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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): m881–m882.
Published online 2008 June 7. doi:  10.1107/S1600536808016516
PMCID: PMC2961840

Tetra-μ-benzoato-bis­[(6-methyl­quino­line)­copper(II)]

Abstract

In the title compound, [Cu2(C7H5O2)4(C10H9N)2], the paddle-wheel-type dinuclear complex is constructed by four bridging benzoate groups and two terminal 6-methyl­quinoline ligands. The asymmetric unit contains one-half of the whole mol­ecule, and there is an inversion center at the mid-point of the Cu(...)Cu bond. The octa­hedral coordination of each Cu atom, with four O atoms in the equatorial plane, is completed by the N atom of the 6-methyl­quinoline mol­ecule [Cu—N = 2.212 (2) Å] and by another Cu atom [Cu(...)Cu = 2.6939 (13) Å]. The Cu atom lies 0.234 Å out of the plane of the four O atoms. The molecular packing is stabilized by one intramolecular C—H(...)O as well as C—H(...)π and π–π interactions.

Related literature

For related literature, see: Batten & Robson (1998 [triangle]); Chun et al. (2005 [triangle]); Cotton & Walton (1993 [triangle]); Janiak (2003 [triangle]); Lee et al. (2008 [triangle]); Mines et al. (2002 [triangle]); Pichon et al. (2007 [triangle]); Yoo et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m881-scheme1.jpg

Experimental

Crystal data

  • [Cu2(C7H5O2)4(C10H9N)2]
  • M r = 897.88
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m881-efi1.jpg
  • a = 10.420 (7) Å
  • b = 10.590 (7) Å
  • c = 10.751 (6) Å
  • α = 70.399 (11)°
  • β = 64.234 (10)°
  • γ = 81.107 (10)°
  • V = 1006.5 (11) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.12 mm−1
  • T = 288 (2) K
  • 0.10 × 0.08 × 0.08 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS: Bruker, 1997 [triangle]) T min = 0.898, T max = 0.915
  • 5579 measured reflections
  • 3848 independent reflections
  • 3001 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.100
  • S = 1.04
  • 3848 reflections
  • 272 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)
Table 2
π–π interactions (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808016516/bx2146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016516/bx2146Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial support from the Environmental Technology Educational Innovation Program (2006) of the Ministry of Environment, the Cooperative Research Program for Agricultural Science and Technology Development (20070301–036-019–02), and the Seoul R&BD Program is gratefully acknowledged.

supplementary crystallographic information

Comment

Coordination polymers comprised of metal ions and bridging ligands represent one of the most active areas of material science and chemical research due to their potential applications as functional materials ranging from catalysis, gas absorption, molecular recognition, optics, and so on (Batten & Robson, 1998; Chun et al., 2005; Mines et al., 2002; Janiak, 2003; Yoo et al., 2003). The continuing interest in this area is also due to their intriguing variety of architectures and topologies through the variation of building blocks and reaction conditions. The dinuclear metal carboxylates, M2(O2CR)4, are one of the important building blocks for the study of structures of coordination polymers (Cotton & Walton, 1993) and copper(II) carboxylates among them are often used as building blocks to form a pillard-grid MOF with large pores (Pichon et al., 2007). We have also used copper(II) benzoate as a building block and reported the structure of copper(II) benzoate with quinoxaline (Lee, et al., 2008). In this work, we have employed 6-methylquinoline to investigate the substituent effect of an organic ligand on the structure of copper-benzoate containing coordination complexes.We report here on the structure of new copper(II) benzoate with 6-methylquinoline.

Asymmetric unit contains half of whole molecule, and there is an inversion center in the middle of Cu—Cu bond. Symmetric operation (-x + 1,-y + 2,-z + 1) produces a paddle-wheel type dinuclear copper-benzoate complex (Fig. 1). The paddle-wheel type dinuclear complex is constructed by four bridging benzoate groups and two terminal 6-methylquinoline ligands. The octahedral coordination of each Cu atom, with four oxygen atoms in the equatorial plane, is completed by nitrogen atom of 6-methylquinoline molecule (Cu—N 2.212 (2) Å) and by another copper atom (Cu···Cu 2.6939 (13) Å). The copper atom is 0.234 Å out of the plane of the four oxygen atoms.In the crystal structure the molecular packing is stabilized by one intramolecular C—H···O as well as C—H···π and π ···π interactions, Table, 1 and 2.

