{1,1′-[Butane-1,4-diylbis(nitrilo­methyl­idyne)]di-2-naphtho­lato}copper(II) ethanol monosolvate

Kargar, H.; Kia, R.

doi:10.1107/S1600536810053183

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page m128

https://doi.org/10.1107/S1600536810053183

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{1,1′-[Butane-1,4-diylbis(nitrilomethylidyne)]di-2-naphtholato}copper(II) ethanol monosolvate

Hadi Kargar ^a ^* and Reza Kia ^b,^c

^aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, ^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^cX-ray Crystallography Laboratory, Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: hkargar@pnu.ac.ir

(Received 15 December 2010; accepted 18 December 2010; online 24 December 2010)

The asymmetric unit of the title compound, [Cu(C₂₆H₂₂N₂O₂)]·C₂H₅OH, comprises a Schiff base complex and an ethanol molecule of crystallization. The Cu^II atom shows a distorted square-planar geometry. The dihedral angle between the two aromatic rings is 48.16 (13)°. The crystal structure is stabilized by intermolecular O—H⋯O and C—H⋯O hydrogen bonds and intermolecular π–π interactions with centroid–centroid distances in the range 3.485 (2)–3.845 (3) Å.

Related literature

For standard values of bond lengths, see: Allen et al. (1987 ). For background to Schiff base–metal complexes, see: Granovski et al. (1993 ); Blower et al. (1998 ); Elmali et al. (2000 ); Kargar et al. (2010 ).

Experimental

Crystal data

[Cu(C₂₆H₂₂N₂O₂)]·C₂H₆O
M_r = 504.06
Monoclinic, C 2/c
a = 13.468 (3) Å
b = 22.606 (5) Å
c = 15.831 (3) Å
β = 95.84 (3)°
V = 4794.9 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 296 K
0.42 × 0.26 × 0.22 mm

Data collection

Stoe IPDS II image plate diffractometer
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009 ) T_min = 0.973, T_max = 1.000
9868 measured reflections
4655 independent reflections
3110 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.126
S = 1.04
4655 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O1	0.90	1.95	2.837 (4)	167
C12—H12A⋯O2ⁱ	0.97	2.52	3.395 (5)	150
Symmetry code: (i) $[-x+2, y, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810053183/jh2247sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810053183/jh2247Isup2.hkl

checkCIF report

Comment top

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with the ease of preparation and structural variations (Granovski et al., 1993). Metal derivatives of the Schiff bases have been studied extensively, and Ni(II) and Cu(II) complexes play a major role in both synthetic and structurel research (Kargar et al., 2010; Elmali et al., 2000; Blower et al., 1998).

The asymmetric unit of the title compound, Fig. 1, comprises one unit of the Schiff base complex and an ethanol molecule of crystallization. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The geometry ground the Cu(II) atom is distorted square-planar which is coordinated by the N₂O₂ donor atoms of the desired potentially tetradenate Schiff base ligand. The dihedral angle between the two aromatic rings is 48.16 (13)°. The crystal structure is stabilized by the intermolecular O—H···O and C—H···O hydrogen bonds and intermolecular π–π interactions [Cg1···Cg1ⁱ = 3.4852 (18) Å, (i) 2 - x, y, 1/2 - z; Cg2···Cg2ⁱ = 3.7183 (6)Å; Cg3···Cg3ⁱ = 3.638 (2)Å; Cg4···Cg4ⁱ = 3.845 (3)Å], Cg1, Cg2, Cg3 and Cg4 are the centroids of the Cu1/O1/C1/C10/C11/N1, Cu1/O2/C26/C17/C16/N2, C17/C18/C23/C24/C25/C26, and C18–C23 rings, respectively.

Related literature top

For standard values of bond lengths, see: Allen et al. (1987). For background to Schiff base–metal complexes, see: Granovski et al. (1993); Blower et al. (1998); Elmali et al. (2000); Kargar et al. (2010).

