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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m802.
Published online 2009 June 20. doi:  10.1107/S1600536809023010
PMCID: PMC2969428

{2,2′-[1,1′-(Ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphtholato}copper(II)

Abstract

The title complex, [Cu(C26H22N2O4)], is isostructural with its Ni analogue. All intramolecular distances and angles are very similar for the two structures, whereas the packing of the molecules, including C—H(...)O and C—H(...)π interactions, are slightly different.

Related literature

For transition metal complexes with multidentate salen-type ligands, see: Akine et al. (2005 [triangle]); Dong et al. (2009a [triangle],b [triangle]); Katsuki (1995 [triangle]); Ray et al. (2003 [triangle]); Sun et al. (2008 [triangle]). For the isostructural Ni complex, see: Dong et al. (2009c [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m802-scheme1.jpg

Experimental

Crystal data

  • [Cu(C26H22N2O4)]
  • M r = 490.00
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m802-efi4.jpg
  • a = 13.0288 (17) Å
  • b = 7.8934 (12) Å
  • c = 21.292 (2) Å
  • β = 103.217 (2)°
  • V = 2131.7 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.06 mm−1
  • T = 298 K
  • 0.41 × 0.17 × 0.07 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.670, T max = 0.929
  • 10698 measured reflections
  • 3753 independent reflections
  • 2278 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.108
  • S = 1.03
  • 3753 reflections
  • 298 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023010/at2815sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023010/at2815Isup2.hkl

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

Acknowledgments

The authors acknowledge finanical support from the ‘Jing Lan’ Talent Engineering Funds of Lanzhou Jiaotong University.

supplementary crystallographic information

Comment

Transition metal complexes with multidentate salen-type ligands are very interesting in modern coordination chemistry because they have mono-, di- or tri-nuclear metal complexes with important stereochemistry (Katsuki et al., 1995; Akine et al., 2005; Dong et al., 2009b). Metal derivatives of salen-type compounds have been investigated extensively, and copper(II) complexes play a major role in both synthetic and structural research (Ray et al., 2003; Dong et al., 2009a).

In this paper, a new mononuclear copper(II) complex with salen-type bisoxime chelating ligand, 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol, has been synthesized (Sun et al., 2008). The X-ray crystallography of the title complex (Fig. 1) reveals the complex crystallizes in the monoclinic system, with P21/c space group. There is a crystallographic twofold screw axis (symmetry code: 1/2 - x, 1/2 + y, 1/2 - z). The dihedral angle between the coordination plane of O3—Cu1—N1 and that of O4—Cu1—N2 is 26.53°, indicating slight distortion toward tetrahedral geometry from the square planar structure [Cu1—O3: 1.876 (3) Å; Cu1—O4: 1.895 (3) Å; Cu1—N1: 1.976 (3) Å; Cu1—N2: 1.947 (3) Å]), with a mean deviation of 0.016 Å from the N2O2 plane. The crystal structure is further stabilized by intermolecular C16—H16A···O3, C23—H23···O2 hydrogen bonds and C4—H4C···π interactions (Table 1), which link neighbouring molecules into extended chains along the c axis.

Experimental

A solution of Cu(II) acetate monohydrate (1.7 mg, 0.0085 mmol) in ethanol (5 ml) was added dropwise to a solution of 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol (3.4 mg, 0.0079 mmol) in dichloromethane (5 ml). The colour of the mixing solution turns to brown, immediately, and was allowed to stand at room temperature for about one week, the solvent was partially evaporated and obtained dark-brown needle-like single crystals suitable for X-ray crystallographic analysis.

Refinement

H atoms were treated as riding atoms with distances C—H = 0.96 (CH3), C—H = 0.97 (CH2), or 0.93 Å (CH), and Uiso(H) = 1.2 Ueq(C) and 1.5 Ueq(Cmethyl).

Figures

Fig. 1.
The molecule structure of the title complex possessing a crystallographic twofold screw axis passing through the middle point of (–O)–H2C—CH2–(O–) unit (symmetry code: 1/2 - x, 1/2 + y, 1/2 - z). Displacement ellipsoids ...