Experimental

19.0 mg (0.1 mmol) of Cu(NO3)2.2.5H2O and 28.0 mg (0.2 mmol) of C6H5COONH4 were dissolved in 4 ml me thanol and carefully layered by 4 ml acetone solution of 6-methylquinoline ligand (29.0 mg, 0.2 mmol). Suitable crystals of the title compound for X-ray analysis were obtained in a few weeks.

Refinement

(type here to add refinement details)

Figures

Fig. 1.
The structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are shown at the 30% probability level.

Crystal data

[Cu2(C7H5O2)4(C10H9N)2]Z = 1
Mr = 897.88F000 = 462
Triclinic, P1Dx = 1.481 Mg m3
a = 10.420 (7) ÅMo Kα radiation λ = 0.71073 Å
b = 10.590 (7) ÅCell parameters from 1441 reflections
c = 10.751 (6) Åθ = 2.4–19.8º
α = 70.399 (11)ºµ = 1.12 mm1
β = 64.234 (10)ºT = 288 (2) K
γ = 81.107 (10)ºBlock, blue
V = 1006.5 (11) Å30.10 × 0.08 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer3848 independent reflections
Radiation source: fine-focus sealed tube3001 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 288(2) Kθmax = 26.0º
phi and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS: Bruker, 1997)h = −12→12
Tmin = 0.898, Tmax = 0.915k = −13→10
5579 measured reflectionsl = −13→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.100  w = 1/[σ2(Fo2) + (0.0506P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3848 reflectionsΔρmax = 0.31 e Å3
272 parametersΔρmin = −0.33 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Cu10.52984 (3)0.89016 (3)0.59215 (4)0.03698 (14)
N10.6052 (2)0.7261 (2)0.7373 (2)0.0381 (6)
C10.6560 (3)0.7658 (3)0.8104 (3)0.0443 (7)
H10.65660.85740.79580.053*
C20.7091 (3)0.6802 (3)0.9084 (3)0.0468 (8)
H20.74340.71440.95720.056*
C30.7097 (3)0.5470 (3)0.9310 (3)0.0442 (7)
H30.74470.48850.99590.053*
C40.6576 (3)0.4967 (3)0.8567 (3)0.0378 (7)
C50.6493 (3)0.3595 (3)0.8781 (3)0.0449 (7)
H50.68340.29800.94210.054*
C60.5935 (3)0.3131 (3)0.8091 (3)0.0442 (7)
C70.5463 (3)0.4077 (3)0.7091 (3)0.0476 (8)
H70.51040.37750.65870.057*
C80.5519 (3)0.5417 (3)0.6840 (3)0.0433 (7)
H80.52030.60160.61690.052*
C90.6053 (3)0.5905 (3)0.7591 (3)0.0366 (6)
C100.5756 (4)0.1656 (3)0.8414 (4)0.0595 (9)
H10A0.66700.12510.80050.089*
H10B0.51500.15330.80010.089*
H10C0.53320.12430.94440.089*
O110.6763 (2)1.01228 (19)0.5543 (2)0.0489 (5)
O120.3714 (2)0.8060 (2)0.5994 (2)0.0487 (5)
C110.6982 (3)1.1320 (3)0.4734 (3)0.0391 (7)
C120.8146 (3)1.2041 (3)0.4667 (3)0.0383 (7)
C130.8366 (3)1.3391 (3)0.3937 (3)0.0469 (8)
H130.77921.38620.34650.056*
C140.9423 (3)1.4042 (3)0.3903 (3)0.0530 (8)
H140.95541.49540.34170.064*
C151.0290 (3)1.3360 (3)0.4580 (3)0.0549 (9)
H151.10121.38050.45490.066*
C161.0084 (3)1.2030 (3)0.5295 (4)0.0576 (9)
H161.06771.15610.57440.069*
C170.9012 (3)1.1371 (3)0.5361 (3)0.0516 (8)