Experimental top

The title compound was synthesized by adding bis(hydroxy naphtylidene)-1,4-butanediamine (2 mmol) to a solution of CuCl₂. 4 H₂O (2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant green solution was filtered. Dark-green block single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Structure description top

For standard values of bond lengths, see: Allen et al. (1987). For background to Schiff base–metal complexes, see: Granovski et al. (1993); Blower et al. (1998); Elmali et al. (2000); Kargar et al. (2010).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The intermolecular interaction is shown as dashed lines.
	Fig. 2. The packing of the title compound viewed down the a-axis showing dimer formation through the intermolecular C—H···O hydrogen bonds. All H atoms were removed for clarity except those involved in the hydrogen bonding. The intermolecular interactions are shown as dashed lines.

Bis(2-hydroxynaphtylidene)-1,4-butanediamine copper (II) ethanol solvate top

Crystal data top

[Cu(C₂₆H₂₂N₂O₂)]·C₂H₆O	F(000) = 2104
M_r = 504.06	D_x = 1.397 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 10437 reflections
a = 13.468 (3) Å	θ = 1.8–29.6°
b = 22.606 (5) Å	µ = 0.94 mm⁻¹
c = 15.831 (3) Å	T = 296 K
β = 95.84 (3)°	Block, dark-green
V = 4794.9 (17) Å³	0.42 × 0.26 × 0.22 mm
Z = 8

Data collection top

Stoe IPDS II image plate diffractometer	4655 independent reflections
Radiation source: fine-focus sealed tube	3110 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 26.0°, θ_min = 1.8°
ω scans	h = −16→16
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009)	k = −27→27
T_min = 0.973, T_max = 1.000	l = −14→19
9868 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0612P)²] where P = (F_o² + 2F_c²)/3
4655 reflections	(Δ/σ)_max = 0.001
308 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Cu(C₂₆H₂₂N₂O₂)]·C₂H₆O	V = 4794.9 (17) Å³
M_r = 504.06	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 13.468 (3) Å	µ = 0.94 mm⁻¹
b = 22.606 (5) Å	T = 296 K
c = 15.831 (3) Å	0.42 × 0.26 × 0.22 mm
β = 95.84 (3)°