Crystal data

[Cu(C26H22N2O4)]F(000) = 1012
Mr = 490.00Dx = 1.527 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2535 reflections
a = 13.0288 (17) Åθ = 3.0–25.3°
b = 7.8934 (12) ŵ = 1.06 mm1
c = 21.292 (2) ÅT = 298 K
β = 103.217 (2)°Needle, dark-brown
V = 2131.7 (5) Å30.41 × 0.17 × 0.07 mm
Z = 4

Data collection

Bruker SMART 1000 CCD area-detector diffractometer3753 independent reflections
Radiation source: fine-focus sealed tube2278 reflections with I > 2σ(I)
graphiteRint = 0.051
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→13
Tmin = 0.670, Tmax = 0.929k = −9→9
10698 measured reflectionsl = −25→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0328P)2 + 2.0905P] where P = (Fo2 + 2Fc2)/3
3753 reflections(Δ/σ)max = 0.001
298 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.41 e Å3

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
Cu10.73155 (4)0.18038 (7)0.77719 (2)0.04608 (19)
N10.7004 (3)0.1798 (4)0.86373 (14)0.0465 (9)
N20.8811 (2)0.2362 (4)0.79867 (15)0.0452 (9)
O10.7720 (2)0.1113 (4)0.91807 (14)0.0680 (9)
O20.9266 (2)0.2769 (4)0.86424 (13)0.0512 (8)
O30.5864 (2)0.1927 (4)0.74053 (12)0.0555 (8)
O40.7494 (2)0.0995 (4)0.69654 (13)0.0562 (8)
C10.8537 (4)0.0179 (6)0.9005 (2)0.0689 (14)
H1A0.8289−0.02660.85720.083*
H1B0.8730−0.07720.92970.083*
C20.9486 (3)0.1269 (6)0.9028 (2)0.0637 (13)
H2A0.97790.15940.94720.076*
H2B1.00150.06100.88820.076*
C30.6172 (3)0.2413 (5)0.87978 (19)0.0465 (11)
C40.6114 (4)0.2381 (7)0.94956 (19)0.0661 (14)
H4A0.64530.13760.96970.099*
H4B0.53890.23840.95230.099*
H4C0.64630.33620.97110.099*
C50.5175 (3)0.2722 (5)0.76545 (19)0.0435 (10)
C60.5294 (3)0.3069 (5)0.83128 (19)0.0447 (10)
C70.4498 (4)0.4048 (6)0.8504 (2)0.0572 (12)
H70.45810.43160.89380.069*
C80.3623 (4)0.4603 (6)0.8078 (2)0.0622 (13)
H80.31290.52480.82250.075*
C90.3450 (3)0.4223 (6)0.7418 (2)0.0532 (12)
C100.4212 (3)0.3260 (5)0.7203 (2)0.0466 (10)
C110.4048 (3)0.2850 (6)0.6547 (2)0.0553 (12)
H110.45460.22030.64040.066*
C120.3158 (4)0.3395 (7)0.6113 (2)0.0737 (15)
H120.30540.31090.56790.088*
C130.2418 (4)0.4369 (7)0.6322 (3)0.0781 (16)
H130.18190.47390.60270.094*
C140.2557 (4)0.4787 (6)0.6952 (3)0.0694 (14)
H140.20570.54580.70820.083*
C150.9430 (3)0.2702 (5)0.7603 (2)0.0441 (10)
C161.0539 (3)0.3300 (6)0.7877 (2)0.0596 (12)
H16A1.05320.44900.79690.089*
H16B1.09610.31030.75690.089*
H16C1.08310.26900.82660.089*
C170.8113 (3)0.1659 (5)0.66393 (18)0.0388 (10)
C180.9056 (3)0.2506 (5)0.69117 (19)0.0418 (10)
C190.9665 (3)0.3161 (6)0.6492 (2)0.0530 (11)
H191.02850.37360.66720.064*
