056* | |
C2 | 0.0752 (3) | 0.32117 (17) | 0.3601 (3) | 0.0445 (6) | |
H2A | 0.1478 | 0.2642 | 0.3767 | 0.053* | |
H2B | 0.0412 | 0.3308 | 0.2526 | 0.053* | |
C3 | 0.2410 (3) | 0.46620 (17) | 0.3184 (3) | 0.0432 (6) | |
H3A | 0.3088 | 0.4226 | 0.2705 | 0.052* | |
H3B | 0.3140 | 0.5166 | 0.3705 | 0.052* | |
C4 | 0.1103 (3) | 0.5138 (2) | 0.1991 (3) | 0.0473 (7) | |
H4A | 0.1638 | 0.5585 | 0.1399 | 0.057* | |
H4B | 0.0521 | 0.4640 | 0.1325 | 0.057* | |
C5 | 0.3000 (3) | 0.38161 (17) | 0.5596 (3) | 0.0372 (6) | |
H5A | 0.2490 | 0.3408 | 0.6258 | 0.045* | |
H5B | 0.3391 | 0.4409 | 0.6144 | 0.045* | |
C6 | 0.4503 (3) | 0.32793 (18) | 0.5259 (3) | 0.0458 (7) | |
H6A | 0.4160 | 0.2672 | 0.4731 | 0.055* | |
H6B | 0.5076 | 0.3680 | 0.4635 | 0.055* | |
O4 | 0.72816 (19) | −0.09995 (11) | 0.55833 (18) | 0.0444 (4) | |
O5 | 0.6251 (2) | 0.11137 (12) | 0.6725 (2) | 0.0618 (6) | |
C7 | 0.6036 (3) | −0.04526 (18) | 0.5272 (3) | 0.0349 (6) | |
C8 | 0.5570 (3) | 0.04978 (19) | 0.5773 (3) | 0.0384 (6) | |
H1 | −0.228 (3) | 0.401 (2) | 0.3388 (16) | 0.061 (9)* | |
H2 | −0.096 (2) | 0.572 (2) | 0.205 (3) | 0.076 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0317 (2) | 0.02944 (19) | 0.0293 (2) | 0.0006 (2) | −0.00655 (14) | −0.0018 (2) |
O1 | 0.0350 (9) | 0.0376 (9) | 0.0374 (11) | 0.0018 (7) | −0.0101 (8) | −0.0018 (8) |
O2 | 0.0397 (10) | 0.0520 (10) | 0.0345 (10) | 0.0127 (8) | −0.0083 (8) | 0.0028 (8) |
O3 | 0.0586 (11) | 0.0494 (11) | 0.0631 (13) | 0.0170 (9) | −0.0281 (10) | −0.0015 (9) |
N1 | 0.0324 (11) | 0.0303 (10) | 0.0284 (11) | 0.0023 (8) | −0.0082 (8) | 0.0003 (8) |
C1 | 0.0484 (15) | 0.0277 (13) | 0.0536 (17) | −0.0028 (11) | −0.0155 (13) | 0.0006 (11) |
C2 | 0.0444 (15) | 0.0334 (13) | 0.0469 (15) | 0.0048 (11) | −0.0134 (12) | −0.0117 (12) |
C3 | 0.0410 (14) | 0.0477 (16) | 0.0387 (15) | 0.0079 (10) | 0.0027 (12) | 0.0026 (11) |
C4 | 0.0514 (14) | 0.0530 (18) | 0.0344 (12) | 0.0119 (14) | 0.0007 (11) | 0.0085 (13) |
C5 | 0.0354 (13) | 0.0356 (13) | 0.0347 (14) | 0.0032 (10) | −0.0075 (10) | 0.0009 (11) |
C6 | 0.0399 (16) | 0.0433 (14) | 0.0468 (17) | 0.0075 (11) | −0.0096 (12) | −0.0019 (12) |
O4 | 0.0387 (10) | 0.0418 (10) | 0.0442 (11) | 0.0055 (8) | −0.0129 (8) | −0.0008 (8) |
O5 | 0.0699 (12) | 0.0376 (10) | 0.0568 (12) | 0.0082 (9) | −0.0396 (10) | −0.0106 (9) |
C7 | 0.0372 (14) | 0.0358 (13) | 0.0265 (13) | −0.0022 (11) | −0.0067 (11) | 0.0037 (11) |
C8 | 0.0403 (15) | 0.0375 (14) | 0.0299 (14) | −0.0007 (12) | −0.0115 (12) | 0.0015 (12) |
Geometric parameters (Å, º) top
Cu1—O1 | 2.0199 (17) | C2—H2A | 0.97 |
Cu1—N1 | 2.0340 (18) | C2—H2B | 0.97 |
Cu1—O2 | 2.288 (2) | C3—C4 | 1.510 (3) |