Data collection top

Stoe IPDS II image plate diffractometer	4655 independent reflections
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009)	3110 reflections with I > 2σ(I)
T_min = 0.973, T_max = 1.000	R_int = 0.053
9868 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	Δρ_max = 0.55 e Å⁻³
4655 reflections	Δρ_min = −0.29 e Å⁻³
308 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
Cu1	0.99074 (3)	0.39671 (2)	0.13736 (3)	0.03967 (16)
O1	1.09554 (19)	0.34050 (11)	0.13087 (19)	0.0462 (7)
O2	1.0912 (2)	0.45001 (11)	0.18187 (19)	0.0475 (7)
N1	0.8934 (2)	0.33537 (13)	0.1535 (2)	0.0402 (8)
N2	0.9081 (2)	0.45888 (13)	0.08166 (19)	0.0368 (7)
C1	1.0894 (3)	0.28282 (16)	0.1258 (2)	0.0370 (9)
C2	1.1777 (3)	0.25202 (17)	0.1090 (3)	0.0465 (10)
H2A	1.2354	0.2734	0.1025	0.056*
C3	1.1793 (3)	0.19265 (17)	0.1022 (3)	0.0475 (10)
H3A	1.2376	0.1741	0.0895	0.057*
C4	1.0948 (3)	0.15794 (16)	0.1140 (3)	0.0419 (9)
C5	1.0986 (3)	0.09535 (18)	0.1096 (3)	0.0535 (11)
H5A	1.1573	0.0769	0.0977	0.064*
C6	1.0179 (4)	0.06193 (19)	0.1226 (3)	0.0627 (13)
H6A	1.0216	0.0209	0.1195	0.075*
C7	0.9301 (4)	0.08883 (17)	0.1405 (3)	0.0596 (13)
H7A	0.8752	0.0658	0.1502	0.072*
C8	0.9236 (3)	0.14926 (17)	0.1440 (3)	0.0506 (11)
H8A	0.8636	0.1665	0.1549	0.061*
C9	1.0052 (3)	0.18599 (17)	0.1315 (2)	0.0380 (8)
C10	1.0024 (3)	0.25057 (16)	0.1367 (3)	0.0372 (8)
C11	0.9126 (3)	0.27942 (16)	0.1541 (2)	0.0395 (9)
H11A	0.8612	0.2548	0.1676	0.047*
C12	0.7936 (3)	0.35263 (18)	0.1772 (3)	0.0470 (10)
H12A	0.8013	0.3864	0.2151	0.056*
H12B	0.7670	0.3203	0.2082	0.056*
C13	0.7198 (3)	0.3680 (2)	0.1035 (3)	0.0630 (13)
H13A	0.6532	0.3625	0.1204	0.076*
H13B	0.7278	0.3403	0.0579	0.076*
C14	0.7270 (3)	0.4312 (2)	0.0682 (3)	0.0595 (12)
H14A	0.6686	0.4387	0.0285	0.071*
H14B	0.7256	0.4590	0.1147	0.071*
C15	0.8183 (3)	0.4431 (2)	0.0241 (3)	0.0486 (10)
H15A	0.8331	0.4082	−0.0079	0.058*
H15B	0.8039	0.4751	−0.0160	0.058*
C16	0.9315 (3)	0.51465 (16)	0.0851 (2)	0.0359 (8)
H16A	0.8889	0.5400	0.0524	0.043*
C17	1.0155 (2)	0.54158 (15)	0.1335 (2)	0.0320 (8)
C18	1.0243 (3)	0.60666 (17)	0.1334 (2)	0.0346 (8)
C19	0.9549 (3)	0.64393 (17)	0.0881 (3)	0.0437 (10)
H19A	0.9002	0.6277	0.0557	0.052*
C20	0.9669 (4)	0.70446 (19)	0.0913 (3)	0.0589 (12)
H20A	0.9195	0.7286	0.0615	0.071*
C21	1.0488 (4)	0.7300 (2)	0.1382 (4)	0.0707 (15)
H21A	1.0564	0.7709	0.1391	0.085*
C22	1.1174 (3)	0.69509 (19)	0.1827 (3)	0.0584 (12)
H22A	1.1716	0.7123	0.2148	0.070*
C23	1.1074 (3)	0.63268 (17)	0.1808 (3)	0.0406 (9)
C24	1.1801 (3)	0.59615 (17)	0.2255 (3)	0.0441 (9)
H24A	1.2346	0.6138	0.2566	0.053*
C25	1.1733 (3)	0.53693 (17)	0.2245 (3)	0.0429 (9)
H25A	1.2232	0.5144	0.2540	0.052*
C26	1.0900 (3)	0.50794 (16)	0.1786 (2)	0.0362 (8)
O3	1.2478 (2)	0.40229 (16)	0.0561 (2)	0.0741 (10)