C200.9390 (3)0.2994 (6)0.5845 (2)0.0564 (12)
H200.98190.34400.55920.068*
C210.8443 (3)0.2135 (5)0.5550 (2)0.0485 (11)
C220.7806 (3)0.1459 (5)0.59432 (19)0.0427 (10)
C230.6864 (3)0.0651 (5)0.5649 (2)0.0502 (11)
H230.64350.02130.59040.060*
C240.6560 (4)0.0493 (6)0.4991 (2)0.0613 (13)
H240.5929−0.00430.48020.074*
C250.7202 (4)0.1138 (7)0.4606 (2)0.0712 (15)
H250.70050.10100.41600.085*
C260.8112 (4)0.1952 (7)0.4879 (2)0.0641 (13)
H260.85240.23980.46150.077*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0401 (3)0.0603 (4)0.0372 (3)−0.0043 (3)0.0077 (2)−0.0032 (3)
N10.046 (2)0.056 (2)0.0345 (19)−0.0113 (19)0.0022 (16)0.0057 (18)
N20.043 (2)0.050 (2)0.039 (2)−0.0019 (17)0.0021 (16)−0.0126 (17)
O10.060 (2)0.093 (3)0.0447 (19)−0.0031 (19)−0.0005 (16)0.0194 (18)
O20.0535 (18)0.051 (2)0.0445 (17)−0.0028 (15)0.0010 (13)−0.0102 (15)
O30.0415 (16)0.087 (2)0.0368 (16)−0.0011 (17)0.0062 (13)−0.0113 (16)
O40.0506 (18)0.077 (2)0.0449 (17)−0.0232 (16)0.0196 (14)−0.0171 (16)
C10.068 (3)0.055 (3)0.070 (3)0.002 (3)−0.012 (3)0.018 (3)
C20.056 (3)0.064 (3)0.062 (3)0.013 (3)−0.005 (2)0.002 (3)
C30.052 (3)0.051 (3)0.037 (2)−0.019 (2)0.011 (2)0.000 (2)
C40.068 (3)0.093 (4)0.039 (3)−0.018 (3)0.015 (2)0.002 (3)
C50.041 (2)0.046 (3)0.044 (2)−0.015 (2)0.011 (2)−0.001 (2)
C60.047 (2)0.048 (3)0.041 (2)−0.010 (2)0.015 (2)−0.005 (2)
C70.066 (3)0.060 (3)0.051 (3)−0.016 (3)0.025 (3)−0.005 (2)
C80.058 (3)0.051 (3)0.085 (4)−0.007 (3)0.032 (3)−0.006 (3)
C90.045 (3)0.043 (3)0.073 (3)−0.011 (2)0.017 (2)0.007 (3)
C100.041 (2)0.047 (3)0.051 (3)−0.013 (2)0.008 (2)0.004 (2)
C110.044 (3)0.060 (3)0.059 (3)−0.012 (2)0.005 (2)0.006 (2)
C120.058 (3)0.090 (4)0.063 (3)−0.021 (3)−0.008 (3)0.018 (3)
C130.048 (3)0.075 (4)0.100 (5)−0.006 (3)−0.006 (3)0.028 (4)
C140.045 (3)0.057 (3)0.106 (4)−0.003 (2)0.016 (3)0.011 (3)
C150.039 (2)0.037 (3)0.056 (3)0.0032 (19)0.008 (2)−0.009 (2)
C160.043 (3)0.062 (3)0.070 (3)−0.004 (2)0.006 (2)−0.008 (3)
C170.033 (2)0.040 (3)0.045 (2)0.0005 (19)0.0113 (18)−0.006 (2)
C180.039 (2)0.042 (3)0.045 (2)0.002 (2)0.0125 (19)−0.003 (2)
C190.043 (2)0.052 (3)0.066 (3)−0.004 (2)0.017 (2)−0.001 (3)
C200.057 (3)0.062 (3)0.057 (3)−0.001 (3)0.026 (2)0.004 (3)
C210.051 (3)0.051 (3)0.046 (3)0.009 (2)0.013 (2)0.006 (2)
C220.044 (2)0.044 (3)0.041 (2)0.006 (2)0.0108 (19)−0.001 (2)
C230.049 (3)0.050 (3)0.050 (3)0.001 (2)0.010 (2)−0.002 (2)
C240.055 (3)0.077 (4)0.045 (3)0.004 (3)−0.004 (2)−0.008 (3)
C250.072 (4)0.094 (4)0.044 (3)0.010 (3)0.005 (3)0.009 (3)
C260.066 (3)0.078 (4)0.051 (3)0.008 (3)0.019 (2)0.016 (3)