H170.88671.04650.58770.062*
O210.6535 (2)0.8478 (2)0.4116 (2)0.0510 (6)
O220.3913 (2)0.9690 (2)0.7424 (2)0.0487 (5)
C210.6732 (3)0.9229 (3)0.2858 (3)0.0391 (7)
C220.7844 (3)0.8779 (3)0.1630 (3)0.0409 (7)
C230.8502 (4)0.7562 (4)0.1888 (4)0.0623 (10)
H230.82240.69910.28310.075*
C240.9574 (4)0.7171 (4)0.0763 (4)0.0760 (12)
H241.00190.63410.09500.091*
C250.9985 (4)0.8004 (4)−0.0633 (4)0.0680 (10)
H251.07120.7743−0.13910.082*
C260.9323 (4)0.9216 (4)−0.0900 (4)0.0617 (10)
H260.95940.9780−0.18460.074*
C270.8256 (3)0.9609 (3)0.0223 (3)0.0502 (8)
H270.78091.04380.00320.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0383 (2)0.0324 (2)0.0399 (2)0.00153 (14)−0.01945 (16)−0.00685 (15)
N10.0415 (14)0.0358 (14)0.0372 (13)0.0001 (10)−0.0181 (11)−0.0090 (10)
C10.0492 (18)0.0365 (17)0.0453 (18)−0.0022 (13)−0.0206 (15)−0.0078 (13)
C20.0510 (19)0.048 (2)0.0507 (19)−0.0009 (14)−0.0295 (16)−0.0147 (15)
C30.0407 (17)0.0497 (19)0.0418 (17)0.0048 (14)−0.0221 (14)−0.0085 (14)
C40.0337 (16)0.0377 (16)0.0379 (16)0.0021 (12)−0.0144 (13)−0.0079 (13)
C50.0423 (17)0.0361 (17)0.0494 (19)0.0059 (13)−0.0197 (15)−0.0062 (14)
C60.0448 (18)0.0392 (17)0.0448 (18)0.0036 (13)−0.0168 (15)−0.0120 (14)
C70.0540 (19)0.0469 (19)0.0497 (19)0.0033 (15)−0.0251 (16)−0.0206 (15)
C80.0528 (19)0.0393 (17)0.0401 (17)−0.0006 (14)−0.0237 (15)−0.0085 (13)
C90.0367 (16)0.0363 (16)0.0331 (15)−0.0026 (12)−0.0133 (13)−0.0068 (12)
C100.073 (2)0.0393 (19)0.070 (2)0.0016 (16)−0.034 (2)−0.0151 (16)
O110.0497 (13)0.0358 (12)0.0616 (14)−0.0046 (9)−0.0312 (11)−0.0022 (10)
O120.0491 (13)0.0398 (12)0.0585 (13)−0.0039 (10)−0.0317 (11)−0.0017 (10)
C110.0379 (16)0.0363 (17)0.0411 (17)0.0006 (13)−0.0132 (14)−0.0137 (13)
C120.0350 (16)0.0367 (16)0.0413 (17)0.0002 (12)−0.0135 (13)−0.0128 (13)
C130.0485 (19)0.0387 (18)0.0525 (19)−0.0006 (14)−0.0221 (16)−0.0104 (14)
C140.058 (2)0.0367 (18)0.058 (2)−0.0102 (15)−0.0184 (17)−0.0102 (15)
C150.0415 (19)0.066 (2)0.058 (2)−0.0121 (16)−0.0134 (16)−0.0248 (18)
C160.048 (2)0.060 (2)0.069 (2)−0.0029 (16)−0.0319 (18)−0.0124 (18)
C170.0471 (19)0.0436 (19)0.061 (2)−0.0037 (15)−0.0251 (17)−0.0070 (15)
O210.0572 (14)0.0438 (13)0.0428 (13)0.0113 (10)−0.0182 (11)−0.0104 (10)
O220.0509 (13)0.0469 (13)0.0484 (12)0.0108 (10)−0.0229 (10)−0.0161 (10)
C210.0363 (16)0.0394 (17)0.0476 (19)−0.0013 (13)−0.0212 (14)−0.0145 (14)
C220.0366 (16)0.0488 (19)0.0424 (18)0.0003 (13)−0.0196 (14)−0.0158 (14)
C230.064 (2)0.067 (2)0.0436 (19)0.0204 (18)−0.0191 (18)−0.0152 (17)
C240.070 (3)0.082 (3)0.068 (3)0.037 (2)−0.027 (2)−0.032 (2)
C250.055 (2)0.094 (3)0.055 (2)0.006 (2)−0.0153 (19)−0.036 (2)
C260.061 (2)0.084 (3)0.0413 (19)−0.017 (2)−0.0191 (18)−0.0156 (18)
C270.053 (2)0.053 (2)0.050 (2)−0.0023 (15)−0.0265 (17)−0.0140 (16)