H1	1.2027	0.3859	0.0872	0.111*
C27	1.3277 (4)	0.4255 (3)	0.1075 (4)	0.0863 (18)
H27A	1.3024	0.4447	0.1557	0.104*
H27B	1.3594	0.4556	0.0758	0.104*
C28	1.4013 (6)	0.3832 (4)	0.1383 (5)	0.131 (3)
H28A	1.4506	0.4021	0.1774	0.197*
H28B	1.4328	0.3673	0.0915	0.197*
H28C	1.3702	0.3519	0.1668	0.197*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0315 (2)	0.0356 (2)	0.0519 (3)	−0.0033 (2)	0.00417 (19)	0.0020 (3)
O1	0.0345 (14)	0.0385 (15)	0.066 (2)	−0.0025 (12)	0.0089 (14)	−0.0030 (13)
O2	0.0387 (15)	0.0332 (14)	0.067 (2)	−0.0018 (12)	−0.0109 (14)	0.0052 (13)
N1	0.0309 (16)	0.0389 (17)	0.052 (2)	−0.0010 (13)	0.0092 (15)	0.0013 (15)
N2	0.0295 (16)	0.0404 (17)	0.0401 (19)	−0.0068 (13)	0.0021 (14)	−0.0015 (14)
C1	0.0316 (18)	0.035 (2)	0.045 (2)	0.0009 (15)	0.0031 (17)	−0.0003 (17)
C2	0.032 (2)	0.044 (2)	0.064 (3)	−0.0017 (16)	0.0079 (19)	0.003 (2)
C3	0.035 (2)	0.045 (2)	0.063 (3)	0.0073 (17)	0.006 (2)	−0.003 (2)
C4	0.043 (2)	0.037 (2)	0.045 (2)	−0.0006 (17)	0.0026 (18)	−0.0003 (17)
C5	0.053 (2)	0.041 (2)	0.066 (3)	0.006 (2)	0.005 (2)	−0.005 (2)
C6	0.075 (3)	0.032 (2)	0.081 (4)	−0.004 (2)	0.011 (3)	−0.005 (2)
C7	0.059 (3)	0.034 (2)	0.087 (4)	−0.0127 (19)	0.011 (3)	−0.009 (2)
C8	0.047 (2)	0.040 (2)	0.066 (3)	−0.0065 (19)	0.008 (2)	−0.002 (2)
C9	0.038 (2)	0.0394 (19)	0.037 (2)	−0.0013 (17)	0.0034 (17)	−0.0035 (18)
C10	0.035 (2)	0.0358 (18)	0.041 (2)	−0.0052 (16)	0.0022 (17)	−0.0029 (18)
C11	0.0342 (19)	0.041 (2)	0.044 (2)	−0.0055 (16)	0.0071 (17)	0.0002 (17)
C12	0.038 (2)	0.045 (2)	0.061 (3)	0.0015 (18)	0.017 (2)	0.000 (2)
C13	0.038 (2)	0.065 (3)	0.086 (4)	−0.013 (2)	0.002 (2)	0.007 (3)
C14	0.042 (2)	0.072 (3)	0.062 (3)	−0.002 (2)	−0.006 (2)	−0.001 (2)
C15	0.039 (2)	0.058 (3)	0.045 (3)	−0.0073 (19)	−0.0100 (19)	−0.001 (2)
C16	0.0298 (19)	0.040 (2)	0.038 (2)	0.0009 (16)	0.0029 (17)	0.0031 (16)
C17	0.0258 (18)	0.0373 (19)	0.033 (2)	−0.0036 (14)	0.0047 (16)	0.0020 (16)
C18	0.0326 (16)	0.0403 (19)	0.0318 (19)	−0.0016 (17)	0.0084 (15)	−0.0026 (18)
C19	0.043 (2)	0.039 (2)	0.048 (3)	0.0026 (18)	0.000 (2)	0.0033 (18)
C20	0.057 (3)	0.042 (2)	0.076 (3)	0.003 (2)	0.000 (3)	0.009 (2)
C21	0.074 (3)	0.038 (2)	0.099 (4)	−0.007 (2)	0.001 (3)	0.003 (3)
C22	0.048 (3)	0.046 (2)	0.079 (4)	−0.009 (2)	0.000 (2)	−0.007 (2)
C23	0.039 (2)	0.043 (2)	0.041 (2)	−0.0053 (17)	0.0078 (18)	−0.0022 (18)
C24	0.038 (2)	0.046 (2)	0.047 (2)	−0.0073 (18)	−0.0022 (17)	−0.0042 (19)
C25	0.035 (2)	0.044 (2)	0.049 (3)	−0.0023 (17)	−0.0026 (18)	0.0040 (18)
C26	0.0293 (18)	0.038 (2)	0.042 (2)	−0.0029 (15)	0.0075 (17)	−0.0005 (17)
O3	0.0546 (19)	0.092 (3)	0.077 (2)	−0.013 (2)	0.0114 (17)	0.008 (2)
C27	0.075 (4)	0.075 (4)	0.110 (5)	−0.018 (3)	0.012 (4)	−0.020 (3)
C28	0.099 (5)	0.142 (7)	0.143 (8)	0.010 (5)	−0.033 (5)	0.022 (6)