Geometric parameters (Å, °)

Cu1—O31.876 (3)C10—C111.402 (6)
Cu1—O41.895 (3)C11—C121.376 (6)
Cu1—N21.947 (3)C11—H110.9300
Cu1—N11.976 (3)C12—C131.385 (7)
N1—C31.302 (5)C12—H120.9300
N1—O11.417 (4)C13—C141.352 (7)
N2—C151.301 (5)C13—H130.9300
N2—O21.423 (4)C14—H140.9300
O1—C11.414 (5)C15—C181.449 (5)
O2—C21.432 (5)C15—C161.504 (5)
O3—C51.304 (5)C16—H16A0.9600
O4—C171.290 (4)C16—H16B0.9600
C1—C21.497 (6)C16—H16C0.9600
C1—H1A0.9700C17—C181.403 (5)
C1—H1B0.9700C17—C221.453 (5)
C2—H2A0.9700C18—C191.422 (5)
C2—H2B0.9700C19—C201.346 (6)
C3—C61.450 (6)C19—H190.9300
C3—C41.505 (5)C20—C211.421 (6)
C4—H4A0.9600C20—H200.9300
C4—H4B0.9600C21—C261.404 (6)
C4—H4C0.9600C21—C221.411 (5)
C5—C61.401 (5)C22—C231.398 (5)
C5—C101.458 (5)C23—C241.372 (5)
C6—C71.426 (6)C23—H230.9300
C7—C81.357 (6)C24—C251.394 (6)
C7—H70.9300C24—H240.9300
C8—C91.402 (6)C25—C261.357 (6)
C8—H80.9300C25—H250.9300
C9—C101.407 (6)C26—H260.9300
C9—C141.417 (6)
O3—Cu1—O487.76 (11)C11—C10—C5120.1 (4)
O3—Cu1—N2160.95 (14)C9—C10—C5120.5 (4)
O4—Cu1—N288.05 (12)C12—C11—C10120.7 (5)
O3—Cu1—N189.17 (12)C12—C11—H11119.7
O4—Cu1—N1159.73 (14)C10—C11—H11119.7
N2—Cu1—N1100.93 (13)C11—C12—C13120.0 (5)
C3—N1—O1111.1 (3)C11—C12—H12120.0
C3—N1—Cu1127.2 (3)C13—C12—H12120.0
O1—N1—Cu1121.7 (3)C14—C13—C12120.6 (5)
C15—N2—O2113.0 (3)C14—C13—H13119.7
C15—N2—Cu1129.1 (3)C12—C13—H13119.7
O2—N2—Cu1116.9 (2)C13—C14—C9121.4 (5)
C1—O1—N1112.2 (3)C13—C14—H14119.3
N2—O2—C2111.0 (3)C9—C14—H14119.3
C5—O3—Cu1125.3 (2)N2—C15—C18120.2 (4)
C17—O4—Cu1124.9 (3)N2—C15—C16120.0 (4)
O1—C1—C2110.9 (4)C18—C15—C16119.8 (4)
O1—C1—H1A109.5C15—C16—H16A109.5
C2—C1—H1A109.5C15—C16—H16B109.5
O1—C1—H1B109.5H16A—C16—H16B109.5
C2—C1—H1B109.5C15—C16—H16C109.5
H1A—C1—H1B108.0H16A—C16—H16C109.5
O2—C2—C1113.6 (3)H16B—C16—H16C109.5
O2—C2—H2A108.8O4—C17—C18124.6 (4)
C1—C2—H2A108.8O4—C17—C22116.4 (3)
O2—C2—H2B108.8C18—C17—C22118.9 (4)
C1—C2—H2B108.8C17—C18—C19118.4 (4)
H2A—C2—H2B107.7C17—C18—C15122.0 (4)
N1—C3—C6121.0 (4)C19—C18—C15119.6 (4)
N1—C3—C4119.0 (4)C20—C19—C18123.4 (4)
C6—C3—C4120.0 (4)C20—C19—H19118.3
C3—C4—H4A109.5C18—C19—H19118.3
C3—C4—H4B109.5C19—C20—C21120.0 (4)
H4A—C4—H4B109.5C19—C20—H20120.0
C3—C4—H4C109.5C21—C20—H20120.0
H4A—C4—H4C109.5C26—C21—C22118.7 (4)
H4B—C4—H4C109.5C26—C21—C20122.2 (4)
O3—C5—C6124.9 (4)C22—C21—C20119.1 (4)
O3—C5—C10116.2 (4)C23—C22—C21118.8 (4)
C6—C5—C10119.0 (4)C23—C22—C17121.0 (4)
C5—C6—C7118.0 (4)C21—C22—C17120.1 (4)
C5—C6—C3122.1 (4)C24—C23—C22121.2 (4)
C7—C6—C3119.8 (4)C24—C23—H23119.4
C8—C7—C6122.6 (4)C22—C23—H23119.4
C8—C7—H7118.7C23—C24—C25119.7 (4)
C6—C7—H7118.7C23—C24—H24120.1
C7—C8—C9121.2 (4)C25—C24—H24120.1