Geometric parameters (Å, °)

Cu1—O121.955 (2)C11—O12i1.254 (3)
Cu1—O211.964 (2)C11—C121.495 (4)
Cu1—O111.971 (2)C12—C131.380 (4)
Cu1—O221.974 (2)C12—C171.381 (4)
Cu1—N12.212 (2)C13—C141.367 (4)
Cu1—Cu1i2.6939 (13)C13—H130.9300
N1—C11.314 (4)C14—C151.373 (4)
N1—C91.375 (4)C14—H140.9300
C1—C21.396 (4)C15—C161.359 (4)
C1—H10.9300C15—H150.9300
C2—C31.347 (4)C16—C171.370 (4)
C2—H20.9300C16—H160.9300
C3—C41.404 (4)C17—H170.9300
C3—H30.9300O21—C211.261 (3)
C4—C51.403 (4)O22—C21i1.250 (3)
C4—C91.419 (4)C21—O22i1.250 (3)
C5—C61.355 (4)C21—C221.495 (4)
C5—H50.9300C22—C231.364 (4)
C6—C71.410 (4)C22—C271.380 (4)
C6—C101.505 (4)C23—C241.379 (5)
C7—C81.358 (4)C23—H230.9300
C7—H70.9300C24—C251.372 (5)
C8—C91.410 (4)C24—H240.9300
C8—H80.9300C25—C261.363 (5)
C10—H10A0.9600C25—H250.9300
C10—H10B0.9600C26—C271.377 (5)
C10—H10C0.9600C26—H260.9300
O11—C111.262 (3)C27—H270.9300
O12—C11i1.254 (3)
O12—Cu1—O2189.07 (10)H10A—C10—H10C109.5
O12—Cu1—O11166.38 (8)H10B—C10—H10C109.5
O21—Cu1—O1189.52 (10)C11—O11—Cu1127.61 (19)
O12—Cu1—O2288.79 (10)C11i—O12—Cu1121.26 (19)
O21—Cu1—O22166.32 (8)O12i—C11—O11124.7 (3)
O11—Cu1—O2289.39 (10)O12i—C11—C12118.4 (3)
O12—Cu1—N1101.96 (9)O11—C11—C12116.9 (3)
O21—Cu1—N197.02 (9)C13—C12—C17118.5 (3)
O11—Cu1—N191.66 (9)C13—C12—C11121.1 (3)
O22—Cu1—N196.64 (10)C17—C12—C11120.4 (3)
O12—Cu1—Cu1i86.24 (7)C14—C13—C12120.4 (3)
O21—Cu1—Cu1i82.33 (7)C14—C13—H13119.8
O11—Cu1—Cu1i80.14 (7)C12—C13—H13119.8
O22—Cu1—Cu1i84.05 (7)C13—C14—C15120.6 (3)
N1—Cu1—Cu1i171.77 (6)C13—C14—H14119.7
C1—N1—C9117.2 (2)C15—C14—H14119.7
C1—N1—Cu1114.60 (19)C16—C15—C14119.3 (3)
C9—N1—Cu1128.17 (19)C16—C15—H15120.4
N1—C1—C2124.6 (3)C14—C15—H15120.4
N1—C1—H1117.7C15—C16—C17120.7 (3)
C2—C1—H1117.7C15—C16—H16119.6
C3—C2—C1118.8 (3)C17—C16—H16119.6
C3—C2—H2120.6C16—C17—C12120.5 (3)
C1—C2—H2120.6C16—C17—H17119.8
C2—C3—C4120.0 (3)C12—C17—H17119.8
C2—C3—H3120.0C21—O21—Cu1125.3 (2)
C4—C3—H3120.0C21i—O22—Cu1123.10 (19)
C5—C4—C3123.6 (3)O22i—C21—O21125.0 (3)
C5—C4—C9118.7 (3)O22i—C21—C22118.6 (3)
C3—C4—C9117.7 (3)O21—C21—C22116.4 (3)
C6—C5—C4122.6 (3)C23—C22—C27119.1 (3)
C6—C5—H5118.7C23—C22—C21120.4 (3)
C4—C5—H5118.7C27—C22—C21120.5 (3)
C5—C6—C7118.0 (3)C22—C23—C24120.6 (3)
C5—C6—C10121.9 (3)C22—C23—H23119.7
C7—C6—C10120.1 (3)C24—C23—H23119.7
C8—C7—C6121.9 (3)C25—C24—C23120.1 (4)
C8—C7—H7119.0C25—C24—H24119.9
C6—C7—H7119.0C23—C24—H24119.9
C7—C8—C9120.3 (3)C26—C25—C24119.6 (3)
C7—C8—H8119.8C26—C25—H25120.2
C9—C8—H8119.8C24—C25—H25120.2
N1—C9—C8119.9 (2)C25—C26—C27120.3 (3)
N1—C9—C4121.7 (3)C25—C26—H26119.9