Geometric parameters (Å, º) top

Cu1—O2	1.893 (3)	C13—H13B	0.9700
Cu1—O1	1.910 (3)	C14—C15	1.498 (6)
Cu1—N1	1.943 (3)	C14—H14A	0.9700
Cu1—N2	1.947 (3)	C14—H14B	0.9700
O1—C1	1.308 (4)	C15—H15A	0.9700
O2—C26	1.311 (4)	C15—H15B	0.9700
N1—C11	1.291 (5)	C16—C17	1.436 (5)
N1—C12	1.485 (4)	C16—H16A	0.9300
N2—C16	1.299 (4)	C17—C26	1.397 (5)
N2—C15	1.481 (5)	C17—C18	1.476 (5)
C1—C10	1.405 (5)	C18—C19	1.400 (5)
C1—C2	1.427 (5)	C18—C23	1.411 (5)
C2—C3	1.347 (5)	C19—C20	1.378 (6)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.411 (5)	C20—C21	1.391 (7)
C3—H3A	0.9300	C20—H20A	0.9300
C4—C9	1.415 (5)	C21—C22	1.357 (7)
C4—C5	1.418 (5)	C21—H21A	0.9300
C5—C6	1.356 (6)	C22—C23	1.417 (6)
C5—H5A	0.9300	C22—H22A	0.9300
C6—C7	1.384 (6)	C23—C24	1.414 (5)
C6—H6A	0.9300	C24—C25	1.342 (5)
C7—C8	1.370 (6)	C24—H24A	0.9300
C7—H7A	0.9300	C25—C26	1.431 (5)
C8—C9	1.406 (5)	C25—H25A	0.9300
C8—H8A	0.9300	O3—C27	1.384 (6)
C9—C10	1.463 (5)	O3—H1	0.9000
C10—C11	1.426 (5)	C27—C28	1.427 (8)
C11—H11A	0.9300	C27—H27A	0.9700
C12—C13	1.495 (6)	C27—H27B	0.9700
C12—H12A	0.9700	C28—H28A	0.9600
C12—H12B	0.9700	C28—H28B	0.9600
C13—C14	1.541 (6)	C28—H28C	0.9600
C13—H13A	0.9700

O2—Cu1—O1	86.54 (12)	C15—C14—C13	114.9 (4)
O2—Cu1—N1	150.64 (14)	C15—C14—H14A	108.6
O1—Cu1—N1	92.55 (12)	C13—C14—H14A	108.6
O2—Cu1—N2	93.61 (12)	C15—C14—H14B	108.6
O1—Cu1—N2	147.92 (13)	C13—C14—H14B	108.6
N1—Cu1—N2	102.26 (13)	H14A—C14—H14B	107.5
C1—O1—Cu1	128.6 (2)	N2—C15—C14	114.5 (4)
C26—O2—Cu1	128.0 (3)	N2—C15—H15A	108.6
C11—N1—C12	116.2 (3)	C14—C15—H15A	108.6
C11—N1—Cu1	124.3 (3)	N2—C15—H15B	108.6
C12—N1—Cu1	119.1 (2)	C14—C15—H15B	108.6
C16—N2—C15	116.0 (3)	H15A—C15—H15B	107.6
C16—N2—Cu1	123.8 (3)	N2—C16—C17	127.4 (4)
C15—N2—Cu1	119.8 (2)	N2—C16—H16A	116.3
O1—C1—C10	124.0 (3)	C17—C16—H16A	116.3
O1—C1—C2	116.7 (3)	C26—C17—C16	121.9 (3)
C10—C1—C2	119.4 (3)	C26—C17—C18	119.3 (3)
C3—C2—C1	121.4 (4)	C16—C17—C18	118.8 (3)
C3—C2—H2A	119.3	C19—C18—C23	118.2 (4)
C1—C2—H2A	119.3	C19—C18—C17	123.4 (3)
C2—C3—C4	121.6 (4)	C23—C18—C17	118.4 (3)
C2—C3—H3A	119.2	C20—C19—C18	120.6 (4)
C4—C3—H3A	119.2	C20—C19—H19A	119.7
C3—C4—C9	119.5 (3)	C18—C19—H19A	119.7
C3—C4—C5	121.0 (4)	C19—C20—C21	121.0 (5)
C9—C4—C5	119.5 (4)	C19—C20—H20A	119.5
C6—C5—C4	121.0 (4)	C21—C20—H20A	119.5
C6—C5—H5A	119.5	C22—C21—C20	119.8 (4)
C4—C5—H5A	119.5	C22—C21—H21A	120.1
C5—C6—C7	120.0 (4)	C20—C21—H21A	120.1
C5—C6—H6A	120.0	C21—C22—C23	120.6 (4)
C7—C6—H6A	120.0	C21—C22—H22A	119.7
C8—C7—C6	120.4 (4)	C23—C22—H22A	119.7
C8—C7—H7A	119.8	C18—C23—C24	119.6 (3)
C6—C7—H7A	119.8	C18—C23—C22	119.7 (4)
C7—C8—C9	121.9 (4)	C24—C23—C22	120.7 (4)
C7—C8—H8A	119.0	C25—C24—C23	122.2 (4)
C9—C8—H8A	119.0	C25—C24—H24A	118.9
C8—C9—C4	117.1 (4)	C23—C24—H24A	118.9
C8—C9—C10	123.9 (4)	C24—C25—C26	120.8 (4)
C4—C9—C10	119.0 (3)	C24—C25—H25A	119.6
C1—C10—C11	121.4 (3)	C26—C25—H25A	119.6
C1—C10—C9	119.0 (3)	O2—C26—C17	124.7 (3)
C11—C10—C9	119.6 (3)	O2—C26—C25	115.6 (4)
N1—C11—C10	128.3 (3)	C17—C26—C25	119.7 (3)
N1—C11—H11A	115.8	C27—O3—H1	111.3
C10—C11—H11A	115.8	O3—C27—C28	114.8 (5)
N1—C12—C13	114.3 (4)	O3—C27—H27A	108.6
N1—C12—H12A	108.7	C28—C27—H27A	108.6
C13—C12—H12A	108.7	O3—C27—H27B	108.6
N1—C12—H12B	108.7	C28—C27—H27B	108.6
C13—C12—H12B	108.7	H27A—C27—H27B	107.6
H12A—C12—H12B	107.6	C27—C28—H28A	109.5
C12—C13—C14	115.9 (4)	C27—C28—H28B	109.5
C12—C13—H13A	108.3	H28A—C28—H28B	109.5
C14—C13—H13A	108.3	C27—C28—H28C	109.5
C12—C13—H13B	108.3	H28A—C28—H28C	109.5
C14—C13—H13B	108.3	H28B—C28—H28C	109.5
H13A—C13—H13B	107.4