C7—C8—H8119.4C26—C25—C24120.3 (4)
C9—C8—H8119.4C26—C25—H25119.9
C8—C9—C10118.5 (4)C24—C25—H25119.9
C8—C9—C14123.5 (5)C25—C26—C21121.3 (4)
C10—C9—C14118.0 (5)C25—C26—H26119.3
C11—C10—C9119.4 (4)C21—C26—H26119.3
O3—Cu1—N1—C3−25.1 (4)C14—C9—C10—C5176.7 (4)
O4—Cu1—N1—C3−106.3 (5)O3—C5—C10—C112.8 (6)
N2—Cu1—N1—C3138.7 (3)C6—C5—C10—C11−176.6 (4)
O3—Cu1—N1—O1156.5 (3)O3—C5—C10—C9−175.8 (4)
O4—Cu1—N1—O175.2 (5)C6—C5—C10—C94.7 (6)
N2—Cu1—N1—O1−39.8 (3)C9—C10—C11—C120.7 (6)
O3—Cu1—N2—C15−51.8 (6)C5—C10—C11—C12−178.0 (4)
O4—Cu1—N2—C1525.6 (4)C10—C11—C12—C130.5 (7)
N1—Cu1—N2—C15−172.7 (4)C11—C12—C13—C14−0.3 (8)
O3—Cu1—N2—O2115.2 (4)C12—C13—C14—C9−1.1 (8)
O4—Cu1—N2—O2−167.5 (3)C8—C9—C14—C13−179.1 (5)
N1—Cu1—N2—O2−5.8 (3)C10—C9—C14—C132.2 (7)
C3—N1—O1—C1169.7 (4)O2—N2—C15—C18−174.5 (3)
Cu1—N1—O1—C1−11.6 (4)Cu1—N2—C15—C18−7.2 (6)
C15—N2—O2—C2−111.8 (4)O2—N2—C15—C165.5 (5)
Cu1—N2—O2—C279.2 (3)Cu1—N2—C15—C16172.9 (3)
O4—Cu1—O3—C5−166.2 (3)Cu1—O4—C17—C1830.4 (5)
N2—Cu1—O3—C5−88.8 (5)Cu1—O4—C17—C22−151.3 (3)
N1—Cu1—O3—C533.8 (3)O4—C17—C18—C19179.4 (4)
O3—Cu1—O4—C17125.2 (3)C22—C17—C18—C191.2 (6)
N2—Cu1—O4—C17−36.2 (3)O4—C17—C18—C150.4 (6)
N1—Cu1—O4—C17−153.3 (4)C22—C17—C18—C15−177.8 (3)
N1—O1—C1—C293.8 (4)N2—C15—C18—C17−12.2 (6)
N2—O2—C2—C1−57.3 (5)C16—C15—C18—C17167.8 (4)
O1—C1—C2—O2−55.4 (5)N2—C15—C18—C19168.8 (4)
O1—N1—C3—C6−175.4 (3)C16—C15—C18—C19−11.2 (6)
Cu1—N1—C3—C66.0 (6)C17—C18—C19—C20−0.9 (6)
O1—N1—C3—C42.4 (5)C15—C18—C19—C20178.1 (4)
Cu1—N1—C3—C4−176.1 (3)C18—C19—C20—C210.5 (7)
Cu1—O3—C5—C6−24.8 (6)C19—C20—C21—C26178.9 (4)
Cu1—O3—C5—C10155.8 (3)C19—C20—C21—C22−0.4 (6)
O3—C5—C6—C7176.0 (4)C26—C21—C22—C23−0.8 (6)
C10—C5—C6—C7−4.6 (6)C20—C21—C22—C23178.5 (4)
O3—C5—C6—C3−6.4 (6)C26—C21—C22—C17−178.6 (4)
C10—C5—C6—C3173.0 (4)C20—C21—C22—C170.7 (6)
N1—C3—C6—C515.5 (6)O4—C17—C22—C232.8 (6)
C4—C3—C6—C5−162.4 (4)C18—C17—C22—C23−178.9 (4)
N1—C3—C6—C7−167.0 (4)O4—C17—C22—C21−179.5 (4)
C4—C3—C6—C715.2 (6)C18—C17—C22—C21−1.1 (6)
C5—C6—C7—C82.0 (6)C21—C22—C23—C240.7 (6)
C3—C6—C7—C8−175.6 (4)C17—C22—C23—C24178.5 (4)
C6—C7—C8—C90.6 (7)C22—C23—C24—C250.3 (7)
C7—C8—C9—C10−0.6 (6)C23—C24—C25—C26−1.4 (7)
C7—C8—C9—C14−179.3 (4)C24—C25—C26—C211.4 (8)
C8—C9—C10—C11179.2 (4)C22—C21—C26—C25−0.3 (7)
C14—C9—C10—C11−2.0 (6)C20—C21—C26—C25−179.5 (5)
C8—C9—C10—C5−2.1 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16A···O3i0.962.643.375 (5)134
C23—H23···O2ii0.932.433.261 (5)149
C4—H4C···Cg8i0.962.683.564 (6)153

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+3/2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2815).

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