O1—C1 | 1.434 (3) | C3—H3A | 0.97 |
O1—H1 | 0.835 (10) | C3—H3B | 0.97 |
O2—C4 | 1.416 (3) | C4—H4A | 0.97 |
O2—H2 | 0.841 (10) | C4—H4B | 0.97 |
O3—C6 | 1.416 (3) | C5—C6 | 1.508 (3) |
O3—H3 | 0.82 | C5—H5A | 0.97 |
N1—C5 | 1.484 (3) | C5—H5B | 0.97 |
N1—C3 | 1.485 (3) | C6—H6A | 0.97 |
N1—C2 | 1.496 (3) | C6—H6B | 0.97 |
C1—C2 | 1.501 (3) | O4—C7 | 1.246 (3) |
C1—H1A | 0.97 | O5—C8 | 1.255 (3) |
C1—H1B | 0.97 | C7—C8 | 1.448 (3) |
| | | |
O1—Cu1—N1 | 84.93 (8) | H2A—C2—H2B | 108.2 |
O1—Cu1—O2 | 94.24 (7) | N1—C3—C4 | 113.02 (19) |
N1—Cu1—O2 | 80.85 (7) | N1—C3—H3A | 109.0 |
C1—O1—Cu1 | 106.68 (13) | C4—C3—H3A | 109.0 |
C1—O1—H1 | 109.1 (19) | N1—C3—H3B | 109.0 |
Cu1—O1—H1 | 118.3 (19) | C4—C3—H3B | 109.0 |
C4—O2—Cu1 | 108.24 (13) | H3A—C3—H3B | 107.8 |
C4—O2—H2 | 109 (2) | O2—C4—C3 | 109.75 (19) |
Cu1—O2—H2 | 121 (2) | O2—C4—H4A | 109.7 |
C6—O3—H3 | 109.5 | C3—C4—H4A | 109.7 |
C5—N1—C3 | 110.47 (17) | O2—C4—H4B | 109.7 |
C5—N1—C2 | 110.91 (17) | C3—C4—H4B | 109.7 |
C3—N1—C2 | 111.61 (19) | H4A—C4—H4B | 108.2 |
C5—N1—Cu1 | 109.47 (14) | N1—C5—C6 | 117.09 (19) |
C3—N1—Cu1 | 106.39 (13) | N1—C5—H5A | 108.0 |
C2—N1—Cu1 | 107.83 (14) | C6—C5—H5A | 108.0 |
O1—C1—C2 | 108.85 (19) | N1—C5—H5B | 108.0 |
O1—C1—H1A | 109.9 | C6—C5—H5B | 108.0 |
C2—C1—H1A | 109.9 | H5A—C5—H5B | 107.3 |
O1—C1—H1B | 109.9 | O3—C6—C5 | 107.20 (19) |
C2—C1—H1B | 109.9 | O3—C6—H6A | 110.3 |
H1A—C1—H1B | 108.3 | C5—C6—H6A | 110.3 |
N1—C2—C1 | 109.92 (19) | O3—C6—H6B | 110.3 |
N1—C2—H2A | 109.7 | C5—C6—H6B | 110.3 |
C1—C2—H2A | 109.7 | H6A—C6—H6B | 108.5 |
N1—C2—H2B | 109.7 | O4—C7—C8 | 135.7 (2) |
C1—C2—H2B | 109.7 | O5—C8—C7 | 135.0 (2) |
| | | |
N1—Cu1—O1—C1 | 25.03 (15) | Cu1—N1—C2—C1 | −27.3 (2) |
O2—Cu1—O1—C1 | 105.44 (15) | O1—C1—C2—N1 | 50.1 (2) |
O1—Cu1—O2—C4 | −86.01 (16) | C5—N1—C3—C4 | −168.6 (2) |
N1—Cu1—O2—C4 | −1.85 (15) | C2—N1—C3—C4 | 67.5 (2) |
O1—Cu1—N1—C5 | −119.12 (14) | Cu1—N1—C3—C4 | −49.9 (2) |
O2—Cu1—N1—C5 | 145.75 (14) | Cu1—O2—C4—C3 | −23.2 (2) |
O1—Cu1—N1—C3 | 121.49 (14) | N1—C3—C4—O2 | 49.8 (3) |
O2—Cu1—N1—C3 | 26.36 (13) | C3—N1—C5—C6 | −53.7 (2) |
O1—Cu1—N1—C2 | 1.63 (14) | C2—N1—C5—C6 | 70.6 (3) |
O2—Cu1—N1—C2 | −93.50 (15) | Cu1—N1—C5—C6 | −170.52 (16) |
Cu1—O1—C1—C2 | −46.7 (2) | N1—C5—C6—O3 | −179.39 (18) |
C5—N1—C2—C1 | 92.6 (2) | O4—C7—C8—O5 | −1.0 (5) |
C3—N1—C2—C1 | −143.79 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O5i | 0.84 (1) | 1.74 (1) | 2.559 (2) | 166 (3) |
O2—H2···O4i | 0.84 (1) | 1.80 (1) | 2.632 (2) | 171 (3) |
O3—H3···O5 | 0.82 | 1.92 | 2.736 (3) | 177 |
Symmetry code: (i) x−1, −y+1/2, z−1/2. |
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