O2—Cu1—O1—C1	160.0 (3)	C4—C9—C10—C11	179.8 (4)
N1—Cu1—O1—C1	9.4 (3)	C12—N1—C11—C10	−178.0 (4)
N2—Cu1—O1—C1	−108.7 (4)	Cu1—N1—C11—C10	−5.7 (6)
O1—Cu1—O2—C26	153.9 (3)	C1—C10—C11—N1	7.9 (7)
N1—Cu1—O2—C26	−117.1 (3)	C9—C10—C11—N1	−173.2 (4)
N2—Cu1—O2—C26	6.0 (3)	C11—N1—C12—C13	−101.9 (4)
O2—Cu1—N1—C11	−89.3 (4)	Cu1—N1—C12—C13	85.4 (4)
O1—Cu1—N1—C11	−1.9 (3)	N1—C12—C13—C14	−81.5 (5)
N2—Cu1—N1—C11	149.5 (3)	C12—C13—C14—C15	69.1 (5)
O2—Cu1—N1—C12	82.7 (4)	C16—N2—C15—C14	−102.7 (4)
O1—Cu1—N1—C12	170.2 (3)	Cu1—N2—C15—C14	83.6 (4)
N2—Cu1—N1—C12	−38.4 (3)	C13—C14—C15—N2	−83.3 (5)
O2—Cu1—N2—C16	−0.6 (3)	C15—N2—C16—C17	−178.3 (3)
O1—Cu1—N2—C16	−89.9 (4)	Cu1—N2—C16—C17	−4.8 (5)
N1—Cu1—N2—C16	154.5 (3)	N2—C16—C17—C26	6.2 (6)
O2—Cu1—N2—C15	172.5 (3)	N2—C16—C17—C18	−175.4 (3)
O1—Cu1—N2—C15	83.3 (3)	C26—C17—C18—C19	178.1 (3)
N1—Cu1—N2—C15	−32.3 (3)	C16—C17—C18—C19	−0.3 (5)
Cu1—O1—C1—C10	−9.7 (6)	C26—C17—C18—C23	−1.3 (5)
Cu1—O1—C1—C2	170.9 (3)	C16—C17—C18—C23	−179.7 (3)
O1—C1—C2—C3	−179.8 (4)	C23—C18—C19—C20	−1.1 (6)
C10—C1—C2—C3	0.8 (6)	C17—C18—C19—C20	179.4 (4)
C1—C2—C3—C4	−1.9 (7)	C18—C19—C20—C21	1.0 (7)
C2—C3—C4—C9	1.4 (7)	C19—C20—C21—C22	−0.9 (8)
C2—C3—C4—C5	−177.8 (4)	C20—C21—C22—C23	1.0 (8)
C3—C4—C5—C6	178.7 (4)	C19—C18—C23—C24	−178.4 (3)
C9—C4—C5—C6	−0.5 (7)	C17—C18—C23—C24	1.1 (5)
C4—C5—C6—C7	0.0 (8)	C19—C18—C23—C22	1.2 (5)
C5—C6—C7—C8	1.0 (8)	C17—C18—C23—C22	−179.4 (4)
C6—C7—C8—C9	−1.4 (8)	C21—C22—C23—C18	−1.1 (7)
C7—C8—C9—C4	0.8 (7)	C21—C22—C23—C24	178.4 (5)
C7—C8—C9—C10	−178.4 (4)	C18—C23—C24—C25	0.0 (6)
C3—C4—C9—C8	−179.1 (4)	C22—C23—C24—C25	−179.5 (4)
C5—C4—C9—C8	0.1 (6)	C23—C24—C25—C26	−1.0 (6)
C3—C4—C9—C10	0.2 (6)	Cu1—O2—C26—C17	−6.3 (5)
C5—C4—C9—C10	179.4 (4)	Cu1—O2—C26—C25	174.7 (3)
O1—C1—C10—C11	0.3 (6)	C16—C17—C26—O2	−0.3 (6)
C2—C1—C10—C11	179.7 (4)	C18—C17—C26—O2	−178.6 (3)
O1—C1—C10—C9	−178.6 (4)	C16—C17—C26—C25	178.7 (3)
C2—C1—C10—C9	0.8 (6)	C18—C17—C26—C25	0.4 (5)
C8—C9—C10—C1	178.0 (4)	C24—C25—C26—O2	179.8 (4)
C4—C9—C10—C1	−1.2 (6)	C24—C25—C26—C17	0.7 (6)
C8—C9—C10—C11	−1.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O1	0.90	1.95	2.837 (4)	167
C12—H12A···O2ⁱ	0.97	2.52	3.395 (5)	150

