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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400354X/ci6336sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680400354X/ci6336Isup2.hkl
Contains datablock I

CCDC reference: 236044

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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 = 473.97Dx = 1.591 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 9392 reflections
a = 8.145 (5) Åθ = 2.3–25.8°
b = 13.634 (5) ŵ = 1.16 mm1
c = 9.082 (5) ÅT = 293 K
β = 101.206 (5)°Prismatic, green
V = 989.3 (9) Å30.4 × 0.3 × 0.2 mm
Z = 2
Data collection top
Stoe IPDS-2
diffractometer
1912 independent reflections
Radiation source: fine-focus sealed tube1256 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 6.67 pixels mm-1θmax = 25.9°, θmin = 2.6°
φ scansh = 99
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 160
Tmin = 0.783, Tmax = 0.928l = 1111
3720 measured reflections
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.050H 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 parametersΔρmax = 0.24 e Å3
2 restraintsΔρmin = 0.32 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.

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*/Ueq
Cu10.00000.50000.50000.03181 (11)
O10.1684 (2)0.39398 (11)0.42375 (19)0.0390 (4)
O20.0055 (2)0.56581 (12)0.26736 (19)0.0442 (4)
O30.5575 (2)0.30807 (13)0.6652 (2)0.0624 (5)
H30.57990.24940.67080.094*
N10.1678 (2)0.40960 (12)0.4296 (2)0.0323 (4)
C10.0764 (3)0.30399 (16)0.4278 (3)0.0467 (7)
H1A0.14630.25370.37170.056*
H1B0.04250.28180.53070.056*
C20.0752 (3)0.32117 (17)0.3601 (3)0.0445 (6)
H2A0.14780.26420.37670.053*
H2B0.04120.33080.25260.053*
C30.2410 (3)0.46620 (17)0.3184 (3)0.0432 (6)
H3A0.30880.42260.27050.052*
H3B0.31400.51660.37050.052*
C40.1103 (3)0.5138 (2)0.1991 (3)0.0473 (7)
H4A0.16380.55850.13990.057*
H4B0.05210.46400.13250.057*
C50.3000 (3)0.38161 (17)0.5596 (3)0.0372 (6)
H5A0.24900.34080.62580.045*
H5B0.33910.44090.61440.045*
C60.4503 (3)0.32793 (18)0.5259 (3)0.0458 (7)
H6A0.41600.26720.47310.055*
H6B0.50760.36800.46350.055*
O40.72816 (19)0.09995 (11)0.55833 (18)0.0444 (4)
O50.6251 (2)0.11137 (12)0.6725 (2)0.0618 (6)
C70.6036 (3)0.04526 (18)0.5272 (3)0.0349 (6)
C80.5570 (3)0.04978 (19)0.5773 (3)0.0384 (6)
H10.228 (3)0.401 (2)0.3388 (16)0.061 (9)*
H20.096 (2)0.572 (2)0.205 (3)0.076 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0317 (2)0.02944 (19)0.0293 (2)0.0006 (2)0.00655 (14)0.0018 (2)
O10.0350 (9)0.0376 (9)0.0374 (11)0.0018 (7)0.0101 (8)0.0018 (8)
O20.0397 (10)0.0520 (10)0.0345 (10)0.0127 (8)0.0083 (8)0.0028 (8)
O30.0586 (11)0.0494 (11)0.0631 (13)0.0170 (9)0.0281 (10)0.0015 (9)
N10.0324 (11)0.0303 (10)0.0284 (11)0.0023 (8)0.0082 (8)0.0003 (8)