C8—C9—C4118.4 (3)C27—C26—H26119.9
C6—C10—H10A109.5C26—C27—C22120.3 (3)
C6—C10—H10B109.5C26—C27—H27119.8
H10A—C10—H10B109.5C22—C27—H27119.8
C6—C10—H10C109.5
O12—Cu1—N1—C1−147.0 (2)Cu1i—Cu1—O12—C11i1.0 (2)
O21—Cu1—N1—C1122.5 (2)Cu1—O11—C11—O12i−0.8 (4)
O11—Cu1—N1—C132.8 (2)Cu1—O11—C11—C12178.41 (18)
O22—Cu1—N1—C1−56.8 (2)O12i—C11—C12—C136.2 (4)
O12—Cu1—N1—C933.2 (2)O11—C11—C12—C13−173.0 (3)
O21—Cu1—N1—C9−57.3 (2)O12i—C11—C12—C17−175.0 (3)
O11—Cu1—N1—C9−147.0 (2)O11—C11—C12—C175.7 (4)
O22—Cu1—N1—C9123.4 (2)C17—C12—C13—C140.2 (5)
C9—N1—C1—C2−0.3 (4)C11—C12—C13—C14179.0 (3)
Cu1—N1—C1—C2179.9 (2)C12—C13—C14—C150.7 (5)
N1—C1—C2—C30.2 (5)C13—C14—C15—C16−0.4 (5)
C1—C2—C3—C40.0 (5)C14—C15—C16—C17−0.9 (5)
C2—C3—C4—C5−177.4 (3)C15—C16—C17—C121.8 (5)
C2—C3—C4—C9−0.1 (4)C13—C12—C17—C16−1.5 (5)
C3—C4—C5—C6177.4 (3)C11—C12—C17—C16179.7 (3)
C9—C4—C5—C60.1 (4)O12—Cu1—O21—C2190.1 (2)
C4—C5—C6—C72.0 (5)O11—Cu1—O21—C21−76.4 (2)
C4—C5—C6—C10−175.4 (3)O22—Cu1—O21—C219.1 (5)
C5—C6—C7—C8−1.9 (5)N1—Cu1—O21—C21−168.0 (2)
C10—C6—C7—C8175.6 (3)Cu1i—Cu1—O21—C213.8 (2)
C6—C7—C8—C9−0.3 (5)O12—Cu1—O22—C21i−85.7 (2)
C1—N1—C9—C8179.9 (3)O21—Cu1—O22—C21i−4.6 (5)
Cu1—N1—C9—C8−0.3 (4)O11—Cu1—O22—C21i80.8 (2)
C1—N1—C9—C40.2 (4)N1—Cu1—O22—C21i172.4 (2)
Cu1—N1—C9—C4−179.98 (18)Cu1i—Cu1—O22—C21i0.6 (2)
C7—C8—C9—N1−177.4 (3)Cu1—O21—C21—O22i−5.7 (4)
C7—C8—C9—C42.3 (4)Cu1—O21—C21—C22173.24 (18)
C5—C4—C9—N1177.5 (2)O22i—C21—C22—C23−175.4 (3)
C3—C4—C9—N10.0 (4)O21—C21—C22—C235.6 (4)
C5—C4—C9—C8−2.2 (4)O22i—C21—C22—C276.9 (4)
C3—C4—C9—C8−179.7 (3)O21—C21—C22—C27−172.1 (3)
O12—Cu1—O11—C11−1.8 (5)C27—C22—C23—C240.8 (5)
O21—Cu1—O11—C1182.3 (3)C21—C22—C23—C24−177.0 (3)
O22—Cu1—O11—C11−84.1 (3)C22—C23—C24—C25−0.3 (6)
N1—Cu1—O11—C11179.3 (2)C23—C24—C25—C26−0.3 (6)
Cu1i—Cu1—O11—C110.0 (2)C24—C25—C26—C270.5 (6)
O21—Cu1—O12—C11i−81.4 (2)C25—C26—C27—C22−0.1 (5)
O11—Cu1—O12—C11i2.7 (5)C23—C22—C27—C26−0.6 (5)
O22—Cu1—O12—C11i85.1 (2)C21—C22—C27—C26177.2 (3)
N1—Cu1—O12—C11i−178.4 (2)

Symmetry codes: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1···O110.932.503.047 (4)118
C2—H2···Cg1ii0.932.823.734 (3)168

Symmetry codes: (ii) x, y, z+1.

Table 2 π–π interactions ( Å, ° )

Cg2 is the centroid of ring C22–C27. The offset is defined as the distance between CgI and the perpendicular projection of CgJ on ring I.

CgICgJCgI···CgJDihedral angleInterplanar distanceOffset
Cg2Cg2i3.967 (4)03.392.06

Symmetry code: (i) -x+2,-y+2,-z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2146).

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