Symmetry code: (i) −x+2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₂₆H₂₂N₂O₂)]·C₂H₆O
M_r	504.06
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	13.468 (3), 22.606 (5), 15.831 (3)
β (°)	95.84 (3)
V (Å³)	4794.9 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.42 × 0.26 × 0.22

Data collection
Diffractometer	Stoe IPDS II image plate
Absorption correction	Multi-scan (MULABS in PLATON; Spek, 2009)
T_min, T_max	0.973, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9868, 4655, 3110
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.126, 1.04
No. of reflections	4655
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.29

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O1	0.90	1.95	2.837 (4)	167
C12—H12A···O2ⁱ	0.97	2.52	3.395 (5)	150

Symmetry code: (i) −x+2, y, −z+1/2.

Acknowledgements

HK thanks PNU for financial support. RK thanks the Science and Research Branch, Islamic Azad University.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Blower, P. J. (1998). Transition Met. Chem. 23, 109–112. CrossRef CAS Google Scholar
Elmali, A., Elerman, Y. & Svoboda, I. (2000). Acta Cryst. C56, 423–424. CSD CrossRef CAS IUCr Journals Google Scholar
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. Google Scholar
Kargar, H., Kia, R., Tahir, M. N. & Sahraei, A. (2010). Acta Cryst. E66, m1246. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{1,1′-[Butane-1,4-diylbis(nitrilo­methyl­­idyne)]di-2-naphtho­lato}copper(II) ethanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{1,1′-[Butane-1,4-diylbis(nitrilomethylidyne)]di-2-naphtholato}copper(II) ethanol monosolvate