C10.0484 (15)0.0277 (13)0.0536 (17)0.0028 (11)0.0155 (13)0.0006 (11)
C20.0444 (15)0.0334 (13)0.0469 (15)0.0048 (11)0.0134 (12)0.0117 (12)
C30.0410 (14)0.0477 (16)0.0387 (15)0.0079 (10)0.0027 (12)0.0026 (11)
C40.0514 (14)0.0530 (18)0.0344 (12)0.0119 (14)0.0007 (11)0.0085 (13)
C50.0354 (13)0.0356 (13)0.0347 (14)0.0032 (10)0.0075 (10)0.0009 (11)
C60.0399 (16)0.0433 (14)0.0468 (17)0.0075 (11)0.0096 (12)0.0019 (12)
O40.0387 (10)0.0418 (10)0.0442 (11)0.0055 (8)0.0129 (8)0.0008 (8)
O50.0699 (12)0.0376 (10)0.0568 (12)0.0082 (9)0.0396 (10)0.0106 (9)
C70.0372 (14)0.0358 (13)0.0265 (13)0.0022 (11)0.0067 (11)0.0037 (11)
C80.0403 (15)0.0375 (14)0.0299 (14)0.0007 (12)0.0115 (12)0.0015 (12)
Geometric parameters (Å, º) top
Cu1—O12.0199 (17)C2—H2A0.97
Cu1—N12.0340 (18)C2—H2B0.97
Cu1—O22.288 (2)C3—C41.510 (3)
O1—C11.434 (3)C3—H3A0.97
O1—H10.835 (10)C3—H3B0.97
O2—C41.416 (3)C4—H4A0.97
O2—H20.841 (10)C4—H4B0.97
O3—C61.416 (3)C5—C61.508 (3)
O3—H30.82C5—H5A0.97
N1—C51.484 (3)C5—H5B0.97
N1—C31.485 (3)C6—H6A0.97
N1—C21.496 (3)C6—H6B0.97
C1—C21.501 (3)O4—C71.246 (3)
C1—H1A0.97O5—C81.255 (3)
C1—H1B0.97C7—C81.448 (3)
O1—Cu1—N184.93 (8)H2A—C2—H2B108.2
O1—Cu1—O294.24 (7)N1—C3—C4113.02 (19)
N1—Cu1—O280.85 (7)N1—C3—H3A109.0
C1—O1—Cu1106.68 (13)C4—C3—H3A109.0
C1—O1—H1109.1 (19)N1—C3—H3B109.0
Cu1—O1—H1118.3 (19)C4—C3—H3B109.0
C4—O2—Cu1108.24 (13)H3A—C3—H3B107.8
C4—O2—H2109 (2)O2—C4—C3109.75 (19)
Cu1—O2—H2121 (2)O2—C4—H4A109.7
C6—O3—H3109.5C3—C4—H4A109.7
C5—N1—C3110.47 (17)O2—C4—H4B109.7
C5—N1—C2110.91 (17)C3—C4—H4B109.7
C3—N1—C2111.61 (19)H4A—C4—H4B108.2
C5—N1—Cu1109.47 (14)N1—C5—C6117.09 (19)
C3—N1—Cu1106.39 (13)N1—C5—H5A108.0
C2—N1—Cu1107.83 (14)C6—C5—H5A108.0
O1—C1—C2108.85 (19)N1—C5—H5B108.0
O1—C1—H1A109.9C6—C5—H5B108.0
C2—C1—H1A109.9H5A—C5—H5B107.3
O1—C1—H1B109.9O3—C6—C5107.20 (19)
C2—C1—H1B109.9O3—C6—H6A110.3
H1A—C1—H1B108.3C5—C6—H6A110.3
N1—C2—C1109.92 (19)O3—C6—H6B110.3
N1—C2—H2A109.7C5—C6—H6B110.3
C1—C2—H2A109.7H6A—C6—H6B108.5
N1—C2—H2B109.7O4—C7—C8135.7 (2)
C1—C2—H2B109.7O5—C8—C7135.0 (2)
N1—Cu1—O1—C125.03 (15)Cu1—N1—C2—C127.3 (2)
O2—Cu1—O1—C1105.44 (15)O1—C1—C2—N150.1 (2)
O1—Cu1—O2—C486.01 (16)C5—N1—C3—C4168.6 (2)
N1—Cu1—O2—C41.85 (15)C2—N1—C3—C467.5 (2)
O1—Cu1—N1—C5119.12 (14)Cu1—N1—C3—C449.9 (2)
O2—Cu1—N1—C5145.75 (14)Cu1—O2—C4—C323.2 (2)
O1—Cu1—N1—C3121.49 (14)N1—C3—C4—O249.8 (3)
O2—Cu1—N1—C326.36 (13)C3—N1—C5—C653.7 (2)
O1—Cu1—N1—C21.63 (14)C2—N1—C5—C670.6 (3)
O2—Cu1—N1—C293.50 (15)Cu1—N1—C5—C6170.52 (16)
Cu1—O1—C1—C246.7 (2)N1—C5—C6—O3179.39 (18)
C5—N1—C2—C192.6 (2)O4—C7—C8—O51.0 (5)
C3—N1—C2—C1143.79 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O5i0.84 (1)1.74 (1)2.559 (2)166 (3)
O2—H2···O4i0.84 (1)1.80 (1)2.632 (2)171 (3)
O3—H3···O50.821.922.736 (3)177
Symmetry code: (i) x1, y+1/2, z1/2.
 

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